#------------------------------------------------------------------------------
#$Date: 2023-05-05 05:53:58 +0300 (Fri, 05 May 2023) $
#$Revision: 283384 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/23/7062394.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_7062394
loop_
_publ_author_name
'Patel, Bhavya'
'Ranjan, Rishi'
'Chauhan, Nimesh R.'
'Mukhopadhyay, Suman'
'Choudhury, Angshuman Roy'
'Vyas, Komal M.'
_publ_section_title
;
 N-coordinated Ru(ii) catalyzed solvent free N-alkylation of primary
 amines with alcohols through borrowing hydrogen strategy
;
_journal_issue                   17
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              8305
_journal_page_last               8317
_journal_paper_doi               10.1039/D3NJ00210A
_journal_volume                  47
_journal_year                    2023
_chemical_formula_moiety         'C20 H20 Cl N O2 Ru'
_chemical_formula_sum            'C20 H20 Cl N O2 Ru'
_chemical_formula_weight         442.89
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2019-11-19
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-12-04 deposited with the CCDC.	2023-03-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 117.668(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.8285(5)
_cell_length_b                   17.5067(5)
_cell_length_c                   10.5960(5)
_cell_measurement_reflns_used    4048
_cell_measurement_temperature    298.0
_cell_measurement_theta_max      28.5650
_cell_measurement_theta_min      3.1360
_cell_volume                     1779.01(16)
_computing_cell_refinement       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_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      298.0
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.919
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -69.00 118.20   0.30   10.00    --   29.89  54.00-150.00  624
  2  ω    -57.00 108.00   0.30   10.00    --   29.89  54.00  90.00  550
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini (ROW)'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0622688000
_diffrn_orient_matrix_UB_12      0.0073249000
_diffrn_orient_matrix_UB_13      0.0044750000
_diffrn_orient_matrix_UB_21      -0.0344621000
_diffrn_orient_matrix_UB_22      -0.0291011000
_diffrn_orient_matrix_UB_23      -0.0509806000
_diffrn_orient_matrix_UB_31      0.0200807000
_diffrn_orient_matrix_UB_32      -0.0272331000
_diffrn_orient_matrix_UB_33      0.0556177000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0306
_diffrn_reflns_av_unetI/netI     0.0455
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.919
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            15820
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.919
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.792
_diffrn_reflns_theta_min         2.509
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.044
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82838
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.35c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'metallic yellowish yellow'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.654
_exptl_crystal_description       plate
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.19
_refine_diff_density_max         1.769
_refine_diff_density_min         -0.777
_refine_diff_density_rms         0.102
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         6065
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.096
_refine_ls_R_factor_all          0.0618
_refine_ls_R_factor_gt           0.0400
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0428P)²+0.5905P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0929
_refine_ls_wR_factor_ref         0.1091
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4506
_reflns_number_total             6065
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3nj00210a2.cif
_cod_data_source_block           bp07
_cod_depositor_comments
'Adding full bibliography for 7062393--7062394.cif.'
_cod_original_cell_volume        1779.01(15)
_cod_database_code               7062394
_shelx_shelxl_version_number     2014/7
_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.
;
_reflns_odcompleteness_completeness 99.79
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.30
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C18(H18)
2.b Aromatic/amide H refined with riding coordinates:
 C16(H16), C11(H11), C14(H14), C2(H2), C8(H8), C13(H13), C7(H7), C5(H5),
 C3(H3), C4(H4)
2.c Idealised Me refined as rotating group:
 C20(H20a,H20b,H20c), C17(H17a,H17b,H17c), C19(H19a,H19b,H19c)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.158
_oxdiff_exptl_absorpt_empirical_full_min 0.881
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
Ru1 Ru 0.37386(2) 0.56663(2) 0.74369(2) 0.02992(8) Uani 1 1 d . . . . .
Cl1 Cl 0.17188(8) 0.53587(4) 0.77287(8) 0.04236(17) Uani 1 1 d . . . . .
O1 O 0.4414(2) 0.63661(11) 0.9227(2) 0.0395(4) Uani 1 1 d . . . . .
N1 N 0.2768(2) 0.67277(11) 0.6566(2) 0.0300(4) Uani 1 1 d . . . . .
O2 O 0.4801(3) 0.75894(13) 0.9894(3) 0.0615(7) Uani 1 1 d . . . . .
C16 C 0.5027(3) 0.57128(15) 0.6370(3) 0.0357(6) Uani 1 1 d . . . . .
H16 H 0.5211 0.6123 0.5925 0.043 Uiso 1 1 calc R . . . .
C9 C 0.3339(3) 0.73071(14) 0.7457(3) 0.0335(5) Uani 1 1 d . . . . .
C15 C 0.5900(3) 0.55742(16) 0.7820(3) 0.0379(6) Uani 1 1 d . . . . .
C1 C 0.1790(3) 0.68766(14) 0.5185(3) 0.0315(5) Uani 1 1 d . . . . .
C11 C 0.3865(3) 0.52327(16) 0.5573(3) 0.0390(6) Uani 1 1 d . . . . .
H11 H 0.3302 0.5334 0.4611 0.047 Uiso 1 1 calc R . . . .
C14 C 0.5563(3) 0.49387(16) 0.8462(3) 0.0406(6) Uani 1 1 d . . . . .
H14 H 0.6126 0.4836 0.9423 0.049 Uiso 1 1 calc R . . . .
C6 C 0.1528(3) 0.76423(14) 0.4670(3) 0.0353(6) Uani 1 1 d . . . . .
C2 C 0.1015(3) 0.62769(16) 0.4264(3) 0.0398(6) Uani 1 1 d . . . . .
H2 H 0.1145 0.5776 0.4595 0.048 Uiso 1 1 calc R . . . .
C10 C 0.4272(3) 0.70874(16) 0.8987(3) 0.0391(6) Uani 1 1 d . . . . .
C8 C 0.3077(3) 0.80730(15) 0.7024(3) 0.0412(6) Uani 1 1 d . . . . .
H8 H 0.3484 0.8463 0.7684 0.049 Uiso 1 1 calc R . . . .
C13 C 0.4411(4) 0.44698(16) 0.7679(4) 0.0441(7) Uani 1 1 d . . . . .
H13 H 0.4211 0.4067 0.8129 0.053 Uiso 1 1 calc R . . . .
C12 C 0.3544(3) 0.46040(16) 0.6206(3) 0.0424(7) Uani 1 1 d . . . . .
C7 C 0.2224(3) 0.82412(15) 0.5634(3) 0.0431(7) Uani 1 1 d . . . . .
H7 H 0.2100 0.8745 0.5320 0.052 Uiso 1 1 calc R . . . .
C18 C 0.7139(3) 0.60676(19) 0.8745(3) 0.0441(7) Uani 1 1 d . . . . .
H18 H 0.7148 0.6125 0.9669 0.053 Uiso 1 1 calc R . . . .
C5 C 0.0572(3) 0.77728(17) 0.3225(3) 0.0454(7) Uani 1 1 d . . . . .
H5 H 0.0418 0.8268 0.2867 0.055 Uiso 1 1 calc R . . . .
C3 C 0.0074(3) 0.64345(18) 0.2885(3) 0.0477(7) Uani 1 1 d . . . . .
H3 H -0.0445 0.6039 0.2288 0.057 Uiso 1 1 calc R . . . .
C4 C -0.0123(4) 0.71837(19) 0.2357(4) 0.0502(8) Uani 1 1 d . . . . .
H4 H -0.0734 0.7276 0.1402 0.060 Uiso 1 1 calc R . . . .
C20 C 0.7111(4) 0.68636(19) 0.8164(4) 0.0564(9) Uani 1 1 d . . . . .
H20A H 0.7196 0.6828 0.7303 0.085 Uiso 1 1 calc GR . . . .
H20B H 0.7873 0.7157 0.8856 0.085 Uiso 1 1 calc GR . . . .
H20C H 0.6246 0.7109 0.7964 0.085 Uiso 1 1 calc GR . . . .
C17 C 0.2281(4) 0.4109(2) 0.5367(4) 0.0601(9) Uani 1 1 d . . . . .
H17A H 0.1871 0.3964 0.5963 0.090 Uiso 1 1 calc GR . . . .
H17B H 0.2558 0.3659 0.5045 0.090 Uiso 1 1 calc GR . . . .
H17C H 0.1613 0.4389 0.4559 0.090 Uiso 1 1 calc GR . . . .
C19 C 0.8474(4) 0.5644(2) 0.9003(5) 0.0661(11) Uani 1 1 d . . . . .
H19A H 0.8497 0.5155 0.9422 0.099 Uiso 1 1 calc GR . . . .
H19B H 0.9271 0.5938 0.9637 0.099 Uiso 1 1 calc GR . . . .
H19C H 0.8492 0.5574 0.8113 0.099 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'
Cl Cl 0.1484 0.1585 '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'
Ru Ru -1.2594 0.8363 '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
O1 Ru1 Cl1 88.28(6) . . ?
O1 Ru1 N1 76.98(8) . . ?
O1 Ru1 C16 114.46(10) . . ?
O1 Ru1 C15 88.94(10) . . ?
O1 Ru1 C11 152.44(10) . . ?
O1 Ru1 C14 92.10(10) . . ?
O1 Ru1 C13 119.84(10) . . ?
O1 Ru1 C12 157.30(10) . . ?
N1 Ru1 Cl1 87.45(6) . . ?
N1 Ru1 C16 92.83(9) . . ?
N1 Ru1 C15 114.60(9) . . ?
N1 Ru1 C11 97.93(10) . . ?
N1 Ru1 C14 151.99(10) . . ?
N1 Ru1 C13 163.18(11) . . ?
N1 Ru1 C12 125.72(10) . . ?
C16 Ru1 Cl1 156.73(8) . . ?
C16 Ru1 C15 37.56(11) . . ?
C16 Ru1 C11 38.13(11) . . ?
C16 Ru1 C14 68.05(11) . . ?
C16 Ru1 C13 80.68(11) . . ?
C16 Ru1 C12 68.53(11) . . ?
C15 Ru1 Cl1 156.49(8) . . ?
C15 Ru1 C13 68.88(12) . . ?
C15 Ru1 C12 81.32(11) . . ?
C11 Ru1 Cl1 118.81(8) . . ?
C11 Ru1 C15 68.31(11) . . ?
C11 Ru1 C13 67.44(11) . . ?
C11 Ru1 C12 37.43(11) . . ?
C14 Ru1 Cl1 118.32(8) . . ?
C14 Ru1 C15 38.48(10) . . ?
C14 Ru1 C11 79.82(11) . . ?
C14 Ru1 C13 37.39(12) . . ?
C14 Ru1 C12 67.61(12) . . ?
C13 Ru1 Cl1 92.47(9) . . ?
C13 Ru1 C12 37.46(12) . . ?
C12 Ru1 Cl1 92.53(8) . . ?
C10 O1 Ru1 116.03(17) . . ?
C9 N1 Ru1 112.76(17) . . ?
C9 N1 C1 119.1(2) . . ?
C1 N1 Ru1 127.53(16) . . ?
C15 C16 Ru1 72.00(17) . . ?
C15 C16 C11 120.7(3) . . ?
C11 C16 Ru1 71.39(16) . . ?
N1 C9 C10 115.3(2) . . ?
N1 C9 C8 122.8(3) . . ?
C8 C9 C10 121.9(2) . . ?
C16 C15 Ru1 70.44(17) . . ?
C16 C15 C14 117.6(3) . . ?
C16 C15 C18 123.7(3) . . ?
C14 C15 Ru1 70.13(16) . . ?
C14 C15 C18 118.7(3) . . ?
C18 C15 Ru1 129.0(2) . . ?
N1 C1 C6 120.2(2) . . ?
N1 C1 C2 120.7(2) . . ?
C2 C1 C6 119.0(2) . . ?
C16 C11 Ru1 70.48(16) . . ?
C12 C11 Ru1 73.03(17) . . ?
C12 C11 C16 121.6(3) . . ?
C15 C14 Ru1 71.38(16) . . ?
C13 C14 Ru1 72.17(16) . . ?
C13 C14 C15 121.8(3) . . ?
C7 C6 C1 118.5(3) . . ?
C7 C6 C5 122.7(3) . . ?
C5 C6 C1 118.8(3) . . ?
C3 C2 C1 119.8(3) . . ?
O1 C10 C9 115.0(2) . . ?
O2 C10 O1 125.4(3) . . ?
O2 C10 C9 119.6(3) . . ?
C7 C8 C9 119.6(3) . . ?
C14 C13 Ru1 70.44(16) . . ?
C14 C13 C12 120.5(3) . . ?
C12 C13 Ru1 72.48(16) . . ?
C11 C12 Ru1 69.54(16) . . ?
C11 C12 C13 117.9(3) . . ?
C11 C12 C17 121.5(3) . . ?
C13 C12 Ru1 70.05(16) . . ?
C13 C12 C17 120.5(3) . . ?
C17 C12 Ru1 129.6(2) . . ?
C8 C7 C6 119.3(2) . . ?
C15 C18 C20 114.7(3) . . ?
C15 C18 C19 108.6(3) . . ?
C20 C18 C19 110.9(3) . . ?
C4 C5 C6 120.6(3) . . ?
C2 C3 C4 121.0(3) . . ?
C5 C4 C3 120.5(3) . . ?
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 2.4077(8) . ?
Ru1 O1 2.0850(19) . ?
Ru1 N1 2.123(2) . ?
Ru1 C16 2.167(3) . ?
Ru1 C15 2.187(3) . ?
Ru1 C11 2.179(3) . ?
Ru1 C14 2.171(3) . ?
Ru1 C13 2.193(3) . ?
Ru1 C12 2.225(3) . ?
O1 C10 1.283(3) . ?
N1 C9 1.327(3) . ?
N1 C1 1.376(3) . ?
O2 C10 1.230(3) . ?
C16 C15 1.402(4) . ?
C16 C11 1.420(4) . ?
C9 C10 1.509(4) . ?
C9 C8 1.403(4) . ?
C15 C14 1.436(4) . ?
C15 C18 1.512(4) . ?
C1 C6 1.425(3) . ?
C1 C2 1.414(4) . ?
C11 C12 1.414(4) . ?
C14 C13 1.399(4) . ?
C6 C7 1.412(4) . ?
C6 C5 1.413(4) . ?
C2 C3 1.366(4) . ?
C8 C7 1.359(4) . ?
C13 C12 1.419(5) . ?
C12 C17 1.511(5) . ?
C18 C20 1.518(5) . ?
C18 C19 1.532(5) . ?
C5 C4 1.354(4) . ?
C3 C4 1.403(5) . ?
