#------------------------------------------------------------------------------
#$Date: 2025-08-18 16:30:32 +0300 (Mon, 18 Aug 2025) $
#$Revision: 301775 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/75/1507571.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_1507571
loop_
_publ_author_name
'Dekorver, Kyle A.'
'Wang, Xiao-Na'
'Walton, Mary C.'
'Hsung, Richard P.'
_publ_section_title
;
 Carbocyclization Cascades of Allyl Ketenimines via Aza-Claisen
 Rearrangements of N-Phosphoryl-N-allyl-ynamides.
;
_journal_issue                   7
_journal_name_full               'Organic letters'
_journal_page_first              1768
_journal_page_last               1771
_journal_paper_doi               10.1021/ol300366e
_journal_volume                  14
_journal_year                    2012
_chemical_formula_moiety         'C18 H24 N O5 P'
_chemical_formula_sum            'C18 H24 N O5 P'
_chemical_formula_weight         365.35
_chemical_name_common            11275a
_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                 93.771(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.8692(15)
_cell_length_b                   5.7913(8)
_cell_length_c                   29.339(4)
_cell_measurement_reflns_used    2199
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      23.50
_cell_measurement_theta_min      2.41
_cell_volume                     1842.8(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0539
_diffrn_reflns_av_sigmaI/netI    0.0634
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            9591
_diffrn_reflns_theta_full        25.11
_diffrn_reflns_theta_max         25.11
_diffrn_reflns_theta_min         1.88
_exptl_absorpt_coefficient_mu    0.177
_exptl_absorpt_correction_T_max  0.996
_exptl_absorpt_correction_T_min  0.983
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008/1)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Needle
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.214
_refine_diff_density_min         -0.295
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     266
_refine_ls_number_reflns         3264
_refine_ls_number_restraints     33
_refine_ls_restrained_S_all      1.014
_refine_ls_R_factor_all          0.0949
_refine_ls_R_factor_gt           0.0475
_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)+(0.0369P)²+0.8485P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0905
_refine_ls_wR_factor_ref         0.1097
_reflns_number_gt                2050
_reflns_number_total             3264
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol300366e_si_003.cif
_cod_data_source_block           11275a
_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 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'Multi-scan'
changed to 'multi-scan' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               1507571
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
N1 N 0.4204(2) 0.4374(4) 0.63578(8) 0.0351(6) Uani 1 1 d . A .
H1A H 0.348(3) 0.379(5) 0.6358(10) 0.042 Uiso 1 1 d . . .
C1 C 0.4836(2) 0.3661(5) 0.59963(11) 0.0374(7) Uani 1 1 d . . .
C2 C 0.4408(10) 0.192(2) 0.5732(5) 0.034(2) Uani 0.588(5) 1 d PD A 1
H2A H 0.4944 0.1267 0.5523 0.041 Uiso 0.588(5) 1 calc PR A 1
C3 C 0.3179(9) 0.0964(12) 0.5743(3) 0.0273(16) Uani 0.588(5) 1 d PD A 1
O1 O 0.2454(15) 0.162(3) 0.6025(4) 0.032(2) Uani 0.588(5) 1 d PD A 1
C4 C 0.2770(7) -0.0806(11) 0.5384(2) 0.0385(17) Uani 0.588(5) 1 d PD A 1
H4A H 0.3507 -0.1711 0.5302 0.046 Uiso 0.588(5) 1 calc PR A 1
C5 C 0.2278(9) 0.0526(13) 0.4969(2) 0.075(3) Uani 0.588(5) 1 d PDU A 1
H5A H 0.2034 -0.0555 0.4722 0.113 Uiso 0.588(5) 1 calc PR A 1
H5B H 0.2920 0.1562 0.4868 0.113 Uiso 0.588(5) 1 calc PR A 1
H5C H 0.1561 0.1436 0.5046 0.113 Uiso 0.588(5) 1 calc PR A 1
C6 C 0.1825(5) -0.2452(9) 0.55486(19) 0.0480(17) Uani 0.588(5) 1 d PDU A 1
H6A H 0.2155 -0.3206 0.5830 0.072 Uiso 0.588(5) 1 calc PR A 1
H6B H 0.1631 -0.3624 0.5314 0.072 Uiso 0.588(5) 1 calc PR A 1
H6C H 0.1075 -0.1600 0.5609 0.072 Uiso 0.588(5) 1 calc PR A 1
C2' C 0.4267(15) 0.244(3) 0.5621(7) 0.034(2) Uani 0.412(5) 1 d PD A 2
H2A' H 0.4715 0.2222 0.5357 0.041 Uiso 0.412(5) 1 calc PR A 2
C3' C 0.3028(13) 0.1512(18) 0.5623(4) 0.0273(16) Uani 0.412(5) 1 d PD A 2
O1' O 0.234(2) 0.190(5) 0.5933(6) 0.032(2) Uani 0.412(5) 1 d PD A 2
C4' C 0.2593(9) 0.0003(19) 0.5220(4) 0.0385(17) Uani 0.412(5) 1 d PD A 2
H4A' H 0.2998 0.0569 0.4945 0.046 Uiso 0.412(5) 1 calc PR A 2
C5' C 0.1219(8) 0.021(2) 0.5125(3) 0.080(4) Uani 0.412(5) 1 d PDU A 2
H5A' H 0.0993 0.1848 0.5099 0.119 Uiso 0.412(5) 1 calc PR A 2
H5B' H 0.0799 -0.0490 0.5376 0.119 Uiso 0.412(5) 1 calc PR A 2
H5C' H 0.0972 -0.0583 0.4839 0.119 Uiso 0.412(5) 1 calc PR A 2
C6' C 0.3015(9) -0.2451(16) 0.5313(3) 0.063(3) Uani 0.412(5) 1 d PDU A 2
H6A' H 0.2806 -0.3406 0.5043 0.095 Uiso 0.412(5) 1 calc PR A 2
H6B' H 0.2603 -0.3066 0.5574 0.095 Uiso 0.412(5) 1 calc PR A 2
H6C' H 0.3910 -0.2471 0.5381 0.095 Uiso 0.412(5) 1 calc PR A 2
C7 C 0.6068(3) 0.4768(5) 0.59165(10) 0.0376(7) Uani 1 1 d . A .
O2 O 0.60589(19) 0.6653(4) 0.57359(9) 0.0575(7) Uani 1 1 d . . .
C8 C 0.7214(2) 0.3457(5) 0.60356(9) 0.0326(7) Uani 1 1 d . . .
C9 C 0.8339(3) 0.4401(5) 0.59277(10) 0.0373(7) Uani 1 1 d . A .
H9A H 0.8361 0.5868 0.5784 0.045 Uiso 1 1 calc R . .
C10 C 0.9421(3) 0.3202(6) 0.60301(11) 0.0437(8) Uani 1 1 d . . .
H10A H 1.0187 0.3839 0.5955 0.052 Uiso 1 1 calc R A .
C11 C 0.9387(3) 0.1072(6) 0.62426(10) 0.0458(8) Uani 1 1 d . A .
H11A H 1.0132 0.0247 0.6312 0.055 Uiso 1 1 calc R . .
C12 C 0.8283(3) 0.0147(6) 0.63531(10) 0.0423(8) Uani 1 1 d . . .
H12A H 0.8267 -0.1309 0.6502 0.051 Uiso 1 1 calc R A .
C13 C 0.7194(3) 0.1320(5) 0.62493(10) 0.0376(7) Uani 1 1 d . A .
H13A H 0.6431 0.0664 0.6324 0.045 Uiso 1 1 calc R . .
P1 P 0.45940(7) 0.62189(13) 0.67693(3) 0.0330(2) Uani 1 1 d . . .
O3 O 0.59157(17) 0.6694(3) 0.68001(7) 0.0428(5) Uani 1 1 d . A .
O4 O 0.40672(17) 0.4992(3) 0.71911(6) 0.0353(5) Uani 1 1 d . A .
C14 C 0.3335(2) 0.6195(5) 0.75206(9) 0.0340(7) Uani 1 1 d . . .
H14A H 0.3883 0.7182 0.7721 0.041 Uiso 1 1 calc R A .
H14B H 0.2943 0.5048 0.7715 0.041 Uiso 1 1 calc R . .
C15 C 0.2347(2) 0.7675(5) 0.72757(10) 0.0329(7) Uani 1 1 d . A .
C16 C 0.2978(3) 0.9436(5) 0.69905(10) 0.0372(7) Uani 1 1 d . . .
H16A H 0.2345 1.0396 0.6823 0.045 Uiso 1 1 calc R A .
H16B H 0.3490 1.0466 0.7195 0.045 Uiso 1 1 calc R . .
O5 O 0.37517(19) 0.8365(3) 0.66667(7) 0.0471(6) Uani 1 1 d . A .
C17 C 0.1653(3) 0.8989(5) 0.76318(11) 0.0478(8) Uani 1 1 d . . .
H17A H 0.1057 1.0043 0.7477 0.072 Uiso 1 1 calc R A .
H17B H 0.2241 0.9877 0.7830 0.072 Uiso 1 1 calc R . .
H17C H 0.1217 0.7888 0.7817 0.072 Uiso 1 1 calc R . .
C18 C 0.1446(3) 0.6177(5) 0.69799(11) 0.0472(8) Uani 1 1 d . . .
H18A H 0.1879 0.5487 0.6731 0.071 Uiso 1 1 calc R A .
H18B H 0.0766 0.7137 0.6852 0.071 Uiso 1 1 calc R . .
H18C H 0.1120 0.4950 0.7168 0.071 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
C1 N1 P1 130.4(2)
C1 N1 H1A 113.1(19)
P1 N1 H1A 116.5(19)
C2 C1 N1 120.4(6)
C2 C1 C2' 19.1(9)
N1 C1 C2' 122.6(9)
C2 C1 C7 120.4(6)
N1 C1 C7 119.1(3)
C2' C1 C7 115.8(8)
C1 C2 C3 124.1(11)
C1 C2 H2A 117.9
C3 C2 H2A 117.9
O1 C3 C2 121.7(11)
O1 C3 C4 120.1(10)
C2 C3 C4 118.1(8)
C6 C4 C5 111.7(6)
C6 C4 C3 112.4(6)
C5 C4 C3 106.7(5)
C6 C4 H4A 108.6
C5 C4 H4A 108.6
C3 C4 H4A 108.6
C1 C2' C3' 122.7(16)
C1 C2' H2A' 118.7
C3' C2' H2A' 118.7
O1' C3' C2' 122.8(16)
O1' C3' C4' 120.4(15)
C2' C3' C4' 116.8(12)
C5' C4' C6' 113.2(10)
C5' C4' C3' 110.6(9)
C6' C4' C3' 109.0(8)
C5' C4' H4A' 108.0
C6' C4' H4A' 108.0
C3' C4' H4A' 108.0
C4' C5' H5A' 109.5
C4' C5' H5B' 109.5
H5A' C5' H5B' 109.5
C4' C5' H5C' 109.5
H5A' C5' H5C' 109.5
H5B' C5' H5C' 109.5
C4' C6' H6A' 109.5
C4' C6' H6B' 109.5
H6A' C6' H6B' 109.5
C4' C6' H6C' 109.5
H6A' C6' H6C' 109.5
H6B' C6' H6C' 109.5
O2 C7 C8 123.2(3)
O2 C7 C1 117.8(3)
C8 C7 C1 119.0(3)
C13 C8 C9 119.5(3)
C13 C8 C7 121.7(3)
C9 C8 C7 118.8(3)
C10 C9 C8 120.0(3)
C10 C9 H9A 120.0
C8 C9 H9A 120.0
C9 C10 C11 119.9(3)
C9 C10 H10A 120.0
C11 C10 H10A 120.0
C12 C11 C10 120.3(3)
C12 C11 H11A 119.9
C10 C11 H11A 119.9
C11 C12 C13 120.4(3)
C11 C12 H12A 119.8
C13 C12 H12A 119.8
C12 C13 C8 119.9(3)
C12 C13 H13A 120.0
C8 C13 H13A 120.0
O3 P1 O5 115.10(12)
O3 P1 O4 116.46(12)
O5 P1 O4 105.84(11)
O3 P1 N1 111.87(12)
O5 P1 N1 104.82(13)
O4 P1 N1 101.25(12)
C14 O4 P1 123.16(16)
O4 C14 C15 110.7(2)
O4 C14 H14A 109.5
C15 C14 H14A 109.5
O4 C14 H14B 109.5
C15 C14 H14B 109.5
H14A C14 H14B 108.1
C16 C15 C14 108.1(2)
C16 C15 C17 107.7(2)
C14 C15 C17 108.8(2)
C16 C15 C18 111.4(2)
C14 C15 C18 110.7(2)
C17 C15 C18 110.0(2)
O5 C16 C15 112.2(2)
O5 C16 H16A 109.2
C15 C16 H16A 109.2
O5 C16 H16B 109.2
C15 C16 H16B 109.2
H16A C16 H16B 107.9
C16 O5 P1 124.94(18)
C15 C17 H17A 109.5
C15 C17 H17B 109.5
H17A C17 H17B 109.5
C15 C17 H17C 109.5
H17A C17 H17C 109.5
H17B C17 H17C 109.5
C15 C18 H18A 109.5
C15 C18 H18B 109.5
H18A C18 H18B 109.5
C15 C18 H18C 109.5
H18A C18 H18C 109.5
H18B C18 H18C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C1 1.365(4)
N1 P1 1.646(2)
N1 H1A 0.86(3)
C1 C2 1.338(14)
C1 C2' 1.42(2)
C1 C7 1.516(4)
C2 C3 1.448(8)
C2 H2A 0.9500
C3 O1 1.240(8)
C3 C4 1.515(8)
C4 C6 1.504(7)
C4 C5 1.510(8)
C4 H4A 1.0000
C5 H5A 0.9800
C5 H5B 0.9800
C5 H5C 0.9800
C6 H6A 0.9800
C6 H6B 0.9800
C6 H6C 0.9800
C2' C3' 1.451(12)
C2' H2A' 0.9500
C3' O1' 1.234(12)
C3' C4' 1.520(11)
C4' C5' 1.505(10)
C4' C6' 1.513(10)
C4' H4A' 1.0000
C5' H5A' 0.9800
C5' H5B' 0.9800
C5' H5C' 0.9800
C6' H6A' 0.9800
C6' H6B' 0.9800
C6' H6C' 0.9800
C7 O2 1.213(3)
C7 C8 1.481(4)
C8 C13 1.388(4)
C8 C9 1.394(4)
C9 C10 1.382(4)
C9 H9A 0.9500
C10 C11 1.383(4)
C10 H10A 0.9500
C11 C12 1.373(4)
C11 H11A 0.9500
C12 C13 1.381(4)
C12 H12A 0.9500
C13 H13A 0.9500
P1 O3 1.460(2)
P1 O5 1.561(2)
P1 O4 1.5675(19)
O4 C14 1.468(3)
C14 C15 1.517(4)
C14 H14A 0.9900
C14 H14B 0.9900
C15 C16 1.512(4)
C15 C17 1.531(4)
C15 C18 1.534(4)
C16 O5 1.449(3)
C16 H16A 0.9900
C16 H16B 0.9900
C17 H17A 0.9800
C17 H17B 0.9800
C17 H17C 0.9800
C18 H18A 0.9800
C18 H18B 0.9800
C18 H18C 0.9800
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N1 H1A O1 0.86(3) 1.90(4) 2.62(2) 140(3)
N1 H1A O1' 0.86(3) 2.02(4) 2.71(3) 137(3)
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
P1 N1 C1 C2 171.6(5)
P1 N1 C1 C2' -166.2(8)
P1 N1 C1 C7 -4.6(4)
N1 C1 C2 C3 12.3(9)
C2' C1 C2 C3 -90(4)
C7 C1 C2 C3 -171.5(5)
C1 C2 C3 O1 -4.6(12)
C1 C2 C3 C4 172.6(7)
O1 C3 C4 C6 -30.7(11)
C2 C3 C4 C6 152.0(6)
O1 C3 C4 C5 92.1(10)
C2 C3 C4 C5 -85.2(8)
C2 C1 C2' C3' 79(4)
N1 C1 C2' C3' -10.7(17)
C7 C1 C2' C3' -172.7(10)
C1 C2' C3' O1' 7(2)
C1 C2' C3' C4' -173.0(11)
O1' C3' C4' C5' 30.3(17)
C2' C3' C4' C5' -149.6(12)
O1' C3' C4' C6' -94.8(16)
C2' C3' C4' C6' 85.4(12)
C2 C1 C7 O2 104.9(5)
N1 C1 C7 O2 -78.8(4)
C2' C1 C7 O2 83.9(8)
C2 C1 C7 C8 -71.5(6)
N1 C1 C7 C8 104.8(3)
C2' C1 C7 C8 -92.5(8)
O2 C7 C8 C13 178.9(3)
C1 C7 C8 C13 -4.9(4)
O2 C7 C8 C9 -1.3(4)
C1 C7 C8 C9 174.8(3)
C13 C8 C9 C10 0.5(4)
C7 C8 C9 C10 -179.2(3)
C8 C9 C10 C11 -0.4(4)
C9 C10 C11 C12 -0.1(4)
C10 C11 C12 C13 0.7(4)
C11 C12 C13 C8 -0.6(4)
C9 C8 C13 C12 0.0(4)
C7 C8 C13 C12 179.7(3)
C1 N1 P1 O3 -16.0(3)
C1 N1 P1 O5 109.4(3)
C1 N1 P1 O4 -140.7(3)
O3 P1 O4 C14 105.5(2)
O5 P1 O4 C14 -23.9(2)
N1 P1 O4 C14 -133.0(2)
P1 O4 C14 C15 46.5(3)
O4 C14 C15 C16 -60.4(3)
O4 C14 C15 C17 -177.1(2)
O4 C14 C15 C18 61.8(3)
C14 C15 C16 O5 57.6(3)
C17 C15 C16 O5 175.0(2)
C18 C15 C16 O5 -64.2(3)
C15 C16 O5 P1 -40.4(3)
O3 P1 O5 C16 -109.4(2)
O4 P1 O5 C16 20.7(2)
N1 P1 O5 C16 127.3(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139040129
