##############################################################################
#                                                                            #
# 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,P,P-Triisopropylphosphinic amide
;
_chemical_name_common     ?
_chemical_formula_moiety     'C9 H22 N O P'
_chemical_formula_sum     'C9 H22 N O P'
_chemical_formula_iupac     'C9 H22 N O P'
_chemical_formula_weight     191.25
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/c'
_symmetry_space_group_name_Hall     '-P 2ybc'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x, -y-1/2, z-1/2'
_cell_length_a     15.030(3)
_cell_length_b     8.4813(17)
_cell_length_c     10.071(2)
_cell_angle_alpha     90.00
_cell_angle_beta     107.36(3)
_cell_angle_gamma     90.00
_cell_volume     1225.3(4)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     5563
_cell_measurement_theta_min     2.07
_cell_measurement_theta_max     29.19
_cell_measurement_temperature     195(2)
_exptl_crystal_description     prism
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.42
_exptl_crystal_size_mid     0.26
_exptl_crystal_size_min     0.20
_exptl_crystal_density_diffrn     1.037
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     424
_exptl_absorpt_coefficient_mu     0.189
_exptl_absorpt_correction_type     none
_exptl_absorpt_process_details     ?
_exptl_absorpt_correction_T_min     ?
_exptl_absorpt_correction_T_max     ?
_exptl_special_details
;
;
_diffrn_ambient_temperature     195(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Stoe IPDS II'
_diffrn_measurement_method     ω
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     19581
_diffrn_reflns_av_R_equivalents     0.0350
_diffrn_reflns_av_sigmaI/netI     0.0370
_diffrn_reflns_theta_min     2.79
_diffrn_reflns_theta_max     27.50
_diffrn_reflns_theta_full     27.50
_diffrn_measured_fraction_theta_max     1.000
_diffrn_measured_fraction_theta_full     1.000
_diffrn_reflns_limit_h_min     -19
_diffrn_reflns_limit_h_max     19
_diffrn_reflns_limit_k_min     -11
_diffrn_reflns_limit_k_max     11
_diffrn_reflns_limit_l_min     -13
_diffrn_reflns_limit_l_max     13
_diffrn_standards_number     ?
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_refine_special_details
;
Refinement of F² against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F², conventional
R-factors R are based on F, with F set to zero for
negative F². The threshold expression of F² >
σ(F²) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F² 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     2807
_reflns_number_gt     2012
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0594
_refine_ls_R_factor_gt     0.0390
_refine_ls_wR_factor_gt     0.0868
_refine_ls_wR_factor_ref     0.0909
_refine_ls_goodness_of_fit_ref     0.894
_refine_ls_restrained_S_all     0.894
_refine_ls_number_reflns     2807
_refine_ls_number_parameters     115
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0547P)²+0.0000P] where P=(Fo²+2Fc²)/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     0.390
_refine_diff_density_min     -0.158
_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'
    'P' 'P' 0.1023 0.0942
                         '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'
_computing_data_collection     'X-AREA (Stoe & Cie, 2005)'
_computing_cell_refinement     'X-AREA (Stoe & Cie, 2005)'
_computing_data_reduction     'X-AREA (Stoe & Cie, 2005)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'XP in SHELXTL (Sheldrick, 2008)'
_computing_publication_material     'SHELXL97 (Sheldrick, 2008)'
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
    C C1 0.70679(12) 0.5276(2) 0.6731(2) 0.0525(4) Uani d . 1 1 . .
    H H1B 0.6513 0.5582 0.5941 0.063 Uiso calc R 1 1 . .
    C C2 0.68976(19) 0.5848(2) 0.8073(3) 0.0830(7) Uani d . 1 1 . .
    H H2A 0.7434 0.5574 0.8868 0.125 Uiso calc R 1 1 . .
    H H2B 0.6336 0.5342 0.8178 0.125 Uiso calc R 1 1 . .
    H H2C 0.6813 0.6995 0.8034 0.125 Uiso calc R 1 1 . .
    C C3 0.79173(16) 0.6067(3) 0.6497(3) 0.0802(7) Uani d . 1 1 . .
    H H3A 0.7812 0.7207 0.6396 0.120 Uiso calc R 1 1 . .
    H H3B 0.8021 0.5645 0.5650 0.120 Uiso calc R 1 1 . .
    H H3C 0.8466 0.5858 0.7294 0.120 Uiso calc R 1 1 . .
    C C4 0.61524(11) 0.22776(19) 0.69367(17) 0.0418(4) Uani d . 1 1 . .
    H H4 0.6119 0.2607 0.7874 0.050 Uiso calc R 1 1 . .
    C C5 0.52745(12) 0.2872(3) 0.5848(2) 0.0653(6) Uani d . 1 1 . .
    H H5A 0.5320 0.2652 0.4915 0.098 Uiso calc R 1 1 . .
    H H5B 0.5213 0.4010 0.5960 0.098 Uiso calc R 1 1 . .
    H H5C 0.4727 0.2333 0.5971 0.098 Uiso calc R 1 1 . .
    C C6 0.62213(15) 0.0496(2) 0.6924(2) 0.0692(6) Uani d . 1 1 . .
    H H6A 0.5651 0.0034 0.7039 0.104 Uiso calc R 1 1 . .
    H H6B 0.6759 0.0151 0.7689 0.104 Uiso calc R 1 1 . .
    H H6C 0.6298 0.0150 0.6037 0.104 Uiso calc R 1 1 . .
    C C7 0.89734(10) 0.2189(2) 0.79953(16) 0.0427(4) Uani d . 1 1 . .
    H H7 0.9106 0.2800 0.7226 0.051 Uiso calc R 1 1 . .
    C C8 0.96785(13) 0.2667(3) 0.9330(2) 0.0733(6) Uani d . 1 1 . .
    H H8A 0.9625 0.3801 0.9478 0.110 Uiso calc R 1 1 . .
    H H8B 1.0306 0.2429 0.9282 0.110 Uiso calc R 1 1 . .
    H H8C 0.9566 0.2083 1.0104 0.110 Uiso calc R 1 1 . .
    C C9 0.90379(17) 0.0463(3) 0.7687(3) 0.0834(7) Uani d . 1 1 . .
    H H9A 0.8915 -0.0166 0.8429 0.125 Uiso calc R 1 1 . .
    H H9B 0.9664 0.0226 0.7633 0.125 Uiso calc R 1 1 . .
    H H9C 0.8576 0.0206 0.6797 0.125 Uiso calc R 1 1 . .
    N N1 0.80376(9) 0.26201(16) 0.80317(13) 0.0398(3) Uani d . 1 1 . .
    H H1A 0.7925 0.2590 0.8840 0.048 Uiso calc R 1 1 . .
    O O1 0.73426(8) 0.26804(15) 0.53446(11) 0.0531(3) Uani d . 1 1 . .
    P P1 0.71920(3) 0.31507(5) 0.66763(4) 0.03470(12) Uani 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
    C1 0.0490(10) 0.0468(9) 0.0619(11) 0.0063(8) 0.0167(9) 0.0155(9)
    C2 0.1089(19) 0.0465(12) 0.1096(19) 0.0121(12) 0.0570(16) -0.0108(12)
    C3 0.0785(15) 0.0565(13) 0.112(2) -0.0137(11) 0.0373(14) 0.0151(12)
    C4 0.0398(8) 0.0532(10) 0.0348(8) -0.0039(7) 0.0148(7) 0.0047(7)
    C5 0.0366(9) 0.0924(16) 0.0629(12) -0.0074(9) 0.0087(8) 0.0160(11)
    C6 0.0697(13) 0.0576(12) 0.0814(15) -0.0150(10) 0.0243(12) 0.0030(10)
    C7 0.0377(8) 0.0581(11) 0.0365(8) 0.0107(7) 0.0174(7) 0.0075(7)
    C8 0.0426(10) 0.1149(19) 0.0573(12) 0.0060(11) 0.0072(9) -0.0030(12)
    C9 0.0787(15) 0.0704(15) 0.1029(19) 0.0283(12) 0.0297(14) -0.0056(13)
    N1 0.0383(7) 0.0593(8) 0.0250(6) 0.0094(6) 0.0143(5) 0.0085(6)
    O1 0.0553(7) 0.0817(9) 0.0270(6) 0.0022(6) 0.0193(5) 0.0009(5)
    P1 0.03607(19) 0.0451(2) 0.02528(19) 0.00340(18) 0.01274(14) 0.00474(18)
_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
    C1 C3 . 1.521(3) ?
    C1 C2 . 1.528(3) ?
    C1 P1 . 1.8150(18) ?
    C1 H1B . 1.0000 ?
    C2 H2A . 0.9800 ?
    C2 H2B . 0.9800 ?
    C2 H2C . 0.9800 ?
    C3 H3A . 0.9800 ?
    C3 H3B . 0.9800 ?
    C3 H3C . 0.9800 ?
    C4 C6 . 1.515(3) ?
    C4 C5 . 1.527(2) ?
    C4 P1 . 1.8175(16) ?
    C4 H4 . 1.0000 ?
    C5 H5A . 0.9800 ?
    C5 H5B . 0.9800 ?
    C5 H5C . 0.9800 ?
    C6 H6A . 0.9800 ?
    C6 H6B . 0.9800 ?
    C6 H6C . 0.9800 ?
    C7 N1 . 1.4644(19) ?
    C7 C8 . 1.498(3) ?
    C7 C9 . 1.505(3) ?
    C7 H7 . 1.0000 ?
    C8 H8A . 0.9800 ?
    C8 H8B . 0.9800 ?
    C8 H8C . 0.9800 ?
    C9 H9A . 0.9800 ?
    C9 H9B . 0.9800 ?
    C9 H9C . 0.9800 ?
    N1 P1 . 1.6265(14) ?
    N1 H1A . 0.8800 ?
    O1 P1 . 1.4799(11) ?
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
    C3 C1 C2 . . 111.54(18) ?
    C3 C1 P1 . . 109.54(13) ?
    C2 C1 P1 . . 112.84(13) ?
    C3 C1 H1B . . 107.6 ?
    C2 C1 H1B . . 107.6 ?
    P1 C1 H1B . . 107.6 ?
    C1 C2 H2A . . 109.5 ?
    C1 C2 H2B . . 109.5 ?
    H2A C2 H2B . . 109.5 ?
    C1 C2 H2C . . 109.5 ?
    H2A C2 H2C . . 109.5 ?
    H2B C2 H2C . . 109.5 ?
    C1 C3 H3A . . 109.5 ?
    C1 C3 H3B . . 109.5 ?
    H3A C3 H3B . . 109.5 ?
    C1 C3 H3C . . 109.5 ?
    H3A C3 H3C . . 109.5 ?
    H3B C3 H3C . . 109.5 ?
    C6 C4 C5 . . 111.69(16) ?
    C6 C4 P1 . . 109.96(12) ?
    C5 C4 P1 . . 110.96(11) ?
    C6 C4 H4 . . 108.0 ?
    C5 C4 H4 . . 108.0 ?
    P1 C4 H4 . . 108.0 ?
    C4 C5 H5A . . 109.5 ?
    C4 C5 H5B . . 109.5 ?
    H5A C5 H5B . . 109.5 ?
    C4 C5 H5C . . 109.5 ?
    H5A C5 H5C . . 109.5 ?
    H5B C5 H5C . . 109.5 ?
    C4 C6 H6A . . 109.5 ?
    C4 C6 H6B . . 109.5 ?
    H6A C6 H6B . . 109.5 ?
    C4 C6 H6C . . 109.5 ?
    H6A C6 H6C . . 109.5 ?
    H6B C6 H6C . . 109.5 ?
    N1 C7 C8 . . 109.72(14) ?
    N1 C7 C9 . . 111.68(15) ?
    C8 C7 C9 . . 112.11(17) ?
    N1 C7 H7 . . 107.7 ?
    C8 C7 H7 . . 107.7 ?
    C9 C7 H7 . . 107.7 ?
    C7 C8 H8A . . 109.5 ?
    C7 C8 H8B . . 109.5 ?
    H8A C8 H8B . . 109.5 ?
    C7 C8 H8C . . 109.5 ?
    H8A C8 H8C . . 109.5 ?
    H8B C8 H8C . . 109.5 ?
    C7 C9 H9A . . 109.5 ?
    C7 C9 H9B . . 109.5 ?
    H9A C9 H9B . . 109.5 ?
    C7 C9 H9C . . 109.5 ?
    H9A C9 H9C . . 109.5 ?
    H9B C9 H9C . . 109.5 ?
    C7 N1 P1 . . 124.33(10) ?
    C7 N1 H1A . . 117.8 ?
    P1 N1 H1A . . 117.8 ?
    O1 P1 N1 . . 113.17(7) ?
    O1 P1 C1 . . 109.89(8) ?
    N1 P1 C1 . . 108.11(8) ?
    O1 P1 C4 . . 113.05(8) ?
    N1 P1 C4 . . 104.85(7) ?
    C1 P1 C4 . . 107.44(8) ?
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 H1A O1 4_566 0.88 1.98 2.8344(17) 165
data_global
_journal_date_recd_electronic     2011-05-04
_journal_date_accepted     2011-05-16
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2011
_journal_volume     67
_journal_issue      6
_journal_page_first     o1474
_journal_page_last     o1474
_journal_paper_category     QO
_journal_coeditor_code     YK2008
_publ_contact_author_name     'Normen Peulecke'
_publ_contact_author_address
;
Leibniz-Institut für Katalyse e.V. an der Universität Rostock
Albert-Einstein-Strasse 29A
18059 Rostock
Germany
;
_publ_contact_author_email     'normen.peulecke@catalysis.de'
_publ_contact_author_fax     '+49(0)381128151161'
_publ_contact_author_phone     '+49(0)3811281161'
_publ_section_title
;
N,P,P-Triisopropylphosphinic amide
;
loop_
    _publ_author_name
    _publ_author_address
    'Peulecke, Normen'
;
Leibniz-Institut für Katalyse e. V. an der Universität Rostock
Albert-Einstein-Strasse 29A
18059 Rostock
Germany
;
    'Aluri, Bhaskar R.'
;
Leibniz-Institut für Katalyse e. V. an der Universität Rostock
Albert-Einstein-Strasse 29A
18059 Rostock
Germany
;
    'Müller, Bernd H.'
;
Leibniz-Institut für Katalyse e. V. an der Universität Rostock
Albert-Einstein-Strasse 29A
18059 Rostock
Germany
;
    'Spannenberg, Anke'
;
Leibniz-Institut für Katalyse e. V. an der Universität Rostock
Albert-Einstein-Strasse 29A
18059 Rostock
Germany
;
    'Rosenthal, Uwe'
;
Leibniz-Institut für Katalyse e. V. an der Universität Rostock
Albert-Einstein-Strasse 29A
18059 Rostock
Germany
;
