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#$Date: 2024-02-04 13:52:45 +0200 (Sun, 04 Feb 2024) $
#$Revision: 289489 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/71/49/7714901.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_7714901
loop_
_publ_author_name
'Mahdavi, Seyedeh Mahbobeh'
'Bockfeld, Dirk'
'Büssing, Rolf'
'Karge, Bianka'
'Bannenberg, Thomas'
'Frank, René'
'Brönstrup, Mark'
'Ott, Ingo'
'Tamm, Matthias'
_publ_section_title
;
 Synthesis of N-heterocyclic carbene gold(I) complexes from the marine
 betaine 1,3-dimethylimidazolium-4-carboxylate.
;
_journal_issue                   5
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              1942
_journal_page_last               1946
_journal_paper_doi               10.1039/d3dt04135b
_journal_volume                  53
_journal_year                    2024
_chemical_formula_moiety         'C6 H8 N2 O2, 2(H2 O)'
_chemical_formula_sum            'C6 H12 N2 O4'
_chemical_formula_weight         176.18
_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     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2023-11-27 deposited with the CCDC.	2024-01-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.656(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.81570(10)
_cell_length_b                   17.5289(3)
_cell_length_c                   10.0642(2)
_cell_measurement_reflns_used    17858
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      77.0640
_cell_measurement_theta_min      5.0930
_cell_volume                     839.88(3)
_computing_cell_refinement       'CrysAlisPro 1.171.40.45a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.45a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.45a (Rigaku OD, 2019)'
_computing_publication_material
'OLEX2 v1.2 (O. V. Dolomanov et al., J. Appl. Cryst., 2009, 42, 339-341)'
_computing_structure_refinement
'SHELXL-2018/3 (G. M. Sheldrick, Acta Cryst., 2015, C71, 3-8)'
_computing_structure_solution
'SHELXT 2018/2 (G. M. Sheldrick, Acta Cryst., 2015, A71, 3-8)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       'ω scan'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_unetI/netI     0.0036
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            3755
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.909
_diffrn_reflns_theta_min         5.112
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.005
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.47044
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.45a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.393
_exptl_crystal_description       irregular
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.183
_exptl_crystal_size_mid          0.087
_exptl_crystal_size_min          0.033
_refine_diff_density_max         0.333
_refine_diff_density_min         -0.312
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.143
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         3755
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.143
_refine_ls_R_factor_all          0.0474
_refine_ls_R_factor_gt           0.0448
_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)+(0.0870P)²+0.0851P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1439
_refine_ls_wR_factor_ref         0.1475
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3322
_reflns_number_total             3755
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3dt04135b3.cif
_cod_data_source_block           sm01db2
_cod_depositor_comments
'Adding full bibliography for 7714901--7714907.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7714901
_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_min   0.838
_shelx_estimated_absorpt_t_max   0.968
_oxdiff_exptl_absorpt_empirical_full_min 0.596
_oxdiff_exptl_absorpt_empirical_full_max 1.760
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
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 0.3431(2) 0.66128(5) 0.75206(10) 0.0263(3) Uani 1 1 d . . . . .
O2 O 0.2489(2) 0.78288(5) 0.79684(10) 0.0233(3) Uani 1 1 d . . . . .
O3 O 0.3581(2) 0.50463(6) 0.74566(12) 0.0323(3) Uani 1 1 d . . . . .
H3A H 0.185(6) 0.4864(13) 0.720(2) 0.050(6) Uiso 1 1 d . . . . .
H3B H 0.343(5) 0.5562(13) 0.738(2) 0.040(5) Uiso 1 1 d . . . . .
N1 N 0.7132(2) 0.71498(6) 0.56781(11) 0.0197(3) Uani 1 1 d . . . . .
N2 N 0.8022(2) 0.83292(6) 0.52579(11) 0.0200(3) Uani 1 1 d . . . . .
C1 C 0.8575(3) 0.76059(7) 0.49749(12) 0.0199(3) Uani 1 1 d . . . . .
H1 H 0.979590 0.744367 0.437170 0.024 Uiso 1 1 calc R U . . .
C2 C 0.5585(3) 0.75973(7) 0.64422(12) 0.0181(3) Uani 1 1 d . . . . .
C3 C 0.6168(3) 0.83373(7) 0.61685(13) 0.0196(3) Uani 1 1 d . . . . .
H3 H 0.542712 0.877741 0.654001 0.023 Uiso 1 1 calc R U . . .
C4 C 0.7242(3) 0.63158(7) 0.55963(14) 0.0243(3) Uani 1 1 d . . . . .
H4A H 0.796460 0.610637 0.648395 0.037 Uiso 1 1 calc R U . . .
H4B H 0.848517 0.616711 0.495407 0.037 Uiso 1 1 calc R U . . .
H4C H 0.535081 0.611629 0.529603 0.037 Uiso 1 1 calc R U . . .
C5 C 0.3677(3) 0.73171(7) 0.73871(12) 0.0187(3) Uani 1 1 d . . . . .
C6 C 0.9199(3) 0.90022(8) 0.46879(14) 0.0252(3) Uani 1 1 d . . . . .
H6A H 0.767558 0.930636 0.419317 0.038 Uiso 1 1 calc R U . . .
H6B H 1.048647 0.884079 0.407481 0.038 Uiso 1 1 calc R U . . .
H6C H 1.022334 0.931031 0.541391 0.038 Uiso 1 1 calc R U . . .
H4D H 0.317(6) 0.9599(14) 0.806(3) 0.061(7) Uiso 1 1 d . . . . .
O4 O 0.1584(2) 0.93666(6) 0.81563(12) 0.0314(3) Uani 1 1 d . . . . .
H4E H 0.192(5) 0.8883(15) 0.803(2) 0.046(6) Uiso 1 1 d . . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
0 -11 -1 0.0095
0 11 1 0.0187
2 -3 5 0.0211
2 -4 -4 0.0684
0 1 -6 0.0697
-2 3 -5 0.0720
-1 2 6 0.0093
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 N1 C2 108.74(11) . . ?
C1 N1 C4 122.89(11) . . ?
C2 N1 C4 128.37(11) . . ?
C1 N2 C3 108.84(11) . . ?
C1 N2 C6 125.50(11) . . ?
C3 N2 C6 125.66(11) . . ?
N1 C1 N2 108.67(11) . . ?
C3 C2 N1 106.33(11) . . ?
C3 C2 C5 127.11(12) . . ?
N1 C2 C5 126.56(11) . . ?
C2 C3 N2 107.42(11) . . ?
O1 C5 O2 126.78(12) . . ?
O1 C5 C2 117.94(12) . . ?
O2 C5 C2 115.28(10) . . ?
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 C5 1.2493(16) . ?
O2 C5 1.2550(15) . ?
N1 C1 1.3309(17) . ?
N1 C2 1.3905(15) . ?
N1 C4 1.4656(17) . ?
N2 C1 1.3352(16) . ?
N2 C3 1.3723(18) . ?
N2 C6 1.4628(17) . ?
C2 C3 1.3640(17) . ?
C2 C5 1.5011(17) . ?
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
C2 N1 C1 N2 0.10(14) . . . . ?
C4 N1 C1 N2 179.55(11) . . . . ?
C3 N2 C1 N1 -0.04(15) . . . . ?
C6 N2 C1 N1 -179.97(11) . . . . ?
C1 N1 C2 C3 -0.11(14) . . . . ?
C4 N1 C2 C3 -179.53(12) . . . . ?
C1 N1 C2 C5 -179.65(12) . . . . ?
C4 N1 C2 C5 0.93(19) . . . . ?
N1 C2 C3 N2 0.09(14) . . . . ?
C5 C2 C3 N2 179.62(11) . . . . ?
C1 N2 C3 C2 -0.03(15) . . . . ?
C6 N2 C3 C2 179.90(11) . . . . ?
C3 C2 C5 O1 -179.10(12) . . . . ?
N1 C2 C5 O1 0.34(18) . . . . ?
C3 C2 C5 O2 0.73(19) . . . . ?
N1 C2 C5 O2 -179.82(11) . . . . ?
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.1592 -11.2814 -0.8279 0.8758 0.0696 0.4776
-0.3670 11.2065 0.9411 -0.8418 -0.0670 -0.5355
1.6999 -3.4437 4.5202 0.0685 -0.8691 0.4898
2.4143 -3.8252 -4.2413 -0.0321 0.3993 0.9163
-0.1406 0.8858 -6.3873 -0.0787 0.9934 0.0839
-1.6500 3.3660 -4.6226 -0.0694 0.8796 -0.4706
-1.3560 1.7710 6.1579 0.0639 -0.8029 -0.5927
