#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:58:33 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202018 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/21/8102166.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_8102166
loop_
_publ_author_name
'Yazdanbakhsh, Mohammad'
'Sabbaghi, Fahimeh'
'Boese, Roland'
_publ_section_title
;
Crystal structure of N-trifluoroacetyl-N',N"-bis(N-cyclohexylmethyl)
phosphoric triamide, CF₃C(O)N(H)P(O)[N(CH₃)(C₆H₁₁)]₂
;
_journal_issue                   3
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              331
_journal_page_last               332
_journal_volume                  222
_journal_year                    2007
_chemical_formula_structural     CF3C(O)N(H)P(O)[N(CH3)(C6H11)]2
_chemical_formula_sum            'C16 H29 F3 N3 O2 P'
_chemical_formula_weight         383.39
_chemical_name_systematic
; 
N-trifluoroacetyl-N',N"-bis(N-cyclohexylmethyl)phosphoric 
triamide, CF3C(O)N(H)P(O)[N(CH3)(C6H11)]2
;
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                106.370(3)
_cell_angle_beta                 103.077(3)
_cell_angle_gamma                109.306(2)
_cell_formula_units_Z            2
_cell_length_a                   8.4051(4)
_cell_length_b                   10.9557(5)
_cell_length_c                   12.4462(9)
_cell_measurement_temperature    203(2)
_cell_volume                     971.07(10)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      203(2)
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.977
_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  0.0239
_diffrn_reflns_av_sigmaI/netI    0.0173
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            46850
_diffrn_reflns_theta_full        33.66
_diffrn_reflns_theta_max         33.66
_diffrn_reflns_theta_min         1.82
_exptl_absorpt_coefficient_mu    0.183
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.765
_refine_diff_density_min         -0.432
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         7535
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0645
_refine_ls_R_factor_gt           0.0518
_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)+(0.0865P)²+0.2503P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1474
_refine_ls_wR_factor_ref         0.1591
_reflns_number_gt                6076
_reflns_number_total             7535
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            1267-2070.cff
_cod_data_source_block           yaz_h
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               8102166
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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_symmetry_multiplicity
_atom_site_Wyckoff_symbol
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.04680(4) 0.63166(3) 0.39106(3) 0.02875(9) Uani 1 2 i d . . .
O1 O 0.03577(12) 0.48946(9) 0.37321(8) 0.03227(18) Uani 1 2 i d . . .
O2 O 0.23020(19) 0.95321(11) 0.57586(12) 0.0547(3) Uani 1 2 i d . . .
N1 N 0.10845(15) 0.71732(11) 0.54222(10) 0.0343(2) Uani 1 2 i d . . .
H1 H 0.0774 0.6650 0.5791 0.041 Uiso 1 2 i d R . .
N2 N -0.14630(13) 0.62939(11) 0.32492(11) 0.0361(2) Uani 1 2 i d . . .
N3 N 0.19745(13) 0.73321(11) 0.35499(10) 0.0327(2) Uani 1 2 i d . . .
F1 F 0.03947(19) 0.83749(19) 0.75015(13) 0.0973(6) Uani 1 2 i d . . .
F2 F 0.2702(2) 1.02700(12) 0.80216(11) 0.0784(4) Uani 1 2 i d . . .
F3 F 0.2979(3) 0.84026(17) 0.79264(12) 0.0873(5) Uani 1 2 i d . . .
C1 C 0.17976(19) 0.85695(13) 0.60818(13) 0.0382(3) Uani 1 2 i d . . .
C2 C 0.1960(2) 0.89179(15) 0.73970(14) 0.0448(3) Uani 1 2 i d . . .
C3 C -0.1689(2) 0.76058(16) 0.3563(2) 0.0526(4) Uani 1 2 i d . . .
H3A H -0.2398 0.7643 0.2850 0.079 Uiso 1 2 i d R . .
H3B H -0.0514 0.8395 0.3912 0.079 Uiso 1 2 i d R . .
H3C H -0.2299 0.7649 0.4138 0.079 Uiso 1 2 i d R . .
C4 C -0.31076(15) 0.49623(13) 0.27031(13) 0.0347(2) Uani 1 2 i d . . .
H4 H -0.2731 0.4216 0.2510 0.042 Uiso 1 2 i d R . .
C5 C -0.4336(2) 0.48391(18) 0.15294(16) 0.0488(3) Uani 1 2 i d . . .
H5A H -0.3691 0.4923 0.0989 0.059 Uiso 1 2 i d R . .
H5B H -0.4718 0.5585 0.1685 0.059 Uiso 1 2 i d R . .
C6 C -0.5996(2) 0.3431(2) 0.09560(18) 0.0606(5) Uani 1 2 i d . . .
H6A H -0.5613 0.2688 0.0757 0.073 Uiso 1 2 i d R . .
H6B H -0.6778 0.3369 0.0230 0.073 Uiso 1 2 i d R . .
C7 C -0.7015(2) 0.3238(2) 0.18025(19) 0.0583(5) Uani 1 2 i d . . .
H7A H -0.8031 0.2339 0.1433 0.070 Uiso 1 2 i d R . .
H7B H -0.7456 0.3949 0.1967 0.070 Uiso 1 2 i d R . .
C8 C -0.5796(2) 0.33572(19) 0.29745(17) 0.0508(4) Uani 1 2 i d . . .
H8A H -0.5431 0.2601 0.2816 0.061 Uiso 1 2 i d R . .
H8B H -0.6447 0.3275 0.3512 0.061 Uiso 1 2 i d R . .
C9 C -0.41185(19) 0.47503(16) 0.35610(15) 0.0431(3) Uani 1 2 i d . . .
H9A H -0.4475 0.5503 0.3798 0.052 Uiso 1 2 i d R . .
H9B H -0.3331 0.4774 0.4266 0.052 Uiso 1 2 i d R . .
C10 C 0.38794(16) 0.77707(16) 0.42241(14) 0.0409(3) Uani 1 2 i d . . .
H10A H 0.4529 0.7690 0.3674 0.061 Uiso 1 2 i d R . .
H10B H 0.3977 0.7174 0.4658 0.061 Uiso 1 2 i d R . .
H10C H 0.4391 0.8738 0.4786 0.061 Uiso 1 2 i d R . .
C11 C 0.15562(16) 0.75732(12) 0.24352(11) 0.0308(2) Uani 1 2 i d . . .
H11 H 0.0268 0.7191 0.2087 0.037 Uiso 1 2 i d R . .
C12 C 0.2259(3) 0.91331(15) 0.26726(15) 0.0533(4) Uani 1 2 i d . . .
H12A H 0.3553 0.9549 0.2974 0.064 Uiso 1 2 i d R . .
H12B H 0.1861 0.9595 0.3263 0.064 Uiso 1 2 i d R . .
C13 C 0.1591(3) 0.9329(2) 0.1511(2) 0.0745(7) Uani 1 2 i d . . .
H13A H 0.2032 1.0311 0.1662 0.089 Uiso 1 2 i d R . .
H13B H 0.0298 0.8940 0.1230 0.089 Uiso 1 2 i d R . .
C14 C 0.2180(4) 0.8623(4) 0.0576(2) 0.0938(10) Uani 1 2 i d . . .
H14A H 0.3468 0.9074 0.0821 0.113 Uiso 1 2 i d R . .
H14B H 0.1672 0.8714 -0.0154 0.113 Uiso 1 2 i d R . .
C15 C 0.1569(4) 0.7076(4) 0.03458(19) 0.0867(8) Uani 1 2 i d . . .
H15A H 0.2055 0.6669 -0.0212 0.104 Uiso 1 2 i d R . .
H15B H 0.0279 0.6605 -0.0009 0.104 Uiso 1 2 i d R . .
C16 C 0.2207(3) 0.6855(2) 0.15126(17) 0.0624(5) Uani 1 2 i d . . .
H16A H 0.1711 0.5869 0.1346 0.075 Uiso 1 2 i d R . .
H16B H 0.3497 0.7215 0.1820 0.075 Uiso 1 2 i d R . .
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'
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 P1 N3 118.22(5) . . ?
O1 P1 N2 112.56(5) . . ?
N3 P1 N2 107.05(5) . . ?
O1 P1 N1 105.63(5) . . ?
N3 P1 N1 104.24(6) . . ?
N2 P1 N1 108.49(6) . . ?
C1 N1 P1 129.09(9) . . ?
C3 N2 C4 117.64(10) . . ?
C3 N2 P1 119.08(10) . . ?
C4 N2 P1 119.66(8) . . ?
C10 N3 C11 117.26(10) . . ?
C10 N3 P1 117.82(9) . . ?
C11 N3 P1 123.45(8) . . ?
O2 C1 N1 128.26(14) . . ?
O2 C1 C2 118.42(13) . . ?
N1 C1 C2 113.32(12) . . ?
F1 C2 F2 108.58(15) . . ?
F1 C2 F3 106.09(17) . . ?
F2 C2 F3 106.36(15) . . ?
F1 C2 C1 111.74(14) . . ?
F2 C2 C1 112.12(13) . . ?
F3 C2 C1 111.61(12) . . ?
N2 C4 C5 111.17(10) . . ?
N2 C4 C9 112.64(12) . . ?
C5 C4 C9 111.49(11) . . ?
C4 C5 C6 110.32(12) . . ?
C7 C6 C5 111.32(17) . . ?
C6 C7 C8 110.93(13) . . ?
C7 C8 C9 111.19(13) . . ?
C8 C9 C4 111.30(14) . . ?
N3 C11 C16 114.14(12) . . ?
N3 C11 C12 111.87(11) . . ?
C16 C11 C12 109.73(14) . . ?
C11 C12 C13 109.87(13) . . ?
C14 C13 C12 111.4(2) . . ?
C13 C14 C15 111.23(17) . . ?
C14 C15 C16 111.4(2) . . ?
C11 C16 C15 109.90(16) . . ?
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 O1 1.4782(8) . ?
P1 N3 1.6279(10) . ?
P1 N2 1.6339(10) . ?
P1 N1 1.7120(12) . ?
O2 C1 1.2143(17) . ?
N1 C1 1.3552(16) . ?
N2 C3 1.4668(17) . ?
N2 C4 1.4777(16) . ?
N3 C10 1.4678(16) . ?
N3 C11 1.4714(15) . ?
F1 C2 1.306(2) . ?
F2 C2 1.3070(18) . ?
F3 C2 1.327(2) . ?
C1 C2 1.535(2) . ?
C4 C5 1.527(2) . ?
C4 C9 1.5283(19) . ?
C5 C6 1.530(2) . ?
C6 C7 1.518(3) . ?
C7 C8 1.524(2) . ?
C8 C9 1.528(2) . ?
C11 C16 1.515(2) . ?
C11 C12 1.5250(18) . ?
C12 C13 1.529(2) . ?
C13 C14 1.484(4) . ?
C14 C15 1.518(4) . ?
C15 C16 1.545(3) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24741331
