# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_170916LT
_database_code_depnum_ccdc_archive 'CCDC 1584500'
_audit_update_record             
;
2017-11-08 deposited with the CCDC.
2018-08-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H15 N3 O3'
_chemical_formula_weight         357.36

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'

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

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

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

_cell_length_a                   10.2072(5)
_cell_length_b                   22.8173(11)
_cell_length_c                   7.0823(3)
_cell_angle_alpha                90
_cell_angle_beta                 90.0090(10)
_cell_angle_gamma                90
_cell_volume                     1649.47(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3614
_cell_measurement_theta_min      2.6772
_cell_measurement_theta_max      25.9483

_exptl_crystal_description       Tabullar
_exptl_crystal_colour            Yellow
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.439
_exptl_crystal_F_000             744
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    0.099
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8737
_exptl_absorpt_correction_T_max  0.9485
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_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       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            10011
_diffrn_reflns_av_unetI/netI     0.0437
_diffrn_reflns_av_R_equivalents  0.0370
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       4
_diffrn_reflns_theta_min         1.785
_diffrn_reflns_theta_max         26.330
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3358
_reflns_number_gt                2802
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0565P)²+1.8388P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3358
_refine_ls_number_parameters     244
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0691
_refine_ls_R_factor_gt           0.0591
_refine_ls_wR_factor_ref         0.1728
_refine_ls_wR_factor_gt          0.1678
_refine_ls_goodness_of_fit_ref   1.264
_refine_ls_restrained_S_all      1.264
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.12303(19) 0.74530(9) 0.1773(3) 0.0276(5) Uani 1 1 d . . . . .
O2 O 0.2995(2) 0.77369(9) 0.0362(3) 0.0319(5) Uani 1 1 d . . . . .
O3 O 0.27288(19) 0.44346(8) 0.1265(3) 0.0257(5) Uani 1 1 d . . . . .
N1 N 0.2283(2) 0.73495(10) 0.0994(3) 0.0194(5) Uani 1 1 d . . . . .
N2 N 0.0683(2) 0.42367(9) 0.2301(3) 0.0165(5) Uani 1 1 d . . . . .
N3 N 0.0138(2) 0.54308(9) 0.2258(3) 0.0170(5) Uani 1 1 d . . . . .
C1 C 0.2709(3) 0.67371(11) 0.0840(4) 0.0175(5) Uani 1 1 d . . . . .
C2 C 0.1852(2) 0.62974(11) 0.1342(3) 0.0164(5) Uani 1 1 d . . . . .
H15 H 0.0987 0.6389 0.1741 0.020 Uiso 1 1 calc R U . . .
C3 C 0.2268(2) 0.57147(12) 0.1257(3) 0.0164(5) Uani 1 1 d . . . . .
C4 C 0.1295(2) 0.52499(11) 0.1781(3) 0.0159(5) Uani 1 1 d . . . . .
C5 C 0.1663(3) 0.46200(12) 0.1754(3) 0.0177(6) Uani 1 1 d . . . . .
C6 C 0.1045(3) 0.36034(11) 0.2234(4) 0.0196(6) Uani 1 1 d . . . . .
H10 H 0.1609 0.3532 0.1120 0.024 Uiso 1 1 calc R U . . .
H9 H 0.0240 0.3366 0.2085 0.024 Uiso 1 1 calc R U . . .
C7 C 0.1763(3) 0.34075(11) 0.3998(4) 0.0180(5) Uani 1 1 d . . . . .
C8 C 0.3121(3) 0.34248(12) 0.4096(4) 0.0244(6) Uani 1 1 d . . . . .
H8 H 0.3610 0.3563 0.3045 0.029 Uiso 1 1 calc R U . . .
C9 C 0.3773(3) 0.32411(13) 0.5716(5) 0.0292(7) Uani 1 1 d . . . . .
H7 H 0.4702 0.3255 0.5770 0.035 Uiso 1 1 calc R U . . .
C10 C 0.3063(3) 0.30380(13) 0.7253(4) 0.0283(7) Uani 1 1 d . . . . .
H1 H 0.3505 0.2916 0.8366 0.034 Uiso 1 1 calc R U . . .
C11 C -0.0802(2) 0.50322(11) 0.2815(3) 0.0165(5) Uani 1 1 d . . . . .
C12 C -0.2042(3) 0.52464(12) 0.3333(4) 0.0195(6) Uani 1 1 d . . . . .
H11 H -0.2215 0.5655 0.3270 0.023 Uiso 1 1 calc R U . . .
C13 C -0.3007(3) 0.48686(13) 0.3929(4) 0.0226(6) Uani 1 1 d . . . . .
H2 H -0.3841 0.5015 0.4292 0.027 Uiso 1 1 calc R U . . .
C14 C -0.2746(3) 0.42634(13) 0.3997(4) 0.0215(6) Uani 1 1 d . . . . .
H3 H -0.3415 0.4002 0.4400 0.026 Uiso 1 1 calc R U . . .
C15 C -0.1547(3) 0.40425(12) 0.3492(4) 0.0197(6) Uani 1 1 d . . . . .
H4 H -0.1390 0.3633 0.3558 0.024 Uiso 1 1 calc R U . . .
C16 C -0.0548(3) 0.44216(11) 0.2877(3) 0.0160(5) Uani 1 1 d . . . . .
C17 C 0.1712(3) 0.30144(12) 0.7159(4) 0.0234(6) Uani 1 1 d . . . . .
H6 H 0.1227 0.2871 0.8205 0.028 Uiso 1 1 calc R U . . .
C18 C 0.1062(3) 0.31986(11) 0.5552(4) 0.0191(6) Uani 1 1 d . . . . .
H5 H 0.0132 0.3183 0.5505 0.023 Uiso 1 1 calc R U . . .
C19 C 0.3562(3) 0.56012(12) 0.0708(4) 0.0214(6) Uani 1 1 d . . . . .
H12 H 0.3873 0.5209 0.0683 0.026 Uiso 1 1 calc R U . . .
C20 C 0.4400(3) 0.60570(13) 0.0198(4) 0.0248(6) Uani 1 1 d . . . . .
H14 H 0.5274 0.5971 -0.0174 0.030 Uiso 1 1 calc R U . . .
C21 C 0.3977(3) 0.66311(12) 0.0225(4) 0.0215(6) Uani 1 1 d . . . . .
H13 H 0.4533 0.6942 -0.0162 0.026 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
O1 N1 1.231(3) . ?
O2 N1 1.229(3) . ?
O3 C5 1.217(3) . ?
N1 C1 1.468(3) . ?
N2 C5 1.384(3) . ?
N2 C16 1.388(3) . ?
N2 C6 1.492(3) . ?
N3 C4 1.296(3) . ?
N3 C11 1.379(3) . ?
C1 C2 1.378(4) . ?
C1 C21 1.387(4) . ?
C2 C3 1.397(4) . ?
C2 H15 0.9500 . ?
C3 C19 1.401(4) . ?
C3 C4 1.500(4) . ?
C4 C5 1.486(4) . ?
C6 C7 1.516(4) . ?
C6 H10 0.9900 . ?
C6 H9 0.9900 . ?
C7 C8 1.388(4) . ?
C7 C18 1.397(4) . ?
C8 C9 1.391(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.387(4) . ?
C9 H7 0.9500 . ?
C10 C17 1.382(4) . ?
C10 H1 0.9500 . ?
C11 C12 1.406(4) . ?
C11 C16 1.418(4) . ?
C12 C13 1.375(4) . ?
C12 H11 0.9500 . ?
C13 C14 1.407(4) . ?
C13 H2 0.9500 . ?
C14 C15 1.372(4) . ?
C14 H3 0.9500 . ?
C15 C16 1.406(4) . ?
C15 H4 0.9500 . ?
C17 C18 1.383(4) . ?
C17 H6 0.9500 . ?
C18 H5 0.9500 . ?
C19 C20 1.394(4) . ?
C19 H12 0.9500 . ?
C20 C21 1.379(4) . ?
C20 H14 0.9500 . ?
C21 H13 0.9500 . ?

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
O2 N1 O1 122.8(2) . . ?
O2 N1 C1 118.9(2) . . ?
O1 N1 C1 118.4(2) . . ?
C5 N2 C16 123.0(2) . . ?
C5 N2 C6 115.1(2) . . ?
C16 N2 C6 121.9(2) . . ?
C4 N3 C11 119.9(2) . . ?
C2 C1 C21 123.1(2) . . ?
C2 C1 N1 119.1(2) . . ?
C21 C1 N1 117.8(2) . . ?
C1 C2 C3 119.2(2) . . ?
C1 C2 H15 120.4 . . ?
C3 C2 H15 120.4 . . ?
C2 C3 C19 118.3(2) . . ?
C2 C3 C4 117.4(2) . . ?
C19 C3 C4 124.2(2) . . ?
N3 C4 C5 122.8(2) . . ?
N3 C4 C3 116.3(2) . . ?
C5 C4 C3 120.9(2) . . ?
O3 C5 N2 120.4(2) . . ?
O3 C5 C4 124.5(2) . . ?
N2 C5 C4 115.1(2) . . ?
N2 C6 C7 112.3(2) . . ?
N2 C6 H10 109.1 . . ?
C7 C6 H10 109.1 . . ?
N2 C6 H9 109.1 . . ?
C7 C6 H9 109.1 . . ?
H10 C6 H9 107.9 . . ?
C8 C7 C18 118.8(3) . . ?
C8 C7 C6 121.0(2) . . ?
C18 C7 C6 120.2(2) . . ?
C7 C8 C9 120.6(3) . . ?
C7 C8 H8 119.7 . . ?
C9 C8 H8 119.7 . . ?
C10 C9 C8 119.9(3) . . ?
C10 C9 H7 120.1 . . ?
C8 C9 H7 120.1 . . ?
C17 C10 C9 119.8(3) . . ?
C17 C10 H1 120.1 . . ?
C9 C10 H1 120.1 . . ?
N3 C11 C12 118.1(2) . . ?
N3 C11 C16 122.0(2) . . ?
C12 C11 C16 119.9(2) . . ?
C13 C12 C11 120.5(3) . . ?
C13 C12 H11 119.8 . . ?
C11 C12 H11 119.8 . . ?
C12 C13 C14 119.4(3) . . ?
C12 C13 H2 120.3 . . ?
C14 C13 H2 120.3 . . ?
C15 C14 C13 121.4(3) . . ?
C15 C14 H3 119.3 . . ?
C13 C14 H3 119.3 . . ?
C14 C15 C16 120.1(3) . . ?
C14 C15 H4 119.9 . . ?
C16 C15 H4 119.9 . . ?
N2 C16 C15 124.1(2) . . ?
N2 C16 C11 117.1(2) . . ?
C15 C16 C11 118.8(2) . . ?
C10 C17 C18 120.4(3) . . ?
C10 C17 H6 119.8 . . ?
C18 C17 H6 119.8 . . ?
C17 C18 C7 120.4(3) . . ?
C17 C18 H5 119.8 . . ?
C7 C18 H5 119.8 . . ?
C20 C19 C3 120.8(3) . . ?
C20 C19 H12 119.6 . . ?
C3 C19 H12 119.6 . . ?
C21 C20 C19 120.8(3) . . ?
C21 C20 H14 119.6 . . ?
C19 C20 H14 119.6 . . ?
C20 C21 C1 117.6(2) . . ?
C20 C21 H13 121.2 . . ?
C1 C21 H13 121.2 . . ?

_refine_diff_density_max         0.357
_refine_diff_density_min         -0.374
_refine_diff_density_rms         0.120

_shelxl_version_number           2014/6

####################################################################### 
# 
# 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_170731LT_0m
_database_code_depnum_ccdc_archive 'CCDC 1584501'
_audit_update_record             
;
2017-11-08 deposited with the CCDC.
2018-08-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H7 N O5'
_chemical_formula_weight         209.16

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'
O O 0.0106 0.0060 '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'

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

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

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

_cell_length_a                   7.2306(4)
_cell_length_b                   7.3257(4)
_cell_length_c                   8.8664(5)
_cell_angle_alpha                106.573(3)
_cell_angle_beta                 100.859(3)
_cell_angle_gamma                94.501(3)
_cell_volume                     437.69(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4772
_cell_measurement_theta_min      2.4572
_cell_measurement_theta_max      26.3994

_exptl_crystal_description       Lump
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.587
_exptl_crystal_F_000             216
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    0.132
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8928
_exptl_absorpt_correction_T_max  0.9485
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_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       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            6864
_diffrn_reflns_av_unetI/netI     0.0166
_diffrn_reflns_av_R_equivalents  0.0210
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.457
_diffrn_reflns_theta_max         26.400
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             1777
_reflns_number_gt                1657
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0398P)²+0.1396P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1777
_refine_ls_number_parameters     137
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0302
_refine_ls_R_factor_gt           0.0283
_refine_ls_wR_factor_ref         0.0786
_refine_ls_wR_factor_gt          0.0767
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.055
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.00699(10) 0.39509(10) 0.64435(9) 0.01801(19) Uani 1 1 d . . . . .
O2 O 0.04513(12) -0.25449(12) 0.97287(10) 0.0260(2) Uani 1 1 d . . . . .
O3 O 0.27712(13) -0.42110(12) 1.00104(11) 0.0279(2) Uani 1 1 d . . . . .
O4 O 0.34933(11) 0.30761(11) 0.63089(10) 0.02176(19) Uani 1 1 d . . . . .
O5 O -0.08772(10) 0.09477(10) 0.64372(9) 0.01816(19) Uani 1 1 d . . . . .
C1 C -0.19053(15) 0.42941(16) 0.61925(14) 0.0201(2) Uani 1 1 d . . . . .
H1 H -0.2679 0.3236 0.5294 0.030 Uiso 1 1 calc R U . . .
H7 H -0.1995 0.5507 0.5940 0.030 Uiso 1 1 calc R U . . .
H6 H -0.2371 0.4371 0.7175 0.030 Uiso 1 1 calc R U . . .
C2 C 0.03468(14) 0.22209(14) 0.65437(12) 0.0142(2) Uani 1 1 d . . . . .
C3 C 0.24809(14) 0.20112(14) 0.67266(12) 0.0147(2) Uani 1 1 d . . . . .
C4 C 0.32048(14) 0.04432(14) 0.73375(12) 0.0140(2) Uani 1 1 d . . . . .
C5 C 0.21972(14) -0.05600(14) 0.81159(12) 0.0150(2) Uani 1 1 d . . . . .
H2 H 0.0974 -0.0286 0.8279 0.018 Uiso 1 1 calc R U . . .
C6 C 0.30359(15) -0.19703(14) 0.86452(12) 0.0155(2) Uani 1 1 d . . . . .
N1 N 0.20051(13) -0.29871(13) 0.95189(11) 0.0187(2) Uani 1 1 d . . . . .
C8 C 0.50197(14) 0.00292(14) 0.71359(12) 0.0156(2) Uani 1 1 d . . . . .
H5 H 0.5715 0.0731 0.6624 0.019 Uiso 1 1 calc R U . . .
C9 C 0.58064(15) -0.13946(15) 0.76776(13) 0.0176(2) Uani 1 1 d . . . . .
H4 H 0.7034 -0.1667 0.7528 0.021 Uiso 1 1 calc R U . . .
C7 C 0.48146(15) -0.24268(14) 0.84375(12) 0.0175(2) Uani 1 1 d . . . . .
H3 H 0.5338 -0.3414 0.8803 0.021 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
O1 C2 1.3235(12) . ?
O1 C1 1.4563(12) . ?
O2 N1 1.2261(13) . ?
O3 N1 1.2291(12) . ?
O4 C3 1.2079(13) . ?
O5 C2 1.2045(13) . ?
C1 H1 0.9800 . ?
C1 H7 0.9800 . ?
C1 H6 0.9800 . ?
C2 C3 1.5453(14) . ?
C3 C4 1.4931(14) . ?
C4 C5 1.3935(14) . ?
C4 C8 1.4021(14) . ?
C5 C6 1.3868(14) . ?
C5 H2 0.9500 . ?
C6 C7 1.3861(15) . ?
C6 N1 1.4731(13) . ?
C8 C9 1.3850(15) . ?
C8 H5 0.9500 . ?
C9 C7 1.3884(15) . ?
C9 H4 0.9500 . ?
C7 H3 0.9500 . ?

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 O1 C1 115.33(8) . . ?
O1 C1 H1 109.5 . . ?
O1 C1 H7 109.5 . . ?
H1 C1 H7 109.5 . . ?
O1 C1 H6 109.5 . . ?
H1 C1 H6 109.5 . . ?
H7 C1 H6 109.5 . . ?
O5 C2 O1 125.74(9) . . ?
O5 C2 C3 124.04(9) . . ?
O1 C2 C3 110.15(8) . . ?
O4 C3 C4 122.15(9) . . ?
O4 C3 C2 118.72(9) . . ?
C4 C3 C2 119.06(9) . . ?
C5 C4 C8 119.80(9) . . ?
C5 C4 C3 123.46(9) . . ?
C8 C4 C3 116.72(9) . . ?
C6 C5 C4 117.91(9) . . ?
C6 C5 H2 121.0 . . ?
C4 C5 H2 121.0 . . ?
C7 C6 C5 123.36(10) . . ?
C7 C6 N1 118.53(9) . . ?
C5 C6 N1 118.08(9) . . ?
O2 N1 O3 124.09(9) . . ?
O2 N1 C6 118.13(9) . . ?
O3 N1 C6 117.77(9) . . ?
C9 C8 C4 120.54(10) . . ?
C9 C8 H5 119.7 . . ?
C4 C8 H5 119.7 . . ?
C8 C9 C7 120.50(10) . . ?
C8 C9 H4 119.7 . . ?
C7 C9 H4 119.7 . . ?
C6 C7 C9 117.87(9) . . ?
C6 C7 H3 121.1 . . ?
C9 C7 H3 121.1 . . ?

_refine_diff_density_max         0.327
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.038

_shelxl_version_number           2014/6

####################################################################### 
# 
# 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_mo_170824lt_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1847226'
_audit_update_record             
;
2018-06-05 deposited with the CCDC.
2018-08-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H12 Cu N2 O6'
_chemical_formula_weight         343.78

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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   5.0866(4)
_cell_length_b                   7.5068(5)
_cell_length_c                   9.0684(6)
_cell_angle_alpha                76.038(2)
_cell_angle_beta                 85.125(2)
_cell_angle_gamma                72.2290(10)
_cell_volume                     319.98(4)
_cell_formula_units_Z            1
_cell_measurement_temperature    99(2)
_cell_measurement_reflns_used    4579
_cell_measurement_theta_min      2.9258
_cell_measurement_theta_max      26.7016

_exptl_crystal_description       tabullar
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.784
_exptl_crystal_F_000             175
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.03
_exptl_absorpt_coefficient_mu    1.738
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.78
_exptl_absorpt_correction_T_max  0.95
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      99(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            5170
_diffrn_reflns_av_unetI/netI     0.0117
_diffrn_reflns_av_R_equivalents  0.0132
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.926
_diffrn_reflns_theta_max         26.702
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             1351
_reflns_number_gt                1349
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0118P)²+0.2585P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1351
_refine_ls_number_parameters     98
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0172
_refine_ls_R_factor_gt           0.0172
_refine_ls_wR_factor_ref         0.0442
_refine_ls_wR_factor_gt          0.0442
_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_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
Cu1 Cu 1.0000 0.0000 0.5000 0.00901(8) Uani 1 2 d S . P . .
N1 N 0.7819(2) 0.22910(16) 0.35908(13) 0.0094(2) Uani 1 1 d . . . . .
O1 O 0.66908(19) 0.04237(14) 0.62701(11) 0.0109(2) Uani 1 1 d . . . . .
O2 O 0.22505(19) 0.21615(14) 0.61649(11) 0.0127(2) Uani 1 1 d . . . . .
O3 O 0.2312(3) 0.0579(2) 0.94147(13) 0.0293(3) Uani 1 1 d . . . . .
C1 C 0.4634(3) 0.17981(19) 0.56442(15) 0.0097(3) Uani 1 1 d . . . . .
C2 C 0.5270(3) 0.30047(19) 0.41425(15) 0.0093(3) Uani 1 1 d . . . . .
C3 C 0.3443(3) 0.4700(2) 0.33966(16) 0.0116(3) Uani 1 1 d . . . . .
H3 H 0.1646 0.5170 0.3800 0.014 Uiso 1 1 calc R U . . .
C4 C 0.4307(3) 0.5698(2) 0.20405(16) 0.0137(3) Uani 1 1 d . . . . .
H4 H 0.3120 0.6886 0.1513 0.016 Uiso 1 1 calc R U . . .
C5 C 0.6918(3) 0.4945(2) 0.14646(16) 0.0140(3) Uani 1 1 d . . . . .
H5 H 0.7530 0.5604 0.0534 0.017 Uiso 1 1 calc R U . . .
C6 C 0.8625(3) 0.3221(2) 0.22603(15) 0.0118(3) Uani 1 1 d . . . . .
H6 H 1.0399 0.2689 0.1856 0.014 Uiso 1 1 calc R U . . .
H7 H 0.2408 0.0891 0.8464 0.050 Uiso 1 1 d . . . . .
H8 H 0.1087 0.0190 0.9790 0.050 Uiso 0.5 1 d . . P A 1
H8' H 0.3881 0.0208 0.9714 0.050 Uiso 0.5 1 d . . P A 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O1 1.9446(9) . ?
Cu1 O1 1.9446(9) 2_756 ?
Cu1 N1 1.9589(11) 2_756 ?
Cu1 N1 1.9589(11) . ?
N1 C6 1.3400(18) . ?
N1 C2 1.3469(17) . ?
O1 C1 1.2809(16) . ?
O2 C1 1.2369(16) . ?
O3 H7 0.8383 . ?
O3 H8 0.7852 . ?
O3 H8' 0.8081 . ?
C1 C2 1.5127(18) . ?
C2 C3 1.3819(19) . ?
C3 C4 1.390(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.387(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.385(2) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?

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
O1 Cu1 O1 180.0 . 2_756 ?
O1 Cu1 N1 96.11(4) . 2_756 ?
O1 Cu1 N1 83.89(4) 2_756 2_756 ?
O1 Cu1 N1 83.89(4) . . ?
O1 Cu1 N1 96.11(4) 2_756 . ?
N1 Cu1 N1 180.0 2_756 . ?
C6 N1 C2 119.62(12) . . ?
C6 N1 Cu1 128.11(9) . . ?
C2 N1 Cu1 112.14(9) . . ?
C1 O1 Cu1 114.33(8) . . ?
H7 O3 H8 118.5 . . ?
H7 O3 H8' 106.4 . . ?
O2 C1 O1 125.04(12) . . ?
O2 C1 C2 119.79(12) . . ?
O1 C1 C2 115.16(11) . . ?
N1 C2 C3 122.27(13) . . ?
N1 C2 C1 113.86(11) . . ?
C3 C2 C1 123.86(12) . . ?
C2 C3 C4 118.19(13) . . ?
C2 C3 H3 120.9 . . ?
C4 C3 H3 120.9 . . ?
C5 C4 C3 119.37(13) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
C6 C5 C4 119.34(13) . . ?
C6 C5 H5 120.3 . . ?
C4 C5 H5 120.3 . . ?
N1 C6 C5 121.16(13) . . ?
N1 C6 H6 119.4 . . ?
C5 C6 H6 119.4 . . ?

_refine_diff_density_max         0.394
_refine_diff_density_min         -0.290
_refine_diff_density_rms         0.051

_shelxl_version_number           2014/6

