#------------------------------------------------------------------------------
#$Date: 2025-11-29 21:52:47 +0100 (Sat 29 de Nov de 2025) $
#$Revision: 303791 $
#$URL: svn://www.crystallography.net/cod/cif/7/71/98/7719853.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_7719853
loop_
_publ_author_name
'Barton, Kyle J.'
'Hedberg, Emma N.'
'Horton, Alexandria R.'
'Allen, Jacqueline N.'
'Wheeler, Kraig A.'
'Cravens, Shannen L.'
'Bailey, Wilson D.'
_publ_section_title
;
 Pyridyl β-ketoenols, pyrazoles and their zinc complexes: synthesis,
 photophysical properties, and DNA binding.
;
_journal_issue                   46
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              17299
_journal_page_last               17310
_journal_paper_doi               10.1039/d5dt01900a
_journal_volume                  54
_journal_year                    2025
_chemical_formula_moiety         'C16 H16 N2 O2'
_chemical_formula_sum            'C16 H16 N2 O2'
_chemical_formula_weight         268.31
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2025-07-24
_audit_creation_method
;
Olex2 1.5
(compiled 2025.07.13 svn.rb7424aed for OlexSys, GUI svn.r7308)
;
_audit_update_record
;
2025-08-08 deposited with the CCDC.	2025-10-31 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.9920(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.6366(3)
_cell_length_b                   14.5962(5)
_cell_length_c                   9.6954(3)
_cell_measurement_reflns_used    1150
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.68
_cell_measurement_theta_min      2.54
_cell_volume                     1346.97(8)
_computing_cell_refinement       'SAINT+ V8.40B (Bruker AXS Inc., 2020)'
_computing_data_collection       'APEX3 Ver.2019.11-0 (Bruker-AXS, 2019)'
_computing_data_reduction        'SAINT+ Ve8.40B (Bruker-AXS, 2020)'
_computing_molecular_graphics    'OLEX2 (Dolomanov et al., 2009)'
_computing_publication_material  'OLEX2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2019/1)'
_computing_structure_solution    'XT (Sheldrick, 2018/2)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 '100 \\times 140 mm^2^ CMOS sensor'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'Bruker PHOTON II'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'κ-geometry four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_collimation    'focusing mirror'
_diffrn_radiation_detector       'Bruker PHOTON II'
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_reflns_av_R_equivalents  0.0271
_diffrn_reflns_av_unetI/netI     0.0141
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            48893
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.141
_diffrn_reflns_theta_min         2.544
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\mS 3.0'
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.7465
_exptl_absorpt_correction_T_min  0.7026
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0763 before and 0.0447 after correction.
The Ratio of minimum to maximum transmission is 0.9412.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.226
_exptl_crystal_size_min          0.113
_refine_diff_density_max         0.460
_refine_diff_density_min         -0.272
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     189
_refine_ls_number_reflns         5122
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0428
_refine_ls_R_factor_gt           0.0386
_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/[σ²(Fo²)+(0.0666P)²+0.2983P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1139
_refine_ls_wR_factor_ref         0.1185
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4579
_reflns_number_total             5122
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d5dt01900a2.cif
_cod_data_source_block           mo_pnwsci03b_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_diffrn_radiation_probe' value 'X-ray' was changed to
'x-ray' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 

 Adding full bibliography for 7719853--7719858.cif.
;
_cod_database_code               7719853
_shelx_shelxl_version_number     2019/3
_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   0.990
_shelx_estimated_absorpt_t_min   0.971
_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, All O(H) groups
2. Others
 Fixed Sof: H1(0.5) H2(0.5)
3.a Aromatic/amide H refined with riding coordinates:
 C1(H1A), C2(H2A), C3(H3), C4(H4), C7(H7), C10(H10), C11(H11), C13(H13),
 C14(H14)
3.b Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C16(H16A,H16B,H16C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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 0.60304(5) 0.61517(4) 0.57476(6) 0.01951(11) Uani 1 1 d . . . . .
H1 H 0.606(3) 0.5901(18) 0.487(3) 0.029 Uiso 0.5 1 d . U P A 1
O2 O 0.54371(5) 0.56440(4) 0.33026(5) 0.01838(11) Uani 1 1 d . . . . .
H2 H 0.584(3) 0.5748(18) 0.423(3) 0.028 Uiso 0.5 1 d . U P B 2
N1 N 0.30431(7) 0.71965(4) 0.68681(6) 0.02010(12) Uani 1 1 d . . . . .
N2 N 0.05642(7) 0.56480(5) -0.19251(6) 0.02161(13) Uani 1 1 d . . . . .
C1 C 0.26839(8) 0.75703(5) 0.80196(8) 0.02275(14) Uani 1 1 d . . . . .
H1A H 0.176096 0.781003 0.797038 0.027 Uiso 1 1 calc R U . . .
C2 C 0.35862(8) 0.76288(5) 0.92900(7) 0.02192(14) Uani 1 1 d . . . . .
H2A H 0.328381 0.790309 1.008063 0.026 Uiso 1 1 calc R U . . .
C3 C 0.49316(8) 0.72786(5) 0.93738(7) 0.02124(14) Uani 1 1 d . . . . .
H3 H 0.557426 0.731069 1.022177 0.025 Uiso 1 1 calc R U . . .
C4 C 0.53231(7) 0.68783(5) 0.81889(7) 0.01839(13) Uani 1 1 d . . . . .
H4 H 0.623666 0.662757 0.821548 0.022 Uiso 1 1 calc R U . . .
C5 C 0.43510(7) 0.68519(4) 0.69628(7) 0.01570(12) Uani 1 1 d . . . . .
C6 C 0.47372(7) 0.64351(4) 0.56739(7) 0.01577(12) Uani 1 1 d . . . . .
C7 C 0.37621(7) 0.63543(5) 0.44626(7) 0.01610(12) Uani 1 1 d . . . . .
H7 H 0.283029 0.657282 0.444053 0.019 Uiso 1 1 calc R U . . .
C8 C 0.41651(7) 0.59440(4) 0.32588(7) 0.01500(12) Uani 1 1 d . . . . .
C9 C 0.31989(7) 0.58501(4) 0.19479(7) 0.01472(12) Uani 1 1 d . . . . .
C10 C 0.18697(7) 0.62653(5) 0.17201(7) 0.01752(12) Uani 1 1 d . . . . .
H10 H 0.156480 0.660199 0.245603 0.021 Uiso 1 1 calc R U . . .
C11 C 0.09942(7) 0.61970(5) 0.04548(7) 0.01843(13) Uani 1 1 d . . . . .
H11 H 0.010362 0.649076 0.033181 0.022 Uiso 1 1 calc R U . . .
C12 C 0.14072(7) 0.56941(5) -0.06634(7) 0.01640(12) Uani 1 1 d . . . . .
C13 C 0.27301(7) 0.52481(5) -0.04200(7) 0.01706(12) Uani 1 1 d . . . . .
H13 H 0.302239 0.488468 -0.113506 0.020 Uiso 1 1 calc R U . . .
C14 C 0.35967(7) 0.53382(5) 0.08489(7) 0.01589(12) Uani 1 1 d . . . . .
H14 H 0.448789 0.504515 0.098135 0.019 Uiso 1 1 calc R U . . .
C15 C -0.08087(8) 0.60801(6) -0.21371(8) 0.02308(14) Uani 1 1 d . . . . .
H15A H -0.069622 0.674688 -0.207700 0.035 Uiso 1 1 calc R U . . .
H15B H -0.134408 0.587048 -0.141663 0.035 Uiso 1 1 calc R U . . .
H15C H -0.131295 0.591474 -0.306078 0.035 Uiso 1 1 calc R U . . .
C16 C 0.09887(10) 0.51382(8) -0.30691(9) 0.0348(2) Uani 1 1 d . . . . .
H16A H 0.028779 0.521956 -0.390819 0.052 Uiso 1 1 calc R U . . .
H16B H 0.106387 0.448656 -0.282517 0.052 Uiso 1 1 calc R U . . .
H16C H 0.190186 0.536302 -0.324877 0.052 Uiso 1 1 calc R U . . .
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_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1.00 -1.00 1.00 0.1140
-1.00 1.00 -1.00 0.0280
1.00 -1.00 -1.00 0.0990
0.00 1.00 1.00 0.0620
0.00 -1.00 -1.00 0.0700
1.00 0.00 1.00 0.1040
0.00 1.00 0.00 0.0190
0.00 -1.00 0.00 0.0660
1.00 0.00 0.00 0.1330
-1.00 -1.00 0.00 0.0160
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
C6 O1 H1 103.7(16) . . ?
C8 O2 H2 103.1(16) . . ?
C1 N1 C5 117.23(6) . . ?
C12 N2 C15 120.60(6) . . ?
C12 N2 C16 120.95(6) . . ?
C16 N2 C15 118.41(6) . . ?
N1 C1 H1A 118.1 . . ?
N1 C1 C2 123.77(7) . . ?
C2 C1 H1A 118.1 . . ?
C1 C2 H2A 120.7 . . ?
C3 C2 C1 118.56(7) . . ?
C3 C2 H2A 120.7 . . ?
C2 C3 H3 120.7 . . ?
C2 C3 C4 118.60(6) . . ?
C4 C3 H3 120.7 . . ?
C3 C4 H4 120.6 . . ?
C3 C4 C5 118.84(7) . . ?
C5 C4 H4 120.6 . . ?
N1 C5 C4 123.00(6) . . ?
N1 C5 C6 116.72(6) . . ?
C4 C5 C6 120.28(6) . . ?
O1 C6 C5 116.47(6) . . ?
O1 C6 C7 122.24(6) . . ?
C7 C6 C5 121.29(6) . . ?
C6 C7 H7 120.2 . . ?
C6 C7 C8 119.68(6) . . ?
C8 C7 H7 120.2 . . ?
O2 C8 C7 119.65(6) . . ?
O2 C8 C9 117.91(6) . . ?
C7 C8 C9 122.44(6) . . ?
C10 C9 C8 122.61(6) . . ?
C10 C9 C14 117.49(6) . . ?
C14 C9 C8 119.90(6) . . ?
C9 C10 H10 119.2 . . ?
C11 C10 C9 121.69(6) . . ?
C11 C10 H10 119.2 . . ?
C10 C11 H11 119.6 . . ?
C10 C11 C12 120.79(6) . . ?
C12 C11 H11 119.6 . . ?
N2 C12 C11 120.94(6) . . ?
N2 C12 C13 121.47(6) . . ?
C11 C12 C13 117.60(6) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 C12 120.49(6) . . ?
C14 C13 H13 119.8 . . ?
C9 C14 H14 119.1 . . ?
C13 C14 C9 121.89(6) . . ?
C13 C14 H14 119.1 . . ?
N2 C15 H15A 109.5 . . ?
N2 C15 H15B 109.5 . . ?
N2 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N2 C16 H16A 109.5 . . ?
N2 C16 H16B 109.5 . . ?
N2 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
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 H1 0.93(3) . ?
O1 C6 1.3043(8) . ?
O2 H2 0.93(3) . ?
O2 C8 1.2961(8) . ?
N1 C1 1.3359(9) . ?
N1 C5 1.3468(9) . ?
N2 C12 1.3602(9) . ?
N2 C15 1.4510(10) . ?
N2 C16 1.4467(10) . ?
C1 H1A 0.9500 . ?
C1 C2 1.3949(10) . ?
C2 H2A 0.9500 . ?
C2 C3 1.3842(11) . ?
C3 H3 0.9500 . ?
C3 C4 1.3925(10) . ?
C4 H4 0.9500 . ?
C4 C5 1.3943(9) . ?
C5 C6 1.4885(9) . ?
C6 C7 1.3897(9) . ?
C7 H7 0.9500 . ?
C7 C8 1.4189(9) . ?
C8 C9 1.4598(9) . ?
C9 C10 1.4030(9) . ?
C9 C14 1.4030(9) . ?
C10 H10 0.9500 . ?
C10 C11 1.3796(9) . ?
C11 H11 0.9500 . ?
C11 C12 1.4169(9) . ?
C12 C13 1.4180(9) . ?
C13 H13 0.9500 . ?
C13 C14 1.3809(9) . ?
C14 H14 0.9500 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
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 C6 C7 C8 0.58(10) . . . . ?
O2 C8 C9 C10 -170.60(6) . . . . ?
O2 C8 C9 C14 8.53(9) . . . . ?
N1 C1 C2 C3 -0.22(12) . . . . ?
N1 C5 C6 O1 176.05(6) . . . . ?
N1 C5 C6 C7 -4.05(9) . . . . ?
N2 C12 C13 C14 177.05(6) . . . . ?
C1 N1 C5 C4 -0.54(11) . . . . ?
C1 N1 C5 C6 179.84(6) . . . . ?
C1 C2 C3 C4 -0.38(11) . . . . ?
C2 C3 C4 C5 0.50(10) . . . . ?
C3 C4 C5 N1 -0.03(10) . . . . ?
C3 C4 C5 C6 179.57(6) . . . . ?
C4 C5 C6 O1 -3.58(9) . . . . ?
C4 C5 C6 C7 176.32(6) . . . . ?
C5 N1 C1 C2 0.67(12) . . . . ?
C5 C6 C7 C8 -179.31(6) . . . . ?
C6 C7 C8 O2 0.36(10) . . . . ?
C6 C7 C8 C9 -179.09(6) . . . . ?
C7 C8 C9 C10 8.87(10) . . . . ?
C7 C8 C9 C14 -172.01(6) . . . . ?
C8 C9 C10 C11 177.47(6) . . . . ?
C8 C9 C14 C13 -178.51(6) . . . . ?
C9 C10 C11 C12 0.55(11) . . . . ?
C10 C9 C14 C13 0.66(10) . . . . ?
C10 C11 C12 N2 -178.04(7) . . . . ?
C10 C11 C12 C13 1.57(10) . . . . ?
C11 C12 C13 C14 -2.56(10) . . . . ?
C12 C13 C14 C9 1.47(10) . . . . ?
C14 C9 C10 C11 -1.67(10) . . . . ?
C15 N2 C12 C11 -2.77(11) . . . . ?
C15 N2 C12 C13 177.64(7) . . . . ?
C16 N2 C12 C11 179.70(8) . . . . ?
C16 N2 C12 C13 0.11(12) . . . . ?
