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#$Date: 2025-08-21 01:40:30 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301839 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/33/96/4339640.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_4339640
loop_
_publ_author_name
'Chakravarty, Manab'
'Suresh, R. Rama'
'Swamy, K. C. Kumara'
_publ_section_title
;
 Molecularly nonstoichiometric crystals in phosphorus compounds.
;
_journal_issue                   23
_journal_name_full               'Inorganic chemistry'
_journal_page_first              9819
_journal_page_last               9826
_journal_paper_doi               10.1021/ic701173x
_journal_volume                  46
_journal_year                    2007
_chemical_formula_sum            'C25 H36 N O3 P'
_chemical_formula_weight         429.52
_space_group_IT_number           62
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2n'
_symmetry_space_group_name_H-M   'P n m a'
_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            4
_cell_length_a                   13.443(3)
_cell_length_b                   23.013(3)
_cell_length_c                   7.885(2)
_cell_measurement_reflns_used    2211
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25
_cell_measurement_theta_min      1.8
_cell_volume                     2439.3(9)
_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      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0555
_diffrn_reflns_av_sigmaI/netI    0.0281
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            13336
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.77
_exptl_absorpt_coefficient_mu    0.137
_exptl_absorpt_correction_T_max  0.9837
_exptl_absorpt_correction_T_min  0.9717
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   'SADABS, Sheldrick(96)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.170
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.450
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     157
_refine_ls_number_reflns         2206
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0754
_refine_ls_R_factor_gt           0.0639
_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)+(0.1203P)²+0.3295P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1735
_refine_ls_wR_factor_ref         0.1843
_reflns_number_gt                1764
_reflns_number_total             2206
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic701173x.cif
_cod_data_source_block           compd13
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      Pnma
_cod_database_code               4339640
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, 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
P P 0.17228(6) 0.2500 0.29371(10) 0.0448(3) Uani 1 2 d S . .
O1 O 0.16999(11) 0.19477(7) 0.4137(2) 0.0542(5) Uani 1 1 d . . .
O2 O 0.25286(16) 0.2500 0.1733(3) 0.0517(6) Uani 1 2 d S . .
N N 0.0628(2) 0.2500 0.2155(4) 0.0738(10) Uani 1 2 d S . .
C1 C 0.25271(17) 0.16934(10) 0.4924(3) 0.0505(6) Uani 1 1 d . . .
C2 C 0.2872(2) 0.19569(10) 0.6376(3) 0.0545(6) Uani 1 1 d . . .
C3 C 0.3674(2) 0.17154(12) 0.7200(3) 0.0681(8) Uani 1 1 d . . .
H3 H 0.3915 0.1889 0.8183 0.082 Uiso 1 1 calc R . .
C4 C 0.4121(2) 0.12236(12) 0.6595(4) 0.0766(8) Uani 1 1 d . . .
C5 C 0.3731(2) 0.09649(12) 0.5177(4) 0.0716(8) Uani 1 1 d . . .
H5 H 0.4035 0.0629 0.4776 0.086 Uiso 1 1 calc R . .
C6 C 0.2915(2) 0.11734(10) 0.4310(3) 0.0571(7) Uani 1 1 d . . .
C7 C 0.2395(3) 0.2500 0.7078(4) 0.0581(9) Uani 1 2 d S . .
H7A H 0.1693 0.2500 0.6797 0.070 Uiso 1 2 calc SR . .
H7B H 0.2455 0.2500 0.8303 0.070 Uiso 1 2 calc SR . .
C8 C 0.5015(3) 0.09724(19) 0.7479(6) 0.1189(14) Uani 1 1 d . . .
H8A H 0.5610 0.1118 0.6957 0.178 Uiso 1 1 calc R . .
H8B H 0.5001 0.0556 0.7390 0.178 Uiso 1 1 calc R . .
H8C H 0.5005 0.1083 0.8653 0.178 Uiso 1 1 calc R . .
C9 C 0.2483(2) 0.08362(11) 0.2797(3) 0.0662(8) Uani 1 1 d . . .
C10 C 0.2925(4) 0.02237(15) 0.2700(5) 0.1154(15) Uani 1 1 d . . .
H10A H 0.2844 0.0033 0.3773 0.173 Uiso 1 1 calc R . .
H10B H 0.3621 0.0249 0.2431 0.173 Uiso 1 1 calc R . .
H10C H 0.2589 0.0006 0.1835 0.173 Uiso 1 1 calc R . .
C11 C 0.2742(4) 0.11272(14) 0.1141(4) 0.1093(14) Uani 1 1 d . . .
H11A H 0.2485 0.0901 0.0217 0.164 Uiso 1 1 calc R . .
H11B H 0.3452 0.1157 0.1040 0.164 Uiso 1 1 calc R . .
H11C H 0.2455 0.1509 0.1113 0.164 Uiso 1 1 calc R . .
C12 C 0.1374(3) 0.07557(19) 0.2981(6) 0.1277(17) Uani 1 1 d . . .
H12A H 0.1050 0.1127 0.2909 0.192 Uiso 1 1 calc R . .
H12B H 0.1232 0.0581 0.4060 0.192 Uiso 1 1 calc R . .
H12C H 0.1135 0.0508 0.2090 0.192 Uiso 1 1 calc R . .
C13 C 0.0407(5) 0.2697(4) 0.0545(9) 0.115(4) Uani 0.50 1 d P A -1
H13A H 0.1011 0.2800 -0.0030 0.173 Uiso 0.50 1 calc PR A -1
H13B H -0.0018 0.3031 0.0621 0.173 Uiso 0.50 1 calc PR A -1
H13C H 0.0074 0.2395 -0.0077 0.173 Uiso 0.50 1 calc PR A -1
C14 C -0.0237(5) 0.2337(9) 0.3230(11) 0.142(9) Uani 0.50 1 d P A -1
H14A H -0.0465 0.1957 0.2915 0.213 Uiso 0.50 1 calc PR A -1
H14B H -0.0763 0.2613 0.3067 0.213 Uiso 0.50 1 calc PR A -1
H14C H -0.0040 0.2336 0.4400 0.213 Uiso 0.50 1 calc PR A -1
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'
P P 0.1023 0.0942 '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'
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
O2 P O1 114.08(7) . .
O2 P O1 114.08(7) . 7_565
O1 P O1 106.67(13) . 7_565
O2 P N 116.04(16) . .
O1 P N 102.28(9) . .
O1 P N 102.28(9) 7_565 .
C1 O1 P 125.73(14) . .
C13 N C13 38.3(7) . 7_565
C13 N C14 105.9(6) . 7_565
C13 N C14 116.0(5) 7_565 7_565
C13 N C14 116.0(5) . .
C13 N C14 105.9(6) 7_565 .
C14 N C14 29.2(15) 7_565 .
C13 N P 123.6(4) . .
C13 N P 123.6(4) 7_565 .
C14 N P 120.1(4) 7_565 .
C14 N P 120.1(4) . .
C2 C1 C6 122.8(2) . .
C2 C1 O1 116.9(2) . .
C6 C1 O1 120.1(2) . .
C3 C2 C1 118.6(2) . .
C3 C2 C7 119.6(3) . .
C1 C2 C7 121.8(3) . .
C4 C3 C2 120.9(3) . .
C4 C3 H3 119.6 . .
C2 C3 H3 119.6 . .
C3 C4 C5 118.5(3) . .
C3 C4 C8 120.5(3) . .
C5 C4 C8 121.1(3) . .
C4 C5 C6 123.9(3) . .
C4 C5 H5 118.1 . .
C6 C5 H5 118.1 . .
C5 C6 C1 115.1(2) . .
C5 C6 C9 120.6(2) . .
C1 C6 C9 124.3(2) . .
C2 C7 C2 111.8(3) 7_565 .
C2 C7 H7A 109.3 7_565 .
C2 C7 H7A 109.3 . .
C2 C7 H7B 109.3 7_565 .
C2 C7 H7B 109.3 . .
H7A C7 H7B 107.9 . .
C4 C8 H8A 109.5 . .
C4 C8 H8B 109.5 . .
H8A C8 H8B 109.5 . .
C4 C8 H8C 109.5 . .
H8A C8 H8C 109.5 . .
H8B C8 H8C 109.5 . .
C11 C9 C12 111.5(3) . .
C11 C9 C10 106.0(3) . .
C12 C9 C10 106.0(3) . .
C11 C9 C6 111.1(2) . .
C12 C9 C6 111.1(3) . .
C10 C9 C6 110.9(3) . .
C9 C10 H10A 109.5 . .
C9 C10 H10B 109.5 . .
H10A C10 H10B 109.5 . .
C9 C10 H10C 109.5 . .
H10A C10 H10C 109.5 . .
H10B C10 H10C 109.5 . .
C9 C11 H11A 109.5 . .
C9 C11 H11B 109.5 . .
H11A C11 H11B 109.5 . .
C9 C11 H11C 109.5 . .
H11A C11 H11C 109.5 . .
H11B C11 H11C 109.5 . .
C9 C12 H12A 109.5 . .
C9 C12 H12B 109.5 . .
H12A C12 H12B 109.5 . .
C9 C12 H12C 109.5 . .
H12A C12 H12C 109.5 . .
H12B C12 H12C 109.5 . .
N C13 H13A 109.5 . .
N C13 H13B 109.5 . .
N C13 H13C 109.5 . .
N C14 H14A 109.5 . .
N C14 H14B 109.5 . .
N C14 H14C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
P O2 1.440(2) .
P O1 1.5847(16) .
P O1 1.5847(16) 7_565
P N 1.596(3) .
O1 C1 1.402(3) .
N C13 1.380(7) .
N C13 1.380(7) 7_565
N C14 1.486(9) 7_565
N C14 1.486(9) .
C1 C2 1.376(3) .
C1 C6 1.392(3) .
C2 C3 1.376(3) .
C2 C7 1.510(3) .
C3 C4 1.367(4) .
C3 H3 0.9300 .
C4 C5 1.371(4) .
C4 C8 1.505(4) .
C5 C6 1.379(4) .
C5 H5 0.9300 .
C6 C9 1.537(4) .
C7 C2 1.509(3) 7_565
C7 H7A 0.9700 .
C7 H7B 0.9700 .
C8 H8A 0.9600 .
C8 H8B 0.9600 .
C8 H8C 0.9600 .
C9 C11 1.508(4) .
C9 C12 1.509(5) .
C9 C10 1.532(4) .
C10 H10A 0.9600 .
C10 H10B 0.9600 .
C10 H10C 0.9600 .
C11 H11A 0.9600 .
C11 H11B 0.9600 .
C11 H11C 0.9600 .
C12 H12A 0.9600 .
C12 H12B 0.9600 .
C12 H12C 0.9600 .
C13 H13A 0.9600 .
C13 H13B 0.9600 .
C13 H13C 0.9600 .
C14 H14A 0.9600 .
C14 H14B 0.9600 .
C14 H14C 0.9600 .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 101450377
