#------------------------------------------------------------------------------
#$Date: 2016-03-23 20:53:20 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179429 $
#$URL: svn://www.crystallography.net/cod/cif/4/33/26/4332626.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided the Crystal Eye server at
# http://wwmm.ch.cam.ac.uk/crystaleye/, created by Nick Day at the
# Peter Murray-Rust laboratory.
#
# 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_4332626
loop_
_publ_author_name
'Wong, Gene W.'
'Harkreader, Jennifer L.'
'Mebi, Charles A.'
'Frost, Brian J.'
_publ_section_title
;
 Synthesis and Coordination Chemistry of a Novel Bidentate
 Phosphine:  6-(Diphenylphosphino)-1,3,5-triaza-7-phosphaadamantane
 (PTA-PPh2)
;
_journal_issue                   17
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              6748
_journal_page_last               6755
_journal_paper_doi               10.1021/ic060576a
_journal_volume                  45
_journal_year                    2006
_chemical_formula_sum            'C18 H21 N3 P2'
_chemical_formula_weight         341.32
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 101.598(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.357(2)
_cell_length_b                   6.2457(9)
_cell_length_c                   19.192(3)
_cell_measurement_reflns_used    3813
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.35
_cell_measurement_theta_min      2.90
_cell_volume                     1685.8(4)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_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      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'CCD area detector'
_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  0.0683
_diffrn_reflns_av_sigmaI/netI    0.0488
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            18907
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.62
_exptl_absorpt_coefficient_mu    0.261
_exptl_absorpt_correction_T_max  0.9912
_exptl_absorpt_correction_T_min  0.9701
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.345
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Rod
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.811
_refine_diff_density_min         -0.586
_refine_diff_density_rms         0.090
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         3324
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0970
_refine_ls_R_factor_gt           0.0659
_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)+(0.1111P)²+1.0947P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1791
_refine_ls_wR_factor_ref         0.1949
_reflns_number_gt                2307
_reflns_number_total             3324
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic060576asup1.cif
_cod_data_source_block           bjf155
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               4332626
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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
P1 P -0.19533(8) 1.04206(19) 0.19664(6) 0.0420(3) Uani 1 1 d .
P2 P 0.01487(6) 0.98488(15) 0.19275(5) 0.0268(3) Uani 1 1 d .
N1 N -0.1243(2) 0.9374(5) 0.06703(17) 0.0340(8) Uani 1 1 d .
N2 N -0.3020(2) 0.9883(6) 0.06005(18) 0.0384(8) Uani 1 1 d .
N3 N -0.1966(2) 1.3057(5) 0.07831(17) 0.0350(7) Uani 1 1 d .
C1 C -0.1084(2) 0.9025(6) 0.14994(18) 0.0275(8) Uani 1 1 d .
H1A H -0.1138 0.7454 0.1583 0.033 Uiso 1 1 calc R
C2 C -0.3019(3) 0.9560(8) 0.1352(2) 0.0477(11) Uani 1 1 d .
H2A H -0.3116 0.8017 0.1431 0.057 Uiso 1 1 calc R
H2B H -0.3569 1.0336 0.1469 0.057 Uiso 1 1 calc R
C3 C -0.1850(3) 1.3038(7) 0.1558(2) 0.0419(10) Uani 1 1 d .
H3A H -0.2333 1.4005 0.1690 0.050 Uiso 1 1 calc R
H3B H -0.1217 1.3639 0.1766 0.050 Uiso 1 1 calc R
C4 C -0.2251(3) 0.8677(7) 0.0376(2) 0.0384(9) Uani 1 1 d .
H4A H -0.2356 0.8744 -0.0149 0.046 Uiso 1 1 calc R
H4B H -0.2311 0.7158 0.0507 0.046 Uiso 1 1 calc R
C5 C -0.2902(3) 1.2176(6) 0.0450(2) 0.0394(10) Uani 1 1 d .
H5A H -0.3000 1.2377 -0.0071 0.047 Uiso 1 1 calc R
H5B H -0.3402 1.3001 0.0621 0.047 Uiso 1 1 calc R
C6 C -0.1234(3) 1.1796(6) 0.0552(2) 0.0368(9) Uani 1 1 d .
H6A H -0.0608 1.2349 0.0799 0.044 Uiso 1 1 calc R
H6B H -0.1282 1.2054 0.0037 0.044 Uiso 1 1 calc R
C7 C 0.0901(2) 0.7949(6) 0.15754(18) 0.0274(8) Uani 1 1 d .
C8 C 0.1881(3) 0.8339(6) 0.17661(19) 0.0327(8) Uani 1 1 d .
H8A H 0.2105 0.9594 0.2026 0.039 Uiso 1 1 calc R
C9 C 0.2523(3) 0.6910(7) 0.1578(2) 0.0366(9) Uani 1 1 d .
H9A H 0.3185 0.7175 0.1721 0.044 Uiso 1 1 calc R
C10 C 0.2215(3) 0.5108(7) 0.1188(2) 0.0389(9) Uani 1 1 d .
H10A H 0.2662 0.4115 0.1073 0.047 Uiso 1 1 calc R
C11 C 0.1243(3) 0.4745(6) 0.0961(2) 0.0405(10) Uani 1 1 d .
H11A H 0.1024 0.3541 0.0672 0.049 Uiso 1 1 calc R
C12 C 0.0600(3) 0.6160(6) 0.1162(2) 0.0386(9) Uani 1 1 d .
H12A H -0.0062 0.5899 0.1013 0.046 Uiso 1 1 calc R
C13 C 0.0220(2) 0.8766(6) 0.28305(18) 0.0269(8) Uani 1 1 d .
C14 C 0.0035(2) 1.0204(6) 0.33442(19) 0.0314(8) Uani 1 1 d .
H14A H -0.0168 1.1618 0.3208 0.038 Uiso 1 1 calc R
C15 C 0.0144(3) 0.9589(7) 0.4049(2) 0.0357(9) Uani 1 1 d .
H15A H 0.0015 1.0583 0.4392 0.043 Uiso 1 1 calc R
C16 C 0.0441(3) 0.7537(7) 0.4259(2) 0.0357(9) Uani 1 1 d .
H16A H 0.0521 0.7120 0.4744 0.043 Uiso 1 1 calc R
C17 C 0.0618(3) 0.6099(7) 0.3751(2) 0.0354(9) Uani 1 1 d .
H17A H 0.0815 0.4683 0.3890 0.042 Uiso 1 1 calc R
C18 C 0.0515(3) 0.6693(6) 0.30454(19) 0.0316(8) Uani 1 1 d .
H18A H 0.0644 0.5689 0.2705 0.038 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
C2 P1 C3 96.7(2)
C2 P1 C1 96.09(19)
C3 P1 C1 95.20(18)
C7 P2 C13 100.62(16)
C7 P2 C1 103.73(16)
C13 P2 C1 100.44(15)
C4 N1 C6 105.4(3)
C4 N1 C1 105.8(3)
C6 N1 C1 106.4(3)
C2 N2 C4 111.6(3)
C2 N2 C5 110.5(3)
C4 N2 C5 108.5(3)
C6 N3 C3 111.4(3)
C6 N3 C5 108.6(3)
C3 N3 C5 110.1(3)
N1 C1 P2 109.8(2)
N1 C1 P1 116.1(2)
P2 C1 P1 108.79(18)
N1 C1 H1A 107.3
P2 C1 H1A 107.3
P1 C1 H1A 107.3
N2 C2 P1 115.8(3)
N2 C2 H2A 108.3
P1 C2 H2A 108.3
N2 C2 H2B 108.3
P1 C2 H2B 108.3
H2A C2 H2B 107.4
N3 C3 P1 116.1(3)
N3 C3 H3A 108.3
P1 C3 H3A 108.3
N3 C3 H3B 108.3
P1 C3 H3B 108.3
H3A C3 H3B 107.4
N2 C4 N1 117.6(3)
N2 C4 H4A 107.9
N1 C4 H4A 107.9
N2 C4 H4B 107.9
N1 C4 H4B 107.9
H4A C4 H4B 107.2
N3 C5 N2 114.1(3)
N3 C5 H5A 108.7
N2 C5 H5A 108.7
N3 C5 H5B 108.7
N2 C5 H5B 108.7
H5A C5 H5B 107.6
N3 C6 N1 117.6(3)
N3 C6 H6A 107.9
N1 C6 H6A 107.9
N3 C6 H6B 107.9
N1 C6 H6B 107.9
H6A C6 H6B 107.2
C12 C7 C8 118.0(3)
C12 C7 P2 126.6(3)
C8 C7 P2 115.4(3)
C9 C8 C7 120.5(4)
C9 C8 H8A 119.8
C7 C8 H8A 119.8
C10 C9 C8 120.8(4)
C10 C9 H9A 119.6
C8 C9 H9A 119.6
C9 C10 C11 119.7(4)
C9 C10 H10A 120.2
C11 C10 H10A 120.2
C12 C11 C10 119.3(4)
C12 C11 H11A 120.3
C10 C11 H11A 120.3
C7 C12 C11 121.5(4)
C7 C12 H12A 119.2
C11 C12 H12A 119.2
C18 C13 C14 118.4(3)
C18 C13 P2 125.0(3)
C14 C13 P2 116.4(3)
C15 C14 C13 120.7(4)
C15 C14 H14A 119.7
C13 C14 H14A 119.7
C16 C15 C14 120.6(4)
C16 C15 H15A 119.7
C14 C15 H15A 119.7
C15 C16 C17 118.9(4)
C15 C16 H16A 120.5
C17 C16 H16A 120.5
C18 C17 C16 121.1(4)
C18 C17 H17A 119.4
C16 C17 H17A 119.5
C17 C18 C13 120.2(3)
C17 C18 H18A 119.9
C13 C18 H18A 119.9
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
P1 C2 1.815(5)
P1 C3 1.832(4)
P1 C1 1.890(4)
P2 C7 1.823(4)
P2 C13 1.844(4)
P2 C1 1.867(4)
N1 C4 1.508(5)
N1 C6 1.530(5)
N1 C1 1.577(5)
N2 C2 1.456(5)
N2 C4 1.471(5)
N2 C5 1.477(5)
N3 C6 1.451(5)
N3 C3 1.463(5)
N3 C5 1.474(5)
C1 H1A 1.0000
C2 H2A 0.9900
C2 H2B 0.9900
C3 H3A 0.9900
C3 H3B 0.9900
C4 H4A 0.9900
C4 H4B 0.9900
C5 H5A 0.9900
C5 H5B 0.9900
C6 H6A 0.9900
C6 H6B 0.9900
C7 C12 1.388(5)
C7 C8 1.402(5)
C8 C9 1.382(5)
C8 H8A 0.9500
C9 C10 1.375(6)
C9 H9A 0.9500
C10 C11 1.394(6)
C10 H10A 0.9500
C11 C12 1.388(5)
C11 H11A 0.9500
C12 H12A 0.9500
C13 C18 1.398(5)
C13 C14 1.398(5)
C14 C15 1.385(5)
C14 H14A 0.9500
C15 C16 1.384(6)
C15 H15A 0.9500
C16 C17 1.387(5)
C16 H16A 0.9500
C17 C18 1.383(5)
C17 H17A 0.9500
C18 H18A 0.9500
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
C4 N1 C1 P2 -179.8(2)
C6 N1 C1 P2 -68.0(3)
C4 N1 C1 P1 -55.9(3)
C6 N1 C1 P1 55.8(3)
C7 P2 C1 N1 -64.9(3)
C13 P2 C1 N1 -168.7(2)
C7 P2 C1 P1 167.11(17)
C13 P2 C1 P1 63.3(2)
C2 P1 C1 N1 48.3(3)
C3 P1 C1 N1 -49.0(3)
C2 P1 C1 P2 172.7(2)
C3 P1 C1 P2 75.4(2)
C4 N2 C2 P1 61.2(4)
C5 N2 C2 P1 -59.5(4)
C3 P1 C2 N2 46.6(4)
C1 P1 C2 N2 -49.4(4)
C6 N3 C3 P1 -62.4(4)
C5 N3 C3 P1 58.2(4)
C2 P1 C3 N3 -46.1(3)
C1 P1 C3 N3 50.6(3)
C2 N2 C4 N1 -67.8(4)
C5 N2 C4 N1 54.1(4)
C6 N1 C4 N2 -49.3(4)
C1 N1 C4 N2 63.1(4)
C6 N3 C5 N2 56.5(4)
C3 N3 C5 N2 -65.7(4)
C2 N2 C5 N3 66.6(4)
C4 N2 C5 N3 -56.0(4)
C3 N3 C6 N1 66.8(4)
C5 N3 C6 N1 -54.6(4)
C4 N1 C6 N3 49.8(4)
C1 N1 C6 N3 -62.2(4)
C13 P2 C7 C12 96.1(3)
C1 P2 C7 C12 -7.5(4)
C13 P2 C7 C8 -82.0(3)
C1 P2 C7 C8 174.4(3)
C12 C7 C8 C9 -3.5(5)
P2 C7 C8 C9 174.8(3)
C7 C8 C9 C10 1.5(6)
C8 C9 C10 C11 1.8(6)
C9 C10 C11 C12 -3.0(6)
C8 C7 C12 C11 2.3(6)
P2 C7 C12 C11 -175.8(3)
C10 C11 C12 C7 1.0(6)
C7 P2 C13 C18 -18.1(3)
C1 P2 C13 C18 88.2(3)
C7 P2 C13 C14 156.6(3)
C1 P2 C13 C14 -97.1(3)
C18 C13 C14 C15 0.2(5)
P2 C13 C14 C15 -174.9(3)
C13 C14 C15 C16 0.1(6)
C14 C15 C16 C17 -0.6(6)
C15 C16 C17 C18 0.8(6)
C16 C17 C18 C13 -0.5(6)
C14 C13 C18 C17 0.0(5)
P2 C13 C18 C17 174.6(3)
