#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/05/23/7052309.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_7052309
loop_
_publ_author_name
'Bhuvan Kumar, N. N.'
'Chakravarty, Manab'
'Kumara Swamy, K. C.'
_publ_section_title
;
 Structure and reactivity of tautomeric forms of zwitterionic species
 from the reaction of phosphorus(iii) compounds with electron deficient
 alkenes and alkynes
;
_journal_issue                   11
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              1614
_journal_paper_doi               10.1039/b605430g
_journal_volume                  30
_journal_year                    2006
_chemical_formula_sum            'C27 H30 N O2 P'
_chemical_formula_weight         431.49
_chemical_name_systematic
;
?
;
_space_group_IT_number           45
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'I 2 -2c'
_symmetry_space_group_name_H-M   'I b a 2'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   19.157(4)
_cell_length_b                   25.897(6)
_cell_length_c                   9.9046(15)
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      23.67
_cell_measurement_theta_min      2.59
_cell_volume                     4913.8(17)
_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      296(2)
_diffrn_measured_fraction_theta_full 0.914
_diffrn_measured_fraction_theta_max 0.914
_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  0.0285
_diffrn_reflns_av_sigmaI/netI    0.0479
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            5658
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         1.57
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 'not applicable'
_diffrn_standards_interval_time  'not applicable'
_diffrn_standards_number         'not applicable'
_exptl_absorpt_coefficient_mu    0.134
_exptl_absorpt_correction_T_max  0.9711
_exptl_absorpt_correction_T_min  0.9446
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS, Sheldrick (1996)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.167
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       blocks
_exptl_crystal_F_000             1840
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.321
_refine_diff_density_min         -0.171
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.02(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.926
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     284
_refine_ls_number_reflns         3486
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.925
_refine_ls_R_factor_all          0.0712
_refine_ls_R_factor_gt           0.0498
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0795P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1232
_refine_ls_wR_factor_ref         0.1325
_reflns_number_gt                2437
_reflns_number_total             3486
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b605430g.txt
_cod_data_source_block           compd5
_cod_original_cell_volume        4913.7(16)
_cod_original_sg_symbol_H-M      Iba2
_cod_database_code               7052309
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, -y+1/2, z+1/2'
'x+1, -y+1, z+1/2'
'-x+1, y+1, 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 0.78939(5) 0.85739(3) 0.92924(11) 0.0498(3) Uani 1 1 d . . .
N N 0.84098(18) 0.87901(13) 0.8265(3) 0.0617(9) Uani 1 1 d . . .
O1 O 0.5764(2) 0.92048(14) 0.7377(4) 0.1015(12) Uani 1 1 d . . .
O2 O 0.65172(17) 0.95136(13) 0.5872(3) 0.0853(10) Uani 1 1 d . . .
C1 C 0.7900(2) 0.88276(15) 1.1001(4) 0.0530(10) Uani 1 1 d . . .
C2 C 0.7626(2) 0.93072(17) 1.1283(5) 0.0734(13) Uani 1 1 d . . .
H2 H 0.7378 0.9481 1.0616 0.088 Uiso 1 1 calc R . .
C3 C 0.7710(3) 0.95367(19) 1.2531(6) 0.0887(16) Uani 1 1 d . . .
H3 H 0.7522 0.9862 1.2698 0.106 Uiso 1 1 calc R . .
C4 C 0.8074(3) 0.9281(2) 1.3525(6) 0.0891(16) Uani 1 1 d . . .
H4 H 0.8133 0.9435 1.4367 0.107 Uiso 1 1 calc R . .
C5 C 0.8352(3) 0.8801(2) 1.3284(5) 0.0785(13) Uani 1 1 d . . .
H5 H 0.8599 0.8629 1.3956 0.094 Uiso 1 1 calc R . .
C6 C 0.8261(2) 0.85758(16) 1.2031(4) 0.0632(11) Uani 1 1 d . . .
H6 H 0.8445 0.8249 1.1871 0.076 Uiso 1 1 calc R . .
C7 C 0.7908(2) 0.78772(13) 0.9502(4) 0.0506(9) Uani 1 1 d . . .
C8 C 0.7498(2) 0.76136(16) 1.0438(4) 0.0610(11) Uani 1 1 d . . .
H8 H 0.7193 0.7798 1.0987 0.073 Uiso 1 1 calc R . .
C9 C 0.7535(3) 0.70873(16) 1.0565(5) 0.0698(12) Uani 1 1 d . . .
H9 H 0.7255 0.6916 1.1189 0.084 Uiso 1 1 calc R . .
C10 C 0.7988(3) 0.68160(17) 0.9769(5) 0.0725(14) Uani 1 1 d . . .
H10 H 0.8014 0.6459 0.9849 0.087 Uiso 1 1 calc R . .
C11 C 0.8399(2) 0.70648(18) 0.8861(5) 0.0740(13) Uani 1 1 d . . .
H11 H 0.8711 0.6876 0.8335 0.089 Uiso 1 1 calc R . .
C12 C 0.8361(2) 0.75958(15) 0.8708(5) 0.0634(11) Uani 1 1 d . . .
H12 H 0.8640 0.7762 0.8073 0.076 Uiso 1 1 calc R . .
C13 C 0.9121(3) 0.8998(2) 0.8295(5) 0.0849(15) Uani 1 1 d . . .
C17 C 0.70158(19) 0.87227(13) 0.8659(4) 0.0481(10) Uani 1 1 d . . .
C18 C 0.6982(2) 0.90607(14) 0.7652(4) 0.0502(9) Uani 1 1 d . . .
H18 H 0.7404 0.9190 0.7333 0.060 Uiso 1 1 calc R . .
C19 C 0.6344(3) 0.92509(16) 0.6991(5) 0.0602(11) Uani 1 1 d . . .
C20 C 0.5956(3) 0.9734(2) 0.5073(7) 0.114(2) Uani 1 1 d . . .
H20A H 0.5544 0.9775 0.5634 0.136 Uiso 1 1 calc R . .
H20B H 0.6093 1.0073 0.4753 0.136 Uiso 1 1 calc R . .
C21 C 0.5794(3) 0.9417(3) 0.3963(8) 0.129(2) Uani 1 1 d . . .
H21A H 0.6214 0.9339 0.3474 0.193 Uiso 1 1 calc R . .
H21B H 0.5473 0.9595 0.3379 0.193 Uiso 1 1 calc R . .
H21C H 0.5585 0.9103 0.4277 0.193 Uiso 1 1 calc R . .
C22 C 0.63933(18) 0.84494(13) 0.9220(4) 0.0514(9) Uani 1 1 d . . .
C23 C 0.6153(3) 0.80104(19) 0.8594(5) 0.0819(14) Uani 1 1 d . . .
H23 H 0.6374 0.7892 0.7817 0.098 Uiso 1 1 calc R . .
C24 C 0.5582(3) 0.7740(2) 0.9109(8) 0.113(2) Uani 1 1 d . . .
H24 H 0.5430 0.7441 0.8683 0.135 Uiso 1 1 calc R . .
C25 C 0.5248(3) 0.7913(3) 1.0228(8) 0.105(2) Uani 1 1 d . . .
H25 H 0.4867 0.7733 1.0569 0.126 Uiso 1 1 calc R . .
C26 C 0.5479(3) 0.8355(3) 1.0854(6) 0.0921(17) Uani 1 1 d . . .
H26 H 0.5246 0.8477 1.1613 0.111 Uiso 1 1 calc R . .
C27 C 0.6048(2) 0.86178(18) 1.0374(5) 0.0710(13) Uani 1 1 d . . .
H27 H 0.6205 0.8911 1.0824 0.085 Uiso 1 1 calc R . .
C14 C 0.9191(4) 0.9435(3) 0.9321(11) 0.160(3) Uani 1 1 d . . .
H14A H 0.8772 0.9639 0.9320 0.239 Uiso 1 1 calc R . .
H14B H 0.9581 0.9649 0.9083 0.239 Uiso 1 1 calc R . .
H14C H 0.9263 0.9292 1.0204 0.239 Uiso 1 1 calc R . .
C15 C 0.9196(4) 0.9292(4) 0.6974(9) 0.214(5) Uani 1 1 d . . .
H15A H 0.8779 0.9488 0.6808 0.322 Uiso 1 1 calc R . .
H15B H 0.9268 0.9052 0.6249 0.322 Uiso 1 1 calc R . .
H15C H 0.9587 0.9522 0.7032 0.322 Uiso 1 1 calc R . .
C16 C 0.9629(3) 0.8613(3) 0.855(2) 0.337(13) Uani 1 1 d . . .
H16A H 0.9524 0.8442 0.9383 0.506 Uiso 1 1 calc R . .
H16B H 1.0082 0.8771 0.8607 0.506 Uiso 1 1 calc R . .
H16C H 0.9626 0.8366 0.7825 0.506 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'
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N P C1 119.04(19) . . ?
N P C7 115.55(19) . . ?
C1 P C7 104.66(18) . . ?
N P C17 106.76(18) . . ?
C1 P C17 104.37(18) . . ?
C7 P C17 105.11(17) . . ?
C13 N P 136.4(3) . . ?
C19 O2 C20 117.8(4) . . ?
C2 C1 C6 117.6(4) . . ?
C2 C1 P 120.9(3) . . ?
C6 C1 P 121.0(3) . . ?
C1 C2 C3 121.7(5) . . ?
C1 C2 H2 119.1 . . ?
C3 C2 H2 119.1 . . ?
C4 C3 C2 119.5(4) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C5 C4 C3 120.4(5) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C4 C5 C6 119.3(5) . . ?
C4 C5 H5 120.3 . . ?
C6 C5 H5 120.3 . . ?
C5 C6 C1 121.5(4) . . ?
C5 C6 H6 119.3 . . ?
C1 C6 H6 119.3 . . ?
C12 C7 C8 118.4(3) . . ?
C12 C7 P 117.9(3) . . ?
C8 C7 P 123.7(3) . . ?
C9 C8 C7 121.3(4) . . ?
C9 C8 H8 119.4 . . ?
C7 C8 H8 119.4 . . ?
C10 C9 C8 119.4(4) . . ?
C10 C9 H9 120.3 . . ?
C8 C9 H9 120.3 . . ?
C11 C10 C9 120.4(4) . . ?
C11 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
C10 C11 C12 120.9(4) . . ?
C10 C11 H11 119.6 . . ?
C12 C11 H11 119.6 . . ?
C7 C12 C11 119.7(4) . . ?
C7 C12 H12 120.2 . . ?
C11 C12 H12 120.2 . . ?
C16 C13 N 112.6(5) . . ?
C16 C13 C15 116.1(10) . . ?
N C13 C15 104.7(5) . . ?
C16 C13 C14 110.1(9) . . ?
N C13 C14 111.6(5) . . ?
C15 C13 C14 101.1(6) . . ?
C18 C17 C22 123.5(4) . . ?
C18 C17 P 116.1(3) . . ?
C22 C17 P 120.3(3) . . ?
C17 C18 C19 126.5(4) . . ?
C17 C18 H18 116.7 . . ?
C19 C18 H18 116.7 . . ?
O1 C19 O2 123.4(4) . . ?
O1 C19 C18 127.1(4) . . ?
O2 C19 C18 109.4(4) . . ?
C21 C20 O2 111.1(5) . . ?
C21 C20 H20A 109.4 . . ?
O2 C20 H20A 109.4 . . ?
C21 C20 H20B 109.4 . . ?
O2 C20 H20B 109.4 . . ?
H20A C20 H20B 108.0 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C23 C22 C27 118.1(4) . . ?
C23 C22 C17 119.4(4) . . ?
C27 C22 C17 122.5(4) . . ?
C22 C23 C24 120.8(5) . . ?
C22 C23 H23 119.6 . . ?
C24 C23 H23 119.6 . . ?
C25 C24 C23 120.3(6) . . ?
C25 C24 H24 119.9 . . ?
C23 C24 H24 119.9 . . ?
C24 C25 C26 119.5(5) . . ?
C24 C25 H25 120.3 . . ?
C26 C25 H25 120.3 . . ?
C27 C26 C25 120.8(6) . . ?
C27 C26 H26 119.6 . . ?
C25 C26 H26 119.6 . . ?
C26 C27 C22 120.5(5) . . ?
C26 C27 H27 119.7 . . ?
C22 C27 H27 119.7 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
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 N 1.525(4) . ?
P C1 1.815(4) . ?
P C7 1.816(4) . ?
P C17 1.836(4) . ?
N C13 1.465(6) . ?
O1 C19 1.181(5) . ?
O2 C19 1.342(5) . ?
O2 C20 1.452(6) . ?
C1 C2 1.377(6) . ?
C1 C6 1.395(6) . ?
C2 C3 1.381(7) . ?
C2 H2 0.9300 . ?
C3 C4 1.377(7) . ?
C3 H3 0.9300 . ?
C4 C5 1.374(7) . ?
C4 H4 0.9300 . ?
C5 C6 1.382(6) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C12 1.380(5) . ?
C7 C8 1.393(6) . ?
C8 C9 1.371(5) . ?
C8 H8 0.9300 . ?
C9 C10 1.367(6) . ?
C9 H9 0.9300 . ?
C10 C11 1.358(6) . ?
C10 H10 0.9300 . ?
C11 C12 1.385(6) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 C16 1.415(8) . ?
C13 C15 1.521(9) . ?
C13 C14 1.527(9) . ?
C17 C18 1.328(5) . ?
C17 C22 1.494(5) . ?
C18 C19 1.471(5) . ?
C18 H18 0.9300 . ?
C20 C21 1.406(8) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 C23 1.374(6) . ?
C22 C27 1.391(6) . ?
C23 C24 1.395(7) . ?
C23 H23 0.9300 . ?
C24 C25 1.354(9) . ?
C24 H24 0.9300 . ?
C25 C26 1.376(8) . ?
C25 H25 0.9300 . ?
C26 C27 1.370(7) . ?
C26 H26 0.9300 . ?
C27 H27 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21189181
