#------------------------------------------------------------------------------
#$Date: 2016-03-26 03:04:30 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180167 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/63/7106349.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_7106349
loop_
_publ_author_name
'Venu Srinivas'
'K. V. Sajna'
'K. C. Kumara Swamy'
_publ_section_title
;
 To stay as allene or go further? Synthesis of novel
 phosphono-heterocycles and polycyclics via propargyl alcohols
;
_journal_name_full               Chem.Commun.
_journal_page_first              5629
_journal_paper_doi               10.1039/c1cc10230c
_journal_volume                  47
_journal_year                    2011
_chemical_formula_sum            'C27 H22 N O5 P'
_chemical_formula_weight         471.43
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 114.460(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.1245(12)
_cell_length_b                   10.1712(12)
_cell_length_c                   24.0509(19)
_cell_measurement_reflns_used    8632
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      26.02
_cell_measurement_theta_min      2.21
_cell_volume                     2254.4(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      298(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0244
_diffrn_reflns_av_sigmaI/netI    0.0238
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            13113
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.86
_diffrn_standards_decay_%        none
_diffrn_standards_interval_count 'not applicable'
_diffrn_standards_interval_time  'not applicable'
_diffrn_standards_number         'not applicable'
_exptl_absorpt_coefficient_mu    0.163
_exptl_absorpt_correction_T_max  0.9651
_exptl_absorpt_correction_T_min  0.9559
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS, Sheldrick(1996)'
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.389
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       blocks
_exptl_crystal_F_000             984
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.248
_refine_diff_density_min         -0.286
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     307
_refine_ls_number_reflns         3950
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0437
_refine_ls_R_factor_gt           0.0386
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0589P)²+0.4968P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1030
_refine_ls_wR_factor_ref         0.1064
_reflns_number_gt                3467
_reflns_number_total             3950
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1cc10230c.txt
_cod_data_source_block           compound-9
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7106349
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'
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 0.87334(5) 0.72298(4) 0.86234(2) 0.04132(15) Uani 1 1 d . . .
O1 O 0.77176(14) 0.83186(12) 0.84528(7) 0.0611(4) Uani 1 1 d . . .
O2 O 0.97781(13) 0.73578(12) 0.82801(5) 0.0468(3) Uani 1 1 d . . .
O3 O 0.98247(12) 0.71490(11) 0.93213(5) 0.0452(3) Uani 1 1 d . . .
O4 O 0.63660(13) 0.33081(12) 0.87632(5) 0.0500(3) Uani 1 1 d . . .
O5 O 0.68265(16) 0.46767(15) 0.95270(6) 0.0653(4) Uani 1 1 d . . .
N1 N 0.68269(15) 0.28519(13) 0.82896(6) 0.0449(3) Uani 1 1 d . . .
C1 C 1.11147(18) 0.78707(15) 0.95868(7) 0.0413(4) Uani 1 1 d . . .
C2 C 1.1216(2) 0.87561(17) 1.00381(7) 0.0479(4) Uani 1 1 d . . .
H2 H 1.0425 0.8907 1.0131 0.057 Uiso 1 1 calc R . .
C3 C 1.2502(2) 0.94112(19) 1.03482(8) 0.0584(5) Uani 1 1 d . . .
H3 H 1.2587 1.0017 1.0651 0.070 Uiso 1 1 calc R . .
C4 C 1.3657(2) 0.9161(2) 1.02066(8) 0.0631(6) Uani 1 1 d . . .
H4 H 1.4527 0.9605 1.0414 0.076 Uiso 1 1 calc R . .
C5 C 1.3549(2) 0.8261(2) 0.97606(8) 0.0568(5) Uani 1 1 d . . .
H5 H 1.4351 0.8101 0.9676 0.068 Uiso 1 1 calc R . .
C6 C 1.22589(19) 0.75848(17) 0.94337(7) 0.0445(4) Uani 1 1 d . . .
C7 C 1.21500(18) 0.65835(18) 0.89710(8) 0.0462(4) Uani 1 1 d . . .
C8 C 1.3279(2) 0.5712(2) 0.90653(9) 0.0607(5) Uani 1 1 d . . .
H8 H 1.4114 0.5757 0.9427 0.073 Uiso 1 1 calc R . .
C9 C 1.3188(2) 0.4781(2) 0.86337(11) 0.0729(6) Uani 1 1 d . . .
H9 H 1.3955 0.4203 0.8709 0.087 Uiso 1 1 calc R . .
C10 C 1.1971(3) 0.4703(2) 0.80944(11) 0.0737(6) Uani 1 1 d . . .
H10 H 1.1914 0.4077 0.7804 0.088 Uiso 1 1 calc R . .
C11 C 1.0839(2) 0.5552(2) 0.79854(9) 0.0596(5) Uani 1 1 d . . .
H11 H 1.0012 0.5506 0.7620 0.072 Uiso 1 1 calc R . .
C12 C 1.09326(18) 0.64710(17) 0.84189(7) 0.0447(4) Uani 1 1 d . . .
C13 C 0.79974(17) 0.55965(15) 0.85042(7) 0.0377(4) Uani 1 1 d . . .
C14 C 0.70148(17) 0.52228(16) 0.79546(7) 0.0397(4) Uani 1 1 d . . .
C15 C 0.6389(2) 0.61119(19) 0.74030(8) 0.0550(5) Uani 1 1 d . . .
H15A H 0.6880 0.6955 0.7503 0.066 Uiso 1 1 calc R . .
H15B H 0.5370 0.6262 0.7305 0.066 Uiso 1 1 calc R . .
C16 C 0.6531(2) 0.5555(2) 0.68477(8) 0.0648(6) Uani 1 1 d . . .
H16A H 0.7546 0.5544 0.6919 0.078 Uiso 1 1 calc R . .
H16B H 0.6017 0.6117 0.6499 0.078 Uiso 1 1 calc R . .
C17 C 0.5925(3) 0.4176(2) 0.67070(8) 0.0676(6) Uani 1 1 d . . .
H17A H 0.6114 0.3818 0.6373 0.081 Uiso 1 1 calc R . .
H17B H 0.4882 0.4202 0.6579 0.081 Uiso 1 1 calc R . .
C18 C 0.6607(2) 0.3295(2) 0.72629(8) 0.0607(5) Uani 1 1 d . . .
H18A H 0.7639 0.3215 0.7372 0.073 Uiso 1 1 calc R . .
H18B H 0.6182 0.2424 0.7166 0.073 Uiso 1 1 calc R . .
C19 C 0.63696(18) 0.38529(17) 0.78040(7) 0.0433(4) Uani 1 1 d . . .
H19 H 0.5319 0.3955 0.7666 0.052 Uiso 1 1 calc R . .
C20 C 0.83580(19) 0.25639(16) 0.85677(7) 0.0415(4) Uani 1 1 d . . .
C21 C 0.8872(2) 0.13785(18) 0.84568(8) 0.0542(5) Uani 1 1 d . . .
H21 H 0.8241 0.0757 0.8198 0.065 Uiso 1 1 calc R . .
C22 C 1.0343(2) 0.1142(2) 0.87394(10) 0.0628(5) Uani 1 1 d . . .
H22 H 1.0712 0.0356 0.8665 0.075 Uiso 1 1 calc R . .
C23 C 1.1274(2) 0.2053(2) 0.91301(10) 0.0627(5) Uani 1 1 d . . .
H23 H 1.2265 0.1881 0.9313 0.075 Uiso 1 1 calc R . .
C24 C 1.07476(19) 0.32259(19) 0.92536(8) 0.0512(4) Uani 1 1 d . . .
H24 H 1.1372 0.3831 0.9526 0.061 Uiso 1 1 calc R . .
C25 C 0.92780(17) 0.34751(16) 0.89642(7) 0.0400(4) Uani 1 1 d . . .
C26 C 0.85181(18) 0.46686(15) 0.90575(7) 0.0404(4) Uani 1 1 d . . .
H26 H 0.9180 0.5146 0.9420 0.048 Uiso 1 1 calc R . .
C27 C 0.71993(19) 0.42505(17) 0.91513(8) 0.0461(4) Uani 1 1 d . . .
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
O1 P1 O3 116.18(8) . . ?
O1 P1 O2 109.64(7) . . ?
O3 P1 O2 103.41(6) . . ?
O1 P1 C13 117.57(8) . . ?
O3 P1 C13 100.52(7) . . ?
O2 P1 C13 108.28(7) . . ?
C12 O2 P1 119.37(10) . . ?
C1 O3 P1 124.44(10) . . ?
C27 O4 N1 116.59(12) . . ?
C20 N1 C19 115.67(13) . . ?
C20 N1 O4 109.23(12) . . ?
C19 N1 O4 107.41(12) . . ?
C2 C1 C6 123.22(16) . . ?
C2 C1 O3 116.87(15) . . ?
C6 C1 O3 119.59(14) . . ?
C3 C2 C1 119.22(18) . . ?
C3 C2 H2 120.4 . . ?
C1 C2 H2 120.4 . . ?
C4 C3 C2 119.26(18) . . ?
C4 C3 H3 120.4 . . ?
C2 C3 H3 120.4 . . ?
C3 C4 C5 120.99(18) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 H4 119.5 . . ?
C4 C5 C6 121.34(19) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
C1 C6 C5 115.96(17) . . ?
C1 C6 C7 122.36(15) . . ?
C5 C6 C7 121.63(17) . . ?
C8 C7 C12 116.54(17) . . ?
C8 C7 C6 121.12(16) . . ?
C12 C7 C6 122.33(16) . . ?
C9 C8 C7 121.41(19) . . ?
C9 C8 H8 119.3 . . ?
C7 C8 H8 119.3 . . ?
C10 C9 C8 120.3(2) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
C11 C10 C9 119.8(2) . . ?
C11 C10 H10 120.1 . . ?
C9 C10 H10 120.1 . . ?
C10 C11 C12 119.59(19) . . ?
C10 C11 H11 120.2 . . ?
C12 C11 H11 120.2 . . ?
C11 C12 C7 122.34(17) . . ?
C11 C12 O2 117.91(16) . . ?
C7 C12 O2 119.69(15) . . ?
C14 C13 C26 121.95(14) . . ?
C14 C13 P1 120.67(12) . . ?
C26 C13 P1 117.37(11) . . ?
C13 C14 C15 124.55(15) . . ?
C13 C14 C19 124.52(14) . . ?
C15 C14 C19 110.93(14) . . ?
C14 C15 C16 113.12(16) . . ?
C14 C15 H15A 109.0 . . ?
C16 C15 H15A 109.0 . . ?
C14 C15 H15B 109.0 . . ?
C16 C15 H15B 109.0 . . ?
H15A C15 H15B 107.8 . . ?
C15 C16 C17 111.57(17) . . ?
C15 C16 H16A 109.3 . . ?
C17 C16 H16A 109.3 . . ?
C15 C16 H16B 109.3 . . ?
C17 C16 H16B 109.3 . . ?
H16A C16 H16B 108.0 . . ?
C16 C17 C18 110.87(16) . . ?
C16 C17 H17A 109.5 . . ?
C18 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C18 C17 H17B 109.5 . . ?
H17A C17 H17B 108.1 . . ?
C17 C18 C19 110.88(16) . . ?
C17 C18 H18A 109.5 . . ?
C19 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C19 C18 H18B 109.5 . . ?
H18A C18 H18B 108.1 . . ?
N1 C19 C14 118.86(13) . . ?
N1 C19 C18 108.07(14) . . ?
C14 C19 C18 109.91(15) . . ?
N1 C19 H19 106.4 . . ?
C14 C19 H19 106.4 . . ?
C18 C19 H19 106.4 . . ?
C25 C20 C21 121.30(17) . . ?
C25 C20 N1 118.24(15) . . ?
C21 C20 N1 120.40(16) . . ?
C22 C21 C20 118.26(19) . . ?
C22 C21 H21 120.9 . . ?
C20 C21 H21 120.9 . . ?
C23 C22 C21 120.87(18) . . ?
C23 C22 H22 119.6 . . ?
C21 C22 H22 119.6 . . ?
C22 C23 C24 120.64(18) . . ?
C22 C23 H23 119.7 . . ?
C24 C23 H23 119.7 . . ?
C25 C24 C23 118.64(19) . . ?
C25 C24 H24 120.7 . . ?
C23 C24 H24 120.7 . . ?
C20 C25 C24 120.26(16) . . ?
C20 C25 C26 113.90(14) . . ?
C24 C25 C26 125.78(16) . . ?
C25 C26 C27 109.57(13) . . ?
C25 C26 C13 112.35(13) . . ?
C27 C26 C13 107.22(13) . . ?
C25 C26 H26 109.2 . . ?
C27 C26 H26 109.2 . . ?
C13 C26 H26 109.2 . . ?
O5 C27 O4 118.30(17) . . ?
O5 C27 C26 126.04(17) . . ?
O4 C27 C26 115.66(14) . . ?
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 O1 1.4501(13) . ?
P1 O3 1.5840(12) . ?
P1 O2 1.5940(13) . ?
P1 C13 1.7946(16) . ?
O2 C12 1.403(2) . ?
O3 C1 1.4007(19) . ?
O4 C27 1.360(2) . ?
O4 N1 1.4732(18) . ?
O5 C27 1.195(2) . ?
N1 C20 1.441(2) . ?
N1 C19 1.472(2) . ?
C1 C2 1.381(2) . ?
C1 C6 1.384(2) . ?
C2 C3 1.375(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.371(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.380(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.395(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.479(2) . ?
C7 C8 1.389(3) . ?
C7 C12 1.393(2) . ?
C8 C9 1.380(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.373(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.370(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.374(3) . ?
C11 H11 0.9300 . ?
C13 C14 1.339(2) . ?
C13 C26 1.536(2) . ?
C14 C15 1.511(2) . ?
C14 C19 1.518(2) . ?
C15 C16 1.511(3) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.512(3) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C18 1.518(3) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 C19 1.527(2) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 H19 0.9800 . ?
C20 C25 1.379(2) . ?
C20 C21 1.382(2) . ?
C21 C22 1.379(3) . ?
C21 H21 0.9300 . ?
C22 C23 1.378(3) . ?
C22 H22 0.9300 . ?
C23 C24 1.388(3) . ?
C23 H23 0.9300 . ?
C24 C25 1.380(2) . ?
C24 H24 0.9300 . ?
C25 C26 1.503(2) . ?
C26 C27 1.505(2) . ?
C26 H26 0.9800 . ?
