#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/14/2221465.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_2221465
loop_
_publ_author_name
'Han, Jun'
'Li, Wenguang'
'Wang, Shufang'
'Jiang, Juli'
_publ_section_title
;
 Tris(3-aminophenyl)phosphine oxide ethanol solvate
;
_journal_coeditor_code           PK2158
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o839
_journal_paper_doi               10.1107/S160053680900909X
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C18 H18 N3 O P, C2 H6 O'
_chemical_formula_moiety         'C18 H18 N3 O P, C2 H6 O'
_chemical_formula_sum            'C20 H24 N3 O2 P'
_chemical_formula_weight         369.39
_chemical_name_systematic
;
Tris(3-aminophenyl)phosphine oxide ethanol solvate
;
_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                109.131(3)
_cell_angle_beta                 94.245(3)
_cell_angle_gamma                114.028(2)
_cell_formula_units_Z            2
_cell_length_a                   9.1046(13)
_cell_length_b                   10.7595(15)
_cell_length_c                   12.020(3)
_cell_measurement_reflns_used    706
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      19.5
_cell_measurement_theta_min      2.6
_cell_volume                     986.3(3)
_computing_cell_refinement       'SMART (Bruker, 2005)'
_computing_data_collection       'SMART (Bruker, 2005)'
_computing_data_reduction        'SAINT (Bruker, 2005)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker SMART 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  0.0581
_diffrn_reflns_av_sigmaI/netI    0.1261
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5014
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.25
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.158
_exptl_absorpt_correction_T_max  0.954
_exptl_absorpt_correction_T_min  0.947
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.244
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.529
_refine_diff_density_min         -0.410
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.845
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         3420
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.845
_refine_ls_R_factor_all          0.1236
_refine_ls_R_factor_gt           0.0591
_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)+(0.0599P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1282
_refine_ls_wR_factor_ref         0.1489
_reflns_number_gt                1659
_reflns_number_total             3420
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            pk2158.cif
_cod_data_source_block           I
_cod_database_code               2221465
_cod_database_fobs_code          2221465
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 0.32847(11) 0.46681(10) 0.24048(9) 0.040 Uani d . 1 . .
O O1 0.2533(3) 0.4519(2) 0.3452(2) 0.048 Uani d . 1 . .
O O2 0.0137(3) 0.2243(3) 0.3724(3) 0.0692(9) Uani d . 1 . .
H H2 0.0879 0.2929 0.3632 0.104 Uiso calc R 1 . .
C C12 0.5751(4) 0.7116(4) 0.2172(3) 0.0450(9) Uani d . 1 . .
H H12 0.6148 0.6475 0.1749 0.054 Uiso calc R 1 . .
C C7 0.4373(4) 0.6580(4) 0.2618(3) 0.0398(9) Uani d . 1 . .
C C1 0.1745(4) 0.3739(4) 0.0993(3) 0.0430(9) Uani d . 1 . .
C C13 0.4720(4) 0.3909(3) 0.2210(3) 0.0380(9) Uani d . 1 . .
C C17 0.6849(4) 0.3539(4) 0.3165(3) 0.046 Uani d . 1 . .
C C11 0.6559(4) 0.8607(4) 0.2346(3) 0.049 Uani d . 1 . .
C C18 0.5679(4) 0.4064(3) 0.3238(3) 0.044 Uani d . 1 . .
H H18 0.5539 0.4528 0.3996 0.052 Uiso calc R 1 . .
N N1 0.7909(4) 0.9160(4) 0.1905(3) 0.076 Uani d . 1 . .
H H1A 0.8373 1.0081 0.2021 0.091 Uiso calc R 1 . .
H H1B 0.8298 0.8588 0.1510 0.091 Uiso calc R 1 . .
C C14 0.4895(4) 0.3209(4) 0.1081(3) 0.048 Uani d . 1 . .
H H14 0.4243 0.3095 0.0387 0.058 Uiso calc R 1 . .
C C16 0.7007(4) 0.2837(4) 0.2010(3) 0.052 Uani d . 1 . .
H H16 0.7776 0.2472 0.1931 0.062 Uiso calc R 1 . .
C C6 0.0464(4) 0.2340(4) 0.0766(3) 0.0486(10) Uani d . 1 . .
H H6 0.0446 0.1908 0.1324 0.058 Uiso calc R 1 . .
C C5 -0.0779(4) 0.1596(4) -0.0291(4) 0.057 Uani d . 1 . .
C C2 0.1779(5) 0.4355(4) 0.0146(4) 0.0548(11) Uani d . 1 . .
H H2A 0.2642 0.5277 0.0288 0.066 Uiso calc R 1 . .
C C10 0.5934(5) 0.9530(4) 0.2983(4) 0.0592(12) Uani d . 1 . .
H H10 0.6457 1.0527 0.3111 0.071 Uiso calc R 1 . .
N N2 0.7780(4) 0.3664(4) 0.4182(3) 0.0764(11) Uani d . 1 . .
H H2B 0.7646 0.4074 0.4886 0.092 Uiso calc R 1 . .
H H2C 0.8497 0.3332 0.4116 0.092 Uiso calc R 1 . .
C C9 0.4574(5) 0.9015(4) 0.3424(4) 0.0599(11) Uani d . 1 . .
H H9 0.4176 0.9657 0.3844 0.072 Uiso calc R 1 . .
C C8 0.3784(5) 0.7539(4) 0.3248(3) 0.0534(10) Uani d . 1 . .
H H8 0.2857 0.7189 0.3553 0.064 Uiso calc R 1 . .
C C15 0.6044(4) 0.2679(4) 0.0989(3) 0.056 Uani d . 1 . .
H H15 0.6170 0.2208 0.0228 0.068 Uiso calc R 1 . .
C C3 0.0530(5) 0.3608(5) -0.0918(4) 0.0677(13) Uani d . 1 . .
H H3 0.0555 0.4027 -0.1486 0.081 Uiso calc R 1 . .
N N3 -0.2044(5) 0.0239(4) -0.0519(4) 0.106 Uani d . 1 . .
H H3A -0.2077 -0.0164 -0.0005 0.127 Uiso calc R 1 . .
H H3B -0.2811 -0.0214 -0.1178 0.127 Uiso calc R 1 . .
C C4 -0.0726(5) 0.2259(5) -0.1117(4) 0.0687(13) Uani d . 1 . .
H H4 -0.1568 0.1768 -0.1822 0.082 Uiso calc R 1 . .
C C20 0.0756(6) 0.2038(6) 0.4755(5) 0.0963(19) Uani d . 1 . .
H H20A 0.1265 0.2969 0.5458 0.116 Uiso calc R 1 . .
H H20B -0.0150 0.1328 0.4941 0.116 Uiso calc R 1 . .
C C19 0.1946(8) 0.1515(7) 0.4477(6) 0.147(3) Uani d . 1 . .
H H19A 0.1414 0.0555 0.3825 0.221 Uiso calc R 1 . .
H H19B 0.2426 0.1447 0.5180 0.221 Uiso calc R 1 . .
H H19C 0.2800 0.2189 0.4239 0.221 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'
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 C13 . . 112.04(15) ?
O1 P1 C7 . . 110.89(16) ?
C13 P1 C7 . . 107.89(16) ?
O1 P1 C1 . . 112.16(15) ?
C13 P1 C1 . . 106.99(16) ?
C7 P1 C1 . . 106.60(16) ?
C20 O2 H2 . . 109.5 ?
C7 C12 C11 . . 121.1(4) ?
C7 C12 H12 . . 119.5 ?
C11 C12 H12 . . 119.5 ?
C12 C7 C8 . . 119.3(3) ?
C12 C7 P1 . . 122.6(3) ?
C8 C7 P1 . . 118.1(3) ?
C2 C1 C6 . . 119.5(3) ?
C2 C1 P1 . . 122.8(3) ?
C6 C1 P1 . . 117.7(3) ?
C14 C13 C18 . . 120.2(3) ?
C14 C13 P1 . . 122.0(3) ?
C18 C13 P1 . . 117.8(3) ?
N2 C17 C18 . . 121.5(3) ?
N2 C17 C16 . . 121.0(3) ?
C18 C17 C16 . . 117.5(3) ?
N1 C11 C10 . . 120.0(4) ?
N1 C11 C12 . . 122.2(4) ?
C10 C11 C12 . . 117.8(4) ?
C13 C18 C17 . . 121.3(3) ?
C13 C18 H18 . . 119.4 ?
C17 C18 H18 . . 119.4 ?
C11 N1 H1A . . 120.0 ?
C11 N1 H1B . . 120.0 ?
H1A N1 H1B . . 120.0 ?
C13 C14 C15 . . 119.4(3) ?
C13 C14 H14 . . 120.3 ?
C15 C14 H14 . . 120.3 ?
C15 C16 C17 . . 121.0(4) ?
C15 C16 H16 . . 119.5 ?
C17 C16 H16 . . 119.5 ?
C5 C6 C1 . . 120.0(4) ?
C5 C6 H6 . . 120.0 ?
C1 C6 H6 . . 120.0 ?
N3 C5 C6 . . 120.6(4) ?
N3 C5 C4 . . 120.3(4) ?
C6 C5 C4 . . 119.1(4) ?
C1 C2 C3 . . 120.6(4) ?
C1 C2 H2A . . 119.7 ?
C3 C2 H2A . . 119.7 ?
C9 C10 C11 . . 121.7(4) ?
C9 C10 H10 . . 119.2 ?
C11 C10 H10 . . 119.2 ?
C17 N2 H2B . . 120.0 ?
C17 N2 H2C . . 120.0 ?
H2B N2 H2C . . 120.0 ?
C10 C9 C8 . . 120.1(4) ?
C10 C9 H9 . . 120.0 ?
C8 C9 H9 . . 120.0 ?
C9 C8 C7 . . 120.0(4) ?
C9 C8 H8 . . 120.0 ?
C7 C8 H8 . . 120.0 ?
C16 C15 C14 . . 120.6(4) ?
C16 C15 H15 . . 119.7 ?
C14 C15 H15 . . 119.7 ?
C4 C3 C2 . . 119.3(4) ?
C4 C3 H3 . . 120.4 ?
C2 C3 H3 . . 120.4 ?
C5 N3 H3A . . 120.0 ?
C5 N3 H3B . . 120.0 ?
H3A N3 H3B . . 120.0 ?
C3 C4 C5 . . 121.6(4) ?
C3 C4 H4 . . 119.2 ?
C5 C4 H4 . . 119.2 ?
C19 C20 O2 . . 109.0(5) ?
C19 C20 H20A . . 109.9 ?
O2 C20 H20A . . 109.9 ?
C19 C20 H20B . . 109.9 ?
O2 C20 H20B . . 109.9 ?
H20A C20 H20B . . 108.3 ?
C20 C19 H19A . . 109.5 ?
C20 C19 H19B . . 109.5 ?
H19A C19 H19B . . 109.5 ?
C20 C19 H19C . . 109.5 ?
H19A C19 H19C . . 109.5 ?
H19B C19 H19C . . 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 O1 . 1.500(2) ?
P1 C13 . 1.794(3) ?
P1 C7 . 1.799(3) ?
P1 C1 . 1.799(4) ?
O2 C20 . 1.441(5) ?
O2 H2 . 0.8200 ?
C12 C7 . 1.381(5) ?
C12 C11 . 1.398(5) ?
C12 H12 . 0.9300 ?
C7 C8 . 1.388(5) ?
C1 C2 . 1.381(5) ?
C1 C6 . 1.399(5) ?
C13 C14 . 1.376(5) ?
C13 C18 . 1.380(4) ?
C17 N2 . 1.370(4) ?
C17 C18 . 1.390(4) ?
C17 C16 . 1.396(5) ?
C11 N1 . 1.362(4) ?
C11 C10 . 1.387(5) ?
C18 H18 . 0.9300 ?
N1 H1A . 0.8600 ?
N1 H1B . 0.8600 ?
C14 C15 . 1.377(5) ?
C14 H14 . 0.9300 ?
C16 C15 . 1.372(5) ?
C16 H16 . 0.9300 ?
C6 C5 . 1.385(5) ?
C6 H6 . 0.9300 ?
C5 N3 . 1.362(5) ?
C5 C4 . 1.393(5) ?
C2 C3 . 1.394(5) ?
C2 H2A . 0.9300 ?
C10 C9 . 1.361(5) ?
C10 H10 . 0.9300 ?
N2 H2B . 0.8600 ?
N2 H2C . 0.8600 ?
C9 C8 . 1.383(5) ?
C9 H9 . 0.9300 ?
C8 H8 . 0.9300 ?
C15 H15 . 0.9300 ?
C3 C4 . 1.361(5) ?
C3 H3 . 0.9300 ?
N3 H3A . 0.8600 ?
N3 H3B . 0.8600 ?
C4 H4 . 0.9300 ?
C20 C19 . 1.424(8) ?
C20 H20A . 0.9700 ?
C20 H20B . 0.9700 ?
C19 H19A . 0.9600 ?
C19 H19B . 0.9600 ?
C19 H19C . 0.9600 ?
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
_geom_hbond_publ_flag
N3 H3A N1 1_445 0.86 2.62 3.469(6) 167.5 y
O2 H2 O1 . 0.82 1.85 2.672(3) 178.3 y
N2 H2B O1 2_666 0.86 2.14 2.987(4) 168.4 y
N2 H2C O2 1_655 0.86 2.23 3.089(5) 172.7 y
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
C11 C12 C7 C8 . . . . 0.0(5) ?
C11 C12 C7 P1 . . . . 179.4(3) ?
O1 P1 C7 C12 . . . . 148.9(3) ?
C13 P1 C7 C12 . . . . 25.9(3) ?
C1 P1 C7 C12 . . . . -88.7(3) ?
O1 P1 C7 C8 . . . . -31.7(3) ?
C13 P1 C7 C8 . . . . -154.7(3) ?
C1 P1 C7 C8 . . . . 90.7(3) ?
O1 P1 C1 C2 . . . . 137.1(3) ?
C13 P1 C1 C2 . . . . -99.7(3) ?
C7 P1 C1 C2 . . . . 15.5(4) ?
O1 P1 C1 C6 . . . . -42.5(3) ?
C13 P1 C1 C6 . . . . 80.8(3) ?
C7 P1 C1 C6 . . . . -164.0(3) ?
O1 P1 C13 C14 . . . . 145.0(3) ?
C7 P1 C13 C14 . . . . -92.6(3) ?
C1 P1 C13 C14 . . . . 21.7(3) ?
O1 P1 C13 C18 . . . . -35.8(3) ?
C7 P1 C13 C18 . . . . 86.5(3) ?
C1 P1 C13 C18 . . . . -159.2(3) ?
C7 C12 C11 N1 . . . . -179.3(3) ?
C7 C12 C11 C10 . . . . 0.1(5) ?
C14 C13 C18 C17 . . . . 0.8(5) ?
P1 C13 C18 C17 . . . . -178.4(3) ?
N2 C17 C18 C13 . . . . -178.7(3) ?
C16 C17 C18 C13 . . . . -0.6(5) ?
C18 C13 C14 C15 . . . . -0.6(5) ?
P1 C13 C14 C15 . . . . 178.5(3) ?
N2 C17 C16 C15 . . . . 178.3(3) ?
C18 C17 C16 C15 . . . . 0.2(5) ?
C2 C1 C6 C5 . . . . -1.4(5) ?
P1 C1 C6 C5 . . . . 178.1(3) ?
C1 C6 C5 N3 . . . . -179.3(4) ?
C1 C6 C5 C4 . . . . 0.3(6) ?
C6 C1 C2 C3 . . . . 1.4(6) ?
P1 C1 C2 C3 . . . . -178.1(3) ?
N1 C11 C10 C9 . . . . 179.1(3) ?
C12 C11 C10 C9 . . . . -0.3(6) ?
C11 C10 C9 C8 . . . . 0.4(6) ?
C10 C9 C8 C7 . . . . -0.2(6) ?
C12 C7 C8 C9 . . . . 0.0(5) ?
P1 C7 C8 C9 . . . . -179.4(3) ?
C17 C16 C15 C14 . . . . -0.1(6) ?
C13 C14 C15 C16 . . . . 0.3(5) ?
C1 C2 C3 C4 . . . . -0.1(6) ?
C2 C3 C4 C5 . . . . -1.0(6) ?
N3 C5 C4 C3 . . . . -179.5(4) ?
C6 C5 C4 C3 . . . . 1.0(6) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30655746
