# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2012

####################################################################### 
# 
# 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_3aa
_audit_block_doi                 10.5517/ccy6syv
_database_code_depnum_ccdc_archive 'CCDC 870478'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/c2cc31700a 2012
_audit_update_record             
;
2015-08-31 deposited with the CCDC.
2015-09-10 downloaded from the CCDC.
;
_audit_creation_date             2015-08-31
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H13 N O4'
_chemical_formula_sum            'C13 H13 N O4'
_chemical_formula_weight         247.24
_chemical_absolute_configuration rm
_chemical_melting_point          ?
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'

_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           5
_space_group_name_H-M_alt        'C 2'
_space_group_name_Hall           'C 2y'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'

_cell_length_a                   14.8379(12)
_cell_length_b                   6.4738(6)
_cell_length_c                   13.3730(11)
_cell_angle_alpha                90
_cell_angle_beta                 98.932(6)
_cell_angle_gamma                90
_cell_volume                     1269.00(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    ?
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      ?
_cell_measurement_theta_min      ?
_shelx_estimated_absorpt_T_max   0.989
_shelx_estimated_absorpt_T_min   0.986
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   0.989
_exptl_transmission_factor_min   0.986
_diffrn_reflns_av_R_equivalents  0.0401
_diffrn_reflns_av_unetI/netI     0.0295
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            19698
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.498
_diffrn_reflns_theta_min         1.541
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.827
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                1743
_reflns_number_total             2360
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.127
_refine_diff_density_min         -0.127
_refine_diff_density_rms         0.028
_refine_ls_abs_structure_details 
;
 Flack x determined using 655 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.6(5)
_refine_ls_extinction_coef       0.011(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     169
_refine_ls_number_reflns         2360
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0668
_refine_ls_R_factor_gt           0.0416
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0442P)²+0.3469P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0918
_refine_ls_wR_factor_ref         0.1013
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B)
2.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C11(H11), C3(H3), C12(H12), C13(H13)
2.d Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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 -0.3489(2) -1.3055(4) -0.2549(2) 0.0849(10) Uani 1 1 d . . . . .
O2 O -0.29514(14) -1.0275(3) -0.16645(17) 0.0506(6) Uani 1 1 d . . . . .
C2 C -0.4049(2) -0.9651(5) -0.3020(3) 0.0510(9) Uani 1 1 d . . . . .
O4 O -0.0696(3) -0.4329(8) -0.1267(3) 0.1205(15) Uani 1 1 d . . . . .
C4 C -0.3080(2) -0.8044(5) -0.1750(2) 0.0405(7) Uani 1 1 d . . . . .
C1 C -0.3509(2) -1.1209(6) -0.2437(3) 0.0528(9) Uani 1 1 d . . . . .
C5 C -0.2164(2) -0.7049(5) -0.1907(2) 0.0450(8) Uani 1 1 d . . . . .
H5 H -0.2267 -0.5554 -0.1947 0.054 Uiso 1 1 calc R . . . .
C8 C -0.1843(2) -0.7682(5) -0.2883(2) 0.0452(8) Uani 1 1 d . . . . .
C9 C -0.1923(3) -0.6285(7) -0.3675(3) 0.0654(11) Uani 1 1 d . . . . .
H9 H -0.2180 -0.4996 -0.3596 0.078 Uiso 1 1 calc R . . . .
C10 C -0.1633(3) -0.6754(10) -0.4572(3) 0.0885(15) Uani 1 1 d . . . . .
H10 H -0.1711 -0.5806 -0.5101 0.106 Uiso 1 1 calc R . . . .
C11 C -0.1235(3) -0.8594(11) -0.4687(4) 0.0921(17) Uani 1 1 d . . . . .
H11 H -0.1019 -0.8888 -0.5288 0.111 Uiso 1 1 calc R . . . .
C3 C -0.3796(2) -0.7843(5) -0.2651(2) 0.0458(8) Uani 1 1 d . . . . .
H3 H -0.4033 -0.6594 -0.2916 0.055 Uiso 1 1 calc R . . . .
C6 C -0.1436(2) -0.7421(7) -0.1004(3) 0.0647(11) Uani 1 1 d . . . . .
H6A H -0.1655 -0.6997 -0.0388 0.078 Uiso 1 1 calc R . . . .
H6B H -0.1287 -0.8880 -0.0950 0.078 Uiso 1 1 calc R . . . .
N1 N -0.0598(3) -0.6193(9) -0.1135(2) 0.0816(13) Uani 1 1 d . . . . .
O3 O 0.0104(2) -0.7087(8) -0.1105(2) 0.1155(14) Uani 1 1 d . . . . .
C12 C -0.1146(3) -1.0039(9) -0.3923(4) 0.0849(14) Uani 1 1 d . . . . .
H12 H -0.0884 -1.1319 -0.4013 0.102 Uiso 1 1 calc R . . . .
C13 C -0.1449(3) -0.9572(7) -0.3013(3) 0.0665(10) Uani 1 1 d . . . . .
H13 H -0.1386 -1.0538 -0.2492 0.080 Uiso 1 1 calc R . . . .
C7 C -0.3419(2) -0.7242(6) -0.0807(3) 0.0626(10) Uani 1 1 d . . . . .
H7A H -0.4001 -0.7846 -0.0759 0.094 Uiso 1 1 calc GR . . . .
H7B H -0.3478 -0.5767 -0.0847 0.094 Uiso 1 1 calc GR . . . .
H7C H -0.2991 -0.7608 -0.0220 0.094 Uiso 1 1 calc GR . . . .
H2 H -0.451(3) -0.998(6) -0.358(3) 0.059(10) 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
O1 C1 1.206(4) . ?
O2 C4 1.459(4) . ?
O2 C1 1.361(4) . ?
C2 C1 1.440(5) . ?
C2 C3 1.303(5) . ?
C2 H2 0.96(4) . ?
O4 N1 1.225(5) . ?
C4 C5 1.547(4) . ?
C4 C3 1.482(4) . ?
C4 C7 1.519(4) . ?
C5 H5 0.9800 . ?
C5 C8 1.514(4) . ?
C5 C6 1.511(4) . ?
C8 C9 1.383(5) . ?
C8 C13 1.378(5) . ?
C9 H9 0.9300 . ?
C9 C10 1.370(6) . ?
C10 H10 0.9300 . ?
C10 C11 1.349(8) . ?
C11 H11 0.9300 . ?
C11 C12 1.377(7) . ?
C3 H3 0.9300 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 N1 1.509(5) . ?
N1 O3 1.186(6) . ?
C12 H12 0.9300 . ?
C12 C13 1.395(6) . ?
C13 H13 0.9300 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?

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 C4 108.9(2) . . ?
C1 C2 H2 122(2) . . ?
C3 C2 C1 108.7(3) . . ?
C3 C2 H2 129(2) . . ?
O2 C4 C5 108.4(2) . . ?
O2 C4 C3 102.7(2) . . ?
O2 C4 C7 109.2(3) . . ?
C3 C4 C5 112.8(2) . . ?
C3 C4 C7 110.9(3) . . ?
C7 C4 C5 112.4(2) . . ?
O1 C1 O2 120.7(4) . . ?
O1 C1 C2 130.5(4) . . ?
O2 C1 C2 108.8(3) . . ?
C4 C5 H5 106.7 . . ?
C8 C5 C4 113.9(3) . . ?
C8 C5 H5 106.7 . . ?
C6 C5 C4 111.1(3) . . ?
C6 C5 H5 106.7 . . ?
C6 C5 C8 111.4(3) . . ?
C9 C8 C5 118.8(3) . . ?
C13 C8 C5 123.0(3) . . ?
C13 C8 C9 118.1(3) . . ?
C8 C9 H9 119.2 . . ?
C10 C9 C8 121.6(4) . . ?
C10 C9 H9 119.2 . . ?
C9 C10 H10 120.1 . . ?
C11 C10 C9 119.9(5) . . ?
C11 C10 H10 120.1 . . ?
C10 C11 H11 119.7 . . ?
C10 C11 C12 120.6(4) . . ?
C12 C11 H11 119.7 . . ?
C2 C3 C4 110.9(3) . . ?
C2 C3 H3 124.5 . . ?
C4 C3 H3 124.5 . . ?
C5 C6 H6A 109.9 . . ?
C5 C6 H6B 109.9 . . ?
H6A C6 H6B 108.3 . . ?
N1 C6 C5 108.9(3) . . ?
N1 C6 H6A 109.9 . . ?
N1 C6 H6B 109.9 . . ?
O4 N1 C6 117.0(4) . . ?
O3 N1 O4 124.8(5) . . ?
O3 N1 C6 118.2(6) . . ?
C11 C12 H12 120.2 . . ?
C11 C12 C13 119.5(5) . . ?
C13 C12 H12 120.2 . . ?
C8 C13 C12 120.2(4) . . ?
C8 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C4 C7 H7A 109.5 . . ?
C4 C7 H7B 109.5 . . ?
C4 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?

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
O2 C4 C5 C8 63.8(3) . . . . ?
O2 C4 C5 C6 -62.9(4) . . . . ?
O2 C4 C3 C2 0.6(3) . . . . ?
C4 O2 C1 O1 176.5(3) . . . . ?
C4 O2 C1 C2 -2.7(3) . . . . ?
C4 C5 C8 C9 105.1(4) . . . . ?
C4 C5 C8 C13 -76.8(4) . . . . ?
C4 C5 C6 N1 -172.7(3) . . . . ?
C1 O2 C4 C5 -118.2(3) . . . . ?
C1 O2 C4 C3 1.4(3) . . . . ?
C1 O2 C4 C7 119.1(3) . . . . ?
C1 C2 C3 C4 -2.3(4) . . . . ?
C5 C4 C3 C2 117.1(3) . . . . ?
C5 C8 C9 C10 179.1(3) . . . . ?
C5 C8 C13 C12 -178.3(3) . . . . ?
C5 C6 N1 O4 55.8(5) . . . . ?
C5 C6 N1 O3 -124.1(4) . . . . ?
C8 C5 C6 N1 59.2(4) . . . . ?
C8 C9 C10 C11 -2.0(7) . . . . ?
C9 C8 C13 C12 -0.2(5) . . . . ?
C9 C10 C11 C12 2.3(7) . . . . ?
C10 C11 C12 C13 -1.6(7) . . . . ?
C11 C12 C13 C8 0.5(6) . . . . ?
C3 C2 C1 O1 -175.9(4) . . . . ?
C3 C2 C1 O2 3.2(4) . . . . ?
C3 C4 C5 C8 -49.2(4) . . . . ?
C3 C4 C5 C6 -175.9(3) . . . . ?
C6 C5 C8 C9 -128.4(3) . . . . ?
C6 C5 C8 C13 49.8(4) . . . . ?
C13 C8 C9 C10 0.9(6) . . . . ?
C7 C4 C5 C8 -175.4(3) . . . . ?
C7 C4 C5 C6 57.9(4) . . . . ?
C7 C4 C3 C2 -115.9(3) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_3ab
_database_code_depnum_ccdc_archive 'CCDC 1420613'
_audit_update_record             
;
2015-08-26 deposited with the CCDC.
2015-09-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H12 Cl N O4'
_chemical_formula_sum            'C13 H12 Cl N O4'
_chemical_formula_weight         281.69

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   7.8664(5)
_cell_length_b                   12.4242(9)
_cell_length_c                   12.8541(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1256.28(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       needle
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.489
_exptl_crystal_F_000             584
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_absorpt_coefficient_mu    0.313
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.945
_exptl_absorpt_correction_T_max  0.963
_exptl_absorpt_process_details   sadabs'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            31554
_diffrn_reflns_av_unetI/netI     0.0204
_diffrn_reflns_av_R_equivalents  0.0471
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.036
_diffrn_reflns_theta_max         27.546
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2900
_reflns_number_gt                2757
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.728
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    1.000

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0451P)²+0.3454P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1132 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.006(15)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         2900
_refine_ls_number_parameters     173
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0325
_refine_ls_R_factor_gt           0.0302
_refine_ls_wR_factor_ref         0.0787
_refine_ls_wR_factor_gt          0.0769
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_restrained_S_all      1.072
_refine_ls_shift/su_max          0.026
_refine_ls_shift/su_mean         0.003

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.93115(7) 0.27810(4) 0.48235(5) 0.03035(16) Uani 1 1 d . . . . .
O1 O -0.1032(2) 0.39809(13) 0.02937(13) 0.0274(4) Uani 1 1 d . . . . .
O2 O 0.14336(19) 0.31959(11) 0.07216(11) 0.0184(3) Uani 1 1 d . . . . .
C10 C 0.4499(3) 0.45884(17) 0.08927(16) 0.0195(4) Uani 1 1 d . . . . .
H10A H 0.4019 0.5083 0.1397 0.023 Uiso 1 1 calc R U . . .
H10B H 0.5692 0.4765 0.0808 0.023 Uiso 1 1 calc R U . . .
O4 O 0.4183(2) 0.42444(13) -0.08776(12) 0.0295(4) Uani 1 1 d . . . . .
O3 O 0.2374(2) 0.53308(12) -0.01611(13) 0.0260(3) Uani 1 1 d . . . . .
C1 C 0.0074(3) 0.38445(16) 0.09225(17) 0.0195(4) Uani 1 1 d . . . . .
C2 C 0.2513(3) 0.31211(15) 0.16417(15) 0.0160(4) Uani 1 1 d . . . . .
C3 C 0.4342(3) 0.34381(15) 0.13059(15) 0.0154(4) Uani 1 1 d . . . . .
H3 H 0.4685 0.2949 0.0746 0.018 Uiso 1 1 calc R U . . .
C4 C 0.5591(3) 0.32925(15) 0.21979(15) 0.0159(4) Uani 1 1 d . . . . .
C5 C 0.5723(3) 0.40384(16) 0.30042(16) 0.0176(4) Uani 1 1 d . . . . .
H9 H 0.5041 0.4650 0.2996 0.021 Uiso 1 1 calc R U . . .
C6 C 0.6854(2) 0.38849(17) 0.38199(16) 0.0187(4) Uani 1 1 d . . . . .
H10 H 0.6936 0.4387 0.4354 0.022 Uiso 1 1 calc R U . . .
C7 C 0.7855(3) 0.29727(17) 0.38229(17) 0.0197(4) Uani 1 1 d . . . . .
C8 C 0.6625(3) 0.23810(16) 0.22225(17) 0.0189(4) Uani 1 1 d . . . . .
H2 H 0.6559 0.1880 0.1686 0.023 Uiso 1 1 calc R U . . .
C9 C 0.7752(3) 0.22120(17) 0.30367(18) 0.0209(4) Uani 1 1 d . . . . .
H1 H 0.8428 0.1598 0.3055 0.025 Uiso 1 1 calc R U . . .
N1 N 0.3607(2) 0.47298(14) -0.01274(14) 0.0194(4) Uani 1 1 d . . . . .
C11 C 0.0272(3) 0.42768(17) 0.19811(17) 0.0209(4) Uani 1 1 d . . . . .
H4 H -0.0468 0.4754 0.2307 0.025 Uiso 1 1 calc R U . . .
C12 C 0.1676(3) 0.38752(16) 0.23937(16) 0.0183(4) Uani 1 1 d . . . . .
H5 H 0.2085 0.4037 0.3054 0.022 Uiso 1 1 calc R U . . .
C13 C 0.2444(3) 0.19587(16) 0.20327(18) 0.0216(4) Uani 1 1 d . . . . .
H6 H 0.1280 0.1751 0.2137 0.032 Uiso 1 1 calc R U . . .
H8 H 0.3049 0.1904 0.2679 0.032 Uiso 1 1 calc R U . . .
H7 H 0.2958 0.1492 0.1528 0.032 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C7 1.739(2) . ?
O1 C1 1.200(3) . ?
O2 C1 1.364(3) . ?
O2 C2 1.459(2) . ?
C10 N1 1.497(3) . ?
C10 C3 1.530(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
O4 N1 1.224(2) . ?
O3 N1 1.225(2) . ?
C1 C11 1.471(3) . ?
C2 C12 1.499(3) . ?
C2 C13 1.530(3) . ?
C2 C3 1.552(3) . ?
C3 C4 1.521(3) . ?
C3 H3 0.9800 . ?
C4 C5 1.394(3) . ?
C4 C8 1.395(3) . ?
C5 C6 1.389(3) . ?
C5 H9 0.9300 . ?
C6 C7 1.380(3) . ?
C6 H10 0.9300 . ?
C7 C9 1.386(3) . ?
C8 C9 1.387(3) . ?
C8 H2 0.9300 . ?
C9 H1 0.9300 . ?
C11 C12 1.323(3) . ?
C11 H4 0.9300 . ?
C12 H5 0.9300 . ?
C13 H6 0.9600 . ?
C13 H8 0.9600 . ?
C13 H7 0.9600 . ?

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 C2 109.91(15) . . ?
N1 C10 C3 112.08(16) . . ?
N1 C10 H10A 109.2 . . ?
C3 C10 H10A 109.2 . . ?
N1 C10 H10B 109.2 . . ?
C3 C10 H10B 109.2 . . ?
H10A C10 H10B 107.9 . . ?
O1 C1 O2 121.7(2) . . ?
O1 C1 C11 130.4(2) . . ?
O2 C1 C11 107.95(18) . . ?
O2 C2 C12 103.13(16) . . ?
O2 C2 C13 107.79(15) . . ?
C12 C2 C13 111.25(17) . . ?
O2 C2 C3 107.32(15) . . ?
C12 C2 C3 115.33(16) . . ?
C13 C2 C3 111.35(17) . . ?
C4 C3 C10 108.71(16) . . ?
C4 C3 C2 111.03(15) . . ?
C10 C3 C2 114.11(17) . . ?
C4 C3 H3 107.6 . . ?
C10 C3 H3 107.6 . . ?
C2 C3 H3 107.6 . . ?
C5 C4 C8 118.65(19) . . ?
C5 C4 C3 121.96(18) . . ?
C8 C4 C3 119.38(18) . . ?
C6 C5 C4 121.17(19) . . ?
C6 C5 H9 119.4 . . ?
C4 C5 H9 119.4 . . ?
C7 C6 C5 118.73(19) . . ?
C7 C6 H10 120.6 . . ?
C5 C6 H10 120.6 . . ?
C6 C7 C9 121.65(19) . . ?
C6 C7 Cl1 119.36(17) . . ?
C9 C7 Cl1 118.98(16) . . ?
C9 C8 C4 120.84(19) . . ?
C9 C8 H2 119.6 . . ?
C4 C8 H2 119.6 . . ?
C7 C9 C8 118.96(19) . . ?
C7 C9 H1 120.5 . . ?
C8 C9 H1 120.5 . . ?
O4 N1 O3 124.42(19) . . ?
O4 N1 C10 117.31(17) . . ?
O3 N1 C10 118.25(18) . . ?
C12 C11 C1 108.73(19) . . ?
C12 C11 H4 125.6 . . ?
C1 C11 H4 125.6 . . ?
C11 C12 C2 110.13(19) . . ?
C11 C12 H5 124.9 . . ?
C2 C12 H5 124.9 . . ?
C2 C13 H6 109.5 . . ?
C2 C13 H8 109.5 . . ?
H6 C13 H8 109.5 . . ?
C2 C13 H7 109.5 . . ?
H6 C13 H7 109.5 . . ?
H8 C13 H7 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 O2 C1 O1 -176.22(18) . . . . ?
C2 O2 C1 C11 3.3(2) . . . . ?
C1 O2 C2 C12 -3.8(2) . . . . ?
C1 O2 C2 C13 113.94(18) . . . . ?
C1 O2 C2 C3 -126.02(16) . . . . ?
N1 C10 C3 C4 167.29(16) . . . . ?
N1 C10 C3 C2 -68.2(2) . . . . ?
O2 C2 C3 C4 -175.22(14) . . . . ?
C12 C2 C3 C4 70.5(2) . . . . ?
C13 C2 C3 C4 -57.5(2) . . . . ?
O2 C2 C3 C10 61.5(2) . . . . ?
C12 C2 C3 C10 -52.8(2) . . . . ?
C13 C2 C3 C10 179.26(16) . . . . ?
C10 C3 C4 C5 47.9(3) . . . . ?
C2 C3 C4 C5 -78.4(2) . . . . ?
C10 C3 C4 C8 -132.91(19) . . . . ?
C2 C3 C4 C8 100.8(2) . . . . ?
C8 C4 C5 C6 -0.1(3) . . . . ?
C3 C4 C5 C6 179.11(18) . . . . ?
C4 C5 C6 C7 -0.1(3) . . . . ?
C5 C6 C7 C9 -0.2(3) . . . . ?
C5 C6 C7 Cl1 178.64(15) . . . . ?
C5 C4 C8 C9 0.6(3) . . . . ?
C3 C4 C8 C9 -178.59(19) . . . . ?
C6 C7 C9 C8 0.7(3) . . . . ?
Cl1 C7 C9 C8 -178.13(16) . . . . ?
C4 C8 C9 C7 -0.9(3) . . . . ?
C3 C10 N1 O4 -66.4(2) . . . . ?
C3 C10 N1 O3 114.62(19) . . . . ?
O1 C1 C11 C12 178.1(2) . . . . ?
O2 C1 C11 C12 -1.4(2) . . . . ?
C1 C11 C12 C2 -1.1(2) . . . . ?
O2 C2 C12 C11 2.9(2) . . . . ?
C13 C2 C12 C11 -112.4(2) . . . . ?
C3 C2 C12 C11 119.6(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C6 H10 O1 0.93 2.46 3.322(3) 153.3 4_565
C12 H5 O3 0.93 2.46 3.378(3) 168.4 4_565
C13 H6 O4 0.96 2.62 3.320(3) 129.8 2_455
C13 H7 O1 0.96 2.54 3.427(3) 153.4 2
C6 H10 O1 0.93 2.46 3.322(3) 153.3 4_565
C12 H5 O3 0.93 2.46 3.378(3) 168.4 4_565
C13 H6 O4 0.96 2.62 3.320(3) 129.8 2_455
C13 H7 O1 0.96 2.54 3.427(3) 153.4 2

_refine_diff_density_max         0.298
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.056

