#------------------------------------------------------------------------------
#$Date: 2025-01-15 04:30:19 +0200 (Wed, 15 Jan 2025) $
#$Revision: 297321 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/33/2023351.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2023351
loop_
_publ_author_name
'Groneck, Erin N.'
'Peek, Nathan'
'Lynch, Will E.'
'Padgett, Clifford W.'
_publ_section_title
;
 Crystal structures of zinc(II) coordination complexes with isoquinoline
 N-oxide
;
_journal_coeditor_code           HB8119
_journal_issue                   2
_journal_name_full
'Acta Crystallographica Section E Crystallographic Communications'
_journal_paper_doi               10.1107/S2056989025000180
_journal_volume                  81
_journal_year                    2025
_chemical_formula_iupac          '[Zn Cl2 (C9 H7 N1 O1)2]'
_chemical_formula_moiety         'C18 H14 Cl2 N2 O2 Zn'
_chemical_formula_sum            'C18 H14 Cl2 N2 O2 Zn'
_chemical_formula_weight         426.58
_chemical_name_systematic
;
Dichloridobis(isoquinoline N-oxide-κO)zinc(II)
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_cell_angle_alpha                96.172(6)
_cell_angle_beta                 92.052(5)
_cell_angle_gamma                96.284(5)
_cell_formula_units_Z            2
_cell_length_a                   7.5164(5)
_cell_length_b                   7.8002(5)
_cell_length_c                   15.1156(10)
_cell_measurement_reflns_used    520
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      22.6030
_cell_measurement_theta_min      2.7150
_cell_volume                     874.77(10)
_computing_cell_refinement
;
CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)
;
_computing_data_collection
;
CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)
;
_computing_data_reduction
;
CrysAlisPro 1.171.40.53 (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_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, HyPix3000'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0289
_diffrn_reflns_av_unetI/netI     0.0619
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            4838
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.348
_diffrn_reflns_theta_min         2.644
_diffrn_source                   'fine-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    1.723
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92940
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlisPro; Rigaku OD, 2019)
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.620
_exptl_crystal_description       irregular
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.546
_refine_diff_density_min         -0.299
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3207
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0747
_refine_ls_R_factor_gt           0.0488
_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)+(0.0519P)²+0.0439P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1087
_refine_ls_wR_factor_ref         0.1237
_reflns_number_gt                2357
_reflns_number_total             3207
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            hb8119.cif
_cod_data_source_block           I
_cod_database_code               2023351
_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.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn Zn1 0.94135(7) 0.67381(7) 0.23426(3) 0.0471(2) Uani d 1 . .
Cl Cl2 1.10215(18) 0.47387(17) 0.27790(8) 0.0642(4) Uani d 1 . .
Cl Cl1 1.0537(2) 0.94814(17) 0.26629(9) 0.0698(4) Uani d 1 . .
O O2 0.8996(4) 0.6204(4) 0.10445(19) 0.0526(8) Uani d 1 . .
O O1 0.6934(4) 0.6319(5) 0.27690(19) 0.0628(9) Uani d 1 . .
N N2 0.7659(5) 0.6628(4) 0.0538(2) 0.0433(9) Uani d 1 . .
N N1 0.6497(5) 0.6711(5) 0.3619(2) 0.0465(9) Uani d 1 . .
C C1 0.4937(6) 0.7275(6) 0.3769(3) 0.0474(11) Uani d 1 . .
H H1 0.417826 0.742590 0.329117 0.057 Uiso calc 1 . .
C C16 0.3419(7) 0.8481(6) 0.0684(3) 0.0558(12) Uani d 1 . .
H H16 0.340539 0.880666 0.129381 0.067 Uiso calc 1 . .
C C10 0.7735(6) 0.6177(6) -0.0366(3) 0.0473(11) Uani d 1 . .
H H10 0.870860 0.566543 -0.059286 0.057 Uiso calc 1 . .
C C2 0.4403(6) 0.7651(5) 0.4644(3) 0.0444(10) Uani d 1 . .
C C7 0.5573(6) 0.7419(5) 0.5355(3) 0.0450(11) Uani d 1 . .
C C11 0.6378(7) 0.6485(6) -0.0920(3) 0.0543(12) Uani d 1 . .
H H11 0.643301 0.618191 -0.152943 0.065 Uiso calc 1 . .
C C18 0.6327(6) 0.7382(6) 0.0875(3) 0.0464(11) Uani d 1 . .
H H18 0.633820 0.769454 0.148655 0.056 Uiso calc 1 . .
C C6 0.5010(8) 0.7816(7) 0.6236(3) 0.0622(14) Uani d 1 . .
H H6 0.575863 0.767927 0.672033 0.075 Uiso calc 1 . .
C C8 0.7216(6) 0.6805(6) 0.5152(3) 0.0528(12) Uani d 1 . .
H H8 0.801520 0.663881 0.561100 0.063 Uiso calc 1 . .
C C3 0.2723(6) 0.8255(6) 0.4807(3) 0.0541(12) Uani d 1 . .
H H3 0.195615 0.841291 0.433315 0.065 Uiso calc 1 . .
C C17 0.4855(6) 0.7738(5) 0.0328(3) 0.0445(11) Uani d 1 . .
C C9 0.7644(6) 0.6456(6) 0.4302(3) 0.0544(12) Uani d 1 . .
H H9 0.873034 0.603814 0.417646 0.065 Uiso calc 1 . .
C C14 0.2034(7) 0.8278(7) -0.0791(4) 0.0684(15) Uani d 1 . .
H H14 0.108847 0.849968 -0.115940 0.082 Uiso calc 1 . .
C C12 0.4906(6) 0.7244(5) -0.0598(3) 0.0467(11) Uani d 1 . .
C C15 0.2012(7) 0.8732(7) 0.0129(4) 0.0640(14) Uani d 1 . .
H H15 0.102906 0.921058 0.036766 0.077 Uiso calc 1 . .
C C5 0.3395(8) 0.8389(7) 0.6375(3) 0.0678(15) Uani d 1 . .
H H5 0.304849 0.864656 0.695408 0.081 Uiso calc 1 . .
C C4 0.2242(7) 0.8599(7) 0.5655(3) 0.0626(14) Uani d 1 . .
H H4 0.113135 0.898061 0.576242 0.075 Uiso calc 1 . .
C C13 0.3403(7) 0.7526(7) -0.1148(3) 0.0615(13) Uani d 1 . .
H H13 0.337385 0.718600 -0.175771 0.074 Uiso calc 1 . .
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'
Cl Cl 0.1484 0.1585 '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'
Zn Zn 0.2839 1.4301 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
Cl1 Zn1 Cl2 . . 117.35(6) ?
O2 Zn1 Cl2 . . 106.39(9) ?
O2 Zn1 Cl1 . . 109.57(10) ?
O2 Zn1 O1 . . 101.78(13) ?
O1 Zn1 Cl2 . . 109.07(12) ?
O1 Zn1 Cl1 . . 111.43(11) ?
N2 O2 Zn1 . . 127.6(2) ?
N1 O1 Zn1 . . 124.0(3) ?
O2 N2 C10 . . 115.9(3) ?
C18 N2 O2 . . 122.4(4) ?
C18 N2 C10 . . 121.6(4) ?
O1 N1 C9 . . 119.7(4) ?
C1 N1 O1 . . 118.8(4) ?
C1 N1 C9 . . 121.5(4) ?
N1 C1 H1 . . 119.6 ?
N1 C1 C2 . . 120.8(4) ?
C2 C1 H1 . . 119.6 ?
C17 C16 H16 . . 120.4 ?
C15 C16 H16 . . 120.4 ?
C15 C16 C17 . . 119.3(5) ?
N2 C10 H10 . . 120.3 ?
C11 C10 N2 . . 119.4(4) ?
C11 C10 H10 . . 120.3 ?
C1 C2 C3 . . 120.8(4) ?
C7 C2 C1 . . 118.6(4) ?
C7 C2 C3 . . 120.5(4) ?
C2 C7 C6 . . 117.7(4) ?
C2 C7 C8 . . 117.9(4) ?
C8 C7 C6 . . 124.3(4) ?
C10 C11 H11 . . 119.2 ?
C10 C11 C12 . . 121.5(4) ?
C12 C11 H11 . . 119.2 ?
N2 C18 H18 . . 119.1 ?
N2 C18 C17 . . 121.7(4) ?
C17 C18 H18 . . 119.1 ?
C7 C6 H6 . . 119.7 ?
C5 C6 C7 . . 120.7(5) ?
C5 C6 H6 . . 119.7 ?
C7 C8 H8 . . 119.7 ?
C9 C8 C7 . . 120.6(4) ?
C9 C8 H8 . . 119.7 ?
C2 C3 H3 . . 120.2 ?
C4 C3 C2 . . 119.6(5) ?
C4 C3 H3 . . 120.2 ?
C16 C17 C18 . . 121.8(4) ?
C16 C17 C12 . . 121.2(4) ?
C12 C17 C18 . . 116.9(4) ?
N1 C9 H9 . . 119.7 ?
C8 C9 N1 . . 120.5(4) ?
C8 C9 H9 . . 119.7 ?
C15 C14 H14 . . 119.6 ?
C13 C14 H14 . . 119.6 ?
C13 C14 C15 . . 120.8(5) ?
C11 C12 C17 . . 118.8(4) ?
C11 C12 C13 . . 123.8(4) ?
C17 C12 C13 . . 117.4(4) ?
C16 C15 C14 . . 120.8(5) ?
C16 C15 H15 . . 119.6 ?
C14 C15 H15 . . 119.6 ?
C6 C5 H5 . . 119.6 ?
C6 C5 C4 . . 120.7(5) ?
C4 C5 H5 . . 119.6 ?
C3 C4 C5 . . 120.8(5) ?
C3 C4 H4 . . 119.6 ?
C5 C4 H4 . . 119.6 ?
C14 C13 C12 . . 120.4(5) ?
C14 C13 H13 . . 119.8 ?
C12 C13 H13 . . 119.8 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Zn1 Cl2 . 2.2147(13) ?
Zn1 Cl1 . 2.2088(14) ?
Zn1 O2 . 1.968(3) ?
Zn1 O1 . 1.999(3) ?
O2 N2 . 1.332(4) ?
O1 N1 . 1.349(4) ?
N2 C10 . 1.378(5) ?
N2 C18 . 1.308(5) ?
N1 C1 . 1.316(5) ?
N1 C9 . 1.366(6) ?
C1 H1 . 0.9300 ?
C1 C2 . 1.405(6) ?
C16 H16 . 0.9300 ?
C16 C17 . 1.379(6) ?
C16 C15 . 1.370(7) ?
C10 H10 . 0.9300 ?
C10 C11 . 1.355(6) ?
C2 C7 . 1.404(6) ?
C2 C3 . 1.416(6) ?
C7 C6 . 1.424(6) ?
C7 C8 . 1.405(6) ?
C11 H11 . 0.9300 ?
C11 C12 . 1.390(6) ?
C18 H18 . 0.9300 ?
C18 C17 . 1.426(6) ?
C6 H6 . 0.9300 ?
C6 C5 . 1.354(7) ?
C8 H8 . 0.9300 ?
C8 C9 . 1.343(6) ?
C3 H3 . 0.9300 ?
C3 C4 . 1.353(6) ?
C17 C12 . 1.414(6) ?
C9 H9 . 0.9300 ?
C14 H14 . 0.9300 ?
C14 C15 . 1.400(7) ?
C14 C13 . 1.340(7) ?
C12 C13 . 1.429(7) ?
C15 H15 . 0.9300 ?
C5 H5 . 0.9300 ?
C5 C4 . 1.401(7) ?
C4 H4 . 0.9300 ?
C13 H13 . 0.9300 ?
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
<i>Cg</i>1 <i>Cg</i>1 3.928(4) . 2_666 yes
<i>Cg</i>1 <i>Cg</i>3 3.966(3) . 2_666 yes
<i>Cg</i>1 <i>Cg</i>3 3.835(3) . 2_676 yes
<i>Cg</i>2 <i>Cg</i>2 3.437(3) . 2_665 yes
<i>Cg</i>3 <i>Cg</i>3 3.845(4) . 2_676 yes
<i>Cg</i>4 <i>Cg</i>4 3.681(4) . 2_675 yes
<i>Cg</i>4 <i>Cg</i>2 3.940(3) . 2_665 yes
<i>Cg</i>4 <i>Cg</i>2 3.906(3) . 2_675 yes
