####################################################################### 
# 
# 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_BPY@PA
_database_code_depnum_ccdc_archive 'CCDC 1046996'
_audit_update_record             
;
2015-02-03 deposited with the CCDC.
2016-01-29 downloaded from the CCDC.
;
_audit_creation_date             2015-01-31
_audit_creation_method           
;
  Olex2 1.2-ac2
  (compiled Nov  7 2012 10:34:12, GUI svn.r4372)
;
_chemical_name_common            BPY@PA
_chemical_name_systematic        
"2,2'-bipyridinium-5,5'-diamino hydrogen Phosphate monohydreate"
_chemical_formula_moiety         'C10 H12 N4, H O4 P, H2 O'
_chemical_formula_sum            'C10 H15 N4 O5 P'
_chemical_formula_weight         302.23
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C10 H15 N4 O5 P'
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'

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

_cell_length_a                   12.9672(5)
_cell_length_b                   4.22937(14)
_cell_length_c                   24.0975(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.972(4)
_cell_angle_gamma                90.00
_cell_volume                     1297.42(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2682
_cell_measurement_temperature    298
_cell_measurement_theta_max      29.0540
_cell_measurement_theta_min      3.9040
_exptl_absorpt_coefficient_mu    0.239
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91424
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33c (release 11-04-2014 CrysAlis171 .NET)
(compiled Apr 11 2014,15:12:41)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.547
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             632
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0223
_diffrn_reflns_av_unetI/netI     0.0366
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            5075
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.93
_diffrn_reflns_theta_min         3.20
_diffrn_ambient_temperature      298
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1640
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9967
_diffrn_measured_fraction_theta_max 0.8586
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   14.00   89.00   1.0000   26.3000
omega____ theta____ kappa____ phi______ frames
    -       19.9032   57.0000  -90.0000 75

#__ type_ start__ end____ width___ exp.time_
  2 omega   51.00   97.00   1.0000   26.3000
omega____ theta____ kappa____ phi______ frames
    -       19.9032  178.0000   90.0000 46

#__ type_ start__ end____ width___ exp.time_
  3 omega    3.00   44.00   1.0000   26.3000
omega____ theta____ kappa____ phi______ frames
    -       19.9032   57.0000  120.0000 41

#__ type_ start__ end____ width___ exp.time_
  4 omega   -9.00   58.00   1.0000   26.3000
omega____ theta____ kappa____ phi______ frames
    -       19.9032  -99.0000 -180.0000 67
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0202217000
_diffrn_orient_matrix_UB_12      0.1472884000
_diffrn_orient_matrix_UB_13      0.0112288000
_diffrn_orient_matrix_UB_21      -0.0364425000
_diffrn_orient_matrix_UB_22      0.0002551000
_diffrn_orient_matrix_UB_23      0.0185416000
_diffrn_orient_matrix_UB_31      0.0369534000
_diffrn_orient_matrix_UB_32      -0.0801781000
_diffrn_orient_matrix_UB_33      0.0207279000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_special_details          ?
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2480
_reflns_number_total             2944
_reflns_odcompleteness_completeness 99.67
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33c (release 11-04-2014 CrysAlis171 .NET)
(compiled Apr 11 2014,15:12:41)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33c (release 11-04-2014 CrysAlis171 .NET)
(compiled Apr 11 2014,15:12:41)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33c (release 11-04-2014 CrysAlis171 .NET)
(compiled Apr 11 2014,15:12:41)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         0.294
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     277
_refine_ls_number_reflns         2944
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0555
_refine_ls_R_factor_gt           0.0465
_refine_ls_restrained_S_all      1.084
_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)+(0.0494P)²+0.5281P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1138
_refine_ls_wR_factor_ref         0.1205
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Others
 Fixed Sof: O5(0.5) O1(0.5) O4(0.5) O2(0.5) O6(0.5) O7(0.5) O8(0.5) O9(0.5)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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
P1 P 0.44432(4) -0.08227(13) 0.13984(2) 0.03098(17) Uani 1 1 d . . .
N2 N 0.53743(13) 0.4352(5) 0.33119(7) 0.0393(4) Uani 1 1 d . . .
N1 N 0.68538(12) 0.0226(4) 0.37928(7) 0.0322(4) Uani 1 1 d . . .
O5 O 0.5202(3) 0.1281(8) 0.17963(14) 0.0529(9) Uani 0.50 1 d P . .
O1 O 0.4247(4) 0.1286(8) 0.19025(13) 0.0623(11) Uani 0.50 1 d P . .
O4 O 0.3784(3) 0.1308(8) 0.09416(13) 0.0375(7) Uani 0.50 1 d P . .
C10 C 0.45492(16) 0.4416(6) 0.41029(9) 0.0354(5) Uani 1 1 d . . .
N3 N 0.87190(15) -0.4511(6) 0.47410(10) 0.0485(6) Uani 1 1 d . . .
O2 O 0.4633(3) 0.1253(8) 0.09273(13) 0.0494(9) Uani 0.50 1 d P . .
O3 O 0.68949(15) 0.0343(6) 0.26169(7) 0.0557(5) Uani 1 1 d . . .
C7 C 0.46187(18) 0.6256(6) 0.30399(9) 0.0409(5) Uani 1 1 d . . .
O6 O 0.5417(2) -0.2793(9) 0.16459(17) 0.0575(10) Uani 0.50 1 d P . .
C6 C 0.53443(14) 0.3448(5) 0.38405(8) 0.0305(4) Uani 1 1 d . . .
C9 C 0.37672(16) 0.6344(6) 0.38274(9) 0.0397(5) Uani 1 1 d . . .
O7 O 0.3791(3) -0.2943(8) 0.16763(15) 0.0447(8) Uani 0.50 1 d P . .
O8 O 0.5136(2) -0.2908(8) 0.10622(15) 0.0483(8) Uani 0.50 1 d P . .
C1 C 0.61988(14) 0.1379(5) 0.41158(8) 0.0308(4) Uani 1 1 d . . .
N4 N 0.30325(19) 0.9239(6) 0.29776(12) 0.0545(6) Uani 1 1 d . . .
C2 C 0.76713(15) -0.1663(6) 0.39821(8) 0.0336(5) Uani 1 1 d . . .
C5 C 0.63979(16) 0.0497(6) 0.46793(9) 0.0362(5) Uani 1 1 d . . .
C4 C 0.72329(16) -0.1422(6) 0.48942(8) 0.0366(5) Uani 1 1 d . . .
C3 C 0.78998(14) -0.2591(5) 0.45461(8) 0.0330(4) Uani 1 1 d . . .
C8 C 0.37890(15) 0.7349(5) 0.32784(9) 0.0352(5) Uani 1 1 d . . .
O9 O 0.3509(2) -0.3063(8) 0.12367(16) 0.0451(8) Uani 0.50 1 d P . .
H4 H 0.7393(16) -0.193(6) 0.5279(10) 0.044(6) Uiso 1 1 d . . .
H2A H 0.8062(16) -0.235(6) 0.3723(9) 0.042(6) Uiso 1 1 d . . .
H5 H 0.6000(18) 0.130(6) 0.4915(10) 0.043(6) Uiso 1 1 d . . .
H3A H 0.8806(19) -0.510(7) 0.5076(11) 0.047(7) Uiso 1 1 d . . .
H1 H 0.6724(17) 0.073(6) 0.3435(11) 0.042(6) Uiso 1 1 d . . .
H7 H 0.4682(18) 0.673(7) 0.2698(11) 0.052(7) Uiso 1 1 d . . .
H3B H 0.909(2) -0.515(7) 0.4541(11) 0.051(8) Uiso 1 1 d . . .
H9 H 0.3161(18) 0.690(7) 0.4016(10) 0.053(7) Uiso 1 1 d . . .
H10 H 0.4537(18) 0.387(7) 0.4459(11) 0.057(8) Uiso 1 1 d . . .
H4A H 0.313(3) 1.014(10) 0.2647(17) 0.102(13) Uiso 1 1 d . . .
H4B H 0.266(3) 1.021(9) 0.3150(14) 0.077(11) Uiso 1 1 d . . .
H H 0.635(2) 0.075(9) 0.2400(14) 0.075(11) Uiso 1 1 d . . .
HA H 0.382(6) 0.27(2) 0.103(3) 0.23(3) Uiso 1 1 d . . .
HB H 0.728(3) -0.178(11) 0.2462(17) 0.115(13) Uiso 1 1 d . . .
H2 H 0.594(6) 0.33(2) 0.302(4) 0.31(4) Uiso 1 1 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 O5 1.523(3) . ?
P1 O1 1.566(3) . ?
P1 O4 1.548(3) . ?
P1 O2 1.492(3) . ?
P1 O6 1.536(3) . ?
P1 O7 1.478(3) . ?
P1 O8 1.586(3) . ?
P1 O9 1.529(3) . ?
P1 HA 1.83(8) . ?
N2 C7 1.339(3) . ?
N2 C6 1.338(3) . ?
N2 H2 1.20(9) . ?
N1 C1 1.348(3) . ?
N1 C2 1.336(3) . ?
N1 H1 0.87(3) . ?
O5 O1 1.311(5) . ?
O5 O6 1.794(5) . ?
O4 O2 1.108(5) . ?
O4 HA 0.61(8) . ?
C10 C6 1.371(3) . ?
C10 C9 1.370(3) . ?
C10 H10 0.89(3) . ?
N3 C3 1.349(3) . ?
N3 H3A 0.83(3) . ?
N3 H3B 0.79(3) . ?
O2 HA 1.28(7) . ?
O3 H 0.82(3) . ?
O3 HB 1.13(5) . ?
C7 C8 1.392(3) . ?
C7 H7 0.87(3) . ?
O6 O8 1.385(5) . ?
C6 C1 1.468(3) . ?
C9 C8 1.395(3) . ?
C9 H9 1.01(2) . ?
O7 O9 1.054(4) . ?
C1 C5 1.384(3) . ?
N4 C8 1.362(3) . ?
N4 H4A 0.91(4) . ?
N4 H4B 0.80(3) . ?
C2 C3 1.391(3) . ?
C2 H2A 0.92(2) . ?
C5 C4 1.373(3) . ?
C5 H5 0.90(2) . ?
C4 C3 1.404(3) . ?
C4 H4 0.94(2) . ?

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
O5 P1 O1 50.2(2) . . ?
O5 P1 O4 108.08(17) . . ?
O5 P1 O6 71.81(18) . . ?
O5 P1 O8 106.6(2) . . ?
O5 P1 O9 155.2(2) . . ?
O5 P1 HA 90(2) . . ?
O1 P1 O8 154.7(2) . . ?
O1 P1 HA 78(2) . . ?
O4 P1 O1 94.1(2) . . ?
O4 P1 O8 104.47(19) . . ?
O4 P1 HA 19(2) . . ?
O2 P1 O5 87.4(2) . . ?
O2 P1 O1 109.25(18) . . ?
O2 P1 O4 42.69(19) . . ?
O2 P1 O6 111.8(2) . . ?
O2 P1 O8 75.36(19) . . ?
O2 P1 O9 114.1(2) . . ?
O2 P1 HA 44(2) . . ?
O6 P1 O1 104.5(2) . . ?
O6 P1 O4 153.4(2) . . ?
O6 P1 O8 52.63(19) . . ?
O6 P1 HA 152(2) . . ?
O7 P1 O5 115.2(2) . . ?
O7 P1 O1 78.61(19) . . ?
O7 P1 O4 112.9(2) . . ?
O7 P1 O2 153.3(2) . . ?
O7 P1 O6 89.7(2) . . ?
O7 P1 O8 108.82(18) . . ?
O7 P1 O9 40.99(17) . . ?
O7 P1 HA 118(2) . . ?
O8 P1 HA 116(2) . . ?
O9 P1 O1 108.2(2) . . ?
O9 P1 O4 82.89(18) . . ?
O9 P1 O6 108.42(18) . . ?
O9 P1 O8 91.34(18) . . ?
O9 P1 HA 97(2) . . ?
C7 N2 H2 115(4) . . ?
C6 N2 C7 119.13(18) . . ?
C6 N2 H2 126(5) . . ?
C1 N1 H1 117.3(16) . . ?
C2 N1 C1 124.41(17) . . ?
C2 N1 H1 118.3(16) . . ?
P1 O5 O6 54.43(15) . . ?
O1 O5 P1 66.6(2) . . ?
O1 O5 O6 103.3(3) . . ?
O5 O1 P1 63.2(2) . . ?
P1 O4 HA 108(7) . . ?
O2 O4 P1 66.0(2) . . ?
O2 O4 HA 92(7) . . ?
C6 C10 H10 121.3(16) . . ?
C9 C10 C6 120.42(19) . . ?
C9 C10 H10 118.2(17) . . ?
C3 N3 H3A 118.0(18) . . ?
C3 N3 H3B 121.7(19) . . ?
H3A N3 H3B 120(3) . . ?
P1 O2 HA 82(4) . . ?
O4 O2 P1 71.3(2) . . ?
O4 O2 HA 28(4) . . ?
H O3 HB 110(3) . . ?
N2 C7 C8 123.3(2) . . ?
N2 C7 H7 114.2(17) . . ?
C8 C7 H7 122.5(17) . . ?
P1 O6 O5 53.76(15) . . ?
O8 O6 P1 65.56(19) . . ?
O8 O6 O5 102.6(3) . . ?
N2 C6 C10 120.99(19) . . ?
N2 C6 C1 116.40(17) . . ?
C10 C6 C1 122.61(18) . . ?
C10 C9 C8 119.61(19) . . ?
C10 C9 H9 119.2(15) . . ?
C8 C9 H9 121.0(15) . . ?
O9 O7 P1 72.1(2) . . ?
O6 O8 P1 61.81(19) . . ?
N1 C1 C6 117.33(17) . . ?
N1 C1 C5 116.66(18) . . ?
C5 C1 C6 126.01(18) . . ?
C8 N4 H4A 120(2) . . ?
C8 N4 H4B 118(2) . . ?
H4A N4 H4B 116(4) . . ?
N1 C2 C3 120.64(19) . . ?
N1 C2 H2A 117.4(14) . . ?
C3 C2 H2A 121.9(14) . . ?
C1 C5 H5 119.6(15) . . ?
C4 C5 C1 121.04(19) . . ?
C4 C5 H5 119.2(15) . . ?
C5 C4 C3 120.92(18) . . ?
C5 C4 H4 121.3(14) . . ?
C3 C4 H4 117.7(14) . . ?
N3 C3 C2 121.14(19) . . ?
N3 C3 C4 122.53(19) . . ?
C2 C3 C4 116.32(19) . . ?
C7 C8 C9 116.57(19) . . ?
N4 C8 C7 120.7(2) . . ?
N4 C8 C9 122.7(2) . . ?
O7 O9 P1 66.9(2) . . ?

####################################################################### 
# 
# 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_BiPy-PA
_database_code_depnum_ccdc_archive 'CCDC 1046997'
_audit_update_record             
;
2015-02-03 deposited with the CCDC.
2016-01-29 downloaded from the CCDC.
;
_audit_creation_date             2015-01-30
_audit_creation_method           
;
  Olex2 1.2-ac2
  (compiled Nov  7 2012 10:34:12, GUI svn.r4372)
;
_chemical_name_common            
"2,2'-bipyridinium-5-amino5'-ammonium bis-dihydrogen Phosphate"
_chemical_name_systematic        BiPy-PA
_chemical_formula_moiety         'C10 H12 N4, 2(H2 O4 P)'
_chemical_formula_sum            'C10 H16 N4 O8 P2'
_chemical_formula_weight         382.21
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C10 H5 O4 N2 P2'
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'

_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_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   8.6237(9)
_cell_length_b                   8.9142(10)
_cell_length_c                   10.2301(8)
_cell_angle_alpha                73.441(9)
_cell_angle_beta                 85.209(8)
_cell_angle_gamma                83.669(9)
_cell_volume                     748.10(13)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3033
_cell_measurement_temperature    298
_cell_measurement_theta_max      28.6480
_cell_measurement_theta_min      3.5080
_exptl_absorpt_coefficient_mu    0.343
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84867
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33c (release 11-04-2014 CrysAlis171 .NET)
(compiled Apr 11 2014,15:12:41)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.692
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             396
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0246
_diffrn_reflns_av_unetI/netI     0.0428
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5795
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         29.08
_diffrn_reflns_theta_min         3.07
_diffrn_ambient_temperature      298
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1640
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9977
_diffrn_measured_fraction_theta_max 0.8548
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   -2.00   89.00   1.0000    2.3800
omega____ theta____ kappa____ phi______ frames
    -       19.9032   57.0000    0.0000 91

#__ type_ start__ end____ width___ exp.time_
  2 omega   60.00   89.00   1.0000    2.3800
omega____ theta____ kappa____ phi______ frames
    -       19.9032   57.0000 -150.0000 29

#__ type_ start__ end____ width___ exp.time_
  3 omega  -11.00   91.00   1.0000    2.3800
omega____ theta____ kappa____ phi______ frames
    -       19.9032   77.0000   60.0000 102

#__ type_ start__ end____ width___ exp.time_
  4 omega  -20.00   63.00   1.0000    2.3800
omega____ theta____ kappa____ phi______ frames
    -       19.9032  -99.0000 -150.0000 83

#__ type_ start__ end____ width___ exp.time_
  5 omega  -41.00   17.00   1.0000    2.3800
omega____ theta____ kappa____ phi______ frames
    -       19.9032  -57.0000  -90.0000 58

#__ type_ start__ end____ width___ exp.time_
  6 omega  -56.00  -21.00   1.0000    2.3800
omega____ theta____ kappa____ phi______ frames
    -      -19.9032  -57.0000   90.0000 35
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0180732000
_diffrn_orient_matrix_UB_12      0.0792417000
_diffrn_orient_matrix_UB_13      -0.0171584000
_diffrn_orient_matrix_UB_21      -0.0807248000
_diffrn_orient_matrix_UB_22      0.0256794000
_diffrn_orient_matrix_UB_23      -0.0041866000
_diffrn_orient_matrix_UB_31      -0.0050689000
_diffrn_orient_matrix_UB_32      -0.0030506000
_diffrn_orient_matrix_UB_33      0.0702569000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2877
_reflns_number_total             3425
_reflns_odcompleteness_completeness 99.77
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33c (release 11-04-2014 CrysAlis171 .NET)
(compiled Apr 11 2014,15:12:41)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33c (release 11-04-2014 CrysAlis171 .NET)
(compiled Apr 11 2014,15:12:41)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33c (release 11-04-2014 CrysAlis171 .NET)
(compiled Apr 11 2014,15:12:41)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    
;
olex2.solve (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard,
H. Puschmann, in preparation, 2011)
;
_refine_diff_density_max         0.415
_refine_diff_density_min         -0.425
_refine_diff_density_rms         0.064
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3425
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0507
_refine_ls_R_factor_gt           0.0414
_refine_ls_restrained_S_all      1.054
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0410P)²+0.4082P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0980
_refine_ls_wR_factor_ref         0.1066
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  H4 of C4, {H3A,H3B} of N3, H9 of C9, H2A of C2, H5 of C5, H10 of C10, H7 of
  C7, {H4A,H4B} of N4
 At 1.5 times of:
  H2B of O2, H1 of O1, H5A of O5, H6 of O6
2.a Rotating group:
 N4(H4A,H4B)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C7(H7), C9(H9), C2(H2A), C5(H5), C10(H10)
2.c Idealised tetrahedral OH refined as rotating group:
 O2(H2B), O1(H1), O5(H5A), O6(H6)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
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
P1 P 0.25223(6) 0.00500(6) 0.98486(5) 0.02325(14) Uani 1 1 d . . .
P2 P 0.12446(6) 0.45174(6) 0.68301(5) 0.02616(15) Uani 1 1 d . . .
O4 O 0.35830(17) 0.11595(18) 0.89023(16) 0.0323(4) Uani 1 1 d . . .
O7 O 0.11983(19) 0.59701(18) 0.56466(16) 0.0355(4) Uani 1 1 d . . .
O2 O 0.34961(17) -0.12206(18) 1.09236(15) 0.0319(4) Uani 1 1 d . . .
H2B H 0.4413 -0.1027 1.0824 0.048 Uiso 1 1 calc R . .
O1 O 0.13914(17) 0.0979(2) 1.06890(17) 0.0354(4) Uani 1 1 d . . .
H1 H 0.0488 0.0801 1.0641 0.053 Uiso 1 1 calc R . .
O5 O 0.29275(18) 0.3646(2) 0.68091(16) 0.0374(4) Uani 1 1 d . . .
H5A H 0.3026 0.2924 0.7512 0.056 Uiso 1 1 calc R . .
O8 O 0.08603(18) 0.4781(2) 0.82160(16) 0.0363(4) Uani 1 1 d . . .
O3 O 0.15850(16) -0.08051(18) 0.91572(15) 0.0305(3) Uani 1 1 d . . .
N2 N 0.2939(2) 0.9168(2) 0.65607(19) 0.0295(4) Uani 1 1 d . . .
N1 N 0.5088(2) 0.7312(2) 0.82540(19) 0.0320(4) Uani 1 1 d . . .
C3 C 0.7001(2) 0.5115(2) 0.8804(2) 0.0259(4) Uani 1 1 d . . .
O6 O 0.01076(19) 0.33521(18) 0.66449(16) 0.0337(4) Uani 1 1 d . . .
H6 H -0.0258 0.3689 0.5891 0.051 Uiso 1 1 calc R . .
C4 C 0.6830(3) 0.4778(3) 0.7591(2) 0.0296(5) Uani 1 1 d . . .
H4 H 0.7392 0.3914 0.7386 0.035 Uiso 1 1 calc R . .
N3 N 0.8183(2) 0.4185(2) 0.9709(2) 0.0285(4) Uani 1 1 d . . .
H3A H 0.917(3) 0.429(3) 0.927(3) 0.034 Uiso 1 1 d . . .
H3B H 0.830(3) 0.452(3) 1.043(3) 0.034 Uiso 1 1 d . . .
N4 N 0.1094(3) 1.1680(2) 0.3561(2) 0.0412(5) Uani 1 1 d . . .
H4A H 0.0891 1.1389 0.2866 0.049 Uiso 1 1 d R . .
H4B H 0.0235 1.1853 0.4009 0.049 Uiso 1 1 d R . .
C7 C 0.1989(3) 1.0306(3) 0.5789(2) 0.0305(5) Uani 1 1 d . . .
H7 H 0.1313 1.0956 0.6191 0.037 Uiso 1 1 calc R . .
C1 C 0.4978(2) 0.7025(2) 0.7050(2) 0.0270(4) Uani 1 1 d . . .
C6 C 0.3950(2) 0.8170(2) 0.6082(2) 0.0269(4) Uani 1 1 d . . .
C8 C 0.2012(3) 1.0518(2) 0.4387(2) 0.0292(5) Uani 1 1 d . . .
C9 C 0.3051(3) 0.9490(3) 0.3864(2) 0.0357(5) Uani 1 1 d . . .
H9 H 0.3099 0.9586 0.2932 0.043 Uiso 1 1 calc R . .
C2 C 0.6108(3) 0.6367(3) 0.9111(2) 0.0308(5) Uani 1 1 d . . .
H2A H 0.6218 0.6561 0.9943 0.037 Uiso 1 1 calc R . .
C5 C 0.5804(3) 0.5757(3) 0.6694(2) 0.0327(5) Uani 1 1 d . . .
H5 H 0.5666 0.5572 0.5862 0.039 Uiso 1 1 calc R . .
C10 C 0.4003(3) 0.8340(3) 0.4694(2) 0.0330(5) Uani 1 1 d . . .
H10 H 0.4688 0.7671 0.4321 0.040 Uiso 1 1 calc R . .
H3C H 0.803(3) 0.312(3) 1.004(3) 0.048(8) Uiso 1 1 d . . .
H2 H 0.283(3) 0.906(3) 0.742(3) 0.048(8) Uiso 1 1 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 O4 1.5026(16) . ?
P1 O2 1.5595(15) . ?
P1 O1 1.5696(15) . ?
P1 O3 1.5078(15) . ?
P2 O7 1.4991(16) . ?
P2 O5 1.5703(16) . ?
P2 O8 1.5066(16) . ?
P2 O6 1.5634(16) . ?
O2 H2B 0.8200 . ?
O1 H1 0.8200 . ?
O5 H5A 0.8200 . ?
N2 C7 1.339(3) . ?
N2 C6 1.341(3) . ?
N2 H2 0.86(3) . ?
N1 C1 1.340(3) . ?
N1 C2 1.340(3) . ?
C3 C4 1.380(3) . ?
C3 N3 1.455(3) . ?
C3 C2 1.381(3) . ?
O6 H6 0.8200 . ?
C4 H4 0.9300 . ?
C4 C5 1.377(3) . ?
N3 H3A 0.93(3) . ?
N3 H3B 0.89(3) . ?
N3 H3C 0.94(3) . ?
N4 H4A 0.8605 . ?
N4 H4B 0.8602 . ?
N4 C8 1.359(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.391(3) . ?
C1 C6 1.476(3) . ?
C1 C5 1.390(3) . ?
C6 C10 1.382(3) . ?
C8 C9 1.395(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.371(3) . ?
C2 H2A 0.9300 . ?
C5 H5 0.9300 . ?
C10 H10 0.9300 . ?

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
O4 P1 O2 109.98(8) . . ?
O4 P1 O1 109.05(9) . . ?
O4 P1 O3 114.83(9) . . ?
O2 P1 O1 105.64(9) . . ?
O3 P1 O2 107.25(9) . . ?
O3 P1 O1 109.68(8) . . ?
O7 P2 O5 107.66(9) . . ?
O7 P2 O8 115.61(10) . . ?
O7 P2 O6 110.58(9) . . ?
O8 P2 O5 109.02(9) . . ?
O8 P2 O6 107.76(9) . . ?
O6 P2 O5 105.77(9) . . ?
P1 O2 H2B 109.5 . . ?
P1 O1 H1 109.5 . . ?
P2 O5 H5A 109.5 . . ?
C7 N2 C6 124.6(2) . . ?
C7 N2 H2 115.5(19) . . ?
C6 N2 H2 119.8(19) . . ?
C1 N1 C2 117.49(19) . . ?
C4 C3 N3 119.01(19) . . ?
C4 C3 C2 119.9(2) . . ?
C2 C3 N3 121.04(19) . . ?
P2 O6 H6 109.5 . . ?
C3 C4 H4 120.9 . . ?
C5 C4 C3 118.1(2) . . ?
C5 C4 H4 120.9 . . ?
C3 N3 H3A 110.0(15) . . ?
C3 N3 H3B 114.7(16) . . ?
C3 N3 H3C 114.4(17) . . ?
H3A N3 H3B 101(2) . . ?
H3A N3 H3C 109(2) . . ?
H3B N3 H3C 106(2) . . ?
H4A N4 H4B 109.4 . . ?
C8 N4 H4A 109.2 . . ?
C8 N4 H4B 109.0 . . ?
N2 C7 H7 120.0 . . ?
N2 C7 C8 120.0(2) . . ?
C8 C7 H7 120.0 . . ?
N1 C1 C6 116.09(19) . . ?
N1 C1 C5 123.0(2) . . ?
C5 C1 C6 120.84(19) . . ?
N2 C6 C1 118.30(19) . . ?
N2 C6 C10 117.1(2) . . ?
C10 C6 C1 124.55(19) . . ?
N4 C8 C7 122.0(2) . . ?
N4 C8 C9 121.5(2) . . ?
C7 C8 C9 116.5(2) . . ?
C8 C9 H9 119.3 . . ?
C10 C9 C8 121.4(2) . . ?
C10 C9 H9 119.3 . . ?
N1 C2 C3 122.4(2) . . ?
N1 C2 H2A 118.8 . . ?
C3 C2 H2A 118.8 . . ?
C4 C5 C1 118.9(2) . . ?
C4 C5 H5 120.5 . . ?
C1 C5 H5 120.5 . . ?
C6 C10 H10 119.8 . . ?
C9 C10 C6 120.4(2) . . ?
C9 C10 H10 119.8 . . ?

