# Electronic Supplementary Material (ESI) for Inorganic Chemistry Frontiers.
# This journal is © the Partner Organisations 2023

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1
_database_code_depnum_ccdc_archive 'CCDC 2254786'
loop_
_audit_author_name
_audit_author_address
'Jianjian Yang'
;China University of Petroleum (East China)
China
;
_audit_update_record             
;
2023-04-07 deposited with the CCDC.	2023-09-07 downloaded from the CCDC.
;
_audit_creation_date             2021-10-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        BPPA-azo
_chemical_formula_moiety         'C12 H10 O6 P2, C12 H12 O6 P2, 2(C2 H4 N3)'
_chemical_formula_sum            'C28 H30 N6 O12 P4'
_chemical_formula_weight         766.46
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.5241(3)
_cell_length_b                   10.4051(6)
_cell_length_c                   17.8775(8)
_cell_angle_alpha                77.976(4)
_cell_angle_beta                 78.130(3)
_cell_angle_gamma                72.036(4)
_cell_volume                     1629.15(14)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    45
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      87
_cell_measurement_theta_min      30
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.792
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73995
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.562
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             792
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method ?
_exptl_crystal_size_max          0.56
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.04
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0235
_diffrn_reflns_av_unetI/netI     0.0317
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            11790
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.473
_diffrn_reflns_theta_min         4.522
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5292
_reflns_number_total             6113
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.337
_refine_diff_density_min         -0.358
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     491
_refine_ls_number_reflns         6113
_refine_ls_number_restraints     10
_refine_ls_R_factor_all          0.0424
_refine_ls_R_factor_gt           0.0366
_refine_ls_restrained_S_all      1.041
_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)+(0.0519P)²+0.6279P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1010
_refine_ls_wR_factor_ref         0.1065
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 O2-H2A = O5-H5 = O6-H6 = O8-H8 = O10-H10 = O11-H11
 0.95 with sigma of 0.01
 N4-H4A = N5-H5B = N2-H2B = N1-H1A
 0.94 with sigma of 0.01
3.a Aromatic/amide H refined with riding coordinates:
 C20(H20), C19(H19), C18(H18), C16(H16), C15(H15), C14(H14), C28(H28),
 C12(H12), C9(H9), C8(H8A), C7(H7), C6(H6A), C5(H5A), C4(H4), C3(H3), C2(H2),
 C1(H1), C27(H27), C26(H26), C25(H25)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.06210(5) 0.30317(5) 0.29289(3) 0.02727(12) Uani 1 1 d . . . . .
O3 O 0.03891(15) 0.16551(13) 0.33285(7) 0.0352(3) Uani 1 1 d . . . . .
O9 O 0.45743(15) 0.32975(13) -0.34802(7) 0.0343(3) Uani 1 1 d . . . . .
P2 P 0.05896(5) 0.85971(5) 0.28337(3) 0.02780(13) Uani 1 1 d . . . . .
P3 P 0.43143(5) 0.19536(5) -0.30501(2) 0.02609(12) Uani 1 1 d . . . . .
O8 O 0.57955(15) 0.07717(14) -0.31021(8) 0.0353(3) Uani 1 1 d D . . . .
P4 P 0.45845(5) 0.63126(5) -0.29363(3) 0.02830(13) Uani 1 1 d . . . . .
O12 O 0.33039(14) 0.66001(15) -0.33640(7) 0.0366(3) Uani 1 1 d . . . . .
O6 O -0.03362(15) 0.75933(15) 0.32635(8) 0.0368(3) Uani 1 1 d D . . . .
O11 O 0.55527(15) 0.48039(14) -0.28744(8) 0.0371(3) Uani 1 1 d D . . . .
O2 O -0.08998(15) 0.41604(14) 0.29830(8) 0.0383(3) Uani 1 1 d D . . . .
O5 O -0.04255(15) 1.00666(14) 0.27731(8) 0.0375(3) Uani 1 1 d D . . . .
O4 O 0.18759(14) 0.83536(14) 0.32569(7) 0.0357(3) Uani 1 1 d . . . . .
O7 O 0.31683(15) 0.15419(15) -0.33418(8) 0.0384(3) Uani 1 1 d . . . . .
C24 C 0.3953(2) 0.6667(2) -0.19656(10) 0.0304(4) Uani 1 1 d . . . . .
N5 N 0.2192(2) 0.63400(17) 0.44806(9) 0.0382(4) Uani 1 1 d D . . . .
O10 O 0.55861(15) 0.72491(15) -0.33440(8) 0.0388(3) Uani 1 1 d D . . . .
N2 N 0.7163(2) 0.9446(2) 0.45194(10) 0.0458(4) Uani 1 1 d D . . . .
O1 O 0.17061(15) 0.34523(15) 0.32558(8) 0.0404(3) Uani 1 1 d . . . . .
C23 C 0.1218(2) 0.8219(2) 0.18663(10) 0.0307(4) Uani 1 1 d . . . . .
C22 C 0.3721(2) 0.20979(19) -0.20427(10) 0.0289(4) Uani 1 1 d . . . . .
N1 N 0.8111(2) 0.95086(19) 0.54755(10) 0.0438(4) Uani 1 1 d D . . . .
N4 N 0.2953(2) 0.47898(18) 0.53969(10) 0.0405(4) Uani 1 1 d D . . . .
C21 C 0.1244(2) 0.29251(19) 0.19183(10) 0.0301(4) Uani 1 1 d . . . . .
C20 C 0.3465(2) 0.5940(2) -0.05941(11) 0.0397(5) Uani 1 1 d . . . . .
H20 H 0.351029 0.522916 -0.017870 0.048 Uiso 1 1 calc R . . . .
C19 C 0.1739(2) 0.6875(2) 0.17335(11) 0.0419(5) Uani 1 1 d . . . . .
H19 H 0.174506 0.616605 0.214819 0.050 Uiso 1 1 calc R . . . .
C18 C 0.4193(2) 0.1687(3) -0.07304(11) 0.0475(6) Uani 1 1 d . . . . .
H18 H 0.485409 0.128894 -0.037551 0.057 Uiso 1 1 calc R . . . .
C17 C 0.2847(2) 0.7284(2) -0.04516(10) 0.0320(4) Uani 1 1 d . . . . .
C16 C 0.4010(2) 0.5631(2) -0.13331(11) 0.0384(4) Uani 1 1 d . . . . .
H16 H 0.441841 0.472338 -0.140687 0.046 Uiso 1 1 calc R . . . .
C15 C 0.0249(2) 0.3300(2) 0.13920(11) 0.0441(5) Uani 1 1 d . . . . .
H15 H -0.076403 0.366358 0.155712 0.053 Uiso 1 1 calc R . . . .
C14 C 0.3337(2) 0.8017(2) -0.18379(11) 0.0398(5) Uani 1 1 d . . . . .
H14 H 0.329116 0.872434 -0.225495 0.048 Uiso 1 1 calc R . . . .
C28 C 0.1831(3) 0.5216(2) 0.44462(12) 0.0481(5) Uani 1 1 d . . . . .
H28 H 0.133139 0.513929 0.406939 0.058 Uiso 1 1 calc R . . . .
C13 C 0.2758(2) 0.24299(19) -0.04764(10) 0.0301(4) Uani 1 1 d . . . . .
C12 C 0.2739(2) 0.2394(3) 0.16499(12) 0.0471(6) Uani 1 1 d . . . . .
H12 H 0.342935 0.213576 0.199133 0.057 Uiso 1 1 calc R . . . .
C11 C 0.2273(2) 0.7608(2) 0.03483(11) 0.0323(4) Uani 1 1 d . . . . .
C10 C 0.2241(2) 0.26105(19) 0.03486(10) 0.0309(4) Uani 1 1 d . . . . .
C9 C 0.1741(3) 0.8948(2) 0.04966(12) 0.0454(5) Uani 1 1 d . . . . .
H9 H 0.173770 0.966042 0.008398 0.055 Uiso 1 1 calc R . . . .
N6 N 0.2267(3) 0.4240(2) 0.50067(12) 0.0571(5) Uani 1 1 d . . . . .
C8 C 0.1817(2) 0.3018(3) -0.10301(12) 0.0478(6) Uani 1 1 d . . . . .
H8A H 0.084735 0.353246 -0.088040 0.057 Uiso 1 1 calc R . . . .
C7 C 0.2792(2) 0.8314(2) -0.10952(11) 0.0409(5) Uani 1 1 d . . . . .
H7 H 0.237965 0.922206 -0.102301 0.049 Uiso 1 1 calc R . . . .
C6 C 0.0743(2) 0.3140(3) 0.06242(12) 0.0456(5) Uani 1 1 d . . . . .
H6A H 0.005133 0.339423 0.028373 0.055 Uiso 1 1 calc R . . . .
C5 C 0.2289(2) 0.2856(3) -0.17986(12) 0.0476(6) Uani 1 1 d . . . . .
H5A H 0.163291 0.326285 -0.215554 0.057 Uiso 1 1 calc R . . . .
C4 C 0.1216(3) 0.9257(2) 0.12368(12) 0.0440(5) Uani 1 1 d . . . . .
H4 H 0.085911 1.016601 0.131345 0.053 Uiso 1 1 calc R . . . .
C3 C 0.3226(2) 0.2240(3) 0.08801(12) 0.0479(6) Uani 1 1 d . . . . .
H3 H 0.423984 0.187884 0.071554 0.057 Uiso 1 1 calc R . . . .
C2 C 0.2251(2) 0.6578(2) 0.09881(11) 0.0420(5) Uani 1 1 d . . . . .
H2 H 0.258960 0.566880 0.091188 0.050 Uiso 1 1 calc R . . . .
C1 C 0.4673(2) 0.1517(3) -0.14979(12) 0.0463(6) Uani 1 1 d . . . . .
H1 H 0.564492 0.100843 -0.164913 0.056 Uiso 1 1 calc R . . . .
C27 C 0.2906(3) 0.6036(2) 0.50793(13) 0.0475(5) Uani 1 1 d . . . . .
H27 H 0.330727 0.661709 0.524551 0.057 Uiso 1 1 calc R . . . .
N3 N 0.7908(3) 1.0764(2) 0.50627(12) 0.0753(8) Uani 1 1 d . . . . .
C26 C 0.7697(3) 0.8724(2) 0.51501(13) 0.0493(6) Uani 1 1 d . . . . .
H26 H 0.776224 0.780495 0.532852 0.059 Uiso 1 1 calc R . . . .
C25 C 0.7339(4) 1.0679(3) 0.44832(14) 0.0715(9) Uani 1 1 d . . . . .
H25 H 0.708059 1.140003 0.408542 0.086 Uiso 1 1 calc R . . . .
H10 H 0.6577(14) 0.700(3) -0.3254(15) 0.064(8) Uiso 1 1 d D . . . .
H6 H -0.1361(12) 0.789(3) 0.3227(14) 0.059(8) Uiso 1 1 d D . . . .
H2A H -0.174(2) 0.383(3) 0.3066(16) 0.077(9) Uiso 1 1 d D . . . .
H5 H -0.009(3) 1.070(2) 0.2961(15) 0.078(9) Uiso 1 1 d D . . . .
H11 H 0.515(3) 0.426(3) -0.3080(15) 0.078(9) Uiso 1 1 d D . . . .
H8 H 0.661(2) 0.111(3) -0.3122(17) 0.082(10) Uiso 1 1 d D . . . .
H5B H 0.212(3) 0.7119(18) 0.4110(12) 0.077(9) Uiso 1 1 d D . . . .
H1A H 0.857(3) 0.925(3) 0.5921(10) 0.060(8) Uiso 1 1 d D . . . .
H2B H 0.682(3) 0.913(3) 0.4156(13) 0.082(9) Uiso 1 1 d D . . . .
H4A H 0.340(3) 0.429(2) 0.5830(10) 0.068(8) Uiso 1 1 d D . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 1.5214(14) . ?
P1 O2 1.5578(14) . ?
P1 O1 1.4949(13) . ?
P1 C21 1.7974(18) . ?
O9 P3 1.5151(13) . ?
P2 O6 1.5536(14) . ?
P2 O5 1.5319(14) . ?
P2 O4 1.4992(13) . ?
P2 C23 1.7933(18) . ?
P3 O8 1.5603(14) . ?
P3 O7 1.5042(13) . ?
P3 C22 1.7964(18) . ?
P4 O12 1.4916(13) . ?
P4 O11 1.5504(14) . ?
P4 C24 1.7915(18) . ?
P4 O10 1.5435(14) . ?
C24 C16 1.387(3) . ?
C24 C14 1.392(3) . ?
N5 C28 1.332(3) . ?
N5 C27 1.316(3) . ?
N2 C26 1.319(3) . ?
N2 C25 1.331(3) . ?
C23 C19 1.386(3) . ?
C23 C4 1.388(3) . ?
C22 C5 1.381(3) . ?
C22 C1 1.384(3) . ?
N1 N3 1.337(3) . ?
N1 C26 1.285(3) . ?
N4 N6 1.351(3) . ?
N4 C27 1.293(3) . ?
C21 C15 1.387(3) . ?
C21 C12 1.381(3) . ?
C20 C17 1.395(3) . ?
C20 C16 1.382(3) . ?
C19 C2 1.386(3) . ?
C18 C13 1.382(3) . ?
C18 C1 1.384(3) . ?
C17 C11 1.491(3) . ?
C17 C7 1.397(3) . ?
C15 C6 1.384(3) . ?
C14 C7 1.384(3) . ?
C28 N6 1.302(3) . ?
C13 C10 1.488(3) . ?
C13 C8 1.389(3) . ?
C12 C3 1.385(3) . ?
C11 C9 1.391(3) . ?
C11 C2 1.397(3) . ?
C10 C6 1.386(3) . ?
C10 C3 1.387(3) . ?
C9 C4 1.382(3) . ?
C8 C5 1.383(3) . ?
N3 C25 1.294(3) . ?

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 O2 109.84(8) . . ?
O3 P1 C21 107.57(8) . . ?
O2 P1 C21 106.49(8) . . ?
O1 P1 O3 113.53(8) . . ?
O1 P1 O2 108.77(8) . . ?
O1 P1 C21 110.40(8) . . ?
O6 P2 C23 106.90(8) . . ?
O5 P2 O6 109.56(8) . . ?
O5 P2 C23 107.03(8) . . ?
O4 P2 O6 107.72(8) . . ?
O4 P2 O5 113.93(8) . . ?
O4 P2 C23 111.49(8) . . ?
O9 P3 O8 110.88(8) . . ?
O9 P3 C22 108.54(8) . . ?
O8 P3 C22 106.59(8) . . ?
O7 P3 O9 113.50(8) . . ?
O7 P3 O8 108.01(8) . . ?
O7 P3 C22 109.09(8) . . ?
O12 P4 O11 113.42(8) . . ?
O12 P4 C24 111.24(8) . . ?
O12 P4 O10 109.30(8) . . ?
O11 P4 C24 106.51(8) . . ?
O10 P4 O11 108.80(8) . . ?
O10 P4 C24 107.36(8) . . ?
C16 C24 P4 121.94(15) . . ?
C16 C24 C14 118.55(18) . . ?
C14 C24 P4 119.48(14) . . ?
C27 N5 C28 105.94(18) . . ?
C26 N2 C25 104.69(19) . . ?
C19 C23 P2 120.37(15) . . ?
C19 C23 C4 118.53(18) . . ?
C4 C23 P2 121.09(15) . . ?
C5 C22 P3 119.66(14) . . ?
C5 C22 C1 118.09(17) . . ?
C1 C22 P3 122.19(15) . . ?
C26 N1 N3 111.16(18) . . ?
C27 N4 N6 110.34(17) . . ?
C15 C21 P1 121.71(14) . . ?
C12 C21 P1 120.38(14) . . ?
C12 C21 C15 117.82(17) . . ?
C16 C20 C17 122.07(18) . . ?
C2 C19 C23 120.56(19) . . ?
C13 C18 C1 121.87(18) . . ?
C20 C17 C11 121.70(18) . . ?
C20 C17 C7 116.76(18) . . ?
C7 C17 C11 121.55(19) . . ?
C20 C16 C24 120.40(19) . . ?
C6 C15 C21 120.82(18) . . ?
C7 C14 C24 120.55(18) . . ?
N6 C28 N5 111.4(2) . . ?
C18 C13 C10 121.88(17) . . ?
C18 C13 C8 116.90(17) . . ?
C8 C13 C10 121.22(18) . . ?
C21 C12 C3 121.04(19) . . ?
C9 C11 C17 121.82(18) . . ?
C9 C11 C2 116.59(18) . . ?
C2 C11 C17 121.59(19) . . ?
C6 C10 C13 121.33(17) . . ?
C6 C10 C3 116.86(18) . . ?
C3 C10 C13 121.80(18) . . ?
C4 C9 C11 122.19(19) . . ?
C28 N6 N4 103.94(18) . . ?
C5 C8 C13 121.61(19) . . ?
C14 C7 C17 121.66(19) . . ?
C15 C6 C10 121.80(18) . . ?
C22 C5 C8 120.85(18) . . ?
C9 C4 C23 120.4(2) . . ?
C12 C3 C10 121.65(19) . . ?
C19 C2 C11 121.74(19) . . ?
C22 C1 C18 120.67(19) . . ?
N4 C27 N5 108.33(19) . . ?
C25 N3 N1 103.2(2) . . ?
N1 C26 N2 108.3(2) . . ?
N3 C25 N2 112.5(2) . . ?

_olex2_submission_original_sample_id BPPA-azo
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2254787'
loop_
_audit_author_name
_audit_author_address
'Jianjian Yang'
;China University of Petroleum (East China)
China
;
_audit_update_record             
;
2023-04-07 deposited with the CCDC.	2023-09-07 downloaded from the CCDC.
;
_audit_creation_date             2019-10-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_chemical_name_systematic        BPPA-gua
_chemical_formula_moiety         'C12 H11 O6 P2, C H6 N3'
_chemical_formula_sum            'C13 H17 N3 O6 P2'
_chemical_formula_weight         373.24
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.01920 0.00962 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.03256 0.01839 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.05239 0.03376 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
P 0.30359 0.43700 6.43450 4.17910 1.78000 1.49080 1.90670 27.15700 0.52600
68.16450 1.11489999294
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 x,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   16.0962(3)
_cell_length_b                   14.3676(3)
_cell_length_c                   6.77280(10)
_cell_angle_alpha                90
_cell_angle_beta                 97.203(2)
_cell_angle_gamma                90
_cell_volume                     1553.94(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    50
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      90
_cell_measurement_theta_min      40
_exptl_absorpt_coefficient_mu    2.905
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73995
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.5953
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             780.9619
_exptl_crystal_size_max          0.51
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.08
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0255
_diffrn_reflns_av_unetI/netI     0.0368
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            5688
_diffrn_reflns_theta_full        70.6065
_diffrn_reflns_theta_max         70.61
_diffrn_reflns_theta_min         4.14
_diffrn_ambient_environment      ?
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.9776
_diffrn_measured_fraction_theta_max 0.9776
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              19
_reflns_limit_h_min              -19
_reflns_limit_k_max              17
_reflns_limit_k_min              0
_reflns_limit_l_max              8
_reflns_limit_l_min              0
_reflns_number_gt                2361
_reflns_number_total             2923
_reflns_threshold_expression     I>=2u(I)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.4891
_refine_diff_density_min         -0.5402
_refine_diff_density_rms         0.0963
_refine_ls_d_res_high            0.8173
_refine_ls_d_res_low             10.6809
_refine_ls_goodness_of_fit_ref   1.0767
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    16
_refine_ls_number_parameters     253
_refine_ls_number_reflns         2923
_refine_ls_number_restraints     9
_refine_ls_R_factor_all          0.0507
_refine_ls_R_factor_gt           0.0379
_refine_ls_restrained_S_all      1.0749
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0477P)²+0.7635P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0941
_refine_ls_wR_factor_ref         0.1044
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 N1-H1a = N1-H1b = N2-H2a = N2-H2b = N3-H3b = N3-H3c
 0.92 with sigma of 0.01
 O3-H3 = O5-H5 = O6-H6
 0.86 with sigma of 0.01
3.a Aromatic/amide H refined with riding coordinates:
 C9(H9), C7(H7), C6(H6a), C5(H5a), C4(H4), C3(H3a), C2(H2), C1(H1)
;
_atom_sites_solution_primary     iterative
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_refinement_flags_posn
P1 P 0.32781(3) 0.13821(4) 0.07055(8) 0.01063(15) Uani 1.000000 .
O6 O -0.26048(10) 0.14180(11) -1.0199(2) 0.0152(3) Uani 1.000000 D
P2 P -0.27589(3) 0.14310(4) -0.79961(8) 0.01215(15) Uani 1.000000 .
O3 O 0.31396(10) 0.13476(11) 0.2950(2) 0.0147(3) Uani 1.000000 D
O5 O -0.32719(10) 0.05585(11) -0.7576(2) 0.0145(3) Uani 1.000000 D
O4 O -0.31972(9) 0.22886(11) -0.7397(2) 0.0155(3) Uani 1.000000 .
O2 O 0.37778(9) 0.05211(10) 0.0267(2) 0.0132(3) Uani 1.000000 .
O1 O 0.36812(9) 0.22847(10) 0.0196(2) 0.0129(3) Uani 1.000000 .
C12 C 0.22539(13) 0.12970(15) -0.0675(3) 0.0122(4) Uani 1.000000 .
N3 N -0.52099(13) 0.12663(15) -0.2769(3) 0.0188(4) Uani 1.000000 D
C11 C -0.01691(14) 0.12377(16) -0.4225(3) 0.0149(5) Uani 1.000000 .
C10 C -0.17541(14) 0.13109(15) -0.6559(3) 0.0137(4) Uani 1.000000 .
N2 N -0.40833(12) 0.05548(14) -0.3927(3) 0.0169(4) Uani 1.000000 D
C9 C -0.02667(15) 0.16026(18) -0.6155(4) 0.0213(5) Uani 1.000000 .
H9 H 0.02003(15) 0.18283(18) -0.6682(4) 0.0256(6) Uiso 1.000000 R
C8 C 0.06649(14) 0.12255(16) -0.3000(3) 0.0146(5) Uani 1.000000 .
C7 C 0.13947(15) 0.13939(19) -0.3847(3) 0.0227(5) Uani 1.000000 .
H7 H 0.13581(15) 0.14878(19) -0.5214(3) 0.0272(7) Uiso 1.000000 R
C6 C -0.08875(15) 0.09085(19) -0.3503(3) 0.0233(5) Uani 1.000000 .
H6a H -0.08435(15) 0.06583(19) -0.2227(3) 0.0280(6) Uiso 1.000000 R
C5 C 0.21713(15) 0.14259(18) -0.2723(4) 0.0221(5) Uani 1.000000 .
H5a H 0.26454(15) 0.15352(18) -0.3345(4) 0.0266(6) Uiso 1.000000 R
C13 C -0.46682(14) 0.12054(16) -0.4099(3) 0.0144(4) Uani 1.000000 .
C4 C 0.07579(15) 0.1070(2) -0.0948(4) 0.0247(6) Uani 1.000000 .
H4 H 0.02862(15) 0.0942(2) -0.0331(4) 0.0297(7) Uiso 1.000000 R
N1 N -0.47315(12) 0.18056(14) -0.5603(3) 0.0182(4) Uani 1.000000 D
C3 C 0.15336(15) 0.1103(2) 0.0190(4) 0.0241(6) Uani 1.000000 .
H3a H 0.15742(15) 0.0994(2) 0.1553(4) 0.0289(7) Uiso 1.000000 R
C2 C -0.10381(15) 0.16357(18) -0.7295(4) 0.0203(5) Uani 1.000000 .
H2 H -0.10810(15) 0.18789(18) -0.8577(4) 0.0243(6) Uiso 1.000000 R
C1 C -0.16653(15) 0.09445(19) -0.4635(3) 0.0227(5) Uani 1.000000 .
H1 H -0.21336(15) 0.07222(19) -0.4109(3) 0.0272(6) Uiso 1.000000 R
H2a H -0.4003(18) 0.0175(17) -0.284(3) 0.032(8) Uiso 1.000000 D
H1a H -0.5117(14) 0.2267(15) -0.554(4) 0.030(8) Uiso 1.000000 D
H2b H -0.3751(13) 0.0487(18) -0.491(3) 0.016(7) Uiso 1.000000 D
H3b H -0.5222(18) 0.0791(14) -0.187(3) 0.030(8) Uiso 1.000000 D
H1b H -0.4278(13) 0.191(2) -0.627(4) 0.037(9) Uiso 1.000000 D
H3c H -0.5655(13) 0.1665(17) -0.297(4) 0.035(9) Uiso 1.000000 D
H5 H -0.342(3) 0.017(2) -0.853(4) 0.088(15) Uiso 1.000000 D
H3 H 0.334(2) 0.1805(18) 0.367(5) 0.064(12) Uiso 1.000000 D
H6 H -0.285(2) 0.1858(19) -1.093(5) 0.061(12) Uiso 1.000000 D


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 1.5649(16) . ?
P1 O2 1.5250(15) . ?
P1 O1 1.5095(15) . ?
P1 C12 1.795(2) . ?
O6 P2 1.5432(16) . ?
P2 O5 1.5470(16) . ?
P2 O4 1.5009(16) . ?
P2 C10 1.788(2) . ?
C12 C5 1.389(3) . ?
C12 C3 1.391(3) . ?
N3 C13 1.333(3) . ?
C11 C9 1.399(3) . ?
C11 C8 1.487(3) . ?
C11 C6 1.393(3) . ?
C10 C2 1.392(3) . ?
C10 C1 1.396(3) . ?
N2 C13 1.321(3) . ?
C9 C2 1.378(3) . ?
C8 C7 1.392(3) . ?
C8 C4 1.397(3) . ?
C7 C5 1.380(3) . ?
C6 C1 1.385(3) . ?
C13 N1 1.329(3) . ?
C4 C3 1.383(3) . ?

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
O2 P1 O3 107.85(8) . . ?
O1 P1 O3 111.54(9) . . ?
O1 P1 O2 113.58(9) . . ?
C12 P1 O3 105.71(9) . . ?
C12 P1 O2 108.40(9) . . ?
C12 P1 O1 109.42(9) . . ?
O5 P2 O6 108.80(9) . . ?
O4 P2 O6 114.17(9) . . ?
O4 P2 O5 109.61(9) . . ?
C10 P2 O6 106.32(10) . . ?
C10 P2 O5 106.80(10) . . ?
C10 P2 O4 110.85(9) . . ?
C5 C12 P1 118.55(17) . . ?
C3 C12 P1 123.61(17) . . ?
C3 C12 C5 117.8(2) . . ?
C8 C11 C9 120.9(2) . . ?
C6 C11 C9 117.0(2) . . ?
C6 C11 C8 122.1(2) . . ?
C2 C10 P2 120.37(17) . . ?
C1 C10 P2 121.61(17) . . ?
C1 C10 C2 117.9(2) . . ?
C2 C9 C11 121.6(2) . . ?
C7 C8 C11 121.2(2) . . ?
C4 C8 C11 122.2(2) . . ?
C4 C8 C7 116.6(2) . . ?
C5 C7 C8 122.1(2) . . ?
C1 C6 C11 121.7(2) . . ?
C7 C5 C12 120.9(2) . . ?
N2 C13 N3 120.4(2) . . ?
N1 C13 N3 118.8(2) . . ?
N1 C13 N2 120.8(2) . . ?
C3 C4 C8 121.7(2) . . ?
C4 C3 C12 120.9(2) . . ?
C9 C2 C10 121.1(2) . . ?
C6 C1 C10 120.7(2) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_restr_distance_atom_site_label_1
_restr_distance_atom_site_label_2
_restr_distance_site_symmetry_2
_restr_distance_target
_restr_distance_target_weight_param
_restr_distance_diff
O6 H6 1 0.8600 0.0100 -0.0034
O3 H3 1 0.8600 0.0100 0.0041
O5 H5 1 0.8600 0.0100 -0.0050
N3 H3b 1 0.9200 0.0100 0.0055
N3 H3c 1 0.9200 0.0100 0.0067
N2 H2a 1 0.9200 0.0100 0.0050
N2 H2b 1 0.9200 0.0100 0.0103
N1 H1a 1 0.9200 0.0100 0.0081
N1 H1b 1 0.9200 0.0100 0.0047

