#------------------------------------------------------------------------------
#$Date: 2025-08-22 18:52:37 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301865 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/22/63/7226391.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_7226391
loop_
_publ_author_name
'Kapdi, Anant'
'Bhilare, Shatrughn'
'Gayakhe, Vijay'
'Ardhapure, Ajay'
'Sanghvi, Yogesh S.'
'Schulzke, Carola'
'Borozdina, Yulia B.'
_publ_section_title
;
 Novel Water-Soluble Phosphatriazenes: Versatile Ligands for
 Suzuki-Miyaura, Sonogashira and Heck Reactions of Nucleosides
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C6RA19039A
_journal_year                    2016
_chemical_formula_sum            'C9 H24 N3 O6 P S'
_chemical_formula_weight         333.34
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2016-06-30 deposited with the CCDC.
2016-08-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.65(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.321(2)
_cell_length_b                   6.3748(13)
_cell_length_c                   22.799(5)
_cell_measurement_reflns_used    16409
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      58.5
_cell_measurement_theta_min      6.2
_cell_volume                     1483.0(5)
_computing_cell_refinement       'X-Area by STOE & Cie GmbH 2010'
_computing_data_collection       'X-Area by STOE & Cie GmbH 2010'
_computing_data_reduction        'X-Area by STOE & Cie GmbH 2010'
_computing_molecular_graphics    'XP Version 5.1 by Bruker AXS 1998'
_computing_publication_material  'CIFTAB (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SIR-92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      170(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'STOE IPDS2T'
_diffrn_measurement_method       ω
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0423
_diffrn_reflns_av_unetI/netI     0.0260
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            15778
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.253
_diffrn_reflns_theta_min         3.321
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.355
_exptl_absorpt_correction_T_max  0.9261
_exptl_absorpt_correction_T_min  0.7377
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'face indexed'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.493
_exptl_crystal_description       platelet
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.434
_exptl_crystal_size_mid          0.301
_exptl_crystal_size_min          0.198
_refine_diff_density_max         0.335
_refine_diff_density_min         -0.636
_refine_diff_density_rms         0.076
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.113
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     205
_refine_ls_number_reflns         4007
_refine_ls_number_restraints     18
_refine_ls_restrained_S_all      1.111
_refine_ls_R_factor_all          0.0423
_refine_ls_R_factor_gt           0.0345
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0523P)²+0.7396P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0901
_refine_ls_wR_factor_ref         0.1050
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3393
_reflns_number_total             4007
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c6ra19039a2.cif
_cod_data_source_block           shelx
_cod_original_cell_volume        1482.9(5)
_cod_database_code               7226391
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.861
_shelx_estimated_absorpt_t_max   0.933
_shelxl_version_number           2013-3
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
C1 C 0.82171(16) -0.0093(3) 0.76799(6) 0.0237(3) Uani 1 1 d . .
H1A H 0.8492 -0.1579 0.7671 0.028 Uiso 1 1 calc R U
H1B H 0.7265 -0.0065 0.7698 0.028 Uiso 1 1 calc R U
C2 C 0.84769(16) 0.0989(3) 0.71135(6) 0.0236(3) Uani 1 1 d . .
H2A H 0.8322 0.2516 0.7139 0.028 Uiso 1 1 calc R U
H2B H 0.9398 0.0765 0.7055 0.028 Uiso 1 1 calc R U
C3 C 0.75533(14) 0.0055(2) 0.65993(6) 0.0195(3) Uani 1 1 d . .
H3A H 0.7766 -0.1451 0.6566 0.023 Uiso 1 1 calc R U
H3B H 0.6647 0.0148 0.6690 0.023 Uiso 1 1 calc R U
C4 C 0.70988(14) 0.3351(2) 0.60111(6) 0.0182(3) Uani 1 1 d . .
H4A H 0.6253 0.3373 0.6166 0.022 Uiso 1 1 calc R U
H4B H 0.7733 0.4205 0.6280 0.022 Uiso 1 1 calc R U
C5 C 0.89589(14) 0.1029(2) 0.58469(6) 0.0183(3) Uani 1 1 d . .
H5A H 0.9263 -0.0445 0.5856 0.022 Uiso 1 1 calc R U
H5B H 0.9556 0.1814 0.6150 0.022 Uiso 1 1 calc R U
C6 C 0.66445(14) -0.0129(2) 0.55481(6) 0.0175(3) Uani 1 1 d . .
H6A H 0.6976 -0.1576 0.5516 0.021 Uiso 1 1 calc R U
H6B H 0.5781 -0.0220 0.5686 0.021 Uiso 1 1 calc R U
C7 C 0.81840(15) 0.4602(2) 0.52168(6) 0.0203(3) Uani 1 1 d . .
H7A H 0.8746 0.5502 0.5504 0.024 Uiso 1 1 calc R U
H7B H 0.8018 0.5366 0.4835 0.024 Uiso 1 1 calc R U
C8 C 0.60224(14) 0.2986(2) 0.50219(7) 0.0202(3) Uani 1 1 d . .
H8A H 0.5155 0.2964 0.5157 0.024 Uiso 1 1 calc R U
H8B H 0.5911 0.3643 0.4624 0.024 Uiso 1 1 calc R U
C9 C 0.76709(14) 0.0721(2) 0.46940(6) 0.0200(3) Uani 1 1 d . .
H9A H 0.7475 0.1313 0.4289 0.024 Uiso 1 1 calc R U
H9B H 0.7916 -0.0769 0.4657 0.024 Uiso 1 1 calc R U
N1 N 0.75979(12) 0.10836(19) 0.60104(5) 0.0161(2) Uani 1 1 d . .
N2 N 0.69240(12) 0.4265(2) 0.54333(5) 0.0184(2) Uani 1 1 d . .
N3 N 0.64804(12) 0.0828(2) 0.49759(5) 0.0181(2) Uani 1 1 d . .
O1 O 0.87119(13) -0.0062(2) 0.88229(5) 0.0325(3) Uani 1 1 d . .
O2 O 1.04511(11) 0.0990(2) 0.82900(5) 0.0286(3) Uani 1 1 d . .
O3 O 0.86150(13) 0.3293(2) 0.83152(6) 0.0317(3) Uani 1 1 d . .
O5 O 0.38388(14) 0.3425(2) 0.62316(6) 0.0347(3) Uani 1 1 d D .
O4 O 0.53915(15) 0.6361(3) 0.69029(8) 0.0432(3) Uani 1 1 d D .
O6 O 0.38602(15) -0.0091(2) 0.69541(7) 0.0409(3) Uani 1 1 d D .
P1 P 0.90836(4) 0.21476(6) 0.51083(2) 0.01878(11) Uani 1 1 d . .
S1 S 0.90698(4) 0.11321(6) 0.83264(2) 0.02096(11) Uani 1 1 d . .
H5O H 0.3018(19) 0.385(4) 0.6206(12) 0.056(8) Uiso 1 1 d D .
H5P H 0.389(3) 0.226(4) 0.6440(14) 0.079(10) Uiso 1 1 d D .
H4O H 0.489(3) 0.546(4) 0.6691(13) 0.083(11) Uiso 1 1 d D .
H6O H 0.306(2) -0.060(5) 0.6902(14) 0.083(11) Uiso 1 1 d D .
H4P H 0.494(3) 0.752(4) 0.6912(15) 0.077(10) Uiso 1 1 d D .
H6P H 0.402(4) 0.031(8) 0.7328(11) 0.15(2) Uiso 1 1 d 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'
S S 0.1246 0.1234 '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
C2 C1 S1 112.05(11)
C3 C2 C1 107.91(12)
N1 C3 C2 114.81(12)
N2 C4 N1 112.31(11)
N1 C5 P1 114.28(10)
N3 C6 N1 112.80(11)
N2 C7 P1 113.97(10)
N3 C8 N2 112.84(12)
N3 C9 P1 113.56(10)
C3 N1 C5 111.49(11)
C3 N1 C4 110.80(11)
C5 N1 C4 110.33(11)
C3 N1 C6 106.92(11)
C5 N1 C6 110.06(11)
C4 N1 C6 107.09(10)
C4 N2 C8 110.09(12)
C4 N2 C7 111.91(12)
C8 N2 C7 111.95(12)
C6 N3 C8 109.36(11)
C6 N3 C9 112.80(12)
C8 N3 C9 111.99(12)
C5 P1 C9 96.76(7)
C5 P1 C7 95.68(7)
C9 P1 C7 96.35(7)
O2 S1 O3 112.18(8)
O2 S1 O1 112.32(8)
O3 S1 O1 112.93(8)
O2 S1 C1 107.13(8)
O3 S1 C1 106.44(8)
O1 S1 C1 105.22(8)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.523(2)
C1 S1 1.7796(16)
C2 C3 1.517(2)
C3 N1 1.5010(17)
C4 N2 1.4270(18)
C4 N1 1.5346(19)
C5 N1 1.5068(18)
C5 P1 1.8509(15)
C6 N3 1.4269(18)
C6 N1 1.5378(18)
C7 N2 1.4743(19)
C7 P1 1.8549(16)
C8 N3 1.4637(19)
C8 N2 1.4657(19)
C9 N3 1.4713(19)
C9 P1 1.8521(16)
O1 S1 1.4571(12)
O2 S1 1.4433(12)
O3 S1 1.4545(14)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139202681
