Phen-2NO, a new C2-symmetric rigid-featured tetradentate ligand, and its application in the asymmetric alkylation reaction of indoles
Chen, Zi-Yue; Xu, Ke-Lan; Wang, Xi-Rui; Hu, Pan; Jiang, Wei-Yan; Dai, Yi-Feng; Peng, Li-Jun; Liu, Xiong-Li; New Journal of Chemistry 48 (2024) 6670–6675; doi:10.1039/D4NJ00088A

data_7063083
_publ_section_title
;
 Phen-2NO, a new C2-symmetric rigid-featured tetradentate ligand, and its
 application in the asymmetric alkylation reaction of indoles
;
_journal_issue                   15
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              6670
_journal_page_last               6675
_journal_paper_doi               10.1039/D4NJ00088A
_journal_volume                  48
_journal_year                    2024
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C38 H36 N6 O2, 2(H2 O)'
_chemical_formula_sum            'C38 H40 N6 O4'
_chemical_formula_weight         644.76
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2023-09-16
_audit_creation_method
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2023-09-25 deposited with the CCDC.	2024-03-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.32674(13)
_cell_length_b                   13.9964(2)
_cell_length_c                   25.3147(3)
_cell_measurement_reflns_used    10762
_cell_measurement_temperature    99.97(13)
_cell_measurement_theta_max      73.9770
_cell_measurement_theta_min      3.4940
_cell_volume                     3304.60(8)
_computing_cell_refinement       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.97(13)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.984
_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    -10.00  31.00   0.50    0.50    --    0.00 -82.00   0.00   82
  2  \w    -28.00  30.00   0.50    0.50    --    0.00 -82.00 -60.00  116
  3  \w    -33.00  17.00   0.50    0.50    --    0.00 -82.00 120.00  100
  4  \w    -19.00   6.00   0.50    0.50    --    0.00 -82.00-180.00   50
  5  \w     12.00  81.00   0.50    0.50    --   95.80 -30.00 120.00  138
  6  \w     98.00 143.00   0.50    0.50    --   95.80  82.00  30.00   90
  7  \w     72.00 107.00   0.50    0.50    --   95.80  15.00 -60.00   70
  8  \w     13.00 104.00   0.50    0.50    --   95.80 -77.00 -90.00  182
  9  \w     72.00 149.00   0.50    0.50    --   95.80  61.00  60.00  154
 10  \w     12.00 117.00   0.50    0.50    --   95.80 -61.00 -90.00  210
 11  \w    146.00 184.00   0.50    0.50    --   95.80  15.00 -60.00   76
 12  \w    129.00 175.50   0.50    0.50    --   95.80  30.00 -90.00   93
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0098127000
_diffrn_orient_matrix_UB_12      0.0679664000
_diffrn_orient_matrix_UB_13      0.0477481000
_diffrn_orient_matrix_UB_21      -0.0663392000
_diffrn_orient_matrix_UB_22      -0.0775282000
_diffrn_orient_matrix_UB_23      0.0355403000
_diffrn_orient_matrix_UB_31      0.1509692000
_diffrn_orient_matrix_UB_32      -0.0386803000
_diffrn_orient_matrix_UB_33      0.0125070000
_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  0.0389
_diffrn_reflns_av_unetI/netI     0.0407
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            16596
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.213
_diffrn_reflns_theta_min         3.492
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.690
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.58358
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.33c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_description       block
_exptl_crystal_F_000             1368
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.394
_refine_diff_density_min         -0.359
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details
;
 Flack x determined using 2512 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     446
_refine_ls_number_reflns         6509
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0463
_refine_ls_R_factor_gt           0.0446
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.005
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0772P)^2^+0.9472P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1248
_refine_ls_wR_factor_ref         0.1264
_reflns_Friedel_coverage         0.746
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.946
_reflns_number_gt                6207
_reflns_number_total             6509
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4nj00088a2.cif
_cod_data_source_block           cyl-pe-3
_cod_depositor_comments          'Adding full bibliography for 7063083.cif.'
_cod_original_cell_volume        3304.59(8)
_cod_database_code               7063083
_shelx_shelxl_version_number     2018/3
_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,H) groups
2. Restrained distances
 O3-H3A = O3-H3B
 0.82 with sigma of 0.01
 O3-H3B
 0.82 with sigma of 0.01
3.a Free rotating group:
 O4(H4A,H4B)
3.b Ternary CH refined with riding coordinates:
 C12(H12), C25(H25), C27(H27), C8(H8)
3.c Secondary CH2 refined with riding coordinates:
 C28(H28A,H28B), C9(H9A,H9B), C11(H11A,H11B), C10(H10A,H10B), C29(H29A,H29B),
 C30(H30A,H30B)
3.d Aromatic/amide H refined with riding coordinates:
 C23(H23), C14(H14), C22(H22), C15(H15), C00O(H00O), C2(H2), C18(H18),
 C17(H17), C6(H6), C32(H32), C34(H34), C4(H4), C33(H33), C5(H5)
3.e Idealised Me refined as rotating group:
 C36(H36A,H36B,H36C), C37(H37A,H37B,H37C)
;
_shelx_res_checksum              10259
_shelx_hkl_checksum              75042
_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 2.000
_oxdiff_exptl_absorpt_empirical_full_min 0.431