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#$Date: 2025-08-22 00:26:11 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301853 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/10/63/7106348.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_7106348
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_moiety         'C20 H23 Cl N O5 P'
_chemical_formula_sum            'C20 H23 Cl N O5 P'
_chemical_formula_weight         423.81
_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                 109.33(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.733(4)
_cell_length_b                   9.887(3)
_cell_length_c                   19.893(12)
_cell_measurement_reflns_used    1072
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      29.3787
_cell_measurement_theta_min      2.8266
_cell_volume                     1992.0(16)
_computing_cell_refinement       'CrysAlisPro, Oxford Diffraction Ltd.'
_computing_data_collection       'CrysAlisPro, Oxford Diffraction Ltd.'
_computing_data_reduction        'CrysAlisPro, Oxford Diffraction Ltd.'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω 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  0.0961
_diffrn_reflns_av_sigmaI/netI    0.1256
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            7946
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.83
_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    0.304
_exptl_absorpt_correction_T_max  0.9530
_exptl_absorpt_correction_T_min  0.9361
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlisPro, Oxford Diffraction Ltd.'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.413
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             888
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.649
_refine_diff_density_min         -0.602
_refine_diff_density_rms         0.093
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.853
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         3507
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.853
_refine_ls_R_factor_all          0.1376
_refine_ls_R_factor_gt           0.0719
_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)+(0.0998P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1616
_refine_ls_wR_factor_ref         0.1864
_reflns_number_gt                1637
_reflns_number_total             3507
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1cc10230c.txt
_cod_data_source_block           compound-7
_cod_original_cell_volume        1992.0(15)
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7106348
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
Cl1 Cl 0.61130(15) 1.10499(14) 0.63327(9) 0.0781(5) Uani 1 1 d . . .
P1 P 0.00953(13) 0.79396(12) 0.57699(7) 0.0454(4) Uani 1 1 d . . .
O1 O -0.1243(3) 0.7655(4) 0.5294(2) 0.0779(12) Uani 1 1 d . . .
O2 O 0.0315(4) 0.7480(3) 0.65579(19) 0.0549(9) Uani 1 1 d . . .
O3 O 0.0387(3) 0.9490(3) 0.58329(16) 0.0467(9) Uani 1 1 d . . .
O4 O 0.2540(3) 0.6297(3) 0.43358(17) 0.0520(9) Uani 1 1 d . . .
O5 O 0.0808(4) 0.7549(3) 0.3786(2) 0.0601(10) Uani 1 1 d . . .
N1 N 0.3546(4) 0.5972(3) 0.5027(2) 0.0474(11) Uani 1 1 d . . .
C1 C 0.1481(6) 0.7979(5) 0.7116(3) 0.0597(15) Uani 1 1 d . . .
H1A H 0.2269 0.7665 0.7027 0.072 Uiso 1 1 d R . .
H1B H 0.1495 0.7622 0.7572 0.072 Uiso 1 1 d R . .
C2 C 0.1482(5) 0.9510(4) 0.7141(3) 0.0452(12) Uani 1 1 d . . .
C3 C 0.1457(5) 1.0033(4) 0.6425(3) 0.0492(13) Uani 1 1 d . . .
H3A H 0.1381 1.1011 0.6422 0.059 Uiso 1 1 calc R . .
H3B H 0.2288 0.9811 0.6358 0.059 Uiso 1 1 calc R . .
C4 C 0.2763(6) 0.9980(6) 0.7693(3) 0.092(2) Uani 1 1 d . . .
H4A H 0.3497 0.9670 0.7561 0.138 Uiso 1 1 calc R . .
H4B H 0.2826 0.9617 0.8150 0.138 Uiso 1 1 calc R . .
H4C H 0.2774 1.0950 0.7715 0.138 Uiso 1 1 calc R . .
C5 C 0.0294(5) 1.0031(5) 0.7331(3) 0.0680(16) Uani 1 1 d . . .
H5A H 0.0312 1.1002 0.7347 0.082 Uiso 1 1 d R . .
H5B H 0.0333 0.9683 0.7788 0.082 Uiso 1 1 d R . .
H5C H -0.0508 0.9735 0.6976 0.082 Uiso 1 1 d R . .
C6 C 0.1402(4) 0.7173(4) 0.5501(2) 0.0338(11) Uani 1 1 d . . .
C7 C 0.1942(4) 0.8072(4) 0.5023(2) 0.0408(12) Uani 1 1 d . . .
H7 H 0.1473 0.8938 0.4935 0.049 Uiso 1 1 calc R . .
C8 C 0.3411(4) 0.8320(4) 0.5351(2) 0.0401(12) Uani 1 1 d . . .
C9 C 0.4008(5) 0.9520(4) 0.5631(3) 0.0461(13) Uani 1 1 d . . .
H9 H 0.3504 1.0296 0.5606 0.055 Uiso 1 1 calc R . .
C10 C 0.5376(5) 0.9562(5) 0.5953(3) 0.0529(14) Uani 1 1 d . . .
C11 C 0.6138(5) 0.8433(5) 0.5954(3) 0.0582(14) Uani 1 1 d . . .
H11 H 0.7051 0.8481 0.6162 0.070 Uiso 1 1 calc R . .
C12 C 0.5559(5) 0.7242(5) 0.5649(3) 0.0542(14) Uani 1 1 d . . .
H12 H 0.6071 0.6487 0.5641 0.065 Uiso 1 1 calc R . .
C13 C 0.4188(5) 0.7193(4) 0.5351(3) 0.0434(12) Uani 1 1 d . . .
C14 C 0.1679(5) 0.7317(5) 0.4322(3) 0.0475(13) Uani 1 1 d . . .
C15 C 0.2847(4) 0.5193(4) 0.5427(3) 0.0434(12) Uani 1 1 d . . .
H15 H 0.2432 0.4420 0.5128 0.052 Uiso 1 1 calc R . .
C16 C 0.3924(5) 0.4617(5) 0.6087(3) 0.0566(14) Uani 1 1 d . . .
H16A H 0.4589 0.4157 0.5940 0.068 Uiso 1 1 calc R . .
H16B H 0.4350 0.5352 0.6403 0.068 Uiso 1 1 calc R . .
C17 C 0.3329(5) 0.3628(5) 0.6485(3) 0.0642(15) Uani 1 1 d . . .
H17A H 0.3009 0.2835 0.6191 0.077 Uiso 1 1 calc R . .
H17B H 0.4007 0.3338 0.6918 0.077 Uiso 1 1 calc R . .
C18 C 0.2197(5) 0.4268(5) 0.6671(3) 0.0564(14) Uani 1 1 d . . .
H18A H 0.1776 0.3584 0.6872 0.068 Uiso 1 1 calc R . .
H18B H 0.2545 0.4961 0.7029 0.068 Uiso 1 1 calc R . .
C19 C 0.1175(5) 0.4895(4) 0.6025(3) 0.0483(13) Uani 1 1 d . . .
H19A H 0.0740 0.4181 0.5696 0.058 Uiso 1 1 calc R . .
H19B H 0.0511 0.5348 0.6175 0.058 Uiso 1 1 calc R . .
C20 C 0.1763(4) 0.5901(4) 0.5640(2) 0.0367(11) 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'
Cl Cl 0.1484 0.1585 '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 111.6(2) . . ?
O1 P1 O2 112.3(2) . . ?
O3 P1 O2 104.11(18) . . ?
O1 P1 C6 114.6(2) . . ?
O3 P1 C6 106.18(17) . . ?
O2 P1 C6 107.21(19) . . ?
C1 O2 P1 118.0(3) . . ?
C3 O3 P1 120.9(3) . . ?
C14 O4 N1 117.5(4) . . ?
C13 N1 O4 109.3(3) . . ?
C13 N1 C15 116.8(3) . . ?
O4 N1 C15 105.6(3) . . ?
O2 C1 C2 110.8(4) . . ?
O2 C1 H1A 109.5 . . ?
C2 C1 H1A 109.5 . . ?
O2 C1 H1B 109.5 . . ?
C2 C1 H1B 109.4 . . ?
H1A C1 H1B 108.1 . . ?
C3 C2 C1 108.2(4) . . ?
C3 C2 C4 107.8(4) . . ?
C1 C2 C4 108.7(5) . . ?
C3 C2 C5 111.2(4) . . ?
C1 C2 C5 110.7(4) . . ?
C4 C2 C5 110.3(4) . . ?
O3 C3 C2 113.7(4) . . ?
O3 C3 H3A 108.8 . . ?
C2 C3 H3A 108.8 . . ?
O3 C3 H3B 108.8 . . ?
C2 C3 H3B 108.8 . . ?
H3A C3 H3B 107.7 . . ?
C2 C4 H4A 109.5 . . ?
C2 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C2 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C2 C5 H5A 109.5 . . ?
C2 C5 H5B 109.4 . . ?
H5A C5 H5B 109.5 . . ?
C2 C5 H5C 109.4 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C20 C6 C7 122.1(3) . . ?
C20 C6 P1 122.5(3) . . ?
C7 C6 P1 115.0(3) . . ?
C8 C7 C14 109.0(4) . . ?
C8 C7 C6 112.1(4) . . ?
C14 C7 C6 106.7(3) . . ?
C8 C7 H7 109.7 . . ?
C14 C7 H7 109.7 . . ?
C6 C7 H7 109.7 . . ?
C9 C8 C13 119.4(4) . . ?
C9 C8 C7 126.4(4) . . ?
C13 C8 C7 114.2(4) . . ?
C8 C9 C10 119.3(4) . . ?
C8 C9 H9 120.3 . . ?
C10 C9 H9 120.3 . . ?
C11 C10 C9 120.6(5) . . ?
C11 C10 Cl1 120.2(4) . . ?
C9 C10 Cl1 119.2(4) . . ?
C12 C11 C10 120.6(5) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C11 C12 C13 118.5(4) . . ?
C11 C12 H12 120.8 . . ?
C13 C12 H12 120.8 . . ?
C8 C13 C12 121.4(4) . . ?
C8 C13 N1 118.3(4) . . ?
C12 C13 N1 120.2(4) . . ?
O5 C14 O4 119.3(5) . . ?
O5 C14 C7 125.5(5) . . ?
O4 C14 C7 115.2(5) . . ?
N1 C15 C20 118.6(3) . . ?
N1 C15 C16 106.2(4) . . ?
C20 C15 C16 110.9(4) . . ?
N1 C15 H15 106.9 . . ?
C20 C15 H15 106.9 . . ?
C16 C15 H15 106.9 . . ?
C17 C16 C15 110.7(4) . . ?
C17 C16 H16A 109.5 . . ?
C15 C16 H16A 109.5 . . ?
C17 C16 H16B 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 108.1 . . ?
C18 C17 C16 111.4(4) . . ?
C18 C17 H17A 109.3 . . ?
C16 C17 H17A 109.3 . . ?
C18 C17 H17B 109.3 . . ?
C16 C17 H17B 109.3 . . ?
H17A C17 H17B 108.0 . . ?
C19 C18 C17 112.0(4) . . ?
C19 C18 H18A 109.2 . . ?
C17 C18 H18A 109.2 . . ?
C19 C18 H18B 109.2 . . ?
C17 C18 H18B 109.2 . . ?
H18A C18 H18B 107.9 . . ?
C20 C19 C18 113.0(4) . . ?
C20 C19 H19A 109.0 . . ?
C18 C19 H19A 109.0 . . ?
C20 C19 H19B 109.0 . . ?
C18 C19 H19B 109.0 . . ?
H19A C19 H19B 107.8 . . ?
C6 C20 C19 126.1(4) . . ?
C6 C20 C15 125.1(3) . . ?
C19 C20 C15 108.7(3) . . ?
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
Cl1 C10 1.722(5) . ?
P1 O1 1.462(4) . ?
P1 O3 1.561(3) . ?
P1 O2 1.573(4) . ?
P1 C6 1.822(4) . ?
O2 C1 1.456(6) . ?
O3 C3 1.449(6) . ?
O4 C14 1.362(5) . ?
O4 N1 1.475(5) . ?
O5 C14 1.185(6) . ?
N1 C13 1.433(5) . ?
N1 C15 1.478(5) . ?
C1 C2 1.515(6) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9699 . ?
C2 C3 1.508(6) . ?
C2 C4 1.520(7) . ?
C2 C5 1.534(6) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C5 H5A 0.9601 . ?
C5 H5B 0.9599 . ?
C5 H5C 0.9601 . ?
C6 C20 1.318(5) . ?
C6 C7 1.549(5) . ?
C7 C8 1.513(6) . ?
C7 C14 1.522(7) . ?
C7 H7 0.9800 . ?
C8 C9 1.377(6) . ?
C8 C13 1.392(6) . ?
C9 C10 1.394(7) . ?
C9 H9 0.9300 . ?
C10 C11 1.384(7) . ?
C11 C12 1.376(6) . ?
C11 H11 0.9300 . ?
C12 C13 1.393(6) . ?
C12 H12 0.9300 . ?
C15 C20 1.533(5) . ?
C15 C16 1.544(7) . ?
C15 H15 0.9800 . ?
C16 C17 1.524(6) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C18 1.520(6) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 C19 1.519(7) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 C20 1.514(6) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139181863
