Regioselective addition of DDQ on a quinoid ring: an entry into chiral zwitterionic bridging ligands
Canard, Gabriel; Chen, Zhongrui; Suryaningtias, Aprilliyani; Jean, Marion; Vanthuyne, Nicolas; Giorgi, Michel; Roussel, Christian; Siri, Olivier; New Journal of Chemistry 42 (2018) 8247–; doi:10.1039/C7NJ03765A

data_7057011
_publ_section_title
;
 Regioselective addition of DDQ on a quinoid ring: an entry into chiral
 zwitterionic bridging ligands
;
_journal_issue                   10
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              8247
_journal_paper_doi               10.1039/C7NJ03765A
_journal_volume                  42
_journal_year                    2018
_chemical_formula_moiety         'C22 H22 Cl2 N4 O4'
_chemical_formula_sum            'C22 H22 Cl2 N4 O4'
_chemical_formula_weight         477.33
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2017-09-05
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3461 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2017-09-06 deposited with the CCDC.
2018-02-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.255(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.4139(16)
_cell_length_b                   19.1246(19)
_cell_length_c                   9.4516(9)
_cell_measurement_reflns_used    2594
_cell_measurement_temperature    293
_cell_measurement_theta_max      60.8010
_cell_measurement_theta_min      4.6130
_cell_volume                     2360.1(4)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3048
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.978
_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   -121.00   9.00   1.00   10.00    --  -32.96 -38.00   0.00  130
  2  \w   -121.00 -89.00   1.00   10.00    --  -32.96 -99.00 120.00   32
  3  \w   -127.00   2.00   1.00   10.00    --  -32.96 -77.00 150.00  129
  4  \w    -83.00 -33.00   1.00   10.00    --  -32.96 -57.00 150.00   50
  5  \w    -64.00  55.00   1.00   10.00    --  -32.96  57.00 120.00  119
  6  \w    -91.00 -63.00   1.00   10.00    --  -32.96 -38.00  60.00   28
  7  \w   -124.00 -95.00   1.00   10.00    --  -32.96 -99.00-150.00   29
  8  \w     99.00 128.00   1.00   10.00    --   32.96 178.00-180.00   29
  9  \w     98.00 175.00   1.00   45.00    --   98.76  77.00 150.00   77
 10  \w     61.00  86.00   1.00   45.00    --   98.76  45.00-180.00   25
 11  \w     95.00 178.00   1.00   45.00    --   98.76  77.00  90.00   83
 12  \w     57.00  85.00   1.00   45.00    --   98.76  77.00 150.00   28
 13  \w     60.00  85.00   1.00   45.00    --   98.76  45.00 120.00   25
 14  \w     57.00  88.00   1.00   45.00    --   98.76  77.00-180.00   31
 15  \w     64.00  95.00   1.00   45.00    --   98.76  61.00-180.00   31
 16  \w     57.00  85.00   1.00   45.00    --   98.76  77.00  90.00   28
 17  \w     59.00  87.00   1.00   45.00    --   98.76  61.00 150.00   28
 18  \w     92.00 163.00   1.00   45.00    --   98.76  77.00  60.00   71
 19  \w     59.00  87.00   1.00   45.00    --   98.76  61.00  90.00   28
 20  \w     61.00  86.00   1.00   45.00    --   98.76  61.00 120.00   25
 21  \w     98.00 172.00   1.00   45.00    --   98.76  77.00 120.00   74
 22  \w    102.00 145.00   1.00   45.00    --   98.76 111.00  30.00   43
 23  \w    102.00 173.00   1.00   45.00    --   98.76  77.00-180.00   71
 24  \w     73.00 174.00   1.00   45.00    --   98.76  61.00-150.00  101
 25  \w     59.00 147.00   1.00   45.00    --   98.76 178.00-120.00   88
 26  \w     60.00  87.00   1.00   45.00    --   98.76  45.00  90.00   27
 27  \w     57.00  85.00   1.00   45.00    --   98.76  77.00 120.00   28
 28  \w     62.00  87.00   1.00   45.00    --   98.76  45.00 150.00   25
 29  \w     57.00  85.00   1.00   45.00    --   98.76  77.00  60.00   28
 30  \w      4.00 139.00   1.00   45.00    --   98.76 -77.00-180.00  135
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1084659000
_diffrn_orient_matrix_UB_12      -0.0220667000
_diffrn_orient_matrix_UB_13      -0.0108622000
_diffrn_orient_matrix_UB_21      -0.0259468000
_diffrn_orient_matrix_UB_22      0.0195179000
_diffrn_orient_matrix_UB_23      -0.1624183000
_diffrn_orient_matrix_UB_31      0.0387391000
_diffrn_orient_matrix_UB_32      0.0749745000
_diffrn_orient_matrix_UB_33      0.0389991000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_unetI/netI     0.0658
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            6451
_diffrn_reflns_point_group_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        66.581
_diffrn_reflns_theta_max         66.581
_diffrn_reflns_theta_min         4.100
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.776
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90947
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_description       prism
_exptl_crystal_F_000             992
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Toluene'
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.445
_refine_diff_density_min         -0.417
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     321
_refine_ls_number_reflns         6451
_refine_ls_number_restraints     27
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.1383
_refine_ls_R_factor_gt           0.0820
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1057P)^2^+1.5351P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2048
_refine_ls_wR_factor_ref         0.2342
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3612
_reflns_number_total             6451
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7nj03765a2.cif
_cod_data_source_block           recri23_2
_cod_depositor_comments          'Adding full bibliography for 7057011.cif.'
_cod_database_code               7057011
_shelx_shelxl_version_number     2016/4
_shelx_estimated_absorpt_t_max   0.973
_shelx_estimated_absorpt_t_min   0.874
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.553(2)
 0.447(2)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
3. Restrained distances
 C24-C25
 1.54 with sigma of 0.02
 C17-C18
 1.54 with sigma of 0.005
 C23-C25
 2.5 with sigma of 0.04
4. Rigid bond restraints
 C20, C21, C22
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C16, C17, C18
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
5. Uiso/Uaniso restraints and constraints
C23 \\sim C24 \\sim C25: within 1.7A with sigma of 0.001 and sigma for terminal
atoms of 0.001
C17 \\sim C18: within 1.7A with sigma of 0.001 and sigma for terminal atoms of
0.001
6. Others
 Fixed Sof: H19A(0.5) H19B(0.5) H19C(0.5) H19D(0.5) C20(0.5) H20A(0.5)
 H20B(0.5) C21(0.5) H21A(0.5) H21B(0.5) C22(0.5) H22A(0.5) H22B(0.5) H22C(0.5)
 C23(0.5) H23A(0.5) H23B(0.5) C24(0.5) H24A(0.5) H24B(0.5) C25(0.5) H25A(0.5)
 H25B(0.5) H25C(0.5)
7.a Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C16(H16A,H16B), C17(H17A,H17B), C19(H19A,H19B), C19(H19C,
 H19D), C20(H20A,H20B), C21(H21A,H21B), C23(H23A,H23B), C24(H24A,H24B)
7.b Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), C4(H4)
7.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C22(H22A,H22B,H22C), C25(H25A,H25B,H25C)
7.d Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_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 1.414
_oxdiff_exptl_absorpt_empirical_full_min 0.781
_oxdiff_twin_integration_method  simultaneous
_oxdiff_twin_items               2
_twin_special_details
;
Component 2 rotated by -179.6263\% 
 around [-0.31 0.00 0.95] (reciprocal) or [-0.00 -0.00 1.00] (direct)
;