Streamlined synthetic assembly of α-chiral CAAC ligands and catalytic performance of their copper and ruthenium complexes.
Madron du Vigné, Adrien; Cramer, Nicolai; Chemical science 15 (2024) 13864–13871; doi:10.1039/d4sc04278f

data_1572162
_publ_section_title
;
 Streamlined synthetic assembly of &#x3b1;-chiral CAAC ligands and
 catalytic performance of their copper and ruthenium complexes.
;
_journal_issue                   34
_journal_name_full               'Chemical science'
_journal_page_first              13864
_journal_page_last               13871
_journal_paper_doi               10.1039/d4sc04278f
_journal_volume                  15
_journal_year                    2024
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C21 H31 Cl Cu N'
_chemical_formula_sum            'C21 H31 Cl Cu N'
_chemical_formula_weight         396.46
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2022-07-27
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2022-07-27 deposited with the CCDC.	2024-07-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.352(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.6227(3)
_cell_length_b                   8.2304(3)
_cell_length_c                   12.9158(3)
_cell_measurement_reflns_used    6895
_cell_measurement_temperature    140.00(10)
_cell_measurement_theta_max      76.2390
_cell_measurement_theta_min      3.3950
_cell_volume                     1012.07(5)
_computing_cell_refinement       'CrysAlisPro 1.171.42.61a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.61a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.61a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT 2018/2 (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      140.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.2665
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -50.00 -25.00   1.00    1.00    --  -43.01  17.00-148.00   25
  2  \w   -112.00   4.00   1.00    1.00    --  -43.01 -17.00  42.00  116
  3  \w     36.00  63.00   1.00    1.00    --   43.01  17.00-148.00   27
  4  \w     97.00 122.00   1.00    3.00    --  112.00  17.00-148.00   25
  5  \w     79.00 104.00   1.00    3.00    --  112.00 -17.00  42.00   25
  6  \w   -108.00 -15.00   1.00    1.00    --  -43.01 -57.00 -60.00   93
  7  \w    -82.00 -15.00   1.00    1.00    --  -43.01 -57.00-120.00   67
  8  \w   -114.00 -28.00   1.00    1.00    --  -43.01 -57.00-150.00   86
  9  \w     22.00  65.00   1.00    1.00    --   43.01  37.00-120.00   43
 10  \w     29.00  96.00   1.00    1.00    --   43.01-125.00  60.00   67
 11  \w      7.00  58.00   1.00    1.00    --   43.01 -99.00   0.00   51
 12  \w     83.00 112.00   1.00    3.00    --  112.00  61.00   0.00   29
 13  \w     41.00 140.00   1.00    3.00    --  112.00 -61.00  90.00   99
 14  \w    147.00 178.00   1.00    3.00    --  112.00  61.00-120.00   31
 15  \w     40.00 104.00   1.00    3.00    --  112.00-111.00 -30.00   64
 16  \w     84.00 110.00   1.00    3.00    --  112.00  61.00 -30.00   26
 17  \w    121.00 178.00   1.00    3.00    --  112.00  61.00 -30.00   57
 18  \w     84.00 109.00   1.00    3.00    --  112.00  61.00 -53.98   25
 19  \w    152.00 177.00   1.00    3.00    --  112.00  61.00 -53.98   25
 20  \w    117.00 170.00   1.00    3.00    --  112.00  45.00 -90.00   53
 21  \w     84.00 109.00   1.00    3.00    --  112.00  61.00 -90.00   25
 22  \w     87.00 112.00   1.00    3.00    --  112.00  45.00 -90.00   25
 23  \w     84.00 125.00   1.00    3.00    --  112.00  66.00  48.83   41
 24  \w     86.00 113.00   1.00    3.00    --  112.00  58.00 -77.30   27
 25  \w     84.00 110.00   1.00    3.00    --  112.00  58.00  -9.49   26
 26  \w     83.00 109.00   1.00    3.00    --  112.00  61.00  30.00   26
 27  \w    119.00 178.00   1.00    3.00    --  112.00  61.00  30.00   59
 28  \w     83.00 109.00   1.00    3.00    --  112.00  61.00 -60.00   26
 29  \w     78.00 118.00   1.00    3.00    --  112.00 -61.00 -90.00   40
 30  \w     88.00 148.00   1.00    3.00    --  112.00  45.00  30.00   60
 31  \w    127.00 154.00   1.00    3.00    --  112.00  30.00 -90.00   27
 32  \w     61.00 125.00   1.00    3.00    --  112.00 178.00   0.00   64
 33  \w     90.00 117.00   1.00    3.00    --  112.00  45.00-120.00   27
 34  \w     84.00 110.00   1.00    3.00    --  112.00  30.00   0.00   26
 35  \w     87.00 112.00   1.00    3.00    --  112.00  45.00   0.00   25
 36  \w     87.00 114.00   1.00    3.00    --  112.00  30.00 -90.00   27
 37  \w     39.00 106.00   1.00    3.00    --  112.00-111.00 -90.00   67
 38  \w     88.00 178.00   1.00    3.00    --  112.00  30.00 -60.00   90
 39  \w    102.00 127.00   1.00    3.00    --  112.00  30.00 -30.00   25
 40  \w    142.00 167.00   1.00    3.00    --  112.00  61.00   0.00   25
 41  \w     83.00 110.00   1.00    3.00    --  112.00  61.00-120.00   27
 42  \w     41.00  66.00   1.00    3.00    --  112.00-111.00-150.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0028014000
_diffrn_orient_matrix_UB_12      -0.0255556000
_diffrn_orient_matrix_UB_13      -0.1177898000
_diffrn_orient_matrix_UB_21      0.1593102000
_diffrn_orient_matrix_UB_22      0.0328099000
_diffrn_orient_matrix_UB_23      0.0164581000
_diffrn_orient_matrix_UB_31      0.0281350000
_diffrn_orient_matrix_UB_32      -0.1825855000
_diffrn_orient_matrix_UB_33      0.0194902000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0330
_diffrn_reflns_av_unetI/netI     0.0354
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            11385
_diffrn_reflns_point_group_measured_fraction_full 0.938
_diffrn_reflns_point_group_measured_fraction_max 0.922
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.457
_diffrn_reflns_theta_min         3.459
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.725
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.403
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.61a (Rigaku Oxford Diffraction, 2022)
Numerical absorption correction based on Gaussian integration over
a multifaceted crystal model.
Empirical absorption correction using spherical harmonics
as implemented in SCALE3 ABSPACK scaling algorithm
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_description       needle
_exptl_crystal_F_000             420
_exptl_crystal_size_max          0.66
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.298
_refine_diff_density_min         -0.294
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details
;
 Flack x determined using 1464 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.028(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         3906
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0343
_refine_ls_R_factor_gt           0.0310
_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^)+(0.0363P)^2^+0.2887P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0756
_refine_ls_wR_factor_ref         0.0777
_reflns_Friedel_coverage         0.734
_reflns_Friedel_fraction_full    0.866
_reflns_Friedel_fraction_max     0.841
_reflns_number_gt                3671
_reflns_number_total             3906
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc04278f2.cif
_cod_data_source_block           amd-r855_2
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Gaussian' was
changed to 'gaussian' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 

 Adding full bibliography for 1572161--1572166.cif.
;
_cod_original_cell_volume        1012.06(5)
_cod_database_code               1572162
_shelx_shelxl_version_number     2018/3
_audit_contact_author            'Farzaneh Fadaei Tirani'
_chemical_oxdiff_formula         'C21 H31 Cl Cu N'
_shelx_estimated_absorpt_t_max   0.899
_shelx_estimated_absorpt_t_min   0.266
_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
2.a Ternary CH refined with riding coordinates:
 C5(H5), C6(H6)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C7(H7A,H7B), C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B), C11(H11A,
 H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C14(H14), C15(H15), C16(H16), C17(H17), C18(H18)
2.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C19(H19A,H19B,H19C), C20(H20A,H20B,H20C), C21(H21A,H21B,
 H21C)
;
_shelx_res_checksum              62846
_shelx_hkl_checksum              65234
_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
- Detector area scaling
- B-factor correction
;
_oxdiff_exptl_absorpt_empirical_full_max 1.523
_oxdiff_exptl_absorpt_empirical_full_min 0.741