Schiff base ligands derived from 1,2-bis(2′-nitro-/amino-phenoxy)-3-R-benzene and 2-hydroxy-1-naphthaldehyde and their Cu/Zn(ii) complexes: synthesis, characterization, X-ray structures and computational studies
Aryaeifar, Mahnaz; Amiri Rudbari, Hadi; Blacque, Olivier; Islam, Mohammad Khairul; Scopelliti, Rosario; Braun, Jason D.; Herbert, David E.; Bruno, Giuseppe; Janiak, Christoph; Enamullah, Mohammed; CrystEngComm 23 (2021) 6322–6339; doi:10.1039/D1CE00829C

data_7243407
_publ_section_title
;
 Schiff base ligands derived from
 1,2-bis(2&#x2032;-nitro-/amino-phenoxy)-3-R-benzene and
 2-hydroxy-1-naphthaldehyde and their Cu/Zn(ii) complexes: synthesis,
 characterization, X-ray structures and computational studies
;
_journal_issue                   36
_journal_name_full               CrystEngComm
_journal_page_first              6322
_journal_page_last               6339
_journal_paper_doi               10.1039/D1CE00829C
_journal_volume                  23
_journal_year                    2021
_chemical_formula_moiety         'C19 H14 N2 O6'
_chemical_formula_sum            'C19 H14 N2 O6'
_chemical_formula_weight         366.32
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-05-03
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-10-23 deposited with the CCDC.	2021-07-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.1250(5)
_cell_length_b                   13.7648(11)
_cell_length_c                   15.2241(11)
_cell_measurement_reflns_used    7125
_cell_measurement_temperature    160.0(10)
_cell_measurement_theta_max      78.5
_cell_measurement_theta_min      4.3
_cell_volume                     1702.6(2)
_computing_cell_refinement       'CrysAlisPro 1.171.40.39a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.39a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.39a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015b)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015a)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      160.0(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_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    -92.00  -9.00   0.50    5.00    --  -54.56 125.00   0.00  166
  2  \w    -51.00 -11.00   0.50   20.00    --  -86.25  45.00  60.00   80
  3  \w    -35.00  -8.00   0.50   20.00    --  -86.25  30.00 120.00   54
  4  \w   -127.00 -41.00   0.50    5.00    --  -54.56 -57.00  30.00  172
  5  \w   -130.00 -82.00   0.50    5.00    --  -54.56 -99.00-120.00   96
  6  \w   -127.00 -39.00   0.50    5.00    --  -54.56 -77.00-180.00  176
  7  \w    -26.00  25.00   0.50    5.00    --  -54.56  19.00-180.00  102
  8  \w    -92.00  -9.00   0.50    5.00    --  -54.56 125.00-180.00  166
  9  \w    101.00 178.00   0.50   20.00    --  107.75 105.00  17.00  154
 10  \w     99.00 178.00   0.50   20.00    --  107.75  30.00 -60.00  158
 11  \w     99.00 178.00   0.50   20.00    --  107.75 111.00 -90.00  158
 12  \w     93.00 178.00   0.50   20.00    --  107.75  61.00  60.00  170
 13  \w     99.00 178.00   0.50   20.00    --  107.75 111.00 120.00  158
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, Pilatus 200K'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1540236000
_diffrn_orient_matrix_UB_12      0.0646563000
_diffrn_orient_matrix_UB_13      -0.0117016000
_diffrn_orient_matrix_UB_21      -0.0981692000
_diffrn_orient_matrix_UB_22      0.0683921000
_diffrn_orient_matrix_UB_23      -0.0599924000
_diffrn_orient_matrix_UB_31      -0.0503447000
_diffrn_orient_matrix_UB_32      0.0605381000
_diffrn_orient_matrix_UB_33      0.0807697000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0403
_diffrn_reflns_av_unetI/netI     0.0283
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            10677
_diffrn_reflns_point_group_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.218
_diffrn_reflns_theta_min         4.330
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.913
_exptl_absorpt_correction_T_max  0.842
_exptl_absorpt_correction_T_min  0.643
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.39a (Rigaku Oxford Diffraction, 2019)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.429
_exptl_crystal_description       plate
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.716
_refine_diff_density_min         -0.341
_refine_diff_density_rms         0.073
_refine_ls_abs_structure_details
;
 Flack x determined using 987 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.3(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         3053
_refine_ls_number_restraints     42
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0974
_refine_ls_R_factor_gt           0.0906
_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^)+(0.1540P)^2^+2.1430P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2590
_refine_ls_wR_factor_ref         0.2660
_reflns_Friedel_coverage         0.701
_reflns_Friedel_fraction_full    0.956
_reflns_Friedel_fraction_max     0.952
_reflns_number_gt                2702
_reflns_number_total             3053
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ce00829c2.cif
_cod_data_source_block           hadi0405
_cod_depositor_comments
'Adding full bibliography for 7243407--7243413.cif.'
_cod_database_code               7243407
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.973
_shelx_estimated_absorpt_t_min   0.898
_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. Uiso/Uaniso restraints and constraints
N2 \\sim O5A \\sim O5B \\sim O6A \\sim O6B: within 2A with sigma of 0.002 and
sigma for terminal atoms of 0.005
3. Others
 Sof(O5B)=Sof(O6B)=1-FVAR(1)
 Sof(O5A)=Sof(O6A)=FVAR(1)
4.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C10(H10), C11(H11), C12(H12), C13(H13), C15(H15),
 C16(H16), C17(H17), C18(H18)
4.b Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C)
;
_shelx_res_checksum              47110
_shelx_hkl_checksum              99608