#------------------------------------------------------------------------------
#$Date: 2021-10-06 17:51:00 +0300 (Wed, 06 Oct 2021) $
#$Revision: 269674 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/34/7243408.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_7243408
loop_
_publ_author_name
'Aryaeifar, Mahnaz'
'Amiri Rudbari, Hadi'
'Blacque, Olivier'
'Islam, Mohammad Khairul'
'Scopelliti, Rosario'
'Braun, Jason D.'
'Herbert, David E.'
'Bruno, Giuseppe'
'Janiak, Christoph'
'Enamullah, Mohammed'
_publ_section_title
;
 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
;
_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 H18 N2 O2'
_chemical_formula_sum            'C19 H18 N2 O2'
_chemical_formula_weight         306.35
_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   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2020-10-23 deposited with the CCDC.	2021-07-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.945(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.0804(10)
_cell_length_b                   18.793(2)
_cell_length_c                   7.5692(3)
_cell_measurement_reflns_used    90
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      22
_cell_measurement_theta_min      3
_cell_volume                     1557.0(2)
_computing_cell_refinement
'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)'
_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_data_reduction        'EvalCCD (Duisenberg & Schreurs, 1990-2000)'
_computing_molecular_graphics    'Mercury 4.3.0 (CCDC, 2019)'
_computing_publication_material  'CIFTab (Sheldrick, 2016)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX II CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0298
_diffrn_reflns_av_unetI/netI     0.0253
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            20946
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.500
_diffrn_reflns_theta_min         2.932
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6940
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker, 2008) was used for absorption correction.
wR2(int) was 0.0576 before and 0.0501 after correction.
The Ration of minimum to maximum transmission is 0.9308.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.307
_exptl_crystal_description       prism
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.227
_exptl_crystal_size_mid          0.226
_exptl_crystal_size_min          0.226
_refine_diff_density_max         0.436
_refine_diff_density_min         -0.482
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     312
_refine_ls_number_reflns         3556
_refine_ls_number_restraints     219
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0573
_refine_ls_R_factor_gt           0.0447
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0270P)²+1.0614P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0916
_refine_ls_wR_factor_ref         0.0995
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2954
_reflns_number_total             3556
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1ce00829c2.cif
_cod_data_source_block           ma-1
_cod_depositor_comments
'Adding full bibliography for 7243407--7243413.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7243408
_shelx_shelxl_version_number     2018/3
_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.
;
_shelx_estimated_absorpt_t_max   0.981
_shelx_estimated_absorpt_t_min   0.981
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
O1 O 0.39115(9) 0.54721(5) 0.59285(13) 0.0200(2) Uani 1 1 d . . . . .
O2 O 0.25105(9) 0.44021(5) 0.69176(12) 0.0218(2) Uani 1 1 d D . . . .
N1 N 0.55396(12) 0.64938(7) 0.73679(19) 0.0257(3) Uani 1 1 d . . . . .
N2 N 0.35136(14) 0.31403(8) 0.8379(2) 0.0249(4) Uani 0.872(3) 1 d D U P A 1
N3 N 0.0104(10) 0.4466(6) 0.6902(15) 0.032(2) Uani 0.128(3) 1 d D U P A 2
C1 C 0.31070(12) 0.51133(7) 0.46221(18) 0.0176(3) Uani 1 1 d . . . . .
C2 C 0.23815(13) 0.45573(7) 0.51047(18) 0.0181(3) Uani 1 1 d . . . . .
C3 C 0.15984(14) 0.41933(8) 0.37898(19) 0.0217(3) Uani 1 1 d . . . . .
C4 C 0.15723(15) 0.43783(8) 0.2001(2) 0.0253(3) Uani 1 1 d . . . . .
C5 C 0.23203(15) 0.49168(8) 0.1518(2) 0.0245(3) Uani 1 1 d . . . . .
C6 C 0.31031(13) 0.52912(7) 0.28257(19) 0.0202(3) Uani 1 1 d . . . . .
C7 C 0.39495(15) 0.58611(8) 0.2332(2) 0.0283(3) Uani 1 1 d . . . . .
C8 C 0.34360(13) 0.60402(7) 0.68038(17) 0.0172(3) Uani 1 1 d . . . . .
C9 C 0.42982(13) 0.65400(7) 0.75902(18) 0.0187(3) Uani 1 1 d . . . . .
C10 C 0.38852(14) 0.71032(7) 0.85483(19) 0.0223(3) Uani 1 1 d . . . . .
C11 C 0.26614(15) 0.71635(8) 0.8746(2) 0.0243(3) Uani 1 1 d . . . . .
C12 C 0.18209(14) 0.66656(8) 0.7952(2) 0.0239(3) Uani 1 1 d . . . . .
C13 C 0.22071(13) 0.61027(8) 0.69671(19) 0.0213(3) Uani 1 1 d . . . . .
C14 C 0.17190(11) 0.38827(6) 0.7469(2) 0.0179(4) Uani 0.872(3) 1 d DG U P A 1
C15 C 0.22363(10) 0.32628(7) 0.82531(19) 0.0186(4) Uani 0.872(3) 1 d G U P A 1
C16 C 0.15107(14) 0.27690(5) 0.89643(15) 0.0208(4) Uani 0.872(3) 1 d G U P A 1
C17 C 0.02678(13) 0.28950(6) 0.88914(16) 0.0240(4) Uani 0.872(3) 1 d G U P A 1
C18 C -0.02495(10) 0.35149(7) 0.81073(18) 0.0254(4) Uani 0.872(3) 1 d G U P A 1
C19 C 0.04761(11) 0.40087(6) 0.7396(2) 0.0216(4) Uani 0.872(3) 1 d G U P A 1
C20 C 0.1983(10) 0.3870(5) 0.7580(17) 0.0212(13) Uani 0.128(3) 1 d DG U P A 2
C21 C 0.2700(8) 0.3294(5) 0.8240(14) 0.0145(12) Uani 0.128(3) 1 d G U P A 2
C22 C 0.2171(10) 0.2716(4) 0.8974(11) 0.0217(14) Uani 0.128(3) 1 d G U P A 2
C23 C 0.0926(10) 0.2715(4) 0.9048(11) 0.0216(13) Uani 0.128(3) 1 d G U P A 2
C24 C 0.0209(8) 0.3292(6) 0.8388(13) 0.0228(12) Uani 0.128(3) 1 d G U P A 2
C25 C 0.0738(9) 0.3870(5) 0.7654(17) 0.0245(13) Uani 0.128(3) 1 d DG U P A 2
H1A H 0.5731(17) 0.6069(11) 0.691(2) 0.034(5) Uiso 1 1 d . . . . .
H1B H 0.6057(19) 0.6590(11) 0.839(3) 0.043(6) Uiso 1 1 d . . . . .
H2A H 0.3900(18) 0.3422(11) 0.775(3) 0.033(6) Uiso 0.872(3) 1 d D . P A 1
H2B H 0.373(2) 0.2693(10) 0.832(3) 0.041(6) Uiso 0.872(3) 1 d D . P A 1
H3 H 0.1085(15) 0.3821(9) 0.411(2) 0.023(4) Uiso 1 1 d . . . . .
H3A H -0.053(6) 0.456(4) 0.743(12) 0.036 Uiso 0.128(3) 1 d D U P A 2
H3B H 0.049(9) 0.487(3) 0.686(18) 0.036 Uiso 0.128(3) 1 d D U P A 2
H4 H 0.1024(16) 0.4128(9) 0.110(2) 0.027(4) Uiso 1 1 d . . . . .
H5 H 0.2313(16) 0.5043(9) 0.027(2) 0.030(5) Uiso 1 1 d . . . . .
H7A H 0.378759 0.630880 0.291677 0.034 Uiso 0.774(18) 1 calc R U P . .
H7B H 0.381190 0.592745 0.103221 0.034 Uiso 0.774(18) 1 calc R U P . .
H7C H 0.479877 0.571744 0.272709 0.034 Uiso 0.774(18) 1 calc R U P . .
H10 H 0.4480(16) 0.7437(9) 0.910(2) 0.027(4) Uiso 1 1 d . . . . .
H11 H 0.2392(15) 0.7545(10) 0.945(2) 0.027(4) Uiso 1 1 d . . . . .
H12 H 0.0965(16) 0.6700(9) 0.807(2) 0.028(4) Uiso 1 1 d . . . . .
H13 H 0.1615(16) 0.5745(10) 0.642(2) 0.031(5) Uiso 1 1 d . . . . .
H16 H 0.1908(18) 0.2342(11) 0.957(3) 0.030(5) Uiso 0.872(3) 1 d . . P A 1
H17 H -0.0235(19) 0.2536(12) 0.944(3) 0.036(6) Uiso 0.872(3) 1 d . . P A 1
H18 H -0.1114(19) 0.3599(11) 0.803(3) 0.034(6) Uiso 0.872(3) 1 d . . P A 1
H19 H 0.012254 0.443239 0.686018 0.026 Uiso 0.872(3) 1 calc R U P A 1
H21 H 0.355131 0.329419 0.818939 0.017 Uiso 0.128(3) 1 calc R U P A 2
H22 H 0.266097 0.232149 0.942450 0.026 Uiso 0.128(3) 1 calc R U P A 2
H23 H 0.056406 0.231997 0.954916 0.026 Uiso 0.128(3) 1 calc R U P A 2
H24 H -0.064253 0.329114 0.843869 0.027 Uiso 0.128(3) 1 calc R U P A 2
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'
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'
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
C1 O1 C8 117.17(10) . . ?
C2 O2 C14 117.53(11) . . ?
C20 O2 C2 124.1(6) . . ?
O1 C1 C2 120.27(12) . . ?
O1 C1 C6 118.52(12) . . ?
C6 C1 C2 121.08(13) . . ?
O2 C2 C1 116.06(12) . . ?
O2 C2 C3 124.03(13) . . ?
C3 C2 C1 119.91(12) . . ?
C4 C3 C2 119.20(14) . . ?
C5 C4 C3 120.88(14) . . ?
C4 C5 C6 120.53(13) . . ?
C1 C6 C5 118.35(13) . . ?
C1 C6 C7 120.14(13) . . ?
C5 C6 C7 121.50(13) . . ?
O1 C8 C9 115.39(12) . . ?
C13 C8 O1 123.45(12) . . ?
C13 C8 C9 121.11(13) . . ?
C8 C9 N1 121.25(13) . . ?
C10 C9 N1 120.70(13) . . ?
C10 C9 C8 118.01(13) . . ?
C11 C10 C9 121.33(14) . . ?
C12 C11 C10 119.81(14) . . ?
C11 C12 C13 120.00(14) . . ?
C8 C13 C12 119.72(14) . . ?
C15 C14 O2 118.02(9) . . ?
C19 C14 O2 121.70(9) . . ?
C19 C14 C15 120.0 . . ?
C14 C15 N2 120.28(10) . . ?
C16 C15 N2 119.69(10) . . ?
C16 C15 C14 120.0 . . ?
C17 C16 C15 120.0 . . ?
C16 C17 C18 120.0 . . ?
C19 C18 C17 120.0 . . ?
C18 C19 C14 120.0 . . ?
O2 C20 C21 118.2(7) . . ?
O2 C20 C25 121.8(7) . . ?
C25 C20 C21 120.0 . . ?
C22 C21 C20 120.0 . . ?
C21 C22 C23 120.0 . . ?
C22 C23 C24 120.0 . . ?
C25 C24 C23 120.0 . . ?
C20 C25 N3 115.0(9) . . ?
C24 C25 N3 125.0(9) . . ?
C24 C25 C20 120.0 . . ?
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
O1 C1 1.3975(16) . ?
O1 C8 1.4018(16) . ?
O2 C2 1.3883(16) . ?
O2 C14 1.4177(13) . ?
O2 C20 1.297(6) . ?
N1 C9 1.4141(19) . ?
N2 C15 1.4224(18) . ?
N3 C25 1.396(14) . ?
C1 C2 1.4010(19) . ?
C1 C6 1.3996(19) . ?
C2 C3 1.394(2) . ?
C3 C4 1.394(2) . ?
C4 C5 1.392(2) . ?
C5 C6 1.400(2) . ?
C6 C7 1.508(2) . ?
C8 C9 1.4044(19) . ?
C8 C13 1.391(2) . ?
C9 C10 1.400(2) . ?
C10 C11 1.392(2) . ?
C11 C12 1.389(2) . ?
C12 C13 1.399(2) . ?
C14 C15 1.3900 . ?
C14 C19 1.3900 . ?
C16 C15 1.3900 . ?
C17 C16 1.3900 . ?
C18 C17 1.3900 . ?
C19 C18 1.3900 . ?
C20 C21 1.3900 . ?
C20 C25 1.3900 . ?
C22 C21 1.3900 . ?
C23 C22 1.3900 . ?
C24 C23 1.3900 . ?
C25 C24 1.3900 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 O2 0.67(18) . . . . ?
O1 C1 C2 C3 -178.79(12) . . . . ?
O1 C1 C6 C5 178.24(12) . . . . ?
O1 C1 C6 C7 -0.29(19) . . . . ?
O1 C8 C9 N1 5.04(19) . . . . ?
O1 C8 C9 C10 -177.36(12) . . . . ?
O1 C8 C13 C12 176.31(13) . . . . ?
O2 C2 C3 C4 -177.83(13) . . . . ?
O2 C14 C15 N2 -4.14(14) . . . . ?
O2 C14 C15 C16 174.02(14) . . . . ?
O2 C14 C19 C18 -173.79(15) . . . . ?
O2 C20 C21 C22 179.5(12) . . . . ?
O2 C20 C25 N3 2.5(9) . . . . ?
O2 C20 C25 C24 -179.5(12) . . . . ?
N1 C9 C10 C11 178.65(13) . . . . ?
N3 C25 C24 C23 177.8(12) . . . . ?
C1 O1 C8 C9 -157.74(12) . . . . ?
C1 O1 C8 C13 24.84(18) . . . . ?
C1 C2 C3 C4 1.6(2) . . . . ?
C2 O2 C14 C15 116.81(11) . . . . ?
C2 O2 C14 C19 -69.27(14) . . . . ?
C2 O2 C20 C21 107.5(6) . . . . ?
C2 O2 C20 C25 -73.0(9) . . . . ?
C2 C1 C6 C5 2.3(2) . . . . ?
C2 C1 C6 C7 -176.18(13) . . . . ?
C2 C3 C4 C5 0.3(2) . . . . ?
C3 C4 C5 C6 -0.9(2) . . . . ?
C4 C5 C6 C1 -0.4(2) . . . . ?
C4 C5 C6 C7 178.11(14) . . . . ?
C6 C1 C2 O2 176.49(12) . . . . ?
C6 C1 C2 C3 -3.0(2) . . . . ?
C8 O1 C1 C2 -85.64(15) . . . . ?
C8 O1 C1 C6 98.43(15) . . . . ?
C8 C9 C10 C11 1.0(2) . . . . ?
C9 C8 C13 C12 -1.0(2) . . . . ?
C9 C10 C11 C12 -1.3(2) . . . . ?
C10 C11 C12 C13 0.5(2) . . . . ?
C11 C12 C13 C8 0.7(2) . . . . ?
C13 C8 C9 N1 -177.48(13) . . . . ?
C13 C8 C9 C10 0.1(2) . . . . ?
C14 O2 C2 C1 174.92(12) . . . . ?
C14 O2 C2 C3 -5.64(19) . . . . ?
C14 C19 C18 C17 0.0 . . . . ?
C15 C14 C19 C18 0.0 . . . . ?
C17 C16 C15 N2 178.16(13) . . . . ?
C17 C16 C15 C14 0.0 . . . . ?
C18 C17 C16 C15 0.0 . . . . ?
C19 C14 C15 N2 -178.15(13) . . . . ?
C19 C14 C15 C16 0.0 . . . . ?
C19 C18 C17 C16 0.0 . . . . ?
C20 O2 C2 C1 -174.4(6) . . . . ?
C20 O2 C2 C3 5.1(6) . . . . ?
C20 C25 C24 C23 0.0 . . . . ?
C21 C20 C25 N3 -178.1(11) . . . . ?
C21 C20 C25 C24 0.0 . . . . ?
C23 C22 C21 C20 0.0 . . . . ?
C24 C23 C22 C21 0.0 . . . . ?
C25 C20 C21 C22 0.0 . . . . ?
C25 C24 C23 C22 0.0 . . . . ?
