#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/01/29/7012916.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_7012916
loop_
_publ_author_name
'Grundy, Joanna'
'Coles, Martyn P.'
'Hitchcock, Peter B.'
_publ_section_title
;
 Synthesis and coordination chemistry of neutral
 phospha(iii)guanidines. Formation of
 1-aza-3-phospha-4-metallacyclobut-1-ene rings at group 6
 metalsElectronic supplementary information (ESI) available: an ORTEP
 representation and bond lengths and angles for 3a; crystal structure
 and refinement data, bond lengths and angles and an ORTEP
 representation of the molecular structure of Mo(CO)4(pip)2. See
 http://www.rsc.org/suppdata/dt/b3/b302554c/
;
_journal_issue                   12
_journal_name_full               'Dalton Transactions'
_journal_page_first              2573
_journal_paper_doi               10.1039/b302554c
_journal_year                    2003
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C25 H33 N2 P1'
_chemical_formula_sum            'C25 H33 N2 P'
_chemical_formula_weight         392.5
_chemical_name_common            '[Ph2PC(NHCy)(NCy)]'
_chemical_name_systematic
;
?
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.2
_audit_creation_date             2002-07-23T16:39:30-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.0943(2)
_cell_length_b                   11.6147(2)
_cell_length_c                   21.0144(4)
_cell_measurement_reflns_used    6473
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      24.713
_cell_measurement_theta_min      3.705
_cell_measurement_wavelength     0.71073
_cell_volume                     2219.70(8)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.956
_diffrn_measured_fraction_theta_max 0.956
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       CCD
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0524
_diffrn_reflns_av_unetI/netI     0.0442
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            11636
_diffrn_reflns_theta_full        24.71
_diffrn_reflns_theta_max         24.71
_diffrn_reflns_theta_min         3.88
_exptl_absorpt_coefficient_mu    0.136
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.175
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.195
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.06(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    'H1 refined; others riding'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         3593
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0406
_refine_ls_R_factor_gt           0.0351
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0266P)²+0.6137P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0751
_refine_ls_wR_factor_ref         0.0778
_reflns_number_gt                3315
_reflns_number_total             3593
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b302554c.txt
_cod_data_source_block           mpc-1a(jul702)
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_original_formula_sum        'C25 H33 N2 P1'
_cod_database_code               7012916
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, 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
_atom_site_disorder_assembly
_atom_site_disorder_group
P P 0.47798(6) 0.05920(4) 0.83780(2) 0.02229(13) Uani 1 1 d . . .
N1 N 0.2618(2) -0.09551(13) 0.80166(8) 0.0246(4) Uani 1 1 d . . .
H1 H 0.322(3) -0.1072(18) 0.7710(11) 0.035(6) Uiso 1 1 d . . .
N2 N 0.2132(2) -0.00246(14) 0.89606(7) 0.0243(4) Uani 1 1 d . . .
C1 C 0.2992(2) -0.01944(14) 0.84839(8) 0.0209(4) Uani 1 1 d . . .
C2 C 0.5266(3) 0.02287(15) 0.75558(8) 0.0240(4) Uani 1 1 d . . .
C3 C 0.4703(3) 0.09429(17) 0.70825(9) 0.0330(5) Uani 1 1 d . . .
H3 H 0.4086 0.157 0.7197 0.04 Uiso 1 1 calc R . .
C4 C 0.5031(3) 0.07509(19) 0.64473(9) 0.0411(6) Uani 1 1 d . . .
H4 H 0.462 0.1234 0.6129 0.049 Uiso 1 1 calc R . .
C5 C 0.5947(3) -0.0137(2) 0.62776(10) 0.0415(6) Uani 1 1 d . . .
H5 H 0.6184 -0.026 0.5843 0.05 Uiso 1 1 calc R . .
C6 C 0.6521(3) -0.0846(2) 0.67369(10) 0.0452(6) Uani 1 1 d . . .
H6 H 0.7155 -0.1459 0.6619 0.054 Uiso 1 1 calc R . .
C7 C 0.6179(3) -0.06722(18) 0.73746(9) 0.0341(5) Uani 1 1 d . . .
H7 H 0.6572 -0.1174 0.7689 0.041 Uiso 1 1 calc R . .
C8 C 0.6000(2) -0.03235(15) 0.88517(8) 0.0215(4) Uani 1 1 d . . .
C9 C 0.7504(3) -0.00734(17) 0.88540(9) 0.0275(5) Uani 1 1 d . . .
H9 H 0.7872 0.0506 0.8577 0.033 Uiso 1 1 calc R . .
C10 C 0.8469(2) -0.06520(19) 0.92510(10) 0.0327(5) Uani 1 1 d . . .
H10 H 0.949 -0.0481 0.9239 0.039 Uiso 1 1 calc R . .
C11 C 0.7941(3) -0.14799(19) 0.96656(10) 0.0355(6) Uani 1 1 d . . .
H11 H 0.8594 -0.1857 0.995 0.043 Uiso 1 1 calc R . .
C12 C 0.6466(3) -0.17563(19) 0.96647(10) 0.0339(5) Uani 1 1 d . . .
H12 H 0.6107 -0.2337 0.9943 0.041 Uiso 1 1 calc R . .
C13 C 0.5498(2) -0.11850(16) 0.92563(9) 0.0279(5) Uani 1 1 d . . .
H13 H 0.4486 -0.1387 0.9255 0.033 Uiso 1 1 calc R . .
C14 C 0.1300(2) -0.16768(15) 0.80269(8) 0.0212(4) Uani 1 1 d . . .
H14 H 0.0428 -0.1176 0.8113 0.025 Uiso 1 1 calc R . .
C15 C 0.1109(3) -0.22316(17) 0.73760(9) 0.0310(5) Uani 1 1 d . . .
H15B H 0.2006 -0.2674 0.7268 0.037 Uiso 1 1 calc R . .
H15A H 0.0983 -0.1623 0.7051 0.037 Uiso 1 1 calc R . .
C16 C -0.0221(3) -0.30346(17) 0.73618(10) 0.0380(6) Uani 1 1 d . . .
H16B H -0.1128 -0.2576 0.742 0.046 Uiso 1 1 calc R . .
H16A H -0.0276 -0.3413 0.694 0.046 Uiso 1 1 calc R . .
C17 C -0.0137(3) -0.39487(17) 0.78763(10) 0.0371(5) Uani 1 1 d . . .
H17B H 0.0704 -0.4467 0.7791 0.045 Uiso 1 1 calc R . .
H17A H -0.1048 -0.4416 0.7871 0.045 Uiso 1 1 calc R . .
C18 C 0.0050(3) -0.33950(18) 0.85275(9) 0.0424(6) Uani 1 1 d . . .
H18B H 0.017 -0.4004 0.8853 0.051 Uiso 1 1 calc R . .
H18A H -0.0845 -0.2949 0.8634 0.051 Uiso 1 1 calc R . .
C19 C 0.1381(3) -0.26001(17) 0.85406(9) 0.0316(5) Uani 1 1 d . . .
H19B H 0.2285 -0.3062 0.8479 0.038 Uiso 1 1 calc R . .
H19A H 0.1445 -0.2226 0.8963 0.038 Uiso 1 1 calc R . .
C20 C 0.2575(2) 0.07745(16) 0.94665(8) 0.0249(4) Uani 1 1 d . . .
H20 H 0.3627 0.0994 0.9401 0.03 Uiso 1 1 calc R . .
C21 C 0.1635(3) 0.18575(17) 0.94561(9) 0.0297(5) Uani 1 1 d . . .
H21B H 0.0587 0.1644 0.9502 0.036 Uiso 1 1 calc R . .
H21A H 0.1757 0.2252 0.9042 0.036 Uiso 1 1 calc R . .
C22 C 0.2068(3) 0.26790(17) 0.99942(10) 0.0343(5) Uani 1 1 d . . .
H22B H 0.3088 0.295 0.9927 0.041 Uiso 1 1 calc R . .
H22A H 0.1411 0.3359 0.9989 0.041 Uiso 1 1 calc R . .
C23 C 0.1957(3) 0.20829(18) 1.06379(9) 0.0372(6) Uani 1 1 d . . .
H23B H 0.2317 0.261 1.0974 0.045 Uiso 1 1 calc R . .
H23A H 0.0913 0.1906 1.0729 0.045 Uiso 1 1 calc R . .
C24 C 0.2846(3) 0.09763(17) 1.06550(9) 0.0348(6) Uani 1 1 d . . .
H24B H 0.2676 0.058 1.1066 0.042 Uiso 1 1 calc R . .
H24A H 0.3906 0.1163 1.0625 0.042 Uiso 1 1 calc R . .
C25 C 0.2424(3) 0.01742(17) 1.01099(9) 0.0296(5) Uani 1 1 d . . .
H25B H 0.1395 -0.0085 1.0167 0.035 Uiso 1 1 calc R . .
H25A H 0.3065 -0.0514 1.0118 0.035 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 0 '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
C8 P C2 103.44(9) . . ?
C8 P C1 100.25(9) . . ?
C2 P C1 102.05(9) . . ?
C1 N1 C14 124.39(17) . . ?
C1 N2 C20 119.63(17) . . ?
N2 C1 N1 120.56(19) . . ?
N2 C1 P 122.97(14) . . ?
N1 C1 P 116.46(14) . . ?
C7 C2 C3 118.21(18) . . ?
C7 C2 P 125.18(15) . . ?
C3 C2 P 116.57(15) . . ?
C4 C3 C2 120.9(2) . . ?
C5 C4 C3 120.1(2) . . ?
C6 C5 C4 119.9(2) . . ?
C5 C6 C7 120.4(2) . . ?
C2 C7 C6 120.5(2) . . ?
C13 C8 C9 117.95(19) . . ?
C13 C8 P 123.47(16) . . ?
C9 C8 P 118.30(15) . . ?
C10 C9 C8 121.40(19) . . ?
C11 C10 C9 119.8(2) . . ?
C12 C11 C10 119.9(2) . . ?
C11 C12 C13 120.2(2) . . ?
C8 C13 C12 120.7(2) . . ?
N1 C14 C15 108.82(16) . . ?
N1 C14 C19 111.97(17) . . ?
C15 C14 C19 110.14(15) . . ?
C14 C15 C16 111.49(18) . . ?
C17 C16 C15 111.96(18) . . ?
C16 C17 C18 110.53(16) . . ?
C17 C18 C19 111.18(18) . . ?
C18 C19 C14 112.04(18) . . ?
N2 C20 C21 111.01(16) . . ?
N2 C20 C25 109.14(16) . . ?
C21 C20 C25 109.87(16) . . ?
C20 C21 C22 111.13(18) . . ?
C23 C22 C21 110.83(17) . . ?
C24 C23 C22 111.75(18) . . ?
C23 C24 C25 111.42(18) . . ?
C24 C25 C20 111.31(17) . . ?
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
P C8 1.831(2) . ?
P C2 1.8327(18) . ?
P C1 1.878(2) . ?
N1 C1 1.364(2) . ?
N1 C14 1.463(3) . ?
N2 C1 1.286(2) . ?
N2 C20 1.468(2) . ?
C2 C7 1.389(3) . ?
C2 C3 1.393(3) . ?
C3 C4 1.386(3) . ?
C4 C5 1.373(3) . ?
C5 C6 1.372(3) . ?
C6 C7 1.390(3) . ?
C8 C13 1.390(3) . ?
C8 C9 1.398(3) . ?
C9 C10 1.385(3) . ?
C10 C11 1.383(3) . ?
C11 C12 1.380(3) . ?
C12 C13 1.397(3) . ?
C14 C15 1.522(2) . ?
C14 C19 1.524(3) . ?
C15 C16 1.527(3) . ?
C16 C17 1.517(3) . ?
C17 C18 1.522(3) . ?
C18 C19 1.523(3) . ?
C20 C21 1.521(3) . ?
C20 C25 1.527(3) . ?
C21 C22 1.531(3) . ?
C22 C23 1.523(3) . ?
C23 C24 1.519(3) . ?
C24 C25 1.525(3) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21146171
