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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/7/10/35/7103585.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_7103585
loop_
_publ_author_name
'Xiang, Dexuan'
'Huang, Peng'
'Wang, Kewei'
'Zhou, Guangyuan'
'Liang, Yongjiu'
'Dong, Dewen'
_publ_section_title
;
 Efficient and divergent synthesis of cyclophosphamide analogues from
 2-arylamino-3-acetyl-5,6-dihydro-4H-pyrans.
;
_journal_issue                   46
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              6236
_journal_page_last               6238
_journal_paper_doi               10.1039/b815416c
_journal_year                    2008
_chemical_formula_sum            'C13 H14 Cl2 N O3 P'
_chemical_formula_weight         334.12
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 104.543(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.560(3)
_cell_length_b                   10.346(3)
_cell_length_c                   15.722(5)
_cell_measurement_reflns_used    8234
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      26.09
_cell_measurement_theta_min      2.27
_cell_volume                     1505.2(8)
_computing_cell_refinement       'RAPID AUTO'
_computing_data_collection       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 0.01
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID IP'
_diffrn_measurement_method       Oscillation
_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  0.0255
_diffrn_reflns_av_sigmaI/netI    0.0302
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            8234
_diffrn_reflns_theta_full        26.09
_diffrn_reflns_theta_max         26.09
_diffrn_reflns_theta_min         2.27
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.542
_exptl_absorpt_correction_T_max  0.912
_exptl_absorpt_correction_T_min  0.883
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR by T.Higashi 8 March, 1995'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.474
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.451
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2975
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.084
_refine_ls_R_factor_all          0.0738
_refine_ls_R_factor_gt           0.0520
_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)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1501
_refine_ls_wR_factor_ref         0.1679
_reflns_number_gt                2179
_reflns_number_total             2975
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b815416c.txt
_cod_data_source_block           xiang3
_cod_original_sg_symbol_H-M      P21/n
_cod_database_code               7103585
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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 0.00051(8) 0.68019(7) 0.11502(5) 0.0483(3) Uani 1 1 d . . .
Cl1 Cl -0.16715(10) 0.55945(9) 0.09638(6) 0.0737(3) Uani 1 1 d . . .
Cl2 Cl -0.47852(15) 1.20753(11) -0.12145(8) 0.1082(5) Uani 1 1 d . . .
N1 N -0.0564(3) 0.8206(2) 0.14417(14) 0.0452(6) Uani 1 1 d . . .
O1 O 0.0170(2) 0.70696(19) 0.01939(13) 0.0559(6) Uani 1 1 d . . .
O2 O -0.1781(2) 1.0088(2) 0.10910(13) 0.0615(6) Uani 1 1 d . . .
O3 O 0.1290(2) 0.6259(2) 0.17400(14) 0.0658(7) Uani 1 1 d . . .
C1 C -0.1481(3) 0.7835(3) 0.2745(2) 0.0554(8) Uani 1 1 d . . .
H1A H -0.2236 0.7350 0.2405 0.066 Uiso 1 1 calc R . .
C2 C -0.1344(4) 0.7992(3) 0.3647(2) 0.0616(9) Uani 1 1 d . . .
H2A H -0.1994 0.7592 0.3914 0.074 Uiso 1 1 calc R . .
C3 C -0.0245(4) 0.8739(3) 0.4133(2) 0.0623(9) Uani 1 1 d . . .
H3A H -0.0150 0.8844 0.4732 0.075 Uiso 1 1 calc R . .
C4 C 0.0720(4) 0.9335(3) 0.3740(2) 0.0607(9) Uani 1 1 d . . .
H4A H 0.1447 0.9856 0.4073 0.073 Uiso 1 1 calc R . .
C5 C 0.0611(3) 0.9162(3) 0.28612(19) 0.0526(7) Uani 1 1 d . . .
H5A H 0.1274 0.9551 0.2599 0.063 Uiso 1 1 calc R . .
C6 C -0.0483(3) 0.8410(3) 0.23695(17) 0.0435(7) Uani 1 1 d . . .
C7 C -0.1301(3) 0.9133(3) 0.08249(18) 0.0460(7) Uani 1 1 d . . .
C8 C -0.1414(3) 0.8883(3) -0.01127(17) 0.0459(7) Uani 1 1 d . . .
C9 C -0.2310(3) 0.9868(3) -0.07406(19) 0.0510(7) Uani 1 1 d . . .
H9A H -0.2166 1.0718 -0.0472 0.061 Uiso 1 1 calc R . .
H9B H -0.1979 0.9897 -0.1275 0.061 Uiso 1 1 calc R . .
C10 C -0.3894(3) 0.9549(3) -0.0969(2) 0.0600(8) Uani 1 1 d . . .
H10A H -0.4226 0.9546 -0.0435 0.072 Uiso 1 1 calc R . .
H10B H -0.4029 0.8685 -0.1216 0.072 Uiso 1 1 calc R . .
C11 C -0.4814(4) 1.0482(3) -0.1616(2) 0.0636(9) Uani 1 1 d . . .
H11A H -0.5804 1.0174 -0.1769 0.076 Uiso 1 1 calc R . .
H11B H -0.4477 1.0490 -0.2149 0.076 Uiso 1 1 calc R . .
C12 C -0.0754(3) 0.7906(3) -0.04005(18) 0.0477(7) Uani 1 1 d . . .
C13 C -0.0765(4) 0.7547(4) -0.1312(2) 0.0620(9) Uani 1 1 d . . .
H13A H -0.1394 0.8121 -0.1714 0.093 Uiso 1 1 calc R . .
H13B H -0.1105 0.6675 -0.1424 0.093 Uiso 1 1 calc R . .
H13C H 0.0196 0.7612 -0.1391 0.093 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'
Cl Cl 0.1484 0.1585 '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
O3 P1 O1 113.96(13) . . ?
O3 P1 N1 116.52(13) . . ?
O1 P1 N1 103.20(11) . . ?
O3 P1 Cl1 111.76(11) . . ?
O1 P1 Cl1 103.83(9) . . ?
N1 P1 Cl1 106.39(10) . . ?
C7 N1 C6 118.6(2) . . ?
C7 N1 P1 123.06(19) . . ?
C6 N1 P1 117.76(17) . . ?
C12 O1 P1 123.0(2) . . ?
C6 C1 C2 119.0(3) . . ?
C6 C1 H1A 120.5 . . ?
C2 C1 H1A 120.5 . . ?
C3 C2 C1 119.6(3) . . ?
C3 C2 H2A 120.2 . . ?
C1 C2 H2A 120.2 . . ?
C4 C3 C2 120.5(3) . . ?
C4 C3 H3A 119.8 . . ?
C2 C3 H3A 119.8 . . ?
C3 C4 C5 120.2(3) . . ?
C3 C4 H4A 119.9 . . ?
C5 C4 H4A 119.9 . . ?
C6 C5 C4 119.6(3) . . ?
C6 C5 H5A 120.2 . . ?
C4 C5 H5A 120.2 . . ?
C5 C6 C1 121.0(3) . . ?
C5 C6 N1 119.1(3) . . ?
C1 C6 N1 119.9(3) . . ?
O2 C7 N1 118.9(3) . . ?
O2 C7 C8 123.5(3) . . ?
N1 C7 C8 117.6(3) . . ?
C12 C8 C7 123.5(2) . . ?
C12 C8 C9 121.7(3) . . ?
C7 C8 C9 114.7(3) . . ?
C10 C9 C8 112.2(2) . . ?
C10 C9 H9A 109.2 . . ?
C8 C9 H9A 109.2 . . ?
C10 C9 H9B 109.2 . . ?
C8 C9 H9B 109.2 . . ?
H9A C9 H9B 107.9 . . ?
C9 C10 C11 113.7(3) . . ?
C9 C10 H10A 108.8 . . ?
C11 C10 H10A 108.8 . . ?
C9 C10 H10B 108.8 . . ?
C11 C10 H10B 108.8 . . ?
H10A C10 H10B 107.7 . . ?
C10 C11 Cl2 113.7(2) . . ?
C10 C11 H11A 108.8 . . ?
Cl2 C11 H11A 108.8 . . ?
C10 C11 H11B 108.8 . . ?
Cl2 C11 H11B 108.8 . . ?
H11A C11 H11B 107.7 . . ?
C8 C12 O1 120.9(3) . . ?
C8 C12 C13 129.2(3) . . ?
O1 C12 C13 109.8(3) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 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
P1 O3 1.453(2) . ?
P1 O1 1.575(2) . ?
P1 N1 1.656(2) . ?
P1 Cl1 1.9949(13) . ?
Cl2 C11 1.763(3) . ?
N1 C7 1.420(3) . ?
N1 C6 1.456(3) . ?
O1 C12 1.410(3) . ?
O2 C7 1.207(4) . ?
C1 C6 1.377(4) . ?
C1 C2 1.399(4) . ?
C1 H1A 0.9300 . ?
C2 C3 1.372(5) . ?
C2 H2A 0.9300 . ?
C3 C4 1.377(5) . ?
C3 H3A 0.9300 . ?
C4 C5 1.372(4) . ?
C4 H4A 0.9300 . ?
C5 C6 1.375(4) . ?
C5 H5A 0.9300 . ?
C7 C8 1.474(4) . ?
C8 C12 1.330(4) . ?
C8 C9 1.524(4) . ?
C9 C10 1.502(4) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.514(4) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.478(4) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139180694
