#------------------------------------------------------------------------------
#$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       'φ and ω'
_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/[σ²(Fo²)+(0.0527P)²+0.0127P] where P=(Fo²+2Fc²)/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>2σ(I)
_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_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
