# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_1HCl
_database_code_depnum_ccdc_archive 'CCDC 1436608'
_audit_update_record             
;
2015-11-12 deposited with the CCDC.
2015-12-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H10 N O2 1+,Cl 1-'
_chemical_formula_sum            'C9 H10 Cl N O2'
_chemical_formula_weight         199.63

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'
Cl Cl 0.1484 0.1585 '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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21/c

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                   5.5837(7)
_cell_length_b                   8.5339(10)
_cell_length_c                   19.865(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.074(11)
_cell_angle_gamma                90.00
_cell_volume                     946.0(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293.15
_cell_measurement_reflns_used    826
_cell_measurement_theta_min      3.1410
_cell_measurement_theta_max      23.7140

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.402
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             416
_exptl_absorpt_coefficient_mu    0.369
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.98441
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      298
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Sapphire3
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean 16.1340
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3904
_diffrn_reflns_av_R_equivalents  0.0425
_diffrn_reflns_av_sigmaI/netI    0.0981
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.15
_diffrn_reflns_theta_max         29.19
_reflns_number_total             2155
_reflns_number_gt                1178
_reflns_threshold_expression     >2σ(I)
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -83.00   11.00   1.0000  150.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.3596  -77.0000  -60.0000 94

#__ type_ start__ end____ width___ exp.time_
  2 omega  -22.00   54.00   1.0000  150.0000
omega____ theta____ kappa____ phi______ frames
    -       17.4534  -99.0000   90.0000 76

#__ type_ start__ end____ width___ exp.time_
  3 omega   59.00   85.00   1.0000  150.0000
omega____ theta____ kappa____ phi______ frames
    -       17.4534   57.0000 -180.0000 26

;

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2005)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0282P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2155
_refine_ls_number_parameters     134
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.1489
_refine_ls_R_factor_gt           0.0700
_refine_ls_wR_factor_ref         0.1218
_refine_ls_wR_factor_gt          0.0975
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1415(6) 0.7301(4) 0.08398(17) 0.0465(9) Uani 1 1 d . . .
H1 H 0.2762 0.7927 0.0792 0.056 Uiso 1 1 calc R . .
C2 C 0.1084(6) 0.6550(4) 0.14393(17) 0.0465(9) Uani 1 1 d . . .
H2 H 0.2196 0.6657 0.1796 0.056 Uiso 1 1 calc R . .
C3 C -0.0920(6) 0.5636(3) 0.15038(16) 0.0375(8) Uani 1 1 d . . .
C4 C -0.2609(6) 0.5487(4) 0.09957(17) 0.0448(9) Uani 1 1 d . . .
H4 H -0.3977 0.4887 0.1052 0.054 Uiso 1 1 calc R . .
C5 C -0.2244(6) 0.6248(4) 0.03957(16) 0.0454(9) Uani 1 1 d . . .
H5 H -0.3385 0.6157 0.0045 0.055 Uiso 1 1 calc R . .
C6 C -0.0224(6) 0.7142(3) 0.03039(16) 0.0395(8) Uani 1 1 d . . .
C7 C 0.0159(6) 0.7837(4) -0.03555(16) 0.0473(9) Uani 1 1 d . . .
H7 H -0.1015 0.7648 -0.0689 0.057 Uiso 1 1 calc R . .
C8 C 0.2000(7) 0.8710(4) -0.05283(16) 0.0489(9) Uani 1 1 d . . .
H8 H 0.3199 0.8949 -0.0208 0.059 Uiso 1 1 calc R . .
C9 C 0.2177(7) 0.9305(4) -0.12184(19) 0.0484(9) Uani 1 1 d . . .
Cl1 Cl 0.38882(16) 0.31000(9) 0.23356(5) 0.0546(3) Uani 1 1 d . . .
N1 N -0.1192(7) 0.4793(4) 0.21416(17) 0.0504(8) Uani 1 1 d D . .
O1 O 0.3929(5) 1.0328(3) -0.12819(14) 0.0637(8) Uani 1 1 d D . .
O2 O 0.0864(5) 0.8891(3) -0.16819(12) 0.0725(8) Uani 1 1 d . . .
H1NA H -0.256(5) 0.429(4) 0.2142(18) 0.091(16) Uiso 1 1 d D . .
H2NB H -0.122(8) 0.546(4) 0.2466(16) 0.107(19) Uiso 1 1 d D . .
H3NC H 0.003(6) 0.417(4) 0.220(2) 0.13(2) Uiso 1 1 d D . .
H1O1 H 0.410(8) 1.066(4) -0.1691(12) 0.102(17) Uiso 1 1 d D . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
C1 C2 1.371(4) . ?
C1 C6 1.385(4) . ?
C2 C3 1.374(4) . ?
C3 C4 1.362(4) . ?
C3 N1 1.469(4) . ?
C4 C5 1.379(4) . ?
C5 C6 1.379(4) . ?
C6 C7 1.461(4) . ?
C7 C8 1.324(4) . ?
C8 C9 1.469(4) . ?
C9 O2 1.209(4) . ?
C9 O1 1.321(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 121.0(3) . . ?
C1 C2 C3 118.9(3) . . ?
C4 C3 C2 121.9(3) . . ?
C4 C3 N1 120.2(3) . . ?
C2 C3 N1 117.9(3) . . ?
C3 C4 C5 118.5(3) . . ?
C4 C5 C6 121.5(3) . . ?
C5 C6 C1 118.2(3) . . ?
C5 C6 C7 119.3(3) . . ?
C1 C6 C7 122.4(3) . . ?
C8 C7 C6 126.9(3) . . ?
C7 C8 C9 121.0(3) . . ?
O2 C9 O1 123.4(3) . . ?
O2 C9 C8 123.4(3) . . ?
O1 C9 C8 113.1(3) . . ?

_diffrn_measured_fraction_theta_max 0.842
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.235
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.049
####################################################################### 
# 
# 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_1HCl_86
_database_code_depnum_ccdc_archive 'CCDC 1436609'
_audit_update_record             
;
2015-11-12 deposited with the CCDC.
2015-12-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H10 Cl N O2'
_chemical_formula_weight         199.63

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'
Cl Cl 0.1484 0.1585 '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'

_symmetry_cell_setting           MONOCLINIC
_symmetry_space_group_name_H-M   P21/C

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                   5.6063(2)
_cell_length_b                   8.5811(7)
_cell_length_c                   19.4662(17)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.595(7)
_cell_angle_gamma                90.00
_cell_volume                     936.12(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    298
_cell_measurement_reflns_used    1118
_cell_measurement_theta_min      3.1580
_cell_measurement_theta_max      24.4520

_exptl_crystal_description       PRISM
_exptl_crystal_colour            YELLOW
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.416
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             416
_exptl_absorpt_coefficient_mu    0.373
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.34976
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      298
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Sapphire3
_diffrn_detector_area_resol_mean 16.1340
_diffrn_reflns_number            4265
_diffrn_reflns_av_R_equivalents  0.0271
_diffrn_reflns_av_sigmaI/netI    0.0556
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.59
_diffrn_reflns_theta_max         29.42
_reflns_number_total             2145
_reflns_number_gt                1472
_reflns_threshold_expression     >2σ(I)
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -24.00   24.00   1.0000  142.5000
omega____ theta____ kappa____ phi______ frames
    -      -16.3596  -99.0000   90.0000 48

#__ type_ start__ end____ width___ exp.time_
  2 omega   12.00   58.00   1.0000  142.5000
omega____ theta____ kappa____ phi______ frames
    -       17.6096  -99.0000   60.0000 46

#__ type_ start__ end____ width___ exp.time_
  3 omega  -49.00   74.00   1.0000  142.5000
omega____ theta____ kappa____ phi______ frames
    -       17.6096    0.0000  120.0000 123

;

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0666P)²+0.5189P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2145
_refine_ls_number_parameters     119
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1382
_refine_ls_R_factor_gt           0.0948
_refine_ls_wR_factor_ref         0.2018
_refine_ls_wR_factor_gt          0.1826
_refine_ls_goodness_of_fit_ref   1.220
_refine_ls_restrained_S_all      1.220
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C7A C 1.0179(8) 0.2120(6) -0.0370(2) 0.0475(13) Uiso 0.860(7) 1 d P A 1
H7A H 0.9033 0.2311 -0.0714 0.057 Uiso 0.860(7) 1 calc PR A 1
C8A C 1.2015(8) 0.1229(6) -0.0537(3) 0.0482(13) Uiso 0.860(7) 1 d P A 1
H8A H 1.3224 0.1028 -0.0212 0.058 Uiso 0.860(7) 1 calc PR A 1
C7B C 0.915(4) 0.115(3) -0.0032(14) 0.041(8) Uiso 0.140(7) 1 d P . 2
H7B H 0.8239 0.1344 -0.0460 0.049 Uiso 0.140(7) 1 calc PR A 2
C8B C 1.155(5) 0.040(4) -0.0227(16) 0.049(8) Uiso 0.140(7) 1 d P . 2
H8B H 1.2883 0.0833 0.0050 0.059 Uiso 0.140(7) 1 calc PR A 2
Cl1 Cl 0.39292(17) 0.70506(14) 0.23245(6) 0.0606(4) Uani 1 1 d . . .
N1 N 0.8857(5) 0.5403(4) 0.21342(18) 0.0571(10) Uani 1 1 d . . .
H1A H 0.9047 0.4782 0.2498 0.086 Uiso 1 1 calc R . .
H1B H 0.7410 0.5828 0.2135 0.086 Uiso 1 1 calc R . .
H1C H 0.9956 0.6151 0.2152 0.086 Uiso 1 1 calc R . .
O2 O 1.3930(6) -0.0402(4) -0.12917(17) 0.0740(10) Uani 1 1 d . A .
H2W H 1.3881 -0.0793 -0.1772 0.111 Uiso 1 1 calc R . .
C5 C 1.1411(7) 0.2743(5) 0.0859(2) 0.0564(12) Uani 1 1 d . A .
H5 H 1.2742 0.2103 0.0824 0.068 Uiso 1 1 calc R . .
O1 O 1.0823(6) 0.0948(4) -0.16761(18) 0.0796(11) Uani 1 1 d . A .
C2 C 0.7419(7) 0.4581(5) 0.0996(2) 0.0499(10) Uani 1 1 d . . .
H2 H 0.6058 0.5185 0.1048 0.060 Uiso 1 1 calc R . .
C1 C 0.9118(6) 0.4498(5) 0.1510(2) 0.0427(9) Uani 1 1 d . . .
C3 C 0.7752(7) 0.3756(5) 0.0399(2) 0.0588(12) Uani 1 1 d . A .
H3 H 0.6598 0.3812 0.0048 0.071 Uiso 1 1 calc R . .
C6 C 1.1093(6) 0.3577(5) 0.1451(2) 0.0501(11) Uani 1 1 d . . .
H6 H 1.2215 0.3516 0.1811 0.060 Uiso 1 1 calc R . .
C9 C 1.2148(7) 0.0582(5) -0.1206(3) 0.0584(12) Uani 1 1 d . . .
C4 C 0.9770(7) 0.2839(5) 0.0308(2) 0.0559(11) Uani 1 1 d . . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
C7A C8A 1.330(6) . ?
C7A C4 1.480(6) . ?
C8A C9 1.418(7) . ?
C7B C8B 1.48(4) 3_755 ?
C7B C8B 1.55(4) . ?
C7B C4 1.62(3) . ?
C8B C7B 1.48(4) 3_755 ?
C8B C9 1.95(3) . ?
N1 C1 1.453(5) . ?
O2 C9 1.322(5) . ?
C5 C6 1.373(6) . ?
C5 C4 1.396(6) . ?
O1 C9 1.205(5) . ?
C2 C1 1.363(5) . ?
C2 C3 1.377(6) . ?
C1 C6 1.368(5) . ?
C3 C4 1.393(6) . ?

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
C8A C7A C4 126.7(4) . . ?
C7A C8A C9 120.7(4) . . ?
C8B C7B C8B 87(2) 3_755 . ?
C8B C7B C4 136(2) 3_755 . ?
C8B C7B C4 107.2(19) . . ?
C7B C8B C7B 93(2) 3_755 . ?
C7B C8B C9 117(2) 3_755 . ?
C7B C8B C9 112.3(19) . . ?
C6 C5 C4 121.1(4) . . ?
C1 C2 C3 118.9(4) . . ?
C2 C1 C6 121.3(4) . . ?
C2 C1 N1 120.1(3) . . ?
C6 C1 N1 118.6(3) . . ?
C2 C3 C4 121.8(4) . . ?
C1 C6 C5 119.7(4) . . ?
O1 C9 O2 121.5(5) . . ?
O1 C9 C8A 123.3(4) . . ?
O2 C9 C8A 115.2(4) . . ?
O1 C9 C8B 130.2(9) . . ?
O2 C9 C8B 102.9(9) . . ?
C8A C9 C8B 28.3(9) . . ?
C3 C4 C5 117.1(4) . . ?
C3 C4 C7A 119.7(4) . . ?
C5 C4 C7A 123.0(4) . . ?
C3 C4 C7B 113.0(9) . . ?
C5 C4 C7B 112.8(10) . . ?
C7A C4 C7B 45.7(10) . . ?

_diffrn_measured_fraction_theta_max 0.830
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.302
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.058
####################################################################### 
# 
# 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_1HCl_80
_database_code_depnum_ccdc_archive 'CCDC 1436610'
_audit_update_record             
;
2015-11-12 deposited with the CCDC.
2015-12-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H10 Cl N O2'
_chemical_formula_weight         199.63

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'
Cl Cl 0.1484 0.1585 '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'

_symmetry_cell_setting           MONOCLINIC
_symmetry_space_group_name_H-M   P21/C

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                   5.6180(3)
_cell_length_b                   8.5855(7)
_cell_length_c                   19.373(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.521(7)
_cell_angle_gamma                90.00
_cell_volume                     934.08(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    298
_cell_measurement_reflns_used    920
_cell_measurement_theta_min      3.1700
_cell_measurement_theta_max      23.7150

_exptl_crystal_description       PRISM
_exptl_crystal_colour            YELLOW
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.420
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             416
_exptl_absorpt_coefficient_mu    0.374
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.69675
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      298
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Sapphire3
_diffrn_detector_area_resol_mean 16.1340
_diffrn_reflns_number            4165
_diffrn_reflns_av_R_equivalents  0.0281
_diffrn_reflns_av_sigmaI/netI    0.0624
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.17
_diffrn_reflns_theta_max         29.12
_reflns_number_total             2131
_reflns_number_gt                1345
_reflns_threshold_expression     >2σ(I)
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -24.00   14.00   1.0000  135.0000
omega____ theta____ kappa____ phi______ frames
    -       17.6096  -57.0000   60.0000 38

#__ type_ start__ end____ width___ exp.time_
  2 omega  -24.00   17.00   1.0000  135.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.3596  -99.0000  150.0000 41

#__ type_ start__ end____ width___ exp.time_
  3 omega  -89.00  -41.00   1.0000  135.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.3596 -179.0000   30.0000 48

#__ type_ start__ end____ width___ exp.time_
  4 omega  -86.00    6.00   1.0000  135.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.3596  -38.0000  -90.0000 92

;

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0533P)²+0.8565P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2131
_refine_ls_number_parameters     119
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1499
_refine_ls_R_factor_gt           0.0925
_refine_ls_wR_factor_ref         0.1923
_refine_ls_wR_factor_gt          0.1679
_refine_ls_goodness_of_fit_ref   1.160
_refine_ls_restrained_S_all      1.160
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C7A C 0.4814(9) 1.2119(6) 0.0371(3) 0.0502(16) Uiso 0.809(8) 1 d P A 1
H7A H 0.5953 1.2313 0.0718 0.060 Uiso 0.809(8) 1 calc PR A 1
C8A C 0.2979(9) 1.1237(7) 0.0542(3) 0.0515(15) Uiso 0.809(8) 1 d P A 1
H8A H 0.1751 1.1064 0.0219 0.062 Uiso 0.809(8) 1 calc PR A 1
C7B C 0.574(4) 1.118(3) 0.0035(12) 0.048(7) Uiso 0.191(8) 1 d P . 2
H7B H 0.6667 1.1374 0.0462 0.057 Uiso 0.191(8) 1 calc PR A 2
C8B C 0.344(4) 1.040(3) 0.0241(12) 0.048(6) Uiso 0.191(8) 1 d P . 2
H8B H 0.2084 1.0801 -0.0035 0.057 Uiso 0.191(8) 1 calc PR A 2
Cl1 Cl 0.89411(18) 0.29143(15) 0.23235(7) 0.0636(4) Uani 1 1 d . . .
O1 O 0.1062(6) 0.9585(5) 0.12674(18) 0.0788(11) Uani 1 1 d . A .
H1 H 0.0920 0.9383 0.1678 0.118 Uiso 1 1 calc R . .
O2 O 0.4192(6) 1.0918(4) 0.1666(2) 0.0845(12) Uani 1 1 d . A .
N1 N 0.6122(6) 1.5456(4) -0.21365(19) 0.0597(11) Uani 1 1 d . . .
H1A H 0.5949 1.4840 -0.2504 0.090 Uiso 1 1 calc R . .
H1B H 0.7557 1.5896 -0.2136 0.090 Uiso 1 1 calc R . .
H1C H 0.5010 1.6194 -0.2153 0.090 Uiso 1 1 calc R . .
C3 C 0.7241(8) 1.3745(6) -0.0405(3) 0.0632(13) Uani 1 1 d . A .
H3 H 0.8396 1.3788 -0.0053 0.076 Uiso 1 1 calc R . .
C2 C 0.7569(7) 1.4589(5) -0.0996(2) 0.0536(11) Uani 1 1 d . . .
H2 H 0.8931 1.5191 -0.1044 0.064 Uiso 1 1 calc R . .
C5 C 0.3601(7) 1.2752(5) -0.0866(3) 0.0604(13) Uani 1 1 d . A .
H5 H 0.2282 1.2104 -0.0835 0.072 Uiso 1 1 calc R . .
C4 C 0.5246(8) 1.2831(5) -0.0317(3) 0.0611(13) Uani 1 1 d . . .
C6 C 0.3898(7) 1.3622(5) -0.1457(2) 0.0525(11) Uani 1 1 d . . .
H6 H 0.2763 1.3587 -0.1815 0.063 Uiso 1 1 calc R A .
C9 C 0.2863(8) 1.0568(5) 0.1193(3) 0.0617(13) Uani 1 1 d . . .
C1 C 0.5877(6) 1.4536(5) -0.1510(2) 0.0451(10) Uani 1 1 d . A .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
C7A C8A 1.328(7) . ?
C7A C4 1.492(7) . ?
C8A C9 1.391(7) . ?
C7B C8B 1.52(3) . ?
C7B C8B 1.53(3) 3_675 ?
C7B C4 1.60(2) . ?
C8B C7B 1.53(3) 3_675 ?
C8B C9 1.89(2) . ?
O1 C9 1.328(5) . ?
O2 C9 1.204(5) . ?
N1 C1 1.458(5) . ?
C3 C2 1.372(6) . ?
C3 C4 1.382(6) . ?
C2 C1 1.359(6) . ?
C5 C6 1.380(6) . ?
C5 C4 1.393(6) . ?
C6 C1 1.367(5) . ?

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
C8A C7A C4 127.0(5) . . ?
C7A C8A C9 121.1(5) . . ?
C8B C7B C8B 88.3(17) . 3_675 ?
C8B C7B C4 111.2(16) . . ?
C8B C7B C4 133.5(17) 3_675 . ?
C7B C8B C7B 91.7(17) . 3_675 ?
C7B C8B C9 113.1(16) . . ?
C7B C8B C9 118.1(15) 3_675 . ?
C2 C3 C4 122.0(4) . . ?
C1 C2 C3 119.1(4) . . ?
C6 C5 C4 121.0(4) . . ?
C3 C4 C5 117.2(5) . . ?
C3 C4 C7A 119.6(4) . . ?
C5 C4 C7A 122.8(4) . . ?
C3 C4 C7B 115.1(8) . . ?
C5 C4 C7B 112.8(9) . . ?
C7A C4 C7B 44.3(8) . . ?
C1 C6 C5 119.3(4) . . ?
O2 C9 O1 122.4(5) . . ?
O2 C9 C8A 123.0(5) . . ?
O1 C9 C8A 114.5(5) . . ?
O2 C9 C8B 130.1(7) . . ?
O1 C9 C8B 102.0(7) . . ?
C8A C9 C8B 29.6(7) . . ?
C2 C1 C6 121.3(4) . . ?
C2 C1 N1 120.8(4) . . ?
C6 C1 N1 117.9(4) . . ?

_diffrn_measured_fraction_theta_max 0.849
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.375
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.052
####################################################################### 
# 
# 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_1HCl_74
_database_code_depnum_ccdc_archive 'CCDC 1436611'
_audit_update_record             
;
2015-11-12 deposited with the CCDC.
2015-12-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H10 Cl N O2'
_chemical_formula_weight         199.63

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'
Cl Cl 0.1484 0.1585 '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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/c

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                   5.6294(5)
_cell_length_b                   8.5824(8)
_cell_length_c                   19.252(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.427(9)
_cell_angle_gamma                90.00
_cell_volume                     929.83(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    298
_cell_measurement_reflns_used    908
_cell_measurement_theta_min      3.1790
_cell_measurement_theta_max      26.4230

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.426
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             416
_exptl_absorpt_coefficient_mu    0.375
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.41812
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      298
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Sapphire3
_diffrn_detector_area_resol_mean 16.1340
_diffrn_reflns_number            3487
_diffrn_reflns_av_R_equivalents  0.0398
_diffrn_reflns_av_sigmaI/netI    0.0760
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.18
_diffrn_reflns_theta_max         24.74
_reflns_number_total             1584
_reflns_number_gt                1026
_reflns_threshold_expression     >2σ(I)
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -37.00   49.00   1.0000  137.5000
omega____ theta____ kappa____ phi______ frames
    -      -16.3596   77.0000  -30.0000 86

#__ type_ start__ end____ width___ exp.time_
  2 omega  -40.00   44.00   1.0000  137.5000
omega____ theta____ kappa____ phi______ frames
    -      -16.3596   77.0000   90.0000 84

#__ type_ start__ end____ width___ exp.time_
  3 omega   13.00   61.00   1.0000  137.5000
omega____ theta____ kappa____ phi______ frames
    -       17.4534   77.0000 -120.0000 48

;

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0614P)²+1.1097P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1584
_refine_ls_number_parameters     118
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1406
_refine_ls_R_factor_gt           0.0854
_refine_ls_wR_factor_ref         0.1914
_refine_ls_wR_factor_gt          0.1701
_refine_ls_goodness_of_fit_ref   1.113
_refine_ls_restrained_S_all      1.113
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C7A C 1.0191(12) -0.2897(8) -0.0374(4) 0.048(2) Uiso 0.739(10) 1 d P A 1
H7A H 0.9067 -0.2693 -0.0725 0.058 Uiso 0.739(10) 1 calc PR A 1
C8A C 1.2027(13) -0.3767(9) -0.0540(4) 0.049(2) Uiso 0.739(10) 1 d P A 1
H8A H 1.3267 -0.3916 -0.0219 0.059 Uiso 0.739(10) 1 calc PR A 1
C7B C 0.924(3) -0.380(2) -0.0030(10) 0.041(6) Uiso 0.261(10) 1 d P . 2
H7B H 0.8309 -0.3581 -0.0456 0.049 Uiso 0.261(10) 1 calc PR A 2
C8B C 1.155(3) -0.454(2) -0.0242(11) 0.047(6) Uiso 0.261(10) 1 d P . 2
H8B H 1.2898 -0.4136 0.0033 0.057 Uiso 0.261(10) 1 calc PR A 2
C1 C 0.9148(8) -0.0421(6) 0.1513(3) 0.0434(13) Uani 1 1 d . A .
C2 C 0.7435(9) -0.0382(7) 0.1002(3) 0.0552(15) Uani 1 1 d . . .
H2 H 0.6084 0.0229 0.1049 0.066 Uiso 1 1 calc R . .
C3 C 0.7745(10) -0.1267(7) 0.0414(3) 0.0668(18) Uani 1 1 d . A .
H3 H 0.6588 -0.1241 0.0061 0.080 Uiso 1 1 calc R . .
C4 C 0.9738(10) -0.2197(7) 0.0334(3) 0.0656(17) Uani 1 1 d . . .
C5 C 1.1379(9) -0.2235(7) 0.0877(3) 0.0639(17) Uani 1 1 d . A .
H5 H 1.2701 -0.2879 0.0847 0.077 Uiso 1 1 calc R . .
C6 C 1.1104(9) -0.1338(6) 0.1464(3) 0.0528(15) Uani 1 1 d . . .
H6 H 1.2244 -0.1360 0.1822 0.063 Uiso 1 1 calc R A .
C9 C 1.2121(10) -0.4448(7) -0.1178(4) 0.0648(17) Uani 1 1 d . . .
Cl1 Cl 0.3956(2) 0.21281(18) 0.23235(8) 0.0653(6) Uani 1 1 d . . .
N1 N 0.8901(7) 0.0513(5) 0.2136(2) 0.0598(13) Uani 1 1 d . . .
H1A H 0.7558 0.1059 0.2105 0.090 Uiso 1 1 calc R A .
H1B H 1.0128 0.1162 0.2180 0.090 Uiso 1 1 calc R . .
H1C H 0.8864 -0.0109 0.2506 0.090 Uiso 1 1 calc R . .
O1 O 1.0779(8) -0.4120(5) -0.1652(3) 0.0848(14) Uani 1 1 d . A .
O2 O 1.3940(8) -0.5409(6) -0.1260(2) 0.0848(14) Uani 1 1 d . A .
H2A H 1.4175 -0.5521 -0.1676 0.127 Uiso 1 1 calc R . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
C7A C8A 1.321(9) . ?
C7A C4 1.517(9) . ?
C8A C9 1.362(9) . ?
C7B C8B 1.52(3) . ?
C7B C4 1.563(19) . ?
C7B C8B 1.59(3) 3_745 ?
C8B C7B 1.59(3) 3_745 ?
C8B C9 1.84(2) . ?
C1 C6 1.358(7) . ?
C1 C2 1.362(7) . ?
C1 N1 1.452(6) . ?
C2 C3 1.378(8) . ?
C3 C4 1.388(7) . ?
C4 C5 1.378(7) . ?
C5 C6 1.380(8) . ?
C9 O1 1.204(6) . ?
C9 O2 1.327(6) . ?

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
C8A C7A C4 126.3(6) . . ?
C7A C8A C9 120.6(7) . . ?
C8B C7B C4 110.3(13) . . ?
C8B C7B C8B 87.6(15) . 3_745 ?
C4 C7B C8B 133.6(15) . 3_745 ?
C7B C8B C7B 92.4(15) . 3_745 ?
C7B C8B C9 114.7(14) . . ?
C7B C8B C9 114.9(13) 3_745 . ?
C6 C1 C2 121.7(5) . . ?
C6 C1 N1 118.2(5) . . ?
C2 C1 N1 120.2(4) . . ?
C1 C2 C3 118.6(5) . . ?
C2 C3 C4 121.8(5) . . ?
C5 C4 C3 117.3(5) . . ?
C5 C4 C7A 123.2(5) . . ?
C3 C4 C7A 118.8(5) . . ?
C5 C4 C7B 115.4(8) . . ?
C3 C4 C7B 114.7(8) . . ?
C7A C4 C7B 44.1(7) . . ?
C6 C5 C4 121.4(5) . . ?
C1 C6 C5 119.2(5) . . ?
O1 C9 O2 121.7(6) . . ?
O1 C9 C8A 123.1(6) . . ?
O2 C9 C8A 115.0(6) . . ?
O1 C9 C8B 129.1(8) . . ?
O2 C9 C8B 104.1(7) . . ?
C8A C9 C8B 28.9(6) . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        24.74
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.410
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.053
####################################################################### 
# 
# 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_1HCl_68
_database_code_depnum_ccdc_archive 'CCDC 1436612'
_audit_update_record             
;
2015-11-12 deposited with the CCDC.
2015-12-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H10 Cl N O2'
_chemical_formula_weight         199.63

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'
Cl Cl 0.1484 0.1585 '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'

_symmetry_cell_setting           MONOCLINIC
_symmetry_space_group_name_H-M   P21/C

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                   5.6409(5)
_cell_length_b                   8.5631(8)
_cell_length_c                   19.131(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.475(10)
_cell_angle_gamma                90.00
_cell_volume                     923.78(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    298
_cell_measurement_reflns_used    1660
_cell_measurement_theta_min      3.1830
_cell_measurement_theta_max      23.7200

_exptl_crystal_description       PRISM
_exptl_crystal_colour            YELLOW
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.435
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             416
_exptl_absorpt_coefficient_mu    0.378
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.79562
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      298
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Sapphire3
_diffrn_detector_area_resol_mean 16.1340
_diffrn_reflns_number            10461
_diffrn_reflns_av_R_equivalents  0.0695
_diffrn_reflns_av_sigmaI/netI    0.0839
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.61
_diffrn_reflns_theta_max         29.47
_reflns_number_total             2304
_reflns_number_gt                1028
_reflns_threshold_expression     >2σ(I)
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -52.00   46.00   1.0000   55.0000
omega____ theta____ kappa____ phi______ frames
    -       17.6096  -77.0000 -120.0000 98

#__ type_ start__ end____ width___ exp.time_
  2 omega   -1.00   86.00   1.0000   55.0000
omega____ theta____ kappa____ phi______ frames
    -       17.6096   57.0000   60.0000 87

#__ type_ start__ end____ width___ exp.time_
  3 omega   -1.00   86.00   1.0000   55.0000
omega____ theta____ kappa____ phi______ frames
    -       17.6096   57.0000    0.0000 87

#__ type_ start__ end____ width___ exp.time_
  4 omega  -11.00   87.00   1.0000   55.0000
omega____ theta____ kappa____ phi______ frames
    -       17.6096   77.0000 -180.0000 98

#__ type_ start__ end____ width___ exp.time_
  5 omega   34.00   92.00   1.0000   55.0000
omega____ theta____ kappa____ phi______ frames
    -       17.6096  179.0000 -120.0000 58

#__ type_ start__ end____ width___ exp.time_
  6 omega   34.00   65.00   1.0000   55.0000
omega____ theta____ kappa____ phi______ frames
    -       17.6096  179.0000   60.0000 31

#__ type_ start__ end____ width___ exp.time_
  7 omega  -25.00   58.00   1.0000   55.0000
omega____ theta____ kappa____ phi______ frames
    -       17.6096  -99.0000   60.0000 83

;

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0565P)²+1.6279P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2304
_refine_ls_number_parameters     119
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1963
_refine_ls_R_factor_gt           0.0877
_refine_ls_wR_factor_ref         0.2345
_refine_ls_wR_factor_gt          0.1908
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C7A C 0.4801(14) 0.7105(9) 0.0377(4) 0.064(2) Uiso 0.674(10) 1 d P A 1
H7A H 0.5903 0.7323 0.0734 0.077 Uiso 0.674(10) 1 calc PR A 1
C8A C 0.2975(14) 0.6231(11) 0.0540(5) 0.066(2) Uiso 0.674(10) 1 d P A 1
H8A H 0.1738 0.6095 0.0215 0.079 Uiso 0.674(10) 1 calc PR A 1
C7B C 0.573(3) 0.6245(19) 0.0031(8) 0.062(5) Uiso 0.326(10) 1 d P . 2
H7B H 0.6617 0.6478 0.0466 0.075 Uiso 0.326(10) 1 calc PR A 2
C8B C 0.342(3) 0.5477(19) 0.0232(8) 0.059(5) Uiso 0.326(10) 1 d P . 2
H8B H 0.2064 0.5872 -0.0046 0.070 Uiso 0.326(10) 1 calc PR A 2
C3 C 0.3621(9) 0.7772(7) -0.0892(3) 0.0772(16) Uani 1 1 d . A .
H3 H 0.2307 0.7120 -0.0866 0.093 Uiso 1 1 calc R . .
C4 C 0.7279(10) 0.8739(7) -0.0418(3) 0.0862(19) Uani 1 1 d . A .
H4 H 0.8438 0.8760 -0.0064 0.103 Uiso 1 1 calc R . .
C1 C 0.5843(8) 0.9620(6) -0.1519(3) 0.0588(13) Uani 1 1 d . A .
C6 C 0.5285(10) 0.7799(7) -0.0346(3) 0.0860(19) Uani 1 1 d . . .
C9 C 0.2867(10) 0.5535(7) 0.1166(4) 0.0832(18) Uani 1 1 d . . .
C2 C 0.3894(9) 0.8697(6) -0.1469(3) 0.0665(14) Uani 1 1 d . . .
H2 H 0.2746 0.8694 -0.1827 0.080 Uiso 1 1 calc R A .
C5 C 0.7562(9) 0.9642(7) -0.1009(3) 0.0714(15) Uani 1 1 d . . .
H5 H 0.8908 1.0256 -0.1056 0.086 Uiso 1 1 calc R A .
Cl1 Cl 0.8971(2) 0.78306(19) 0.23243(8) 0.0801(6) Uani 1 1 d . . .
O2 O 0.1073(7) 0.4582(6) 0.1268(3) 0.1059(15) Uani 1 1 d . A .
H2A H 0.1198 0.4146 0.1748 0.159 Uiso 1 1 calc R . .
O1 O 0.4240(7) 0.5861(5) 0.1637(3) 0.0997(15) Uani 1 1 d . A .
N1 N 0.6079(7) 1.0571(6) -0.2141(2) 0.0765(14) Uani 1 1 d . . .
H1A H 0.4980 1.1316 -0.2146 0.115 Uiso 1 1 calc R A .
H1B H 0.5889 0.9974 -0.2519 0.115 Uiso 1 1 calc R . .
H1C H 0.7513 1.1005 -0.2139 0.115 Uiso 1 1 calc R . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
C7A C8A 1.317(10) . ?
C7A C6 1.537(9) . ?
C8A C9 1.340(10) . ?
C7B C8B 1.52(2) . ?
C7B C6 1.531(16) . ?
C7B C8B 1.64(3) 3_665 ?
C8B C7B 1.64(3) 3_665 ?
C8B C9 1.821(18) . ?
C3 C2 1.372(7) . ?
C3 C6 1.386(7) . ?
C4 C5 1.381(8) . ?
C4 C6 1.393(7) . ?
C1 C5 1.358(7) . ?
C1 C2 1.359(6) . ?
C1 N1 1.451(6) . ?
C9 O1 1.206(7) . ?
C9 O2 1.318(6) . ?

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
C8A C7A C6 126.2(7) . . ?
C7A C8A C9 121.2(8) . . ?
C8B C7B C6 111.4(11) . . ?
C8B C7B C8B 87.1(12) . 3_665 ?
C6 C7B C8B 133.2(13) . 3_665 ?
C7B C8B C7B 92.9(12) . 3_665 ?
C7B C8B C9 113.9(11) . . ?
C7B C8B C9 112.7(10) 3_665 . ?
C2 C3 C6 120.6(5) . . ?
C5 C4 C6 121.0(5) . . ?
C5 C1 C2 121.4(5) . . ?
C5 C1 N1 120.2(5) . . ?
C2 C1 N1 118.4(5) . . ?
C3 C6 C4 117.9(5) . . ?
C3 C6 C7B 116.1(7) . . ?
C4 C6 C7B 115.2(7) . . ?
C3 C6 C7A 122.6(5) . . ?
C4 C6 C7A 118.4(6) . . ?
C7B C6 C7A 43.1(6) . . ?
O1 C9 O2 120.9(7) . . ?
O1 C9 C8A 121.4(6) . . ?
O2 C9 C8A 117.4(7) . . ?
O1 C9 C8B 128.1(7) . . ?
O2 C9 C8B 106.3(7) . . ?
C8A C9 C8B 28.7(6) . . ?
C1 C2 C3 120.0(5) . . ?
C1 C5 C4 119.0(5) . . ?

_diffrn_measured_fraction_theta_max 0.896
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.380
_refine_diff_density_min         -0.277
_refine_diff_density_rms         0.056
####################################################################### 
# 
# 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_1HCl_51
_database_code_depnum_ccdc_archive 'CCDC 1436613'
_audit_update_record             
;
2015-11-12 deposited with the CCDC.
2015-12-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H10 Cl N O2'
_chemical_formula_weight         199.63

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'
Cl Cl 0.1484 0.1585 '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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/c

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                   5.6523(7)
_cell_length_b                   8.5616(14)
_cell_length_c                   19.105(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.471(17)
_cell_angle_gamma                90.00
_cell_volume                     924.3(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    298
_cell_measurement_reflns_used    767
_cell_measurement_theta_min      3.1890
_cell_measurement_theta_max      21.0210

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.435
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             416
_exptl_absorpt_coefficient_mu    0.378
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.23052
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      298
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Sapphire3
_diffrn_detector_area_resol_mean 16.1340
_diffrn_reflns_number            3256
_diffrn_reflns_av_R_equivalents  0.0478
_diffrn_reflns_av_sigmaI/netI    0.0779
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.20
_diffrn_reflns_theta_max         24.74
_reflns_number_total             1580
_reflns_number_gt                1139
_reflns_threshold_expression     >2σ(I)
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -74.00    1.00   1.0000  150.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.5159  -57.0000  -60.0000 75

#__ type_ start__ end____ width___ exp.time_
  2 omega   -7.00   22.00   1.0000  150.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.5159  -99.0000  120.0000 29

#__ type_ start__ end____ width___ exp.time_
  3 omega  -63.00  -34.00   1.0000  150.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.5159 -179.0000   90.0000 29

#__ type_ start__ end____ width___ exp.time_
  4 omega  -27.00   52.00   1.0000  150.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.5159   57.0000   90.0000 79

;


_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0456P)²+2.9816P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1580
_refine_ls_number_parameters     119
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1532
_refine_ls_R_factor_gt           0.1149
_refine_ls_wR_factor_ref         0.2367
_refine_ls_wR_factor_gt          0.2164
_refine_ls_goodness_of_fit_ref   1.173
_refine_ls_restrained_S_all      1.173
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C7A C 0.5241(19) 0.2115(14) -0.0383(6) 0.035(3) Uiso 0.512(9) 1 d P A 1
H7A H 0.4181 0.2373 -0.0745 0.043 Uiso 0.512(9) 1 calc PR A 1
C8A C 0.702(2) 0.1267(15) -0.0546(7) 0.033(3) Uiso 0.488(9) 1 d P A 1
H8A H 0.8278 0.1176 -0.0226 0.040 Uiso 0.488(9) 1 calc PR A 1
C7B C 0.429(3) 0.124(2) -0.0046(9) 0.077(5) Uiso 0.512(9) 1 d P . 2
H7B H 0.3339 0.1484 -0.0468 0.092 Uiso 0.512(9) 1 calc PR A 2
C8B C 0.661(3) 0.050(2) -0.0271(9) 0.065(5) Uiso 0.488(9) 1 d P . 2
H8B H 0.7965 0.0912 0.0002 0.078 Uiso 0.488(9) 1 calc PR A 2
C1 C 0.4165(11) 0.4662(8) 0.1517(4) 0.0491(17) Uani 1 1 d . A .
C2 C 0.2448(12) 0.4673(9) 0.1008(4) 0.062(2) Uani 1 1 d . . .
H2 H 0.1109 0.5294 0.1049 0.074 Uiso 1 1 calc R . .
C3 C 0.2736(13) 0.3746(10) 0.0433(5) 0.081(3) Uani 1 1 d . A .
H3 H 0.1602 0.3775 0.0071 0.097 Uiso 1 1 calc R . .
C4 C 0.4659(14) 0.2773(10) 0.0374(5) 0.083(3) Uani 1 1 d . . .
C5 C 0.6326(13) 0.2791(10) 0.0915(5) 0.074(2) Uani 1 1 d . A .
H5 H 0.7634 0.2136 0.0889 0.088 Uiso 1 1 calc R . .
C6 C 0.6122(11) 0.3723(8) 0.1477(4) 0.0562(19) Uani 1 1 d . . .
H6 H 0.7284 0.3731 0.1831 0.067 Uiso 1 1 calc R A .
C9 C 0.7123(13) 0.0530(10) -0.1137(5) 0.073(3) Uani 1 1 d . . .
Cl1 Cl 0.8987(3) 0.7207(3) 0.23235(11) 0.0679(7) Uani 1 1 d . . .
N1 N 0.3938(9) 0.5643(8) 0.2143(3) 0.0662(19) Uani 1 1 d . . .
H1A H 0.5091 0.6351 0.2156 0.099 Uiso 1 1 calc R A .
H1B H 0.4043 0.5047 0.2524 0.099 Uiso 1 1 calc R . .
H1C H 0.2542 0.6124 0.2127 0.099 Uiso 1 1 calc R . .
O1 O 0.8989(11) -0.0372(11) -0.1238(3) 0.112(3) Uani 1 1 d . A .
H1 H 0.9152 -0.0506 -0.1659 0.169 Uiso 1 1 calc R . .
O2 O 0.5762(10) 0.0847(7) -0.1617(4) 0.090(2) Uani 1 1 d . A .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
C7A C8A 1.283(15) . ?
C7A C4 1.595(13) . ?
C8A C9 1.297(14) . ?
C7B C8B 1.53(2) . ?
C7B C4 1.547(18) . ?
C7B C8B 1.70(2) 3_655 ?
C8B C7B 1.70(2) 3_655 ?
C8B C9 1.688(19) . ?
C1 C2 1.356(9) . ?
C1 C6 1.371(9) . ?
C1 N1 1.468(9) . ?
C2 C3 1.370(10) . ?
C3 C4 1.376(10) . ?
C4 C5 1.380(10) . ?
C5 C6 1.346(10) . ?
C9 O2 1.212(9) . ?
C9 O1 1.326(9) . ?

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
C8A C7A C4 126.9(10) . . ?
C7A C8A C9 122.7(11) . . ?
C8B C7B C4 113.2(13) . . ?
C8B C7B C8B 90.1(13) . 3_655 ?
C4 C7B C8B 126.7(13) . 3_655 ?
C7B C8B C7B 89.9(13) . 3_655 ?
C7B C8B C9 116.1(13) . . ?
C7B C8B C9 115.1(12) 3_655 . ?
C2 C1 C6 121.8(7) . . ?
C2 C1 N1 120.2(6) . . ?
C6 C1 N1 117.9(6) . . ?
C1 C2 C3 118.3(7) . . ?
C2 C3 C4 121.7(7) . . ?
C3 C4 C5 117.3(7) . . ?
C3 C4 C7B 117.3(9) . . ?
C5 C4 C7B 118.5(9) . . ?
C3 C4 C7A 118.0(8) . . ?
C5 C4 C7A 122.0(7) . . ?
C7B C4 C7A 42.1(7) . . ?
C6 C5 C4 122.2(7) . . ?
C5 C6 C1 118.5(7) . . ?
O2 C9 C8A 120.5(9) . . ?
O2 C9 O1 120.9(9) . . ?
C8A C9 O1 117.7(9) . . ?
O2 C9 C8B 128.6(8) . . ?
C8A C9 C8B 30.6(7) . . ?
O1 C9 C8B 106.9(8) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        24.74
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.456
_refine_diff_density_min         -0.368
_refine_diff_density_rms         0.065
####################################################################### 
# 
# 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_1HCl_41
_database_code_depnum_ccdc_archive 'CCDC 1436614'
_audit_update_record             
;
2015-11-12 deposited with the CCDC.
2015-12-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H10 Cl N O2'
_chemical_formula_weight         199.63

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'
Cl Cl 0.1484 0.1585 '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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/c

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                   5.6822(5)
_cell_length_b                   8.5112(12)
_cell_length_c                   18.888(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.591(10)
_cell_angle_gamma                90.00
_cell_volume                     913.1(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    298
_cell_measurement_reflns_used    1627
_cell_measurement_theta_min      3.2060
_cell_measurement_theta_max      22.8610

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.452
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             416
_exptl_absorpt_coefficient_mu    0.382
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.84543
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      298
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Sapphire3
_diffrn_detector_area_resol_mean 16.1340
_diffrn_reflns_number            8472
_diffrn_reflns_av_R_equivalents  0.0644
_diffrn_reflns_av_sigmaI/netI    0.0533
_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       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.22
_diffrn_reflns_theta_max         24.74
_reflns_number_total             1561
_reflns_number_gt                1030
_reflns_threshold_expression     >2σ(I)
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -25.00   24.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.3596  -99.0000 -120.0000 49

#__ type_ start__ end____ width___ exp.time_
  2 omega   -1.00   86.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -       17.6096   57.0000 -120.0000 87

#__ type_ start__ end____ width___ exp.time_
  3 omega  -52.00   46.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -       17.6096  -77.0000  120.0000 98

#__ type_ start__ end____ width___ exp.time_
  4 omega   -1.00   86.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -       17.6096   57.0000   60.0000 87

#__ type_ start__ end____ width___ exp.time_
  5 omega   -1.00   86.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -       17.6096   57.0000  150.0000 87

#__ type_ start__ end____ width___ exp.time_
  6 omega   34.00   86.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -       17.6096  179.0000  120.0000 52

#__ type_ start__ end____ width___ exp.time_
  7 omega  -25.00   49.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -       17.6096  -99.0000  -60.0000 74

;

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0515P)²+2.4123P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1561
_refine_ls_number_parameters     119
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1281
_refine_ls_R_factor_gt           0.0875
_refine_ls_wR_factor_ref         0.2163
_refine_ls_wR_factor_gt          0.1971
_refine_ls_goodness_of_fit_ref   1.124
_refine_ls_restrained_S_all      1.124
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C7A C 0.5696(16) 1.1217(12) 0.0030(5) 0.057(3) Uiso 0.591(12) 1 d P . 1
H7A H 0.6574 1.1486 0.0467 0.068 Uiso 0.591(12) 1 calc PR . 1
C8A C 0.3399(18) 1.0423(14) 0.0233(6) 0.058(3) Uiso 0.591(12) 1 d P . 1
H8A H 0.2057 1.0802 -0.0056 0.070 Uiso 0.591(12) 1 calc PR . 1
C7B C 0.480(2) 1.2139(16) 0.0375(7) 0.052(4) Uiso 0.409(12) 1 d P . 2
H7B H 0.5764 1.2473 0.0751 0.062 Uiso 0.409(12) 1 calc PR . 2
C8B C 0.303(3) 1.124(2) 0.0510(9) 0.059(4) Uiso 0.409(12) 1 d P . 2
H8B H 0.1840 1.1123 0.0168 0.071 Uiso 0.409(12) 1 calc PR . 2
C1 C 0.7540(11) 1.4719(8) -0.1024(4) 0.073(2) Uani 1 1 d . . .
H1 H 0.8842 1.5376 -0.1053 0.088 Uiso 1 1 calc R . .
C2 C 0.7314(12) 1.3714(9) -0.0465(4) 0.090(3) Uani 1 1 d . . .
H2 H 0.8469 1.3704 -0.0107 0.108 Uiso 1 1 calc R . .
C3 C 0.5428(12) 1.2721(9) -0.0421(4) 0.093(3) Uani 1 1 d . . .
C4 C 0.3704(11) 1.2779(8) -0.0948(4) 0.076(2) Uani 1 1 d . . .
H4 H 0.2406 1.2118 -0.0924 0.092 Uiso 1 1 calc R . .
C5 C 0.3865(10) 1.3784(7) -0.1503(3) 0.0631(17) Uani 1 1 d . . .
H5 H 0.2682 1.3829 -0.1852 0.076 Uiso 1 1 calc R . .
C6 C 0.5815(9) 1.4735(7) -0.1537(3) 0.0554(15) Uani 1 1 d . . .
C9 C 0.2865(12) 1.0501(8) 0.1094(5) 0.079(2) Uani 1 1 d . . .
Cl1 Cl 0.0986(3) 0.7706(2) 0.26735(10) 0.0761(7) Uani 1 1 d . . .
N1 N 0.6031(8) 1.5747(6) -0.2158(3) 0.0682(15) Uani 1 1 d . . .
H1A H 0.5958 1.5163 -0.2549 0.102 Uiso 1 1 calc R . .
H1B H 0.7404 1.6250 -0.2133 0.102 Uiso 1 1 calc R . .
H1C H 0.4863 1.6444 -0.2170 0.102 Uiso 1 1 calc R . .
O1 O 0.4240(8) 1.0811(6) 0.1571(3) 0.0901(16) Uani 1 1 d . . .
O2 O 0.0924(11) 0.9773(12) 0.1205(3) 0.162(4) Uani 1 1 d . . .
H2A H 0.0585 0.9811 0.1718 0.243 Uiso 1 1 calc R . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
C7A C8A 1.528(13) . ?
C7A C3 1.543(12) . ?
C7A C8A 1.573(16) 3_675 ?
C8A C7A 1.573(16) 3_675 ?
C8A C9 1.665(14) . ?
C7B C8B 1.294(19) . ?
C7B C3 1.631(15) . ?
C8B C9 1.275(16) . ?
C1 C6 1.358(8) . ?
C1 C2 1.368(9) . ?
C2 C3 1.369(9) . ?
C3 C4 1.379(9) . ?
C4 C5 1.357(8) . ?
C5 C6 1.375(8) . ?
C6 N1 1.464(7) . ?
C9 O1 1.204(8) . ?
C9 O2 1.287(8) . ?

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
C8A C7A C3 115.7(8) . . ?
C8A C7A C8A 88.6(8) . 3_675 ?
C3 C7A C8A 126.2(9) . 3_675 ?
C7A C8A C7A 91.4(8) . 3_675 ?
C7A C8A C9 114.1(8) . . ?
C7A C8A C9 114.5(8) 3_675 . ?
C8B C7B C3 123.5(13) . . ?
C9 C8B C7B 122.7(14) . . ?
C6 C1 C2 118.3(6) . . ?
C1 C2 C3 121.6(6) . . ?
C2 C3 C4 118.3(6) . . ?
C2 C3 C7A 118.7(6) . . ?
C4 C3 C7A 119.1(7) . . ?
C2 C3 C7B 115.8(7) . . ?
C4 C3 C7B 120.5(7) . . ?
C7A C3 C7B 42.3(6) . . ?
C5 C4 C3 121.3(6) . . ?
C4 C5 C6 118.6(6) . . ?
C1 C6 C5 121.9(6) . . ?
C1 C6 N1 120.1(5) . . ?
C5 C6 N1 118.0(5) . . ?
O1 C9 C8B 118.4(10) . . ?
O1 C9 O2 121.7(8) . . ?
C8B C9 O2 117.6(10) . . ?
O1 C9 C8A 127.4(6) . . ?
C8B C9 C8A 32.2(8) . . ?
O2 C9 C8A 108.7(7) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        24.74
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.443
_refine_diff_density_min         -0.469
_refine_diff_density_rms         0.061
####################################################################### 
# 
# 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_1HCl_37
_database_code_depnum_ccdc_archive 'CCDC 1436615'
_audit_update_record             
;
2015-11-12 deposited with the CCDC.
2015-12-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H10 Cl N O2'
_chemical_formula_weight         199.63

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'
Cl Cl 0.1484 0.1585 '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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/c

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                   5.6907(5)
_cell_length_b                   8.4732(18)
_cell_length_c                   18.860(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.741(9)
_cell_angle_gamma                90.00
_cell_volume                     909.0(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    298
_cell_measurement_reflns_used    964
_cell_measurement_theta_min      3.2220
_cell_measurement_theta_max      24.9390

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.459
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             416
_exptl_absorpt_coefficient_mu    0.384
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.39957
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      298
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Sapphire3
_diffrn_detector_area_resol_mean 16.1340
_diffrn_reflns_number            3408
_diffrn_reflns_av_R_equivalents  0.0387
_diffrn_reflns_av_sigmaI/netI    0.0573
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.64
_diffrn_reflns_theta_max         24.74
_reflns_number_total             1554
_reflns_number_gt                1252
_reflns_threshold_expression     >2σ(I)
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -21.00   14.00   1.0000  200.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.3596  -99.0000   30.0000 35

#__ type_ start__ end____ width___ exp.time_
  2 omega  -68.00  -36.00   1.0000  200.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.3596 -179.0000    0.0000 32

#__ type_ start__ end____ width___ exp.time_
  3 omega  -44.00   39.00   1.0000  200.0000
omega____ theta____ kappa____ phi______ frames
    -       17.6096  -38.0000 -150.0000 83

#__ type_ start__ end____ width___ exp.time_
  4 omega   -1.00   74.00   1.0000  200.0000
omega____ theta____ kappa____ phi______ frames
    -       17.6096   57.0000    0.0000 75

;

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0636P)²+2.5912P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1554
_refine_ls_number_parameters     129
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1249
_refine_ls_R_factor_gt           0.1019
_refine_ls_wR_factor_ref         0.2266
_refine_ls_wR_factor_gt          0.2137
_refine_ls_goodness_of_fit_ref   1.173
_refine_ls_restrained_S_all      1.173
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C7A C 0.9310(13) 1.3794(10) -0.0026(4) 0.034(2) Uiso 0.628(13) 1 d P . 1
H7A H 0.8435 1.3508 -0.0463 0.041 Uiso 0.628(13) 1 calc PR . 1
C8A C 1.1596(15) 1.4587(12) -0.0228(5) 0.040(2) Uiso 0.628(13) 1 d P . 1
H8A H 1.2930 1.4215 0.0067 0.048 Uiso 0.628(13) 1 calc PR . 1
C7B C 1.022(3) 1.288(2) -0.0369(9) 0.053(5) Uiso 0.372(13) 1 d P . 2
H7B H 0.9317 1.2511 -0.0753 0.063 Uiso 0.372(13) 1 calc PR . 2
C8B C 1.197(3) 1.382(2) -0.0490(10) 0.052(5) Uiso 0.372(13) 1 d P . 2
H8B H 1.3110 1.3991 -0.0134 0.062 Uiso 0.372(13) 1 calc PR . 2
Cl1 Cl 0.4023(2) 0.7655(2) 0.23292(9) 0.0631(6) Uani 1 1 d . . .
N1 N 0.8999(10) 0.9196(8) 0.2164(3) 0.0514(14) Uani 1 1 d . . .
C1 C 0.9197(9) 1.0229(7) 0.1553(3) 0.0438(14) Uani 1 1 d . . .
O2 O 1.0776(8) 1.4194(6) -0.1542(3) 0.0758(15) Uani 1 1 d . . .
C5 C 1.1277(11) 1.2235(9) 0.0964(4) 0.063(2) Uani 1 1 d . . .
H5 H 1.2573 1.2899 0.0939 0.076 Uiso 1 1 calc R . .
C6 C 1.1140(9) 1.1186(8) 0.1512(3) 0.0500(16) Uani 1 1 d . . .
H6 H 1.2350 1.1119 0.1854 0.060 Uiso 1 1 calc R . .
C2 C 0.7447(10) 1.0283(8) 0.1042(4) 0.0585(18) Uani 1 1 d . . .
H2 H 0.6136 0.9635 0.1074 0.070 Uiso 1 1 calc R . .
C3 C 0.7638(12) 1.1294(9) 0.0487(4) 0.076(2) Uani 1 1 d . . .
H3 H 0.6485 1.1296 0.0127 0.091 Uiso 1 1 calc R . .
C9 C 1.2146(11) 1.4483(9) -0.1072(4) 0.064(2) Uani 1 1 d . . .
O1 O 1.4150(10) 1.5108(13) -0.1169(3) 0.176(5) Uani 1 1 d . . .
H1 H 1.4923 1.4530 -0.1422 0.263 Uiso 1 1 calc R . .
C4 C 0.9517(12) 1.2317(10) 0.0449(4) 0.081(3) Uani 1 1 d . . .
H1NA H 0.771(14) 0.869(9) 0.220(4) 0.08(3) Uiso 1 1 d . . .
H1NC H 0.931(11) 0.959(8) 0.257(4) 0.06(2) Uiso 1 1 d . . .
H1NB H 1.056(18) 0.849(11) 0.224(5) 0.13(3) Uiso 1 1 d . . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
C7A C8A 1.522(11) . ?
C7A C4 1.542(11) . ?
C7A C8A 1.547(14) 3_785 ?
C8A C7A 1.547(14) 3_785 ?
C8A C9 1.634(12) . ?
C7B C8B 1.30(2) . ?
C7B C4 1.675(18) . ?
C8B C9 1.242(18) . ?
N1 C1 1.454(8) . ?
C1 C2 1.365(8) . ?
C1 C6 1.375(8) . ?
O2 C9 1.188(8) . ?
C5 C6 1.367(8) . ?
C5 C4 1.376(9) . ?
C2 C3 1.360(9) . ?
C3 C4 1.380(9) . ?
C9 O1 1.275(8) . ?

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
C8A C7A C4 116.9(7) . . ?
C8A C7A C8A 89.0(7) . 3_785 ?
C4 C7A C8A 124.1(7) . 3_785 ?
C7A C8A C7A 91.0(7) . 3_785 ?
C7A C8A C9 114.3(7) . . ?
C7A C8A C9 115.2(7) 3_785 . ?
C8B C7B C4 122.8(15) . . ?
C9 C8B C7B 121.0(17) . . ?
C2 C1 C6 120.7(6) . . ?
C2 C1 N1 120.5(5) . . ?
C6 C1 N1 118.8(5) . . ?
C6 C5 C4 120.7(6) . . ?
C5 C6 C1 119.3(5) . . ?
C3 C2 C1 119.4(6) . . ?
C2 C3 C4 121.1(6) . . ?
O2 C9 C8B 119.8(10) . . ?
O2 C9 O1 123.3(8) . . ?
C8B C9 O1 114.3(11) . . ?
O2 C9 C8A 126.6(6) . . ?
C8B C9 C8A 30.6(9) . . ?
O1 C9 C8A 108.4(6) . . ?
C3 C4 C5 118.7(6) . . ?
C3 C4 C7A 119.7(6) . . ?
C5 C4 C7A 119.5(6) . . ?
C3 C4 C7B 115.8(8) . . ?
C5 C4 C7B 118.4(8) . . ?
C7A C4 C7B 41.3(6) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        24.74
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.528
_refine_diff_density_min         -0.499
_refine_diff_density_rms         0.069
####################################################################### 
# 
# 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_1HCl_25
_database_code_depnum_ccdc_archive 'CCDC 1436616'
_audit_update_record             
;
2015-11-12 deposited with the CCDC.
2015-12-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H10 Cl N O2'
_chemical_formula_weight         199.63

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'
Cl Cl 0.1484 0.1585 '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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/c

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                   5.7167(6)
_cell_length_b                   8.417(2)
_cell_length_c                   18.889(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.904(10)
_cell_angle_gamma                90.00
_cell_volume                     908.4(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    964
_cell_measurement_theta_min      3.2200
_cell_measurement_theta_max      27.0840

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.460
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             416
_exptl_absorpt_coefficient_mu    0.384
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.95384
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      298
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Sapphire3
_diffrn_detector_area_resol_mean 16.1340
_diffrn_reflns_number            3420
_diffrn_reflns_av_R_equivalents  0.0366
_diffrn_reflns_av_sigmaI/netI    0.0564
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.65
_diffrn_reflns_theta_max         24.75
_reflns_number_total             1551
_reflns_number_gt                1276
_reflns_threshold_expression     >2σ(I)
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -19.00   12.00   1.0000  130.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.3596  -99.0000 -180.0000 31

#__ type_ start__ end____ width___ exp.time_
  2 omega  -47.00   -7.00   1.0000  130.0000
omega____ theta____ kappa____ phi______ frames
    -       17.6096  -57.0000 -120.0000 40

#__ type_ start__ end____ width___ exp.time_
  3 omega    3.00   33.00   1.0000  130.0000
omega____ theta____ kappa____ phi______ frames
    -       17.6096  -57.0000 -120.0000 30

#__ type_ start__ end____ width___ exp.time_
  4 omega  -51.00   24.00   1.0000  130.0000
omega____ theta____ kappa____ phi______ frames
    -       17.6096  -38.0000  -30.0000 75

#__ type_ start__ end____ width___ exp.time_
  5 omega   38.00   92.00   1.0000  130.0000
omega____ theta____ kappa____ phi______ frames
    -       17.6096  179.0000 -150.0000 54

;

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0548P)²+2.5138P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1551
_refine_ls_number_parameters     129
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1244
_refine_ls_R_factor_gt           0.1034
_refine_ls_wR_factor_ref         0.2125
_refine_ls_wR_factor_gt          0.2014
_refine_ls_goodness_of_fit_ref   1.200
_refine_ls_restrained_S_all      1.200
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C7A C 0.9315(12) 0.8766(10) -0.0022(4) 0.040(2) Uani 0.747(13) 1 d P . 1
H7A H 0.8428 0.8456 -0.0453 0.048 Uiso 0.747(13) 1 calc PR . 1
C8A C 1.1611(12) 0.9561(11) -0.0235(4) 0.037(2) Uani 0.747(13) 1 d P . 1
H8A H 1.2941 0.9193 0.0063 0.045 Uiso 0.747(13) 1 calc PR . 1
C7B C 1.021(4) 0.785(3) -0.0381(12) 0.042(7) Uiso 0.253(13) 1 d P . 2
H7B H 0.9306 0.7474 -0.0763 0.051 Uiso 0.253(13) 1 calc PR . 2
C8B C 1.199(4) 0.875(4) -0.0495(15) 0.044(7) Uiso 0.253(13) 1 d P . 2
H8B H 1.3178 0.8843 -0.0148 0.053 Uiso 0.253(13) 1 calc PR . 2
C1 C 0.9198(9) 0.5202(7) 0.1565(3) 0.0391(13) Uani 1 1 d . . .
C2 C 1.1124(9) 0.6152(7) 0.1524(3) 0.0456(15) Uani 1 1 d . . .
H2 H 1.2340 0.6066 0.1861 0.055 Uiso 1 1 calc R . .
C3 C 1.1263(10) 0.7236(8) 0.0982(4) 0.0588(19) Uani 1 1 d . . .
H3 H 1.2561 0.7898 0.0957 0.071 Uiso 1 1 calc R . .
C4 C 0.9475(11) 0.7340(9) 0.0475(4) 0.068(2) Uani 1 1 d . . .
C5 C 0.7604(11) 0.6316(9) 0.0510(4) 0.073(2) Uani 1 1 d . . .
H5 H 0.6433 0.6345 0.0156 0.087 Uiso 1 1 calc R . .
C6 C 0.7437(11) 0.5260(8) 0.1053(3) 0.0588(18) Uani 1 1 d . . .
H6 H 0.6150 0.4589 0.1076 0.071 Uiso 1 1 calc R . .
C9 C 1.2154(10) 0.9467(9) -0.1041(4) 0.0588(19) Uani 1 1 d . . .
Cl1 Cl 0.4030(2) 0.2599(2) 0.23288(9) 0.0598(6) Uani 1 1 d . . .
N1 N 0.9015(8) 0.4162(6) 0.2178(2) 0.0462(13) Uani 1 1 d . . .
H1A H 1.0172 0.3455 0.2180 0.069 Uiso 1 1 calc R . .
H1B H 0.7646 0.3658 0.2155 0.069 Uiso 1 1 calc R . .
H1C H 0.9115 0.4739 0.2572 0.069 Uiso 1 1 calc R . .
O1 O 1.0780(8) 0.9191(6) -0.1520(2) 0.0682(14) Uani 1 1 d . . .
O2 O 1.4244(11) 0.9957(14) -0.1138(3) 0.178(5) Uani 1 1 d . . .
H2W H 1.4706 0.9598 -0.1512 0.266 Uiso 1 1 calc R . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
C7A C4 1.525(10) . ?
C7A C8A 1.538(10) . ?
C7A C8A 1.586(13) 3_775 ?
C8A C9 1.566(11) . ?
C8A C7A 1.586(13) 3_775 ?
C7B C8B 1.29(3) . ?
C7B C4 1.74(2) . ?
C8B C9 1.20(3) . ?
C1 C2 1.365(8) . ?
C1 C6 1.374(8) . ?
C1 N1 1.458(7) . ?
C2 C3 1.376(8) . ?
C3 C4 1.380(8) . ?
C4 C5 1.377(9) . ?
C5 C6 1.362(9) . ?
C9 O1 1.202(7) . ?
C9 O2 1.282(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
C4 C7A C8A 118.0(6) . . ?
C4 C7A C8A 121.6(6) . 3_775 ?
C8A C7A C8A 89.4(6) . 3_775 ?
C7A C8A C9 115.5(6) . . ?
C7A C8A C7A 90.6(6) . 3_775 ?
C9 C8A C7A 114.9(6) . 3_775 ?
C8B C7B C4 121(2) . . ?
C9 C8B C7B 121(2) . . ?
C2 C1 C6 120.8(5) . . ?
C2 C1 N1 118.4(5) . . ?
C6 C1 N1 120.7(5) . . ?
C1 C2 C3 119.8(5) . . ?
C2 C3 C4 119.9(6) . . ?
C5 C4 C3 119.1(6) . . ?
C5 C4 C7A 119.4(6) . . ?
C3 C4 C7A 120.4(6) . . ?
C5 C4 C7B 114.3(9) . . ?
C3 C4 C7B 117.7(9) . . ?
C7A C4 C7B 40.8(8) . . ?
C6 C5 C4 121.2(6) . . ?
C5 C6 C1 119.0(6) . . ?
C8B C9 O1 118.9(14) . . ?
C8B C9 O2 112.5(14) . . ?
O1 C9 O2 122.9(7) . . ?
C8B C9 C8A 33.6(14) . . ?
O1 C9 C8A 126.6(6) . . ?
O2 C9 C8A 109.8(6) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        24.75
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.412
_refine_diff_density_min         -0.357
_refine_diff_density_rms         0.070
####################################################################### 
# 
# 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_1HCl_0
_database_code_depnum_ccdc_archive 'CCDC 1436617'
_audit_update_record             
;
2015-11-12 deposited with the CCDC.
2015-12-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H10 N O2 1+,Cl 1-'
_chemical_formula_sum            'C9 H10 Cl N O2'
_chemical_formula_weight         199.64

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 0.0020 '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'
Cl Cl 0.1480 0.1590 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0110 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21/c

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                   5.7431(17)
_cell_length_b                   8.221(3)
_cell_length_c                   19.012(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.47(3)
_cell_angle_gamma                90.00
_cell_volume                     896.8(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    298
_cell_measurement_reflns_used    551
_cell_measurement_theta_min      3.2050
_cell_measurement_theta_max      22.6210

_exptl_crystal_description       prism
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.479
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             416
_exptl_absorpt_coefficient_mu    0.389
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.37876
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      298
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Sapphire3
_diffrn_detector_area_resol_mean 16.1340
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6135
_diffrn_reflns_av_R_equivalents  0.1473
_diffrn_reflns_av_sigmaI/netI    0.2498
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.70
_diffrn_reflns_theta_max         29.41
_reflns_number_total             2136
_reflns_number_gt                609
_reflns_threshold_expression     >2σ(I)
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -15.00   12.00   1.0000  250.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.5159  -99.0000 -150.0000 27

#__ type_ start__ end____ width___ exp.time_
  2 omega   -9.00   23.00   1.0000  250.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.5159  -99.0000  -30.0000 32

#__ type_ start__ end____ width___ exp.time_
  3 omega  -64.00  -38.00   1.0000  250.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.5159 -179.0000  -90.0000 26

#__ type_ start__ end____ width___ exp.time_
  4 omega    3.00   83.00   1.0000  250.0000
omega____ theta____ kappa____ phi______ frames
    -       17.7659   57.0000  -30.0000 80

#__ type_ start__ end____ width___ exp.time_
  5 omega  -43.00   36.00   1.0000  250.0000
omega____ theta____ kappa____ phi______ frames
    -       17.7659  -57.0000   60.0000 79

#__ type_ start__ end____ width___ exp.time_
  6 omega    7.00   33.00   1.0000  250.0000
omega____ theta____ kappa____ phi______ frames
    -       17.7659  -57.0000   90.0000 26

#__ type_ start__ end____ width___ exp.time_
  7 omega   -4.00   88.00   1.0000  250.0000
omega____ theta____ kappa____ phi______ frames
    -       17.7659   38.0000 -120.0000 92

;

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1564P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2136
_refine_ls_number_parameters     120
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.3096
_refine_ls_R_factor_gt           0.1088
_refine_ls_wR_factor_ref         0.3918
_refine_ls_wR_factor_gt          0.2650
_refine_ls_goodness_of_fit_ref   0.965
_refine_ls_restrained_S_all      0.965
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2535(17) 0.3663(14) 0.0565(5) 0.070(3) Uani 1 1 d . . .
H1 H 0.1330 0.3607 0.0223 0.084 Uiso 1 1 calc R . .
C2 C 0.2391(17) 0.4770(12) 0.1100(5) 0.065(3) Uani 1 1 d . . .
H2 H 0.1088 0.5435 0.1127 0.078 Uiso 1 1 calc R . .
C3 C 0.4203(17) 0.4887(12) 0.1600(5) 0.059(3) Uani 1 1 d . . .
C4 C 0.6102(16) 0.3917(12) 0.1552(5) 0.065(3) Uani 1 1 d . . .
H4 H 0.7340 0.4025 0.1880 0.078 Uiso 1 1 calc R . .
C5 C 0.6228(16) 0.2769(12) 0.1021(5) 0.063(3) Uani 1 1 d . . .
H5 H 0.7525 0.2096 0.1003 0.075 Uiso 1 1 calc R . .
C6 C 0.4423(17) 0.2625(13) 0.0518(4) 0.063(3) Uani 1 1 d . . .
C7 C 0.4328(15) 0.1274(13) -0.0021(5) 0.064(3) Uani 1 1 d . . .
H7 H 0.3455 0.1637 -0.0446 0.077 Uiso 1 1 calc R . .
C8 C 0.3358(15) -0.0461(11) 0.0224(4) 0.055(3) Uani 1 1 d . . .
H8 H 0.2040 -0.0826 -0.0080 0.067 Uiso 1 1 calc R . .
C9 C 0.284(2) -0.0618(12) 0.0993(6) 0.069(3) Uani 1 1 d . . .
Cl1 Cl 0.0950(4) 0.2556(4) 0.26773(12) 0.0729(10) Uani 1 1 d . . .
N1 N 0.4054(12) 0.5922(9) 0.2216(3) 0.061(2) Uani 1 1 d . . .
H1A H 0.4051 0.5308 0.2601 0.092 Uiso 1 1 calc R . .
H1B H 0.2745 0.6502 0.2181 0.092 Uiso 1 1 calc R . .
H1C H 0.5273 0.6591 0.2242 0.092 Uiso 1 1 calc R . .
O1 O 0.0557(14) -0.0469(14) 0.1074(4) 0.116(3) Uani 1 1 d . . .
H1O H 0.0249 -0.0750 0.1473 0.174 Uiso 1 1 calc R . .
O2 O 0.4199(13) -0.0833(9) 0.1474(4) 0.077(2) Uani 1 1 d . . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
C1 C2 1.371(13) . ?
C1 C6 1.386(13) . ?
C2 C3 1.382(12) . ?
C3 C4 1.357(12) . ?
C3 N1 1.453(11) . ?
C4 C5 1.385(12) . ?
C5 C6 1.386(13) . ?
C6 C7 1.509(13) . ?
C7 C8 1.552(12) 3_655 ?
C7 C8 1.608(12) . ?
C8 C9 1.509(13) . ?
C8 C7 1.552(12) 3_655 ?
C9 O2 1.187(11) . ?
C9 O1 1.335(12) . ?

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 C1 C6 121.9(9) . . ?
C1 C2 C3 119.3(9) . . ?
C4 C3 C2 119.7(9) . . ?
C4 C3 N1 118.3(9) . . ?
C2 C3 N1 121.7(8) . . ?
C3 C4 C5 121.1(9) . . ?
C4 C5 C6 120.0(9) . . ?
C5 C6 C1 117.8(9) . . ?
C5 C6 C7 122.4(9) . . ?
C1 C6 C7 119.4(9) . . ?
C6 C7 C8 118.7(7) . 3_655 ?
C6 C7 C8 117.3(7) . . ?
C8 C7 C8 90.1(7) 3_655 . ?
C9 C8 C7 114.2(8) . 3_655 ?
C9 C8 C7 116.2(7) . . ?
C7 C8 C7 89.9(7) 3_655 . ?
O2 C9 O1 122.7(10) . . ?
O2 C9 C8 127.6(10) . . ?
O1 C9 C8 109.7(10) . . ?

_diffrn_measured_fraction_theta_max 0.864
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.540
_refine_diff_density_min         -0.396
_refine_diff_density_rms         0.129
#end




####################################################################### 
# 
# 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_1H2SO4-h2O_1
_database_code_depnum_ccdc_archive 'CCDC 1436618'
_audit_update_record             
;
2015-11-26 deposited with the CCDC.
2015-12-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H22 N2 O9 S'
_chemical_formula_weight         442.44

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/c

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                   13.1014(6)
_cell_length_b                   11.7129(4)
_cell_length_c                   13.2735(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.385(4)
_cell_angle_gamma                90.00
_cell_volume                     2003.52(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    298
_cell_measurement_reflns_used    2288
_cell_measurement_theta_min      3.1580
_cell_measurement_theta_max      23.7960

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.467
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             928
_exptl_absorpt_coefficient_mu    0.217
_exptl_absorpt_correction_T_min  0.98533
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      298
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_method       'omega scan'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Sapphire3
_diffrn_detector_area_resol_mean 16.1340
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9219
_diffrn_reflns_av_R_equivalents  0.0401
_diffrn_reflns_av_sigmaI/netI    0.0745
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.66
_diffrn_reflns_theta_max         29.43
_reflns_number_total             4638
_reflns_number_gt                2480
_reflns_threshold_expression     >2σ(I)
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   39.00   65.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       17.6096  179.0000   30.0000 26

#__ type_ start__ end____ width___ exp.time_
  2 omega  -26.00   80.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       17.6096    0.0000  120.0000 106

#__ type_ start__ end____ width___ exp.time_
  3 omega    0.00   81.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       17.6096   38.0000 -180.0000 81

;

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2005)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1106P)²+0.6259P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4638
_refine_ls_number_parameters     283
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1461
_refine_ls_R_factor_gt           0.0761
_refine_ls_wR_factor_ref         0.2476
_refine_ls_wR_factor_gt          0.1887
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 1.1382(4) 0.6668(3) -0.0741(3) 0.0549(11) Uani 1 1 d . . .
C2 C 1.2045(4) 0.5746(4) -0.0522(3) 0.0599(12) Uani 1 1 d . . .
H2 H 1.1780 0.5010 -0.0519 0.072 Uiso 1 1 calc R . .
C3 C 1.3095(4) 0.5924(4) -0.0311(3) 0.0626(12) Uani 1 1 d . . .
H3 H 1.3535 0.5300 -0.0164 0.075 Uiso 1 1 calc R . .
C4 C 1.3521(4) 0.7005(3) -0.0310(3) 0.0555(11) Uani 1 1 d . . .
C5 C 1.2835(4) 0.7918(3) -0.0543(3) 0.0618(12) Uani 1 1 d . . .
H5 H 1.3099 0.8654 -0.0551 0.074 Uiso 1 1 calc R . .
C6 C 1.1780(4) 0.7759(4) -0.0761(3) 0.0626(12) Uani 1 1 d . . .
H6 H 1.1337 0.8379 -0.0921 0.075 Uiso 1 1 calc R . .
C7 C 1.4639(4) 0.7152(4) -0.0061(3) 0.0629(12) Uani 1 1 d . . .
H7 H 1.5026 0.6482 0.0033 0.075 Uiso 1 1 calc R . .
C8 C 1.5174(4) 0.8099(4) 0.0050(4) 0.0666(13) Uani 1 1 d . . .
H8 H 1.4806 0.8782 -0.0046 0.080 Uiso 1 1 calc R . .
C9 C 1.6316(4) 0.8172(4) 0.0317(4) 0.0628(12) Uani 1 1 d . . .
C10 C 0.7633(3) 1.0084(3) -0.1872(3) 0.0467(9) Uani 1 1 d . . .
C11 C 0.7134(3) 0.9050(4) -0.2047(4) 0.0618(12) Uani 1 1 d . . .
H11 H 0.7515 0.8375 -0.1990 0.074 Uiso 1 1 calc R . .
C12 C 0.6083(4) 0.9020(4) -0.2302(4) 0.0704(13) Uani 1 1 d . . .
H12 H 0.5752 0.8316 -0.2415 0.084 Uiso 1 1 calc R . .
C13 C 0.5489(3) 1.0001(4) -0.2398(3) 0.0551(10) Uani 1 1 d . . .
C14 C 0.6007(3) 1.1026(4) -0.2236(3) 0.0593(11) Uani 1 1 d . . .
H14 H 0.5626 1.1701 -0.2306 0.071 Uiso 1 1 calc R . .
C15 C 0.7076(3) 1.1084(3) -0.1974(3) 0.0552(11) Uani 1 1 d . . .
H15 H 0.7412 1.1785 -0.1869 0.066 Uiso 1 1 calc R . .
C16 C 0.4358(4) 0.9885(4) -0.2628(3) 0.0656(12) Uani 1 1 d . . .
H16 H 0.4103 0.9149 -0.2590 0.079 Uiso 1 1 calc R . .
C17 C 0.3675(4) 1.0663(4) -0.2874(4) 0.0715(13) Uani 1 1 d . . .
H17 H 0.3912 1.1406 -0.2925 0.086 Uiso 1 1 calc R . .
C18 C 0.2539(4) 1.0481(5) -0.3083(4) 0.0627(12) Uani 1 1 d . . .
N1 N 1.0255(3) 0.6495(3) -0.0970(2) 0.0558(9) Uani 1 1 d . . .
H1A H 0.9984 0.6674 -0.0422 0.084 Uiso 1 1 calc R . .
H1B H 1.0119 0.5767 -0.1134 0.084 Uiso 1 1 calc R . .
H1C H 0.9979 0.6939 -0.1492 0.084 Uiso 1 1 calc R . .
N2 N 0.8742(2) 1.0101(3) -0.1535(3) 0.0509(8) Uani 1 1 d . . .
H2A H 0.8982 1.0799 -0.1618 0.076 Uiso 1 1 calc R . .
H2B H 0.9037 0.9606 -0.1904 0.076 Uiso 1 1 calc R . .
H2C H 0.8893 0.9908 -0.0877 0.076 Uiso 1 1 calc R . .
O1 O 1.6774(3) 0.9073(3) 0.0456(3) 0.0789(10) Uani 1 1 d . . .
O2 O 1.6793(3) 0.7175(3) 0.0384(3) 0.0893(12) Uani 1 1 d . . .
H2D H 1.7392 0.7254 0.0686 0.134 Uiso 1 1 calc R . .
O1W O 0.8907(3) 0.9524(3) 0.0480(3) 0.0682(10) Uani 1 1 d . . .
O3 O 0.2274(2) 0.9412(3) -0.2919(3) 0.0823(10) Uani 1 1 d . . .
H3A H 0.1640 0.9363 -0.2999 0.123 Uiso 1 1 calc R . .
O4 O 0.1931(3) 1.1201(3) -0.3396(3) 0.0898(12) Uani 1 1 d . . .
O5 O 1.0232(2) 0.5799(3) 0.1420(3) 0.0881(12) Uani 1 1 d . . .
O6 O 0.9433(3) 0.6795(3) 0.2564(3) 0.0909(12) Uani 1 1 d . . .
O7 O 0.8935(4) 0.7088(3) 0.0782(4) 0.136(2) Uani 1 1 d . . .
O8 O 1.0510(3) 0.7781(3) 0.1696(3) 0.1058(14) Uani 1 1 d . . .
S1 S 0.97544(7) 0.68762(7) 0.16121(7) 0.0421(3) Uani 1 1 d . . .
H2W H 0.841(4) 0.951(5) 0.055(4) 0.062(19) Uiso 1 1 d . . .
H1W H 0.908(6) 0.874(7) 0.048(6) 0.16(3) Uiso 1 1 d . . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
C1 C6 1.382(5) . ?
C1 C2 1.384(6) . ?
C1 N1 1.467(5) . ?
C2 C3 1.369(6) . ?
C3 C4 1.383(6) . ?
C4 C5 1.396(6) . ?
C4 C7 1.453(6) . ?
C5 C6 1.373(6) . ?
C7 C8 1.307(6) . ?
C8 C9 1.477(7) . ?
C9 O1 1.210(5) . ?
C9 O2 1.320(6) . ?
C10 C15 1.373(6) . ?
C10 C11 1.376(5) . ?
C10 N2 1.442(5) . ?
C11 C12 1.359(6) . ?
C12 C13 1.381(6) . ?
C13 C14 1.377(6) . ?
C13 C16 1.464(6) . ?
C14 C15 1.383(6) . ?
C16 C17 1.277(6) . ?
C17 C18 1.480(6) . ?
C18 O4 1.183(5) . ?
C18 O3 1.328(5) . ?
O5 S1 1.451(3) . ?
O6 S1 1.405(3) . ?
O7 S1 1.415(3) . ?
O8 S1 1.440(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 120.0(4) . . ?
C6 C1 N1 119.5(4) . . ?
C2 C1 N1 120.4(4) . . ?
C3 C2 C1 119.6(4) . . ?
C2 C3 C4 122.0(4) . . ?
C3 C4 C5 117.2(4) . . ?
C3 C4 C7 119.9(4) . . ?
C5 C4 C7 122.9(4) . . ?
C6 C5 C4 121.8(4) . . ?
C5 C6 C1 119.4(4) . . ?
C8 C7 C4 128.7(5) . . ?
C7 C8 C9 125.2(5) . . ?
O1 C9 O2 123.1(5) . . ?
O1 C9 C8 122.6(5) . . ?
O2 C9 C8 114.3(4) . . ?
C15 C10 C11 120.5(4) . . ?
C15 C10 N2 120.4(4) . . ?
C11 C10 N2 119.1(4) . . ?
C12 C11 C10 119.6(4) . . ?
C11 C12 C13 122.0(4) . . ?
C14 C13 C12 117.3(4) . . ?
C14 C13 C16 124.4(4) . . ?
C12 C13 C16 118.3(4) . . ?
C13 C14 C15 122.0(4) . . ?
C10 C15 C14 118.6(4) . . ?
C17 C16 C13 128.5(5) . . ?
C16 C17 C18 125.4(5) . . ?
O4 C18 O3 123.4(4) . . ?
O4 C18 C17 123.6(5) . . ?
O3 C18 C17 112.9(4) . . ?
O6 S1 O7 113.8(3) . . ?
O6 S1 O8 107.1(2) . . ?
O7 S1 O8 110.2(3) . . ?
O6 S1 O5 108.0(2) . . ?
O7 S1 O5 107.8(2) . . ?
O8 S1 O5 109.9(2) . . ?

_diffrn_measured_fraction_theta_max 0.836
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.637
_refine_diff_density_min         -0.555
_refine_diff_density_rms         0.086
####################################################################### 
# 
# 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_1H2SO4-H2O_2
_database_code_depnum_ccdc_archive 'CCDC 1436619'
_audit_update_record             
;
2015-11-12 deposited with the CCDC.
2015-12-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H22 N2 O9 S'
_chemical_formula_weight         442.44

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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.3374(8)
_cell_length_b                   10.5566(12)
_cell_length_c                   13.8798(15)
_cell_angle_alpha                103.793(10)
_cell_angle_beta                 99.924(9)
_cell_angle_gamma                102.838(10)
_cell_volume                     988.76(19)
_cell_formula_units_Z            2
_cell_measurement_temperature    298
_cell_measurement_reflns_used    1642
_cell_measurement_theta_min      3.4000
_cell_measurement_theta_max      27.4020

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.486
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             464
_exptl_absorpt_coefficient_mu    0.219
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.97150
_exptl_absorpt_correction_T_max  1.000000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      298
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Sapphire3
_diffrn_detector_area_resol_mean 16.1340
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8036
_diffrn_reflns_av_R_equivalents  0.0361
_diffrn_reflns_av_sigmaI/netI    0.0789
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.92
_diffrn_reflns_theta_max         29.39
_reflns_number_total             4494
_reflns_number_gt                2801
_reflns_threshold_expression     >2σ(I)
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -25.00   17.00   1.0000    1.7500
omega____ theta____ kappa____ phi______ frames
    -      -16.5159  -99.0000   30.0000 42

#__ type_ start__ end____ width___ exp.time_
  2 omega  -12.00   24.00   1.0000    1.7500
omega____ theta____ kappa____ phi______ frames
    -      -16.5159  -99.0000  120.0000 36

#__ type_ start__ end____ width___ exp.time_
  3 omega   39.00   91.00   1.0000    1.7500
omega____ theta____ kappa____ phi______ frames
    -       17.7659 -179.0000   90.0000 52

#__ type_ start__ end____ width___ exp.time_
  4 omega   10.00   58.00   1.0000    1.7500
omega____ theta____ kappa____ phi______ frames
    -       17.7659  -99.0000  -90.0000 48

#__ type_ start__ end____ width___ exp.time_
  5 omega  -49.00   20.00   1.0000    1.7500
omega____ theta____ kappa____ phi______ frames
    -       17.7659  -57.0000  120.0000 69

#__ type_ start__ end____ width___ exp.time_
  6 omega  -53.00   72.00   1.0000    1.7500
omega____ theta____ kappa____ phi______ frames
    -       17.7659    0.0000  150.0000 125

;

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2005)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0517P)²+0.8044P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.019(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4494
_refine_ls_number_parameters     312
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1119
_refine_ls_R_factor_gt           0.0681
_refine_ls_wR_factor_ref         0.1686
_refine_ls_wR_factor_gt          0.1422
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.7678(5) 0.9643(3) 0.1544(2) 0.0343(7) Uani 1 1 d . . .
C2 C 0.6390(5) 0.9310(4) 0.2110(2) 0.0441(9) Uani 1 1 d . . .
H2 H 0.5186 0.8703 0.1794 0.053 Uiso 1 1 calc R . .
C3 C 0.6900(5) 0.9885(4) 0.3158(2) 0.0446(9) Uani 1 1 d . . .
H3 H 0.6025 0.9661 0.3543 0.054 Uiso 1 1 calc R . .
C4 C 0.8687(5) 1.0785(3) 0.3644(2) 0.0355(7) Uani 1 1 d . . .
C5 C 0.9935(5) 1.1093(4) 0.3045(3) 0.0491(9) Uani 1 1 d . . .
H5 H 1.1145 1.1695 0.3357 0.059 Uiso 1 1 calc R . .
C6 C 0.9454(5) 1.0540(4) 0.1999(3) 0.0486(9) Uani 1 1 d . . .
H6 H 1.0318 1.0770 0.1610 0.058 Uiso 1 1 calc R . .
C7 C 0.9246(5) 1.1396(3) 0.4751(2) 0.0402(8) Uani 1 1 d . . .
H7 H 1.0425 1.2053 0.5005 0.048 Uiso 1 1 calc R . .
C8 C 0.8302(5) 1.1136(4) 0.5425(2) 0.0460(9) Uani 1 1 d . . .
H8 H 0.7111 1.0491 0.5198 0.055 Uiso 1 1 calc R . .
C9 C 0.9027(5) 1.1816(4) 0.6532(3) 0.0428(9) Uani 1 1 d . . .
C10 C 0.3310(5) 0.5357(3) -0.7445(2) 0.0346(7) Uani 1 1 d . . .
C11 C 0.1890(5) 0.4609(4) -0.7130(3) 0.0468(9) Uani 1 1 d . . .
H11 H 0.0893 0.3922 -0.7603 0.056 Uiso 1 1 calc R . .
C12 C 0.1949(5) 0.4883(4) -0.6100(3) 0.0469(9) Uani 1 1 d . . .
H12 H 0.0978 0.4371 -0.5887 0.056 Uiso 1 1 calc R . .
C13 C 0.3409(5) 0.5896(3) -0.5376(2) 0.0351(7) Uani 1 1 d . . .
C14 C 0.4846(5) 0.6617(4) -0.5720(2) 0.0444(9) Uani 1 1 d . . .
H14 H 0.5859 0.7293 -0.5248 0.053 Uiso 1 1 calc R . .
C15 C 0.4817(5) 0.6360(4) -0.6747(3) 0.0455(9) Uani 1 1 d . . .
H15 H 0.5799 0.6854 -0.6964 0.055 Uiso 1 1 calc R . .
C16 C 0.3368(5) 0.6136(4) -0.4296(2) 0.0414(8) Uani 1 1 d . . .
H16 H 0.2393 0.5531 -0.4154 0.050 Uiso 1 1 calc R . .
C17 C 0.4537(5) 0.7099(4) -0.3503(3) 0.0450(9) Uani 1 1 d . . .
H17 H 0.5501 0.7741 -0.3619 0.054 Uiso 1 1 calc R . .
C18 C 0.4400(5) 0.7215(4) -0.2436(3) 0.0447(9) Uani 1 1 d . . .
N1 N 0.7110(5) 0.9064(4) 0.0434(2) 0.0413(7) Uani 1 1 d . . .
N2 N 0.3208(5) 0.5123(4) -0.8539(2) 0.0404(7) Uani 1 1 d . . .
O1 O 1.0555(4) 1.2634(3) 0.69167(19) 0.0617(8) Uani 1 1 d . . .
O2 O 0.7783(4) 1.1393(3) 0.7051(2) 0.0583(8) Uani 1 1 d . . .
O1W O 0.3148(5) 0.4035(5) -0.1096(3) 0.0678(9) Uani 1 1 d . . .
O3 O 0.2755(5) 0.6517(4) -0.2370(2) 0.0788(11) Uani 1 1 d . . .
O4 O 0.5690(4) 0.7864(4) -0.1714(2) 0.0830(10) Uani 1 1 d . . .
O5 O 0.1535(4) 0.7099(2) 0.10665(16) 0.0467(6) Uani 1 1 d . . .
O6 O 0.2800(5) 0.8699(3) 0.0225(3) 0.1028(14) Uani 1 1 d . . .
O7 O 0.1892(5) 0.6356(4) -0.0615(2) 0.0858(11) Uani 1 1 d . . .
O8 O -0.0522(4) 0.7466(3) -0.03368(18) 0.0533(7) Uani 1 1 d . . .
S1 S 0.14201(12) 0.74401(9) 0.00931(6) 0.0359(3) Uani 1 1 d . . .
H1NB H 0.782(6) 0.851(4) 0.023(3) 0.057(12) Uiso 1 1 d . . .
H2NB H 0.461(6) 0.529(3) -0.864(3) 0.050(10) Uiso 1 1 d . . .
H2NC H 0.273(6) 0.563(4) -0.878(3) 0.067(14) Uiso 1 1 d . . .
H1WB H 0.285(6) 0.470(4) -0.089(3) 0.053(15) Uiso 1 1 d . . .
H1NA H 0.585(6) 0.857(4) 0.023(3) 0.062(13) Uiso 1 1 d . . .
H2NA H 0.261(6) 0.428(4) -0.890(3) 0.053(12) Uiso 1 1 d . . .
H1NC H 0.731(6) 0.975(4) 0.016(3) 0.068(14) Uiso 1 1 d . . .
H1WA H 0.247(9) 0.372(6) -0.164(5) 0.12(3) Uiso 1 1 d . . .
H2O H 0.821(7) 1.185(4) 0.769(4) 0.082(15) Uiso 1 1 d . . .
H3O H 0.271(8) 0.651(5) -0.184(4) 0.10(2) Uiso 1 1 d . . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
C1 C2 1.369(5) . ?
C1 C6 1.370(5) . ?
C1 N1 1.463(4) . ?
C2 C3 1.383(4) . ?
C3 C4 1.383(5) . ?
C4 C5 1.376(5) . ?
C4 C7 1.463(4) . ?
C5 C6 1.379(5) . ?
C7 C8 1.300(5) . ?
C8 C9 1.477(5) . ?
C9 O1 1.196(4) . ?
C9 O2 1.324(4) . ?
C10 C11 1.363(5) . ?
C10 C15 1.380(5) . ?
C10 N2 1.465(4) . ?
C11 C12 1.380(5) . ?
C12 C13 1.382(5) . ?
C13 C14 1.381(5) . ?
C13 C16 1.466(4) . ?
C14 C15 1.381(4) . ?
C16 C17 1.317(5) . ?
C17 C18 1.479(5) . ?
C18 O4 1.194(4) . ?
C18 O3 1.298(5) . ?
O5 S1 1.472(2) . ?
O6 S1 1.430(3) . ?
O7 S1 1.467(3) . ?
O8 S1 1.456(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 121.0(3) . . ?
C2 C1 N1 119.1(3) . . ?
C6 C1 N1 119.9(3) . . ?
C1 C2 C3 119.3(3) . . ?
C2 C3 C4 121.3(3) . . ?
C5 C4 C3 117.5(3) . . ?
C5 C4 C7 120.7(3) . . ?
C3 C4 C7 121.8(3) . . ?
C4 C5 C6 122.2(3) . . ?
C1 C6 C5 118.7(3) . . ?
C8 C7 C4 128.1(3) . . ?
C7 C8 C9 123.2(4) . . ?
O1 C9 O2 123.9(3) . . ?
O1 C9 C8 124.6(4) . . ?
O2 C9 C8 111.5(3) . . ?
C11 C10 C15 120.7(3) . . ?
C11 C10 N2 119.7(3) . . ?
C15 C10 N2 119.5(3) . . ?
C10 C11 C12 119.3(3) . . ?
C11 C12 C13 121.9(3) . . ?
C14 C13 C12 117.3(3) . . ?
C14 C13 C16 123.8(3) . . ?
C12 C13 C16 118.8(3) . . ?
C15 C14 C13 121.7(3) . . ?
C10 C15 C14 119.0(3) . . ?
C17 C16 C13 128.2(4) . . ?
C16 C17 C18 123.6(4) . . ?
O4 C18 O3 123.8(4) . . ?
O4 C18 C17 123.2(4) . . ?
O3 C18 C17 113.0(3) . . ?
O6 S1 O8 111.56(18) . . ?
O6 S1 O7 108.7(2) . . ?
O8 S1 O7 108.12(17) . . ?
O6 S1 O5 110.56(17) . . ?
O8 S1 O5 111.06(15) . . ?
O7 S1 O5 106.67(15) . . ?

_diffrn_measured_fraction_theta_max 0.822
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.659
_refine_diff_density_min         -0.460
_refine_diff_density_rms         0.067

####################################################################### 
# 
# 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_1H2SO4-H2O_2_88
_database_code_depnum_ccdc_archive 'CCDC 1436620'
_audit_update_record             
;
2015-11-12 deposited with the CCDC.
2015-12-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H22 N O9 S'
_chemical_formula_weight         428.43

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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.3066(9)
_cell_length_b                   10.5681(17)
_cell_length_c                   13.8909(16)
_cell_angle_alpha                104.253(12)
_cell_angle_beta                 99.577(10)
_cell_angle_gamma                102.609(12)
_cell_volume                     986.7(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    298
_cell_measurement_reflns_used    1356
_cell_measurement_theta_min      3.4340
_cell_measurement_theta_max      23.5400

_exptl_crystal_description       block
_exptl_crystal_colour            YELLOW
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.442
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             450
_exptl_absorpt_coefficient_mu    0.216
_exptl_absorpt_correction_T_min  0.91953
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      298
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Sapphire3
_diffrn_detector_area_resol_mean 16.1340
_diffrn_reflns_number            7514
_diffrn_reflns_av_R_equivalents  0.0366
_diffrn_reflns_av_sigmaI/netI    0.0944
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.93
_diffrn_reflns_theta_max         29.27
_reflns_number_total             4446
_reflns_number_gt                2143
_reflns_threshold_expression     >2σ(I)
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega    0.00   76.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -       17.6096   57.0000  150.0000 76

#__ type_ start__ end____ width___ exp.time_
  2 omega  -20.00   86.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -       17.6096   19.0000   90.0000 106

#__ type_ start__ end____ width___ exp.time_
  3 omega  -25.00    0.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      -16.5159  -99.0000 -120.0000 25

#__ type_ start__ end____ width___ exp.time_
  4 omega  -23.00   23.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      -16.5159  -99.0000    0.0000 46

#__ type_ start__ end____ width___ exp.time_
  5 omega  -44.00   36.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -       17.6096  -57.0000  -90.0000 80

#__ type_ start__ end____ width___ exp.time_
  6 omega  -88.00  -51.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      -16.5159 -179.0000  120.0000 37

;

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0923P)²+0.4284P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4446
_refine_ls_number_parameters     310
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1600
_refine_ls_R_factor_gt           0.0776
_refine_ls_wR_factor_ref         0.2375
_refine_ls_wR_factor_gt          0.1814
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_restrained_S_all      1.005
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C7A C -0.4258(8) -0.1409(5) -0.4745(4) 0.0481(15) Uiso 0.884(10) 1 d P A 1
H7A H -0.5424 -0.2078 -0.4994 0.058 Uiso 0.884(10) 1 calc PR A 1
C8A C -0.3305(8) -0.1140(6) -0.5418(4) 0.0541(16) Uiso 0.884(10) 1 d P A 1
H8A H -0.2109 -0.0500 -0.5191 0.065 Uiso 0.884(10) 1 calc PR A 1
C7B C -0.495(7) -0.070(5) -0.459(4) 0.070(15) Uiso 0.116(10) 1 d P . 2
H7B H -0.5913 -0.1583 -0.4899 0.084 Uiso 0.116(10) 1 calc PR A 2
C8B C -0.400(8) -0.044(5) -0.532(4) 0.077(16) Uiso 0.116(10) 1 d P . 2
H8B H -0.2649 0.0013 -0.4977 0.092 Uiso 0.116(10) 1 calc PR A 2
C1 C -0.2655(7) 0.0353(4) -0.1533(3) 0.0470(10) Uani 1 1 d . . .
C2 C -0.4433(7) -0.0530(5) -0.1980(4) 0.0625(13) Uani 1 1 d . . .
H2 H -0.5293 -0.0763 -0.1587 0.075 Uiso 1 1 calc R . .
C3 C -0.1392(6) 0.0682(4) -0.2110(3) 0.0556(12) Uani 1 1 d . . .
H3 H -0.0186 0.1288 -0.1798 0.067 Uiso 1 1 calc R . .
C4 C -0.4922(7) -0.1069(5) -0.3026(4) 0.0654(14) Uani 1 1 d . A .
H4 H -0.6139 -0.1662 -0.3335 0.078 Uiso 1 1 calc R . .
C5 C -0.3686(6) -0.0766(4) -0.3631(3) 0.0486(11) Uani 1 1 d . . .
C6 C -0.1900(7) 0.0118(5) -0.3151(4) 0.0600(13) Uani 1 1 d . A .
H6 H -0.1023 0.0337 -0.3538 0.072 Uiso 1 1 calc R . .
C9 C -0.4039(8) -0.1801(5) -0.6517(4) 0.0587(12) Uani 1 1 d . . .
C10 C 0.1701(6) 0.4640(4) 0.7443(3) 0.0484(11) Uani 1 1 d . . .
C11 C 0.0210(7) 0.3639(5) 0.6744(4) 0.0599(13) Uani 1 1 d . . .
H11 H -0.0763 0.3139 0.6963 0.072 Uiso 1 1 calc R . .
C12 C 0.3117(7) 0.5395(5) 0.7126(4) 0.0595(13) Uani 1 1 d . . .
H12 H 0.4111 0.6083 0.7600 0.071 Uiso 1 1 calc R . .
C13 C 0.0165(7) 0.3380(5) 0.5714(3) 0.0571(12) Uani 1 1 d . . .
H13 H -0.0849 0.2706 0.5241 0.069 Uiso 1 1 calc R . .
C14 C 0.1609(6) 0.4111(4) 0.5376(3) 0.0482(11) Uani 1 1 d . . .
C15 C 0.3062(6) 0.5127(5) 0.6095(4) 0.0585(13) Uani 1 1 d . . .
H15 H 0.4027 0.5645 0.5882 0.070 Uiso 1 1 calc R . .
C16 C 0.1642(7) 0.3873(5) 0.4291(3) 0.0535(12) Uani 1 1 d . . .
H16 H 0.2604 0.4484 0.4145 0.064 Uiso 1 1 calc R . .
C17 C 0.0483(7) 0.2909(5) 0.3504(4) 0.0587(12) Uani 1 1 d . . .
H17 H -0.0465 0.2263 0.3627 0.070 Uiso 1 1 calc R . .
C18 C 0.0592(7) 0.2786(5) 0.2437(4) 0.0586(13) Uani 1 1 d . . .
N1 N -0.2100(8) 0.0931(5) -0.0423(3) 0.0530(10) Uani 1 1 d . . .
N2 N 0.1800(7) 0.4865(5) 0.8537(3) 0.0533(10) Uani 1 1 d . . .
O1 O -0.2801(5) -0.1379(4) -0.7043(3) 0.0725(11) Uani 1 1 d . A .
O2 O -0.5550(5) -0.2627(4) -0.6894(3) 0.0791(11) Uani 1 1 d . A .
O3 O 0.2242(6) 0.3498(5) 0.2356(3) 0.0913(15) Uani 1 1 d . . .
O4 O -0.0680(6) 0.2126(5) 0.1721(3) 0.0962(14) Uani 1 1 d . . .
O5 O 0.5529(5) 0.2551(3) 0.0330(3) 0.0652(9) Uani 1 1 d . . .
O6 O 0.3497(5) 0.2899(3) -0.1072(2) 0.0580(9) Uani 1 1 d . . .
O7 O 0.2230(6) 0.1303(4) -0.0239(3) 0.1158(18) Uani 1 1 d . . .
O8 O 0.3105(7) 0.3649(4) 0.0605(3) 0.0994(14) Uani 1 1 d . . .
S1 S 0.35942(17) 0.25658(11) -0.01021(8) 0.0500(4) Uani 1 1 d . . .
O1W O 0.1849(7) 0.5979(6) 0.1102(4) 0.0820(13) Uani 1 1 d . . .
H1W H 0.266(15) 0.643(10) 0.169(8) 0.20(5) Uiso 1 1 d . . .
H2W H 0.218(7) 0.538(5) 0.098(4) 0.043(17) Uiso 1 1 d . . .
H1X H -0.356(10) -0.195(7) -0.778(6) 0.15(3) Uiso 1 1 d . . .
H3X H 0.19(2) 0.332(13) 0.183(9) 0.26(7) Uiso 1 1 d . . .
H1NA H -0.278(8) 0.158(6) -0.024(4) 0.10(2) Uiso 1 1 d . . .
H1NB H -0.086(9) 0.135(5) -0.025(4) 0.08(2) Uiso 1 1 d . . .
H2NA H 0.037(7) 0.476(4) 0.867(3) 0.066(14) Uiso 1 1 d . . .
H1NC H -0.215(8) 0.024(6) -0.012(4) 0.081(18) Uiso 1 1 d . . .
H2NC H 0.254(8) 0.570(6) 0.887(4) 0.078(17) Uiso 1 1 d . . .
H2NB H 0.210(9) 0.426(6) 0.878(5) 0.10(2) Uiso 1 1 d . . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
C7A C8A 1.305(7) . ?
C7A C5 1.474(6) . ?
C8A C9 1.465(7) . ?
C7B C8B 1.36(6) . ?
C7B C5 1.52(5) . ?
C7B C8B 1.58(8) 2_454 ?
C8B C7B 1.58(8) 2_454 ?
C8B C9 1.90(5) . ?
C1 C3 1.363(6) . ?
C1 C2 1.364(6) . ?
C1 N1 1.461(6) . ?
C2 C4 1.377(6) . ?
C3 C6 1.373(6) . ?
C4 C5 1.372(6) . ?
C5 C6 1.375(6) . ?
C9 O2 1.190(5) . ?
C9 O1 1.325(6) . ?
C10 C12 1.366(6) . ?
C10 C11 1.374(6) . ?
C10 N2 1.465(6) . ?
C11 C13 1.383(6) . ?
C12 C15 1.381(6) . ?
C13 C14 1.385(6) . ?
C14 C15 1.379(6) . ?
C14 C16 1.470(6) . ?
C16 C17 1.310(6) . ?
C17 C18 1.473(7) . ?
C18 O4 1.185(5) . ?
C18 O3 1.313(7) . ?
O5 S1 1.446(3) . ?
O6 S1 1.468(3) . ?
O7 S1 1.428(4) . ?
O8 S1 1.465(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8A C7A C5 127.1(5) . . ?
C7A C8A C9 122.8(5) . . ?
C8B C7B C5 115(4) . . ?
C8B C7B C8B 91(4) . 2_454 ?
C5 C7B C8B 126(4) . 2_454 ?
C7B C8B C7B 89(4) . 2_454 ?
C7B C8B C9 123(4) . . ?
C7B C8B C9 120(4) 2_454 . ?
C3 C1 C2 120.7(4) . . ?
C3 C1 N1 120.0(4) . . ?
C2 C1 N1 119.3(4) . . ?
C1 C2 C4 118.3(5) . . ?
C1 C3 C6 120.0(4) . . ?
C5 C4 C2 122.6(4) . . ?
C4 C5 C6 117.3(4) . . ?
C4 C5 C7A 120.4(4) . . ?
C6 C5 C7A 122.3(4) . . ?
C4 C5 C7B 105.5(18) . . ?
C6 C5 C7B 124.2(19) . . ?
C7A C5 C7B 38.5(17) . . ?
C3 C6 C5 121.1(5) . . ?
O2 C9 O1 124.0(5) . . ?
O2 C9 C8A 124.4(5) . . ?
O1 C9 C8A 111.6(5) . . ?
O2 C9 C8B 114.8(17) . . ?
O1 C9 C8B 113.5(16) . . ?
C8A C9 C8B 30.5(17) . . ?
C12 C10 C11 120.4(4) . . ?
C12 C10 N2 120.0(4) . . ?
C11 C10 N2 119.6(4) . . ?
C10 C11 C13 119.7(5) . . ?
C10 C12 C15 119.5(4) . . ?
C11 C13 C14 120.9(4) . . ?
C15 C14 C13 118.0(4) . . ?
C15 C14 C16 118.8(4) . . ?
C13 C14 C16 123.3(4) . . ?
C14 C15 C12 121.5(5) . . ?
C17 C16 C14 128.1(5) . . ?
C16 C17 C18 124.0(5) . . ?
O4 C18 O3 123.1(5) . . ?
O4 C18 C17 123.9(5) . . ?
O3 C18 C17 113.0(5) . . ?
O7 S1 O5 111.4(2) . . ?
O7 S1 O8 109.1(3) . . ?
O5 S1 O8 107.8(2) . . ?
O7 S1 O6 110.6(2) . . ?
O5 S1 O6 110.9(2) . . ?
O8 S1 O6 106.9(2) . . ?

_diffrn_measured_fraction_theta_max 0.828
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.549
_refine_diff_density_min         -0.461
_refine_diff_density_rms         0.065


####################################################################### 
# 
# 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_1H2SO4-H2O_2_70
_database_code_depnum_ccdc_archive 'CCDC 1436621'
_audit_update_record             
;
2015-11-12 deposited with the CCDC.
2015-12-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H22 N2 O9 S'
_chemical_formula_weight         442.44

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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.2590(10)
_cell_length_b                   10.5719(15)
_cell_length_c                   13.8895(18)
_cell_angle_alpha                104.423(12)
_cell_angle_beta                 98.792(11)
_cell_angle_gamma                102.601(12)
_cell_volume                     982.9(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    298
_cell_measurement_reflns_used    1423
_cell_measurement_theta_min      2.9330
_cell_measurement_theta_max      25.0060

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.495
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             464
_exptl_absorpt_coefficient_mu    0.221
_exptl_absorpt_correction_T_min  0.79518
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      298
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Sapphire3
_diffrn_detector_area_resol_mean 16.1340
_diffrn_reflns_number            7872
_diffrn_reflns_av_R_equivalents  0.0562
_diffrn_reflns_av_sigmaI/netI    0.1041
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.92
_diffrn_reflns_theta_max         29.21
_reflns_number_total             4480
_reflns_number_gt                1995
_reflns_threshold_expression     >2σ(I)
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -19.00   18.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.5159  -99.0000   60.0000 37

#__ type_ start__ end____ width___ exp.time_
  2 omega  -19.00   20.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.5159  -99.0000  -60.0000 39

#__ type_ start__ end____ width___ exp.time_
  3 omega    6.00   51.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       17.6096   57.0000  -90.0000 45

#__ type_ start__ end____ width___ exp.time_
  4 omega  -45.00   34.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       17.6096  -57.0000  150.0000 79

#__ type_ start__ end____ width___ exp.time_
  5 omega    2.00   86.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       17.6096   57.0000   60.0000 84

#__ type_ start__ end____ width___ exp.time_
  6 omega  -51.00   36.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       17.6096  -57.0000  -90.0000 87

;


_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1968P)²+0.0241P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4480
_refine_ls_number_parameters     280
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1985
_refine_ls_R_factor_gt           0.1049
_refine_ls_wR_factor_ref         0.3746
_refine_ls_wR_factor_gt          0.2810
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.023
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C7A C -0.4245(11) -0.1406(8) 0.0265(5) 0.050(2) Uiso 0.732(15) 1 d P A 1
H7A H -0.5398 -0.2091 0.0024 0.060 Uiso 0.732(15) 1 calc PR A 1
C8A C -0.3300(11) -0.1143(9) -0.0421(5) 0.054(2) Uiso 0.732(15) 1 d P A 1
H8A H -0.2085 -0.0525 -0.0203 0.065 Uiso 0.732(15) 1 calc PR A 1
C8B C -0.381(4) -0.041(3) -0.034(2) 0.081(9) Uiso 0.268(15) 1 d P . 2
H8B H -0.2444 0.0021 -0.0018 0.097 Uiso 0.268(15) 1 calc PR A 2
C7B C -0.500(4) -0.081(3) 0.047(2) 0.087(9) Uiso 0.268(15) 1 d P . 2
H7B H -0.5893 -0.1714 0.0182 0.105 Uiso 0.268(15) 1 calc PR A 2
C1 C -0.2643(8) 0.0340(6) 0.3475(4) 0.0562(14) Uani 1 1 d . A .
C2 C -0.4425(10) -0.0534(7) 0.3053(5) 0.0766(19) Uani 1 1 d . . .
H2 H -0.5280 -0.0757 0.3458 0.092 Uiso 1 1 calc R . .
C3 C -0.4932(9) -0.1085(7) 0.2000(5) 0.076(2) Uani 1 1 d . A .
H3 H -0.6134 -0.1701 0.1700 0.091 Uiso 1 1 calc R . .
C4 C -0.3699(9) -0.0742(6) 0.1390(4) 0.0639(16) Uani 1 1 d . . .
C5 C -0.1912(10) 0.0104(7) 0.1847(5) 0.080(2) Uani 1 1 d . A .
H5 H -0.1030 0.0311 0.1452 0.096 Uiso 1 1 calc R . .
C6 C -0.1385(9) 0.0664(7) 0.2903(4) 0.0727(19) Uani 1 1 d . . .
H6 H -0.0170 0.1260 0.3209 0.087 Uiso 1 1 calc R A .
C9 C -0.4041(10) -0.1756(7) -0.1489(4) 0.0673(17) Uani 1 1 d . . .
C10 C 0.1728(8) 0.4637(6) 1.2444(4) 0.0575(14) Uani 1 1 d . . .
C11 C 0.0235(9) 0.3618(7) 1.1743(4) 0.0712(18) Uani 1 1 d . . .
H11 H -0.0740 0.3111 1.1963 0.085 Uiso 1 1 calc R . .
C12 C 0.0210(9) 0.3366(7) 1.0727(4) 0.0703(17) Uani 1 1 d . . .
H12 H -0.0790 0.2678 1.0262 0.084 Uiso 1 1 calc R . .
C13 C 0.1621(9) 0.4099(6) 1.0369(4) 0.0604(15) Uani 1 1 d . . .
C14 C 0.3094(9) 0.5162(7) 1.1088(5) 0.0710(18) Uani 1 1 d . . .
H14 H 0.4030 0.5708 1.0870 0.085 Uiso 1 1 calc R . .
C15 C 0.3142(9) 0.5391(7) 1.2117(5) 0.0707(17) Uani 1 1 d . . .
H15 H 0.4147 0.6064 1.2590 0.085 Uiso 1 1 calc R . .
C16 C 0.1649(9) 0.3892(7) 0.9285(4) 0.0658(16) Uani 1 1 d . . .
H16 H 0.2582 0.4527 0.9137 0.079 Uiso 1 1 calc R . .
C17 C 0.0507(9) 0.2912(7) 0.8499(4) 0.0691(17) Uani 1 1 d . . .
H17 H -0.0426 0.2254 0.8625 0.083 Uiso 1 1 calc R . .
C18 C 0.0619(10) 0.2797(7) 0.7434(5) 0.0684(17) Uani 1 1 d . . .
N1 N -0.2046(7) 0.0941(5) 0.4595(3) 0.0655(13) Uani 1 1 d . . .
H1A H -0.0777 0.1326 0.4771 0.098 Uiso 1 1 calc R A .
H1B H -0.2332 0.0295 0.4896 0.098 Uiso 1 1 calc R . .
H1C H -0.2670 0.1565 0.4792 0.098 Uiso 1 1 calc R . .
N2 N 0.1825(7) 0.4863(5) 1.3536(3) 0.0644(13) Uani 1 1 d . . .
H2B H 0.0639 0.4774 1.3653 0.077 Uiso 1 1 calc R . .
H2C H 0.2559 0.5695 1.3876 0.077 Uiso 1 1 calc R . .
H2D H 0.2336 0.4257 1.3742 0.077 Uiso 1 1 calc R . .
O1 O -0.5548(7) -0.2614(5) -0.1854(4) 0.0922(16) Uani 1 1 d . A .
O2 O -0.2830(7) -0.1371(5) -0.2035(3) 0.0856(15) Uani 1 1 d . A .
H2A H -0.2140 -0.0606 -0.1729 0.128 Uiso 1 1 calc R . .
O1W O 0.1875(7) 0.5982(6) 0.6112(4) 0.0974(16) Uani 1 1 d G . .
H1WA H 0.2551 0.6768 0.5912 0.146 Uiso 1 1 d G . .
H1WB H 0.2153 0.5272 0.5800 0.146 Uiso 1 1 d G . .
O3 O -0.0664(8) 0.2147(6) 0.6729(3) 0.110(2) Uani 1 1 d . . .
O4 O 0.2202(8) 0.3513(6) 0.7346(4) 0.0999(19) Uani 1 1 d . . .
O5 O 0.2265(8) 0.1308(6) 0.4751(4) 0.128(2) Uani 1 1 d . . .
O6 O 0.3557(6) 0.2909(4) 0.3931(3) 0.0702(12) Uani 1 1 d . . .
O7 O 0.3082(9) 0.3643(7) 0.5588(4) 0.1093(19) Uani 1 1 d . . .
O8 O 0.5550(6) 0.2580(5) 0.5328(3) 0.0789(13) Uani 1 1 d . . .
S1 S 0.3609(2) 0.25734(16) 0.48864(10) 0.0601(6) Uani 1 1 d . . .
H4 H 0.244(9) 0.339(6) 0.678(5) 0.063(19) Uiso 1 1 d . . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
C7A C8A 1.306(10) . ?
C7A C4 1.496(9) . ?
C8A C9 1.426(9) . ?
C8B C7B 1.61(4) . ?
C8B C7B 1.72(5) 2_455 ?
C8B C9 1.81(3) . ?
C7B C4 1.44(3) . ?
C7B C8B 1.72(5) 2_455 ?
C1 C6 1.343(8) . ?
C1 C2 1.359(8) . ?
C1 N1 1.481(7) . ?
C2 C3 1.391(9) . ?
C3 C4 1.375(8) . ?
C4 C5 1.358(8) . ?
C5 C6 1.394(8) . ?
C9 O1 1.202(7) . ?
C9 O2 1.309(7) . ?
C10 C15 1.363(8) . ?
C10 C11 1.389(8) . ?
C10 N2 1.463(7) . ?
C11 C12 1.366(8) . ?
C12 C13 1.378(8) . ?
C13 C14 1.412(8) . ?
C13 C16 1.470(8) . ?
C14 C15 1.383(8) . ?
C16 C17 1.319(8) . ?
C17 C18 1.470(9) . ?
C18 O3 1.185(7) . ?
C18 O4 1.272(8) . ?
O5 S1 1.423(5) . ?
O6 S1 1.455(4) . ?
O7 S1 1.459(5) . ?
O8 S1 1.446(5) . ?

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
C8A C7A C4 127.9(7) . . ?
C7A C8A C9 123.2(7) . . ?
C7B C8B C7B 92(2) . 2_455 ?
C7B C8B C9 116(2) . . ?
C7B C8B C9 116.5(19) 2_455 . ?
C4 C7B C8B 111(2) . . ?
C4 C7B C8B 125(2) . 2_455 ?
C8B C7B C8B 88(2) . 2_455 ?
C6 C1 C2 121.7(5) . . ?
C6 C1 N1 118.7(5) . . ?
C2 C1 N1 119.6(5) . . ?
C1 C2 C3 118.1(5) . . ?
C4 C3 C2 121.6(6) . . ?
C5 C4 C3 118.2(5) . . ?
C5 C4 C7B 129.8(13) . . ?
C3 C4 C7B 103.0(13) . . ?
C5 C4 C7A 121.1(6) . . ?
C3 C4 C7A 120.3(6) . . ?
C7B C4 C7A 37.6(12) . . ?
C4 C5 C6 120.7(6) . . ?
C1 C6 C5 119.7(6) . . ?
O1 C9 O2 122.8(6) . . ?
O1 C9 C8A 124.1(6) . . ?
O2 C9 C8A 112.9(6) . . ?
O1 C9 C8B 120.1(11) . . ?
O2 C9 C8B 111.1(10) . . ?
C8A C9 C8B 30.3(9) . . ?
C15 C10 C11 120.1(5) . . ?
C15 C10 N2 120.0(5) . . ?
C11 C10 N2 119.8(5) . . ?
C12 C11 C10 119.5(6) . . ?
C11 C12 C13 122.0(6) . . ?
C12 C13 C14 117.9(5) . . ?
C12 C13 C16 124.4(6) . . ?
C14 C13 C16 117.6(5) . . ?
C15 C14 C13 119.8(6) . . ?
C10 C15 C14 120.6(6) . . ?
C17 C16 C13 127.6(6) . . ?
C16 C17 C18 123.9(7) . . ?
O3 C18 O4 123.2(6) . . ?
O3 C18 C17 123.5(7) . . ?
O4 C18 C17 113.2(6) . . ?
O5 S1 O8 111.3(3) . . ?
O5 S1 O6 111.2(3) . . ?
O8 S1 O6 110.5(3) . . ?
O5 S1 O7 109.2(4) . . ?
O8 S1 O7 107.4(3) . . ?
O6 S1 O7 107.0(3) . . ?

_diffrn_measured_fraction_theta_max 0.842
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.491
_refine_diff_density_min         -0.427
_refine_diff_density_rms         0.104

####################################################################### 
# 
# 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_1H2SO4-H2O_2_58
_database_code_depnum_ccdc_archive 'CCDC 1436622'
_audit_update_record             
;
2015-11-12 deposited with the CCDC.
2015-12-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H22 N2 O9 S'
_chemical_formula_weight         442.44

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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.2497(10)
_cell_length_b                   10.6164(17)
_cell_length_c                   13.902(2)
_cell_angle_alpha                104.762(14)
_cell_angle_beta                 98.258(13)
_cell_angle_gamma                102.574(13)
_cell_volume                     987.2(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    298
_cell_measurement_reflns_used    1411
_cell_measurement_theta_min      2.9020
_cell_measurement_theta_max      26.5320

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.488
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             464
_exptl_absorpt_coefficient_mu    0.220
_exptl_absorpt_correction_T_min  0.81950
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      298
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Sapphire3
_diffrn_detector_area_resol_mean 16.1340
_diffrn_reflns_number            7418
_diffrn_reflns_av_R_equivalents  0.0526
_diffrn_reflns_av_sigmaI/netI    0.1018
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.92
_diffrn_reflns_theta_max         29.30
_reflns_number_total             4469
_reflns_number_gt                2013
_reflns_threshold_expression     >2σ(I)
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -45.00  -18.00   1.0000   37.5000
omega____ theta____ kappa____ phi______ frames
    -      -16.5159   77.0000   30.0000 27

#__ type_ start__ end____ width___ exp.time_
  2 omega  -24.00    9.00   1.0000   37.5000
omega____ theta____ kappa____ phi______ frames
    -      -16.5159  -99.0000 -180.0000 33

#__ type_ start__ end____ width___ exp.time_
  3 omega   20.00   50.00   1.0000   37.5000
omega____ theta____ kappa____ phi______ frames
    -      -16.5159   77.0000   30.0000 30

#__ type_ start__ end____ width___ exp.time_
  4 omega  -83.00   12.00   1.0000   37.5000
omega____ theta____ kappa____ phi______ frames
    -      -16.5159  -77.0000  -90.0000 95

#__ type_ start__ end____ width___ exp.time_
  5 omega  -20.00   68.00   1.0000   37.5000
omega____ theta____ kappa____ phi______ frames
    -       17.6096   19.0000 -120.0000 88

#__ type_ start__ end____ width___ exp.time_
  6 omega   -1.00   26.00   1.0000   37.5000
omega____ theta____ kappa____ phi______ frames
    -       17.6096   57.0000 -180.0000 27

#__ type_ start__ end____ width___ exp.time_
  7 omega   32.00   92.00   1.0000   37.5000
omega____ theta____ kappa____ phi______ frames
    -       17.6096 -179.0000  150.0000 60

;

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.2000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4469
_refine_ls_number_parameters     280
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2188
_refine_ls_R_factor_gt           0.1282
_refine_ls_wR_factor_ref         0.4098
_refine_ls_wR_factor_gt          0.3363
_refine_ls_goodness_of_fit_ref   1.149
_refine_ls_restrained_S_all      1.149
_refine_ls_shift/su_max          0.003
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C7A C 0.4274(15) 0.1397(11) -0.0283(8) 0.054(3) Uiso 0.598(15) 1 d P A 1
H7A H 0.5417 0.2085 -0.0048 0.064 Uiso 0.598(15) 1 calc PR A 1
C8A C 0.3269(17) 0.1137(12) 0.0425(8) 0.059(3) Uiso 0.598(15) 1 d P A 1
H8A H 0.2031 0.0554 0.0212 0.071 Uiso 0.598(15) 1 calc PR A 1
C8B C 0.388(3) 0.044(2) 0.0385(15) 0.080(6) Uiso 0.402(15) 1 d P . 2
H8B H 0.2520 0.0002 0.0065 0.096 Uiso 0.402(15) 1 calc PR A 2
C7B C 0.504(3) 0.068(2) -0.0469(17) 0.095(7) Uiso 0.402(15) 1 d P . 2
H7B H 0.5993 0.1562 -0.0193 0.114 Uiso 0.402(15) 1 calc PR A 2
C1 C 0.2621(11) -0.0350(7) -0.3491(5) 0.0662(18) Uani 1 1 d . A .
C2 C 0.1370(11) -0.0680(7) -0.2903(5) 0.077(2) Uani 1 1 d . . .
H2 H 0.0140 -0.1251 -0.3199 0.092 Uiso 1 1 calc R . .
C3 C 0.1944(11) -0.0159(8) -0.1856(5) 0.082(2) Uani 1 1 d . A .
H3 H 0.1094 -0.0390 -0.1449 0.099 Uiso 1 1 calc R . .
C4 C 0.3741(11) 0.0691(7) -0.1412(5) 0.076(2) Uani 1 1 d . . .
C5 C 0.4931(11) 0.1026(8) -0.2054(6) 0.081(2) Uani 1 1 d . A .
H5 H 0.6146 0.1623 -0.1762 0.097 Uiso 1 1 calc R . .
C6 C 0.4427(12) 0.0536(8) -0.3083(6) 0.083(2) Uani 1 1 d . . .
H6 H 0.5258 0.0785 -0.3493 0.100 Uiso 1 1 calc R A .
C9 C 0.4034(12) 0.1715(9) 0.1456(6) 0.078(2) Uani 1 1 d . . .
C10 C 0.0290(12) 0.3613(8) 1.1739(5) 0.083(2) Uani 1 1 d . . .
H10 H -0.0672 0.3100 1.1964 0.100 Uiso 1 1 calc R . .
C11 C 0.1751(10) 0.4634(7) 1.2439(5) 0.0647(17) Uani 1 1 d . . .
C12 C 0.3149(11) 0.5388(8) 1.2108(5) 0.079(2) Uani 1 1 d . . .
H12 H 0.4161 0.6056 1.2575 0.095 Uiso 1 1 calc R . .
C13 C 0.3065(11) 0.5159(8) 1.1072(5) 0.077(2) Uani 1 1 d . . .
H13 H 0.3981 0.5716 1.0852 0.093 Uiso 1 1 calc R . .
C14 C 0.1642(10) 0.4115(7) 1.0359(5) 0.0672(17) Uani 1 1 d . . .
C15 C 0.0242(11) 0.3346(8) 1.0706(5) 0.082(2) Uani 1 1 d . . .
H15 H -0.0737 0.2646 1.0244 0.099 Uiso 1 1 calc R . .
C16 C 0.1663(11) 0.3901(7) 0.9286(5) 0.0699(18) Uani 1 1 d . . .
H16 H 0.2599 0.4529 0.9134 0.084 Uiso 1 1 calc R . .
C17 C 0.0504(11) 0.2914(8) 0.8492(5) 0.078(2) Uani 1 1 d . . .
H17 H -0.0426 0.2259 0.8620 0.094 Uiso 1 1 calc R . .
C18 C 0.0610(12) 0.2804(8) 0.7436(5) 0.0754(19) Uani 1 1 d . . .
O1 O 0.5540(9) 0.2586(7) 0.1806(5) 0.1067(19) Uani 1 1 d . A .
O2 O 0.2822(9) 0.1339(6) 0.2007(4) 0.0935(17) Uani 1 1 d . A .
H2A H 0.3128 0.1881 0.2578 0.140 Uiso 1 1 calc R . .
O3 O 0.2193(9) 0.3536(7) 0.7324(4) 0.110(2) Uani 1 1 d . . .
O4 O -0.0645(9) 0.2122(7) 0.6730(4) 0.113(2) Uani 1 1 d . . .
O5 O 0.2300(10) 0.1310(6) 0.4725(5) 0.131(3) Uani 1 1 d . . .
O6 O 0.3097(11) 0.3682(7) 0.5562(4) 0.111(2) Uani 1 1 d . . .
O7 O 0.5556(7) 0.2595(5) 0.5301(4) 0.0819(14) Uani 1 1 d . . .
O8 O 0.3613(7) 0.2907(5) 0.3919(3) 0.0789(14) Uani 1 1 d . . .
S1 S 0.3632(3) 0.25771(17) 0.48740(12) 0.0650(6) Uani 1 1 d . . .
N1 N 0.2015(9) -0.0924(6) -0.4611(4) 0.0739(16) Uani 1 1 d . . .
H1A H 0.0759 -0.1346 -0.4779 0.111 Uiso 1 1 calc R A .
H1B H 0.2685 -0.1508 -0.4830 0.111 Uiso 1 1 calc R . .
H1C H 0.2235 -0.0261 -0.4898 0.111 Uiso 1 1 calc R . .
N2 N 0.1862(8) 0.4867(6) 1.3523(4) 0.0693(15) Uani 1 1 d . . .
H2B H 0.2569 0.4371 1.3748 0.104 Uiso 1 1 calc R . .
H2C H 0.0677 0.4635 1.3638 0.104 Uiso 1 1 calc R . .
H2D H 0.2409 0.5738 1.3849 0.104 Uiso 1 1 calc R . .
O1W O 0.1850(9) 0.5974(8) 0.6113(5) 0.109(2) Uani 1 1 d G . .
H1WA H 0.1391 0.6619 0.6029 0.164 Uiso 1 1 d G . .
H1WB H 0.1716 0.5399 0.5539 0.164 Uiso 1 1 d G . .
H3A H 0.229(7) 0.354(5) 0.669(4) 0.037(13) Uiso 1 1 d . . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
C7A C8A 1.353(13) . ?
C7A C4 1.509(12) . ?
C8A C9 1.384(13) . ?
C8B C7B 1.57(3) 2_655 ?
C8B C7B 1.59(3) . ?
C8B C9 1.71(2) . ?
C7B C4 1.51(2) . ?
C7B C8B 1.57(3) 2_655 ?
C1 C2 1.354(10) . ?
C1 C6 1.378(11) . ?
C1 N1 1.481(8) . ?
C2 C3 1.382(10) . ?
C3 C4 1.366(10) . ?
C4 C5 1.384(10) . ?
C5 C6 1.356(11) . ?
C9 O1 1.209(9) . ?
C9 O2 1.309(9) . ?
C10 C11 1.382(10) . ?
C10 C15 1.384(9) . ?
C11 C12 1.360(9) . ?
C11 N2 1.451(8) . ?
C12 C13 1.388(9) . ?
C13 C14 1.387(10) . ?
C14 C15 1.383(9) . ?
C14 C16 1.453(9) . ?
C16 C17 1.336(10) . ?
C17 C18 1.457(10) . ?
C18 O4 1.187(9) . ?
C18 O3 1.292(10) . ?
O5 S1 1.421(5) . ?
O6 S1 1.474(6) . ?
O7 S1 1.430(5) . ?
O8 S1 1.455(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8A C7A C4 127.1(10) . . ?
C7A C8A C9 121.8(11) . . ?
C7B C8B C7B 86.9(15) 2_655 . ?
C7B C8B C9 119.1(15) 2_655 . ?
C7B C8B C9 121.8(15) . . ?
C4 C7B C8B 125.7(18) . 2_655 ?
C4 C7B C8B 112.2(16) . . ?
C8B C7B C8B 93.1(15) 2_655 . ?
C2 C1 C6 122.1(7) . . ?
C2 C1 N1 119.2(7) . . ?
C6 C1 N1 118.6(6) . . ?
C1 C2 C3 119.3(7) . . ?
C4 C3 C2 120.9(7) . . ?
C3 C4 C5 117.2(7) . . ?
C3 C4 C7B 126.3(11) . . ?
C5 C4 C7B 106.6(11) . . ?
C3 C4 C7A 120.7(7) . . ?
C5 C4 C7A 121.4(7) . . ?
C7B C4 C7A 40.4(8) . . ?
C6 C5 C4 123.8(7) . . ?
C5 C6 C1 116.7(7) . . ?
O1 C9 O2 123.6(7) . . ?
O1 C9 C8A 124.0(8) . . ?
O2 C9 C8A 111.9(8) . . ?
O1 C9 C8B 118.6(9) . . ?
O2 C9 C8B 111.9(9) . . ?
C8A C9 C8B 33.2(7) . . ?
C11 C10 C15 120.8(7) . . ?
C12 C11 C10 119.5(7) . . ?
C12 C11 N2 119.7(6) . . ?
C10 C11 N2 120.8(6) . . ?
C11 C12 C13 120.0(7) . . ?
C14 C13 C12 121.3(6) . . ?
C15 C14 C13 118.0(6) . . ?
C15 C14 C16 123.2(7) . . ?
C13 C14 C16 118.8(6) . . ?
C14 C15 C10 120.3(7) . . ?
C17 C16 C14 128.0(7) . . ?
C16 C17 C18 123.9(8) . . ?
O4 C18 O3 121.9(7) . . ?
O4 C18 C17 123.9(8) . . ?
O3 C18 C17 114.2(7) . . ?
O5 S1 O7 111.8(4) . . ?
O5 S1 O8 110.8(3) . . ?
O7 S1 O8 109.2(3) . . ?
O5 S1 O6 111.3(4) . . ?
O7 S1 O6 107.9(4) . . ?
O8 S1 O6 105.7(3) . . ?

_diffrn_measured_fraction_theta_max 0.830
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.591
_refine_diff_density_min         -0.455
_refine_diff_density_rms         0.114


####################################################################### 
# 
# 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_1H2SO4-H2O_2_27
_database_code_depnum_ccdc_archive 'CCDC 1436623'
_audit_update_record             
;
2015-11-12 deposited with the CCDC.
2015-12-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H22 N2 O9 S'
_chemical_formula_weight         442.45

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 0.0020 '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 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0110 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1250 0.1230 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.1238(19)
_cell_length_b                   10.631(2)
_cell_length_c                   13.925(3)
_cell_angle_alpha                106.010(17)
_cell_angle_beta                 95.898(18)
_cell_angle_gamma                102.081(19)
_cell_volume                     976.7(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    298
_cell_measurement_reflns_used    1506
_cell_measurement_theta_min      3.0660
_cell_measurement_theta_max      25.1470

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.504
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             464
_exptl_absorpt_coefficient_mu    0.222
_exptl_absorpt_correction_T_min  0.57177
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      298
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Sapphire3
_diffrn_detector_area_resol_mean 16.1340
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7796
_diffrn_reflns_av_R_equivalents  0.0537
_diffrn_reflns_av_sigmaI/netI    0.0953
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.93
_diffrn_reflns_theta_max         29.40
_reflns_number_total             4453
_reflns_number_gt                1990
_reflns_threshold_expression     >2σ(I)
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -17.00   88.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -       17.7659   19.0000   30.0000 105

#__ type_ start__ end____ width___ exp.time_
  2 omega   30.00   57.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -       17.7659  -99.0000  -30.0000 27

#__ type_ start__ end____ width___ exp.time_
  3 omega  -15.00   23.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.5159  -99.0000 -120.0000 38

#__ type_ start__ end____ width___ exp.time_
  4 omega   -4.00   88.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -       17.7659   38.0000  -90.0000 92

#__ type_ start__ end____ width___ exp.time_
  5 omega   18.00   57.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -       17.7659   57.0000 -180.0000 39

#__ type_ start__ end____ width___ exp.time_
  6 omega  -22.00   58.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -       17.7659  -99.0000   90.0000 80

;

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2005)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1343P)²+2.0494P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4453
_refine_ls_number_parameters     279
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1893
_refine_ls_R_factor_gt           0.1032
_refine_ls_wR_factor_ref         0.3381
_refine_ls_wR_factor_gt          0.2711
_refine_ls_goodness_of_fit_ref   0.975
_refine_ls_restrained_S_all      0.975
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C7A C 1.0046(13) 0.5731(9) 0.9563(6) 0.059(3) Uiso 0.738(15) 1 d P . 1
H7A H 1.0961 0.6623 0.9839 0.071 Uiso 0.738(15) 1 calc PR . 1
C8A C 1.1127(13) 0.4574(10) 0.9644(6) 0.061(3) Uiso 0.738(15) 1 d P . 1
H8A H 1.2511 0.4960 0.9935 0.073 Uiso 0.738(15) 1 calc PR . 1
C7B C 0.919(4) 0.640(3) 0.9753(19) 0.062(8) Uiso 0.262(15) 1 d P . 2
H7B H 1.0176 0.7196 0.9975 0.075 Uiso 0.262(15) 1 calc PR . 2
C8B C 0.833(4) 0.616(3) 1.0408(18) 0.061(7) Uiso 0.262(15) 1 d P . 2
H8B H 0.7049 0.5651 1.0228 0.073 Uiso 0.262(15) 1 calc PR . 2
C1 C 0.7517(9) 0.4694(6) 0.6480(4) 0.0565(15) Uani 1 1 d . . .
C2 C 0.9384(11) 0.5514(7) 0.6849(5) 0.075(2) Uani 1 1 d . . .
H2 H 1.0180 0.5759 0.6408 0.090 Uiso 1 1 calc R . .
C3 C 0.6375(10) 0.4369(7) 0.7119(5) 0.0710(19) Uani 1 1 d . . .
H3 H 0.5112 0.3837 0.6867 0.085 Uiso 1 1 calc R . .
C4 C 1.0039(11) 0.5957(7) 0.7870(5) 0.076(2) Uani 1 1 d . . .
H4 H 1.1270 0.6540 0.8117 0.091 Uiso 1 1 calc R . .
C5 C 0.7046(11) 0.4812(7) 0.8155(5) 0.076(2) Uani 1 1 d . . .
H5 H 0.6227 0.4603 0.8598 0.091 Uiso 1 1 calc R . .
C6 C 0.8974(10) 0.5581(6) 0.8531(5) 0.0669(18) Uani 1 1 d . . .
C9 C 1.0842(12) 0.3388(8) 0.8616(5) 0.075(2) Uani 1 1 d . . .
C10 C 0.1842(10) 0.9543(7) 0.7936(5) 0.0694(18) Uani 1 1 d . . .
H10 H 0.0897 0.8824 0.7486 0.083 Uiso 1 1 calc R . .
C11 C 0.3113(10) 1.0332(6) 0.7578(5) 0.0642(17) Uani 1 1 d . . .
C12 C 0.4551(11) 1.1395(7) 0.8269(5) 0.081(2) Uani 1 1 d . . .
H12 H 0.5475 1.1943 0.8037 0.097 Uiso 1 1 calc R . .
C13 C 0.1909(11) 0.9779(7) 0.8968(5) 0.074(2) Uani 1 1 d . . .
H13 H 0.1010 0.9209 0.9197 0.089 Uiso 1 1 calc R . .
C14 C 0.3291(10) 1.0849(7) 0.9674(5) 0.0647(17) Uani 1 1 d . . .
C15 C 0.4586(11) 1.1619(7) 0.9284(5) 0.077(2) Uani 1 1 d . . .
H15 H 0.5542 1.2334 0.9731 0.093 Uiso 1 1 calc R . .
C16 C 0.3281(10) 1.1056(7) 1.0746(5) 0.0673(18) Uani 1 1 d . . .
H16 H 0.2403 1.0405 1.0916 0.081 Uiso 1 1 calc R . .
C17 C 0.4383(10) 1.2067(7) 1.1508(5) 0.0722(19) Uani 1 1 d . . .
H17 H 0.5237 1.2751 1.1360 0.087 Uiso 1 1 calc R . .
C18 C 0.4329(12) 1.2169(8) 1.2582(6) 0.0740(19) Uani 1 1 d . . .
N1 N 0.6870(13) 0.4136(7) 0.5378(4) 0.0672(16) Uani 1 1 d . . .
H1NB H 0.724(9) 0.492(7) 0.508(5) 0.064(18) Uiso 1 1 d . . .
H1NA H 0.778(10) 0.380(7) 0.530(5) 0.07(3) Uiso 1 1 d . . .
H1NC H 0.568(9) 0.379(6) 0.532(4) 0.048(18) Uiso 1 1 d . . .
N2 N 0.3024(9) 1.0158(5) 0.6504(4) 0.0680(15) Uani 1 1 d . . .
H2A H 0.2325 0.9330 0.6151 0.102 Uiso 1 1 calc R . .
H2B H 0.4224 1.0274 0.6359 0.102 Uiso 1 1 calc R . .
H2C H 0.2468 1.0765 0.6342 0.102 Uiso 1 1 calc R . .
O1 O 0.9451(9) 0.2464(6) 0.8334(4) 0.0984(18) Uani 1 1 d . . .
O2 O 1.2100(9) 0.3710(6) 0.8049(4) 0.0809(17) Uani 1 1 d . . .
O1W O 0.3232 0.8958 0.3873 0.111 Uani 1 1 d . . .
H1WA H 0.2830 0.9512 0.4231 0.131 Uiso 1 1 d . . .
H1WB H 0.2254 0.8076 0.3677 0.141 Uiso 1 1 d . . .
O3 O 0.2820(9) 1.1378(7) 1.2714(4) 0.1037(19) Uani 1 1 d . . .
H3A H 0.2802 1.1530 1.3323 0.156 Uiso 1 1 calc R . .
O4 O 0.5589(9) 1.2899(6) 1.3271(4) 0.106(2) Uani 1 1 d . . .
O5 O 0.1953(9) 0.1316(6) 0.4489(4) 0.0990(18) Uani 1 1 d . . .
O6 O 0.1239(7) 0.2112(4) 0.6138(3) 0.0717(13) Uani 1 1 d . . .
O7 O -0.0621(7) 0.2412(5) 0.4726(3) 0.0745(13) Uani 1 1 d . . .
O8 O 0.2643(8) 0.3682(5) 0.5315(4) 0.0947(18) Uani 1 1 d . . .
S1 S 0.1312(2) 0.24057(16) 0.51717(12) 0.0616(5) Uani 1 1 d . . .
H2X H 1.220(11) 0.340(7) 0.756(6) 0.06(3) Uiso 1 1 d . . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
C7A C8A 1.516(12) 2_767 ?
C7A C6 1.507(10) . ?
C7A C8A 1.605(15) . ?
C8A C7A 1.516(12) 2_767 ?
C8A C9 1.587(12) . ?
C7B C8B 1.20(3) . ?
C7B C6 1.66(3) . ?
C8B C9 1.34(2) 2_767 ?
C1 C3 1.331(9) . ?
C1 C2 1.386(9) . ?
C1 N1 1.470(8) . ?
C2 C4 1.364(9) . ?
C3 C5 1.386(9) . ?
C4 C6 1.342(9) . ?
C5 C6 1.405(9) . ?
C9 O1 1.183(8) . ?
C9 O2 1.307(9) . ?
C9 C8B 1.34(3) 2_767 ?
C10 C11 1.333(9) . ?
C10 C13 1.382(9) . ?
C11 C12 1.402(9) . ?
C11 N2 1.449(8) . ?
C12 C15 1.363(9) . ?
C13 C14 1.395(9) . ?
C14 C15 1.359(9) . ?
C14 C16 1.449(9) . ?
C16 C17 1.321(9) . ?
C17 C18 1.474(10) . ?
C18 O4 1.203(8) . ?
C18 O3 1.282(9) . ?
O5 S1 1.469(6) . ?
O6 S1 1.467(4) . ?
O7 S1 1.454(5) . ?
O8 S1 1.433(5) . ?

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
C8A C7A C6 118.6(7) 2_767 . ?
C8A C7A C8A 89.4(7) 2_767 . ?
C6 C7A C8A 116.7(7) . . ?
C7A C8A C9 116.7(7) 2_767 . ?
C7A C8A C7A 90.6(7) 2_767 . ?
C9 C8A C7A 114.4(7) . . ?
C8B C7B C6 133(2) . . ?
C7B C8B C9 122(2) . 2_767 ?
C3 C1 C2 120.1(6) . . ?
C3 C1 N1 121.0(6) . . ?
C2 C1 N1 118.8(6) . . ?
C4 C2 C1 119.0(7) . . ?
C1 C3 C5 120.8(6) . . ?
C6 C4 C2 122.5(6) . . ?
C3 C5 C6 119.4(7) . . ?
C4 C6 C5 117.8(6) . . ?
C4 C6 C7A 117.2(7) . . ?
C5 C6 C7A 123.4(6) . . ?
C4 C6 C7B 126.9(10) . . ?
C5 C6 C7B 109.6(11) . . ?
C7A C6 C7B 37.5(9) . . ?
O1 C9 O2 124.7(7) . . ?
O1 C9 C8B 119.7(13) . 2_767 ?
O2 C9 C8B 110.7(13) . 2_767 ?
O1 C9 C8A 122.9(8) . . ?
O2 C9 C8A 111.0(7) . . ?
C8B C9 C8A 35.9(12) 2_767 . ?
C11 C10 C13 120.9(6) . . ?
C10 C11 C12 118.7(6) . . ?
C10 C11 N2 122.4(6) . . ?
C12 C11 N2 118.8(6) . . ?
C15 C12 C11 119.6(7) . . ?
C10 C13 C14 121.7(7) . . ?
C15 C14 C13 115.9(6) . . ?
C15 C14 C16 124.8(6) . . ?
C13 C14 C16 119.3(6) . . ?
C12 C15 C14 123.2(6) . . ?
C17 C16 C14 127.1(7) . . ?
C16 C17 C18 123.4(7) . . ?
O4 C18 O3 122.8(7) . . ?
O4 C18 C17 123.8(7) . . ?
O3 C18 C17 113.4(6) . . ?
O8 S1 O7 109.9(3) . . ?
O8 S1 O5 110.2(4) . . ?
O7 S1 O5 108.6(3) . . ?
O8 S1 O6 110.8(3) . . ?
O7 S1 O6 109.9(3) . . ?
O5 S1 O6 107.4(3) . . ?

_diffrn_measured_fraction_theta_max 0.827
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.654
_refine_diff_density_min         -0.675
_refine_diff_density_rms         0.083


####################################################################### 
# 
# 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_1H2SO4-H2O_2_20
_database_code_depnum_ccdc_archive 'CCDC 1436624'
_audit_update_record             
;
2015-11-12 deposited with the CCDC.
2015-12-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H22 N2 O9 S'
_chemical_formula_weight         442.44

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'

_symmetry_cell_setting           TRICLINIC
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.0960(5)
_cell_length_b                   10.6518(9)
_cell_length_c                   13.9338(12)
_cell_angle_alpha                106.307(8)
_cell_angle_beta                 95.377(7)
_cell_angle_gamma                101.948(7)
_cell_volume                     975.91(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    298
_cell_measurement_reflns_used    3573
_cell_measurement_theta_min      3.0640
_cell_measurement_theta_max      27.5260

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.506
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             464
_exptl_absorpt_coefficient_mu    0.222
_exptl_absorpt_correction_T_min  0.47098
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Sapphire3
_diffrn_detector_area_resol_mean 16.1340
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            14762
_diffrn_reflns_av_R_equivalents  0.0808
_diffrn_reflns_av_sigmaI/netI    0.0749
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.93
_diffrn_reflns_theta_max         29.31
_reflns_number_total             4647
_reflns_number_gt                2743
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1593P)²+0.8141P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4647
_refine_ls_number_parameters     291
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1522
_refine_ls_R_factor_gt           0.1009
_refine_ls_wR_factor_ref         0.3155
_refine_ls_wR_factor_gt          0.2728
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C7A C 0.4939(8) -0.0722(6) 0.0446(4) 0.0448(16) Uiso 0.791(14) 1 d P . 1
H7A H 0.4031 -0.1614 0.0180 0.054 Uiso 0.791(14) 1 calc PR . 1
C8A C 0.3870(8) 0.0416(6) 0.0366(4) 0.0434(16) Uiso 0.791(14) 1 d P . 1
H8A H 0.2480 0.0041 0.0091 0.052 Uiso 0.791(14) 1 calc PR . 1
C7B C 0.556(6) -0.137(4) 0.027(3) 0.095(12) Uiso 0.209(14) 1 d P . 2
H7B H 0.4449 -0.2085 0.0038 0.114 Uiso 0.209(14) 1 calc PR . 2
C8B C 0.662(5) -0.113(3) -0.041(2) 0.075(9) Uiso 0.209(14) 1 d P . 2
H8B H 0.7927 -0.0661 -0.0219 0.090 Uiso 0.209(14) 1 calc PR . 2
C1 C 0.7474(7) 0.0303(4) 0.3527(3) 0.0482(10) Uani 1 1 d . . .
C2 C 0.8638(7) 0.0631(5) 0.2877(4) 0.0609(13) Uani 1 1 d . . .
H2 H 0.9919 0.1133 0.3117 0.073 Uiso 1 1 calc R . .
C3 C 0.7914(8) 0.0216(6) 0.1846(4) 0.0686(15) Uani 1 1 d . . .
H3 H 0.8715 0.0437 0.1396 0.082 Uiso 1 1 calc R . .
C4 C 0.4924(7) -0.0930(5) 0.2158(4) 0.0632(13) Uani 1 1 d . . .
H4 H 0.3682 -0.1497 0.1917 0.076 Uiso 1 1 calc R . .
C5 C 0.5999(7) -0.0528(5) 0.1484(3) 0.0543(11) Uani 1 1 d . . .
C6 C 0.5623(8) -0.0518(5) 0.3187(4) 0.0656(14) Uani 1 1 d . . .
H6 H 0.4863 -0.0790 0.3635 0.079 Uiso 1 1 calc R . .
C9 C 0.4197(7) 0.1575(5) 0.1359(4) 0.0579(12) Uani 1 1 d . . .
C10 C 0.9502(8) 0.6400(6) 0.8274(4) 0.0710(15) Uani 1 1 d . . .
H10 H 1.0399 0.6960 0.8035 0.085 Uiso 1 1 calc R . .
C11 C 0.8094(7) 0.5334(5) 0.7601(3) 0.0540(11) Uani 1 1 d . . .
C12 C 0.6812(7) 0.4514(5) 0.7951(4) 0.0631(13) Uani 1 1 d . . .
H12 H 0.5875 0.3794 0.7500 0.076 Uiso 1 1 calc R . .
C13 C 0.6901(8) 0.4751(6) 0.8984(4) 0.0653(14) Uani 1 1 d . . .
H13 H 0.6031 0.4172 0.9221 0.078 Uiso 1 1 calc R . .
C14 C 0.8256(7) 0.5831(5) 0.9675(4) 0.0563(12) Uani 1 1 d . . .
C15 C 0.9558(8) 0.6620(5) 0.9290(4) 0.0714(15) Uani 1 1 d . . .
H15 H 1.0515 0.7330 0.9737 0.086 Uiso 1 1 calc R . .
C16 C 0.8261(7) 0.6036(5) 1.0764(4) 0.0603(12) Uani 1 1 d . . .
H16 H 0.7411 0.5381 1.0943 0.072 Uiso 1 1 calc R . .
C17 C 0.9362(8) 0.7065(6) 1.1514(4) 0.0645(13) Uani 1 1 d . . .
H17 H 1.0203 0.7751 1.1361 0.077 Uiso 1 1 calc R . .
C18 C 0.9294(8) 0.7156(6) 1.2592(4) 0.0650(13) Uani 1 1 d . . .
N1 N 0.8161(8) 0.0849(6) 0.4621(3) 0.0565(11) Uani 1 1 d . . .
N2 N 0.7985(6) 0.5149(4) 0.6519(3) 0.0586(10) Uani 1 1 d . . .
H2B H 0.7349 0.4305 0.6173 0.088 Uiso 1 1 calc R . .
H2C H 0.9186 0.5311 0.6369 0.088 Uiso 1 1 calc R . .
H2D H 0.7352 0.5717 0.6353 0.088 Uiso 1 1 calc R . .
O1 O 0.5533(6) 0.2529(4) 0.1619(3) 0.0857(13) Uani 1 1 d . . .
O2 O 0.2904(5) 0.1282(4) 0.1945(3) 0.0704(10) Uani 1 1 d . . .
H2A H 0.3166 0.1874 0.2495 0.106 Uiso 1 1 calc R . .
O3 O 1.0553(7) 0.7908(5) 1.3267(3) 0.1005(15) Uani 1 1 d . . .
O4 O 0.7804(6) 0.6345(5) 1.2734(3) 0.0909(14) Uani 1 1 d . . .
O5 O 0.5644(5) 0.2587(4) 0.5262(3) 0.0658(9) Uani 1 1 d . . .
O6 O 0.3785(5) 0.2879(3) 0.3840(2) 0.0625(9) Uani 1 1 d . . .
O7 O 0.2358(5) 0.1326(4) 0.4662(3) 0.0775(12) Uani 1 1 d . . .
O8 O 0.3081(7) 0.3725(5) 0.5494(3) 0.0859(13) Uani 1 1 d . . .
S1 S 0.37105(17) 0.26050(12) 0.48108(8) 0.0514(4) Uani 1 1 d . . .
O1W O 1.1742(8) 0.6052(6) 0.6124(5) 0.1050(16) Uani 1 1 d G . .
H1WA H 1.2272 0.5489 0.5755 0.157 Uiso 1 1 d G . .
H1WB H 1.1899 0.6020 0.6728 0.157 Uiso 1 1 d G . .
H1A H 0.738(8) 0.129(5) 0.471(4) 0.053(17) Uiso 1 1 d . . .
H1B H 0.787(9) 0.012(7) 0.473(5) 0.08(2) Uiso 1 1 d . . .
H1C H 0.947(9) 0.126(5) 0.474(4) 0.061(15) Uiso 1 1 d . . .
H H 0.753(5) 0.715(3) 1.481(3) 0.008(7) Uiso 1 1 d . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C7A C5 1.504(7) . ?
C7A C8A 1.541(7) 2_655 ?
C7A C8A 1.580(9) . ?
C8A C7A 1.541(7) 2_655 ?
C8A C9 1.535(7) . ?
C7B C8B 1.31(4) . ?
C7B C5 1.65(4) . ?
C8B C9 1.30(3) 2_655 ?
C1 C2 1.351(6) . ?
C1 C6 1.374(6) . ?
C1 N1 1.465(6) . ?
C2 C3 1.391(7) . ?
C3 C5 1.389(7) . ?
C4 C5 1.368(7) . ?
C4 C6 1.385(7) . ?
C9 O1 1.180(6) . ?
C9 C8B 1.30(3) 2_655 ?
C9 O2 1.331(6) . ?
C10 C15 1.364(7) . ?
C10 C11 1.387(7) . ?
C11 C12 1.349(7) . ?
C11 N2 1.458(6) . ?
C12 C13 1.382(7) . ?
C13 C14 1.387(7) . ?
C14 C15 1.368(7) . ?
C14 C16 1.470(7) . ?
C16 C17 1.324(7) . ?
C17 C18 1.483(7) . ?
C18 O3 1.203(6) . ?
C18 O4 1.289(7) . ?
O5 S1 1.461(4) . ?
O6 S1 1.465(3) . ?
O7 S1 1.443(4) . ?
O8 S1 1.480(5) . ?

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 C7A C8A 119.0(4) . 2_655 ?
C5 C7A C8A 115.2(5) . . ?
C8A C7A C8A 89.0(4) 2_655 . ?
C7A C8A C9 115.5(4) 2_655 . ?
C7A C8A C7A 91.0(4) 2_655 . ?
C9 C8A C7A 113.6(4) . . ?
C8B C7B C5 126(3) . . ?
C7B C8B C9 118(3) . 2_655 ?
C2 C1 C6 121.4(4) . . ?
C2 C1 N1 120.0(4) . . ?
C6 C1 N1 118.6(4) . . ?
C1 C2 C3 119.7(5) . . ?
C5 C3 C2 120.3(5) . . ?
C5 C4 C6 122.2(4) . . ?
C4 C5 C3 117.9(4) . . ?
C4 C5 C7A 117.5(4) . . ?
C3 C5 C7A 123.8(4) . . ?
C4 C5 C7B 122.2(14) . . ?
C3 C5 C7B 114.7(14) . . ?
C7A C5 C7B 32.3(13) . . ?
C4 C6 C1 118.1(4) . . ?
O1 C9 C8B 118.4(14) . 2_655 ?
O1 C9 O2 124.1(5) . . ?
C8B C9 O2 110.3(14) 2_655 . ?
O1 C9 C8A 124.8(5) . . ?
C8B C9 C8A 35.5(14) 2_655 . ?
O2 C9 C8A 110.6(4) . . ?
C15 C10 C11 119.3(5) . . ?
C12 C11 C10 120.2(5) . . ?
C12 C11 N2 120.9(4) . . ?
C10 C11 N2 118.9(4) . . ?
C11 C12 C13 119.6(5) . . ?
C14 C13 C12 121.5(5) . . ?
C15 C14 C13 117.0(5) . . ?
C15 C14 C16 124.0(5) . . ?
C13 C14 C16 118.9(5) . . ?
C10 C15 C14 122.3(5) . . ?
C17 C16 C14 126.2(5) . . ?
C16 C17 C18 121.9(5) . . ?
O3 C18 O4 123.5(5) . . ?
O3 C18 C17 122.2(5) . . ?
O4 C18 C17 114.3(4) . . ?
O7 S1 O5 109.8(2) . . ?
O7 S1 O6 109.8(2) . . ?
O5 S1 O6 110.6(2) . . ?
O7 S1 O8 111.2(3) . . ?
O5 S1 O8 108.3(2) . . ?
O6 S1 O8 107.0(2) . . ?

_diffrn_measured_fraction_theta_max 0.868
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.483
_refine_diff_density_min         -0.456
_refine_diff_density_rms         0.104

####################################################################### 
# 
# 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_1H2SO4-H2O_2_0
_database_code_depnum_ccdc_archive 'CCDC 1436625'
_audit_update_record             
;
2015-11-12 deposited with the CCDC.
2015-12-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H22 N2 O9 S'
_chemical_formula_weight         442.44

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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.0956(7)
_cell_length_b                   10.6597(13)
_cell_length_c                   13.9430(15)
_cell_angle_alpha                106.348(10)
_cell_angle_beta                 95.271(9)
_cell_angle_gamma                101.923(10)
_cell_volume                     977.41(19)
_cell_formula_units_Z            2
_cell_measurement_temperature    298
_cell_measurement_reflns_used    1928
_cell_measurement_theta_min      3.0860
_cell_measurement_theta_max      28.7490

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.503
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             464
_exptl_absorpt_coefficient_mu    0.222
_exptl_absorpt_correction_T_min  0.61192
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      298
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Sapphire3
_diffrn_detector_area_resol_mean 16.1340
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7914
_diffrn_reflns_av_R_equivalents  0.0465
_diffrn_reflns_av_sigmaI/netI    0.0668
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.97
_diffrn_reflns_theta_max         29.11
_reflns_number_total             4462
_reflns_number_gt                3499
_reflns_threshold_expression     >2σ(I)
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -87.00    6.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.5159  -38.0000 -150.0000 93

#__ type_ start__ end____ width___ exp.time_
  2 omega  -18.00   14.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.5159  -99.0000    0.0000 32

#__ type_ start__ end____ width___ exp.time_
  3 omega  -32.00   51.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.5159   57.0000    0.0000 83

#__ type_ start__ end____ width___ exp.time_
  4 omega  -10.00   86.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       17.6096   77.0000  120.0000 96

#__ type_ start__ end____ width___ exp.time_
  5 omega    6.00   83.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       17.6096   57.0000 -120.0000 77

;

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2005)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1122P)²+1.2026P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4462
_refine_ls_number_parameters     292
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1349
_refine_ls_R_factor_gt           0.1076
_refine_ls_wR_factor_ref         0.2698
_refine_ls_wR_factor_gt          0.2511
_refine_ls_goodness_of_fit_ref   1.176
_refine_ls_restrained_S_all      1.176
_refine_ls_shift/su_max          0.170
_refine_ls_shift/su_mean         0.023

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.7468(7) 0.0300(4) 0.3528(3) 0.0365(10) Uani 1 1 d . . .
C2 C 0.8637(7) 0.0634(5) 0.2882(3) 0.0477(12) Uani 1 1 d . . .
H2 H 0.9917 0.1136 0.3123 0.057 Uiso 1 1 calc R . .
C3 C 0.7906(7) 0.0220(5) 0.1848(3) 0.0490(13) Uani 1 1 d . . .
H3 H 0.8701 0.0442 0.1396 0.059 Uiso 1 1 calc R . .
C4 C 0.5990(7) -0.0525(5) 0.1496(3) 0.0413(11) Uani 1 1 d . . .
C5 C 0.4916(7) -0.0923(5) 0.2172(4) 0.0504(13) Uani 1 1 d . . .
H5 H 0.3673 -0.1488 0.1936 0.060 Uiso 1 1 calc R . .
C6 C 0.5623(7) -0.0512(5) 0.3188(4) 0.0493(12) Uani 1 1 d . . .
H6 H 0.4864 -0.0780 0.3638 0.059 Uiso 1 1 calc R . .
C7 C 0.4961(7) -0.0729(5) 0.0443(3) 0.0481(12) Uani 1 1 d . . .
H7 H 0.4060 -0.1624 0.0177 0.058 Uiso 1 1 calc R . .
C8 C 0.3850(7) 0.0424(5) 0.0366(3) 0.0483(12) Uani 1 1 d . . .
H8 H 0.2459 0.0047 0.0094 0.058 Uiso 1 1 calc R . .
C9 C 0.4186(7) 0.1571(5) 0.1363(4) 0.0463(12) Uani 1 1 d . . .
C10 C 0.9490(8) 0.6405(5) 0.8271(4) 0.0562(14) Uani 1 1 d . . .
H10 H 1.0386 0.6961 0.8030 0.067 Uiso 1 1 calc R . .
C11 C 0.8087(7) 0.5342(5) 0.7605(3) 0.0395(10) Uani 1 1 d . . .
C12 C 0.6795(7) 0.4509(5) 0.7955(4) 0.0471(12) Uani 1 1 d . . .
H12 H 0.5863 0.3788 0.7504 0.057 Uiso 1 1 calc R . .
C13 C 0.6885(7) 0.4746(5) 0.8989(4) 0.0486(12) Uani 1 1 d . . .
H13 H 0.6010 0.4173 0.9227 0.058 Uiso 1 1 calc R . .
C14 C 0.8249(7) 0.5820(5) 0.9677(4) 0.0430(11) Uani 1 1 d . . .
C15 C 0.9546(8) 0.6629(6) 0.9297(4) 0.0588(15) Uani 1 1 d . . .
H15 H 1.0487 0.7348 0.9745 0.071 Uiso 1 1 calc R . .
C16 C 0.8257(7) 0.6029(5) 1.0759(4) 0.0483(12) Uani 1 1 d . . .
H16 H 0.7398 0.5374 1.0934 0.058 Uiso 1 1 calc R . .
C17 C 0.9349(8) 0.7047(6) 1.1520(4) 0.0538(13) Uani 1 1 d . . .
H17 H 1.0186 0.7731 1.1365 0.065 Uiso 1 1 calc R . .
C18 C 0.9322(8) 0.7162(6) 1.2593(4) 0.0515(13) Uani 1 1 d . . .
N1 N 0.8157(6) 0.0847(4) 0.4624(3) 0.0424(9) Uani 1 1 d . . .
H1A H 0.9431 0.1225 0.4738 0.064 Uiso 1 1 calc R . .
H1B H 0.7933 0.0184 0.4901 0.064 Uiso 1 1 calc R . .
H1C H 0.7524 0.1464 0.4898 0.064 Uiso 1 1 calc R . .
N2 N 0.7966(8) 0.5148(5) 0.6518(3) 0.0444(10) Uani 1 1 d . . .
O1 O 0.5545(6) 0.2529(4) 0.1611(3) 0.0712(12) Uani 1 1 d . . .
O2 O 0.2896(6) 0.1282(5) 0.1940(3) 0.0563(10) Uani 1 1 d . . .
O1W O 1.1720(7) 0.6040(6) 0.6144(6) 0.0945(17) Uani 1 1 d G . .
H1WA H 1.2133 0.6846 0.6140 0.142 Uiso 1 1 d G . .
H1WB H 1.2461 0.5562 0.5867 0.142 Uiso 1 1 d G . .
O3 O 1.0546(7) 0.7906(5) 1.3272(3) 0.0860(15) Uani 1 1 d . . .
O4 O 0.7804(6) 0.6334(5) 1.2736(3) 0.0779(14) Uani 1 1 d . . .
H4 H 0.7754 0.6512 1.3343 0.117 Uiso 1 1 calc R . .
O5 O 0.5646(5) 0.2595(4) 0.5259(3) 0.0520(9) Uani 1 1 d . . .
O6 O 0.2350(5) 0.1325(4) 0.4661(3) 0.0625(11) Uani 1 1 d . . .
O7 O 0.3782(5) 0.2885(3) 0.3837(2) 0.0496(9) Uani 1 1 d . . .
O8 O 0.3076(7) 0.3707(4) 0.5482(3) 0.0698(12) Uani 1 1 d . . .
S1 S 0.37140(16) 0.26096(11) 0.48062(8) 0.0354(3) Uani 1 1 d . . .
H2B H 0.731(7) 0.578(5) 0.639(4) 0.042(13) Uiso 1 1 d . . .
H2C H 0.914(9) 0.534(6) 0.645(4) 0.054(18) Uiso 1 1 d . . .
H2D H 0.754(10) 0.434(7) 0.616(5) 0.07(2) Uiso 1 1 d . . .
H2A H 0.328(14) 0.181(10) 0.239(8) 0.13(4) Uiso 1 1 d . . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
C1 C2 1.350(7) . ?
C1 C6 1.369(6) . ?
C1 N1 1.469(5) . ?
C2 C3 1.397(6) . ?
C3 C4 1.390(6) . ?
C4 C5 1.369(7) . ?
C4 C7 1.514(6) . ?
C5 C6 1.370(6) . ?
C7 C8 1.537(7) 2_655 ?
C7 C8 1.613(8) . ?
C8 C9 1.531(7) . ?
C8 C7 1.537(7) 2_655 ?
C9 O1 1.194(6) . ?
C9 O2 1.319(6) . ?
C10 C11 1.381(7) . ?
C10 C15 1.378(7) . ?
C11 C12 1.363(7) . ?
C11 N2 1.462(6) . ?
C12 C13 1.385(7) . ?
C13 C14 1.386(7) . ?
C14 C15 1.375(7) . ?
C14 C16 1.462(7) . ?
C16 C17 1.326(7) . ?
C17 C18 1.468(7) . ?
C18 O3 1.192(6) . ?
C18 O4 1.313(7) . ?
O5 S1 1.460(3) . ?
O6 S1 1.454(4) . ?
O7 S1 1.465(3) . ?
O8 S1 1.462(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 121.5(4) . . ?
C2 C1 N1 119.7(4) . . ?
C6 C1 N1 118.8(4) . . ?
C1 C2 C3 119.4(4) . . ?
C4 C3 C2 119.9(4) . . ?
C5 C4 C3 118.3(4) . . ?
C5 C4 C7 118.5(4) . . ?
C3 C4 C7 122.5(4) . . ?
C4 C5 C6 121.8(4) . . ?
C1 C6 C5 118.8(4) . . ?
C4 C7 C8 119.9(4) . 2_655 ?
C4 C7 C8 114.2(4) . . ?
C8 C7 C8 89.5(4) 2_655 . ?
C9 C8 C7 115.7(4) . 2_655 ?
C9 C8 C7 113.0(4) . . ?
C7 C8 C7 90.5(4) 2_655 . ?
O1 C9 O2 125.2(5) . . ?
O1 C9 C8 123.8(5) . . ?
O2 C9 C8 110.7(4) . . ?
C11 C10 C15 119.2(5) . . ?
C12 C11 C10 120.6(4) . . ?
C12 C11 N2 120.3(4) . . ?
C10 C11 N2 119.1(5) . . ?
C11 C12 C13 119.3(4) . . ?
C14 C13 C12 121.4(5) . . ?
C15 C14 C13 117.7(5) . . ?
C15 C14 C16 123.4(4) . . ?
C13 C14 C16 118.9(5) . . ?
C14 C15 C10 121.8(5) . . ?
C17 C16 C14 127.3(5) . . ?
C16 C17 C18 124.1(6) . . ?
O3 C18 O4 122.6(5) . . ?
O3 C18 C17 124.6(6) . . ?
O4 C18 C17 112.8(5) . . ?
O6 S1 O8 110.5(3) . . ?
O6 S1 O5 109.9(2) . . ?
O8 S1 O5 108.4(2) . . ?
O6 S1 O7 110.0(2) . . ?
O8 S1 O7 107.1(2) . . ?
O5 S1 O7 111.0(2) . . ?

_diffrn_measured_fraction_theta_max 0.847
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.991
_refine_diff_density_min         -0.280
_refine_diff_density_rms         0.097


# END

####################################################################### 
# 
# 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_1HBF4_1
_database_code_depnum_ccdc_archive 'CCDC 1436626'
_audit_update_record             
;
2015-11-26 deposited with the CCDC.
2015-12-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H10 B F4 N O2'
_chemical_formula_weight         250.99

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'
B B 0.0013 0.0007 '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'
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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   I2/a

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

_cell_length_a                   7.262(5)
_cell_length_b                   10.026(5)
_cell_length_c                   30.424(5)
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 96.193(5)
_cell_angle_gamma                90.000(5)
_cell_volume                     2202.2(19)
_cell_formula_units_Z            8
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    818
_cell_measurement_theta_min      2.8530
_cell_measurement_theta_max      21.7290

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.04
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.01
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.514
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1024
_exptl_absorpt_coefficient_mu    0.148
_exptl_absorpt_correction_T_min  0.99318
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      295(2)
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_method       'omega scan'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Sapphire3
_diffrn_detector_area_resol_mean 16.1340
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4341
_diffrn_reflns_av_R_equivalents  0.0396
_diffrn_reflns_av_sigmaI/netI    0.0724
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_theta_min         2.69
_diffrn_reflns_theta_max         24.99
_reflns_number_total             1933
_reflns_number_gt                1077
_reflns_threshold_expression     >2σ(I)
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -25.00   10.00   1.0000  150.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.3596  -99.0000   90.0000 35

#__ type_ start__ end____ width___ exp.time_
  2 omega  -19.00   24.00   1.0000  150.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.3596  -99.0000  150.0000 43

#__ type_ start__ end____ width___ exp.time_
  3 omega  -34.00    3.00   1.0000  150.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.3596   57.0000   30.0000 37

#__ type_ start__ end____ width___ exp.time_
  4 omega  -17.00   90.00   1.0000  150.0000
omega____ theta____ kappa____ phi______ frames
    -       17.6096   19.0000 -120.0000 107

;

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2005)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0362P)²+0.7152P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1933
_refine_ls_number_parameters     159
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1203
_refine_ls_R_factor_gt           0.0567
_refine_ls_wR_factor_ref         0.1242
_refine_ls_wR_factor_gt          0.0976
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4165(5) 0.8893(3) 0.08066(10) 0.0471(9) Uani 1 1 d . . .
H1 H 0.4389 0.8724 0.0516 0.056 Uiso 1 1 calc R . .
C2 C 0.4066(4) 0.7844(4) 0.10925(10) 0.0475(9) Uani 1 1 d . . .
H2 H 0.4230 0.6972 0.1000 0.057 Uiso 1 1 calc R . .
C3 C 0.3724(4) 0.8108(3) 0.15154(10) 0.0397(8) Uani 1 1 d . . .
C4 C 0.3458(4) 0.9381(3) 0.16580(10) 0.0448(9) Uani 1 1 d . . .
H4 H 0.3206 0.9538 0.1947 0.054 Uiso 1 1 calc R . .
C5 C 0.3568(4) 1.0420(3) 0.13709(10) 0.0445(9) Uani 1 1 d . . .
H5 H 0.3392 1.1288 0.1466 0.053 Uiso 1 1 calc R . .
C6 C 0.3941(4) 1.0194(3) 0.09395(9) 0.0393(8) Uani 1 1 d . . .
C7 C 0.4176(4) 1.1296(4) 0.06384(10) 0.0469(9) Uani 1 1 d . . .
H7 H 0.4477 1.1063 0.0359 0.056 Uiso 1 1 calc R . .
C8 C 0.4014(5) 1.2585(4) 0.07139(10) 0.0520(10) Uani 1 1 d . . .
H8 H 0.3633 1.2855 0.0982 0.062 Uiso 1 1 calc R . .
C9 C 0.4407(5) 1.3606(4) 0.03949(12) 0.0528(10) Uani 1 1 d . . .
B1 B -0.0941(6) 0.6299(4) 0.20790(13) 0.0487(11) Uani 1 1 d . . .
F1 F 0.0331(3) 0.7204(2) 0.22788(6) 0.0754(7) Uani 1 1 d . . .
F2 F -0.0149(3) 0.5746(2) 0.17257(6) 0.0762(7) Uani 1 1 d . . .
F3 F -0.2534(3) 0.6919(2) 0.19285(8) 0.0953(9) Uani 1 1 d . . .
F4 F -0.1264(3) 0.5306(2) 0.23713(6) 0.0710(7) Uani 1 1 d . . .
N1 N 0.3683(4) 0.6997(3) 0.18298(8) 0.0520(8) Uani 1 1 d . . .
H1A H 0.2525 0.6704 0.1829 0.078 Uiso 1 1 calc R . .
H1B H 0.4099 0.7277 0.2100 0.078 Uiso 1 1 calc R . .
H1C H 0.4399 0.6338 0.1751 0.078 Uiso 1 1 calc R . .
O1 O 0.4130(5) 1.4820(3) 0.05094(8) 0.0759(9) Uani 1 1 d . . .
O2 O 0.4981(4) 1.3314(2) 0.00352(8) 0.0670(8) Uani 1 1 d . . .
H1X H 0.450(9) 1.550(6) 0.0372(18) 0.21(3) Uiso 1 1 d . . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
C1 C2 1.372(4) . ?
C1 C6 1.380(4) . ?
C2 C3 1.363(4) . ?
C3 C4 1.368(4) . ?
C3 N1 1.470(4) . ?
C4 C5 1.367(4) . ?
C5 C6 1.387(4) . ?
C6 C7 1.457(4) . ?
C7 C8 1.320(4) . ?
C8 C9 1.460(5) . ?
C9 O2 1.247(4) . ?
C9 O1 1.288(4) . ?
B1 F3 1.349(4) . ?
B1 F4 1.372(4) . ?
B1 F1 1.387(4) . ?
B1 F2 1.388(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 121.5(3) . . ?
C3 C2 C1 118.5(3) . . ?
C2 C3 C4 121.8(3) . . ?
C2 C3 N1 119.1(3) . . ?
C4 C3 N1 119.1(3) . . ?
C5 C4 C3 119.2(3) . . ?
C4 C5 C6 120.7(3) . . ?
C1 C6 C5 118.2(3) . . ?
C1 C6 C7 120.4(3) . . ?
C5 C6 C7 121.3(3) . . ?
C8 C7 C6 127.9(3) . . ?
C7 C8 C9 122.9(3) . . ?
O2 C9 O1 122.4(3) . . ?
O2 C9 C8 121.8(4) . . ?
O1 C9 C8 115.8(4) . . ?
F3 B1 F4 110.7(3) . . ?
F3 B1 F1 110.7(3) . . ?
F4 B1 F1 110.0(3) . . ?
F3 B1 F2 109.4(3) . . ?
F4 B1 F2 109.0(3) . . ?
F1 B1 F2 106.8(3) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.216
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.042
####################################################################### 
# 
# 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_1HBF4_2
_database_code_depnum_ccdc_archive 'CCDC 1436627'
_audit_update_record             
;
2015-11-12 deposited with the CCDC.
2015-12-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H10 B F4 N O2'
_chemical_formula_weight         250.99

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'
B B 0.0013 0.0007 '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'
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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.2802(11)
_cell_length_b                   9.0670(15)
_cell_length_c                   9.7329(16)
_cell_angle_alpha                115.130(16)
_cell_angle_beta                 100.802(13)
_cell_angle_gamma                101.825(14)
_cell_volume                     541.32(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    298
_cell_measurement_reflns_used    990
_cell_measurement_theta_min      3.0160
_cell_measurement_theta_max      26.5450

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.540
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             256
_exptl_absorpt_coefficient_mu    0.150
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.04297
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      298

_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Sapphire3
_diffrn_detector_area_resol_mean 16.1340
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4239
_diffrn_reflns_av_R_equivalents  0.0685
_diffrn_reflns_av_sigmaI/netI    0.1206
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.01
_diffrn_reflns_theta_max         29.14
_reflns_number_total             2441
_reflns_number_gt                1092
_reflns_threshold_expression     >2σ(I)
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -33.00   52.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.3596   57.0000  -60.0000 85

#__ type_ start__ end____ width___ exp.time_
  2 omega   -5.00   23.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.3596  -99.0000 -180.0000 28

#__ type_ start__ end____ width___ exp.time_
  3 omega  -20.00   11.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.3596  -99.0000  -30.0000 31

#__ type_ start__ end____ width___ exp.time_
  4 omega  -34.00   48.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.3596   57.0000   60.0000 82

#__ type_ start__ end____ width___ exp.time_
  5 omega   -6.00   21.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.3596  -99.0000   60.0000 27

#__ type_ start__ end____ width___ exp.time_
  6 omega  -85.00  -59.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.3596 -179.0000 -150.0000 26

#__ type_ start__ end____ width___ exp.time_
  7 omega  -85.00   -4.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.3596  -57.0000  150.0000 81

;

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2005)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1062P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2441
_refine_ls_number_parameters     170
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1684
_refine_ls_R_factor_gt           0.0857
_refine_ls_wR_factor_ref         0.2686
_refine_ls_wR_factor_gt          0.2020
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.021
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2508(6) -0.2049(5) 1.3240(5) 0.0356(9) Uani 1 1 d . . .
C2 C 0.2520(6) -0.0399(5) 1.3593(5) 0.0398(10) Uani 1 1 d . . .
H2 H 0.2541 0.0376 1.4604 0.048 Uiso 1 1 calc R . .
C3 C 0.2500(7) 0.0077(5) 1.2429(5) 0.0453(11) Uani 1 1 d . . .
H3 H 0.2533 0.1192 1.2668 0.054 Uiso 1 1 calc R . .
C4 C 0.2432(6) -0.1059(5) 1.0913(5) 0.0397(10) Uani 1 1 d . . .
C5 C 0.2397(7) -0.2716(5) 1.0591(5) 0.0467(11) Uani 1 1 d . . .
H5 H 0.2344 -0.3504 0.9575 0.056 Uiso 1 1 calc R . .
C6 C 0.2441(7) -0.3212(5) 1.1754(5) 0.0451(11) Uani 1 1 d . . .
H6 H 0.2424 -0.4320 1.1529 0.054 Uiso 1 1 calc R . .
C7 C 0.2405(6) -0.0568(5) 0.9661(5) 0.0421(10) Uani 1 1 d . . .
H7 H 0.2219 -0.1440 0.8643 0.050 Uiso 1 1 calc R . .
C8 C 0.2617(7) 0.0976(5) 0.9828(5) 0.0458(11) Uani 1 1 d . . .
H8 H 0.2815 0.1881 1.0830 0.055 Uiso 1 1 calc R . .
C9 C 0.2552(6) 0.1319(5) 0.8478(5) 0.0419(10) Uani 1 1 d . . .
B1 B -0.2782(8) -0.4545(6) 1.4082(6) 0.0426(12) Uani 1 1 d . . .
F1 F -0.1562(5) -0.4037(4) 1.3311(4) 0.0783(10) Uani 1 1 d . . .
F2 F -0.3593(5) -0.6295(3) 1.3269(3) 0.0707(10) Uani 1 1 d . . .
F3 F -0.1714(5) -0.4010(3) 1.5622(3) 0.0747(10) Uani 1 1 d . . .
F4 F -0.4236(5) -0.3791(4) 1.4041(4) 0.0839(11) Uani 1 1 d . . .
N1 N 0.2544(6) -0.2575(5) 1.4477(5) 0.0450(10) Uani 1 1 d . . .
O1 O 0.2657(6) 0.2949(4) 0.8912(5) 0.0651(11) Uani 1 1 d . . .
O2 O 0.2436(5) 0.0313(4) 0.7149(4) 0.0563(9) Uani 1 1 d . . .
H1N H 0.120(13) -0.341(10) 1.431(10) 0.15(3) Uiso 1 1 d . . .
H1X H 0.278(8) 0.311(6) 0.810(6) 0.066(16) Uiso 1 1 d . . .
H2N H 0.350(7) -0.295(5) 1.472(6) 0.056(14) Uiso 1 1 d . . .
H3N H 0.256(6) -0.183(5) 1.543(5) 0.043(12) Uiso 1 1 d . . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
C1 C6 1.364(5) . ?
C1 C2 1.383(5) . ?
C1 N1 1.470(5) . ?
C2 C3 1.372(5) . ?
C3 C4 1.379(6) . ?
C4 C5 1.392(5) . ?
C4 C7 1.463(5) . ?
C5 C6 1.382(5) . ?
C7 C8 1.312(5) . ?
C8 C9 1.467(5) . ?
C9 O2 1.199(5) . ?
C9 O1 1.335(5) . ?
B1 F2 1.367(6) . ?
B1 F4 1.375(5) . ?
B1 F3 1.371(6) . ?
B1 F1 1.393(5) . ?

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 C1 C2 121.3(4) . . ?
C6 C1 N1 119.0(3) . . ?
C2 C1 N1 119.6(3) . . ?
C3 C2 C1 119.0(4) . . ?
C2 C3 C4 121.5(4) . . ?
C3 C4 C5 118.0(4) . . ?
C3 C4 C7 122.1(3) . . ?
C5 C4 C7 119.9(3) . . ?
C6 C5 C4 121.2(4) . . ?
C1 C6 C5 118.9(4) . . ?
C8 C7 C4 126.6(4) . . ?
C7 C8 C9 121.9(4) . . ?
O2 C9 O1 122.5(4) . . ?
O2 C9 C8 126.5(4) . . ?
O1 C9 C8 111.0(4) . . ?
F2 B1 F4 110.1(4) . . ?
F2 B1 F3 110.2(3) . . ?
F4 B1 F3 111.1(4) . . ?
F2 B1 F1 109.0(4) . . ?
F4 B1 F1 106.3(3) . . ?
F3 B1 F1 110.0(4) . . ?

_diffrn_measured_fraction_theta_max 0.839
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.374
_refine_diff_density_min         -0.312
_refine_diff_density_rms         0.080
####################################################################### 
# 
# 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_1HNO3
_database_code_depnum_ccdc_archive 'CCDC 1436628'
_audit_update_record             
;
2015-11-13 deposited with the CCDC.
2015-12-08 downloaded from the CCDC.
;
_chemical_formula_sum            'C9 H10 N2 O5'
_chemical_formula_weight         226.19
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 -x,-y,-z
2 -x,1/2+y,1/2-z
3 x,1/2-y,1/2+z
4 x,y,z
_cell_length_a                   5.14519(11)
_cell_length_b                   28.63202(68)
_cell_length_c                   7.01640(22)
_cell_angle_alpha                90
_cell_angle_beta                 104.5048(22)
_cell_angle_gamma                90
_cell_volume                     1000.69
_cell_formula_units_Z            4
_cell_measurement_temperature    298
_exptl_crystal_colour            'white powder'


_exptl_special_details           'powder data'
_diffrn_ambient_temperature      298
_diffrn_radiation_type           'Cu K\a1 and K\a2'
_diffrn_radiation_wavelength     1.54056
_diffrn_measurement_device       
'powder diffractometer in bragg-brentano geometry'
_diffrn_measurement_device_type  "Panalytical X'pert, xcelerator"
_diffrn_radiation_monochromator  none
_refine_special_details          
;
capillary(glass) spinner' 
;


_computing_data_collection       "EXPO2010 (Altomare, 2010)'"
_computing_cell_refinement       'TOPAS (Coelho ,2007)'
_computing_structure_solution    'EXPO2010 (Altomare, 2010)'
_computing_structure_refinement  'TOPAS (Coelho ,2007)'

_pd_proc_2theta_range_min        5
_pd_proc_2theta_range_max        70

_pd_proc_info_excluded_regions   no
_pd_proc_ls_background_function  Chebyschev
_pd_proc_ls_pref_orient_corr     
;                                 
Spherical Harmonics               
;
_refine_ls_structure_factor_coef Fsqd
_pd_proc_ls_prof_R_factor        0.051
_pd_proc_ls_prof_wR_expected     0.034
_refine_ls_number_parameters     34
_refine_ls_goodness_of_fit_all   1.5
_refine_ls_number_restraints     4
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr
_pd_spec_mount_mode              transmission
_pd_spec_mounting                
;
capillary spinner
;
_pd_spec_shape                   cylinder



loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
C1 C 0.1187625 0.0870408 0.2753762
C2 C 0.09873802 0.1154571 0.4286344
C3 C 0.2393529 0.156682 0.4596404
C4 C 0.3956217 0.1693549 0.3375731
C5 C 0.418332 0.1413007 0.1824928
C6 C 0.2785606 0.09855862 0.1518053
C7 C 0.2975037 0.06785442 -0.008181604
C8 C 0.4814511 0.06947564 -0.1107924
C9 C 0.4815336 0.03885376 -0.2764634
N1 N 0.2253329 0.187713 0.6224395
O1 O 0.2986104 0.009906538 -0.3395281
O2 O 0.6826304 0.04351866 -0.3530211
H2 H -0.02788036 0.1053656 0.5250178
H1 H 0.005261685 0.05454555 0.2509581
H5 H 0.5424918 0.1520645 0.0853372
H4 H 0.5048266 0.2022794 0.3628395
H7 H 0.1453508 0.04070413 -0.04822649
H8 H 0.6416309 0.09517613 -0.068777
H2x H 0.6643621 0.02126429 -0.4641453
H1c H 0.3944305 0.1963303 0.7261518
H1b H 0.1531989 0.2206949 0.5954068
H1a H 0.1135953 0.1788124 0.7173083
N2 N -0.1434915 0.2128672 0.9193649
O3 O 0.090229 0.2290531 0.9369098
O4 O -0.2967584 0.2307661 0.9996979
O5 O -0.2046497 0.1768813 0.8174254


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
C3 C2 1.3730 . ?
C3 C4 1.3626 . ?
C4 C5 1.3808 . ?
C5 C6 1.4084 . ?
C6 C1 1.3761 . ?
C1 C2 1.3727 . ?
C6 C7 1.4482 . ?
C7 C8 1.3257 . ?
C8 C9 1.4561 . ?
C9 O1 1.2490 . ?
C9 O2 1.2866 . ?
C3 N1 1.4631 . ?
N2 O4 1.1937 . ?
N2 O3 1.2656 . ?
N2 O5 1.2488 . ?

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 C1 C6 121.70 . . ?
C1 C2 C3 119.58 . . ?
C2 C3 C4 119.99 . . ?
C2 C3 N1 121.24 . . ?
C4 C3 N1 118.77 . . ?
C3 C4 C5 121.34 . . ?
C4 C5 C6 119.03 . . ?
C1 C6 C5 118.34 . . ?
C1 C6 C7 120.65 . . ?
C5 C6 C7 121.00 . . ?
C6 C7 C8 126.55 . . ?
C7 C8 C9 123.74 . . ?
C8 C9 O1 122.11 . . ?
C8 C9 O2 115.59 . . ?
O1 C9 O2 122.30 . . ?
O3 N2 O4 121.39 . . ?
O3 N2 O5 117.05 . . ?
O4 N2 O5 121.55 . . ?


#END
####################################################################### 
# 
# 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_1HPF6
_database_code_depnum_ccdc_archive 'CCDC 1436629'
_audit_update_record             
;
2015-11-12 deposited with the CCDC.
2015-12-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H10 F3 N O2 P0.50'
_chemical_formula_weight         236.67

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'
F F 0.0171 0.0103 '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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.5647(5)
_cell_length_b                   5.8519(8)
_cell_length_c                   15.8200(15)
_cell_angle_alpha                85.376(9)
_cell_angle_beta                 86.255(7)
_cell_angle_gamma                72.178(10)
_cell_volume                     488.40(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    298
_cell_measurement_reflns_used    1405
_cell_measurement_theta_min      3.6530
_cell_measurement_theta_max      28.1040

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.609
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             243
_exptl_absorpt_coefficient_mu    0.227
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.93685
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      298
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Sapphire3
_diffrn_detector_area_resol_mean 16.1340
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3631
_diffrn_reflns_av_R_equivalents  0.0361
_diffrn_reflns_av_sigmaI/netI    0.0629
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.66
_diffrn_reflns_theta_max         28.98
_reflns_number_total             2181
_reflns_number_gt                1618
_reflns_threshold_expression     >2σ(I)
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -74.00   -1.00   1.0000   45.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.3596  -57.0000 -180.0000 73

#__ type_ start__ end____ width___ exp.time_
  2 omega  -23.00   23.00   1.0000   45.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.3596  -99.0000   90.0000 46

#__ type_ start__ end____ width___ exp.time_
  3 omega  -22.00    8.00   1.0000   45.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.3596  -99.0000  -46.0000 30

#__ type_ start__ end____ width___ exp.time_
  4 omega  -35.00   41.00   1.0000   45.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.3596   57.0000   60.0000 76

#__ type_ start__ end____ width___ exp.time_
  5 omega  -53.00   56.00   1.0000   45.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.3596   19.0000    0.0000 109

;

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2005)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0759P)²+0.2935P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2181
_refine_ls_number_parameters     158
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0956
_refine_ls_R_factor_gt           0.0703
_refine_ls_wR_factor_ref         0.1832
_refine_ls_wR_factor_gt          0.1637
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_restrained_S_all      1.087
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.0189(6) 0.0558(6) 0.6758(2) 0.0306(7) Uani 1 1 d . . .
C2 C -0.1287(6) -0.1138(6) 0.6554(2) 0.0379(8) Uani 1 1 d . . .
H2 H -0.1006 -0.1730 0.6017 0.045 Uiso 1 1 calc R . .
C3 C -0.2791(6) -0.1940(6) 0.7150(2) 0.0367(8) Uani 1 1 d . . .
H3 H -0.3544 -0.3069 0.7013 0.044 Uiso 1 1 calc R . .
C4 C -0.3205(6) -0.1087(6) 0.7957(2) 0.0346(7) Uani 1 1 d . . .
C5 C -0.2035(7) 0.0584(6) 0.8147(2) 0.0408(8) Uani 1 1 d . . .
H5 H -0.2266 0.1150 0.8689 0.049 Uiso 1 1 calc R . .
C6 C -0.0536(6) 0.1421(6) 0.7546(2) 0.0381(8) Uani 1 1 d . . .
H6 H 0.0223 0.2553 0.7677 0.046 Uiso 1 1 calc R . .
C7 C -0.4821(6) -0.1883(6) 0.8602(2) 0.0396(8) Uani 1 1 d . . .
H7 H -0.5058 -0.1172 0.9118 0.048 Uiso 1 1 calc R . .
C8 C -0.5979(7) -0.3509(7) 0.8528(2) 0.0429(9) Uani 1 1 d . . .
H8 H -0.5710 -0.4285 0.8024 0.051 Uiso 1 1 calc R . .
C9 C -0.7656(7) -0.4171(7) 0.9184(2) 0.0416(8) Uani 1 1 d . . .
F1 F 0.2394(4) 0.4557(5) 0.46937(15) 0.0596(7) Uani 1 1 d . . .
F2 F 0.5846(4) 0.5440(4) 0.39719(12) 0.0440(5) Uani 1 1 d . . .
F3 F 0.3481(5) 0.7935(4) 0.50296(15) 0.0654(8) Uani 1 1 d . . .
N1 N 0.1251(6) 0.1504(6) 0.6083(2) 0.0389(7) Uani 1 1 d . . .
H1NB H 0.222(9) 0.205(10) 0.627(3) 0.085(18) Uiso 1 1 d . . .
H1NC H 0.211(7) 0.026(8) 0.577(2) 0.050(11) Uiso 1 1 d . . .
H1NA H 0.024(10) 0.260(10) 0.568(3) 0.104(19) Uiso 1 1 d . . .
O1 O -0.8530(6) -0.5855(5) 0.90552(18) 0.0614(8) Uani 1 1 d . . .
O2 O -0.8150(6) -0.3045(6) 0.98538(18) 0.0570(8) Uani 1 1 d . . .
H1X H -0.933(13) -0.328(13) 1.016(5) 0.15(3) Uiso 1 1 d . . .
P1 P 0.5000 0.5000 0.5000 0.0320(3) Uani 1 2 d S . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
C1 C6 1.363(5) . ?
C1 C2 1.382(4) . ?
C1 N1 1.468(4) . ?
C2 C3 1.370(4) . ?
C3 C4 1.387(5) . ?
C4 C5 1.391(5) . ?
C4 C7 1.459(4) . ?
C5 C6 1.382(5) . ?
C7 C8 1.318(5) . ?
C8 C9 1.459(5) . ?
C9 O1 1.260(4) . ?
C9 O2 1.263(5) . ?
F1 P1 1.657(2) . ?
F2 P1 1.6853(19) . ?
F3 P1 1.669(2) . ?
P1 F1 1.657(2) 2_666 ?
P1 F3 1.669(2) 2_666 ?
P1 F2 1.6853(19) 2_666 ?

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 C1 C2 121.3(3) . . ?
C6 C1 N1 120.8(3) . . ?
C2 C1 N1 117.7(3) . . ?
C3 C2 C1 119.5(3) . . ?
C2 C3 C4 120.8(3) . . ?
C3 C4 C5 118.3(3) . . ?
C3 C4 C7 122.1(3) . . ?
C5 C4 C7 119.6(3) . . ?
C6 C5 C4 121.2(3) . . ?
C1 C6 C5 118.8(3) . . ?
C8 C7 C4 126.6(3) . . ?
C7 C8 C9 124.3(3) . . ?
O1 C9 O2 123.2(3) . . ?
O1 C9 C8 118.1(3) . . ?
O2 C9 C8 118.7(4) . . ?
F1 P1 F1 180.00(15) . 2_666 ?
F1 P1 F3 90.34(13) . 2_666 ?
F1 P1 F3 89.66(13) 2_666 2_666 ?
F1 P1 F3 89.66(13) . . ?
F1 P1 F3 90.34(13) 2_666 . ?
F3 P1 F3 180.00(16) 2_666 . ?
F1 P1 F2 88.97(10) . . ?
F1 P1 F2 91.03(10) 2_666 . ?
F3 P1 F2 90.33(11) 2_666 . ?
F3 P1 F2 89.67(11) . . ?
F1 P1 F2 91.03(10) . 2_666 ?
F1 P1 F2 88.97(10) 2_666 2_666 ?
F3 P1 F2 89.67(11) 2_666 2_666 ?
F3 P1 F2 90.33(11) . 2_666 ?
F2 P1 F2 180.000(1) . 2_666 ?

_diffrn_measured_fraction_theta_max 0.840
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.557
_refine_diff_density_min         -0.395
_refine_diff_density_rms         0.068
