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#$Date: 2021-10-01 02:48:56 +0300 (Fri, 01 Oct 2021) $
#$Revision: 269414 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/36/7243650.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_7243650
loop_
_publ_author_name
'Orecchia, Patrizio'
'Petkova, Desislava Slavcheva'
'Goetz, Roland'
'Rominger, Frank'
'Hashmi, A. Stephen K.'
'Schaub, Thomas'
_publ_section_title
;
 Pd-Catalysed Suzuki--Miyaura cross-coupling of aryl chlorides at low
 catalyst loadings in water for the synthesis of industrially important
 fungicides
;
_journal_name_full               'Green Chemistry'
_journal_paper_doi               10.1039/D1GC02602J
_journal_year                    2021
_chemical_formula_sum            'C18 H12 Cl2 F3 N3 O'
_chemical_formula_weight         414.21
_chemical_name_common            Bixafen
_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
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2021-05-27 deposited with the CCDC.	2021-08-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 110.0924(15)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.8929(7)
_cell_length_b                   18.0476(11)
_cell_length_c                   8.6239(5)
_cell_measurement_reflns_used    2652
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      21.59
_cell_measurement_theta_min      2.76
_cell_volume                     1738.37(18)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick 2015)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II Quazar area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0695
_diffrn_reflns_av_unetI/netI     0.0624
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            17929
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.367
_diffrn_reflns_theta_min         1.823
_diffrn_source                   'ImuS microsource'
_exptl_absorpt_coefficient_mu    0.418
_exptl_absorpt_correction_T_max  0.9590
_exptl_absorpt_correction_T_min  0.9268
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Sheldrick, G. M. (2008). SADABS. University of Göttingen, Germany.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.583
_exptl_crystal_description       plank
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.143
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.021
_refine_diff_density_max         0.304
_refine_diff_density_min         -0.326
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         3545
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0968
_refine_ls_R_factor_gt           0.0523
_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)+(0.0368P)²+1.9244P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1039
_refine_ls_wR_factor_ref         0.1227
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2247
_reflns_number_total             3545
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1gc02602j2.cif
_cod_data_source_block           po3
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7243650
_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   0.943
_shelx_estimated_absorpt_t_max   0.991
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
C1 C 0.5690(3) 0.56795(16) 0.7531(4) 0.0237(7) Uani 1 1 d . . . . .
O1 O 0.46832(19) 0.55193(12) 0.7495(3) 0.0339(6) Uani 1 1 d . . . . .
N1 N 0.5901(2) 0.62103(14) 0.6543(3) 0.0268(6) Uani 1 1 d . . . . .
H1 H 0.655(3) 0.6348(19) 0.676(4) 0.040 Uiso 1 1 d . U . . .
C2 C 0.6734(3) 0.52895(15) 0.8670(4) 0.0223(7) Uani 1 1 d . . . . .
C3 C 0.7939(3) 0.52060(16) 0.8781(4) 0.0247(7) Uani 1 1 d . . . . .
N4 N 0.8539(2) 0.47566(14) 1.0009(3) 0.0310(6) Uani 1 1 d . . . . .
N5 N 0.7734(2) 0.45550(14) 1.0708(3) 0.0297(6) Uani 1 1 d . . . . .
C6 C 0.6658(3) 0.48514(16) 0.9949(4) 0.0266(7) Uani 1 1 d . . . . .
H6 H 0.596323 0.477575 1.023523 0.032 Uiso 1 1 calc R U . . .
C7 C 0.8600(3) 0.54681(19) 0.7704(4) 0.0380(9) Uani 1 1 d . . . . .
H7 H 0.945209 0.529884 0.815452 0.046 Uiso 1 1 calc R U . . .
F8 F 0.80684(19) 0.52097(13) 0.6135(3) 0.0569(6) Uani 1 1 d . . . . .
F9 F 0.85543(18) 0.62188(12) 0.7569(3) 0.0598(7) Uani 1 1 d . . . . .
C10 C 0.8091(3) 0.4050(2) 1.2113(5) 0.0492(10) Uani 1 1 d . . . . .
H10A H 0.744286 0.401008 1.256704 0.074 Uiso 1 1 calc R U . . .
H10B H 0.881266 0.424071 1.296433 0.074 Uiso 1 1 calc R U . . .
H10C H 0.825856 0.356014 1.175310 0.074 Uiso 1 1 calc R U . . .
C11 C 0.5011(3) 0.65805(16) 0.5234(4) 0.0245(7) Uani 1 1 d . . . . .
C12 C 0.5172(3) 0.73233(16) 0.4866(4) 0.0230(7) Uani 1 1 d . . . . .
C13 C 0.4287(3) 0.76592(17) 0.3542(4) 0.0267(7) Uani 1 1 d . . . . .
H13 H 0.437412 0.816019 0.326442 0.032 Uiso 1 1 calc R U . . .
C14 C 0.3291(3) 0.72623(17) 0.2643(4) 0.0285(7) Uani 1 1 d . . . . .
C15 C 0.3115(3) 0.65441(17) 0.3004(4) 0.0300(8) Uani 1 1 d . . . . .
H15 H 0.240949 0.628571 0.237602 0.036 Uiso 1 1 calc R U . . .
C16 C 0.3985(3) 0.62014(17) 0.4303(4) 0.0281(7) Uani 1 1 d . . . . .
H16 H 0.387912 0.570041 0.456162 0.034 Uiso 1 1 calc R U . . .
F18 F 0.24566(16) 0.75975(10) 0.1340(2) 0.0417(5) Uani 1 1 d . . . . .
C21 C 0.6257(3) 0.77654(16) 0.5807(4) 0.0245(7) Uani 1 1 d . . . . .
C22 C 0.7370(3) 0.75925(17) 0.5726(4) 0.0328(8) Uani 1 1 d . . . . .
H22 H 0.744806 0.718240 0.507978 0.039 Uiso 1 1 calc R U . . .
C23 C 0.8370(3) 0.80089(18) 0.6573(4) 0.0354(8) Uani 1 1 d . . . . .
C24 C 0.8264(3) 0.86087(18) 0.7524(4) 0.0336(8) Uani 1 1 d . . . . .
C25 C 0.7156(3) 0.88014(18) 0.7584(4) 0.0345(8) Uani 1 1 d . . . . .
H25 H 0.707855 0.921938 0.820887 0.041 Uiso 1 1 calc R U . . .
C26 C 0.6153(3) 0.83807(17) 0.6725(4) 0.0291(7) Uani 1 1 d . . . . .
H26 H 0.539086 0.851467 0.676499 0.035 Uiso 1 1 calc R U . . .
Cl1 Cl 0.97339(8) 0.77686(6) 0.64143(16) 0.0614(3) Uani 1 1 d . . . . .
Cl2 Cl 0.95136(9) 0.91211(6) 0.86195(12) 0.0544(3) 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'
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'
F F 0.0171 0.0103 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 N1 122.7(3) . . ?
O1 C1 C2 119.9(3) . . ?
N1 C1 C2 117.4(3) . . ?
C1 N1 C11 125.5(3) . . ?
C1 N1 H1 117(3) . . ?
C11 N1 H1 117(3) . . ?
C6 C2 C3 103.1(3) . . ?
C6 C2 C1 122.3(3) . . ?
C3 C2 C1 134.5(3) . . ?
N4 C3 C2 112.0(3) . . ?
N4 C3 C7 115.9(3) . . ?
C2 C3 C7 131.9(3) . . ?
C3 N4 N5 104.6(2) . . ?
C6 N5 N4 112.5(2) . . ?
C6 N5 C10 128.0(3) . . ?
N4 N5 C10 119.5(3) . . ?
N5 C6 C2 107.8(3) . . ?
N5 C6 H6 126.1 . . ?
C2 C6 H6 126.1 . . ?
F9 C7 F8 105.3(3) . . ?
F9 C7 C3 110.9(3) . . ?
F8 C7 C3 110.3(3) . . ?
F9 C7 H7 110.1 . . ?
F8 C7 H7 110.1 . . ?
C3 C7 H7 110.1 . . ?
N5 C10 H10A 109.5 . . ?
N5 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
N5 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C16 C11 C12 120.0(3) . . ?
C16 C11 N1 119.6(3) . . ?
C12 C11 N1 120.4(3) . . ?
C13 C12 C11 118.4(3) . . ?
C13 C12 C21 118.6(3) . . ?
C11 C12 C21 123.0(3) . . ?
C14 C13 C12 119.8(3) . . ?
C14 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
F18 C14 C15 119.0(3) . . ?
F18 C14 C13 118.5(3) . . ?
C15 C14 C13 122.4(3) . . ?
C14 C15 C16 118.6(3) . . ?
C14 C15 H15 120.7 . . ?
C16 C15 H15 120.7 . . ?
C15 C16 C11 120.8(3) . . ?
C15 C16 H16 119.6 . . ?
C11 C16 H16 119.6 . . ?
C22 C21 C26 118.7(3) . . ?
C22 C21 C12 120.9(3) . . ?
C26 C21 C12 120.3(3) . . ?
C23 C22 C21 121.0(3) . . ?
C23 C22 H22 119.5 . . ?
C21 C22 H22 119.5 . . ?
C22 C23 C24 119.9(3) . . ?
C22 C23 Cl1 118.8(3) . . ?
C24 C23 Cl1 121.3(3) . . ?
C25 C24 C23 120.0(3) . . ?
C25 C24 Cl2 119.8(3) . . ?
C23 C24 Cl2 120.3(3) . . ?
C24 C25 C26 119.8(3) . . ?
C24 C25 H25 120.1 . . ?
C26 C25 H25 120.1 . . ?
C21 C26 C25 120.6(3) . . ?
C21 C26 H26 119.7 . . ?
C25 C26 H26 119.7 . . ?
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
C1 O1 1.222(3) . ?
C1 N1 1.361(4) . ?
C1 C2 1.471(4) . ?
N1 C11 1.421(4) . ?
N1 H1 0.77(3) . ?
C2 C6 1.385(4) . ?
C2 C3 1.411(4) . ?
C3 N4 1.330(4) . ?
C3 C7 1.485(4) . ?
N4 N5 1.346(3) . ?
N5 C6 1.333(4) . ?
N5 C10 1.458(4) . ?
C6 H6 0.9500 . ?
C7 F9 1.359(4) . ?
C7 F8 1.364(4) . ?
C7 H7 1.0000 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C16 1.389(4) . ?
C11 C12 1.406(4) . ?
C12 C13 1.398(4) . ?
C12 C21 1.497(4) . ?
C13 C14 1.373(4) . ?
C13 H13 0.9500 . ?
C14 F18 1.359(3) . ?
C14 C15 1.366(4) . ?
C15 C16 1.382(4) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C21 C22 1.385(4) . ?
C21 C26 1.394(4) . ?
C22 C23 1.385(4) . ?
C22 H22 0.9500 . ?
C23 C24 1.390(5) . ?
C23 Cl1 1.729(3) . ?
C24 C25 1.381(5) . ?
C24 Cl2 1.729(3) . ?
C25 C26 1.394(4) . ?
C25 H25 0.9500 . ?
C26 H26 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
O1 C1 N1 C11 -7.8(5) . . . . ?
C2 C1 N1 C11 171.9(3) . . . . ?
O1 C1 C2 C6 -13.5(4) . . . . ?
N1 C1 C2 C6 166.8(3) . . . . ?
O1 C1 C2 C3 162.8(3) . . . . ?
N1 C1 C2 C3 -16.9(5) . . . . ?
C6 C2 C3 N4 0.2(3) . . . . ?
C1 C2 C3 N4 -176.5(3) . . . . ?
C6 C2 C3 C7 173.8(3) . . . . ?
C1 C2 C3 C7 -2.9(6) . . . . ?
C2 C3 N4 N5 -0.7(3) . . . . ?
C7 C3 N4 N5 -175.4(3) . . . . ?
C3 N4 N5 C6 1.0(3) . . . . ?
C3 N4 N5 C10 179.6(3) . . . . ?
N4 N5 C6 C2 -0.8(4) . . . . ?
C10 N5 C6 C2 -179.4(3) . . . . ?
C3 C2 C6 N5 0.3(3) . . . . ?
C1 C2 C6 N5 177.6(3) . . . . ?
N4 C3 C7 F9 -127.8(3) . . . . ?
C2 C3 C7 F9 58.8(5) . . . . ?
N4 C3 C7 F8 115.9(3) . . . . ?
C2 C3 C7 F8 -57.5(5) . . . . ?
C1 N1 C11 C16 -34.0(4) . . . . ?
C1 N1 C11 C12 146.7(3) . . . . ?
C16 C11 C12 C13 -0.8(4) . . . . ?
N1 C11 C12 C13 178.4(3) . . . . ?
C16 C11 C12 C21 -179.6(3) . . . . ?
N1 C11 C12 C21 -0.4(4) . . . . ?
C11 C12 C13 C14 0.2(4) . . . . ?
C21 C12 C13 C14 179.0(3) . . . . ?
C12 C13 C14 F18 -178.7(3) . . . . ?
C12 C13 C14 C15 0.9(5) . . . . ?
F18 C14 C15 C16 178.2(3) . . . . ?
C13 C14 C15 C16 -1.4(5) . . . . ?
C14 C15 C16 C11 0.7(5) . . . . ?
C12 C11 C16 C15 0.4(5) . . . . ?
N1 C11 C16 C15 -178.9(3) . . . . ?
C13 C12 C21 C22 -111.4(3) . . . . ?
C11 C12 C21 C22 67.4(4) . . . . ?
C13 C12 C21 C26 65.7(4) . . . . ?
C11 C12 C21 C26 -115.5(3) . . . . ?
C26 C21 C22 C23 1.7(5) . . . . ?
C12 C21 C22 C23 178.9(3) . . . . ?
C21 C22 C23 C24 0.1(5) . . . . ?
C21 C22 C23 Cl1 -179.7(2) . . . . ?
C22 C23 C24 C25 -1.9(5) . . . . ?
Cl1 C23 C24 C25 177.9(3) . . . . ?
C22 C23 C24 Cl2 178.7(3) . . . . ?
Cl1 C23 C24 Cl2 -1.5(4) . . . . ?
C23 C24 C25 C26 1.7(5) . . . . ?
Cl2 C24 C25 C26 -178.9(2) . . . . ?
C22 C21 C26 C25 -1.9(5) . . . . ?
C12 C21 C26 C25 -179.1(3) . . . . ?
C24 C25 C26 C21 0.2(5) . . . . ?
