# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_dock1l
_database_code_depnum_ccdc_archive 'CCDC 2004020'
loop_
_audit_author_name
_audit_author_address
'Sergey Lindeman'
;Marquette University
United States of America
;
_audit_update_record             
;
2020-05-14 deposited with the CCDC.	2020-08-13 downloaded from the CCDC.
;
_audit_creation_date             2019-04-16
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H13 N O3'
_chemical_formula_sum            'C15 H13 N O3'
_chemical_formula_weight         255.26
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C15 H13 N O3'
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                   7.04830(16)
_cell_length_b                   9.6420(2)
_cell_length_c                   17.8160(4)
_cell_angle_alpha                90
_cell_angle_beta                 93.573(2)
_cell_angle_gamma                90
_cell_volume                     1208.42(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8470
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      29.3010
_cell_measurement_theta_min      3.7760
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94549
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.403
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.25
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0210
_diffrn_reflns_av_unetI/netI     0.0184
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.913
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            13941
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.913
_diffrn_reflns_theta_full        27.000
_diffrn_reflns_theta_max         29.550
_diffrn_reflns_theta_min         3.579
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3756
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.913
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -64.00  35.00   1.00    6.00    --   10.69 -37.00 -60.00   99
  2  ω    -77.00  99.00   1.00    6.00    --   10.69   0.00 150.00  176
  3  ω    -64.00  35.00   1.00    6.00    --   10.69 -37.00  60.00   99
  4  ω    -20.00  22.00   1.00    6.00    --  -10.77 -99.00 150.00   42
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0730657000
_diffrn_orient_matrix_UB_12      0.0503433000
_diffrn_orient_matrix_UB_13      0.0014998000
_diffrn_orient_matrix_UB_21      -0.0359802000
_diffrn_orient_matrix_UB_22      -0.0198910000
_diffrn_orient_matrix_UB_23      -0.0364828000
_diffrn_orient_matrix_UB_31      -0.0594069000
_diffrn_orient_matrix_UB_32      -0.0498378000
_diffrn_orient_matrix_UB_33      0.0160590000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2745
_reflns_number_total             3100
_reflns_odcompleteness_completeness 99.70
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.274
_refine_diff_density_min         -0.245
_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    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         3100
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0427
_refine_ls_R_factor_gt           0.0377
_refine_ls_restrained_S_all      1.066
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0415P)²+0.5156P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0931
_refine_ls_wR_factor_ref         0.0966
_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:
 C2(H2), C5(H5), C6(H6), C7(H7), C8(H8), C9(H9), C11(H11), C12(H12), C13(H13),
 C14(H14)
2.b Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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 0.30098(13) 0.73124(8) 0.40963(5) 0.0233(2) Uani 1 1 d . . . . .
O2 O 0.30905(11) 0.51305(8) 0.36447(4) 0.01848(18) Uani 1 1 d . . . . .
O3 O -0.05182(11) 0.77598(8) 0.55617(4) 0.01786(18) Uani 1 1 d . . . . .
N1 N 0.26831(13) 0.73805(9) 0.56572(5) 0.01415(19) Uani 1 1 d . . . . .
C1 C 0.28654(15) 0.60790(11) 0.41886(6) 0.0161(2) Uani 1 1 d . . . . .
C2 C 0.24362(15) 0.53313(11) 0.48844(6) 0.0160(2) Uani 1 1 d . . . . .
H2 H 0.221455 0.436128 0.484585 0.019 Uiso 1 1 calc R . . . .
C3 C 0.23358(14) 0.59119(11) 0.55622(6) 0.0141(2) Uani 1 1 d . . . . .
C4 C 0.19821(14) 0.51468(11) 0.62594(6) 0.0144(2) Uani 1 1 d . . . . .
C5 C 0.20733(16) 0.58411(11) 0.69498(6) 0.0176(2) Uani 1 1 d . . . . .
H5 H 0.227970 0.681475 0.696190 0.021 Uiso 1 1 calc R . . . .
C6 C 0.18673(16) 0.51317(12) 0.76174(6) 0.0191(2) Uani 1 1 d . . . . .
H6 H 0.193260 0.562100 0.808114 0.023 Uiso 1 1 calc R . . . .
C7 C 0.15660(15) 0.37084(12) 0.76096(6) 0.0183(2) Uani 1 1 d . . . . .
H7 H 0.145158 0.321638 0.806658 0.022 Uiso 1 1 calc R . . . .
C8 C 0.14337(15) 0.30113(12) 0.69242(6) 0.0178(2) Uani 1 1 d . . . . .
H8 H 0.120218 0.204062 0.691469 0.021 Uiso 1 1 calc R . . . .
C9 C 0.16356(15) 0.37158(11) 0.62543(6) 0.0158(2) Uani 1 1 d . . . . .
H9 H 0.153858 0.322593 0.579079 0.019 Uiso 1 1 calc R . . . .
C10 C 0.11009(15) 0.82543(11) 0.56523(6) 0.0143(2) Uani 1 1 d . . . . .
C11 C 0.15586(16) 0.96994(11) 0.57618(6) 0.0169(2) Uani 1 1 d . . . . .
H11 H 0.055640 1.035505 0.577999 0.020 Uiso 1 1 calc R . . . .
C12 C 0.33904(17) 1.01486(11) 0.58400(6) 0.0184(2) Uani 1 1 d . . . . .
H12 H 0.364338 1.111077 0.590263 0.022 Uiso 1 1 calc R . . . .
C13 C 0.49226(16) 0.92040(12) 0.58293(6) 0.0184(2) Uani 1 1 d . . . . .
H13 H 0.620004 0.952109 0.588303 0.022 Uiso 1 1 calc R . . . .
C14 C 0.45287(15) 0.78387(11) 0.57409(6) 0.0170(2) Uani 1 1 d . . . . .
H14 H 0.554113 0.718885 0.573670 0.020 Uiso 1 1 calc R . . . .
C15 C 0.34572(17) 0.56821(13) 0.29157(6) 0.0221(2) Uani 1 1 d . . . . .
H15A H 0.372916 0.491887 0.257537 0.033 Uiso 1 1 calc GR . . . .
H15B H 0.455295 0.630855 0.296367 0.033 Uiso 1 1 calc GR . . . .
H15C H 0.233876 0.619382 0.271244 0.033 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
O1 C1 1.2057(14) . ?
O2 C1 1.3489(13) . ?
O2 C15 1.4417(13) . ?
O3 C10 1.2380(13) . ?
N1 C3 1.4451(13) . ?
N1 C10 1.3972(13) . ?
N1 C14 1.3731(14) . ?
C1 C2 1.4814(14) . ?
C2 C3 1.3370(15) . ?
C3 C4 1.4791(14) . ?
C4 C5 1.3984(15) . ?
C4 C9 1.4012(15) . ?
C5 C6 1.3876(15) . ?
C6 C7 1.3886(16) . ?
C7 C8 1.3920(16) . ?
C8 C9 1.3883(15) . ?
C10 C11 1.4408(15) . ?
C11 C12 1.3607(16) . ?
C12 C13 1.4137(16) . ?
C13 C14 1.3526(15) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O2 C15 115.65(9) . . ?
C10 N1 C3 117.44(9) . . ?
C14 N1 C3 118.71(9) . . ?
C14 N1 C10 123.85(9) . . ?
O1 C1 O2 123.78(10) . . ?
O1 C1 C2 128.13(10) . . ?
O2 C1 C2 108.09(9) . . ?
C3 C2 C1 125.24(10) . . ?
N1 C3 C4 115.25(9) . . ?
C2 C3 N1 119.86(9) . . ?
C2 C3 C4 124.80(10) . . ?
C5 C4 C3 119.93(10) . . ?
C5 C4 C9 118.40(10) . . ?
C9 C4 C3 121.61(9) . . ?
C6 C5 C4 121.10(10) . . ?
C5 C6 C7 120.18(10) . . ?
C6 C7 C8 119.20(10) . . ?
C9 C8 C7 120.87(10) . . ?
C8 C9 C4 120.22(10) . . ?
O3 C10 N1 119.83(9) . . ?
O3 C10 C11 125.94(10) . . ?
N1 C10 C11 114.23(9) . . ?
C12 C11 C10 121.65(10) . . ?
C11 C12 C13 120.95(10) . . ?
C14 C13 C12 118.50(10) . . ?
C13 C14 N1 120.80(10) . . ?

_olex2_date_sample_submission    2019-04-15
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.221
_oxdiff_exptl_absorpt_empirical_full_min 0.844
####################################################################### 
# 
# 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_dock1n
_database_code_depnum_ccdc_archive 'CCDC 2004022'
loop_
_audit_author_name
_audit_author_address
'Sergey Lindeman'
;Marquette University
United States of America
;
_audit_update_record             
;
2020-05-14 deposited with the CCDC.	2020-08-13 downloaded from the CCDC.
;
_audit_creation_date             2019-08-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H11 N O3'
_chemical_formula_sum            'C14 H11 N O3'
_chemical_formula_weight         241.24
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C14 H11 N O3'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   11.1412(2)
_cell_length_b                   8.63104(12)
_cell_length_c                   12.6120(2)
_cell_angle_alpha                90
_cell_angle_beta                 98.0678(17)
_cell_angle_gamma                90
_cell_volume                     1200.77(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6113
_cell_measurement_temperature    100.00(14)
_cell_measurement_theta_max      70.4640
_cell_measurement_theta_min      4.9400
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.783
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87413
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.18
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0209
_diffrn_reflns_av_unetI/netI     0.0135
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            11444
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        70.502
_diffrn_reflns_theta_max         70.502
_diffrn_reflns_theta_min         4.008
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(14)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3756
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -115.00 -14.00   1.00    1.00    --  -42.58 -57.00 -30.00  101
  2  ω    -34.00  75.00   1.00    1.00    --   42.58 -77.00-180.00  109
  3  ω     27.00 126.00   1.00    4.00    --  100.00 -45.00  90.00   99
  4  ω     72.00 176.00   1.00    4.00    --  100.00  30.00 -90.00  104
  5  ω     17.00 110.00   1.00    4.00    --  100.00 -94.00  60.00   93
  6  ω     94.00 173.00   1.00    4.00    --  100.00 125.00 -90.00   79
  7  ω     17.00 110.00   1.00    4.00    --  100.00 -94.00 -30.00   93
  8  ω     94.00 173.00   1.00    4.00    --  100.00 125.00  30.00   79
  9  ω   -115.00 -14.00   1.00    1.00    --  -42.58 -57.00 150.00  101
 10  ω   -125.00 -79.00   1.00    1.00    --  -42.58 -88.00-111.00   46
 11  ω     47.00 178.00   1.00    4.00    --  100.00  15.00 120.00  131
 12  ω     74.00 173.00   1.00    4.00    --  100.00  45.00   0.00   99
 13  ω     71.00 172.00   1.00    4.00    --  100.00  61.00-150.00  101
 14  ω     67.00 176.00   1.00    4.00    --  100.00  77.00 150.00  109
 15  ω   -119.00 -44.00   1.00    1.00    --  -42.58 -77.00  90.00   75
 16  ω   -115.00 -14.00   1.00    1.00    --  -42.58 -57.00-120.00  101
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0328752000
_diffrn_orient_matrix_UB_12      0.1395957000
_diffrn_orient_matrix_UB_13      -0.0663672000
_diffrn_orient_matrix_UB_21      -0.0276207000
_diffrn_orient_matrix_UB_22      0.1106018000
_diffrn_orient_matrix_UB_23      0.0893807000
_diffrn_orient_matrix_UB_31      0.1328925000
_diffrn_orient_matrix_UB_32      -0.0115851000
_diffrn_orient_matrix_UB_33      0.0531971000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2100
_reflns_number_total             2276
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.239
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.034
_refine_ls_extinction_coef       0.0022(3)
_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   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     168
_refine_ls_number_reflns         2276
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0326
_refine_ls_R_factor_gt           0.0300
_refine_ls_restrained_S_all      1.041
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0356P)²+0.4238P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0752
_refine_ls_wR_factor_ref         0.0771
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C6(H6), C7(H7), C8(H8), C9(H9), C11(H11), C12(H12), C13(H13),
 C14(H14)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_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 0.06953(7) -0.09244(9) 0.68031(6) 0.02243(19) Uani 1 1 d . . . . .
H1 H -0.0038(16) -0.1224(19) 0.6964(13) 0.042(4) Uiso 1 1 d . . . . .
O2 O -0.03755(7) 0.10665(9) 0.60096(6) 0.0226(2) Uani 1 1 d . . . . .
O3 O 0.12921(7) 0.32161(9) 0.75351(6) 0.02057(19) Uani 1 1 d . . . . .
N1 N 0.16722(8) 0.27379(10) 0.58496(7) 0.0173(2) Uani 1 1 d . . . . .
C1 C 0.05828(10) 0.04310(12) 0.63027(8) 0.0182(2) Uani 1 1 d . . . . .
C2 C 0.17718(10) 0.11322(12) 0.61516(8) 0.0181(2) Uani 1 1 d . . . . .
C3 C 0.28263(10) 0.03729(13) 0.63173(8) 0.0214(2) Uani 1 1 d . . . . .
H3 H 0.275724 -0.069386 0.648420 0.026 Uiso 1 1 calc R . . . .
C4 C 0.40736(10) 0.09013(14) 0.62861(9) 0.0243(3) Uani 1 1 d . . . . .
C5 C 0.44350(11) 0.24443(15) 0.61875(10) 0.0293(3) Uani 1 1 d . . . . .
H5 H 0.384350 0.324427 0.612116 0.035 Uiso 1 1 calc R . . . .
C6 C 0.56475(11) 0.28176(19) 0.61858(10) 0.0367(3) Uani 1 1 d . . . . .
H6 H 0.587603 0.386754 0.610860 0.044 Uiso 1 1 calc R . . . .
C7 C 0.65238(11) 0.1674(2) 0.62956(10) 0.0395(4) Uani 1 1 d . . . . .
H7 H 0.735194 0.193472 0.629368 0.047 Uiso 1 1 calc R . . . .
C8 C 0.61883(12) 0.0149(2) 0.64079(10) 0.0388(3) Uani 1 1 d . . . . .
H8 H 0.678941 -0.063882 0.649118 0.047 Uiso 1 1 calc R . . . .
C9 C 0.49756(11) -0.02397(16) 0.64001(9) 0.0302(3) Uani 1 1 d . . . . .
H9 H 0.475638 -0.129399 0.647300 0.036 Uiso 1 1 calc R . . . .
C10 C 0.14179(9) 0.37608(12) 0.66332(8) 0.0179(2) Uani 1 1 d . . . . .
C11 C 0.13417(10) 0.53518(13) 0.63333(9) 0.0224(2) Uani 1 1 d . . . . .
H11 H 0.119143 0.610864 0.684559 0.027 Uiso 1 1 calc R . . . .
C12 C 0.14810(10) 0.58059(13) 0.53233(10) 0.0255(3) Uani 1 1 d . . . . .
H12 H 0.142888 0.687393 0.514058 0.031 Uiso 1 1 calc R . . . .
C13 C 0.17020(10) 0.47053(14) 0.45454(9) 0.0250(3) Uani 1 1 d . . . . .
H13 H 0.178986 0.502167 0.383890 0.030 Uiso 1 1 calc R . . . .
C14 C 0.17866(10) 0.31878(13) 0.48255(9) 0.0216(2) Uani 1 1 d . . . . .
H14 H 0.192593 0.243168 0.430909 0.026 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 H1 0.907(18) . ?
O1 C1 1.3268(13) . ?
O2 C1 1.2111(13) . ?
O3 C10 1.2567(13) . ?
N1 C2 1.4375(13) . ?
N1 C10 1.3838(14) . ?
N1 C14 1.3717(14) . ?
C1 C2 1.4927(15) . ?
C2 C3 1.3358(16) . ?
C3 H3 0.9500 . ?
C3 C4 1.4684(16) . ?
C4 C5 1.4018(18) . ?
C4 C9 1.3999(17) . ?
C5 H5 0.9500 . ?
C5 C6 1.3891(18) . ?
C6 H6 0.9500 . ?
C6 C7 1.382(2) . ?
C7 H7 0.9500 . ?
C7 C8 1.381(2) . ?
C8 H8 0.9500 . ?
C8 C9 1.3909(19) . ?
C9 H9 0.9500 . ?
C10 C11 1.4237(15) . ?
C11 H11 0.9500 . ?
C11 C12 1.3623(16) . ?
C12 H12 0.9500 . ?
C12 C13 1.4119(18) . ?
C13 H13 0.9500 . ?
C13 C14 1.3564(16) . ?
C14 H14 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 H1 109.2(10) . . ?
C10 N1 C2 116.22(8) . . ?
C14 N1 C2 120.56(9) . . ?
C14 N1 C10 123.18(9) . . ?
O1 C1 C2 113.07(9) . . ?
O2 C1 O1 124.39(10) . . ?
O2 C1 C2 122.52(10) . . ?
N1 C2 C1 112.82(9) . . ?
C3 C2 N1 123.23(10) . . ?
C3 C2 C1 123.91(10) . . ?
C2 C3 H3 114.4 . . ?
C2 C3 C4 131.17(11) . . ?
C4 C3 H3 114.4 . . ?
C5 C4 C3 125.60(11) . . ?
C9 C4 C3 116.56(11) . . ?
C9 C4 C5 117.80(11) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 C4 120.79(12) . . ?
C6 C5 H5 119.6 . . ?
C5 C6 H6 119.7 . . ?
C7 C6 C5 120.52(14) . . ?
C7 C6 H6 119.7 . . ?
C6 C7 H7 120.2 . . ?
C8 C7 C6 119.57(12) . . ?
C8 C7 H7 120.2 . . ?
C7 C8 H8 119.8 . . ?
C7 C8 C9 120.40(13) . . ?
C9 C8 H8 119.8 . . ?
C4 C9 H9 119.6 . . ?
C8 C9 C4 120.90(13) . . ?
C8 C9 H9 119.6 . . ?
O3 C10 N1 117.89(9) . . ?
O3 C10 C11 126.24(10) . . ?
N1 C10 C11 115.86(9) . . ?
C10 C11 H11 119.5 . . ?
C12 C11 C10 121.03(10) . . ?
C12 C11 H11 119.5 . . ?
C11 C12 H12 119.7 . . ?
C11 C12 C13 120.67(10) . . ?
C13 C12 H12 119.7 . . ?
C12 C13 H13 120.6 . . ?
C14 C13 C12 118.76(10) . . ?
C14 C13 H13 120.6 . . ?
N1 C14 H14 119.8 . . ?
C13 C14 N1 120.42(10) . . ?
C13 C14 H14 119.8 . . ?

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
O1 H1 O3 0.907(18) 1.683(18) 2.5822(11) 170.9(16) 2_546 yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 N1 -165.99(8) . . . . ?
O1 C1 C2 C3 11.62(15) . . . . ?
O2 C1 C2 N1 12.77(14) . . . . ?
O2 C1 C2 C3 -169.62(10) . . . . ?
O3 C10 C11 C12 -179.24(11) . . . . ?
N1 C2 C3 C4 2.46(18) . . . . ?
N1 C10 C11 C12 1.72(16) . . . . ?
C1 C2 C3 C4 -174.91(10) . . . . ?
C2 N1 C10 O3 -0.18(14) . . . . ?
C2 N1 C10 C11 178.94(9) . . . . ?
C2 N1 C14 C13 -179.46(10) . . . . ?
C2 C3 C4 C5 8.13(19) . . . . ?
C2 C3 C4 C9 -174.06(11) . . . . ?
C3 C4 C5 C6 178.83(11) . . . . ?
C3 C4 C9 C8 -178.39(10) . . . . ?
C4 C5 C6 C7 -0.85(19) . . . . ?
C5 C4 C9 C8 -0.40(17) . . . . ?
C5 C6 C7 C8 0.0(2) . . . . ?
C6 C7 C8 C9 0.66(19) . . . . ?
C7 C8 C9 C4 -0.45(19) . . . . ?
C9 C4 C5 C6 1.05(17) . . . . ?
C10 N1 C2 C1 70.35(11) . . . . ?
C10 N1 C2 C3 -107.28(12) . . . . ?
C10 N1 C14 C13 2.81(16) . . . . ?
C10 C11 C12 C13 0.17(17) . . . . ?
C11 C12 C13 C14 -0.72(17) . . . . ?
C12 C13 C14 N1 -0.71(16) . . . . ?
C14 N1 C2 C1 -107.53(10) . . . . ?
C14 N1 C2 C3 74.84(14) . . . . ?
C14 N1 C10 O3 177.64(9) . . . . ?
C14 N1 C10 C11 -3.23(15) . . . . ?

_olex2_date_sample_data_collection 2019-08-27
_olex2_date_sample_submission    2019-08-15
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.279
_oxdiff_exptl_absorpt_empirical_full_min 0.849
####################################################################### 
# 
# 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_dock1m
_database_code_depnum_ccdc_archive 'CCDC 2004021'
loop_
_audit_author_name
_audit_author_address
'Sergey Lindeman'
;Marquette University
United States of America
;
_audit_update_record             
;
2020-05-14 deposited with the CCDC.	2020-08-13 downloaded from the CCDC.
;
_audit_creation_date             2019-04-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H13 N O4, 2(H2 O)'
_chemical_formula_sum            'C14 H17 N O6'
_chemical_formula_weight         295.28
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C14 H17 N O6'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   23.1618(8)
_cell_length_b                   6.1459(2)
_cell_length_c                   20.0176(6)
_cell_angle_alpha                90
_cell_angle_beta                 95.672(3)
_cell_angle_gamma                90
_cell_volume                     2835.54(16)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4399
_cell_measurement_temperature    99.8(3)
_cell_measurement_theta_max      70.2010
_cell_measurement_theta_min      4.4090
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.922
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.709
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.383
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1248
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-7 0 -11 0.0134
7 0 11 0.0104
2 -4 0 0.1719
-2 4 0 0.1719
15 0 -3 0.0883
-15 0 3 0.0883

_exptl_crystal_size_max          0.369
_exptl_crystal_size_mid          0.196
_exptl_crystal_size_min          0.024
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-6.9949 -0.0006 -11.0010 0.8613 -0.5233 0.0728
6.9949 0.0006 11.0010 -0.8613 0.5233 -0.0728
1.9942 -4.0020 0.0113 0.0742 0.3955 0.9287
-1.9942 4.0020 -0.0113 -0.0742 -0.3955 -0.9287
15.0007 -0.0005 -2.9898 0.1982 0.9473 -0.2765
-15.0007 0.0005 2.9898 -0.1982 -0.9473 0.2765

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0388
_diffrn_reflns_av_unetI/netI     0.0263
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            12120
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        70.721
_diffrn_reflns_theta_max         70.721
_diffrn_reflns_theta_min         3.836
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.8(3)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3756
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -116.00 -17.00   1.00    8.00    --  -41.71 -37.00   0.00   99
  2  ω    -83.00  38.00   1.00    8.00    --  -41.71  19.00-150.00  121
  3  ω     27.00 126.00   1.00   32.00    --  100.00 -45.00-150.00   99
  4  ω     94.00 173.00   1.00   32.00    --  100.00 125.00-150.00   79
  5  ω     17.00 110.00   1.00   32.00    --  100.00 -94.00 -30.00   93
  6  ω     72.00 176.00   1.00   32.00    --  100.00  30.00  30.00  104
  7  ω     74.00 173.00   1.00   32.00    --  100.00  45.00 -30.00   99
  8  ω     94.00 173.00   1.00   32.00    --  100.00 125.00-180.00   79
  9  ω     24.00 133.00   1.00   32.00    --  100.00 -77.00 120.00  109
 10  ω   -116.00 -17.00   1.00    8.00    --  -41.71 -37.00-180.00   99
 11  ω   -114.00 -14.00   1.00    8.00    --  -41.71 -57.00 120.00  100
 12  ω     47.00 178.00   1.00   32.00    --  100.00  15.00-180.00  131
 13  ω     71.00 172.00   1.00   32.00    --  100.00  61.00  60.00  101
 14  ω     71.00 170.00   1.00   32.00    --  100.00  61.00-150.00   99
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0021223000
_diffrn_orient_matrix_UB_12      -0.0198173000
_diffrn_orient_matrix_UB_13      -0.0769381000
_diffrn_orient_matrix_UB_21      0.0644592000
_diffrn_orient_matrix_UB_22      -0.0666768000
_diffrn_orient_matrix_UB_23      0.0065901000
_diffrn_orient_matrix_UB_31      -0.0175367000
_diffrn_orient_matrix_UB_32      -0.2407786000
_diffrn_orient_matrix_UB_33      0.0045418000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2302
_reflns_number_total             2702
_reflns_odcompleteness_completeness 99.75
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.263
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     214
_refine_ls_number_reflns         2702
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0492
_refine_ls_R_factor_gt           0.0414
_refine_ls_restrained_S_all      1.037
_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)+(0.0684P)²+1.8284P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1088
_refine_ls_wR_factor_ref         0.1174
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2A), C3(H3)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C8(H8), C9(H9), C11(H11), C12(H12), C13(H13), C14(H14)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_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 0.43420(5) 0.55094(19) 0.27445(5) 0.0265(3) Uani 1 1 d . . . . .
O2 O 0.43379(5) 0.84264(18) 0.20708(6) 0.0274(3) Uani 1 1 d . . . . .
H2 H 0.4371(11) 0.923(4) 0.2459(13) 0.047(6) Uiso 1 1 d . . . . .
O3 O 0.44990(5) 0.71211(18) 0.00951(5) 0.0260(3) Uani 1 1 d . . . . .
O4 O 0.41390(5) 0.28485(18) 0.16705(6) 0.0254(3) Uani 1 1 d . . . . .
H4 H 0.4338(12) 0.214(5) 0.1380(14) 0.058(7) Uiso 1 1 d . . . . .
N1 N 0.37786(5) 0.4864(2) 0.03892(6) 0.0210(3) Uani 1 1 d . . . . .
C1 C 0.43089(6) 0.6337(3) 0.21911(8) 0.0225(3) Uani 1 1 d . . . . .
C2 C 0.42468(7) 0.5050(2) 0.15395(8) 0.0218(3) Uani 1 1 d . . . . .
H2A H 0.462485 0.513551 0.133896 0.026 Uiso 1 1 calc R . . . .
C3 C 0.37760(6) 0.6063(2) 0.10331(7) 0.0209(3) Uani 1 1 d . . . . .
H3 H 0.390414 0.758213 0.094711 0.025 Uiso 1 1 calc R . . . .
C4 C 0.31725(6) 0.6228(2) 0.12587(7) 0.0218(3) Uani 1 1 d . . . . .
C5 C 0.28094(7) 0.7826(3) 0.09579(9) 0.0289(4) Uani 1 1 d . . . . .
H5 H 0.294472 0.872369 0.061975 0.035 Uiso 1 1 calc R . . . .
C6 C 0.22551(8) 0.8135(3) 0.11420(10) 0.0350(4) Uani 1 1 d . . . . .
H6 H 0.201445 0.924107 0.093259 0.042 Uiso 1 1 calc R . . . .
C7 C 0.20512(7) 0.6833(3) 0.16306(9) 0.0323(4) Uani 1 1 d . . . . .
H7 H 0.167091 0.704064 0.175850 0.039 Uiso 1 1 calc R . . . .
C8 C 0.24049(8) 0.5225(3) 0.19320(9) 0.0335(4) Uani 1 1 d . . . . .
H8 H 0.226542 0.432241 0.226626 0.040 Uiso 1 1 calc R . . . .
C9 C 0.29647(7) 0.4920(3) 0.17486(8) 0.0288(4) Uani 1 1 d . . . . .
H9 H 0.320485 0.381407 0.195923 0.035 Uiso 1 1 calc R . . . .
C10 C 0.41710(6) 0.5528(3) -0.00524(7) 0.0219(3) Uani 1 1 d . . . . .
C11 C 0.41695(7) 0.4302(3) -0.06591(8) 0.0247(3) Uani 1 1 d . . . . .
H11 H 0.441737 0.473603 -0.098583 0.030 Uiso 1 1 calc R . . . .
C12 C 0.38236(7) 0.2534(3) -0.07815(8) 0.0265(4) Uani 1 1 d . . . . .
H12 H 0.383714 0.172988 -0.118497 0.032 Uiso 1 1 calc R . . . .
C13 C 0.34431(8) 0.1893(3) -0.03071(8) 0.0283(4) Uani 1 1 d . . . . .
H13 H 0.319897 0.065971 -0.038750 0.034 Uiso 1 1 calc R . . . .
C14 C 0.34327(7) 0.3069(3) 0.02643(8) 0.0263(3) Uani 1 1 d . . . . .
H14 H 0.317966 0.264039 0.058609 0.032 Uiso 1 1 calc R . . . .
O2W O 0.48488(5) 0.0931(2) 0.08097(6) 0.0261(3) Uani 1 1 d . . . . .
H2WA H 0.4724(11) -0.031(5) 0.0639(13) 0.051(7) Uiso 1 1 d . . . . .
H2WB H 0.5044(12) 0.157(4) 0.0498(13) 0.054(7) Uiso 1 1 d . . . . .
O1W O 0.43598(5) 0.10115(19) 0.30547(6) 0.0263(3) Uani 1 1 d . . . . .
H1WA H 0.4389(10) 0.233(4) 0.2870(12) 0.043(6) Uiso 1 1 d . . . . .
H1WB H 0.4631(12) 0.096(4) 0.3403(14) 0.055(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
O1 C1 1.2144(19) . ?
O2 C1 1.310(2) . ?
O3 C10 1.257(2) . ?
O4 C2 1.4050(18) . ?
N1 C3 1.4851(19) . ?
N1 C10 1.3901(19) . ?
N1 C14 1.372(2) . ?
C1 C2 1.520(2) . ?
C2 C3 1.545(2) . ?
C3 C4 1.514(2) . ?
C4 C5 1.391(2) . ?
C4 C9 1.390(2) . ?
C5 C6 1.383(2) . ?
C6 C7 1.382(3) . ?
C7 C8 1.383(3) . ?
C8 C9 1.395(2) . ?
C10 C11 1.429(2) . ?
C11 C12 1.358(2) . ?
C12 C13 1.414(2) . ?
C13 C14 1.355(2) . ?

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
C10 N1 C3 117.72(12) . . ?
C14 N1 C3 120.31(12) . . ?
C14 N1 C10 121.80(13) . . ?
O1 C1 O2 125.36(14) . . ?
O1 C1 C2 123.84(14) . . ?
O2 C1 C2 110.77(13) . . ?
O4 C2 C1 110.14(12) . . ?
O4 C2 C3 112.56(12) . . ?
C1 C2 C3 110.74(12) . . ?
N1 C3 C2 107.86(12) . . ?
N1 C3 C4 112.03(12) . . ?
C4 C3 C2 116.35(12) . . ?
C5 C4 C3 117.04(14) . . ?
C9 C4 C3 124.45(14) . . ?
C9 C4 C5 118.50(15) . . ?
C6 C5 C4 121.25(16) . . ?
C7 C6 C5 120.00(17) . . ?
C6 C7 C8 119.55(16) . . ?
C7 C8 C9 120.47(16) . . ?
C4 C9 C8 120.23(16) . . ?
O3 C10 N1 119.83(14) . . ?
O3 C10 C11 124.13(14) . . ?
N1 C10 C11 116.04(14) . . ?
C12 C11 C10 121.80(14) . . ?
C11 C12 C13 119.84(15) . . ?
C14 C13 C12 118.86(15) . . ?
C13 C14 N1 121.59(15) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O2 H2 O1W 0.92(3) 1.62(3) 2.5272(16) 169(2) 1_565 yes
O4 H4 O2W 0.89(3) 1.88(3) 2.7606(16) 171(3) . yes
O2W H2WA O3 0.87(3) 1.96(3) 2.8204(17) 169(2) 1_545 yes
O2W H2WB O3 0.90(3) 1.85(3) 2.7454(16) 175(2) 5_665 yes
O1W H1WA O1 0.89(3) 1.97(3) 2.8327(17) 161(2) . yes
O1W H1WA O4 0.89(3) 2.44(2) 2.9889(16) 120.4(19) . yes
O1W H1WB O2W 0.89(3) 1.89(3) 2.7761(17) 175(2) 2_655 yes

_olex2_date_sample_data_collection 2019-04-23
_olex2_date_sample_submission    2019-04-23
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.718
_oxdiff_exptl_absorpt_empirical_full_min 0.683

# start Validation Reply Form
_vrf_PLAT414_dock1m              
;
PROBLEM: Short Intra D-H..H-X       H2A      ..H4               1.96 Ang.  
RESPONSE: this is a 1,4 intramolecular distance in cisoid moiety H-C-O-H
;
# end Validation Reply Form
####################################################################### 
# 
# 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_dock1o
_database_code_depnum_ccdc_archive 'CCDC 2004023'
loop_
_audit_author_name
_audit_author_address
'Sergey Lindeman'
;Marquette University
United States of America
;
_audit_update_record             
;
2020-05-14 deposited with the CCDC.	2020-08-13 downloaded from the CCDC.
;
_audit_creation_date             2019-12-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H25 N3 O3'
_chemical_formula_sum            'C20 H25 N3 O3'
_chemical_formula_weight         355.43
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C20 H25 N3 O3'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   13.9620(3)
_cell_length_b                   8.28868(13)
_cell_length_c                   17.5984(3)
_cell_angle_alpha                90
_cell_angle_beta                 112.379(2)
_cell_angle_gamma                90
_cell_volume                     1883.22(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8540
_cell_measurement_temperature    101(2)
_cell_measurement_theta_max      70.4890
_cell_measurement_theta_min      5.1810
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.689
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.414
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.254
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             760
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
2 -1 -11 0.1112
-6 1 10 0.1141
-8 1 1 0.0717
8 -1 2 0.0805
-3 -5 4 0.1704
-5 4 -2 0.1381
3 0 -11 0.0859
6 1 4 0.1067

_exptl_crystal_size_max          0.485
_exptl_crystal_size_mid          0.258
_exptl_crystal_size_min          0.175
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
2.0000 -1.0000 -11.0000 0.3516 0.7511 0.5464
-6.0000 1.0000 10.0000 -0.3875 -0.8805 -0.0434
-8.0000 1.0000 1.0000 -0.0464 -0.5158 0.7860
8.0000 -1.0000 2.0000 -0.0803 0.3642 -0.9900
-3.0000 -5.0000 4.0000 -0.9888 0.1903 0.1353
-5.0000 4.0000 -2.0000 0.5957 -0.5456 0.6151
3.0000 -0.0000 -11.0000 0.5233 0.6907 0.4215
6.0000 1.0000 4.0000 0.1005 -0.0377 -0.9408

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0241
_diffrn_reflns_av_unetI/netI     0.0149
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            17568
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        70.471
_diffrn_reflns_theta_max         70.471
_diffrn_reflns_theta_min         3.423
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      101(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3756
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -117.00 -18.00   0.50    1.00    --  -42.46 -37.00   0.00  198
  2  ω    -92.00  -2.00   0.50    1.00    --  -42.46 125.00-180.00  180
  3  ω   -117.00 -18.00   0.50    1.00    --  -42.46 -37.00  90.00  198
  4  ω     22.00  97.00   0.50    1.00    --   42.46-123.00 -74.00  150
  5  ω     74.00 173.00   0.50    4.00    --  100.00  45.00-150.00  198
  6  ω     24.00 128.00   0.50    4.00    --  100.00 -30.00  90.00  208
  7  ω     27.00 126.00   0.50    4.00    --  100.00 -45.00 -60.00  198
  8  ω     94.00 173.00   0.50    4.00    --  100.00 125.00 -60.00  158
  9  ω     17.00 110.00   0.50    4.00    --  100.00 -94.00   0.00  186
 10  ω     17.00 110.00   0.50    4.00    --  100.00 -94.00 -90.00  186
 11  ω     71.00 172.00   0.50    4.00    --  100.00  61.00  90.00  202
 12  ω    -92.00  -2.00   0.50    1.00    --  -42.46 125.00  60.00  180
 13  ω   -115.00 -14.00   0.50    1.00    --  -42.46 -57.00 -90.00  202
 14  ω   -119.00 -10.00   0.50    1.00    --  -42.46 -77.00-150.00  218
 15  ω     71.00  98.00   0.50    4.00    --  100.00  61.00 150.00   54
 16  ω     74.00 173.00   0.50    4.00    --  100.00  45.00  30.00  198
 17  ω     74.00 173.00   0.50    4.00    --  100.00  45.00 -90.00  198
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0195464000
_diffrn_orient_matrix_UB_12      0.1522267000
_diffrn_orient_matrix_UB_13      -0.0422453000
_diffrn_orient_matrix_UB_21      0.0449728000
_diffrn_orient_matrix_UB_22      -0.1054571000
_diffrn_orient_matrix_UB_23      -0.0505223000
_diffrn_orient_matrix_UB_31      -0.1087757000
_diffrn_orient_matrix_UB_32      -0.0161763000
_diffrn_orient_matrix_UB_33      -0.0679837000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3156
_reflns_number_total             3541
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.291
_refine_diff_density_min         -0.475
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     326
_refine_ls_number_reflns         3541
_refine_ls_number_restraints     14
_refine_ls_R_factor_all          0.0524
_refine_ls_R_factor_gt           0.0479
_refine_ls_restrained_S_all      1.054
_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)+(0.0684P)²+0.7578P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1260
_refine_ls_wR_factor_ref         0.1307
_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
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid bond restraints
 C5, C6, C7, C8, C9
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C5A, C6A, C7A, C8A, C9A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
Uanis(C5) = Uanis(C5A)
4. Others
 Fixed Sof: N3(0.5) N3A(0.5) C5(0.5) H5(0.5) C5A(0.5) H5A(0.5) C6(0.5) H6(0.5)
 C6A(0.5) H6A(0.5) C7(0.5) H7(0.5) C7A(0.5) H7A(0.5) C8(0.5) H8(0.5) C8A(0.5)
 H8A(0.5) C9(0.5) H9(0.5) C9A(0.5) H9A(0.5) H15A(0.5) H15B(0.5) H15C(0.5)
 H15D(0.5) C16(0.5) H16A(0.5) H16B(0.5) C16A(0.5) H16C(0.5) H16D(0.5) C17(0.5)
 H17A(0.5) H17B(0.5) C17A(0.5) H17C(0.5) H17D(0.5) C18(0.5) H18A(0.5) H18B(0.5)
 H18C(0.5) C18A(0.5) H18D(0.5) H18E(0.5) H18F(0.5) C19(0.5) H19A(0.5) H19B(0.5)
 C19A(0.5) H19C(0.5) H19D(0.5) C20(0.5) H20A(0.5) H20B(0.5) H20C(0.5) C20A(0.5)
 H20D(0.5) H20E(0.5) H20F(0.5)
5.a Ternary CH refined with riding coordinates:
 C1(H1)
5.b Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C15(H15C,H15D), C16(H16A,H16B), C16A(H16C,H16D), C17(H17A,
 H17B), C17A(H17C,H17D), C19(H19A,H19B), C19A(H19C,H19D)
5.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C5A(H5A), C6(H6), C6A(H6A), C7(H7), C7A(H7A), C8(H8), C8A(H8A),
 C9(H9), C9A(H9A), C11(H11), C12(H12), C13(H13), C14(H14)
5.d Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C18A(H18D,H18E,H18F), C20(H20A,H20B,H20C), C20A(H20D,
 H20E,H20F)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_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 0.28839(10) -0.17178(18) 0.26465(8) 0.0582(4) Uani 1 1 d . . . . .
O2 O 0.25205(7) 0.24134(12) 0.27290(6) 0.0329(3) Uani 1 1 d . . . . .
O3 O 0.49372(7) -0.17948(11) 0.45440(6) 0.0290(2) Uani 1 1 d . . . . .
N1 N 0.45112(9) 0.00783(16) 0.35212(8) 0.0341(3) Uani 1 1 d . . . . .
N2 N 0.35913(10) 0.31702(14) 0.40138(8) 0.0335(3) Uani 1 1 d . . . . .
H2 H 0.4053(15) 0.283(2) 0.4489(12) 0.041(5) Uiso 1 1 d . . . . .
N3 N 0.24388(19) 0.4419(3) 0.48666(17) 0.0222(6) Uiso 0.5 1 d . . P A 1
N3A N 0.2538(2) 0.4771(3) 0.50905(18) 0.0251(6) Uiso 0.5 1 d . . P B 2
C1 C 0.35419(10) 0.03569(16) 0.36423(8) 0.0262(3) Uani 1 1 d . . . . .
H1 H 0.366944 0.017106 0.423445 0.031 Uiso 1 1 calc R . . . .
C2 C 0.27115(11) -0.08289(17) 0.31213(9) 0.0309(3) Uani 1 1 d . . . . .
C3 C 0.31638(10) 0.21051(17) 0.34183(9) 0.0276(3) Uani 1 1 d . . . . .
C4 C 0.17114(11) -0.08781(17) 0.32365(9) 0.0320(3) Uani 1 1 d . . . . .
C5 C 0.1527(10) 0.0171(11) 0.3801(9) 0.0345(13) Uani 0.5 1 d . U P C 1
H5 H 0.206161 0.089486 0.410897 0.041 Uiso 0.5 1 calc R . P C 1
C5A C 0.1563(10) -0.0265(11) 0.3897(9) 0.0345(13) Uani 0.5 1 d . U P C 2
H5A H 0.208328 0.034169 0.430727 0.041 Uiso 0.5 1 calc R . P C 2
C6 C 0.0594(4) 0.0195(6) 0.3929(3) 0.0429(11) Uani 0.5 1 d . U P C 1
H6 H 0.051594 0.088051 0.433411 0.052 Uiso 0.5 1 calc R . P C 1
C6A C 0.0604(4) -0.0573(6) 0.3940(4) 0.0523(12) Uani 0.5 1 d . U P C 2
H6A H 0.046197 -0.015680 0.438958 0.063 Uiso 0.5 1 calc R . P C 2
C7 C -0.0206(5) -0.0788(7) 0.3459(5) 0.0449(14) Uani 0.5 1 d . U P C 1
H7 H -0.085032 -0.075394 0.352402 0.054 Uiso 0.5 1 calc R . P C 1
C7A C -0.0142(5) -0.1464(9) 0.3349(6) 0.0515(16) Uani 0.5 1 d . U P C 2
H7A H -0.079103 -0.164635 0.339196 0.062 Uiso 0.5 1 calc R . P C 2
C8 C -0.0076(9) -0.1816(16) 0.2897(7) 0.043(2) Uani 0.5 1 d . U P C 1
H8 H -0.060870 -0.253654 0.258418 0.052 Uiso 0.5 1 calc R . P C 1
C8A C 0.0045(8) -0.2094(17) 0.2694(7) 0.044(2) Uani 0.5 1 d . U P C 2
H8A H -0.049132 -0.267823 0.228529 0.053 Uiso 0.5 1 calc R . P C 2
C9 C 0.0880(11) -0.1761(17) 0.2803(6) 0.0357(18) Uani 0.5 1 d . U P C 1
H9 H 0.094173 -0.242545 0.238381 0.043 Uiso 0.5 1 calc R . P C 1
C9A C 0.0962(10) -0.1911(16) 0.2612(7) 0.0340(16) Uani 0.5 1 d . U P C 2
H9A H 0.111173 -0.241129 0.218402 0.041 Uiso 0.5 1 calc R . P C 2
C10 C 0.51873(10) -0.10596(17) 0.40302(9) 0.0290(3) Uani 1 1 d . . . . .
C11 C 0.61373(11) -0.12785(19) 0.39058(10) 0.0353(4) Uani 1 1 d . . . . .
H11 H 0.664890 -0.199006 0.425582 0.042 Uiso 1 1 calc R . . . .
C12 C 0.63194(13) -0.0490(2) 0.32985(12) 0.0465(4) Uani 1 1 d . . . . .
H12 H 0.695649 -0.064978 0.323158 0.056 Uiso 1 1 calc R . . . .
C13 C 0.55708(16) 0.0566(3) 0.27654(15) 0.0639(7) Uani 1 1 d . . . . .
H13 H 0.568650 0.108946 0.232776 0.077 Uiso 1 1 calc R . . . .
C14 C 0.46877(15) 0.0814(3) 0.28907(13) 0.0562(6) Uani 1 1 d . . . . .
H14 H 0.417639 0.151652 0.253301 0.067 Uiso 1 1 calc R . . . .
C15 C 0.32770(12) 0.48630(17) 0.39201(9) 0.0336(3) Uani 1 1 d . . . . .
H15A H 0.382486 0.553342 0.432060 0.040 Uiso 0.5 1 calc R . P D 1
H15B H 0.316931 0.524073 0.335983 0.040 Uiso 0.5 1 calc R . P D 1
H15C H 0.259810 0.495498 0.345709 0.040 Uiso 0.5 1 calc R . P E 2
H15D H 0.378544 0.549012 0.377361 0.040 Uiso 0.5 1 calc R . P E 2
C16 C 0.2337(2) 0.5012(3) 0.40583(15) 0.0235(5) Uani 0.5 1 d . . P A 1
H16A H 0.178301 0.439947 0.362997 0.028 Uiso 0.5 1 calc R . P A 1
H16B H 0.212685 0.616094 0.400773 0.028 Uiso 0.5 1 calc R . P A 1
C16A C 0.3181(2) 0.5687(3) 0.47510(17) 0.0299(6) Uani 0.5 1 d . . P B 2
H16C H 0.388450 0.579663 0.518079 0.036 Uiso 0.5 1 calc R . P B 2
H16D H 0.288753 0.678458 0.460968 0.036 Uiso 0.5 1 calc R . P B 2
C17 C 0.3296(2) 0.5209(3) 0.55437(16) 0.0249(5) Uani 0.5 1 d . . P A 1
H17A H 0.395611 0.488122 0.550231 0.030 Uiso 0.5 1 calc R . P A 1
H17B H 0.329994 0.478001 0.607008 0.030 Uiso 0.5 1 calc R . P A 1
C17A C 0.2522(2) 0.5579(4) 0.58320(17) 0.0311(6) Uani 0.5 1 d . . P B 2
H17C H 0.324435 0.584850 0.619055 0.037 Uiso 0.5 1 calc R . P B 2
H17D H 0.226167 0.480009 0.613437 0.037 Uiso 0.5 1 calc R . P B 2
C18 C 0.3277(2) 0.7044(4) 0.55836(19) 0.0345(7) Uani 0.5 1 d . . P A 1
H18A H 0.334680 0.749762 0.509273 0.052 Uiso 0.5 1 calc GR . P A 1
H18B H 0.385334 0.741752 0.607485 0.052 Uiso 0.5 1 calc GR . P A 1
H18C H 0.262044 0.739811 0.560872 0.052 Uiso 0.5 1 calc GR . P A 1
C18A C 0.1872(3) 0.7119(4) 0.56944(19) 0.0387(7) Uani 0.5 1 d . . P B 2
H18D H 0.114293 0.686110 0.537759 0.058 Uiso 0.5 1 calc GR . P B 2
H18E H 0.211370 0.790409 0.539076 0.058 Uiso 0.5 1 calc GR . P B 2
H18F H 0.194308 0.757647 0.622661 0.058 Uiso 0.5 1 calc GR . P B 2
C19 C 0.1437(2) 0.4586(4) 0.4962(2) 0.0302(6) Uani 0.5 1 d . . P A 1
H19A H 0.088209 0.414705 0.446549 0.036 Uiso 0.5 1 calc R . P A 1
H19B H 0.129302 0.574677 0.499781 0.036 Uiso 0.5 1 calc R . P A 1
C19A C 0.1497(2) 0.4435(4) 0.4486(2) 0.0311(6) Uani 0.5 1 d . . P B 2
H19C H 0.155204 0.386763 0.400923 0.037 Uiso 0.5 1 calc R . P B 2
H19D H 0.112984 0.546708 0.428695 0.037 Uiso 0.5 1 calc R . P B 2
C20 C 0.1401(3) 0.3740(5) 0.5706(2) 0.0470(9) Uani 0.5 1 d . . P A 1
H20A H 0.069168 0.376420 0.568912 0.070 Uiso 0.5 1 calc GR . P A 1
H20B H 0.186483 0.428696 0.620353 0.070 Uiso 0.5 1 calc GR . P A 1
H20C H 0.162332 0.261761 0.570943 0.070 Uiso 0.5 1 calc GR . P A 1
C20A C 0.0873(3) 0.3411(4) 0.4845(2) 0.0409(7) Uani 0.5 1 d . . P B 2
H20D H 0.023874 0.303931 0.440190 0.061 Uiso 0.5 1 calc GR . P B 2
H20E H 0.069106 0.405396 0.523742 0.061 Uiso 0.5 1 calc GR . P B 2
H20F H 0.128561 0.247611 0.512647 0.061 Uiso 0.5 1 calc GR . P B 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.2050(19) . ?
O2 C3 1.2304(17) . ?
O3 C10 1.2456(17) . ?
N1 C1 1.4663(17) . ?
N1 C10 1.3926(18) . ?
N1 C14 1.368(2) . ?
N2 H2 0.88(2) . ?
N2 C3 1.326(2) . ?
N2 C15 1.4607(19) . ?
N3 C16 1.460(4) . ?
N3 C17 1.481(4) . ?
N3 C19 1.477(4) . ?
N3A C16A 1.465(4) . ?
N3A C17A 1.475(4) . ?
N3A C19A 1.465(4) . ?
C1 H1 1.0000 . ?
C1 C2 1.530(2) . ?
C1 C3 1.5412(18) . ?
C2 C4 1.486(2) . ?
C4 C5 1.416(15) . ?
C4 C5A 1.355(16) . ?
C4 C9 1.339(14) . ?
C4 C9A 1.469(12) . ?
C5 H5 0.9500 . ?
C5 C6 1.404(15) . ?
C5A H5A 0.9500 . ?
C5A C6A 1.394(14) . ?
C6 H6 0.9500 . ?
C6 C7 1.376(8) . ?
C6A H6A 0.9500 . ?
C6A C7A 1.373(9) . ?
C7 H7 0.9500 . ?
C7 C8 1.368(10) . ?
C7A H7A 0.9500 . ?
C7A C8A 1.377(10) . ?
C8 H8 0.9500 . ?
C8 C9 1.407(13) . ?
C8A H8A 0.9500 . ?
C8A C9A 1.352(14) . ?
C9 H9 0.9500 . ?
C9A H9A 0.9500 . ?
C10 C11 1.436(2) . ?
C11 H11 0.9500 . ?
C11 C12 1.357(2) . ?
C12 H12 0.9500 . ?
C12 C13 1.411(2) . ?
C13 H13 0.9500 . ?
C13 C14 1.349(2) . ?
C14 H14 0.9500 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 H15C 0.9900 . ?
C15 H15D 0.9900 . ?
C15 C16 1.429(3) . ?
C15 C16A 1.665(3) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16A H16C 0.9900 . ?
C16A H16D 0.9900 . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C18 1.524(4) . ?
C17A H17C 0.9900 . ?
C17A H17D 0.9900 . ?
C17A C18A 1.531(4) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C18A H18D 0.9800 . ?
C18A H18E 0.9800 . ?
C18A H18F 0.9800 . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C19 C20 1.503(5) . ?
C19A H19C 0.9900 . ?
C19A H19D 0.9900 . ?
C19A C20A 1.515(5) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C20A H20D 0.9800 . ?
C20A H20E 0.9800 . ?
C20A H20F 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
C10 N1 C1 116.76(11) . . ?
C14 N1 C1 120.59(12) . . ?
C14 N1 C10 122.43(13) . . ?
C3 N2 H2 119.0(12) . . ?
C3 N2 C15 121.67(12) . . ?
C15 N2 H2 119.3(13) . . ?
C16 N3 C17 112.6(2) . . ?
C16 N3 C19 109.5(2) . . ?
C19 N3 C17 112.2(3) . . ?
C16A N3A C17A 110.1(3) . . ?
C16A N3A C19A 113.3(3) . . ?
C19A N3A C17A 112.6(3) . . ?
N1 C1 H1 108.6 . . ?
N1 C1 C2 110.02(12) . . ?
N1 C1 C3 110.86(11) . . ?
C2 C1 H1 108.6 . . ?
C2 C1 C3 110.06(11) . . ?
C3 C1 H1 108.6 . . ?
O1 C2 C1 120.16(14) . . ?
O1 C2 C4 121.60(14) . . ?
C4 C2 C1 118.22(12) . . ?
O2 C3 N2 125.52(13) . . ?
O2 C3 C1 119.86(13) . . ?
N2 C3 C1 114.62(12) . . ?
C5 C4 C2 120.7(5) . . ?
C5A C4 C2 124.4(6) . . ?
C5A C4 C9A 124.2(7) . . ?
C9 C4 C2 126.4(4) . . ?
C9 C4 C5 112.7(7) . . ?
C9A C4 C2 110.6(4) . . ?
C4 C5 H5 118.4 . . ?
C6 C5 C4 123.3(10) . . ?
C6 C5 H5 118.4 . . ?
C4 C5A H5A 121.9 . . ?
C4 C5A C6A 116.2(10) . . ?
C6A C5A H5A 121.9 . . ?
C5 C6 H6 120.5 . . ?
C7 C6 C5 119.0(8) . . ?
C7 C6 H6 120.5 . . ?
C5A C6A H6A 119.2 . . ?
C7A C6A C5A 121.6(8) . . ?
C7A C6A H6A 119.2 . . ?
C6 C7 H7 119.9 . . ?
C8 C7 C6 120.2(7) . . ?
C8 C7 H7 119.9 . . ?
C6A C7A H7A 119.7 . . ?
C6A C7A C8A 120.5(8) . . ?
C8A C7A H7A 119.7 . . ?
C7 C8 H8 121.4 . . ?
C7 C8 C9 117.3(9) . . ?
C9 C8 H8 121.4 . . ?
C7A C8A H8A 118.8 . . ?
C9A C8A C7A 122.4(9) . . ?
C9A C8A H8A 118.8 . . ?
C4 C9 C8 127.3(7) . . ?
C4 C9 H9 116.4 . . ?
C8 C9 H9 116.4 . . ?
C4 C9A H9A 122.6 . . ?
C8A C9A C4 114.8(6) . . ?
C8A C9A H9A 122.6 . . ?
O3 C10 N1 119.31(12) . . ?
O3 C10 C11 125.42(13) . . ?
N1 C10 C11 115.27(12) . . ?
C10 C11 H11 119.3 . . ?
C12 C11 C10 121.35(14) . . ?
C12 C11 H11 119.3 . . ?
C11 C12 H12 119.7 . . ?
C11 C12 C13 120.59(15) . . ?
C13 C12 H12 119.7 . . ?
C12 C13 H13 120.7 . . ?
C14 C13 C12 118.55(16) . . ?
C14 C13 H13 120.7 . . ?
N1 C14 H14 119.2 . . ?
C13 C14 N1 121.51(15) . . ?
C13 C14 H14 119.2 . . ?
N2 C15 H15A 110.0 . . ?
N2 C15 H15B 110.0 . . ?
N2 C15 H15C 108.6 . . ?
N2 C15 H15D 108.6 . . ?
N2 C15 C16A 114.59(15) . . ?
H15A C15 H15B 108.3 . . ?
H15C C15 H15D 107.6 . . ?
C16 C15 N2 108.67(15) . . ?
C16 C15 H15A 110.0 . . ?
C16 C15 H15B 110.0 . . ?
C16A C15 H15C 108.6 . . ?
C16A C15 H15D 108.6 . . ?
N3 C16 H16A 109.1 . . ?
N3 C16 H16B 109.1 . . ?
C15 C16 N3 112.4(2) . . ?
C15 C16 H16A 109.1 . . ?
C15 C16 H16B 109.1 . . ?
H16A C16 H16B 107.9 . . ?
N3A C16A C15 114.4(2) . . ?
N3A C16A H16C 108.7 . . ?
N3A C16A H16D 108.7 . . ?
C15 C16A H16C 108.7 . . ?
C15 C16A H16D 108.7 . . ?
H16C C16A H16D 107.6 . . ?
N3 C17 H17A 108.0 . . ?
N3 C17 H17B 108.0 . . ?
N3 C17 C18 117.1(2) . . ?
H17A C17 H17B 107.3 . . ?
C18 C17 H17A 108.0 . . ?
C18 C17 H17B 108.0 . . ?
N3A C17A H17C 108.2 . . ?
N3A C17A H17D 108.2 . . ?
N3A C17A C18A 116.5(2) . . ?
H17C C17A H17D 107.3 . . ?
C18A C17A H17C 108.2 . . ?
C18A C17A H17D 108.2 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17A C18A H18D 109.5 . . ?
C17A C18A H18E 109.5 . . ?
C17A C18A H18F 109.5 . . ?
H18D C18A H18E 109.5 . . ?
H18D C18A H18F 109.5 . . ?
H18E C18A H18F 109.5 . . ?
N3 C19 H19A 108.8 . . ?
N3 C19 H19B 108.8 . . ?
N3 C19 C20 113.7(2) . . ?
H19A C19 H19B 107.7 . . ?
C20 C19 H19A 108.8 . . ?
C20 C19 H19B 108.8 . . ?
N3A C19A H19C 109.2 . . ?
N3A C19A H19D 109.2 . . ?
N3A C19A C20A 111.9(3) . . ?
H19C C19A H19D 107.9 . . ?
C20A C19A H19C 109.2 . . ?
C20A C19A H19D 109.2 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C19A C20A H20D 109.5 . . ?
C19A C20A H20E 109.5 . . ?
C19A C20A H20F 109.5 . . ?
H20D C20A H20E 109.5 . . ?
H20D C20A H20F 109.5 . . ?
H20E C20A H20F 109.5 . . ?

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
N2 H2 O3 0.88(2) 1.95(2) 2.8269(16) 171.7(18) 3_656 yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C2 C4 C5 179.6(4) . . . . ?
O1 C2 C4 C5A 161.0(4) . . . . ?
O1 C2 C4 C9 -6.1(8) . . . . ?
O1 C2 C4 C9A -9.6(6) . . . . ?
O3 C10 C11 C12 176.17(16) . . . . ?
N1 C1 C2 O1 -5.78(19) . . . . ?
N1 C1 C2 C4 172.53(11) . . . . ?
N1 C1 C3 O2 95.65(15) . . . . ?
N1 C1 C3 N2 -83.84(15) . . . . ?
N1 C10 C11 C12 -3.8(2) . . . . ?
N2 C15 C16 N3 57.6(2) . . . . ?
N2 C15 C16A N3A -51.9(3) . . . . ?
C1 N1 C10 O3 1.3(2) . . . . ?
C1 N1 C10 C11 -178.82(13) . . . . ?
C1 N1 C14 C13 -179.5(2) . . . . ?
C1 C2 C4 C5 1.4(4) . . . . ?
C1 C2 C4 C5A -17.3(4) . . . . ?
C1 C2 C4 C9 175.6(8) . . . . ?
C1 C2 C4 C9A 172.2(6) . . . . ?
C2 C1 C3 O2 -26.30(17) . . . . ?
C2 C1 C3 N2 154.21(12) . . . . ?
C2 C4 C5 C6 179.2(5) . . . . ?
C2 C4 C5A C6A -173.4(4) . . . . ?
C2 C4 C9 C8 -179.5(11) . . . . ?
C2 C4 C9A C8A 176.8(10) . . . . ?
C3 N2 C15 C16 79.85(19) . . . . ?
C3 N2 C15 C16A 139.25(17) . . . . ?
C3 C1 C2 O1 116.67(15) . . . . ?
C3 C1 C2 C4 -65.02(16) . . . . ?
C4 C5 C6 C7 -3.2(9) . . . . ?
C4 C5A C6A C7A 0.6(10) . . . . ?
C5 C4 C9 C8 -4.8(17) . . . . ?
C5 C6 C7 C8 2.4(11) . . . . ?
C5A C4 C9A C8A 6.2(16) . . . . ?
C5A C6A C7A C8A 0.6(15) . . . . ?
C6 C7 C8 C9 -2.7(16) . . . . ?
C6A C7A C8A C9A 2(2) . . . . ?
C7 C8 C9 C4 4(2) . . . . ?
C7A C8A C9A C4 -5(2) . . . . ?
C9 C4 C5 C6 4.1(10) . . . . ?
C9A C4 C5A C6A -4.2(10) . . . . ?
C10 N1 C1 C2 -87.93(15) . . . . ?
C10 N1 C1 C3 150.10(13) . . . . ?
C10 N1 C14 C13 -5.1(3) . . . . ?
C10 C11 C12 C13 -0.5(3) . . . . ?
C11 C12 C13 C14 2.2(4) . . . . ?
C12 C13 C14 N1 0.4(4) . . . . ?
C14 N1 C1 C2 86.84(19) . . . . ?
C14 N1 C1 C3 -35.1(2) . . . . ?
C14 N1 C10 O3 -173.41(17) . . . . ?
C14 N1 C10 C11 6.5(2) . . . . ?
C15 N2 C3 O2 4.1(2) . . . . ?
C15 N2 C3 C1 -176.46(12) . . . . ?
C16 N3 C17 C18 55.6(3) . . . . ?
C16 N3 C19 C20 169.5(3) . . . . ?
C16A N3A C17A C18A 74.0(3) . . . . ?
C16A N3A C19A C20A 176.9(3) . . . . ?
C17 N3 C16 C15 55.4(3) . . . . ?
C17 N3 C19 C20 -64.7(3) . . . . ?
C17A N3A C16A C15 178.7(2) . . . . ?
C17A N3A C19A C20A -57.4(3) . . . . ?
C19 N3 C16 C15 -179.1(2) . . . . ?
C19 N3 C17 C18 -68.4(3) . . . . ?
C19A N3A C16A C15 -54.3(3) . . . . ?
C19A N3A C17A C18A -53.4(4) . . . . ?

_olex2_date_sample_data_collection 2019-12-11
_olex2_date_sample_submission    2019-12-11
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.608
_oxdiff_exptl_absorpt_empirical_full_min 0.763
