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#$Date: 2025-08-20 16:06:16 +0300 (Wed, 20 Aug 2025) $
#$Revision: 301830 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/07/82/4078231.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_4078231
loop_
_publ_author_name
'Filthaus, Matthias'
'Schwertmann, Larissa'
'Neuhaus, Patrik'
'Seidel, Rüdiger W.'
'Oppel, Iris M.'
'Bettinger, Holger F.'
_publ_section_title
;
 C--H Bond Amination by Photochemically Generated Transient Borylnitrenes
 at Room Temperature: A Combined Experimental and Theoretical
 Investigation of the Insertion Mechanism and Influence of Substituents
;
_journal_issue                   10
_journal_name_full               Organometallics
_journal_page_first              3894
_journal_paper_doi               10.1021/om300063y
_journal_volume                  31
_journal_year                    2012
_chemical_formula_moiety         'C6 H2 Cl4 O2, 3(H2 O)'
_chemical_formula_sum            'C6 H8 Cl4 O5'
_chemical_formula_weight         301.92
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                108.021(15)
_cell_angle_beta                 110.272(16)
_cell_angle_gamma                91.240(13)
_cell_formula_units_Z            2
_cell_length_a                   6.6762(11)
_cell_length_b                   9.5002(15)
_cell_length_c                   9.5558(17)
_cell_measurement_reflns_used    1286
_cell_measurement_temperature    115(2)
_cell_measurement_theta_max      28.2329
_cell_measurement_theta_min      3.2668
_cell_volume                     534.98(18)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_publication_material  'enCIFer (Allen et al., 2004)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      115(2)
_diffrn_detector_area_resol_mean 8.4171
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'XcaliburTM2, Oxford Diffraction'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0424
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            2893
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.28
_exptl_absorpt_coefficient_mu    1.102
_exptl_absorpt_correction_T_max  0.9469
_exptl_absorpt_correction_T_min  0.6859
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.874
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             304
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.563
_refine_diff_density_min         -0.382
_refine_diff_density_rms         0.116
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2893
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.099
_refine_ls_R_factor_all          0.0412
_refine_ls_R_factor_gt           0.0344
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0546P)²+0.1583P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1018
_refine_ls_wR_factor_ref         0.1067
_reflns_number_gt                2446
_reflns_number_total             2893
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om300063y_si_001.cif
_cod_data_source_block           tetrachlorocatechol
_cod_original_cell_volume        534.97(18)
_cod_database_code               4078231
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Cl1 Cl 0.25722(11) 0.74810(8) 0.48384(9) 0.01574(19) Uani 1 1 d .
Cl2 Cl 0.41113(12) 0.69105(8) 0.80936(9) 0.01836(19) Uani 1 1 d .
Cl3 Cl 0.39463(12) 0.36345(9) 0.81217(9) 0.0190(2) Uani 1 1 d .
Cl4 Cl 0.22467(12) 0.09601(8) 0.48815(9) 0.0178(2) Uani 1 1 d .
O5 O 0.0889(3) 0.1924(2) 0.2043(2) 0.0161(5) Uani 1 1 d .
H5 H 0.0170 0.1209 0.2079 0.019 Uiso 1 1 calc R
O6 O 0.1065(3) 0.4796(2) 0.2087(2) 0.0157(4) Uani 1 1 d .
H6 H 0.0633 0.3989 0.1318 0.019 Uiso 1 1 calc R
C1 C 0.2493(4) 0.5683(3) 0.4897(3) 0.0127(6) Uani 1 1 d .
C2 C 0.3162(4) 0.5424(3) 0.6334(3) 0.0121(6) Uani 1 1 d .
C3 C 0.3082(4) 0.3974(3) 0.6354(3) 0.0133(6) Uani 1 1 d .
C4 C 0.2312(4) 0.2782(3) 0.4910(4) 0.0126(6) Uani 1 1 d .
C5 C 0.1601(4) 0.3034(3) 0.3476(3) 0.0124(6) Uani 1 1 d .
C6 C 0.1710(4) 0.4500(3) 0.3455(3) 0.0118(6) Uani 1 1 d .
O1 O 0.0509(4) 0.7236(3) 0.0839(3) 0.0178(5) Uani 1 1 d D
H1A H 0.073(6) 0.665(3) 0.132(4) 0.021 Uiso 1 1 d D
H1B H 0.161(4) 0.768(4) 0.093(5) 0.021 Uiso 1 1 d D
O2 O 0.7974(3) 0.9554(3) 0.1164(3) 0.0196(6) Uani 1 1 d D
H2A H 0.860(5) 0.879(3) 0.111(5) 0.024 Uiso 1 1 d D
H2B H 0.706(5) 0.954(5) 0.152(5) 0.024 Uiso 1 1 d D
O3 O 0.3866(4) 0.9497(3) 0.1450(3) 0.0199(6) Uani 1 1 d D
H3A H 0.386(6) 1.005(4) 0.230(3) 0.024 Uiso 1 1 d D
H3B H 0.316(5) 0.978(5) 0.068(4) 0.024 Uiso 1 1 d D
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cl1 0.0180(4) 0.0092(4) 0.0209(4) 0.0065(3) 0.0070(3) 0.0023(3)
Cl2 0.0224(4) 0.0125(4) 0.0157(4) 0.0015(3) 0.0049(3) 0.0001(3)
Cl3 0.0240(4) 0.0172(4) 0.0156(4) 0.0083(3) 0.0045(3) 0.0024(3)
Cl4 0.0224(4) 0.0107(4) 0.0217(4) 0.0079(3) 0.0077(3) 0.0023(3)
O5 0.0202(11) 0.0106(11) 0.0163(12) 0.0036(9) 0.0067(10) -0.0030(10)
O6 0.0210(11) 0.0099(11) 0.0142(11) 0.0047(9) 0.0037(10) 0.0002(9)
C1 0.0105(13) 0.0111(15) 0.0197(16) 0.0072(12) 0.0076(13) 0.0014(12)
C2 0.0087(13) 0.0109(15) 0.0143(15) 0.0009(12) 0.0044(12) -0.0008(12)
C3 0.0102(13) 0.0194(16) 0.0140(15) 0.0097(13) 0.0055(12) 0.0028(12)
C4 0.0112(13) 0.0091(14) 0.0195(16) 0.0062(12) 0.0068(13) 0.0020(12)
C5 0.0079(13) 0.0123(15) 0.0159(16) 0.0026(12) 0.0051(12) 0.0001(12)
C6 0.0102(14) 0.0135(15) 0.0142(16) 0.0069(12) 0.0054(13) 0.0038(12)
O1 0.0199(11) 0.0144(12) 0.0202(12) 0.0090(9) 0.0061(10) 0.0021(10)
O2 0.0162(11) 0.0191(16) 0.0253(16) 0.0086(13) 0.0085(11) 0.0050(10)
O3 0.0242(12) 0.0143(15) 0.0199(16) 0.0037(12) 0.0084(11) 0.0041(11)
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'
O O 0.0106 0.0060 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C2 C1 C6 121.2(3)
C2 C1 Cl1 121.0(2)
C6 C1 Cl1 117.8(2)
C3 C2 C1 120.1(3)
C3 C2 Cl2 119.9(2)
C1 C2 Cl2 120.0(2)
C2 C3 C4 119.0(3)
C2 C3 Cl3 120.6(2)
C4 C3 Cl3 120.4(2)
C5 C4 C3 121.2(3)
C5 C4 Cl4 118.3(2)
C3 C4 Cl4 120.5(2)
O5 C5 C4 123.7(3)
O5 C5 C6 116.4(3)
C4 C5 C6 119.8(3)
O6 C6 C1 119.5(3)
O6 C6 C5 121.8(2)
C1 C6 C5 118.8(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C1 1.726(3)
Cl2 C2 1.725(3)
Cl3 C3 1.720(3)
Cl4 C4 1.722(3)
O5 C5 1.359(4)
O6 C6 1.348(3)
C1 C2 1.391(4)
C1 C6 1.397(4)
C2 C3 1.384(4)
C3 C4 1.403(4)
C4 C5 1.385(4)
C5 C6 1.400(4)
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
O1 H1B O3 0.805(18) 2.08(2) 2.844(4) 158(4) .
O1 H1A O6 0.808(18) 2.10(2) 2.894(3) 168(4) .
O2 H2A O1 0.840(19) 1.99(2) 2.813(3) 167(4) 1_655
O2 H2B O3 0.796(18) 2.11(2) 2.850(3) 155(4) .
O3 H3A Cl4 0.819(19) 2.93(2) 3.681(3) 154(3) 1_565
O3 H3B O2 0.852(19) 1.97(2) 2.806(4) 169(3) 2_675
O5 H5 O2 0.84 1.88 2.659(3) 153.0 1_445
O6 H6 O1 0.84 1.89 2.681(3) 156.2 2_565
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30659834
2 PubChem 139107027
