#------------------------------------------------------------------------------
#$Date: 2025-08-19 13:01:59 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301802 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/10/56/2105688.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2105688
loop_
_publ_author_name
'Małecka, Magdalena'
'Mondal, Swastik'
'van Smaalen, Sander'
'Paulmann, Carsten'
_publ_section_title
;
 Charge density distribution of
 3-(1-aminoethylidene)-2-methoxy-2-oxo-2,3-dihydro-2λ⁵-benzo[e][1,2]oxaphosphinin-4-one
;
_journal_coeditor_code           GW5021
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section B'
_journal_page_first              621
_journal_page_last               628
_journal_paper_doi               10.1107/S2052519213027267
_journal_volume                  69
_journal_year                    2013
_chemical_formula_moiety         'C11 H12 N O4 P'
_chemical_formula_sum            'C11 H12 N O4 P'
_chemical_formula_weight         253.19
_chemical_name_systematic
; 
3-(1-amino-ethylidene)-2-methoxy-2-oxo-2,3-dihydro-2λ⁵-benzo[e][1,2]
oxaphosphinin-4-one
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_audit_creation_method           SHELXL-97
_audit_update_record
;
2013-10-14 # Formatted by IUCr publCIF

;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.2532(10)
_cell_length_b                   10.1555(16)
_cell_length_c                   12.6610(12)
_cell_measurement_temperature    100(2)
_cell_volume                     1189.8(3)
_computing_cell_refinement       'EVAL 15 (Schreurs, 2010)'
_computing_data_collection       'MarCCD (Paulmann & Morgenroth, 2006)'
_computing_data_reduction        'EVAL 15 (Schreurs, 2010)'
_computing_molecular_graphics    'Volkov et al, (2006)'
_computing_publication_material  'Volkov et al, (2006)'
_computing_structure_refinement  'Volkov et al, (2006)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_type            'MarCCD detector'
_diffrn_measured_fraction_theta_full 0.942
_diffrn_measured_fraction_theta_max 0.942
_diffrn_measurement_device_type  'Huber diffractometer'
_diffrn_measurement_method       'φ scan'
_diffrn_radiation_source         synchrotron
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.60000
_diffrn_reflns_av_R_equivalents  0.0350
_diffrn_reflns_av_sigmaI/netI    0.0184
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            98994
_diffrn_reflns_theta_full        48.57
_diffrn_reflns_theta_max         48.57
_diffrn_reflns_theta_min         2.17
_exptl_absorpt_coefficient_mu    0.233
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.413
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.134
_refine_diff_density_min         -0.298
_refine_diff_density_rms         0.028
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.372
_refine_ls_matrix_type           full
_refine_ls_number_parameters     534
_refine_ls_number_reflns         14864
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.018
_refine_ls_R_factor_gt           0.015
_refine_ls_R_Fsqd_factor         0.023
_refine_ls_shift/su_max          0
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details
;
calc w1 = 1/[s²(Fo)]
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.017
_reflns_number_gt                16534
_reflns_number_total             17584
_reflns_threshold_expression     >2sigma(I)
_publcif_datablock.id            {718aa8e3-ed5f-43f6-b69b-30521a7c4ae0}
_publcif_info_exptl_table_max_cols 4
_publcif_info_exptl_table_use_headnotes n
_cod_data_source_file            gw5021.cif
_cod_data_source_block           I
_cod_database_code               2105688
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
loop_
_atom_local_axes_atom_label
_atom_local_axes_atom0
_atom_local_axes_ax1
_atom_local_axes_atom1
_atom_local_axes_atom2
_atom_local_axes_ax2
P(2) O(21) Z P(2) O(22) Y
O(1) P(2) Z O(1) O(22) Y
O(4) C(4) Z O(4) H(1) Y
O(21) P(2) Z O(21) O(1) Y
O(22) C(23) Z O(22) P(2) Y
N(1) H(1) -Z N(1) H(2) Y
C(3) C(31) Z C(3) C(4) Y
C(4) O(4) Z C(4) C(10) Y
C(5) C(10) Y C(5) C(6) X
C(6) C(5) Y C(6) C(7) X
C(7) C(6) Y C(7) C(8) X
C(8) C(7) Y C(8) C(9) X
C(9) C(8) Y C(9) C(10) X
C(10) C(9) Y C(10) C(5) X
C(23) O(22) Z C(23) O(1) Y
C(31) C(311) -Z C(31) C(3) Y
C(311) C(31) Z C(311) C(3) Y
H(1) N(1) -Z H(1) O(4) Y
H(2) N(1) Z H(2) C(31) Y
H(5) C(5) Z H(5) C(10) Y
H(6) C(6) Z H(6) C(5) Y
H(7) C(7) Z H(7) C(6) Y
H(8) C(8) Z H(8) C(7) Y
H(23A) C(23) Z H(23A) H(23B) Y
H(23B) C(23) Z H(23B) H(23C) Y
H(23C) C(23) Z H(23C) H(23A) Y
H(31A) C(311) Z H(31A) H(31B) Y
H(31B) C(311) Z H(31B) H(31C) Y
H(31C) C(311) Z H(31C) H(31A) Y
loop_
_atom_rho_multipole_atom_label
_atom_rho_multipole_coeff_Pv
_atom_rho_multipole_coeff_P00
_atom_rho_multipole_coeff_P11
_atom_rho_multipole_coeff_P1-1
_atom_rho_multipole_coeff_P10
_atom_rho_multipole_coeff_P20
_atom_rho_multipole_coeff_P21
_atom_rho_multipole_coeff_P2-1
_atom_rho_multipole_coeff_P22
_atom_rho_multipole_coeff_P2-2
_atom_rho_multipole_coeff_P30
_atom_rho_multipole_coeff_P31
_atom_rho_multipole_coeff_P3-1
_atom_rho_multipole_coeff_P32
_atom_rho_multipole_coeff_P3-2
_atom_rho_multipole_coeff_P33
_atom_rho_multipole_coeff_P3-3
_atom_rho_multipole_coeff_P40
_atom_rho_multipole_coeff_P41
_atom_rho_multipole_coeff_P4-1
_atom_rho_multipole_coeff_P42
_atom_rho_multipole_coeff_P4-2
_atom_rho_multipole_coeff_P43
_atom_rho_multipole_coeff_P4-3
_atom_rho_multipole_coeff_P44
_atom_rho_multipole_coeff_P4-4
_atom_rho_multipole_kappa
_atom_rho_multipole_kappa_prime0
_atom_rho_multipole_kappa_prime1
_atom_rho_multipole_kappa_prime2
_atom_rho_multipole_kappa_prime3
_atom_rho_multipole_kappa_prime4
_atom_rho_multipole_radial_slater_n0
_atom_rho_multipole_radial_slater_zeta0
_atom_rho_multipole_radial_slater_n1
_atom_rho_multipole_radial_slater_zeta1
_atom_rho_multipole_radial_slater_n2
_atom_rho_multipole_radial_slater_zeta2
_atom_rho_multipole_radial_slater_n3
_atom_rho_multipole_radial_slater_zeta3
_atom_rho_multipole_radial_slater_n4
_atom_rho_multipole_radial_slater_zeta4
P(2) 4.57(4) 0 -0.042(11) -0.001(12) 0.081(13) 0.083(12) 0.018(10) -0.035(11)
-0.042(10) 0.102(10) 0.387(14) -0.041(9) -0.043(14) -0.011(10) -0.086(11)
0.081(13) -0.299(9) 0.015(10) -0.001(9) 0.014(9) 0.016(9) 0.002(9) 0.003(9)
0.140(9) 0.033(9) 0.006(8) 0.9917 1 1 1 1 1 4 3.45904 4 3.45904 4 3.45904 4
3.45904 4 3.45904
O(1) 6.202(12) 0 0.074(6) -0.015(7) 0.051(6) -0.006(6) -0.063(6) 0.037(7)
-0.038(6) 0.048(7) 0.029(6) -0.013(5) 0.007(7) -0.029(5) 0.035(6) 0.003(6)
-0.001(6) -0.023(7) 0.009(7) -0.020(8) -0.005(7) 0.010(7) -0.006(7) -0.005(7)
-0.017(7) 0.020(7) 0.996287 1 1 1 1 1 2 4.466 2 4.466 2 4.466 3 4.466 4 4.466
O(4) 6.113(14) 0 0.051(8) 0.008(7) -0.040(7) -0.020(8) 0.012(7) -0.030(7)
-0.065(7) -0.010(7) 0.027(7) 0.008(7) -0.003(6) 0.058(6) -0.013(6) 0.060(6)
0.026(7) 0.031(9) 0.008(8) -0.019(7) 0.007(8) 0.015(8) 0.008(8) 0.014(8)
-0.002(8) -0.011(7) 0.998624 1 1 1 1 1 2 4.466 2 4.466 2 4.466 3 4.466 4 4.466
O(21) 6.200(12) 0 -0.023(7) -0.047(7) -0.007(7) -0.018(7) 0.026(6) -0.022(6)
0.006(7) 0.008(7) -0.033(7) 0.023(6) -0.006(6) -0.009(6) -0.010(6) 0.018(6)
0.008(6) -0.025(8) 0.001(7) 0.033(7) -0.008(7) -0.002(7) 0.009(7) -0.012(7)
-0.012(7) 0.007(8) 0.996029 1 1 1 1 1 2 4.466 2 4.466 2 4.466 3 4.466 4 4.466
O(22) 6.164(12) 0 0.023(7) -0.050(6) -0.057(6) -0.050(6) -0.009(7) -0.008(6)
-0.023(6) 0.002(7) 0.071(6) -0.026(6) -0.032(5) -0.003(6) -0.033(6) -0.005(6)
-0.007(5) -0.002(8) -0.005(7) -0.014(7) 0.010(7) -0.013(7) 0.018(7) -0.002(7)
0.012(7) 0.021(7) 0.998757 1 1 1 1 1 2 4.466 2 4.466 2 4.466 3 4.466 4 4.466
N(1) 5.08(2) 0 0.029(8) 0.030(8) 0.020(9) 0.009(8) 0.016(8) -0.009(7) -0.041(8)
-0.004(7) 0.179(8) 0.020(7) 0.030(7) 0.092(9) -0.015(8) -0.002(7) -0.046(7)
0.033(10) 0.019(9) 0.007(9) -0.002(9) 0.011(9) 0.016(9) -0.013(10) 0.025(8)
-0.004(8) 0.999064 1 1 1 1 1 2 3.83936 2 3.83936 2 3.83936 3 3.83936 4 3.83936
C(3) 4.15(3) 0 0.029(9) 0.028(10) -0.007(10) 0.041(9) 0.020(8) 0.049(8)
-0.043(8) -0.013(8) 0.160(11) 0.021(9) -0.016(10) 0.144(9) 0.006(9) -0.019(9)
-0.055(9) 0.062(14) -0.042(12) 0.026(13) -0.015(12) -0.035(12) -0.004(11)
0.057(11) 0.017(10) 0.022(10) 0.998116 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3
3.1762 4 3.1762
C(4) 4.07(2) 0 -0.004(9) 0.018(10) 0.024(10) 0.186(9) -0.010(8) -0.029(8)
-0.158(8) -0.017(8) 0.263(12) -0.014(10) -0.041(10) 0.149(10) 0.014(9) -0.001(8)
-0.063(9) -0.083(14) -0.004(12) 0.011(14) -0.070(12) -0.025(12) 0.003(11)
0.005(11) 0.005(11) 0.004(10) 0.99732 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3
3.1762 4 3.1762
C(5) 4.06(3) 0 0.044(11) 0.031(10) 0 -0.190(10) 0 0 0.005(9) -0.015(9) 0
0.034(10) 0.016(10) 0 0 0.010(10) -0.234(11) 0.064(13) 0 0 -0.075(12) 0.019(13)
0 0 0.045(13) 0.066(13) 0.999063 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4
3.1762
C(6) 4.16(3) 0 0.048(12) 0.007(11) 0 -0.156(10) 0 0 -0.038(10) -0.033(10) 0
0.003(10) 0.079(10) 0 0 -0.000(11) -0.288(12) 0.019(14) 0 0 -0.034(13) 0.022(12)
0 0 -0.024(13) -0.015(14) 0.999063 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762
4 3.1762
C(7) 3.96(3) 0 0.088(12) -0.017(13) 0 -0.139(11) 0 0 0.008(11) -0.003(11) 0
0.001(11) 0.061(11) 0 0 -0.015(11) -0.239(13) 0.006(14) 0 0 -0.018(13) 0.047(13)
0 0 0.034(15) -0.018(14) 0.999063 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762
4 3.1762
C(8) 4.06(3) 0 0.007(11) -0.013(12) 0 -0.116(10) 0 0 0.044(10) 0.007(10) 0
0.080(10) 0.045(11) 0 0 -0.003(11) -0.224(12) -0.019(13) 0 0 -0.001(13)
-0.003(13) 0 0 -0.004(14) 0.027(13) 0.999063 1 1 1 1 1 2 3.1762 2 3.1762 2
3.1762 3 3.1762 4 3.1762
C(9) 4.09(3) 0 0.091(10) 0.015(11) 0 -0.135(8) 0 0 -0.073(9) -0.072(9) 0
0.069(9) 0.023(10) 0 0 -0.032(10) -0.296(11) 0.075(12) 0 0 -0.013(12) -0.037(11)
0 0 -0.040(14) 0.040(14) 1.000558 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762
4 3.1762
C(10) 4.02(2) 0 0.051(10) 0.034(10) 0 -0.143(9) 0 0 -0.015(9) 0.024(9) 0
-0.004(10) 0.025(10) 0 0 0.017(11) -0.138(11) 0.007(12) 0 0 -0.017(12) 0.008(12)
0 0 0.026(14) -0.064(13) 1.005037 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762
4 3.1762
C(23) 3.95(3) 0 0.088(9) -0.010(8) -0.126(9) -0.086(9) -0.009(9) 0.019(7)
-0.032(8) 0.000(8) 0.272(11) -0.076(10) 0.013(8) 0.087(9) 0.019(9) -0.025(10)
-0.054(10) 0.074(12) -0.028(12) 0.028(12) -0.010(12) 0.029(12) -0.013(12)
0.065(12) -0.093(11) 0.020(11) 1.00301 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3
3.1762 4 3.1762
C(31) 3.96(2) 0 -0.001(9) 0.008(10) -0.012(10) 0.088(9) -0.011(9) 0.004(9)
-0.183(9) 0.024(8) 0.198(11) 0.007(10) 0.006(11) 0.185(12) -0.001(10) -0.001(9)
0.009(9) 0.015(13) -0.022(12) -0.011(14) 0.023(14) 0.034(13) -0.027(12)
-0.011(13) -0.014(11) 0.053(12) 0.997268 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3
3.1762 4 3.1762
C(311) 4.14(3) 0 -0.062(10) -0.005(9) -0.035(10) -0.045(9) -0.002(10) -0.041(9)
0.010(9) 0.030(8) 0.251(11) 0.034(10) 0.045(10) 0.022(11) -0.087(10) -0.058(9)
-0.001(10) 0.120(14) 0.012(12) 0.014(12) -0.069(13) 0.033(12) -0.038(12)
0.081(13) 0.048(10) -0.100(11) 0.996586 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3
3.1762 4 3.1762
H(1) 0.782(15) 0 0 0 0.101(10) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.1
1.18 1.18 1.18 1.18 1.18 0 2 1 2 2 2 3 2 4 2
H(2) 0.922(15) 0 0 0 0.132(11) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.1
1.18 1.18 1.18 1.18 1.18 0 2 1 2 2 2 3 2 4 2
H(5) 0.970(17) 0 0 0 0.160(11) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.1
1.18 1.18 1.18 1.18 1.18 0 2 1 2 2 2 3 2 4 2
H(6) 0.904(16) 0 0 0 0.152(11) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.1
1.18 1.18 1.18 1.18 1.18 0 2 1 2 2 2 3 2 4 2
H(7) 1.030(18) 0 0 0 0.174(13) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.1
1.18 1.18 1.18 1.18 1.18 0 2 1 2 2 2 3 2 4 2
H(8) 0.957(19) 0 0 0 0.099(13) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.1
1.18 1.18 1.18 1.18 1.18 0 2 1 2 2 2 3 2 4 2
H(23A) 0.922(12) 0 0 0 0.121(8) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.1
1.18 1.18 1.18 1.18 1.18 0 2 1 2 2 2 3 2 4 2
H(23B) 0.9217 0 0 0 0.1207 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.1 1.18
1.18 1.18 1.18 1.18 0 2 1 2 2 2 3 2 4 2
H(23C) 0.9217 0 0 0 0.1207 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.1 1.18
1.18 1.18 1.18 1.18 0 2 1 2 2 2 3 2 4 2
H(31A) 0.902(10) 0 0 0 0.115(7) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.1
1.18 1.18 1.18 1.18 1.18 0 2 1 2 2 2 3 2 4 2
H(31B) 0.9019 0 0 0 0.1153 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.1 1.18
1.18 1.18 1.18 1.18 0 2 1 2 2 2 3 2 4 2
H(31C) 0.9019 0 0 0 0.1153 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.1 1.18
1.18 1.18 1.18 1.18 0 2 1 2 2 2 3 2 4 2
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_U_iso_or_equiv
P(2) 0.661925(5) 0.482849(4) 0.074523(4) 1 4 0.014
O(1) 0.79064(2) 0.589242(19) 0.07178(2) 1 4 0.018
O(4) 0.94685(3) 0.24666(3) 0.20485(2) 1 4 0.021
O(21) 0.53019(3) 0.55035(3) 0.11139(2) 1 4 0.021
O(22) 0.65057(3) 0.43039(2) -0.042492(16) 1 4 0.019
N(1) 0.68818(3) 0.17020(2) 0.264657(19) 1 4 0.020
C(3) 0.73085(2) 0.350744(18) 0.147879(15) 1 4 0.015
C(4) 0.88637(2) 0.334200(19) 0.151694(15) 1 4 0.015
C(5) 1.12308(2) 0.38966(2) 0.066650(18) 1 4 0.018
C(6) 1.21239(3) 0.47156(3) 0.00743(2) 1 4 0.022
C(7) 1.16036(3) 0.59292(3) -0.02899(2) 1 4 0.023
C(8) 1.01866(3) 0.63147(2) -0.00725(2) 1 4 0.021
C(9) 0.93004(2) 0.546727(18) 0.050172(16) 1 4 0.016
C(10) 0.97952(2) 0.425563(18) 0.088410(14) 1 4 0.015
C(23) 0.60537(4) 0.51966(3) -0.12529(2) 1 4 0.025
C(31) 0.63736(2) 0.26343(2) 0.201981(16) 1 4 0.017
C(311) 0.47572(3) 0.26942(3) 0.19046(2) 1 4 0.025
H(1) 0.796474 0.16279 0.271845 1 4 0.035
H(2) 0.614406 0.117774 0.305578 1 4 0.040
H(5) 1.161608 0.295929 0.096151 1 4 0.036
H(6) 1.322238 0.441658 -0.009789 1 4 0.043
H(7) 1.22733 0.659594 -0.074373 1 4 0.044
H(8) 0.973804 0.723838 -0.034655 1 4 0.038
H(23A) 0.586691 0.460366 -0.192751 1 4 0.046
H(23B) 0.691586 0.586417 -0.137821 1 4 0.043
H(23C) 0.509378 0.567889 -0.10134 1 4 0.045
H(31A) 0.422351 0.191569 0.23015 1 4 0.046
H(31B) 0.451524 0.260552 0.10902 1 4 0.041
H(31C) 0.432393 0.362726 0.210244 1 4 0.042
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O(1) P(2) O(21) 107.861(14) 1_555 1_555 1_555 yes
O(1) P(2) O(22) 104.823(13) 1_555 1_555 1_555 yes
O(1) P(2) C(3) 104.851(11) 1_555 1_555 1_555 yes
O(21) P(2) O(22) 113.525(16) 1_555 1_555 1_555 yes
O(21) P(2) C(3) 119.290(13) 1_555 1_555 1_555 yes
O(22) P(2) C(3) 105.276(10) 1_555 1_555 1_555 yes
P(2) O(1) C(9) 118.922(15) 1_555 1_555 1_555 yes
C(31) N(1) H(1) 117.44 1_555 1_555 1_555 yes
C(31) N(1) H(2) 116.46 1_555 1_555 1_555 yes
H(1) N(1) H(2) 125.89 1_555 1_555 1_555 yes
P(2) C(3) C(4) 117.891(14) 1_555 1_555 1_555 yes
P(2) C(3) C(31) 120.916(16) 1_555 1_555 1_555 yes
C(4) C(3) C(31) 121.193(17) 1_555 1_555 1_555 yes
O(4) C(4) C(3) 123.08(2) 1_555 1_555 1_555 yes
O(4) C(4) C(10) 118.14(2) 1_555 1_555 1_555 yes
C(3) C(4) C(10) 118.775(17) 1_555 1_555 1_555 yes
C(6) C(5) C(10) 120.80(2) 1_555 1_555 1_555 yes
C(6) C(5) H(5) 121.04 1_555 1_555 1_555 yes
C(10) C(5) H(5) 118.15 1_555 1_555 1_555 yes
C(5) C(6) C(7) 119.93(2) 1_555 1_555 1_555 yes
C(5) C(6) H(6) 119.88 1_555 1_555 1_555 yes
C(7) C(6) H(6) 120.19 1_555 1_555 1_555 yes
C(6) C(7) C(8) 120.30(2) 1_555 1_555 1_555 yes
C(6) C(7) H(7) 121.87 1_555 1_555 1_555 yes
C(8) C(7) H(7) 117.83 1_555 1_555 1_555 yes
C(7) C(8) C(9) 118.85(2) 1_555 1_555 1_555 yes
C(7) C(8) H(8) 122.67 1_555 1_555 1_555 yes
C(9) C(8) H(8) 118.47 1_555 1_555 1_555 yes
O(1) C(9) C(8) 117.24(2) 1_555 1_555 1_555 yes
O(1) C(9) C(10) 120.639(19) 1_555 1_555 1_555 yes
C(8) C(9) C(10) 122.08(2) 1_555 1_555 1_555 yes
C(4) C(10) C(5) 119.209(18) 1_555 1_555 1_555 yes
C(4) C(10) C(9) 122.768(18) 1_555 1_555 1_555 yes
C(5) C(10) C(9) 118.022(19) 1_555 1_555 1_555 yes
H(23A) C(23) H(23B) 111.47 1_555 1_555 1_555 yes
H(23A) C(23) H(23C) 110.92 1_555 1_555 1_555 yes
H(23B) C(23) H(23C) 112.27 1_555 1_555 1_555 yes
N(1) C(31) C(3) 121.45(2) 1_555 1_555 1_555 yes
N(1) C(31) C(311) 116.16(2) 1_555 1_555 1_555 yes
C(3) C(31) C(311) 122.38(2) 1_555 1_555 1_555 yes
C(31) C(311) H(31A) 112.81 1_555 1_555 1_555 yes
C(31) C(311) H(31B) 107.53 1_555 1_555 1_555 yes
C(31) C(311) H(31C) 112.94 1_555 1_555 1_555 yes
H(31A) C(311) H(31B) 107.45 1_555 1_555 1_555 yes
H(31A) C(311) H(31C) 112.29 1_555 1_555 1_555 yes
H(31B) C(311) H(31C) 103.08 1_555 1_555 1_555 yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P(2) O(1) 1.6085(2) 1_555 1_555 yes
P(2) O(21) 1.4743(2) 1_555 1_555 yes
P(2) O(22) 1.5779(2) 1_555 1_555 yes
P(2) C(3) 1.75191(19) 1_555 1_555 yes
O(1) C(9) 1.3874(3) 1_555 1_555 yes
O(4) C(4) 1.2476(3) 1_555 1_555 yes
N(1) C(31) 1.3218(3) 1_555 1_555 yes
N(1) H(1) 1.0090 1_555 1_555 yes
N(1) H(2) 1.0089 1_555 1_555 yes
C(3) C(4) 1.4497(3) 1_555 1_555 yes
C(3) C(31) 1.4155(3) 1_555 1_555 yes
C(4) C(10) 1.4986(3) 1_555 1_555 yes
C(5) C(6) 1.3918(3) 1_555 1_555 yes
C(5) C(10) 1.4048(3) 1_555 1_555 yes
C(5) H(5) 1.0829 1_555 1_555 yes
C(6) C(7) 1.4012(4) 1_555 1_555 yes
C(6) H(6) 1.0830 1_555 1_555 yes
C(7) C(8) 1.3959(4) 1_555 1_555 yes
C(7) H(7) 1.0829 1_555 1_555 yes
C(8) C(9) 1.3934(3) 1_555 1_555 yes
C(8) H(8) 1.0828 1_555 1_555 yes
C(9) C(10) 1.3993(3) 1_555 1_555 yes
C(23) H(23A) 1.0593 1_555 1_555 yes
C(23) H(23B) 1.0589 1_555 1_555 yes
C(23) H(23C) 1.0586 1_555 1_555 yes
C(31) C(311) 1.5040(3) 1_555 1_555 yes
C(311) H(31A) 1.0589 1_555 1_555 yes
C(311) H(31B) 1.0590 1_555 1_555 yes
C(311) H(31C) 1.0590 1_555 1_555 yes
loop_
_publcif_info_datablock.id
_publcif_info_datablock.publ_exptl
_publcif_info_datablock.publ_geom
_publcif_info_datablock.structure
{718aa8e3-ed5f-43f6-b69b-30521a7c4ae0} y y y
loop_
_publcif_info_exptl_table_extra_item
sin_theta_over_lambda_max
loop_
_publcif_info_tables.block_id
_publcif_info_tables.reference_item
{718aa8e3-ed5f-43f6-b69b-30521a7c4ae0} '_publcif_info_datablock.publ_exptl'
{718aa8e3-ed5f-43f6-b69b-30521a7c4ae0} '_geom_bond_atom_site_label_1'
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139064202
