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#$Date: 2019-11-23 21:18:52 +0200 (Sat, 23 Nov 2019) $
#$Revision: 235051 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/66/4036660.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_4036660
loop_
_publ_author_name
'Dziuganowska, Zofia A.'
'Ślepokura, Katarzyna'
'Volle, Jean-Noël'
'Virieux, David'
'Pirat, Jean-Luc'
'Kafarski, Paweł'
_publ_section_title
;
 Structural Analogues of Selfotel.
;
_journal_issue                   12
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              4947
_journal_page_last               4954
_journal_paper_doi               10.1021/acs.joc.6b00220
_journal_volume                  81
_journal_year                    2016
_chemical_formula_moiety         'C6 H6 N O5 P'
_chemical_formula_sum            'C6 H6 N O5 P'
_chemical_formula_weight         203.09
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                68.53(3)
_cell_angle_beta                 63.42(3)
_cell_angle_gamma                88.31(3)
_cell_formula_units_Z            2
_cell_length_a                   7.462(2)
_cell_length_b                   7.805(2)
_cell_length_c                   8.031(2)
_cell_measurement_reflns_used    8190
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.80
_cell_measurement_theta_min      2.84
_cell_volume                     384.2(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXs-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.937
_diffrn_measurement_device_type
;
Xcalibur R kappa-geometry diffractometer with a Ruby 
CCD camera 
;
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0162
_diffrn_reflns_av_unetI/netI     0.0115
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.937
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            9957
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.937
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         28.863
_diffrn_reflns_theta_min         2.842
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.346
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.979
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.756
_exptl_crystal_description       block
_exptl_crystal_F_000             208
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.392
_refine_diff_density_min         -0.416
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     120
_refine_ls_number_reflns         1887
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.087
_refine_ls_R_factor_all          0.0274
_refine_ls_R_factor_gt           0.0264
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0353P)²+0.2780P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0718
_refine_ls_wR_factor_ref         0.0727
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1808
_reflns_number_total             1887
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo6b00220_si_003.cif
_cod_data_source_block           09_zd097
_cod_database_code               4036660
_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   0.846
_shelx_estimated_absorpt_t_max   0.909
_shelxl_version_number           2013-4
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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
P1 P 0.01326(4) 0.21674(4) 0.61298(4) 0.00747(10) Uani 1 1 d . .
O1 O -0.08570(14) 0.01913(12) 0.74917(13) 0.01147(19) Uani 1 1 d . .
O2 O -0.05579(13) 0.31379(12) 0.45605(13) 0.00989(18) Uani 1 1 d . .
O3 O -0.00995(14) 0.33312(12) 0.74285(13) 0.01045(18) Uani 1 1 d . .
H3 H 0.0088 0.4473 0.6709 0.016 Uiso 1 1 calc R U
O4 O 0.46230(16) 0.30667(15) 0.78243(14) 0.0188(2) Uani 1 1 d . .
O5 O 0.22122(14) 0.07080(13) 0.88245(13) 0.01251(19) Uani 1 1 d . .
H5 H 0.1912 0.0602 1.0002 0.019 Uiso 1 1 calc R U
N1 N 0.62451(16) 0.25896(15) 0.41323(16) 0.0095(2) Uani 1 1 d . .
H1N H 0.7092 0.2624 0.4611 0.011 Uiso 1 1 calc R U
C2 C 0.42363(18) 0.23305(16) 0.53762(18) 0.0085(2) Uani 1 1 d . .
C3 C 0.28628(18) 0.23278(16) 0.46468(18) 0.0081(2) Uani 1 1 d . .
C4 C 0.36495(19) 0.25963(17) 0.26109(18) 0.0100(2) Uani 1 1 d . .
H4A H 0.2749 0.2636 0.2060 0.012 Uiso 1 1 calc R U
C5 C 0.57229(19) 0.28048(18) 0.13856(19) 0.0118(2) Uani 1 1 d . .
H5A H 0.6246 0.2950 0.0016 0.014 Uiso 1 1 calc R U
C6 C 0.70082(19) 0.27966(18) 0.21948(19) 0.0115(2) Uani 1 1 d . .
H6A H 0.8434 0.2937 0.1382 0.014 Uiso 1 1 calc R U
C7 C 0.36877(19) 0.20752(17) 0.75229(18) 0.0097(2) 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'
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
O1 P1 O2 115.73(6)
O1 P1 O3 109.92(6)
O2 P1 O3 110.40(5)
O1 P1 C3 111.17(7)
O2 P1 C3 104.13(6)
O3 P1 C3 104.84(6)
P1 O3 H3 109.5
C7 O5 H5 109.5
C6 N1 C2 122.78(11)
C6 N1 H1N 118.6
C2 N1 H1N 118.6
N1 C2 C3 119.95(11)
N1 C2 C7 114.50(11)
C3 C2 C7 125.55(11)
C2 C3 C4 117.61(11)
C2 C3 P1 123.79(9)
C4 C3 P1 118.45(9)
C5 C4 C3 121.02(12)
C5 C4 H4A 119.5
C3 C4 H4A 119.5
C6 C5 C4 118.66(12)
C6 C5 H5A 120.7
C4 C5 H5A 120.7
N1 C6 C5 119.93(12)
N1 C6 H6A 120.0
C5 C6 H6A 120.0
O4 C7 O5 128.83(12)
O4 C7 C2 120.38(12)
O5 C7 C2 110.77(11)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
P1 O1 1.4933(12)
P1 O2 1.5122(10)
P1 O3 1.5701(10)
P1 C3 1.8219(14)
O3 H3 0.8400
O4 C7 1.2102(16)
O5 C7 1.2909(17)
O5 H5 0.8400
N1 C6 1.3416(16)
N1 C2 1.3475(17)
N1 H1N 0.8800
C2 C3 1.3900(17)
C2 C7 1.5170(17)
C3 C4 1.3997(17)
C4 C5 1.3869(18)
C4 H4A 0.9500
C5 C6 1.3772(18)
C5 H5A 0.9500
C6 H6A 0.9500
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
_geom_hbond_site_symmetry_A
O3 H3 O2 0.84 1.72 2.5579(17) 172.8 2_566
O5 H5 O1 0.84 1.66 2.4723(16) 162.2 2_557
N1 H1N O2 0.88 1.79 2.6258(15) 157.9 1_655
C4 H4A O1 0.95 2.48 3.1041(18) 123.4 2_556
C5 H5A O3 0.95 2.52 3.200(2) 128.3 1_654
C5 H5A O4 0.95 2.52 3.2494(18) 133.5 1_554
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
C6 N1 C2 C3 -2.03(18)
C6 N1 C2 C7 178.44(11)
N1 C2 C3 C4 0.13(17)
C7 C2 C3 C4 179.61(11)
N1 C2 C3 P1 -175.19(9)
C7 C2 C3 P1 4.29(18)
O1 P1 C3 C2 -81.82(12)
O2 P1 C3 C2 152.90(10)
O3 P1 C3 C2 36.90(12)
O1 P1 C3 C4 102.89(10)
O2 P1 C3 C4 -22.39(11)
O3 P1 C3 C4 -138.39(10)
C2 C3 C4 C5 1.77(18)
P1 C3 C4 C5 177.35(10)
C3 C4 C5 C6 -1.85(19)
C2 N1 C6 C5 1.96(19)
C4 C5 C6 N1 0.00(19)
N1 C2 C7 O4 43.62(17)
C3 C2 C7 O4 -135.88(14)
N1 C2 C7 O5 -135.05(11)
C3 C2 C7 O5 45.44(16)
