#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/31/34/4313411.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_4313411
loop_
_publ_author_name
'Zhaofu Fei'
'Rosario Scopelliti'
'Paul J. Dyson'
_publ_contact_author_address
;
Faculté des sciences de base
Institut de Chimie Moléculaire et Biologique
EPFL-BCH
CH-1015 Lausanne
Switzerland 
;
_publ_contact_author_email       paul.dyson@epfl.ch
_publ_contact_author_fax         '+41 21 69 39885'
_publ_contact_author_name        'Paul J. Dyson'
_publ_contact_author_phone       '+41 21 69 39854'
_publ_section_title
;
 Understanding Structure Does Not Always Explain Reactivity: A
 Phosphinoamide Anion Reacts as an Iminophosphide Anion
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              2125
_journal_page_last               2130
_journal_paper_doi               10.1021/ic0262841
_journal_volume                  42
_journal_year                    2003
_chemical_formula_sum            'C19 H15 N2 P'
_chemical_formula_weight         302.30
_chemical_name_systematic
; 
 ? 
;
_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                94.107(12)
_cell_angle_beta                 111.894(9)
_cell_angle_gamma                107.422(8)
_cell_formula_units_Z            2
_cell_length_a                   8.5332(8)
_cell_length_b                   9.5074(9)
_cell_length_c                   11.2744(14)
_cell_measurement_reflns_used    3682
_cell_measurement_temperature    140(2)
_cell_measurement_theta_max      28.81545
_cell_measurement_theta_min      2.1156
_cell_volume                     792.23(17)
_computing_cell_refinement       'Oxford Diffraction CrysAlis RED'
_computing_data_collection       'Oxford Diffraction CrysAlis CCD'
_computing_data_reduction        'Oxford Diffraction CrysAlis RED'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      140(2)
_diffrn_measured_fraction_theta_full 0.876
_diffrn_measured_fraction_theta_max 0.876
_diffrn_measurement_device_type  'Oxford Diffraction KM4/Sapphire CCD'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0280
_diffrn_reflns_av_sigmaI/netI    0.0252
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4686
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         3.85
_exptl_absorpt_coefficient_mu    0.171
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.267
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             316
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.304
_refine_diff_density_min         -0.316
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       0.005(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2453
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.108
_refine_ls_R_factor_all          0.0389
_refine_ls_R_factor_gt           0.0350
_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)+(0.0655P)²+0.2178P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1054
_refine_ls_wR_factor_ref         0.1086
_reflns_number_gt                2200
_reflns_number_total             2453
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic0262841si20021219_041453_2.cif
_cod_data_source_block           1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_original_cell_volume        792.23(14)
_cod_database_code               4313411
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_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P -0.02947(6) -0.16325(4) 0.33880(4) 0.02123(18) Uani 1 1 d . . .
N1 N 0.09151(19) -0.04875(15) 0.26839(14) 0.0239(4) Uani 1 1 d . . .
H1 H 0.0533 -0.0703 0.1829 0.029 Uiso 1 1 calc R . .
N2 N 0.1358(2) 0.16495(18) 0.02839(17) 0.0342(4) Uani 1 1 d . . .
C1 C 0.2468(2) 0.07644(17) 0.33891(16) 0.0196(4) Uani 1 1 d . . .
C2 C 0.3121(2) 0.18875(18) 0.27659(16) 0.0204(4) Uani 1 1 d . . .
C3 C 0.4676(2) 0.3162(2) 0.34782(18) 0.0278(4) Uani 1 1 d . . .
H3 H 0.5090 0.3910 0.3042 0.033 Uiso 1 1 calc R . .
C4 C 0.5603(2) 0.3332(2) 0.48082(19) 0.0329(5) Uani 1 1 d . . .
H4 H 0.6656 0.4190 0.5292 0.040 Uiso 1 1 calc R . .
C5 C 0.4971(2) 0.2229(2) 0.54279(19) 0.0324(5) Uani 1 1 d . . .
H5 H 0.5599 0.2345 0.6345 0.039 Uiso 1 1 calc R . .
C6 C 0.3451(2) 0.0965(2) 0.47418(17) 0.0267(4) Uani 1 1 d . . .
H6 H 0.3064 0.0222 0.5192 0.032 Uiso 1 1 calc R . .
C7 C 0.2159(2) 0.17556(18) 0.13855(18) 0.0231(4) Uani 1 1 d . . .
C8 C -0.2577(2) -0.17467(18) 0.23076(16) 0.0217(4) Uani 1 1 d . . .
C9 C -0.3975(2) -0.3055(2) 0.14804(18) 0.0270(4) Uani 1 1 d . . .
H9 H -0.3763 -0.3978 0.1423 0.032 Uiso 1 1 calc R . .
C10 C -0.5676(2) -0.3014(2) 0.07389(19) 0.0329(5) Uani 1 1 d . . .
H10 H -0.6618 -0.3908 0.0180 0.039 Uiso 1 1 calc R . .
C11 C -0.5998(3) -0.1678(2) 0.0813(2) 0.0357(5) Uani 1 1 d . . .
H11 H -0.7160 -0.1653 0.0306 0.043 Uiso 1 1 calc R . .
C12 C -0.4622(3) -0.0369(2) 0.1630(2) 0.0348(5) Uani 1 1 d . . .
H12 H -0.4837 0.0553 0.1678 0.042 Uiso 1 1 calc R . .
C13 C -0.2936(3) -0.04131(19) 0.23757(19) 0.0285(4) Uani 1 1 d . . .
H13 H -0.2006 0.0482 0.2944 0.034 Uiso 1 1 calc R . .
C14 C -0.0307(2) -0.35009(18) 0.28667(16) 0.0207(4) Uani 1 1 d . . .
C15 C 0.0453(2) -0.38362(19) 0.20300(17) 0.0241(4) Uani 1 1 d . . .
H15 H 0.0954 -0.3076 0.1638 0.029 Uiso 1 1 calc R . .
C16 C 0.0478(2) -0.5281(2) 0.17671(18) 0.0267(4) Uani 1 1 d . . .
H16 H 0.1011 -0.5498 0.1206 0.032 Uiso 1 1 calc R . .
C17 C -0.0274(2) -0.64069(19) 0.23214(18) 0.0279(4) Uani 1 1 d . . .
H17 H -0.0256 -0.7392 0.2138 0.033 Uiso 1 1 calc R . .
C18 C -0.1048(2) -0.6090(2) 0.31425(19) 0.0296(4) Uani 1 1 d . . .
H18 H -0.1581 -0.6862 0.3511 0.036 Uiso 1 1 calc R . .
C19 C -0.1045(2) -0.46435(19) 0.34261(18) 0.0251(4) Uani 1 1 d . . .
H19 H -0.1551 -0.4426 0.4007 0.030 Uiso 1 1 calc 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'
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 P1 C14 103.99(7) . . ?
N1 P1 C8 99.36(7) . . ?
C14 P1 C8 102.02(8) . . ?
C1 N1 P1 123.68(12) . . ?
C1 N1 H1 118.2 . . ?
P1 N1 H1 118.2 . . ?
N1 C1 C6 121.88(15) . . ?
N1 C1 C2 120.94(15) . . ?
C6 C1 C2 117.18(14) . . ?
C3 C2 C1 121.06(16) . . ?
C3 C2 C7 119.15(15) . . ?
C1 C2 C7 119.77(14) . . ?
C4 C3 C2 120.33(16) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C3 C4 C5 118.94(16) . . ?
C3 C4 H4 120.5 . . ?
C5 C4 H4 120.5 . . ?
C6 C5 C4 121.50(17) . . ?
C6 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?
C5 C6 C1 120.98(16) . . ?
C5 C6 H6 119.5 . . ?
C1 C6 H6 119.5 . . ?
N2 C7 C2 178.63(18) . . ?
C13 C8 C9 118.37(16) . . ?
C13 C8 P1 115.99(13) . . ?
C9 C8 P1 125.59(14) . . ?
C10 C9 C8 120.43(17) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
C11 C10 C9 120.25(17) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C10 C11 C12 119.91(18) . . ?
C10 C11 H11 120.0 . . ?
C12 C11 H11 120.0 . . ?
C13 C12 C11 119.84(18) . . ?
C13 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
C12 C13 C8 121.19(17) . . ?
C12 C13 H13 119.4 . . ?
C8 C13 H13 119.4 . . ?
C15 C14 C19 118.74(16) . . ?
C15 C14 P1 125.02(13) . . ?
C19 C14 P1 116.13(13) . . ?
C16 C15 C14 120.27(16) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C17 C16 C15 120.33(16) . . ?
C17 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
C18 C17 C16 119.87(17) . . ?
C18 C17 H17 120.1 . . ?
C16 C17 H17 120.1 . . ?
C17 C18 C19 119.93(16) . . ?
C17 C18 H18 120.0 . . ?
C19 C18 H18 120.0 . . ?
C18 C19 C14 120.85(16) . . ?
C18 C19 H19 119.6 . . ?
C14 C19 H19 119.6 . . ?
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 N1 1.7155(14) . ?
P1 C14 1.8264(17) . ?
P1 C8 1.8370(18) . ?
N1 C1 1.393(2) . ?
N1 H1 0.8800 . ?
N2 C7 1.152(2) . ?
C1 C6 1.405(2) . ?
C1 C2 1.410(2) . ?
C2 C3 1.406(2) . ?
C2 C7 1.439(2) . ?
C3 C4 1.380(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.387(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.382(2) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C8 C13 1.394(3) . ?
C8 C9 1.398(2) . ?
C9 C10 1.394(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.381(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.389(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.385(3) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 C15 1.396(2) . ?
C14 C19 1.400(2) . ?
C15 C16 1.393(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.390(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.386(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.389(3) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 N2 0.88 2.25 3.086(2) 159.6 2
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C14 P1 N1 C1 -122.41(14) . . . . ?
C8 P1 N1 C1 132.61(14) . . . . ?
P1 N1 C1 C6 17.7(2) . . . . ?
P1 N1 C1 C2 -162.34(13) . . . . ?
N1 C1 C2 C3 179.18(15) . . . . ?
C6 C1 C2 C3 -0.9(2) . . . . ?
N1 C1 C2 C7 0.9(2) . . . . ?
C6 C1 C2 C7 -179.12(15) . . . . ?
C1 C2 C3 C4 0.4(3) . . . . ?
C7 C2 C3 C4 178.66(17) . . . . ?
C2 C3 C4 C5 -0.2(3) . . . . ?
C3 C4 C5 C6 0.6(3) . . . . ?
C4 C5 C6 C1 -1.1(3) . . . . ?
N1 C1 C6 C5 -178.85(16) . . . . ?
C2 C1 C6 C5 1.2(3) . . . . ?
C3 C2 C7 N2 -120(7) . . . . ?
C1 C2 C7 N2 59(7) . . . . ?
N1 P1 C8 C13 -67.02(14) . . . . ?
C14 P1 C8 C13 -173.61(13) . . . . ?
N1 P1 C8 C9 115.76(15) . . . . ?
C14 P1 C8 C9 9.17(16) . . . . ?
C13 C8 C9 C10 0.4(3) . . . . ?
P1 C8 C9 C10 177.60(14) . . . . ?
C8 C9 C10 C11 0.1(3) . . . . ?
C9 C10 C11 C12 0.0(3) . . . . ?
C10 C11 C12 C13 -0.5(3) . . . . ?
C11 C12 C13 C8 1.1(3) . . . . ?
C9 C8 C13 C12 -1.0(3) . . . . ?
P1 C8 C13 C12 -178.45(14) . . . . ?
N1 P1 C14 C15 -2.79(17) . . . . ?
C8 P1 C14 C15 100.18(15) . . . . ?
N1 P1 C14 C19 173.16(13) . . . . ?
C8 P1 C14 C19 -83.87(14) . . . . ?
C19 C14 C15 C16 -0.3(2) . . . . ?
P1 C14 C15 C16 175.52(13) . . . . ?
C14 C15 C16 C17 0.9(3) . . . . ?
C15 C16 C17 C18 -0.2(3) . . . . ?
C16 C17 C18 C19 -1.1(3) . . . . ?
C17 C18 C19 C14 1.6(3) . . . . ?
C15 C14 C19 C18 -0.9(3) . . . . ?
P1 C14 C19 C18 -177.12(14) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 4908792
