# Electronic Supplementary Material (ESI) for MedChemComm.
# 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_cbu1702
_database_code_depnum_ccdc_archive 'CCDC 1812776'
_audit_update_record             
;
2017-12-20 deposited with the CCDC.
2018-06-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        
N-(2-{3-(benzyloxy)-2-methyl-4-oxopyridin-1(4H)-yl}ethyl)-2-methylprop-2-enamide
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H22 N2 O3'
_chemical_formula_sum            'C19 H22 N2 O3'
_chemical_formula_weight         326.38

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'

_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, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   7.24927(18)
_cell_length_b                   12.5565(3)
_cell_length_c                   19.2992(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1756.72(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9847
_cell_measurement_theta_min      4.20
_cell_measurement_theta_max      73.71

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.234
_exptl_crystal_F_000             696
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.546
_exptl_crystal_size_mid          0.196
_exptl_crystal_size_min          0.142
_exptl_absorpt_coefficient_mu    0.679
_shelx_estimated_absorpt_T_min   0.708
_shelx_estimated_absorpt_T_max   0.910
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.7087
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'SADABS 2016/2 (Krause et al., 2015)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12699
_diffrn_reflns_av_unetI/netI     0.0281
_diffrn_reflns_av_R_equivalents  0.0373
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         4.200
_diffrn_reflns_theta_max         74.071
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3548
_reflns_number_gt                3497
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.732
_reflns_Friedel_fraction_max     0.995
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXD (Schneider & Sheldrick, 2002)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.0499P)²+0.1872P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1465 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.01(4)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3548
_refine_ls_number_parameters     223
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0322
_refine_ls_R_factor_gt           0.0318
_refine_ls_wR_factor_ref         0.0841
_refine_ls_wR_factor_gt          0.0836
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.062
_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 0.5394(2) -0.09809(11) 0.08569(8) 0.0507(4) Uani 1 1 d . . . . .
O2 O -0.15076(15) 0.18658(8) 0.16739(6) 0.0299(2) Uani 1 1 d . . . . .
O3 O -0.41697(15) 0.09418(10) 0.25142(6) 0.0352(3) Uani 1 1 d . . . . .
N1 N 0.44857(19) -0.22656(12) 0.15938(8) 0.0341(3) Uani 1 1 d . . . . .
H1N H 0.469(3) -0.284(2) 0.1810(12) 0.045(6) Uiso 1 1 d . . . . .
N2 N 0.09181(17) -0.04338(10) 0.23403(6) 0.0273(3) Uani 1 1 d . . . . .
C1 C 0.5713(2) -0.18202(13) 0.11592(8) 0.0326(3) Uani 1 1 d . . . . .
C2 C 0.7481(2) -0.24263(13) 0.10520(9) 0.0333(3) Uani 1 1 d . . . . .
C3 C 0.8512(3) -0.2158(2) 0.04955(11) 0.0552(5) Uani 1 1 d . . . . .
H3A H 0.963188 -0.252527 0.040366 0.066 Uiso 1 1 calc R U . . .
H3B H 0.811789 -0.160256 0.019605 0.066 Uiso 1 1 calc R U . . .
C4 C 0.8006(2) -0.32767(15) 0.15371(10) 0.0388(4) Uani 1 1 d . . . . .
H4A H 0.918548 -0.358667 0.139298 0.047 Uiso 1 1 calc R U . . .
H4B H 0.705299 -0.383049 0.153726 0.047 Uiso 1 1 calc R U . . .
H4C H 0.812794 -0.297991 0.200450 0.047 Uiso 1 1 calc R U . . .
C5 C 0.2686(2) -0.17904(13) 0.17028(9) 0.0353(4) Uani 1 1 d . . . . .
H5A H 0.178354 -0.235674 0.181480 0.042 Uiso 1 1 calc R U . . .
H5B H 0.227795 -0.143759 0.127036 0.042 Uiso 1 1 calc R U . . .
C6 C 0.2721(2) -0.09765(13) 0.22890(8) 0.0304(3) Uani 1 1 d . . . . .
H6A H 0.300151 -0.133922 0.273207 0.036 Uiso 1 1 calc R U . . .
H6B H 0.370179 -0.044500 0.220053 0.036 Uiso 1 1 calc R U . . .
C7 C 0.0532(2) 0.04687(12) 0.19629(7) 0.0257(3) Uani 1 1 d . . . . .
C8 C -0.1185(2) 0.09180(11) 0.20143(8) 0.0258(3) Uani 1 1 d . . . . .
C9 C -0.2631(2) 0.04930(12) 0.24493(8) 0.0280(3) Uani 1 1 d . . . . .
C10 C -0.2131(2) -0.04696(13) 0.27990(8) 0.0331(3) Uani 1 1 d . . . . .
H10 H -0.301883 -0.082172 0.307933 0.040 Uiso 1 1 calc R U . . .
C11 C -0.0416(2) -0.08891(13) 0.27382(8) 0.0317(3) Uani 1 1 d . . . . .
H11 H -0.013410 -0.152521 0.298274 0.038 Uiso 1 1 calc R U . . .
C12 C 0.2030(2) 0.09518(13) 0.15309(9) 0.0329(3) Uani 1 1 d . . . . .
H12A H 0.150790 0.151091 0.123592 0.039 Uiso 1 1 calc R U . . .
H12B H 0.259016 0.040009 0.123979 0.039 Uiso 1 1 calc R U . . .
H12C H 0.297293 0.126044 0.183443 0.039 Uiso 1 1 calc R U . . .
C13 C -0.2687(2) 0.17571(13) 0.10734(9) 0.0352(4) Uani 1 1 d . . . . .
H13A H -0.388771 0.144323 0.120795 0.042 Uiso 1 1 calc R U . . .
H13B H -0.210170 0.128767 0.072482 0.042 Uiso 1 1 calc R U . . .
C14 C -0.2962(3) 0.28519(13) 0.07807(8) 0.0339(3) Uani 1 1 d . . . . .
C15 C -0.1461(3) 0.34226(16) 0.05217(9) 0.0434(4) Uani 1 1 d . . . . .
H15 H -0.026895 0.310781 0.052065 0.052 Uiso 1 1 calc R U . . .
C16 C -0.1694(4) 0.44391(19) 0.02675(10) 0.0563(6) Uani 1 1 d . . . . .
H16 H -0.066417 0.482211 0.009229 0.068 Uiso 1 1 calc R U . . .
C17 C -0.3424(4) 0.49024(16) 0.02672(11) 0.0601(7) Uani 1 1 d . . . . .
H17 H -0.358044 0.560385 0.009237 0.072 Uiso 1 1 calc R U . . .
C18 C -0.4917(4) 0.43521(18) 0.05188(11) 0.0553(6) Uani 1 1 d . . . . .
H18 H -0.610569 0.467120 0.051625 0.066 Uiso 1 1 calc R U . . .
C19 C -0.4687(3) 0.33233(16) 0.07782(10) 0.0430(4) Uani 1 1 d . . . . .
H19 H -0.572014 0.294460 0.095409 0.052 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 C1 1.226(2) . ?
O2 C8 1.3794(18) . ?
O2 C13 1.4468(19) . ?
O3 C9 1.2558(19) . ?
N1 C1 1.345(2) . ?
N1 C5 1.450(2) . ?
N2 C11 1.3606(19) . ?
N2 C7 1.376(2) . ?
N2 C6 1.4772(19) . ?
C1 C2 1.505(2) . ?
C2 C3 1.351(3) . ?
C2 C4 1.470(2) . ?
C5 C6 1.525(2) . ?
C7 C8 1.370(2) . ?
C7 C12 1.498(2) . ?
C8 C9 1.445(2) . ?
C9 C10 1.431(2) . ?
C10 C11 1.355(2) . ?
C13 C14 1.499(2) . ?
C14 C19 1.383(3) . ?
C14 C15 1.396(3) . ?
C15 C16 1.378(3) . ?
C16 C17 1.383(4) . ?
C17 C18 1.373(4) . ?
C18 C19 1.395(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
C8 O2 C13 113.61(11) . . ?
C1 N1 C5 120.98(14) . . ?
C11 N2 C7 120.00(13) . . ?
C11 N2 C6 118.22(13) . . ?
C7 N2 C6 121.64(12) . . ?
O1 C1 N1 121.96(16) . . ?
O1 C1 C2 121.98(16) . . ?
N1 C1 C2 116.04(14) . . ?
C3 C2 C4 122.97(17) . . ?
C3 C2 C1 117.03(17) . . ?
C4 C2 C1 120.00(14) . . ?
N1 C5 C6 111.61(13) . . ?
N2 C6 C5 110.13(12) . . ?
C8 C7 N2 119.07(13) . . ?
C8 C7 C12 122.16(13) . . ?
N2 C7 C12 118.72(13) . . ?
C7 C8 O2 118.36(13) . . ?
C7 C8 C9 123.30(13) . . ?
O2 C8 C9 118.16(13) . . ?
O3 C9 C10 123.86(14) . . ?
O3 C9 C8 122.45(14) . . ?
C10 C9 C8 113.69(13) . . ?
C11 C10 C9 121.33(14) . . ?
C10 C11 N2 122.51(15) . . ?
O2 C13 C14 107.09(12) . . ?
C19 C14 C15 118.94(17) . . ?
C19 C14 C13 120.92(16) . . ?
C15 C14 C13 120.12(17) . . ?
C16 C15 C14 120.5(2) . . ?
C15 C16 C17 120.1(2) . . ?
C18 C17 C16 120.23(18) . . ?
C17 C18 C19 119.9(2) . . ?
C14 C19 C18 120.4(2) . . ?

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
C5 N1 C1 O1 2.6(3) . . . . ?
C5 N1 C1 C2 -175.96(14) . . . . ?
O1 C1 C2 C3 -15.4(3) . . . . ?
N1 C1 C2 C3 163.17(18) . . . . ?
O1 C1 C2 C4 165.41(17) . . . . ?
N1 C1 C2 C4 -16.1(2) . . . . ?
C1 N1 C5 C6 -88.8(2) . . . . ?
C11 N2 C6 C5 87.40(17) . . . . ?
C7 N2 C6 C5 -88.23(17) . . . . ?
N1 C5 C6 N2 174.47(13) . . . . ?
C11 N2 C7 C8 2.3(2) . . . . ?
C6 N2 C7 C8 177.88(13) . . . . ?
C11 N2 C7 C12 179.90(14) . . . . ?
C6 N2 C7 C12 -4.5(2) . . . . ?
N2 C7 C8 O2 175.22(12) . . . . ?
C12 C7 C8 O2 -2.3(2) . . . . ?
N2 C7 C8 C9 0.1(2) . . . . ?
C12 C7 C8 C9 -177.38(14) . . . . ?
C13 O2 C8 C7 108.05(15) . . . . ?
C13 O2 C8 C9 -76.58(17) . . . . ?
C7 C8 C9 O3 176.73(13) . . . . ?
O2 C8 C9 O3 1.6(2) . . . . ?
C7 C8 C9 C10 -2.6(2) . . . . ?
O2 C8 C9 C10 -177.72(12) . . . . ?
O3 C9 C10 C11 -176.46(15) . . . . ?
C8 C9 C10 C11 2.9(2) . . . . ?
C9 C10 C11 N2 -0.7(3) . . . . ?
C7 N2 C11 C10 -2.1(2) . . . . ?
C6 N2 C11 C10 -177.79(15) . . . . ?
C8 O2 C13 C14 177.83(13) . . . . ?
O2 C13 C14 C19 -114.93(16) . . . . ?
O2 C13 C14 C15 63.41(19) . . . . ?
C19 C14 C15 C16 0.0(3) . . . . ?
C13 C14 C15 C16 -178.40(16) . . . . ?
C14 C15 C16 C17 0.0(3) . . . . ?
C15 C16 C17 C18 -0.1(3) . . . . ?
C16 C17 C18 C19 0.3(3) . . . . ?
C15 C14 C19 C18 0.2(3) . . . . ?
C13 C14 C19 C18 178.53(16) . . . . ?
C17 C18 C19 C14 -0.3(3) . . . . ?

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
N1 H1N O3 0.85(2) 2.04(2) 2.8429(19) 157(2) 3_545

_refine_diff_density_max         0.119
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.047

####################################################################### 
# 
# 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_cbu1801
_database_code_depnum_ccdc_archive 'CCDC 1830658'
_audit_update_record             
;
2018-03-18 deposited with the CCDC.
2018-06-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H16 N2 O3, H2 O'
_chemical_formula_sum            'C12 H18 N2 O4'
_chemical_formula_weight         254.28

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.13370(10)
_cell_length_b                   25.5550(5)
_cell_length_c                   7.17780(10)
_cell_angle_alpha                90
_cell_angle_beta                 101.3314(7)
_cell_angle_gamma                90
_cell_volume                     1283.02(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9868
_cell_measurement_theta_min      6.52
_cell_measurement_theta_max      72.26

_exptl_crystal_description       fragment
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_F_000             544
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.267
_exptl_crystal_size_mid          0.209
_exptl_crystal_size_min          0.162
_exptl_absorpt_coefficient_mu    0.827
_shelx_estimated_absorpt_T_min   0.809
_shelx_estimated_absorpt_T_max   0.878
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.8467
_exptl_absorpt_correction_T_max  0.9495
_exptl_absorpt_process_details   SADABS-2016/2
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8816
_diffrn_reflns_av_unetI/netI     0.0125
_diffrn_reflns_av_R_equivalents  0.0144
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         3.459
_diffrn_reflns_theta_max         72.438
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2540
_reflns_number_gt                2441
_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       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick 2015)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.0531P)²+0.4452P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2540
_refine_ls_number_parameters     183
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0390
_refine_ls_R_factor_gt           0.0379
_refine_ls_wR_factor_ref         0.1028
_refine_ls_wR_factor_gt          0.1017
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.007
_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 0.48600(13) 0.67979(4) 0.00344(15) 0.0411(3) Uani 1 1 d . . . . .
O2 O 0.37649(12) 0.53926(4) 0.73713(13) 0.0339(2) Uani 1 1 d . . . . .
H2O H 0.383(2) 0.5260(7) 0.850(3) 0.046(5) Uiso 1 1 d . . . . .
O3 O 0.68100(12) 0.48017(3) 0.91591(12) 0.0305(2) Uani 1 1 d . . . . .
N1 N 0.77134(15) 0.63969(4) 0.02933(14) 0.0264(2) Uani 1 1 d . . . . .
H1N H 0.887(2) 0.6389(6) 0.006(2) 0.035(4) Uiso 1 1 d . . . . .
N2 N 0.75192(14) 0.58764(4) 0.51424(13) 0.0264(2) Uani 1 1 d . . . . .
C1 C 0.64530(17) 0.67707(4) -0.03971(16) 0.0273(3) Uani 1 1 d . . . . .
C2 C 0.70605(19) 0.71698(5) -0.17004(17) 0.0327(3) Uani 1 1 d . . . . .
C3 C 0.8695(3) 0.71234(7) -0.2394(2) 0.0568(5) Uani 1 1 d . . . . .
H3A H 0.905060 0.739156 -0.317298 0.068 Uiso 1 1 calc R U . . .
H3B H 0.948075 0.682283 -0.209933 0.068 Uiso 1 1 calc R U . . .
C4 C 0.5824(3) 0.76142(8) -0.2100(4) 0.0769(7) Uani 1 1 d . . . . .
H4A H 0.626014 0.783750 -0.304000 0.092 Uiso 0.86(2) 1 calc R U P . .
H4B H 0.585017 0.781347 -0.092825 0.092 Uiso 0.86(2) 1 calc R U P . .
H4C H 0.451627 0.749583 -0.260379 0.092 Uiso 0.86(2) 1 calc R U P . .
H4D H 0.482425 0.759370 -0.134136 0.092 Uiso 0.14(2) 1 calc R U P . .
H4E H 0.523422 0.761773 -0.345311 0.092 Uiso 0.14(2) 1 calc R U P . .
H4F H 0.656811 0.793537 -0.177757 0.092 Uiso 0.14(2) 1 calc R U P . .
C5 C 0.73074(18) 0.60171(4) 0.16683(16) 0.0281(3) Uani 1 1 d . . . . .
H5A H 0.804838 0.569315 0.158743 0.034 Uiso 1 1 calc R U . . .
H5B H 0.593091 0.592695 0.138657 0.034 Uiso 1 1 calc R U . . .
C6 C 0.78476(18) 0.62479(5) 0.36655(16) 0.0291(3) Uani 1 1 d . . . . .
H6A H 0.921376 0.634905 0.391437 0.035 Uiso 1 1 calc R U . . .
H6B H 0.708421 0.656818 0.373712 0.035 Uiso 1 1 calc R U . . .
C7 C 0.57502(16) 0.58193(4) 0.56190(15) 0.0248(2) Uani 1 1 d . . . . .
C8 C 0.55240(16) 0.54509(4) 0.69461(15) 0.0242(2) Uani 1 1 d . . . . .
C9 C 0.70665(16) 0.51303(4) 0.79044(15) 0.0235(2) Uani 1 1 d . . . . .
C10 C 0.88410(17) 0.52194(5) 0.73583(17) 0.0288(3) Uani 1 1 d . . . . .
H10 H 0.993053 0.502372 0.794404 0.035 Uiso 1 1 calc R U . . .
C11 C 0.90136(17) 0.55800(5) 0.60106(17) 0.0296(3) Uani 1 1 d . . . . .
H11 H 1.022221 0.562597 0.566538 0.036 Uiso 1 1 calc R U . . .
C12 C 0.41243(19) 0.61671(6) 0.47400(19) 0.0372(3) Uani 1 1 d . . . . .
H12A H 0.459741 0.652398 0.464089 0.045 Uiso 0.593(17) 1 calc R U P . .
H12B H 0.315322 0.616781 0.553463 0.045 Uiso 0.593(17) 1 calc R U P . .
H12C H 0.355876 0.603677 0.346974 0.045 Uiso 0.593(17) 1 calc R U P . .
H12D H 0.294218 0.596173 0.445594 0.045 Uiso 0.407(17) 1 calc R U P . .
H12E H 0.438637 0.631789 0.356221 0.045 Uiso 0.407(17) 1 calc R U P . .
H12F H 0.398083 0.644894 0.562710 0.045 Uiso 0.407(17) 1 calc R U P . .
O1S O 0.15536(14) 0.61932(4) 0.00528(17) 0.0427(3) Uani 1 1 d . . . . .
H1SA H 0.258(3) 0.6372(8) -0.004(3) 0.058(5) Uiso 1 1 d . . . . .
H1SB H 0.191(3) 0.5883(9) 0.023(3) 0.065(6) 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 1.2372(15) . ?
O2 C8 1.3567(14) . ?
O3 C9 1.2708(14) . ?
N1 C1 1.3384(16) . ?
N1 C5 1.4534(14) . ?
N2 C11 1.3555(16) . ?
N2 C7 1.3785(15) . ?
N2 C6 1.4757(14) . ?
C1 C2 1.5041(17) . ?
C2 C3 1.360(2) . ?
C2 C4 1.432(2) . ?
C5 C6 1.5279(16) . ?
C7 C8 1.3712(16) . ?
C7 C12 1.4985(17) . ?
C8 C9 1.4345(16) . ?
C9 C10 1.4152(16) . ?
C10 C11 1.3591(17) . ?

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 N1 C5 121.27(10) . . ?
C11 N2 C7 120.16(10) . . ?
C11 N2 C6 117.92(10) . . ?
C7 N2 C6 121.91(10) . . ?
O1 C1 N1 122.05(11) . . ?
O1 C1 C2 120.57(11) . . ?
N1 C1 C2 117.36(11) . . ?
C3 C2 C4 122.31(14) . . ?
C3 C2 C1 122.75(12) . . ?
C4 C2 C1 114.89(13) . . ?
N1 C5 C6 109.40(9) . . ?
N2 C6 C5 112.29(9) . . ?
C8 C7 N2 118.91(10) . . ?
C8 C7 C12 120.84(11) . . ?
N2 C7 C12 120.23(10) . . ?
O2 C8 C7 118.17(10) . . ?
O2 C8 C9 119.05(10) . . ?
C7 C8 C9 122.78(11) . . ?
O3 C9 C10 124.32(11) . . ?
O3 C9 C8 120.90(10) . . ?
C10 C9 C8 114.77(10) . . ?
C11 C10 C9 121.15(11) . . ?
N2 C11 C10 122.21(11) . . ?

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
C5 N1 C1 O1 -3.13(18) . . . . ?
C5 N1 C1 C2 175.53(10) . . . . ?
O1 C1 C2 C3 -172.06(15) . . . . ?
N1 C1 C2 C3 9.3(2) . . . . ?
O1 C1 C2 C4 10.3(2) . . . . ?
N1 C1 C2 C4 -168.42(16) . . . . ?
C1 N1 C5 C6 -84.78(13) . . . . ?
C11 N2 C6 C5 94.82(13) . . . . ?
C7 N2 C6 C5 -83.94(14) . . . . ?
N1 C5 C6 N2 -178.48(10) . . . . ?
C11 N2 C7 C8 -1.52(17) . . . . ?
C6 N2 C7 C8 177.21(10) . . . . ?
C11 N2 C7 C12 176.60(11) . . . . ?
C6 N2 C7 C12 -4.68(17) . . . . ?
N2 C7 C8 O2 -178.71(10) . . . . ?
C12 C7 C8 O2 3.19(17) . . . . ?
N2 C7 C8 C9 1.77(17) . . . . ?
C12 C7 C8 C9 -176.33(11) . . . . ?
O2 C8 C9 O3 -1.20(16) . . . . ?
C7 C8 C9 O3 178.32(10) . . . . ?
O2 C8 C9 C10 179.80(10) . . . . ?
C7 C8 C9 C10 -0.68(16) . . . . ?
O3 C9 C10 C11 -179.63(11) . . . . ?
C8 C9 C10 C11 -0.66(17) . . . . ?
C7 N2 C11 C10 0.20(18) . . . . ?
C6 N2 C11 C10 -178.58(11) . . . . ?
C9 C10 C11 N2 0.92(19) . . . . ?

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
O2 H2O O3 0.869(19) 1.834(19) 2.6492(12) 155.3(17) 3_667
N1 H1N O1S 0.874(17) 1.979(17) 2.8270(15) 163.2(15) 1_655
O1S H1SA O1 0.88(2) 1.95(2) 2.8221(14) 173.6(19) .
O1S H1SB O3 0.83(2) 1.98(2) 2.8083(13) 170(2) 3_666

_refine_diff_density_max         0.273
_refine_diff_density_min         -0.318
_refine_diff_density_rms         0.039

