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#$Date: 2020-07-08 02:21:58 +0300 (Wed, 08 Jul 2020) $
#$Revision: 254090 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/85/4038557.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_4038557
loop_
_publ_author_name
'Mitrofanov, Alexander'
'Bychkova, Valentina A.'
'Nefedov, Sergey E.'
'Beletskaya, Irina P.'
_publ_section_title
;
 Selective Metal-Controlled Synthesis of Trifluoromethylated
 (Indolin-2-ylidene)methyl- and Quinolin-3-ylphosphonates.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c00913
_journal_year                    2020
_chemical_formula_sum            'C14 H16 Cl F3 N O4 P'
_chemical_formula_weight         385.70
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2ya'
_space_group_name_H-M_alt        'I 1 2/a 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 105.5990(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   11.7704(4)
_cell_length_b                   15.6900(5)
_cell_length_c                   18.6268(6)
_cell_measurement_reflns_used    7054
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      30.50
_cell_measurement_theta_min      2.60
_cell_volume                     3313.25(19)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0409
_diffrn_reflns_av_unetI/netI     0.0407
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            19990
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.000
_diffrn_reflns_theta_min         2.216
_exptl_absorpt_coefficient_mu    0.377
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.546
_exptl_crystal_description       needls
_exptl_crystal_F_000             1584
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.612
_refine_diff_density_min         -0.558
_refine_diff_density_rms         0.078
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     252
_refine_ls_number_reflns         4818
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0895
_refine_ls_R_factor_gt           0.0714
_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)+(0.0992P)²+12.8473P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1991
_refine_ls_wR_factor_ref         0.2109
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3826
_reflns_number_total             4818
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo0c00913_si_001.cif
_cod_data_source_block           1
_cod_original_sg_symbol_H-M      'I 2/a'
_cod_database_code               4038557
_shelx_shelxl_version_number     2014/7
_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   0.912
_shelx_estimated_absorpt_t_max   0.970
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'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
P1 P 0.89332(7) 0.14211(5) 0.41721(4) 0.0240(2) Uani 1 1 d . . . . .
Cl1 Cl 1.21418(10) 0.03484(7) 0.90059(5) 0.0490(3) Uani 1 1 d . . . . .
F1 F 1.23279(19) 0.24660(13) 0.56853(11) 0.0335(5) Uani 1 1 d . . . . .
F2 F 1.29713(19) 0.22326(14) 0.68612(11) 0.0376(5) Uani 1 1 d . . . . .
F3 F 1.12007(19) 0.26855(12) 0.64087(12) 0.0347(5) Uani 1 1 d . . . . .
O1 O 1.24987(18) 0.07932(15) 0.59982(13) 0.0252(4) Uani 1 1 d . . . . .
O2 O 0.8007(2) 0.08643(15) 0.43054(15) 0.0362(6) Uani 1 1 d . . . . .
O3 O 0.8960(5) 0.1155(4) 0.3382(3) 0.0299(10) Uani 0.55 1 d . . P A 1
C11 C 0.8539(5) 0.1497(4) 0.2715(3) 0.0292(12) Uani 0.55 1 d . . P A 1
H11A H 0.7990 0.1942 0.2796 0.035 Uiso 0.55 1 calc R U P A 1
H11B H 0.8030 0.1044 0.2426 0.035 Uiso 0.55 1 calc R U P A 1
O3A O 0.9425(5) 0.1385(4) 0.3429(3) 0.0202(11) Uani 0.45 1 d . . P A 2
C11A C 0.9655(6) 0.1613(5) 0.3000(4) 0.0262(13) Uani 0.45 1 d . . P A 2
H11C H 1.0263 0.1203 0.2940 0.031 Uiso 0.45 1 calc R U P A 2
H11D H 1.0097 0.2135 0.3204 0.031 Uiso 0.45 1 calc R U P A 2
O4 O 0.8513(2) 0.23783(15) 0.41298(15) 0.0349(6) Uani 1 1 d . . . . .
C13 C 0.9331(8) 0.3110(5) 0.4132(5) 0.0425(18) Uani 0.5 1 d . . P B 1
H13A H 1.0125 0.2896 0.4140 0.051 Uiso 0.5 1 calc R U P B 1
H13B H 0.9034 0.3459 0.3677 0.051 Uiso 0.5 1 calc R U P B 1
C13A C 0.8386(8) 0.2880(5) 0.4689(5) 0.0463(19) Uani 0.5 1 d . . P B 2
H13C H 0.8497 0.2543 0.5152 0.056 Uiso 0.5 1 calc R U P B 2
H13D H 0.7586 0.3133 0.4561 0.056 Uiso 0.5 1 calc R U P B 2
N1 N 0.9530(2) 0.10497(19) 0.59119(14) 0.0259(5) Uani 1 1 d . . . . .
C1 C 1.0002(3) 0.0867(2) 0.66679(16) 0.0230(6) Uani 1 1 d . . . . .
C2 C 0.9419(3) 0.0624(3) 0.71895(18) 0.0359(8) Uani 1 1 d . . . . .
H2A H 0.8585 0.0566 0.7058 0.043 Uiso 1 1 calc R U . . .
C3 C 1.0099(3) 0.0466(3) 0.79129(18) 0.0363(8) Uani 1 1 d . . . . .
H3A H 0.9726 0.0295 0.8283 0.044 Uiso 1 1 calc R U . . .
C4 C 1.1324(3) 0.0558(2) 0.80998(16) 0.0305(7) Uani 1 1 d . . . . .
C5 C 1.1896(3) 0.08024(19) 0.75744(16) 0.0247(6) Uani 1 1 d . . . . .
H5A H 1.2729 0.0863 0.7704 0.030 Uiso 1 1 calc R U . . .
C6 C 1.1222(2) 0.09560(18) 0.68553(15) 0.0203(5) Uani 1 1 d . . . . .
C7 C 1.1582(2) 0.12398(18) 0.61733(15) 0.0190(5) Uani 1 1 d . . . . .
C8 C 1.2027(3) 0.21645(19) 0.62784(17) 0.0252(6) Uani 1 1 d . . . . .
C9 C 1.0391(2) 0.12099(18) 0.55647(15) 0.0195(5) Uani 1 1 d . . . . .
C10 C 1.0289(3) 0.13378(19) 0.48341(16) 0.0231(6) Uani 1 1 d . . . . .
H10A H 1.0988 0.1384 0.4674 0.028 Uiso 1 1 calc R U . . .
C12 C 0.9057(4) 0.1863(3) 0.2206(2) 0.0470(10) Uani 1 1 d . . . . .
H12B H 0.9284 0.1364 0.1981 0.071 Uiso 1 1 d R U . A .
H12C H 0.9631 0.2279 0.2161 0.071 Uiso 1 1 d R U . . .
H12A H 0.8440 0.2047 0.1767 0.071 Uiso 1 1 d R U . . .
C14 C 0.9396(5) 0.3637(3) 0.4807(3) 0.0604(13) Uani 1 1 d . . . . .
H14A H 0.8741 0.3978 0.4540 0.091 Uiso 1 1 d R U . B .
H14B H 0.9461 0.3666 0.5331 0.091 Uiso 1 1 d R U . . .
H14D H 1.0109 0.3850 0.4714 0.091 Uiso 1 1 d R U . . .
H1 H 0.886(4) 0.100(3) 0.568(2) 0.027(10) Uiso 1 1 d . . . . .
H2 H 1.230(4) 0.029(3) 0.589(3) 0.042(12) 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 0.0033 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'
P P 0.1023 0.0942 '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
O2 P1 O3 102.0(3) . . ?
O2 P1 O4 109.75(14) . . ?
O3 P1 O4 107.3(2) . . ?
O2 P1 O3A 124.7(2) . . ?
O4 P1 O3A 99.7(2) . . ?
O2 P1 C10 114.61(14) . . ?
O3 P1 C10 114.0(2) . . ?
O4 P1 C10 108.82(15) . . ?
O3A P1 C10 97.5(2) . . ?
C11 O3 P1 133.6(5) . . ?
O3 C11 C12 133.7(6) . . ?
C11A O3A P1 156.4(7) . . ?
O3A C11A C12 137.6(7) . . ?
C13A O4 P1 128.1(4) . . ?
C13 O4 P1 122.5(4) . . ?
C14 C13 O4 108.4(5) . . ?
O4 C13A C14 107.3(6) . . ?
C9 N1 C1 111.8(2) . . ?
C2 C1 C6 121.6(3) . . ?
C2 C1 N1 128.7(3) . . ?
C6 C1 N1 109.6(2) . . ?
C1 C2 C3 117.6(3) . . ?
C2 C3 C4 120.6(3) . . ?
C5 C4 C3 121.2(3) . . ?
C5 C4 Cl1 119.5(3) . . ?
C3 C4 Cl1 119.3(3) . . ?
C6 C5 C4 118.2(3) . . ?
C5 C6 C1 120.7(3) . . ?
C5 C6 C7 130.5(3) . . ?
C1 C6 C7 108.8(2) . . ?
O1 C7 C6 117.2(2) . . ?
O1 C7 C8 104.2(2) . . ?
C6 C7 C8 109.5(2) . . ?
O1 C7 C9 114.7(2) . . ?
C6 C7 C9 101.7(2) . . ?
C8 C7 C9 109.4(2) . . ?
F2 C8 F1 107.3(2) . . ?
F2 C8 F3 106.9(2) . . ?
F1 C8 F3 107.5(3) . . ?
F2 C8 C7 111.1(3) . . ?
F1 C8 C7 112.7(2) . . ?
F3 C8 C7 111.1(2) . . ?
C10 C9 N1 129.0(3) . . ?
C10 C9 C7 123.5(3) . . ?
N1 C9 C7 107.5(2) . . ?
C9 C10 P1 122.8(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
P1 O2 1.470(3) . ?
P1 O3 1.537(5) . ?
P1 O4 1.576(2) . ?
P1 O3A 1.638(5) . ?
P1 C10 1.740(3) . ?
Cl1 C4 1.735(3) . ?
F1 C8 1.334(3) . ?
F2 C8 1.333(4) . ?
F3 C8 1.342(4) . ?
O1 C7 1.397(3) . ?
O3 C11 1.322(7) . ?
C11 C12 1.382(7) . ?
O3A C11A 0.978(9) . ?
C11A C12 1.508(8) . ?
O4 C13A 1.345(8) . ?
O4 C13 1.498(7) . ?
C13 C14 1.489(9) . ?
C13A C14 1.654(11) . ?
N1 C9 1.365(4) . ?
N1 C1 1.398(4) . ?
C1 C2 1.385(4) . ?
C1 C6 1.392(4) . ?
C2 C3 1.392(5) . ?
C3 C4 1.396(5) . ?
C4 C5 1.383(5) . ?
C5 C6 1.382(4) . ?
C6 C7 1.510(4) . ?
C7 C8 1.537(4) . ?
C7 C9 1.548(4) . ?
C9 C10 1.349(4) . ?
