##############################################################################
# #
# This CIF contains the data in a paper accepted for publication in #
# Acta Crystallographica Section E. It conforms to the requirements of #
# Notes for Authors for Acta Crystallographica Section E, and has been #
# peer reviewed under the auspices of the IUCr Commission on Journals. #
# #
# Full details of the Crystallographic Information File format #
# are given in the paper "The Crystallographic Information File (CIF): #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H. #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685]. #
# #
# The current version of the core CIF dictionary is obtainable from #
# ftp://ftp.iucr.org/pub/cif_core.dic. #
# #
# Software is freely available for graphical display of the structure(s) #
# in this CIF. For information consult the CIF software page #
# http://www.iucr.org/resources/cif/software. #
# #
# This file may be used for bona fide research purposes within the #
# scientific community so long as proper attribution is given to the journal #
# article from which it was obtained. #
# #
##############################################################################
data_I
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
N-[(morpholin-4-ylamino)(phenoxy)phosphoryl]morpholin-4-amine
;
_chemical_name_common
;
Phenyl bis(morpholin-4-ylamido)phosphinate
;
_chemical_formula_moiety 'C14 H23 N4 O4 P'
_chemical_formula_sum 'C14 H23 N4 O4 P'
_chemical_formula_iupac 'C14 H23 N4 O4 P'
_chemical_formula_weight 342.33
_chemical_melting_point ?
_symmetry_cell_setting triclinic
_symmetry_space_group_name_H-M 'P -1'
_symmetry_space_group_name_hall '-P 1'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
_cell_length_a 4.7469(2)
_cell_length_b 12.3528(5)
_cell_length_c 14.2149(5)
_cell_angle_alpha 90.542(3)
_cell_angle_beta 98.389(4)
_cell_angle_gamma 93.009(4)
_cell_volume 823.35(6)
_cell_formula_units_Z 2
_cell_measurement_reflns_used 5042
_cell_measurement_theta_min 3.2910
_cell_measurement_theta_max 27.1870
_cell_measurement_temperature 120(2)
_exptl_crystal_description prism
_exptl_crystal_colour colorless
_exptl_crystal_size_max 0.20
_exptl_crystal_size_mid 0.10
_exptl_crystal_size_min 0.10
_exptl_crystal_density_diffrn 1.381
_exptl_crystal_density_meas ?
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 364
_exptl_absorpt_coefficient_mu 0.193
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details '(CrysAlis RED; Oxford Diffraction, 2009)'
_exptl_absorpt_correction_T_min 0.877
_exptl_absorpt_correction_T_max 1.000
_exptl_special_details ?
_diffrn_ambient_temperature 120(2)
_diffrn_radiation_type 'MoK\a'
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_source 'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator 'graphite'
_diffrn_measurement_device_type 'Oxford Diffraction Xcalibur S'
_diffrn_measurement_method \w
_diffrn_detector_area_resol_mean 8.4353
_diffrn_reflns_number 10043
_diffrn_reflns_av_R_equivalents 0.0212
_diffrn_reflns_av_sigmaI/netI 0.0369
_diffrn_reflns_theta_min 3.30
_diffrn_reflns_theta_max 25.00
_diffrn_reflns_theta_full 25.00
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_limit_h_min -5
_diffrn_reflns_limit_h_max 5
_diffrn_reflns_limit_k_min -14
_diffrn_reflns_limit_k_max 14
_diffrn_reflns_limit_l_min -16
_diffrn_reflns_limit_l_max 9
_diffrn_standards_number 0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time .
_diffrn_standards_decay_% .
_refine_special_details
;
Refinement of F^2^ against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F^2^, conventional
R-factors R are based on F, with F set to zero for
negative F^2^. The threshold expression of F^2^ >
\s(F^2^) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F^2^ are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger.
;
_reflns_number_total 2888
_reflns_number_gt 2272
_reflns_threshold_expression I>2sigma(I)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_R_factor_all 0.0404
_refine_ls_R_factor_gt 0.0287
_refine_ls_wR_factor_gt 0.0680
_refine_ls_wR_factor_ref 0.0697
_refine_ls_goodness_of_fit_ref 0.987
_refine_ls_restrained_S_all 0.962
_refine_ls_number_reflns 2888
_refine_ls_number_parameters 262
_refine_ls_number_restraints 162
_refine_ls_hydrogen_treatment mixed
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0404P)^2^P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_refine_ls_shift/su_max 0.001
_refine_ls_shift/su_mean 0.000
_refine_diff_density_max 0.222
_refine_diff_density_min -0.319
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
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'
_computing_data_collection 'CrysAlis CCD (Oxford Diffraction, 2009)'
_computing_cell_refinement 'CrysAlis RED (Oxford Diffraction, 2009)'
_computing_data_reduction 'CrysAlis RED (Oxford Diffraction, 2009)'
_computing_structure_solution 'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics 'Mercury (Macrae et al., 2008)'
_computing_publication_material 'enCIFer (Allen et al., 2004)'
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_symmetry_multiplicity
_atom_site_disorder_assembly
_atom_site_disorder_group
P P1 0.34183(7) 0.63069(3) 0.29935(3) 0.01615(12) Uani d . 1 1 . .
O O1 0.55619(19) 0.55524(7) 0.33888(7) 0.0196(2) Uani d . 1 1 . .
O O2 0.11776(19) 0.58245(7) 0.21233(7) 0.0196(3) Uani d . 1 1 A .
O O3 0.1822(2) 0.80213(10) 0.63761(8) 0.0382(3) Uani d . 1 1 . .
O O4 0.3795(2) 1.01932(8) 0.11186(8) 0.0310(3) Uani d . 1 1 . .
N N3 0.1088(3) 0.67116(10) 0.36409(9) 0.0180(3) Uani d . 1 1 . .
C C1 0.1500(3) 0.48228(11) 0.16832(11) 0.0169(3) Uani d U 1 1 . .
C C2A 0.1144(7) 0.3882(2) 0.2144(3) 0.0201(8) Uani d PU 0.500(2) 1 A 1
H H2AA 0.0754 0.3896 0.2781 0.024 Uiso calc PR 0.500(2) 1 A 1
C C3A 0.1348(8) 0.2902(2) 0.1688(3) 0.0228(8) Uani d PU 0.500(2) 1 A 1
H H3AA 0.1112 0.2236 0.2004 0.027 Uiso calc PR 0.500(2) 1 A 1
C C4A 0.192(5) 0.2917(13) 0.0735(11) 0.0236(19) Uani d PU 0.500(2) 1 A 1
H H4AA 0.2198 0.2253 0.0426 0.028 Uiso calc PR 0.500(2) 1 A 1
C C5A 0.2073(6) 0.3829(2) 0.0270(2) 0.0222(8) Uani d PU 0.500(2) 1 A 1
H H5AA 0.2332 0.3813 -0.0381 0.027 Uiso calc PR 0.500(2) 1 A 1
C C6A 0.1858(6) 0.4815(2) 0.0724(2) 0.0193(8) Uani d PU 0.500(2) 1 A 1
H H6AA 0.1953 0.5475 0.0388 0.023 Uiso calc PR 0.500(2) 1 A 1
C C2B -0.0552(7) 0.4023(2) 0.1721(2) 0.0220(8) Uani d PU 0.500(2) 1 A 2
H H2BA -0.2160 0.4145 0.2028 0.026 Uiso calc PR 0.500(2) 1 A 2
C C3B -0.0253(8) 0.3024(3) 0.1303(3) 0.0276(9) Uani d PU 0.500(2) 1 A 2
H H3BA -0.1718 0.2470 0.1306 0.033 Uiso calc PR 0.500(2) 1 A 2
C C4B 0.203(5) 0.2816(13) 0.0897(11) 0.023(2) Uani d PU 0.500(2) 1 A 2
H H4BA 0.2230 0.2116 0.0642 0.027 Uiso calc PR 0.500(2) 1 A 2
C C5B 0.4184(6) 0.3673(2) 0.0852(2) 0.0255(9) Uani d PU 0.500(2) 1 A 2
H H5BA 0.5776 0.3553 0.0538 0.031 Uiso calc PR 0.500(2) 1 A 2
C C6B 0.3922(6) 0.4675(2) 0.1271(2) 0.0214(8) Uani d PU 0.500(2) 1 A 2
H H6BA 0.5358 0.5241 0.1274 0.026 Uiso calc PR 0.500(2) 1 A 2
N N1 0.2242(2) 0.72689(9) 0.45092(9) 0.0187(3) Uani d . 1 1 . .
C C8 0.0377(3) 0.81391(12) 0.46689(12) 0.0274(4) Uani d . 1 1 . .
H H8A -0.1571 0.7832 0.4706 0.033 Uiso calc R 1 1 . .
H H8B 0.0268 0.8651 0.4134 0.033 Uiso calc R 1 1 . .
C C9 0.1576(4) 0.87271(13) 0.55883(13) 0.0374(5) Uani d . 1 1 . .
H H9A 0.3480 0.9064 0.5530 0.045 Uiso calc R 1 1 . .
H H9B 0.0319 0.9314 0.5703 0.045 Uiso calc R 1 1 . .
C C10 0.3616(4) 0.71670(14) 0.62119(12) 0.0330(4) Uani d . 1 1 . .
H H10A 0.3772 0.6673 0.6759 0.040 Uiso calc R 1 1 . .
H H10B 0.5552 0.7478 0.6160 0.040 Uiso calc R 1 1 . .
C C11 0.2460(3) 0.65330(12) 0.53168(11) 0.0257(4) Uani d . 1 1 . .
H H11A 0.3746 0.5950 0.5217 0.031 Uiso calc R 1 1 . .
H H11B 0.0557 0.6194 0.5373 0.031 Uiso calc R 1 1 . .
N N4 0.5044(3) 0.73922(10) 0.26441(10) 0.0217(3) Uani d . 1 1 . .
N N2 0.3561(2) 0.82518(9) 0.21815(9) 0.0182(3) Uani d . 1 1 . .
C C13 0.3853(3) 0.82364(12) 0.11680(11) 0.0219(4) Uani d . 1 1 . .
H H13A 0.2914 0.7562 0.0862 0.026 Uiso calc R 1 1 . .
H H13B 0.5898 0.8251 0.1096 0.026 Uiso calc R 1 1 . .
C C14 0.2503(3) 0.92070(12) 0.06897(12) 0.0280(4) Uani d . 1 1 . .
H H14A 0.2714 0.9192 0.0007 0.034 Uiso calc R 1 1 . .
H H14B 0.0440 0.9171 0.0737 0.034 Uiso calc R 1 1 . .
C C15 0.3467(4) 1.02243(12) 0.20977(13) 0.0334(4) Uani d . 1 1 . .
H H15A 0.1412 1.0206 0.2156 0.040 Uiso calc R 1 1 . .
H H15B 0.4364 1.0911 0.2393 0.040 Uiso calc R 1 1 . .
C C16 0.4816(3) 0.92776(12) 0.26208(12) 0.0267(4) Uani d . 1 1 . .
H H16A 0.6896 0.9322 0.2603 0.032 Uiso calc R 1 1 . .
H H16B 0.4514 0.9308 0.3295 0.032 Uiso calc R 1 1 . .
H H3N -0.035(3) 0.6311(12) 0.3652(11) 0.024(4) Uiso d . 1 1 . .
H H4N 0.674(4) 0.7378(13) 0.2627(12) 0.032(5) Uiso d . 1 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 0.01465(19) 0.01504(19) 0.0181(3) 0.00138(14) -0.00015(16) 0.00092(16)
O1 0.0163(5) 0.0179(5) 0.0238(7) 0.0023(4) -0.0004(4) 0.0032(5)
O2 0.0187(5) 0.0187(5) 0.0201(7) 0.0048(4) -0.0027(5) -0.0049(5)
O3 0.0424(7) 0.0456(7) 0.0272(8) -0.0048(6) 0.0110(6) -0.0135(6)
O4 0.0410(7) 0.0185(6) 0.0328(8) -0.0035(5) 0.0047(6) 0.0074(5)
N3 0.0157(6) 0.0174(6) 0.0196(8) -0.0032(5) -0.0004(6) -0.0047(6)
C1 0.0163(7) 0.0169(7) 0.0168(9) 0.0032(6) -0.0004(6) -0.0007(7)
C2A 0.0189(16) 0.0240(16) 0.0173(19) 0.0026(13) 0.0012(15) 0.0018(14)
C3A 0.0257(18) 0.0142(15) 0.026(2) -0.0001(14) -0.0026(18) 0.0050(15)
C4A 0.028(3) 0.023(4) 0.020(4) 0.006(3) 0.000(4) -0.005(3)
C5A 0.0229(17) 0.0264(17) 0.0173(19) 0.0017(13) 0.0037(15) -0.0025(14)
C6A 0.0189(16) 0.0177(14) 0.0203(19) -0.0018(12) 0.0000(15) 0.0051(13)
C2B 0.0207(17) 0.0256(16) 0.020(2) 0.0007(13) 0.0047(16) 0.0038(14)
C3B 0.0274(19) 0.0203(16) 0.033(2) -0.0035(15) 0.0000(18) 0.0058(16)
C4B 0.033(3) 0.012(2) 0.022(5) 0.009(2) -0.003(4) 0.005(3)
C5B 0.0223(16) 0.0326(17) 0.022(2) 0.0087(13) 0.0020(15) -0.0064(15)
C6B 0.0180(16) 0.0232(15) 0.022(2) 0.0006(12) 0.0003(14) 0.0008(14)
N1 0.0203(6) 0.0183(6) 0.0169(8) 0.0005(5) 0.0007(6) -0.0030(6)
C8 0.0283(8) 0.0213(8) 0.0322(11) 0.0036(7) 0.0028(8) -0.0077(7)
C9 0.0410(10) 0.0298(9) 0.0412(13) 0.0025(8) 0.0063(9) -0.0134(9)
C10 0.0393(10) 0.0366(10) 0.0228(11) -0.0037(8) 0.0059(8) -0.0001(8)
C11 0.0318(9) 0.0248(8) 0.0207(10) -0.0010(7) 0.0052(8) 0.0026(8)
N4 0.0140(6) 0.0227(7) 0.0279(9) 0.0020(5) 0.0007(6) 0.0088(6)
N2 0.0222(6) 0.0142(6) 0.0172(8) 0.0013(5) -0.0011(6) 0.0035(6)
C13 0.0272(8) 0.0201(8) 0.0177(10) -0.0015(6) 0.0022(7) -0.0006(7)
C14 0.0341(9) 0.0240(8) 0.0241(11) -0.0027(7) -0.0006(8) 0.0055(7)
C15 0.0449(10) 0.0179(8) 0.0381(12) -0.0018(7) 0.0097(9) -0.0020(8)
C16 0.0345(9) 0.0223(8) 0.0224(10) -0.0063(7) 0.0040(8) -0.0034(7)
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes.
;
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 O1 . 1.4705(10) ?
P1 O2 . 1.5975(10) ?
P1 N4 . 1.6295(13) ?
P1 N3 . 1.6331(13) ?
O2 C1 . 1.4068(16) ?
O3 C9 . 1.421(2) ?
O3 C10 . 1.4286(19) ?
O4 C15 . 1.4233(19) ?
O4 C14 . 1.4249(17) ?
N3 N1 . 1.4297(17) ?
N3 H3N . 0.823(15) ?
C1 C2A . 1.354(3) ?
C1 C2B . 1.358(3) ?
C1 C6B . 1.384(3) ?
C1 C6A . 1.399(3) ?
C2A C3A . 1.382(4) ?
C2A H2AA . 0.9500 ?
C3A C4A . 1.421(17) ?
C3A H3AA . 0.9500 ?
C4A C5A . 1.316(15) ?
C4A H4AA . 0.9500 ?
C5A C6A . 1.389(4) ?
C5A H5AA . 0.9500 ?
C6A H6AA . 0.9500 ?
C2B C3B . 1.388(4) ?
C2B H2BA . 0.9500 ?
C3B C4B . 1.33(2) ?
C3B H3BA . 0.9500 ?
C4B C5B . 1.44(2) ?
C4B H4BA . 0.9500 ?
C5B C6B . 1.387(4) ?
C5B H5BA . 0.9500 ?
C6B H6BA . 0.9500 ?
N1 C8 . 1.4645(17) ?
N1 C11 . 1.4663(19) ?
C8 C9 . 1.510(2) ?
C8 H8A . 0.9900 ?
C8 H8B . 0.9900 ?
C9 H9A . 0.9900 ?
C9 H9B . 0.9900 ?
C10 C11 . 1.505(2) ?
C10 H10A . 0.9900 ?
C10 H10B . 0.9900 ?
C11 H11A . 0.9900 ?
C11 H11B . 0.9900 ?
N4 N2 . 1.4186(16) ?
N4 H4N . 0.811(16) ?
N2 C16 . 1.4656(18) ?
N2 C13 . 1.4674(18) ?
C13 C14 . 1.510(2) ?
C13 H13A . 0.9900 ?
C13 H13B . 0.9900 ?
C14 H14A . 0.9900 ?
C14 H14B . 0.9900 ?
C15 C16 . 1.512(2) ?
C15 H15A . 0.9900 ?
C15 H15B . 0.9900 ?
C16 H16A . 0.9900 ?
C16 H16B . 0.9900 ?
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
O1 P1 O2 . . 114.63(5) ?
O1 P1 N4 . . 108.95(6) ?
O2 P1 N4 . . 108.62(6) ?
O1 P1 N3 . . 119.86(6) ?
O2 P1 N3 . . 96.87(6) ?
N4 P1 N3 . . 106.95(7) ?
C1 O2 P1 . . 122.17(8) ?
C9 O3 C10 . . 109.51(13) ?
C15 O4 C14 . . 109.64(12) ?
N1 N3 P1 . . 115.73(9) ?
N1 N3 H3N . . 116.7(11) ?
P1 N3 H3N . . 116.9(11) ?
C2A C1 C6B . . 103.2(2) ?
C2B C1 C6B . . 122.9(2) ?
C2A C1 C6A . . 120.6(2) ?
C2B C1 C6A . . 103.1(2) ?
C2A C1 O2 . . 120.66(18) ?
C2B C1 O2 . . 117.71(18) ?
C6B C1 O2 . . 119.37(17) ?
C6A C1 O2 . . 118.26(16) ?
C1 C2A C3A . . 120.0(3) ?
C1 C2A H2AA . . 120.0 ?
C3A C2A H2AA . . 120.0 ?
C2A C3A C4A . . 118.2(7) ?
C2A C3A H3AA . . 120.9 ?
C4A C3A H3AA . . 120.9 ?
C5A C4A C3A . . 121.4(13) ?
C5A C4A H4AA . . 119.3 ?
C3A C4A H4AA . . 119.3 ?
C4A C5A C6A . . 120.4(8) ?
C4A C5A H5AA . . 119.8 ?
C6A C5A H5AA . . 119.8 ?
C5A C6A C1 . . 119.0(3) ?
C5A C6A H6AA . . 120.5 ?
C1 C6A H6AA . . 120.5 ?
C1 C2B C3B . . 118.6(3) ?
C1 C2B H2BA . . 120.7 ?
C3B C2B H2BA . . 120.7 ?
C4B C3B C2B . . 122.1(8) ?
C4B C3B H3BA . . 119.0 ?
C2B C3B H3BA . . 119.0 ?
C3B C4B C5B . . 118.9(13) ?
C3B C4B H4BA . . 120.6 ?
C5B C4B H4BA . . 120.6 ?
C6B C5B C4B . . 119.7(9) ?
C6B C5B H5BA . . 120.2 ?
C4B C5B H5BA . . 120.2 ?
C1 C6B C5B . . 117.8(3) ?
C1 C6B H6BA . . 121.1 ?
C5B C6B H6BA . . 121.1 ?
N3 N1 C8 . . 108.48(11) ?
N3 N1 C11 . . 111.34(11) ?
C8 N1 C11 . . 109.63(13) ?
N1 C8 C9 . . 108.73(13) ?
N1 C8 H8A . . 109.9 ?
C9 C8 H8A . . 109.9 ?
N1 C8 H8B . . 109.9 ?
C9 C8 H8B . . 109.9 ?
H8A C8 H8B . . 108.3 ?
O3 C9 C8 . . 112.07(14) ?
O3 C9 H9A . . 109.2 ?
C8 C9 H9A . . 109.2 ?
O3 C9 H9B . . 109.2 ?
C8 C9 H9B . . 109.2 ?
H9A C9 H9B . . 107.9 ?
O3 C10 C11 . . 111.43(13) ?
O3 C10 H10A . . 109.3 ?
C11 C10 H10A . . 109.3 ?
O3 C10 H10B . . 109.3 ?
C11 C10 H10B . . 109.3 ?
H10A C10 H10B . . 108.0 ?
N1 C11 C10 . . 109.01(13) ?
N1 C11 H11A . . 109.9 ?
C10 C11 H11A . . 109.9 ?
N1 C11 H11B . . 109.9 ?
C10 C11 H11B . . 109.9 ?
H11A C11 H11B . . 108.3 ?
N2 N4 P1 . . 122.73(9) ?
N2 N4 H4N . . 118.0(12) ?
P1 N4 H4N . . 117.8(12) ?
N4 N2 C16 . . 108.27(11) ?
N4 N2 C13 . . 109.67(11) ?
C16 N2 C13 . . 109.55(11) ?
N2 C13 C14 . . 109.89(12) ?
N2 C13 H13A . . 109.7 ?
C14 C13 H13A . . 109.7 ?
N2 C13 H13B . . 109.7 ?
C14 C13 H13B . . 109.7 ?
H13A C13 H13B . . 108.2 ?
O4 C14 C13 . . 111.09(12) ?
O4 C14 H14A . . 109.4 ?
C13 C14 H14A . . 109.4 ?
O4 C14 H14B . . 109.4 ?
C13 C14 H14B . . 109.4 ?
H14A C14 H14B . . 108.0 ?
O4 C15 C16 . . 111.29(13) ?
O4 C15 H15A . . 109.4 ?
C16 C15 H15A . . 109.4 ?
O4 C15 H15B . . 109.4 ?
C16 C15 H15B . . 109.4 ?
H15A C15 H15B . . 108.0 ?
N2 C16 C15 . . 110.24(13) ?
N2 C16 H16A . . 109.6 ?
C15 C16 H16A . . 109.6 ?
N2 C16 H16B . . 109.6 ?
C15 C16 H16B . . 109.6 ?
H16A C16 H16B . . 108.1 ?
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
N3 H3N O1 1_455 0.823(15) 2.093(16) 2.8951(16) 164.9(15)
_iucr_refine_instructions_details
;
TITL mn227 in P-1
CELL 0.71073 4.7469 12.3528 14.2149 90.542 98.389 93.009
ZERR 2.00 0.0002 0.0005 0.0005 0.003 0.004 0.004
LATT 1
SFAC C H N O P
UNIT 28 46 8 8 2
L.S. 40
BOND $H
FMAP 2
PLAN 10
temp -153
size 0.1 0.1 0.2
omit 0 50
acta
simu 0.015 C1 > C6B
delu 0.008 C1 > C6B
eqiv $1 x-1, y, z
eqiv $2 x+1, y, z
htab N3 O1_$1
htab N3 N4_$1
htab N4 N3_$2
WGHT 0.040400
FVAR 0.30454 0.50003
P1 5 0.341832 0.630689 0.299348 11.00000 0.01465 0.01504 =
0.01809 0.00092 -0.00015 0.00138
O1 4 0.556188 0.555242 0.338879 11.00000 0.01631 0.01791 =
0.02376 0.00318 -0.00037 0.00231
O2 4 0.117764 0.582453 0.212334 11.00000 0.01865 0.01872 =
0.02007 -0.00493 -0.00268 0.00482
O3 4 0.182243 0.802129 0.637607 11.00000 0.04240 0.04565 =
0.02717 -0.01345 0.01097 -0.00477
O4 4 0.379482 1.019318 0.111857 11.00000 0.04100 0.01847 =
0.03285 0.00743 0.00472 -0.00351
N3 3 0.108808 0.671157 0.364093 11.00000 0.01570 0.01738 =
0.01958 -0.00472 -0.00043 -0.00323
C1 1 0.150027 0.482282 0.168323 11.00000 0.01628 0.01690 =
0.01683 -0.00071 -0.00041 0.00320
PART 1
C2A 1 0.114425 0.388196 0.214398 21.00000 0.01889 0.02398 =
0.01731 0.00180 0.00115 0.00261
AFIX 43
H2AA 2 0.075431 0.389567 0.278064 21.00000 -1.20000
AFIX 0
C3A 1 0.134796 0.290206 0.168842 21.00000 0.02574 0.01423 =
0.02637 0.00502 -0.00258 -0.00006
AFIX 43
H3AA 2 0.111200 0.223638 0.200442 21.00000 -1.20000
AFIX 0
C4A 1 0.191990 0.291669 0.073453 21.00000 0.02768 0.02314 =
0.01955 -0.00475 0.00035 0.00592
AFIX 43
H4AA 2 0.219769 0.225343 0.042593 21.00000 -1.20000
AFIX 0
C5A 1 0.207304 0.382887 0.026950 21.00000 0.02293 0.02643 =
0.01735 -0.00252 0.00373 0.00174
AFIX 43
H5AA 2 0.233207 0.381278 -0.038058 21.00000 -1.20000
AFIX 0
C6A 1 0.185805 0.481530 0.072393 21.00000 0.01885 0.01771 =
0.02029 0.00515 0.00002 -0.00184
AFIX 43
H6AA 2 0.195258 0.547450 0.038829 21.00000 -1.20000
AFIX 0
PART 2
C2B 1 -0.055234 0.402338 0.172136 -21.00000 0.02066 0.02564 =
0.02031 0.00383 0.00470 0.00074
AFIX 43
H2BA 2 -0.215995 0.414545 0.202769 -21.00000 -1.20000
AFIX 0
C3B 1 -0.025308 0.302387 0.130342 -21.00000 0.02744 0.02027 =
0.03332 0.00583 0.00004 -0.00349
AFIX 43
H3BA 2 -0.171847 0.247029 0.130645 -21.00000 -1.20000
AFIX 0
C4B 1 0.202919 0.281628 0.089741 -21.00000 0.03291 0.01166 =
0.02237 0.00533 -0.00337 0.00853
AFIX 43
H4BA 2 0.223026 0.211555 0.064249 -21.00000 -1.20000
AFIX 0
C5B 1 0.418392 0.367338 0.085226 -21.00000 0.02230 0.03260 =
0.02200 -0.00637 0.00204 0.00869
AFIX 43
H5BA 2 0.577574 0.355271 0.053756 -21.00000 -1.20000
AFIX 0
C6B 1 0.392202 0.467517 0.127051 -21.00000 0.01798 0.02320 =
0.02212 0.00079 0.00025 0.00065
AFIX 43
H6BA 2 0.535760 0.524130 0.127358 -21.00000 -1.20000
AFIX 0
PART 0
N1 3 0.224170 0.726889 0.450916 11.00000 0.02032 0.01829 =
0.01690 -0.00297 0.00071 0.00048
C8 1 0.037671 0.813914 0.466888 11.00000 0.02826 0.02133 =
0.03222 -0.00770 0.00281 0.00361
AFIX 23
H8A 2 -0.157129 0.783157 0.470629 11.00000 -1.20000
H8B 2 0.026812 0.865060 0.413441 11.00000 -1.20000
AFIX 0
C9 1 0.157604 0.872706 0.558829 11.00000 0.04096 0.02983 =
0.04121 -0.01338 0.00632 0.00250
AFIX 23
H9A 2 0.348018 0.906400 0.553000 11.00000 -1.20000
H9B 2 0.031918 0.931409 0.570319 11.00000 -1.20000
AFIX 0
C10 1 0.361643 0.716701 0.621189 11.00000 0.03932 0.03659 =
0.02281 -0.00011 0.00594 -0.00369
AFIX 23
H10A 2 0.377234 0.667340 0.675949 11.00000 -1.20000
H10B 2 0.555160 0.747797 0.615999 11.00000 -1.20000
AFIX 0
C11 1 0.246047 0.653300 0.531681 11.00000 0.03178 0.02476 =
0.02075 0.00257 0.00519 -0.00105
AFIX 23
H11A 2 0.374564 0.595031 0.521655 11.00000 -1.20000
H11B 2 0.055736 0.619386 0.537327 11.00000 -1.20000
AFIX 0
N4 3 0.504396 0.739220 0.264408 11.00000 0.01400 0.02274 =
0.02791 0.00877 0.00065 0.00200
N2 3 0.356075 0.825184 0.218150 11.00000 0.02220 0.01418 =
0.01717 0.00354 -0.00115 0.00135
C13 1 0.385316 0.823644 0.116801 11.00000 0.02720 0.02015 =
0.01772 -0.00059 0.00222 -0.00154
AFIX 23
H13A 2 0.291420 0.756158 0.086229 11.00000 -1.20000
H13B 2 0.589774 0.825086 0.109580 11.00000 -1.20000
AFIX 0
C14 1 0.250278 0.920695 0.068970 11.00000 0.03406 0.02395 =
0.02407 0.00546 -0.00059 -0.00269
AFIX 23
H14A 2 0.271360 0.919219 0.000707 11.00000 -1.20000
H14B 2 0.043994 0.917101 0.073709 11.00000 -1.20000
AFIX 0
C15 1 0.346692 1.022429 0.209769 11.00000 0.04495 0.01786 =
0.03805 -0.00200 0.00973 -0.00177
AFIX 23
H15A 2 0.141175 1.020555 0.215553 11.00000 -1.20000
H15B 2 0.436436 1.091107 0.239254 11.00000 -1.20000
AFIX 0
C16 1 0.481649 0.927758 0.262080 11.00000 0.03452 0.02226 =
0.02245 -0.00338 0.00403 -0.00634
AFIX 23
H16A 2 0.689628 0.932205 0.260269 11.00000 -1.20000
H16B 2 0.451369 0.930816 0.329481 11.00000 -1.20000
AFIX 0
H3N 2 -0.034790 0.631130 0.365195 11.00000 0.02442
H4N 2 0.674230 0.737811 0.262653 11.00000 0.03185
HKLF 4
REM mn227 in P-1
REM R1 = 0.0287 for 2272 Fo > 4sig(Fo) and 0.0404 for all 2888 data
REM 262 parameters refined using 162 restraints
END
WGHT 0.0393 0.0000
REM Highest difference peak 0.222, deepest hole -0.319, 1-sigma level 0.036
Q1 1 0.4154 0.6861 0.2587 11.00000 0.05 0.22
Q2 1 0.4471 0.6993 0.2917 11.00000 0.05 0.19
Q3 1 0.1725 0.6979 0.4044 11.00000 0.05 0.18
Q4 1 0.2400 0.6427 0.3602 11.00000 0.05 0.17
;
data_global
_journal_date_recd_electronic 2011-07-01
_journal_date_accepted 2011-07-22
_journal_name_full 'Acta Crystallographica, Section E'
_journal_year 2011
_journal_volume 67
_journal_issue 8
_journal_page_first o2202
_journal_page_last o2202
_journal_paper_category QO
_journal_coeditor_code GK2392
_publ_contact_author_name 'Mehrdad Pourayoubi'
_publ_contact_author_address
;
Department of Chemistry, Ferdowsi University of Mashhad, Mashhad, 91779, Iran
;
_publ_contact_author_email mehrdad_pourayoubi@yahoo.com
_publ_contact_author_fax '(+98)-511-8796416'
_publ_contact_author_phone '(+98)9155143058'
_publ_section_title
;
Phenyl bis(morpholin-4-ylamido)phosphinate
;
loop_
_publ_author_name
_publ_author_address
'Pourayoubi, Mehrdad'
;
Department of Chemistry, Ferdowsi University of Mashhad, Mashhad 91779, Iran
;
'Eshtiagh-Hosseini, Hossein'
;
Department of Chemistry, Ferdowsi University of Mashhad, Mashhad 91779, Iran
;
'Negari, Monireh'
;
Department of Chemistry, Ferdowsi University of Mashhad, Mashhad 91779, Iran
;
'Ne\