#------------------------------------------------------------------------------
#$Date: 2021-10-01 02:48:56 +0300 (Fri, 01 Oct 2021) $
#$Revision: 269414 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/36/7243649.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_7243649
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 F5 N3 O'
_chemical_formula_weight         381.31
_chemical_name_common            Fluxapyroxad
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   12.8826(6)
_cell_length_b                   9.2515(5)
_cell_length_c                   28.4963(12)
_cell_measurement_reflns_used    7606
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      66.56
_cell_measurement_theta_min      5.89
_cell_volume                     3396.3(3)
_computing_cell_refinement       'X-Area Recipe 1.33.0.0 (STOE, 2015)'
_computing_data_collection       'X-Area Pilatus3_SV 1.31.153.0 (STOE, 2018)'
_computing_data_reduction        'X-Area Integrate 1.74.2.0 (STOE, 2018)'
_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, 2018)'
_diffrn_ambient_temperature      200(2)
_diffrn_detector_area_resol_mean 5.81
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type  'STOE Stadivari'
_diffrn_measurement_method       'rotation method, ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0529
_diffrn_reflns_av_unetI/netI     0.0480
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            10749
_diffrn_reflns_point_group_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        66.676
_diffrn_reflns_theta_max         66.676
_diffrn_reflns_theta_min         6.090
_diffrn_source                   'Genix3D Cu HF'
_exptl_absorpt_coefficient_mu    1.163
_exptl_absorpt_correction_T_max  0.982
_exptl_absorpt_correction_T_min  0.439
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'STOE X-AREA LANA'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.491
_exptl_crystal_description       needle
_exptl_crystal_F_000             1552
_exptl_crystal_size_max          0.110
_exptl_crystal_size_mid          0.055
_exptl_crystal_size_min          0.024
_refine_diff_density_max         0.256
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     288
_refine_ls_number_reflns         2929
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.1054
_refine_ls_R_factor_gt           0.0510
_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)+(0.0477P)²+1.3541P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0997
_refine_ls_wR_factor_ref         0.1203
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1728
_reflns_number_total             2929
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1gc02602j2.cif
_cod_data_source_block           po2
_cod_database_code               7243649
_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   0.883
_shelx_estimated_absorpt_t_max   0.973
_exptl_absorpt_special_details   'X-Area LANA 1.70.0.0 (STOE, 2017)'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, 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_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 0.1933(2) 0.7062(3) 0.61241(9) 0.0368(7) Uani 1 1 d . . . . .
C2 C 0.2591(2) 0.6701(3) 0.57521(9) 0.0406(7) Uani 1 1 d . . . . .
C3 C 0.2140(3) 0.6283(4) 0.53253(11) 0.0511(8) Uani 1 1 d . . . . .
H3 H 0.256(3) 0.606(4) 0.5032(12) 0.077 Uiso 1 1 d . U . . .
C4 C 0.1069(3) 0.6271(4) 0.52714(12) 0.0531(9) Uani 1 1 d . . . . .
H4 H 0.079(3) 0.599(4) 0.4956(13) 0.080 Uiso 1 1 d . U . . .
C5 C 0.0436(3) 0.6651(4) 0.56379(11) 0.0499(8) Uani 1 1 d . . . . .
H5 H -0.032(3) 0.673(4) 0.5598(12) 0.075 Uiso 1 1 d . U . . .
C6 C 0.0865(2) 0.7040(3) 0.60674(11) 0.0446(8) Uani 1 1 d . . . . .
H6 H 0.042(3) 0.730(4) 0.6330(12) 0.067 Uiso 1 1 d . U . . .
N7 N 0.23312(19) 0.7495(3) 0.65694(8) 0.0393(6) Uani 1 1 d . . . . .
H7 H 0.216(2) 0.830(4) 0.6654(11) 0.059 Uiso 1 1 d . U . . .
O8 O 0.32225(15) 0.5443(2) 0.67342(6) 0.0423(5) Uani 1 1 d . . . . .
C8 C 0.2919(2) 0.6658(3) 0.68473(9) 0.0349(6) Uani 1 1 d . . . . .
C9 C 0.3205(2) 0.7292(3) 0.73050(9) 0.0337(6) Uani 1 1 d . . . . .
C10 C 0.4043(2) 0.6902(3) 0.75960(10) 0.0393(7) Uani 1 1 d . . . . .
N11 N 0.40680(18) 0.7676(3) 0.79901(9) 0.0456(6) Uani 1 1 d . . . . .
N12 N 0.32339(18) 0.8553(3) 0.79556(8) 0.0420(6) Uani 1 1 d . . . . .
C13 C 0.2708(2) 0.8355(3) 0.75542(10) 0.0403(7) Uani 1 1 d . . . . .
H13 H 0.210(2) 0.891(3) 0.7488(10) 0.060 Uiso 1 1 d . U . . .
C14 C 0.4861(2) 0.5806(4) 0.75041(14) 0.0587(9) Uani 1 1 d . . . . .
H14 H 0.480525 0.541430 0.717805 0.070 Uiso 1 1 calc R U . A 1
F15A F 0.4742(7) 0.4704(6) 0.7838(3) 0.091(3) Uani 0.656(18) 1 d . . P B 1
F16A F 0.5790(3) 0.6331(7) 0.7583(4) 0.086(3) Uani 0.656(18) 1 d . . P B 1
F15B F 0.5435(17) 0.544(2) 0.7847(5) 0.125(10) Uani 0.344(18) 1 d . . P B 2
F16B F 0.5640(9) 0.6646(12) 0.7197(10) 0.125(7) Uani 0.344(18) 1 d . . P B 2
C17 C 0.3009(3) 0.9578(4) 0.83294(11) 0.0609(9) Uani 1 1 d . . . . .
H17A H 0.356916 1.029311 0.834814 0.091 Uiso 1 1 calc R U . . .
H17B H 0.295544 0.906228 0.862872 0.091 Uiso 1 1 calc R U . . .
H17C H 0.235175 1.007039 0.826296 0.091 Uiso 1 1 calc R U . . .
C21 C 0.3744(2) 0.6773(3) 0.57893(10) 0.0428(7) Uani 1 1 d . . . . .
C22 C 0.4337(3) 0.5613(4) 0.56306(11) 0.0493(8) Uani 1 1 d . . . . .
H22 H 0.402(3) 0.468(4) 0.5518(12) 0.074 Uiso 1 1 d . U . . .
F23 F 0.59956(15) 0.4574(2) 0.55127(7) 0.0785(6) Uani 1 1 d . . . . .
C23 C 0.5402(3) 0.5699(4) 0.56559(11) 0.0548(9) Uani 1 1 d . . . . .
F24 F 0.69406(14) 0.6948(2) 0.58495(8) 0.0829(7) Uani 1 1 d . . . . .
C24 C 0.5890(2) 0.6887(4) 0.58310(12) 0.0582(9) Uani 1 1 d . . . . .
F25 F 0.58001(15) 0.9199(2) 0.61522(9) 0.0891(8) Uani 1 1 d . . . . .
C25 C 0.5300(3) 0.8023(4) 0.59852(12) 0.0572(9) Uani 1 1 d . . . . .
C26 C 0.4240(2) 0.7989(4) 0.59683(12) 0.0507(8) Uani 1 1 d . . . . .
H26 H 0.387(3) 0.881(4) 0.6071(12) 0.076 Uiso 1 1 d . U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'
F F 0.0727 0.0534 '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
C6 C1 C2 120.7(3) . . ?
C6 C1 N7 117.7(3) . . ?
C2 C1 N7 121.6(3) . . ?
C1 C2 C3 118.2(3) . . ?
C1 C2 C21 122.7(3) . . ?
C3 C2 C21 119.2(3) . . ?
C4 C3 C2 120.7(3) . . ?
C4 C3 H3 116(2) . . ?
C2 C3 H3 123(2) . . ?
C5 C4 C3 120.3(3) . . ?
C5 C4 H4 123(2) . . ?
C3 C4 H4 117(2) . . ?
C4 C5 C6 120.0(3) . . ?
C4 C5 H5 121(2) . . ?
C6 C5 H5 118(2) . . ?
C1 C6 C5 120.1(3) . . ?
C1 C6 H6 120(2) . . ?
C5 C6 H6 120(2) . . ?
C8 N7 C1 124.5(2) . . ?
C8 N7 H7 121(2) . . ?
C1 N7 H7 115(2) . . ?
O8 C8 N7 123.4(3) . . ?
O8 C8 C9 120.9(2) . . ?
N7 C8 C9 115.6(2) . . ?
C13 C9 C10 103.7(2) . . ?
C13 C9 C8 128.7(3) . . ?
C10 C9 C8 127.6(2) . . ?
N11 C10 C9 112.2(2) . . ?
N11 C10 C14 119.8(3) . . ?
C9 C10 C14 128.0(3) . . ?
C10 N11 N12 104.0(2) . . ?
C13 N12 N11 112.5(2) . . ?
C13 N12 C17 127.7(3) . . ?
N11 N12 C17 119.8(2) . . ?
N12 C13 C9 107.6(2) . . ?
N12 C13 H13 120.7(19) . . ?
C9 C13 H13 131.7(19) . . ?
F16A C14 F15A 104.7(4) . . ?
F15B C14 C10 117.3(5) . . ?
F16A C14 C10 111.4(3) . . ?
F15A C14 C10 107.4(3) . . ?
F15B C14 F16B 101.1(9) . . ?
C10 C14 F16B 102.6(5) . . ?
F16A C14 H14 111.1 . . ?
F15A C14 H14 111.1 . . ?
C10 C14 H14 111.1 . . ?
N12 C17 H17A 109.5 . . ?
N12 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
N12 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C26 C21 C22 119.4(3) . . ?
C26 C21 C2 121.4(3) . . ?
C22 C21 C2 119.3(3) . . ?
C23 C22 C21 119.0(3) . . ?
C23 C22 H22 118.4(19) . . ?
C21 C22 H22 122(2) . . ?
F23 C23 C24 118.0(3) . . ?
F23 C23 C22 120.2(3) . . ?
C24 C23 C22 121.8(3) . . ?
F24 C24 C23 120.6(4) . . ?
F24 C24 C25 120.7(4) . . ?
C23 C24 C25 118.7(3) . . ?
F25 C25 C26 120.5(3) . . ?
F25 C25 C24 117.8(3) . . ?
C26 C25 C24 121.7(3) . . ?
C25 C26 C21 119.4(3) . . ?
C25 C26 H26 118(2) . . ?
C21 C26 H26 122(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
C1 C6 1.386(4) . ?
C1 C2 1.398(4) . ?
C1 N7 1.426(3) . ?
C2 C3 1.402(4) . ?
C2 C21 1.490(4) . ?
C3 C4 1.388(4) . ?
C3 H3 1.02(3) . ?
C4 C5 1.371(5) . ?
C4 H4 1.00(4) . ?
C5 C6 1.390(4) . ?
C5 H5 0.98(3) . ?
C6 H6 0.98(3) . ?
N7 C8 1.342(4) . ?
N7 H7 0.82(3) . ?
O8 C8 1.233(3) . ?
C8 C9 1.477(4) . ?
C9 C13 1.372(4) . ?
C9 C10 1.408(4) . ?
C10 N11 1.332(4) . ?
C10 C14 1.486(4) . ?
N11 N12 1.350(3) . ?
N12 C13 1.342(3) . ?
N12 C17 1.455(4) . ?
C13 H13 0.96(3) . ?
C14 F15B 1.271(9) . ?
C14 F16A 1.311(5) . ?
C14 F15A 1.403(5) . ?
C14 F16B 1.542(15) . ?
C14 H14 1.0000 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C21 C26 1.390(4) . ?
C21 C22 1.394(4) . ?
C22 C23 1.376(5) . ?
C22 H22 1.01(4) . ?
F23 C23 1.355(4) . ?
C23 C24 1.361(5) . ?
F24 C24 1.355(4) . ?
C24 C25 1.369(5) . ?
F25 C25 1.351(4) . ?
C25 C26 1.367(4) . ?
C26 H26 0.94(4) . ?
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
C6 C1 C2 C3 -1.6(4) . . . . ?
N7 C1 C2 C3 179.9(3) . . . . ?
C6 C1 C2 C21 177.1(3) . . . . ?
N7 C1 C2 C21 -1.4(4) . . . . ?
C1 C2 C3 C4 1.9(5) . . . . ?
C21 C2 C3 C4 -176.9(3) . . . . ?
C2 C3 C4 C5 -0.9(5) . . . . ?
C3 C4 C5 C6 -0.5(5) . . . . ?
C2 C1 C6 C5 0.3(4) . . . . ?
N7 C1 C6 C5 178.9(3) . . . . ?
C4 C5 C6 C1 0.8(5) . . . . ?
C6 C1 N7 C8 119.3(3) . . . . ?
C2 C1 N7 C8 -62.1(4) . . . . ?
C1 N7 C8 O8 4.0(4) . . . . ?
C1 N7 C8 C9 -177.0(2) . . . . ?
O8 C8 C9 C13 -156.9(3) . . . . ?
N7 C8 C9 C13 24.0(4) . . . . ?
O8 C8 C9 C10 20.7(4) . . . . ?
N7 C8 C9 C10 -158.3(3) . . . . ?
C13 C9 C10 N11 -0.8(3) . . . . ?
C8 C9 C10 N11 -178.9(3) . . . . ?
C13 C9 C10 C14 -179.1(3) . . . . ?
C8 C9 C10 C14 2.8(5) . . . . ?
C9 C10 N11 N12 0.9(3) . . . . ?
C14 C10 N11 N12 179.4(3) . . . . ?
C10 N11 N12 C13 -0.7(3) . . . . ?
C10 N11 N12 C17 -179.7(3) . . . . ?
N11 N12 C13 C9 0.2(3) . . . . ?
C17 N12 C13 C9 179.2(3) . . . . ?
C10 C9 C13 N12 0.3(3) . . . . ?
C8 C9 C13 N12 178.4(3) . . . . ?
N11 C10 C14 F15B 14.1(17) . . . . ?
C9 C10 C14 F15B -167.7(16) . . . . ?
N11 C10 C14 F16A -47.3(7) . . . . ?
C9 C10 C14 F16A 130.9(6) . . . . ?
N11 C10 C14 F15A 66.7(6) . . . . ?
C9 C10 C14 F15A -115.0(6) . . . . ?
N11 C10 C14 F16B -95.7(10) . . . . ?
C9 C10 C14 F16B 82.6(11) . . . . ?
C1 C2 C21 C26 -48.8(4) . . . . ?
C3 C2 C21 C26 129.9(3) . . . . ?
C1 C2 C21 C22 132.8(3) . . . . ?
C3 C2 C21 C22 -48.5(4) . . . . ?
C26 C21 C22 C23 0.1(4) . . . . ?
C2 C21 C22 C23 178.5(3) . . . . ?
C21 C22 C23 F23 178.7(3) . . . . ?
C21 C22 C23 C24 -0.1(5) . . . . ?
F23 C23 C24 F24 1.6(5) . . . . ?
C22 C23 C24 F24 -179.6(3) . . . . ?
F23 C23 C24 C25 -178.8(3) . . . . ?
C22 C23 C24 C25 -0.1(5) . . . . ?
F24 C24 C25 F25 0.4(5) . . . . ?
C23 C24 C25 F25 -179.2(3) . . . . ?
F24 C24 C25 C26 179.7(3) . . . . ?
C23 C24 C25 C26 0.2(5) . . . . ?
F25 C25 C26 C21 179.2(3) . . . . ?
C24 C25 C26 C21 -0.2(5) . . . . ?
C22 C21 C26 C25 0.0(5) . . . . ?
C2 C21 C26 C25 -178.4(3) . . . . ?
