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

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

data_1b
_database_code_depnum_ccdc_archive 'CCDC 1839144'

_audit_update_record             
;
2018-04-24 deposited with the CCDC.
2018-08-29 downloaded from the CCDC.
;
# publcif _publ_body_element loop end
_audit_creation_date             2018-03-09
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2018/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H17 N3 O4'
_chemical_formula_sum            'C13 H17 N3 O4'
_chemical_formula_weight         279.29
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   8.0980(5)
_cell_length_b                   10.0379(7)
_cell_length_c                   10.4154(7)
_cell_angle_alpha                116.381(4)
_cell_angle_beta                 111.697(3)
_cell_angle_gamma                92.496(4)
_cell_volume                     682.41(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4017
_cell_measurement_temperature    150
_cell_measurement_theta_max      30.126
_cell_measurement_theta_min      2.339
_shelx_estimated_absorpt_T_max   0.995
_shelx_estimated_absorpt_T_min   0.980
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.5847
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.359
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             296
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0679
_diffrn_reflns_av_unetI/netI     0.0606
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            17574
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.126
_diffrn_reflns_theta_min         2.339
_diffrn_ambient_temperature      150.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker kappa APEXII CCD Diffractometer'
_diffrn_measurement_method       'φ scans, and ω scans with κ offsets'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Incoatec I\mS microfocus X-ray source'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2791
_reflns_number_total             4017
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       'APEX3 (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.364
_refine_diff_density_min         -0.310
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         4017
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0878
_refine_ls_R_factor_gt           0.0516
_refine_ls_restrained_S_all      1.050
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0469P)²+0.2753P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1145
_refine_ls_wR_factor_ref         0.1328
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 N3(H3), C11(H11), C7(H7)
2.b Aromatic/amide H refined with riding coordinates:
 C10(H10), C9(H9)
2.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C3(H3A,H3B,H3C), C13(H13A,H13B,H13C), C2(H2A,H2B,H2C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O2 O 0.76951(15) 0.05324(12) 0.70447(12) 0.0197(2) Uani 1 1 d . . . . .
O1 O 1.30888(16) 0.42061(14) 1.04658(13) 0.0253(3) Uani 1 1 d . . . . .
O3 O 0.88476(15) 0.49308(13) 0.66411(13) 0.0221(3) Uani 1 1 d . . . . .
O4 O 0.76364(17) 0.12425(16) 0.32996(14) 0.0309(3) Uani 1 1 d . . . . .
N2 N 1.09726(17) 0.45882(15) 0.85747(15) 0.0176(3) Uani 1 1 d . . . . .
N3 N 0.33292(17) 0.22837(15) 0.54033(15) 0.0166(3) Uani 1 1 d . . . . .
H3 H 0.285608 0.120263 0.449926 0.020 Uiso 1 1 calc R . . . .
N1 N 1.03849(18) 0.23812(15) 0.87541(15) 0.0187(3) Uani 1 1 d . . . . .
C4 C 0.8663(2) 0.17968(17) 0.74329(17) 0.0158(3) Uani 1 1 d . . . . .
C5 C 0.9264(2) 0.41010(18) 0.72522(17) 0.0161(3) Uani 1 1 d . . . . .
C1 C 1.1573(2) 0.37491(18) 0.93323(17) 0.0177(3) Uani 1 1 d . . . . .
C11 C 0.4925(2) 0.30408(17) 0.53383(17) 0.0156(3) Uani 1 1 d . . . . .
H11 H 0.552970 0.408092 0.630459 0.019 Uiso 1 1 calc R . . . .
C7 C 0.6349(2) 0.20735(17) 0.52292(17) 0.0153(3) Uani 1 1 d . . . . .
H7 H 0.576670 0.103219 0.497039 0.018 Uiso 1 1 calc R . . . .
C6 C 0.8140(2) 0.26653(17) 0.66891(17) 0.0153(3) Uani 1 1 d . . . . .
C10 C 0.4310(2) 0.31896(18) 0.38617(18) 0.0200(3) Uani 1 1 d . . . . .
H10 H 0.335315 0.365757 0.356043 0.024 Uiso 1 1 calc R . . . .
C8 C 0.6578(2) 0.18927(19) 0.37681(18) 0.0205(3) Uani 1 1 d . . . . .
C12 C 0.3924(2) 0.2221(2) 0.69092(19) 0.0220(3) Uani 1 1 d . . . . .
H12A H 0.436166 0.326776 0.781722 0.033 Uiso 1 1 calc GR . . . .
H12B H 0.491796 0.169585 0.701230 0.033 Uiso 1 1 calc GR . . . .
H12C H 0.288464 0.165922 0.688688 0.033 Uiso 1 1 calc GR . . . .
C9 C 0.5258(2) 0.2592(2) 0.30292(19) 0.0232(4) Uani 1 1 d . . . . .
H9 H 0.510432 0.261319 0.208966 0.028 Uiso 1 1 calc R . . . .
C3 C 1.2236(2) 0.60349(19) 0.9161(2) 0.0228(3) Uani 1 1 d . . . . .
H3A H 1.238639 0.677848 1.022663 0.034 Uiso 1 1 calc GR . . . .
H3B H 1.173555 0.644300 0.843853 0.034 Uiso 1 1 calc GR . . . .
H3C H 1.343003 0.585022 0.920802 0.034 Uiso 1 1 calc GR . . . .
C13 C 0.1788(2) 0.3051(2) 0.5209(2) 0.0266(4) Uani 1 1 d . . . . .
H13A H 0.127434 0.293410 0.414166 0.040 Uiso 1 1 calc GR . . . .
H13B H 0.224612 0.414500 0.600793 0.040 Uiso 1 1 calc GR . . . .
H13C H 0.083202 0.257736 0.534937 0.040 Uiso 1 1 calc GR . . . .
C2 C 1.0982(3) 0.1497(2) 0.9570(2) 0.0294(4) Uani 1 1 d . . . . .
H2A H 1.199006 0.108465 0.936842 0.044 Uiso 1 1 calc GR . . . .
H2B H 0.995253 0.064771 0.916939 0.044 Uiso 1 1 calc GR . . . .
H2C H 1.140240 0.216631 1.071650 0.044 Uiso 1 1 calc GR . . . .


_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
O2 C4 1.2694(18) . ?
O1 C1 1.2286(19) . ?
O3 C5 1.2448(18) . ?
O4 C8 1.2137(19) . ?
N2 C5 1.4087(19) . ?
N2 C1 1.382(2) . ?
N2 C3 1.466(2) . ?
N3 H3 1.0000 . ?
N3 C11 1.5092(19) . ?
N3 C12 1.4924(19) . ?
N3 C13 1.492(2) . ?
N1 C4 1.4054(19) . ?
N1 C1 1.377(2) . ?
N1 C2 1.465(2) . ?
C4 C6 1.389(2) . ?
C5 C6 1.410(2) . ?
C11 H11 1.0000 . ?
C11 C7 1.543(2) . ?
C11 C10 1.510(2) . ?
C7 H7 1.0000 . ?
C7 C6 1.503(2) . ?
C7 C8 1.533(2) . ?
C10 H10 0.9500 . ?
C10 C9 1.331(2) . ?
C8 C9 1.471(2) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C9 H9 0.9500 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 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
C5 N2 C3 119.04(13) . . ?
C1 N2 C5 123.71(13) . . ?
C1 N2 C3 117.20(13) . . ?
C11 N3 H3 107.6 . . ?
C12 N3 H3 107.6 . . ?
C12 N3 C11 111.13(12) . . ?
C13 N3 H3 107.6 . . ?
C13 N3 C11 112.42(13) . . ?
C13 N3 C12 110.22(12) . . ?
C4 N1 C2 119.09(14) . . ?
C1 N1 C4 123.63(13) . . ?
C1 N1 C2 117.28(13) . . ?
O2 C4 N1 116.93(13) . . ?
O2 C4 C6 125.47(14) . . ?
C6 C4 N1 117.58(14) . . ?
O3 C5 N2 119.10(14) . . ?
O3 C5 C6 124.18(14) . . ?
N2 C5 C6 116.71(13) . . ?
O1 C1 N2 121.52(15) . . ?
O1 C1 N1 121.87(14) . . ?
N1 C1 N2 116.61(13) . . ?
N3 C11 H11 109.6 . . ?
N3 C11 C7 111.90(12) . . ?
N3 C11 C10 111.30(12) . . ?
C7 C11 H11 109.6 . . ?
C10 C11 H11 109.6 . . ?
C10 C11 C7 104.79(12) . . ?
C11 C7 H7 107.4 . . ?
C6 C7 C11 116.99(12) . . ?
C6 C7 H7 107.4 . . ?
C6 C7 C8 113.25(13) . . ?
C8 C7 C11 103.97(12) . . ?
C8 C7 H7 107.4 . . ?
C4 C6 C5 121.72(13) . . ?
C4 C6 C7 120.17(14) . . ?
C5 C6 C7 118.10(13) . . ?
C11 C10 H10 123.8 . . ?
C9 C10 C11 112.45(14) . . ?
C9 C10 H10 123.8 . . ?
O4 C8 C7 125.01(15) . . ?
O4 C8 C9 127.02(15) . . ?
C9 C8 C7 107.94(13) . . ?
N3 C12 H12A 109.5 . . ?
N3 C12 H12B 109.5 . . ?
N3 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C10 C9 C8 110.49(14) . . ?
C10 C9 H9 124.8 . . ?
C8 C9 H9 124.8 . . ?
N2 C3 H3A 109.5 . . ?
N2 C3 H3B 109.5 . . ?
N2 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
N3 C13 H13A 109.5 . . ?
N3 C13 H13B 109.5 . . ?
N3 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N1 C2 H2A 109.5 . . ?
N1 C2 H2B 109.5 . . ?
N1 C2 H2C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?


_olex2_submission_special_instructions 'No special instructions were received'



_publcif_funding_html            
;
;
####################################################################### 
# 
# 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_14b
_database_code_depnum_ccdc_archive 'CCDC 1839147'
_audit_update_record             
;
2018-04-24 deposited with the CCDC.
2018-08-29 downloaded from the CCDC.
;
_audit_creation_date             2018-04-09
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H21 N3 O5'
_chemical_formula_sum            'C19 H21 N3 O5'
_chemical_formula_weight         371.39
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   6.6950(13)
_cell_length_b                   10.327(2)
_cell_length_c                   13.555(3)
_cell_angle_alpha                107.40(3)
_cell_angle_beta                 92.61(3)
_cell_angle_gamma                102.79(3)
_cell_volume                     865.8(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4159
_cell_measurement_temperature    100
_cell_measurement_theta_max      31.8
_cell_measurement_theta_min      3.3
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.425
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             392
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method 
'prepared by addition of hexane to a solution of EDF3 in dichloromethane'
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0263
_diffrn_reflns_av_unetI/netI     0.0216
_diffrn_reflns_Laue_measured_fraction_full 0.911
_diffrn_reflns_Laue_measured_fraction_max 0.707
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            15948
_diffrn_reflns_point_group_measured_fraction_full 0.911
_diffrn_reflns_point_group_measured_fraction_max 0.707
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         31.763
_diffrn_reflns_theta_min         3.335
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.911
_diffrn_measured_fraction_theta_max 0.707
_diffrn_measurement_device_type  'ADSC Quantum 210r'
_diffrn_measurement_method       'Phi Scan'
_diffrn_radiation_monochromator  'Silicon Double Crystal'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'MX1 Beamline Australian Synchrotron'
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3621
_reflns_number_total             4159
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'XDS (Kabsch, 1993)'
_computing_data_collection       'BluIce (McPhillips, 2002)'
_computing_data_reduction        'XDS (Kabsch, 1993)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.295
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         4159
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0576
_refine_ls_R_factor_gt           0.0506
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0832P)²+0.3150P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1359
_refine_ls_wR_factor_ref         0.1425
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7), C6(H6), C11(H11)
2.b Aromatic/amide H refined with riding coordinates:
 C10(H10), C14(H14), C17(H17), C18(H18), C9(H9), C15(H15)
2.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C19(H19A,H19B,H19C), C2(H2A,H2B,H2C), C3(H3A,H3B,H3C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O4 O 1.05914(17) 0.81877(11) 0.39562(8) 0.0288(2) Uani 1 1 d . . . . .
O3 O 0.78657(18) 0.54537(11) 0.45452(7) 0.0302(2) Uani 1 1 d . . . . .
O2 O 0.78036(18) 0.47586(11) 0.09641(7) 0.0289(2) Uani 1 1 d . . . . .
O1 O 0.66147(18) 0.11156(11) 0.22263(9) 0.0331(3) Uani 1 1 d . . . . .
O5 O 0.10837(18) 0.01332(10) 0.12873(8) 0.0309(2) Uani 1 1 d . . . . .
N2 N 0.7380(2) 0.32887(12) 0.33997(9) 0.0258(3) Uani 1 1 d . . . . .
N3 N 0.35492(19) 0.59545(11) 0.24164(8) 0.0228(2) Uani 1 1 d . . . . .
N1 N 0.72987(19) 0.29283(12) 0.15842(9) 0.0244(2) Uani 1 1 d . . . . .
C7 C 0.7448(2) 0.66225(13) 0.29265(9) 0.0216(2) Uani 1 1 d . . . . .
H7 H 0.745867 0.679510 0.225383 0.026 Uiso 1 1 calc R . . . .
C8 C 0.8751(2) 0.79418(14) 0.37250(10) 0.0235(3) Uani 1 1 d . . . . .
C10 C 0.5432(2) 0.81175(14) 0.38132(10) 0.0249(3) Uani 1 1 d . . . . .
H10 H 0.430203 0.850359 0.393669 0.030 Uiso 1 1 calc R . . . .
C13 C 0.2933(2) 0.44757(13) 0.21292(10) 0.0221(3) Uani 1 1 d . . . . .
C6 C 0.8290(2) 0.53340(13) 0.28001(10) 0.0222(3) Uani 1 1 d . . . . .
H6 H 0.979417 0.568097 0.289237 0.027 Uiso 1 1 calc R . . . .
C4 C 0.7755(2) 0.43330(14) 0.17050(10) 0.0233(3) Uani 1 1 d . . . . .
C14 C 0.2578(2) 0.38330(14) 0.28971(10) 0.0243(3) Uani 1 1 d . . . . .
H14 H 0.274852 0.438717 0.359118 0.029 Uiso 1 1 calc R . . . .
C11 C 0.5260(2) 0.66012(13) 0.32386(9) 0.0217(3) Uani 1 1 d . . . . .
H11 H 0.505752 0.609372 0.374675 0.026 Uiso 1 1 calc R . . . .
C17 C 0.1946(2) 0.21831(14) 0.08459(10) 0.0257(3) Uani 1 1 d . . . . .
H17 H 0.170650 0.162669 0.015098 0.031 Uiso 1 1 calc R . . . .
C18 C 0.2572(2) 0.36223(14) 0.10927(10) 0.0242(3) Uani 1 1 d . . . . .
H18 H 0.275399 0.402414 0.056366 0.029 Uiso 1 1 calc R . . . .
C9 C 0.7368(2) 0.88447(14) 0.41249(10) 0.0258(3) Uani 1 1 d . . . . .
H9 H 0.778442 0.978060 0.453309 0.031 Uiso 1 1 calc R . . . .
C16 C 0.1671(2) 0.15578(14) 0.16191(11) 0.0250(3) Uani 1 1 d . . . . .
C5 C 0.7817(2) 0.47147(14) 0.36546(10) 0.0242(3) Uani 1 1 d . . . . .
C1 C 0.7070(2) 0.23625(14) 0.23894(11) 0.0252(3) Uani 1 1 d . . . . .
C15 C 0.1979(2) 0.23921(14) 0.26520(10) 0.0253(3) Uani 1 1 d . . . . .
H15 H 0.178527 0.198558 0.317802 0.030 Uiso 1 1 calc R . . . .
C12 C 0.3634(2) 0.65566(15) 0.15741(11) 0.0280(3) Uani 1 1 d . . . . .
H12A H 0.463891 0.624908 0.113812 0.042 Uiso 1 1 calc GR . . . .
H12B H 0.401370 0.755953 0.185836 0.042 Uiso 1 1 calc GR . . . .
H12C H 0.230446 0.625939 0.116894 0.042 Uiso 1 1 calc GR . . . .
C19 C 0.0780(3) -0.05228(16) 0.20654(13) 0.0354(3) Uani 1 1 d . . . . .
H19A H 0.042361 -0.152080 0.174584 0.053 Uiso 1 1 calc GR . . . .
H19B H -0.031599 -0.024648 0.244315 0.053 Uiso 1 1 calc GR . . . .
H19C H 0.202664 -0.024640 0.253571 0.053 Uiso 1 1 calc GR . . . .
C2 C 0.6933(3) 0.19375(16) 0.05255(11) 0.0315(3) Uani 1 1 d . . . . .
H2A H 0.548333 0.166026 0.028789 0.047 Uiso 1 1 calc GR . . . .
H2B H 0.741306 0.112719 0.052432 0.047 Uiso 1 1 calc GR . . . .
H2C H 0.766467 0.237574 0.007024 0.047 Uiso 1 1 calc GR . . . .
C3 C 0.7018(3) 0.26842(17) 0.42383(12) 0.0380(4) Uani 1 1 d . . . . .
H3A H 0.803083 0.320984 0.482790 0.057 Uiso 1 1 calc GR . . . .
H3B H 0.711899 0.172956 0.400574 0.057 Uiso 1 1 calc GR . . . .
H3C H 0.566451 0.271499 0.443387 0.057 Uiso 1 1 calc GR . . . .


_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
O4 C8 1.2085(19) . ?
O3 C5 1.2146(16) . ?
O2 C4 1.2097(16) . ?
O1 C1 1.2041(17) . ?
O5 C16 1.3614(17) . ?
O5 C19 1.4137(19) . ?
N2 C5 1.3672(18) . ?
N2 C1 1.3915(18) . ?
N2 C3 1.4572(18) . ?
N3 C13 1.4160(17) . ?
N3 C11 1.4491(18) . ?
N3 C12 1.4520(17) . ?
N1 C4 1.3718(17) . ?
N1 C1 1.3831(18) . ?
N1 C2 1.4647(17) . ?
C7 H7 0.9800 . ?
C7 C8 1.515(2) . ?
C7 C6 1.5238(17) . ?
C7 C11 1.5404(19) . ?
C8 C9 1.4648(19) . ?
C10 H10 0.9300 . ?
C10 C11 1.5014(18) . ?
C10 C9 1.323(2) . ?
C13 C14 1.3952(18) . ?
C13 C18 1.3939(18) . ?
C6 H6 0.9800 . ?
C6 C4 1.5069(18) . ?
C6 C5 1.4958(18) . ?
C14 H14 0.9300 . ?
C14 C15 1.3832(19) . ?
C11 H11 0.9800 . ?
C17 H17 0.9300 . ?
C17 C18 1.3823(19) . ?
C17 C16 1.3853(19) . ?
C18 H18 0.9300 . ?
C9 H9 0.9300 . ?
C16 C15 1.3852(19) . ?
C15 H15 0.9300 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 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
C16 O5 C19 116.69(11) . . ?
C5 N2 C1 124.94(12) . . ?
C5 N2 C3 117.67(12) . . ?
C1 N2 C3 117.12(12) . . ?
C13 N3 C11 114.48(11) . . ?
C13 N3 C12 116.64(11) . . ?
C11 N3 C12 114.75(11) . . ?
C4 N1 C1 124.91(11) . . ?
C4 N1 C2 118.28(12) . . ?
C1 N1 C2 116.76(12) . . ?
C8 C7 H7 106.6 . . ?
C8 C7 C6 114.04(11) . . ?
C8 C7 C11 102.71(10) . . ?
C6 C7 H7 106.6 . . ?
C6 C7 C11 119.41(11) . . ?
C11 C7 H7 106.6 . . ?
O4 C8 C7 125.25(12) . . ?
O4 C8 C9 127.69(13) . . ?
C9 C8 C7 107.05(12) . . ?
C11 C10 H10 123.7 . . ?
C9 C10 H10 123.7 . . ?
C9 C10 C11 112.66(12) . . ?
C14 C13 N3 119.70(11) . . ?
C18 C13 N3 122.33(12) . . ?
C18 C13 C14 117.91(12) . . ?
C7 C6 H6 105.3 . . ?
C4 C6 C7 111.54(11) . . ?
C4 C6 H6 105.3 . . ?
C5 C6 C7 112.07(11) . . ?
C5 C6 H6 105.3 . . ?
C5 C6 C4 116.24(11) . . ?
O2 C4 N1 121.65(12) . . ?
O2 C4 C6 120.96(12) . . ?
N1 C4 C6 117.34(12) . . ?
C13 C14 H14 119.2 . . ?
C15 C14 C13 121.64(12) . . ?
C15 C14 H14 119.2 . . ?
N3 C11 C7 117.29(10) . . ?
N3 C11 C10 114.67(11) . . ?
N3 C11 H11 107.3 . . ?
C7 C11 H11 107.3 . . ?
C10 C11 C7 102.26(11) . . ?
C10 C11 H11 107.3 . . ?
C18 C17 H17 119.5 . . ?
C18 C17 C16 120.93(12) . . ?
C16 C17 H17 119.5 . . ?
C13 C18 H18 119.8 . . ?
C17 C18 C13 120.46(13) . . ?
C17 C18 H18 119.8 . . ?
C8 C9 H9 125.4 . . ?
C10 C9 C8 109.20(12) . . ?
C10 C9 H9 125.4 . . ?
O5 C16 C17 115.91(12) . . ?
O5 C16 C15 124.76(13) . . ?
C15 C16 C17 119.33(12) . . ?
O3 C5 N2 121.33(13) . . ?
O3 C5 C6 121.16(12) . . ?
N2 C5 C6 117.49(11) . . ?
O1 C1 N2 120.98(13) . . ?
O1 C1 N1 121.49(13) . . ?
N1 C1 N2 117.53(12) . . ?
C14 C15 C16 119.67(13) . . ?
C14 C15 H15 120.2 . . ?
C16 C15 H15 120.2 . . ?
N3 C12 H12A 109.5 . . ?
N3 C12 H12B 109.5 . . ?
N3 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O5 C19 H19A 109.5 . . ?
O5 C19 H19B 109.5 . . ?
O5 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N1 C2 H2A 109.5 . . ?
N1 C2 H2B 109.5 . . ?
N1 C2 H2C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
N2 C3 H3A 109.5 . . ?
N2 C3 H3B 109.5 . . ?
N2 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?

# end Validation Reply Form
_olex2_submission_original_sample_id EDF3
_olex2_submission_special_instructions 'No special instructions were received'
_vrf_PLAT029_14b                 
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.911 Why?  
RESPONSE: The data collection was carried out at the Australian Synchrotron. The
 diffraction was measured along one axis, giving rise to a lower completeness
 value, which is typical of data collected at the Synchrotron.
;
####################################################################### 
# 
# 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_12a
_database_code_depnum_ccdc_archive 'CCDC 1839146'

_audit_update_record             
;
2018-04-24 deposited with the CCDC.
2018-08-29 downloaded from the CCDC.
;
# publcif _publ_body_element loop end
_audit_creation_date             2018-04-03
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2018/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H19 N3 O4'
_chemical_formula_sum            'C15 H19 N3 O4'
_chemical_formula_weight         305.33
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   9.999(2)
_cell_length_b                   17.469(4)
_cell_length_c                   8.5210(17)
_cell_angle_alpha                90
_cell_angle_beta                 98.76(3)
_cell_angle_gamma                90
_cell_volume                     1471.0(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3202
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.102
_cell_measurement_theta_min      2.061
_shelx_estimated_absorpt_T_max   0.995
_shelx_estimated_absorpt_T_min   0.988
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'dark violet'
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    violet
_exptl_crystal_density_diffrn    1.379
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0361
_diffrn_reflns_av_unetI/netI     0.0205
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            20733
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.102
_diffrn_reflns_theta_min         2.061
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'ADSC Quantum 210r'
_diffrn_measurement_method       'Phi Scan'
_diffrn_radiation_monochromator  'Silicon Double Crystal'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'MX1 Beamline Australian Synchrotron'
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2721
_reflns_number_total             3202
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'XDS (Kabsch, 1993)'
_computing_data_collection       'AS QEGUI'
_computing_data_reduction        'XDS (Kabsch, 1993)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.317
_refine_diff_density_min         -0.306
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     205
_refine_ls_number_reflns         3202
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0575
_refine_ls_R_factor_gt           0.0485
_refine_ls_restrained_S_all      1.066
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0620P)²+0.8450P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1211
_refine_ls_wR_factor_ref         0.1275
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C14(H14A,H14B), C12(H12A,H12B), C13(H13A,H13B)
2.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C7(H7), C11(H11), C10(H10)
2.c Idealised Me refined as rotating group:
 C3(H3A,H3B,H3C), C2(H2A,H2B,H2C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O2 O 0.42678(11) 0.37029(7) 0.58102(14) 0.0286(3) Uani 1 1 d . . . . .
O3 O 0.71170(12) 0.43835(7) 0.20556(14) 0.0312(3) Uani 1 1 d . . . . .
O4 O 0.24568(12) 0.44530(7) 0.40130(15) 0.0297(3) Uani 1 1 d . . . . .
O1 O 0.86275(12) 0.29163(7) 0.63438(14) 0.0312(3) Uani 1 1 d . . . . .
N1 N 0.64351(13) 0.33174(8) 0.60434(16) 0.0236(3) Uani 1 1 d . . . . .
N2 N 0.78846(13) 0.37112(8) 0.42839(16) 0.0242(3) Uani 1 1 d . . . . .
N3 N -0.06184(13) 0.62655(8) 0.04822(16) 0.0238(3) Uani 1 1 d . . . . .
C4 C 0.53397(15) 0.37237(8) 0.52276(19) 0.0222(3) Uani 1 1 d . . . . .
C6 C 0.68469(16) 0.40933(9) 0.32960(19) 0.0240(3) Uani 1 1 d . . . . .
C5 C 0.55349(16) 0.41147(8) 0.38083(19) 0.0221(3) Uani 1 1 d . . . . .
C9 C 0.24904(17) 0.52029(9) 0.17296(19) 0.0263(3) Uani 1 1 d . . . . .
H9 H 0.295039 0.537234 0.089661 0.032 Uiso 1 1 calc R . . . .
C7 C 0.45292(16) 0.45483(9) 0.28271(19) 0.0232(3) Uani 1 1 d . . . . .
H7 H 0.484903 0.477067 0.193681 0.028 Uiso 1 1 calc R . . . .
C1 C 0.77073(16) 0.32937(9) 0.56024(19) 0.0238(3) Uani 1 1 d . . . . .
C11 C 0.05969(16) 0.59662(9) 0.05640(19) 0.0246(3) Uani 1 1 d . . . . .
H11 H 0.112058 0.611216 -0.022817 0.030 Uiso 1 1 calc R . . . .
C8 C 0.31918(16) 0.47145(9) 0.28921(19) 0.0236(3) Uani 1 1 d . . . . .
C10 C 0.11788(16) 0.54506(9) 0.17239(19) 0.0255(3) Uani 1 1 d . . . . .
H10 H 0.067298 0.527086 0.250699 0.031 Uiso 1 1 calc R . . . .
C15 C -0.11959(16) 0.68150(10) -0.07543(19) 0.0266(3) Uani 1 1 d . . . . .
H15A H -0.155619 0.654932 -0.175602 0.032 Uiso 1 1 calc R . . . .
H15B H -0.051237 0.719577 -0.096722 0.032 Uiso 1 1 calc R . . . .
C14 C -0.23246(18) 0.71909(10) -0.0020(2) 0.0329(4) Uani 1 1 d . . . . .
H14A H -0.304772 0.738388 -0.084949 0.039 Uiso 1 1 calc R . . . .
H14B H -0.197497 0.761982 0.068422 0.039 Uiso 1 1 calc R . . . .
C12 C -0.15527(17) 0.61165(10) 0.1627(2) 0.0295(4) Uani 1 1 d . . . . .
H12A H -0.118552 0.631993 0.268945 0.035 Uiso 1 1 calc R . . . .
H12B H -0.172278 0.556109 0.171620 0.035 Uiso 1 1 calc R . . . .
C13 C -0.28427(17) 0.65378(11) 0.0927(2) 0.0302(4) Uani 1 1 d . . . . .
H13A H -0.332096 0.673903 0.177512 0.036 Uiso 1 1 calc R . . . .
H13B H -0.346161 0.619755 0.022616 0.036 Uiso 1 1 calc R . . . .
C3 C 0.92495(17) 0.36997(12) 0.3847(2) 0.0330(4) Uani 1 1 d . . . . .
H3A H 0.939156 0.321434 0.332014 0.050 Uiso 1 1 calc GR . . . .
H3B H 0.992163 0.375149 0.480656 0.050 Uiso 1 1 calc GR . . . .
H3C H 0.934615 0.412550 0.312444 0.050 Uiso 1 1 calc GR . . . .
C2 C 0.62340(18) 0.29176(11) 0.7501(2) 0.0346(4) Uani 1 1 d . . . . .
H2A H 0.582413 0.326821 0.818965 0.052 Uiso 1 1 calc GR . . . .
H2B H 0.710906 0.273939 0.805712 0.052 Uiso 1 1 calc GR . . . .
H2C H 0.563448 0.247777 0.723223 0.052 Uiso 1 1 calc GR . . . .
H4 H 0.309(3) 0.4158(16) 0.471(3) 0.058(7) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 C4 1.2484(19) . ?
O3 C6 1.239(2) . ?
O4 C8 1.369(2) . ?
O4 H4 0.95(3) . ?
O1 C1 1.226(2) . ?
N1 C4 1.398(2) . ?
N1 C1 1.381(2) . ?
N1 C2 1.466(2) . ?
N2 C6 1.402(2) . ?
N2 C1 1.374(2) . ?
N2 C3 1.468(2) . ?
N3 C11 1.315(2) . ?
N3 C15 1.476(2) . ?
N3 C12 1.473(2) . ?
C4 C5 1.428(2) . ?
C6 C5 1.445(2) . ?
C5 C7 1.424(2) . ?
C9 H9 0.9500 . ?
C9 C8 1.410(2) . ?
C9 C10 1.380(2) . ?
C7 H7 0.9500 . ?
C7 C8 1.378(2) . ?
C11 H11 0.9500 . ?
C11 C10 1.397(2) . ?
C10 H10 0.9500 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C14 1.520(2) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C13 1.533(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.525(2) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 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
C8 O4 H4 104.0(16) . . ?
C4 N1 C2 117.72(13) . . ?
C1 N1 C4 124.36(13) . . ?
C1 N1 C2 117.87(13) . . ?
C6 N2 C3 119.08(13) . . ?
C1 N2 C6 124.62(14) . . ?
C1 N2 C3 116.15(14) . . ?
C11 N3 C15 123.65(14) . . ?
C11 N3 C12 124.68(14) . . ?
C12 N3 C15 111.65(13) . . ?
O2 C4 N1 116.27(14) . . ?
O2 C4 C5 125.95(14) . . ?
N1 C4 C5 117.78(14) . . ?
O3 C6 N2 118.01(15) . . ?
O3 C6 C5 124.98(15) . . ?
N2 C6 C5 117.00(14) . . ?
C4 C5 C6 119.41(14) . . ?
C7 C5 C4 125.19(14) . . ?
C7 C5 C6 115.39(14) . . ?
C8 C9 H9 117.9 . . ?
C10 C9 H9 117.9 . . ?
C10 C9 C8 124.24(16) . . ?
C5 C7 H7 113.1 . . ?
C8 C7 C5 133.74(15) . . ?
C8 C7 H7 113.1 . . ?
O1 C1 N1 121.74(15) . . ?
O1 C1 N2 121.79(15) . . ?
N2 C1 N1 116.47(14) . . ?
N3 C11 H11 117.4 . . ?
N3 C11 C10 125.15(15) . . ?
C10 C11 H11 117.4 . . ?
O4 C8 C9 115.43(14) . . ?
O4 C8 C7 125.81(15) . . ?
C7 C8 C9 118.76(15) . . ?
C9 C10 C11 119.85(15) . . ?
C9 C10 H10 120.1 . . ?
C11 C10 H10 120.1 . . ?
N3 C15 H15A 111.2 . . ?
N3 C15 H15B 111.2 . . ?
N3 C15 C14 102.78(13) . . ?
H15A C15 H15B 109.1 . . ?
C14 C15 H15A 111.2 . . ?
C14 C15 H15B 111.2 . . ?
C15 C14 H14A 111.1 . . ?
C15 C14 H14B 111.1 . . ?
C15 C14 C13 103.11(14) . . ?
H14A C14 H14B 109.1 . . ?
C13 C14 H14A 111.1 . . ?
C13 C14 H14B 111.1 . . ?
N3 C12 H12A 111.0 . . ?
N3 C12 H12B 111.0 . . ?
N3 C12 C13 103.88(13) . . ?
H12A C12 H12B 109.0 . . ?
C13 C12 H12A 111.0 . . ?
C13 C12 H12B 111.0 . . ?
C14 C13 H13A 111.1 . . ?
C14 C13 H13B 111.1 . . ?
C12 C13 C14 103.38(14) . . ?
C12 C13 H13A 111.1 . . ?
C12 C13 H13B 111.1 . . ?
H13A C13 H13B 109.1 . . ?
N2 C3 H3A 109.5 . . ?
N2 C3 H3B 109.5 . . ?
N2 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
N1 C2 H2A 109.5 . . ?
N1 C2 H2B 109.5 . . ?
N1 C2 H2C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?


_olex2_submission_special_instructions 'No special instructions were received'



_publcif_funding_html            
;
;
####################################################################### 
# 
# 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_2b
_database_code_depnum_ccdc_archive 'CCDC 1839145'
_audit_update_record             
;
2018-04-24 deposited with the CCDC.
2018-08-29 downloaded from the CCDC.
;
_audit_creation_date             2018-03-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2018/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H19 N3 O4, 2(H2 O)'
_chemical_formula_sum            'C14 H23 N3 O6'
_chemical_formula_weight         329.35
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   8.7890(18)
_cell_length_b                   10.706(2)
_cell_length_c                   17.342(4)
_cell_angle_alpha                90
_cell_angle_beta                 99.97(3)
_cell_angle_gamma                90
_cell_volume                     1607.2(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4008
_cell_measurement_temperature    100
_cell_measurement_theta_max      28.698
_cell_measurement_theta_min      2.245
_shelx_estimated_absorpt_T_max   0.999
_shelx_estimated_absorpt_T_min   0.995
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0690
_diffrn_reflns_av_unetI/netI     0.0359
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            21320
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_min         3.051
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'ADSC Quantum 210r'
_diffrn_measurement_method       'Phi Scan'
_diffrn_radiation_monochromator  'Silicon Double Crystal'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'MX1 Beamline Australian Synchrotron'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2328
_reflns_number_total             3253
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'XDS (Kabsch, 1993)'
_computing_data_collection       'AS QEGUI'
_computing_data_reduction        'XDS (Kabsch, 1993)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.287
_refine_diff_density_min         -0.390
_refine_diff_density_rms         0.065
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     242
_refine_ls_number_reflns         3253
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0818
_refine_ls_R_factor_gt           0.0552
_refine_ls_restrained_S_all      1.050
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0734P)²+0.7856P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1305
_refine_ls_wR_factor_ref         0.1465
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2. Others
 Sof(H3B)=Sof(C13B)=Sof(H13C)=Sof(H13D)=Sof(C14B)=Sof(H14D)=Sof(H14E)=
 Sof(H14F)=1-FVAR(1)
 Sof(H3A)=Sof(C13A)=Sof(H13A)=Sof(H13B)=Sof(C14A)=Sof(H14A)=Sof(H14B)=
 Sof(H14C)=FVAR(1)
3.a Free rotating group:
 O6(H6A,H6B)
3.b Ternary CH refined with riding coordinates:
 N3(H3A), N3(H3B), C7(H7), C11(H11)
3.c Secondary CH2 refined with riding coordinates:
 C13A(H13A,H13B), C13B(H13C,H13D)
3.d Aromatic/amide H refined with riding coordinates:
 C10(H10), C9(H9)
3.e Idealised Me refined with riding coordinates:
 C3(H3C,H3D,H3E)
3.f Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C), C12(H12A,H12B,H12C), C14A(H14A,H14B,H14C), C14B(H14D,H14E,
 H14F)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.17059(17) 0.34802(14) 0.57464(10) 0.0329(4) Uani 1 1 d . . . . .
O2 O 0.12025(17) 0.77235(14) 0.58492(10) 0.0324(4) Uani 1 1 d . . . . .
O3 O 0.35618(18) 0.58169(14) 0.39142(10) 0.0327(4) Uani 1 1 d . . . . .
O4 O 0.46653(18) 0.87581(16) 0.57744(11) 0.0402(4) Uani 1 1 d . . . . .
O5 O 0.5533(2) 0.72705(18) 0.32955(11) 0.0402(4) Uani 1 1 d . . . . .
O6 O 0.1072(2) 0.92129(16) 0.70784(11) 0.0416(4) Uani 1 1 d . . . . .
H6A H 0.082295 0.874837 0.743392 0.062 Uiso 1 1 d G . . . .
H6B H 0.123784 0.870835 0.672353 0.062 Uiso 1 1 d G . . . .
N2 N 0.2624(2) 0.46664(16) 0.48360(11) 0.0288(4) Uani 1 1 d . . . . .
N1 N 0.1456(2) 0.55923(17) 0.58075(11) 0.0281(4) Uani 1 1 d . . . . .
N3 N 0.1185(2) 0.90894(18) 0.33592(13) 0.0401(5) Uani 1 1 d . . . . .
H3A H 0.029610 0.967279 0.320381 0.048 Uiso 0.640(11) 1 calc R . P A 1
H3B H 0.028322 0.965738 0.319636 0.048 Uiso 0.360(11) 1 calc R . P A 2
C4 C 0.1695(2) 0.67966(19) 0.55219(13) 0.0266(5) Uani 1 1 d . . . . .
C1 C 0.1920(2) 0.4525(2) 0.54771(14) 0.0280(5) Uani 1 1 d . . . . .
C5 C 0.2929(2) 0.58320(19) 0.45139(14) 0.0270(5) Uani 1 1 d . . . . .
C6 C 0.2472(2) 0.68986(19) 0.48859(14) 0.0266(5) Uani 1 1 d . . . . .
C10 C 0.1566(3) 1.0218(2) 0.46258(15) 0.0324(5) Uani 1 1 d . . . . .
H10 H 0.092001 1.091506 0.446569 0.039 Uiso 1 1 calc R . . . .
C7 C 0.2795(2) 0.81879(19) 0.46180(14) 0.0278(5) Uani 1 1 d . . . . .
H7 H 0.351603 0.811422 0.423307 0.033 Uiso 1 1 calc R . . . .
C8 C 0.3554(2) 0.9037(2) 0.52893(14) 0.0304(5) Uani 1 1 d . . . . .
C9 C 0.2738(3) 1.0240(2) 0.52215(15) 0.0325(5) Uani 1 1 d . . . . .
H9 H 0.301100 1.093628 0.555683 0.039 Uiso 1 1 calc R . . . .
C11 C 0.1380(2) 0.8964(2) 0.42340(15) 0.0333(5) Uani 1 1 d . . . . .
H11 H 0.042878 0.856243 0.436428 0.040 Uiso 1 1 calc R . . . .
C2 C 0.0744(3) 0.5446(2) 0.65089(14) 0.0330(5) Uani 1 1 d . . . . .
H2A H 0.146928 0.502244 0.691903 0.049 Uiso 1 1 calc GR . . . .
H2B H -0.020042 0.494648 0.637918 0.049 Uiso 1 1 calc GR . . . .
H2C H 0.048813 0.626990 0.669639 0.049 Uiso 1 1 calc GR . . . .
C3 C 0.3122(3) 0.3524(2) 0.44807(16) 0.0396(6) Uani 1 1 d . . . . .
H3C H 0.386936 0.307581 0.486812 0.059 Uiso 1 1 calc R . . . .
H3D H 0.360607 0.374701 0.403102 0.059 Uiso 1 1 calc R . . . .
H3E H 0.222442 0.298907 0.430606 0.059 Uiso 1 1 calc R . . . .
C12 C 0.2535(3) 0.9680(3) 0.30802(15) 0.0447(6) Uani 1 1 d . . . . .
H12A H 0.286826 1.041730 0.339997 0.067 Uiso 1 1 calc GR . . . .
H12B H 0.223342 0.993032 0.253140 0.067 Uiso 1 1 calc GR . . . .
H12C H 0.338672 0.907881 0.312637 0.067 Uiso 1 1 calc GR . . . .
C13A C 0.0622(6) 0.7817(4) 0.3053(4) 0.0291(12) Uani 0.640(11) 1 d . . P A 1
H13A H 0.151307 0.725334 0.304533 0.035 Uiso 0.640(11) 1 calc R . P A 1
H13B H -0.004510 0.744464 0.339670 0.035 Uiso 0.640(11) 1 calc R . P A 1
C14A C -0.0276(7) 0.7970(5) 0.2236(3) 0.0502(16) Uani 0.640(11) 1 d . . P A 1
H14A H 0.031853 0.848418 0.192674 0.075 Uiso 0.640(11) 1 calc GR . P A 1
H14B H -0.126465 0.837913 0.225996 0.075 Uiso 0.640(11) 1 calc GR . P A 1
H14C H -0.046704 0.714810 0.199005 0.075 Uiso 0.640(11) 1 calc GR . P A 1
C13B C 0.1001(11) 0.7970(7) 0.2747(6) 0.0266(19) Uani 0.360(11) 1 d . . P A 2
H13C H 0.127679 0.824174 0.224362 0.032 Uiso 0.360(11) 1 calc R . P A 2
H13D H 0.166864 0.725775 0.295264 0.032 Uiso 0.360(11) 1 calc R . P A 2
C14B C -0.0666(8) 0.7614(7) 0.2645(6) 0.034(3) Uani 0.360(11) 1 d . . P A 2
H14D H -0.086868 0.692196 0.227112 0.051 Uiso 0.360(11) 1 calc GR . P A 2
H14E H -0.130671 0.833265 0.244561 0.051 Uiso 0.360(11) 1 calc GR . P A 2
H14F H -0.091719 0.735438 0.314988 0.051 Uiso 0.360(11) 1 calc GR . P A 2
H5A H 0.480(5) 0.677(4) 0.351(2) 0.091(13) Uiso 1 1 d . . . . .
H5B H 0.643(4) 0.712(3) 0.3586(19) 0.061(10) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.239(3) . ?
O2 C4 1.257(3) . ?
O3 C5 1.262(3) . ?
O4 C8 1.211(3) . ?
O5 H5A 0.95(4) . ?
O5 H5B 0.88(4) . ?
O6 H6A 0.8496 . ?
O6 H6B 0.8503 . ?
N2 C1 1.371(3) . ?
N2 C5 1.412(3) . ?
N2 C3 1.470(3) . ?
N1 C4 1.410(3) . ?
N1 C1 1.372(3) . ?
N1 C2 1.470(3) . ?
N3 H3A 1.0000 . ?
N3 H3B 1.0000 . ?
N3 C11 1.503(3) . ?
N3 C12 1.497(4) . ?
N3 C13A 1.514(5) . ?
N3 C13B 1.591(8) . ?
C4 C6 1.398(3) . ?
C5 C6 1.404(3) . ?
C6 C7 1.499(3) . ?
C10 H10 0.9500 . ?
C10 C9 1.327(4) . ?
C10 C11 1.500(3) . ?
C7 H7 1.0000 . ?
C7 C8 1.535(3) . ?
C7 C11 1.547(3) . ?
C8 C9 1.470(3) . ?
C9 H9 0.9500 . ?
C11 H11 1.0000 . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 H3C 0.9800 . ?
C3 H3D 0.9800 . ?
C3 H3E 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13A H13A 0.9900 . ?
C13A H13B 0.9900 . ?
C13A C14A 1.506(8) . ?
C14A H14A 0.9800 . ?
C14A H14B 0.9800 . ?
C14A H14C 0.9800 . ?
C13B H13C 0.9900 . ?
C13B H13D 0.9900 . ?
C13B C14B 1.494(13) . ?
C14B H14D 0.9800 . ?
C14B H14E 0.9800 . ?
C14B H14F 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
H5A O5 H5B 106(3) . . ?
H6A O6 H6B 104.6 . . ?
C1 N2 C5 124.19(18) . . ?
C1 N2 C3 117.20(19) . . ?
C5 N2 C3 118.59(19) . . ?
C4 N1 C2 119.94(18) . . ?
C1 N1 C4 122.83(19) . . ?
C1 N1 C2 117.17(18) . . ?
C11 N3 H3A 106.0 . . ?
C11 N3 H3B 106.6 . . ?
C11 N3 C13A 104.3(3) . . ?
C11 N3 C13B 125.9(4) . . ?
C12 N3 H3A 106.0 . . ?
C12 N3 H3B 106.6 . . ?
C12 N3 C11 113.94(18) . . ?
C12 N3 C13A 119.7(3) . . ?
C12 N3 C13B 95.6(4) . . ?
C13A N3 H3A 106.0 . . ?
C13B N3 H3B 106.6 . . ?
O2 C4 N1 118.7(2) . . ?
O2 C4 C6 123.2(2) . . ?
C6 C4 N1 118.11(18) . . ?
O1 C1 N2 121.7(2) . . ?
O1 C1 N1 121.3(2) . . ?
N2 C1 N1 117.06(19) . . ?
O3 C5 N2 117.13(19) . . ?
O3 C5 C6 126.2(2) . . ?
C6 C5 N2 116.6(2) . . ?
C4 C6 C5 121.1(2) . . ?
C4 C6 C7 117.44(19) . . ?
C5 C6 C7 121.5(2) . . ?
C9 C10 H10 123.9 . . ?
C9 C10 C11 112.2(2) . . ?
C11 C10 H10 123.9 . . ?
C6 C7 H7 108.1 . . ?
C6 C7 C8 113.01(19) . . ?
C6 C7 C11 116.52(17) . . ?
C8 C7 H7 108.1 . . ?
C8 C7 C11 102.71(17) . . ?
C11 C7 H7 108.1 . . ?
O4 C8 C7 125.0(2) . . ?
O4 C8 C9 126.5(2) . . ?
C9 C8 C7 108.43(19) . . ?
C10 C9 C8 110.4(2) . . ?
C10 C9 H9 124.8 . . ?
C8 C9 H9 124.8 . . ?
N3 C11 C7 115.15(19) . . ?
N3 C11 H11 108.2 . . ?
C10 C11 N3 111.21(19) . . ?
C10 C11 C7 105.60(18) . . ?
C10 C11 H11 108.2 . . ?
C7 C11 H11 108.2 . . ?
N1 C2 H2A 109.5 . . ?
N1 C2 H2B 109.5 . . ?
N1 C2 H2C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
N2 C3 H3C 109.5 . . ?
N2 C3 H3D 109.5 . . ?
N2 C3 H3E 109.5 . . ?
H3C C3 H3D 109.5 . . ?
H3C C3 H3E 109.5 . . ?
H3D C3 H3E 109.5 . . ?
N3 C12 H12A 109.5 . . ?
N3 C12 H12B 109.5 . . ?
N3 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N3 C13A H13A 110.0 . . ?
N3 C13A H13B 110.0 . . ?
H13A C13A H13B 108.4 . . ?
C14A C13A N3 108.5(4) . . ?
C14A C13A H13A 110.0 . . ?
C14A C13A H13B 110.0 . . ?
C13A C14A H14A 109.5 . . ?
C13A C14A H14B 109.5 . . ?
C13A C14A H14C 109.5 . . ?
H14A C14A H14B 109.5 . . ?
H14A C14A H14C 109.5 . . ?
H14B C14A H14C 109.5 . . ?
N3 C13B H13C 110.8 . . ?
N3 C13B H13D 110.8 . . ?
H13C C13B H13D 108.9 . . ?
C14B C13B N3 104.8(7) . . ?
C14B C13B H13C 110.8 . . ?
C14B C13B H13D 110.8 . . ?
C13B C14B H14D 109.5 . . ?
C13B C14B H14E 109.5 . . ?
C13B C14B H14F 109.5 . . ?
H14D C14B H14E 109.5 . . ?
H14D C14B H14F 109.5 . . ?
H14E C14B H14F 109.5 . . ?

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

data_FBA
_database_code_depnum_ccdc_archive 'CCDC 1839148'

_audit_update_record             
;
2018-04-24 deposited with the CCDC.
2018-08-29 downloaded from the CCDC.
;
# publcif _publ_body_element loop end
_audit_creation_date             2018-04-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.04.03 svn.r3497 for OlexSys, GUI svn.r5486)
;
_shelx_SHELXL_version_number     2018/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C11 H10 N2 O4'
_chemical_formula_sum            'C11 H10 N2 O4'
_chemical_formula_weight         234.21
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   12.8188(8)
_cell_length_b                   6.1493(4)
_cell_length_c                   13.1714(8)
_cell_angle_alpha                90
_cell_angle_beta                 99.328(2)
_cell_angle_gamma                90
_cell_volume                     1024.53(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2367
_cell_measurement_temperature    150
_cell_measurement_theta_max      27.592
_cell_measurement_theta_min      2.057
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.118
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6489
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light yellow'
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.518
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0421
_diffrn_reflns_av_unetI/netI     0.0234
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            19375
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.592
_diffrn_reflns_theta_min         2.057
_diffrn_ambient_temperature      149.61
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker kappa APEXII CCD Diffractometer'
_diffrn_measurement_method       'φ scans, and ω scans with κ offsets'
_diffrn_radiation_monochromator  'Silicon Double Crystal'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Incoatec I\mS microfocus X-ray source'
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2012
_reflns_number_total             2367
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       'APEX3 (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.346
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         2367
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0534
_refine_ls_R_factor_gt           0.0446
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0477P)²+0.8317P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1121
_refine_ls_wR_factor_ref         0.1203
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C7(H7), C9(H9), C11(H11), C10(H10)
2.b Idealised Me refined as rotating group:
 C3(H3A,H3B,H3C), C2(H2A,H2B,H2C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O4 O 0.38270(9) 1.01797(19) 0.43449(9) 0.0282(3) Uani 1 1 d . . . . .
O1 O 0.25669(10) -0.0416(2) 0.70159(10) 0.0359(3) Uani 1 1 d . . . . .
O3 O 0.50064(9) 0.4717(2) 0.66888(11) 0.0373(3) Uani 1 1 d . . . . .
O2 O 0.15158(9) 0.5189(2) 0.48785(11) 0.0367(3) Uani 1 1 d . . . . .
N2 N 0.38146(10) 0.2074(2) 0.67983(10) 0.0248(3) Uani 1 1 d . . . . .
N1 N 0.20588(10) 0.2315(2) 0.59010(10) 0.0261(3) Uani 1 1 d . . . . .
C6 C 0.33209(11) 0.5122(2) 0.56590(11) 0.0218(3) Uani 1 1 d . . . . .
C7 C 0.36501(11) 0.6958(3) 0.52308(11) 0.0225(3) Uani 1 1 d . . . . .
H7 H 0.436747 0.730626 0.548241 0.027 Uiso 1 1 calc R . . . .
C8 C 0.31549(12) 0.8475(3) 0.44873(12) 0.0227(3) Uani 1 1 d . . . . .
C4 C 0.22383(12) 0.4281(3) 0.54328(12) 0.0245(3) Uani 1 1 d . . . . .
C1 C 0.27982(13) 0.1235(3) 0.65983(12) 0.0251(3) Uani 1 1 d . . . . .
C9 C 0.22187(12) 0.8776(3) 0.38375(12) 0.0263(3) Uani 1 1 d . . . . .
H9 H 0.161625 0.785633 0.377406 0.032 Uiso 1 1 calc R . . . .
C5 C 0.41144(12) 0.4008(3) 0.64124(12) 0.0247(3) Uani 1 1 d . . . . .
C11 C 0.32933(13) 1.1485(3) 0.36185(12) 0.0275(4) Uani 1 1 d . . . . .
H11 H 0.357015 1.278418 0.337644 0.033 Uiso 1 1 calc R . . . .
C10 C 0.23134(13) 1.0707(3) 0.32790(12) 0.0284(4) Uani 1 1 d . . . . .
H10 H 0.179252 1.133230 0.276718 0.034 Uiso 1 1 calc R . . . .
C3 C 0.45599(14) 0.0927(3) 0.75796(15) 0.0361(4) Uani 1 1 d . . . . .
H3A H 0.437391 0.119832 0.826130 0.054 Uiso 1 1 calc GR . . . .
H3B H 0.527859 0.145308 0.756303 0.054 Uiso 1 1 calc GR . . . .
H3C H 0.452528 -0.063769 0.743644 0.054 Uiso 1 1 calc GR . . . .
C2 C 0.09937(14) 0.1394(3) 0.57103(15) 0.0371(4) Uani 1 1 d . . . . .
H2A H 0.069953 0.138418 0.635224 0.056 Uiso 1 1 calc GR . . . .
H2B H 0.102420 -0.009777 0.545460 0.056 Uiso 1 1 calc GR . . . .
H2C H 0.054315 0.227729 0.519628 0.056 Uiso 1 1 calc GR . . . .


_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
O4 C8 1.3889(18) . ?
O4 C11 1.3475(19) . ?
O1 C1 1.214(2) . ?
O3 C5 1.2229(19) . ?
O2 C4 1.218(2) . ?
N2 C1 1.386(2) . ?
N2 C5 1.372(2) . ?
N2 C3 1.467(2) . ?
N1 C4 1.393(2) . ?
N1 C1 1.378(2) . ?
N1 C2 1.462(2) . ?
C6 C7 1.359(2) . ?
C6 C4 1.466(2) . ?
C6 C5 1.470(2) . ?
C7 H7 0.9500 . ?
C7 C8 1.425(2) . ?
C8 C9 1.369(2) . ?
C9 H9 0.9500 . ?
C9 C10 1.412(2) . ?
C11 H11 0.9500 . ?
C11 C10 1.351(2) . ?
C10 H10 0.9500 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 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
C11 O4 C8 106.92(12) . . ?
C1 N2 C3 116.07(14) . . ?
C5 N2 C1 124.28(14) . . ?
C5 N2 C3 119.15(14) . . ?
C4 N1 C2 118.48(14) . . ?
C1 N1 C4 124.59(13) . . ?
C1 N1 C2 116.76(14) . . ?
C7 C6 C4 123.79(14) . . ?
C7 C6 C5 116.09(13) . . ?
C4 C6 C5 120.09(14) . . ?
C6 C7 H7 113.0 . . ?
C6 C7 C8 134.03(14) . . ?
C8 C7 H7 113.0 . . ?
O4 C8 C7 111.71(13) . . ?
C9 C8 O4 108.26(14) . . ?
C9 C8 C7 140.01(15) . . ?
O2 C4 N1 119.94(14) . . ?
O2 C4 C6 124.26(15) . . ?
N1 C4 C6 115.80(14) . . ?
O1 C1 N2 121.08(16) . . ?
O1 C1 N1 120.82(15) . . ?
N1 C1 N2 118.10(14) . . ?
C8 C9 H9 126.3 . . ?
C8 C9 C10 107.39(14) . . ?
C10 C9 H9 126.3 . . ?
O3 C5 N2 120.23(15) . . ?
O3 C5 C6 123.08(15) . . ?
N2 C5 C6 116.69(13) . . ?
O4 C11 H11 124.4 . . ?
O4 C11 C10 111.21(14) . . ?
C10 C11 H11 124.4 . . ?
C9 C10 H10 126.9 . . ?
C11 C10 C9 106.22(14) . . ?
C11 C10 H10 126.9 . . ?
N2 C3 H3A 109.5 . . ?
N2 C3 H3B 109.5 . . ?
N2 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
N1 C2 H2A 109.5 . . ?
N1 C2 H2B 109.5 . . ?
N1 C2 H2C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?


_olex2_submission_special_instructions 'No special instructions were received'



_publcif_funding_html            
;
;
####################################################################### 
# 
# 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
_database_code_depnum_ccdc_archive 'CCDC 1839149'
_audit_update_record             
;
2018-04-24 deposited with the CCDC.
2018-08-29 downloaded from the CCDC.
;
_audit_creation_date             2018-03-15
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2018/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H23 N3 O4, C4 H8 O'
_chemical_formula_sum            'C24 H31 N3 O5'
_chemical_formula_weight         441.52
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   11.8801(13)
_cell_length_b                   9.9317(11)
_cell_length_c                   20.246(2)
_cell_angle_alpha                90
_cell_angle_beta                 104.310(4)
_cell_angle_gamma                90
_cell_volume                     2314.7(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9920
_cell_measurement_temperature    150
_cell_measurement_theta_max      25.663
_cell_measurement_theta_min      2.372
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.6412
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            violet
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    violet
_exptl_crystal_density_diffrn    1.267
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0904
_diffrn_reflns_av_unetI/netI     0.0546
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            73739
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         28.824
_diffrn_reflns_theta_min         1.769
_diffrn_ambient_temperature      150
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker kappa APEXII CCD Diffractometer'
_diffrn_measurement_method       'φ scans, and ω scans with κ offsets'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Incoatec I\mS microfocus X-ray source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3490
_reflns_number_total             6001
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       'APEX3 (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.836
_refine_diff_density_min         -0.457
_refine_diff_density_rms         0.078
_refine_ls_extinction_coef       0.0032(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/1 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     294
_refine_ls_number_reflns         6001
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1396
_refine_ls_R_factor_gt           0.0764
_refine_ls_restrained_S_all      1.028
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1210P)²+1.8257P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1998
_refine_ls_wR_factor_ref         0.2460
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C14(H14A,H14B), C21(H21A,H21B), C22(H22A,H22B), C23(H23A,
 H23B), C24(H24A,H24B)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C9(H9), C10(H10), C11(H11), C16(H16), C17(H17), C18(H18), C19(H19),
 C20(H20)
2.c Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C), C3(H3A,H3B,H3C), C12(H12A,H12B,H12C)
2.d Idealised tetrahedral OH refined as rotating group:
 O4(H4)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.16179(19) 1.00467(19) 0.19901(10) 0.0400(5) Uani 1 1 d . . . . .
O2 O 0.10828(18) 0.57663(17) 0.25974(9) 0.0335(5) Uani 1 1 d . . . . .
O3 O 0.1246(2) 0.93629(19) 0.41358(9) 0.0408(5) Uani 1 1 d . . . . .
O4 O 0.1366(2) 0.42893(18) 0.36597(9) 0.0395(5) Uani 1 1 d . . . . .
H4 H 0.126609 0.465616 0.327574 0.059 Uiso 1 1 calc GR . . . .
N1 N 0.1253(2) 0.7923(2) 0.22924(10) 0.0283(5) Uani 1 1 d . . . . .
N2 N 0.1471(2) 0.9701(2) 0.30726(10) 0.0282(5) Uani 1 1 d . . . . .
N3 N 0.1605(2) 0.1852(2) 0.59181(10) 0.0288(5) Uani 1 1 d . . . . .
C1 C 0.1457(2) 0.9275(2) 0.24285(13) 0.0288(6) Uani 1 1 d . . . . .
C2 C 0.1201(3) 0.7488(3) 0.15932(13) 0.0391(7) Uani 1 1 d . . . . .
H2A H 0.076728 0.815191 0.127097 0.059 Uiso 1 1 calc GR . . . .
H2B H 0.081140 0.661241 0.150940 0.059 Uiso 1 1 calc GR . . . .
H2C H 0.199172 0.740804 0.153199 0.059 Uiso 1 1 calc GR . . . .
C3 C 0.1680(3) 1.1132(3) 0.32198(15) 0.0405(7) Uani 1 1 d . . . . .
H3A H 0.245525 1.137287 0.317119 0.061 Uiso 1 1 calc GR . . . .
H3B H 0.162991 1.131890 0.368700 0.061 Uiso 1 1 calc GR . . . .
H3C H 0.109422 1.166466 0.289991 0.061 Uiso 1 1 calc GR . . . .
C4 C 0.1184(2) 0.6970(2) 0.27846(12) 0.0257(5) Uani 1 1 d . . . . .
C5 C 0.1296(2) 0.8858(2) 0.35924(12) 0.0273(5) Uani 1 1 d . . . . .
C6 C 0.1224(2) 0.7434(2) 0.34522(12) 0.0255(5) Uani 1 1 d . . . . .
C7 C 0.1229(2) 0.6599(2) 0.40232(13) 0.0280(6) Uani 1 1 d . . . . .
H7 H 0.116088 0.709259 0.441342 0.034 Uiso 1 1 calc R . . . .
C8 C 0.1312(2) 0.5235(3) 0.41328(12) 0.0298(6) Uani 1 1 d . . . . .
C9 C 0.1369(3) 0.4743(3) 0.47961(13) 0.0317(6) Uani 1 1 d . . . . .
H9 H 0.133742 0.538544 0.513863 0.038 Uiso 1 1 calc R . . . .
C10 C 0.1467(3) 0.3422(3) 0.49830(13) 0.0321(6) Uani 1 1 d . . . . .
H10 H 0.148439 0.274309 0.465527 0.038 Uiso 1 1 calc R . . . .
C11 C 0.1540(2) 0.3073(3) 0.56651(12) 0.0291(6) Uani 1 1 d . . . . .
H11 H 0.154270 0.379444 0.597382 0.035 Uiso 1 1 calc R . . . .
C12 C 0.1575(3) 0.0658(3) 0.55003(15) 0.0466(8) Uani 1 1 d . . . . .
H12A H 0.122373 0.088122 0.502227 0.070 Uiso 1 1 calc GR . . . .
H12B H 0.111202 -0.004189 0.565081 0.070 Uiso 1 1 calc GR . . . .
H12C H 0.236758 0.032745 0.554597 0.070 Uiso 1 1 calc GR . . . .
C13 C 0.1718(2) 0.1639(3) 0.66483(13) 0.0303(6) Uani 1 1 d . . . . .
H13A H 0.108178 0.104505 0.670815 0.036 Uiso 1 1 calc R . . . .
H13B H 0.163648 0.251401 0.686587 0.036 Uiso 1 1 calc R . . . .
C14 C 0.2873(3) 0.1012(3) 0.70023(14) 0.0361(6) Uani 1 1 d . . . . .
H14A H 0.293213 0.098348 0.749842 0.043 Uiso 1 1 calc R . . . .
H14B H 0.288884 0.007228 0.684215 0.043 Uiso 1 1 calc R . . . .
C15 C 0.3911(3) 0.1740(3) 0.68849(13) 0.0338(6) Uani 1 1 d . . . . .
C16 C 0.4721(3) 0.1077(3) 0.66158(17) 0.0463(8) Uani 1 1 d . . . . .
H16 H 0.461485 0.014720 0.650779 0.056 Uiso 1 1 calc R . . . .
C17 C 0.5681(3) 0.1736(4) 0.6500(2) 0.0573(9) Uani 1 1 d . . . . .
H17 H 0.622601 0.125844 0.631556 0.069 Uiso 1 1 calc R . . . .
C18 C 0.5847(3) 0.3089(4) 0.66541(19) 0.0553(9) Uani 1 1 d . . . . .
H18 H 0.649636 0.355377 0.656969 0.066 Uiso 1 1 calc R . . . .
C19 C 0.5055(3) 0.3752(4) 0.69316(17) 0.0498(8) Uani 1 1 d . . . . .
H19 H 0.517388 0.467559 0.704996 0.060 Uiso 1 1 calc R . . . .
C20 C 0.4095(3) 0.3101(3) 0.70407(15) 0.0401(7) Uani 1 1 d . . . . .
H20 H 0.355181 0.358405 0.722397 0.048 Uiso 1 1 calc R . . . .
O5 O 0.3533(4) 0.7925(4) 0.5782(2) 0.1034(12) Uani 1 1 d . . . . .
C21 C 0.3970(5) 0.8163(6) 0.5212(3) 0.0944(17) Uani 1 1 d . . . . .
H21A H 0.387117 0.912352 0.507932 0.113 Uiso 1 1 calc R . . . .
H21B H 0.354639 0.760970 0.482279 0.113 Uiso 1 1 calc R . . . .
C22 C 0.5223(5) 0.7802(8) 0.5393(3) 0.117(2) Uani 1 1 d . . . . .
H22A H 0.571356 0.859225 0.556948 0.140 Uiso 1 1 calc R . . . .
H22B H 0.546322 0.742717 0.499620 0.140 Uiso 1 1 calc R . . . .
C23 C 0.5290(6) 0.6761(8) 0.5936(4) 0.140(3) Uani 1 1 d . . . . .
H23A H 0.593341 0.696847 0.633780 0.169 Uiso 1 1 calc R . . . .
H23B H 0.542406 0.585821 0.576327 0.169 Uiso 1 1 calc R . . . .
C24 C 0.4143(5) 0.6802(6) 0.6125(3) 0.0990(17) Uani 1 1 d . . . . .
H24A H 0.370207 0.596230 0.598119 0.119 Uiso 1 1 calc R . . . .
H24B H 0.426539 0.690316 0.662455 0.119 Uiso 1 1 calc R . . . .


_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 1.223(3) . ?
O2 C4 1.251(3) . ?
O3 C5 1.224(3) . ?
O4 H4 0.8400 . ?
O4 C8 1.354(3) . ?
N1 C1 1.380(3) . ?
N1 C2 1.467(3) . ?
N1 C4 1.392(3) . ?
N2 C1 1.367(3) . ?
N2 C3 1.461(3) . ?
N2 C5 1.400(3) . ?
N3 C11 1.311(3) . ?
N3 C12 1.452(3) . ?
N3 C13 1.466(3) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 C6 1.418(3) . ?
C5 C6 1.441(3) . ?
C6 C7 1.421(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.373(3) . ?
C8 C9 1.415(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.362(4) . ?
C10 H10 0.9500 . ?
C10 C11 1.405(3) . ?
C11 H11 0.9500 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.516(4) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.498(4) . ?
C15 C16 1.384(4) . ?
C15 C20 1.392(4) . ?
C16 H16 0.9500 . ?
C16 C17 1.385(5) . ?
C17 H17 0.9500 . ?
C17 C18 1.383(5) . ?
C18 H18 0.9500 . ?
C18 C19 1.377(5) . ?
C19 H19 0.9500 . ?
C19 C20 1.376(4) . ?
C20 H20 0.9500 . ?
O5 C21 1.398(6) . ?
O5 C24 1.415(6) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C21 C22 1.486(8) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C22 C23 1.497(8) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C23 C24 1.504(8) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 O4 H4 109.5 . . ?
C1 N1 C2 116.3(2) . . ?
C1 N1 C4 123.9(2) . . ?
C4 N1 C2 119.7(2) . . ?
C1 N2 C3 117.2(2) . . ?
C1 N2 C5 124.2(2) . . ?
C5 N2 C3 118.5(2) . . ?
C11 N3 C12 122.5(2) . . ?
C11 N3 C13 120.6(2) . . ?
C12 N3 C13 116.9(2) . . ?
O1 C1 N1 121.1(2) . . ?
O1 C1 N2 122.1(2) . . ?
N2 C1 N1 116.9(2) . . ?
N1 C2 H2A 109.5 . . ?
N1 C2 H2B 109.5 . . ?
N1 C2 H2C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
N2 C3 H3A 109.5 . . ?
N2 C3 H3B 109.5 . . ?
N2 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
O2 C4 N1 116.8(2) . . ?
O2 C4 C6 125.3(2) . . ?
N1 C4 C6 117.9(2) . . ?
O3 C5 N2 118.7(2) . . ?
O3 C5 C6 124.4(2) . . ?
N2 C5 C6 116.8(2) . . ?
C4 C6 C5 119.6(2) . . ?
C4 C6 C7 125.3(2) . . ?
C7 C6 C5 115.1(2) . . ?
C6 C7 H7 113.1 . . ?
C8 C7 C6 133.8(2) . . ?
C8 C7 H7 113.1 . . ?
O4 C8 C7 125.7(2) . . ?
O4 C8 C9 115.6(2) . . ?
C7 C8 C9 118.6(2) . . ?
C8 C9 H9 117.4 . . ?
C10 C9 C8 125.2(2) . . ?
C10 C9 H9 117.4 . . ?
C9 C10 H10 120.3 . . ?
C9 C10 C11 119.4(2) . . ?
C11 C10 H10 120.3 . . ?
N3 C11 C10 126.5(2) . . ?
N3 C11 H11 116.7 . . ?
C10 C11 H11 116.7 . . ?
N3 C12 H12A 109.5 . . ?
N3 C12 H12B 109.5 . . ?
N3 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N3 C13 H13A 109.1 . . ?
N3 C13 H13B 109.1 . . ?
N3 C13 C14 112.5(2) . . ?
H13A C13 H13B 107.8 . . ?
C14 C13 H13A 109.1 . . ?
C14 C13 H13B 109.1 . . ?
C13 C14 H14A 108.7 . . ?
C13 C14 H14B 108.7 . . ?
H14A C14 H14B 107.6 . . ?
C15 C14 C13 114.3(2) . . ?
C15 C14 H14A 108.7 . . ?
C15 C14 H14B 108.7 . . ?
C16 C15 C14 120.8(3) . . ?
C16 C15 C20 117.8(3) . . ?
C20 C15 C14 121.4(3) . . ?
C15 C16 H16 119.2 . . ?
C15 C16 C17 121.6(3) . . ?
C17 C16 H16 119.2 . . ?
C16 C17 H17 120.0 . . ?
C18 C17 C16 119.9(3) . . ?
C18 C17 H17 120.0 . . ?
C17 C18 H18 120.6 . . ?
C19 C18 C17 118.9(3) . . ?
C19 C18 H18 120.6 . . ?
C18 C19 H19 119.4 . . ?
C20 C19 C18 121.2(3) . . ?
C20 C19 H19 119.4 . . ?
C15 C20 H20 119.7 . . ?
C19 C20 C15 120.6(3) . . ?
C19 C20 H20 119.7 . . ?
C21 O5 C24 106.8(4) . . ?
O5 C21 H21A 110.1 . . ?
O5 C21 H21B 110.1 . . ?
O5 C21 C22 108.0(5) . . ?
H21A C21 H21B 108.4 . . ?
C22 C21 H21A 110.1 . . ?
C22 C21 H21B 110.1 . . ?
C21 C22 H22A 111.3 . . ?
C21 C22 H22B 111.3 . . ?
C21 C22 C23 102.5(5) . . ?
H22A C22 H22B 109.2 . . ?
C23 C22 H22A 111.3 . . ?
C23 C22 H22B 111.3 . . ?
C22 C23 H23A 110.5 . . ?
C22 C23 H23B 110.5 . . ?
C22 C23 C24 106.3(5) . . ?
H23A C23 H23B 108.7 . . ?
C24 C23 H23A 110.5 . . ?
C24 C23 H23B 110.5 . . ?
O5 C24 C23 106.4(5) . . ?
O5 C24 H24A 110.4 . . ?
O5 C24 H24B 110.4 . . ?
C23 C24 H24A 110.4 . . ?
C23 C24 H24B 110.4 . . ?
H24A C24 H24B 108.6 . . ?

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
_geom_hbond_publ_flag
O4 H4 O2 0.84 1.73 2.556(2) 166.2 . yes

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

data_14a
_database_code_depnum_ccdc_archive 'CCDC 1839152'

_audit_update_record             
;
2018-04-24 deposited with the CCDC.
2018-08-29 downloaded from the CCDC.
;
# publcif _publ_body_element loop end
_audit_creation_date             2018-03-09
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2018/1
_chemical_name_common            ?
_chemical_name_systematic        OMe-a
_chemical_formula_moiety         'C Cl3 D, C19 H21 N3 O5'
_chemical_formula_sum            'C20 H21 Cl3 D N3 O5'
_chemical_formula_weight         491.76
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
D D 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   6.7470(14)
_cell_length_b                   22.937(5)
_cell_length_c                   13.927(3)
_cell_angle_alpha                90
_cell_angle_beta                 90.66(3)
_cell_angle_gamma                90
_cell_volume                     2155.1(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4009
_cell_measurement_temperature    100
_cell_measurement_theta_max      26.37
_cell_measurement_theta_min      1.522
_shelx_estimated_absorpt_T_max   0.995
_shelx_estimated_absorpt_T_min   0.955
_exptl_absorpt_coefficient_mu    0.464
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'dark blue'
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    1.516
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1016
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0380
_diffrn_reflns_av_unetI/netI     0.0208
_diffrn_reflns_Laue_measured_fraction_full 0.913
_diffrn_reflns_Laue_measured_fraction_max 0.907
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            28933
_diffrn_reflns_point_group_measured_fraction_full 0.913
_diffrn_reflns_point_group_measured_fraction_max 0.907
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.370
_diffrn_reflns_theta_min         1.711
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.913
_diffrn_measured_fraction_theta_max 0.907
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3591
_reflns_number_total             4009
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'XDS (Kabsch, 1993)'
_computing_data_collection       'AS QEGUI'
_computing_data_reduction        'XDS (Kabsch, 1993)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.321
_refine_diff_density_min         -0.445
_refine_diff_density_rms         0.077
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.110
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     284
_refine_ls_number_reflns         4009
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0500
_refine_ls_R_factor_gt           0.0452
_refine_ls_restrained_S_all      1.110
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0566P)²+2.9306P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1194
_refine_ls_wR_factor_ref         0.1225
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C20(D20)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C9(H9), C14(H14), C11(H11), C18(H18), C10(H10), C17(H17), C15(H15)
2.c Tetrahedral OH refined with riding coordinates:
 O4(H4)
2.d Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C), C12(H12A,H12B,H12C), C3(H3A,H3B,H3C), C19(H19A,H19B,H19C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.65737(9) 0.40683(3) 0.68873(5) 0.02820(18) Uani 1 1 d . . . . .
Cl2 Cl 0.89743(10) 0.33681(3) 0.56125(5) 0.02776(17) Uani 1 1 d . . . . .
Cl3 Cl 0.93888(10) 0.32455(3) 0.76906(5) 0.03049(18) Uani 1 1 d . . . . .
O3 O 0.8887(3) 0.31212(8) 0.33201(14) 0.0248(4) Uani 1 1 d . . . . .
O4 O 0.7647(3) 0.53388(7) 0.29271(14) 0.0237(4) Uani 1 1 d . . . . .
H4 H 0.752666 0.520015 0.237121 0.036 Uiso 1 1 calc R . . . .
O1 O 0.9126(3) 0.30271(8) 0.00640(14) 0.0254(4) Uani 1 1 d . . . . .
O2 O 0.8587(3) 0.48238(7) 0.13918(14) 0.0258(4) Uani 1 1 d . . . . .
O5 O 0.5939(3) 0.61696(9) 1.03584(15) 0.0338(5) Uani 1 1 d . . . . .
N2 N 0.8990(3) 0.30766(8) 0.16914(16) 0.0195(4) Uani 1 1 d . . . . .
N1 N 0.8874(3) 0.39279(9) 0.07438(15) 0.0195(4) Uani 1 1 d . . . . .
N3 N 0.6468(3) 0.61445(9) 0.63551(16) 0.0194(4) Uani 1 1 d . . . . .
C7 C 0.8322(3) 0.43163(10) 0.33357(18) 0.0191(5) Uani 1 1 d . . . . .
H7 H 0.844558 0.407050 0.388214 0.023 Uiso 1 1 calc R . . . .
C6 C 0.8612(3) 0.40182(10) 0.24666(18) 0.0184(5) Uani 1 1 d . . . . .
C4 C 0.8679(3) 0.42886(10) 0.15381(18) 0.0192(5) Uani 1 1 d . . . . .
C8 C 0.7891(3) 0.48938(10) 0.35738(19) 0.0191(5) Uani 1 1 d . . . . .
C13 C 0.6347(3) 0.61533(10) 0.73727(19) 0.0190(5) Uani 1 1 d . . . . .
C1 C 0.9002(3) 0.33246(10) 0.07906(19) 0.0194(5) Uani 1 1 d . . . . .
C9 C 0.7656(3) 0.50320(10) 0.45366(19) 0.0212(5) Uani 1 1 d . . . . .
H9 H 0.784853 0.472674 0.498923 0.025 Uiso 1 1 calc R . . . .
C5 C 0.8839(3) 0.33876(10) 0.25530(18) 0.0184(5) Uani 1 1 d . . . . .
C14 C 0.6242(4) 0.56396(11) 0.79163(19) 0.0221(5) Uani 1 1 d . . . . .
H14 H 0.625769 0.527229 0.760136 0.027 Uiso 1 1 calc R . . . .
C16 C 0.6071(3) 0.61982(12) 0.9380(2) 0.0250(6) Uani 1 1 d . . . . .
C11 C 0.6994(3) 0.56609(10) 0.58724(19) 0.0196(5) Uani 1 1 d . . . . .
H11 H 0.729117 0.532944 0.625687 0.024 Uiso 1 1 calc R . . . .
C18 C 0.6296(4) 0.66846(11) 0.7859(2) 0.0232(5) Uani 1 1 d . . . . .
H18 H 0.636660 0.703733 0.750381 0.028 Uiso 1 1 calc R . . . .
C10 C 0.7158(3) 0.55828(11) 0.48994(19) 0.0213(5) Uani 1 1 d . . . . .
H10 H 0.693508 0.590023 0.447359 0.026 Uiso 1 1 calc R . . . .
C17 C 0.6145(4) 0.67090(11) 0.8848(2) 0.0255(6) Uani 1 1 d . . . . .
H17 H 0.609131 0.707591 0.916337 0.031 Uiso 1 1 calc R . . . .
C15 C 0.6116(4) 0.56624(12) 0.8903(2) 0.0259(6) Uani 1 1 d . . . . .
H15 H 0.605896 0.531070 0.926205 0.031 Uiso 1 1 calc R . . . .
C2 C 0.8959(4) 0.41924(11) -0.0215(2) 0.0258(5) Uani 1 1 d . . . . .
H2A H 1.029579 0.414623 -0.047226 0.039 Uiso 1 1 calc GR . . . .
H2B H 0.863825 0.460818 -0.017026 0.039 Uiso 1 1 calc GR . . . .
H2C H 0.799967 0.399942 -0.064235 0.039 Uiso 1 1 calc GR . . . .
C12 C 0.6023(4) 0.66871(11) 0.5824(2) 0.0278(6) Uani 1 1 d . . . . .
H12A H 0.716016 0.695186 0.587230 0.042 Uiso 1 1 calc GR . . . .
H12B H 0.485545 0.687461 0.609981 0.042 Uiso 1 1 calc GR . . . .
H12C H 0.575917 0.659486 0.514750 0.042 Uiso 1 1 calc GR . . . .
C3 C 0.9216(4) 0.24417(11) 0.1741(2) 0.0281(6) Uani 1 1 d . . . . .
H3A H 1.043133 0.232626 0.141268 0.042 Uiso 1 1 calc GR . . . .
H3B H 0.807262 0.225456 0.142944 0.042 Uiso 1 1 calc GR . . . .
H3C H 0.929527 0.231980 0.241504 0.042 Uiso 1 1 calc GR . . . .
C20 C 0.8911(4) 0.37303(11) 0.6735(2) 0.0240(5) Uani 1 1 d . . . . .
D20 D 0.995651 0.403944 0.674213 0.029 Uiso 1 1 calc R . . . .
C19 C 0.5889(5) 0.67129(15) 1.0875(2) 0.0388(7) Uani 1 1 d . . . . .
H19A H 0.588765 0.663475 1.156678 0.058 Uiso 1 1 calc GR . . . .
H19B H 0.468621 0.692844 1.069541 0.058 Uiso 1 1 calc GR . . . .
H19C H 0.705755 0.694534 1.071447 0.058 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C20 1.772(3) . ?
Cl2 C20 1.771(3) . ?
Cl3 C20 1.761(3) . ?
O3 C5 1.231(3) . ?
O4 H4 0.8400 . ?
O4 C8 1.370(3) . ?
O1 C1 1.224(3) . ?
O2 C4 1.246(3) . ?
O5 C16 1.368(4) . ?
O5 C19 1.439(4) . ?
N2 C1 1.378(3) . ?
N2 C5 1.401(3) . ?
N2 C3 1.466(3) . ?
N1 C4 1.389(3) . ?
N1 C1 1.388(3) . ?
N1 C2 1.468(3) . ?
N3 C13 1.421(4) . ?
N3 C11 1.347(3) . ?
N3 C12 1.477(3) . ?
C7 H7 0.9500 . ?
C7 C6 1.406(4) . ?
C7 C8 1.397(3) . ?
C6 C4 1.435(4) . ?
C6 C5 1.459(3) . ?
C8 C9 1.389(4) . ?
C13 C14 1.403(3) . ?
C13 C18 1.395(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.403(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.379(4) . ?
C16 C17 1.388(4) . ?
C16 C15 1.397(4) . ?
C11 H11 0.9500 . ?
C11 C10 1.373(4) . ?
C18 H18 0.9500 . ?
C18 C17 1.383(4) . ?
C10 H10 0.9500 . ?
C17 H17 0.9500 . ?
C15 H15 0.9500 . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C20 D20 1.0000 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 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
C8 O4 H4 109.5 . . ?
C16 O5 C19 117.3(2) . . ?
C1 N2 C5 124.8(2) . . ?
C1 N2 C3 116.9(2) . . ?
C5 N2 C3 118.3(2) . . ?
C4 N1 C2 118.9(2) . . ?
C1 N1 C4 124.3(2) . . ?
C1 N1 C2 116.8(2) . . ?
C13 N3 C12 118.3(2) . . ?
C11 N3 C13 121.9(2) . . ?
C11 N3 C12 119.8(2) . . ?
C6 C7 H7 112.9 . . ?
C8 C7 H7 112.9 . . ?
C8 C7 C6 134.2(2) . . ?
C7 C6 C4 124.9(2) . . ?
C7 C6 C5 115.2(2) . . ?
C4 C6 C5 119.9(2) . . ?
O2 C4 N1 117.5(2) . . ?
O2 C4 C6 124.8(2) . . ?
N1 C4 C6 117.7(2) . . ?
O4 C8 C7 125.0(2) . . ?
O4 C8 C9 116.8(2) . . ?
C9 C8 C7 118.2(2) . . ?
C14 C13 N3 122.0(2) . . ?
C18 C13 N3 119.9(2) . . ?
C18 C13 C14 118.0(2) . . ?
O1 C1 N2 121.6(2) . . ?
O1 C1 N1 121.4(2) . . ?
N2 C1 N1 117.0(2) . . ?
C8 C9 H9 117.1 . . ?
C8 C9 C10 125.7(2) . . ?
C10 C9 H9 117.1 . . ?
O3 C5 N2 119.3(2) . . ?
O3 C5 C6 124.4(2) . . ?
N2 C5 C6 116.3(2) . . ?
C13 C14 H14 119.7 . . ?
C15 C14 C13 120.7(2) . . ?
C15 C14 H14 119.7 . . ?
O5 C16 C17 125.1(2) . . ?
O5 C16 C15 115.7(3) . . ?
C17 C16 C15 119.2(3) . . ?
N3 C11 H11 115.7 . . ?
N3 C11 C10 128.7(2) . . ?
C10 C11 H11 115.7 . . ?
C13 C18 H18 119.3 . . ?
C17 C18 C13 121.4(2) . . ?
C17 C18 H18 119.3 . . ?
C9 C10 H10 120.1 . . ?
C11 C10 C9 119.7(2) . . ?
C11 C10 H10 120.1 . . ?
C16 C17 H17 120.0 . . ?
C18 C17 C16 120.1(2) . . ?
C18 C17 H17 120.0 . . ?
C14 C15 C16 120.6(3) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 H15 119.7 . . ?
N1 C2 H2A 109.5 . . ?
N1 C2 H2B 109.5 . . ?
N1 C2 H2C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
N3 C12 H12A 109.5 . . ?
N3 C12 H12B 109.5 . . ?
N3 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N2 C3 H3A 109.5 . . ?
N2 C3 H3B 109.5 . . ?
N2 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
Cl1 C20 D20 108.5 . . ?
Cl2 C20 Cl1 109.95(14) . . ?
Cl2 C20 D20 108.5 . . ?
Cl3 C20 Cl1 109.94(15) . . ?
Cl3 C20 Cl2 111.39(14) . . ?
Cl3 C20 D20 108.5 . . ?
O5 C19 H19A 109.5 . . ?
O5 C19 H19B 109.5 . . ?
O5 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?


_olex2_submission_special_instructions 'No special instructions were received'

# start Validation Reply Form
_vrf_PLAT029_14a                 
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.913 Why?  
RESPONSE: The data collection was carried out at the Australian Synchrotron. The
 diffraction was measured along one axis, giving rise to a lower completeness
 value, which is typical of data collected at the Synchrotron.
;
# end Validation Reply Form



_publcif_funding_html            
;
;
####################################################################### 
# 
# 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_9b
_database_code_depnum_ccdc_archive 'CCDC 1839151'
#Added by publCIF



_audit_update_record             
;
2018-04-24 deposited with the CCDC.
2018-08-29 downloaded from the CCDC.
;


_cell_special_details            ?
# publcif _publ_body_element loop end
_audit_creation_date             2018-04-16
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.04.03 svn.r3497 for OlexSys, GUI svn.r5486)
;
_shelx_SHELXL_version_number     2018/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C19 H21 N3 O4), 7(H2 O)'
_chemical_formula_sum            'C38 H56 N6 O15'
_chemical_formula_weight         836.88
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   11.253(2)
_cell_length_b                   15.863(3)
_cell_length_c                   22.909(5)
_cell_angle_alpha                90
_cell_angle_beta                 99.957(3)
_cell_angle_gamma                90
_cell_volume                     4027.9(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9576
_cell_measurement_temperature    150
_cell_measurement_theta_max      27.877
_cell_measurement_theta_min      1.569
_shelx_estimated_absorpt_T_max   0.988
_shelx_estimated_absorpt_T_min   0.972
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.6117
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.380
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1784
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0729
_diffrn_reflns_av_unetI/netI     0.0365
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            108223
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.877
_diffrn_reflns_theta_min         1.569
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker kappa APEXII CCD Diffractometer'
_diffrn_measurement_method       'φ scans, and ω scans with κ offsets'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Incoatec I\mS microfocus X-ray source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6975
_reflns_number_total             9576
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       'APEX3 (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.432
_refine_diff_density_min         -0.795
_refine_diff_density_rms         0.075
_refine_ls_extinction_coef       0.0020(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/1 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     549
_refine_ls_number_reflns         9576
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1013
_refine_ls_R_factor_gt           0.0732
_refine_ls_restrained_S_all      1.053
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0837P)²+7.0807P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1872
_refine_ls_wR_factor_ref         0.2083
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2.a Riding coordinates:
 O1A(H1AA,H1AB), O2A(H2AA,H2AB), O3A(H3AA,H3AB), O4A(H4AA,H4AB), O5A(H5AA,
 H5AB), O6A(H6AA,H6AB), O7A(H7AA,H7AB)
2.b Ternary CH refined with riding coordinates:
 C7(H7), C11(H11), C7'(H7'), C11'(H11')
2.c Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C13'(H13C,H13D)
2.d Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C15(H15), C16(H16), C17(H17), C18(H18), C19(H19), C9'(H9'),
 C10'(H10'), C15'(H15'), C16'(H16'), C17'(H17'), C18'(H18'), C19'(H19')
2.e Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C), C3(H3A,H3B,H3C), C12(H12A,H12B,H12C), C2'(H2'A,H2'B,H2'C),
 C3'(H3'A,H3'B,H3'C), C12'(H12D,H12E,H12F)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.50718(18) 0.61500(13) 0.44387(10) 0.0338(5) Uani 1 1 d . . . . .
O2 O 0.15345(17) 0.47562(12) 0.44112(8) 0.0274(4) Uani 1 1 d . . . . .
O3 O 0.35122(17) 0.60642(12) 0.61425(8) 0.0265(4) Uani 1 1 d . . . . .
O4 O 0.07564(17) 0.64705(11) 0.58149(9) 0.0270(4) Uani 1 1 d . . . . .
N1 N 0.3280(2) 0.54916(14) 0.44199(10) 0.0244(5) Uani 1 1 d . . . . .
N2 N 0.43325(19) 0.60682(14) 0.52945(10) 0.0239(5) Uani 1 1 d . . . . .
N3 N 0.1447(2) 0.34969(14) 0.58929(10) 0.0235(5) Uani 1 1 d . . . . .
C1 C 0.4270(2) 0.59135(16) 0.47041(12) 0.0248(5) Uani 1 1 d . . . . .
C2 C 0.3195(3) 0.5364(2) 0.37803(13) 0.0351(7) Uani 1 1 d . . . . .
H2A H 0.336604 0.589656 0.359388 0.053 Uiso 1 1 calc GR . . . .
H2B H 0.237982 0.517424 0.361086 0.053 Uiso 1 1 calc GR . . . .
H2C H 0.378263 0.493745 0.370863 0.053 Uiso 1 1 calc GR . . . .
C3 C 0.5371(2) 0.65519(18) 0.55891(14) 0.0317(6) Uani 1 1 d . . . . .
H3A H 0.528437 0.714173 0.546169 0.048 Uiso 1 1 calc GR . . . .
H3B H 0.611144 0.631773 0.548379 0.048 Uiso 1 1 calc GR . . . .
H3C H 0.541275 0.652042 0.601944 0.048 Uiso 1 1 calc GR . . . .
C4 C 0.2367(2) 0.51762(15) 0.47058(12) 0.0220(5) Uani 1 1 d . . . . .
C5 C 0.3416(2) 0.58362(15) 0.56086(11) 0.0208(5) Uani 1 1 d . . . . .
C6 C 0.2458(2) 0.53666(15) 0.53095(11) 0.0212(5) Uani 1 1 d . . . . .
C7 C 0.1500(2) 0.50698(15) 0.56372(11) 0.0208(5) Uani 1 1 d . . . . .
H7 H 0.081758 0.485143 0.533687 0.025 Uiso 1 1 calc R . . . .
C8 C 0.0990(2) 0.57608(16) 0.59904(12) 0.0230(5) Uani 1 1 d . . . . .
C9 C 0.0836(3) 0.54034(18) 0.65620(12) 0.0288(6) Uani 1 1 d . . . . .
H9 H 0.046660 0.568594 0.684969 0.035 Uiso 1 1 calc R . . . .
C10 C 0.1284(3) 0.46298(18) 0.66208(12) 0.0309(6) Uani 1 1 d . . . . .
H10 H 0.125465 0.427904 0.695403 0.037 Uiso 1 1 calc R . . . .
C11 C 0.1844(2) 0.43730(16) 0.61006(11) 0.0237(5) Uani 1 1 d . . . . .
H11 H 0.274088 0.437273 0.622413 0.028 Uiso 1 1 calc R . . . .
C12 C 0.0110(2) 0.34051(17) 0.57203(13) 0.0283(6) Uani 1 1 d . . . . .
H12A H -0.028988 0.369802 0.600961 0.043 Uiso 1 1 calc GR . . . .
H12B H -0.010532 0.280595 0.571151 0.043 Uiso 1 1 calc GR . . . .
H12C H -0.015239 0.365104 0.532667 0.043 Uiso 1 1 calc GR . . . .
C13 C 0.2077(3) 0.32000(17) 0.53999(13) 0.0268(6) Uani 1 1 d . . . . .
H13A H 0.175541 0.351256 0.503238 0.032 Uiso 1 1 calc R . . . .
H13B H 0.294963 0.332415 0.550502 0.032 Uiso 1 1 calc R . . . .
C14 C 0.1903(2) 0.22698(16) 0.52894(12) 0.0251(5) Uani 1 1 d . . . . .
C15 C 0.1091(3) 0.19730(18) 0.48117(13) 0.0321(6) Uani 1 1 d . . . . .
H15 H 0.062945 0.235913 0.454739 0.038 Uiso 1 1 calc R . . . .
C16 C 0.0947(3) 0.1113(2) 0.47174(15) 0.0388(7) Uani 1 1 d . . . . .
H16 H 0.038179 0.091097 0.439093 0.047 Uiso 1 1 calc R . . . .
C17 C 0.1628(3) 0.05477(19) 0.50992(16) 0.0424(8) Uani 1 1 d . . . . .
H17 H 0.153616 -0.004146 0.503191 0.051 Uiso 1 1 calc R . . . .
C18 C 0.2433(3) 0.0841(2) 0.55737(16) 0.0403(7) Uani 1 1 d . . . . .
H18 H 0.289549 0.045470 0.583717 0.048 Uiso 1 1 calc R . . . .
C19 C 0.2573(3) 0.16938(19) 0.56691(14) 0.0332(6) Uani 1 1 d . . . . .
H19 H 0.313511 0.189191 0.599839 0.040 Uiso 1 1 calc R . . . .
O1' O 0.2186(2) -0.01435(15) 0.35402(12) 0.0481(6) Uani 1 1 d . . . . .
O2' O -0.1895(2) 0.00316(14) 0.30694(12) 0.0459(6) Uani 1 1 d . . . . .
O3' O 0.05127(19) 0.23821(13) 0.29087(10) 0.0355(5) Uani 1 1 d . . . . .
O4' O -0.1323(2) 0.18780(17) 0.17291(10) 0.0462(6) Uani 1 1 d . . . . .
N1' N 0.0153(2) -0.00533(16) 0.33157(14) 0.0394(6) Uani 1 1 d . . . . .
N2' N 0.1365(2) 0.11198(16) 0.32350(12) 0.0331(5) Uani 1 1 d . . . . .
N3' N -0.3032(2) 0.23257(14) 0.34974(10) 0.0235(5) Uani 1 1 d . . . . .
C1' C 0.1282(3) 0.02839(19) 0.33706(15) 0.0360(7) Uani 1 1 d . . . . .
C2' C 0.0050(4) -0.0937(2) 0.3486(2) 0.0584(11) Uani 1 1 d . . . . .
H2'A H -0.071355 -0.102100 0.362848 0.088 Uiso 1 1 calc GR . . . .
H2'B H 0.072388 -0.108075 0.380176 0.088 Uiso 1 1 calc GR . . . .
H2'C H 0.007209 -0.129942 0.314174 0.088 Uiso 1 1 calc GR . . . .
C3' C 0.2572(3) 0.1489(2) 0.33249(18) 0.0442(8) Uani 1 1 d . . . . .
H3'A H 0.302533 0.125631 0.303357 0.066 Uiso 1 1 calc GR . . . .
H3'B H 0.299274 0.135761 0.372565 0.066 Uiso 1 1 calc GR . . . .
H3'C H 0.250740 0.210238 0.327590 0.066 Uiso 1 1 calc GR . . . .
C4' C -0.0908(3) 0.04019(19) 0.31053(14) 0.0347(7) Uani 1 1 d . . . . .
C5' C 0.0352(3) 0.16242(18) 0.30291(13) 0.0296(6) Uani 1 1 d . . . . .
C6' C -0.0771(3) 0.12475(17) 0.29629(12) 0.0279(6) Uani 1 1 d . . . . .
C7' C -0.1858(3) 0.17591(17) 0.27125(12) 0.0270(6) Uani 1 1 d . . . . .
H7' H -0.257144 0.137351 0.264828 0.032 Uiso 1 1 calc R . . . .
C8' C -0.1780(3) 0.2185(2) 0.21207(13) 0.0321(6) Uani 1 1 d . . . . .
C9' C -0.2375(3) 0.3009(2) 0.21101(13) 0.0337(6) Uani 1 1 d . . . . .
H9' H -0.255648 0.336485 0.177300 0.040 Uiso 1 1 calc R . . . .
C10' C -0.2621(3) 0.31806(18) 0.26426(12) 0.0284(6) Uani 1 1 d . . . . .
H10' H -0.303848 0.367020 0.273449 0.034 Uiso 1 1 calc R . . . .
C11' C -0.2159(2) 0.25075(17) 0.30810(12) 0.0248(5) Uani 1 1 d . . . . .
H11' H -0.138946 0.271347 0.332363 0.030 Uiso 1 1 calc R . . . .
C12' C -0.4263(3) 0.2098(2) 0.31923(13) 0.0326(6) Uani 1 1 d . . . . .
H12D H -0.456466 0.253376 0.290103 0.049 Uiso 1 1 calc GR . . . .
H12E H -0.480230 0.205328 0.348423 0.049 Uiso 1 1 calc GR . . . .
H12F H -0.423601 0.155537 0.299007 0.049 Uiso 1 1 calc GR . . . .
C13' C -0.2511(3) 0.16695(18) 0.39459(12) 0.0291(6) Uani 1 1 d . . . . .
H13C H -0.261205 0.110547 0.375885 0.035 Uiso 1 1 calc R . . . .
H13D H -0.163570 0.177345 0.406718 0.035 Uiso 1 1 calc R . . . .
C14' C -0.3099(3) 0.16738(17) 0.44857(12) 0.0263(6) Uani 1 1 d . . . . .
C15' C -0.4074(3) 0.11555(18) 0.45295(14) 0.0322(6) Uani 1 1 d . . . . .
H15' H -0.439350 0.079315 0.421069 0.039 Uiso 1 1 calc R . . . .
C16' C -0.4580(3) 0.1169(2) 0.50408(16) 0.0400(7) Uani 1 1 d . . . . .
H16' H -0.525416 0.082019 0.507033 0.048 Uiso 1 1 calc R . . . .
C17' C -0.4102(3) 0.1690(2) 0.55080(14) 0.0421(8) Uani 1 1 d . . . . .
H17' H -0.444958 0.169854 0.585747 0.051 Uiso 1 1 calc R . . . .
C18' C -0.3132(3) 0.2193(2) 0.54688(13) 0.0380(7) Uani 1 1 d . . . . .
H18' H -0.280214 0.254516 0.579194 0.046 Uiso 1 1 calc R . . . .
C19' C -0.2631(3) 0.21895(18) 0.49565(12) 0.0301(6) Uani 1 1 d . . . . .
H19' H -0.196222 0.254344 0.492889 0.036 Uiso 1 1 calc R . . . .
O1A O 0.2927(3) 0.3770(2) 0.25997(15) 0.0836(12) Uani 1 1 d . . . . .
H1AA H 0.269874 0.424759 0.243048 0.125 Uiso 1 1 d R . . . .
H1AB H 0.257124 0.374979 0.290808 0.125 Uiso 1 1 d R . . . .
O2A O 0.1937(2) 0.35310(15) 0.35852(11) 0.0431(6) Uani 1 1 d . . . . .
H2AA H 0.142149 0.310551 0.355541 0.085(17) Uiso 1 1 d R . . . .
H2AB H 0.185209 0.386841 0.390441 0.11(2) Uiso 1 1 d R . . . .
O3A O 0.1715(3) 0.24012(18) 0.19173(12) 0.0570(7) Uani 1 1 d . . . . .
H3AA H 0.238010 0.274599 0.208128 0.085 Uiso 1 1 d R . . . .
H3AB H 0.146310 0.223689 0.223338 0.085 Uiso 1 1 d R . . . .
O4A O 0.5431(3) 0.67277(17) 0.80230(13) 0.0583(7) Uani 1 1 d . . . . .
H4AA H 0.578337 0.721810 0.806654 0.087 Uiso 1 1 d R . . . .
H4AB H 0.576507 0.647430 0.775674 0.087 Uiso 1 1 d R . . . .
O5A O 0.4581(4) 0.3379(2) 0.66715(15) 0.0837(11) Uani 1 1 d . . . . .
H5AA H 0.456398 0.358493 0.631891 0.126 Uiso 1 1 d R . . . .
H5AB H 0.443078 0.380823 0.688391 0.126 Uiso 1 1 d R . . . .
O6A O 0.4424(5) 0.4859(3) 0.7191(2) 0.1217(17) Uani 1 1 d . . . . .
H6AA H 0.433847 0.538698 0.709045 0.183 Uiso 1 1 d R . . . .
H6AB H 0.465047 0.486768 0.757356 0.183 Uiso 1 1 d R . . . .
O7A O 0.4622(2) 0.52129(17) 0.83897(12) 0.0495(6) Uani 1 1 d . . . . .
H7AA H 0.471635 0.574573 0.831778 0.074 Uiso 1 1 d R . . . .
H7AB H 0.388205 0.517413 0.844988 0.074 Uiso 1 1 d R . . . .
H3 H 0.165(3) 0.316(2) 0.6205(16) 0.034(9) Uiso 1 1 d . . . . .
H3' H -0.312(3) 0.283(2) 0.3675(14) 0.031(8) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.230(3) . ?
O2 C4 1.248(3) . ?
O3 C5 1.262(3) . ?
O4 C8 1.209(3) . ?
N1 C1 1.365(4) . ?
N1 C2 1.466(4) . ?
N1 C4 1.403(3) . ?
N2 C1 1.365(4) . ?
N2 C3 1.462(3) . ?
N2 C5 1.405(3) . ?
N3 C11 1.511(3) . ?
N3 C12 1.496(4) . ?
N3 C13 1.509(3) . ?
N3 H3 0.89(4) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 C6 1.402(4) . ?
C5 C6 1.390(3) . ?
C6 C7 1.493(3) . ?
C7 H7 1.0000 . ?
C7 C8 1.532(3) . ?
C7 C11 1.535(4) . ?
C8 C9 1.465(4) . ?
C9 H9 0.9500 . ?
C9 C10 1.325(4) . ?
C10 H10 0.9500 . ?
C10 C11 1.497(4) . ?
C11 H11 1.0000 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.504(4) . ?
C14 C15 1.382(4) . ?
C14 C19 1.390(4) . ?
C15 H15 0.9500 . ?
C15 C16 1.386(4) . ?
C16 H16 0.9500 . ?
C16 C17 1.387(5) . ?
C17 H17 0.9500 . ?
C17 C18 1.371(5) . ?
C18 H18 0.9500 . ?
C18 C19 1.375(4) . ?
C19 H19 0.9500 . ?
O1' C1' 1.228(4) . ?
O2' C4' 1.246(4) . ?
O3' C5' 1.254(4) . ?
O4' C8' 1.211(4) . ?
N1' C1' 1.365(4) . ?
N1' C2' 1.464(4) . ?
N1' C4' 1.407(4) . ?
N2' C1' 1.369(4) . ?
N2' C3' 1.461(4) . ?
N2' C5' 1.406(4) . ?
N3' C11' 1.510(3) . ?
N3' C12' 1.485(4) . ?
N3' C13' 1.508(3) . ?
N3' H3' 0.91(4) . ?
C2' H2'A 0.9800 . ?
C2' H2'B 0.9800 . ?
C2' H2'C 0.9800 . ?
C3' H3'A 0.9800 . ?
C3' H3'B 0.9800 . ?
C3' H3'C 0.9800 . ?
C4' C6' 1.395(4) . ?
C5' C6' 1.382(4) . ?
C6' C7' 1.497(4) . ?
C7' H7' 1.0000 . ?
C7' C8' 1.531(4) . ?
C7' C11' 1.529(4) . ?
C8' C9' 1.467(5) . ?
C9' H9' 0.9500 . ?
C9' C10' 1.325(4) . ?
C10' H10' 0.9500 . ?
C10' C11' 1.496(4) . ?
C11' H11' 1.0000 . ?
C12' H12D 0.9800 . ?
C12' H12E 0.9800 . ?
C12' H12F 0.9800 . ?
C13' H13C 0.9900 . ?
C13' H13D 0.9900 . ?
C13' C14' 1.500(4) . ?
C14' C15' 1.389(4) . ?
C14' C19' 1.383(4) . ?
C15' H15' 0.9500 . ?
C15' C16' 1.389(4) . ?
C16' H16' 0.9500 . ?
C16' C17' 1.386(5) . ?
C17' H17' 0.9500 . ?
C17' C18' 1.367(5) . ?
C18' H18' 0.9500 . ?
C18' C19' 1.387(4) . ?
C19' H19' 0.9500 . ?
O1A H1AA 0.8698 . ?
O1A H1AB 0.8705 . ?
O2A H2AA 0.8847 . ?
O2A H2AB 0.9243 . ?
O3A H3AA 0.9508 . ?
O3A H3AB 0.8621 . ?
O4A H4AA 0.8711 . ?
O4A H4AB 0.8686 . ?
O5A H5AA 0.8688 . ?
O5A H5AB 0.8708 . ?
O6A H6AA 0.8695 . ?
O6A H6AB 0.8699 . ?
O7A H7AA 0.8710 . ?
O7A H7AB 0.8699 . ?

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 C2 116.8(2) . . ?
C1 N1 C4 123.8(2) . . ?
C4 N1 C2 119.4(2) . . ?
C1 N2 C3 116.9(2) . . ?
C1 N2 C5 123.0(2) . . ?
C5 N2 C3 120.0(2) . . ?
C11 N3 H3 106(2) . . ?
C12 N3 C11 113.7(2) . . ?
C12 N3 C13 110.7(2) . . ?
C12 N3 H3 105(2) . . ?
C13 N3 C11 111.8(2) . . ?
C13 N3 H3 109(2) . . ?
O1 C1 N1 121.4(3) . . ?
O1 C1 N2 121.2(3) . . ?
N1 C1 N2 117.3(2) . . ?
N1 C2 H2A 109.5 . . ?
N1 C2 H2B 109.5 . . ?
N1 C2 H2C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
N2 C3 H3A 109.5 . . ?
N2 C3 H3B 109.5 . . ?
N2 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
O2 C4 N1 118.7(2) . . ?
O2 C4 C6 124.6(2) . . ?
C6 C4 N1 116.7(2) . . ?
O3 C5 N2 118.3(2) . . ?
O3 C5 C6 124.1(2) . . ?
C6 C5 N2 117.6(2) . . ?
C4 C6 C7 119.5(2) . . ?
C5 C6 C4 121.3(2) . . ?
C5 C6 C7 119.2(2) . . ?
C6 C7 H7 107.4 . . ?
C6 C7 C8 114.1(2) . . ?
C6 C7 C11 117.2(2) . . ?
C8 C7 H7 107.4 . . ?
C8 C7 C11 102.9(2) . . ?
C11 C7 H7 107.4 . . ?
O4 C8 C7 124.8(2) . . ?
O4 C8 C9 127.3(2) . . ?
C9 C8 C7 108.0(2) . . ?
C8 C9 H9 124.8 . . ?
C10 C9 C8 110.3(2) . . ?
C10 C9 H9 124.8 . . ?
C9 C10 H10 123.9 . . ?
C9 C10 C11 112.1(2) . . ?
C11 C10 H10 123.9 . . ?
N3 C11 C7 114.8(2) . . ?
N3 C11 H11 108.5 . . ?
C7 C11 H11 108.5 . . ?
C10 C11 N3 111.0(2) . . ?
C10 C11 C7 105.3(2) . . ?
C10 C11 H11 108.5 . . ?
N3 C12 H12A 109.5 . . ?
N3 C12 H12B 109.5 . . ?
N3 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N3 C13 H13A 109.3 . . ?
N3 C13 H13B 109.3 . . ?
H13A C13 H13B 108.0 . . ?
C14 C13 N3 111.6(2) . . ?
C14 C13 H13A 109.3 . . ?
C14 C13 H13B 109.3 . . ?
C15 C14 C13 121.1(3) . . ?
C15 C14 C19 119.0(3) . . ?
C19 C14 C13 119.9(3) . . ?
C14 C15 H15 119.9 . . ?
C14 C15 C16 120.1(3) . . ?
C16 C15 H15 119.9 . . ?
C15 C16 H16 120.0 . . ?
C15 C16 C17 120.1(3) . . ?
C17 C16 H16 120.0 . . ?
C16 C17 H17 120.1 . . ?
C18 C17 C16 119.8(3) . . ?
C18 C17 H17 120.1 . . ?
C17 C18 H18 119.9 . . ?
C17 C18 C19 120.1(3) . . ?
C19 C18 H18 119.9 . . ?
C14 C19 H19 119.6 . . ?
C18 C19 C14 120.8(3) . . ?
C18 C19 H19 119.6 . . ?
C1' N1' C2' 117.7(3) . . ?
C1' N1' C4' 123.5(3) . . ?
C4' N1' C2' 118.7(3) . . ?
C1' N2' C3' 117.0(3) . . ?
C1' N2' C5' 123.0(3) . . ?
C5' N2' C3' 119.9(3) . . ?
C11' N3' H3' 104(2) . . ?
C12' N3' C11' 113.9(2) . . ?
C12' N3' C13' 111.9(2) . . ?
C12' N3' H3' 105(2) . . ?
C13' N3' C11' 110.1(2) . . ?
C13' N3' H3' 111(2) . . ?
O1' C1' N1' 121.3(3) . . ?
O1' C1' N2' 121.4(3) . . ?
N1' C1' N2' 117.2(3) . . ?
N1' C2' H2'A 109.5 . . ?
N1' C2' H2'B 109.5 . . ?
N1' C2' H2'C 109.5 . . ?
H2'A C2' H2'B 109.5 . . ?
H2'A C2' H2'C 109.5 . . ?
H2'B C2' H2'C 109.5 . . ?
N2' C3' H3'A 109.5 . . ?
N2' C3' H3'B 109.5 . . ?
N2' C3' H3'C 109.5 . . ?
H3'A C3' H3'B 109.5 . . ?
H3'A C3' H3'C 109.5 . . ?
H3'B C3' H3'C 109.5 . . ?
O2' C4' N1' 118.3(3) . . ?
O2' C4' C6' 124.8(3) . . ?
C6' C4' N1' 116.8(3) . . ?
O3' C5' N2' 118.7(3) . . ?
O3' C5' C6' 123.7(3) . . ?
C6' C5' N2' 117.6(3) . . ?
C4' C6' C7' 119.6(3) . . ?
C5' C6' C4' 121.7(3) . . ?
C5' C6' C7' 118.6(3) . . ?
C6' C7' H7' 107.9 . . ?
C6' C7' C8' 114.3(2) . . ?
C6' C7' C11' 117.0(2) . . ?
C8' C7' H7' 107.9 . . ?
C11' C7' H7' 107.9 . . ?
C11' C7' C8' 101.5(2) . . ?
O4' C8' C7' 125.1(3) . . ?
O4' C8' C9' 126.7(3) . . ?
C9' C8' C7' 108.2(2) . . ?
C8' C9' H9' 125.2 . . ?
C10' C9' C8' 109.6(3) . . ?
C10' C9' H9' 125.2 . . ?
C9' C10' H10' 124.2 . . ?
C9' C10' C11' 111.6(3) . . ?
C11' C10' H10' 124.2 . . ?
N3' C11' C7' 115.6(2) . . ?
N3' C11' H11' 107.9 . . ?
C7' C11' H11' 107.9 . . ?
C10' C11' N3' 111.8(2) . . ?
C10' C11' C7' 105.5(2) . . ?
C10' C11' H11' 107.9 . . ?
N3' C12' H12D 109.5 . . ?
N3' C12' H12E 109.5 . . ?
N3' C12' H12F 109.5 . . ?
H12D C12' H12E 109.5 . . ?
H12D C12' H12F 109.5 . . ?
H12E C12' H12F 109.5 . . ?
N3' C13' H13C 109.1 . . ?
N3' C13' H13D 109.1 . . ?
H13C C13' H13D 107.8 . . ?
C14' C13' N3' 112.6(2) . . ?
C14' C13' H13C 109.1 . . ?
C14' C13' H13D 109.1 . . ?
C15' C14' C13' 121.6(3) . . ?
C19' C14' C13' 118.9(3) . . ?
C19' C14' C15' 119.5(3) . . ?
C14' C15' H15' 120.1 . . ?
C16' C15' C14' 119.8(3) . . ?
C16' C15' H15' 120.1 . . ?
C15' C16' H16' 120.0 . . ?
C17' C16' C15' 119.9(3) . . ?
C17' C16' H16' 120.0 . . ?
C16' C17' H17' 119.8 . . ?
C18' C17' C16' 120.4(3) . . ?
C18' C17' H17' 119.8 . . ?
C17' C18' H18' 120.0 . . ?
C17' C18' C19' 119.9(3) . . ?
C19' C18' H18' 120.0 . . ?
C14' C19' C18' 120.5(3) . . ?
C14' C19' H19' 119.8 . . ?
C18' C19' H19' 119.8 . . ?
H1AA O1A H1AB 104.6 . . ?
H2AA O2A H2AB 110.3 . . ?
H3AA O3A H3AB 101.1 . . ?
H4AA O4A H4AB 104.5 . . ?
H5AA O5A H5AB 104.4 . . ?
H6AA O6A H6AB 104.5 . . ?
H7AA O7A H7AB 104.4 . . ?


_olex2_submission_special_instructions 'No special instructions were received'



_publcif_funding_html            
;
;
####################################################################### 
# 
# 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_12b
_database_code_depnum_ccdc_archive 'CCDC 1839150'
_audit_update_record             
;
2018-04-24 deposited with the CCDC.
2018-08-29 downloaded from the CCDC.
;
_audit_creation_date             2018-04-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H19 N3 O4, 0.5(C H2 Cl2), 0.56(H2 O)'
_chemical_formula_sum            'C15.50 H20.27 Cl N3 O4.64'
_chemical_formula_weight         358.23
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   10.420(2)
_cell_length_b                   13.200(3)
_cell_length_c                   13.900(3)
_cell_angle_alpha                89.03(3)
_cell_angle_beta                 85.92(3)
_cell_angle_gamma                75.68(3)
_cell_volume                     1847.7(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    10155
_cell_measurement_temperature    100
_cell_measurement_theta_max      29.57
_cell_measurement_theta_min      1.469
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.233
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.288
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             753
_exptl_crystal_size_max          0.9
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0456
_diffrn_reflns_av_unetI/netI     0.0271
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            61226
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.271
_diffrn_reflns_theta_min         1.469
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  MX1
_diffrn_measurement_method       'Phi Scan'
_diffrn_radiation_monochromator  'Silicon Double Crystal'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'MX1 Beamline Australian Synchrotron'
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                7177
_reflns_number_total             9130
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'XDS (Kabsch, 1993)'
_computing_data_collection       'BluIce (McPhillips, 2002)'
_computing_data_reduction        'XDS (Kabsch, 1993)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         2.362
_refine_diff_density_min         -0.949
_refine_diff_density_rms         0.125
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     465
_refine_ls_number_reflns         9130
_refine_ls_number_restraints     43
_refine_ls_R_factor_all          0.1089
_refine_ls_R_factor_gt           0.0935
_refine_ls_restrained_S_all      1.068
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1886P)²+2.1259P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2851
_refine_ls_wR_factor_ref         0.3019
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2. Rigid bond restraints
 C14, C15
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
C15 \\sim C14: within 1.7A with sigma of 0.005 and sigma for terminal atoms of
0.08
C13 \\sim C12: within 1.7A with sigma of 0.004 and sigma for terminal atoms of
0.08
Uanis(N3) \\sim Ueq, Uanis(C15) \\sim Ueq, Uanis(C14) \\sim Ueq, Uanis(C13)
\\sim Ueq, Uanis(C12) \\sim Ueq: with sigma of 0.01 and sigma for terminal
atoms of 0.2
Uanis(C14) \\sim Ueq, Uanis(C13) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.2
4. Others
 Sof(H31C)=Sof(H31D)=Sof(Cl1A)=Sof(Cl2A)=1-FVAR(1)
 Sof(H31A)=Sof(H31B)=Sof(Cl2)=Sof(Cl1)=FVAR(1)
 Fixed Sof: O10(0.64691) H10A(0.64691) H10B(0.64691) O9(0.46361) H9A(0.46361)
 H9B(0.46361)
5.a Riding coordinates:
 O10(H10A,H10B), O9(H9A,H9B)
5.b Ternary CH refined with riding coordinates:
 N3(H3), N6(H6), C22(H22), C11(H11), C7(H7), C26(H26)
5.c Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C27(H27A,H27B), C15(H15A,H15B), C30(H30A,H30B), C31(H31A,
 H31B), C31(H31C,H31D), C28(H28A,H28B), C13(H13A,H13B), C29(H29A,H29B),
 C14(H14A,H14B)
5.d Aromatic/amide H refined with riding coordinates:
 C10(H10), C9(H9), C25(H25), C24(H24)
5.e Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C), C17(H17A,H17B,H17C), C3(H3A,H3B,H3C), C18(H18A,H18B,H18C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O2 O 0.50037(19) 0.37034(15) 0.58938(14) 0.0299(4) Uani 1 1 d . . . . .
O7 O 0.70744(19) 0.43472(17) 1.00350(15) 0.0349(5) Uani 1 1 d . . . . .
O3 O 0.6941(2) 0.04696(15) 0.43719(15) 0.0327(4) Uani 1 1 d . . . . .
O6 O 0.64729(19) 0.19973(17) 0.77064(16) 0.0368(5) Uani 1 1 d . . . . .
O4 O 0.3435(2) 0.30357(18) 0.41324(16) 0.0388(5) Uani 1 1 d . . . . .
O1 O 0.9283(2) 0.29433(19) 0.4598(2) 0.0468(6) Uani 1 1 d . . . . .
O5 O 1.06201(19) 0.2238(2) 0.83488(18) 0.0468(6) Uani 1 1 d . . . . .
N1 N 0.7142(2) 0.33351(17) 0.52391(17) 0.0292(5) Uani 1 1 d . . . . .
N4 N 0.8557(2) 0.2132(2) 0.80039(18) 0.0324(5) Uani 1 1 d . . . . .
N2 N 0.8120(2) 0.17032(18) 0.45305(18) 0.0303(5) Uani 1 1 d . . . . .
O8 O 0.4983(3) 0.1943(2) 0.9944(2) 0.0517(6) Uani 1 1 d . . . . .
N3 N 0.4349(3) 0.05852(19) 0.67112(17) 0.0322(5) Uani 1 1 d . U . . .
H3 H 0.395168 0.018809 0.627891 0.039 Uiso 1 1 calc R . . . .
N6 N 0.4082(3) 0.5176(2) 0.82215(17) 0.0362(5) Uani 1 1 d . . . . .
H6 H 0.360684 0.542251 0.884067 0.043 Uiso 1 1 calc R . . . .
N5 N 0.8842(2) 0.3261(2) 0.92107(19) 0.0385(6) Uani 1 1 d . . . . .
C6 C 0.5852(2) 0.20660(19) 0.51455(17) 0.0240(5) Uani 1 1 d . . . . .
C4 C 0.5930(2) 0.30617(19) 0.54567(18) 0.0252(5) Uani 1 1 d . . . . .
C21 C 0.6646(2) 0.3193(2) 0.88875(18) 0.0255(5) Uani 1 1 d . . . . .
C22 C 0.5173(2) 0.3531(2) 0.90726(18) 0.0250(5) Uani 1 1 d . . . . .
H22 H 0.498383 0.405946 0.958446 0.030 Uiso 1 1 calc R . . . .
C20 C 0.7466(2) 0.3630(2) 0.94086(19) 0.0294(5) Uani 1 1 d . . . . .
C11 C 0.4036(3) 0.1696(2) 0.63828(19) 0.0276(5) Uani 1 1 d . . . . .
H11 H 0.443760 0.210644 0.679872 0.033 Uiso 1 1 calc R . . . .
C5 C 0.6924(2) 0.1371(2) 0.46737(18) 0.0260(5) Uani 1 1 d . . . . .
C19 C 0.7162(2) 0.2423(2) 0.81785(19) 0.0281(5) Uani 1 1 d . . . . .
C7 C 0.4544(2) 0.1802(2) 0.53235(18) 0.0252(5) Uani 1 1 d . . . . .
H7 H 0.461956 0.112910 0.500846 0.030 Uiso 1 1 calc R . . . .
C1 C 0.8239(3) 0.2676(2) 0.4781(2) 0.0319(6) Uani 1 1 d . . . . .
C26 C 0.4373(3) 0.4008(2) 0.8217(2) 0.0316(6) Uani 1 1 d . . . . .
H26 H 0.487095 0.373831 0.761126 0.038 Uiso 1 1 calc R . . . .
C16 C 0.9410(3) 0.2523(3) 0.8511(2) 0.0350(6) Uani 1 1 d . . . . .
C23 C 0.4519(3) 0.2651(2) 0.9412(2) 0.0357(6) Uani 1 1 d . . . . .
C10 C 0.2563(3) 0.2170(3) 0.6396(2) 0.0372(6) Uani 1 1 d . . . . .
H10 H 0.196710 0.211178 0.691298 0.045 Uiso 1 1 calc R . . . .
C8 C 0.3378(3) 0.2589(2) 0.4906(2) 0.0314(5) Uani 1 1 d . . . . .
C12 C 0.5824(3) 0.0086(2) 0.6683(2) 0.0386(6) Uani 1 1 d . U . . .
H12A H 0.616901 -0.015236 0.603748 0.046 Uiso 1 1 calc R . . . .
H12B H 0.630645 0.057249 0.689758 0.046 Uiso 1 1 calc R . . . .
C9 C 0.2209(3) 0.2683(3) 0.5584(2) 0.0379(6) Uani 1 1 d . . . . .
H9 H 0.134944 0.304633 0.546565 0.045 Uiso 1 1 calc R . . . .
C25 C 0.3130(3) 0.3610(3) 0.8343(3) 0.0429(8) Uani 1 1 d . . . . .
H25 H 0.237705 0.387309 0.800779 0.051 Uiso 1 1 calc R . . . .
C2 C 0.7228(3) 0.4392(2) 0.5493(3) 0.0404(7) Uani 1 1 d . . . . .
H2A H 0.642033 0.488767 0.535300 0.061 Uiso 1 1 calc GR . . . .
H2B H 0.796188 0.455939 0.512272 0.061 Uiso 1 1 calc GR . . . .
H2C H 0.735931 0.441751 0.616751 0.061 Uiso 1 1 calc GR . . . .
C27 C 0.5296(4) 0.5588(3) 0.8119(2) 0.0439(7) Uani 1 1 d . . . . .
H27A H 0.589363 0.526028 0.758356 0.053 Uiso 1 1 calc R . . . .
H27B H 0.576472 0.548579 0.870488 0.053 Uiso 1 1 calc R . . . .
C24 C 0.3231(3) 0.2853(3) 0.8977(3) 0.0441(8) Uani 1 1 d . . . . .
H24 H 0.258115 0.249392 0.913057 0.053 Uiso 1 1 calc R . . . .
C17 C 0.9147(3) 0.1365(3) 0.7248(3) 0.0471(8) Uani 1 1 d . . . . .
H17A H 0.976431 0.078673 0.752044 0.071 Uiso 1 1 calc GR . . . .
H17B H 0.960421 0.168632 0.675388 0.071 Uiso 1 1 calc GR . . . .
H17C H 0.846038 0.111861 0.697331 0.071 Uiso 1 1 calc GR . . . .
C3 C 0.9278(3) 0.1010(3) 0.4028(3) 0.0471(8) Uani 1 1 d . . . . .
H3A H 0.917647 0.030708 0.404618 0.071 Uiso 1 1 calc GR . . . .
H3B H 1.006309 0.103805 0.433866 0.071 Uiso 1 1 calc GR . . . .
H3C H 0.935680 0.123133 0.336960 0.071 Uiso 1 1 calc GR . . . .
C15 C 0.3834(5) 0.0423(3) 0.7733(2) 0.0532(9) Uani 1 1 d . U . . .
H15A H 0.392731 0.097722 0.815135 0.064 Uiso 1 1 calc R . . . .
H15B H 0.290517 0.041144 0.775393 0.064 Uiso 1 1 calc R . . . .
C18 C 0.9752(3) 0.3678(4) 0.9750(3) 0.0683(14) Uani 1 1 d . . . . .
H18A H 0.925181 0.418735 1.020656 0.102 Uiso 1 1 calc GR . . . .
H18B H 1.028470 0.400073 0.931089 0.102 Uiso 1 1 calc GR . . . .
H18C H 1.031807 0.311904 1.008542 0.102 Uiso 1 1 calc GR . . . .
C30 C 0.3236(5) 0.5700(3) 0.7432(3) 0.0605(11) Uani 1 1 d . . . . .
H30A H 0.229907 0.580317 0.762338 0.073 Uiso 1 1 calc R . . . .
H30B H 0.344221 0.529078 0.684274 0.073 Uiso 1 1 calc R . . . .
C31 C 1.0868(4) 0.3979(4) 0.2996(3) 0.0642(11) Uani 1 1 d . . . . .
H31A H 1.025610 0.354325 0.315025 0.077 Uiso 0.500(6) 1 calc R . P A -1
H31B H 1.150425 0.387260 0.348714 0.077 Uiso 0.500(6) 1 calc R . P A -1
H31C H 1.174910 0.385300 0.322925 0.077 Uiso 0.500(6) 1 calc R . P A 1
H31D H 1.026074 0.389864 0.353726 0.077 Uiso 0.500(6) 1 calc R . P A 1
C28 C 0.4713(6) 0.6743(3) 0.7928(3) 0.0665(12) Uani 1 1 d . . . . .
H28A H 0.438027 0.711626 0.852517 0.080 Uiso 1 1 calc R . . . .
H28B H 0.537243 0.705835 0.760331 0.080 Uiso 1 1 calc R . . . .
C13 C 0.5919(5) -0.0822(3) 0.7371(3) 0.0672(11) Uani 1 1 d . U . . .
H13A H 0.668271 -0.090037 0.775147 0.081 Uiso 1 1 calc R . . . .
H13B H 0.600236 -0.146708 0.702008 0.081 Uiso 1 1 calc R . . . .
C29 C 0.3612(7) 0.6756(4) 0.7299(4) 0.0883(18) Uani 1 1 d . . . . .
H29A H 0.389466 0.684760 0.663004 0.106 Uiso 1 1 calc R . . . .
H29B H 0.285320 0.732756 0.748046 0.106 Uiso 1 1 calc R . . . .
O10 O 0.2201(9) 0.0435(6) 1.0115(5) 0.113(3) Uani 0.6469 1 d . . P . .
H10A H 0.270671 0.038007 1.057676 0.169 Uiso 0.6469 1 d R . P . .
H10B H 0.258961 0.002527 0.966066 0.169 Uiso 0.6469 1 d R . P . .
C14 C 0.4630(7) -0.0561(5) 0.8020(4) 0.0995(17) Uani 1 1 d . U . . .
H14A H 0.415326 -0.109968 0.796112 0.119 Uiso 1 1 calc R . . . .
H14B H 0.482957 -0.052934 0.868794 0.119 Uiso 1 1 calc R . . . .
O9 O 0.1418(8) -0.1003(9) 0.8916(7) 0.103(3) Uani 0.4636 1 d . . P B 1
H9A H 0.071638 -0.108146 0.922657 0.154 Uiso 0.4636 1 d R . P B 1
H9B H 0.165758 -0.049646 0.915528 0.154 Uiso 0.4636 1 d R . P B 1
Cl2 Cl 1.0028(4) 0.5249(3) 0.2971(4) 0.0778(13) Uani 0.500(6) 1 d . . P A -1
Cl1 Cl 1.1751(3) 0.3610(3) 0.1787(2) 0.0833(12) Uani 0.500(6) 1 d . . P A -1
Cl1A Cl 1.0873(5) 0.3073(4) 0.2162(2) 0.116(2) Uani 0.500(6) 1 d . . P A 1
Cl2A Cl 1.0407(7) 0.5266(6) 0.2575(6) 0.126(3) Uani 0.500(6) 1 d . . P A 1


_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
O2 C4 1.244(3) . ?
O7 C20 1.268(3) . ?
O3 C5 1.264(3) . ?
O6 C19 1.241(3) . ?
O4 C8 1.222(4) . ?
O1 C1 1.232(3) . ?
O5 C16 1.229(3) . ?
N1 C4 1.408(3) . ?
N1 C1 1.376(4) . ?
N1 C2 1.470(3) . ?
N4 C19 1.412(3) . ?
N4 C16 1.373(3) . ?
N4 C17 1.465(3) . ?
N2 C5 1.420(3) . ?
N2 C1 1.373(4) . ?
N2 C3 1.462(4) . ?
O8 C23 1.207(4) . ?
N3 H3 0.9800 . ?
N3 C11 1.492(4) . ?
N3 C12 1.513(4) . ?
N3 C15 1.512(4) . ?
N6 H6 0.9800 . ?
N6 C26 1.497(4) . ?
N6 C27 1.493(4) . ?
N6 C30 1.506(4) . ?
N5 C20 1.404(3) . ?
N5 C16 1.381(3) . ?
N5 C18 1.462(3) . ?
C6 C4 1.414(3) . ?
C6 C5 1.389(3) . ?
C6 C7 1.491(3) . ?
C21 C22 1.493(3) . ?
C21 C20 1.390(3) . ?
C21 C19 1.408(3) . ?
C22 H22 0.9800 . ?
C22 C26 1.537(4) . ?
C22 C23 1.538(4) . ?
C11 H11 0.9800 . ?
C11 C7 1.545(4) . ?
C11 C10 1.506(4) . ?
C7 H7 0.9800 . ?
C7 C8 1.533(4) . ?
C26 H26 0.9800 . ?
C26 C25 1.512(4) . ?
C23 C24 1.473(4) . ?
C10 H10 0.9300 . ?
C10 C9 1.334(5) . ?
C8 C9 1.468(4) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.510(5) . ?
C9 H9 0.9300 . ?
C25 H25 0.9300 . ?
C25 C24 1.310(6) . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
C27 C28 1.521(5) . ?
C24 H24 0.9300 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C14 1.425(7) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C30 H30A 0.9700 . ?
C30 H30B 0.9700 . ?
C30 C29 1.543(8) . ?
C31 H31A 0.9700 . ?
C31 H31B 0.9700 . ?
C31 H31C 0.9700 . ?
C31 H31D 0.9700 . ?
C31 Cl2 1.689(6) . ?
C31 Cl1 1.868(6) . ?
C31 Cl1A 1.678(7) . ?
C31 Cl2A 1.750(8) . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?
C28 C29 1.488(8) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.532(8) . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
O10 H10A 0.8499 . ?
O10 H10B 0.8500 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
O9 H9A 0.8502 . ?
O9 H9B 0.8497 . ?
Cl2 Cl2A 0.658(7) . ?
Cl1 Cl1A 1.360(6) . ?

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
C4 N1 C2 118.2(2) . . ?
C1 N1 C4 123.6(2) . . ?
C1 N1 C2 118.2(2) . . ?
C19 N4 C17 119.1(2) . . ?
C16 N4 C19 123.7(2) . . ?
C16 N4 C17 117.2(2) . . ?
C5 N2 C3 119.1(2) . . ?
C1 N2 C5 123.9(2) . . ?
C1 N2 C3 116.9(2) . . ?
C11 N3 H3 107.9 . . ?
C11 N3 C12 113.0(2) . . ?
C11 N3 C15 114.7(2) . . ?
C12 N3 H3 107.9 . . ?
C15 N3 H3 107.9 . . ?
C15 N3 C12 105.0(3) . . ?
C26 N6 H6 107.8 . . ?
C26 N6 C30 114.5(3) . . ?
C27 N6 H6 107.8 . . ?
C27 N6 C26 113.6(2) . . ?
C27 N6 C30 105.1(3) . . ?
C30 N6 H6 107.8 . . ?
C20 N5 C18 119.7(2) . . ?
C16 N5 C20 123.7(2) . . ?
C16 N5 C18 116.6(2) . . ?
C4 C6 C7 116.8(2) . . ?
C5 C6 C4 122.1(2) . . ?
C5 C6 C7 121.1(2) . . ?
O2 C4 N1 118.8(2) . . ?
O2 C4 C6 124.4(2) . . ?
N1 C4 C6 116.8(2) . . ?
C20 C21 C22 120.3(2) . . ?
C20 C21 C19 121.9(2) . . ?
C19 C21 C22 117.8(2) . . ?
C21 C22 H22 107.4 . . ?
C21 C22 C26 116.7(2) . . ?
C21 C22 C23 114.5(2) . . ?
C26 C22 H22 107.4 . . ?
C26 C22 C23 103.0(2) . . ?
C23 C22 H22 107.4 . . ?
O7 C20 N5 117.3(2) . . ?
O7 C20 C21 125.4(2) . . ?
C21 C20 N5 117.3(2) . . ?
N3 C11 H11 109.4 . . ?
N3 C11 C7 112.0(2) . . ?
N3 C11 C10 112.2(2) . . ?
C7 C11 H11 109.4 . . ?
C10 C11 H11 109.4 . . ?
C10 C11 C7 104.4(2) . . ?
O3 C5 N2 117.1(2) . . ?
O3 C5 C6 126.3(2) . . ?
C6 C5 N2 116.6(2) . . ?
O6 C19 N4 119.0(2) . . ?
O6 C19 C21 124.3(2) . . ?
C21 C19 N4 116.7(2) . . ?
C6 C7 C11 117.6(2) . . ?
C6 C7 H7 107.1 . . ?
C6 C7 C8 114.5(2) . . ?
C11 C7 H7 107.1 . . ?
C8 C7 C11 102.9(2) . . ?
C8 C7 H7 107.1 . . ?
O1 C1 N1 121.8(3) . . ?
O1 C1 N2 121.3(3) . . ?
N2 C1 N1 116.9(2) . . ?
N6 C26 C22 111.6(2) . . ?
N6 C26 H26 109.5 . . ?
N6 C26 C25 112.6(2) . . ?
C22 C26 H26 109.5 . . ?
C25 C26 C22 103.9(2) . . ?
C25 C26 H26 109.5 . . ?
O5 C16 N4 121.8(3) . . ?
O5 C16 N5 121.5(2) . . ?
N4 C16 N5 116.7(2) . . ?
O8 C23 C22 125.6(3) . . ?
O8 C23 C24 127.5(3) . . ?
C24 C23 C22 106.9(3) . . ?
C11 C10 H10 123.8 . . ?
C9 C10 C11 112.4(3) . . ?
C9 C10 H10 123.8 . . ?
O4 C8 C7 124.8(3) . . ?
O4 C8 C9 127.2(3) . . ?
C9 C8 C7 108.0(2) . . ?
N3 C12 H12A 111.1 . . ?
N3 C12 H12B 111.1 . . ?
H12A C12 H12B 109.1 . . ?
C13 C12 N3 103.3(3) . . ?
C13 C12 H12A 111.1 . . ?
C13 C12 H12B 111.1 . . ?
C10 C9 C8 109.9(3) . . ?
C10 C9 H9 125.1 . . ?
C8 C9 H9 125.1 . . ?
C26 C25 H25 123.8 . . ?
C24 C25 C26 112.5(3) . . ?
C24 C25 H25 123.8 . . ?
N1 C2 H2A 109.5 . . ?
N1 C2 H2B 109.5 . . ?
N1 C2 H2C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
N6 C27 H27A 111.4 . . ?
N6 C27 H27B 111.4 . . ?
N6 C27 C28 101.9(3) . . ?
H27A C27 H27B 109.2 . . ?
C28 C27 H27A 111.4 . . ?
C28 C27 H27B 111.4 . . ?
C23 C24 H24 124.7 . . ?
C25 C24 C23 110.6(3) . . ?
C25 C24 H24 124.7 . . ?
N4 C17 H17A 109.5 . . ?
N4 C17 H17B 109.5 . . ?
N4 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N2 C3 H3A 109.5 . . ?
N2 C3 H3B 109.5 . . ?
N2 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
N3 C15 H15A 110.7 . . ?
N3 C15 H15B 110.7 . . ?
H15A C15 H15B 108.8 . . ?
C14 C15 N3 105.2(4) . . ?
C14 C15 H15A 110.7 . . ?
C14 C15 H15B 110.7 . . ?
N5 C18 H18A 109.5 . . ?
N5 C18 H18B 109.5 . . ?
N5 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N6 C30 H30A 111.1 . . ?
N6 C30 H30B 111.1 . . ?
N6 C30 C29 103.4(4) . . ?
H30A C30 H30B 109.1 . . ?
C29 C30 H30A 111.1 . . ?
C29 C30 H30B 111.1 . . ?
H31A C31 H31B 108.3 . . ?
H31A C31 H31C 124.2 . . ?
H31A C31 H31D 43.6 . . ?
H31B C31 H31C 25.1 . . ?
H31B C31 H31D 82.9 . . ?
H31C C31 H31D 107.6 . . ?
Cl2 C31 H31A 109.9 . . ?
Cl2 C31 H31B 109.9 . . ?
Cl2 C31 H31C 114.9 . . ?
Cl2 C31 H31D 86.9 . . ?
Cl2 C31 Cl1 108.9(3) . . ?
Cl2 C31 Cl2A 22.0(3) . . ?
Cl1 C31 H31A 109.9 . . ?
Cl1 C31 H31B 109.9 . . ?
Cl1 C31 H31C 85.4 . . ?
Cl1 C31 H31D 153.5 . . ?
Cl1A C31 H31A 65.2 . . ?
Cl1A C31 H31B 122.8 . . ?
Cl1A C31 H31C 108.8 . . ?
Cl1A C31 H31D 108.8 . . ?
Cl1A C31 Cl2 126.0(3) . . ?
Cl1A C31 Cl1 44.7(2) . . ?
Cl1A C31 Cl2A 114.0(4) . . ?
Cl2A C31 H31A 124.6 . . ?
Cl2A C31 H31B 114.0 . . ?
Cl2A C31 H31C 108.8 . . ?
Cl2A C31 H31D 108.8 . . ?
Cl2A C31 Cl1 87.7(4) . . ?
C27 C28 H28A 110.9 . . ?
C27 C28 H28B 110.9 . . ?
H28A C28 H28B 108.9 . . ?
C29 C28 C27 104.3(4) . . ?
C29 C28 H28A 110.9 . . ?
C29 C28 H28B 110.9 . . ?
C12 C13 H13A 110.6 . . ?
C12 C13 H13B 110.6 . . ?
C12 C13 C14 105.7(4) . . ?
H13A C13 H13B 108.7 . . ?
C14 C13 H13A 110.6 . . ?
C14 C13 H13B 110.6 . . ?
C30 C29 H29A 110.2 . . ?
C30 C29 H29B 110.2 . . ?
C28 C29 C30 107.4(4) . . ?
C28 C29 H29A 110.2 . . ?
C28 C29 H29B 110.2 . . ?
H29A C29 H29B 108.5 . . ?
H10A O10 H10B 109.5 . . ?
C15 C14 C13 108.8(4) . . ?
C15 C14 H14A 109.9 . . ?
C15 C14 H14B 109.9 . . ?
C13 C14 H14A 109.9 . . ?
C13 C14 H14B 109.9 . . ?
H14A C14 H14B 108.3 . . ?
H9A O9 H9B 109.5 . . ?
Cl2A Cl2 C31 84.2(8) . . ?
Cl1A Cl1 C31 60.2(2) . . ?
Cl1 Cl1A C31 75.1(3) . . ?
Cl2 Cl2A C31 73.8(7) . . ?

_olex2_submission_special_instructions 'No special instructions were received'

# start Validation Reply Form
_vrf_PLAT097_12b                 
;
PROBLEM: Large Reported Max.  (Positive) Residual Density       2.38 eA-3  
RESPONSE: There are a number of partial occupancy, disordered solvent water 
molecules present in the asymmetric unit. Attempts were made to model those 
peaks with the highest occupancy, however some residual electron density 
remains.
;
_vrf_PLAT420_12b                 
;
PROBLEM: D-H Without Acceptor       O01C     --H01Z           Please Check 
RESPONSE: See above response
;
_vrf_PLAT934_12b                 
;
PROBLEM: Number of (Iobs-Icalc)/SigmaW > 10 Outliers ....          3 Check 
RESPONSE: See above response
;
# end Validation Reply Form
