# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_NHSO4
_database_code_depnum_ccdc_archive 'CCDC 1474924'
_audit_update_record             
;
2016-04-19 deposited with the CCDC.
2016-07-05 downloaded from the CCDC.
;
_audit_creation_date             2016-04-16
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_formula_moiety         '2(C6 H9 N3 O), 2(O4 S), H2 O'
_chemical_formula_sum            'C12 H20 N6 O11 S2'
_chemical_formula_weight         488.46
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
S 0.12424 0.12443 6.90530 5.20340 1.43790 1.58630 1.46790 22.21510 0.25360
56.17200 0.866900026798
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

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

_symmetry_Int_Tables_number      14
_cell_length_a                   6.9562(3)
_cell_length_b                   19.7321(8)
_cell_length_c                   13.4459(6)
_cell_angle_alpha                90
_cell_angle_beta                 93.4175(13)
_cell_angle_gamma                90
_cell_volume                     1842.31(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9827
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      26.72
_cell_measurement_theta_min      3.04
_exptl_absorpt_coefficient_mu    0.367
_exptl_crystal_density_diffrn    1.7609
_exptl_crystal_F_000             1017.6278
_exptl_crystal_description       prism
_exptl_crystal_colour_primary    colourless
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_diffrn_reflns_av_R_equivalents  0.0550
_diffrn_reflns_av_unetI/netI     0.0448
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            10216
_diffrn_reflns_theta_full        26.0000
_diffrn_reflns_theta_max         26.71
_diffrn_reflns_theta_min         2.56
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.9865
_diffrn_measured_fraction_theta_max 0.9793
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.0
_reflns_number_gt                3282
_reflns_number_total             3830
_reflns_threshold_expression     I>=2u(I)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'SIR2004 (Burla et al., 2007)'
_refine_diff_density_max         0.4715
_refine_diff_density_min         -0.6114
_refine_diff_density_rms         0.0989
_refine_ls_d_res_high            0.7906
_refine_ls_d_res_low             7.9495
_refine_ls_goodness_of_fit_ref   1.0594
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    30
_refine_ls_number_parameters     282
_refine_ls_number_reflns         3830
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0460
_refine_ls_R_factor_gt           0.0366
_refine_ls_restrained_S_all      1.0594
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0476P)²+1.4319P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0929
_refine_ls_wR_factor_ref         0.0986
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All N(H,H,H) groups
 At 1.5 times of:
  All O(H,H) groups
2.a Riding coordinates:
 N1'(H1',H3'a,H3'b,H3'c,H2',H3a,H2,H3b,H1,H3c)
2.b Free rotating group:
 OW1(HW1a,HW1b)
2.c Aromatic/amide H refined with riding coordinates:
 C6'(H6'), C6(H6), C3'(H3'), C5(H5), C4(H4), C3(H3), C5'(H5'), C4'(H4')
;
_atom_sites_solution_primary     direct
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_refinement_flags_posn
S1' S 0.10376(7) 0.05973(2) 0.17072(4) 0.00745(13) Uani 1.000000 .
S1 S 0.36643(7) 0.41524(2) 0.07329(3) 0.00703(13) Uani 1.000000 .
O3' O 0.1679(2) 0.05817(7) 0.27685(10) 0.0124(3) Uani 1.000000 .
O4 O 0.5337(2) 0.41006(7) 0.01001(10) 0.0107(3) Uani 1.000000 .
OW1 O 0.3195(2) 0.50870(7) 0.45376(11) 0.0116(3) Uani 1.000000 .
HW1a H 0.2042(12) 0.5079(11) 0.4249(14) 0.0174(5) Uiso 1.000000 G
HW1b H 0.323(3) 0.4828(10) 0.5062(11) 0.0174(5) Uiso 1.000000 G
O1' O 0.5269(2) 0.20040(7) 0.19253(11) 0.0148(3) Uani 1.000000 .
O1 O -0.0997(2) 0.30544(7) 0.12386(10) 0.0120(3) Uani 1.000000 .
O4' O 0.2671(2) 0.08021(7) 0.11220(10) 0.0107(3) Uani 1.000000 .
N1 N -0.0734(2) 0.40567(8) 0.20407(12) 0.0090(3) Uani 1.000000 .
N3 N -0.1293(2) 0.44204(8) 0.11592(12) 0.0081(3) Uani 1.000000 .
O5 O 0.4271(2) 0.45187(7) 0.16521(10) 0.0120(3) Uani 1.000000 .
O3 O 0.3066(2) 0.34592(7) 0.10064(10) 0.0122(3) Uani 1.000000 .
O2' O -0.0596(2) 0.10665(7) 0.15347(11) 0.0121(3) Uani 1.000000 .
O5' O 0.0391(2) -0.00936(7) 0.13810(10) 0.0105(3) Uani 1.000000 .
N2' N 0.6337(2) 0.36845(8) 0.45911(13) 0.0105(4) Uani 1.000000 .
N3' N 0.5924(2) 0.07662(8) 0.25272(12) 0.0090(3) Uani 1.000000 .
O2 O 0.2056(2) 0.44934(7) 0.01805(11) 0.0137(3) Uani 1.000000 .
N2 N 0.1566(2) 0.23169(8) 0.45845(12) 0.0097(3) Uani 1.000000 .
C6' C 0.5264(3) 0.31565(10) 0.30855(15) 0.0101(4) Uani 1.000000 .
H6' H 0.4756(3) 0.31865(10) 0.24313(15) 0.0122(5) Uiso 1.000000 R
C2 C -0.0559(3) 0.33813(10) 0.19894(14) 0.0083(4) Uani 1.000000 .
C6 C 0.0407(3) 0.23329(10) 0.28974(15) 0.0105(4) Uani 1.000000 .
H6 H 0.0085(3) 0.21006(10) 0.23090(15) 0.0126(5) Uiso 1.000000 R
C2' C 0.5575(3) 0.19243(10) 0.28191(14) 0.0085(4) Uani 1.000000 .
C1' C 0.5740(3) 0.25277(10) 0.35095(15) 0.0084(4) Uani 1.000000 .
C3' C 0.6493(3) 0.24929(10) 0.44884(15) 0.0099(4) Uani 1.000000 .
H3' H 0.6782(3) 0.20764(10) 0.47846(15) 0.0119(5) Uiso 1.000000 R
C5 C 0.1081(3) 0.19850(10) 0.37376(15) 0.0110(4) Uani 1.000000 .
H5 H 0.1200(3) 0.15158(10) 0.37156(15) 0.0133(5) Uiso 1.000000 R
C4 C 0.1417(3) 0.29930(10) 0.46480(15) 0.0103(4) Uani 1.000000 .
H4 H 0.1772(3) 0.32111(10) 0.52442(15) 0.0124(5) Uiso 1.000000 R
C1 C 0.0212(3) 0.30346(10) 0.29379(15) 0.0084(4) Uani 1.000000 .
C3 C 0.0741(3) 0.33665(10) 0.38331(15) 0.0094(4) Uani 1.000000 .
H3 H 0.0638(3) 0.38353(10) 0.38781(15) 0.0113(5) Uiso 1.000000 R
C5' C 0.5561(3) 0.37307(10) 0.36555(15) 0.0110(4) Uani 1.000000 .
H5' H 0.5224(3) 0.41526(10) 0.33909(15) 0.0132(5) Uiso 1.000000 R
C4' C 0.6806(3) 0.30882(10) 0.50138(15) 0.0109(4) Uani 1.000000 .
H4' H 0.7344(3) 0.30746(10) 0.56635(15) 0.0131(5) Uiso 1.000000 R
N1' N 0.5926(2) 0.13092(8) 0.32319(12) 0.0095(3) Uani 1.000000 .
H1' H 0.5678(2) 0.12190(8) 0.38332(12) 0.0114(4) Uiso 1.000000 R
H3'a H 0.7018(2) 0.08056(8) 0.21755(12) 0.0114(4) Uiso 1.000000 R
H3'b H 0.4934(2) 0.07909(8) 0.20402(12) 0.0114(4) Uiso 1.000000 R
H3'c H 0.5915(2) 0.03586(8) 0.28613(12) 0.0114(4) Uiso 1.000000 R
H2' H 0.6596(2) 0.40442(8) 0.49186(12) 0.0114(4) Uiso 1.000000 R
H3a H -0.1478(2) 0.48598(8) 0.13742(12) 0.0114(4) Uiso 1.000000 R
H2 H 0.2080(2) 0.20673(8) 0.51494(12) 0.0114(4) Uiso 1.000000 R
H3b H -0.0246(2) 0.44386(8) 0.07353(12) 0.0114(4) Uiso 1.000000 R
H1 H -0.0501(2) 0.43012(8) 0.25422(12) 0.0114(4) Uiso 1.000000 R
H3c H -0.2391(2) 0.42457(8) 0.08412(12) 0.0114(4) Uiso 1.000000 R


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
S1' O3' 1.4698(14) . ?
S1' O4' 1.4766(15) . ?
S1' O2' 1.4732(14) . ?
S1' O5' 1.4933(14) . ?
S1 O4 1.4852(14) . ?
S1 O5 1.4716(14) . ?
S1 O3 1.4827(14) . ?
S1 O2 1.4685(14) . ?
OW1 HW1a 0.8700 . ?
OW1 HW1b 0.8699 . ?
O1' C2' 1.218(2) . ?
O1 C2 1.221(2) . ?
N1 N3 1.420(2) . ?
N1 C2 1.340(3) . ?
N1 H1 0.837(2) . ?
N3 H3a 0.925(2) . ?
N3 H3b 0.952(2) . ?
N3 H3c 0.920(2) . ?
N2' C5' 1.342(3) . ?
N2' C4' 1.339(3) . ?
N2' H2' 0.849(2) . ?
N3' N1' 1.430(2) . ?
N3' H3'a 0.923(2) . ?
N3' H3'b 0.923(2) . ?
N3' H3'c 0.921(2) . ?
N2 C5 1.339(3) . ?
N2 C4 1.341(3) . ?
N2 H2 0.956(2) . ?
C6' H6' 0.9300 . ?
C6' C1' 1.397(3) . ?
C6' C5' 1.377(3) . ?
C2 C1 1.517(3) . ?
C6 H6 0.9300 . ?
C6 C5 1.380(3) . ?
C6 C1 1.393(3) . ?
C2' C1' 1.510(3) . ?
C2' N1' 1.351(3) . ?
C1' C3' 1.389(3) . ?
C3' H3' 0.9300 . ?
C3' C4' 1.381(3) . ?
C5 H5 0.9300 . ?
C4 H4 0.9300 . ?
C4 C3 1.380(3) . ?
C1 C3 1.400(3) . ?
C3 H3 0.9300 . ?
C5' H5' 0.9300 . ?
C4' H4' 0.9300 . ?
N1' H1' 0.8554 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O4' S1' O3' 108.93(8) . . ?
O2' S1' O3' 110.65(9) . . ?
O2' S1' O4' 110.78(8) . . ?
O5' S1' O3' 109.56(8) . . ?
O5' S1' O4' 108.74(8) . . ?
O5' S1' O2' 108.15(8) . . ?
O5 S1 O4 108.65(8) . . ?
O3 S1 O4 108.65(8) . . ?
O3 S1 O5 108.39(8) . . ?
O2 S1 O4 109.93(8) . . ?
O2 S1 O5 111.80(9) . . ?
O2 S1 O3 109.36(8) . . ?
HW1b OW1 HW1a 109.5 . . ?
C2 N1 N3 118.74(15) . . ?
H1 N1 N3 114.3(2) . . ?
H1 N1 C2 126.9(2) . . ?
H3a N3 N1 104.41(18) . . ?
H3b N3 N1 109.73(18) . . ?
H3b N3 H3a 106.1(2) . . ?
H3c N3 N1 112.15(19) . . ?
H3c N3 H3a 111.7(2) . . ?
H3c N3 H3b 112.3(2) . . ?
C4' N2' C5' 122.13(17) . . ?
H2' N2' C5' 119.4(2) . . ?
H2' N2' C4' 118.4(2) . . ?
H3'a N3' N1' 107.93(19) . . ?
H3'b N3' N1' 113.7(2) . . ?
H3'b N3' H3'a 103.6(2) . . ?
H3'c N3' N1' 109.3(2) . . ?
H3'c N3' H3'a 110.7(2) . . ?
H3'c N3' H3'b 111.5(2) . . ?
C4 N2 C5 121.60(17) . . ?
H2 N2 C5 119.13(19) . . ?
H2 N2 C4 119.2(2) . . ?
C1' C6' H6' 120.67(12) . . ?
C5' C6' H6' 120.67(12) . . ?
C5' C6' C1' 118.66(18) . . ?
N1 C2 O1 123.27(18) . . ?
C1 C2 O1 121.01(17) . . ?
C1 C2 N1 115.72(16) . . ?
C5 C6 H6 120.28(12) . . ?
C1 C6 H6 120.28(12) . . ?
C1 C6 C5 119.45(18) . . ?
C1' C2' O1' 120.47(18) . . ?
N1' C2' O1' 122.56(18) . . ?
N1' C2' C1' 116.79(17) . . ?
C2' C1' C6' 116.23(17) . . ?
C3' C1' C6' 119.83(18) . . ?
C3' C1' C2' 123.65(17) . . ?
H3' C3' C1' 120.60(11) . . ?
C4' C3' C1' 118.80(18) . . ?
C4' C3' H3' 120.60(12) . . ?
C6 C5 N2 120.59(18) . . ?
H5 C5 N2 119.70(11) . . ?
H5 C5 C6 119.70(12) . . ?
H4 C4 N2 119.84(11) . . ?
C3 C4 N2 120.31(18) . . ?
C3 C4 H4 119.84(12) . . ?
C6 C1 C2 116.48(17) . . ?
C3 C1 C2 124.99(17) . . ?
C3 C1 C6 118.53(18) . . ?
C1 C3 C4 119.51(18) . . ?
H3 C3 C4 120.25(12) . . ?
H3 C3 C1 120.25(11) . . ?
C6' C5' N2' 120.31(18) . . ?
H5' C5' N2' 119.84(11) . . ?
H5' C5' C6' 119.84(12) . . ?
C3' C4' N2' 120.22(18) . . ?
H4' C4' N2' 119.89(11) . . ?
H4' C4' C3' 119.89(12) . . ?
C2' N1' N3' 114.06(15) . . ?
H1' N1' N3' 118.6 . . ?
H1' N1' C2' 122.25(11) . . ?

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

data_INH_bromide
_database_code_depnum_ccdc_archive 'CCDC 1474926'
_audit_update_record             
;
2016-04-19 deposited with the CCDC.
2016-07-05 downloaded from the CCDC.
;

_audit_creation_date             2015-07-29T00:37:05-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'C6 H8 N3 O, Br'
_chemical_formula_sum            'C6 H8 Br N3 O'
_chemical_formula_weight         218.06
_chemical_compound_source        'synthesis as described'

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   6.6307(4)
_cell_length_b                   16.3280(13)
_cell_length_c                   7.4836(5)
_cell_angle_alpha                90
_cell_angle_beta                 92.183(7)
_cell_angle_gamma                90
_cell_volume                     809.63(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    290(2)
_cell_measurement_reflns_used    3647
_cell_measurement_theta_min      2.901
_cell_measurement_theta_max      25.242
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.01
_exptl_crystal_density_diffrn    1.789
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             432
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 1 0 0.009
0 -1 0 0.004
16 1 0 0.048
-16 -1 0 0.1
0 0 -1 0.144
0 0 1 0.162
-1 0 3 0.126
1 -1 -4 0.112


#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    5.022
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
        P. Coppens, L. Leiserowitz, D Rabinovich, Acta Cryst.
        (1965), 18, 1035-1038
;
_exptl_absorpt_correction_T_min  0.458
_exptl_absorpt_correction_T_max  0.937

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'Enraf Nonius FR590'
_diffrn_ambient_temperature      290(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 9
_diffrn_orient_matrix_type       'by Bruker AXS Collect from scalepack cell'
_diffrn_orient_matrix_ub_11      -0.043523
_diffrn_orient_matrix_ub_12      -0.03446
_diffrn_orient_matrix_ub_13      0.102058
_diffrn_orient_matrix_ub_21      -0.141443
_diffrn_orient_matrix_ub_22      0
_diffrn_orient_matrix_ub_23      -0.051386
_diffrn_orient_matrix_ub_31      0.029623
_diffrn_orient_matrix_ub_32      -0.05063
_diffrn_orient_matrix_ub_33      -0.069465
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_reflns_av_R_equivalents  0.0802
_diffrn_reflns_av_unetI/netI     0.0656
_diffrn_reflns_number            5442
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.996
_diffrn_reflns_theta_max         26.385
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_reflns_Friedel_coverage         0
_reflns_number_total             1654
_reflns_number_gt                1010
_reflns_threshold_expression     'I > 2σ(I)'
_diffrn_reflns_reduction_process 
;
        Scaled and merged with SORTAV
        R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
        R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0558P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         1654
_refine_ls_number_parameters     100
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.086
_refine_ls_R_factor_gt           0.0448
_refine_ls_wR_factor_ref         0.125
_refine_ls_wR_factor_gt          0.1056
_refine_ls_goodness_of_fit_ref   0.979
_refine_ls_restrained_S_all      0.979
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.504
_refine_diff_density_min         -0.397
_refine_diff_density_rms         0.082

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 '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'

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 0.75891(5) 0.03289(3) 0.74413(5) 0.0664(3) Uani 1 1 d . . . . .
O1 O -0.2592(4) 0.23376(19) 0.3309(5) 0.0684(9) Uani 1 1 d . . . . .
N2 N 0.4174(5) 0.2760(2) 0.5971(4) 0.0571(9) Uani 1 1 d . . . . .
C5 C 0.3961(6) 0.1955(3) 0.5881(5) 0.0558(11) Uani 1 1 d . . . . .
H5 H 0.4981 0.1618 0.6347 0.067 Uiso 1 1 calc R U . . .
C3 C 0.1032(6) 0.2970(3) 0.4496(5) 0.0525(10) Uani 1 1 d . . . . .
H3 H 0.0047 0.3324 0.4028 0.063 Uiso 1 1 calc R U . . .
C1 C 0.0749(5) 0.2135(3) 0.4388(5) 0.0466(10) Uani 1 1 d . . . . .
C6 C 0.2244(5) 0.1612(3) 0.5101(5) 0.0526(10) Uani 1 1 d . . . . .
H6 H 0.2084 0.1047 0.5051 0.063 Uiso 1 1 calc R U . . .
C2 C -0.1184(5) 0.1853(3) 0.3490(5) 0.0488(10) Uani 1 1 d . . . . .
C4 C 0.2773(6) 0.3281(3) 0.5296(5) 0.0588(11) Uani 1 1 d . . . . .
H4 H 0.2977 0.3843 0.5369 0.071 Uiso 1 1 calc R U . . .
N3 N -0.3087(5) 0.0843(2) 0.2018(5) 0.0661(10) Uani 1 1 d . . . . .
N1 N -0.1285(5) 0.1086(2) 0.2903(4) 0.0551(9) Uani 1 1 d . . . . .
H1 H -0.0317 0.0693 0.3031 0.066 Uiso 1 1 d R U . . .
H2 H 0.5463 0.3031 0.6553 0.066 Uiso 1 1 d R U . . .
H3B H -0.279 0.0486 0.1055 0.066 Uiso 1 1 d R U . . .
H3A H -0.3614 0.047 0.2834 0.066 Uiso 1 1 d R U . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 C2 1.227(4) . ?
N2 C5 1.322(5) . ?
N2 C4 1.344(5) . ?
N2 H2 1.043 . ?
C5 C6 1.378(5) . ?
C5 H5 0.93 . ?
C3 C4 1.377(5) . ?
C3 C1 1.378(5) . ?
C3 H3 0.93 . ?
C1 C6 1.399(5) . ?
C1 C2 1.497(5) . ?
C6 H6 0.93 . ?
C2 N1 1.328(5) . ?
C4 H4 0.93 . ?
N3 N1 1.401(5) . ?
N3 H3B 0.9535 . ?
N3 H3A 0.9396 . ?
N1 H1 0.9099 . ?

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 N2 C4 122.6(4) . . ?
C5 N2 H2 121.8 . . ?
C4 N2 H2 115.6 . . ?
N2 C5 C6 120.7(4) . . ?
N2 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C4 C3 C1 120.0(4) . . ?
C4 C3 H3 120 . . ?
C1 C3 H3 120 . . ?
C3 C1 C6 119.3(4) . . ?
C3 C1 C2 116.3(3) . . ?
C6 C1 C2 124.5(4) . . ?
C5 C6 C1 118.4(4) . . ?
C5 C6 H6 120.8 . . ?
C1 C6 H6 120.8 . . ?
O1 C2 N1 122.9(3) . . ?
O1 C2 C1 119.1(4) . . ?
N1 C2 C1 118.0(3) . . ?
N2 C4 C3 119.1(4) . . ?
N2 C4 H4 120.5 . . ?
C3 C4 H4 120.5 . . ?
N1 N3 H3B 109.5 . . ?
N1 N3 H3A 102 . . ?
H3B N3 H3A 100.8 . . ?
C2 N1 N3 117.0(3) . . ?
C2 N1 H1 127.1 . . ?
N3 N1 H1 115.8 . . ?

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
C4 N2 C5 C6 -1.1(6) . . . . ?
C4 C3 C1 C6 0.1(6) . . . . ?
C4 C3 C1 C2 -179.8(4) . . . . ?
N2 C5 C6 C1 0.9(6) . . . . ?
C3 C1 C6 C5 -0.4(6) . . . . ?
C2 C1 C6 C5 179.5(3) . . . . ?
C3 C1 C2 O1 -18.0(5) . . . . ?
C6 C1 C2 O1 162.1(4) . . . . ?
C3 C1 C2 N1 161.2(3) . . . . ?
C6 C1 C2 N1 -18.7(6) . . . . ?
C5 N2 C4 C3 0.8(6) . . . . ?
C1 C3 C4 N2 -0.3(6) . . . . ?
O1 C2 N1 N3 1.1(6) . . . . ?
C1 C2 N1 N3 -178.1(3) . . . . ?

####################################################################### 
# 
# 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_isonitrate
_database_code_depnum_ccdc_archive 'CCDC 1474927'
_audit_update_record             
;
2016-04-19 deposited with the CCDC.
2016-07-05 downloaded from the CCDC.
;

_audit_creation_date             2016-04-14T06:18:23-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'C6 H8 N3 O, N O3'
_chemical_formula_sum            'C6 H8 N4 O4'
_chemical_formula_weight         200.16
_chemical_compound_source        'synthesis as described'

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C c'
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_Int_Tables_number      9
loop_
_symmetry_equiv_pos_as_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'

_cell_length_a                   6.3630(13)
_cell_length_b                   15.970(6)
_cell_length_c                   8.043(2)
_cell_angle_alpha                90
_cell_angle_beta                 92.151(16)
_cell_angle_gamma                90
_cell_volume                     816.7(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    290(2)
_cell_measurement_reflns_used    771
_cell_measurement_theta_min      0.407
_cell_measurement_theta_max      27.485
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.03
_exptl_crystal_density_diffrn    1.628
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             416
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 0 -2 0.055
1 0 2 0.07
-1 0 1 0.252
3 0 -4 0.16
0 -1 0 0.011
0 1 0 0.015
-1 -1 16 0.15
-1 0 2 0.214


#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.138
_exptl_absorpt_correction_type   none

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'Enraf Nonius FR590'
_diffrn_ambient_temperature      290(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 9
_diffrn_orient_matrix_type       'by Bruker AXS Collect from scalepack cell'
_diffrn_orient_matrix_ub_11      -0.0331356
_diffrn_orient_matrix_ub_12      -0.0229982
_diffrn_orient_matrix_ub_13      0.111657
_diffrn_orient_matrix_ub_21      0.153174
_diffrn_orient_matrix_ub_22      0
_diffrn_orient_matrix_ub_23      0.0327152
_diffrn_orient_matrix_ub_31      -0.013085
_diffrn_orient_matrix_ub_32      0.058239
_diffrn_orient_matrix_ub_33      0.0440926
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_reflns_av_R_equivalents  0.0494
_diffrn_reflns_av_unetI/netI     0.0492
_diffrn_reflns_number            1462
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         3.449
_diffrn_reflns_theta_max         25.331
_diffrn_reflns_theta_full        25.24
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 0.97
_reflns_Friedel_fraction_full    0.947
_reflns_Friedel_fraction_max     0.945
_reflns_Friedel_coverage         0.939
_reflns_number_total             1454
_reflns_number_gt                1183
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0781P)²+0.1872P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_coef       0.062(15)
_refine_ls_number_reflns         1454
_refine_ls_number_parameters     128
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0636
_refine_ls_R_factor_gt           0.0495
_refine_ls_wR_factor_ref         0.1374
_refine_ls_wR_factor_gt          0.1261
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.054
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.161
_refine_diff_density_min         -0.148
_refine_diff_density_rms         0.041

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
O3 0.0830(6) 0.2894(3) 0.2428(5) 0.0700(11) Uani d 1 . . O
O1 0.6802(6) -0.0030(3) 0.3215(6) 0.0750(12) Uani d 1 . . O
N1 0.6155(6) 0.1263(3) 0.4177(5) 0.0611(11) Uani d 1 . . N
N2 0.0468(6) -0.0538(3) 0.6410(5) 0.0569(11) Uani d 1 . . N
O2 0.4184(6) 0.2891(3) 0.2143(6) 0.0826(13) Uani d 1 . . O
N4 0.2657(7) 0.2842(3) 0.3064(5) 0.0584(11) Uani d 1 . . N
C1 0.3894(7) 0.0123(3) 0.4942(6) 0.0495(11) Uani d 1 . . C
C6 0.2390(7) 0.0646(3) 0.5628(6) 0.0564(12) Uani d 1 . . C
H6 0.2535 0.1225 0.5583 0.068 Uiso calc 1 . . H
C4 0.1870(8) -0.1058(3) 0.5752(7) 0.0603(13) Uani d 1 . . C
H4 0.168 -0.1634 0.5809 0.072 Uiso calc 1 . . H
C2 0.5772(7) 0.0452(3) 0.4051(6) 0.0526(11) Uani d 1 . . C
C3 0.3591(7) -0.0732(3) 0.4992(6) 0.0578(12) Uani d 1 . . C
H3 0.4551 -0.1089 0.4511 0.069 Uiso calc 1 . . H
O4 0.2913(7) 0.2733(3) 0.4567(5) 0.0915(14) Uani d 1 . . O
C5 0.0700(8) 0.0293(3) 0.6367(6) 0.0598(12) Uani d 1 . . C
H5 -0.0296 0.0634 0.6843 0.072 Uiso calc 1 . . H
N3 0.7840(6) 0.1608(3) 0.3313(5) 0.0606(12) Uani d 1 . . N
H3B 0.8629 0.183 0.4154 0.073 Uiso d 1 . . H
H3A 0.7388 0.1987 0.2472 0.073 Uiso d 1 . . H
H1 0.5374 0.1541 0.4707 0.073 Uiso d 1 . . H
H2 -0.0774 -0.0805 0.7263 0.073 Uiso d 1 . . H



#==============================================================================

# MOLECULAR GEOMETRY

_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O3 N4 . 1.255(6) ?
O1 C2 . 1.227(6) ?
N1 C2 . 1.322(6) ?
N1 N3 . 1.412(5) ?
N2 C5 . 1.335(7) ?
N2 C4 . 1.341(7) ?
O2 N4 . 1.246(6) ?
N4 O4 . 1.226(5) ?
C1 C3 . 1.381(7) ?
C1 C6 . 1.399(7) ?
C1 C2 . 1.511(7) ?
C6 C5 . 1.370(7) ?
C4 C3 . 1.376(7) ?

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 N3 119.1(4) . . ?
C5 N2 C4 121.9(4) . . ?
O4 N4 O2 121.2(5) . . ?
O4 N4 O3 119.9(4) . . ?
O2 N4 O3 119.0(4) . . ?
C3 C1 C6 118.8(4) . . ?
C3 C1 C2 118.1(4) . . ?
C6 C1 C2 123.0(4) . . ?
C5 C6 C1 119.0(5) . . ?
N2 C4 C3 119.6(5) . . ?
O1 C2 N1 123.8(5) . . ?
O1 C2 C1 119.4(4) . . ?
N1 C2 C1 116.8(4) . . ?
C4 C3 C1 120.0(4) . . ?
N2 C5 C6 120.7(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
C3 C1 C6 C5 1.9(7) . . . . ?
C2 C1 C6 C5 178.1(4) . . . . ?
C5 N2 C4 C3 -0.7(8) . . . . ?
N3 N1 C2 O1 -0.1(8) . . . . ?
N3 N1 C2 C1 -177.3(4) . . . . ?
C3 C1 C2 O1 9.9(7) . . . . ?
C6 C1 C2 O1 -166.2(5) . . . . ?
C3 C1 C2 N1 -172.7(4) . . . . ?
C6 C1 C2 N1 11.1(7) . . . . ?
N2 C4 C3 C1 1.4(8) . . . . ?
C6 C1 C3 C4 -2.0(7) . . . . ?
C2 C1 C3 C4 -178.3(4) . . . . ?
C4 N2 C5 C6 0.7(8) . . . . ?
C1 C6 C5 N2 -1.3(8) . . . . ?



# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
####################################################################### 
# 
# 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_INH_sulfate
_database_code_depnum_ccdc_archive 'CCDC 1474928'
_audit_update_record             
;
2016-04-19 deposited with the CCDC.
2016-07-05 downloaded from the CCDC.
;

_audit_creation_date             2016-04-14T04:36:39-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#


_chemical_formula_moiety         'C6 H9 N3 O1, O4 S'
_chemical_formula_sum            'C6 H9 N3 O5 S'
_chemical_formula_weight         235.22

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_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                   7.3259(2)
_cell_length_b                   6.3982(2)
_cell_length_c                   19.5779(7)
_cell_angle_alpha                90
_cell_angle_beta                 98.2460(10)
_cell_angle_gamma                90
_cell_volume                     908.18(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    290(2)
_cell_measurement_reflns_used    2174
_cell_measurement_theta_min      2.902
_cell_measurement_theta_max      25.242
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.03
_exptl_crystal_density_diffrn    1.72
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             488
_exptl_crystal_description       'Plate shaped'
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.365
_exptl_absorpt_correction_type   none

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'Enraf Nonius FR590'
_diffrn_ambient_temperature      290(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 9
_diffrn_orient_matrix_ub_11      0.047335
_diffrn_orient_matrix_ub_12      -0.059123
_diffrn_orient_matrix_ub_13      -0.041373
_diffrn_orient_matrix_ub_21      -0.128099
_diffrn_orient_matrix_ub_22      0
_diffrn_orient_matrix_ub_23      -0.025812
_diffrn_orient_matrix_ub_31      0.019343
_diffrn_orient_matrix_ub_32      0.14468
_diffrn_orient_matrix_ub_33      -0.016907
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_reflns_av_R_equivalents  0.101
_diffrn_reflns_av_unetI/netI     0.0588
_diffrn_reflns_number            1859
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         3.138
_diffrn_reflns_theta_max         26.399
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_reflns_Friedel_coverage         0
_reflns_number_total             1859
_reflns_number_gt                1424
_reflns_threshold_expression     'I > 2σ(I)'
_diffrn_reflns_reduction_process 
;
        Scaled and merged with Sortav
        R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
        R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0735P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         1859
_refine_ls_number_parameters     136
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0636
_refine_ls_R_factor_gt           0.0463
_refine_ls_wR_factor_ref         0.1291
_refine_ls_wR_factor_gt          0.1206
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.475
_refine_diff_density_min         -0.418
_refine_diff_density_rms         0.07

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 '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'

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
S1 S 0.50895(7) 0.45188(8) 0.32094(3) 0.0321(2) Uani 1 1 d . . . . .
O1 O 0.4829(2) 0.9607(2) 0.08371(8) 0.0456(5) Uani 1 1 d . . . . .
O2 O 0.4683(2) 0.4297(2) 0.39247(8) 0.0445(4) Uani 1 1 d . . . . .
O3 O 0.64952(19) 0.6164(2) 0.31897(7) 0.0390(4) Uani 1 1 d . . . . .
C1 C 0.3362(3) 0.6338(3) 0.05926(10) 0.0300(5) Uani 1 1 d . . . . .
N2 N 0.1652(2) 0.3491(3) -0.03232(9) 0.0370(5) Uani 1 1 d . . . . .
N1 N 0.4593(2) 0.7522(3) 0.17367(9) 0.0330(5) Uani 1 1 d . . . . .
O4 O 0.3407(2) 0.5138(3) 0.27570(9) 0.0584(6) Uani 1 1 d . . . . .
C2 C 0.4306(3) 0.7988(3) 0.10612(10) 0.0299(5) Uani 1 1 d . . . . .
C3 C 0.2871(3) 0.4384(3) 0.08198(11) 0.0358(5) Uani 1 1 d . . . . .
H3 H 0.3129 0.4024 0.1284 0.043 Uiso 1 1 calc R U . . .
C5 C 0.2141(3) 0.5362(3) -0.05549(11) 0.0367(5) Uani 1 1 d . . . . .
H5 H 0.1892 0.5673 -0.1023 0.044 Uiso 1 1 calc R U . . .
O5 O 0.5817(3) 0.2543(3) 0.29992(9) 0.0575(5) Uani 1 1 d . . . . .
C6 C 0.2997(3) 0.6801(3) -0.01055(10) 0.0344(5) Uani 1 1 d . . . . .
H6 H 0.3337 0.809 -0.0267 0.041 Uiso 1 1 calc R U . . .
C4 C 0.2000(3) 0.2997(4) 0.03463(11) 0.0398(6) Uani 1 1 d . . . . .
H4 H 0.1647 0.1695 0.0493 0.048 Uiso 1 1 calc R U . . .
N3 N 0.5363(2) 0.9109(3) 0.21944(8) 0.0321(4) Uani 1 1 d . . . . .
H3B H 0.6243 0.9853 0.1988 0.039 Uiso 1 1 d R U . . .
H2 H 0.0952 0.2431 -0.0669 0.039 Uiso 1 1 d R U . . .
H3C H 0.5805 0.8448 0.2571 0.039 Uiso 1 1 d R U . . .
H3A H 0.4466 1.0074 0.2295 0.039 Uiso 1 1 d R U . . .
H1 H 0.3889 0.6539 0.1914 0.039 Uiso 1 1 d R U . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
S1 O5 1.4540(17) . ?
S1 O4 1.4652(16) . ?
S1 O3 1.4768(15) . ?
S1 O2 1.4797(16) . ?
O1 C2 1.208(2) . ?
C1 C6 1.387(3) . ?
C1 C3 1.391(3) . ?
C1 C2 1.501(3) . ?
N2 C4 1.337(3) . ?
N2 C5 1.346(3) . ?
N2 H2 1.0406 . ?
N1 C2 1.343(3) . ?
N1 N3 1.417(2) . ?
N1 H1 0.9132 . ?
C3 C4 1.373(3) . ?
C3 H3 0.93 . ?
C5 C6 1.363(3) . ?
C5 H5 0.93 . ?
C6 H6 0.93 . ?
C4 H4 0.93 . ?
N3 H3B 0.9385 . ?
N3 H3C 0.8703 . ?
N3 H3A 0.9431 . ?

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 S1 O4 111.99(12) . . ?
O5 S1 O3 109.09(10) . . ?
O4 S1 O3 108.71(9) . . ?
O5 S1 O2 108.42(10) . . ?
O4 S1 O2 109.40(10) . . ?
O3 S1 O2 109.19(9) . . ?
C6 C1 C3 119.02(19) . . ?
C6 C1 C2 117.31(18) . . ?
C3 C1 C2 123.66(18) . . ?
C4 N2 C5 121.21(19) . . ?
C4 N2 H2 119.4 . . ?
C5 N2 H2 119.4 . . ?
C2 N1 N3 117.12(16) . . ?
C2 N1 H1 120.7 . . ?
N3 N1 H1 116.6 . . ?
O1 C2 N1 122.36(19) . . ?
O1 C2 C1 121.55(18) . . ?
N1 C2 C1 116.04(18) . . ?
C4 C3 C1 118.8(2) . . ?
C4 C3 H3 120.6 . . ?
C1 C3 H3 120.6 . . ?
N2 C5 C6 120.2(2) . . ?
N2 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C5 C6 C1 119.9(2) . . ?
C5 C6 H6 120.1 . . ?
C1 C6 H6 120.1 . . ?
N2 C4 C3 120.9(2) . . ?
N2 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?
N1 N3 H3B 109.1 . . ?
N1 N3 H3C 104.6 . . ?
H3B N3 H3C 114.6 . . ?
N1 N3 H3A 112 . . ?
H3B N3 H3A 107.5 . . ?
H3C N3 H3A 109.1 . . ?

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
N3 N1 C2 O1 6.7(3) . . . . ?
N3 N1 C2 C1 -175.66(17) . . . . ?
C6 C1 C2 O1 -4.3(3) . . . . ?
C3 C1 C2 O1 174.6(2) . . . . ?
C6 C1 C2 N1 178.10(19) . . . . ?
C3 C1 C2 N1 -3.1(3) . . . . ?
C6 C1 C3 C4 -1.6(3) . . . . ?
C2 C1 C3 C4 179.6(2) . . . . ?
C4 N2 C5 C6 -0.4(3) . . . . ?
N2 C5 C6 C1 -0.2(3) . . . . ?
C3 C1 C6 C5 1.2(3) . . . . ?
C2 C1 C6 C5 -179.92(19) . . . . ?
C5 N2 C4 C3 -0.1(3) . . . . ?
C1 C3 C4 N2 1.1(3) . . . . ?



# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF

