#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/93/2229356.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2229356
loop_
_publ_author_name
'Pourayoubi, Mehrdad'
'Saneei, Anahid'
_publ_section_title
;
N-(2-Chloro-2,2-difluoroacetyl)-N',N''-diisopropylphosphoric
triamide
;
_journal_coeditor_code DN2655
_journal_issue 3
_journal_name_full 'Acta Crystallographica Section E'
_journal_page_first o665
_journal_paper_doi 10.1107/S1600536811005435
_journal_volume 67
_journal_year 2011
_chemical_formula_iupac 'C8 H17 Cl F2 N3 O2 P'
_chemical_formula_moiety 'C8 H17 Cl F2 N3 O2 P'
_chemical_formula_sum 'C8 H17 Cl F2 N3 O2 P'
_chemical_formula_weight 291.67
_chemical_name_systematic
;
N-(2-Chloro-2,2-difluoroacetyl)-N',N''-
diisopropylphosphoric triamide
;
_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
_cell_angle_alpha 99.784(2)
_cell_angle_beta 105.999(2)
_cell_angle_gamma 110.770(2)
_cell_formula_units_Z 2
_cell_length_a 8.1993(7)
_cell_length_b 9.6735(9)
_cell_length_c 9.8331(9)
_cell_measurement_reflns_used 2867
_cell_measurement_temperature 100(2)
_cell_measurement_theta_max 30.93
_cell_measurement_theta_min 2.26
_cell_volume 669.18(11)
_computing_cell_refinement 'SAINT (Bruker, 2005)'
_computing_data_collection 'APEX2 (Bruker, 2005)'
_computing_data_reduction 'SAINT (Bruker, 2005)'
_computing_molecular_graphics
'XP in SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)'
_computing_publication_material 'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement 'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution 'SHELXL97 (Sheldrick, 2008)'
_diffrn_ambient_temperature 100(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type 'Bruker SMART APEXII CCD area-detector'
_diffrn_measurement_method '\f and \w'
_diffrn_radiation_monochromator graphite
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_reflns_av_R_equivalents 0.0243
_diffrn_reflns_av_sigmaI/netI 0.0373
_diffrn_reflns_limit_h_max 11
_diffrn_reflns_limit_h_min -11
_diffrn_reflns_limit_k_max 14
_diffrn_reflns_limit_k_min -14
_diffrn_reflns_limit_l_max 14
_diffrn_reflns_limit_l_min -14
_diffrn_reflns_number 9089
_diffrn_reflns_theta_full 31.03
_diffrn_reflns_theta_max 31.03
_diffrn_reflns_theta_min 2.26
_exptl_absorpt_coefficient_mu 0.424
_exptl_absorpt_correction_T_max 0.750
_exptl_absorpt_correction_T_min 0.602
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details '(SADABS; Bruker, 2005)'
_exptl_crystal_colour colorless
_exptl_crystal_density_diffrn 1.448
_exptl_crystal_density_method 'not measured'
_exptl_crystal_description prizm
_exptl_crystal_F_000 304
_exptl_crystal_size_max 0.26
_exptl_crystal_size_mid 0.19
_exptl_crystal_size_min 0.16
_refine_diff_density_max 0.558
_refine_diff_density_min -0.298
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.036
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 158
_refine_ls_number_reflns 4218
_refine_ls_number_restraints 0
_refine_ls_restrained_S_all 1.036
_refine_ls_R_factor_all 0.0510
_refine_ls_R_factor_gt 0.0362
_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/[\s^2^(Fo^2^)+(0.0527P)^2^+0.0127P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.0882
_refine_ls_wR_factor_ref 0.0945
_reflns_number_gt 3337
_reflns_number_total 4218
_reflns_threshold_expression I>2\s(I)
_iucr_refine_instructions_details
;
TITL s4 in P-1
CELL 0.71073 8.1993 9.6735 9.8331 99.784 105.999 110.770
ZERR 2.00 0.0007 0.0009 0.0009 0.002 0.002 0.002
LATT 1
SFAC C H N O P CL F
UNIT 16 34 6 4 2 2 4
MERG 2
FMAP 2
PLAN 20
EQIV $1 -x+1, -y+2, -z
EQIV $2 -x, -y+1, -z
HTAB N1 O2_$1
HTAB N3 O1_$2
ACTA
BOND $H
CONF
L.S. 8
TEMP -173.00
WGHT 0.052700 0.012700
FVAR 0.99987
P1 5 0.232573 0.869718 0.037141 11.00000 0.01625 0.00992 =
0.01683 0.00433 0.01039 0.00349
CL1 6 0.304768 0.566303 -0.368901 11.00000 0.04248 0.03451 =
0.02119 0.00824 0.01803 0.01780
F1 7 0.547175 0.631810 -0.115617 11.00000 0.02076 0.03052 =
0.03578 0.00646 0.01169 0.01333
F2 7 0.314653 0.406751 -0.191411 11.00000 0.04691 0.01619 =
0.04894 0.01466 0.02995 0.01858
O1 4 0.108013 0.529866 -0.105736 11.00000 0.02466 0.01276 =
0.03184 0.00398 0.01867 0.00049
O2 4 0.378341 1.030151 0.108230 11.00000 0.02368 0.01152 =
0.02327 0.00299 0.01576 0.00256
N1 3 0.330892 0.774593 -0.051825 11.00000 0.01484 0.01081 =
0.01952 0.00426 0.01094 0.00339
AFIX 43
H1 2 0.436811 0.829190 -0.060882 11.00000 -1.20000
AFIX 0
N2 3 0.038165 0.835571 -0.092895 11.00000 0.02030 0.02226 =
0.01907 0.00910 0.01261 0.01115
AFIX 3
H2 2 -0.048260 0.842029 -0.066127 11.00000 -1.20000
AFIX 0
N3 3 0.164591 0.790080 0.155661 11.00000 0.01528 0.01254 =
0.01614 0.00421 0.00815 0.00115
AFIX 3
H3 2 0.075323 0.699284 0.122496 11.00000 -1.20000
AFIX 0
C1 1 0.253437 0.619602 -0.108777 11.00000 0.01782 0.01190 =
0.01708 0.00465 0.00889 0.00536
C2 1 0.361837 0.555033 -0.186560 11.00000 0.02435 0.01338 =
0.02457 0.00758 0.01312 0.00895
C3 1 0.023812 0.844686 -0.243936 11.00000 0.02547 0.02438 =
0.01775 0.00762 0.01184 0.01509
AFIX 13
H3A 2 0.070352 0.772062 -0.287423 11.00000 -1.20000
AFIX 0
C4 1 -0.181640 0.789610 -0.337790 11.00000 0.02619 0.02813 =
0.02217 0.00451 0.00664 0.01314
AFIX 137
H4A 2 -0.252470 0.683665 -0.338570 11.00000 -1.50000
H4B 2 -0.193919 0.791590 -0.439357 11.00000 -1.50000
H4C 2 -0.230928 0.858081 -0.295923 11.00000 -1.50000
AFIX 0
C5 1 0.142701 1.006570 -0.243150 11.00000 0.02757 0.03291 =
0.02259 0.01475 0.01291 0.01208
AFIX 137
H5A 2 0.275032 1.034141 -0.188878 11.00000 -1.50000
H5B 2 0.105078 1.080883 -0.194745 11.00000 -1.50000
H5C 2 0.124623 1.009031 -0.345320 11.00000 -1.50000
AFIX 0
C6 1 0.295787 0.820865 0.305956 11.00000 0.01759 0.02199 =
0.01796 0.00694 0.00571 0.00322
AFIX 13
H6A 2 0.397593 0.927680 0.336140 11.00000 -1.20000
AFIX 0
C7 1 0.194078 0.815684 0.413845 11.00000 0.03516 0.03336 =
0.01798 0.00994 0.01243 0.01813
AFIX 137
H7A 2 0.136619 0.888787 0.408123 11.00000 -1.50000
H7B 2 0.283403 0.844160 0.514763 11.00000 -1.50000
H7C 2 0.096481 0.710756 0.388372 11.00000 -1.50000
AFIX 0
C8 1 0.384788 0.707980 0.309044 11.00000 0.03946 0.06691 =
0.03548 0.02779 0.02122 0.03844
AFIX 137
H8A 2 0.456818 0.719483 0.243731 11.00000 -1.50000
H8B 2 0.286727 0.601956 0.274906 11.00000 -1.50000
H8C 2 0.468455 0.729398 0.410495 11.00000 -1.50000
HKLF 4
REM s4 in P-1
REM R1 = 0.0362 for 3338 Fo > 4sig(Fo) and 0.0510 for all 4218 data
REM 158 parameters refined using 0 restraints
END
WGHT 0.0527 0.0127
REM Highest difference peak 0.558, deepest hole -0.298, 1-sigma level 0.063
Q1 1 0.3165 0.5933 -0.1405 11.00000 0.05 0.56
Q2 1 0.2645 0.8091 -0.0004 11.00000 0.05 0.52
Q3 1 0.1338 0.8477 -0.0396 11.00000 0.05 0.47
Q4 1 0.3349 0.7658 0.3148 11.00000 0.05 0.40
Q5 1 0.3379 0.4993 -0.3815 11.00000 0.05 0.40
Q6 1 0.2443 0.8132 0.3621 11.00000 0.05 0.35
Q7 1 0.2527 0.9645 0.0821 11.00000 0.05 0.35
Q8 1 0.2365 0.7995 0.2355 11.00000 0.05 0.34
Q9 1 0.2219 0.8001 0.1071 11.00000 0.05 0.33
Q10 1 0.3120 0.6971 -0.0587 11.00000 0.05 0.33
Q11 1 0.2104 0.5215 -0.4124 11.00000 0.05 0.32
Q12 1 0.3401 0.9452 0.1076 11.00000 0.05 0.32
Q13 1 0.3603 0.5619 -0.2813 11.00000 0.05 0.31
Q14 1 -0.0915 0.8073 -0.2954 11.00000 0.05 0.31
Q15 1 0.5821 0.5804 -0.1486 11.00000 0.05 0.28
Q16 1 0.2924 0.6523 -0.3321 11.00000 0.05 0.28
Q17 1 0.1826 0.5788 -0.1017 11.00000 0.05 0.26
Q18 1 0.1383 0.8627 0.1939 11.00000 0.05 0.25
Q19 1 0.0438 0.7560 -0.1133 11.00000 0.05 0.25
Q20 1 0.1662 0.8437 0.0976 11.00000 0.05 0.25
;
_cod_data_source_file dn2655.cif
_cod_data_source_block I
_cod_original_cell_volume 669.18(10)
_cod_database_code 2229356
_cod_database_fobs_code 2229356
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P P1 0.23257(4) 0.86972(4) 0.03714(4) 0.01390(8) Uani d . 1 . .
Cl Cl1 0.30477(6) 0.56630(4) -0.36890(4) 0.03081(10) Uani d . 1 . .
F F1 0.54717(11) 0.63181(10) -0.11562(10) 0.0284(2) Uani d . 1 . .
F F2 0.31465(14) 0.40675(9) -0.19141(11) 0.0322(2) Uani d . 1 . .
O O1 0.10801(14) 0.52987(10) -0.10574(11) 0.0238(2) Uani d . 1 . .
O O2 0.37834(13) 1.03015(10) 0.10823(10) 0.0196(2) Uani d . 1 . .
N N1 0.33089(14) 0.77459(12) -0.05183(12) 0.0146(2) Uani d . 1 . .
H H1 0.4368 0.8292 -0.0609 0.018 Uiso calc R 1 . .
N N2 0.03816(15) 0.83557(13) -0.09290(12) 0.0182(2) Uani d . 1 . .
H H2 -0.0483 0.8420 -0.0661 0.022 Uiso d R 1 . .
N N3 0.16459(15) 0.79008(12) 0.15566(12) 0.0155(2) Uani d . 1 . .
H H3 0.0753 0.6993 0.1225 0.019 Uiso d R 1 . .
C C1 0.25344(17) 0.61960(14) -0.10878(14) 0.0153(2) Uani d . 1 . .
C C2 0.36184(19) 0.55503(15) -0.18656(15) 0.0192(3) Uani d . 1 . .
C C3 0.02381(19) 0.84469(16) -0.24394(15) 0.0201(3) Uani d . 1 . .
H H3A 0.0704 0.7721 -0.2874 0.024 Uiso calc R 1 . .
C C4 -0.1816(2) 0.78961(18) -0.33779(16) 0.0259(3) Uani d . 1 . .
H H4A -0.2525 0.6837 -0.3386 0.039 Uiso calc R 1 . .
H H4B -0.1939 0.7916 -0.4394 0.039 Uiso calc R 1 . .
H H4C -0.2309 0.8581 -0.2959 0.039 Uiso calc R 1 . .
C C5 0.1427(2) 1.00657(18) -0.24315(16) 0.0262(3) Uani d . 1 . .
H H5A 0.2750 1.0341 -0.1889 0.039 Uiso calc R 1 . .
H H5B 0.1051 1.0809 -0.1947 0.039 Uiso calc R 1 . .
H H5C 0.1246 1.0090 -0.3453 0.039 Uiso calc R 1 . .
C C6 0.29579(18) 0.82087(16) 0.30596(15) 0.0208(3) Uani d . 1 . .
H H6A 0.3976 0.9277 0.3361 0.025 Uiso calc R 1 . .
C C7 0.1941(2) 0.81568(18) 0.41385(16) 0.0268(3) Uani d . 1 . .
H H7A 0.1366 0.8888 0.4081 0.040 Uiso calc R 1 . .
H H7B 0.2834 0.8442 0.5148 0.040 Uiso calc R 1 . .
H H7C 0.0965 0.7108 0.3884 0.040 Uiso calc R 1 . .
C C8 0.3848(3) 0.7080(2) 0.3090(2) 0.0390(4) Uani d . 1 . .
H H8A 0.4568 0.7195 0.2437 0.058 Uiso calc R 1 . .
H H8B 0.2867 0.6020 0.2749 0.058 Uiso calc R 1 . .
H H8C 0.4685 0.7294 0.4105 0.058 Uiso calc R 1 . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
P1 0.01625(15) 0.00992(14) 0.01683(16) 0.00349(11) 0.01039(12) 0.00433(11)
Cl1 0.0425(2) 0.0345(2) 0.02119(18) 0.01780(18) 0.01803(16) 0.00824(15)
F1 0.0208(4) 0.0305(5) 0.0358(5) 0.0133(4) 0.0117(4) 0.0065(4)
F2 0.0469(6) 0.0162(4) 0.0489(6) 0.0186(4) 0.0300(5) 0.0147(4)
O1 0.0247(5) 0.0128(4) 0.0318(5) 0.0005(4) 0.0187(4) 0.0040(4)
O2 0.0237(5) 0.0115(4) 0.0233(5) 0.0026(4) 0.0158(4) 0.0030(4)
N1 0.0148(5) 0.0108(5) 0.0195(5) 0.0034(4) 0.0109(4) 0.0043(4)
N2 0.0203(5) 0.0223(5) 0.0191(5) 0.0112(5) 0.0126(4) 0.0091(4)
N3 0.0153(5) 0.0125(5) 0.0161(5) 0.0012(4) 0.0081(4) 0.0042(4)
C1 0.0178(6) 0.0119(5) 0.0171(6) 0.0054(5) 0.0089(5) 0.0047(4)
C2 0.0243(7) 0.0134(6) 0.0246(7) 0.0089(5) 0.0131(5) 0.0076(5)
C3 0.0255(7) 0.0244(7) 0.0177(6) 0.0151(6) 0.0118(5) 0.0076(5)
C4 0.0262(7) 0.0281(7) 0.0222(7) 0.0131(6) 0.0066(6) 0.0045(6)
C5 0.0276(7) 0.0329(8) 0.0226(7) 0.0121(6) 0.0129(6) 0.0148(6)
C6 0.0176(6) 0.0220(6) 0.0180(6) 0.0032(5) 0.0057(5) 0.0069(5)
C7 0.0352(8) 0.0334(8) 0.0180(6) 0.0181(7) 0.0124(6) 0.0099(6)
C8 0.0395(9) 0.0669(12) 0.0355(9) 0.0384(9) 0.0212(8) 0.0278(9)
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'
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'
F F 0.0171 0.0103 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O2 P1 N3 . . 112.27(5) ?
O2 P1 N2 . . 119.69(6) ?
N3 P1 N2 . . 103.94(6) ?
O2 P1 N1 . . 105.13(5) ?
N3 P1 N1 . . 112.31(5) ?
N2 P1 N1 . . 103.30(6) ?
C1 N1 P1 . . 122.76(9) ?
C1 N1 H1 . . 118.6 ?
P1 N1 H1 . . 118.6 ?
C3 N2 P1 . . 123.77(9) ?
C3 N2 H2 . . 116.2 ?
P1 N2 H2 . . 117.0 ?
C6 N3 P1 . . 121.89(8) ?
C6 N3 H3 . . 112.7 ?
P1 N3 H3 . . 117.9 ?
O1 C1 N1 . . 126.01(12) ?
O1 C1 C2 . . 118.79(11) ?
N1 C1 C2 . . 115.19(10) ?
F2 C2 F1 . . 107.66(11) ?
F2 C2 C1 . . 109.72(10) ?
F1 C2 C1 . . 112.14(11) ?
F2 C2 Cl1 . . 108.56(10) ?
F1 C2 Cl1 . . 108.94(9) ?
C1 C2 Cl1 . . 109.74(9) ?
N2 C3 C5 . . 111.99(11) ?
N2 C3 C4 . . 108.48(11) ?
C5 C3 C4 . . 112.00(12) ?
N2 C3 H3A . . 108.1 ?
C5 C3 H3A . . 108.1 ?
C4 C3 H3A . . 108.1 ?
C3 C4 H4A . . 109.5 ?
C3 C4 H4B . . 109.5 ?
H4A C4 H4B . . 109.5 ?
C3 C4 H4C . . 109.5 ?
H4A C4 H4C . . 109.5 ?
H4B C4 H4C . . 109.5 ?
C3 C5 H5A . . 109.5 ?
C3 C5 H5B . . 109.5 ?
H5A C5 H5B . . 109.5 ?
C3 C5 H5C . . 109.5 ?
H5A C5 H5C . . 109.5 ?
H5B C5 H5C . . 109.5 ?
N3 C6 C8 . . 111.29(12) ?
N3 C6 C7 . . 109.51(11) ?
C8 C6 C7 . . 111.49(12) ?
N3 C6 H6A . . 108.1 ?
C8 C6 H6A . . 108.1 ?
C7 C6 H6A . . 108.1 ?
C6 C7 H7A . . 109.5 ?
C6 C7 H7B . . 109.5 ?
H7A C7 H7B . . 109.5 ?
C6 C7 H7C . . 109.5 ?
H7A C7 H7C . . 109.5 ?
H7B C7 H7C . . 109.5 ?
C6 C8 H8A . . 109.5 ?
C6 C8 H8B . . 109.5 ?
H8A C8 H8B . . 109.5 ?
C6 C8 H8C . . 109.5 ?
H8A C8 H8C . . 109.5 ?
H8B C8 H8C . . 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
P1 O2 . 1.4768(9) ?
P1 N3 . 1.6190(11) ?
P1 N2 . 1.6262(12) ?
P1 N1 . 1.7039(11) ?
Cl1 C2 . 1.7566(14) ?
F1 C2 . 1.3366(16) ?
F2 C2 . 1.3351(15) ?
O1 C1 . 1.2127(15) ?
N1 C1 . 1.3447(15) ?
N1 H1 . 0.8800 ?
N2 C3 . 1.4775(17) ?
N2 H2 . 0.8390 ?
N3 C6 . 1.4754(17) ?
N3 H3 . 0.8536 ?
C1 C2 . 1.5399(17) ?
C3 C5 . 1.520(2) ?
C3 C4 . 1.5207(19) ?
C3 H3A . 1.0000 ?
C4 H4A . 0.9800 ?
C4 H4B . 0.9800 ?
C4 H4C . 0.9800 ?
C5 H5A . 0.9800 ?
C5 H5B . 0.9800 ?
C5 H5C . 0.9800 ?
C6 C8 . 1.513(2) ?
C6 C7 . 1.5164(19) ?
C6 H6A . 1.0000 ?
C7 H7A . 0.9800 ?
C7 H7B . 0.9800 ?
C7 H7C . 0.9800 ?
C8 H8A . 0.9800 ?
C8 H8B . 0.9800 ?
C8 H8C . 0.9800 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N1 H1 O2 2_675 0.88 1.87 2.7295(13) 164
N3 H3 O1 2_565 0.85 2.14 2.9645(14) 163
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O2 P1 N1 C1 . . . . 168.43(10) ?
N3 P1 N1 C1 . . . . 46.05(12) ?
N2 P1 N1 C1 . . . . -65.33(11) ?
O2 P1 N2 C3 . . . . 72.29(12) ?
N3 P1 N2 C3 . . . . -161.47(10) ?
N1 P1 N2 C3 . . . . -44.04(11) ?
O2 P1 N3 C6 . . . . -36.29(12) ?
N2 P1 N3 C6 . . . . -167.07(10) ?
N1 P1 N3 C6 . . . . 81.94(11) ?
P1 N1 C1 O1 . . . . 0.56(19) ?
P1 N1 C1 C2 . . . . 179.37(9) ?
O1 C1 C2 F2 . . . . -22.92(17) ?
N1 C1 C2 F2 . . . . 158.19(11) ?
O1 C1 C2 F1 . . . . -142.50(13) ?
N1 C1 C2 F1 . . . . 38.60(15) ?
O1 C1 C2 Cl1 . . . . 96.28(13) ?
N1 C1 C2 Cl1 . . . . -82.62(12) ?
P1 N2 C3 C5 . . . . -61.53(14) ?
P1 N2 C3 C4 . . . . 174.35(9) ?
P1 N3 C6 C8 . . . . -89.23(13) ?
P1 N3 C6 C7 . . . . 147.05(10) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656518