# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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. 
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data_A4
_database_code_depnum_ccdc_archive 'CCDC 1566062'
_audit_update_record             
;
2017-08-14 deposited with the CCDC.
2017-09-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C6 H6 F3 N3 O2'
_chemical_formula_weight         209.14

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'
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'
F F 0.0171 0.0103 '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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.778(8)
_cell_length_b                   10.165(9)
_cell_length_c                   10.918(9)
_cell_angle_alpha                78.86(2)
_cell_angle_beta                 69.57(3)
_cell_angle_gamma                72.29(4)
_cell_volume                     865.5(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    558
_cell_measurement_theta_min      2.56
_cell_measurement_theta_max      20.57

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.605
_exptl_crystal_F_000             424
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.04
_exptl_absorpt_coefficient_mu    0.162
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.792
_exptl_absorpt_correction_T_max  0.994
_exptl_absorpt_process_details   
'Blessing, R. H. (1995) Acta Cryst., A51, 33-38'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5968
_diffrn_reflns_av_unetI/netI     0.0863
_diffrn_reflns_av_R_equivalents  0.0599
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.000
_diffrn_reflns_theta_max         25.039
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measured_fraction_theta_full 0.969
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_Laue_measured_fraction_full 0.969
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_point_group_measured_fraction_full 0.969
_reflns_number_total             2963
_reflns_number_gt                1193
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1066P)²+0.5136P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2963
_refine_ls_number_parameters     298
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1914
_refine_ls_R_factor_gt           0.0804
_refine_ls_wR_factor_ref         0.2692
_refine_ls_wR_factor_gt          0.2085
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
O4 O 0.1625(5) 0.4192(4) 0.2491(4) 0.0786(13) Uani 1 1 d . . . . .
O3 O 0.3363(5) 0.3615(4) 0.0519(4) 0.0785(13) Uani 1 1 d . . . . .
F5 F 0.1332(6) 0.5807(4) -0.0458(5) 0.1247(17) Uani 1 1 d . . . . .
O2 O 0.0459(6) 0.1131(5) 0.6043(5) 0.1106(18) Uani 1 1 d . . . . .
O1 O -0.1981(5) 0.1086(4) 0.7599(4) 0.0782(13) Uani 1 1 d . . . . .
C5B6 C 0.6723(7) -0.0975(6) 0.1383(6) 0.0750(18) Uani 1 1 d . . . . .
H5B6 H 0.7649 -0.1572 0.0860 0.090 Uiso 1 1 calc R U . . .
N4B1 N 0.6059(6) -0.1427(5) 0.2647(5) 0.0724(14) Uani 1 1 d . . . . .
N1B4 N 0.4778(5) 0.1163(5) 0.1620(4) 0.0632(13) Uani 1 1 d . . . . .
H1B H 0.4382 0.1983 0.1292 0.076 Uiso 1 1 calc R U . . .
N1A4 N 0.3238(6) 0.6305(5) 0.3346(5) 0.0695(14) Uani 1 1 d . . . . .
H1A H 0.2848 0.7137 0.3040 0.083 Uiso 1 1 calc R U . . .
C11 C 0.2227(7) 0.4394(6) 0.1297(6) 0.0595(15) Uani 1 1 d . . . . .
C3B2 C 0.4746(7) -0.0545(6) 0.3390(6) 0.0701(17) Uani 1 1 d . . . . .
H3B2 H 0.4277 -0.0819 0.4272 0.084 Uiso 0.5 1 calc R U P A 2
C2B3 C 0.4060(7) 0.0795(6) 0.2861(6) 0.0657(16) Uani 1 1 d . . . . .
H2B3 H 0.3129 0.1398 0.3374 0.079 Uiso 0.5 1 calc R U P B 1
C9 C -0.0456(8) 0.0611(6) 0.7012(6) 0.0652(17) Uani 1 1 d . . . . .
C6A5 C 0.4746(7) 0.5585(6) 0.2669(6) 0.0727(18) Uani 1 1 d . . . . .
H6A5 H 0.5364 0.5957 0.1870 0.087 Uiso 1 1 calc R U . . .
C2A3 C 0.2314(7) 0.5795(6) 0.4467(6) 0.0635(16) Uani 1 1 d . . . . .
H2A3 H 0.1248 0.6309 0.4906 0.076 Uiso 0.5 1 calc R U P C 1
F6 F 0.2644(8) 0.6581(5) 0.0336(6) 0.161(2) Uani 1 1 d . . . . .
C12 C 0.1536(9) 0.5833(7) 0.0671(7) 0.085(2) Uani 1 1 d . . . . .
F4 F 0.0180(7) 0.6523(6) 0.1367(5) 0.204(3) Uani 1 1 d . . . . .
C6B5 C 0.6114(7) 0.0307(6) 0.0832(6) 0.0677(17) Uani 1 1 d . . . . .
H6B5 H 0.6593 0.0585 -0.0048 0.081 Uiso 1 1 calc R U . . .
C10 C 0.0359(11) -0.0795(9) 0.7627(9) 0.083(2) Uani 1 1 d . . . . .
C5A6 C 0.5349(8) 0.4284(6) 0.3192(6) 0.0761(19) Uani 1 1 d . . . . .
H5A6 H 0.6396 0.3766 0.2723 0.091 Uiso 1 1 calc R U . . .
N4A1 N 0.4511(7) 0.3701(5) 0.4355(5) 0.0797(16) Uani 1 1 d . . . . .
C3A2 C 0.3006(8) 0.4428(7) 0.4982(6) 0.0794(19) Uani 1 1 d . . . . .
H3A2 H 0.2383 0.4046 0.5772 0.095 Uiso 0.5 1 calc R U P D 2
N2B N 0.2791(11) 0.1527(9) 0.3689(8) 0.066(3) Uani 0.5 1 d . . P E 2
HB1 H 0.2316 0.2362 0.3444 0.079 Uiso 0.5 1 calc R U P E 2
HB2 H 0.2420 0.1180 0.4485 0.079 Uiso 0.5 1 calc R U P E 2
N2'B N 0.3936(13) -0.0780(10) 0.4629(9) 0.092(4) Uani 0.5 1 d . . P F 1
HB'1 H 0.4236 -0.1570 0.5050 0.110 Uiso 0.5 1 calc R U P F 1
HB'2 H 0.3103 -0.0144 0.5026 0.110 Uiso 0.5 1 calc R U P F 1
N2A N 0.0822(12) 0.6350(11) 0.5192(9) 0.088(3) Uani 0.5 1 d . . P G 2
HA1 H 0.0292 0.7169 0.4959 0.106 Uiso 0.5 1 calc R U P G 2
HA2 H 0.0357 0.5901 0.5908 0.106 Uiso 0.5 1 calc R U P G 2
N2'A N 0.1996(13) 0.4050(10) 0.6082(10) 0.097(4) Uani 0.5 1 d . . P H 1
HA'1 H 0.2287 0.3244 0.6483 0.116 Uiso 0.5 1 calc R U P H 1
HA'2 H 0.1031 0.4603 0.6416 0.116 Uiso 0.5 1 calc R U P H 1
F1 F -0.026(3) -0.1747(15) 0.768(2) 0.145(8) Uani 0.6 1 d . . P I 1
F3 F 0.0189(17) -0.0621(13) 0.8898(10) 0.122(5) Uani 0.6 1 d . . P I 1
F1A F 0.147(5) -0.088(2) 0.800(5) 0.180(16) Uani 0.4 1 d . . P I 2
F2 F 0.1963(19) -0.1168(19) 0.7135(19) 0.149(9) Uani 0.6 1 d . . P I 1
F2A F -0.083(3) -0.144(2) 0.839(2) 0.109(9) Uani 0.4 1 d . . P I 2
F3A F 0.107(4) -0.1743(17) 0.6605(17) 0.148(8) Uani 0.4 1 d . . P I 2


_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
O4 C11 1.226(6) . ?
O3 C11 1.237(6) . ?
F5 C12 1.312(8) . ?
O2 C9 1.221(6) . ?
O1 C9 1.250(6) . ?
C5B6 N4B1 1.346(7) . ?
C5B6 C6B5 1.358(7) . ?
C5B6 H5B6 0.9300 . ?
N4B1 C3B2 1.337(7) . ?
N1B4 C2B3 1.313(7) . ?
N1B4 C6B5 1.355(6) . ?
N1B4 H1B 0.8600 . ?
N1A4 C2A3 1.319(7) . ?
N1A4 C6A5 1.331(7) . ?
N1A4 H1A 0.8600 . ?
C11 C12 1.529(8) . ?
C3B2 N2'B 1.304(10) . ?
C3B2 C2B3 1.411(8) . ?
C3B2 H3B2 0.9300 . ?
C2B3 N2B 1.290(9) . ?
C2B3 H2B3 0.9300 . ?
C9 C10 1.533(8) . ?
C6A5 C5A6 1.360(7) . ?
C6A5 H6A5 0.9300 . ?
C2A3 N2A 1.288(10) . ?
C2A3 C3A2 1.428(8) . ?
C2A3 H2A3 0.9300 . ?
F6 C12 1.324(8) . ?
C12 F4 1.246(7) . ?
C6B5 H6B5 0.9300 . ?
C10 F1A 1.15(2) . ?
C10 F1 1.229(16) . ?
C10 F2 1.281(17) . ?
C10 F2A 1.35(3) . ?
C10 F3 1.383(16) . ?
C10 F3A 1.458(18) . ?
C5A6 N4A1 1.351(7) . ?
C5A6 H5A6 0.9300 . ?
N4A1 C3A2 1.316(7) . ?
C3A2 N2'A 1.290(10) . ?
C3A2 H3A2 0.9300 . ?
N2B HB1 0.8600 . ?
N2B HB2 0.8600 . ?
N2'B HB'1 0.8600 . ?
N2'B HB'2 0.8600 . ?
N2A HA1 0.8600 . ?
N2A HA2 0.8600 . ?
N2'A HA'1 0.8600 . ?
N2'A HA'2 0.8600 . ?

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
N4B1 C5B6 C6B5 123.5(6) . . ?
N4B1 C5B6 H5B6 118.3 . . ?
C6B5 C5B6 H5B6 118.3 . . ?
C3B2 N4B1 C5B6 117.4(5) . . ?
C2B3 N1B4 C6B5 122.9(5) . . ?
C2B3 N1B4 H1B 118.5 . . ?
C6B5 N1B4 H1B 118.5 . . ?
C2A3 N1A4 C6A5 122.8(5) . . ?
C2A3 N1A4 H1A 118.6 . . ?
C6A5 N1A4 H1A 118.6 . . ?
O4 C11 O3 129.4(5) . . ?
O4 C11 C12 116.0(5) . . ?
O3 C11 C12 114.6(5) . . ?
N2'B C3B2 N4B1 126.7(7) . . ?
N2'B C3B2 C2B3 112.0(7) . . ?
N4B1 C3B2 C2B3 121.3(5) . . ?
N4B1 C3B2 H3B2 119.4 . . ?
C2B3 C3B2 H3B2 119.4 . . ?
N2B C2B3 N1B4 127.7(7) . . ?
N2B C2B3 C3B2 114.4(6) . . ?
N1B4 C2B3 C3B2 117.8(5) . . ?
N1B4 C2B3 H2B3 121.1 . . ?
C3B2 C2B3 H2B3 121.1 . . ?
O2 C9 O1 128.7(5) . . ?
O2 C9 C10 116.6(6) . . ?
O1 C9 C10 114.6(6) . . ?
N1A4 C6A5 C5A6 117.4(6) . . ?
N1A4 C6A5 H6A5 121.3 . . ?
C5A6 C6A5 H6A5 121.3 . . ?
N2A C2A3 N1A4 129.3(7) . . ?
N2A C2A3 C3A2 112.9(7) . . ?
N1A4 C2A3 C3A2 117.8(5) . . ?
N1A4 C2A3 H2A3 121.1 . . ?
C3A2 C2A3 H2A3 121.1 . . ?
F4 C12 F5 107.0(7) . . ?
F4 C12 F6 107.6(8) . . ?
F5 C12 F6 102.2(6) . . ?
F4 C12 C11 115.3(6) . . ?
F5 C12 C11 113.4(6) . . ?
F6 C12 C11 110.4(6) . . ?
N1B4 C6B5 C5B6 117.1(5) . . ?
N1B4 C6B5 H6B5 121.4 . . ?
C5B6 C6B5 H6B5 121.4 . . ?
F1 C10 F2 110.8(14) . . ?
F1A C10 F2A 118(2) . . ?
F1 C10 F3 107.6(13) . . ?
F2 C10 F3 101.1(14) . . ?
F1A C10 F3A 104(2) . . ?
F2A C10 F3A 95.8(17) . . ?
F1A C10 C9 119.1(12) . . ?
F1 C10 C9 115.3(11) . . ?
F2 C10 C9 113.7(11) . . ?
F2A C10 C9 110.0(12) . . ?
F3 C10 C9 107.2(8) . . ?
F3A C10 C9 106.8(9) . . ?
N4A1 C5A6 C6A5 123.6(5) . . ?
N4A1 C5A6 H5A6 118.2 . . ?
C6A5 C5A6 H5A6 118.2 . . ?
C3A2 N4A1 C5A6 117.4(5) . . ?
N2'A C3A2 N4A1 126.9(8) . . ?
N2'A C3A2 C2A3 112.1(7) . . ?
N4A1 C3A2 C2A3 121.0(6) . . ?
N4A1 C3A2 H3A2 119.5 . . ?
C2A3 C3A2 H3A2 119.5 . . ?
C2B3 N2B HB1 120.0 . . ?
C2B3 N2B HB2 120.0 . . ?
HB1 N2B HB2 120.0 . . ?
C3B2 N2'B HB'1 120.0 . . ?
C3B2 N2'B HB'2 120.0 . . ?
HB'1 N2'B HB'2 120.0 . . ?
C2A3 N2A HA1 120.0 . . ?
C2A3 N2A HA2 120.0 . . ?
HA1 N2A HA2 120.0 . . ?
C3A2 N2'A HA'1 120.0 . . ?
C3A2 N2'A HA'2 120.0 . . ?
HA'1 N2'A HA'2 120.0 . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6B5 C5B6 N4B1 C3B2 -1.1(10) . . . . ?
C5B6 N4B1 C3B2 N2'B -179.6(8) . . . . ?
C5B6 N4B1 C3B2 C2B3 1.5(9) . . . . ?
C6B5 N1B4 C2B3 N2B 180.0(7) . . . . ?
C6B5 N1B4 C2B3 C3B2 1.3(8) . . . . ?
N4B1 C3B2 C2B3 N2B 179.5(7) . . . . ?
N2'B C3B2 C2B3 N1B4 179.3(7) . . . . ?
N4B1 C3B2 C2B3 N1B4 -1.7(9) . . . . ?
C2A3 N1A4 C6A5 C5A6 -1.6(9) . . . . ?
C6A5 N1A4 C2A3 N2A -177.0(8) . . . . ?
C6A5 N1A4 C2A3 C3A2 2.1(9) . . . . ?
O4 C11 C12 F4 -16.6(11) . . . . ?
O3 C11 C12 F4 165.7(7) . . . . ?
O4 C11 C12 F5 -140.5(6) . . . . ?
O3 C11 C12 F5 41.9(8) . . . . ?
O4 C11 C12 F6 105.5(7) . . . . ?
O3 C11 C12 F6 -72.2(8) . . . . ?
C2B3 N1B4 C6B5 C5B6 -0.9(9) . . . . ?
N4B1 C5B6 C6B5 N1B4 0.8(10) . . . . ?
O2 C9 C10 F1A 59(3) . . . . ?
O1 C9 C10 F1A -119(3) . . . . ?
O2 C9 C10 F1 -121.2(15) . . . . ?
O1 C9 C10 F1 60.3(16) . . . . ?
O2 C9 C10 F2 8.3(19) . . . . ?
O1 C9 C10 F2 -170.2(15) . . . . ?
O2 C9 C10 F2A -160.8(15) . . . . ?
O1 C9 C10 F2A 20.7(18) . . . . ?
O2 C9 C10 F3 119.1(10) . . . . ?
O1 C9 C10 F3 -59.4(12) . . . . ?
O2 C9 C10 F3A -58(2) . . . . ?
O1 C9 C10 F3A 123.5(17) . . . . ?
N1A4 C6A5 C5A6 N4A1 -0.8(10) . . . . ?
C6A5 C5A6 N4A1 C3A2 2.5(10) . . . . ?
C5A6 N4A1 C3A2 N2'A 178.4(9) . . . . ?
C5A6 N4A1 C3A2 C2A3 -1.9(10) . . . . ?
N1A4 C2A3 C3A2 N2'A 179.5(8) . . . . ?
N2A C2A3 C3A2 N4A1 179.0(8) . . . . ?
N1A4 C2A3 C3A2 N4A1 -0.3(9) . . . . ?

_refine_diff_density_max         0.280
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.059

####################################################################### 
# 
# 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_B3
_database_code_depnum_ccdc_archive 'CCDC 1566065'
_audit_update_record             
;
2017-08-14 deposited with the CCDC.
2017-09-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H19 N2 O12 P3'
_chemical_formula_weight         476.20

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'
S S 0.1246 0.1234 '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           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   21.4140(16)
_cell_length_b                   9.4256(9)
_cell_length_c                   9.4548(7)
_cell_angle_alpha                90
_cell_angle_beta                 99.380(5)
_cell_angle_gamma                90
_cell_volume                     1882.8(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    812
_cell_measurement_theta_min      3.11
_cell_measurement_theta_max      24.05

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.680
_exptl_crystal_F_000             984
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    0.384
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.741
_exptl_absorpt_correction_T_max  0.981
_exptl_absorpt_process_details   
'Blessing, R. H. (1995) Acta Cryst., A51, 33-38'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3051
_diffrn_reflns_av_unetI/netI     0.0396
_diffrn_reflns_av_R_equivalents  0.0255
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         1.928
_diffrn_reflns_theta_max         25.049
_diffrn_reflns_theta_full        25.049
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measured_fraction_theta_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_point_group_measured_fraction_full 0.974
_reflns_number_total             1626
_reflns_number_gt                1264
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0502P)²+3.3769P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1626
_refine_ls_number_parameters     141
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0599
_refine_ls_R_factor_gt           0.0435
_refine_ls_wR_factor_ref         0.1143
_refine_ls_wR_factor_gt          0.1031
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
P2 P 0.5000 0.03256(11) 0.2500 0.0235(3) Uani 1 2 d S T P . .
P1 P 0.29002(4) 0.04987(8) 0.30811(8) 0.0228(2) Uani 1 1 d . . . . .
O1 O 0.25264(10) -0.0827(2) 0.3190(2) 0.0347(6) Uani 1 1 d . . . . .
O3 O 0.32732(10) 0.0590(2) 0.1871(2) 0.0332(6) Uani 1 1 d . . . . .
O6 O 0.44404(10) 0.1385(2) 0.2274(2) 0.0346(6) Uani 1 1 d . . . . .
H6P H 0.4105 0.0946 0.2156 0.052 Uiso 1 1 calc R U . . .
O5 O 0.50079(12) -0.0608(2) 0.1208(2) 0.0399(6) Uani 1 1 d . . . . .
H5P H 0.5012 -0.0111 0.0498 0.060 Uiso 0.5 1 calc R U P . .
N1 N 0.65917(12) 0.5455(3) -0.0268(3) 0.0330(7) Uani 1 1 d . . . . .
H1N H 0.6886 0.5484 -0.0787 0.040 Uiso 1 1 calc R U . . .
C1 C 0.63638(17) 0.6663(4) 0.0147(4) 0.0431(9) Uani 1 1 d . . . . .
H1 H 0.6525 0.7524 -0.0111 0.052 Uiso 1 1 calc R U . . .
C2 C 0.58910(19) 0.6639(5) 0.0955(4) 0.0574(12) Uani 1 1 d . . . . .
H2 H 0.5725 0.7487 0.1233 0.069 Uiso 1 1 calc R U . . .
C3 C 0.56575(17) 0.5373(6) 0.1362(4) 0.0568(13) Uani 1 1 d . . . . .
C5 C 0.63816(17) 0.4198(4) 0.0091(4) 0.0399(9) Uani 1 1 d . . . . .
H5 H 0.6553 0.3368 -0.0216 0.048 Uiso 1 1 calc R U . . .
C4 C 0.59134(18) 0.4134(5) 0.0911(4) 0.0534(11) Uani 1 1 d . . . . .
H4 H 0.5766 0.3258 0.1167 0.064 Uiso 1 1 calc R U . . .
O4 O 0.24074(11) 0.1716(3) 0.3006(3) 0.0518(8) Uani 1 1 d . . . . .
H4P H 0.2585 0.2480 0.2949 0.078 Uiso 1 1 calc R U . . .
O2 O 0.33889(12) 0.0728(3) 0.4479(2) 0.0474(7) Uani 1 1 d . . . . .
H2P H 0.3201 0.0794 0.5166 0.071 Uiso 1 1 calc R U . . .
C6 C 0.5138(3) 0.4847(8) 0.2180(6) 0.0287(15) Uani 0.5 1 d . . P . .
H6 H 0.5052 0.3888 0.2280 0.034 Uiso 0.5 1 calc R U P . .
C6A C 0.5175(3) 0.5846(8) 0.2276(8) 0.0350(17) Uani 0.5 1 d . . P . .
H6A H 0.5105 0.6801 0.2442 0.042 Uiso 0.5 1 calc R U P . .


_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
P2 O5 1.508(2) . ?
P2 O5 1.508(2) 2_655 ?
P2 O6 1.548(2) 2_655 ?
P2 O6 1.548(2) . ?
P1 O1 1.497(2) . ?
P1 O3 1.501(2) . ?
P1 O4 1.553(2) . ?
P1 O2 1.562(2) . ?
O6 H6P 0.8200 . ?
O5 H5P 0.8200 . ?
N1 C1 1.323(4) . ?
N1 C5 1.331(4) . ?
N1 H1N 0.8600 . ?
C1 C2 1.365(5) . ?
C1 H1 0.9300 . ?
C2 C3 1.373(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.386(6) . ?
C3 C6A 1.518(7) . ?
C3 C6 1.537(7) . ?
C5 C4 1.365(5) . ?
C5 H5 0.9300 . ?
C4 H4 0.9300 . ?
O4 H4P 0.8200 . ?
O2 H2P 0.8200 . ?
C6 C6A 1.309(8) 2_655 ?
C6 H6 0.9300 . ?
C6A C6 1.309(8) 2_655 ?
C6A H6A 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
O5 P2 O5 108.61(19) . 2_655 ?
O5 P2 O6 112.18(13) . 2_655 ?
O5 P2 O6 112.05(13) 2_655 2_655 ?
O5 P2 O6 112.05(13) . . ?
O5 P2 O6 112.18(13) 2_655 . ?
O6 P2 O6 99.63(17) 2_655 . ?
O1 P1 O3 117.21(12) . . ?
O1 P1 O4 104.66(13) . . ?
O3 P1 O4 111.42(13) . . ?
O1 P1 O2 110.44(14) . . ?
O3 P1 O2 105.73(13) . . ?
O4 P1 O2 107.05(16) . . ?
P2 O6 H6P 109.5 . . ?
P2 O5 H5P 109.5 . . ?
C1 N1 C5 122.3(3) . . ?
C1 N1 H1N 118.9 . . ?
C5 N1 H1N 118.9 . . ?
N1 C1 C2 119.7(4) . . ?
N1 C1 H1 120.2 . . ?
C2 C1 H1 120.2 . . ?
C1 C2 C3 120.6(4) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 H2 119.7 . . ?
C2 C3 C4 117.8(3) . . ?
C2 C3 C6A 102.5(5) . . ?
C4 C3 C6A 139.7(5) . . ?
C2 C3 C6 138.4(5) . . ?
C4 C3 C6 103.8(5) . . ?
N1 C5 C4 119.6(3) . . ?
N1 C5 H5 120.2 . . ?
C4 C5 H5 120.2 . . ?
C5 C4 C3 120.1(4) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
P1 O4 H4P 109.5 . . ?
P1 O2 H2P 109.5 . . ?
C6A C6 C3 115.1(6) 2_655 . ?
C6A C6 H6 122.4 2_655 . ?
C3 C6 H6 122.4 . . ?
C6 C6A C3 116.8(5) 2_655 . ?
C6 C6A H6A 121.6 2_655 . ?
C3 C6A H6A 121.6 . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C1 C2 -0.9(5) . . . . ?
N1 C1 C2 C3 1.1(6) . . . . ?
C1 C2 C3 C4 -0.7(6) . . . . ?
C1 C2 C3 C6A 177.5(4) . . . . ?
C1 C2 C3 C6 -177.1(5) . . . . ?
C1 N1 C5 C4 0.2(5) . . . . ?
N1 C5 C4 C3 0.2(6) . . . . ?
C2 C3 C4 C5 0.0(6) . . . . ?
C6A C3 C4 C5 -177.3(6) . . . . ?
C6 C3 C4 C5 177.6(4) . . . . ?
C2 C3 C6 C6A -3.6(9) . . . 2_655 ?
C4 C3 C6 C6A 179.7(5) . . . 2_655 ?
C6A C3 C6 C6A 5.3(9) . . . 2_655 ?
C2 C3 C6A C6 179.4(6) . . . 2_655 ?
C4 C3 C6A C6 -3.1(10) . . . 2_655 ?
C6 C3 C6A C6 5.5(7) . . . 2_655 ?

_refine_diff_density_max         0.327
_refine_diff_density_min         -0.329
_refine_diff_density_rms         0.063

####################################################################### 
# 
# 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_A5
_database_code_depnum_ccdc_archive 'CCDC 1566064'
_audit_update_record             
;
2017-08-14 deposited with the CCDC.
2017-09-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C6 H6 Cl3 N3 O2'
_chemical_formula_weight         258.49

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'
Cl Cl 0.1484 0.1585 '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 21/n'
_space_group_name_Hall           '-P 2yn'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   13.6957(3)
_cell_length_b                   5.53110(10)
_cell_length_c                   14.3450(3)
_cell_angle_alpha                90
_cell_angle_beta                 109.2240(10)
_cell_angle_gamma                90
_cell_volume                     1026.07(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4292
_cell_measurement_theta_min      3.01
_cell_measurement_theta_max      25.35

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.673
_exptl_crystal_F_000             520
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.04
_exptl_absorpt_coefficient_mu    0.870
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.912
_exptl_absorpt_correction_T_max  0.966
_exptl_absorpt_process_details   
'Blessing, R. H. (1995) Acta Cryst., A51, 33-38'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10544
_diffrn_reflns_av_unetI/netI     0.0130
_diffrn_reflns_av_R_equivalents  0.0197
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.784
_diffrn_reflns_theta_max         25.351
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             1864
_reflns_number_gt                1620
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0468P)²+0.8834P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1864
_refine_ls_number_parameters     127
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0436
_refine_ls_R_factor_gt           0.0369
_refine_ls_wR_factor_ref         0.1012
_refine_ls_wR_factor_gt          0.0938
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
Cl1 Cl 0.59940(6) 0.63284(13) 0.35137(5) 0.0639(3) Uani 1 1 d . . . . .
Cl2 Cl 0.47979(6) 0.20996(12) 0.27400(5) 0.0561(2) Uani 1 1 d . . . . .
Cl3 Cl 0.64227(7) 0.34524(18) 0.20187(8) 0.0832(3) Uani 1 1 d . . . . .
O2 O 0.49232(16) 0.7045(4) 0.09898(14) 0.0598(5) Uani 1 1 d . . . . .
O1 O 0.38392(12) 0.6647(3) 0.18359(13) 0.0452(4) Uani 1 1 d . . . . .
N1 N 0.23309(14) -0.4536(4) 0.40949(13) 0.0369(4) Uani 1 1 d . . . . .
H1 H 0.1999 -0.5832 0.3849 0.044 Uiso 1 1 calc R U . . .
N2 N 0.12266(17) -0.3880(5) 0.49748(18) 0.0585(7) Uani 1 1 d . . . . .
HA H 0.0893 -0.5170 0.4723 0.070 Uiso 1 1 calc R U . . .
HB H 0.1034 -0.3030 0.5385 0.070 Uiso 1 1 calc R U . . .
C7 C 0.46512(17) 0.6256(4) 0.16649(16) 0.0355(5) Uani 1 1 d . . . . .
C6 C 0.3152(2) -0.3852(5) 0.3834(2) 0.0523(7) Uani 1 1 d . . . . .
H6 H 0.3353 -0.4767 0.3384 0.063 Uiso 1 1 calc R U . . .
C2 C 0.20274(17) -0.3213(4) 0.47343(16) 0.0373(5) Uani 1 1 d . . . . .
C3 C 0.2617(2) -0.1104(5) 0.51126(19) 0.0463(6) Uani 1 1 d . . . . .
H3 H 0.2423 -0.0155 0.5558 0.056 Uiso 1 1 calc R U . . .
N4 N 0.34070(18) -0.0428(4) 0.48729(17) 0.0540(6) Uani 1 1 d . . . . .
C5 C 0.3679(2) -0.1832(6) 0.4230(2) 0.0613(8) Uani 1 1 d . . . . .
H5 H 0.4250 -0.1393 0.4053 0.074 Uiso 1 1 calc R U . . .
C8 C 0.54396(18) 0.4580(4) 0.24363(17) 0.0389(5) Uani 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
Cl1 C8 1.768(2) . ?
Cl2 C8 1.760(2) . ?
Cl3 C8 1.758(2) . ?
O2 C7 1.227(3) . ?
O1 C7 1.234(3) . ?
N1 C2 1.342(3) . ?
N1 C6 1.352(3) . ?
N1 H1 0.8600 . ?
N2 C2 1.306(3) . ?
N2 HA 0.8600 . ?
N2 HB 0.8600 . ?
C7 C8 1.569(3) . ?
C6 C5 1.350(4) . ?
C6 H6 0.9300 . ?
C2 C3 1.421(3) . ?
C3 N4 1.294(3) . ?
C3 H3 0.9300 . ?
N4 C5 1.349(4) . ?
C5 H5 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
C2 N1 C6 120.7(2) . . ?
C2 N1 H1 119.7 . . ?
C6 N1 H1 119.7 . . ?
C2 N2 HA 120.0 . . ?
C2 N2 HB 120.0 . . ?
HA N2 HB 120.0 . . ?
O2 C7 O1 128.5(2) . . ?
O2 C7 C8 116.7(2) . . ?
O1 C7 C8 114.79(19) . . ?
C5 C6 N1 119.6(2) . . ?
C5 C6 H6 120.2 . . ?
N1 C6 H6 120.2 . . ?
N2 C2 N1 120.2(2) . . ?
N2 C2 C3 123.5(2) . . ?
N1 C2 C3 116.4(2) . . ?
N4 C3 C2 123.7(2) . . ?
N4 C3 H3 118.1 . . ?
C2 C3 H3 118.1 . . ?
C3 N4 C5 117.3(2) . . ?
C6 C5 N4 122.3(3) . . ?
C6 C5 H5 118.8 . . ?
N4 C5 H5 118.8 . . ?
C7 C8 Cl3 113.30(16) . . ?
C7 C8 Cl2 110.56(16) . . ?
Cl3 C8 Cl2 107.98(13) . . ?
C7 C8 Cl1 106.93(16) . . ?
Cl3 C8 Cl1 109.58(13) . . ?
Cl2 C8 Cl1 108.40(13) . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 N1 C6 C5 0.8(4) . . . . ?
C6 N1 C2 N2 179.4(2) . . . . ?
C6 N1 C2 C3 -0.3(3) . . . . ?
N2 C2 C3 N4 -179.6(3) . . . . ?
N1 C2 C3 N4 0.1(4) . . . . ?
C2 C3 N4 C5 -0.3(4) . . . . ?
N1 C6 C5 N4 -1.1(5) . . . . ?
C3 N4 C5 C6 0.8(5) . . . . ?
O2 C7 C8 Cl3 -16.6(3) . . . . ?
O1 C7 C8 Cl3 164.94(18) . . . . ?
O2 C7 C8 Cl2 -138.0(2) . . . . ?
O1 C7 C8 Cl2 43.6(2) . . . . ?
O2 C7 C8 Cl1 104.2(2) . . . . ?
O1 C7 C8 Cl1 -74.2(2) . . . . ?

_refine_diff_density_max         0.470
_refine_diff_density_min         -0.390
_refine_diff_density_rms         0.048

####################################################################### 
# 
# 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_A6
_database_code_depnum_ccdc_archive 'CCDC 1566061'
_audit_update_record             
;
2017-08-14 deposited with the CCDC.
2017-09-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C4 H8 N3 O4 P'
_chemical_formula_weight         193.10

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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'

_cell_length_a                   4.5002(2)
_cell_length_b                   8.7726(3)
_cell_length_c                   19.7107(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     778.15(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2109
_cell_measurement_theta_min      3.11
_cell_measurement_theta_max      25.15

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.648
_exptl_crystal_F_000             400
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.04
_exptl_absorpt_coefficient_mu    0.334
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.902
_exptl_absorpt_correction_T_max  0.987
_exptl_absorpt_process_details   
'Blessing, R. H. (1995) Acta Cryst., A51, 33-38'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4005
_diffrn_reflns_av_unetI/netI     0.0253
_diffrn_reflns_av_R_equivalents  0.0220
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.066
_diffrn_reflns_theta_max         25.352
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             1420
_reflns_number_gt                1360
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.627
_reflns_Friedel_fraction_max     0.987
_reflns_Friedel_fraction_full    0.987

_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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0359P)²+0.1538P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 496 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.07(5)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         1420
_refine_ls_number_parameters     109
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0293
_refine_ls_R_factor_gt           0.0279
_refine_ls_wR_factor_ref         0.0687
_refine_ls_wR_factor_gt          0.0680
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.065
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.12838(14) -0.09617(7) 0.42868(4) 0.0260(2) Uani 1 1 d . . . . .
O2 O 0.0134(5) -0.0572(2) 0.50130(11) 0.0404(5) Uani 1 1 d . . . . .
H2P H -0.0913 -0.1271 0.5152 0.061 Uiso 1 1 calc R U . . .
O4 O -0.1332(4) -0.0785(2) 0.37818(10) 0.0404(5) Uani 1 1 d . . . . .
H4P H -0.2713 -0.0343 0.3969 0.061 Uiso 1 1 calc R U . . .
O1 O 0.2301(4) -0.2596(2) 0.42569(11) 0.0342(5) Uani 1 1 d . . . . .
O3 O 0.3646(4) 0.0181(2) 0.41202(11) 0.0357(5) Uani 1 1 d . . . . .
N1 N 0.4343(5) -0.0224(2) 0.64006(13) 0.0320(6) Uani 1 1 d . . . . .
H1 H 0.5083 -0.0896 0.6131 0.038 Uiso 1 1 calc R U . . .
N2 N 0.7043(6) 0.1686(3) 0.58642(14) 0.0461(7) Uani 1 1 d . . . . .
HA H 0.7785 0.1035 0.5586 0.055 Uiso 1 1 calc R U . . .
HB H 0.7528 0.2632 0.5835 0.055 Uiso 1 1 calc R U . . .
N4 N 0.2035(7) 0.1867(3) 0.72810(15) 0.0461(8) Uani 1 1 d . . . . .
C5 C 0.1259(8) 0.0361(3) 0.73117(16) 0.0437(7) Uani 1 1 d . . . . .
H5 H -0.0083 0.0043 0.7641 0.052 Uiso 1 1 calc R U . . .
C6 C 0.2379(7) -0.0668(3) 0.68800(16) 0.0366(7) Uani 1 1 d . . . . .
H6 H 0.1807 -0.1685 0.6910 0.044 Uiso 1 1 calc R U . . .
C2 C 0.5167(6) 0.1235(3) 0.63348(15) 0.0313(6) Uani 1 1 d . . . . .
C3 C 0.3903(8) 0.2269(3) 0.68105(16) 0.0386(7) Uani 1 1 d . . . . .
H3 H 0.4443 0.3291 0.6783 0.046 Uiso 1 1 calc R U . . .


_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 1.498(2) . ?
P1 O1 1.5063(18) . ?
P1 O4 1.549(2) . ?
P1 O2 1.560(2) . ?
O2 H2P 0.8200 . ?
O4 H4P 0.8200 . ?
N1 C2 1.339(3) . ?
N1 C6 1.351(4) . ?
N1 H1 0.8600 . ?
N2 C2 1.315(4) . ?
N2 HA 0.8600 . ?
N2 HB 0.8600 . ?
N4 C3 1.300(4) . ?
N4 C5 1.368(4) . ?
C5 C6 1.339(4) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C2 C3 1.423(4) . ?
C3 H3 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
O3 P1 O1 114.40(12) . . ?
O3 P1 O4 109.36(12) . . ?
O1 P1 O4 107.52(12) . . ?
O3 P1 O2 106.85(11) . . ?
O1 P1 O2 110.19(12) . . ?
O4 P1 O2 108.39(12) . . ?
P1 O2 H2P 109.5 . . ?
P1 O4 H4P 109.5 . . ?
C2 N1 C6 121.6(2) . . ?
C2 N1 H1 119.2 . . ?
C6 N1 H1 119.2 . . ?
C2 N2 HA 120.0 . . ?
C2 N2 HB 120.0 . . ?
HA N2 HB 120.0 . . ?
C3 N4 C5 117.3(3) . . ?
C6 C5 N4 121.8(3) . . ?
C6 C5 H5 119.1 . . ?
N4 C5 H5 119.1 . . ?
C5 C6 N1 119.8(3) . . ?
C5 C6 H6 120.1 . . ?
N1 C6 H6 120.1 . . ?
N2 C2 N1 122.2(3) . . ?
N2 C2 C3 122.0(3) . . ?
N1 C2 C3 115.8(3) . . ?
N4 C3 C2 123.7(3) . . ?
N4 C3 H3 118.1 . . ?
C2 C3 H3 118.1 . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 N4 C5 C6 0.4(5) . . . . ?
N4 C5 C6 N1 0.4(5) . . . . ?
C2 N1 C6 C5 -1.4(4) . . . . ?
C6 N1 C2 N2 -179.0(3) . . . . ?
C6 N1 C2 C3 1.5(4) . . . . ?
C5 N4 C3 C2 -0.2(5) . . . . ?
N2 C2 C3 N4 179.8(3) . . . . ?
N1 C2 C3 N4 -0.7(5) . . . . ?

_refine_diff_density_max         0.160
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.040

####################################################################### 
# 
# 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_B2
_database_code_depnum_ccdc_archive 'CCDC 1566060'
_audit_update_record             
;
2017-08-14 deposited with the CCDC.
2017-09-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H16 N2 O8 P2'
_chemical_formula_weight         378.21

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'
Cl Cl 0.1484 0.1585 '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'
S S 0.1246 0.1234 '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 21/n'
_space_group_name_Hall           '-P 2yn'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.2640(7)
_cell_length_b                   4.7949(3)
_cell_length_c                   17.7033(13)
_cell_angle_alpha                90
_cell_angle_beta                 90.536(2)
_cell_angle_gamma                90
_cell_volume                     786.35(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    832
_cell_measurement_theta_min      2.30
_cell_measurement_theta_max      23.82

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.597
_exptl_crystal_F_000             392
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    0.322
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.895
_exptl_absorpt_correction_T_max  0.984
_exptl_absorpt_process_details   
'Blessing, R. H. (1995) Acta Cryst., A51, 33-38'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3423
_diffrn_reflns_av_unetI/netI     0.0439
_diffrn_reflns_av_R_equivalents  0.0344
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.301
_diffrn_reflns_theta_max         25.339
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measured_fraction_theta_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_point_group_measured_fraction_full 0.982
_reflns_number_total             1408
_reflns_number_gt                1128
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0535P)²+0.5415P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1408
_refine_ls_number_parameters     109
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0616
_refine_ls_R_factor_gt           0.0477
_refine_ls_wR_factor_ref         0.1193
_refine_ls_wR_factor_gt          0.1116
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_restrained_S_all      1.076
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
O1 O 0.4964(2) -1.0705(5) 0.88689(11) 0.0402(6) Uani 1 1 d . . . . .
N1 N -0.3184(3) 0.6849(5) 1.07859(14) 0.0322(6) Uani 1 1 d . . . . .
H1N H -0.3798 0.8128 1.0896 0.039 Uiso 1 1 calc R U . . .
C1 C -0.3180(3) 0.5781(7) 1.00938(17) 0.0345(8) Uani 1 1 d . . . . .
H1 H -0.3835 0.6421 0.9732 0.041 Uiso 1 1 calc R U . . .
C2 C -0.2201(4) 0.3714(7) 0.99113(18) 0.0382(8) Uani 1 1 d . . . . .
H2 H -0.2204 0.2951 0.9428 0.046 Uiso 1 1 calc R U . . .
C3 C -0.1213(3) 0.2781(7) 1.04496(19) 0.0343(8) Uani 1 1 d . . . . .
C6 C -0.0080(4) 0.0649(7) 1.03162(18) 0.0417(9) Uani 1 1 d . . . . .
H6 H 0.0551 0.0226 1.0711 0.050 Uiso 1 1 calc R U . . .
C4 C -0.1257(4) 0.3982(7) 1.11586(18) 0.0406(8) Uani 1 1 d . . . . .
H4 H -0.0604 0.3426 1.1531 0.049 Uiso 1 1 calc R U . . .
C5 C -0.2258(4) 0.5981(7) 1.13107(18) 0.0392(8) Uani 1 1 d . . . . .
H5 H -0.2292 0.6752 1.1792 0.047 Uiso 1 1 calc R U . . .
O3 O 0.5864(2) -0.8310(4) 0.76914(12) 0.0355(6) Uani 1 1 d . . . . .
O4 O 0.7293(2) -1.2121(5) 0.83584(11) 0.0352(6) Uani 1 1 d . . . . .
H4P H 0.7775 -1.2295 0.7975 0.053 Uiso 1 1 calc R U . . .
O2 O 0.5046(2) -1.3158(5) 0.76049(12) 0.0415(6) Uani 1 1 d . . . . .
H2P H 0.5045 -1.4688 0.7812 0.062 Uiso 1 1 calc R U . . .
P1 P 0.57651(8) -1.09549(16) 0.81434(4) 0.0252(3) Uani 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
O1 P1 1.494(2) . ?
N1 C5 1.326(4) . ?
N1 C1 1.328(4) . ?
N1 H1N 0.8600 . ?
C1 C2 1.384(5) . ?
C1 H1 0.9300 . ?
C2 C3 1.389(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.382(5) . ?
C3 C6 1.486(5) . ?
C6 C6 1.291(6) 3_557 ?
C6 H6 0.9300 . ?
C4 C5 1.362(5) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
O3 P1 1.503(2) . ?
O4 P1 1.565(2) . ?
O4 H4P 0.8200 . ?
O2 P1 1.568(2) . ?
O2 H2P 0.8200 . ?

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
C5 N1 C1 121.2(3) . . ?
C5 N1 H1N 119.4 . . ?
C1 N1 H1N 119.4 . . ?
N1 C1 C2 119.9(3) . . ?
N1 C1 H1 120.0 . . ?
C2 C1 H1 120.0 . . ?
C1 C2 C3 120.0(3) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
C4 C3 C2 117.7(3) . . ?
C4 C3 C6 117.2(3) . . ?
C2 C3 C6 125.0(3) . . ?
C6 C6 C3 123.9(4) 3_557 . ?
C6 C6 H6 118.1 3_557 . ?
C3 C6 H6 118.1 . . ?
C5 C4 C3 119.9(3) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
N1 C5 C4 121.3(3) . . ?
N1 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?
P1 O4 H4P 109.5 . . ?
P1 O2 H2P 109.5 . . ?
O1 P1 O3 115.03(13) . . ?
O1 P1 O4 105.97(12) . . ?
O3 P1 O4 111.82(13) . . ?
O1 P1 O2 111.41(14) . . ?
O3 P1 O2 105.81(12) . . ?
O4 P1 O2 106.58(12) . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C1 C2 0.2(5) . . . . ?
N1 C1 C2 C3 -0.7(5) . . . . ?
C1 C2 C3 C4 0.1(5) . . . . ?
C1 C2 C3 C6 -177.9(3) . . . . ?
C4 C3 C6 C6 179.6(4) . . . 3_557 ?
C2 C3 C6 C6 -2.4(7) . . . 3_557 ?
C2 C3 C4 C5 0.8(5) . . . . ?
C6 C3 C4 C5 179.0(3) . . . . ?
C1 N1 C5 C4 0.7(5) . . . . ?
C3 C4 C5 N1 -1.3(6) . . . . ?

_refine_diff_density_max         0.728
_refine_diff_density_min         -0.325
_refine_diff_density_rms         0.066

####################################################################### 
# 
# 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_A2
_database_code_depnum_ccdc_archive 'CCDC 1566063'
_audit_update_record             
;
2017-08-14 deposited with the CCDC.
2017-09-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C4 H6 Br N3'
_chemical_formula_weight         176.02

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'
Br Br -0.2901 2.4595 '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'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.0554(9)
_cell_length_b                   7.5644(13)
_cell_length_c                   9.0290(14)
_cell_angle_alpha                72.096(11)
_cell_angle_beta                 79.191(11)
_cell_angle_gamma                80.625(11)
_cell_volume                     320.68(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1725
_cell_measurement_theta_min      3.16
_cell_measurement_theta_max      25.34

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.813
_exptl_crystal_F_000             172
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.04
_exptl_absorpt_coefficient_mu    6.304
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.609
_exptl_absorpt_correction_T_max  0.777
_exptl_absorpt_process_details   
'Blessing, R. H. (1995) Acta Cryst., A51, 33-38'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3007
_diffrn_reflns_av_unetI/netI     0.0312
_diffrn_reflns_av_R_equivalents  0.0346
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.396
_diffrn_reflns_theta_max         25.428
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             1163
_reflns_number_gt                1048
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0326P)²+0.0856P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1163
_refine_ls_number_parameters     73
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0310
_refine_ls_R_factor_gt           0.0259
_refine_ls_wR_factor_ref         0.0642
_refine_ls_wR_factor_gt          0.0623
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_restrained_S_all      1.088
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
Br1 Br 0.35272(6) 0.15887(4) 1.19689(3) 0.04350(14) Uani 1 1 d . . . . .
N1 N 0.6963(5) 0.3798(3) 0.6649(3) 0.0365(6) Uani 1 1 d . . . . .
N2 N 0.7912(5) 0.3265(4) 0.4216(3) 0.0483(7) Uani 1 1 d . . . . .
HA H 0.6451 0.3966 0.3964 0.058 Uiso 1 1 calc R U . . .
HB H 0.8935 0.2751 0.3552 0.058 Uiso 1 1 calc R U . . .
N4 N 1.1530(5) 0.1594(4) 0.7488(3) 0.0443(7) Uani 1 1 d . . . . .
H4 H 1.2989 0.0902 0.7756 0.053 Uiso 1 1 calc R U . . .
C5 C 0.9943(7) 0.2353(5) 0.8533(4) 0.0472(8) Uani 1 1 d . . . . .
H5 H 1.0368 0.2138 0.9537 0.057 Uiso 1 1 calc R U . . .
C6 C 0.7649(7) 0.3469(4) 0.8065(4) 0.0437(7) Uani 1 1 d . . . . .
H6 H 0.6517 0.4022 0.8777 0.052 Uiso 1 1 calc R U . . .
C2 C 0.8590(5) 0.2979(4) 0.5630(3) 0.0338(6) Uani 1 1 d . . . . .
C3 C 1.0988(6) 0.1845(4) 0.6070(4) 0.0413(7) Uani 1 1 d . . . . .
H3 H 1.2153 0.1290 0.5371 0.050 Uiso 1 1 calc R U . . .


_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
N1 C6 1.326(4) . ?
N1 C2 1.345(4) . ?
N2 C2 1.328(4) . ?
N2 HA 0.8600 . ?
N2 HB 0.8600 . ?
N4 C3 1.310(4) . ?
N4 C5 1.327(4) . ?
N4 H4 0.8600 . ?
C5 C6 1.372(4) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C2 C3 1.413(4) . ?
C3 H3 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
C6 N1 C2 118.1(3) . . ?
C2 N2 HA 120.0 . . ?
C2 N2 HB 120.0 . . ?
HA N2 HB 120.0 . . ?
C3 N4 C5 123.3(3) . . ?
C3 N4 H4 118.3 . . ?
C5 N4 H4 118.3 . . ?
N4 C5 C6 117.0(3) . . ?
N4 C5 H5 121.5 . . ?
C6 C5 H5 121.5 . . ?
N1 C6 C5 123.3(3) . . ?
N1 C6 H6 118.4 . . ?
C5 C6 H6 118.4 . . ?
N2 C2 N1 119.0(3) . . ?
N2 C2 C3 121.2(3) . . ?
N1 C2 C3 119.8(3) . . ?
N4 C3 C2 118.4(3) . . ?
N4 C3 H3 120.8 . . ?
C2 C3 H3 120.8 . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 N4 C5 C6 -0.8(5) . . . . ?
C2 N1 C6 C5 0.7(5) . . . . ?
N4 C5 C6 N1 0.5(5) . . . . ?
C6 N1 C2 N2 178.8(3) . . . . ?
C6 N1 C2 C3 -1.6(4) . . . . ?
C5 N4 C3 C2 -0.1(5) . . . . ?
N2 C2 C3 N4 -179.1(3) . . . . ?
N1 C2 C3 N4 1.3(4) . . . . ?

_refine_diff_density_max         0.602
_refine_diff_density_min         -0.369
_refine_diff_density_rms         0.073

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1566066'
_audit_update_record             
;
2017-09-13 deposited with the CCDC.
2017-09-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C7 H13 N3 O4 S1'
_chemical_formula_weight         235.26

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'
S S 0.3331 0.5567 '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 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

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'

_cell_length_a                   9.0017(7)
_cell_length_b                   21.128(2)
_cell_length_c                   11.7627(9)
_cell_angle_alpha                90
_cell_angle_beta                 90.617(5)
_cell_angle_gamma                90
_cell_volume                     2237.0(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3102
_cell_measurement_theta_min      4.18
_cell_measurement_theta_max      66.44

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.397
_exptl_crystal_F_000             992
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.02
_exptl_absorpt_coefficient_mu    2.626
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.728
_exptl_absorpt_correction_T_max  0.949
_exptl_absorpt_process_details   
'Blessing, R. H. (1995) Acta Cryst., A51, 33-38'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10410
_diffrn_reflns_av_unetI/netI     0.0393
_diffrn_reflns_av_R_equivalents  0.0344
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         4.185
_diffrn_reflns_theta_max         66.615
_diffrn_reflns_theta_full        66.615
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measured_fraction_theta_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_point_group_measured_fraction_full 0.975
_reflns_number_total             3851
_reflns_number_gt                2640
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3851
_refine_ls_number_parameters     289
_refine_ls_number_restraints     306
_refine_ls_R_factor_all          0.1262
_refine_ls_R_factor_gt           0.0923
_refine_ls_wR_factor_ref         0.3268
_refine_ls_wR_factor_gt          0.2829
_refine_ls_goodness_of_fit_ref   1.274
_refine_ls_restrained_S_all      1.306
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
O6 O 0.4427(4) 0.4091(2) 0.6700(3) 0.0639(10) Uani 1 1 d . U . . .
S2 S 0.55912(15) 0.38006(7) 0.73581(10) 0.0556(5) Uani 1 1 d . U . . .
S1 S 0.06187(15) 0.41508(7) 0.40774(10) 0.0572(5) Uani 1 1 d . U . . .
O8 O 0.5428(5) 0.3842(3) 0.8555(3) 0.0957(16) Uani 1 1 d . U . . .
O5 O 0.7008(5) 0.3989(3) 0.6950(3) 0.1015(19) Uani 1 1 d . U . . .
N4A N 0.6404(5) 0.4504(3) 0.1558(3) 0.0659(13) Uani 1 1 d . U . . .
N2A N 0.6168(5) 0.4386(2) 0.4601(3) 0.0599(12) Uani 1 1 d . U . . .
HA2A H 0.5510 0.4336 0.5119 0.072 Uiso 1 1 calc R U . . .
HA2B H 0.7093 0.4411 0.4786 0.072 Uiso 1 1 calc R U . . .
N2B N 0.1163(6) 0.4116(2) 0.7040(3) 0.0624(13) Uani 1 1 d . U . . .
HB2A H 0.0497 0.4126 0.6510 0.075 Uiso 1 1 calc R U . . .
HB2B H 0.2087 0.4093 0.6868 0.075 Uiso 1 1 calc R U . . .
O2 O 0.0478(5) 0.4522(3) 0.3077(3) 0.0949(17) Uani 1 1 d . U . . .
O1 O 0.2049(4) 0.4203(3) 0.4614(3) 0.0907(17) Uani 1 1 d . U . . .
O4 O -0.0559(4) 0.4212(2) 0.4866(3) 0.0694(12) Uani 1 1 d . U . . .
C6A C 0.3909(6) 0.4418(3) 0.2108(4) 0.0572(13) Uani 1 1 d . U . . .
H6A H 0.2906 0.4402 0.1912 0.069 Uiso 1 1 calc R U . . .
C5A C 0.4932(7) 0.4472(3) 0.1293(4) 0.0668(15) Uani 1 1 d . U . . .
H5A H 0.4629 0.4488 0.0535 0.080 Uiso 1 1 calc R U . . .
C3A C 0.6790(6) 0.4486(3) 0.2628(4) 0.0546(12) Uani 1 1 d . U . . .
H3A H 0.7794 0.4514 0.2814 0.066 Uiso 1 1 calc R U . . .
C2A C 0.5757(5) 0.4424(2) 0.3524(4) 0.0467(11) Uani 1 1 d . U . . .
N1A N 0.4332(5) 0.4386(2) 0.3214(3) 0.0512(10) Uani 1 1 d . U . . .
H1A H 0.3667 0.4341 0.3728 0.061 Uiso 1 1 calc R U . . .
C2B C 0.0769(6) 0.4134(2) 0.8107(4) 0.0502(12) Uani 1 1 d . U . . .
C3B C 0.1812(6) 0.4116(3) 0.9036(4) 0.0604(14) Uani 1 1 d . U . . .
H3B H 0.2819 0.4087 0.8878 0.072 Uiso 1 1 calc R U . . .
N4B N 0.1401(6) 0.4138(3) 1.0093(4) 0.0723(14) Uani 1 1 d . U . . .
C5B C -0.0083(7) 0.4183(3) 1.0322(4) 0.0724(18) Uani 1 1 d . U . . .
H5B H -0.0383 0.4206 1.1075 0.087 Uiso 1 1 calc R U . . .
C6B C -0.1112(7) 0.4195(3) 0.9496(4) 0.0625(14) Uani 1 1 d . U . . .
H6B H -0.2115 0.4220 0.9671 0.075 Uiso 1 1 calc R U . . .
N1B N -0.0671(5) 0.4170(2) 0.8394(3) 0.0545(11) Uani 1 1 d . U . . .
H1B H -0.1335 0.4177 0.7863 0.065 Uiso 1 1 calc R U . . .
O7 O 0.5437(9) 0.3087(3) 0.7194(6) 0.167(3) Uani 1 1 d D U . . .
C13A C 0.5276(16) 0.2732(5) 0.6142(12) 0.182(7) Uani 0.6 1 d D U P A 1
H13A H 0.5763 0.2985 0.5557 0.219 Uiso 0.6 1 calc R U P A 1
C12 C 0.3727(15) 0.2631(8) 0.5730(13) 0.266(9) Uani 1 1 d D U . . .
H12A H 0.3740 0.2392 0.5035 0.399 Uiso 0.5 1 calc R U P A 1
H12B H 0.3180 0.2401 0.6292 0.399 Uiso 0.5 1 calc R U P A 1
H12C H 0.3261 0.3033 0.5595 0.399 Uiso 0.5 1 calc R U P A 1
H12D H 0.3047 0.2825 0.6247 0.399 Uiso 0.5 1 calc R U P A 1
H12E H 0.3607 0.2816 0.4989 0.399 Uiso 0.5 1 calc R U P A 1
H12F H 0.3526 0.2185 0.5686 0.399 Uiso 0.5 1 calc R U P A 1
C14 C 0.6091(18) 0.2106(6) 0.6173(16) 0.304(9) Uani 1 1 d D U . . .
H14A H 0.5949 0.1891 0.5462 0.456 Uiso 0.5 1 calc R U P A 1
H14B H 0.7132 0.2180 0.6300 0.456 Uiso 0.5 1 calc R U P A 1
H14C H 0.5709 0.1850 0.6778 0.456 Uiso 0.5 1 calc R U P A 1
H14D H 0.6577 0.2056 0.6898 0.456 Uiso 0.5 1 calc R U P A 1
H14E H 0.5395 0.1767 0.6059 0.456 Uiso 0.5 1 calc R U P A 1
H14F H 0.6817 0.2097 0.5582 0.456 Uiso 0.5 1 calc R U P A 1
C10A C -0.0344(18) 0.2972(6) 0.3295(14) 0.241(8) Uani 0.6 1 d D U P B 1
H10A H -0.1133 0.3174 0.2844 0.290 Uiso 0.6 1 calc R U P B 1
O3 O 0.0678(10) 0.3473(3) 0.3699(7) 0.195(4) Uani 1 1 d D U . . .
C11 C -0.1057(19) 0.2619(7) 0.4251(16) 0.318(10) Uani 1 1 d D U . . .
H11A H -0.1708 0.2300 0.3945 0.476 Uiso 0.5 1 calc R U P B 1
H11B H -0.0302 0.2422 0.4713 0.476 Uiso 0.5 1 calc R U P B 1
H11C H -0.1618 0.2908 0.4706 0.476 Uiso 0.5 1 calc R U P B 1
H11D H -0.0711 0.2787 0.4964 0.476 Uiso 0.5 1 calc R U P B 1
H11E H -0.2117 0.2665 0.4197 0.476 Uiso 0.5 1 calc R U P B 1
H11F H -0.0801 0.2178 0.4203 0.476 Uiso 0.5 1 calc R U P B 1
C9 C 0.050(2) 0.2523(8) 0.2521(15) 0.316(10) Uani 1 1 d D U . . .
H9A H -0.0161 0.2197 0.2255 0.473 Uiso 0.5 1 calc R U P B 1
H9B H 0.0874 0.2755 0.1883 0.473 Uiso 0.5 1 calc R U P B 1
H9C H 0.1309 0.2336 0.2936 0.473 Uiso 0.5 1 calc R U P B 1
H9D H 0.1509 0.2662 0.2461 0.473 Uiso 0.5 1 calc R U P B 1
H9E H 0.0474 0.2104 0.2833 0.473 Uiso 0.5 1 calc R U P B 1
H9F H 0.0038 0.2522 0.1780 0.473 Uiso 0.5 1 calc R U P B 1
C10B C 0.041(2) 0.2774(6) 0.3719(16) 0.269(9) Uani 0.4 1 d D U P B 2
H10B H 0.1201 0.2575 0.4173 0.323 Uiso 0.4 1 calc R U P B 2
C13B C 0.4855(17) 0.2508(7) 0.6641(16) 0.217(9) Uani 0.4 1 d D U P A 2
H13B H 0.4365 0.2259 0.7231 0.261 Uiso 0.4 1 calc R U P A 2


_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
O6 S2 1.434(4) . ?
S2 O8 1.420(4) . ?
S2 O5 1.424(5) . ?
S2 O7 1.525(7) . ?
S1 O2 1.420(4) . ?
S1 O4 1.422(3) . ?
S1 O1 1.432(4) . ?
S1 O3 1.501(7) . ?
N4A C3A 1.302(7) . ?
N4A C5A 1.360(7) . ?
N2A C2A 1.318(6) . ?
N2A HA2A 0.8600 . ?
N2A HA2B 0.8600 . ?
N2B C2B 1.309(6) . ?
N2B HB2A 0.8600 . ?
N2B HB2B 0.8600 . ?
C6A C5A 1.341(7) . ?
C6A N1A 1.353(6) . ?
C6A H6A 0.9300 . ?
C5A H5A 0.9300 . ?
C3A C2A 1.419(6) . ?
C3A H3A 0.9300 . ?
C2A N1A 1.333(6) . ?
N1A H1A 0.8600 . ?
C2B N1B 1.345(6) . ?
C2B C3B 1.434(7) . ?
C3B N4B 1.302(7) . ?
C3B H3B 0.9300 . ?
N4B C5B 1.368(8) . ?
C5B C6B 1.336(9) . ?
C5B H5B 0.9300 . ?
C6B N1B 1.361(6) . ?
C6B H6B 0.9300 . ?
N1B H1B 0.8600 . ?
O7 C13A 1.453(9) . ?
O7 C13B 1.479(10) . ?
C13A C12 1.487(9) . ?
C13A C14 1.512(9) . ?
C13A H13A 0.9800 . ?
C12 C13B 1.492(10) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C12 H12D 0.9600 . ?
C12 H12E 0.9600 . ?
C12 H12F 0.9600 . ?
C14 C13B 1.509(10) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C14 H14D 0.9600 . ?
C14 H14E 0.9600 . ?
C14 H14F 0.9600 . ?
C10A O3 1.477(10) . ?
C10A C11 1.500(10) . ?
C10A C9 1.522(10) . ?
C10A H10A 0.9800 . ?
O3 C10B 1.497(10) . ?
C11 C10B 1.505(10) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C11 H11D 0.9600 . ?
C11 H11E 0.9600 . ?
C11 H11F 0.9600 . ?
C9 C10B 1.508(10) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C9 H9D 0.9600 . ?
C9 H9E 0.9600 . ?
C9 H9F 0.9600 . ?
C10B H10B 0.9800 . ?
C13B H13B 0.9800 . ?

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
O8 S2 O5 114.8(3) . . ?
O8 S2 O6 115.2(3) . . ?
O5 S2 O6 110.5(3) . . ?
O8 S2 O7 100.2(4) . . ?
O5 S2 O7 108.3(4) . . ?
O6 S2 O7 106.8(3) . . ?
O2 S1 O4 115.5(3) . . ?
O2 S1 O1 113.3(3) . . ?
O4 S1 O1 112.3(2) . . ?
O2 S1 O3 106.6(4) . . ?
O4 S1 O3 108.0(3) . . ?
O1 S1 O3 99.7(5) . . ?
C3A N4A C5A 117.9(4) . . ?
C2A N2A HA2A 120.0 . . ?
C2A N2A HA2B 120.0 . . ?
HA2A N2A HA2B 120.0 . . ?
C2B N2B HB2A 120.0 . . ?
C2B N2B HB2B 120.0 . . ?
HB2A N2B HB2B 120.0 . . ?
C5A C6A N1A 120.2(5) . . ?
C5A C6A H6A 119.9 . . ?
N1A C6A H6A 119.9 . . ?
C6A C5A N4A 121.0(5) . . ?
C6A C5A H5A 119.5 . . ?
N4A C5A H5A 119.5 . . ?
N4A C3A C2A 123.4(5) . . ?
N4A C3A H3A 118.3 . . ?
C2A C3A H3A 118.3 . . ?
N2A C2A N1A 121.2(4) . . ?
N2A C2A C3A 122.7(5) . . ?
N1A C2A C3A 116.0(4) . . ?
C2A N1A C6A 121.3(4) . . ?
C2A N1A H1A 119.3 . . ?
C6A N1A H1A 119.3 . . ?
N2B C2B N1B 120.9(5) . . ?
N2B C2B C3B 123.3(5) . . ?
N1B C2B C3B 115.8(4) . . ?
N4B C3B C2B 122.5(5) . . ?
N4B C3B H3B 118.8 . . ?
C2B C3B H3B 118.8 . . ?
C3B N4B C5B 118.6(5) . . ?
C6B C5B N4B 121.9(5) . . ?
C6B C5B H5B 119.1 . . ?
N4B C5B H5B 119.1 . . ?
C5B C6B N1B 119.1(6) . . ?
C5B C6B H6B 120.5 . . ?
N1B C6B H6B 120.5 . . ?
C2B N1B C6B 122.2(5) . . ?
C2B N1B H1B 118.9 . . ?
C6B N1B H1B 118.9 . . ?
C13A O7 S2 128.8(8) . . ?
C13B O7 S2 154.8(8) . . ?
O7 C13A C12 115.9(10) . . ?
O7 C13A C14 112.8(9) . . ?
C12 C13A C14 109.6(8) . . ?
O7 C13A H13A 105.9 . . ?
C12 C13A H13A 105.9 . . ?
C14 C13A H13A 105.9 . . ?
C13A C12 H12A 109.5 . . ?
C13A C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C13A C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C13A C12 H12D 109.5 . . ?
H12A C12 H12D 141.1 . . ?
H12B C12 H12D 56.3 . . ?
H12C C12 H12D 56.3 . . ?
C13A C12 H12E 109.5 . . ?
H12A C12 H12E 56.3 . . ?
H12B C12 H12E 141.1 . . ?
H12C C12 H12E 56.3 . . ?
H12D C12 H12E 109.5 . . ?
C13A C12 H12F 109.5 . . ?
H12A C12 H12F 56.3 . . ?
H12B C12 H12F 56.3 . . ?
H12C C12 H12F 141.1 . . ?
H12D C12 H12F 109.5 . . ?
H12E C12 H12F 109.5 . . ?
C13A C14 H14A 109.5 . . ?
C13A C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13A C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13A C14 H14D 109.5 . . ?
H14A C14 H14D 141.1 . . ?
H14B C14 H14D 56.3 . . ?
H14C C14 H14D 56.3 . . ?
C13A C14 H14E 109.5 . . ?
H14A C14 H14E 56.3 . . ?
H14B C14 H14E 141.1 . . ?
H14C C14 H14E 56.3 . . ?
H14D C14 H14E 109.5 . . ?
C13A C14 H14F 109.5 . . ?
H14A C14 H14F 56.3 . . ?
H14B C14 H14F 56.3 . . ?
H14C C14 H14F 141.1 . . ?
H14D C14 H14F 109.5 . . ?
H14E C14 H14F 109.5 . . ?
O3 C10A C11 112.7(10) . . ?
O3 C10A C9 109.1(9) . . ?
C11 C10A C9 111.0(10) . . ?
O3 C10A H10A 108.0 . . ?
C11 C10A H10A 108.0 . . ?
C9 C10A H10A 108.0 . . ?
C10A O3 S1 139.0(9) . . ?
C10B O3 S1 158.6(7) . . ?
C10A C11 H11A 109.5 . . ?
C10A C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10A C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10A C11 H11D 109.5 . . ?
H11A C11 H11D 141.1 . . ?
H11B C11 H11D 56.3 . . ?
H11C C11 H11D 56.3 . . ?
C10A C11 H11E 109.5 . . ?
H11A C11 H11E 56.3 . . ?
H11B C11 H11E 141.1 . . ?
H11C C11 H11E 56.3 . . ?
H11D C11 H11E 109.5 . . ?
C10A C11 H11F 109.5 . . ?
H11A C11 H11F 56.3 . . ?
H11B C11 H11F 56.3 . . ?
H11C C11 H11F 141.1 . . ?
H11D C11 H11F 109.5 . . ?
H11E C11 H11F 109.5 . . ?
C10A C9 H9A 109.5 . . ?
C10A C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C10A C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C10A C9 H9D 109.5 . . ?
H9A C9 H9D 141.1 . . ?
H9B C9 H9D 56.3 . . ?
H9C C9 H9D 56.3 . . ?
C10A C9 H9E 109.5 . . ?
H9A C9 H9E 56.3 . . ?
H9B C9 H9E 141.1 . . ?
H9C C9 H9E 56.3 . . ?
H9D C9 H9E 109.5 . . ?
C10A C9 H9F 109.5 . . ?
H9A C9 H9F 56.3 . . ?
H9B C9 H9F 56.3 . . ?
H9C C9 H9F 141.1 . . ?
H9D C9 H9F 109.5 . . ?
H9E C9 H9F 109.5 . . ?
O3 C10B C11 111.3(10) . . ?
O3 C10B C9 108.8(9) . . ?
C11 C10B C9 111.5(10) . . ?
O3 C10B H10B 108.4 . . ?
C11 C10B H10B 108.4 . . ?
C9 C10B H10B 108.4 . . ?
O7 C13B C12 114.1(10) . . ?
O7 C13B C14 111.6(10) . . ?
C12 C13B C14 109.5(10) . . ?
O7 C13B H13B 107.1 . . ?
C12 C13B H13B 107.1 . . ?
C14 C13B H13B 107.1 . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1A C6A C5A N4A -0.8(9) . . . . ?
C3A N4A C5A C6A -0.5(9) . . . . ?
C5A N4A C3A C2A 1.0(9) . . . . ?
N4A C3A C2A N2A 177.9(5) . . . . ?
N4A C3A C2A N1A -0.2(8) . . . . ?
N2A C2A N1A C6A -179.3(5) . . . . ?
C3A C2A N1A C6A -1.2(7) . . . . ?
C5A C6A N1A C2A 1.7(8) . . . . ?
N2B C2B C3B N4B 179.7(5) . . . . ?
N1B C2B C3B N4B -0.6(8) . . . . ?
C2B C3B N4B C5B -0.3(9) . . . . ?
C3B N4B C5B C6B 1.0(10) . . . . ?
N4B C5B C6B N1B -0.8(10) . . . . ?
N2B C2B N1B C6B -179.5(5) . . . . ?
C3B C2B N1B C6B 0.8(8) . . . . ?
C5B C6B N1B C2B -0.1(9) . . . . ?
O8 S2 O7 C13A 169.9(9) . . . . ?
O5 S2 O7 C13A -69.6(10) . . . . ?
O6 S2 O7 C13A 49.4(10) . . . . ?
O8 S2 O7 C13B 133(2) . . . . ?
O5 S2 O7 C13B -106(2) . . . . ?
O6 S2 O7 C13B 13(2) . . . . ?
S2 O7 C13A C12 -89.4(15) . . . . ?
S2 O7 C13A C14 143.1(12) . . . . ?
C11 C10A O3 S1 -84.8(18) . . . . ?
C9 C10A O3 S1 151.5(12) . . . . ?
O2 S1 O3 C10A -77.5(12) . . . . ?
O4 S1 O3 C10A 47.1(13) . . . . ?
O1 S1 O3 C10A 164.5(12) . . . . ?
O2 S1 O3 C10B -143(3) . . . . ?
O4 S1 O3 C10B -18(3) . . . . ?
O1 S1 O3 C10B 99(3) . . . . ?
S1 O3 C10B C11 32(4) . . . . ?
S1 O3 C10B C9 155(3) . . . . ?
S2 O7 C13B C12 -4(3) . . . . ?
S2 O7 C13B C14 121(2) . . . . ?

_refine_diff_density_max         0.935
_refine_diff_density_min         -0.584
_refine_diff_density_rms         0.114



# start Validation Reply Form
_vrf_PLAT241_A3                  
;
PROBLEM: High   'MainMol' Ueq as Compared to Neighbors of         C9 Check
RESPONSE: The packing in this structure is featured by layers assembled with weaks vdW interactions between methyl groups of neighboring isopropyl
sulfate counterions. These methyl groups are therefore slightly disordered due to these weak interactions, leading to this alert.
;
_vrf_PLAT242_A3                  
;
PROBLEM: Low    'MainMol' Ueq as Compared to Neighbors of         S1 Check
RESPONSE: This is due to a slight disorder affecting isopropyl sulfate
counterion. We used the split position model and the refinement resulted in two disordered sites with occupancy factors of 0.6 and 0.4 for C10A and
C10B and for C13A and C13B. Even so, ADPs of the counterion carbons are still higher than that of sulfur atom, generating this alert. 
;
# end Validation Reply Form
####################################################################### 
# 
# 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_A1
_database_code_depnum_ccdc_archive 'CCDC 1566067'
_audit_update_record             
;
2017-08-14 deposited with the CCDC.
2017-09-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C4 H6 Cl1 N3'
_chemical_formula_weight         131.57

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'
Cl Cl 0.1484 0.1585 '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'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   4.9992(4)
_cell_length_b                   7.3893(7)
_cell_length_c                   8.8313(8)
_cell_angle_alpha                72.451(6)
_cell_angle_beta                 78.656(5)
_cell_angle_gamma                79.410(6)
_cell_volume                     302.26(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1405
_cell_measurement_theta_min      2.92
_cell_measurement_theta_max      24.71

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.446
_exptl_crystal_F_000             136
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    0.520
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.878
_exptl_absorpt_correction_T_max  0.974
_exptl_absorpt_process_details   
'Blessing, R. H. (1995) Acta Cryst., A51, 33-38'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4926
_diffrn_reflns_av_unetI/netI     0.0411
_diffrn_reflns_av_R_equivalents  0.0324
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.447
_diffrn_reflns_theta_max         29.178
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             1565
_reflns_number_gt                1184
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0620P)²+0.8903P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1565
_refine_ls_number_parameters     74
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0818
_refine_ls_R_factor_gt           0.0631
_refine_ls_wR_factor_ref         0.2115
_refine_ls_wR_factor_gt          0.2025
_refine_ls_goodness_of_fit_ref   1.179
_refine_ls_restrained_S_all      1.179
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
Cl1 Cl 0.1563(2) -0.15526(17) 0.30279(14) 0.0420(4) Uani 1 1 d . . . . .
N1 N 0.2007(7) 0.3779(5) 0.1673(4) 0.0364(8) Uani 1 1 d . . . . .
N2 N 0.2968(8) 0.3207(6) -0.0812(5) 0.0448(10) Uani 1 1 d . . . . .
HA H 0.1460 0.3914 -0.1058 0.054 Uiso 1 1 calc R U . . .
HB H 0.4023 0.2672 -0.1495 0.054 Uiso 1 1 calc R U . . .
N4 N 0.6702(7) 0.1499(5) 0.2495(5) 0.0408(9) Uani 1 1 d . . . . .
H4 H 0.8202 0.0788 0.2751 0.049 Uiso 1 1 calc R U . . .
C2 C 0.3672(8) 0.2938(6) 0.0635(5) 0.0322(8) Uani 1 1 d . . . . .
C3 C 0.6113(8) 0.1755(6) 0.1058(6) 0.0377(10) Uani 1 1 d . . . . .
H3 H 0.7280 0.1169 0.0334 0.045 Uiso 1 1 calc R U . . .
C5 C 0.5086(10) 0.2289(7) 0.3573(6) 0.0437(11) Uani 1 1 d . . . . .
H5 H 0.5531 0.2071 0.4593 0.052 Uiso 1 1 calc R U . . .
C6 C 0.2730(10) 0.3442(7) 0.3121(6) 0.0424(10) Uani 1 1 d . . . . .
H6 H 0.1581 0.4017 0.3859 0.051 Uiso 1 1 calc R U . . .


_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
N1 C2 1.331(6) . ?
N1 C6 1.336(6) . ?
N2 C2 1.340(5) . ?
N2 HA 0.8600 . ?
N2 HB 0.8600 . ?
N4 C3 1.309(6) . ?
N4 C5 1.327(6) . ?
N4 H4 0.8600 . ?
C2 C3 1.408(5) . ?
C3 H3 0.9300 . ?
C5 C6 1.372(6) . ?
C5 H5 0.9300 . ?
C6 H6 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
C2 N1 C6 117.5(4) . . ?
C2 N2 HA 120.0 . . ?
C2 N2 HB 120.0 . . ?
HA N2 HB 120.0 . . ?
C3 N4 C5 122.9(4) . . ?
C3 N4 H4 118.6 . . ?
C5 N4 H4 118.6 . . ?
N1 C2 N2 119.0(4) . . ?
N1 C2 C3 120.7(4) . . ?
N2 C2 C3 120.4(4) . . ?
N4 C3 C2 118.5(4) . . ?
N4 C3 H3 120.8 . . ?
C2 C3 H3 120.7 . . ?
N4 C5 C6 117.2(4) . . ?
N4 C5 H5 121.4 . . ?
C6 C5 H5 121.4 . . ?
N1 C6 C5 123.2(4) . . ?
N1 C6 H6 118.4 . . ?
C5 C6 H6 118.4 . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 N1 C2 N2 178.3(4) . . . . ?
C6 N1 C2 C3 -0.6(6) . . . . ?
C5 N4 C3 C2 0.7(7) . . . . ?
N1 C2 C3 N4 0.2(6) . . . . ?
N2 C2 C3 N4 -178.7(4) . . . . ?
C3 N4 C5 C6 -1.1(7) . . . . ?
C2 N1 C6 C5 0.3(7) . . . . ?
N4 C5 C6 N1 0.5(7) . . . . ?

_refine_diff_density_max         0.591
_refine_diff_density_min         -0.286
_refine_diff_density_rms         0.087


# start Validation Reply Form
_vrf_PLAT930_A1                  
;
PROBLEM: Check Twin Law ( 0 1  1)[-2 5  3] Estimated BASF       0.26       
RESPONSE: The twin law was found and added to the refinement, 
but did not lead to improves in the statistical parameters. 
;
# end Validation Reply Form
####################################################################### 
# 
# 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_B1
_database_code_depnum_ccdc_archive 'CCDC 1566068'

_audit_update_record             
;
2017-08-14 deposited with the CCDC.
2017-09-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H12 Br2 N2'
_chemical_formula_weight         344.04

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'
Br Br -0.2901 2.4595 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

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'

_cell_length_a                   5.1052(8)
_cell_length_b                   10.2491(15)
_cell_length_c                   12.6953(18)
_cell_angle_alpha                90
_cell_angle_beta                 93.053(2)
_cell_angle_gamma                90
_cell_volume                     663.32(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1210
_cell_measurement_theta_min      2.56
_cell_measurement_theta_max      25.08

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.722
_exptl_crystal_F_000             336
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.04
_exptl_absorpt_coefficient_mu    6.086
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.646
_exptl_absorpt_correction_T_max  0.784
_exptl_absorpt_process_details   
'Blessing, R. H. (1995) Acta Cryst., A51, 33-38'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            2912
_diffrn_reflns_av_unetI/netI     0.0509
_diffrn_reflns_av_R_equivalents  0.0441
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.555
_diffrn_reflns_theta_max         25.332
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             1203
_reflns_number_gt                1011
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0569P)²+0.0582P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1203
_refine_ls_number_parameters     82
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0444
_refine_ls_R_factor_gt           0.0367
_refine_ls_wR_factor_ref         0.1050
_refine_ls_wR_factor_gt          0.0993
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.057
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
Br1 Br 0.58118(8) 0.48806(4) 0.67782(3) 0.0556(2) Uani 1 1 d . . . . .
N1 N 0.1457(6) 0.3098(3) 0.5617(3) 0.0539(9) Uani 1 1 d . . . . .
H1N H 0.2660 0.3678 0.5720 0.065 Uiso 1 1 calc R U . . .
C4 C -0.0886(8) 0.1360(4) 0.6247(3) 0.0598(11) Uani 1 1 d . . . . .
H4 H -0.1211 0.0786 0.6792 0.072 Uiso 1 1 calc R U . . .
C3 C -0.2325(7) 0.1270(4) 0.5303(4) 0.0566(11) Uani 1 1 d . . . . .
C1 C 0.0114(9) 0.3054(5) 0.4688(4) 0.0685(13) Uani 1 1 d . . . . .
H1 H 0.0484 0.3639 0.4156 0.082 Uiso 1 1 calc R U . . .
C2 C -0.1813(9) 0.2139(5) 0.4525(4) 0.0705(13) Uani 1 1 d . . . . .
H2 H -0.2778 0.2109 0.3884 0.085 Uiso 1 1 calc R U . . .
C5 C 0.0987(8) 0.2273(4) 0.6383(4) 0.0577(10) Uani 1 1 d . . . . .
H5 H 0.1961 0.2325 0.7022 0.069 Uiso 1 1 calc R U . . .
C6 C -0.4265(16) 0.0163(8) 0.5417(7) 0.0406(14) Uani 0.6 1 d . . P . .
H6 H -0.3804 -0.0057 0.6113 0.049 Uiso 0.6 1 calc R U P . .
C6A C -0.443(3) 0.0448(10) 0.4706(12) 0.0406(19) Uani 0.4 1 d . . P . .
H6A H -0.4315 0.0783 0.4029 0.049 Uiso 0.4 1 calc R U P . .


_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
N1 C5 1.320(5) . ?
N1 C1 1.333(5) . ?
N1 H1N 0.8600 . ?
C4 C5 1.343(5) . ?
C4 C3 1.375(6) . ?
C4 H4 0.9300 . ?
C3 C2 1.365(6) . ?
C3 C6 1.518(11) . ?
C3 C6A 1.534(17) . ?
C1 C2 1.366(6) . ?
C1 H1 0.9300 . ?
C2 H2 0.9300 . ?
C5 H5 0.9300 . ?
C6 C6A 0.921(10) 3_456 ?
C6 H6 0.9300 . ?
C6A C6 0.921(10) 3_456 ?
C6A H6A 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
C5 N1 C1 121.7(3) . . ?
C5 N1 H1N 119.2 . . ?
C1 N1 H1N 119.2 . . ?
C5 C4 C3 120.2(4) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C2 C3 C4 118.2(4) . . ?
C2 C3 C6 135.0(5) . . ?
C4 C3 C6 106.7(5) . . ?
C2 C3 C6A 99.1(6) . . ?
C4 C3 C6A 142.7(6) . . ?
N1 C1 C2 119.3(4) . . ?
N1 C1 H1 120.4 . . ?
C2 C1 H1 120.4 . . ?
C3 C2 C1 120.2(4) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
N1 C5 C4 120.5(4) . . ?
N1 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C6A C6 C3 164.0(17) 3_456 . ?
C6A C6 H6 98.0 3_456 . ?
C3 C6 H6 98.0 . . ?
C6 C6A C3 159.7(17) 3_456 . ?
C6 C6A H6A 100.1 3_456 . ?
C3 C6A H6A 100.1 . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 C4 C3 C2 -0.8(6) . . . . ?
C5 C4 C3 C6 -179.4(4) . . . . ?
C5 C4 C3 C6A 175.2(7) . . . . ?
C5 N1 C1 C2 0.5(6) . . . . ?
C4 C3 C2 C1 1.0(7) . . . . ?
C6 C3 C2 C1 179.1(5) . . . . ?
C6A C3 C2 C1 -176.5(6) . . . . ?
N1 C1 C2 C3 -0.9(7) . . . . ?
C1 N1 C5 C4 -0.3(6) . . . . ?
C3 C4 C5 N1 0.4(6) . . . . ?
C2 C3 C6 C6A 3(3) . . . 3_456 ?
C4 C3 C6 C6A -179(3) . . . 3_456 ?
C6A C3 C6 C6A -4(3) . . . 3_456 ?
C2 C3 C6A C6 -171(3) . . . 3_456 ?
C4 C3 C6A C6 12(3) . . . 3_456 ?
C6 C3 C6A C6 3(3) . . . 3_456 ?

_refine_diff_density_max         0.492
_refine_diff_density_min         -0.542
_refine_diff_density_rms         0.107


# start Validation Reply Form
_vrf_PLAT410_B1                  
;
PROBLEM: Short Intra H...H Contact   H2     ..  H6A     .       1.58 Ang.  
RESPONSE: This error message appears because of disorder around central CH
 moieties, which approximates the CH hydrogens in query.
;
# end Validation Reply Form
