# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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_2bMeOHexp2084
_database_code_depnum_ccdc_archive 'CCDC 1588275'
_audit_update_record             
;
2017-11-29 deposited with the CCDC.
2018-02-12 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         'C14 H13 N3 O3, C H4 O'
_chemical_formula_sum            'C15 H17 N3 O4'
_chemical_formula_weight         303.32

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/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                   8.7634(6)
_cell_length_b                   19.3464(11)
_cell_length_c                   8.8479(7)
_cell_angle_alpha                90
_cell_angle_beta                 96.305(7)
_cell_angle_gamma                90
_cell_volume                     1491.00(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3062
_cell_measurement_theta_min      4.6790
_cell_measurement_theta_max      31.7900


_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_F_000             640
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.63
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.24
_exptl_absorpt_coefficient_mu    0.100
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.98216
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35.
Empirical absorption correction using 
spherical harmonics,
implemented in SCALE3 ABSPACK 
scaling algorithm.
;

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4751
_diffrn_reflns_av_unetI/netI     0.0512
_diffrn_reflns_av_R_equivalents  0.0231
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         4.432
_diffrn_reflns_theta_max         27.498
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.934
_diffrn_measured_fraction_theta_full 0.908
_diffrn_reflns_Laue_measured_fraction_max 0.908
_diffrn_reflns_Laue_measured_fraction_full 0.934
_diffrn_reflns_point_group_measured_fraction_max 0.908
_diffrn_reflns_point_group_measured_fraction_full 0.934
_reflns_number_total             3114
_reflns_number_gt                1935
_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.
 

;

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_structure_solution    'SHELXT-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'MERCURY 3.8. (CCDC, 2016)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'


_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)+(0.0536P)²+0.0834P] 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     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.059(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3114
_refine_ls_number_parameters     211
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0950
_refine_ls_R_factor_gt           0.0529
_refine_ls_wR_factor_ref         0.1304
_refine_ls_wR_factor_gt          0.1132
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_restrained_S_all      1.016
_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
N1 N 0.99081(18) 0.00999(9) 0.77112(19) 0.0473(4) Uani 1 1 d D . . . .
H11N H 1.051(2) 0.0426(10) 0.808(2) 0.057 Uiso 1 1 d D U . . .
N2 N 1.05080(18) -0.03958(8) 0.68342(18) 0.0457(4) Uani 1 1 d . . . . .
N3 N 0.54492(18) 0.10435(10) 0.9735(2) 0.0569(5) Uani 1 1 d . . . . .
O1 O 0.75961(16) -0.04239(8) 0.7371(2) 0.0673(5) Uani 1 1 d . . . . .
O2 O 1.02711(16) -0.15202(8) 0.51836(18) 0.0596(4) Uani 1 1 d D . . . .
H12O H 0.997(3) -0.1202(12) 0.570(3) 0.089 Uiso 1 1 d D U . . .
O3 O 1.15756(16) -0.24059(8) 0.34856(17) 0.0585(4) Uani 1 1 d . . . . .
O4 O 0.22427(16) 0.11270(8) 0.8724(2) 0.0675(5) Uani 1 1 d D . . . .
H14O H 0.314(2) 0.1075(14) 0.916(3) 0.081 Uiso 1 1 d D U . . .
C1 C 0.8403(2) 0.00453(10) 0.7928(2) 0.0433(5) Uani 1 1 d . . . . .
C2 C 0.7773(2) 0.05907(10) 0.8882(2) 0.0403(5) Uani 1 1 d . . . . .
C3 C 0.6205(2) 0.05768(11) 0.8990(2) 0.0492(5) Uani 1 1 d . . . . .
H3 H 0.5640 0.0217 0.8510 0.059 Uiso 1 1 calc R U . . .
C4 C 0.6285(2) 0.15510(12) 1.0440(3) 0.0584(6) Uani 1 1 d . . . . .
H4 H 0.5788 0.1887 1.0958 0.070 Uiso 1 1 calc R U . . .
C5 C 0.7847(2) 0.15969(12) 1.0430(3) 0.0607(6) Uani 1 1 d . . . . .
H5 H 0.8391 0.1952 1.0954 0.073 Uiso 1 1 calc R U . . .
C6 C 0.8604(2) 0.11172(11) 0.9645(2) 0.0505(5) Uani 1 1 d . . . . .
H6 H 0.9661 0.1146 0.9626 0.061 Uiso 1 1 calc R U . . .
C7 C 1.1913(2) -0.03497(10) 0.6605(2) 0.0464(5) Uani 1 1 d . . . . .
H7 H 1.2499 0.0018 0.7023 0.056 Uiso 1 1 calc R U . . .
C8 C 1.2617(2) -0.08613(10) 0.5702(2) 0.0402(5) Uani 1 1 d . . . . .
C9 C 1.1769(2) -0.14136(10) 0.5019(2) 0.0408(5) Uani 1 1 d . . . . .
C10 C 1.2497(2) -0.18853(10) 0.4120(2) 0.0426(5) Uani 1 1 d . . . . .
C11 C 1.4024(2) -0.18058(11) 0.3931(2) 0.0477(5) Uani 1 1 d . . . . .
H11 H 1.4496 -0.2117 0.3330 0.057 Uiso 1 1 calc R U . . .
C12 C 1.4863(2) -0.12629(12) 0.4633(2) 0.0530(6) Uani 1 1 d . . . . .
H12 H 1.5897 -0.1215 0.4510 0.064 Uiso 1 1 calc R U . . .
C13 C 1.4172(2) -0.08001(11) 0.5504(2) 0.0491(5) Uani 1 1 d . . . . .
H13 H 1.4744 -0.0439 0.5972 0.059 Uiso 1 1 calc R U . . .
C14 C 1.2297(3) -0.29466(13) 0.2727(3) 0.0677(7) Uani 1 1 d . . . . .
H14A H 1.2696 -0.2764 0.1842 0.101 Uiso 1 1 calc R U . . .
H14B H 1.1559 -0.3301 0.2429 0.101 Uiso 1 1 calc R U . . .
H14C H 1.3122 -0.3138 0.3402 0.101 Uiso 1 1 calc R U . . .
C15 C 0.2166(3) 0.17869(14) 0.8041(3) 0.0669(7) Uani 1 1 d . . . . .
H15A H 0.1339 0.2045 0.8393 0.100 Uiso 1 1 calc R U . . .
H15B H 0.1992 0.1738 0.6956 0.100 Uiso 1 1 calc R U . . .
H15C H 0.3116 0.2027 0.8309 0.100 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
N1 C1 1.358(2) . ?
N1 N2 1.374(2) . ?
N1 H11N 0.861(15) . ?
N2 C7 1.273(2) . ?
N3 C3 1.336(3) . ?
N3 C4 1.338(3) . ?
O1 C1 1.220(2) . ?
O2 C9 1.353(2) . ?
O2 H12O 0.826(17) . ?
O3 C10 1.372(2) . ?
O3 C14 1.427(3) . ?
O4 C15 1.411(3) . ?
O4 H14O 0.841(16) . ?
C1 C2 1.494(3) . ?
C2 C6 1.384(3) . ?
C2 C3 1.388(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.373(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.373(3) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C8 1.451(3) . ?
C7 H7 0.9300 . ?
C8 C13 1.398(2) . ?
C8 C9 1.400(3) . ?
C9 C10 1.408(3) . ?
C10 C11 1.375(2) . ?
C11 C12 1.389(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.365(3) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 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 N1 N2 117.60(16) . . ?
C1 N1 H11N 124.6(15) . . ?
N2 N1 H11N 117.8(15) . . ?
C7 N2 N1 118.55(16) . . ?
C3 N3 C4 116.76(17) . . ?
C9 O2 H12O 108.7(18) . . ?
C10 O3 C14 117.32(16) . . ?
C15 O4 H14O 107.6(18) . . ?
O1 C1 N1 121.97(19) . . ?
O1 C1 C2 121.31(18) . . ?
N1 C1 C2 116.72(16) . . ?
C6 C2 C3 116.89(18) . . ?
C6 C2 C1 126.01(17) . . ?
C3 C2 C1 117.08(17) . . ?
N3 C3 C2 124.71(19) . . ?
N3 C3 H3 117.6 . . ?
C2 C3 H3 117.6 . . ?
N3 C4 C5 122.7(2) . . ?
N3 C4 H4 118.7 . . ?
C5 C4 H4 118.7 . . ?
C4 C5 C6 119.8(2) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
C5 C6 C2 119.11(18) . . ?
C5 C6 H6 120.4 . . ?
C2 C6 H6 120.4 . . ?
N2 C7 C8 121.12(18) . . ?
N2 C7 H7 119.4 . . ?
C8 C7 H7 119.4 . . ?
C13 C8 C9 119.26(18) . . ?
C13 C8 C7 119.35(17) . . ?
C9 C8 C7 121.39(17) . . ?
O2 C9 C8 123.02(17) . . ?
O2 C9 C10 117.86(16) . . ?
C8 C9 C10 119.11(17) . . ?
O3 C10 C11 124.69(18) . . ?
O3 C10 C9 115.08(16) . . ?
C11 C10 C9 120.24(17) . . ?
C10 C11 C12 120.28(19) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C13 C12 C11 120.19(18) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C12 C13 C8 120.91(18) . . ?
C12 C13 H13 119.5 . . ?
C8 C13 H13 119.5 . . ?
O3 C14 H14A 109.5 . . ?
O3 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O3 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O4 C15 H15A 109.5 . . ?
O4 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O4 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 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
C1 N1 N2 C7 179.29(18) . . . . ?
N2 N1 C1 O1 0.0(3) . . . . ?
N2 N1 C1 C2 -179.86(16) . . . . ?
O1 C1 C2 C6 175.5(2) . . . . ?
N1 C1 C2 C6 -4.6(3) . . . . ?
O1 C1 C2 C3 -5.8(3) . . . . ?
N1 C1 C2 C3 174.04(18) . . . . ?
C4 N3 C3 C2 -1.1(3) . . . . ?
C6 C2 C3 N3 2.1(3) . . . . ?
C1 C2 C3 N3 -176.73(19) . . . . ?
C3 N3 C4 C5 -0.8(3) . . . . ?
N3 C4 C5 C6 1.5(4) . . . . ?
C4 C5 C6 C2 -0.4(3) . . . . ?
C3 C2 C6 C5 -1.2(3) . . . . ?
C1 C2 C6 C5 177.47(19) . . . . ?
N1 N2 C7 C8 179.37(18) . . . . ?
N2 C7 C8 C13 -178.63(18) . . . . ?
N2 C7 C8 C9 1.6(3) . . . . ?
C13 C8 C9 O2 178.34(17) . . . . ?
C7 C8 C9 O2 -1.9(3) . . . . ?
C13 C8 C9 C10 -1.5(3) . . . . ?
C7 C8 C9 C10 178.30(17) . . . . ?
C14 O3 C10 C11 7.8(3) . . . . ?
C14 O3 C10 C9 -172.18(18) . . . . ?
O2 C9 C10 O3 0.8(3) . . . . ?
C8 C9 C10 O3 -179.43(16) . . . . ?
O2 C9 C10 C11 -179.21(17) . . . . ?
C8 C9 C10 C11 0.6(3) . . . . ?
O3 C10 C11 C12 -179.49(19) . . . . ?
C9 C10 C11 C12 0.5(3) . . . . ?
C10 C11 C12 C13 -0.7(3) . . . . ?
C11 C12 C13 C8 -0.2(3) . . . . ?
C9 C8 C13 C12 1.3(3) . . . . ?
C7 C8 C13 C12 -178.5(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
N1 H11N O4 0.861(15) 2.070(16) 2.921(2) 170(2) 1_655
O2 H12O N2 0.826(17) 1.89(2) 2.615(2) 146(2) .
O4 H14O N3 0.841(16) 2.035(17) 2.858(2) 166(2) .
C4 H4 O3 0.93 2.57 3.433(3) 153.6 2_656
C6 H6 O4 0.93 2.48 3.377(3) 161.9 1_655
C7 H7 O4 0.93 2.64 3.412(3) 140.3 1_655
C13 H13 O1 0.93 2.67 3.343(2) 130.4 1_655
C14 H14B O1 0.96 2.63 3.182(3) 116.8 4_655
C15 H15B O2 0.96 2.62 3.410(3) 139.7 3_656


_refine_diff_density_max         0.157
_refine_diff_density_min         -0.146
_refine_diff_density_rms         0.032

####################################################################### 
# 
# 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_4bMeOHexp1965
_database_code_depnum_ccdc_archive 'CCDC 1588281'
_audit_update_record             
;
2017-11-29 deposited with the CCDC.
2018-02-12 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         'C15 H15 N3 O3, C H4 O'
_chemical_formula_sum            'C16 H19 N3 O4'
_chemical_formula_weight         317.34

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                   18.819(2)
_cell_length_b                   12.3035(8)
_cell_length_c                   15.245(2)
_cell_angle_alpha                90
_cell_angle_beta                 113.799(16)
_cell_angle_gamma                90
_cell_volume                     3229.6(7)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    6784
_cell_measurement_theta_min      4.4370
_cell_measurement_theta_max      31.1840


_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.305
_exptl_crystal_F_000             1344
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.04
_exptl_absorpt_coefficient_mu    0.095
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.97841
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35.
Empirical absorption correction using 
spherical harmonics,
 implemented in SCALE3 ABSPACK 
scaling algorithm.
;




_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            31536
_diffrn_reflns_av_unetI/netI     0.0454
_diffrn_reflns_av_R_equivalents  0.0458
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         4.257
_diffrn_reflns_theta_max         27.500
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             7385
_reflns_number_gt                5199
_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.
 

;

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_structure_solution    'SHELXT-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'MERCURY 3.8. (CCDC, 2016)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'


_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)+(0.0384P)²+0.4272P] 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         7385
_refine_ls_number_parameters     449
_refine_ls_number_restraints     10
_refine_ls_R_factor_all          0.0790
_refine_ls_R_factor_gt           0.0488
_refine_ls_wR_factor_ref         0.1034
_refine_ls_wR_factor_gt          0.0930
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.024
_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
N12 N 0.43581(7) 0.09122(11) 0.36702(9) 0.0283(3) Uani 1 1 d . . . . .
N11 N 0.46216(8) 0.06357(11) 0.29787(9) 0.0287(3) Uani 1 1 d D . . . .
N13 N 0.62692(8) -0.00036(13) 0.00798(10) 0.0329(3) Uani 1 1 d D . . . .
N21 N 0.02785(8) 0.47560(11) -0.16534(9) 0.0282(3) Uani 1 1 d D . . . .
N22 N 0.05595(7) 0.44833(11) -0.07010(9) 0.0273(3) Uani 1 1 d . . . . .
N23 N -0.12554(8) 0.51442(13) -0.62243(10) 0.0349(3) Uani 1 1 d D . . . .
O1ME O 0.38477(7) 0.88180(9) 0.18051(8) 0.0350(3) Uani 1 1 d D . . . .
O2ME O 0.10988(7) 0.63742(9) -0.22061(8) 0.0348(3) Uani 1 1 d D . . . .
O11 O 0.50510(7) 0.23570(9) 0.29826(8) 0.0363(3) Uani 1 1 d . . . . .
O12 O 0.39205(7) 0.23414(9) 0.45930(8) 0.0328(3) Uani 1 1 d D . . . .
H12O H 0.4116(10) 0.2093(14) 0.4214(12) 0.039 Uiso 1 1 d D U . . .
O13 O 0.32760(7) 0.27964(9) 0.57646(8) 0.0359(3) Uani 1 1 d . . . . .
O21 O -0.01702(7) 0.30325(9) -0.20148(8) 0.0348(3) Uani 1 1 d . . . . .
O22 O 0.07791(7) 0.30280(9) 0.05923(8) 0.0352(3) Uani 1 1 d D . . . .
O23 O 0.14565(7) 0.24350(10) 0.23664(8) 0.0396(3) Uani 1 1 d . . . . .
C1ME C 0.30998(11) 0.83796(17) 0.16061(16) 0.0544(6) Uani 1 1 d . . . . .
H1ME H 0.3142 0.7810 0.2074 0.082 Uiso 1 1 calc R U . . .
H2ME H 0.2885 0.8069 0.0959 0.082 Uiso 1 1 calc R U . . .
H3ME H 0.2756 0.8957 0.1648 0.082 Uiso 1 1 calc R U . . .
C2ME C 0.18676(11) 0.66881(17) -0.16078(14) 0.0509(5) Uani 1 1 d . . . . .
H4ME H 0.2126 0.6976 -0.2003 0.076 Uiso 1 1 calc R U . . .
H5ME H 0.2155 0.6055 -0.1247 0.076 Uiso 1 1 calc R U . . .
H6ME H 0.1854 0.7250 -0.1160 0.076 Uiso 1 1 calc R U . . .
C11 C 0.49873(9) 0.14147(13) 0.26724(11) 0.0270(4) Uani 1 1 d . . . . .
C12 C 0.53063(9) 0.10366(12) 0.19900(10) 0.0249(3) Uani 1 1 d . . . . .
C13 C 0.55173(8) -0.00524(13) 0.19590(10) 0.0256(3) Uani 1 1 d . . . . .
H13 H 0.5438 -0.0567 0.2375 0.031 Uiso 1 1 calc R U . . .
C14 C 0.58377(9) -0.03886(13) 0.13363(10) 0.0267(3) Uani 1 1 d . . . . .
H14 H 0.5989 -0.1126 0.1343 0.032 Uiso 1 1 calc R U . . .
C15 C 0.59433(8) 0.03404(13) 0.06923(10) 0.0261(3) Uani 1 1 d . . . . .
C16 C 0.57271(9) 0.14335(13) 0.07168(11) 0.0294(4) Uani 1 1 d . . . . .
H16 H 0.5791 0.1945 0.0288 0.035 Uiso 1 1 calc R U . . .
C17 C 0.54226(9) 0.17669(13) 0.13595(11) 0.0293(4) Uani 1 1 d . . . . .
H17 H 0.5290 0.2510 0.1373 0.035 Uiso 1 1 calc R U . . .
C18 C 0.40925(9) 0.01428(13) 0.40300(11) 0.0284(4) Uani 1 1 d . . . . .
H18 H 0.4103 -0.0588 0.3835 0.034 Uiso 1 1 calc R U . . .
C19 C 0.37777(8) 0.03986(12) 0.47355(10) 0.0250(3) Uani 1 1 d . . . . .
C21 C -0.01047(9) 0.39565(13) -0.22985(11) 0.0272(4) Uani 1 1 d . . . . .
C22 C -0.04115(9) 0.42845(13) -0.33146(11) 0.0261(3) Uani 1 1 d . . . . .
C23 C -0.05886(9) 0.53660(13) -0.36097(11) 0.0272(4) Uani 1 1 d . . . . .
H23 H -0.0513 0.5916 -0.3143 0.033 Uiso 1 1 calc R U . . .
C24 C -0.08697(9) 0.56447(14) -0.45642(11) 0.0295(4) Uani 1 1 d . . . . .
H24 H -0.0997 0.6381 -0.4748 0.035 Uiso 1 1 calc R U . . .
C25 C -0.09705(9) 0.48577(14) -0.52671(10) 0.0282(4) Uani 1 1 d . . . . .
C26 C -0.07935(9) 0.37712(13) -0.49762(11) 0.0310(4) Uani 1 1 d . . . . .
H26 H -0.0862 0.3223 -0.5442 0.037 Uiso 1 1 calc R U . . .
C27 C -0.05202(9) 0.34954(14) -0.40183(11) 0.0298(4) Uani 1 1 d . . . . .
H27 H -0.0404 0.2757 -0.3834 0.036 Uiso 1 1 calc R U . . .
C28 C 0.09417(9) 0.51887(13) -0.00675(11) 0.0277(4) Uani 1 1 d . . . . .
H28 H 0.1007 0.5906 -0.0253 0.033 Uiso 1 1 calc R U . . .
C29 C 0.12738(8) 0.48781(13) 0.09393(10) 0.0258(3) Uani 1 1 d . . . . .
C110 C 0.36950(9) 0.14766(13) 0.49709(10) 0.0250(3) Uani 1 1 d . . . . .
C111 C 0.33407(9) 0.17092(13) 0.56095(11) 0.0266(3) Uani 1 1 d . . . . .
C112 C 0.30855(9) 0.08640(14) 0.60063(11) 0.0294(4) Uani 1 1 d . . . . .
H112 H 0.2842 0.1015 0.6431 0.035 Uiso 1 1 calc R U . . .
C113 C 0.31845(9) -0.02132(14) 0.57844(11) 0.0315(4) Uani 1 1 d . . . . .
H113 H 0.3014 -0.0789 0.6067 0.038 Uiso 1 1 calc R U . . .
C114 C 0.35249(9) -0.04477(13) 0.51637(11) 0.0297(4) Uani 1 1 d . . . . .
H114 H 0.3591 -0.1183 0.5022 0.036 Uiso 1 1 calc R U . . .
C115 C 0.28846(11) 0.30823(15) 0.63635(14) 0.0429(5) Uani 1 1 d . . . . .
H15A H 0.2360 0.2773 0.6098 0.064 Uiso 1 1 calc R U . . .
H15B H 0.2852 0.3875 0.6393 0.064 Uiso 1 1 calc R U . . .
H15C H 0.3174 0.2794 0.7010 0.064 Uiso 1 1 calc R U . . .
C210 C 0.11945(9) 0.38138(13) 0.12182(10) 0.0263(3) Uani 1 1 d . . . . .
C211 C 0.15721(9) 0.35033(14) 0.21857(11) 0.0299(4) Uani 1 1 d . . . . .
C212 C 0.20210(9) 0.42507(15) 0.28592(11) 0.0331(4) Uani 1 1 d . . . . .
H212 H 0.2285 0.4038 0.3510 0.040 Uiso 1 1 calc R U . . .
C213 C 0.20868(10) 0.53151(15) 0.25865(12) 0.0348(4) Uani 1 1 d . . . . .
H213 H 0.2392 0.5825 0.3055 0.042 Uiso 1 1 calc R U . . .
C214 C 0.17134(9) 0.56333(14) 0.16438(11) 0.0312(4) Uani 1 1 d . . . . .
H214 H 0.1752 0.6365 0.1468 0.037 Uiso 1 1 calc R U . . .
C215 C 0.18556(11) 0.20570(17) 0.33281(12) 0.0478(5) Uani 1 1 d . . . . .
H25A H 0.2413 0.2193 0.3541 0.072 Uiso 1 1 calc R U . . .
H25B H 0.1766 0.1275 0.3354 0.072 Uiso 1 1 calc R U . . .
H25C H 0.1662 0.2444 0.3749 0.072 Uiso 1 1 calc R U . . .
H1 H 0.4167(11) 0.8285(14) 0.1884(14) 0.057 Uiso 1 1 d D U . . .
H2 H 0.0829(11) 0.6956(14) -0.2431(14) 0.057 Uiso 1 1 d D U . . .
H11N H 0.4463(11) 0.0011(13) 0.2667(13) 0.057 Uiso 1 1 d D U . . .
H13A H 0.6281(12) -0.0721(12) -0.0003(14) 0.057 Uiso 1 1 d D U . . .
H13B H 0.6198(12) 0.0415(15) -0.0425(12) 0.057 Uiso 1 1 d D U . . .
H21N H 0.0461(11) 0.5345(13) -0.1840(13) 0.057 Uiso 1 1 d D U . . .
H22 H 0.0618(11) 0.3357(15) 0.0042(11) 0.057 Uiso 1 1 d D U . . .
H23B H -0.1151(11) 0.4677(14) -0.6604(13) 0.057 Uiso 1 1 d D U . . .
H23A H -0.1200(12) 0.5844(13) -0.6338(14) 0.057 Uiso 1 1 d D 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
N12 C18 1.291(2) . ?
N12 N11 1.3765(17) . ?
N11 C11 1.367(2) . ?
N11 H11N 0.890(14) . ?
N13 C15 1.374(2) . ?
N13 H13A 0.893(15) . ?
N13 H13B 0.890(14) . ?
N21 N22 1.3713(17) . ?
N21 C21 1.372(2) . ?
N21 H21N 0.895(14) . ?
N22 C28 1.2816(19) . ?
N23 C25 1.382(2) . ?
N23 H23B 0.892(15) . ?
N23 H23A 0.893(15) . ?
O1ME C1ME 1.421(2) . ?
O1ME H1 0.863(15) . ?
O2ME C2ME 1.417(2) . ?
O2ME H2 0.864(15) . ?
O11 C11 1.2396(18) . ?
O12 C110 1.3570(18) . ?
O12 H12O 0.856(14) . ?
O13 C111 1.3723(18) . ?
O13 C115 1.4292(19) . ?
O21 C21 1.2401(18) . ?
O22 C210 1.3618(18) . ?
O22 H22 0.868(14) . ?
O23 C211 1.378(2) . ?
O23 C215 1.429(2) . ?
C1ME H1ME 0.9800 . ?
C1ME H2ME 0.9800 . ?
C1ME H3ME 0.9800 . ?
C2ME H4ME 0.9800 . ?
C2ME H5ME 0.9800 . ?
C2ME H6ME 0.9800 . ?
C11 C12 1.471(2) . ?
C12 C17 1.396(2) . ?
C12 C13 1.404(2) . ?
C13 C14 1.378(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.402(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.410(2) . ?
C16 C17 1.382(2) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 C19 1.456(2) . ?
C18 H18 0.9500 . ?
C19 C110 1.399(2) . ?
C19 C114 1.410(2) . ?
C21 C22 1.474(2) . ?
C22 C27 1.399(2) . ?
C22 C23 1.401(2) . ?
C23 C24 1.376(2) . ?
C23 H23 0.9500 . ?
C24 C25 1.399(2) . ?
C24 H24 0.9500 . ?
C25 C26 1.405(2) . ?
C26 C27 1.381(2) . ?
C26 H26 0.9500 . ?
C27 H27 0.9500 . ?
C28 C29 1.455(2) . ?
C28 H28 0.9500 . ?
C29 C210 1.403(2) . ?
C29 C214 1.409(2) . ?
C110 C111 1.414(2) . ?
C111 C112 1.383(2) . ?
C112 C113 1.399(2) . ?
C112 H112 0.9500 . ?
C113 C114 1.370(2) . ?
C113 H113 0.9500 . ?
C114 H114 0.9500 . ?
C115 H15A 0.9800 . ?
C115 H15B 0.9800 . ?
C115 H15C 0.9800 . ?
C210 C211 1.407(2) . ?
C211 C212 1.383(2) . ?
C212 C213 1.395(2) . ?
C212 H212 0.9500 . ?
C213 C214 1.378(2) . ?
C213 H213 0.9500 . ?
C214 H214 0.9500 . ?
C215 H25A 0.9800 . ?
C215 H25B 0.9800 . ?
C215 H25C 0.9800 . ?

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
C18 N12 N11 117.70(13) . . ?
C11 N11 N12 118.35(13) . . ?
C11 N11 H11N 121.9(13) . . ?
N12 N11 H11N 118.5(13) . . ?
C15 N13 H13A 116.3(13) . . ?
C15 N13 H13B 117.1(13) . . ?
H13A N13 H13B 117.0(18) . . ?
N22 N21 C21 116.75(13) . . ?
N22 N21 H21N 120.1(12) . . ?
C21 N21 H21N 120.7(12) . . ?
C28 N22 N21 119.44(13) . . ?
C25 N23 H23B 115.3(13) . . ?
C25 N23 H23A 115.2(13) . . ?
H23B N23 H23A 114.8(18) . . ?
C1ME O1ME H1 108.3(14) . . ?
C2ME O2ME H2 108.2(14) . . ?
C110 O12 H12O 107.4(12) . . ?
C111 O13 C115 117.03(13) . . ?
C210 O22 H22 103.0(13) . . ?
C211 O23 C215 117.10(13) . . ?
O1ME C1ME H1ME 109.5 . . ?
O1ME C1ME H2ME 109.5 . . ?
H1ME C1ME H2ME 109.5 . . ?
O1ME C1ME H3ME 109.5 . . ?
H1ME C1ME H3ME 109.5 . . ?
H2ME C1ME H3ME 109.5 . . ?
O2ME C2ME H4ME 109.5 . . ?
O2ME C2ME H5ME 109.5 . . ?
H4ME C2ME H5ME 109.5 . . ?
O2ME C2ME H6ME 109.5 . . ?
H4ME C2ME H6ME 109.5 . . ?
H5ME C2ME H6ME 109.5 . . ?
O11 C11 N11 120.65(14) . . ?
O11 C11 C12 124.16(14) . . ?
N11 C11 C12 115.17(14) . . ?
C17 C12 C13 117.78(14) . . ?
C17 C12 C11 120.37(14) . . ?
C13 C12 C11 121.83(14) . . ?
C14 C13 C12 121.21(14) . . ?
C14 C13 H13 119.4 . . ?
C12 C13 H13 119.4 . . ?
C13 C14 C15 121.04(15) . . ?
C13 C14 H14 119.5 . . ?
C15 C14 H14 119.5 . . ?
N13 C15 C14 120.46(15) . . ?
N13 C15 C16 121.63(15) . . ?
C14 C15 C16 117.88(14) . . ?
C17 C16 C15 120.58(15) . . ?
C17 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?
C16 C17 C12 121.48(15) . . ?
C16 C17 H17 119.3 . . ?
C12 C17 H17 119.3 . . ?
N12 C18 C19 119.85(15) . . ?
N12 C18 H18 120.1 . . ?
C19 C18 H18 120.1 . . ?
C110 C19 C114 119.23(14) . . ?
C110 C19 C18 120.98(14) . . ?
C114 C19 C18 119.75(14) . . ?
O21 C21 N21 120.32(14) . . ?
O21 C21 C22 124.44(14) . . ?
N21 C21 C22 115.25(14) . . ?
C27 C22 C23 118.06(14) . . ?
C27 C22 C21 119.31(14) . . ?
C23 C22 C21 122.61(14) . . ?
C24 C23 C22 121.10(15) . . ?
C24 C23 H23 119.5 . . ?
C22 C23 H23 119.5 . . ?
C23 C24 C25 120.85(15) . . ?
C23 C24 H24 119.6 . . ?
C25 C24 H24 119.6 . . ?
N23 C25 C24 120.47(15) . . ?
N23 C25 C26 121.15(15) . . ?
C24 C25 C26 118.36(14) . . ?
C27 C26 C25 120.47(15) . . ?
C27 C26 H26 119.8 . . ?
C25 C26 H26 119.8 . . ?
C26 C27 C22 121.15(15) . . ?
C26 C27 H27 119.4 . . ?
C22 C27 H27 119.4 . . ?
N22 C28 C29 119.24(14) . . ?
N22 C28 H28 120.4 . . ?
C29 C28 H28 120.4 . . ?
C210 C29 C214 119.08(14) . . ?
C210 C29 C28 120.78(14) . . ?
C214 C29 C28 120.06(15) . . ?
O12 C110 C19 123.25(13) . . ?
O12 C110 C111 116.67(14) . . ?
C19 C110 C111 120.05(14) . . ?
O13 C111 C112 125.94(14) . . ?
O13 C111 C110 114.54(13) . . ?
C112 C111 C110 119.51(15) . . ?
C111 C112 C113 120.21(15) . . ?
C111 C112 H112 119.9 . . ?
C113 C112 H112 119.9 . . ?
C114 C113 C112 120.76(15) . . ?
C114 C113 H113 119.6 . . ?
C112 C113 H113 119.6 . . ?
C113 C114 C19 120.22(15) . . ?
C113 C114 H114 119.9 . . ?
C19 C114 H114 119.9 . . ?
O13 C115 H15A 109.5 . . ?
O13 C115 H15B 109.5 . . ?
H15A C115 H15B 109.5 . . ?
O13 C115 H15C 109.5 . . ?
H15A C115 H15C 109.5 . . ?
H15B C115 H15C 109.5 . . ?
O22 C210 C29 123.46(13) . . ?
O22 C210 C211 116.48(14) . . ?
C29 C210 C211 120.04(14) . . ?
O23 C211 C212 125.74(14) . . ?
O23 C211 C210 114.51(14) . . ?
C212 C211 C210 119.75(15) . . ?
C211 C212 C213 120.27(15) . . ?
C211 C212 H212 119.9 . . ?
C213 C212 H212 119.9 . . ?
C214 C213 C212 120.57(15) . . ?
C214 C213 H213 119.7 . . ?
C212 C213 H213 119.7 . . ?
C213 C214 C29 120.23(16) . . ?
C213 C214 H214 119.9 . . ?
C29 C214 H214 119.9 . . ?
O23 C215 H25A 109.5 . . ?
O23 C215 H25B 109.5 . . ?
H25A C215 H25B 109.5 . . ?
O23 C215 H25C 109.5 . . ?
H25A C215 H25C 109.5 . . ?
H25B C215 H25C 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
C18 N12 N11 C11 -172.44(14) . . . . ?
C21 N21 N22 C28 178.01(14) . . . . ?
N12 N11 C11 O11 -2.9(2) . . . . ?
N12 N11 C11 C12 175.39(12) . . . . ?
O11 C11 C12 C17 -26.1(2) . . . . ?
N11 C11 C12 C17 155.69(14) . . . . ?
O11 C11 C12 C13 152.65(15) . . . . ?
N11 C11 C12 C13 -25.6(2) . . . . ?
C17 C12 C13 C14 0.8(2) . . . . ?
C11 C12 C13 C14 -177.97(14) . . . . ?
C12 C13 C14 C15 -1.9(2) . . . . ?
C13 C14 C15 N13 179.50(14) . . . . ?
C13 C14 C15 C16 1.4(2) . . . . ?
N13 C15 C16 C17 -177.98(14) . . . . ?
C14 C15 C16 C17 0.1(2) . . . . ?
C15 C16 C17 C12 -1.2(2) . . . . ?
C13 C12 C17 C16 0.7(2) . . . . ?
C11 C12 C17 C16 179.49(14) . . . . ?
N11 N12 C18 C19 -177.51(13) . . . . ?
N12 C18 C19 C110 5.6(2) . . . . ?
N12 C18 C19 C114 -176.75(14) . . . . ?
N22 N21 C21 O21 -1.5(2) . . . . ?
N22 N21 C21 C22 178.89(13) . . . . ?
O21 C21 C22 C27 -25.4(2) . . . . ?
N21 C21 C22 C27 154.20(14) . . . . ?
O21 C21 C22 C23 155.80(15) . . . . ?
N21 C21 C22 C23 -24.6(2) . . . . ?
C27 C22 C23 C24 0.7(2) . . . . ?
C21 C22 C23 C24 179.60(14) . . . . ?
C22 C23 C24 C25 -1.5(2) . . . . ?
C23 C24 C25 N23 179.80(15) . . . . ?
C23 C24 C25 C26 1.4(2) . . . . ?
N23 C25 C26 C27 -179.02(15) . . . . ?
C24 C25 C26 C27 -0.6(2) . . . . ?
C25 C26 C27 C22 -0.1(2) . . . . ?
C23 C22 C27 C26 0.0(2) . . . . ?
C21 C22 C27 C26 -178.87(15) . . . . ?
N21 N22 C28 C29 -176.78(13) . . . . ?
N22 C28 C29 C210 1.4(2) . . . . ?
N22 C28 C29 C214 178.29(14) . . . . ?
C114 C19 C110 O12 -179.88(14) . . . . ?
C18 C19 C110 O12 -2.2(2) . . . . ?
C114 C19 C110 C111 -1.9(2) . . . . ?
C18 C19 C110 C111 175.79(14) . . . . ?
C115 O13 C111 C112 -2.4(2) . . . . ?
C115 O13 C111 C110 176.72(14) . . . . ?
O12 C110 C111 O13 -0.28(19) . . . . ?
C19 C110 C111 O13 -178.44(13) . . . . ?
O12 C110 C111 C112 178.89(13) . . . . ?
C19 C110 C111 C112 0.7(2) . . . . ?
O13 C111 C112 C113 179.69(14) . . . . ?
C110 C111 C112 C113 0.6(2) . . . . ?
C111 C112 C113 C114 -0.9(2) . . . . ?
C112 C113 C114 C19 -0.3(2) . . . . ?
C110 C19 C114 C113 1.6(2) . . . . ?
C18 C19 C114 C113 -176.04(14) . . . . ?
C214 C29 C210 O22 179.68(14) . . . . ?
C28 C29 C210 O22 -3.4(2) . . . . ?
C214 C29 C210 C211 -2.0(2) . . . . ?
C28 C29 C210 C211 174.83(14) . . . . ?
C215 O23 C211 C212 -2.2(2) . . . . ?
C215 O23 C211 C210 177.05(15) . . . . ?
O22 C210 C211 O23 -0.9(2) . . . . ?
C29 C210 C211 O23 -179.28(13) . . . . ?
O22 C210 C211 C212 178.38(14) . . . . ?
C29 C210 C211 C212 0.0(2) . . . . ?
O23 C211 C212 C213 -179.43(15) . . . . ?
C210 C211 C212 C213 1.4(2) . . . . ?
C211 C212 C213 C214 -0.7(2) . . . . ?
C212 C213 C214 C29 -1.4(2) . . . . ?
C210 C29 C214 C213 2.8(2) . . . . ?
C28 C29 C214 C213 -174.13(15) . . . . ?

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
O12 H12O N12 0.856(14) 1.820(15) 2.5855(17) 147.9(17) .
C14 H14 O12 0.95 2.41 3.2456(19) 146.4 2_645
C24 H24 O22 0.95 2.52 3.361(2) 147.5 2_554
C215 H25A O12 0.98 2.64 3.591(2) 163.1 .
O1ME H1 O11 0.863(15) 1.809(15) 2.6627(16) 169(2) 2_655
O2ME H2 O21 0.864(15) 1.778(15) 2.6367(16) 172(2) 2_554
N11 H11N O1ME 0.890(14) 1.998(15) 2.8672(18) 165.0(19) 1_545
N13 H13A O12 0.893(15) 2.531(16) 3.345(2) 151.8(17) 2_645
N13 H13A O13 0.893(15) 2.481(17) 3.2566(19) 145.5(17) 2_645
N13 H13B O1ME 0.890(14) 2.276(15) 3.1500(19) 167.3(18) 3_665
N21 H21N O2ME 0.895(14) 1.975(15) 2.8472(18) 164.4(19) .
O22 H22 N21 0.868(14) 2.953(15) 3.8111(18) 170.1(17) .
O22 H22 N22 0.868(14) 1.765(16) 2.5702(17) 153.2(19) .
O22 H22 O21 0.868(14) 2.905(17) 3.6410(17) 143.7(16) .
N23 H23B O2ME 0.892(15) 2.262(15) 3.142(2) 168.8(18) 3_564
N23 H23A O22 0.893(15) 2.900(17) 3.691(2) 148.4(16) 2_554
N23 H23A O23 0.893(15) 2.431(16) 3.254(2) 153.3(17) 2_554

_refine_diff_density_max         0.223
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.040

####################################################################### 
# 
# 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_4a_exp_2032
_database_code_depnum_ccdc_archive 'CCDC 1588278'
_audit_update_record             
;
2017-11-29 deposited with the CCDC.
2018-02-12 downloaded from the CCDC.
;

_vrf_PLAT480                     
;
PROBLEM: 
Long H...A H-Bond Reported H12O ..O1 3.34 Ang
Long H...A H-Bond Reported H6 ..N3 3.48 Ang.
Long H...A H-Bond Reported H11 ..N1 3.28 Ang.
Long H...A H-Bond Reported H12O ..N1 3.15 Ang.
Long D...A H-Bond Reported O2 ..O1 4.11 Ang.
Long H...A H-Bond Reported H111 ..O21 3.07 Ang.
RESPONSE: 

These distances do not represent geometrical 
parameters of hydrogen bonds, already distances 
among certain atoms within molecule.

;
# end Validation Reply Form 



_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H13 N3 O2'
_chemical_formula_sum            'C14 H13 N3 O2'
_chemical_formula_weight         255.27

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      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

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

_cell_length_a                   20.911(2)
_cell_length_b                   5.3366(5)
_cell_length_c                   10.8719(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1213.25(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2086
_cell_measurement_theta_min      4.4240
_cell_measurement_theta_max      28.5500

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.398
_exptl_crystal_F_000             536
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.65
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.04
_exptl_absorpt_coefficient_mu    0.097
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.86454
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35.
Empirical absorption correction 
using spherical harmonics,
 implemented in SCALE3 ABSPACK 
scaling algorithm.
;

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10403
_diffrn_reflns_av_unetI/netI     0.0748
_diffrn_reflns_av_R_equivalents  0.0509
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         4.254
_diffrn_reflns_theta_max         27.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             2899
_reflns_number_gt                2038
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.902
_reflns_Friedel_fraction_max     0.997
_reflns_Friedel_fraction_full    0.996

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 

;

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_structure_solution    'SHELXT-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'MERCURY 3.8. (CCDC, 2016)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'

_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)+(0.0152P)²] 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 648 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -1.4(10)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2899
_refine_ls_number_parameters     184
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.0766
_refine_ls_R_factor_gt           0.0470
_refine_ls_wR_factor_ref         0.0802
_refine_ls_wR_factor_gt          0.0698
_refine_ls_goodness_of_fit_ref   0.992
_refine_ls_restrained_S_all      0.992
_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
N1 N 0.31299(13) 0.5763(5) 0.2347(2) 0.0369(7) Uani 1 1 d D . . . .
H1N H 0.3115(15) 0.590(6) 0.314(2) 0.044 Uiso 1 1 d D U . . .
N2 N 0.27382(14) 0.3930(5) 0.1853(2) 0.0373(7) Uani 1 1 d . . . . .
N3 N 0.53734(19) 1.3457(7) 0.3787(3) 0.0629(10) Uani 1 1 d D . . . .
H13N H 0.553(2) 1.456(6) 0.328(3) 0.075 Uiso 1 1 d D U . . .
H23N H 0.5619(19) 1.283(7) 0.435(3) 0.075 Uiso 1 1 d D U . . .
O2 O 0.21075(14) 0.1592(4) 0.0074(2) 0.0493(7) Uani 1 1 d D . . . .
H12O H 0.2352(17) 0.261(6) 0.041(3) 0.059 Uiso 1 1 d D U . . .
O1 O 0.34281(13) 0.7231(5) 0.04775(19) 0.0574(8) Uani 1 1 d . . . . .
C1 C 0.34839(17) 0.7271(6) 0.1599(3) 0.0379(8) Uani 1 1 d . . . . .
C2 C 0.39546(15) 0.8912(6) 0.2226(3) 0.0342(7) Uani 1 1 d . . . . .
C3 C 0.42343(16) 0.8298(6) 0.3353(3) 0.0369(8) Uani 1 1 d . . . . .
H3 H 0.4099 0.6872 0.3770 0.044 Uiso 1 1 calc R U . . .
C4 C 0.47079(17) 0.9773(6) 0.3855(3) 0.0404(9) Uani 1 1 d . . . . .
H4 H 0.4892 0.9320 0.4601 0.048 Uiso 1 1 calc R U . . .
C5 C 0.49141(16) 1.1933(6) 0.3256(3) 0.0399(8) Uani 1 1 d . . . . .
C6 C 0.46401(18) 1.2532(6) 0.2130(4) 0.0450(9) Uani 1 1 d . . . . .
H6 H 0.4777 1.3951 0.1709 0.054 Uiso 1 1 calc R U . . .
C7 C 0.41708(18) 1.1052(6) 0.1633(3) 0.0412(9) Uani 1 1 d . . . . .
H7 H 0.3993 1.1493 0.0879 0.049 Uiso 1 1 calc R U . . .
C8 C 0.24427(17) 0.2536(6) 0.2622(3) 0.0353(8) Uani 1 1 d . . . . .
H8 H 0.2498 0.2813 0.3460 0.042 Uiso 1 1 calc R U . . .
C9 C 0.20226(15) 0.0528(6) 0.2218(3) 0.0326(7) Uani 1 1 d . . . . .
C10 C 0.18683(17) 0.0116(6) 0.0986(3) 0.0362(8) Uani 1 1 d . . . . .
C11 C 0.14608(18) -0.1819(6) 0.0662(3) 0.0459(10) Uani 1 1 d . . . . .
H11 H 0.1355 -0.2064 -0.0160 0.055 Uiso 1 1 calc R U . . .
C12 C 0.12105(18) -0.3387(6) 0.1550(3) 0.0465(10) Uani 1 1 d . . . . .
H12 H 0.0935 -0.4675 0.1324 0.056 Uiso 1 1 calc R U . . .
C13 C 0.13680(19) -0.3050(6) 0.2771(3) 0.0454(9) Uani 1 1 d . . . . .
H13 H 0.1208 -0.4133 0.3367 0.054 Uiso 1 1 calc R U . . .
C14 C 0.17638(17) -0.1101(6) 0.3104(3) 0.0397(8) Uani 1 1 d . . . . .
H14 H 0.1862 -0.0859 0.3930 0.048 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
N1 C1 1.363(4) . ?
N1 N2 1.385(3) . ?
N1 H1N 0.87(2) . ?
N2 C8 1.279(4) . ?
N3 C5 1.384(5) . ?
N3 H13N 0.87(2) . ?
N3 H23N 0.87(2) . ?
O2 C10 1.361(4) . ?
O2 H12O 0.83(2) . ?
O1 C1 1.225(4) . ?
C1 C2 1.484(4) . ?
C2 C7 1.387(4) . ?
C2 C3 1.397(4) . ?
C3 C4 1.378(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.392(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.390(5) . ?
C6 C7 1.371(5) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 C9 1.453(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.395(4) . ?
C9 C14 1.406(4) . ?
C10 C11 1.385(4) . ?
C11 C12 1.381(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.380(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.378(5) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?

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 N2 120.4(3) . . ?
C1 N1 H1N 124(2) . . ?
N2 N1 H1N 115(2) . . ?
C8 N2 N1 116.3(3) . . ?
C5 N3 H13N 113(3) . . ?
C5 N3 H23N 119(3) . . ?
H13N N3 H23N 119(4) . . ?
C10 O2 H12O 107(3) . . ?
O1 C1 N1 122.2(3) . . ?
O1 C1 C2 122.1(3) . . ?
N1 C1 C2 115.7(3) . . ?
C7 C2 C3 117.7(3) . . ?
C7 C2 C1 119.2(3) . . ?
C3 C2 C1 122.9(3) . . ?
C4 C3 C2 121.0(3) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C3 C4 C5 120.7(3) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
N3 C5 C6 121.2(3) . . ?
N3 C5 C4 120.4(3) . . ?
C6 C5 C4 118.3(3) . . ?
C7 C6 C5 120.7(3) . . ?
C7 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
C6 C7 C2 121.6(3) . . ?
C6 C7 H7 119.2 . . ?
C2 C7 H7 119.2 . . ?
N2 C8 C9 121.6(3) . . ?
N2 C8 H8 119.2 . . ?
C9 C8 H8 119.2 . . ?
C10 C9 C14 118.1(3) . . ?
C10 C9 C8 123.1(3) . . ?
C14 C9 C8 118.8(3) . . ?
O2 C10 C11 118.2(3) . . ?
O2 C10 C9 121.5(3) . . ?
C11 C10 C9 120.3(3) . . ?
C12 C11 C10 120.5(3) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C13 C12 C11 120.2(3) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C14 C13 C12 119.6(3) . . ?
C14 C13 H13 120.2 . . ?
C12 C13 H13 120.2 . . ?
C13 C14 C9 121.2(3) . . ?
C13 C14 H14 119.4 . . ?
C9 C14 H14 119.4 . . ?

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
C1 N1 N2 C8 177.3(3) . . . . ?
N2 N1 C1 O1 6.8(5) . . . . ?
N2 N1 C1 C2 -171.5(3) . . . . ?
O1 C1 C2 C7 23.8(5) . . . . ?
N1 C1 C2 C7 -157.9(3) . . . . ?
O1 C1 C2 C3 -150.7(3) . . . . ?
N1 C1 C2 C3 27.6(5) . . . . ?
C7 C2 C3 C4 0.1(5) . . . . ?
C1 C2 C3 C4 174.6(3) . . . . ?
C2 C3 C4 C5 0.8(5) . . . . ?
C3 C4 C5 N3 177.6(3) . . . . ?
C3 C4 C5 C6 -1.4(5) . . . . ?
N3 C5 C6 C7 -177.9(4) . . . . ?
C4 C5 C6 C7 1.1(5) . . . . ?
C5 C6 C7 C2 -0.3(5) . . . . ?
C3 C2 C7 C6 -0.3(5) . . . . ?
C1 C2 C7 C6 -175.1(3) . . . . ?
N1 N2 C8 C9 -179.4(3) . . . . ?
N2 C8 C9 C10 -5.7(5) . . . . ?
N2 C8 C9 C14 173.5(3) . . . . ?
C14 C9 C10 O2 -179.1(3) . . . . ?
C8 C9 C10 O2 0.2(5) . . . . ?
C14 C9 C10 C11 1.3(4) . . . . ?
C8 C9 C10 C11 -179.5(3) . . . . ?
O2 C10 C11 C12 179.3(3) . . . . ?
C9 C10 C11 C12 -1.0(5) . . . . ?
C10 C11 C12 C13 -0.4(6) . . . . ?
C11 C12 C13 C14 1.6(6) . . . . ?
C12 C13 C14 C9 -1.4(5) . . . . ?
C10 C9 C14 C13 -0.1(5) . . . . ?
C8 C9 C14 C13 -179.4(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 O2 0.87(2) 2.19(2) 3.039(3) 169(3) 3
N3 H23N O1 0.87(2) 2.34(3) 3.129(4) 152(4) 2_675
O2 H12O N1 0.83(2) 3.15(3) 3.954(3) 164(3) .
O2 H12O N2 0.83(2) 1.90(3) 2.652(3) 150(4) .
O2 H12O O1 0.83(2) 3.34(3) 4.108(3) 155(3) .
C6 H6 N3 0.93 3.48 4.218(5) 138.2 2_684
C8 H8 O2 0.93 2.80 3.561(4) 140.0 3
C8 H8 O1 0.93 2.94 3.603(4) 129.2 3_545
C11 H11 N1 0.93 3.28 3.952(4) 130.6 3_544

_refine_diff_density_max         0.149
_refine_diff_density_min         -0.144
_refine_diff_density_rms         0.036

####################################################################### 
# 
# 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_3b_exp_1100
_database_code_depnum_ccdc_archive 'CCDC 1588277'
_audit_update_record             
;
2017-11-29 deposited with the CCDC.
2018-02-12 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         'C15 H15 N3 O3'
_chemical_formula_sum            'C15 H15 N3 O3'
_chemical_formula_weight         285.30

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      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

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

_cell_length_a                   9.8994(7)
_cell_length_b                   6.8199(3)
_cell_length_c                   20.3396(15)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1373.19(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2212
_cell_measurement_theta_min      4.5510
_cell_measurement_theta_max      24.2960

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.380
_exptl_crystal_F_000             600
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.62
_exptl_crystal_size_mid          0.14
_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   ?
_exptl_absorpt_correction_T_min  0.80468
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35.
Empirical absorption correction 
using spherical harmonics,
 implemented in SCALE3 ABSPACK 
scaling algorithm.
;

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13177
_diffrn_reflns_av_unetI/netI     0.0627
_diffrn_reflns_av_R_equivalents  0.0625
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         4.237
_diffrn_reflns_theta_max         28.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.848
_diffrn_reflns_point_group_measured_fraction_full 0.873
_reflns_number_total             2797
_reflns_number_gt                1834
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.658
_reflns_Friedel_fraction_max     0.692
_reflns_Friedel_fraction_full    0.744

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 

;

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_structure_solution    'SHELXT-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'MERCURY 3.8. (CCDC, 2016)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'


_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)+(0.0313P)²] 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 484 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.4(10)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2797
_refine_ls_number_parameters     202
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.0926
_refine_ls_R_factor_gt           0.0535
_refine_ls_wR_factor_ref         0.1075
_refine_ls_wR_factor_gt          0.0925
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_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
N1 N 0.5217(3) -1.2636(4) -1.49071(18) 0.0469(9) Uani 1 1 d D . . . .
H1N H 0.467(3) -1.358(4) -1.501(2) 0.056 Uiso 1 1 d D U . . .
N2 N 0.6258(3) -1.2895(4) -1.44654(16) 0.0447(8) Uani 1 1 d . . . . .
N3 N 0.3327(4) -0.7194(6) -1.5228(2) 0.0635(11) Uani 1 1 d D . . . .
H13N H 0.394(4) -0.735(6) -1.492(2) 0.076 Uiso 1 1 d D U . . .
H23N H 0.261(3) -0.654(6) -1.512(2) 0.076 Uiso 1 1 d D U . . .
O1 O 0.5568(3) -0.9359(4) -1.48838(18) 0.0596(8) Uani 1 1 d . . . . .
O2 O 0.8161(3) -1.1527(4) -1.37224(16) 0.0521(8) Uani 1 1 d D . . . .
H12O H 0.748(3) -1.153(6) -1.396(2) 0.063 Uiso 1 1 d D U . . .
O3 O 1.0069(3) -1.2188(3) -1.28605(17) 0.0542(8) Uani 1 1 d . . . . .
C1 C 0.4924(4) -1.0763(5) -1.5103(2) 0.0450(10) Uani 1 1 d . . . . .
C2 C 0.3804(4) -1.0568(6) -1.5578(2) 0.0467(10) Uani 1 1 d . . . . .
C3 C 0.3044(4) -0.8817(6) -1.5610(2) 0.0511(11) Uani 1 1 d . . . . .
C4 C 0.1951(4) -0.8752(7) -1.6059(2) 0.0619(13) Uani 1 1 d . . . . .
H4 H 0.1427 -0.7621 -1.6081 0.074 Uiso 1 1 calc R U . . .
C5 C 0.1643(4) -1.0275(8) -1.6455(3) 0.0688(14) Uani 1 1 d . . . . .
H5 H 0.0914 -1.0179 -1.6742 0.083 Uiso 1 1 calc R U . . .
C6 C 0.2406(5) -1.1989(8) -1.6438(3) 0.0693(14) Uani 1 1 d . . . . .
H6 H 0.2209 -1.3024 -1.6720 0.083 Uiso 1 1 calc R U . . .
C7 C 0.3454(4) -1.2125(7) -1.5997(2) 0.0577(12) Uani 1 1 d . . . . .
H7 H 0.3947 -1.3284 -1.5976 0.069 Uiso 1 1 calc R U . . .
C8 C 0.6471(4) -1.4623(5) -1.4238(2) 0.0452(10) Uani 1 1 d . . . . .
H8 H 0.5919 -1.5658 -1.4367 0.054 Uiso 1 1 calc R U . . .
C9 C 0.7571(4) -1.4968(5) -1.3780(2) 0.0403(8) Uani 1 1 d . . . . .
C10 C 0.8362(4) -1.3434(5) -1.3543(2) 0.0399(9) Uani 1 1 d . . . . .
C11 C 0.9401(4) -1.3811(5) -1.30911(19) 0.0425(10) Uani 1 1 d . . . . .
C12 C 0.9671(4) -1.5725(5) -1.2903(2) 0.0495(10) Uani 1 1 d . . . . .
H12 H 1.0373 -1.5983 -1.2612 0.059 Uiso 1 1 calc R U . . .
C13 C 0.8894(4) -1.7264(5) -1.3148(2) 0.0537(11) Uani 1 1 d . . . . .
H13 H 0.9086 -1.8547 -1.3024 0.064 Uiso 1 1 calc R U . . .
C14 C 0.7840(4) -1.6889(5) -1.3575(2) 0.0493(11) Uani 1 1 d . . . . .
H14 H 0.7307 -1.7916 -1.3727 0.059 Uiso 1 1 calc R U . . .
C15 C 1.1082(5) -1.2512(6) -1.2366(3) 0.0627(12) Uani 1 1 d . . . . .
H15A H 1.1478 -1.1281 -1.2243 0.094 Uiso 1 1 calc R U . . .
H15B H 1.0674 -1.3109 -1.1988 0.094 Uiso 1 1 calc R U . . .
H15C H 1.1769 -1.3363 -1.2538 0.094 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
N1 C1 1.369(4) . ?
N1 N2 1.378(4) . ?
N1 H1N 0.87(2) . ?
N2 C8 1.284(4) . ?
N3 C3 1.382(6) . ?
N3 H13N 0.88(2) . ?
N3 H23N 0.87(2) . ?
O1 C1 1.233(4) . ?
O2 C10 1.365(4) . ?
O2 H12O 0.83(2) . ?
O3 C11 1.371(4) . ?
O3 C15 1.437(5) . ?
C1 C2 1.478(5) . ?
C2 C7 1.405(6) . ?
C2 C3 1.413(5) . ?
C3 C4 1.415(6) . ?
C4 C5 1.350(7) . ?
C4 H4 0.9300 . ?
C5 C6 1.392(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.374(6) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 C9 1.452(6) . ?
C8 H8 0.9300 . ?
C9 C10 1.393(5) . ?
C9 C14 1.400(5) . ?
C10 C11 1.404(5) . ?
C11 C12 1.386(4) . ?
C12 C13 1.394(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.381(6) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 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 N1 N2 117.9(3) . . ?
C1 N1 H1N 119(3) . . ?
N2 N1 H1N 122(3) . . ?
C8 N2 N1 118.4(3) . . ?
C3 N3 H13N 117(3) . . ?
C3 N3 H23N 113(3) . . ?
H13N N3 H23N 116(5) . . ?
C10 O2 H12O 106(3) . . ?
C11 O3 C15 116.8(3) . . ?
O1 C1 N1 120.7(4) . . ?
O1 C1 C2 123.6(3) . . ?
N1 C1 C2 115.7(4) . . ?
C7 C2 C3 118.7(4) . . ?
C7 C2 C1 120.9(4) . . ?
C3 C2 C1 120.4(4) . . ?
N3 C3 C2 122.9(4) . . ?
N3 C3 C4 119.5(4) . . ?
C2 C3 C4 117.6(4) . . ?
C5 C4 C3 122.2(4) . . ?
C5 C4 H4 118.9 . . ?
C3 C4 H4 118.9 . . ?
C4 C5 C6 120.6(5) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C7 C6 C5 118.9(5) . . ?
C7 C6 H6 120.6 . . ?
C5 C6 H6 120.6 . . ?
C6 C7 C2 122.0(4) . . ?
C6 C7 H7 119.0 . . ?
C2 C7 H7 119.0 . . ?
N2 C8 C9 120.2(4) . . ?
N2 C8 H8 119.9 . . ?
C9 C8 H8 119.9 . . ?
C10 C9 C14 119.5(4) . . ?
C10 C9 C8 121.4(3) . . ?
C14 C9 C8 119.0(3) . . ?
O2 C10 C9 122.8(3) . . ?
O2 C10 C11 117.1(3) . . ?
C9 C10 C11 120.1(3) . . ?
O3 C11 C12 125.0(4) . . ?
O3 C11 C10 115.4(3) . . ?
C12 C11 C10 119.6(3) . . ?
C11 C12 C13 120.3(4) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 H12 119.8 . . ?
C14 C13 C12 120.1(3) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C13 C14 C9 120.3(4) . . ?
C13 C14 H14 119.9 . . ?
C9 C14 H14 119.9 . . ?
O3 C15 H15A 109.5 . . ?
O3 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O3 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 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
C1 N1 N2 C8 174.5(4) . . . . ?
N2 N1 C1 O1 -0.6(6) . . . . ?
N2 N1 C1 C2 179.8(4) . . . . ?
O1 C1 C2 C7 155.2(4) . . . . ?
N1 C1 C2 C7 -25.1(5) . . . . ?
O1 C1 C2 C3 -26.2(6) . . . . ?
N1 C1 C2 C3 153.5(4) . . . . ?
C7 C2 C3 N3 -178.7(4) . . . . ?
C1 C2 C3 N3 2.7(6) . . . . ?
C7 C2 C3 C4 1.1(6) . . . . ?
C1 C2 C3 C4 -177.6(4) . . . . ?
N3 C3 C4 C5 178.5(5) . . . . ?
C2 C3 C4 C5 -1.2(7) . . . . ?
C3 C4 C5 C6 -0.3(8) . . . . ?
C4 C5 C6 C7 1.8(8) . . . . ?
C5 C6 C7 C2 -2.0(8) . . . . ?
C3 C2 C7 C6 0.5(7) . . . . ?
C1 C2 C7 C6 179.1(4) . . . . ?
N1 N2 C8 C9 178.9(4) . . . . ?
N2 C8 C9 C10 4.2(6) . . . . ?
N2 C8 C9 C14 -175.6(4) . . . . ?
C14 C9 C10 O2 179.9(4) . . . . ?
C8 C9 C10 O2 0.0(6) . . . . ?
C14 C9 C10 C11 -1.4(6) . . . . ?
C8 C9 C10 C11 178.8(4) . . . . ?
C15 O3 C11 C12 -2.8(6) . . . . ?
C15 O3 C11 C10 176.2(4) . . . . ?
O2 C10 C11 O3 2.4(5) . . . . ?
C9 C10 C11 O3 -176.5(3) . . . . ?
O2 C10 C11 C12 -178.6(4) . . . . ?
C9 C10 C11 C12 2.6(6) . . . . ?
O3 C11 C12 C13 177.4(4) . . . . ?
C10 C11 C12 C13 -1.6(6) . . . . ?
C11 C12 C13 C14 -0.7(7) . . . . ?
C12 C13 C14 C9 2.0(7) . . . . ?
C10 C9 C14 C13 -0.9(6) . . . . ?
C8 C9 C14 C13 178.9(4) . . . . ?

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
N3 H13N O1 0.88(2) 2.12(4) 2.755(5) 129(4) .
N3 H23N O1 0.87(2) 2.17(3) 3.012(5) 165(4) 3_435
O2 H12O N2 0.83(2) 1.84(3) 2.589(5) 150(4) .

_refine_diff_density_max         0.160
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.038

####################################################################### 
# 
# 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_4bEtOHexp1970
_database_code_depnum_ccdc_archive 'CCDC 1588279'
_audit_update_record             
;
2017-11-29 deposited with the CCDC.
2018-02-12 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         ?
_chemical_formula_sum            'C17 H21 N3 O4'
_chemical_formula_weight         331.37

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                   19.2494(10)
_cell_length_b                   12.8121(6)
_cell_length_c                   15.0103(7)
_cell_angle_alpha                90
_cell_angle_beta                 112.476(6)
_cell_angle_gamma                90
_cell_volume                     3420.7(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2897
_cell_measurement_theta_min      4.5130
_cell_measurement_theta_max      27.1470


_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.287
_exptl_crystal_F_000             1408
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.39
_exptl_crystal_size_min          0.08
_exptl_absorpt_coefficient_mu    0.093
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.87735
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35.
Empirical absorption correction 
using spherical harmonics,
 implemented in SCALE3 ABSPACK 
scaling algorithm.
;

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18940
_diffrn_reflns_av_unetI/netI     0.0726
_diffrn_reflns_av_R_equivalents  0.0380
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         4.343
_diffrn_reflns_theta_max         28.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             9062
_reflns_number_gt                5122
_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.

;

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_structure_solution    'SHELXT-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'MERCURY 3.8. (CCDC, 2016)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'


_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)+(0.0518P)²] 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         9062
_refine_ls_number_parameters     467
_refine_ls_number_restraints     10
_refine_ls_R_factor_all          0.1202
_refine_ls_R_factor_gt           0.0594
_refine_ls_wR_factor_ref         0.1373
_refine_ls_wR_factor_gt          0.1142
_refine_ls_goodness_of_fit_ref   0.984
_refine_ls_restrained_S_all      0.984
_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
C11 C 0.50819(10) 0.87134(17) 0.27893(12) 0.0313(4) Uani 1 1 d . . . . .
C12 C 0.53969(10) 0.90807(16) 0.20880(12) 0.0304(4) Uani 1 1 d . . . . .
C13 C 0.54365(11) 0.83855(17) 0.13889(12) 0.0338(5) Uani 1 1 d . . . . .
H13 H 0.5281 0.7682 0.1393 0.041 Uiso 1 1 calc R U . . .
C14 C 0.56972(11) 0.87038(17) 0.06930(13) 0.0350(5) Uani 1 1 d . . . . .
H14 H 0.5715 0.8220 0.0223 0.042 Uiso 1 1 calc R U . . .
C15 C 0.59350(10) 0.97350(17) 0.06764(12) 0.0330(5) Uani 1 1 d . . . . .
C16 C 0.59066(10) 1.04265(17) 0.13845(13) 0.0346(5) Uani 1 1 d . . . . .
H16 H 0.6078 1.1124 0.1396 0.042 Uiso 1 1 calc R U . . .
C17 C 0.56323(11) 1.01073(16) 0.20659(13) 0.0324(4) Uani 1 1 d . . . . .
H17 H 0.5603 1.0595 0.2527 0.039 Uiso 1 1 calc R U . . .
C18 C 0.40920(10) 0.98461(17) 0.40854(12) 0.0324(4) Uani 1 1 d . . . . .
H18 H 0.4074 1.0555 0.3893 0.039 Uiso 1 1 calc R U . . .
C19 C 0.37239(10) 0.95210(16) 0.47283(12) 0.0298(4) Uani 1 1 d . . . . .
C110 C 0.37364(10) 0.84778(17) 0.50044(12) 0.0311(4) Uani 1 1 d . . . . .
C111 C 0.33595(11) 0.81757(18) 0.56056(13) 0.0354(5) Uani 1 1 d . . . . .
C112 C 0.29476(11) 0.88948(19) 0.58795(13) 0.0404(5) Uani 1 1 d . . . . .
H112 H 0.2678 0.8684 0.6263 0.048 Uiso 1 1 calc R U . . .
C113 C 0.29269(11) 0.99313(19) 0.55927(14) 0.0422(6) Uani 1 1 d . . . . .
H113 H 0.2642 1.0425 0.5782 0.051 Uiso 1 1 calc R U . . .
C114 C 0.33152(11) 1.02486(18) 0.50374(12) 0.0384(5) Uani 1 1 d . . . . .
H114 H 0.3307 1.0962 0.4862 0.046 Uiso 1 1 calc R U . . .
C115 C 0.31052(14) 0.6789(2) 0.64955(17) 0.0595(7) Uani 1 1 d . . . . .
H15A H 0.3337 0.7163 0.7108 0.089 Uiso 1 1 calc R U . . .
H15B H 0.3191 0.6038 0.6607 0.089 Uiso 1 1 calc R U . . .
H15C H 0.2563 0.6928 0.6223 0.089 Uiso 1 1 calc R U . . .
N11 N 0.47548(9) 0.94721(14) 0.31401(11) 0.0331(4) Uani 1 1 d D . . . .
N12 N 0.44404(8) 0.91677(13) 0.37812(10) 0.0318(4) Uani 1 1 d . . . . .
N13 N 0.62126(11) 1.00613(16) -0.00035(12) 0.0408(4) Uani 1 1 d D . . . .
O11 O 0.51032(8) 0.78001(12) 0.30590(10) 0.0412(4) Uani 1 1 d . . . . .
O12 O 0.40874(8) 0.77090(12) 0.47090(9) 0.0387(4) Uani 1 1 d D . . . .
O13 O 0.34303(8) 0.71336(12) 0.58392(10) 0.0447(4) Uani 1 1 d . . . . .
O1 O 0.10182(8) 0.39329(12) 0.29589(9) 0.0370(3) Uani 1 1 d D . . . .
C21 C -0.00296(10) 0.64549(16) 0.26773(12) 0.0309(4) Uani 1 1 d . . . . .
C22 C -0.03417(10) 0.60578(16) 0.16785(12) 0.0281(4) Uani 1 1 d . . . . .
C23 C -0.05380(10) 0.50084(16) 0.14756(12) 0.0288(4) Uani 1 1 d . . . . .
H23 H -0.0466 0.4536 0.1991 0.035 Uiso 1 1 calc R U . . .
C24 C -0.08362(10) 0.46466(17) 0.05336(12) 0.0309(4) Uani 1 1 d . . . . .
H24 H -0.0983 0.3936 0.0411 0.037 Uiso 1 1 calc R U . . .
C25 C -0.09229(10) 0.53181(17) -0.02394(12) 0.0298(4) Uani 1 1 d . . . . .
C26 C -0.07248(11) 0.63720(17) -0.00378(12) 0.0322(5) Uani 1 1 d . . . . .
H26 H -0.0783 0.6843 -0.0550 0.039 Uiso 1 1 calc R U . . .
C27 C -0.04444(10) 0.67274(17) 0.09072(12) 0.0318(4) Uani 1 1 d . . . . .
H27 H -0.0319 0.7445 0.1031 0.038 Uiso 1 1 calc R U . . .
C28 C 0.08673(10) 0.52998(17) 0.49582(13) 0.0320(4) Uani 1 1 d . . . . .
H28 H 0.0855 0.4592 0.4763 0.038 Uiso 1 1 calc R U . . .
C29 C 0.11997(10) 0.55661(16) 0.59791(12) 0.0291(4) Uani 1 1 d . . . . .
C210 C 0.12623(10) 0.66059(16) 0.62803(12) 0.0290(4) Uani 1 1 d . . . . .
C211 C 0.16259(10) 0.68538(16) 0.72716(13) 0.0306(4) Uani 1 1 d . . . . .
C212 C 0.19183(11) 0.60635(17) 0.79335(13) 0.0341(5) Uani 1 1 d . . . . .
H212 H 0.2166 0.6227 0.8598 0.041 Uiso 1 1 calc R U . . .
C213 C 0.18534(11) 0.50255(17) 0.76336(13) 0.0358(5) Uani 1 1 d . . . . .
H213 H 0.2056 0.4486 0.8094 0.043 Uiso 1 1 calc R U . . .
C214 C 0.14954(11) 0.47797(17) 0.66704(13) 0.0338(5) Uani 1 1 d . . . . .
H214 H 0.1449 0.4070 0.6474 0.041 Uiso 1 1 calc R U . . .
C215 C 0.20670(14) 0.81988(19) 0.84549(14) 0.0510(6) Uani 1 1 d . . . . .
H25A H 0.1809 0.7917 0.8853 0.076 Uiso 1 1 calc R U . . .
H25B H 0.2084 0.8962 0.8502 0.076 Uiso 1 1 calc R U . . .
H25C H 0.2581 0.7923 0.8683 0.076 Uiso 1 1 calc R U . . .
N21 N 0.03157(9) 0.57223(14) 0.33670(10) 0.0320(4) Uani 1 1 d D . . . .
N22 N 0.05900(8) 0.60161(14) 0.43194(10) 0.0312(4) Uani 1 1 d . . . . .
N23 N -0.12167(10) 0.49475(15) -0.11732(11) 0.0361(4) Uani 1 1 d D . . . .
O21 O -0.00719(8) 0.73747(11) 0.29036(9) 0.0422(4) Uani 1 1 d . . . . .
O22 O 0.10231(8) 0.74243(11) 0.56635(9) 0.0372(4) Uani 1 1 d D . . . .
O23 O 0.16690(8) 0.78975(12) 0.74711(9) 0.0411(4) Uani 1 1 d . . . . .
C1ET C 0.17385(11) 0.35604(19) 0.36022(14) 0.0423(5) Uani 1 1 d . . . . .
H1ET H 0.1664 0.3030 0.4037 0.051 Uiso 1 1 calc R U . . .
H2ET H 0.2023 0.4148 0.4005 0.051 Uiso 1 1 calc R U . . .
C2ET C 0.21900(14) 0.3093(2) 0.30895(18) 0.0641(7) Uani 1 1 d . . . . .
H3ET H 0.1914 0.2506 0.2694 0.096 Uiso 1 1 calc R U . . .
H4ET H 0.2671 0.2845 0.3562 0.096 Uiso 1 1 calc R U . . .
H5ET H 0.2282 0.3621 0.2675 0.096 Uiso 1 1 calc R U . . .
C3ET C 0.33115(13) 0.1519(2) 0.19185(17) 0.0521(6) Uani 1 1 d . . . . .
H6ET H 0.3368 0.1898 0.2517 0.063 Uiso 1 1 calc R U . . .
H7ET H 0.2998 0.0894 0.1880 0.063 Uiso 1 1 calc R U . . .
C4ET C 0.29208(15) 0.2185(3) 0.11004(18) 0.0727(9) Uani 1 1 d . . . . .
H8ET H 0.3194 0.2846 0.1172 0.109 Uiso 1 1 calc R U . . .
H9ET H 0.2411 0.2324 0.1069 0.109 Uiso 1 1 calc R U . . .
H10E H 0.2893 0.1837 0.0506 0.109 Uiso 1 1 calc R U . . .
O2 O 0.40355(8) 0.11863(12) 0.19831(10) 0.0390(4) Uani 1 1 d D . . . .
H10 H 0.0732(11) 0.3438(15) 0.2707(14) 0.047 Uiso 1 1 d D U . . .
H11 H 0.4279(12) 0.1712(14) 0.1966(15) 0.047 Uiso 1 1 d D U . . .
H11N H 0.4622(12) 1.0088(13) 0.2844(14) 0.047 Uiso 1 1 d D U . . .
H12O H 0.4303(11) 0.7984(16) 0.4327(14) 0.047 Uiso 1 1 d D U . . .
H13N H 0.6102(12) 0.9665(16) -0.0528(12) 0.047 Uiso 1 1 d D U . . .
H21N H 0.0453(12) 0.5100(13) 0.3229(14) 0.047 Uiso 1 1 d D U . . .
H23N H 0.6204(13) 1.0728(13) -0.0092(15) 0.047 Uiso 1 1 d D U . . .
H33N H -0.1136(12) 0.5320(16) -0.1611(13) 0.047 Uiso 1 1 d D U . . .
H43N H -0.1221(13) 0.4264(13) -0.1238(15) 0.047 Uiso 1 1 d D U . . .
H22O H 0.0842(12) 0.7155(17) 0.5116(12) 0.047 Uiso 1 1 d D 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
C11 O11 1.234(2) . ?
C11 N11 1.368(2) . ?
C11 C12 1.478(2) . ?
C12 C17 1.396(3) . ?
C12 C13 1.400(3) . ?
C13 C14 1.382(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.402(3) . ?
C14 H14 0.9500 . ?
C15 N13 1.385(2) . ?
C15 C16 1.401(3) . ?
C16 C17 1.380(2) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 N12 1.284(2) . ?
C18 C19 1.459(2) . ?
C18 H18 0.9500 . ?
C19 C110 1.397(3) . ?
C19 C114 1.408(3) . ?
C110 O12 1.361(2) . ?
C110 C111 1.411(3) . ?
C111 O13 1.374(3) . ?
C111 C112 1.377(3) . ?
C112 C113 1.392(3) . ?
C112 H112 0.9500 . ?
C113 C114 1.377(3) . ?
C113 H113 0.9500 . ?
C114 H114 0.9500 . ?
C115 O13 1.425(2) . ?
C115 H15A 0.9800 . ?
C115 H15B 0.9800 . ?
C115 H15C 0.9800 . ?
N11 N12 1.375(2) . ?
N11 H11N 0.894(15) . ?
N13 H13N 0.892(15) . ?
N13 H23N 0.864(15) . ?
O12 H12O 0.899(15) . ?
O1 C1ET 1.435(2) . ?
O1 H10 0.830(15) . ?
C21 O21 1.238(2) . ?
C21 N21 1.367(2) . ?
C21 C22 1.476(2) . ?
C22 C27 1.393(3) . ?
C22 C23 1.398(3) . ?
C23 C24 1.387(2) . ?
C23 H23 0.9500 . ?
C24 C25 1.402(3) . ?
C24 H24 0.9500 . ?
C25 N23 1.380(2) . ?
C25 C26 1.404(3) . ?
C26 C27 1.388(2) . ?
C26 H26 0.9500 . ?
C27 H27 0.9500 . ?
C28 N22 1.287(2) . ?
C28 C29 1.458(2) . ?
C28 H28 0.9500 . ?
C29 C210 1.397(3) . ?
C29 C214 1.402(3) . ?
C210 O22 1.357(2) . ?
C210 C211 1.417(2) . ?
C211 O23 1.366(2) . ?
C211 C212 1.379(3) . ?
C212 C213 1.394(3) . ?
C212 H212 0.9500 . ?
C213 C214 1.379(3) . ?
C213 H213 0.9500 . ?
C214 H214 0.9500 . ?
C215 O23 1.432(2) . ?
C215 H25A 0.9800 . ?
C215 H25B 0.9800 . ?
C215 H25C 0.9800 . ?
N21 N22 1.374(2) . ?
N21 H21N 0.889(15) . ?
N23 H33N 0.873(14) . ?
N23 H43N 0.881(15) . ?
O22 H22O 0.835(15) . ?
C1ET C2ET 1.489(3) . ?
C1ET H1ET 0.9900 . ?
C1ET H2ET 0.9900 . ?
C2ET H3ET 0.9800 . ?
C2ET H4ET 0.9800 . ?
C2ET H5ET 0.9800 . ?
C3ET O2 1.425(2) . ?
C3ET C4ET 1.448(3) . ?
C3ET H6ET 0.9900 . ?
C3ET H7ET 0.9900 . ?
C4ET H8ET 0.9800 . ?
C4ET H9ET 0.9800 . ?
C4ET H10E 0.9800 . ?
O2 H11 0.827(15) . ?

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
O11 C11 N11 120.67(16) . . ?
O11 C11 C12 124.36(18) . . ?
N11 C11 C12 114.97(18) . . ?
C17 C12 C13 118.06(16) . . ?
C17 C12 C11 122.83(17) . . ?
C13 C12 C11 119.06(18) . . ?
C14 C13 C12 121.21(19) . . ?
C14 C13 H13 119.4 . . ?
C12 C13 H13 119.4 . . ?
C13 C14 C15 120.46(18) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 H14 119.8 . . ?
N13 C15 C16 120.4(2) . . ?
N13 C15 C14 121.21(18) . . ?
C16 C15 C14 118.37(16) . . ?
C17 C16 C15 120.8(2) . . ?
C17 C16 H16 119.6 . . ?
C15 C16 H16 119.6 . . ?
C16 C17 C12 121.10(18) . . ?
C16 C17 H17 119.5 . . ?
C12 C17 H17 119.5 . . ?
N12 C18 C19 119.59(19) . . ?
N12 C18 H18 120.2 . . ?
C19 C18 H18 120.2 . . ?
C110 C19 C114 118.96(17) . . ?
C110 C19 C18 120.77(17) . . ?
C114 C19 C18 120.18(19) . . ?
O12 C110 C19 123.38(16) . . ?
O12 C110 C111 116.78(19) . . ?
C19 C110 C111 119.83(18) . . ?
O13 C111 C112 125.90(17) . . ?
O13 C111 C110 113.86(17) . . ?
C112 C111 C110 120.2(2) . . ?
C111 C112 C113 119.85(18) . . ?
C111 C112 H112 120.1 . . ?
C113 C112 H112 120.1 . . ?
C114 C113 C112 120.7(2) . . ?
C114 C113 H113 119.6 . . ?
C112 C113 H113 119.6 . . ?
C113 C114 C19 120.3(2) . . ?
C113 C114 H114 119.8 . . ?
C19 C114 H114 119.8 . . ?
O13 C115 H15A 109.5 . . ?
O13 C115 H15B 109.5 . . ?
H15A C115 H15B 109.5 . . ?
O13 C115 H15C 109.5 . . ?
H15A C115 H15C 109.5 . . ?
H15B C115 H15C 109.5 . . ?
C11 N11 N12 117.28(16) . . ?
C11 N11 H11N 121.5(13) . . ?
N12 N11 H11N 118.7(13) . . ?
C18 N12 N11 119.12(17) . . ?
C15 N13 H13N 116.8(14) . . ?
C15 N13 H23N 115.0(14) . . ?
H13N N13 H23N 116(2) . . ?
C110 O12 H12O 109.4(14) . . ?
C111 O13 C115 116.81(17) . . ?
C1ET O1 H10 110.8(16) . . ?
O21 C21 N21 120.65(16) . . ?
O21 C21 C22 124.27(18) . . ?
N21 C21 C22 115.08(17) . . ?
C27 C22 C23 118.06(16) . . ?
C27 C22 C21 120.35(18) . . ?
C23 C22 C21 121.59(17) . . ?
C24 C23 C22 121.04(18) . . ?
C24 C23 H23 119.5 . . ?
C22 C23 H23 119.5 . . ?
C23 C24 C25 120.70(19) . . ?
C23 C24 H24 119.6 . . ?
C25 C24 H24 119.6 . . ?
N23 C25 C24 120.16(19) . . ?
N23 C25 C26 121.46(18) . . ?
C24 C25 C26 118.35(16) . . ?
C27 C26 C25 120.23(18) . . ?
C27 C26 H26 119.9 . . ?
C25 C26 H26 119.9 . . ?
C26 C27 C22 121.58(19) . . ?
C26 C27 H27 119.2 . . ?
C22 C27 H27 119.2 . . ?
N22 C28 C29 120.45(18) . . ?
N22 C28 H28 119.8 . . ?
C29 C28 H28 119.8 . . ?
C210 C29 C214 119.05(16) . . ?
C210 C29 C28 120.82(18) . . ?
C214 C29 C28 120.06(18) . . ?
O22 C210 C29 123.45(16) . . ?
O22 C210 C211 116.45(18) . . ?
C29 C210 C211 120.02(18) . . ?
O23 C211 C212 125.95(17) . . ?
O23 C211 C210 114.44(17) . . ?
C212 C211 C210 119.58(19) . . ?
C211 C212 C213 120.42(17) . . ?
C211 C212 H212 119.8 . . ?
C213 C212 H212 119.8 . . ?
C214 C213 C212 120.22(19) . . ?
C214 C213 H213 119.9 . . ?
C212 C213 H213 119.9 . . ?
C213 C214 C29 120.71(19) . . ?
C213 C214 H214 119.6 . . ?
C29 C214 H214 119.6 . . ?
O23 C215 H25A 109.5 . . ?
O23 C215 H25B 109.5 . . ?
H25A C215 H25B 109.5 . . ?
O23 C215 H25C 109.5 . . ?
H25A C215 H25C 109.5 . . ?
H25B C215 H25C 109.5 . . ?
C21 N21 N22 118.83(16) . . ?
C21 N21 H21N 122.7(13) . . ?
N22 N21 H21N 117.3(14) . . ?
C28 N22 N21 117.71(17) . . ?
C25 N23 H33N 117.1(14) . . ?
C25 N23 H43N 116.0(14) . . ?
H33N N23 H43N 117(2) . . ?
C210 O22 H22O 104.9(16) . . ?
C211 O23 C215 116.97(16) . . ?
O1 C1ET C2ET 113.00(17) . . ?
O1 C1ET H1ET 109.0 . . ?
C2ET C1ET H1ET 109.0 . . ?
O1 C1ET H2ET 109.0 . . ?
C2ET C1ET H2ET 109.0 . . ?
H1ET C1ET H2ET 107.8 . . ?
C1ET C2ET H3ET 109.5 . . ?
C1ET C2ET H4ET 109.5 . . ?
H3ET C2ET H4ET 109.5 . . ?
C1ET C2ET H5ET 109.5 . . ?
H3ET C2ET H5ET 109.5 . . ?
H4ET C2ET H5ET 109.5 . . ?
O2 C3ET C4ET 114.28(18) . . ?
O2 C3ET H6ET 108.7 . . ?
C4ET C3ET H6ET 108.7 . . ?
O2 C3ET H7ET 108.7 . . ?
C4ET C3ET H7ET 108.7 . . ?
H6ET C3ET H7ET 107.6 . . ?
C3ET C4ET H8ET 109.5 . . ?
C3ET C4ET H9ET 109.5 . . ?
H8ET C4ET H9ET 109.5 . . ?
C3ET C4ET H10E 109.5 . . ?
H8ET C4ET H10E 109.5 . . ?
H9ET C4ET H10E 109.5 . . ?
C3ET O2 H11 107.9(16) . . ?

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
O11 C11 C12 C17 -154.3(2) . . . . ?
N11 C11 C12 C17 25.4(3) . . . . ?
O11 C11 C12 C13 28.2(3) . . . . ?
N11 C11 C12 C13 -152.04(18) . . . . ?
C17 C12 C13 C14 -0.3(3) . . . . ?
C11 C12 C13 C14 177.28(18) . . . . ?
C12 C13 C14 C15 0.5(3) . . . . ?
C13 C14 C15 N13 178.63(18) . . . . ?
C13 C14 C15 C16 0.5(3) . . . . ?
N13 C15 C16 C17 -179.87(18) . . . . ?
C14 C15 C16 C17 -1.7(3) . . . . ?
C15 C16 C17 C12 2.0(3) . . . . ?
C13 C12 C17 C16 -0.9(3) . . . . ?
C11 C12 C17 C16 -178.41(17) . . . . ?
N12 C18 C19 C110 -1.0(3) . . . . ?
N12 C18 C19 C114 -177.53(17) . . . . ?
C114 C19 C110 O12 177.07(16) . . . . ?
C18 C19 C110 O12 0.5(3) . . . . ?
C114 C19 C110 C111 -1.7(3) . . . . ?
C18 C19 C110 C111 -178.29(16) . . . . ?
O12 C110 C111 O13 2.5(2) . . . . ?
C19 C110 C111 O13 -178.64(17) . . . . ?
O12 C110 C111 C112 -175.47(17) . . . . ?
C19 C110 C111 C112 3.4(3) . . . . ?
O13 C111 C112 C113 179.80(19) . . . . ?
C110 C111 C112 C113 -2.5(3) . . . . ?
C111 C112 C113 C114 -0.1(3) . . . . ?
C112 C113 C114 C19 1.8(3) . . . . ?
C110 C19 C114 C113 -0.8(3) . . . . ?
C18 C19 C114 C113 175.78(17) . . . . ?
O11 C11 N11 N12 -1.4(3) . . . . ?
C12 C11 N11 N12 178.80(15) . . . . ?
C19 C18 N12 N11 176.94(15) . . . . ?
C11 N11 N12 C18 -176.20(17) . . . . ?
C112 C111 O13 C115 -6.2(3) . . . . ?
C110 C111 O13 C115 175.99(18) . . . . ?
O21 C21 C22 C27 25.1(3) . . . . ?
N21 C21 C22 C27 -155.56(17) . . . . ?
O21 C21 C22 C23 -155.32(19) . . . . ?
N21 C21 C22 C23 24.0(2) . . . . ?
C27 C22 C23 C24 -0.9(3) . . . . ?
C21 C22 C23 C24 179.49(16) . . . . ?
C22 C23 C24 C25 2.4(3) . . . . ?
C23 C24 C25 N23 179.66(17) . . . . ?
C23 C24 C25 C26 -2.2(3) . . . . ?
N23 C25 C26 C27 178.73(17) . . . . ?
C24 C25 C26 C27 0.6(3) . . . . ?
C25 C26 C27 C22 0.9(3) . . . . ?
C23 C22 C27 C26 -0.7(3) . . . . ?
C21 C22 C27 C26 178.91(17) . . . . ?
N22 C28 C29 C210 -3.6(3) . . . . ?
N22 C28 C29 C214 179.53(17) . . . . ?
C214 C29 C210 O22 177.08(16) . . . . ?
C28 C29 C210 O22 0.2(3) . . . . ?
C214 C29 C210 C211 0.5(3) . . . . ?
C28 C29 C210 C211 -176.37(16) . . . . ?
O22 C210 C211 O23 1.5(2) . . . . ?
C29 C210 C211 O23 178.31(16) . . . . ?
O22 C210 C211 C212 -176.62(16) . . . . ?
C29 C210 C211 C212 0.2(3) . . . . ?
O23 C211 C212 C213 -178.32(18) . . . . ?
C210 C211 C212 C213 -0.5(3) . . . . ?
C211 C212 C213 C214 0.0(3) . . . . ?
C212 C213 C214 C29 0.7(3) . . . . ?
C210 C29 C214 C213 -0.9(3) . . . . ?
C28 C29 C214 C213 175.94(17) . . . . ?
O21 C21 N21 N22 2.5(3) . . . . ?
C22 C21 N21 N22 -176.93(15) . . . . ?
C29 C28 N22 N21 177.10(15) . . . . ?
C21 N21 N22 C28 175.43(17) . . . . ?
C212 C211 O23 C215 1.3(3) . . . . ?
C210 C211 O23 C215 -176.67(16) . . . . ?

_refine_diff_density_max         0.276
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.046

####################################################################### 
# 
# 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_4bH2Oexp3070
_database_code_depnum_ccdc_archive 'CCDC 1588280'
_audit_update_record             
;
2017-11-29 deposited with the CCDC.
2018-02-12 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         ?
_chemical_formula_sum            'C15 H17 N3 O4'
_chemical_formula_weight         303.32

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      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

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

_cell_length_a                   24.185(3)
_cell_length_b                   12.6631(18)
_cell_length_c                   4.7046(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1440.8(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    640
_cell_measurement_theta_min      4.4580
_cell_measurement_theta_max      22.4290

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.398
_exptl_crystal_F_000             640
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.02
_exptl_absorpt_coefficient_mu    0.103
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.49624
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35.
Empirical absorption correction 
using spherical harmonics,
 implemented in SCALE3 ABSPACK 
scaling algorithm.
;

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6479
_diffrn_reflns_av_unetI/netI     0.1906
_diffrn_reflns_av_R_equivalents  0.0864
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_theta_min         4.511
_diffrn_reflns_theta_max         28.499
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_point_group_measured_fraction_full 0.971
_reflns_number_total             3564
_reflns_number_gt                1467
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.751
_reflns_Friedel_fraction_max     0.947
_reflns_Friedel_fraction_full    0.942

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 

;

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_structure_solution    'SHELXT-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'MERCURY 3.8. (CCDC, 2016)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'

_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)] 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 332 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.4(10)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3564
_refine_ls_number_parameters     218
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.2087
_refine_ls_R_factor_gt           0.0769
_refine_ls_wR_factor_ref         0.1091
_refine_ls_wR_factor_gt          0.0780
_refine_ls_goodness_of_fit_ref   0.929
_refine_ls_restrained_S_all      0.929
_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
N1 N 0.7542(2) 0.5287(4) 0.4836(12) 0.0405(15) Uani 1 1 d D . . . .
N2 N 0.71221(17) 0.5620(4) 0.6652(12) 0.0381(13) Uani 1 1 d . . . . .
N3 N 0.9485(2) 0.4636(5) -0.4298(16) 0.0611(19) Uani 1 1 d D . . . .
O1 O 0.77975(15) 0.6977(3) 0.4015(10) 0.0476(12) Uani 1 1 d . . . . .
O2 O 0.63365(16) 0.6909(3) 0.8703(11) 0.0510(13) Uani 1 1 d . . . . .
O3 O 0.54979(16) 0.7159(4) 1.2063(11) 0.0564(14) Uani 1 1 d . . . . .
O4 O 0.7527(2) 0.8050(4) 0.8969(14) 0.0545(12) Uani 1 1 d D . . . .
C1 C 0.7860(2) 0.6021(5) 0.3557(14) 0.0356(15) Uani 1 1 d . . . . .
C2 C 0.8285(2) 0.5628(5) 0.1531(14) 0.0351(15) Uani 1 1 d . . . . .
C3 C 0.8652(2) 0.6340(5) 0.0399(14) 0.0451(18) Uani 1 1 d . . . . .
H3 H 0.8633 0.7046 0.0936 0.054 Uiso 1 1 calc R U . . .
C4 C 0.9050(2) 0.6021(5) -0.1533(15) 0.0479(19) Uani 1 1 d . . . . .
H4 H 0.9299 0.6512 -0.2257 0.057 Uiso 1 1 calc R U . . .
C5 C 0.9081(2) 0.4984(5) -0.2394(14) 0.0422(18) Uani 1 1 d . . . . .
C6 C 0.8715(2) 0.4268(5) -0.1276(16) 0.0532(19) Uani 1 1 d . . . . .
H6 H 0.8732 0.3564 -0.1829 0.064 Uiso 1 1 calc R U . . .
C7 C 0.8321(2) 0.4589(6) 0.0669(16) 0.052(2) Uani 1 1 d . . . . .
H7 H 0.8075 0.4096 0.1409 0.063 Uiso 1 1 calc R U . . .
C8 C 0.6891(2) 0.4873(5) 0.8046(14) 0.0400(18) Uani 1 1 d . . . . .
H8 H 0.7022 0.4187 0.7833 0.048 Uiso 1 1 calc R U . . .
C9 C 0.6431(2) 0.5068(5) 0.9946(13) 0.0360(16) Uani 1 1 d . . . . .
C10 C 0.6181(2) 0.6043(5) 1.0209(14) 0.0380(16) Uani 1 1 d . . . . .
C11 C 0.5725(2) 0.6174(6) 1.2050(15) 0.0418(17) Uani 1 1 d . . . . .
C12 C 0.5550(2) 0.5333(5) 1.3658(16) 0.0423(16) Uani 1 1 d . . . . .
H12 H 0.5260 0.5423 1.4936 0.051 Uiso 1 1 calc R U . . .
C13 C 0.5798(2) 0.4356(5) 1.3401(15) 0.0481(19) Uani 1 1 d . . . . .
H13 H 0.5669 0.3790 1.4470 0.058 Uiso 1 1 calc R U . . .
C14 C 0.6234(2) 0.4217(5) 1.1585(15) 0.0441(17) Uani 1 1 d . . . . .
H14 H 0.6400 0.3557 1.1430 0.053 Uiso 1 1 calc R U . . .
C15 C 0.5111(3) 0.7401(6) 1.4270(18) 0.071(3) Uani 1 1 d . . . . .
H15A H 0.4779 0.7002 1.3982 0.106 Uiso 1 1 calc R U . . .
H15B H 0.5027 0.8142 1.4229 0.106 Uiso 1 1 calc R U . . .
H15C H 0.5269 0.7222 1.6079 0.106 Uiso 1 1 calc R U . . .
H11N H 0.758(3) 0.461(2) 0.471(18) 0.085 Uiso 1 1 d D U . . .
H14O H 0.759(3) 0.765(6) 1.029(13) 0.085 Uiso 1 1 d D U . . .
H13N H 0.965(2) 0.512(4) -0.535(14) 0.085 Uiso 1 1 d D U . . .
H23N H 0.944(3) 0.400(3) -0.485(17) 0.085 Uiso 1 1 d D U . . .
H24O H 0.763(3) 0.774(6) 0.754(11) 0.085 Uiso 1 1 d D U . . .
H12O H 0.670(2) 0.673(5) 0.809(17) 0.085 Uiso 1 1 d . 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
N1 C1 1.349(7) . ?
N1 N2 1.392(6) . ?
N1 H11N 0.86(3) . ?
N2 C8 1.279(7) . ?
N3 C5 1.396(8) . ?
N3 H13N 0.88(3) . ?
N3 H23N 0.85(3) . ?
O1 C1 1.238(7) . ?
O2 C10 1.358(7) . ?
O2 H12O 0.96(6) . ?
O3 C11 1.363(7) . ?
O3 C15 1.430(8) . ?
O4 H14O 0.82(3) . ?
O4 H24O 0.82(3) . ?
C1 C2 1.488(7) . ?
C2 C3 1.372(7) . ?
C2 C7 1.379(8) . ?
C3 C4 1.384(8) . ?
C3 H3 0.9300 . ?
C4 C5 1.377(8) . ?
C4 H4 0.9300 . ?
C5 C6 1.372(8) . ?
C6 C7 1.383(8) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 C9 1.449(7) . ?
C8 H8 0.9300 . ?
C9 C10 1.381(8) . ?
C9 C14 1.409(8) . ?
C10 C11 1.413(8) . ?
C11 C12 1.374(8) . ?
C12 C13 1.381(8) . ?
C12 H12 0.9300 . ?
C13 C14 1.367(8) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 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 N1 N2 118.7(5) . . ?
C1 N1 H11N 126(5) . . ?
N2 N1 H11N 115(5) . . ?
C8 N2 N1 114.1(5) . . ?
C5 N3 H13N 117(5) . . ?
C5 N3 H23N 114(5) . . ?
H13N N3 H23N 123(8) . . ?
C10 O2 H12O 103(4) . . ?
C11 O3 C15 117.5(6) . . ?
H14O O4 H24O 106(7) . . ?
O1 C1 N1 121.8(6) . . ?
O1 C1 C2 121.5(6) . . ?
N1 C1 C2 116.7(6) . . ?
C3 C2 C7 118.2(6) . . ?
C3 C2 C1 118.4(6) . . ?
C7 C2 C1 123.4(6) . . ?
C2 C3 C4 120.8(6) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
C5 C4 C3 120.7(6) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
C6 C5 C4 118.8(6) . . ?
C6 C5 N3 119.3(7) . . ?
C4 C5 N3 121.9(6) . . ?
C5 C6 C7 120.3(7) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 H6 119.9 . . ?
C2 C7 C6 121.2(6) . . ?
C2 C7 H7 119.4 . . ?
C6 C7 H7 119.4 . . ?
N2 C8 C9 121.7(6) . . ?
N2 C8 H8 119.2 . . ?
C9 C8 H8 119.2 . . ?
C10 C9 C14 119.1(6) . . ?
C10 C9 C8 123.0(6) . . ?
C14 C9 C8 117.9(6) . . ?
O2 C10 C9 123.7(5) . . ?
O2 C10 C11 116.2(6) . . ?
C9 C10 C11 120.1(6) . . ?
O3 C11 C12 125.6(6) . . ?
O3 C11 C10 115.2(6) . . ?
C12 C11 C10 119.2(6) . . ?
C11 C12 C13 120.8(6) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 H12 119.6 . . ?
C14 C13 C12 120.4(6) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C13 C14 C9 120.3(6) . . ?
C13 C14 H14 119.8 . . ?
C9 C14 H14 119.8 . . ?
O3 C15 H15A 109.5 . . ?
O3 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O3 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 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
C1 N1 N2 C8 -171.3(6) . . . . ?
N2 N1 C1 O1 1.9(9) . . . . ?
N2 N1 C1 C2 -177.2(5) . . . . ?
O1 C1 C2 C3 7.1(9) . . . . ?
N1 C1 C2 C3 -173.8(6) . . . . ?
O1 C1 C2 C7 -171.0(6) . . . . ?
N1 C1 C2 C7 8.1(9) . . . . ?
C7 C2 C3 C4 -0.7(9) . . . . ?
C1 C2 C3 C4 -178.9(6) . . . . ?
C2 C3 C4 C5 1.0(10) . . . . ?
C3 C4 C5 C6 -0.8(10) . . . . ?
C3 C4 C5 N3 -178.8(6) . . . . ?
C4 C5 C6 C7 0.3(10) . . . . ?
N3 C5 C6 C7 178.3(7) . . . . ?
C3 C2 C7 C6 0.2(10) . . . . ?
C1 C2 C7 C6 178.3(6) . . . . ?
C5 C6 C7 C2 0.0(11) . . . . ?
N1 N2 C8 C9 -177.4(5) . . . . ?
N2 C8 C9 C10 5.6(9) . . . . ?
N2 C8 C9 C14 -174.5(6) . . . . ?
C14 C9 C10 O2 -179.2(6) . . . . ?
C8 C9 C10 O2 0.7(9) . . . . ?
C14 C9 C10 C11 -1.5(9) . . . . ?
C8 C9 C10 C11 178.4(5) . . . . ?
C15 O3 C11 C12 11.8(9) . . . . ?
C15 O3 C11 C10 -167.7(6) . . . . ?
O2 C10 C11 O3 0.2(8) . . . . ?
C9 C10 C11 O3 -177.6(6) . . . . ?
O2 C10 C11 C12 -179.4(6) . . . . ?
C9 C10 C11 C12 2.8(9) . . . . ?
O3 C11 C12 C13 177.6(6) . . . . ?
C10 C11 C12 C13 -2.8(10) . . . . ?
C11 C12 C13 C14 1.6(10) . . . . ?
C12 C13 C14 C9 -0.3(10) . . . . ?
C10 C9 C14 C13 0.2(9) . . . . ?
C8 C9 C14 C13 -179.6(6) . . . . ?

_refine_diff_density_max         0.177
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.045

####################################################################### 
# 
# 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_2cMeOHexp2628
_database_code_depnum_ccdc_archive 'CCDC 1588276'
_audit_update_record             
;
2017-11-29 deposited with the CCDC.
2018-02-12 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         'C14 H13 N3 O3, C H4 O'
_chemical_formula_sum            'C15 H17 N3 O4'
_chemical_formula_weight         303.32

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                   15.6285(5)
_cell_length_b                   12.4516(4)
_cell_length_c                   7.3947(3)
_cell_angle_alpha                90
_cell_angle_beta                 93.187(3)
_cell_angle_gamma                90
_cell_volume                     1436.78(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2026
_cell_measurement_theta_min      4.5300
_cell_measurement_theta_max      31.7320


_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.402
_exptl_crystal_F_000             640
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.11
_exptl_absorpt_coefficient_mu    0.104
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.95575
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35.
Empirical absorption correction 
using spherical harmonics,
 implemented in SCALE3 ABSPACK 
scaling algorithm.
;


_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6958
_diffrn_reflns_av_unetI/netI     0.0381
_diffrn_reflns_av_R_equivalents  0.0237
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         4.188
_diffrn_reflns_theta_max         28.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             3460
_reflns_number_gt                2589
_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.
 
 
;

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_structure_solution    'SHELXT-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'MERCURY 3.8. (CCDC, 2016)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'

_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)+(0.0501P)²+0.1481P] 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         3460
_refine_ls_number_parameters     210
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0651
_refine_ls_R_factor_gt           0.0449
_refine_ls_wR_factor_ref         0.1148
_refine_ls_wR_factor_gt          0.1046
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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 0.66592(7) 0.58257(8) 0.28935(16) 0.0406(3) Uani 1 1 d . . . . .
O2 O 0.89967(6) 0.58916(8) 0.51362(16) 0.0350(3) Uani 1 1 d . . . . .
O3 O 1.16798(6) 0.72957(8) 0.74504(15) 0.0330(3) Uani 1 1 d . . . . .
O4 O 0.31393(7) 0.48075(8) 0.13709(16) 0.0357(3) Uani 1 1 d . . . . .
N1 N 0.69853(7) 0.75578(10) 0.35776(16) 0.0255(3) Uani 1 1 d . . . . .
N2 N 0.77978(7) 0.72706(9) 0.42433(16) 0.0255(3) Uani 1 1 d . . . . .
N3 N 0.42371(8) 0.65118(10) 0.08376(17) 0.0333(3) Uani 1 1 d . . . . .
C1 C 0.64624(9) 0.67754(11) 0.28887(19) 0.0257(3) Uani 1 1 d . . . . .
C2 C 0.56021(8) 0.71358(11) 0.21119(18) 0.0236(3) Uani 1 1 d . . . . .
C3 C 0.50344(9) 0.63332(12) 0.15190(19) 0.0292(3) Uani 1 1 d . . . . .
H3 H 0.5226 0.5610 0.1604 0.035 Uiso 1 1 calc R U . . .
C4 C 0.39794(9) 0.75353(13) 0.0714(2) 0.0317(3) Uani 1 1 d . . . . .
H4 H 0.3414 0.7681 0.0241 0.038 Uiso 1 1 calc R U . . .
C5 C 0.44970(9) 0.83877(12) 0.1242(2) 0.0330(4) Uani 1 1 d . . . . .
H5 H 0.4291 0.9103 0.1123 0.040 Uiso 1 1 calc R U . . .
C6 C 0.53196(9) 0.81894(12) 0.1947(2) 0.0290(3) Uani 1 1 d . . . . .
H6 H 0.5687 0.8767 0.2313 0.035 Uiso 1 1 calc R U . . .
C7 C 0.82962(8) 0.80322(11) 0.48344(18) 0.0253(3) Uani 1 1 d . . . . .
H7 H 0.8092 0.8751 0.4828 0.030 Uiso 1 1 calc R U . . .
C8 C 0.91616(8) 0.78026(11) 0.55066(18) 0.0232(3) Uani 1 1 d . . . . .
C9 C 0.94849(8) 0.67547(11) 0.56328(19) 0.0246(3) Uani 1 1 d . . . . .
C10 C 1.03228(8) 0.65553(11) 0.62816(19) 0.0268(3) Uani 1 1 d . . . . .
H10 H 1.0533 0.5840 0.6362 0.032 Uiso 1 1 calc R U . . .
C11 C 1.08471(8) 0.74083(11) 0.68082(18) 0.0256(3) Uani 1 1 d . . . . .
C12 C 1.05403(9) 0.84608(12) 0.6701(2) 0.0298(3) Uani 1 1 d . . . . .
H12 H 1.0901 0.9045 0.7068 0.036 Uiso 1 1 calc R U . . .
C13 C 0.97124(9) 0.86424(11) 0.60576(19) 0.0283(3) Uani 1 1 d . . . . .
H13 H 0.9507 0.9360 0.5984 0.034 Uiso 1 1 calc R U . . .
C14 C 1.20078(10) 0.62299(13) 0.7650(2) 0.0399(4) Uani 1 1 d . . . . .
H14A H 1.1673 0.5834 0.8512 0.060 Uiso 1 1 calc R U . . .
H14B H 1.2609 0.6259 0.8100 0.060 Uiso 1 1 calc R U . . .
H14C H 1.1966 0.5865 0.6473 0.060 Uiso 1 1 calc R U . . .
C15 C 0.27700(11) 0.52378(14) 0.2925(2) 0.0431(4) Uani 1 1 d . . . . .
H15A H 0.3186 0.5198 0.3964 0.065 Uiso 1 1 calc R U . . .
H15B H 0.2258 0.4823 0.3186 0.065 Uiso 1 1 calc R U . . .
H15C H 0.2610 0.5989 0.2699 0.065 Uiso 1 1 calc R U . . .
H11N H 0.6852(11) 0.8266(16) 0.361(2) 0.052 Uiso 1 1 d . U . . .
H12O H 0.8511(13) 0.6144(15) 0.475(2) 0.052 Uiso 1 1 d . U . . .
H14O H 0.3457(12) 0.5306(15) 0.094(3) 0.052 Uiso 1 1 d . 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 1.2217(16) . ?
O2 C9 1.3568(16) . ?
O2 H12O 0.86(2) . ?
O3 C11 1.3676(16) . ?
O3 C14 1.4273(18) . ?
O4 C15 1.420(2) . ?
O4 H14O 0.867(19) . ?
N1 C1 1.3528(18) . ?
N1 N2 1.3833(15) . ?
N1 H11N 0.906(19) . ?
N2 C7 1.2880(17) . ?
N3 C3 1.3365(18) . ?
N3 C4 1.3381(19) . ?
C1 C2 1.5010(18) . ?
C2 C6 1.3875(19) . ?
C2 C3 1.3910(19) . ?
C3 H3 0.9500 . ?
C4 C5 1.378(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.3825(19) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.4433(18) . ?
C7 H7 0.9500 . ?
C8 C9 1.4005(18) . ?
C8 C13 1.4006(18) . ?
C9 C10 1.3917(18) . ?
C10 C11 1.3840(19) . ?
C10 H10 0.9500 . ?
C11 C12 1.3961(19) . ?
C12 C13 1.3721(19) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?

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
C9 O2 H12O 105.9(13) . . ?
C11 O3 C14 117.43(11) . . ?
C15 O4 H14O 107.2(12) . . ?
C1 N1 N2 118.11(11) . . ?
C1 N1 H11N 125.1(11) . . ?
N2 N1 H11N 116.8(11) . . ?
C7 N2 N1 117.15(11) . . ?
C3 N3 C4 117.07(12) . . ?
O1 C1 N1 123.31(13) . . ?
O1 C1 C2 120.69(12) . . ?
N1 C1 C2 115.99(12) . . ?
C6 C2 C3 117.22(12) . . ?
C6 C2 C1 126.17(12) . . ?
C3 C2 C1 116.61(12) . . ?
N3 C3 C2 124.35(13) . . ?
N3 C3 H3 117.8 . . ?
C2 C3 H3 117.8 . . ?
N3 C4 C5 123.00(13) . . ?
N3 C4 H4 118.5 . . ?
C5 C4 H4 118.5 . . ?
C4 C5 C6 119.23(13) . . ?
C4 C5 H5 120.4 . . ?
C6 C5 H5 120.4 . . ?
C5 C6 C2 119.13(13) . . ?
C5 C6 H6 120.4 . . ?
C2 C6 H6 120.4 . . ?
N2 C7 C8 120.56(13) . . ?
N2 C7 H7 119.7 . . ?
C8 C7 H7 119.7 . . ?
C9 C8 C13 117.55(12) . . ?
C9 C8 C7 122.36(12) . . ?
C13 C8 C7 120.09(12) . . ?
O2 C9 C10 117.15(12) . . ?
O2 C9 C8 121.63(12) . . ?
C10 C9 C8 121.22(12) . . ?
C11 C10 C9 119.41(12) . . ?
C11 C10 H10 120.3 . . ?
C9 C10 H10 120.3 . . ?
O3 C11 C10 123.78(12) . . ?
O3 C11 C12 115.67(12) . . ?
C10 C11 C12 120.55(12) . . ?
C13 C12 C11 119.25(13) . . ?
C13 C12 H12 120.4 . . ?
C11 C12 H12 120.4 . . ?
C12 C13 C8 122.02(13) . . ?
C12 C13 H13 119.0 . . ?
C8 C13 H13 119.0 . . ?
O3 C14 H14A 109.5 . . ?
O3 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O3 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O4 C15 H15A 109.5 . . ?
O4 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O4 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 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
C1 N1 N2 C7 177.61(12) . . . . ?
N2 N1 C1 O1 3.1(2) . . . . ?
N2 N1 C1 C2 -177.47(11) . . . . ?
O1 C1 C2 C6 -176.64(14) . . . . ?
N1 C1 C2 C6 3.9(2) . . . . ?
O1 C1 C2 C3 4.0(2) . . . . ?
N1 C1 C2 C3 -175.46(12) . . . . ?
C4 N3 C3 C2 0.5(2) . . . . ?
C6 C2 C3 N3 -1.2(2) . . . . ?
C1 C2 C3 N3 178.20(13) . . . . ?
C3 N3 C4 C5 0.4(2) . . . . ?
N3 C4 C5 C6 -0.5(2) . . . . ?
C4 C5 C6 C2 -0.3(2) . . . . ?
C3 C2 C6 C5 1.1(2) . . . . ?
C1 C2 C6 C5 -178.31(13) . . . . ?
N1 N2 C7 C8 -178.36(12) . . . . ?
N2 C7 C8 C9 -3.2(2) . . . . ?
N2 C7 C8 C13 176.65(13) . . . . ?
C13 C8 C9 O2 179.76(13) . . . . ?
C7 C8 C9 O2 -0.4(2) . . . . ?
C13 C8 C9 C10 0.0(2) . . . . ?
C7 C8 C9 C10 179.83(12) . . . . ?
O2 C9 C10 C11 -179.92(13) . . . . ?
C8 C9 C10 C11 -0.1(2) . . . . ?
C14 O3 C11 C10 -2.6(2) . . . . ?
C14 O3 C11 C12 177.57(13) . . . . ?
C9 C10 C11 O3 -179.53(12) . . . . ?
C9 C10 C11 C12 0.3(2) . . . . ?
O3 C11 C12 C13 179.55(12) . . . . ?
C10 C11 C12 C13 -0.3(2) . . . . ?
C11 C12 C13 C8 0.1(2) . . . . ?
C9 C8 C13 C12 0.0(2) . . . . ?
C7 C8 C13 C12 -179.83(13) . . . . ?

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 H6 O4 0.95 2.41 3.328(2) 163.2 2_655
C7 H7 O4 0.95 2.46 3.2392(17) 139.7 2_655
C10 H10 O2 0.95 2.55 3.4113(18) 150.7 3_766
C15 H15A O1 0.98 2.65 3.435(2) 137.4 3_666
C15 H15B O2 0.98 2.54 3.478(2) 160.3 3_666
C15 H15C O3 0.98 2.58 3.520(2) 159.7 4_475
N1 H11N O4 0.906(19) 1.92(2) 2.8084(16) 166.3(17) 2_655
O2 H12O N2 0.86(2) 1.82(2) 2.5995(15) 151.1(18) .
O4 H14O N3 0.867(19) 1.94(2) 2.7708(16) 160.5(17) .

_refine_diff_density_max         0.246
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.041

####################################################################### 
# 
# 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_4c_exp_1978
_database_code_depnum_ccdc_archive 'CCDC 1588282'
_audit_update_record             
;
2017-11-29 deposited with the CCDC.
2018-02-12 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         ?
_chemical_formula_sum            'C15 H15 N3 O3'
_chemical_formula_weight         285.30

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           7
_space_group_name_H-M_alt        'P c'
_space_group_name_Hall           'P -2yc'

_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+1/2'

_cell_length_a                   11.9715(5)
_cell_length_b                   12.5059(6)
_cell_length_c                   9.3710(4)
_cell_angle_alpha                90
_cell_angle_beta                 97.453(4)
_cell_angle_gamma                90
_cell_volume                     1391.12(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2564
_cell_measurement_theta_min      4.5920
_cell_measurement_theta_max      23.6170


_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.362
_exptl_crystal_F_000             600
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.59
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.12
_exptl_absorpt_coefficient_mu    0.097
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.81891
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35.
Empirical absorption correction 
using spherical harmonics,
 implemented in SCALE3 ABSPACK 
scaling algorithm.
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15432
_diffrn_reflns_av_unetI/netI     0.0890
_diffrn_reflns_av_R_equivalents  0.0488
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         4.400
_diffrn_reflns_theta_max         28.997
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.869
_diffrn_reflns_point_group_measured_fraction_full 0.901
_reflns_number_total             6435
_reflns_number_gt                3484
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.741
_reflns_Friedel_fraction_max     0.742
_reflns_Friedel_fraction_full    0.806

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 

;

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_structure_solution    'SHELXT-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'MERCURY 3.8. (CCDC, 2016)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'

_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)+(0.0205P)²] 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 1038 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.2(9)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         6435
_refine_ls_number_parameters     408
_refine_ls_number_restraints     9
_refine_ls_R_factor_all          0.1242
_refine_ls_R_factor_gt           0.0552
_refine_ls_wR_factor_ref         0.0969
_refine_ls_wR_factor_gt          0.0779
_refine_ls_goodness_of_fit_ref   0.971
_refine_ls_restrained_S_all      0.970
_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
N21 N 0.4603(3) 0.4833(3) 0.5328(4) 0.0482(9) Uani 1 1 d . . . . .
N22 N 0.5640(3) 0.4548(3) 0.4959(3) 0.0467(9) Uani 1 1 d . . . . .
N23 N -0.0626(3) 0.5944(4) 0.5462(5) 0.0682(12) Uani 1 1 d D . . . .
O21 O 0.4235(2) 0.5867(3) 0.3335(3) 0.0586(8) Uani 1 1 d . . . . .
O22 O 0.7176(3) 0.4451(3) 0.3212(3) 0.0645(10) Uani 1 1 d D . . . .
O23 O 1.0356(2) 0.2227(3) 0.4634(3) 0.0689(10) Uani 1 1 d . . . . .
C115 C 0.3898(4) 0.2622(5) 0.2781(5) 0.0706(16) Uani 1 1 d . . . . .
H15A H 0.3683 0.1884 0.2816 0.106 Uiso 1 1 calc R U . . .
H15B H 0.3239 0.3052 0.2515 0.106 Uiso 1 1 calc R U . . .
H15C H 0.4258 0.2841 0.3710 0.106 Uiso 1 1 calc R U . . .
C215 C 1.0855(4) 0.2539(4) 0.3394(6) 0.0722(15) Uani 1 1 d . . . . .
H15D H 1.0335 0.2407 0.2543 0.108 Uiso 1 1 calc R U . . .
H15E H 1.1531 0.2133 0.3350 0.108 Uiso 1 1 calc R U . . .
H15F H 1.1036 0.3287 0.3454 0.108 Uiso 1 1 calc R U . . .
C11 C 1.1117(3) 0.0213(4) 0.0343(4) 0.0428(10) Uani 1 1 d . . . . .
C12 C 1.2256(3) -0.0244(3) 0.0706(4) 0.0399(10) Uani 1 1 d . . . . .
C13 C 1.3154(3) 0.0282(4) 0.0222(4) 0.0523(11) Uani 1 1 d . . . . .
H13 H 1.3017 0.0880 -0.0363 0.063 Uiso 1 1 calc R U . . .
C14 C 1.4244(4) -0.0064(4) 0.0589(5) 0.0566(12) Uani 1 1 d . . . . .
H14 H 1.4831 0.0311 0.0260 0.068 Uiso 1 1 calc R U . . .
C15 C 1.4479(3) -0.0955(4) 0.1436(4) 0.0493(11) Uani 1 1 d . . . . .
C16 C 1.3578(3) -0.1526(4) 0.1869(4) 0.0533(12) Uani 1 1 d . . . . .
H16 H 1.3713 -0.2155 0.2393 0.064 Uiso 1 1 calc R U . . .
C17 C 1.2491(3) -0.1159(4) 0.1522(4) 0.0516(12) Uani 1 1 d . . . . .
H17 H 1.1901 -0.1535 0.1843 0.062 Uiso 1 1 calc R U . . .
C18 C 0.8747(3) 0.0523(4) 0.2154(4) 0.0476(11) Uani 1 1 d . . . . .
H18 H 0.8995 0.0135 0.2981 0.057 Uiso 1 1 calc R U . . .
C19 C 0.7671(3) 0.1070(3) 0.2027(4) 0.0410(10) Uani 1 1 d . . . . .
C110 C 0.7287(3) 0.1724(4) 0.0846(4) 0.0445(10) Uani 1 1 d . . . . .
C111 C 0.6291(3) 0.2280(4) 0.0789(4) 0.0494(11) Uani 1 1 d . . . . .
H111 H 0.6050 0.2710 -0.0001 0.059 Uiso 1 1 calc R U . . .
C112 C 0.5641(4) 0.2197(4) 0.1918(4) 0.0505(11) Uani 1 1 d . . . . .
C113 C 0.6005(3) 0.1557(4) 0.3106(4) 0.0540(12) Uani 1 1 d . . . . .
H113 H 0.5576 0.1497 0.3861 0.065 Uiso 1 1 calc R U . . .
C114 C 0.7009(3) 0.1017(4) 0.3145(4) 0.0493(11) Uani 1 1 d . . . . .
H114 H 0.7255 0.0600 0.3947 0.059 Uiso 1 1 calc R U . . .
N11 N 1.0416(3) 0.0106(3) 0.1369(3) 0.0454(9) Uani 1 1 d D . . . .
N12 N 0.9358(3) 0.0572(3) 0.1126(3) 0.0447(9) Uani 1 1 d . . . . .
N13 N 1.5584(4) -0.1309(4) 0.1810(5) 0.0715(13) Uani 1 1 d D . . . .
O11 O 1.0808(2) 0.0695(2) -0.0791(3) 0.0521(8) Uani 1 1 d . . . . .
O12 O 0.7893(3) 0.1832(3) -0.0289(3) 0.0591(9) Uani 1 1 d D . . . .
O13 O 0.4660(2) 0.2756(3) 0.1740(3) 0.0688(10) Uani 1 1 d . . . . .
H11N H 1.071(3) -0.016(3) 0.217(3) 0.044(12) Uiso 1 1 d D . . . .
H12O H 0.854(3) 0.152(4) -0.011(5) 0.090(19) Uiso 1 1 d D . . . .
H13N H 1.610(5) -0.082(4) 0.177(8) 0.16(3) Uiso 1 1 d D . . . .
C21 C 0.3916(3) 0.5463(4) 0.4414(4) 0.0466(10) Uani 1 1 d . . . . .
C22 C 0.2757(3) 0.5592(4) 0.4779(4) 0.0448(10) Uani 1 1 d . . . . .
C23 C 0.2241(3) 0.4849(4) 0.5569(4) 0.0520(11) Uani 1 1 d . . . . .
H23 H 0.2652 0.4261 0.5953 0.062 Uiso 1 1 calc R U . . .
C24 C 0.1124(4) 0.4958(4) 0.5805(5) 0.0592(13) Uani 1 1 d . . . . .
H24 H 0.0799 0.4448 0.6345 0.071 Uiso 1 1 calc R U . . .
C25 C 0.0490(4) 0.5828(4) 0.5237(5) 0.0508(12) Uani 1 1 d . . . . .
C26 C 0.1013(4) 0.6595(4) 0.4482(5) 0.0595(13) Uani 1 1 d . . . . .
H26 H 0.0617 0.7199 0.4129 0.071 Uiso 1 1 calc R U . . .
C27 C 0.2119(3) 0.6462(4) 0.4254(5) 0.0579(13) Uani 1 1 d . . . . .
H27 H 0.2449 0.6977 0.3727 0.069 Uiso 1 1 calc R U . . .
C28 C 0.6269(3) 0.3974(4) 0.5852(4) 0.0453(10) Uani 1 1 d . . . . .
H28 H 0.6035 0.3808 0.6734 0.054 Uiso 1 1 calc R U . . .
C29 C 0.7342(3) 0.3574(3) 0.5521(4) 0.0428(10) Uani 1 1 d . . . . .
C210 C 0.7746(3) 0.3804(3) 0.4212(4) 0.0459(11) Uani 1 1 d . . . . .
C211 C 0.8748(3) 0.3373(4) 0.3890(4) 0.0507(11) Uani 1 1 d . . . . .
H211 H 0.9005 0.3532 0.3019 0.061 Uiso 1 1 calc R U . . .
C212 C 0.9364(3) 0.2707(4) 0.4866(5) 0.0517(11) Uani 1 1 d . . . . .
C213 C 0.8983(4) 0.2465(4) 0.6165(5) 0.0573(12) Uani 1 1 d . . . . .
H213 H 0.9400 0.2015 0.6823 0.069 Uiso 1 1 calc R U . . .
C214 C 0.7989(3) 0.2893(4) 0.6473(4) 0.0520(12) Uani 1 1 d . . . . .
H214 H 0.7737 0.2724 0.7343 0.062 Uiso 1 1 calc R U . . .
H21N H 0.443(3) 0.466(4) 0.619(4) 0.062 Uiso 1 1 d . U . . .
H22O H 0.658(2) 0.462(4) 0.351(4) 0.062 Uiso 1 1 d D U . . .
H23N H 1.571(4) -0.174(3) 0.252(4) 0.062 Uiso 1 1 d D U . . .
H33N H -0.094(3) 0.534(2) 0.568(5) 0.062 Uiso 1 1 d D U . . .
H43N H -0.099(3) 0.644(3) 0.497(4) 0.062 Uiso 1 1 d D 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
N21 C21 1.359(5) . ?
N21 N22 1.378(4) . ?
N21 H21N 0.88(4) . ?
N22 C28 1.273(5) . ?
N23 C25 1.388(6) . ?
N23 H33N 0.88(2) . ?
N23 H43N 0.86(2) . ?
O21 C21 1.234(5) . ?
O22 C210 1.353(5) . ?
O22 H22O 0.83(2) . ?
O23 C212 1.373(4) . ?
O23 C215 1.429(5) . ?
C115 O13 1.429(4) . ?
C115 H15A 0.9600 . ?
C115 H15B 0.9600 . ?
C115 H15C 0.9600 . ?
C215 H15D 0.9600 . ?
C215 H15E 0.9600 . ?
C215 H15F 0.9600 . ?
C11 O11 1.236(4) . ?
C11 N11 1.362(4) . ?
C11 C12 1.478(5) . ?
C12 C17 1.385(5) . ?
C12 C13 1.385(5) . ?
C13 C14 1.375(6) . ?
C13 H13 0.9300 . ?
C14 C15 1.376(6) . ?
C14 H14 0.9300 . ?
C15 N13 1.397(6) . ?
C15 C16 1.397(6) . ?
C16 C17 1.379(5) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 N12 1.284(4) . ?
C18 C19 1.450(5) . ?
C18 H18 0.9300 . ?
C19 C114 1.395(5) . ?
C19 C110 1.405(5) . ?
C110 O12 1.370(4) . ?
C110 C111 1.375(5) . ?
C111 C112 1.396(5) . ?
C111 H111 0.9300 . ?
C112 O13 1.359(5) . ?
C112 C113 1.394(6) . ?
C113 C114 1.375(5) . ?
C113 H113 0.9300 . ?
C114 H114 0.9300 . ?
N11 N12 1.386(4) . ?
N11 H11N 0.85(2) . ?
N13 H13N 0.88(3) . ?
N13 H23N 0.86(2) . ?
O12 H12O 0.86(2) . ?
C21 C22 1.480(5) . ?
C22 C27 1.383(6) . ?
C22 C23 1.383(5) . ?
C23 C24 1.390(5) . ?
C23 H23 0.9300 . ?
C24 C25 1.393(6) . ?
C24 H24 0.9300 . ?
C25 C26 1.388(6) . ?
C26 C27 1.378(5) . ?
C26 H26 0.9300 . ?
C27 H27 0.9300 . ?
C28 C29 1.449(5) . ?
C28 H28 0.9300 . ?
C29 C214 1.393(5) . ?
C29 C210 1.406(5) . ?
C210 C211 1.384(5) . ?
C211 C212 1.378(5) . ?
C211 H211 0.9300 . ?
C212 C213 1.388(6) . ?
C213 C214 1.370(6) . ?
C213 H213 0.9300 . ?
C214 H214 0.9300 . ?

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
C21 N21 N22 118.9(3) . . ?
C21 N21 H21N 121(3) . . ?
N22 N21 H21N 119(3) . . ?
C28 N22 N21 117.1(3) . . ?
C25 N23 H33N 113(3) . . ?
C25 N23 H43N 115(3) . . ?
H33N N23 H43N 123(4) . . ?
C210 O22 H22O 107(3) . . ?
C212 O23 C215 118.1(3) . . ?
O13 C115 H15A 109.5 . . ?
O13 C115 H15B 109.5 . . ?
H15A C115 H15B 109.5 . . ?
O13 C115 H15C 109.5 . . ?
H15A C115 H15C 109.5 . . ?
H15B C115 H15C 109.5 . . ?
O23 C215 H15D 109.5 . . ?
O23 C215 H15E 109.5 . . ?
H15D C215 H15E 109.5 . . ?
O23 C215 H15F 109.5 . . ?
H15D C215 H15F 109.5 . . ?
H15E C215 H15F 109.5 . . ?
O11 C11 N11 120.9(4) . . ?
O11 C11 C12 123.4(3) . . ?
N11 C11 C12 115.7(3) . . ?
C17 C12 C13 117.5(4) . . ?
C17 C12 C11 124.2(4) . . ?
C13 C12 C11 118.3(4) . . ?
C14 C13 C12 121.4(4) . . ?
C14 C13 H13 119.3 . . ?
C12 C13 H13 119.3 . . ?
C13 C14 C15 121.0(4) . . ?
C13 C14 H14 119.5 . . ?
C15 C14 H14 119.5 . . ?
C14 C15 N13 121.2(4) . . ?
C14 C15 C16 118.3(4) . . ?
N13 C15 C16 120.4(5) . . ?
C17 C16 C15 120.1(4) . . ?
C17 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
C16 C17 C12 121.5(4) . . ?
C16 C17 H17 119.2 . . ?
C12 C17 H17 119.2 . . ?
N12 C18 C19 120.2(4) . . ?
N12 C18 H18 119.9 . . ?
C19 C18 H18 119.9 . . ?
C114 C19 C110 117.4(4) . . ?
C114 C19 C18 120.1(4) . . ?
C110 C19 C18 122.4(3) . . ?
O12 C110 C111 117.6(4) . . ?
O12 C110 C19 121.1(4) . . ?
C111 C110 C19 121.2(4) . . ?
C110 C111 C112 119.9(4) . . ?
C110 C111 H111 120.0 . . ?
C112 C111 H111 120.0 . . ?
O13 C112 C113 124.7(4) . . ?
O13 C112 C111 115.2(4) . . ?
C113 C112 C111 120.0(4) . . ?
C114 C113 C112 119.0(4) . . ?
C114 C113 H113 120.5 . . ?
C112 C113 H113 120.5 . . ?
C113 C114 C19 122.4(4) . . ?
C113 C114 H114 118.8 . . ?
C19 C114 H114 118.8 . . ?
C11 N11 N12 118.4(3) . . ?
C11 N11 H11N 116(2) . . ?
N12 N11 H11N 124(2) . . ?
C18 N12 N11 117.0(3) . . ?
C15 N13 H13N 115(5) . . ?
C15 N13 H23N 117(3) . . ?
H13N N13 H23N 115(6) . . ?
C110 O12 H12O 111(3) . . ?
C112 O13 C115 118.3(4) . . ?
O21 C21 N21 121.8(4) . . ?
O21 C21 C22 122.9(4) . . ?
N21 C21 C22 115.2(4) . . ?
C27 C22 C23 117.0(4) . . ?
C27 C22 C21 119.7(4) . . ?
C23 C22 C21 123.2(4) . . ?
C22 C23 C24 121.7(4) . . ?
C22 C23 H23 119.2 . . ?
C24 C23 H23 119.2 . . ?
C23 C24 C25 120.2(4) . . ?
C23 C24 H24 119.9 . . ?
C25 C24 H24 119.9 . . ?
N23 C25 C26 120.8(4) . . ?
N23 C25 C24 120.8(4) . . ?
C26 C25 C24 118.4(4) . . ?
C27 C26 C25 120.1(4) . . ?
C27 C26 H26 120.0 . . ?
C25 C26 H26 120.0 . . ?
C26 C27 C22 122.5(4) . . ?
C26 C27 H27 118.7 . . ?
C22 C27 H27 118.7 . . ?
N22 C28 C29 121.3(4) . . ?
N22 C28 H28 119.3 . . ?
C29 C28 H28 119.3 . . ?
C214 C29 C210 117.2(3) . . ?
C214 C29 C28 120.6(4) . . ?
C210 C29 C28 122.1(4) . . ?
O22 C210 C211 117.1(4) . . ?
O22 C210 C29 121.8(4) . . ?
C211 C210 C29 121.1(4) . . ?
C212 C211 C210 119.7(4) . . ?
C212 C211 H211 120.2 . . ?
C210 C211 H211 120.2 . . ?
O23 C212 C211 123.9(4) . . ?
O23 C212 C213 115.6(4) . . ?
C211 C212 C213 120.4(4) . . ?
C214 C213 C212 119.5(4) . . ?
C214 C213 H213 120.3 . . ?
C212 C213 H213 120.3 . . ?
C213 C214 C29 122.1(4) . . ?
C213 C214 H214 119.0 . . ?
C29 C214 H214 119.0 . . ?

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
C21 N21 N22 C28 178.8(4) . . . . ?
O11 C11 C12 C17 -147.9(4) . . . . ?
N11 C11 C12 C17 34.3(6) . . . . ?
O11 C11 C12 C13 33.2(6) . . . . ?
N11 C11 C12 C13 -144.6(4) . . . . ?
C17 C12 C13 C14 -2.8(6) . . . . ?
C11 C12 C13 C14 176.2(4) . . . . ?
C12 C13 C14 C15 0.9(7) . . . . ?
C13 C14 C15 N13 179.9(4) . . . . ?
C13 C14 C15 C16 2.5(6) . . . . ?
C14 C15 C16 C17 -3.9(6) . . . . ?
N13 C15 C16 C17 178.7(4) . . . . ?
C15 C16 C17 C12 2.0(6) . . . . ?
C13 C12 C17 C16 1.3(6) . . . . ?
C11 C12 C17 C16 -177.6(4) . . . . ?
N12 C18 C19 C114 -179.9(4) . . . . ?
N12 C18 C19 C110 -4.3(6) . . . . ?
C114 C19 C110 O12 179.2(4) . . . . ?
C18 C19 C110 O12 3.4(6) . . . . ?
C114 C19 C110 C111 -0.7(6) . . . . ?
C18 C19 C110 C111 -176.5(4) . . . . ?
O12 C110 C111 C112 180.0(4) . . . . ?
C19 C110 C111 C112 -0.1(7) . . . . ?
C110 C111 C112 O13 -178.5(4) . . . . ?
C110 C111 C112 C113 0.4(7) . . . . ?
O13 C112 C113 C114 178.9(4) . . . . ?
C111 C112 C113 C114 0.2(7) . . . . ?
C112 C113 C114 C19 -1.0(7) . . . . ?
C110 C19 C114 C113 1.3(6) . . . . ?
C18 C19 C114 C113 177.2(4) . . . . ?
O11 C11 N11 N12 -1.5(6) . . . . ?
C12 C11 N11 N12 176.4(3) . . . . ?
C19 C18 N12 N11 174.7(4) . . . . ?
C11 N11 N12 C18 -175.2(4) . . . . ?
C113 C112 O13 C115 -5.2(7) . . . . ?
C111 C112 O13 C115 173.6(4) . . . . ?
N22 N21 C21 O21 -7.0(6) . . . . ?
N22 N21 C21 C22 170.9(4) . . . . ?
O21 C21 C22 C27 -23.8(7) . . . . ?
N21 C21 C22 C27 158.3(4) . . . . ?
O21 C21 C22 C23 152.6(4) . . . . ?
N21 C21 C22 C23 -25.3(6) . . . . ?
C27 C22 C23 C24 1.2(6) . . . . ?
C21 C22 C23 C24 -175.3(4) . . . . ?
C22 C23 C24 C25 0.3(7) . . . . ?
C23 C24 C25 N23 179.9(4) . . . . ?
C23 C24 C25 C26 -2.4(7) . . . . ?
N23 C25 C26 C27 -179.3(4) . . . . ?
C24 C25 C26 C27 2.9(7) . . . . ?
C25 C26 C27 C22 -1.4(7) . . . . ?
C23 C22 C27 C26 -0.6(7) . . . . ?
C21 C22 C27 C26 176.0(4) . . . . ?
N21 N22 C28 C29 175.8(4) . . . . ?
N22 C28 C29 C214 -176.0(4) . . . . ?
N22 C28 C29 C210 0.5(6) . . . . ?
C214 C29 C210 O22 179.6(4) . . . . ?
C28 C29 C210 O22 2.9(6) . . . . ?
C214 C29 C210 C211 -0.3(6) . . . . ?
C28 C29 C210 C211 -177.0(4) . . . . ?
O22 C210 C211 C212 -179.9(4) . . . . ?
C29 C210 C211 C212 0.0(6) . . . . ?
C215 O23 C212 C211 8.3(7) . . . . ?
C215 O23 C212 C213 -173.0(5) . . . . ?
C210 C211 C212 O23 178.8(4) . . . . ?
C210 C211 C212 C213 0.2(7) . . . . ?
O23 C212 C213 C214 -178.7(4) . . . . ?
C211 C212 C213 C214 0.0(7) . . . . ?
C212 C213 C214 C29 -0.3(7) . . . . ?
C210 C29 C214 C213 0.5(6) . . . . ?
C28 C29 C214 C213 177.2(4) . . . . ?

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
C215 H15D N12 0.96 2.83 3.577(7) 135.5 .
C16 H16 O21 0.93 2.67 3.585(6) 166.9 1_645
C18 H18 O11 0.93 2.54 3.300(5) 138.7 2
C111 H111 O21 0.93 3.07 3.905(5) 149.8 2_564
N11 H11N O11 0.85(2) 2.01(2) 2.825(4) 159(3) 2
O12 H12O N12 0.86(2) 1.85(4) 2.591(5) 143(5) .
C26 H26 O11 0.93 2.64 3.405(6) 139.6 2_465
C28 H28 O21 0.93 2.81 3.586(5) 141.4 2_565
C211 H211 N23 0.93 2.58 3.497(6) 170.5 2_664
N21 H21N O21 0.88(4) 2.16(4) 3.037(4) 172(4) 2_565
O22 H22O N22 0.83(2) 1.87(3) 2.619(4) 149(4) .
N23 H43N O12 0.86(2) 2.53(3) 3.323(6) 154(4) 2_465

_refine_diff_density_max         0.154
_refine_diff_density_min         -0.159
_refine_diff_density_rms         0.036

