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#$Date: 2024-12-24 04:15:53 +0200 (Tue, 24 Dec 2024) $
#$Revision: 296957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/97/7249712.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_7249712
loop_
_publ_author_name
'Gradenegger, A.'
'Schachner, J. A.'
'Belaj, F.'
'Mösch-Zanetti, N. C.'
_publ_section_title
;
 An oxidorhenium(v) complex with an electron-withdrawing ligand: benefits
 and drawbacks for a dual role catalyst
;
_journal_issue                   54
_journal_name_full               'RSC Advances'
_journal_page_first              40058
_journal_page_last               40068
_journal_paper_doi               10.1039/D4RA07391F
_journal_volume                  14
_journal_year                    2024
_chemical_compound_source        'synthetical product'
_chemical_formula_moiety         'C11 H11 Cl2 N O2'
_chemical_formula_sum            'C11 H11 Cl2 N O2'
_chemical_formula_weight         260.11
_chemical_name_common
' 2,4-dichloro-6-(4,4-dimethyl-4,5-dihydro-1,3-oxazol-2-yl)phenol'
_chemical_name_systematic
' 2,4-dichloro-6-(4,4-dimethyl-4,5-dihydro-1,3-oxazol-2-yl)phenol'
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           'manual edited SHELXL-2014/6.cif file'
_audit_update_record
;
2019-05-03 deposited with the CCDC.	2024-12-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 107.136(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.4471(9)
_cell_length_b                   23.852(4)
_cell_length_c                   6.8468(8)
_cell_measurement_reflns_used    4813
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.73
_cell_measurement_theta_min      2.99
_cell_volume                     1162.2(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'modified ORTEP (Johnson, 1965)'
_computing_publication_material  'SHELXL-2014/6 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'multilayer monochromator'
_diffrn_radiation_source         'Incoatec microfocus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0857
_diffrn_reflns_av_unetI/netI     0.0675
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            17577
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         29.99
_diffrn_reflns_theta_min         2.99
_exptl_absorpt_coefficient_mu    0.542
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.613
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.487
_exptl_crystal_description       plate
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.277
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details
;
 Flack x determined using 1228 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_hydrogen_treatment    refU
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         3384
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.008
_refine_ls_R_factor_all          0.0505
_refine_ls_R_factor_gt           0.0365
_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)+(0.0257P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0713
_refine_ls_wR_factor_ref         0.0762
_reflns_Friedel_coverage         0.991
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                2846
_reflns_number_total             3384
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ra07391f2.cif
_cod_data_source_block           JSJZ15
_cod_original_sg_symbol_H-M      'C c'
_cod_database_code               7249712
_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   0.829
_shelx_estimated_absorpt_t_max   0.984
_shelxl_version_number           2014/6
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, 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
O11 O 0.8783(4) 0.59340(9) 0.6223(5) 0.0218(5) Uani 1 1 d . . . . .
C12 C 0.7050(5) 0.61298(14) 0.5225(5) 0.0163(6) Uani 1 1 d . . . . .
N13 N 0.6813(4) 0.66574(11) 0.5083(5) 0.0192(6) Uani 1 1 d . . . . .
C14 C 0.8611(5) 0.69260(13) 0.6287(6) 0.0200(6) Uani 1 1 d . . . . .
C15 C 0.9979(6) 0.64295(13) 0.6658(6) 0.0233(6) Uani 1 1 d . . . . .
H151 H 1.0780 0.6449 0.5735 0.031(7) Uiso 1 1 calc R U . . .
H152 H 1.0795 0.6426 0.8090 0.031(7) Uiso 1 1 calc R U . . .
C16 C 0.8351(6) 0.71422(15) 0.8286(6) 0.0269(7) Uani 1 1 d . . . . .
H161 H 0.7377 0.7433 0.7988 0.041(6) Uiso 1 1 calc R U . . .
H162 H 0.9537 0.7301 0.9138 0.041(6) Uiso 1 1 calc R U . . .
H163 H 0.7971 0.6832 0.9016 0.041(6) Uiso 1 1 calc R U . . .
C17 C 0.9151(5) 0.73938(15) 0.5063(6) 0.0305(8) Uani 1 1 d . . . . .
H171 H 0.9265 0.7242 0.3774 0.035(6) Uiso 1 1 calc R U . . .
H172 H 1.0355 0.7556 0.5852 0.035(6) Uiso 1 1 calc R U . . .
H173 H 0.8179 0.7685 0.4772 0.035(6) Uiso 1 1 calc R U . . .
O21 O 0.32681(2) 0.64586(9) 0.33599(2) 0.0219(5) Uani 1 1 d D . . . .
H21 H 0.4186(9) 0.6657(3) 0.400(2) 0.062(15) Uiso 1 1 d D . . . .
C21 C 0.3715(5) 0.59158(14) 0.3558(5) 0.0146(6) Uani 1 1 d . . . . .
C22 C 0.5559(5) 0.57147(13) 0.4429(5) 0.0153(6) Uani 1 1 d . . . . .
C23 C 0.5936(5) 0.51418(14) 0.4592(5) 0.0177(7) Uani 1 1 d . . . . .
H23 H 0.7184 0.5011 0.5176 0.027(7) Uiso 1 1 calc R U . . .
C24 C 0.4483(5) 0.47671(14) 0.3898(6) 0.0176(6) Uani 1 1 d . . . . .
C25 C 0.2648(5) 0.49450(14) 0.3024(5) 0.0177(6) Uani 1 1 d . . . . .
H25 H 0.1659 0.4681 0.2548 0.027(7) Uiso 1 1 calc R U . . .
C26 C 0.2292(5) 0.55124(14) 0.2863(5) 0.0165(6) Uani 1 1 d . . . . .
Cl24 Cl 0.4959(3) 0.40493(3) 0.4123(3) 0.02213(17) Uani 1 1 d . . . . .
Cl26 Cl 0.0013(3) 0.57500(4) 0.1728(4) 0.02665(19) Uani 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 0.0033 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'
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
C12 O11 C15 104.9(3) . . ?
N13 C12 O11 118.1(3) . . ?
N13 C12 C22 124.6(3) . . ?
O11 C12 C22 117.3(3) . . ?
C12 N13 C14 107.5(3) . . ?
N13 C14 C17 110.5(3) . . ?
N13 C14 C16 108.0(2) . . ?
C17 C14 C16 111.8(3) . . ?
N13 C14 C15 101.7(3) . . ?
C17 C14 C15 112.8(3) . . ?
C16 C14 C15 111.5(3) . . ?
O11 C15 C14 104.9(3) . . ?
O11 C15 H151 110.8 . . ?
C14 C15 H151 110.8 . . ?
O11 C15 H152 110.8 . . ?
C14 C15 H152 110.8 . . ?
H151 C15 H152 108.8 . . ?
C14 C16 H161 109.5 . . ?
C14 C16 H162 109.5 . . ?
H161 C16 H162 109.5 . . ?
C14 C16 H163 109.5 . . ?
H161 C16 H163 109.5 . . ?
H162 C16 H163 109.5 . . ?
C14 C17 H171 109.5 . . ?
C14 C17 H172 109.5 . . ?
H171 C17 H172 109.5 . . ?
C14 C17 H173 109.5 . . ?
H171 C17 H173 109.5 . . ?
H172 C17 H173 109.5 . . ?
C21 O21 H21 110.6(7) . . ?
O21 C21 C26 119.3(3) . . ?
O21 C21 C22 123.8(3) . . ?
C26 C21 C22 116.9(3) . . ?
C23 C22 C21 121.0(3) . . ?
C23 C22 C12 121.3(3) . . ?
C21 C22 C12 117.6(3) . . ?
C24 C23 C22 119.4(3) . . ?
C24 C23 H23 120.3 . . ?
C22 C23 H23 120.3 . . ?
C23 C24 C25 121.7(3) . . ?
C23 C24 Cl24 119.2(2) . . ?
C25 C24 Cl24 119.1(2) . . ?
C26 C25 C24 118.5(3) . . ?
C26 C25 H25 120.7 . . ?
C24 C25 H25 120.7 . . ?
C25 C26 C21 122.5(3) . . ?
C25 C26 Cl26 119.7(2) . . ?
C21 C26 Cl26 117.8(2) . . ?
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
O11 C12 1.353(4) . ?
O11 C15 1.457(4) . ?
C12 N13 1.270(4) . ?
C12 C22 1.467(4) . ?
N13 C14 1.494(4) . ?
C14 C17 1.519(4) . ?
C14 C16 1.528(4) . ?
C14 C15 1.533(5) . ?
C15 H151 0.99 . ?
C15 H152 0.99 . ?
C16 H161 0.98 . ?
C16 H162 0.98 . ?
C16 H163 0.98 . ?
C17 H171 0.98 . ?
C17 H172 0.98 . ?
C17 H173 0.98 . ?
O21 C21 1.334(4) . ?
O21 H21 0.84 . ?
C21 C26 1.406(4) . ?
C21 C22 1.411(4) . ?
C22 C23 1.393(4) . ?
C23 C24 1.375(4) . ?
C23 H23 0.95 . ?
C24 C25 1.387(4) . ?
C24 Cl24 1.746(3) . ?
C25 C26 1.377(5) . ?
C25 H25 0.95 . ?
C26 Cl26 1.740(3) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O21 H21 N13 0.84 1.877(6) 2.598(3) 143.1(9) .
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
C15 O11 C12 N13 -6.7(3) . . . . ?
C15 O11 C12 C22 174.9(2) . . . . ?
O11 C12 N13 C14 -4.7(3) . . . . ?
C22 C12 N13 C14 173.6(2) . . . . ?
C12 N13 C14 C17 133.2(3) . . . . ?
C12 N13 C14 C16 -104.3(3) . . . . ?
C12 N13 C14 C15 13.1(3) . . . . ?
C12 O11 C15 C14 14.5(3) . . . . ?
N13 C14 C15 O11 -16.5(3) . . . . ?
C17 C14 C15 O11 -134.9(3) . . . . ?
C16 C14 C15 O11 98.4(3) . . . . ?
O21 C21 C22 C23 -179.9(2) . . . . ?
C26 C21 C22 C23 -0.2(4) . . . . ?
O21 C21 C22 C12 2.3(4) . . . . ?
C26 C21 C22 C12 -178.0(2) . . . . ?
N13 C12 C22 C23 178.2(3) . . . . ?
O11 C12 C22 C23 -3.6(4) . . . . ?
N13 C12 C22 C21 -4.1(4) . . . . ?
O11 C12 C22 C21 174.2(2) . . . . ?
C21 C22 C23 C24 -0.2(4) . . . . ?
C12 C22 C23 C24 177.4(3) . . . . ?
C22 C23 C24 C25 0.5(4) . . . . ?
C22 C23 C24 Cl24 -179.5(2) . . . . ?
C23 C24 C25 C26 -0.2(4) . . . . ?
Cl24 C24 C25 C26 179.77(19) . . . . ?
C24 C25 C26 C21 -0.3(4) . . . . ?
C24 C25 C26 Cl26 178.7(2) . . . . ?
O21 C21 C26 C25 -179.8(2) . . . . ?
C22 C21 C26 C25 0.5(4) . . . . ?
O21 C21 C26 Cl26 1.2(3) . . . . ?
C22 C21 C26 Cl26 -178.5(2) . . . . ?
