#------------------------------------------------------------------------------
#$Date: 2025-04-05 05:56:02 +0300 (Sat, 05 Apr 2025) $
#$Revision: 298884 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/71/74/7717473.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_7717473
loop_
_publ_author_name
'Duffin, Rebekah N.'
'Kelderman, Jenisi T. A.'
'Herdman, Megan E.'
'Andrews, Philip C.'
_publ_section_title
;
 Highly selective organo-gallium hydroxamate mediated inhibition of
 antibiotic resistant Klebsiella pneumoniae.
;
_journal_issue                   2
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              649
_journal_page_last               661
_journal_paper_doi               10.1039/d4dt02440k
_journal_volume                  54
_journal_year                    2025
_chemical_formula_moiety         'C15 H16 Ga N O2'
_chemical_formula_sum            'C15 H16 Ga N O2'
_chemical_formula_weight         312.01
_chemical_name_systematic        'Dimethylgallium N-phenylbenzohydroxamate'
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-09-21
_audit_creation_method
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2024-08-28 deposited with the CCDC.	2024-11-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.174(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.7967(3)
_cell_length_b                   13.9100(3)
_cell_length_c                   10.3884(3)
_cell_measurement_reflns_used    10857
_cell_measurement_temperature    123.00(10)
_cell_measurement_theta_max      30.6160
_cell_measurement_theta_min      3.2760
_cell_volume                     1413.48(7)
_computing_cell_refinement       'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      123.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.892
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -59.00  59.00   0.50    2.03    --   22.09 -53.00 -19.00  236
  2  ω    -16.00 103.00   0.50    2.03    --   22.09  53.00 124.00  238
  3  ω     42.00 105.00   0.50    2.03    --   22.09 178.00  30.00  126
  4  ω    -13.00 102.00   0.50    2.03    --   22.09  57.00 -30.00  230
  5  ω    -64.00  48.00   0.50    2.03    --   22.09 -38.00 120.00  224
  6  ω    -23.00  31.00   0.50    2.03    --  -22.17 -99.00-150.00  108
  7  ω   -117.00 -63.00   0.50    2.03    --  -22.17-178.00 150.00  108
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0031794000
_diffrn_orient_matrix_UB_12      0.0201406000
_diffrn_orient_matrix_UB_13      -0.0628345000
_diffrn_orient_matrix_UB_21      0.0611366000
_diffrn_orient_matrix_UB_22      0.0258631000
_diffrn_orient_matrix_UB_23      0.0153184000
_diffrn_orient_matrix_UB_31      0.0388601000
_diffrn_orient_matrix_UB_32      -0.0390669000
_diffrn_orient_matrix_UB_33      -0.0221923000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0404
_diffrn_reflns_av_unetI/netI     0.0363
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.892
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            19008
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.892
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.004
_diffrn_reflns_theta_min         3.144
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.943
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73328
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.113a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear whiteish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.466
_exptl_crystal_description       block
_exptl_crystal_F_000             640
_exptl_crystal_preparation       hexane
_exptl_crystal_recrystallization_method hexane
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.416
_refine_diff_density_min         -0.420
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         4017
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.086
_refine_ls_R_factor_all          0.0442
_refine_ls_R_factor_gt           0.0303
_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)+(0.0349P)²+0.1604P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0702
_refine_ls_wR_factor_ref         0.0741
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3207
_reflns_number_total             4017
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4dt02440k2.cif
_cod_data_source_block           rd-game2bpha_auto
_cod_depositor_comments
'Adding full bibliography for 7717469--7717476.cif.'
_cod_database_code               7717473
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'Ga C H N O'
_chemical_oxdiff_usercomment     dimethyl
_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   0.909
_shelx_estimated_absorpt_t_min   0.800
_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.a Aromatic/amide H refined with riding coordinates:
 C9(H9), C8(H8), C12(H12), C7(H7), C11(H11), C5(H5), C15(H15), C6(H6),
 C13(H13), C14(H14)
2.b Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C), C1(H1A,H1B,H1C)
;
_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 1.495
_oxdiff_exptl_absorpt_empirical_full_min 0.795
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
Ga1 Ga 0.36207(2) 0.42297(2) 0.06120(2) 0.01957(7) Uani 1 1 d . . . . .
O1 O 0.52562(12) 0.49351(8) 0.12335(11) 0.0208(3) Uani 1 1 d . . . . .
O2 O 0.37724(12) 0.37944(9) 0.25121(11) 0.0229(3) Uani 1 1 d . . . . .
N1 N 0.57698(14) 0.45582(10) 0.23928(13) 0.0183(3) Uani 1 1 d . . . . .
C10 C 0.71119(16) 0.48960(12) 0.27923(15) 0.0172(3) Uani 1 1 d . . . . .
C3 C 0.49485(17) 0.39972(12) 0.30309(16) 0.0178(3) Uani 1 1 d . . . . .
C9 C 0.61186(17) 0.40627(12) 0.52793(16) 0.0190(3) Uani 1 1 d . . . . .
H9 H 0.640564 0.470540 0.514370 0.023 Uiso 1 1 calc R U . . .
C2 C 0.20539(18) 0.50965(13) 0.04692(17) 0.0231(4) Uani 1 1 d . . . . .
H2A H 0.154657 0.505488 0.125429 0.035 Uiso 1 1 calc R U . . .
H2B H 0.145446 0.491264 -0.027673 0.035 Uiso 1 1 calc R U . . .
H2C H 0.237366 0.575735 0.035839 0.035 Uiso 1 1 calc R U . . .
C4 C 0.53710(16) 0.35707(12) 0.42969(15) 0.0178(3) Uani 1 1 d . . . . .
C8 C 0.64399(17) 0.36147(13) 0.64471(16) 0.0219(4) Uani 1 1 d . . . . .
H8 H 0.693071 0.395589 0.711613 0.026 Uiso 1 1 calc R U . . .
C12 C 0.94952(18) 0.46155(14) 0.32510(17) 0.0256(4) Uani 1 1 d . . . . .
H12 H 1.025093 0.418783 0.333502 0.031 Uiso 1 1 calc R U . . .
C7 C 0.60481(18) 0.26678(13) 0.66457(17) 0.0238(4) Uani 1 1 d . . . . .
H7 H 0.629354 0.235733 0.743952 0.029 Uiso 1 1 calc R U . . .
C11 C 0.82054(18) 0.42656(12) 0.28795(16) 0.0210(3) Uani 1 1 d . . . . .
H11 H 0.807583 0.360290 0.268812 0.025 Uiso 1 1 calc R U . . .
C5 C 0.49455(18) 0.26291(12) 0.45234(16) 0.0215(4) Uani 1 1 d . . . . .
H5 H 0.440976 0.229662 0.387614 0.026 Uiso 1 1 calc R U . . .
C1 C 0.4026(2) 0.30067(12) -0.01996(18) 0.0269(4) Uani 1 1 d . . . . .
H1A H 0.493690 0.303515 -0.054253 0.040 Uiso 1 1 calc R U . . .
H1B H 0.334306 0.287998 -0.090450 0.040 Uiso 1 1 calc R U . . .
H1C H 0.400104 0.249011 0.044011 0.040 Uiso 1 1 calc R U . . .
C15 C 0.72853(19) 0.58646(12) 0.30474(18) 0.0234(4) Uani 1 1 d . . . . .
H15 H 0.652538 0.628958 0.298434 0.028 Uiso 1 1 calc R U . . .
C6 C 0.52972(18) 0.21767(13) 0.56817(17) 0.0243(4) Uani 1 1 d . . . . .
H6 H 0.502513 0.153069 0.581713 0.029 Uiso 1 1 calc R U . . .
C13 C 0.96825(19) 0.55832(14) 0.34984(18) 0.0280(4) Uani 1 1 d . . . . .
H13 H 1.056909 0.582113 0.373951 0.034 Uiso 1 1 calc R U . . .
C14 C 0.85801(19) 0.62084(14) 0.33960(19) 0.0282(4) Uani 1 1 d . . . . .
H14 H 0.871296 0.687402 0.356527 0.034 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'
Ga Ga 0.2307 1.6083 '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
O1 Ga1 O1 68.86(5) . 3_665 ?
O1 Ga1 O2 79.47(5) . . ?
O2 Ga1 O1 147.60(4) . 3_665 ?
C2 Ga1 O1 109.96(7) . . ?
C2 Ga1 O1 91.82(6) . 3_665 ?
C2 Ga1 O2 105.60(7) . . ?
C1 Ga1 O1 113.43(7) . . ?
C1 Ga1 O1 88.03(6) . 3_665 ?
C1 Ga1 O2 98.75(7) . . ?
C1 Ga1 C2 133.20(8) . . ?
N1 O1 Ga1 110.42(9) . . ?
C3 O2 Ga1 110.78(10) . . ?
O1 N1 C10 114.27(13) . . ?
C3 N1 O1 117.23(13) . . ?
C3 N1 C10 128.32(14) . . ?
C11 C10 N1 120.33(15) . . ?
C15 C10 N1 118.38(15) . . ?
C15 C10 C11 121.27(16) . . ?
O2 C3 N1 118.56(15) . . ?
O2 C3 C4 119.21(14) . . ?
N1 C3 C4 122.19(15) . . ?
C4 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
C8 C9 C4 120.17(15) . . ?
Ga1 C2 H2A 109.5 . . ?
Ga1 C2 H2B 109.5 . . ?
Ga1 C2 H2C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C9 C4 C3 124.08(15) . . ?
C5 C4 C3 116.96(14) . . ?
C5 C4 C9 118.92(15) . . ?
C9 C8 H8 119.8 . . ?
C9 C8 C7 120.34(16) . . ?
C7 C8 H8 119.8 . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C13 C12 C11 120.20(17) . . ?
C8 C7 H7 120.0 . . ?
C6 C7 C8 119.90(16) . . ?
C6 C7 H7 120.0 . . ?
C10 C11 C12 119.03(16) . . ?
C10 C11 H11 120.5 . . ?
C12 C11 H11 120.5 . . ?
C4 C5 H5 119.7 . . ?
C6 C5 C4 120.65(16) . . ?
C6 C5 H5 119.7 . . ?
Ga1 C1 H1A 109.5 . . ?
Ga1 C1 H1B 109.5 . . ?
Ga1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C10 C15 H15 120.4 . . ?
C10 C15 C14 119.20(17) . . ?
C14 C15 H15 120.4 . . ?
C7 C6 H6 120.0 . . ?
C5 C6 C7 119.96(16) . . ?
C5 C6 H6 120.0 . . ?
C12 C13 H13 119.9 . . ?
C12 C13 C14 120.16(17) . . ?
C14 C13 H13 119.9 . . ?
C15 C14 C13 120.13(17) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
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
Ga1 O1 1.9576(11) . ?
Ga1 O1 2.5435(12) 3_665 ?
Ga1 O2 2.0621(12) . ?
Ga1 C2 1.9511(17) . ?
Ga1 C1 1.9492(18) . ?
O1 N1 1.3825(17) . ?
O2 C3 1.2762(19) . ?
N1 C10 1.436(2) . ?
N1 C3 1.325(2) . ?
C10 C11 1.383(2) . ?
C10 C15 1.382(2) . ?
C3 C4 1.481(2) . ?
C9 H9 0.9500 . ?
C9 C4 1.401(2) . ?
C9 C8 1.385(2) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C4 C5 1.398(2) . ?
C8 H8 0.9500 . ?
C8 C7 1.390(3) . ?
C12 H12 0.9500 . ?
C12 C11 1.389(2) . ?
C12 C13 1.381(3) . ?
C7 H7 0.9500 . ?
C7 C6 1.389(3) . ?
C11 H11 0.9500 . ?
C5 H5 0.9500 . ?
C5 C6 1.384(2) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C15 H15 0.9500 . ?
C15 C14 1.385(2) . ?
C6 H6 0.9500 . ?
C13 H13 0.9500 . ?
C13 C14 1.386(3) . ?
C14 H14 0.9500 . ?
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
Ga1 O1 N1 C10 168.00(11) . . . . ?
Ga1 O1 N1 C3 -16.60(17) . . . . ?
Ga1 O2 C3 N1 10.27(19) . . . . ?
Ga1 O2 C3 C4 -167.41(12) . . . . ?
O1 N1 C10 C11 -115.04(17) . . . . ?
O1 N1 C10 C15 63.1(2) . . . . ?
O1 N1 C3 O2 3.9(2) . . . . ?
O1 N1 C3 C4 -178.51(14) . . . . ?
O2 C3 C4 C9 -141.44(17) . . . . ?
O2 C3 C4 C5 36.2(2) . . . . ?
N1 C10 C11 C12 179.09(15) . . . . ?
N1 C10 C15 C14 -178.06(16) . . . . ?
N1 C3 C4 C9 41.0(2) . . . . ?
N1 C3 C4 C5 -141.39(17) . . . . ?
C10 N1 C3 O2 178.54(15) . . . . ?
C10 N1 C3 C4 -3.8(3) . . . . ?
C10 C15 C14 C13 -0.6(3) . . . . ?
C3 N1 C10 C11 70.2(2) . . . . ?
C3 N1 C10 C15 -111.7(2) . . . . ?
C3 C4 C5 C6 179.95(16) . . . . ?
C9 C4 C5 C6 -2.3(2) . . . . ?
C9 C8 C7 C6 -1.8(3) . . . . ?
C4 C9 C8 C7 1.3(3) . . . . ?
C4 C5 C6 C7 1.8(3) . . . . ?
C8 C9 C4 C3 178.34(16) . . . . ?
C8 C9 C4 C5 0.7(2) . . . . ?
C8 C7 C6 C5 0.3(3) . . . . ?
C12 C13 C14 C15 0.1(3) . . . . ?
C11 C10 C15 C14 0.0(3) . . . . ?
C11 C12 C13 C14 1.0(3) . . . . ?
C15 C10 C11 C12 1.0(3) . . . . ?
C13 C12 C11 C10 -1.5(3) . . . . ?
