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

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

data_exp_17348
_database_code_depnum_ccdc_archive 'CCDC 1499016'
_audit_update_record             
;
2016-08-13 deposited with the CCDC.
2016-11-02 downloaded from the CCDC.
;
_audit_creation_date             2016-08-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C11 H9 N2 O4, Cl, H2 O'
_chemical_formula_sum            'C11 H11 Cl N2 O5'
_chemical_formula_weight         286.67
_chemical_melting_point          ?
_chemical_oxdiff_formula         'N C H O Cl'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   6.98145(13)
_cell_length_b                   21.3099(4)
_cell_length_c                   8.10016(14)
_cell_angle_alpha                90
_cell_angle_beta                 97.9679(17)
_cell_angle_gamma                90
_cell_volume                     1193.46(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2831
_cell_measurement_temperature    100.0(3)
_cell_measurement_theta_max      73.2540
_cell_measurement_theta_min      5.5140
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.051
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77014
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     ?
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.595
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             592
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.25
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0141
_diffrn_reflns_av_unetI/netI     0.0185
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -4
_diffrn_reflns_number            4256
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.218
_diffrn_reflns_theta_min         4.149
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(3)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.5594
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -50.00   36.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.1492   38.0000  120.0000 86

#__ type_ start__ end____ width___ exp.time_
  2 omega   15.00   46.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.1492  -99.0000   30.0000 31

#__ type_ start__ end____ width___ exp.time_
  3 omega   34.00   94.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.2872  -45.0000  120.0000 60

#__ type_ start__ end____ width___ exp.time_
  4 omega   42.00   85.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.2872  -45.0000   60.0000 43

#__ type_ start__ end____ width___ exp.time_
  5 omega   45.00   76.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.2872  -30.0000  150.0000 31

#__ type_ start__ end____ width___ exp.time_
  6 omega   33.00   90.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.2872  -30.0000    0.0000 57

#__ type_ start__ end____ width___ exp.time_
  7 omega   30.00   90.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.2872  -30.0000  -60.0000 60

#__ type_ start__ end____ width___ exp.time_
  8 omega   40.00  134.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.2872  -77.0000 -120.0000 94

#__ type_ start__ end____ width___ exp.time_
  9 omega   59.00   93.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.1492 -125.0000 -120.0000 34

#__ type_ start__ end____ width___ exp.time_
 10 omega   36.00   88.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.2872  -30.0000 -120.0000 52

#__ type_ start__ end____ width___ exp.time_
 11 omega  -50.00   19.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.1492   77.0000 -180.0000 69
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.1422291000
_diffrn_orient_matrix_UB_12      -0.0462194000
_diffrn_orient_matrix_UB_13      0.0985996000
_diffrn_orient_matrix_UB_21      0.1592343000
_diffrn_orient_matrix_UB_22      0.0505755000
_diffrn_orient_matrix_UB_23      0.0150366000
_diffrn_orient_matrix_UB_31      -0.0639600000
_diffrn_orient_matrix_UB_32      0.0231046000
_diffrn_orient_matrix_UB_33      0.1640106000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2171
_reflns_number_total             2327
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.281
_refine_diff_density_min         -0.289
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         2327
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0306
_refine_ls_R_factor_gt           0.0285
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0419P)²+0.5619P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0746
_refine_ls_wR_factor_ref         0.0758
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups, All O(H,H) groups
2.a Free rotating group:
 O5(H5A,H5B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C6(H6), C9(H9), C10(H10), C11(H11)
2.c Idealised tetrahedral OH refined as rotating group:
 O2(H2), O4(H4)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 1.45938(15) 0.42056(5) 0.02355(14) 0.0184(2) Uani 1 1 d . . . . .
O2 O 1.23411(15) 0.34559(5) -0.00074(13) 0.0177(2) Uani 1 1 d . . . . .
H2 H 1.305623 0.329581 -0.061101 0.027 Uiso 1 1 calc GR . . . .
O3 O 0.85032(15) 0.62257(5) 0.37927(13) 0.0182(2) Uani 1 1 d . . . . .
O4 O 0.65540(15) 0.54213(5) 0.41921(13) 0.0159(2) Uani 1 1 d . . . . .
H4 H 0.592119 0.569684 0.457185 0.024 Uiso 1 1 calc GR . . . .
N1 N 0.95534(16) 0.35195(5) 0.19588(14) 0.0102(2) Uani 1 1 d . . . . .
N2 N 0.81568(17) 0.26591(6) 0.10904(15) 0.0134(3) Uani 1 1 d . . . . .
H2A H 0.736(3) 0.2374(9) 0.052(2) 0.022(5) Uiso 1 1 d . . . . .
C1 C 1.3054(2) 0.40056(6) 0.05328(17) 0.0119(3) Uani 1 1 d . . . . .
C2 C 1.17599(19) 0.43869(6) 0.14820(16) 0.0110(3) Uani 1 1 d . . . . .
C3 C 1.22519(19) 0.50185(7) 0.17137(17) 0.0128(3) Uani 1 1 d . . . . .
H3 H 1.338652 0.516791 0.137404 0.015 Uiso 1 1 calc R . . . .
C4 C 1.1071(2) 0.54249(6) 0.24428(17) 0.0129(3) Uani 1 1 d . . . . .
H4A H 1.143(3) 0.5861(9) 0.262(2) 0.016(4) Uiso 1 1 d . . . . .
C5 C 0.93551(19) 0.52094(6) 0.29458(16) 0.0112(3) Uani 1 1 d . . . . .
C6 C 0.88617(19) 0.45761(6) 0.27772(16) 0.0106(3) Uani 1 1 d . . . . .
H6 H 0.773847 0.442670 0.313741 0.013 Uiso 1 1 calc R . . . .
C7 C 1.00710(19) 0.41737(6) 0.20649(16) 0.0104(3) Uani 1 1 d . . . . .
C8 C 0.8112(2) 0.56735(6) 0.36839(17) 0.0119(3) Uani 1 1 d . . . . .
C9 C 1.0560(2) 0.30372(7) 0.28303(17) 0.0136(3) Uani 1 1 d . . . . .
H9 H 1.163663 0.307674 0.363928 0.016 Uiso 1 1 calc R . . . .
C10 C 0.9681(2) 0.24992(7) 0.22816(18) 0.0145(3) Uani 1 1 d . . . . .
H10 H 1.003622 0.209576 0.263975 0.017 Uiso 1 1 calc R . . . .
C11 C 0.80951(19) 0.32776(7) 0.09144(17) 0.0123(3) Uani 1 1 d . . . . .
H11 H 0.719579 0.350266 0.019176 0.015 Uiso 1 1 calc R . . . .
Cl1 Cl 0.44320(4) 0.65668(2) 0.55702(4) 0.01349(11) Uani 1 1 d . . . . .
O5 O 0.53263(15) 0.70687(5) 0.18916(12) 0.0156(2) Uani 1 1 d . . . . .
H5A H 0.542508 0.692621 0.288094 0.023 Uiso 1 1 d G . . . .
H5B H 0.528305 0.746712 0.191778 0.023 Uiso 1 1 d G . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.2112(17) . ?
O2 H2 0.8200 . ?
O2 C1 1.3232(17) . ?
O3 C8 1.2085(17) . ?
O4 H4 0.8200 . ?
O4 C8 1.3287(17) . ?
N1 C7 1.4398(17) . ?
N1 C9 1.3823(17) . ?
N1 C11 1.3338(18) . ?
N2 H2A 0.91(2) . ?
N2 C10 1.3764(18) . ?
N2 C11 1.3257(18) . ?
C1 C2 1.5035(19) . ?
C2 C3 1.3952(19) . ?
C2 C7 1.4050(19) . ?
C3 H3 0.9300 . ?
C3 C4 1.383(2) . ?
C4 H4A 0.970(18) . ?
C4 C5 1.395(2) . ?
C5 C6 1.3949(18) . ?
C5 C8 1.4941(19) . ?
C6 H6 0.9300 . ?
C6 C7 1.3843(19) . ?
C9 H9 0.9300 . ?
C9 C10 1.347(2) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
O5 H5A 0.8508 . ?
O5 H5B 0.8499 . ?

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
C1 O2 H2 109.5 . . ?
C8 O4 H4 109.5 . . ?
C9 N1 C7 125.71(11) . . ?
C11 N1 C7 125.11(12) . . ?
C11 N1 C9 109.03(11) . . ?
C10 N2 H2A 123.5(12) . . ?
C11 N2 H2A 127.1(12) . . ?
C11 N2 C10 109.39(12) . . ?
O1 C1 O2 123.32(13) . . ?
O1 C1 C2 121.62(13) . . ?
O2 C1 C2 114.98(12) . . ?
C3 C2 C1 115.84(12) . . ?
C3 C2 C7 117.98(12) . . ?
C7 C2 C1 126.08(12) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 C2 120.74(13) . . ?
C4 C3 H3 119.6 . . ?
C3 C4 H4A 120.4(11) . . ?
C3 C4 C5 120.35(13) . . ?
C5 C4 H4A 119.2(11) . . ?
C4 C5 C8 117.96(12) . . ?
C6 C5 C4 120.01(13) . . ?
C6 C5 C8 122.02(12) . . ?
C5 C6 H6 120.5 . . ?
C7 C6 C5 118.92(13) . . ?
C7 C6 H6 120.5 . . ?
C2 C7 N1 120.57(12) . . ?
C6 C7 N1 117.53(12) . . ?
C6 C7 C2 121.90(12) . . ?
O3 C8 O4 123.90(13) . . ?
O3 C8 C5 122.39(13) . . ?
O4 C8 C5 113.71(11) . . ?
N1 C9 H9 126.6 . . ?
C10 C9 N1 106.75(12) . . ?
C10 C9 H9 126.6 . . ?
N2 C10 H10 126.5 . . ?
C9 C10 N2 107.05(12) . . ?
C9 C10 H10 126.5 . . ?
N1 C11 H11 126.1 . . ?
N2 C11 N1 107.78(12) . . ?
N2 C11 H11 126.1 . . ?
H5A O5 H5B 109.4 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 11.8(2) . . . . ?
O1 C1 C2 C7 -171.79(13) . . . . ?
O2 C1 C2 C3 -165.16(12) . . . . ?
O2 C1 C2 C7 11.2(2) . . . . ?
N1 C9 C10 N2 -0.05(16) . . . . ?
C1 C2 C3 C4 174.43(12) . . . . ?
C1 C2 C7 N1 7.7(2) . . . . ?
C1 C2 C7 C6 -173.17(13) . . . . ?
C2 C3 C4 C5 -0.6(2) . . . . ?
C3 C2 C7 N1 -176.00(12) . . . . ?
C3 C2 C7 C6 3.12(19) . . . . ?
C3 C4 C5 C6 2.6(2) . . . . ?
C3 C4 C5 C8 -178.38(12) . . . . ?
C4 C5 C6 C7 -1.8(2) . . . . ?
C4 C5 C8 O3 3.1(2) . . . . ?
C4 C5 C8 O4 -177.22(12) . . . . ?
C5 C6 C7 N1 178.01(11) . . . . ?
C5 C6 C7 C2 -1.1(2) . . . . ?
C6 C5 C8 O3 -177.95(13) . . . . ?
C6 C5 C8 O4 1.75(18) . . . . ?
C7 N1 C9 C10 -175.49(13) . . . . ?
C7 N1 C11 N2 175.40(12) . . . . ?
C7 C2 C3 C4 -2.2(2) . . . . ?
C8 C5 C6 C7 179.29(12) . . . . ?
C9 N1 C7 C2 66.77(18) . . . . ?
C9 N1 C7 C6 -112.39(15) . . . . ?
C9 N1 C11 N2 -0.41(16) . . . . ?
C10 N2 C11 N1 0.37(16) . . . . ?
C11 N1 C7 C2 -108.34(16) . . . . ?
C11 N1 C7 C6 72.50(18) . . . . ?
C11 N1 C9 C10 0.28(16) . . . . ?
C11 N2 C10 C9 -0.20(16) . . . . ?

_shelx_SHELXL_version_number     2016/4
_olex2_submission_special_instructions 'No special instructions were received'
