# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_alex_DL-Pro_H2O
_database_code_depnum_ccdc_archive 'CCDC 2247553'
loop_
_audit_author_name
_audit_author_address
'Koen Robeyns'
;Universite catholique de Louvain
Belgium
;
_audit_update_record             
;
2023-04-17 deposited with the CCDC.	2023-04-28 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_THETM01_alex_DL-Pro_H2O     
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.550
RESPONSE: A data cut-off of 0.93A was imposed during integration beyond which the crystal diffracted poorly
;
# Added during the CSD deposition process: Monday 17 April 2023 10:26 AM
# end Validation Reply Form


_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C5 H9 N O2, H2 O'
_chemical_formula_weight         133.15

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   10.468(4)
_cell_length_b                   5.3181(19)
_cell_length_c                   12.162(5)
_cell_angle_alpha                90
_cell_angle_beta                 104.68(4)
_cell_angle_gamma                90
_cell_volume                     655.0(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    758
_cell_measurement_theta_min      3.4380
_cell_measurement_theta_max      22.4680

_exptl_crystal_description       rod
_exptl_crystal_colour            yellow-brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.350
_exptl_crystal_F_000             288
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    0.111
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.80930
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?



_diffrn_ambient_temperature      297(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Incoatec microfocus source'
_diffrn_measurement_device_type  'MAR345 image plate'
_diffrn_measurement_method       
;
'40 images, ΔΦ 5.0° '
;
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3271
_diffrn_reflns_av_unetI/netI     0.0679
_diffrn_reflns_av_R_equivalents  0.1008
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.463
_diffrn_reflns_theta_max         22.439
_diffrn_reflns_theta_full        22.439
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measured_fraction_theta_full 0.973
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_Laue_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_point_group_measured_fraction_full 0.973
_reflns_number_total             828
_reflns_number_gt                554
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       MAR
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_atom_sites_solution_primary     'dual space'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'MERCURY (Macrae et al., 2008)'
_computing_publication_material  
;
'MERCURY (Macrae et al., 2008), Platon (Spek, 2009)'
;


_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0587P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         828
_refine_ls_number_parameters     113
_refine_ls_number_restraints     60
_refine_ls_R_factor_all          0.0903
_refine_ls_R_factor_gt           0.0513
_refine_ls_wR_factor_ref         0.1395
_refine_ls_wR_factor_gt          0.1209
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.028
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.6127(3) 0.7798(5) 0.4411(2) 0.0294(8) Uani 1 1 d D U . . .
H1A H 0.547517 0.687569 0.454830 0.035 Uiso 0.877(12) 1 calc R U P A 1
H1B H 0.579929 0.928649 0.414597 0.035 Uiso 0.877(12) 1 calc R U P A 1
H1C H 0.537581 0.707661 0.445834 0.035 Uiso 0.123(12) 1 calc R U P A 2
H1D H 0.598358 0.942207 0.424920 0.035 Uiso 0.123(12) 1 calc R U P A 2
C2 C 0.7195(5) 0.8142(15) 0.5486(4) 0.043(2) Uani 0.877(12) 1 d D U P A 1
H2A H 0.728871 0.666005 0.596487 0.051 Uiso 0.877(12) 1 calc R U P A 1
H2B H 0.702284 0.959047 0.591174 0.051 Uiso 0.877(12) 1 calc R U P A 1
C3 C 0.8398(5) 0.8544(13) 0.5042(4) 0.0435(17) Uani 0.877(12) 1 d D U P A 1
H3A H 0.919994 0.816802 0.562099 0.052 Uiso 0.877(12) 1 calc R U P A 1
H3B H 0.844039 1.026332 0.478682 0.052 Uiso 0.877(12) 1 calc R U P A 1
C4 C 0.8207(5) 0.6708(13) 0.4050(5) 0.0417(19) Uani 0.877(12) 1 d D U P A 1
H4A H 0.857818 0.507713 0.431081 0.050 Uiso 0.877(12) 1 calc R U P A 1
H4B H 0.863127 0.733212 0.348157 0.050 Uiso 0.877(12) 1 calc R U P A 1
C2B C 0.720(2) 0.743(14) 0.5481(16) 0.045(8) Uani 0.123(12) 1 d D U P A 2
H2C H 0.698112 0.604030 0.591798 0.054 Uiso 0.123(12) 1 calc R U P A 2
H2D H 0.730291 0.893740 0.594588 0.054 Uiso 0.123(12) 1 calc R U P A 2
C3B C 0.844(3) 0.688(10) 0.512(3) 0.046(7) Uani 0.123(12) 1 d D U P A 2
H3C H 0.867985 0.512088 0.523981 0.056 Uiso 0.123(12) 1 calc R U P A 2
H3D H 0.916828 0.789845 0.555264 0.056 Uiso 0.123(12) 1 calc R U P A 2
C4B C 0.812(2) 0.755(9) 0.386(2) 0.034(8) Uani 0.123(12) 1 d D U P A 2
H4C H 0.868608 0.668317 0.346827 0.040 Uiso 0.123(12) 1 calc R U P A 2
H4D H 0.814848 0.934668 0.373803 0.040 Uiso 0.123(12) 1 calc R U P A 2
C5 C 0.6701(4) 0.6511(6) 0.3555(3) 0.0295(10) Uani 1 1 d D U . . .
H5 H 0.643807 0.738480 0.282247 0.035 Uiso 0.877(12) 1 calc R U P A 1
H5B H 0.627283 0.730692 0.282790 0.035 Uiso 0.123(12) 1 calc R U P A 2
C6 C 0.6260(4) 0.3744(7) 0.3416(3) 0.0311(10) Uani 1 1 d . . . . .
O7 O 0.5606(3) 0.2898(4) 0.4082(2) 0.0374(8) Uani 1 1 d . . . . .
O8 O 0.6619(3) 0.2503(4) 0.2666(2) 0.0434(9) Uani 1 1 d . . . . .
O11 O 0.9203(4) 0.1881(6) 0.2285(3) 0.0634(10) Uani 1 1 d G . . . .
H11A H 0.953602 0.328506 0.232777 0.095 Uiso 1 1 d G U . . .
H11B H 0.845420 0.212686 0.235536 0.095 Uiso 1 1 d G U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C5 1.494(4) . ?
N1 C2B 1.499(11) . ?
N1 C2 1.500(5) . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 H1C 0.8900 . ?
N1 H1D 0.8900 . ?
C2 C3 1.507(7) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.525(7) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.542(6) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C2B C3B 1.505(12) . ?
C2B H2C 0.9700 . ?
C2B H2D 0.9700 . ?
C3B C4B 1.524(12) . ?
C3B H3C 0.9700 . ?
C3B H3D 0.9700 . ?
C4B C5 1.539(11) . ?
C4B H4C 0.9700 . ?
C4B H4D 0.9700 . ?
C5 C6 1.539(5) . ?
C5 H5 0.9800 . ?
C5 H5B 0.9800 . ?
C6 O8 1.258(4) . ?
C6 O7 1.268(4) . ?
O11 H11A 0.8200 . ?
O11 H11B 0.8200 . ?

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 N1 C2B 101.7(15) . . ?
C5 N1 C2 108.7(3) . . ?
C5 N1 H1A 109.9 . . ?
C2 N1 H1A 109.9 . . ?
C5 N1 H1B 109.9 . . ?
C2 N1 H1B 109.9 . . ?
H1A N1 H1B 108.3 . . ?
C5 N1 H1C 111.4 . . ?
C2B N1 H1C 111.4 . . ?
C5 N1 H1D 111.4 . . ?
C2B N1 H1D 111.4 . . ?
H1C N1 H1D 109.3 . . ?
N1 C2 C3 102.2(3) . . ?
N1 C2 H2A 111.3 . . ?
C3 C2 H2A 111.3 . . ?
N1 C2 H2B 111.3 . . ?
C3 C2 H2B 111.3 . . ?
H2A C2 H2B 109.2 . . ?
C2 C3 C4 103.8(4) . . ?
C2 C3 H3A 111.0 . . ?
C4 C3 H3A 111.0 . . ?
C2 C3 H3B 111.0 . . ?
C4 C3 H3B 111.0 . . ?
H3A C3 H3B 109.0 . . ?
C3 C4 C5 105.6(4) . . ?
C3 C4 H4A 110.6 . . ?
C5 C4 H4A 110.6 . . ?
C3 C4 H4B 110.6 . . ?
C5 C4 H4B 110.6 . . ?
H4A C4 H4B 108.8 . . ?
N1 C2B C3B 106.6(15) . . ?
N1 C2B H2C 110.4 . . ?
C3B C2B H2C 110.4 . . ?
N1 C2B H2D 110.4 . . ?
C3B C2B H2D 110.4 . . ?
H2C C2B H2D 108.6 . . ?
C2B C3B C4B 104.9(14) . . ?
C2B C3B H3C 110.8 . . ?
C4B C3B H3C 110.8 . . ?
C2B C3B H3D 110.8 . . ?
C4B C3B H3D 110.8 . . ?
H3C C3B H3D 108.8 . . ?
C3B C4B C5 97(2) . . ?
C3B C4B H4C 112.4 . . ?
C5 C4B H4C 112.4 . . ?
C3B C4B H4D 112.4 . . ?
C5 C4B H4D 112.4 . . ?
H4C C4B H4D 110.0 . . ?
N1 C5 C6 110.6(3) . . ?
N1 C5 C4B 101.4(16) . . ?
C6 C5 C4B 127.9(19) . . ?
N1 C5 C4 104.4(3) . . ?
C6 C5 C4 110.9(4) . . ?
N1 C5 H5 110.3 . . ?
C6 C5 H5 110.3 . . ?
C4 C5 H5 110.3 . . ?
N1 C5 H5B 105.0 . . ?
C6 C5 H5B 105.0 . . ?
C4B C5 H5B 105.0 . . ?
O8 C6 O7 125.8(3) . . ?
O8 C6 C5 116.4(3) . . ?
O7 C6 C5 117.7(3) . . ?
H11A O11 H11B 104.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C2 C3 33.4(5) . . . . ?
N1 C2 C3 C4 -39.1(6) . . . . ?
C2 C3 C4 C5 31.4(7) . . . . ?
C5 N1 C2B C3B 20(4) . . . . ?
N1 C2B C3B C4B 13(5) . . . . ?
C2B C3B C4B C5 -39(5) . . . . ?
C2B N1 C5 C6 92(3) . . . . ?
C2 N1 C5 C6 105.4(4) . . . . ?
C2B N1 C5 C4B -46(3) . . . . ?
C2 N1 C5 C4 -13.9(5) . . . . ?
C3B C4B C5 N1 53(3) . . . . ?
C3B C4B C5 C6 -75(3) . . . . ?
C3 C4 C5 N1 -10.9(7) . . . . ?
C3 C4 C5 C6 -130.0(5) . . . . ?
N1 C5 C6 O8 175.9(3) . . . . ?
C4B C5 C6 O8 -60.0(15) . . . . ?
C4 C5 C6 O8 -68.8(5) . . . . ?
N1 C5 C6 O7 -6.0(5) . . . . ?
C4B C5 C6 O7 118.1(15) . . . . ?
C4 C5 C6 O7 109.3(4) . . . . ?

_refine_diff_density_max         0.186
_refine_diff_density_min         -0.167
_refine_diff_density_rms         0.047

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

data_alex_fl184A
_database_code_depnum_ccdc_archive 'CCDC 2247554'
loop_
_audit_author_name
_audit_author_address
'Koen Robeyns'
;Universite catholique de Louvain
Belgium
;
_audit_update_record             
;
2023-03-09 deposited with the CCDC.	2023-04-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H7 Cl O3, C8 H14 N2 O2'
_chemical_formula_sum            'C16 H21 Cl N2 O5'
_chemical_formula_weight         356.80

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

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

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

_cell_length_a                   11.8318(7)
_cell_length_b                   5.8252(3)
_cell_length_c                   13.9008(8)
_cell_angle_alpha                90
_cell_angle_beta                 113.879(7)
_cell_angle_gamma                90
_cell_volume                     876.06(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    5282
_cell_measurement_theta_min      2.9080
_cell_measurement_theta_max      25.2750

_exptl_crystal_description       rod
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_F_000             376
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.02
_exptl_absorpt_coefficient_mu    0.246
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.60286
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?


_diffrn_ambient_temperature      297(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Incoatec microfocus source'
_diffrn_measurement_device_type  'MAR345 image plate'
_diffrn_measurement_method       
;
'180 images, ΔΦ 2.0° '
;
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11897
_diffrn_reflns_av_unetI/netI     0.0382
_diffrn_reflns_av_R_equivalents  0.0451
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.925
_diffrn_reflns_theta_max         25.685
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3314
_reflns_number_gt                2886
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.810
_reflns_Friedel_fraction_max     0.998
_reflns_Friedel_fraction_full    0.998

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

_computing_data_collection       MAR
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_atom_sites_solution_primary     'dual space'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'MERCURY (Macrae et al., 2008)'
_computing_publication_material  
;
'MERCURY (Macrae et al., 2008), Platon (Spek, 2009)'
;







_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0837P)²+0.4971P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1100 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(4)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3314
_refine_ls_number_parameters     219
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0659
_refine_ls_R_factor_gt           0.0581
_refine_ls_wR_factor_ref         0.1620
_refine_ls_wR_factor_gt          0.1563
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_restrained_S_all      1.068
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl -0.03037(19) 0.6470(3) 0.77615(13) 0.0785(6) Uani 1 1 d . . . . .
C2 C -0.0500(5) 0.8697(10) 0.6875(4) 0.0482(12) Uani 1 1 d . . . . .
C3 C -0.1565(6) 0.8761(14) 0.5947(5) 0.0665(18) Uani 1 1 d . . . . .
H3 H -0.217535 0.765117 0.581160 0.080 Uiso 1 1 calc R U . . .
C4 C -0.1699(6) 1.0453(17) 0.5247(5) 0.078(2) Uani 1 1 d . . . . .
H4 H -0.241499 1.050357 0.463070 0.094 Uiso 1 1 calc R U . . .
C5 C -0.0809(8) 1.2105(14) 0.5420(5) 0.080(2) Uani 1 1 d . . . . .
H5 H -0.091442 1.326345 0.493028 0.096 Uiso 1 1 calc R U . . .
C6 C 0.0238(6) 1.1996(11) 0.6333(5) 0.0637(16) Uani 1 1 d . . . . .
H6 H 0.084746 1.310277 0.645763 0.076 Uiso 1 1 calc R U . . .
C7 C 0.0421(4) 1.0287(9) 0.7083(4) 0.0424(11) Uani 1 1 d . . . . .
C8 C 0.1622(5) 1.0295(11) 0.8077(4) 0.0518(13) Uani 1 1 d . . . . .
H8 H 0.211048 1.158240 0.799657 0.062 Uiso 1 1 calc R U . . .
O9 O 0.1412(4) 1.0767(9) 0.8943(3) 0.0712(13) Uani 1 1 d . . . . .
H9 H 0.200751 1.145591 0.937191 0.107 Uiso 1 1 calc R U . . .
C10 C 0.2401(4) 0.8159(10) 0.8183(3) 0.0434(11) Uani 1 1 d . . . . .
O11 O 0.2358(4) 0.7407(8) 0.7275(3) 0.0605(11) Uani 1 1 d . . . . .
H11 H 0.279070 0.625874 0.737323 0.091 Uiso 1 1 calc R U . . .
O12 O 0.3085(4) 0.7409(8) 0.9011(3) 0.0641(12) Uani 1 1 d . . . . .
O21 O 0.6646(4) -0.2124(7) 0.9384(3) 0.0588(10) Uani 1 1 d . . . . .
C22 C 0.7089(4) -0.0571(9) 0.9063(4) 0.0396(11) Uani 1 1 d . . . . .
C23 C 0.8442(5) 0.0026(12) 0.9439(5) 0.0588(16) Uani 1 1 d . . . . .
H23A H 0.881089 0.022962 1.019682 0.071 Uiso 1 1 calc R U . . .
H23B H 0.888494 -0.117622 0.925441 0.071 Uiso 1 1 calc R U . . .
C24 C 0.8480(5) 0.2223(12) 0.8894(5) 0.0643(17) Uani 1 1 d . . . . .
H24A H 0.907636 0.211225 0.858094 0.077 Uiso 1 1 calc R U . . .
H24B H 0.871531 0.348650 0.939091 0.077 Uiso 1 1 calc R U . . .
C25 C 0.7197(5) 0.2612(11) 0.8052(5) 0.0543(14) Uani 1 1 d . . . . .
H25A H 0.691331 0.415910 0.808678 0.065 Uiso 1 1 calc R U . . .
H25B H 0.717840 0.235228 0.735594 0.065 Uiso 1 1 calc R U . . .
N26 N 0.6444(3) 0.0911(7) 0.8302(3) 0.0373(9) Uani 1 1 d . . . . .
C27 C 0.5111(4) 0.0793(8) 0.7730(3) 0.0367(10) Uani 1 1 d . . . . .
H27 H 0.483122 -0.055673 0.799363 0.044 Uiso 1 1 calc R U . . .
C28 C 0.4716(5) 0.0436(12) 0.6548(4) 0.0545(14) Uani 1 1 d . . . . .
H28A H 0.382028 0.038266 0.620870 0.065 Uiso 1 1 calc R U . . .
H28B H 0.498893 0.173710 0.626236 0.065 Uiso 1 1 calc R U . . .
C29 C 0.5235(7) -0.1748(14) 0.6291(6) 0.079(2) Uani 1 1 d . . . . .
H29A H 0.496251 -0.188243 0.554236 0.118 Uiso 1 1 calc R U . . .
H29B H 0.494848 -0.304841 0.655388 0.118 Uiso 1 1 calc R U . . .
H29C H 0.612114 -0.169683 0.661434 0.118 Uiso 1 1 calc R U . . .
C30 C 0.4492(4) 0.2875(9) 0.7974(3) 0.0396(10) Uani 1 1 d . . . . .
N32 N 0.4891(4) 0.3534(10) 0.8948(3) 0.0614(14) Uani 1 1 d . . . . .
H32A H 0.453086 0.464499 0.911964 0.074 Uiso 1 1 calc R U . . .
H32B H 0.551546 0.285983 0.942143 0.074 Uiso 1 1 calc R U . . .
O31 O 0.3604(4) 0.3766(8) 0.7259(3) 0.0612(12) Uani 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
Cl1 C2 1.739(6) . ?
C2 C7 1.369(8) . ?
C2 C3 1.391(8) . ?
C3 C4 1.348(11) . ?
C3 H3 0.9300 . ?
C4 C5 1.374(12) . ?
C4 H4 0.9300 . ?
C5 C6 1.370(9) . ?
C5 H5 0.9300 . ?
C6 C7 1.393(8) . ?
C6 H6 0.9300 . ?
C7 C8 1.529(7) . ?
C8 O9 1.353(7) . ?
C8 C10 1.520(8) . ?
C8 H8 0.9800 . ?
O9 H9 0.8200 . ?
C10 O12 1.191(6) . ?
C10 O11 1.316(6) . ?
O11 H11 0.8200 . ?
O21 C22 1.217(7) . ?
C22 N26 1.339(6) . ?
C22 C23 1.510(7) . ?
C23 C24 1.497(10) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C24 C25 1.512(8) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C25 N26 1.466(6) . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
N26 C27 1.453(5) . ?
C27 C30 1.524(7) . ?
C27 C28 1.530(7) . ?
C27 H27 0.9800 . ?
C28 C29 1.517(10) . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
C30 O31 1.231(6) . ?
C30 N32 1.298(7) . ?
N32 H32A 0.8600 . ?
N32 H32B 0.8600 . ?

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
C7 C2 C3 121.5(6) . . ?
C7 C2 Cl1 119.2(4) . . ?
C3 C2 Cl1 119.2(5) . . ?
C4 C3 C2 119.1(6) . . ?
C4 C3 H3 120.4 . . ?
C2 C3 H3 120.4 . . ?
C3 C4 C5 121.9(6) . . ?
C3 C4 H4 119.1 . . ?
C5 C4 H4 119.1 . . ?
C6 C5 C4 118.1(7) . . ?
C6 C5 H5 121.0 . . ?
C4 C5 H5 121.0 . . ?
C5 C6 C7 122.3(7) . . ?
C5 C6 H6 118.8 . . ?
C7 C6 H6 118.8 . . ?
C2 C7 C6 117.1(5) . . ?
C2 C7 C8 124.2(5) . . ?
C6 C7 C8 118.7(5) . . ?
O9 C8 C10 113.8(5) . . ?
O9 C8 C7 111.5(4) . . ?
C10 C8 C7 113.0(4) . . ?
O9 C8 H8 106.0 . . ?
C10 C8 H8 106.0 . . ?
C7 C8 H8 106.0 . . ?
C8 O9 H9 109.5 . . ?
O12 C10 O11 123.5(5) . . ?
O12 C10 C8 122.9(5) . . ?
O11 C10 C8 113.1(4) . . ?
C10 O11 H11 109.5 . . ?
O21 C22 N26 125.3(4) . . ?
O21 C22 C23 126.7(5) . . ?
N26 C22 C23 108.1(5) . . ?
C24 C23 C22 105.4(5) . . ?
C24 C23 H23A 110.7 . . ?
C22 C23 H23A 110.7 . . ?
C24 C23 H23B 110.7 . . ?
C22 C23 H23B 110.7 . . ?
H23A C23 H23B 108.8 . . ?
C23 C24 C25 107.1(5) . . ?
C23 C24 H24A 110.3 . . ?
C25 C24 H24A 110.3 . . ?
C23 C24 H24B 110.3 . . ?
C25 C24 H24B 110.3 . . ?
H24A C24 H24B 108.5 . . ?
N26 C25 C24 103.3(4) . . ?
N26 C25 H25A 111.1 . . ?
C24 C25 H25A 111.1 . . ?
N26 C25 H25B 111.1 . . ?
C24 C25 H25B 111.1 . . ?
H25A C25 H25B 109.1 . . ?
C22 N26 C27 123.1(4) . . ?
C22 N26 C25 114.7(4) . . ?
C27 N26 C25 122.1(4) . . ?
N26 C27 C30 110.7(4) . . ?
N26 C27 C28 112.7(4) . . ?
C30 C27 C28 112.4(4) . . ?
N26 C27 H27 106.8 . . ?
C30 C27 H27 106.8 . . ?
C28 C27 H27 106.8 . . ?
C29 C28 C27 113.0(5) . . ?
C29 C28 H28A 109.0 . . ?
C27 C28 H28A 109.0 . . ?
C29 C28 H28B 109.0 . . ?
C27 C28 H28B 109.0 . . ?
H28A C28 H28B 107.8 . . ?
C28 C29 H29A 109.5 . . ?
C28 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C28 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
O31 C30 N32 123.2(5) . . ?
O31 C30 C27 119.1(4) . . ?
N32 C30 C27 117.6(4) . . ?
C30 N32 H32A 120.0 . . ?
C30 N32 H32B 120.0 . . ?
H32A N32 H32B 120.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 C2 C3 C4 -1.2(9) . . . . ?
Cl1 C2 C3 C4 -178.2(5) . . . . ?
C2 C3 C4 C5 0.6(11) . . . . ?
C3 C4 C5 C6 0.0(11) . . . . ?
C4 C5 C6 C7 -0.2(10) . . . . ?
C3 C2 C7 C6 1.1(8) . . . . ?
Cl1 C2 C7 C6 178.0(4) . . . . ?
C3 C2 C7 C8 -179.0(5) . . . . ?
Cl1 C2 C7 C8 -2.1(7) . . . . ?
C5 C6 C7 C2 -0.4(9) . . . . ?
C5 C6 C7 C8 179.7(6) . . . . ?
C2 C7 C8 O9 -67.2(7) . . . . ?
C6 C7 C8 O9 112.7(6) . . . . ?
C2 C7 C8 C10 62.4(7) . . . . ?
C6 C7 C8 C10 -117.7(6) . . . . ?
O9 C8 C10 O12 -23.1(8) . . . . ?
C7 C8 C10 O12 -151.6(5) . . . . ?
O9 C8 C10 O11 164.8(5) . . . . ?
C7 C8 C10 O11 36.4(7) . . . . ?
O21 C22 C23 C24 -173.2(5) . . . . ?
N26 C22 C23 C24 7.0(6) . . . . ?
C22 C23 C24 C25 -11.5(7) . . . . ?
C23 C24 C25 N26 11.4(7) . . . . ?
O21 C22 N26 C27 -2.1(8) . . . . ?
C23 C22 N26 C27 177.7(5) . . . . ?
O21 C22 N26 C25 -179.4(5) . . . . ?
C23 C22 N26 C25 0.4(6) . . . . ?
C24 C25 N26 C22 -7.5(6) . . . . ?
C24 C25 N26 C27 175.2(5) . . . . ?
C22 N26 C27 C30 113.7(5) . . . . ?
C25 N26 C27 C30 -69.2(6) . . . . ?
C22 N26 C27 C28 -119.4(5) . . . . ?
C25 N26 C27 C28 57.7(6) . . . . ?
N26 C27 C28 C29 59.1(7) . . . . ?
C30 C27 C28 C29 -174.8(5) . . . . ?
N26 C27 C30 O31 140.7(5) . . . . ?
C28 C27 C30 O31 13.6(7) . . . . ?
N26 C27 C30 N32 -43.2(6) . . . . ?
C28 C27 C30 N32 -170.3(5) . . . . ?

_refine_diff_density_max         0.613
_refine_diff_density_min         -0.341
_refine_diff_density_rms         0.056

####################################################################### 
# 
# 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_alex_fl173
_database_code_depnum_ccdc_archive 'CCDC 2247555'
loop_
_audit_author_name
_audit_author_address
'Koen Robeyns'
;Universite catholique de Louvain
Belgium
;
_audit_update_record             
;
2023-03-09 deposited with the CCDC.	2023-04-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H10 O3, C5 H9 N O2'
_chemical_formula_sum            'C14 H19 N O5'
_chemical_formula_weight         281.30

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   11.2568(8)
_cell_length_b                   5.7371(3)
_cell_length_c                   22.5561(18)
_cell_angle_alpha                90
_cell_angle_beta                 103.029(8)
_cell_angle_gamma                90
_cell_volume                     1419.21(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    1270
_cell_measurement_theta_min      3.6470
_cell_measurement_theta_max      22.3590

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_F_000             600
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.02
_exptl_absorpt_coefficient_mu    0.100
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.95435
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?




_diffrn_ambient_temperature      297(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Incoatec microfocus source'
_diffrn_measurement_device_type  'MAR345 image plate'
_diffrn_measurement_method       
;
'108 images, ΔΦ 1.2° '
;
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6149
_diffrn_reflns_av_unetI/netI     0.0440
_diffrn_reflns_av_R_equivalents  0.0473
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         3.670
_diffrn_reflns_theta_max         23.262
_diffrn_reflns_theta_full        23.262
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             2030
_reflns_number_gt                1327
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       MAR
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_atom_sites_solution_primary     dual
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'MERCURY (Macrae et al., 2008)'
_computing_publication_material  
;
'MERCURY (Macrae et al., 2008), Platon (Spek, 2009)'
;




_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0550P)²+2.9000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2030
_refine_ls_number_parameters     218
_refine_ls_number_restraints     27
_refine_ls_R_factor_all          0.1258
_refine_ls_R_factor_gt           0.0809
_refine_ls_wR_factor_ref         0.1990
_refine_ls_wR_factor_gt          0.1781
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_restrained_S_all      1.088
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.4007(4) 0.8156(7) 0.41078(18) 0.0547(11) Uani 1 1 d . . . . .
H1A H 0.477759 0.771430 0.414272 0.066 Uiso 1 1 calc R U . . .
H1AB H 0.400346 0.943210 0.433165 0.066 Uiso 1 1 calc R U . . .
C2 C 0.3433(6) 0.8676(11) 0.3453(2) 0.0778(18) Uani 1 1 d . . . . .
H2A H 0.302441 1.017510 0.341379 0.093 Uiso 1 1 calc R U . . .
H2AB H 0.404097 0.868378 0.320933 0.093 Uiso 1 1 calc R U . . .
C3 C 0.2552(6) 0.6772(12) 0.3266(3) 0.092(2) Uani 1 1 d . . . . .
H3A H 0.293800 0.544707 0.311951 0.110 Uiso 1 1 calc R U . . .
H3AB H 0.187313 0.728510 0.294721 0.110 Uiso 1 1 calc R U . . .
C4 C 0.2132(5) 0.6152(11) 0.3827(3) 0.088(2) Uani 1 1 d . . . . .
H4A H 0.178846 0.459451 0.379817 0.106 Uiso 1 1 calc R U . . .
H4AB H 0.153029 0.725398 0.390259 0.106 Uiso 1 1 calc R U . . .
C5 C 0.3321(4) 0.6288(8) 0.4328(2) 0.0524(13) Uani 1 1 d . . . . .
H5 H 0.315117 0.668728 0.472305 0.063 Uiso 1 1 calc R U . . .
C6 C 0.4048(4) 0.3968(9) 0.4363(2) 0.0488(12) Uani 1 1 d . . . . .
O7 O 0.4895(4) 0.3904(6) 0.41033(19) 0.0775(12) Uani 1 1 d . . . . .
O8 O 0.3688(4) 0.2350(6) 0.46448(17) 0.0712(11) Uani 1 1 d . . . . .
C11 C 0.8524(14) -0.2519(16) 0.3140(5) 0.0570(18) Uani 0.836(5) 1 d D . P A 1
H11 H 0.807965 -0.374380 0.325204 0.068 Uiso 0.836(5) 1 calc R U P A 1
C12 C 0.8797(13) -0.252(2) 0.2571(5) 0.066(3) Uani 0.836(5) 1 d D . P A 1
H12 H 0.854333 -0.375269 0.230552 0.079 Uiso 0.836(5) 1 calc R U P A 1
C13 C 0.9436(7) -0.072(2) 0.2396(3) 0.068(3) Uani 0.836(5) 1 d D . P A 1
H13 H 0.959799 -0.071162 0.200938 0.082 Uiso 0.836(5) 1 calc R U P A 1
C14 C 0.9837(12) 0.1070(17) 0.2797(4) 0.073(2) Uani 0.836(5) 1 d D . P A 1
H14 H 1.028733 0.227891 0.268111 0.088 Uiso 0.836(5) 1 calc R U P A 1
C15 C 0.9582(7) 0.1102(13) 0.3367(3) 0.0575(17) Uani 0.836(5) 1 d D . P A 1
H15 H 0.985963 0.232444 0.363287 0.069 Uiso 0.836(5) 1 calc R U P A 1
C16 C 0.8910(6) -0.0696(12) 0.3543(3) 0.0430(16) Uani 0.836(5) 1 d D . P A 1
C17 C 0.8588(5) -0.0540(11) 0.4164(2) 0.0476(15) Uani 0.836(5) 1 d D . P A 1
H17 H 0.905014 0.075896 0.438646 0.057 Uiso 0.836(5) 1 calc R U P A 1
C18 C 0.7254(6) 0.0034(17) 0.4065(3) 0.0488(16) Uani 0.836(5) 1 d D . P A 1
O19 O 0.6423(4) -0.1306(10) 0.3890(2) 0.0752(14) Uani 0.836(5) 1 d D . P A 1
O20 O 0.7059(4) 0.2223(8) 0.4192(2) 0.0746(15) Uani 0.836(5) 1 d D . P A 1
H20 H 0.634222 0.239067 0.420572 0.112 Uiso 0.836(5) 1 calc R U P A 1
C21 C 0.8905(11) -0.270(3) 0.4543(4) 0.0690(19) Uani 0.836(5) 1 d D . P A 1
H21A H 0.840873 -0.398579 0.434455 0.083 Uiso 0.836(5) 1 calc R U P A 1
H21B H 0.975241 -0.309608 0.456487 0.083 Uiso 0.836(5) 1 calc R U P A 1
O22 O 0.8725(10) -0.2452(16) 0.5140(3) 0.085(3) Uani 0.836(5) 1 d D . P A 1
H22 H 0.801410 -0.275321 0.514231 0.127 Uiso 0.836(5) 1 calc R U P A 1
C11B C 0.853(8) -0.303(9) 0.303(2) 0.0570(18) Uani 0.164(5) 1 d D . P A 2
H11B H 0.816973 -0.447218 0.305858 0.068 Uiso 0.164(5) 1 calc R U P A 2
C12B C 0.906(9) -0.256(12) 0.255(3) 0.066(3) Uani 0.164(5) 1 d D . P A 2
H12B H 0.896550 -0.359474 0.222586 0.079 Uiso 0.164(5) 1 calc R U P A 2
C13B C 0.974(5) -0.058(11) 0.2548(19) 0.068(3) Uani 0.164(5) 1 d D . P A 2
H13B H 1.021980 -0.038852 0.226678 0.082 Uiso 0.164(5) 1 calc R U P A 2
C14B C 0.969(7) 0.112(9) 0.297(3) 0.073(2) Uani 0.164(5) 1 d D . P A 2
H14B H 0.998055 0.260862 0.292316 0.088 Uiso 0.164(5) 1 calc R U P A 2
C15B C 0.921(5) 0.064(7) 0.347(2) 0.0575(17) Uani 0.164(5) 1 d D . P A 2
H15B H 0.935848 0.165144 0.380514 0.069 Uiso 0.164(5) 1 calc R U P A 2
C16B C 0.852(3) -0.135(6) 0.3478(12) 0.0430(16) Uani 0.164(5) 1 d D . P A 2
C17B C 0.807(2) -0.193(4) 0.4052(10) 0.0476(15) Uani 0.164(5) 1 d D . P A 2
H17B H 0.747618 -0.320674 0.394783 0.057 Uiso 0.164(5) 1 calc R U P A 2
C18B C 0.739(2) 0.013(7) 0.4222(15) 0.0488(16) Uani 0.164(5) 1 d D . P A 2
O19B O 0.7810(19) 0.154(4) 0.4612(11) 0.0752(14) Uani 0.164(5) 1 d D . P A 2
O20B O 0.6240(18) 0.023(5) 0.3924(11) 0.0746(15) Uani 0.164(5) 1 d D . P A 2
H20B H 0.588181 0.122289 0.407830 0.112 Uiso 0.164(5) 1 calc R U P A 2
C21B C 0.906(5) -0.276(14) 0.4572(17) 0.0690(19) Uani 0.164(5) 1 d D . P A 2
H21C H 0.941533 -0.416406 0.445052 0.083 Uiso 0.164(5) 1 calc R U P A 2
H21D H 0.969078 -0.157817 0.466087 0.083 Uiso 0.164(5) 1 calc R U P A 2
O22B O 0.864(6) -0.322(12) 0.5106(15) 0.085(3) Uani 0.164(5) 1 d D . P A 2
H22B H 0.793262 -0.275914 0.506059 0.127 Uiso 0.164(5) 1 calc R U P A 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C5 1.470(6) . ?
N1 C2 1.502(6) . ?
N1 H1A 0.8900 . ?
N1 H1AB 0.8900 . ?
C2 C3 1.472(8) . ?
C2 H2A 0.9700 . ?
C2 H2AB 0.9700 . ?
C3 C4 1.489(9) . ?
C3 H3A 0.9700 . ?
C3 H3AB 0.9700 . ?
C4 C5 1.547(7) . ?
C4 H4A 0.9700 . ?
C4 H4AB 0.9700 . ?
C5 C6 1.555(7) . ?
C5 H5 0.9800 . ?
C6 O7 1.227(6) . ?
C6 O8 1.243(6) . ?
C11 C12 1.386(9) . ?
C11 C16 1.390(9) . ?
C11 H11 0.9300 . ?
C12 C13 1.363(9) . ?
C12 H12 0.9300 . ?
C13 C14 1.377(10) . ?
C13 H13 0.9300 . ?
C14 C15 1.380(9) . ?
C14 H14 0.9300 . ?
C15 C16 1.389(9) . ?
C15 H15 0.9300 . ?
C16 C17 1.527(7) . ?
C17 C18 1.504(8) . ?
C17 C21 1.504(12) . ?
C17 H17 0.9800 . ?
C18 O19 1.207(10) . ?
C18 O20 1.318(9) . ?
O20 H20 0.8200 . ?
C21 O22 1.415(8) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
O22 H22 0.8200 . ?
C11B C12B 1.385(12) . ?
C11B C16B 1.392(13) . ?
C11B H11B 0.9300 . ?
C12B C13B 1.364(13) . ?
C12B H12B 0.9300 . ?
C13B C14B 1.379(13) . ?
C13B H13B 0.9300 . ?
C14B C15B 1.381(12) . ?
C14B H14B 0.9300 . ?
C15B C16B 1.391(13) . ?
C15B H15B 0.9300 . ?
C16B C17B 1.528(11) . ?
C17B C21B 1.502(17) . ?
C17B C18B 1.503(12) . ?
C17B H17B 0.9800 . ?
C18B O19B 1.210(14) . ?
C18B O20B 1.318(13) . ?
O20B H20B 0.8200 . ?
C21B O22B 1.414(12) . ?
C21B H21C 0.9700 . ?
C21B H21D 0.9700 . ?
O22B H22B 0.8200 . ?

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 N1 C2 109.5(4) . . ?
C5 N1 H1A 109.8 . . ?
C2 N1 H1A 109.8 . . ?
C5 N1 H1AB 109.8 . . ?
C2 N1 H1AB 109.8 . . ?
H1A N1 H1AB 108.2 . . ?
C3 C2 N1 104.3(5) . . ?
C3 C2 H2A 110.9 . . ?
N1 C2 H2A 110.9 . . ?
C3 C2 H2AB 110.9 . . ?
N1 C2 H2AB 110.9 . . ?
H2A C2 H2AB 108.9 . . ?
C2 C3 C4 104.8(5) . . ?
C2 C3 H3A 110.8 . . ?
C4 C3 H3A 110.8 . . ?
C2 C3 H3AB 110.8 . . ?
C4 C3 H3AB 110.8 . . ?
H3A C3 H3AB 108.9 . . ?
C3 C4 C5 102.7(4) . . ?
C3 C4 H4A 111.2 . . ?
C5 C4 H4A 111.2 . . ?
C3 C4 H4AB 111.2 . . ?
C5 C4 H4AB 111.2 . . ?
H4A C4 H4AB 109.1 . . ?
N1 C5 C4 102.9(4) . . ?
N1 C5 C6 109.3(4) . . ?
C4 C5 C6 110.6(4) . . ?
N1 C5 H5 111.2 . . ?
C4 C5 H5 111.2 . . ?
C6 C5 H5 111.2 . . ?
O7 C6 O8 126.8(5) . . ?
O7 C6 C5 117.3(5) . . ?
O8 C6 C5 115.9(4) . . ?
C12 C11 C16 120.2(6) . . ?
C12 C11 H11 119.9 . . ?
C16 C11 H11 119.9 . . ?
C13 C12 C11 120.7(6) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C12 C13 C14 119.4(6) . . ?
C12 C13 H13 120.3 . . ?
C14 C13 H13 120.3 . . ?
C13 C14 C15 121.0(6) . . ?
C13 C14 H14 119.5 . . ?
C15 C14 H14 119.5 . . ?
C14 C15 C16 119.8(6) . . ?
C14 C15 H15 120.1 . . ?
C16 C15 H15 120.1 . . ?
C15 C16 C11 118.9(5) . . ?
C15 C16 C17 118.4(6) . . ?
C11 C16 C17 122.7(6) . . ?
C18 C17 C21 111.5(7) . . ?
C18 C17 C16 108.2(4) . . ?
C21 C17 C16 113.5(5) . . ?
C18 C17 H17 107.8 . . ?
C21 C17 H17 107.8 . . ?
C16 C17 H17 107.8 . . ?
O19 C18 O20 121.6(6) . . ?
O19 C18 C17 125.7(7) . . ?
O20 C18 C17 112.7(8) . . ?
C18 O20 H20 109.5 . . ?
O22 C21 C17 113.0(10) . . ?
O22 C21 H21A 109.0 . . ?
C17 C21 H21A 109.0 . . ?
O22 C21 H21B 109.0 . . ?
C17 C21 H21B 109.0 . . ?
H21A C21 H21B 107.8 . . ?
C21 O22 H22 109.5 . . ?
C12B C11B C16B 120.7(14) . . ?
C12B C11B H11B 119.6 . . ?
C16B C11B H11B 119.6 . . ?
C13B C12B C11B 120.3(14) . . ?
C13B C12B H12B 119.8 . . ?
C11B C12B H12B 119.8 . . ?
C12B C13B C14B 118.5(15) . . ?
C12B C13B H13B 120.7 . . ?
C14B C13B H13B 120.7 . . ?
C13B C14B C15B 120.7(16) . . ?
C13B C14B H14B 119.6 . . ?
C15B C14B H14B 119.6 . . ?
C14B C15B C16B 119.6(14) . . ?
C14B C15B H15B 120.2 . . ?
C16B C15B H15B 120.2 . . ?
C15B C16B C11B 117.7(14) . . ?
C15B C16B C17B 118.7(16) . . ?
C11B C16B C17B 121.4(16) . . ?
C21B C17B C18B 112.2(18) . . ?
C21B C17B C16B 113.6(15) . . ?
C18B C17B C16B 109.1(14) . . ?
C21B C17B H17B 107.2 . . ?
C18B C17B H17B 107.2 . . ?
C16B C17B H17B 107.2 . . ?
O19B C18B O20B 121.4(15) . . ?
O19B C18B C17B 125.1(15) . . ?
O20B C18B C17B 113.4(16) . . ?
C18B O20B H20B 109.5 . . ?
O22B C21B C17B 113.1(19) . . ?
O22B C21B H21C 109.0 . . ?
C17B C21B H21C 109.0 . . ?
O22B C21B H21D 109.0 . . ?
C17B C21B H21D 109.0 . . ?
H21C C21B H21D 107.8 . . ?
C21B O22B H22B 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C2 C3 -10.6(6) . . . . ?
N1 C2 C3 C4 31.7(6) . . . . ?
C2 C3 C4 C5 -40.2(6) . . . . ?
C2 N1 C5 C4 -13.7(6) . . . . ?
C2 N1 C5 C6 103.9(5) . . . . ?
C3 C4 C5 N1 32.6(6) . . . . ?
C3 C4 C5 C6 -84.1(6) . . . . ?
N1 C5 C6 O7 -13.9(6) . . . . ?
C4 C5 C6 O7 98.7(5) . . . . ?
N1 C5 C6 O8 167.3(4) . . . . ?
C4 C5 C6 O8 -80.0(6) . . . . ?
C16 C11 C12 C13 -1(2) . . . . ?
C11 C12 C13 C14 1.7(19) . . . . ?
C12 C13 C14 C15 -1.3(17) . . . . ?
C13 C14 C15 C16 0.0(16) . . . . ?
C14 C15 C16 C11 1.0(13) . . . . ?
C14 C15 C16 C17 -176.8(9) . . . . ?
C12 C11 C16 C15 -0.6(18) . . . . ?
C12 C11 C16 C17 177.1(12) . . . . ?
C15 C16 C17 C18 106.4(8) . . . . ?
C11 C16 C17 C18 -71.3(11) . . . . ?
C15 C16 C17 C21 -129.3(10) . . . . ?
C11 C16 C17 C21 53.0(12) . . . . ?
C21 C17 C18 O19 -50.0(10) . . . . ?
C16 C17 C18 O19 75.5(9) . . . . ?
C21 C17 C18 O20 130.0(9) . . . . ?
C16 C17 C18 O20 -104.6(6) . . . . ?
C18 C17 C21 O22 -63.9(13) . . . . ?
C16 C17 C21 O22 173.6(7) . . . . ?
C16B C11B C12B C13B 9(14) . . . . ?
C11B C12B C13B C14B -12(13) . . . . ?
C12B C13B C14B C15B 15(11) . . . . ?
C13B C14B C15B C16B -16(11) . . . . ?
C14B C15B C16B C11B 13(9) . . . . ?
C14B C15B C16B C17B 176(5) . . . . ?
C12B C11B C16B C15B -9(12) . . . . ?
C12B C11B C16B C17B -173(7) . . . . ?
C15B C16B C17B C21B -72(5) . . . . ?
C11B C16B C17B C21B 91(6) . . . . ?
C15B C16B C17B C18B 54(4) . . . . ?
C11B C16B C17B C18B -143(6) . . . . ?
C21B C17B C18B O19B 27(6) . . . . ?
C16B C17B C18B O19B -100(4) . . . . ?
C21B C17B C18B O20B -149(4) . . . . ?
C16B C17B C18B O20B 84(4) . . . . ?
C18B C17B C21B O22B 54(8) . . . . ?
C16B C17B C21B O22B 178(6) . . . . ?

_refine_diff_density_max         0.347
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.053

####################################################################### 
# 
# 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_alex_A4_A12
_database_code_depnum_ccdc_archive 'CCDC 2247556'
loop_
_audit_author_name
_audit_author_address
'Koen Robeyns'
;Universite catholique de Louvain
Belgium
;
_audit_update_record             
;
2023-03-09 deposited with the CCDC.	2023-04-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H10 O3'
_chemical_formula_sum            'C9 H10 O3'
_chemical_formula_weight         166.17

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

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

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

_cell_length_a                   8.4198(11)
_cell_length_b                   5.8428(7)
_cell_length_c                   8.6049(9)
_cell_angle_alpha                90
_cell_angle_beta                 91.920(11)
_cell_angle_gamma                90
_cell_volume                     423.08(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    3352
_cell_measurement_theta_min      3.2860
_cell_measurement_theta_max      26.1070

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_F_000             176
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.15
_exptl_absorpt_coefficient_mu    0.098
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.42972
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?



_diffrn_ambient_temperature      297(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Incoatec microfocus source'
_diffrn_measurement_device_type  'MAR345 image plate'
_diffrn_measurement_method       
;
'120 images, ΔΦ 3.0° '
'54 images, ΔΦ 3.0° (2nd orientation)'
;
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8426
_diffrn_reflns_av_unetI/netI     0.0231
_diffrn_reflns_av_R_equivalents  0.0402
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.330
_diffrn_reflns_theta_max         26.278
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measured_fraction_theta_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_point_group_measured_fraction_full 0.988
_reflns_number_total             1673
_reflns_number_gt                1567
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.817
_reflns_Friedel_fraction_max     0.977
_reflns_Friedel_fraction_full    0.994

_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection       MAR
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_atom_sites_solution_primary     'dual space'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'MERCURY (Macrae et al., 2008)'
_computing_publication_material  
;
'MERCURY (Macrae et al., 2008), Platon (Spek, 2009)'
;


_refine_special_details          'Refined as a 2-component inversion twin.,Twin'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0356P)²+0.0582P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.3(16)
_chemical_absolute_configuration .
_refine_ls_number_reflns         1673
_refine_ls_number_parameters     114
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0352
_refine_ls_R_factor_gt           0.0325
_refine_ls_wR_factor_ref         0.0834
_refine_ls_wR_factor_gt          0.0822
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_restrained_S_all      1.082
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4387(3) 0.7723(5) 0.2793(3) 0.0574(6) Uani 1 1 d . . . . .
H1 H 0.383591 0.909465 0.287675 0.069 Uiso 1 1 calc R U . . .
C2 C 0.5791(3) 0.7426(7) 0.3645(4) 0.0708(8) Uani 1 1 d . . . . .
H2 H 0.616991 0.857887 0.430443 0.085 Uiso 1 1 calc R U . . .
C3 C 0.6619(4) 0.5432(6) 0.3515(4) 0.0713(9) Uani 1 1 d . . . . .
H3 H 0.756452 0.522227 0.408746 0.086 Uiso 1 1 calc R U . . .
C4 C 0.6058(4) 0.3740(6) 0.2541(3) 0.0712(8) Uani 1 1 d . . . . .
H4 H 0.663002 0.238722 0.244890 0.085 Uiso 1 1 calc R U . . .
C5 C 0.4642(3) 0.4030(5) 0.1691(3) 0.0581(7) Uani 1 1 d . . . . .
H5 H 0.427140 0.287166 0.103223 0.070 Uiso 1 1 calc R U . . .
C6 C 0.3778(3) 0.6034(4) 0.1817(2) 0.0449(5) Uani 1 1 d . . . . .
C7 C 0.2218(3) 0.6341(4) 0.0931(2) 0.0464(5) Uani 1 1 d . . . . .
H7A H 0.215633 0.522535 0.009687 0.056 Uiso 1 1 calc R U . . .
H7B H 0.220328 0.784957 0.046019 0.056 Uiso 1 1 calc R U . . .
C8 C 0.0750(2) 0.6089(4) 0.1909(2) 0.0391(5) Uani 1 1 d . . . . .
H8 H -0.019368 0.615510 0.121165 0.047 Uiso 1 1 calc R U . . .
O9 O 0.0682(2) 0.7940(3) 0.2966(2) 0.0497(5) Uani 1 1 d . . . . .
H9 H 0.0401(12) 0.748(2) 0.379(4) 0.061(9) Uiso 1 1 calc R . . . .
C10 C 0.0725(2) 0.3850(4) 0.2779(2) 0.0363(4) Uani 1 1 d . . . . .
O11 O 0.0672(2) 0.3725(3) 0.41662(17) 0.0488(4) Uani 1 1 d . . . . .
O12 O 0.0734(2) 0.2087(3) 0.1835(2) 0.0556(5) Uani 1 1 d . . . . .
H12 H 0.0716(2) 0.087(5) 0.236(2) 0.056(8) 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
C1 C2 1.382(4) . ?
C1 C6 1.383(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.364(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.370(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.388(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.384(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.507(3) . ?
C7 C8 1.526(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 O9 1.415(3) . ?
C8 C10 1.508(3) . ?
C8 H8 0.9800 . ?
O9 H9 0.80(3) . ?
C10 O11 1.199(2) . ?
C10 O12 1.312(3) . ?
O12 H12 0.84(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 121.7(3) . . ?
C2 C1 H1 119.1 . . ?
C6 C1 H1 119.1 . . ?
C3 C2 C1 119.6(3) . . ?
C3 C2 H2 120.2 . . ?
C1 C2 H2 120.2 . . ?
C2 C3 C4 120.0(3) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C3 C4 C5 120.4(3) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C6 C5 C4 120.4(3) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C1 C6 C5 117.8(2) . . ?
C1 C6 C7 121.4(2) . . ?
C5 C6 C7 120.8(2) . . ?
C6 C7 C8 114.73(16) . . ?
C6 C7 H7A 108.6 . . ?
C8 C7 H7A 108.6 . . ?
C6 C7 H7B 108.6 . . ?
C8 C7 H7B 108.6 . . ?
H7A C7 H7B 107.6 . . ?
O9 C8 C10 110.03(16) . . ?
O9 C8 C7 109.36(18) . . ?
C10 C8 C7 112.47(18) . . ?
O9 C8 H8 108.3 . . ?
C10 C8 H8 108.3 . . ?
C7 C8 H8 108.3 . . ?
C8 O9 H9 109.5 . . ?
O11 C10 O12 124.8(2) . . ?
O11 C10 C8 123.29(19) . . ?
O12 C10 C8 111.94(17) . . ?
C10 O12 H12 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 0.9(4) . . . . ?
C1 C2 C3 C4 0.1(5) . . . . ?
C2 C3 C4 C5 -0.5(4) . . . . ?
C3 C4 C5 C6 0.0(4) . . . . ?
C2 C1 C6 C5 -1.4(4) . . . . ?
C2 C1 C6 C7 178.0(2) . . . . ?
C4 C5 C6 C1 0.9(4) . . . . ?
C4 C5 C6 C7 -178.4(2) . . . . ?
C1 C6 C7 C8 -75.6(3) . . . . ?
C5 C6 C7 C8 103.7(2) . . . . ?
C6 C7 C8 O9 68.1(2) . . . . ?
C6 C7 C8 C10 -54.4(3) . . . . ?
O9 C8 C10 O11 -0.7(3) . . . . ?
C7 C8 C10 O11 121.5(2) . . . . ?
O9 C8 C10 O12 177.92(19) . . . . ?
C7 C8 C10 O12 -59.9(2) . . . . ?

_refine_diff_density_max         0.103
_refine_diff_density_min         -0.093
_refine_diff_density_rms         0.025

####################################################################### 
# 
# 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_alex_fl177
_database_code_depnum_ccdc_archive 'CCDC 2247557'
loop_
_audit_author_name
_audit_author_address
'Koen Robeyns'
;Universite catholique de Louvain
Belgium
;
_audit_update_record             
;
2023-03-09 deposited with the CCDC.	2023-04-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H14 N2 O2, C8 H7 Cl O3'
_chemical_formula_sum            'C16 H21 Cl N2 O5'
_chemical_formula_weight         356.80

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   7.7370(14)
_cell_length_b                   10.7279(12)
_cell_length_c                   11.583(2)
_cell_angle_alpha                63.137(16)
_cell_angle_beta                 86.083(15)
_cell_angle_gamma                84.134(13)
_cell_volume                     852.9(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    3263
_cell_measurement_theta_min      3.3200
_cell_measurement_theta_max      26.0970

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.389
_exptl_crystal_F_000             376
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.25
_exptl_absorpt_coefficient_mu    0.253
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.71940
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      297(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Incoatec microfocus source'
_diffrn_measurement_device_type  'MAR345 image plate'
_diffrn_measurement_method       
;
'60 images, ΔΦ 3.0° '
'54 images, ΔΦ 3.0° (2nd orientation)'
;
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11062
_diffrn_reflns_av_unetI/netI     0.0163
_diffrn_reflns_av_R_equivalents  0.0195
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.262
_diffrn_reflns_theta_max         26.147
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             3378
_reflns_number_gt                3113
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       MAR
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_atom_sites_solution_primary     'dual space'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'MERCURY (Macrae et al., 2008)'
_computing_publication_material  
;
'MERCURY (Macrae et al., 2008), Platon (Spek, 2009)'
;



_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0456P)²+0.4248P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3378
_refine_ls_number_parameters     232
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.0438
_refine_ls_R_factor_gt           0.0405
_refine_ls_wR_factor_ref         0.1045
_refine_ls_wR_factor_gt          0.1019
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 1.13086(8) -0.28239(5) 0.59329(5) 0.05955(18) Uani 1 1 d . . . . .
C2 C 1.1646(2) -0.11671(17) 0.46823(16) 0.0372(4) Uani 1 1 d . . . . .
C3 C 1.0922(2) -0.07624(16) 0.34915(15) 0.0329(3) Uani 1 1 d . . . . .
H3 H 1.024440 -0.136091 0.337258 0.039 Uiso 1 1 calc R U . . .
C4 C 1.12109(19) 0.05361(16) 0.24789(15) 0.0307(3) Uani 1 1 d . . . . .
C5 C 1.2244(2) 0.14119(17) 0.26720(18) 0.0389(4) Uani 1 1 d . . . . .
H5 H 1.246493 0.227901 0.199421 0.047 Uiso 1 1 calc R U . . .
C6 C 1.2942(3) 0.0992(2) 0.3871(2) 0.0466(4) Uani 1 1 d . . . . .
H6 H 1.362378 0.158642 0.399376 0.056 Uiso 1 1 calc R U . . .
C7 C 1.2643(2) -0.0296(2) 0.48910(18) 0.0448(4) Uani 1 1 d . . . . .
H7 H 1.310386 -0.056862 0.569889 0.054 Uiso 1 1 calc R U . . .
C8 C 1.0421(2) 0.09992(15) 0.11641(15) 0.0311(3) Uani 1 1 d . . . . .
H8 H 0.983397 0.022625 0.117530 0.037 Uiso 1 1 calc R U . . .
O9 O 1.16920(16) 0.14244(12) 0.01434(11) 0.0396(3) Uani 1 1 d . . . . .
H9 H 1.238(3) 0.075(2) 0.0239(13) 0.059 Uiso 1 1 calc R U . . .
C10 C 0.9093(2) 0.22414(16) 0.09209(15) 0.0308(3) Uani 1 1 d . . . . .
O11 O 0.76783(15) 0.18325(12) 0.16376(11) 0.0366(3) Uani 1 1 d . . . . .
H11 H 0.701(2) 0.253(2) 0.1541(17) 0.055 Uiso 1 1 calc R U . . .
O12 O 0.93432(16) 0.34406(12) 0.01946(13) 0.0473(3) Uani 1 1 d . . . . .
O21 O 0.34707(16) 0.88478(12) 0.07797(12) 0.0425(3) Uani 1 1 d . . . . .
C22 C 0.4547(2) 0.82455(15) 0.16294(15) 0.0306(3) Uani 1 1 d D . . . .
C23 C 0.5454(13) 0.8875(4) 0.2329(8) 0.0407(7) Uani 0.785(5) 1 d D . P A 1
H23A H 0.466371 0.905635 0.293281 0.049 Uiso 0.785(5) 1 calc R U P A 1
H23B H 0.593131 0.974313 0.172316 0.049 Uiso 0.785(5) 1 calc R U P A 1
C24 C 0.6892(3) 0.7757(3) 0.3040(3) 0.0447(6) Uani 0.785(5) 1 d D . P A 1
H24A H 0.711416 0.774309 0.385971 0.054 Uiso 0.785(5) 1 calc R U P A 1
H24B H 0.795967 0.791396 0.252099 0.054 Uiso 0.785(5) 1 calc R U P A 1
C25 C 0.6173(11) 0.6393(5) 0.3248(7) 0.0418(10) Uani 0.785(5) 1 d D . P A 1
H25A H 0.709762 0.570676 0.325720 0.050 Uiso 0.785(5) 1 calc R U P A 1
H25B H 0.549172 0.599566 0.404851 0.050 Uiso 0.785(5) 1 calc R U P A 1
C23B C 0.556(5) 0.8871(12) 0.229(3) 0.0407(7) Uani 0.215(5) 1 d D . P A 2
H23C H 0.482332 0.955574 0.246568 0.049 Uiso 0.215(5) 1 calc R U P A 2
H23D H 0.654609 0.931804 0.175321 0.049 Uiso 0.215(5) 1 calc R U P A 2
C24B C 0.6147(14) 0.7617(10) 0.3540(10) 0.0447(6) Uani 0.215(5) 1 d D . P A 2
H24C H 0.528237 0.744586 0.423081 0.054 Uiso 0.215(5) 1 calc R U P A 2
H24D H 0.724291 0.775057 0.381164 0.054 Uiso 0.215(5) 1 calc R U P A 2
C25B C 0.634(4) 0.6418(18) 0.315(3) 0.0418(10) Uani 0.215(5) 1 d D . P A 2
H25C H 0.751647 0.631017 0.283427 0.050 Uiso 0.215(5) 1 calc R U P A 2
H25D H 0.606906 0.553807 0.387519 0.050 Uiso 0.215(5) 1 calc R U P A 2
N26 N 0.50846(16) 0.68676(13) 0.21193(13) 0.0300(3) Uani 1 1 d D . . . .
C27 C 0.43241(19) 0.59000(15) 0.17687(16) 0.0306(3) Uani 1 1 d . . . . .
H27 H 0.364227 0.646959 0.099376 0.037 Uiso 1 1 calc R U . . .
C28 C 0.57310(19) 0.50160(15) 0.14061(15) 0.0298(3) Uani 1 1 d . . . . .
O29 O 0.54337(15) 0.38223(12) 0.16004(13) 0.0412(3) Uani 1 1 d . . . . .
N30 N 0.71996(18) 0.55800(15) 0.08786(14) 0.0388(3) Uani 1 1 d . . . . .
H30A H 0.800589 0.511482 0.065181 0.047 Uiso 1 1 calc R U . . .
H30B H 0.735029 0.641260 0.076169 0.047 Uiso 1 1 calc R U . . .
C31 C 0.3076(2) 0.49780(19) 0.2816(2) 0.0470(5) Uani 1 1 d . . . . .
H31A H 0.256261 0.439348 0.251452 0.056 Uiso 1 1 calc R U . . .
H31B H 0.372457 0.436511 0.358454 0.056 Uiso 1 1 calc R U . . .
C32 C 0.1633(3) 0.5827(3) 0.3171(3) 0.0677(7) Uani 1 1 d . . . . .
H32A H 0.100242 0.645211 0.240998 0.102 Uiso 1 1 calc R U . . .
H32B H 0.212882 0.636153 0.352421 0.102 Uiso 1 1 calc R U . . .
H32C H 0.085653 0.520510 0.380150 0.102 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C2 1.7441(18) . ?
C2 C7 1.381(3) . ?
C2 C3 1.385(2) . ?
C3 C4 1.385(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.393(2) . ?
C4 C8 1.524(2) . ?
C5 C6 1.382(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.382(3) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 O9 1.4207(19) . ?
C8 C10 1.527(2) . ?
C8 H8 0.9800 . ?
O9 H9 0.83(3) . ?
C10 O12 1.2045(19) . ?
C10 O11 1.3134(19) . ?
O11 H11 0.83(2) . ?
O21 C22 1.228(2) . ?
C22 N26 1.3522(19) . ?
C22 C23 1.508(3) . ?
C22 C23B 1.513(8) . ?
C23 C24 1.521(6) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C24 C25 1.529(6) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C25 N26 1.463(3) . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C23B C24B 1.525(11) . ?
C23B H23C 0.9700 . ?
C23B H23D 0.9700 . ?
C24B C25B 1.535(10) . ?
C24B H24C 0.9700 . ?
C24B H24D 0.9700 . ?
C25B N26 1.467(8) . ?
C25B H25C 0.9700 . ?
C25B H25D 0.9700 . ?
N26 C27 1.4585(19) . ?
C27 C31 1.528(2) . ?
C27 C28 1.532(2) . ?
C27 H27 0.9800 . ?
C28 O29 1.2394(18) . ?
C28 N30 1.320(2) . ?
N30 H30A 0.8600 . ?
N30 H30B 0.8600 . ?
C31 C32 1.521(3) . ?
C31 H31A 0.9700 . ?
C31 H31B 0.9700 . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 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
C7 C2 C3 121.39(16) . . ?
C7 C2 Cl1 119.57(14) . . ?
C3 C2 Cl1 119.03(14) . . ?
C4 C3 C2 119.80(15) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C3 C4 C5 119.26(15) . . ?
C3 C4 C8 120.47(14) . . ?
C5 C4 C8 120.27(14) . . ?
C6 C5 C4 120.01(16) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C7 C6 C5 121.07(17) . . ?
C7 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
C2 C7 C6 118.46(17) . . ?
C2 C7 H7 120.8 . . ?
C6 C7 H7 120.8 . . ?
O9 C8 C4 112.13(13) . . ?
O9 C8 C10 108.52(12) . . ?
C4 C8 C10 108.08(12) . . ?
O9 C8 H8 109.4 . . ?
C4 C8 H8 109.4 . . ?
C10 C8 H8 109.4 . . ?
C8 O9 H9 109.5 . . ?
O12 C10 O11 124.83(14) . . ?
O12 C10 C8 124.04(14) . . ?
O11 C10 C8 111.09(13) . . ?
C10 O11 H11 109.5 . . ?
O21 C22 N26 124.65(15) . . ?
O21 C22 C23 127.0(2) . . ?
N26 C22 C23 108.3(2) . . ?
O21 C22 C23B 128.0(6) . . ?
N26 C22 C23B 107.3(6) . . ?
C22 C23 C24 103.7(3) . . ?
C22 C23 H23A 111.0 . . ?
C24 C23 H23A 111.0 . . ?
C22 C23 H23B 111.0 . . ?
C24 C23 H23B 111.0 . . ?
H23A C23 H23B 109.0 . . ?
C23 C24 C25 103.6(3) . . ?
C23 C24 H24A 111.0 . . ?
C25 C24 H24A 111.0 . . ?
C23 C24 H24B 111.0 . . ?
C25 C24 H24B 111.0 . . ?
H24A C24 H24B 109.0 . . ?
N26 C25 C24 101.9(3) . . ?
N26 C25 H25A 111.4 . . ?
C24 C25 H25A 111.4 . . ?
N26 C25 H25B 111.4 . . ?
C24 C25 H25B 111.4 . . ?
H25A C25 H25B 109.3 . . ?
C22 C23B C24B 104.1(8) . . ?
C22 C23B H23C 110.9 . . ?
C24B C23B H23C 110.9 . . ?
C22 C23B H23D 110.9 . . ?
C24B C23B H23D 110.9 . . ?
H23C C23B H23D 109.0 . . ?
C23B C24B C25B 102.3(10) . . ?
C23B C24B H24C 111.3 . . ?
C25B C24B H24C 111.3 . . ?
C23B C24B H24D 111.3 . . ?
C25B C24B H24D 111.3 . . ?
H24C C24B H24D 109.2 . . ?
N26 C25B C24B 103.3(8) . . ?
N26 C25B H25C 111.1 . . ?
C24B C25B H25C 111.1 . . ?
N26 C25B H25D 111.1 . . ?
C24B C25B H25D 111.1 . . ?
H25C C25B H25D 109.1 . . ?
C22 N26 C27 123.02(13) . . ?
C22 N26 C25 112.64(18) . . ?
C27 N26 C25 122.7(2) . . ?
C22 N26 C25B 113.1(5) . . ?
C27 N26 C25B 123.4(6) . . ?
N26 C27 C31 112.55(13) . . ?
N26 C27 C28 111.36(12) . . ?
C31 C27 C28 111.39(13) . . ?
N26 C27 H27 107.1 . . ?
C31 C27 H27 107.1 . . ?
C28 C27 H27 107.1 . . ?
O29 C28 N30 123.14(14) . . ?
O29 C28 C27 118.96(13) . . ?
N30 C28 C27 117.89(13) . . ?
C28 N30 H30A 120.0 . . ?
C28 N30 H30B 120.0 . . ?
H30A N30 H30B 120.0 . . ?
C32 C31 C27 112.64(16) . . ?
C32 C31 H31A 109.1 . . ?
C27 C31 H31A 109.1 . . ?
C32 C31 H31B 109.1 . . ?
C27 C31 H31B 109.1 . . ?
H31A C31 H31B 107.8 . . ?
C31 C32 H32A 109.5 . . ?
C31 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C31 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 C2 C3 C4 0.6(2) . . . . ?
Cl1 C2 C3 C4 -178.47(12) . . . . ?
C2 C3 C4 C5 0.7(2) . . . . ?
C2 C3 C4 C8 -179.84(14) . . . . ?
C3 C4 C5 C6 -1.2(2) . . . . ?
C8 C4 C5 C6 179.30(15) . . . . ?
C4 C5 C6 C7 0.5(3) . . . . ?
C3 C2 C7 C6 -1.3(3) . . . . ?
Cl1 C2 C7 C6 177.74(14) . . . . ?
C5 C6 C7 C2 0.8(3) . . . . ?
C3 C4 C8 O9 -126.48(15) . . . . ?
C5 C4 C8 O9 53.02(18) . . . . ?
C3 C4 C8 C10 113.95(15) . . . . ?
C5 C4 C8 C10 -66.55(18) . . . . ?
O9 C8 C10 O12 -17.6(2) . . . . ?
C4 C8 C10 O12 104.17(18) . . . . ?
O9 C8 C10 O11 164.45(13) . . . . ?
C4 C8 C10 O11 -73.74(16) . . . . ?
O21 C22 C23 C24 -168.2(3) . . . . ?
N26 C22 C23 C24 13.4(7) . . . . ?
C22 C23 C24 C25 -27.2(8) . . . . ?
C23 C24 C25 N26 30.7(7) . . . . ?
O21 C22 C23B C24B 160.0(10) . . . . ?
N26 C22 C23B C24B -22(3) . . . . ?
C22 C23B C24B C25B 31(3) . . . . ?
C23B C24B C25B N26 -28(3) . . . . ?
O21 C22 N26 C27 -5.6(2) . . . . ?
C23 C22 N26 C27 172.9(5) . . . . ?
C23B C22 N26 C27 176.3(19) . . . . ?
O21 C22 N26 C25 -171.4(5) . . . . ?
C23 C22 N26 C25 7.0(7) . . . . ?
O21 C22 N26 C25B -178.4(18) . . . . ?
C23B C22 N26 C25B 4(3) . . . . ?
C24 C25 N26 C22 -24.2(6) . . . . ?
C24 C25 N26 C27 169.9(2) . . . . ?
C24B C25B N26 C22 16(3) . . . . ?
C24B C25B N26 C27 -156.5(11) . . . . ?
C22 N26 C27 C31 -102.78(18) . . . . ?
C25 N26 C27 C31 61.6(5) . . . . ?
C25B N26 C27 C31 69(2) . . . . ?
C22 N26 C27 C28 131.31(15) . . . . ?
C25 N26 C27 C28 -64.3(5) . . . . ?
C25B N26 C27 C28 -57(2) . . . . ?
N26 C27 C28 O29 150.55(14) . . . . ?
C31 C27 C28 O29 24.0(2) . . . . ?
N26 C27 C28 N30 -30.5(2) . . . . ?
C31 C27 C28 N30 -157.08(15) . . . . ?
N26 C27 C31 C32 55.7(2) . . . . ?
C28 C27 C31 C32 -178.40(17) . . . . ?

_refine_diff_density_max         0.341
_refine_diff_density_min         -0.366
_refine_diff_density_rms         0.041

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

data_alex_fl180
_database_code_depnum_ccdc_archive 'CCDC 2247559'
loop_
_audit_author_name
_audit_author_address
'Koen Robeyns'
;Universite catholique de Louvain
Belgium
;
_audit_update_record             
;
2023-03-09 deposited with the CCDC.	2023-04-28 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_THETM01_alex_fl180          
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.550
RESPONSE: A data cut-off of 0.95A was imposed during integration beyond which the crystal diffracted poorly
;
# Added during the CSD deposition process: Thursday 09 March 2023 01:41 PM
# end Validation Reply Form


_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H12 O2, C5 H9 N O2'
_chemical_formula_sum            'C15 H21 N O4'
_chemical_formula_weight         279.33

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'

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

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

_cell_length_a                   10.1357(7)
_cell_length_b                   17.1919(16)
_cell_length_c                   9.1265(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1590.3(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    1769
_cell_measurement_theta_min      3.0950
_cell_measurement_theta_max      21.4820

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.167
_exptl_crystal_F_000             600
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.01
_exptl_absorpt_coefficient_mu    0.084
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.00963
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?




_diffrn_ambient_temperature      297(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Incoatec microfocus source'
_diffrn_measurement_device_type  'MAR345 image plate'
_diffrn_measurement_method       
;
'90 images, ΔΦ 2.0° '
;
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6801
_diffrn_reflns_av_unetI/netI     0.0485
_diffrn_reflns_av_R_equivalents  0.0660
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         3.107
_diffrn_reflns_theta_max         21.958
_diffrn_reflns_theta_full        21.958
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measured_fraction_theta_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_point_group_measured_fraction_full 0.982
_reflns_number_total             1906
_reflns_number_gt                1454
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.845
_reflns_Friedel_fraction_max     0.980
_reflns_Friedel_fraction_full    0.980

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

_computing_data_collection       MAR
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_atom_sites_solution_primary     dual
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'MERCURY (Macrae et al., 2008)'
_computing_publication_material  
;
'MERCURY (Macrae et al., 2008), Platon (Spek, 2009)'
;




_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0739P)²+0.4869P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 534 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -1.3(10)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         1906
_refine_ls_number_parameters     241
_refine_ls_number_restraints     148
_refine_ls_R_factor_all          0.0779
_refine_ls_R_factor_gt           0.0567
_refine_ls_wR_factor_ref         0.1544
_refine_ls_wR_factor_gt          0.1433
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.085
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.9909(5) 0.5630(3) 0.8448(6) 0.0544(14) Uani 1 1 d D U . . .
H1A H 1.027055 0.552873 0.931541 0.065 Uiso 1 1 calc R U . A 3
H1B H 1.043364 0.543893 0.775389 0.065 Uiso 1 1 calc R U . A 3
C2 C 0.9761(12) 0.6485(5) 0.825(4) 0.064(5) Uani 0.74(2) 1 d D U P B 3
H2A H 0.983831 0.663234 0.723150 0.077 Uiso 0.74(2) 1 calc R U P B 3
H2B H 1.041277 0.676822 0.882189 0.077 Uiso 0.74(2) 1 calc R U P B 3
C3 C 0.8383(10) 0.6630(6) 0.8824(17) 0.072(4) Uani 0.74(2) 1 d D U P B 3
H3A H 0.803951 0.712498 0.848781 0.086 Uiso 0.74(2) 1 calc R U P B 3
H3B H 0.835489 0.661350 0.988640 0.086 Uiso 0.74(2) 1 calc R U P B 3
C4 C 0.7626(12) 0.5944(7) 0.815(3) 0.080(6) Uani 0.74(2) 1 d D U P B 3
H4A H 0.680069 0.585297 0.865426 0.096 Uiso 0.74(2) 1 calc R U P B 3
H4B H 0.744626 0.603496 0.711562 0.096 Uiso 0.74(2) 1 calc R U P B 3
C2B C 0.975(3) 0.6491(8) 0.842(12) 0.070(11) Uani 0.26(2) 1 d D U P B 4
H2C H 1.042423 0.673315 0.781711 0.084 Uiso 0.26(2) 1 calc R U P B 4
H2D H 0.980500 0.670654 0.940564 0.084 Uiso 0.26(2) 1 calc R U P B 4
C3B C 0.840(3) 0.660(2) 0.778(5) 0.075(9) Uani 0.26(2) 1 d D U P B 4
H3C H 0.840639 0.653923 0.672114 0.091 Uiso 0.26(2) 1 calc R U P B 4
H3D H 0.803427 0.710583 0.802297 0.091 Uiso 0.26(2) 1 calc R U P B 4
C4B C 0.762(3) 0.5942(13) 0.852(8) 0.070(10) Uani 0.26(2) 1 d D U P B 4
H4C H 0.744473 0.605626 0.954301 0.084 Uiso 0.26(2) 1 calc R U P B 4
H4D H 0.679045 0.584111 0.802114 0.084 Uiso 0.26(2) 1 calc R U P B 4
C5 C 0.8580(6) 0.5261(4) 0.8352(8) 0.0534(17) Uani 1 1 d D U . . .
H5 H 0.837877 0.498643 0.926615 0.064 Uiso 1 1 calc R U . B 3
C6 C 0.8514(7) 0.4701(4) 0.7070(7) 0.0543(18) Uani 1 1 d . . . . .
O7 O 0.9501(5) 0.4635(3) 0.6288(6) 0.0689(14) Uani 1 1 d . . . . .
O8 O 0.7428(5) 0.4363(3) 0.6894(5) 0.0715(15) Uani 1 1 d . . . . .
C11 C 0.6199(7) 0.3106(4) 0.4470(9) 0.0637(19) Uani 1 1 d . . . . .
O12 O 0.5301(5) 0.3562(3) 0.4632(7) 0.0855(17) Uani 1 1 d . . . . .
O13 O 0.7339(4) 0.3186(3) 0.5132(6) 0.0754(16) Uani 1 1 d . . . . .
H13 H 0.730128 0.355292 0.570463 0.113 Uiso 1 1 calc R U . . .
C14 C 0.6098(7) 0.2388(4) 0.3556(10) 0.075(2) Uani 1 1 d D . . . .
H14 H 0.695103 0.228091 0.309144 0.090 Uiso 0.704(15) 1 calc R U P C 1
H14B H 0.689725 0.243512 0.295767 0.090 Uiso 0.296(15) 1 calc R U P C 2
C15 C 0.5026(9) 0.2466(6) 0.2374(10) 0.089(3) Uani 1 1 d . . . . .
H15A H 0.417277 0.251095 0.284824 0.107 Uiso 1 1 calc R U . . .
H15B H 0.517757 0.294010 0.182395 0.107 Uiso 1 1 calc R U . . .
C16 C 0.4992(11) 0.1791(7) 0.1329(17) 0.134(4) Uani 1 1 d . . . . .
H16A H 0.436123 0.189272 0.056855 0.201 Uiso 1 1 calc R U . . .
H16B H 0.474284 0.132776 0.184851 0.201 Uiso 1 1 calc R U . . .
H16C H 0.584972 0.172038 0.090385 0.201 Uiso 1 1 calc R U . . .
C17 C 0.5744(11) 0.1714(5) 0.4635(12) 0.083(4) Uani 0.704(15) 1 d DG U P C 1
C18 C 0.6529(11) 0.1052(6) 0.4694(14) 0.124(5) Uani 0.704(15) 1 d G U P C 1
H18 H 0.726164 0.100851 0.408617 0.149 Uiso 0.704(15) 1 calc R U P C 1
C19 C 0.6218(15) 0.0455(6) 0.5661(18) 0.145(7) Uani 0.704(15) 1 d G U P C 1
H19 H 0.674325 0.001168 0.570002 0.174 Uiso 0.704(15) 1 calc R U P C 1
C21 C 0.5123(17) 0.0520(7) 0.6569(17) 0.184(9) Uani 0.704(15) 1 d G U P C 1
H21 H 0.491509 0.012032 0.721589 0.220 Uiso 0.704(15) 1 calc R U P C 1
C22 C 0.4338(13) 0.1182(8) 0.6510(14) 0.156(7) Uani 0.704(15) 1 d G U P C 1
H22 H 0.360532 0.122580 0.711793 0.187 Uiso 0.704(15) 1 calc R U P C 1
C20 C 0.4649(11) 0.1779(6) 0.5543(14) 0.109(5) Uani 0.704(15) 1 d G U P C 1
H20 H 0.412369 0.222264 0.550409 0.130 Uiso 0.704(15) 1 calc R U P C 1
C17B C 0.632(3) 0.1601(11) 0.426(3) 0.102(12) Uani 0.296(15) 1 d DG U P C 2
C18B C 0.729(3) 0.1074(14) 0.384(3) 0.112(10) Uani 0.296(15) 1 d G U P C 2
H18B H 0.783896 0.118591 0.304901 0.134 Uiso 0.296(15) 1 calc R U P C 2
C19B C 0.744(3) 0.0378(12) 0.460(4) 0.132(12) Uani 0.296(15) 1 d G U P C 2
H19B H 0.808555 0.002522 0.431648 0.158 Uiso 0.296(15) 1 calc R U P C 2
C21B C 0.662(4) 0.0210(14) 0.578(4) 0.166(16) Uani 0.296(15) 1 d G U P C 2
H21B H 0.671563 -0.025516 0.628328 0.200 Uiso 0.296(15) 1 calc R U P C 2
C22B C 0.565(4) 0.0738(18) 0.619(4) 0.168(17) Uani 0.296(15) 1 d G U P C 2
H22B H 0.509911 0.062515 0.698262 0.202 Uiso 0.296(15) 1 calc R U P C 2
C20B C 0.550(3) 0.1433(16) 0.543(4) 0.141(19) Uani 0.296(15) 1 d G U P C 2
H20B H 0.485249 0.178584 0.571515 0.169 Uiso 0.296(15) 1 calc R U P C 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
N1 C2 1.488(10) . ?
N1 C2B 1.488(15) . ?
N1 C5 1.492(8) . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
C2 C3 1.51(2) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.537(18) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.533(12) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C2B C3B 1.51(3) . ?
C2B H2C 0.9700 . ?
C2B H2D 0.9700 . ?
C3B C4B 1.54(2) . ?
C3B H3C 0.9700 . ?
C3B H3D 0.9700 . ?
C4B C5 1.531(16) . ?
C4B H4C 0.9700 . ?
C4B H4D 0.9700 . ?
C5 C6 1.516(9) . ?
C5 H5 0.9800 . ?
C6 O7 1.234(8) . ?
C6 O8 1.256(8) . ?
C11 O12 1.210(8) . ?
C11 O13 1.312(8) . ?
C11 C14 1.494(11) . ?
O13 H13 0.8200 . ?
C14 C17B 1.513(16) . ?
C14 C15 1.537(11) . ?
C14 C17 1.562(11) . ?
C14 H14 0.9800 . ?
C14 H14B 0.9800 . ?
C15 C16 1.502(14) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 C18 1.3900 . ?
C17 C20 1.3900 . ?
C18 C19 1.3900 . ?
C18 H18 0.9300 . ?
C19 C21 1.3900 . ?
C19 H19 0.9300 . ?
C21 C22 1.3900 . ?
C21 H21 0.9300 . ?
C22 C20 1.3900 . ?
C22 H22 0.9300 . ?
C20 H20 0.9300 . ?
C17B C18B 1.3900 . ?
C17B C20B 1.3900 . ?
C18B C19B 1.3900 . ?
C18B H18B 0.9300 . ?
C19B C21B 1.3900 . ?
C19B H19B 0.9300 . ?
C21B C22B 1.3900 . ?
C21B H21B 0.9300 . ?
C22B C20B 1.3900 . ?
C22B H22B 0.9300 . ?
C20B H20B 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C5 108.8(6) . . ?
C2B N1 C5 109.1(12) . . ?
C2 N1 H1A 109.9 . . ?
C5 N1 H1A 109.9 . . ?
C2 N1 H1B 109.9 . . ?
C5 N1 H1B 109.9 . . ?
H1A N1 H1B 108.3 . . ?
N1 C2 C3 102.4(12) . . ?
N1 C2 H2A 111.3 . . ?
C3 C2 H2A 111.3 . . ?
N1 C2 H2B 111.3 . . ?
C3 C2 H2B 111.3 . . ?
H2A C2 H2B 109.2 . . ?
C2 C3 C4 101.3(13) . . ?
C2 C3 H3A 111.5 . . ?
C4 C3 H3A 111.5 . . ?
C2 C3 H3B 111.5 . . ?
C4 C3 H3B 111.5 . . ?
H3A C3 H3B 109.3 . . ?
C5 C4 C3 102.9(11) . . ?
C5 C4 H4A 111.2 . . ?
C3 C4 H4A 111.2 . . ?
C5 C4 H4B 111.2 . . ?
C3 C4 H4B 111.2 . . ?
H4A C4 H4B 109.1 . . ?
N1 C2B C3B 103(2) . . ?
N1 C2B H2C 111.2 . . ?
C3B C2B H2C 111.2 . . ?
N1 C2B H2D 111.2 . . ?
C3B C2B H2D 111.2 . . ?
H2C C2B H2D 109.1 . . ?
C2B C3B C4B 102(2) . . ?
C2B C3B H3C 111.4 . . ?
C4B C3B H3C 111.4 . . ?
C2B C3B H3D 111.4 . . ?
C4B C3B H3D 111.4 . . ?
H3C C3B H3D 109.3 . . ?
C5 C4B C3B 101(2) . . ?
C5 C4B H4C 111.6 . . ?
C3B C4B H4C 111.6 . . ?
C5 C4B H4D 111.6 . . ?
C3B C4B H4D 111.6 . . ?
H4C C4B H4D 109.4 . . ?
N1 C5 C6 110.8(5) . . ?
N1 C5 C4B 104.1(14) . . ?
C6 C5 C4B 122(3) . . ?
N1 C5 C4 104.5(7) . . ?
C6 C5 C4 111.3(10) . . ?
N1 C5 H5 110.0 . . ?
C6 C5 H5 110.0 . . ?
C4 C5 H5 110.0 . . ?
O7 C6 O8 126.4(7) . . ?
O7 C6 C5 118.0(6) . . ?
O8 C6 C5 115.5(6) . . ?
O12 C11 O13 122.6(7) . . ?
O12 C11 C14 123.5(7) . . ?
O13 C11 C14 113.8(6) . . ?
C11 O13 H13 109.5 . . ?
C11 C14 C17B 119.5(14) . . ?
C11 C14 C15 111.6(7) . . ?
C17B C14 C15 118.7(14) . . ?
C11 C14 C17 106.0(8) . . ?
C15 C14 C17 110.2(7) . . ?
C11 C14 H14 109.7 . . ?
C15 C14 H14 109.7 . . ?
C17 C14 H14 109.7 . . ?
C11 C14 H14B 100.7 . . ?
C17B C14 H14B 100.7 . . ?
C15 C14 H14B 100.7 . . ?
C16 C15 C14 113.2(8) . . ?
C16 C15 H15A 108.9 . . ?
C14 C15 H15A 108.9 . . ?
C16 C15 H15B 108.9 . . ?
C14 C15 H15B 108.9 . . ?
H15A C15 H15B 107.7 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C18 C17 C20 120.0 . . ?
C18 C17 C14 120.0(7) . . ?
C20 C17 C14 120.0(7) . . ?
C19 C18 C17 120.0 . . ?
C19 C18 H18 120.0 . . ?
C17 C18 H18 120.0 . . ?
C18 C19 C21 120.0 . . ?
C18 C19 H19 120.0 . . ?
C21 C19 H19 120.0 . . ?
C22 C21 C19 120.0 . . ?
C22 C21 H21 120.0 . . ?
C19 C21 H21 120.0 . . ?
C21 C22 C20 120.0 . . ?
C21 C22 H22 120.0 . . ?
C20 C22 H22 120.0 . . ?
C22 C20 C17 120.0 . . ?
C22 C20 H20 120.0 . . ?
C17 C20 H20 120.0 . . ?
C18B C17B C20B 120.0 . . ?
C18B C17B C14 124.9(19) . . ?
C20B C17B C14 115.0(19) . . ?
C19B C18B C17B 120.0 . . ?
C19B C18B H18B 120.0 . . ?
C17B C18B H18B 120.0 . . ?
C21B C19B C18B 120.0 . . ?
C21B C19B H19B 120.0 . . ?
C18B C19B H19B 120.0 . . ?
C19B C21B C22B 120.0 . . ?
C19B C21B H21B 120.0 . . ?
C22B C21B H21B 120.0 . . ?
C20B C22B C21B 120.0 . . ?
C20B C22B H22B 120.0 . . ?
C21B C22B H22B 120.0 . . ?
C22B C20B C17B 120.0 . . ?
C22B C20B H20B 120.0 . . ?
C17B C20B H20B 120.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C2 C3 28(2) . . . . ?
N1 C2 C3 C4 -43(2) . . . . ?
C2 C3 C4 C5 42(2) . . . . ?
C5 N1 C2B C3B -20(6) . . . . ?
N1 C2B C3B C4B 40(6) . . . . ?
C2B C3B C4B C5 -45(5) . . . . ?
C2 N1 C5 C6 118.1(15) . . . . ?
C2B N1 C5 C6 124(4) . . . . ?
C2B N1 C5 C4B -9(5) . . . . ?
C2 N1 C5 C4 -1.9(18) . . . . ?
C3B C4B C5 N1 33(4) . . . . ?
C3B C4B C5 C6 -93(3) . . . . ?
C3 C4 C5 N1 -24.8(16) . . . . ?
C3 C4 C5 C6 -144.4(12) . . . . ?
N1 C5 C6 O7 -1.4(8) . . . . ?
C4B C5 C6 O7 121.9(17) . . . . ?
C4 C5 C6 O7 114.5(9) . . . . ?
N1 C5 C6 O8 -179.7(6) . . . . ?
C4B C5 C6 O8 -56.4(18) . . . . ?
C4 C5 C6 O8 -63.9(10) . . . . ?
O12 C11 C14 C17B -120.4(16) . . . . ?
O13 C11 C14 C17B 57.1(17) . . . . ?
O12 C11 C14 C15 24.4(11) . . . . ?
O13 C11 C14 C15 -158.0(7) . . . . ?
O12 C11 C14 C17 -95.5(9) . . . . ?
O13 C11 C14 C17 82.0(8) . . . . ?
C11 C14 C15 C16 173.8(9) . . . . ?
C17B C14 C15 C16 -41.0(18) . . . . ?
C17 C14 C15 C16 -68.7(11) . . . . ?
C11 C14 C17 C18 -125.1(8) . . . . ?
C15 C14 C17 C18 114.0(9) . . . . ?
C11 C14 C17 C20 54.5(9) . . . . ?
C15 C14 C17 C20 -66.4(10) . . . . ?
C20 C17 C18 C19 0.0 . . . . ?
C14 C17 C18 C19 179.6(11) . . . . ?
C17 C18 C19 C21 0.0 . . . . ?
C18 C19 C21 C22 0.0 . . . . ?
C19 C21 C22 C20 0.0 . . . . ?
C21 C22 C20 C17 0.0 . . . . ?
C18 C17 C20 C22 0.0 . . . . ?
C14 C17 C20 C22 -179.6(11) . . . . ?
C11 C14 C17B C18B -121(2) . . . . ?
C15 C14 C17B C18B 97(2) . . . . ?
C11 C14 C17B C20B 57(2) . . . . ?
C15 C14 C17B C20B -85.3(18) . . . . ?
C20B C17B C18B C19B 0.0 . . . . ?
C14 C17B C18B C19B 178(3) . . . . ?
C17B C18B C19B C21B 0.0 . . . . ?
C18B C19B C21B C22B 0.0 . . . . ?
C19B C21B C22B C20B 0.0 . . . . ?
C21B C22B C20B C17B 0.0 . . . . ?
C18B C17B C20B C22B 0.0 . . . . ?
C14 C17B C20B C22B -178(3) . . . . ?

_refine_diff_density_max         0.117
_refine_diff_density_min         -0.145
_refine_diff_density_rms         0.032

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

data_alex_A129_AA22
_database_code_depnum_ccdc_archive 'CCDC 2247565'
loop_
_audit_author_name
_audit_author_address
'Koen Robeyns'
;Universite catholique de Louvain
Belgium
;
_audit_update_record             
;
2023-03-09 deposited with the CCDC.	2023-04-28 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_THETM01_alex_A129_AA22      
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.550
RESPONSE: A data cut-off of 1.1A was imposed during integration beyond which the crystal diffracted poorly
;
# Added during the CSD deposition process: Thursday 09 March 2023 01:41 PM
# end Validation Reply Form


_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H10 O4, C5 H9 N O2'
_chemical_formula_sum            'C30 H38 N2 O12'
_chemical_formula_weight         618.62

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_H-M_alt        'C c'
_space_group_name_Hall           'C -2yc'

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

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

_cell_length_a                   5.7579(8)
_cell_length_b                   19.399(3)
_cell_length_c                   27.176(3)
_cell_angle_alpha                90
_cell_angle_beta                 90.640(12)
_cell_angle_gamma                90
_cell_volume                     3035.3(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    1084
_cell_measurement_theta_min      2.9670
_cell_measurement_theta_max      21.6180

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_F_000             1312
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.01
_exptl_absorpt_coefficient_mu    0.105
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.67936
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      297(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Incoatec microfocus source'
_diffrn_measurement_device_type  'MAR345 image plate'
_diffrn_measurement_method       
;
'120 images, ΔΦ 1.5° '
;
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            2332
_diffrn_reflns_av_unetI/netI     0.1135
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.998
_diffrn_reflns_theta_max         18.939
_diffrn_reflns_theta_full        18.939
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_point_group_measured_fraction_full 0.958
_reflns_number_total             2332
_reflns_number_gt                1783
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.947
_reflns_Friedel_fraction_max     0.950
_reflns_Friedel_fraction_full    0.935

_reflns_special_details          
;
 _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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection       MAR
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_atom_sites_solution_primary     dual
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'MERCURY (Macrae et al., 2008)'
_computing_publication_material  
;
'MERCURY (Macrae et al., 2008), Platon (Spek, 2009)'
;




_refine_special_details          'Refined as a 2-component twin.,Twin'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0800P)²+18.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 562 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -1.3(10)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2332
_refine_ls_number_parameters     398
_refine_ls_number_restraints     366
_refine_ls_R_factor_all          0.1125
_refine_ls_R_factor_gt           0.0819
_refine_ls_wR_factor_ref         0.2203
_refine_ls_wR_factor_gt          0.1907
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_restrained_S_all      1.055
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.836(4) 0.7981(11) 0.4575(8) 0.043(5) Uani 1 1 d . U . . .
H1A H 0.791826 0.762162 0.439339 0.051 Uiso 1 1 calc R U . . .
H1B H 0.964891 0.815717 0.444825 0.051 Uiso 1 1 calc R U . . .
C2 C 0.877(6) 0.7771(16) 0.5083(10) 0.061(8) Uani 1 1 d . U . . .
H2A H 0.871903 0.727260 0.510771 0.073 Uiso 1 1 calc R U . . .
H2AB H 1.028744 0.792613 0.519286 0.073 Uiso 1 1 calc R U . . .
C3 C 0.700(7) 0.8069(18) 0.5390(12) 0.076(9) Uani 1 1 d . U . . .
H3A H 0.762159 0.818934 0.571144 0.092 Uiso 1 1 calc R U . . .
H3AB H 0.570474 0.775438 0.542977 0.092 Uiso 1 1 calc R U . . .
C4 C 0.627(6) 0.8701(15) 0.5108(10) 0.057(7) Uani 1 1 d . U . . .
H4A H 0.467839 0.882429 0.517993 0.069 Uiso 1 1 calc R U . . .
H4AB H 0.727110 0.908874 0.518832 0.069 Uiso 1 1 calc R U . . .
C5 C 0.651(5) 0.8505(15) 0.4588(10) 0.048(6) Uani 1 1 d . U . . .
H5 H 0.692935 0.890561 0.438819 0.057 Uiso 1 1 calc R U . . .
C6 C 0.421(6) 0.8186(16) 0.4400(10) 0.046(7) Uani 1 1 d . U . . .
O7 O 0.415(4) 0.7537(10) 0.4365(7) 0.061(5) Uani 1 1 d . U . . .
O8 O 0.249(4) 0.8572(9) 0.4315(7) 0.057(5) Uani 1 1 d . U . . .
N11 N 0.367(4) 0.5885(11) 0.5460(8) 0.046(5) Uani 1 1 d . U . . .
H11A H 0.239922 0.568800 0.557839 0.055 Uiso 1 1 calc R U . . .
H11B H 0.405177 0.623870 0.565332 0.055 Uiso 1 1 calc R U . . .
C12 C 0.322(6) 0.6133(16) 0.4947(11) 0.062(8) Uani 1 1 d . U . . .
H12A H 0.158095 0.610435 0.486625 0.075 Uiso 1 1 calc R U . . .
H12B H 0.372070 0.660814 0.491161 0.075 Uiso 1 1 calc R U . . .
C13 C 0.449(8) 0.571(2) 0.4644(13) 0.096(10) Uani 1 1 d . U . . .
H13A H 0.558383 0.598471 0.446069 0.115 Uiso 1 1 calc R U . . .
H13B H 0.344359 0.549104 0.440806 0.115 Uiso 1 1 calc R U . . .
C14 C 0.573(6) 0.5188(16) 0.4895(10) 0.058(7) Uani 1 1 d . U . . .
H14A H 0.731925 0.517204 0.478313 0.069 Uiso 1 1 calc R U . . .
H14B H 0.501462 0.474248 0.483488 0.069 Uiso 1 1 calc R U . . .
C15 C 0.566(5) 0.5363(15) 0.5448(10) 0.049(6) Uani 1 1 d . U . . .
H15 H 0.527759 0.495353 0.564129 0.059 Uiso 1 1 calc R U . . .
C16 C 0.786(5) 0.5677(15) 0.5628(9) 0.041(6) Uani 1 1 d . U . . .
O17 O 0.787(4) 0.6321(10) 0.5696(7) 0.065(6) Uani 1 1 d . U . . .
O18 O 0.955(4) 0.5295(10) 0.5673(7) 0.061(6) Uani 1 1 d . U . . .
C21 C -0.464(6) 0.5424(17) 0.2526(11) 0.069(8) Uani 1 1 d . U . . .
H21 H -0.573494 0.572167 0.265797 0.083 Uiso 1 1 calc R U . . .
C22 C -0.505(6) 0.5119(19) 0.2068(12) 0.076(8) Uani 1 1 d . U . . .
H22 H -0.636069 0.524014 0.188385 0.091 Uiso 1 1 calc R U . . .
C23 C -0.362(7) 0.4668(19) 0.1903(11) 0.074(9) Uani 1 1 d . U . . .
H23 H -0.400758 0.444928 0.160900 0.089 Uiso 1 1 calc R U . . .
C24 C -0.162(7) 0.4491(18) 0.2122(11) 0.075(8) Uani 1 1 d . U . . .
H24 H -0.060803 0.417258 0.198399 0.090 Uiso 1 1 calc R U . . .
C25 C -0.113(5) 0.4818(15) 0.2574(10) 0.053(7) Uani 1 1 d . U . . .
H25 H 0.025134 0.471757 0.274071 0.064 Uiso 1 1 calc R U . . .
C26 C -0.268(5) 0.5291(15) 0.2777(10) 0.056(6) Uani 1 1 d . U . . .
C27 C -0.206(6) 0.5615(15) 0.3272(10) 0.058(6) Uani 1 1 d . U . . .
H27 H -0.346522 0.584811 0.338306 0.070 Uiso 1 1 calc R U . . .
C28 C -0.152(7) 0.5070(18) 0.3651(11) 0.057(7) Uani 1 1 d . U . . .
O29 O -0.326(4) 0.4634(11) 0.3730(7) 0.069(6) Uani 1 1 d . U . . .
H29 H -0.285935 0.435328 0.394027 0.104 Uiso 1 1 calc R U . . .
O30 O 0.029(5) 0.5010(12) 0.3847(9) 0.085(7) Uani 1 1 d . U . . .
C31 C -0.027(7) 0.6154(17) 0.3228(12) 0.069(8) Uani 1 1 d . U . . .
H31A H -0.077774 0.648481 0.298146 0.083 Uiso 1 1 calc R U . . .
H31B H 0.115260 0.594507 0.311373 0.083 Uiso 1 1 calc R U . . .
C32 C 0.023(7) 0.6533(18) 0.3700(13) 0.063(8) Uani 1 1 d . U . . .
O33 O -0.106(5) 0.6643(12) 0.4033(9) 0.085(7) Uani 1 1 d . U . . .
O34 O 0.237(4) 0.6778(11) 0.3667(7) 0.073(6) Uani 1 1 d . U . . .
H34 H 0.270402 0.699062 0.391892 0.110 Uiso 1 1 calc R U . . .
C41 C 1.413(6) 0.7005(15) 0.7373(11) 0.061(7) Uani 1 1 d . U . . .
H41 H 1.528383 0.700048 0.713610 0.073 Uiso 1 1 calc R U . . .
C42 C 1.439(7) 0.6604(17) 0.7802(12) 0.076(9) Uani 1 1 d . U . . .
H42 H 1.566423 0.631532 0.783979 0.092 Uiso 1 1 calc R U . . .
C43 C 1.287(7) 0.6637(17) 0.8136(12) 0.077(9) Uani 1 1 d . U . . .
H43 H 1.311776 0.638283 0.842150 0.093 Uiso 1 1 calc R U . . .
C44 C 1.093(6) 0.7021(18) 0.8099(12) 0.077(8) Uani 1 1 d . U . . .
H44 H 0.982593 0.703334 0.834632 0.092 Uiso 1 1 calc R U . . .
C45 C 1.068(6) 0.7410(17) 0.7654(11) 0.070(8) Uani 1 1 d . U . . .
H45 H 0.937287 0.768622 0.761074 0.084 Uiso 1 1 calc R U . . .
C46 C 1.223(5) 0.7392(15) 0.7304(9) 0.049(6) Uani 1 1 d . U . . .
C47 C 1.193(6) 0.7820(14) 0.6822(10) 0.053(6) Uani 1 1 d . U . . .
H47 H 1.056986 0.811925 0.685229 0.064 Uiso 1 1 calc R U . . .
C48 C 1.153(6) 0.7314(15) 0.6395(11) 0.045(6) Uani 1 1 d . U . . .
O49 O 0.934(4) 0.7136(10) 0.6404(6) 0.062(6) Uani 1 1 d . U . . .
H49 H 0.906906 0.686493 0.617952 0.093 Uiso 1 1 calc R U . . .
O50 O 1.290(4) 0.7101(11) 0.6121(7) 0.072(6) Uani 1 1 d . U . . .
C51 C 1.404(6) 0.8259(14) 0.6715(11) 0.053(7) Uani 1 1 d . U . . .
H51A H 1.532299 0.796538 0.661753 0.063 Uiso 1 1 calc R U . . .
H51B H 1.451328 0.850682 0.700952 0.063 Uiso 1 1 calc R U . . .
C52 C 1.350(6) 0.8777(17) 0.6301(11) 0.058(8) Uani 1 1 d . U . . .
O53 O 1.518(4) 0.9236(10) 0.6272(7) 0.064(6) Uani 1 1 d . U . . .
H53 H 1.486564 0.951421 0.605381 0.095 Uiso 1 1 calc R U . . .
O54 O 1.180(4) 0.8781(11) 0.6056(7) 0.068(6) Uani 1 1 d . U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C2 1.46(3) . ?
N1 C5 1.47(3) . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
C2 C3 1.44(4) . ?
C2 H2A 0.9700 . ?
C2 H2AB 0.9700 . ?
C3 C4 1.50(4) . ?
C3 H3A 0.9700 . ?
C3 H3AB 0.9700 . ?
C4 C5 1.47(4) . ?
C4 H4A 0.9700 . ?
C4 H4AB 0.9700 . ?
C5 C6 1.54(4) . ?
C5 H5 0.9800 . ?
C6 O8 1.26(3) . ?
C6 O7 1.26(3) . ?
N11 C12 1.49(4) . ?
N11 C15 1.53(3) . ?
N11 H11A 0.8900 . ?
N11 H11B 0.8900 . ?
C12 C13 1.38(4) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.40(4) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.54(4) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.48(4) . ?
C15 H15 0.9800 . ?
C16 O18 1.23(3) . ?
C16 O17 1.26(3) . ?
C21 C26 1.34(4) . ?
C21 C22 1.40(4) . ?
C21 H21 0.9300 . ?
C22 C23 1.29(5) . ?
C22 H22 0.9300 . ?
C23 C24 1.34(5) . ?
C23 H23 0.9300 . ?
C24 C25 1.41(4) . ?
C24 H24 0.9300 . ?
C25 C26 1.40(4) . ?
C25 H25 0.9300 . ?
C26 C27 1.52(4) . ?
C27 C31 1.47(4) . ?
C27 C28 1.50(4) . ?
C27 H27 0.9800 . ?
C28 O30 1.17(4) . ?
C28 O29 1.33(4) . ?
O29 H29 0.8200 . ?
C31 C32 1.50(5) . ?
C31 H31A 0.9700 . ?
C31 H31B 0.9700 . ?
C32 O33 1.20(4) . ?
C32 O34 1.32(4) . ?
O34 H34 0.8200 . ?
C41 C46 1.34(4) . ?
C41 C42 1.41(4) . ?
C41 H41 0.9300 . ?
C42 C43 1.27(4) . ?
C42 H42 0.9300 . ?
C43 C44 1.35(4) . ?
C43 H43 0.9300 . ?
C44 C45 1.43(4) . ?
C44 H44 0.9300 . ?
C45 C46 1.31(4) . ?
C45 H45 0.9300 . ?
C46 C47 1.56(4) . ?
C47 C51 1.52(4) . ?
C47 C48 1.54(4) . ?
C47 H47 0.9800 . ?
C48 O50 1.17(3) . ?
C48 O49 1.31(4) . ?
O49 H49 0.8200 . ?
C51 C52 1.54(4) . ?
C51 H51A 0.9700 . ?
C51 H51B 0.9700 . ?
C52 O54 1.18(4) . ?
C52 O53 1.32(4) . ?
O53 H53 0.8200 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C5 106(2) . . ?
C2 N1 H1A 110.5 . . ?
C5 N1 H1A 110.5 . . ?
C2 N1 H1B 110.5 . . ?
C5 N1 H1B 110.5 . . ?
H1A N1 H1B 108.7 . . ?
C3 C2 N1 109(3) . . ?
C3 C2 H2A 109.8 . . ?
N1 C2 H2A 109.8 . . ?
C3 C2 H2AB 109.8 . . ?
N1 C2 H2AB 109.8 . . ?
H2A C2 H2AB 108.3 . . ?
C2 C3 C4 103(3) . . ?
C2 C3 H3A 111.1 . . ?
C4 C3 H3A 111.1 . . ?
C2 C3 H3AB 111.1 . . ?
C4 C3 H3AB 111.1 . . ?
H3A C3 H3AB 109.1 . . ?
C5 C4 C3 104(2) . . ?
C5 C4 H4A 110.9 . . ?
C3 C4 H4A 110.9 . . ?
C5 C4 H4AB 110.9 . . ?
C3 C4 H4AB 110.9 . . ?
H4A C4 H4AB 108.9 . . ?
C4 C5 N1 106(2) . . ?
C4 C5 C6 109(3) . . ?
N1 C5 C6 110(2) . . ?
C4 C5 H5 110.6 . . ?
N1 C5 H5 110.6 . . ?
C6 C5 H5 110.6 . . ?
O8 C6 O7 124(3) . . ?
O8 C6 C5 119(3) . . ?
O7 C6 C5 116(3) . . ?
C12 N11 C15 108(2) . . ?
C12 N11 H11A 110.0 . . ?
C15 N11 H11A 110.0 . . ?
C12 N11 H11B 110.0 . . ?
C15 N11 H11B 110.0 . . ?
H11A N11 H11B 108.4 . . ?
C13 C12 N11 106(3) . . ?
C13 C12 H12A 110.5 . . ?
N11 C12 H12A 110.5 . . ?
C13 C12 H12B 110.5 . . ?
N11 C12 H12B 110.5 . . ?
H12A C12 H12B 108.7 . . ?
C12 C13 C14 114(3) . . ?
C12 C13 H13A 108.8 . . ?
C14 C13 H13A 108.8 . . ?
C12 C13 H13B 108.8 . . ?
C14 C13 H13B 108.8 . . ?
H13A C13 H13B 107.6 . . ?
C13 C14 C15 107(3) . . ?
C13 C14 H14A 110.2 . . ?
C15 C14 H14A 110.2 . . ?
C13 C14 H14B 110.2 . . ?
C15 C14 H14B 110.2 . . ?
H14A C14 H14B 108.5 . . ?
C16 C15 N11 111(2) . . ?
C16 C15 C14 113(2) . . ?
N11 C15 C14 101(2) . . ?
C16 C15 H15 110.6 . . ?
N11 C15 H15 110.6 . . ?
C14 C15 H15 110.6 . . ?
O18 C16 O17 125(3) . . ?
O18 C16 C15 117(3) . . ?
O17 C16 C15 117(3) . . ?
C26 C21 C22 120(3) . . ?
C26 C21 H21 119.8 . . ?
C22 C21 H21 119.8 . . ?
C23 C22 C21 120(3) . . ?
C23 C22 H22 120.2 . . ?
C21 C22 H22 120.2 . . ?
C22 C23 C24 125(3) . . ?
C22 C23 H23 117.5 . . ?
C24 C23 H23 117.5 . . ?
C23 C24 C25 116(3) . . ?
C23 C24 H24 122.1 . . ?
C25 C24 H24 122.1 . . ?
C26 C25 C24 121(3) . . ?
C26 C25 H25 119.4 . . ?
C24 C25 H25 119.4 . . ?
C21 C26 C25 118(3) . . ?
C21 C26 C27 124(3) . . ?
C25 C26 C27 118(3) . . ?
C31 C27 C28 115(3) . . ?
C31 C27 C26 112(3) . . ?
C28 C27 C26 111(2) . . ?
C31 C27 H27 106.1 . . ?
C28 C27 H27 106.1 . . ?
C26 C27 H27 106.1 . . ?
O30 C28 O29 122(3) . . ?
O30 C28 C27 124(3) . . ?
O29 C28 C27 114(3) . . ?
C28 O29 H29 109.5 . . ?
C27 C31 C32 114(3) . . ?
C27 C31 H31A 108.7 . . ?
C32 C31 H31A 108.7 . . ?
C27 C31 H31B 108.7 . . ?
C32 C31 H31B 108.7 . . ?
H31A C31 H31B 107.6 . . ?
O33 C32 O34 125(3) . . ?
O33 C32 C31 128(4) . . ?
O34 C32 C31 107(3) . . ?
C32 O34 H34 109.5 . . ?
C46 C41 C42 120(3) . . ?
C46 C41 H41 119.9 . . ?
C42 C41 H41 119.9 . . ?
C43 C42 C41 120(4) . . ?
C43 C42 H42 120.0 . . ?
C41 C42 H42 120.0 . . ?
C42 C43 C44 124(4) . . ?
C42 C43 H43 118.2 . . ?
C44 C43 H43 118.2 . . ?
C43 C44 C45 115(3) . . ?
C43 C44 H44 122.3 . . ?
C45 C44 H44 122.3 . . ?
C46 C45 C44 122(3) . . ?
C46 C45 H45 118.8 . . ?
C44 C45 H45 118.8 . . ?
C45 C46 C41 118(3) . . ?
C45 C46 C47 122(3) . . ?
C41 C46 C47 120(3) . . ?
C51 C47 C48 109(3) . . ?
C51 C47 C46 112(3) . . ?
C48 C47 C46 108(2) . . ?
C51 C47 H47 109.1 . . ?
C48 C47 H47 109.1 . . ?
C46 C47 H47 109.1 . . ?
O50 C48 O49 125(3) . . ?
O50 C48 C47 128(3) . . ?
O49 C48 C47 107(3) . . ?
C48 O49 H49 109.5 . . ?
C47 C51 C52 111(3) . . ?
C47 C51 H51A 109.5 . . ?
C52 C51 H51A 109.5 . . ?
C47 C51 H51B 109.5 . . ?
C52 C51 H51B 109.5 . . ?
H51A C51 H51B 108.1 . . ?
O54 C52 O53 125(3) . . ?
O54 C52 C51 125(3) . . ?
O53 C52 C51 110(3) . . ?
C52 O53 H53 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C2 C3 9(3) . . . . ?
N1 C2 C3 C4 -26(4) . . . . ?
C2 C3 C4 C5 33(4) . . . . ?
C3 C4 C5 N1 -29(3) . . . . ?
C3 C4 C5 C6 89(3) . . . . ?
C2 N1 C5 C4 13(3) . . . . ?
C2 N1 C5 C6 -105(3) . . . . ?
C4 C5 C6 O8 74(3) . . . . ?
N1 C5 C6 O8 -170(2) . . . . ?
C4 C5 C6 O7 -102(3) . . . . ?
N1 C5 C6 O7 13(3) . . . . ?
C15 N11 C12 C13 11(3) . . . . ?
N11 C12 C13 C14 1(4) . . . . ?
C12 C13 C14 C15 -12(5) . . . . ?
C12 N11 C15 C16 103(3) . . . . ?
C12 N11 C15 C14 -16(3) . . . . ?
C13 C14 C15 C16 -102(3) . . . . ?
C13 C14 C15 N11 17(3) . . . . ?
N11 C15 C16 O18 175(2) . . . . ?
C14 C15 C16 O18 -73(3) . . . . ?
N11 C15 C16 O17 -10(3) . . . . ?
C14 C15 C16 O17 103(3) . . . . ?
C26 C21 C22 C23 5(5) . . . . ?
C21 C22 C23 C24 -5(6) . . . . ?
C22 C23 C24 C25 2(5) . . . . ?
C23 C24 C25 C26 1(5) . . . . ?
C22 C21 C26 C25 -3(5) . . . . ?
C22 C21 C26 C27 178(3) . . . . ?
C24 C25 C26 C21 0(5) . . . . ?
C24 C25 C26 C27 179(3) . . . . ?
C21 C26 C27 C31 -105(4) . . . . ?
C25 C26 C27 C31 76(4) . . . . ?
C21 C26 C27 C28 125(3) . . . . ?
C25 C26 C27 C28 -54(4) . . . . ?
C31 C27 C28 O30 -11(5) . . . . ?
C26 C27 C28 O30 118(4) . . . . ?
C31 C27 C28 O29 172(3) . . . . ?
C26 C27 C28 O29 -59(4) . . . . ?
C28 C27 C31 C32 -57(4) . . . . ?
C26 C27 C31 C32 175(3) . . . . ?
C27 C31 C32 O33 -30(5) . . . . ?
C27 C31 C32 O34 155(3) . . . . ?
C46 C41 C42 C43 -4(5) . . . . ?
C41 C42 C43 C44 3(6) . . . . ?
C42 C43 C44 C45 -1(5) . . . . ?
C43 C44 C45 C46 0(5) . . . . ?
C44 C45 C46 C41 -1(5) . . . . ?
C44 C45 C46 C47 -180(3) . . . . ?
C42 C41 C46 C45 3(5) . . . . ?
C42 C41 C46 C47 -179(3) . . . . ?
C45 C46 C47 C51 127(3) . . . . ?
C41 C46 C47 C51 -51(4) . . . . ?
C45 C46 C47 C48 -112(3) . . . . ?
C41 C46 C47 C48 69(4) . . . . ?
C51 C47 C48 O50 26(4) . . . . ?
C46 C47 C48 O50 -97(4) . . . . ?
C51 C47 C48 O49 -157(2) . . . . ?
C46 C47 C48 O49 81(3) . . . . ?
C48 C47 C51 C52 72(3) . . . . ?
C46 C47 C51 C52 -169(2) . . . . ?
C47 C51 C52 O54 -9(5) . . . . ?
C47 C51 C52 O53 168(2) . . . . ?

_refine_diff_density_max         0.222
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.059

####################################################################### 
# 
# 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_alex_A173_AA22
_database_code_depnum_ccdc_archive 'CCDC 2247561'
loop_
_audit_author_name
_audit_author_address
'Koen Robeyns'
;Universite catholique de Louvain
Belgium
;
_audit_update_record             
;
2023-03-09 deposited with the CCDC.	2023-04-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H7 Cl O3, C5 H9 N O2'
_chemical_formula_sum            'C13 H16 Cl N O5'
_chemical_formula_weight         301.72

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   7.0457(14)
_cell_length_b                   8.2146(9)
_cell_length_c                   13.342(3)
_cell_angle_alpha                106.407(14)
_cell_angle_beta                 90.268(16)
_cell_angle_gamma                106.101(14)
_cell_volume                     708.8(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    1843
_cell_measurement_theta_min      3.1750
_cell_measurement_theta_max      25.1600

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.414
_exptl_crystal_F_000             316
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.02
_exptl_absorpt_coefficient_mu    0.288
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.91457
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?




_diffrn_ambient_temperature      297(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Incoatec microfocus source'
_diffrn_measurement_device_type  'MAR345 image plate'
_diffrn_measurement_method       
;
'80 images, ΔΦ 3.0° '
'40 images, ΔΦ 3.0° (2nd orientation)'
;
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9168
_diffrn_reflns_av_unetI/netI     0.0422
_diffrn_reflns_av_R_equivalents  0.0457
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.022
_diffrn_reflns_theta_max         25.237
_diffrn_reflns_theta_full        25.237
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             2557
_reflns_number_gt                1983
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       MAR
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_atom_sites_solution_primary     'dual space'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'MERCURY (Macrae et al., 2008)'
_computing_publication_material  
;
'MERCURY (Macrae et al., 2008), Platon (Spek, 2009)'
;






_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0573P)²+0.5189P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2557
_refine_ls_number_parameters     253
_refine_ls_number_restraints     143
_refine_ls_R_factor_all          0.0782
_refine_ls_R_factor_gt           0.0577
_refine_ls_wR_factor_ref         0.1441
_refine_ls_wR_factor_gt          0.1343
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.107
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.4554(3) -0.0373(3) 0.63071(16) 0.0355(5) Uani 1 1 d D . . . .
H1A H 0.435376 -0.135497 0.577116 0.043 Uiso 1 1 calc R U . A 3
H1AB H 0.521197 0.054510 0.609449 0.043 Uiso 1 1 calc R U . A 3
C2 C 0.573(2) -0.049(3) 0.7198(6) 0.048(6) Uani 0.539(13) 1 d D . P B 3
H2A H 0.714644 -0.009563 0.713541 0.058 Uiso 0.539(13) 1 calc R U P B 3
H2B H 0.537924 -0.169209 0.725228 0.058 Uiso 0.539(13) 1 calc R U P B 3
C3 C 0.5120(11) 0.0743(13) 0.8106(5) 0.056(2) Uani 0.539(13) 1 d D U P B 3
H3A H 0.521012 0.038891 0.873520 0.067 Uiso 0.539(13) 1 calc R U P B 3
H3AB H 0.597879 0.194281 0.823151 0.067 Uiso 0.539(13) 1 calc R U P B 3
C4 C 0.3077(13) 0.0660(16) 0.7842(4) 0.043(3) Uani 0.539(13) 1 d D U P B 3
H4A H 0.291677 0.184145 0.806008 0.052 Uiso 0.539(13) 1 calc R U P B 3
H4AB H 0.218050 -0.006365 0.820349 0.052 Uiso 0.539(13) 1 calc R U P B 3
C2B C 0.575(2) -0.029(4) 0.7250(7) 0.050(7) Uani 0.461(13) 1 d D . P B 4
H2C H 0.679925 0.082481 0.747845 0.059 Uiso 0.461(13) 1 calc R U P B 4
H2D H 0.635585 -0.125268 0.709294 0.059 Uiso 0.461(13) 1 calc R U P B 4
C3B C 0.4363(14) -0.0452(18) 0.8090(6) 0.062(3) Uani 0.461(13) 1 d D U P B 4
H3BA H 0.389324 -0.167322 0.810064 0.074 Uiso 0.461(13) 1 calc R U P B 4
H3BB H 0.502850 0.027775 0.877265 0.074 Uiso 0.461(13) 1 calc R U P B 4
C4B C 0.2705(16) 0.0153(19) 0.7835(5) 0.051(4) Uani 0.461(13) 1 d D U P B 4
H4BA H 0.293033 0.139892 0.820560 0.061 Uiso 0.461(13) 1 calc R U P B 4
H4BB H 0.147775 -0.052114 0.803136 0.061 Uiso 0.461(13) 1 calc R U P B 4
C5 C 0.2601(4) -0.0144(4) 0.6661(2) 0.0388(6) Uani 1 1 d D . . . .
H5 H 0.158794 -0.129592 0.649663 0.047 Uiso 1 1 calc R U . B 3
C6 C 0.1937(4) 0.1098(3) 0.6172(2) 0.0365(6) Uani 1 1 d . . . . .
O7 O 0.2892(3) 0.1532(2) 0.54509(15) 0.0443(5) Uani 1 1 d . . . . .
O8 O 0.0493(3) 0.1550(3) 0.65351(18) 0.0626(6) Uani 1 1 d . . . . .
C11 C 0.2389(3) 0.4919(3) 0.46398(19) 0.0310(5) Uani 1 1 d . . . . .
O12 O 0.3271(3) 0.5841(2) 0.54752(14) 0.0422(5) Uani 1 1 d . . . . .
O13 O 0.1808(3) 0.3181(2) 0.43361(15) 0.0403(5) Uani 1 1 d . . . . .
H13 H 0.221(4) 0.2758(15) 0.487(2) 0.060 Uiso 1 1 calc R U . . .
C14 C 0.1674(4) 0.5657(3) 0.3829(2) 0.0345(6) Uani 1 1 d . . . . .
H14 H 0.022284 0.532879 0.379384 0.041 Uiso 1 1 calc R U . C 1
O15 O 0.2398(3) 0.7534(2) 0.41740(14) 0.0386(5) Uani 1 1 d . . . . .
H15 H 0.152(4) 0.7961(17) 0.404(2) 0.058 Uiso 1 1 calc R U . . .
C16 C 0.227(2) 0.4848(15) 0.2726(7) 0.037(4) Uani 0.54(3) 1 d G U P D 1
C17 C 0.4189(19) 0.4758(18) 0.2572(10) 0.035(2) Uani 0.54(3) 1 d G U P D 1
H17 H 0.512041 0.510125 0.314452 0.042 Uiso 0.54(3) 1 calc R U P D 1
C18 C 0.4720(15) 0.4156(18) 0.1562(12) 0.063(3) Uani 0.54(3) 1 d G U P D 1
H18 H 0.600679 0.409644 0.145839 0.076 Uiso 0.54(3) 1 calc R U P D 1
C19 C 0.3329(19) 0.3644(17) 0.0705(9) 0.073(3) Uani 0.54(3) 1 d G U P D 1
H19 H 0.368422 0.324130 0.002952 0.088 Uiso 0.54(3) 1 calc R U P D 1
C20 C 0.1406(19) 0.3734(19) 0.0860(7) 0.063(3) Uani 0.54(3) 1 d G U P D 1
C21 C 0.0875(16) 0.4336(17) 0.1870(8) 0.051(2) Uani 0.54(3) 1 d G U P D 1
H21 H -0.041117 0.439577 0.197291 0.062 Uiso 0.54(3) 1 calc R U P D 1
Cl22 Cl -0.042(2) 0.290(3) -0.0162(5) 0.139(3) Uani 0.54(3) 1 d . U P D 1
C16B C 0.221(2) 0.4916(16) 0.2754(8) 0.037(5) Uani 0.46(3) 1 d G U P D 2
C17B C 0.417(2) 0.5150(18) 0.2526(12) 0.034(2) Uani 0.46(3) 1 d G U P D 2
H17B H 0.519352 0.582064 0.304802 0.040 Uiso 0.46(3) 1 calc R U P D 2
C18B C 0.4609(17) 0.4383(19) 0.1519(14) 0.050(3) Uani 0.46(3) 1 d G U P D 2
H18B H 0.592222 0.453996 0.136618 0.060 Uiso 0.46(3) 1 calc R U P D 2
C19B C 0.308(2) 0.3381(18) 0.0739(10) 0.076(4) Uani 0.46(3) 1 d G U P D 2
H19B H 0.337399 0.286769 0.006434 0.092 Uiso 0.46(3) 1 calc R U P D 2
C20B C 0.1119(18) 0.315(2) 0.0966(9) 0.060(3) Uani 0.46(3) 1 d G U P D 2
C21B C 0.0682(18) 0.391(2) 0.1974(10) 0.053(3) Uani 0.46(3) 1 d G U P D 2
H21B H -0.063170 0.375676 0.212616 0.064 Uiso 0.46(3) 1 calc R U P D 2
Cl2B Cl -0.0695(13) 0.201(3) -0.0039(6) 0.132(4) Uani 0.46(3) 1 d . U P D 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
N1 C2B 1.488(7) . ?
N1 C2 1.488(6) . ?
N1 C5 1.500(3) . ?
N1 H1A 0.8900 . ?
N1 H1AB 0.8900 . ?
C2 C3 1.497(12) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.458(7) . ?
C3 H3A 0.9700 . ?
C3 H3AB 0.9700 . ?
C4 C5 1.523(6) . ?
C4 H4A 0.9700 . ?
C4 H4AB 0.9700 . ?
C2B C3B 1.502(12) . ?
C2B H2C 0.9700 . ?
C2B H2D 0.9700 . ?
C3B C4B 1.462(8) . ?
C3B H3BA 0.9700 . ?
C3B H3BB 0.9700 . ?
C4B C5 1.515(7) . ?
C4B H4BA 0.9700 . ?
C4B H4BB 0.9700 . ?
C5 C6 1.524(3) . ?
C5 H5 0.9800 . ?
C6 O8 1.233(3) . ?
C6 O7 1.253(3) . ?
C11 O12 1.207(3) . ?
C11 O13 1.310(3) . ?
C11 C14 1.525(3) . ?
O13 H13 0.95(3) . ?
C14 O15 1.418(3) . ?
C14 C16B 1.486(12) . ?
C14 C16 1.546(10) . ?
C14 H14 0.9800 . ?
O15 H15 0.83(3) . ?
C16 C17 1.3900 . ?
C16 C21 1.3900 . ?
C17 C18 1.3900 . ?
C17 H17 0.9300 . ?
C18 C19 1.3900 . ?
C18 H18 0.9300 . ?
C19 C20 1.3900 . ?
C19 H19 0.9300 . ?
C20 C21 1.3900 . ?
C20 Cl22 1.719(11) . ?
C21 H21 0.9300 . ?
C16B C17B 1.3900 . ?
C16B C21B 1.3900 . ?
C17B C18B 1.3900 . ?
C17B H17B 0.9300 . ?
C18B C19B 1.3900 . ?
C18B H18B 0.9300 . ?
C19B C20B 1.3900 . ?
C19B H19B 0.9300 . ?
C20B C21B 1.3900 . ?
C20B Cl2B 1.709(12) . ?
C21B H21B 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2B N1 C5 106.8(4) . . ?
C2 N1 C5 109.0(4) . . ?
C2 N1 H1A 109.9 . . ?
C5 N1 H1A 109.9 . . ?
C2 N1 H1AB 109.9 . . ?
C5 N1 H1AB 109.9 . . ?
H1A N1 H1AB 108.3 . . ?
N1 C2 C3 101.0(7) . . ?
N1 C2 H2A 111.6 . . ?
C3 C2 H2A 111.6 . . ?
N1 C2 H2B 111.6 . . ?
C3 C2 H2B 111.6 . . ?
H2A C2 H2B 109.4 . . ?
C4 C3 C2 107.5(6) . . ?
C4 C3 H3A 110.2 . . ?
C2 C3 H3A 110.2 . . ?
C4 C3 H3AB 110.2 . . ?
C2 C3 H3AB 110.2 . . ?
H3A C3 H3AB 108.5 . . ?
C3 C4 C5 108.5(5) . . ?
C3 C4 H4A 110.0 . . ?
C5 C4 H4A 110.0 . . ?
C3 C4 H4AB 110.0 . . ?
C5 C4 H4AB 110.0 . . ?
H4A C4 H4AB 108.4 . . ?
N1 C2B C3B 106.9(7) . . ?
N1 C2B H2C 110.3 . . ?
C3B C2B H2C 110.3 . . ?
N1 C2B H2D 110.3 . . ?
C3B C2B H2D 110.3 . . ?
H2C C2B H2D 108.6 . . ?
C4B C3B C2B 106.6(7) . . ?
C4B C3B H3BA 110.4 . . ?
C2B C3B H3BA 110.4 . . ?
C4B C3B H3BB 110.4 . . ?
C2B C3B H3BB 110.4 . . ?
H3BA C3B H3BB 108.6 . . ?
C3B C4B C5 106.1(5) . . ?
C3B C4B H4BA 110.5 . . ?
C5 C4B H4BA 110.5 . . ?
C3B C4B H4BB 110.5 . . ?
C5 C4B H4BB 110.5 . . ?
H4BA C4B H4BB 108.7 . . ?
N1 C5 C4B 107.1(4) . . ?
N1 C5 C4 102.1(3) . . ?
N1 C5 C6 111.5(2) . . ?
C4B C5 C6 121.3(5) . . ?
C4 C5 C6 111.5(4) . . ?
N1 C5 H5 110.5 . . ?
C4 C5 H5 110.5 . . ?
C6 C5 H5 110.5 . . ?
O8 C6 O7 127.5(2) . . ?
O8 C6 C5 115.2(2) . . ?
O7 C6 C5 117.2(2) . . ?
O12 C11 O13 125.4(2) . . ?
O12 C11 C14 123.3(2) . . ?
O13 C11 C14 111.2(2) . . ?
C11 O13 H13 109.5 . . ?
O15 C14 C16B 111.6(5) . . ?
O15 C14 C11 109.0(2) . . ?
C16B C14 C11 113.5(6) . . ?
O15 C14 C16 112.6(5) . . ?
C11 C14 C16 111.5(5) . . ?
O15 C14 H14 107.8 . . ?
C11 C14 H14 107.8 . . ?
C16 C14 H14 107.8 . . ?
C14 O15 H15 109.5 . . ?
C17 C16 C21 120.0 . . ?
C17 C16 C14 121.3(8) . . ?
C21 C16 C14 118.5(8) . . ?
C18 C17 C16 120.0 . . ?
C18 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
C19 C18 C17 120.0 . . ?
C19 C18 H18 120.0 . . ?
C17 C18 H18 120.0 . . ?
C18 C19 C20 120.0 . . ?
C18 C19 H19 120.0 . . ?
C20 C19 H19 120.0 . . ?
C19 C20 C21 120.0 . . ?
C19 C20 Cl22 121.5(7) . . ?
C21 C20 Cl22 118.2(7) . . ?
C20 C21 C16 120.0 . . ?
C20 C21 H21 120.0 . . ?
C16 C21 H21 120.0 . . ?
C17B C16B C21B 120.0 . . ?
C17B C16B C14 121.8(10) . . ?
C21B C16B C14 118.2(10) . . ?
C18B C17B C16B 120.0 . . ?
C18B C17B H17B 120.0 . . ?
C16B C17B H17B 120.0 . . ?
C17B C18B C19B 120.0 . . ?
C17B C18B H18B 120.0 . . ?
C19B C18B H18B 120.0 . . ?
C20B C19B C18B 120.0 . . ?
C20B C19B H19B 120.0 . . ?
C18B C19B H19B 120.0 . . ?
C19B C20B C21B 120.0 . . ?
C19B C20B Cl2B 118.0(8) . . ?
C21B C20B Cl2B 121.9(9) . . ?
C20B C21B C16B 120.0 . . ?
C20B C21B H21B 120.0 . . ?
C16B C21B H21B 120.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C2 C3 -34.6(16) . . . . ?
N1 C2 C3 C4 31.5(16) . . . . ?
C2 C3 C4 C5 -17.9(13) . . . . ?
C5 N1 C2B C3B 13(2) . . . . ?
N1 C2B C3B C4B -24(2) . . . . ?
C2B C3B C4B C5 25.6(16) . . . . ?
C2B N1 C5 C4B 2.4(14) . . . . ?
C2 N1 C5 C4 24.1(12) . . . . ?
C2B N1 C5 C6 137.3(12) . . . . ?
C2 N1 C5 C6 143.2(11) . . . . ?
C3B C4B C5 N1 -17.4(10) . . . . ?
C3B C4B C5 C6 -146.9(7) . . . . ?
C3 C4 C5 N1 -3.5(8) . . . . ?
C3 C4 C5 C6 -122.6(6) . . . . ?
N1 C5 C6 O8 -170.2(2) . . . . ?
C4B C5 C6 O8 -42.7(7) . . . . ?
C4 C5 C6 O8 -56.8(5) . . . . ?
N1 C5 C6 O7 10.2(3) . . . . ?
C4B C5 C6 O7 137.8(6) . . . . ?
C4 C5 C6 O7 123.6(5) . . . . ?
O12 C11 C14 O15 6.2(3) . . . . ?
O13 C11 C14 O15 -177.93(19) . . . . ?
O12 C11 C14 C16B 131.3(7) . . . . ?
O13 C11 C14 C16B -52.9(7) . . . . ?
O12 C11 C14 C16 131.2(6) . . . . ?
O13 C11 C14 C16 -52.9(6) . . . . ?
O15 C14 C16 C17 74.9(8) . . . . ?
C11 C14 C16 C17 -48.0(8) . . . . ?
O15 C14 C16 C21 -100.0(8) . . . . ?
C11 C14 C16 C21 137.1(7) . . . . ?
C21 C16 C17 C18 0.0 . . . . ?
C14 C16 C17 C18 -174.8(9) . . . . ?
C16 C17 C18 C19 0.0 . . . . ?
C17 C18 C19 C20 0.0 . . . . ?
C18 C19 C20 C21 0.0 . . . . ?
C18 C19 C20 Cl22 -173.2(7) . . . . ?
C19 C20 C21 C16 0.0 . . . . ?
Cl22 C20 C21 C16 173.5(6) . . . . ?
C17 C16 C21 C20 0.0 . . . . ?
C14 C16 C21 C20 175.0(9) . . . . ?
O15 C14 C16B C17B 62.0(10) . . . . ?
C11 C14 C16B C17B -61.7(9) . . . . ?
O15 C14 C16B C21B -120.2(8) . . . . ?
C11 C14 C16B C21B 116.1(8) . . . . ?
C21B C16B C17B C18B 0.0 . . . . ?
C14 C16B C17B C18B 177.7(11) . . . . ?
C16B C17B C18B C19B 0.0 . . . . ?
C17B C18B C19B C20B 0.0 . . . . ?
C18B C19B C20B C21B 0.0 . . . . ?
C18B C19B C20B Cl2B 176.4(7) . . . . ?
C19B C20B C21B C16B 0.0 . . . . ?
Cl2B C20B C21B C16B -176.3(7) . . . . ?
C17B C16B C21B C20B 0.0 . . . . ?
C14 C16B C21B C20B -177.8(11) . . . . ?

_refine_diff_density_max         0.358
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.045

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

data_alex_fl170
_database_code_depnum_ccdc_archive 'CCDC 2247560'
loop_
_audit_author_name
_audit_author_address
'Koen Robeyns'
;Universite catholique de Louvain
Belgium
;
_audit_update_record             
;
2023-03-09 deposited with the CCDC.	2023-04-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H10 O3, C5 H9 N O2'
_chemical_formula_sum            'C14 H19 N O5'
_chemical_formula_weight         281.30

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

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

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

_cell_length_a                   10.4273(3)
_cell_length_b                   9.0611(3)
_cell_length_c                   30.1865(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2852.10(16)
_cell_formula_units_Z            8
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    4819
_cell_measurement_theta_min      3.0360
_cell_measurement_theta_max      25.0310

_exptl_crystal_description       'thick plate'
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_F_000             1200
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.03
_exptl_absorpt_coefficient_mu    0.100
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.61234
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?



_diffrn_ambient_temperature      297(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Incoatec microfocus source'
_diffrn_measurement_device_type  'MAR345 image plate'
_diffrn_measurement_method       
;
'150 images, ΔΦ 1.2° '
;
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17328
_diffrn_reflns_av_unetI/netI     0.0220
_diffrn_reflns_av_R_equivalents  0.0483
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_theta_min         3.054
_diffrn_reflns_theta_max         25.235
_diffrn_reflns_theta_full        25.235
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             2572
_reflns_number_gt                1906
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       MAR
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_atom_sites_solution_primary     'dual space'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'MERCURY (Macrae et al., 2008)'
_computing_publication_material  
;
'MERCURY (Macrae et al., 2008), Platon (Spek, 2009)'
;



_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0457P)²+2.9020P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2572
_refine_ls_number_parameters     212
_refine_ls_number_restraints     33
_refine_ls_R_factor_all          0.0714
_refine_ls_R_factor_gt           0.0531
_refine_ls_wR_factor_ref         0.1453
_refine_ls_wR_factor_gt          0.1350
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.99062(19) 0.8878(2) 0.78773(7) 0.0467(5) Uani 1 1 d D U . . .
H1A H 1.037805 0.811605 0.778742 0.056 Uiso 1 1 calc R U . A 1
H1B H 1.031172 0.970515 0.780219 0.056 Uiso 1 1 calc R U . A 1
C2 C 0.9741(5) 0.8818(16) 0.83657(12) 0.060(2) Uani 0.799(9) 1 d D . P B 1
H2A H 1.035872 0.944674 0.851445 0.072 Uiso 0.799(9) 1 calc R U P B 1
H2B H 0.983016 0.781722 0.847522 0.072 Uiso 0.799(9) 1 calc R U P B 1
C3 C 0.8391(4) 0.9381(6) 0.84301(11) 0.0582(13) Uani 0.799(9) 1 d D . P B 1
H3A H 0.835821 1.045016 0.841693 0.070 Uiso 0.799(9) 1 calc R U P B 1
H3B H 0.803565 0.905222 0.871028 0.070 Uiso 0.799(9) 1 calc R U P B 1
C4 C 0.7688(5) 0.8685(13) 0.80392(14) 0.067(3) Uani 0.799(9) 1 d D . P B 1
H4A H 0.749246 0.765718 0.809781 0.081 Uiso 0.799(9) 1 calc R U P B 1
H4B H 0.689657 0.920751 0.797688 0.081 Uiso 0.799(9) 1 calc R U P B 1
C2B C 0.9684(19) 0.896(6) 0.8364(3) 0.052(6) Uani 0.201(9) 1 d D U P B 2
H2C H 0.966221 0.997738 0.846446 0.062 Uiso 0.201(9) 1 calc R U P B 2
H2D H 1.034386 0.843301 0.852546 0.062 Uiso 0.201(9) 1 calc R U P B 2
C3B C 0.8388(14) 0.823(2) 0.8419(4) 0.060(5) Uani 0.201(9) 1 d D U P B 2
H3C H 0.799840 0.847862 0.870138 0.071 Uiso 0.201(9) 1 calc R U P B 2
H3D H 0.844916 0.716349 0.839311 0.071 Uiso 0.201(9) 1 calc R U P B 2
C4B C 0.7650(14) 0.890(4) 0.8031(4) 0.046(5) Uani 0.201(9) 1 d D U P B 2
H4C H 0.688850 0.833438 0.796149 0.055 Uiso 0.201(9) 1 calc R U P B 2
H4D H 0.740398 0.991613 0.809272 0.055 Uiso 0.201(9) 1 calc R U P B 2
C5 C 0.8619(2) 0.8829(3) 0.76585(8) 0.0398(6) Uani 1 1 d D U . . .
H5 H 0.846419 0.976297 0.750362 0.048 Uiso 1 1 calc R U . B 1
C6 C 0.8529(2) 0.7556(3) 0.73295(8) 0.0388(5) Uani 1 1 d . . . . .
O7 O 0.9496(2) 0.6800(2) 0.72676(7) 0.0678(6) Uani 1 1 d . . . . .
O8 O 0.74675(18) 0.7431(2) 0.71375(6) 0.0571(5) Uani 1 1 d . . . . .
C11 C 0.4012(3) 0.5702(3) 0.56025(11) 0.0638(8) Uani 1 1 d . . . . .
H11 H 0.359704 0.482950 0.567883 0.077 Uiso 1 1 calc R U . . .
C12 C 0.3298(3) 0.6946(4) 0.55085(11) 0.0735(9) Uani 1 1 d . . . . .
H12 H 0.240793 0.690633 0.552547 0.088 Uiso 1 1 calc R U . . .
C13 C 0.3883(3) 0.8227(4) 0.53913(10) 0.0680(9) Uani 1 1 d . . . . .
H13 H 0.339844 0.905750 0.532219 0.082 Uiso 1 1 calc R U . . .
C14 C 0.5188(3) 0.8282(4) 0.53762(12) 0.0762(10) Uani 1 1 d . . . . .
H14 H 0.559732 0.915849 0.530089 0.091 Uiso 1 1 calc R U . . .
C15 C 0.5906(3) 0.7040(3) 0.54722(10) 0.0647(8) Uani 1 1 d . . . . .
H15 H 0.679617 0.709304 0.546007 0.078 Uiso 1 1 calc R U . . .
C16 C 0.5333(3) 0.5735(3) 0.55849(8) 0.0453(6) Uani 1 1 d . . . . .
C17 C 0.6139(3) 0.4384(3) 0.56774(9) 0.0565(7) Uani 1 1 d . . . . .
H17A H 0.703024 0.463010 0.562163 0.068 Uiso 1 1 calc R U . . .
H17B H 0.589846 0.361901 0.546865 0.068 Uiso 1 1 calc R U . . .
C18 C 0.6036(3) 0.3754(3) 0.61441(9) 0.0554(7) Uani 1 1 d . . . . .
H18 H 0.673506 0.304484 0.618478 0.066 Uiso 1 1 calc R U . . .
O19 O 0.4862(2) 0.2988(3) 0.61935(9) 0.0827(8) Uani 1 1 d . . . . .
H19 H 0.470(2) 0.286(5) 0.6481(15) 0.124 Uiso 1 1 calc R U . . .
C20 C 0.6157(3) 0.4920(3) 0.64981(9) 0.0465(6) Uani 1 1 d . . . . .
O21 O 0.52987(19) 0.5184(2) 0.67555(7) 0.0653(6) Uani 1 1 d . . . . .
O22 O 0.72651(18) 0.5589(2) 0.64959(6) 0.0565(5) Uani 1 1 d . . . . .
H22 H 0.7330(3) 0.620(2) 0.6748(9) 0.085 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C2 1.485(4) . ?
N1 C2B 1.489(9) . ?
N1 C5 1.497(3) . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
C2 C3 1.510(9) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.525(8) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.509(4) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C2B C3B 1.515(13) . ?
C2B H2C 0.9700 . ?
C2B H2D 0.9700 . ?
C3B C4B 1.532(11) . ?
C3B H3C 0.9700 . ?
C3B H3D 0.9700 . ?
C4B C5 1.512(9) . ?
C4B H4C 0.9700 . ?
C4B H4D 0.9700 . ?
C5 C6 1.525(3) . ?
C5 H5 0.9800 . ?
C6 O7 1.233(3) . ?
C6 O8 1.254(3) . ?
C11 C16 1.379(4) . ?
C11 C12 1.381(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.358(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.362(5) . ?
C13 H13 0.9300 . ?
C14 C15 1.382(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.368(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.511(4) . ?
C17 C18 1.524(4) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 O19 1.415(3) . ?
C18 C20 1.508(4) . ?
C18 H18 0.9800 . ?
O19 H19 0.89(5) . ?
C20 O21 1.209(3) . ?
C20 O22 1.305(3) . ?
O22 H22 0.94(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C5 109.4(3) . . ?
C2B N1 C5 107.3(8) . . ?
C2 N1 H1A 109.8 . . ?
C5 N1 H1A 109.8 . . ?
C2 N1 H1B 109.8 . . ?
C5 N1 H1B 109.8 . . ?
H1A N1 H1B 108.2 . . ?
N1 C2 C3 102.9(5) . . ?
N1 C2 H2A 111.2 . . ?
C3 C2 H2A 111.2 . . ?
N1 C2 H2B 111.2 . . ?
C3 C2 H2B 111.2 . . ?
H2A C2 H2B 109.1 . . ?
C2 C3 C4 102.0(5) . . ?
C2 C3 H3A 111.4 . . ?
C4 C3 H3A 111.4 . . ?
C2 C3 H3B 111.4 . . ?
C4 C3 H3B 111.4 . . ?
H3A C3 H3B 109.2 . . ?
C5 C4 C3 104.2(4) . . ?
C5 C4 H4A 110.9 . . ?
C3 C4 H4A 110.9 . . ?
C5 C4 H4B 110.9 . . ?
C3 C4 H4B 110.9 . . ?
H4A C4 H4B 108.9 . . ?
N1 C2B C3B 103.1(11) . . ?
N1 C2B H2C 111.1 . . ?
C3B C2B H2C 111.1 . . ?
N1 C2B H2D 111.1 . . ?
C3B C2B H2D 111.1 . . ?
H2C C2B H2D 109.1 . . ?
C2B C3B C4B 100.8(13) . . ?
C2B C3B H3C 111.6 . . ?
C4B C3B H3C 111.6 . . ?
C2B C3B H3D 111.6 . . ?
C4B C3B H3D 111.6 . . ?
H3C C3B H3D 109.4 . . ?
C5 C4B C3B 102.4(10) . . ?
C5 C4B H4C 111.3 . . ?
C3B C4B H4C 111.3 . . ?
C5 C4B H4D 111.3 . . ?
C3B C4B H4D 111.3 . . ?
H4C C4B H4D 109.2 . . ?
N1 C5 C4 104.1(3) . . ?
N1 C5 C4B 105.7(7) . . ?
N1 C5 C6 111.38(19) . . ?
C4 C5 C6 113.0(4) . . ?
C4B C5 C6 118.5(15) . . ?
N1 C5 H5 109.4 . . ?
C4 C5 H5 109.4 . . ?
C6 C5 H5 109.4 . . ?
O7 C6 O8 127.0(2) . . ?
O7 C6 C5 117.9(2) . . ?
O8 C6 C5 115.0(2) . . ?
C16 C11 C12 120.9(3) . . ?
C16 C11 H11 119.6 . . ?
C12 C11 H11 119.6 . . ?
C13 C12 C11 120.6(3) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C12 C13 C14 119.2(3) . . ?
C12 C13 H13 120.4 . . ?
C14 C13 H13 120.4 . . ?
C13 C14 C15 120.3(3) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 H14 119.9 . . ?
C16 C15 C14 121.3(3) . . ?
C16 C15 H15 119.4 . . ?
C14 C15 H15 119.4 . . ?
C15 C16 C11 117.7(3) . . ?
C15 C16 C17 120.2(3) . . ?
C11 C16 C17 122.1(3) . . ?
C16 C17 C18 115.8(2) . . ?
C16 C17 H17A 108.3 . . ?
C18 C17 H17A 108.3 . . ?
C16 C17 H17B 108.3 . . ?
C18 C17 H17B 108.3 . . ?
H17A C17 H17B 107.4 . . ?
O19 C18 C20 110.0(2) . . ?
O19 C18 C17 110.0(2) . . ?
C20 C18 C17 112.8(2) . . ?
O19 C18 H18 108.0 . . ?
C20 C18 H18 108.0 . . ?
C17 C18 H18 108.0 . . ?
C18 O19 H19 109.5 . . ?
O21 C20 O22 124.6(3) . . ?
O21 C20 C18 122.1(3) . . ?
O22 C20 C18 113.3(2) . . ?
C20 O22 H22 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C2 C3 -23.3(9) . . . . ?
N1 C2 C3 C4 38.7(9) . . . . ?
C2 C3 C4 C5 -40.7(8) . . . . ?
C5 N1 C2B C3B 27(3) . . . . ?
N1 C2B C3B C4B -43(3) . . . . ?
C2B C3B C4B C5 43(2) . . . . ?
C2 N1 C5 C4 -1.9(8) . . . . ?
C2B N1 C5 C4B 1(3) . . . . ?
C2 N1 C5 C6 -123.9(6) . . . . ?
C2B N1 C5 C6 -129(2) . . . . ?
C3 C4 C5 N1 26.2(7) . . . . ?
C3 C4 C5 C6 147.2(5) . . . . ?
C3B C4B C5 N1 -27(2) . . . . ?
C3B C4B C5 C6 98.3(18) . . . . ?
N1 C5 C6 O7 -3.5(3) . . . . ?
C4 C5 C6 O7 -120.3(4) . . . . ?
C4B C5 C6 O7 -126.4(9) . . . . ?
N1 C5 C6 O8 179.0(2) . . . . ?
C4 C5 C6 O8 62.2(4) . . . . ?
C4B C5 C6 O8 56.1(9) . . . . ?
C16 C11 C12 C13 0.8(5) . . . . ?
C11 C12 C13 C14 -1.3(5) . . . . ?
C12 C13 C14 C15 1.0(5) . . . . ?
C13 C14 C15 C16 -0.1(5) . . . . ?
C14 C15 C16 C11 -0.5(5) . . . . ?
C14 C15 C16 C17 178.5(3) . . . . ?
C12 C11 C16 C15 0.1(5) . . . . ?
C12 C11 C16 C17 -178.8(3) . . . . ?
C15 C16 C17 C18 118.0(3) . . . . ?
C11 C16 C17 C18 -63.1(4) . . . . ?
C16 C17 C18 O19 75.4(3) . . . . ?
C16 C17 C18 C20 -47.8(3) . . . . ?
O19 C18 C20 O21 -5.2(4) . . . . ?
C17 C18 C20 O21 118.0(3) . . . . ?
O19 C18 C20 O22 174.5(2) . . . . ?
C17 C18 C20 O22 -62.2(3) . . . . ?

_refine_diff_density_max         0.255
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.039

####################################################################### 
# 
# 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_alexA35_A22
_database_code_depnum_ccdc_archive 'CCDC 2247562'
loop_
_audit_author_name
_audit_author_address
'Koen Robeyns'
;Universite catholique de Louvain
Belgium
;
_audit_update_record             
;
2023-03-09 deposited with the CCDC.	2023-04-28 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_THETM01_alexA35_A22         
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.550
RESPONSE: A data cut-off of 0.93A was imposed during integration beyond which the crystal diffracted poorly
;
# Added during the CSD deposition process: Thursday 09 March 2023 01:41 PM
# end Validation Reply Form


_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H18 O2, C5 H9 N O2'
_chemical_formula_sum            'C18 H27 N O4'
_chemical_formula_weight         321.40

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   9.4241(7)
_cell_length_b                   37.399(2)
_cell_length_c                   10.4169(11)
_cell_angle_alpha                90
_cell_angle_beta                 90.501(8)
_cell_angle_gamma                90
_cell_volume                     3671.3(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    700
_cell_measurement_theta_min      2.9180
_cell_measurement_theta_max      22.3700

_exptl_crystal_description       needle
_exptl_crystal_colour            ?colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.163
_exptl_crystal_F_000             1392
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.01
_exptl_absorpt_coefficient_mu    0.081
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.127
_exptl_absorpt_correction_T_max  0.999
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?



_diffrn_ambient_temperature      297(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Incoatec microfocus source'
_diffrn_measurement_device_type  'MAR345 image plate'
_diffrn_measurement_method       
;
'140 images, ΔΦ 0.75° '
;
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15139
_diffrn_reflns_av_unetI/netI     0.0771
_diffrn_reflns_av_R_equivalents  0.0788
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -38
_diffrn_reflns_limit_k_max       40
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         2.928
_diffrn_reflns_theta_max         22.439
_diffrn_reflns_theta_full        22.439
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measured_fraction_theta_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_point_group_measured_fraction_full 0.982
_reflns_number_total             4669
_reflns_number_gt                3074
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       MAR
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_atom_sites_solution_primary     dual
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'MERCURY (Macrae et al., 2008)'
_computing_publication_material  
;
'MERCURY (Macrae et al., 2008), Platon (Spek, 2009)'
;



_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0391P)²+2.2733P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4669
_refine_ls_number_parameters     591
_refine_ls_number_restraints     350
_refine_ls_R_factor_all          0.0994
_refine_ls_R_factor_gt           0.0611
_refine_ls_wR_factor_ref         0.1631
_refine_ls_wR_factor_gt          0.1410
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.4031(3) 0.22096(7) 0.4732(3) 0.0485(8) Uani 1 1 d . . . . .
H1A H 0.320291 0.225986 0.435651 0.058 Uiso 1 1 calc R U . . .
H1AB H 0.472181 0.229160 0.423450 0.058 Uiso 1 1 calc R U . . .
C2 C 0.4179(4) 0.18135(9) 0.4900(4) 0.0631(11) Uani 1 1 d . . . . .
H2A H 0.516285 0.173899 0.484309 0.076 Uiso 0.563(15) 1 calc R U P A 1
H2B H 0.361906 0.168388 0.426808 0.076 Uiso 0.563(15) 1 calc R U P A 1
H2C H 0.326075 0.169766 0.483358 0.076 Uiso 0.437(15) 1 calc R U P A 2
H2D H 0.479678 0.171469 0.424945 0.076 Uiso 0.437(15) 1 calc R U P A 2
C3 C 0.3611(15) 0.17602(19) 0.6239(7) 0.070(4) Uani 0.563(15) 1 d . . P A 1
H3A H 0.258197 0.175175 0.622651 0.084 Uiso 0.563(15) 1 calc R U P A 1
H3AB H 0.396940 0.153972 0.660972 0.084 Uiso 0.563(15) 1 calc R U P A 1
C3B C 0.4800(19) 0.1760(2) 0.6193(9) 0.065(4) Uani 0.437(15) 1 d . . P A 2
H3BA H 0.582581 0.178047 0.617962 0.078 Uiso 0.437(15) 1 calc R U P A 2
H3BB H 0.454113 0.152915 0.654223 0.078 Uiso 0.437(15) 1 calc R U P A 2
C4 C 0.4120(5) 0.20719(10) 0.6978(4) 0.0726(12) Uani 1 1 d . . . . .
H4A H 0.507061 0.202970 0.730926 0.087 Uiso 0.563(15) 1 calc R U P A 1
H4B H 0.349636 0.212058 0.769308 0.087 Uiso 0.563(15) 1 calc R U P A 1
H4C H 0.316397 0.201176 0.723940 0.087 Uiso 0.437(15) 1 calc R U P A 2
H4D H 0.468524 0.212733 0.773506 0.087 Uiso 0.437(15) 1 calc R U P A 2
C5 C 0.4113(3) 0.23849(9) 0.6031(3) 0.0447(9) Uani 1 1 d . . . . .
H5 H 0.326127 0.253001 0.616346 0.054 Uiso 1 1 calc R U . . .
C6 C 0.5431(4) 0.26227(9) 0.6153(4) 0.0451(9) Uani 1 1 d . . . . .
O7 O 0.6214(3) 0.26497(7) 0.5196(3) 0.0612(7) Uani 1 1 d . . . . .
O8 O 0.5590(3) 0.27763(7) 0.7220(3) 0.0613(7) Uani 1 1 d . . . . .
C11 C 0.9160(4) 0.36417(9) 0.8381(4) 0.0542(10) Uani 1 1 d . . . . .
H11 H 0.966765 0.362410 0.756670 0.065 Uiso 0.49(3) 1 calc R U P B 7
H11B H 0.967676 0.361675 0.757393 0.065 Uiso 0.51(3) 1 calc R U P B 8
C12 C 1.0248(4) 0.35960(11) 0.9481(5) 0.0805(14) Uani 1 1 d . . . . .
H12A H 1.101026 0.376331 0.937186 0.121 Uiso 1 1 calc R U . . .
H12B H 1.061859 0.335688 0.946899 0.121 Uiso 1 1 calc R U . . .
H12C H 0.979437 0.363925 1.028775 0.121 Uiso 1 1 calc R U . . .
C13 C 0.8061(4) 0.33487(9) 0.8411(4) 0.0516(10) Uani 1 1 d . . . . .
O14 O 0.7747(3) 0.31813(8) 0.9365(3) 0.0830(9) Uani 1 1 d . . . . .
O15 O 0.7438(3) 0.32940(6) 0.7286(3) 0.0651(8) Uani 1 1 d . . . . .
H15 H 0.680107 0.314664 0.736633 0.098 Uiso 1 1 calc R U . . .
C16 C 0.8401(17) 0.4028(3) 0.8434(15) 0.062(5) Uani 0.49(3) 1 d DG U P B 7
C17 C 0.7644(18) 0.4122(3) 0.9522(15) 0.057(4) Uani 0.49(3) 1 d DG U P B 7
H17 H 0.752853 0.395735 1.018282 0.068 Uiso 0.49(3) 1 calc R U P B 7
C18 C 0.7059(15) 0.4462(3) 0.9623(14) 0.056(3) Uani 0.49(3) 1 d DG U P B 7
H18 H 0.655249 0.452475 1.035068 0.067 Uiso 0.49(3) 1 calc R U P B 7
C19 C 0.7231(13) 0.4707(3) 0.8635(13) 0.046(3) Uani 0.49(3) 1 d DG U P B 7
C20 C 0.7988(19) 0.4613(3) 0.7547(10) 0.060(4) Uani 0.49(3) 1 d DG U P B 7
H20 H 0.810344 0.477761 0.688618 0.072 Uiso 0.49(3) 1 calc R U P B 7
C21 C 0.8573(19) 0.4273(3) 0.7446(12) 0.060(3) Uani 0.49(3) 1 d DG U P B 7
H21 H 0.907950 0.421022 0.671830 0.072 Uiso 0.49(3) 1 calc R U P B 7
C22 C 0.6581(15) 0.5089(3) 0.8786(19) 0.068(4) Uani 0.49(3) 1 d D U P B 7
H22A H 0.588753 0.511968 0.810139 0.082 Uiso 0.49(3) 1 calc R U P B 7
H22B H 0.606502 0.509184 0.958713 0.082 Uiso 0.49(3) 1 calc R U P B 7
C23 C 0.7496(19) 0.5398(3) 0.878(2) 0.092(5) Uani 0.49(3) 1 d D U P B 7
H23 H 0.793247 0.539202 0.792809 0.111 Uiso 0.49(3) 1 calc R U P B 7
C24 C 0.668(3) 0.5750(4) 0.879(3) 0.098(6) Uani 0.49(3) 1 d D U P B 7
H24A H 0.588563 0.573442 0.820316 0.147 Uiso 0.49(3) 1 calc R U P B 7
H24B H 0.729189 0.594100 0.852462 0.147 Uiso 0.49(3) 1 calc R U P B 7
H24C H 0.633959 0.579677 0.963716 0.147 Uiso 0.49(3) 1 calc R U P B 7
C25 C 0.870(2) 0.5403(6) 0.966(3) 0.117(9) Uani 0.49(3) 1 d D U P B 7
H25A H 0.907727 0.516580 0.974851 0.176 Uiso 0.49(3) 1 calc R U P B 7
H25B H 0.839590 0.548726 1.048668 0.176 Uiso 0.49(3) 1 calc R U P B 7
H25C H 0.941964 0.555946 0.933723 0.176 Uiso 0.49(3) 1 calc R U P B 7
C16B C 0.8513(13) 0.4007(3) 0.8386(13) 0.035(4) Uani 0.51(3) 1 d DG U P B 8
C17B C 0.7488(14) 0.4110(3) 0.9263(14) 0.046(3) Uani 0.51(3) 1 d DG U P B 8
H17B H 0.715651 0.394689 0.986407 0.056 Uiso 0.51(3) 1 calc R U P B 8
C18B C 0.6957(13) 0.4457(3) 0.9243(16) 0.052(3) Uani 0.51(3) 1 d DG U P B 8
H18B H 0.627152 0.452571 0.983051 0.062 Uiso 0.51(3) 1 calc R U P B 8
C19B C 0.7452(15) 0.4701(2) 0.8346(14) 0.062(4) Uani 0.51(3) 1 d DG U P B 8
C20B C 0.8477(18) 0.4598(3) 0.7468(11) 0.069(3) Uani 0.51(3) 1 d DG U P B 8
H20B H 0.880808 0.476134 0.686740 0.083 Uiso 0.51(3) 1 calc R U P B 8
C21B C 0.9007(16) 0.4251(3) 0.7488(12) 0.063(3) Uani 0.51(3) 1 d DG U P B 8
H21B H 0.969309 0.418252 0.690094 0.075 Uiso 0.51(3) 1 calc R U P B 8
C22B C 0.6811(14) 0.5087(3) 0.831(2) 0.072(4) Uani 0.51(3) 1 d D U P B 8
H22C H 0.625326 0.510798 0.752401 0.087 Uiso 0.51(3) 1 calc R U P B 8
H22D H 0.615741 0.510780 0.901802 0.087 Uiso 0.51(3) 1 calc R U P B 8
C23B C 0.7761(16) 0.5392(3) 0.8365(14) 0.061(3) Uani 0.51(3) 1 d D U P B 8
H23B H 0.826050 0.538090 0.754488 0.074 Uiso 0.51(3) 1 calc R U P B 8
C24B C 0.700(2) 0.5751(3) 0.831(2) 0.091(6) Uani 0.51(3) 1 d D U P B 8
H24D H 0.768742 0.593929 0.823967 0.136 Uiso 0.51(3) 1 calc R U P B 8
H24E H 0.646254 0.578347 0.908088 0.136 Uiso 0.51(3) 1 calc R U P B 8
H24F H 0.637412 0.575612 0.758058 0.136 Uiso 0.51(3) 1 calc R U P B 8
C25B C 0.8904(19) 0.5390(5) 0.931(2) 0.077(4) Uani 0.51(3) 1 d D U P B 8
H25D H 0.944927 0.517502 0.922448 0.092 Uiso 0.51(3) 1 calc R U P B 8
H25E H 0.851101 0.540133 1.015738 0.092 Uiso 0.51(3) 1 calc R U P B 8
H25F H 0.950539 0.559373 0.917607 0.092 Uiso 0.51(3) 1 calc R U P B 8
N31 N -0.0983(3) 0.27972(7) 0.4582(3) 0.0498(8) Uani 1 1 d . . . . .
H31A H -0.179770 0.273988 0.495547 0.060 Uiso 1 1 calc R U . . .
H31B H -0.027291 0.272032 0.507893 0.060 Uiso 1 1 calc R U . . .
C32 C -0.0887(4) 0.31952(10) 0.4415(4) 0.0646(11) Uani 1 1 d . . . . .
H32A H 0.008614 0.327718 0.449204 0.077 Uiso 0.566(17) 1 calc R U P C 3
H32B H -0.146270 0.331912 0.504202 0.077 Uiso 0.566(17) 1 calc R U P C 3
H32C H -0.025816 0.329942 0.505520 0.077 Uiso 0.434(17) 1 calc R U P C 4
H32D H -0.181598 0.330497 0.448698 0.077 Uiso 0.434(17) 1 calc R U P C 4
C33 C -0.1458(16) 0.32512(19) 0.3071(8) 0.067(3) Uani 0.566(17) 1 d . . P C 3
H33A H -0.248728 0.325174 0.306113 0.081 Uiso 0.566(17) 1 calc R U P C 3
H33B H -0.112096 0.347518 0.271622 0.081 Uiso 0.566(17) 1 calc R U P C 3
C33B C -0.030(2) 0.3245(3) 0.3088(11) 0.079(5) Uani 0.434(17) 1 d . . P C 4
H33C H -0.061477 0.347092 0.272455 0.094 Uiso 0.434(17) 1 calc R U P C 4
H33D H 0.072520 0.323969 0.310416 0.094 Uiso 0.434(17) 1 calc R U P C 4
C34 C -0.0887(5) 0.29371(10) 0.2328(4) 0.0760(13) Uani 1 1 d . . . . .
H34A H 0.007035 0.298456 0.203813 0.091 Uiso 0.566(17) 1 calc R U P C 3
H34B H -0.148376 0.288593 0.158764 0.091 Uiso 0.566(17) 1 calc R U P C 3
H34C H -0.028558 0.288395 0.160154 0.091 Uiso 0.434(17) 1 calc R U P C 4
H34D H -0.183732 0.298913 0.201650 0.091 Uiso 0.434(17) 1 calc R U P C 4
C35 C -0.0901(3) 0.26247(9) 0.3276(3) 0.0444(9) Uani 1 1 d . . . . .
H35 H -0.175999 0.248233 0.312860 0.053 Uiso 1 1 calc R U . . .
C36 C 0.0392(4) 0.23826(9) 0.3169(4) 0.0446(9) Uani 1 1 d . . . . .
O37 O 0.0528(3) 0.22247(7) 0.2105(3) 0.0628(7) Uani 1 1 d . . . . .
O38 O 0.1210(2) 0.23591(6) 0.4121(2) 0.0593(7) Uani 1 1 d . . . . .
C41 C 0.4154(4) 0.13863(9) 0.0979(4) 0.0524(10) Uani 1 1 d . . . . .
H41 H 0.475442 0.143376 0.173277 0.063 Uiso 0.640(17) 1 calc R U P D 5
H41B H 0.476801 0.144832 0.170978 0.063 Uiso 0.360(17) 1 calc R U P D 6
C42 C 0.5095(5) 0.14027(11) -0.0224(5) 0.0837(14) Uani 1 1 d . . . . .
H42A H 0.588045 0.124129 -0.012194 0.126 Uiso 1 1 calc R U . . .
H42B H 0.544528 0.164174 -0.033241 0.126 Uiso 1 1 calc R U . . .
H42C H 0.454603 0.133520 -0.096546 0.126 Uiso 1 1 calc R U . . .
C43 C 0.3002(4) 0.16657(10) 0.0931(4) 0.0538(10) Uani 1 1 d . . . . .
O44 O 0.2631(3) 0.18208(8) -0.0037(3) 0.0863(10) Uani 1 1 d . . . . .
O45 O 0.2440(3) 0.17278(7) 0.2060(3) 0.0670(8) Uani 1 1 d . . . . .
H45 H 0.180691 0.187703 0.198424 0.101 Uiso 1 1 calc R U . . .
C46 C 0.3548(17) 0.1010(3) 0.1107(15) 0.045(3) Uani 0.640(17) 1 d . U P D 5
C47 C 0.3897(16) 0.0785(4) 0.2114(15) 0.067(3) Uani 0.640(17) 1 d . U P D 5
H47 H 0.454671 0.086525 0.272636 0.080 Uiso 0.640(17) 1 calc R U P D 5
C48 C 0.3321(14) 0.0443(3) 0.2258(12) 0.067(3) Uani 0.640(17) 1 d . U P D 5
H48 H 0.359474 0.030348 0.295622 0.081 Uiso 0.640(17) 1 calc R U P D 5
C49 C 0.2349(12) 0.0309(3) 0.1376(12) 0.052(2) Uani 0.640(17) 1 d . U P D 5
C50 C 0.1982(11) 0.0532(3) 0.0369(11) 0.055(2) Uani 0.640(17) 1 d . U P D 5
H50 H 0.133061 0.045023 -0.024025 0.066 Uiso 0.640(17) 1 calc R U P D 5
C51 C 0.2549(14) 0.0872(3) 0.0230(12) 0.053(3) Uani 0.640(17) 1 d . U P D 5
H51 H 0.225975 0.101203 -0.046173 0.064 Uiso 0.640(17) 1 calc R U P D 5
C52 C 0.1731(11) -0.0063(3) 0.1515(12) 0.070(3) Uani 0.640(17) 1 d . U P D 5
H52A H 0.118945 -0.011680 0.074258 0.084 Uiso 0.640(17) 1 calc R U P D 5
H52B H 0.107000 -0.005988 0.222346 0.084 Uiso 0.640(17) 1 calc R U P D 5
C53 C 0.2780(11) -0.03687(18) 0.1744(11) 0.070(3) Uani 0.640(17) 1 d . U P D 5
H53 H 0.336910 -0.032044 0.250394 0.084 Uiso 0.640(17) 1 calc R U P D 5
C54 C 0.3683(18) -0.0396(7) 0.057(2) 0.089(5) Uani 0.640(17) 1 d . U P D 5
H54A H 0.312772 -0.049007 -0.012771 0.133 Uiso 0.640(17) 1 calc R U P D 5
H54B H 0.447117 -0.055159 0.074252 0.133 Uiso 0.640(17) 1 calc R U P D 5
H54C H 0.402818 -0.016257 0.034714 0.133 Uiso 0.640(17) 1 calc R U P D 5
C55 C 0.2012(15) -0.0723(4) 0.1886(14) 0.094(4) Uani 0.640(17) 1 d . U P D 5
H55A H 0.153004 -0.078039 0.109652 0.140 Uiso 0.640(17) 1 calc R U P D 5
H55B H 0.133409 -0.070579 0.256525 0.140 Uiso 0.640(17) 1 calc R U P D 5
H55C H 0.268726 -0.090773 0.208538 0.140 Uiso 0.640(17) 1 calc R U P D 5
C46B C 0.348(3) 0.1019(5) 0.130(2) 0.044(6) Uani 0.360(17) 1 d G U P D 6
C47B C 0.411(2) 0.0818(5) 0.227(2) 0.052(5) Uani 0.360(17) 1 d G U P D 6
H47B H 0.484750 0.091534 0.276192 0.062 Uiso 0.360(17) 1 calc R U P D 6
C48B C 0.365(2) 0.0472(5) 0.2511(16) 0.056(5) Uani 0.360(17) 1 d G U P D 6
H48B H 0.407100 0.033763 0.316176 0.067 Uiso 0.360(17) 1 calc R U P D 6
C49B C 0.255(2) 0.0326(4) 0.1779(16) 0.050(5) Uani 0.360(17) 1 d G U P D 6
C50B C 0.1921(19) 0.0527(5) 0.0806(16) 0.060(5) Uani 0.360(17) 1 d G U P D 6
H50B H 0.118778 0.042979 0.031624 0.072 Uiso 0.360(17) 1 calc R U P D 6
C51B C 0.239(2) 0.0873(5) 0.0567(18) 0.050(5) Uani 0.360(17) 1 d G U P D 6
H51B H 0.196427 0.100750 -0.008361 0.060 Uiso 0.360(17) 1 calc R U P D 6
C52B C 0.197(2) -0.0052(5) 0.2113(18) 0.063(4) Uani 0.360(17) 1 d . U P D 6
H52C H 0.095960 -0.003023 0.228603 0.076 Uiso 0.360(17) 1 calc R U P D 6
H52D H 0.242549 -0.013284 0.289764 0.076 Uiso 0.360(17) 1 calc R U P D 6
C53B C 0.2171(18) -0.0344(3) 0.1060(19) 0.062(4) Uani 0.360(17) 1 d . U P D 6
H53B H 0.175314 -0.026246 0.024648 0.075 Uiso 0.360(17) 1 calc R U P D 6
C54B C 0.402(3) -0.0379(13) 0.091(4) 0.084(7) Uani 0.360(17) 1 d . U P D 6
H54D H 0.423879 -0.047442 0.008043 0.127 Uiso 0.360(17) 1 calc R U P D 6
H54E H 0.438111 -0.053606 0.156455 0.127 Uiso 0.360(17) 1 calc R U P D 6
H54F H 0.443829 -0.014723 0.100522 0.127 Uiso 0.360(17) 1 calc R U P D 6
C55B C 0.144(3) -0.0705(7) 0.149(3) 0.092(7) Uani 0.360(17) 1 d . U P D 6
H55D H 0.161889 -0.088751 0.086592 0.138 Uiso 0.360(17) 1 calc R U P D 6
H55E H 0.043626 -0.066881 0.156628 0.138 Uiso 0.360(17) 1 calc R U P D 6
H55F H 0.182398 -0.077815 0.230847 0.138 Uiso 0.360(17) 1 calc R U P D 6


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C2 1.498(4) . ?
N1 C5 1.505(4) . ?
N1 H1A 0.8900 . ?
N1 H1AB 0.8900 . ?
C2 C3B 1.477(11) . ?
C2 C3 1.512(10) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 H2C 0.9700 . ?
C2 H2D 0.9700 . ?
C3 C4 1.475(8) . ?
C3 H3A 0.9700 . ?
C3 H3AB 0.9700 . ?
C3B C4 1.564(12) . ?
C3B H3BA 0.9700 . ?
C3B H3BB 0.9700 . ?
C4 C5 1.531(5) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 H4C 0.9700 . ?
C4 H4D 0.9700 . ?
C5 C6 1.532(5) . ?
C5 H5 0.9800 . ?
C6 O7 1.249(4) . ?
C6 O8 1.259(4) . ?
C11 C16B 1.497(10) . ?
C11 C13 1.508(5) . ?
C11 C12 1.540(5) . ?
C11 C16 1.612(10) . ?
C11 H11 0.9800 . ?
C11 H11B 0.9800 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 O14 1.213(4) . ?
C13 O15 1.322(4) . ?
O15 H15 0.8200 . ?
C16 C17 1.3900 . ?
C16 C21 1.3900 . ?
C17 C18 1.3900 . ?
C17 H17 0.9300 . ?
C18 C19 1.3900 . ?
C18 H18 0.9300 . ?
C19 C20 1.3900 . ?
C19 C22 1.560(7) . ?
C20 C21 1.3900 . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C22 C23 1.444(9) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 C25 1.455(9) . ?
C23 C24 1.526(9) . ?
C23 H23 0.9800 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C16B C17B 1.3900 . ?
C16B C21B 1.3900 . ?
C17B C18B 1.3900 . ?
C17B H17B 0.9300 . ?
C18B C19B 1.3900 . ?
C18B H18B 0.9300 . ?
C19B C20B 1.3900 . ?
C19B C22B 1.566(7) . ?
C20B C21B 1.3900 . ?
C20B H20B 0.9300 . ?
C21B H21B 0.9300 . ?
C22B C23B 1.450(8) . ?
C22B H22C 0.9700 . ?
C22B H22D 0.9700 . ?
C23B C25B 1.453(8) . ?
C23B C24B 1.524(8) . ?
C23B H23B 0.9800 . ?
C24B H24D 0.9600 . ?
C24B H24E 0.9600 . ?
C24B H24F 0.9600 . ?
C25B H25D 0.9600 . ?
C25B H25E 0.9600 . ?
C25B H25F 0.9600 . ?
N31 C32 1.501(4) . ?
N31 C35 1.508(4) . ?
N31 H31A 0.8900 . ?
N31 H31B 0.8900 . ?
C32 C33B 1.504(12) . ?
C32 C33 1.510(9) . ?
C32 H32A 0.9700 . ?
C32 H32B 0.9700 . ?
C32 H32C 0.9700 . ?
C32 H32D 0.9700 . ?
C33 C34 1.508(9) . ?
C33 H33A 0.9700 . ?
C33 H33B 0.9700 . ?
C33B C34 1.499(13) . ?
C33B H33C 0.9700 . ?
C33B H33D 0.9700 . ?
C34 C35 1.530(5) . ?
C34 H34A 0.9700 . ?
C34 H34B 0.9700 . ?
C34 H34C 0.9700 . ?
C34 H34D 0.9700 . ?
C35 C36 1.523(5) . ?
C35 H35 0.9800 . ?
C36 O38 1.254(4) . ?
C36 O37 1.264(4) . ?
C41 C43 1.507(5) . ?
C41 C46 1.524(11) . ?
C41 C42 1.543(5) . ?
C41 C46B 1.551(14) . ?
C41 H41 0.9800 . ?
C41 H41B 0.9800 . ?
C42 H42A 0.9600 . ?
C42 H42B 0.9600 . ?
C42 H42C 0.9600 . ?
C43 O44 1.212(4) . ?
C43 O45 1.315(4) . ?
O45 H45 0.8200 . ?
C46 C47 1.383(9) . ?
C46 C51 1.404(9) . ?
C47 C48 1.398(11) . ?
C47 H47 0.9300 . ?
C48 C49 1.385(11) . ?
C48 H48 0.9300 . ?
C49 C50 1.380(10) . ?
C49 C52 1.518(12) . ?
C50 C51 1.389(9) . ?
C50 H50 0.9300 . ?
C51 H51 0.9300 . ?
C52 C53 1.528(16) . ?
C52 H52A 0.9700 . ?
C52 H52B 0.9700 . ?
C53 C54 1.50(2) . ?
C53 C55 1.518(14) . ?
C53 H53 0.9800 . ?
C54 H54A 0.9600 . ?
C54 H54B 0.9600 . ?
C54 H54C 0.9600 . ?
C55 H55A 0.9600 . ?
C55 H55B 0.9600 . ?
C55 H55C 0.9600 . ?
C46B C47B 1.3900 . ?
C46B C51B 1.3900 . ?
C47B C48B 1.3900 . ?
C47B H47B 0.9300 . ?
C48B C49B 1.3900 . ?
C48B H48B 0.9300 . ?
C49B C50B 1.3900 . ?
C49B C52B 1.56(2) . ?
C50B C51B 1.3900 . ?
C50B H50B 0.9300 . ?
C51B H51B 0.9300 . ?
C52B C53B 1.56(3) . ?
C52B H52C 0.9700 . ?
C52B H52D 0.9700 . ?
C53B C55B 1.58(3) . ?
C53B C54B 1.75(4) . ?
C53B H53B 0.9800 . ?
C54B H54D 0.9600 . ?
C54B H54E 0.9600 . ?
C54B H54F 0.9600 . ?
C55B H55D 0.9600 . ?
C55B H55E 0.9600 . ?
C55B H55F 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
C2 N1 C5 108.8(3) . . ?
C2 N1 H1A 109.9 . . ?
C5 N1 H1A 109.9 . . ?
C2 N1 H1AB 109.9 . . ?
C5 N1 H1AB 109.9 . . ?
H1A N1 H1AB 108.3 . . ?
C3B C2 N1 106.0(4) . . ?
N1 C2 C3 101.8(4) . . ?
N1 C2 H2A 111.4 . . ?
C3 C2 H2A 111.4 . . ?
N1 C2 H2B 111.4 . . ?
C3 C2 H2B 111.4 . . ?
H2A C2 H2B 109.3 . . ?
C3B C2 H2C 110.5 . . ?
N1 C2 H2C 110.5 . . ?
C3B C2 H2D 110.5 . . ?
N1 C2 H2D 110.5 . . ?
H2C C2 H2D 108.7 . . ?
C4 C3 C2 105.1(6) . . ?
C4 C3 H3A 110.7 . . ?
C2 C3 H3A 110.7 . . ?
C4 C3 H3AB 110.7 . . ?
C2 C3 H3AB 110.7 . . ?
H3A C3 H3AB 108.8 . . ?
C2 C3B C4 102.5(8) . . ?
C2 C3B H3BA 111.3 . . ?
C4 C3B H3BA 111.3 . . ?
C2 C3B H3BB 111.3 . . ?
C4 C3B H3BB 111.3 . . ?
H3BA C3B H3BB 109.2 . . ?
C3 C4 C5 105.6(4) . . ?
C5 C4 C3B 103.4(5) . . ?
C3 C4 H4A 110.6 . . ?
C5 C4 H4A 110.6 . . ?
C3 C4 H4B 110.6 . . ?
C5 C4 H4B 110.6 . . ?
H4A C4 H4B 108.8 . . ?
C5 C4 H4C 111.1 . . ?
C3B C4 H4C 111.1 . . ?
C5 C4 H4D 111.1 . . ?
C3B C4 H4D 111.1 . . ?
H4C C4 H4D 109.0 . . ?
N1 C5 C4 104.3(3) . . ?
N1 C5 C6 111.3(3) . . ?
C4 C5 C6 113.1(3) . . ?
N1 C5 H5 109.4 . . ?
C4 C5 H5 109.4 . . ?
C6 C5 H5 109.4 . . ?
O7 C6 O8 127.0(3) . . ?
O7 C6 C5 117.7(3) . . ?
O8 C6 C5 115.3(3) . . ?
C16B C11 C13 112.5(6) . . ?
C16B C11 C12 111.6(6) . . ?
C13 C11 C12 110.9(3) . . ?
C13 C11 C16 110.1(7) . . ?
C12 C11 C16 111.5(6) . . ?
C13 C11 H11 108.0 . . ?
C12 C11 H11 108.0 . . ?
C16 C11 H11 108.0 . . ?
C16B C11 H11B 107.2 . . ?
C13 C11 H11B 107.2 . . ?
C12 C11 H11B 107.2 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O14 C13 O15 122.5(4) . . ?
O14 C13 C11 124.3(4) . . ?
O15 C13 C11 113.2(3) . . ?
C13 O15 H15 109.5 . . ?
C17 C16 C21 120.0 . . ?
C17 C16 C11 119.1(9) . . ?
C21 C16 C11 120.8(9) . . ?
C16 C17 C18 120.0 . . ?
C16 C17 H17 120.0 . . ?
C18 C17 H17 120.0 . . ?
C19 C18 C17 120.0 . . ?
C19 C18 H18 120.0 . . ?
C17 C18 H18 120.0 . . ?
C18 C19 C20 120.0 . . ?
C18 C19 C22 118.8(6) . . ?
C20 C19 C22 121.2(6) . . ?
C19 C20 C21 120.0 . . ?
C19 C20 H20 120.0 . . ?
C21 C20 H20 120.0 . . ?
C20 C21 C16 120.0 . . ?
C20 C21 H21 120.0 . . ?
C16 C21 H21 120.0 . . ?
C23 C22 C19 119.8(9) . . ?
C23 C22 H22A 107.4 . . ?
C19 C22 H22A 107.4 . . ?
C23 C22 H22B 107.4 . . ?
C19 C22 H22B 107.4 . . ?
H22A C22 H22B 106.9 . . ?
C22 C23 C25 118.0(10) . . ?
C22 C23 C24 113.0(10) . . ?
C25 C23 C24 112.1(9) . . ?
C22 C23 H23 104.0 . . ?
C25 C23 H23 104.0 . . ?
C24 C23 H23 104.0 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C23 C25 H25A 109.5 . . ?
C23 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C23 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C17B C16B C21B 120.0 . . ?
C17B C16B C11 122.7(8) . . ?
C21B C16B C11 117.3(8) . . ?
C16B C17B C18B 120.0 . . ?
C16B C17B H17B 120.0 . . ?
C18B C17B H17B 120.0 . . ?
C19B C18B C17B 120.0 . . ?
C19B C18B H18B 120.0 . . ?
C17B C18B H18B 120.0 . . ?
C18B C19B C20B 120.0 . . ?
C18B C19B C22B 119.4(6) . . ?
C20B C19B C22B 120.6(6) . . ?
C19B C20B C21B 120.0 . . ?
C19B C20B H20B 120.0 . . ?
C21B C20B H20B 120.0 . . ?
C20B C21B C16B 120.0 . . ?
C20B C21B H21B 120.0 . . ?
C16B C21B H21B 120.0 . . ?
C23B C22B C19B 119.0(8) . . ?
C23B C22B H22C 107.6 . . ?
C19B C22B H22C 107.6 . . ?
C23B C22B H22D 107.6 . . ?
C19B C22B H22D 107.6 . . ?
H22C C22B H22D 107.0 . . ?
C22B C23B C25B 118.7(8) . . ?
C22B C23B C24B 113.6(8) . . ?
C25B C23B C24B 111.9(8) . . ?
C22B C23B H23B 103.5 . . ?
C25B C23B H23B 103.5 . . ?
C24B C23B H23B 103.5 . . ?
C23B C24B H24D 109.5 . . ?
C23B C24B H24E 109.5 . . ?
H24D C24B H24E 109.5 . . ?
C23B C24B H24F 109.5 . . ?
H24D C24B H24F 109.5 . . ?
H24E C24B H24F 109.5 . . ?
C23B C25B H25D 109.5 . . ?
C23B C25B H25E 109.5 . . ?
H25D C25B H25E 109.5 . . ?
C23B C25B H25F 109.5 . . ?
H25D C25B H25F 109.5 . . ?
H25E C25B H25F 109.5 . . ?
C32 N31 C35 108.4(3) . . ?
C32 N31 H31A 110.0 . . ?
C35 N31 H31A 110.0 . . ?
C32 N31 H31B 110.0 . . ?
C35 N31 H31B 110.0 . . ?
H31A N31 H31B 108.4 . . ?
N31 C32 C33B 104.6(5) . . ?
N31 C32 C33 102.9(4) . . ?
N31 C32 H32A 111.2 . . ?
C33 C32 H32A 111.2 . . ?
N31 C32 H32B 111.2 . . ?
C33 C32 H32B 111.2 . . ?
H32A C32 H32B 109.1 . . ?
N31 C32 H32C 110.8 . . ?
C33B C32 H32C 110.8 . . ?
N31 C32 H32D 110.8 . . ?
C33B C32 H32D 110.8 . . ?
H32C C32 H32D 108.9 . . ?
C34 C33 C32 104.0(6) . . ?
C34 C33 H33A 111.0 . . ?
C32 C33 H33A 111.0 . . ?
C34 C33 H33B 111.0 . . ?
C32 C33 H33B 111.0 . . ?
H33A C33 H33B 109.0 . . ?
C34 C33B C32 104.8(9) . . ?
C34 C33B H33C 110.8 . . ?
C32 C33B H33C 110.8 . . ?
C34 C33B H33D 110.8 . . ?
C32 C33B H33D 110.8 . . ?
H33C C33B H33D 108.9 . . ?
C33B C34 C35 104.5(5) . . ?
C33 C34 C35 105.0(4) . . ?
C33 C34 H34A 110.8 . . ?
C35 C34 H34A 110.8 . . ?
C33 C34 H34B 110.8 . . ?
C35 C34 H34B 110.8 . . ?
H34A C34 H34B 108.8 . . ?
C33B C34 H34C 110.8 . . ?
C35 C34 H34C 110.8 . . ?
C33B C34 H34D 110.8 . . ?
C35 C34 H34D 110.8 . . ?
H34C C34 H34D 108.9 . . ?
N31 C35 C36 111.6(3) . . ?
N31 C35 C34 104.9(3) . . ?
C36 C35 C34 113.3(3) . . ?
N31 C35 H35 109.0 . . ?
C36 C35 H35 109.0 . . ?
C34 C35 H35 109.0 . . ?
O38 C36 O37 126.5(3) . . ?
O38 C36 C35 118.1(3) . . ?
O37 C36 C35 115.4(3) . . ?
C43 C41 C46 111.9(7) . . ?
C43 C41 C42 111.4(3) . . ?
C46 C41 C42 109.0(7) . . ?
C43 C41 C46B 109.1(11) . . ?
C42 C41 C46B 116.7(11) . . ?
C43 C41 H41 108.2 . . ?
C46 C41 H41 108.2 . . ?
C42 C41 H41 108.2 . . ?
C43 C41 H41B 106.4 . . ?
C42 C41 H41B 106.4 . . ?
C46B C41 H41B 106.4 . . ?
C41 C42 H42A 109.5 . . ?
C41 C42 H42B 109.5 . . ?
H42A C42 H42B 109.5 . . ?
C41 C42 H42C 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 109.5 . . ?
O44 C43 O45 122.9(4) . . ?
O44 C43 C41 124.2(4) . . ?
O45 C43 C41 112.9(3) . . ?
C43 O45 H45 109.5 . . ?
C47 C46 C51 115.0(7) . . ?
C47 C46 C41 122.8(10) . . ?
C51 C46 C41 122.2(9) . . ?
C46 C47 C48 123.3(8) . . ?
C46 C47 H47 118.4 . . ?
C48 C47 H47 118.4 . . ?
C49 C48 C47 120.9(8) . . ?
C49 C48 H48 119.5 . . ?
C47 C48 H48 119.5 . . ?
C50 C49 C48 116.5(7) . . ?
C50 C49 C52 122.1(8) . . ?
C48 C49 C52 121.4(9) . . ?
C49 C50 C51 122.5(7) . . ?
C49 C50 H50 118.8 . . ?
C51 C50 H50 118.8 . . ?
C50 C51 C46 121.8(7) . . ?
C50 C51 H51 119.1 . . ?
C46 C51 H51 119.1 . . ?
C49 C52 C53 117.0(9) . . ?
C49 C52 H52A 108.1 . . ?
C53 C52 H52A 108.1 . . ?
C49 C52 H52B 108.1 . . ?
C53 C52 H52B 108.1 . . ?
H52A C52 H52B 107.3 . . ?
C54 C53 C55 107.2(13) . . ?
C54 C53 C52 107.1(14) . . ?
C55 C53 C52 111.1(8) . . ?
C54 C53 H53 110.4 . . ?
C55 C53 H53 110.4 . . ?
C52 C53 H53 110.4 . . ?
C53 C54 H54A 109.5 . . ?
C53 C54 H54B 109.5 . . ?
H54A C54 H54B 109.5 . . ?
C53 C54 H54C 109.5 . . ?
H54A C54 H54C 109.5 . . ?
H54B C54 H54C 109.5 . . ?
C53 C55 H55A 109.5 . . ?
C53 C55 H55B 109.5 . . ?
H55A C55 H55B 109.5 . . ?
C53 C55 H55C 109.5 . . ?
H55A C55 H55C 109.5 . . ?
H55B C55 H55C 109.5 . . ?
C47B C46B C51B 120.0 . . ?
C47B C46B C41 117.6(13) . . ?
C51B C46B C41 122.1(13) . . ?
C46B C47B C48B 120.0 . . ?
C46B C47B H47B 120.0 . . ?
C48B C47B H47B 120.0 . . ?
C49B C48B C47B 120.0 . . ?
C49B C48B H48B 120.0 . . ?
C47B C48B H48B 120.0 . . ?
C50B C49B C48B 120.0 . . ?
C50B C49B C52B 120.2(11) . . ?
C48B C49B C52B 119.7(11) . . ?
C49B C50B C51B 120.0 . . ?
C49B C50B H50B 120.0 . . ?
C51B C50B H50B 120.0 . . ?
C50B C51B C46B 120.0 . . ?
C50B C51B H51B 120.0 . . ?
C46B C51B H51B 120.0 . . ?
C49B C52B C53B 115.5(14) . . ?
C49B C52B H52C 108.4 . . ?
C53B C52B H52C 108.4 . . ?
C49B C52B H52D 108.4 . . ?
C53B C52B H52D 108.4 . . ?
H52C C52B H52D 107.5 . . ?
C52B C53B C55B 109.9(16) . . ?
C52B C53B C54B 104(2) . . ?
C55B C53B C54B 113(2) . . ?
C52B C53B H53B 109.8 . . ?
C55B C53B H53B 109.8 . . ?
C54B C53B H53B 109.8 . . ?
C53B C54B H54D 109.5 . . ?
C53B C54B H54E 109.5 . . ?
H54D C54B H54E 109.5 . . ?
C53B C54B H54F 109.5 . . ?
H54D C54B H54F 109.5 . . ?
H54E C54B H54F 109.5 . . ?
C53B C55B H55D 109.5 . . ?
C53B C55B H55E 109.5 . . ?
H55D C55B H55E 109.5 . . ?
C53B C55B H55F 109.5 . . ?
H55D C55B H55F 109.5 . . ?
H55E C55B H55F 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C2 C3B -17.8(8) . . . . ?
C5 N1 C2 C3 27.5(6) . . . . ?
N1 C2 C3 C4 -38.0(9) . . . . ?
N1 C2 C3B C4 34.5(10) . . . . ?
C2 C3 C4 C5 34.5(9) . . . . ?
C2 C3B C4 C5 -38.8(9) . . . . ?
C2 N1 C5 C4 -7.2(4) . . . . ?
C2 N1 C5 C6 115.0(3) . . . . ?
C3 C4 C5 N1 -16.8(7) . . . . ?
C3B C4 C5 N1 27.8(7) . . . . ?
C3 C4 C5 C6 -137.8(7) . . . . ?
C3B C4 C5 C6 -93.2(7) . . . . ?
N1 C5 C6 O7 2.1(4) . . . . ?
C4 C5 C6 O7 119.0(4) . . . . ?
N1 C5 C6 O8 -179.2(3) . . . . ?
C4 C5 C6 O8 -62.2(4) . . . . ?
C16B C11 C13 O14 -101.4(7) . . . . ?
C12 C11 C13 O14 24.4(5) . . . . ?
C16 C11 C13 O14 -99.5(7) . . . . ?
C16B C11 C13 O15 77.5(7) . . . . ?
C12 C11 C13 O15 -156.8(3) . . . . ?
C16 C11 C13 O15 79.3(7) . . . . ?
C13 C11 C16 C17 64.2(10) . . . . ?
C12 C11 C16 C17 -59.4(10) . . . . ?
C13 C11 C16 C21 -120.1(9) . . . . ?
C12 C11 C16 C21 116.3(9) . . . . ?
C21 C16 C17 C18 0.0 . . . . ?
C11 C16 C17 C18 175.8(12) . . . . ?
C16 C17 C18 C19 0.0 . . . . ?
C17 C18 C19 C20 0.0 . . . . ?
C17 C18 C19 C22 -179.1(11) . . . . ?
C18 C19 C20 C21 0.0 . . . . ?
C22 C19 C20 C21 179.1(11) . . . . ?
C19 C20 C21 C16 0.0 . . . . ?
C17 C16 C21 C20 0.0 . . . . ?
C11 C16 C21 C20 -175.7(12) . . . . ?
C18 C19 C22 C23 119.0(13) . . . . ?
C20 C19 C22 C23 -60.1(16) . . . . ?
C19 C22 C23 C25 -53(2) . . . . ?
C19 C22 C23 C24 173.6(12) . . . . ?
C13 C11 C16B C17B 49.9(9) . . . . ?
C12 C11 C16B C17B -75.6(9) . . . . ?
C13 C11 C16B C21B -132.0(7) . . . . ?
C12 C11 C16B C21B 102.5(8) . . . . ?
C21B C16B C17B C18B 0.0 . . . . ?
C11 C16B C17B C18B 178.1(11) . . . . ?
C16B C17B C18B C19B 0.0 . . . . ?
C17B C18B C19B C20B 0.0 . . . . ?
C17B C18B C19B C22B 178.1(11) . . . . ?
C18B C19B C20B C21B 0.0 . . . . ?
C22B C19B C20B C21B -178.1(11) . . . . ?
C19B C20B C21B C16B 0.0 . . . . ?
C17B C16B C21B C20B 0.0 . . . . ?
C11 C16B C21B C20B -178.2(10) . . . . ?
C18B C19B C22B C23B 127.2(11) . . . . ?
C20B C19B C22B C23B -54.7(14) . . . . ?
C19B C22B C23B C25B -45.7(19) . . . . ?
C19B C22B C23B C24B 179.6(11) . . . . ?
C35 N31 C32 C33B -17.0(10) . . . . ?
C35 N31 C32 C33 26.5(7) . . . . ?
N31 C32 C33 C34 -38.1(9) . . . . ?
N31 C32 C33B C34 32.8(14) . . . . ?
C32 C33B C34 C35 -36.0(14) . . . . ?
C32 C33 C34 C35 35.6(10) . . . . ?
C32 N31 C35 C36 118.1(3) . . . . ?
C32 N31 C35 C34 -4.9(4) . . . . ?
C33B C34 C35 N31 25.0(10) . . . . ?
C33 C34 C35 N31 -18.9(7) . . . . ?
C33B C34 C35 C36 -96.9(9) . . . . ?
C33 C34 C35 C36 -140.8(7) . . . . ?
N31 C35 C36 O38 -1.0(4) . . . . ?
C34 C35 C36 O38 117.1(4) . . . . ?
N31 C35 C36 O37 179.3(3) . . . . ?
C34 C35 C36 O37 -62.7(4) . . . . ?
C46 C41 C43 O44 -105.0(8) . . . . ?
C42 C41 C43 O44 17.3(5) . . . . ?
C46B C41 C43 O44 -112.9(10) . . . . ?
C46 C41 C43 O45 75.5(7) . . . . ?
C42 C41 C43 O45 -162.2(3) . . . . ?
C46B C41 C43 O45 67.6(10) . . . . ?
C43 C41 C46 C47 -121.9(10) . . . . ?
C42 C41 C46 C47 114.5(10) . . . . ?
C43 C41 C46 C51 55.7(13) . . . . ?
C42 C41 C46 C51 -67.9(12) . . . . ?
C51 C46 C47 C48 0.6(12) . . . . ?
C41 C46 C47 C48 178.4(15) . . . . ?
C46 C47 C48 C49 0.0(13) . . . . ?
C47 C48 C49 C50 -0.4(12) . . . . ?
C47 C48 C49 C52 179.3(12) . . . . ?
C48 C49 C50 C51 0.1(12) . . . . ?
C52 C49 C50 C51 -179.6(11) . . . . ?
C49 C50 C51 C46 0.6(13) . . . . ?
C47 C46 C51 C50 -1.0(12) . . . . ?
C41 C46 C51 C50 -178.7(14) . . . . ?
C50 C49 C52 C53 130.0(11) . . . . ?
C48 C49 C52 C53 -49.7(15) . . . . ?
C49 C52 C53 C54 -64.2(17) . . . . ?
C49 C52 C53 C55 179.0(9) . . . . ?
C43 C41 C46B C47B -131.1(10) . . . . ?
C42 C41 C46B C47B 101.7(11) . . . . ?
C43 C41 C46B C51B 55.6(17) . . . . ?
C42 C41 C46B C51B -71.6(17) . . . . ?
C51B C46B C47B C48B 0.0 . . . . ?
C41 C46B C47B C48B -173(2) . . . . ?
C46B C47B C48B C49B 0.0 . . . . ?
C47B C48B C49B C50B 0.0 . . . . ?
C47B C48B C49B C52B -175.8(18) . . . . ?
C48B C49B C50B C51B 0.0 . . . . ?
C52B C49B C50B C51B 175.8(18) . . . . ?
C49B C50B C51B C46B 0.0 . . . . ?
C47B C46B C51B C50B 0.0 . . . . ?
C41 C46B C51B C50B 173(2) . . . . ?
C50B C49B C52B C53B 68(2) . . . . ?
C48B C49B C52B C53B -116.5(17) . . . . ?
C49B C52B C53B C55B -176.4(14) . . . . ?
C49B C52B C53B C54B 62(3) . . . . ?

_refine_diff_density_max         0.217
_refine_diff_density_min         -0.161
_refine_diff_density_rms         0.038

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

data_alex_fl175
_database_code_depnum_ccdc_archive 'CCDC 2247558'
loop_
_audit_author_name
_audit_author_address
'Koen Robeyns'
;Universite catholique de Louvain
Belgium
;
_audit_update_record             
;
2023-03-09 deposited with the CCDC.	2023-04-28 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_THETM01_alex_fl175          
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.550
RESPONSE: A data cut-off of 1A was imposed during integration beyond which the crystal diffracted poorly
;
# Added during the CSD deposition process: Thursday 09 March 2023 01:41 PM
# end Validation Reply Form


_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C15 H13 F O2), C8 H14 N2 O2'
_chemical_formula_sum            'C38 H40 F2 N2 O6'
_chemical_formula_weight         658.72

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   5.9135(3)
_cell_length_b                   18.5470(9)
_cell_length_c                   31.3947(16)
_cell_angle_alpha                90
_cell_angle_beta                 94.307(5)
_cell_angle_gamma                90
_cell_volume                     3433.6(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    2283
_cell_measurement_theta_min      2.8140
_cell_measurement_theta_max      20.5350

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.274
_exptl_crystal_F_000             1392
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_exptl_absorpt_coefficient_mu    0.093
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.91282
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?



_diffrn_ambient_temperature      297(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Incoatec microfocus source'
_diffrn_measurement_device_type  'MAR345 image plate'
_diffrn_measurement_method       
;
'150 images, ΔΦ 1.2° '
;
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12226
_diffrn_reflns_av_unetI/netI     0.0548
_diffrn_reflns_av_R_equivalents  0.0571
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         2.825
_diffrn_reflns_theta_max         20.821
_diffrn_reflns_theta_full        20.821
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             3561
_reflns_number_gt                2377
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       MAR
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_atom_sites_solution_primary     dual
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'MERCURY (Macrae et al., 2008)'
_computing_publication_material  
;
'MERCURY (Macrae et al., 2008), Platon (Spek, 2009)'
;




_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0232P)²+4.9350P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3561
_refine_ls_number_parameters     436
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1154
_refine_ls_R_factor_gt           0.0707
_refine_ls_wR_factor_ref         0.1414
_refine_ls_wR_factor_gt          0.1271
_refine_ls_goodness_of_fit_ref   1.143
_refine_ls_restrained_S_all      1.143
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.3264(5) 0.95764(18) 0.45525(10) 0.0768(10) Uani 1 1 d . . . . .
C2 C 0.1588(9) 0.9243(3) 0.47527(18) 0.0488(14) Uani 1 1 d . . . . .
C3 C -0.0297(9) 0.8996(3) 0.45055(17) 0.0493(14) Uani 1 1 d . . . . .
C4 C -0.1978(9) 0.8695(3) 0.47338(18) 0.0552(15) Uani 1 1 d . . . . .
H4 H -0.331113 0.853595 0.458753 0.066 Uiso 1 1 calc R U . . .
C5 C -0.1723(10) 0.8624(3) 0.51767(19) 0.0600(16) Uani 1 1 d . . . . .
H5 H -0.287300 0.841255 0.532018 0.072 Uiso 1 1 calc R U . . .
C6 C 0.0229(10) 0.8865(3) 0.54059(17) 0.0535(15) Uani 1 1 d . . . . .
C7 C 0.1882(9) 0.9182(3) 0.51840(19) 0.0555(15) Uani 1 1 d . . . . .
H7 H 0.320080 0.935445 0.532928 0.067 Uiso 1 1 calc R U . . .
C8 C 0.0596(10) 0.8760(3) 0.58890(18) 0.0675(17) Uani 1 1 d . . . . .
H8 H 0.185909 0.907158 0.599186 0.081 Uiso 1 1 calc R U . . .
C9 C -0.1385(12) 0.8951(3) 0.6133(2) 0.096(2) Uani 1 1 d . . . . .
H9A H -0.176313 0.944962 0.608565 0.144 Uiso 1 1 calc R U . . .
H9B H -0.101004 0.887160 0.643206 0.144 Uiso 1 1 calc R U . . .
H9C H -0.265794 0.865587 0.603820 0.144 Uiso 1 1 calc R U . . .
C10 C 0.1367(12) 0.7981(3) 0.59600(18) 0.0617(16) Uani 1 1 d . . . . .
O11 O 0.3309(8) 0.7820(2) 0.60303(15) 0.0927(15) Uani 1 1 d . . . . .
O12 O -0.0265(6) 0.7499(2) 0.59126(12) 0.0755(12) Uani 1 1 d . . . . .
H12 H 0.026807 0.709486 0.595520 0.113 Uiso 1 1 calc R U . . .
C13 C -0.0532(10) 0.9063(3) 0.40320(18) 0.0531(15) Uani 1 1 d . . . . .
C14 C 0.1145(10) 0.8837(3) 0.3777(2) 0.0644(17) Uani 1 1 d . . . . .
H14 H 0.249632 0.864962 0.390167 0.077 Uiso 1 1 calc R U . . .
C15 C 0.0810(12) 0.8889(3) 0.3341(2) 0.082(2) Uani 1 1 d . . . . .
H15 H 0.193472 0.872910 0.317187 0.098 Uiso 1 1 calc R U . . .
C16 C -0.1153(14) 0.9173(4) 0.3149(2) 0.092(2) Uani 1 1 d . . . . .
H16 H -0.136042 0.920751 0.285333 0.110 Uiso 1 1 calc R U . . .
C17 C -0.2804(12) 0.9407(4) 0.3401(2) 0.085(2) Uani 1 1 d . . . . .
H17 H -0.413203 0.960759 0.327497 0.102 Uiso 1 1 calc R U . . .
C18 C -0.2507(10) 0.9344(3) 0.38387(19) 0.0635(16) Uani 1 1 d . . . . .
H18 H -0.365258 0.949411 0.400581 0.076 Uiso 1 1 calc R U . . .
F21 F 1.0985(5) 0.85976(18) 0.87589(10) 0.0787(10) Uani 1 1 d . . . . .
C22 C 1.2592(10) 0.8268(3) 0.8534(2) 0.0590(16) Uani 1 1 d . . . . .
C23 C 1.4435(9) 0.7973(3) 0.87665(18) 0.0483(14) Uani 1 1 d . . . . .
C24 C 1.6031(10) 0.7661(3) 0.8522(2) 0.0637(17) Uani 1 1 d . . . . .
H24 H 1.731316 0.744843 0.865811 0.076 Uiso 1 1 calc R U . . .
C25 C 1.5771(11) 0.7658(3) 0.8085(2) 0.0711(18) Uani 1 1 d . . . . .
H25 H 1.687464 0.744067 0.793196 0.085 Uiso 1 1 calc R U . . .
C26 C 1.3917(12) 0.7968(3) 0.78658(19) 0.0664(17) Uani 1 1 d . . . . .
C27 C 1.2287(10) 0.8279(3) 0.8099(2) 0.0648(17) Uani 1 1 d . . . . .
H27 H 1.100616 0.849177 0.796217 0.078 Uiso 1 1 calc R U . . .
C28 C 1.3678(12) 0.7984(4) 0.73777(19) 0.095(2) Uani 1 1 d . . . . .
H28 H 1.491244 0.767834 0.728984 0.114 Uiso 1 1 calc R U . . .
C29 C 1.4027(14) 0.8670(4) 0.7180(2) 0.139(4) Uani 1 1 d . . . . .
H29A H 1.552355 0.884220 0.726598 0.208 Uiso 1 1 calc R U . . .
H29B H 1.292533 0.900865 0.726816 0.208 Uiso 1 1 calc R U . . .
H29C H 1.386516 0.861758 0.687549 0.208 Uiso 1 1 calc R U . . .
C30 C 1.1544(12) 0.7601(4) 0.7216(2) 0.0731(19) Uani 1 1 d . . . . .
O31 O 1.0071(10) 0.7869(3) 0.70062(19) 0.150(3) Uani 1 1 d . . . . .
O32 O 1.1447(7) 0.6931(3) 0.73253(14) 0.0995(16) Uani 1 1 d . . . . .
H32 H 1.024370 0.675689 0.722695 0.149 Uiso 1 1 calc R U . . .
C33 C 1.4733(9) 0.7994(3) 0.92401(17) 0.0480(14) Uani 1 1 d . . . . .
C34 C 1.6745(9) 0.8239(3) 0.94428(19) 0.0593(16) Uani 1 1 d . . . . .
H34 H 1.790157 0.839601 0.928043 0.071 Uiso 1 1 calc R U . . .
C35 C 1.7058(11) 0.8253(3) 0.9882(2) 0.0708(18) Uani 1 1 d . . . . .
H35 H 1.842416 0.841670 1.001346 0.085 Uiso 1 1 calc R U . . .
C36 C 1.5369(13) 0.8028(3) 1.0126(2) 0.0755(19) Uani 1 1 d . . . . .
H36 H 1.557509 0.804350 1.042202 0.091 Uiso 1 1 calc R U . . .
C37 C 1.3375(11) 0.7781(3) 0.9929(2) 0.0686(17) Uani 1 1 d . . . . .
H37 H 1.223119 0.762245 1.009422 0.082 Uiso 1 1 calc R U . . .
C38 C 1.3038(10) 0.7764(3) 0.94905(19) 0.0599(16) Uani 1 1 d . . . . .
H38 H 1.166855 0.759882 0.936175 0.072 Uiso 1 1 calc R U . . .
O41 O 0.1043(7) 0.6128(2) 0.59685(14) 0.0811(14) Uani 1 1 d . . . . .
C42 C 0.2683(11) 0.5743(3) 0.59291(19) 0.0603(17) Uani 1 1 d . . . . .
C43 C 0.3198(12) 0.5320(3) 0.5544(2) 0.086(2) Uani 1 1 d . . . . .
H43A H 0.299229 0.561536 0.528847 0.104 Uiso 1 1 calc R U . . .
H43B H 0.221592 0.490233 0.550916 0.104 Uiso 1 1 calc R U . . .
C44 C 0.5655(12) 0.5091(4) 0.5623(2) 0.090(2) Uani 1 1 d . . . . .
H44A H 0.665319 0.542139 0.548759 0.108 Uiso 1 1 calc R U . . .
H44B H 0.588336 0.460834 0.551548 0.108 Uiso 1 1 calc R U . . .
C45 C 0.6070(10) 0.5117(3) 0.6105(2) 0.081(2) Uani 1 1 d . . . . .
H45A H 0.587425 0.464429 0.622980 0.097 Uiso 1 1 calc R U . . .
H45B H 0.758543 0.529041 0.618938 0.097 Uiso 1 1 calc R U . . .
N46 N 0.4357(7) 0.5619(2) 0.62344(14) 0.0565(12) Uani 1 1 d . . . . .
C47 C 0.4324(9) 0.5874(3) 0.66693(17) 0.0566(15) Uani 1 1 d . . . . .
H47 H 0.295215 0.616622 0.668421 0.068 Uiso 1 1 calc R U . . .
C48 C 0.6356(10) 0.6370(3) 0.67772(19) 0.0580(16) Uani 1 1 d . . . . .
O49 O 0.7831(7) 0.6202(2) 0.70571(13) 0.0803(13) Uani 1 1 d . . . . .
N50 N 0.6419(8) 0.6969(3) 0.65595(14) 0.0740(15) Uani 1 1 d . . . . .
H50A H 0.752566 0.726538 0.660939 0.089 Uiso 1 1 calc R U . . .
H50B H 0.535483 0.706657 0.636638 0.089 Uiso 1 1 calc R U . . .
C51 C 0.4210(10) 0.5273(3) 0.69940(19) 0.0781(19) Uani 1 1 d . . . . .
H51A H 0.419135 0.548236 0.727681 0.094 Uiso 1 1 calc R U . . .
H51B H 0.556331 0.497841 0.698932 0.094 Uiso 1 1 calc R U . . .
C52 C 0.2141(11) 0.4797(4) 0.6911(2) 0.114(3) Uani 1 1 d . . . . .
H52A H 0.218674 0.456858 0.663774 0.171 Uiso 1 1 calc R U . . .
H52B H 0.079433 0.508483 0.691457 0.171 Uiso 1 1 calc R U . . .
H52C H 0.213257 0.443453 0.712989 0.171 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C2 1.361(5) . ?
C2 C7 1.357(7) . ?
C2 C3 1.387(7) . ?
C3 C4 1.386(7) . ?
C3 C13 1.488(7) . ?
C4 C5 1.394(7) . ?
C4 H4 0.9300 . ?
C5 C6 1.388(7) . ?
C5 H5 0.9300 . ?
C6 C7 1.374(7) . ?
C6 C8 1.529(7) . ?
C7 H7 0.9300 . ?
C8 C9 1.490(7) . ?
C8 C10 1.525(7) . ?
C8 H8 0.9800 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 O11 1.191(6) . ?
C10 O12 1.316(6) . ?
O12 H12 0.8200 . ?
C13 C18 1.377(7) . ?
C13 C14 1.385(7) . ?
C14 C15 1.373(7) . ?
C14 H14 0.9300 . ?
C15 C16 1.372(8) . ?
C15 H15 0.9300 . ?
C16 C17 1.371(8) . ?
C16 H16 0.9300 . ?
C17 C18 1.378(7) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
F21 C22 1.370(6) . ?
C22 C27 1.365(7) . ?
C22 C23 1.379(7) . ?
C23 C24 1.388(7) . ?
C23 C33 1.485(7) . ?
C24 C25 1.369(7) . ?
C24 H24 0.9300 . ?
C25 C26 1.376(8) . ?
C25 H25 0.9300 . ?
C26 C27 1.379(8) . ?
C26 C28 1.529(8) . ?
C27 H27 0.9300 . ?
C28 C29 1.437(8) . ?
C28 C30 1.502(8) . ?
C28 H28 0.9800 . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
C30 O31 1.163(7) . ?
C30 O32 1.292(7) . ?
O32 H32 0.8200 . ?
C33 C34 1.383(7) . ?
C33 C38 1.386(7) . ?
C34 C35 1.378(7) . ?
C34 H34 0.9300 . ?
C35 C36 1.368(8) . ?
C35 H35 0.9300 . ?
C36 C37 1.368(8) . ?
C36 H36 0.9300 . ?
C37 C38 1.377(7) . ?
C37 H37 0.9300 . ?
C38 H38 0.9300 . ?
O41 C42 1.218(6) . ?
C42 N46 1.345(6) . ?
C42 C43 1.493(8) . ?
C43 C44 1.516(8) . ?
C43 H43A 0.9700 . ?
C43 H43B 0.9700 . ?
C44 C45 1.517(8) . ?
C44 H44A 0.9700 . ?
C44 H44B 0.9700 . ?
C45 N46 1.456(6) . ?
C45 H45A 0.9700 . ?
C45 H45B 0.9700 . ?
N46 C47 1.446(6) . ?
C47 C51 1.515(7) . ?
C47 C48 1.531(7) . ?
C47 H47 0.9800 . ?
C48 O49 1.231(6) . ?
C48 N50 1.307(6) . ?
N50 H50A 0.8600 . ?
N50 H50B 0.8600 . ?
C51 C52 1.515(7) . ?
C51 H51A 0.9700 . ?
C51 H51B 0.9700 . ?
C52 H52A 0.9600 . ?
C52 H52B 0.9600 . ?
C52 H52C 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
C7 C2 F1 117.1(5) . . ?
C7 C2 C3 124.6(5) . . ?
F1 C2 C3 118.3(5) . . ?
C4 C3 C2 114.9(5) . . ?
C4 C3 C13 122.2(5) . . ?
C2 C3 C13 122.8(5) . . ?
C3 C4 C5 121.7(5) . . ?
C3 C4 H4 119.1 . . ?
C5 C4 H4 119.1 . . ?
C6 C5 C4 120.7(5) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C7 C6 C5 118.1(5) . . ?
C7 C6 C8 120.3(5) . . ?
C5 C6 C8 121.6(6) . . ?
C2 C7 C6 119.9(5) . . ?
C2 C7 H7 120.0 . . ?
C6 C7 H7 120.0 . . ?
C9 C8 C10 112.9(5) . . ?
C9 C8 C6 114.9(5) . . ?
C10 C8 C6 106.6(5) . . ?
C9 C8 H8 107.4 . . ?
C10 C8 H8 107.4 . . ?
C6 C8 H8 107.4 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O11 C10 O12 122.6(6) . . ?
O11 C10 C8 122.6(6) . . ?
O12 C10 C8 114.8(6) . . ?
C10 O12 H12 109.5 . . ?
C18 C13 C14 118.7(6) . . ?
C18 C13 C3 119.0(6) . . ?
C14 C13 C3 122.3(5) . . ?
C15 C14 C13 119.9(6) . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C16 C15 C14 121.2(7) . . ?
C16 C15 H15 119.4 . . ?
C14 C15 H15 119.4 . . ?
C17 C16 C15 119.0(6) . . ?
C17 C16 H16 120.5 . . ?
C15 C16 H16 120.5 . . ?
C16 C17 C18 120.4(6) . . ?
C16 C17 H17 119.8 . . ?
C18 C17 H17 119.8 . . ?
C13 C18 C17 120.8(6) . . ?
C13 C18 H18 119.6 . . ?
C17 C18 H18 119.6 . . ?
C27 C22 F21 117.7(6) . . ?
C27 C22 C23 125.1(6) . . ?
F21 C22 C23 117.1(5) . . ?
C22 C23 C24 114.6(5) . . ?
C22 C23 C33 123.3(5) . . ?
C24 C23 C33 122.1(5) . . ?
C25 C24 C23 121.8(6) . . ?
C25 C24 H24 119.1 . . ?
C23 C24 H24 119.1 . . ?
C24 C25 C26 121.6(6) . . ?
C24 C25 H25 119.2 . . ?
C26 C25 H25 119.2 . . ?
C25 C26 C27 118.2(6) . . ?
C25 C26 C28 121.2(7) . . ?
C27 C26 C28 120.6(7) . . ?
C22 C27 C26 118.7(6) . . ?
C22 C27 H27 120.7 . . ?
C26 C27 H27 120.7 . . ?
C29 C28 C30 114.7(6) . . ?
C29 C28 C26 116.3(6) . . ?
C30 C28 C26 109.9(6) . . ?
C29 C28 H28 104.9 . . ?
C30 C28 H28 104.9 . . ?
C26 C28 H28 104.9 . . ?
C28 C29 H29A 109.5 . . ?
C28 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C28 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
O31 C30 O32 120.9(6) . . ?
O31 C30 C28 124.4(7) . . ?
O32 C30 C28 114.7(6) . . ?
C30 O32 H32 109.5 . . ?
C34 C33 C38 118.3(5) . . ?
C34 C33 C23 120.1(5) . . ?
C38 C33 C23 121.6(5) . . ?
C35 C34 C33 120.9(6) . . ?
C35 C34 H34 119.6 . . ?
C33 C34 H34 119.6 . . ?
C36 C35 C34 120.3(6) . . ?
C36 C35 H35 119.8 . . ?
C34 C35 H35 119.8 . . ?
C35 C36 C37 119.4(6) . . ?
C35 C36 H36 120.3 . . ?
C37 C36 H36 120.3 . . ?
C36 C37 C38 120.9(6) . . ?
C36 C37 H37 119.6 . . ?
C38 C37 H37 119.6 . . ?
C37 C38 C33 120.3(5) . . ?
C37 C38 H38 119.9 . . ?
C33 C38 H38 119.9 . . ?
O41 C42 N46 125.2(6) . . ?
O41 C42 C43 127.1(6) . . ?
N46 C42 C43 107.7(6) . . ?
C42 C43 C44 105.4(5) . . ?
C42 C43 H43A 110.7 . . ?
C44 C43 H43A 110.7 . . ?
C42 C43 H43B 110.7 . . ?
C44 C43 H43B 110.7 . . ?
H43A C43 H43B 108.8 . . ?
C43 C44 C45 103.7(5) . . ?
C43 C44 H44A 111.0 . . ?
C45 C44 H44A 111.0 . . ?
C43 C44 H44B 111.0 . . ?
C45 C44 H44B 111.0 . . ?
H44A C44 H44B 109.0 . . ?
N46 C45 C44 103.5(5) . . ?
N46 C45 H45A 111.1 . . ?
C44 C45 H45A 111.1 . . ?
N46 C45 H45B 111.1 . . ?
C44 C45 H45B 111.1 . . ?
H45A C45 H45B 109.0 . . ?
C42 N46 C47 123.7(5) . . ?
C42 N46 C45 113.6(5) . . ?
C47 N46 C45 122.1(5) . . ?
N46 C47 C51 113.5(5) . . ?
N46 C47 C48 109.8(5) . . ?
C51 C47 C48 111.5(5) . . ?
N46 C47 H47 107.2 . . ?
C51 C47 H47 107.2 . . ?
C48 C47 H47 107.2 . . ?
O49 C48 N50 122.9(5) . . ?
O49 C48 C47 120.5(5) . . ?
N50 C48 C47 116.6(5) . . ?
C48 N50 H50A 120.0 . . ?
C48 N50 H50B 120.0 . . ?
H50A N50 H50B 120.0 . . ?
C47 C51 C52 113.0(5) . . ?
C47 C51 H51A 109.0 . . ?
C52 C51 H51A 109.0 . . ?
C47 C51 H51B 109.0 . . ?
C52 C51 H51B 109.0 . . ?
H51A C51 H51B 107.8 . . ?
C51 C52 H52A 109.5 . . ?
C51 C52 H52B 109.5 . . ?
H52A C52 H52B 109.5 . . ?
C51 C52 H52C 109.5 . . ?
H52A C52 H52C 109.5 . . ?
H52B C52 H52C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 C2 C3 C4 2.4(8) . . . . ?
F1 C2 C3 C4 -177.0(4) . . . . ?
C7 C2 C3 C13 -178.9(5) . . . . ?
F1 C2 C3 C13 1.7(8) . . . . ?
C2 C3 C4 C5 -2.4(8) . . . . ?
C13 C3 C4 C5 178.9(5) . . . . ?
C3 C4 C5 C6 1.0(8) . . . . ?
C4 C5 C6 C7 0.7(8) . . . . ?
C4 C5 C6 C8 -176.9(5) . . . . ?
F1 C2 C7 C6 178.6(4) . . . . ?
C3 C2 C7 C6 -0.8(8) . . . . ?
C5 C6 C7 C2 -0.8(8) . . . . ?
C8 C6 C7 C2 176.9(5) . . . . ?
C7 C6 C8 C9 136.0(6) . . . . ?
C5 C6 C8 C9 -46.4(8) . . . . ?
C7 C6 C8 C10 -98.3(6) . . . . ?
C5 C6 C8 C10 79.3(7) . . . . ?
C9 C8 C10 O11 -134.1(6) . . . . ?
C6 C8 C10 O11 99.0(7) . . . . ?
C9 C8 C10 O12 49.8(7) . . . . ?
C6 C8 C10 O12 -77.2(6) . . . . ?
C4 C3 C13 C18 48.0(8) . . . . ?
C2 C3 C13 C18 -130.6(6) . . . . ?
C4 C3 C13 C14 -130.4(6) . . . . ?
C2 C3 C13 C14 51.0(8) . . . . ?
C18 C13 C14 C15 -0.6(8) . . . . ?
C3 C13 C14 C15 177.8(5) . . . . ?
C13 C14 C15 C16 1.0(10) . . . . ?
C14 C15 C16 C17 -0.2(11) . . . . ?
C15 C16 C17 C18 -1.1(11) . . . . ?
C14 C13 C18 C17 -0.6(9) . . . . ?
C3 C13 C18 C17 -179.1(5) . . . . ?
C16 C17 C18 C13 1.5(10) . . . . ?
C27 C22 C23 C24 -1.0(8) . . . . ?
F21 C22 C23 C24 -178.6(5) . . . . ?
C27 C22 C23 C33 178.0(5) . . . . ?
F21 C22 C23 C33 0.4(8) . . . . ?
C22 C23 C24 C25 0.5(8) . . . . ?
C33 C23 C24 C25 -178.5(5) . . . . ?
C23 C24 C25 C26 0.4(9) . . . . ?
C24 C25 C26 C27 -0.8(9) . . . . ?
C24 C25 C26 C28 178.0(6) . . . . ?
F21 C22 C27 C26 178.2(5) . . . . ?
C23 C22 C27 C26 0.6(9) . . . . ?
C25 C26 C27 C22 0.3(9) . . . . ?
C28 C26 C27 C22 -178.5(5) . . . . ?
C25 C26 C28 C29 -106.8(9) . . . . ?
C27 C26 C28 C29 72.0(9) . . . . ?
C25 C26 C28 C30 120.8(7) . . . . ?
C27 C26 C28 C30 -60.4(8) . . . . ?
C29 C28 C30 O31 -12.8(11) . . . . ?
C26 C28 C30 O31 120.4(8) . . . . ?
C29 C28 C30 O32 166.5(7) . . . . ?
C26 C28 C30 O32 -60.3(8) . . . . ?
C22 C23 C33 C34 -129.1(6) . . . . ?
C24 C23 C33 C34 49.9(7) . . . . ?
C22 C23 C33 C38 51.5(8) . . . . ?
C24 C23 C33 C38 -129.5(6) . . . . ?
C38 C33 C34 C35 0.2(8) . . . . ?
C23 C33 C34 C35 -179.2(5) . . . . ?
C33 C34 C35 C36 -0.4(9) . . . . ?
C34 C35 C36 C37 0.7(10) . . . . ?
C35 C36 C37 C38 -0.8(9) . . . . ?
C36 C37 C38 C33 0.5(9) . . . . ?
C34 C33 C38 C37 -0.2(8) . . . . ?
C23 C33 C38 C37 179.2(5) . . . . ?
O41 C42 C43 C44 166.4(6) . . . . ?
N46 C42 C43 C44 -14.2(7) . . . . ?
C42 C43 C44 C45 23.1(7) . . . . ?
C43 C44 C45 N46 -23.4(6) . . . . ?
O41 C42 N46 C47 6.4(9) . . . . ?
C43 C42 N46 C47 -173.0(5) . . . . ?
O41 C42 N46 C45 178.0(6) . . . . ?
C43 C42 N46 C45 -1.4(7) . . . . ?
C44 C45 N46 C42 16.2(7) . . . . ?
C44 C45 N46 C47 -172.0(5) . . . . ?
C42 N46 C47 C51 114.4(6) . . . . ?
C45 N46 C47 C51 -56.5(7) . . . . ?
C42 N46 C47 C48 -120.0(6) . . . . ?
C45 N46 C47 C48 69.1(6) . . . . ?
N46 C47 C48 O49 -116.4(6) . . . . ?
C51 C47 C48 O49 10.4(8) . . . . ?
N46 C47 C48 N50 63.8(6) . . . . ?
C51 C47 C48 N50 -169.4(5) . . . . ?
N46 C47 C51 C52 -58.6(7) . . . . ?
C48 C47 C51 C52 176.7(5) . . . . ?

_refine_diff_density_max         0.280
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.037

####################################################################### 
# 
# 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_alex_fl177_F
_database_code_depnum_ccdc_archive 'CCDC 2247563'
loop_
_audit_author_name
_audit_author_address
'Koen Robeyns'
;Universite catholique de Louvain
Belgium
;
_audit_update_record             
;
2023-03-09 deposited with the CCDC.	2023-04-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H7 F O3, C8 H14 N2 O2'
_chemical_formula_sum            'C16 H21 F N2 O5'
_chemical_formula_weight         340.35

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

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

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

_cell_length_a                   11.8613(14)
_cell_length_b                   5.7602(7)
_cell_length_c                   13.2858(14)
_cell_angle_alpha                90
_cell_angle_beta                 110.458(12)
_cell_angle_gamma                90
_cell_volume                     850.48(18)
_cell_formula_units_Z            2
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    2305
_cell_measurement_theta_min      3.1190
_cell_measurement_theta_max      23.3620

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_F_000             360
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.01
_exptl_absorpt_coefficient_mu    0.106
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.47542
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      297(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Incoatec microfocus source'
_diffrn_measurement_device_type  'MAR345 image plate'
_diffrn_measurement_method       
;
'120 images, ΔΦ 3.0° '
;
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11056
_diffrn_reflns_av_unetI/netI     0.0755
_diffrn_reflns_av_R_equivalents  0.0912
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.143
_diffrn_reflns_theta_max         25.230
_diffrn_reflns_theta_full        25.231
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3062
_reflns_number_gt                2103
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.804
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    0.999

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

_computing_data_collection       MAR
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_atom_sites_solution_primary     dual
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'MERCURY (Macrae et al., 2008)'
_computing_publication_material  
;
'MERCURY (Macrae et al., 2008), Platon (Spek, 2009)'
;




_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0435P)²+0.1754P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 672 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.2(10)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         3062
_refine_ls_number_parameters     220
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1045
_refine_ls_R_factor_gt           0.0642
_refine_ls_wR_factor_ref         0.1298
_refine_ls_wR_factor_gt          0.1171
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_restrained_S_all      1.077
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.9930(3) 0.6663(6) 0.2190(3) 0.0750(12) Uani 1 1 d . . . . .
C2 C 1.0298(5) 0.8307(11) 0.2965(4) 0.0463(14) Uani 1 1 d . . . . .
C3 C 1.1370(5) 0.7996(13) 0.3794(5) 0.0619(18) Uani 1 1 d . . . . .
H3 H 1.184394 0.669361 0.382457 0.074 Uiso 1 1 calc R U . . .
C4 C 1.1721(6) 0.9686(15) 0.4584(5) 0.076(2) Uani 1 1 d . . . . .
H4 H 1.245051 0.953177 0.514811 0.091 Uiso 1 1 calc R U . . .
C5 C 1.1021(7) 1.1551(15) 0.4548(5) 0.078(2) Uani 1 1 d . . . . .
H5 H 1.126515 1.266176 0.508905 0.094 Uiso 1 1 calc R U . . .
C6 C 0.9932(5) 1.1817(11) 0.3699(4) 0.0568(16) Uani 1 1 d . . . . .
H6 H 0.945392 1.310918 0.367614 0.068 Uiso 1 1 calc R U . . .
C7 C 0.9556(4) 1.0165(10) 0.2886(4) 0.0386(13) Uani 1 1 d . . . . .
C8 C 0.8366(4) 1.0453(10) 0.1961(4) 0.0460(14) Uani 1 1 d . . . . .
H8 H 0.796060 1.181515 0.211775 0.055 Uiso 1 1 calc R U . . .
O9 O 0.8589(4) 1.0912(8) 0.1017(3) 0.0638(13) Uani 1 1 d . . . . .
H9 H 0.789(5) 1.150(4) 0.050(4) 0.096 Uiso 1 1 calc R U . . .
C10 C 0.7545(4) 0.8412(10) 0.1845(4) 0.0428(14) Uani 1 1 d . . . . .
O11 O 0.6833(3) 0.7750(8) 0.0999(3) 0.0643(12) Uani 1 1 d . . . . .
O12 O 0.7597(3) 0.7478(8) 0.2769(3) 0.0631(14) Uani 1 1 d . . . . .
H12 H 0.707(5) 0.686(6) 0.2698(8) 0.095 Uiso 1 1 calc R U . . .
O21 O 0.3210(3) -0.1835(8) 0.0581(3) 0.0584(11) Uani 1 1 d . . . . .
C22 C 0.2793(4) -0.0218(10) 0.0949(4) 0.0415(14) Uani 1 1 d . . . . .
C23 C 0.1492(5) 0.0461(12) 0.0651(5) 0.0576(17) Uani 1 1 d . . . . .
H23A H 0.112773 0.070497 -0.011784 0.069 Uiso 1 1 calc R U . . .
H23B H 0.104491 -0.073783 0.086284 0.069 Uiso 1 1 calc R U . . .
C24 C 0.1498(5) 0.2675(12) 0.1250(5) 0.0652(18) Uani 1 1 d . . . . .
H24A H 0.129647 0.398280 0.075906 0.078 Uiso 1 1 calc R U . . .
H24B H 0.091628 0.259423 0.161145 0.078 Uiso 1 1 calc R U . . .
C25 C 0.2742(5) 0.2942(12) 0.2051(4) 0.0585(16) Uani 1 1 d . . . . .
H25A H 0.304279 0.450050 0.202996 0.070 Uiso 1 1 calc R U . . .
H25B H 0.275719 0.262117 0.277191 0.070 Uiso 1 1 calc R U . . .
N26 N 0.3459(3) 0.1228(8) 0.1718(3) 0.0372(10) Uani 1 1 d . . . . .
C27 C 0.4756(4) 0.1006(10) 0.2240(4) 0.0405(13) Uani 1 1 d . . . . .
H27 H 0.499861 -0.035060 0.191953 0.049 Uiso 1 1 calc R U . . .
C28 C 0.5427(4) 0.3068(10) 0.2015(4) 0.0394(13) Uani 1 1 d . . . . .
N29 N 0.5032(4) 0.3945(10) 0.1052(3) 0.0599(15) Uani 1 1 d . . . . .
H29A H 0.540823 0.508154 0.089077 0.072 Uiso 1 1 calc R U . . .
H29B H 0.439541 0.338774 0.057577 0.072 Uiso 1 1 calc R U . . .
O30 O 0.6342(3) 0.3810(7) 0.2729(3) 0.0592(12) Uani 1 1 d . . . . .
C31 C 0.5144(6) 0.0522(11) 0.3450(4) 0.0590(17) Uani 1 1 d . . . . .
H31A H 0.601497 0.043391 0.375197 0.071 Uiso 1 1 calc R U . . .
H31B H 0.488924 0.180024 0.379530 0.071 Uiso 1 1 calc R U . . .
C32 C 0.4616(7) -0.1715(16) 0.3687(5) 0.086(2) Uani 1 1 d . . . . .
H32A H 0.375391 -0.161330 0.341404 0.129 Uiso 1 1 calc R U . . .
H32B H 0.489217 -0.196347 0.444946 0.129 Uiso 1 1 calc R U . . .
H32C H 0.486729 -0.298637 0.334845 0.129 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C2 1.354(6) . ?
C2 C7 1.366(7) . ?
C2 C3 1.373(7) . ?
C3 C4 1.385(10) . ?
C3 H3 0.9300 . ?
C4 C5 1.348(10) . ?
C4 H4 0.9300 . ?
C5 C6 1.395(8) . ?
C5 H5 0.9300 . ?
C6 C7 1.390(7) . ?
C6 H6 0.9300 . ?
C7 C8 1.523(7) . ?
C8 O9 1.395(6) . ?
C8 C10 1.499(8) . ?
C8 H8 0.9800 . ?
O9 H9 0.93(7) . ?
C10 O11 1.208(5) . ?
C10 O12 1.323(6) . ?
O12 H12 0.70(7) . ?
O21 C22 1.233(6) . ?
C22 N26 1.341(6) . ?
C22 C23 1.505(7) . ?
C23 C24 1.502(8) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C24 C25 1.495(7) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C25 N26 1.468(7) . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
N26 C27 1.456(6) . ?
C27 C28 1.517(7) . ?
C27 C31 1.535(6) . ?
C27 H27 0.9800 . ?
C28 O30 1.241(5) . ?
C28 N29 1.301(6) . ?
N29 H29A 0.8600 . ?
N29 H29B 0.8600 . ?
C31 C32 1.513(9) . ?
C31 H31A 0.9700 . ?
C31 H31B 0.9700 . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 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
F1 C2 C7 117.5(4) . . ?
F1 C2 C3 118.7(6) . . ?
C7 C2 C3 123.7(6) . . ?
C2 C3 C4 117.8(7) . . ?
C2 C3 H3 121.1 . . ?
C4 C3 H3 121.1 . . ?
C5 C4 C3 121.0(6) . . ?
C5 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?
C4 C5 C6 120.1(7) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C7 C6 C5 120.5(6) . . ?
C7 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
C2 C7 C6 117.0(5) . . ?
C2 C7 C8 122.5(5) . . ?
C6 C7 C8 120.5(5) . . ?
O9 C8 C10 112.1(5) . . ?
O9 C8 C7 109.4(4) . . ?
C10 C8 C7 112.5(4) . . ?
O9 C8 H8 107.5 . . ?
C10 C8 H8 107.5 . . ?
C7 C8 H8 107.5 . . ?
C8 O9 H9 109.5 . . ?
O11 C10 O12 121.7(5) . . ?
O11 C10 C8 124.1(5) . . ?
O12 C10 C8 113.9(4) . . ?
C10 O12 H12 109.5 . . ?
O21 C22 N26 124.1(5) . . ?
O21 C22 C23 127.5(5) . . ?
N26 C22 C23 108.5(5) . . ?
C24 C23 C22 105.4(5) . . ?
C24 C23 H23A 110.7 . . ?
C22 C23 H23A 110.7 . . ?
C24 C23 H23B 110.7 . . ?
C22 C23 H23B 110.7 . . ?
H23A C23 H23B 108.8 . . ?
C25 C24 C23 106.6(5) . . ?
C25 C24 H24A 110.4 . . ?
C23 C24 H24A 110.4 . . ?
C25 C24 H24B 110.4 . . ?
C23 C24 H24B 110.4 . . ?
H24A C24 H24B 108.6 . . ?
N26 C25 C24 104.4(5) . . ?
N26 C25 H25A 110.9 . . ?
C24 C25 H25A 110.9 . . ?
N26 C25 H25B 110.9 . . ?
C24 C25 H25B 110.9 . . ?
H25A C25 H25B 108.9 . . ?
C22 N26 C27 123.5(4) . . ?
C22 N26 C25 113.4(4) . . ?
C27 N26 C25 122.9(4) . . ?
N26 C27 C28 112.2(4) . . ?
N26 C27 C31 113.2(4) . . ?
C28 C27 C31 111.3(4) . . ?
N26 C27 H27 106.5 . . ?
C28 C27 H27 106.5 . . ?
C31 C27 H27 106.5 . . ?
O30 C28 N29 122.5(5) . . ?
O30 C28 C27 119.8(4) . . ?
N29 C28 C27 117.7(4) . . ?
C28 N29 H29A 120.0 . . ?
C28 N29 H29B 120.0 . . ?
H29A N29 H29B 120.0 . . ?
C32 C31 C27 112.2(5) . . ?
C32 C31 H31A 109.2 . . ?
C27 C31 H31A 109.2 . . ?
C32 C31 H31B 109.2 . . ?
C27 C31 H31B 109.2 . . ?
H31A C31 H31B 107.9 . . ?
C31 C32 H32A 109.5 . . ?
C31 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C31 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F1 C2 C3 C4 -179.3(5) . . . . ?
C7 C2 C3 C4 -1.0(9) . . . . ?
C2 C3 C4 C5 1.2(10) . . . . ?
C3 C4 C5 C6 -0.8(11) . . . . ?
C4 C5 C6 C7 0.2(10) . . . . ?
F1 C2 C7 C6 178.7(4) . . . . ?
C3 C2 C7 C6 0.4(8) . . . . ?
F1 C2 C7 C8 -1.2(7) . . . . ?
C3 C2 C7 C8 -179.4(5) . . . . ?
C5 C6 C7 C2 0.0(8) . . . . ?
C5 C6 C7 C8 179.9(5) . . . . ?
C2 C7 C8 O9 -69.3(6) . . . . ?
C6 C7 C8 O9 110.8(6) . . . . ?
C2 C7 C8 C10 56.1(6) . . . . ?
C6 C7 C8 C10 -123.8(5) . . . . ?
O9 C8 C10 O11 -24.6(7) . . . . ?
C7 C8 C10 O11 -148.5(5) . . . . ?
O9 C8 C10 O12 160.4(5) . . . . ?
C7 C8 C10 O12 36.5(6) . . . . ?
O21 C22 C23 C24 -174.3(5) . . . . ?
N26 C22 C23 C24 6.8(6) . . . . ?
C22 C23 C24 C25 -12.2(6) . . . . ?
C23 C24 C25 N26 12.9(6) . . . . ?
O21 C22 N26 C27 -2.3(8) . . . . ?
C23 C22 N26 C27 176.6(5) . . . . ?
O21 C22 N26 C25 -177.4(5) . . . . ?
C23 C22 N26 C25 1.6(6) . . . . ?
C24 C25 N26 C22 -9.3(6) . . . . ?
C24 C25 N26 C27 175.6(5) . . . . ?
C22 N26 C27 C28 115.9(5) . . . . ?
C25 N26 C27 C28 -69.5(6) . . . . ?
C22 N26 C27 C31 -117.1(5) . . . . ?
C25 N26 C27 C31 57.6(7) . . . . ?
N26 C27 C28 O30 143.0(5) . . . . ?
C31 C27 C28 O30 15.0(7) . . . . ?
N26 C27 C28 N29 -39.2(6) . . . . ?
C31 C27 C28 N29 -167.3(5) . . . . ?
N26 C27 C31 C32 60.3(7) . . . . ?
C28 C27 C31 C32 -172.2(5) . . . . ?

_refine_diff_density_max         0.164
_refine_diff_density_min         -0.141
_refine_diff_density_rms         0.037

####################################################################### 
# 
# 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_alex_fl171
_database_code_depnum_ccdc_archive 'CCDC 2247566'
loop_
_audit_author_name
_audit_author_address
'Koen Robeyns'
;Universite catholique de Louvain
Belgium
;
_audit_update_record             
;
2023-03-09 deposited with the CCDC.	2023-04-28 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_THETM01_alex_fl171          
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.550
RESPONSE: A data cut-off of 1A was imposed during integration beyond which the crystal diffracted poorly
;
# Added during the CSD deposition process: Thursday 09 March 2023 01:41 PM
# end Validation Reply Form


_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C5 H8 O4, C5 H9 N O2'
_chemical_formula_sum            'C10 H17 N O6'
_chemical_formula_weight         247.24

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

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

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

_cell_length_a                   9.8806(18)
_cell_length_b                   9.6156(19)
_cell_length_c                   25.364(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2409.8(8)
_cell_formula_units_Z            8
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    1660
_cell_measurement_theta_min      2.5910
_cell_measurement_theta_max      20.4730

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.363
_exptl_crystal_F_000             1056
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.01
_exptl_absorpt_coefficient_mu    0.113
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.21080
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?



_diffrn_ambient_temperature      297(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Incoatec microfocus source'
_diffrn_measurement_device_type  'MAR345 image plate'
_diffrn_measurement_method       
;
'143 images, ΔΦ 1.2° '
;
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7426
_diffrn_reflns_av_unetI/netI     0.0623
_diffrn_reflns_av_R_equivalents  0.1096
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.613
_diffrn_reflns_theta_max         20.944
_diffrn_reflns_theta_full        20.944
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             1270
_reflns_number_gt                1015
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       MAR
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_atom_sites_solution_primary     dual
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'MERCURY (Macrae et al., 2008)'
_computing_publication_material  
;
'MERCURY (Macrae et al., 2008), Platon (Spek, 2009)'
;



_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0470P)²+6.3277P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1270
_refine_ls_number_parameters     157
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1073
_refine_ls_R_factor_gt           0.0819
_refine_ls_wR_factor_ref         0.1773
_refine_ls_wR_factor_gt          0.1632
_refine_ls_goodness_of_fit_ref   1.151
_refine_ls_restrained_S_all      1.151
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.4876(4) 0.3680(4) 0.79463(17) 0.0351(12) Uani 1 1 d . . . . .
H1A H 0.542819 0.435868 0.784335 0.042 Uiso 1 1 calc R U . . .
H1B H 0.527142 0.286884 0.787746 0.042 Uiso 1 1 calc R U . . .
C3 C 0.4597(6) 0.3803(7) 0.8526(2) 0.0504(18) Uani 1 1 d . . . . .
H3A H 0.523983 0.326245 0.872910 0.060 Uiso 1 1 calc R U . . .
H3B H 0.463818 0.476569 0.863918 0.060 Uiso 1 1 calc R U . . .
C4 C 0.3228(8) 0.3248(11) 0.8582(3) 0.090(3) Uani 1 1 d . . . . .
H4A H 0.278248 0.365395 0.888578 0.109 Uiso 1 1 calc R U . . .
H4B H 0.325283 0.224635 0.862530 0.109 Uiso 1 1 calc R U . . .
C5 C 0.2496(7) 0.3626(7) 0.8088(2) 0.058(2) Uani 1 1 d . . . . .
H5A H 0.200735 0.449248 0.813425 0.070 Uiso 1 1 calc R U . . .
H5B H 0.185310 0.290420 0.799434 0.070 Uiso 1 1 calc R U . . .
C6 C 0.3562(6) 0.3780(6) 0.7658(2) 0.0370(16) Uani 1 1 d . . . . .
H00C H 0.348706 0.299558 0.741299 0.044 Uiso 1 1 calc R U . . .
C7 C 0.3458(7) 0.5152(6) 0.7345(2) 0.0354(15) Uani 1 1 d . . . . .
O8 O 0.4448(4) 0.5955(4) 0.73588(17) 0.0532(13) Uani 1 1 d . . . . .
O9 O 0.2363(4) 0.5329(4) 0.71064(15) 0.0417(11) Uani 1 1 d . . . . .
C10 C 0.1660(6) 0.8962(5) 0.5810(2) 0.0360(15) Uani 1 1 d . . . . .
H10 H 0.239044 0.950074 0.597276 0.043 Uiso 1 1 calc R U . . .
C11 C 0.1665(6) 0.7517(6) 0.6047(2) 0.0371(15) Uani 1 1 d . . . . .
O12 O 0.1018(5) 0.6548(4) 0.58725(18) 0.0594(14) Uani 1 1 d . . . . .
O13 O 0.2386(4) 0.7438(4) 0.64786(16) 0.0472(12) Uani 1 1 d . . . . .
H13 H 0.227204 0.667514 0.661632 0.071 Uiso 1 1 calc R U . . .
C14 C 0.0301(6) 0.9649(6) 0.5953(3) 0.0522(18) Uani 1 1 d . . . . .
H14A H 0.029180 1.058977 0.582735 0.078 Uiso 1 1 calc R U . . .
H14B H 0.018944 0.964504 0.632949 0.078 Uiso 1 1 calc R U . . .
H14C H -0.042635 0.913879 0.579318 0.078 Uiso 1 1 calc R U . . .
C15 C 0.1865(6) 0.8974(6) 0.5215(2) 0.0446(17) Uani 1 1 d . . . . .
H15A H 0.120794 0.835864 0.505273 0.054 Uiso 1 1 calc R U . . .
H15B H 0.170269 0.990564 0.508309 0.054 Uiso 1 1 calc R U . . .
C16 C 0.3272(7) 0.8520(7) 0.5056(3) 0.0479(18) Uani 1 1 d . . . . .
O17 O 0.4000(5) 0.7815(5) 0.53158(19) 0.0724(16) Uani 1 1 d . . . . .
O18 O 0.3576(5) 0.8948(6) 0.45687(19) 0.0772(18) Uani 1 1 d . . . . .
H18 H 0.431(9) 0.884(9) 0.4519(15) 0.116 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C6 1.493(7) . ?
N1 C3 1.499(7) . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
C3 C4 1.461(9) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.492(9) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.523(8) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C7 1.544(8) . ?
C6 H00C 0.9800 . ?
C7 O8 1.247(7) . ?
C7 O9 1.250(7) . ?
C10 C11 1.514(8) . ?
C10 C15 1.523(8) . ?
C10 C14 1.540(8) . ?
C10 H10 0.9800 . ?
C11 O12 1.213(7) . ?
C11 O13 1.309(7) . ?
O13 H13 0.8200 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 C16 1.511(9) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 O17 1.189(7) . ?
C16 O18 1.336(7) . ?
O18 H18 0.74(9) . ?

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
C6 N1 C3 108.4(4) . . ?
C6 N1 H1A 110.0 . . ?
C3 N1 H1A 110.0 . . ?
C6 N1 H1B 110.0 . . ?
C3 N1 H1B 110.0 . . ?
H1A N1 H1B 108.4 . . ?
C4 C3 N1 103.7(5) . . ?
C4 C3 H3A 111.0 . . ?
N1 C3 H3A 111.0 . . ?
C4 C3 H3B 111.0 . . ?
N1 C3 H3B 111.0 . . ?
H3A C3 H3B 109.0 . . ?
C3 C4 C5 106.1(6) . . ?
C3 C4 H4A 110.5 . . ?
C5 C4 H4A 110.5 . . ?
C3 C4 H4B 110.5 . . ?
C5 C4 H4B 110.5 . . ?
H4A C4 H4B 108.7 . . ?
C4 C5 C6 106.8(5) . . ?
C4 C5 H5A 110.4 . . ?
C6 C5 H5A 110.4 . . ?
C4 C5 H5B 110.4 . . ?
C6 C5 H5B 110.4 . . ?
H5A C5 H5B 108.6 . . ?
N1 C6 C5 104.1(4) . . ?
N1 C6 C7 111.4(5) . . ?
C5 C6 C7 113.9(5) . . ?
N1 C6 H00C 109.1 . . ?
C5 C6 H00C 109.1 . . ?
C7 C6 H00C 109.1 . . ?
O8 C7 O9 127.5(5) . . ?
O8 C7 C6 117.5(5) . . ?
O9 C7 C6 115.0(5) . . ?
C11 C10 C15 113.6(5) . . ?
C11 C10 C14 107.6(5) . . ?
C15 C10 C14 110.3(5) . . ?
C11 C10 H10 108.4 . . ?
C15 C10 H10 108.4 . . ?
C14 C10 H10 108.4 . . ?
O12 C11 O13 123.2(5) . . ?
O12 C11 C10 124.0(6) . . ?
O13 C11 C10 112.8(5) . . ?
C11 O13 H13 109.5 . . ?
C10 C14 H14A 109.5 . . ?
C10 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C10 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C16 C15 C10 112.7(5) . . ?
C16 C15 H15A 109.1 . . ?
C10 C15 H15A 109.1 . . ?
C16 C15 H15B 109.1 . . ?
C10 C15 H15B 109.1 . . ?
H15A C15 H15B 107.8 . . ?
O17 C16 O18 123.6(6) . . ?
O17 C16 C15 124.9(6) . . ?
O18 C16 C15 111.4(6) . . ?
C16 O18 H18 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 N1 C3 C4 28.8(7) . . . . ?
N1 C3 C4 C5 -33.3(8) . . . . ?
C3 C4 C5 C6 26.1(9) . . . . ?
C3 N1 C6 C5 -12.7(6) . . . . ?
C3 N1 C6 C7 110.5(5) . . . . ?
C4 C5 C6 N1 -7.8(7) . . . . ?
C4 C5 C6 C7 -129.4(6) . . . . ?
N1 C6 C7 O8 1.7(7) . . . . ?
C5 C6 C7 O8 119.2(6) . . . . ?
N1 C6 C7 O9 -177.7(5) . . . . ?
C5 C6 C7 O9 -60.3(7) . . . . ?
C15 C10 C11 O12 -48.0(8) . . . . ?
C14 C10 C11 O12 74.4(7) . . . . ?
C15 C10 C11 O13 135.5(5) . . . . ?
C14 C10 C11 O13 -102.1(6) . . . . ?
C11 C10 C15 C16 -68.1(7) . . . . ?
C14 C10 C15 C16 171.0(5) . . . . ?
C10 C15 C16 O17 23.4(9) . . . . ?
C10 C15 C16 O18 -160.1(6) . . . . ?

_refine_diff_density_max         0.369
_refine_diff_density_min         -0.264
_refine_diff_density_rms         0.055

####################################################################### 
# 
# 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_alex_Lena_Ltar
_database_code_depnum_ccdc_archive 'CCDC 2247564'
loop_
_audit_author_name
_audit_author_address
'Koen Robeyns'
;Universite catholique de Louvain
Belgium
;
_audit_update_record             
;
2023-03-09 deposited with the CCDC.	2023-04-28 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_THETM01_alex_Lena_Ltar      
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.550
RESPONSE: A data cut-off of 1.1A was imposed during integration beyond which the crystal diffracted poorly
;
# Added during the CSD deposition process: Thursday 09 March 2023 01:41 PM
# end Validation Reply Form


_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H7 F O3, C5 H9 N O2'
_chemical_formula_sum            'C13 H16 F N O5'
_chemical_formula_weight         285.27

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   7.406(5)
_cell_length_b                   8.459(2)
_cell_length_c                   12.281(7)
_cell_angle_alpha                102.89(4)
_cell_angle_beta                 101.66(6)
_cell_angle_gamma                103.44(4)
_cell_volume                     702.8(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    286
_cell_measurement_theta_min      3.2740
_cell_measurement_theta_max      18.1940

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.348
_exptl_crystal_F_000             300
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_exptl_absorpt_coefficient_mu    0.112
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.93501
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?



_diffrn_ambient_temperature      297(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Incoatec microfocus source'
_diffrn_measurement_device_type  'MAR345 image plate'
_diffrn_measurement_method       
;
'65 images, ΔΦ 3.0° '
;
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            2190
_diffrn_reflns_av_unetI/netI     0.1494
_diffrn_reflns_av_R_equivalents  0.1060
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.993
_diffrn_reflns_theta_max         18.845
_diffrn_reflns_theta_full        18.845
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measured_fraction_theta_full 0.961
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_Laue_measured_fraction_full 0.961
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_point_group_measured_fraction_full 0.961
_reflns_number_total             1057
_reflns_number_gt                525
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       MAR
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_atom_sites_solution_primary     dual
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'MERCURY (Macrae et al., 2008)'
_computing_publication_material  
;
'MERCURY (Macrae et al., 2008), Platon (Spek, 2009)'
;


_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0524P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1057
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1647
_refine_ls_R_factor_gt           0.0706
_refine_ls_wR_factor_ref         0.1526
_refine_ls_wR_factor_gt          0.1209
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_restrained_S_all      1.002
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.9872(12) -0.0455(9) 0.6398(6) 0.063(2) Uani 1 1 d . . . . .
H1A H 1.033582 0.040067 0.612570 0.075 Uiso 1 1 calc R U . . .
H1AB H 0.949526 -0.141184 0.582316 0.075 Uiso 1 1 calc R U . . .
C2 C 1.1418(15) -0.0547(13) 0.7389(10) 0.077(3) Uani 1 1 d . . . . .
H2A H 1.171701 -0.161488 0.719394 0.093 Uiso 1 1 calc R U . . .
H2AB H 1.258762 0.037206 0.755362 0.093 Uiso 1 1 calc R U . . .
C3 C 1.0596(18) -0.0398(17) 0.8410(10) 0.117(5) Uani 1 1 d . . . . .
H3A H 1.157840 0.031180 0.910919 0.141 Uiso 1 1 calc R U . . .
H3AB H 1.011497 -0.150767 0.851440 0.141 Uiso 1 1 calc R U . . .
C4 C 0.8982(17) 0.0380(13) 0.8174(10) 0.084(4) Uani 1 1 d . . . . .
H4A H 0.945817 0.160633 0.845925 0.101 Uiso 1 1 calc R U . . .
H4AB H 0.799699 -0.001807 0.854443 0.101 Uiso 1 1 calc R U . . .
C5 C 0.8182(14) -0.0189(11) 0.6861(9) 0.055(3) Uani 1 1 d . . . . .
H5 H 0.719539 -0.128481 0.664230 0.066 Uiso 1 1 calc R U . . .
O7 O 0.7929(9) 0.1544(7) 0.5517(6) 0.063(2) Uani 1 1 d . . . . .
C6 C 0.7276(17) 0.1064(12) 0.6317(10) 0.059(3) Uani 1 1 d . . . . .
O8 O 0.5982(11) 0.1444(9) 0.6752(6) 0.088(3) Uani 1 1 d . . . . .
F11 F 0.3242(12) 0.3731(11) 0.1624(7) 0.160(4) Uani 1 1 d . . . . .
C12 C 0.510(2) 0.3983(19) 0.1512(17) 0.091(4) Uani 1 1 d . . . . .
C13 C 0.534(3) 0.3277(18) 0.0410(14) 0.128(6) Uani 1 1 d . . . . .
H13 H 0.427274 0.265177 -0.021013 0.153 Uiso 1 1 calc R U . . .
C14 C 0.718(4) 0.353(2) 0.0274(16) 0.119(6) Uani 1 1 d . . . . .
H14 H 0.737401 0.308820 -0.044360 0.143 Uiso 1 1 calc R U . . .
C15 C 0.876(2) 0.4460(19) 0.1217(17) 0.094(5) Uani 1 1 d . . . . .
H15 H 1.000027 0.464969 0.112794 0.112 Uiso 1 1 calc R U . . .
C16 C 0.847(2) 0.5107(12) 0.2304(11) 0.069(4) Uani 1 1 d . . . . .
H16 H 0.953517 0.568359 0.293178 0.083 Uiso 1 1 calc R U . . .
C17 C 0.662(2) 0.4915(14) 0.2476(12) 0.056(3) Uani 1 1 d . . . . .
C18 C 0.6328(14) 0.5703(12) 0.3647(9) 0.058(3) Uani 1 1 d . . . . .
H18 H 0.493939 0.543567 0.356837 0.070 Uiso 1 1 calc R U . . .
O19 O 0.7125(8) 0.7526(7) 0.4025(5) 0.061(2) Uani 1 1 d . . . . .
H19 H 0.628193 0.796299 0.382431 0.092 Uiso 1 1 calc R U . . .
C20 C 0.7235(16) 0.4961(13) 0.4611(11) 0.053(3) Uani 1 1 d . . . . .
O21 O 0.8382(11) 0.5836(8) 0.5520(6) 0.070(2) Uani 1 1 d . . . . .
O22 O 0.6450(8) 0.3289(8) 0.4293(5) 0.065(2) Uani 1 1 d . . . . .
H22 H 0.704216 0.287606 0.473819 0.097 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C5 1.517(10) . ?
N1 C2 1.523(10) . ?
N1 H1A 0.8900 . ?
N1 H1AB 0.8900 . ?
C2 C3 1.495(12) . ?
C2 H2A 0.9700 . ?
C2 H2AB 0.9700 . ?
C3 C4 1.502(12) . ?
C3 H3A 0.9700 . ?
C3 H3AB 0.9700 . ?
C4 C5 1.523(11) . ?
C4 H4A 0.9700 . ?
C4 H4AB 0.9700 . ?
C5 C6 1.576(12) . ?
C5 H5 0.9800 . ?
O7 C6 1.282(11) . ?
C6 O8 1.257(11) . ?
F11 C12 1.382(13) . ?
C12 C17 1.386(15) . ?
C12 C13 1.415(16) . ?
C13 C14 1.385(17) . ?
C13 H13 0.9300 . ?
C14 C15 1.392(16) . ?
C14 H14 0.9300 . ?
C15 C16 1.404(14) . ?
C15 H15 0.9300 . ?
C16 C17 1.405(13) . ?
C16 H16 0.9300 . ?
C17 C18 1.524(12) . ?
C18 O19 1.445(9) . ?
C18 C20 1.566(12) . ?
C18 H18 0.9800 . ?
O19 H19 0.8200 . ?
C20 O21 1.213(10) . ?
C20 O22 1.331(10) . ?
O22 H22 0.8200 . ?

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 N1 C2 108.0(7) . . ?
C5 N1 H1A 110.1 . . ?
C2 N1 H1A 110.1 . . ?
C5 N1 H1AB 110.1 . . ?
C2 N1 H1AB 110.1 . . ?
H1A N1 H1AB 108.4 . . ?
C3 C2 N1 105.9(8) . . ?
C3 C2 H2A 110.6 . . ?
N1 C2 H2A 110.6 . . ?
C3 C2 H2AB 110.6 . . ?
N1 C2 H2AB 110.6 . . ?
H2A C2 H2AB 108.7 . . ?
C2 C3 C4 107.3(9) . . ?
C2 C3 H3A 110.3 . . ?
C4 C3 H3A 110.3 . . ?
C2 C3 H3AB 110.3 . . ?
C4 C3 H3AB 110.3 . . ?
H3A C3 H3AB 108.5 . . ?
C3 C4 C5 105.1(8) . . ?
C3 C4 H4A 110.7 . . ?
C5 C4 H4A 110.7 . . ?
C3 C4 H4AB 110.7 . . ?
C5 C4 H4AB 110.7 . . ?
H4A C4 H4AB 108.8 . . ?
N1 C5 C4 104.8(8) . . ?
N1 C5 C6 110.8(9) . . ?
C4 C5 C6 115.9(8) . . ?
N1 C5 H5 108.4 . . ?
C4 C5 H5 108.4 . . ?
C6 C5 H5 108.4 . . ?
O8 C6 O7 129.4(10) . . ?
O8 C6 C5 113.1(10) . . ?
O7 C6 C5 117.5(10) . . ?
F11 C12 C17 118.5(15) . . ?
F11 C12 C13 117.8(18) . . ?
C17 C12 C13 123.7(14) . . ?
C14 C13 C12 118.7(16) . . ?
C14 C13 H13 120.6 . . ?
C12 C13 H13 120.6 . . ?
C13 C14 C15 119.7(18) . . ?
C13 C14 H14 120.2 . . ?
C15 C14 H14 120.2 . . ?
C14 C15 C16 120.0(16) . . ?
C14 C15 H15 120.0 . . ?
C16 C15 H15 120.0 . . ?
C15 C16 C17 122.3(12) . . ?
C15 C16 H16 118.8 . . ?
C17 C16 H16 118.8 . . ?
C12 C17 C16 115.5(12) . . ?
C12 C17 C18 122.9(14) . . ?
C16 C17 C18 121.6(14) . . ?
O19 C18 C17 112.4(8) . . ?
O19 C18 C20 108.7(8) . . ?
C17 C18 C20 111.8(8) . . ?
O19 C18 H18 107.9 . . ?
C17 C18 H18 107.9 . . ?
C20 C18 H18 107.9 . . ?
C18 O19 H19 109.5 . . ?
O21 C20 O22 127.5(10) . . ?
O21 C20 C18 123.2(9) . . ?
O22 C20 C18 109.1(10) . . ?
C20 O22 H22 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C2 C3 2.0(11) . . . . ?
N1 C2 C3 C4 -19.8(12) . . . . ?
C2 C3 C4 C5 29.9(13) . . . . ?
C2 N1 C5 C4 16.0(9) . . . . ?
C2 N1 C5 C6 141.7(8) . . . . ?
C3 C4 C5 N1 -27.9(11) . . . . ?
C3 C4 C5 C6 -150.3(10) . . . . ?
N1 C5 C6 O8 -174.0(9) . . . . ?
C4 C5 C6 O8 -54.7(13) . . . . ?
N1 C5 C6 O7 6.1(12) . . . . ?
C4 C5 C6 O7 125.3(11) . . . . ?
F11 C12 C13 C14 179.2(13) . . . . ?
C17 C12 C13 C14 -1(2) . . . . ?
C12 C13 C14 C15 1(2) . . . . ?
C13 C14 C15 C16 1(2) . . . . ?
C14 C15 C16 C17 -2.6(17) . . . . ?
F11 C12 C17 C16 179.3(9) . . . . ?
C13 C12 C17 C16 -1.0(17) . . . . ?
F11 C12 C17 C18 -1.3(16) . . . . ?
C13 C12 C17 C18 178.4(11) . . . . ?
C15 C16 C17 C12 2.5(14) . . . . ?
C15 C16 C17 C18 -176.9(9) . . . . ?
C12 C17 C18 O19 -119.5(10) . . . . ?
C16 C17 C18 O19 59.8(11) . . . . ?
C12 C17 C18 C20 117.9(11) . . . . ?
C16 C17 C18 C20 -62.7(12) . . . . ?
O19 C18 C20 O21 1.4(14) . . . . ?
C17 C18 C20 O21 126.0(12) . . . . ?
O19 C18 C20 O22 177.4(7) . . . . ?
C17 C18 C20 O22 -58.0(11) . . . . ?

_refine_diff_density_max         0.208
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.043

####################################################################### 
# 
# 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_Alex_RS-DL
_database_code_depnum_ccdc_archive 'CCDC 2247567'
loop_
_audit_author_name
_audit_author_address
'Koen Robeyns'
;Universite catholique de Louvain
Belgium
;
_audit_update_record             
;
2023-03-09 deposited with the CCDC.	2023-04-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H8 O3, C5 H9 N O2'
_chemical_formula_sum            'C13 H17 N O5'
_chemical_formula_weight         267.27

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   7.0962(13)
_cell_length_b                   8.306(2)
_cell_length_c                   12.120(3)
_cell_angle_alpha                103.74(2)
_cell_angle_beta                 99.820(18)
_cell_angle_gamma                105.63(2)
_cell_volume                     646.9(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1521
_cell_measurement_theta_min      2.6540
_cell_measurement_theta_max      25.8760

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.372
_exptl_crystal_F_000             284
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    0.106
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.79878
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?





_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Incoatec microfocus source'
_diffrn_measurement_device_type  'MAR345 image plate'
_diffrn_measurement_method       
;
'60 images, ΔΦ 3.0° '
'60 images, ΔΦ 3.0° (2nd orientation)'
;
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8814
_diffrn_reflns_av_unetI/netI     0.0366
_diffrn_reflns_av_R_equivalents  0.0546
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.668
_diffrn_reflns_theta_max         26.212
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measured_fraction_theta_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_point_group_measured_fraction_full 0.980
_reflns_number_total             2534
_reflns_number_gt                2040
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       MAR
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_atom_sites_solution_primary     'dual space'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'MERCURY (Macrae et al., 2008)'
_computing_publication_material  
;
'MERCURY (Macrae et al., 2008), Platon (Spek, 2009)'
;





_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0841P)²+0.3023P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2534
_refine_ls_number_parameters     195
_refine_ls_number_restraints     60
_refine_ls_R_factor_all          0.0715
_refine_ls_R_factor_gt           0.0590
_refine_ls_wR_factor_ref         0.1740
_refine_ls_wR_factor_gt          0.1638
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_restrained_S_all      1.071
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.4929(3) -0.0376(2) 0.64126(16) 0.0380(4) Uani 1 1 d . . . . .
H1A H 0.457208 -0.136378 0.582607 0.046 Uiso 1 1 calc R U . . .
H1AB H 0.547509 0.051534 0.615536 0.046 Uiso 1 1 calc R U . . .
C2 C 0.6427(4) -0.0434(4) 0.7425(2) 0.0497(6) Uani 1 1 d . . . . .
H2A H 0.690304 -0.142451 0.719619 0.060 Uiso 1 1 calc R U . . .
H2AB H 0.757856 0.063295 0.770705 0.060 Uiso 1 1 calc R U . . .
C3 C 0.5305(5) -0.0616(4) 0.8348(3) 0.0647(8) Uani 1 1 d . . . . .
H3A H 0.621030 -0.007972 0.912639 0.078 Uiso 1 1 calc R U . . .
H3AB H 0.462068 -0.183858 0.825495 0.078 Uiso 1 1 calc R U . . .
C4 C 0.3798(5) 0.0340(4) 0.8145(2) 0.0603(7) Uani 1 1 d . . . . .
H4A H 0.267265 -0.004061 0.848168 0.072 Uiso 1 1 calc R U . . .
H4AB H 0.443401 0.159702 0.848301 0.072 Uiso 1 1 calc R U . . .
C5 C 0.3105(3) -0.0155(3) 0.6824(2) 0.0411(5) Uani 1 1 d . . . . .
H5 H 0.204219 -0.129948 0.654836 0.049 Uiso 1 1 calc R U . . .
C6 C 0.2287(3) 0.1125(3) 0.6334(2) 0.0421(5) Uani 1 1 d . . . . .
O7 O 0.2985(3) 0.1568(2) 0.55247(16) 0.0498(5) Uani 1 1 d . . . . .
O8 O 0.1017(3) 0.1593(3) 0.67848(19) 0.0661(6) Uani 1 1 d . . . . .
C11 C 0.1461(11) 0.484(3) 0.2460(9) 0.0404(13) Uani 0.733(13) 1 d D U P A 1
C12 C 0.3307(10) 0.4932(19) 0.2203(7) 0.0487(10) Uani 0.733(13) 1 d D U P A 1
H12 H 0.449130 0.548528 0.279773 0.058 Uiso 0.733(13) 1 calc R U P A 1
C13 C 0.3412(11) 0.4208(12) 0.1068(6) 0.0602(15) Uani 0.733(13) 1 d D U P A 1
H13 H 0.466410 0.426537 0.091330 0.072 Uiso 0.733(13) 1 calc R U P A 1
C14 C 0.1716(13) 0.3422(11) 0.0187(5) 0.0793(18) Uani 0.733(13) 1 d D U P A 1
H14 H 0.179251 0.291169 -0.056791 0.095 Uiso 0.733(13) 1 calc R U P A 1
C15 C -0.0117(11) 0.3384(10) 0.0415(5) 0.0910(19) Uani 0.733(13) 1 d D U P A 1
H15 H -0.128604 0.287626 -0.019332 0.109 Uiso 0.733(13) 1 calc R U P A 1
C16 C -0.0248(9) 0.4099(9) 0.1551(5) 0.0667(14) Uani 0.733(13) 1 d D U P A 1
H16 H -0.150066 0.407263 0.169386 0.080 Uiso 0.733(13) 1 calc R U P A 1
C11B C 0.171(3) 0.485(9) 0.251(3) 0.0404(13) Uani 0.267(13) 1 d D . P A 2
C12B C 0.368(3) 0.514(6) 0.2400(19) 0.0487(10) Uani 0.267(13) 1 d D . P A 2
H12B H 0.475486 0.575321 0.305410 0.058 Uiso 0.267(13) 1 calc R U P A 2
C13B C 0.404(2) 0.452(4) 0.132(2) 0.0602(15) Uani 0.267(13) 1 d D . P A 2
H13B H 0.535740 0.481104 0.123006 0.072 Uiso 0.267(13) 1 calc R U P A 2
C14B C 0.249(3) 0.349(3) 0.0387(16) 0.0793(18) Uani 0.267(13) 1 d D . P A 2
H14B H 0.273368 0.314287 -0.034895 0.095 Uiso 0.267(13) 1 calc R U P A 2
C15B C 0.056(3) 0.295(3) 0.0519(14) 0.0910(19) Uani 0.267(13) 1 d D . P A 2
H15B H -0.048141 0.214075 -0.009972 0.109 Uiso 0.267(13) 1 calc R U P A 2
C16B C 0.019(2) 0.364(2) 0.1598(14) 0.0667(14) Uani 0.267(13) 1 d D . P A 2
H16B H -0.111531 0.326918 0.169914 0.080 Uiso 0.267(13) 1 calc R U P A 2
C17 C 0.1304(3) 0.5656(3) 0.3679(2) 0.0366(5) Uani 1 1 d . . . . .
H17 H -0.013893 0.535320 0.365576 0.044 Uiso 0.733(13) 1 calc R U P A 1
H17B H -0.015891 0.530747 0.359697 0.044 Uiso 0.267(13) 1 calc R U P A 2
O18 O 0.2112(2) 0.75127(18) 0.40453(15) 0.0419(4) Uani 1 1 d . . . . .
H18 H 0.109(4) 0.7980(17) 0.384(2) 0.063 Uiso 1 1 calc R U . . .
C19 C 0.2270(3) 0.4969(3) 0.4610(2) 0.0356(5) Uani 1 1 d . . . . .
O20 O 0.1554(3) 0.32516(19) 0.43065(16) 0.0452(4) Uani 1 1 d . . . . .
H20 H 0.207(4) 0.2899(15) 0.484(3) 0.068 Uiso 1 1 calc R U . . .
O21 O 0.3462(3) 0.5895(2) 0.55177(15) 0.0467(4) Uani 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
N1 C2 1.500(3) . ?
N1 C5 1.504(3) . ?
N1 H1A 0.8900 . ?
N1 H1AB 0.8900 . ?
C2 C3 1.492(4) . ?
C2 H2A 0.9700 . ?
C2 H2AB 0.9700 . ?
C3 C4 1.516(4) . ?
C3 H3A 0.9700 . ?
C3 H3AB 0.9700 . ?
C4 C5 1.511(4) . ?
C4 H4A 0.9700 . ?
C4 H4AB 0.9700 . ?
C5 C6 1.528(3) . ?
C5 H5 0.9800 . ?
C6 O8 1.232(3) . ?
C6 O7 1.258(3) . ?
C11 C16 1.372(8) . ?
C11 C12 1.384(4) . ?
C11 C17 1.508(7) . ?
C12 C13 1.387(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.350(6) . ?
C13 H13 0.9300 . ?
C14 C15 1.369(7) . ?
C14 H14 0.9300 . ?
C15 C16 1.393(6) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C11B C16B 1.371(11) . ?
C11B C12B 1.384(8) . ?
C11B C17 1.530(17) . ?
C12B C13B 1.386(9) . ?
C12B H12B 0.9300 . ?
C13B C14B 1.351(10) . ?
C13B H13B 0.9300 . ?
C14B C15B 1.371(10) . ?
C14B H14B 0.9300 . ?
C15B C16B 1.397(10) . ?
C15B H15B 0.9300 . ?
C16B H16B 0.9300 . ?
C17 O18 1.419(2) . ?
C17 C19 1.524(3) . ?
C17 H17 0.9800 . ?
C17 H17B 0.9800 . ?
O18 H18 0.94(3) . ?
C19 O21 1.203(3) . ?
C19 O20 1.313(3) . ?
O20 H20 0.84(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C5 108.32(18) . . ?
C2 N1 H1A 110.0 . . ?
C5 N1 H1A 110.0 . . ?
C2 N1 H1AB 110.0 . . ?
C5 N1 H1AB 110.0 . . ?
H1A N1 H1AB 108.4 . . ?
C3 C2 N1 105.2(2) . . ?
C3 C2 H2A 110.7 . . ?
N1 C2 H2A 110.7 . . ?
C3 C2 H2AB 110.7 . . ?
N1 C2 H2AB 110.7 . . ?
H2A C2 H2AB 108.8 . . ?
C2 C3 C4 103.7(2) . . ?
C2 C3 H3A 111.0 . . ?
C4 C3 H3A 111.0 . . ?
C2 C3 H3AB 111.0 . . ?
C4 C3 H3AB 111.0 . . ?
H3A C3 H3AB 109.0 . . ?
C5 C4 C3 103.8(2) . . ?
C5 C4 H4A 111.0 . . ?
C3 C4 H4A 111.0 . . ?
C5 C4 H4AB 111.0 . . ?
C3 C4 H4AB 111.0 . . ?
H4A C4 H4AB 109.0 . . ?
N1 C5 C4 104.02(19) . . ?
N1 C5 C6 112.17(18) . . ?
C4 C5 C6 116.01(19) . . ?
N1 C5 H5 108.1 . . ?
C4 C5 H5 108.1 . . ?
C6 C5 H5 108.1 . . ?
O8 C6 O7 128.1(2) . . ?
O8 C6 C5 115.5(2) . . ?
O7 C6 C5 116.40(19) . . ?
C16 C11 C12 118.1(5) . . ?
C16 C11 C17 119.8(5) . . ?
C12 C11 C17 121.9(5) . . ?
C11 C12 C13 120.8(4) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 H12 119.6 . . ?
C14 C13 C12 120.7(4) . . ?
C14 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
C13 C14 C15 119.4(4) . . ?
C13 C14 H14 120.3 . . ?
C15 C14 H14 120.3 . . ?
C14 C15 C16 120.6(4) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 H15 119.7 . . ?
C11 C16 C15 120.4(5) . . ?
C11 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
C16B C11B C12B 118.0(13) . . ?
C16B C11B C17 121.2(15) . . ?
C12B C11B C17 120.2(13) . . ?
C11B C12B C13B 120.1(11) . . ?
C11B C12B H12B 119.9 . . ?
C13B C12B H12B 119.9 . . ?
C14B C13B C12B 120.2(11) . . ?
C14B C13B H13B 119.9 . . ?
C12B C13B H13B 119.9 . . ?
C13B C14B C15B 120.5(10) . . ?
C13B C14B H14B 119.7 . . ?
C15B C14B H14B 119.7 . . ?
C14B C15B C16B 119.0(10) . . ?
C14B C15B H15B 120.5 . . ?
C16B C15B H15B 120.5 . . ?
C11B C16B C15B 120.8(11) . . ?
C11B C16B H16B 119.6 . . ?
C15B C16B H16B 119.6 . . ?
O18 C17 C11 112.8(11) . . ?
O18 C17 C19 108.82(18) . . ?
C11 C17 C19 113.8(11) . . ?
O18 C17 C11B 112(3) . . ?
C19 C17 C11B 109(3) . . ?
O18 C17 H17 107.0 . . ?
C11 C17 H17 107.0 . . ?
C19 C17 H17 107.0 . . ?
O18 C17 H17B 109.1 . . ?
C19 C17 H17B 109.1 . . ?
C11B C17 H17B 109.1 . . ?
C17 O18 H18 109.5 . . ?
O21 C19 O20 125.3(2) . . ?
O21 C19 C17 123.86(19) . . ?
O20 C19 C17 110.77(19) . . ?
C19 O20 H20 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C2 C3 11.3(3) . . . . ?
N1 C2 C3 C4 -31.1(3) . . . . ?
C2 C3 C4 C5 39.5(3) . . . . ?
C2 N1 C5 C4 13.1(2) . . . . ?
C2 N1 C5 C6 139.2(2) . . . . ?
C3 C4 C5 N1 -32.0(3) . . . . ?
C3 C4 C5 C6 -155.7(2) . . . . ?
N1 C5 C6 O8 -168.3(2) . . . . ?
C4 C5 C6 O8 -49.0(3) . . . . ?
N1 C5 C6 O7 11.7(3) . . . . ?
C4 C5 C6 O7 131.1(2) . . . . ?
C16 C11 C12 C13 -3(3) . . . . ?
C17 C11 C12 C13 -178.4(17) . . . . ?
C11 C12 C13 C14 1(2) . . . . ?
C12 C13 C14 C15 1.7(15) . . . . ?
C13 C14 C15 C16 -2.0(11) . . . . ?
C12 C11 C16 C15 3(3) . . . . ?
C17 C11 C16 C15 178.2(14) . . . . ?
C14 C15 C16 C11 -0.5(17) . . . . ?
C16B C11B C12B C13B 14(10) . . . . ?
C17 C11B C12B C13B -175(5) . . . . ?
C11B C12B C13B C14B -6(7) . . . . ?
C12B C13B C14B C15B -4(5) . . . . ?
C13B C14B C15B C16B 7(4) . . . . ?
C12B C11B C16B C15B -11(9) . . . . ?
C17 C11B C16B C15B 178(4) . . . . ?
C14B C15B C16B C11B 1(5) . . . . ?
C16 C11 C17 O18 -108(2) . . . . ?
C12 C11 C17 O18 66(3) . . . . ?
C16 C11 C17 C19 126.9(19) . . . . ?
C12 C11 C17 C19 -58(3) . . . . ?
C16B C11B C17 O18 -129(6) . . . . ?
C12B C11B C17 O18 60(7) . . . . ?
C16B C11B C17 C19 110(6) . . . . ?
C12B C11B C17 C19 -61(7) . . . . ?
O18 C17 C19 O21 2.6(3) . . . . ?
C11 C17 C19 O21 129.3(7) . . . . ?
C11B C17 C19 O21 124.8(18) . . . . ?
O18 C17 C19 O20 179.67(17) . . . . ?
C11 C17 C19 O20 -53.6(7) . . . . ?
C11B C17 C19 O20 -58.1(18) . . . . ?

_refine_diff_density_max         0.373
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.048

####################################################################### 
# 
# 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_alex_A173_A201_1
_database_code_depnum_ccdc_archive 'CCDC 2247568'
loop_
_audit_author_name
_audit_author_address
'Koen Robeyns'
;Universite catholique de Louvain
Belgium
;
_audit_update_record             
;
2023-03-09 deposited with the CCDC.	2023-04-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H7 Cl O3'
_chemical_formula_sum            'C8 H7 Cl O3'
_chemical_formula_weight         186.59

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   16.6605(13)
_cell_length_b                   9.1572(5)
_cell_length_c                   11.4407(8)
_cell_angle_alpha                90
_cell_angle_beta                 109.810(8)
_cell_angle_gamma                90
_cell_volume                     1642.1(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    2218
_cell_measurement_theta_min      3.3980
_cell_measurement_theta_max      24.7070

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.509
_exptl_crystal_F_000             768
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_exptl_absorpt_coefficient_mu    0.425
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.92807
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?




_diffrn_ambient_temperature      297(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Incoatec microfocus source'
_diffrn_measurement_device_type  'MAR345 image plate'
_diffrn_measurement_method       
;
'90 images, ΔΦ 2.0° '
;
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9586
_diffrn_reflns_av_unetI/netI     0.0449
_diffrn_reflns_av_R_equivalents  0.0513
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.924
_diffrn_reflns_theta_max         25.254
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             2932
_reflns_number_gt                2017
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       MAR
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_atom_sites_solution_primary     dual
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'MERCURY (Macrae et al., 2008)'
_computing_publication_material  
;
'MERCURY (Macrae et al., 2008), Platon (Spek, 2009)'
;




_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0936P)²+1.5319P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2932
_refine_ls_number_parameters     247
_refine_ls_number_restraints     154
_refine_ls_R_factor_all          0.1053
_refine_ls_R_factor_gt           0.0685
_refine_ls_wR_factor_ref         0.1993
_refine_ls_wR_factor_gt          0.1778
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.9221(8) 0.508(2) 0.3127(14) 0.077(3) Uani 0.55(4) 1 d D U P A 1
C2 C 0.8604(6) 0.388(3) 0.199(2) 0.044(2) Uani 0.55(4) 1 d D U P A 1
C3 C 0.9013(7) 0.291(3) 0.148(2) 0.059(2) Uani 0.55(4) 1 d D U P A 1
H3 H 0.960537 0.289104 0.172685 0.071 Uiso 0.55(4) 1 calc R U P A 1
C4 C 0.8536(8) 0.196(3) 0.060(2) 0.065(3) Uani 0.55(4) 1 d D U P A 1
H4 H 0.880435 0.130555 0.022896 0.078 Uiso 0.55(4) 1 calc R U P A 1
C5 C 0.7655(8) 0.198(3) 0.024(3) 0.052(3) Uani 0.55(4) 1 d D U P A 1
H5 H 0.733662 0.133964 -0.037700 0.063 Uiso 0.55(4) 1 calc R U P A 1
C6 C 0.7244(4) 0.291(3) 0.079(2) 0.0348(14) Uani 0.55(4) 1 d D U P A 1
C7 C 0.7729(7) 0.391(3) 0.166(2) 0.035(3) Uani 0.55(4) 1 d D U P A 1
H7 H 0.746560 0.459315 0.201232 0.042 Uiso 0.55(4) 1 calc R U P A 1
Cl1B Cl 0.9271(8) 0.471(3) 0.3047(17) 0.071(3) Uani 0.45(4) 1 d D U P A 2
C2B C 0.8622(8) 0.356(4) 0.189(3) 0.044(2) Uani 0.45(4) 1 d D U P A 2
C3B C 0.8978(9) 0.274(4) 0.120(3) 0.059(2) Uani 0.45(4) 1 d D U P A 2
H3B H 0.956463 0.275542 0.136104 0.071 Uiso 0.45(4) 1 calc R U P A 2
C4B C 0.8466(11) 0.190(3) 0.026(3) 0.065(3) Uani 0.45(4) 1 d D U P A 2
H4B H 0.870474 0.131425 -0.020225 0.078 Uiso 0.45(4) 1 calc R U P A 2
C5B C 0.7590(10) 0.191(4) -0.001(3) 0.052(3) Uani 0.45(4) 1 d D U P A 2
H5B H 0.724435 0.132435 -0.065274 0.063 Uiso 0.45(4) 1 calc R U P A 2
C6B C 0.7231(5) 0.277(4) 0.066(3) 0.0348(14) Uani 0.45(4) 1 d D U P A 2
C7B C 0.7754(8) 0.358(3) 0.165(3) 0.035(3) Uani 0.45(4) 1 d D U P A 2
H7B H 0.752302 0.412660 0.214429 0.042 Uiso 0.45(4) 1 calc R U P A 2
C8 C 0.6273(2) 0.2851(4) 0.0372(3) 0.0380(9) Uani 1 1 d D U . . .
H8 H 0.604033 0.254994 -0.050028 0.046 Uiso 1 1 calc R U . A 1
O9 O 0.59516(17) 0.4241(3) 0.0518(2) 0.0448(7) Uani 1 1 d . . . . .
H9 H 0.589503 0.473577 -0.010259 0.067 Uiso 1 1 calc R U . . .
C10 C 0.5977(2) 0.1811(4) 0.1167(4) 0.0418(9) Uani 1 1 d . . . . .
O11 O 0.57133(18) 0.2192(3) 0.1971(3) 0.0559(8) Uani 1 1 d . . . . .
O12 O 0.6047(2) 0.0432(3) 0.0854(4) 0.0629(10) Uani 1 1 d . . . . .
H12 H 0.580(4) 0.000(4) 0.107(6) 0.094 Uiso 1 1 calc R U . . .
Cl21 Cl 0.89047(10) 1.02012(18) 0.34392(14) 0.0884(5) Uani 1 1 d . U . . .
C22 C 0.8420(3) 0.9031(5) 0.4150(4) 0.0519(11) Uani 1 1 d . U . . .
C23 C 0.8892(3) 0.8171(5) 0.5127(5) 0.0657(13) Uani 1 1 d . U . . .
H23 H 0.948436 0.823960 0.542151 0.079 Uiso 1 1 calc R U . . .
C24 C 0.8498(3) 0.7233(6) 0.5657(5) 0.0814(17) Uani 1 1 d . U . . .
H24 H 0.881912 0.665616 0.631965 0.098 Uiso 1 1 calc R U . . .
C25 C 0.7621(3) 0.7120(5) 0.5223(4) 0.0611(12) Uani 1 1 d . U . . .
H25 H 0.735451 0.647826 0.560579 0.073 Uiso 1 1 calc R U . . .
C26 C 0.7135(2) 0.7944(4) 0.4232(3) 0.0388(9) Uani 1 1 d . U . . .
C27 C 0.7539(3) 0.8921(5) 0.3702(4) 0.0486(10) Uani 1 1 d . U . . .
H27 H 0.721970 0.950735 0.304494 0.058 Uiso 1 1 calc R U . . .
C28 C 0.6188(2) 0.7731(4) 0.3688(3) 0.0395(9) Uani 1 1 d . U . . .
H28 H 0.599283 0.714858 0.425811 0.047 Uiso 1 1 calc R U . . .
O29 O 0.57678(17) 0.9117(3) 0.3486(3) 0.0507(8) Uani 1 1 d . . . . .
H29 H 0.525048 0.899293 0.327072 0.076 Uiso 1 1 calc R U . . .
C30 C 0.5970(2) 0.6952(4) 0.2457(4) 0.0390(9) Uani 1 1 d . . . . .
O31 O 0.57299(18) 0.7566(3) 0.1464(2) 0.0510(7) Uani 1 1 d . . . . .
O32 O 0.61157(19) 0.5541(3) 0.2612(3) 0.0531(8) Uani 1 1 d . . . . .
H32 H 0.603293 0.515285 0.193528 0.080 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C2 1.748(6) . ?
C2 C3 1.366(9) . ?
C2 C7 1.377(7) . ?
C3 C4 1.361(9) . ?
C3 H3 0.9300 . ?
C4 C5 1.384(8) . ?
C4 H4 0.9300 . ?
C5 C6 1.373(8) . ?
C5 H5 0.9300 . ?
C6 C7 1.393(8) . ?
C6 C8 1.526(7) . ?
C7 H7 0.9300 . ?
Cl1B C2B 1.749(7) . ?
C2B C3B 1.366(10) . ?
C2B C7B 1.378(8) . ?
C3B C4B 1.360(9) . ?
C3B H3B 0.9300 . ?
C4B C5B 1.384(9) . ?
C4B H4B 0.9300 . ?
C5B C6B 1.372(8) . ?
C5B H5B 0.9300 . ?
C6B C7B 1.390(8) . ?
C6B C8 1.519(8) . ?
C7B H7B 0.9300 . ?
C8 O9 1.412(4) . ?
C8 C10 1.510(5) . ?
C8 H8 0.9800 . ?
O9 H9 0.8200 . ?
C10 O11 1.198(5) . ?
C10 O12 1.328(5) . ?
O12 H12 0.68(6) . ?
Cl21 C22 1.705(5) . ?
C22 C23 1.376(6) . ?
C22 C27 1.386(6) . ?
C23 C24 1.344(7) . ?
C23 H23 0.9300 . ?
C24 C25 1.380(7) . ?
C24 H24 0.9300 . ?
C25 C26 1.374(6) . ?
C25 H25 0.9300 . ?
C26 C27 1.377(6) . ?
C26 C28 1.499(5) . ?
C27 H27 0.9300 . ?
C28 O29 1.430(4) . ?
C28 C30 1.509(5) . ?
C28 H28 0.9800 . ?
O29 H29 0.8200 . ?
C30 O31 1.207(5) . ?
C30 O32 1.316(4) . ?
O32 H32 0.8200 . ?

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
C3 C2 C7 122.2(7) . . ?
C3 C2 Cl1 118.4(7) . . ?
C7 C2 Cl1 119.4(7) . . ?
C4 C3 C2 118.7(7) . . ?
C4 C3 H3 120.7 . . ?
C2 C3 H3 120.7 . . ?
C3 C4 C5 120.5(8) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C6 C5 C4 120.9(7) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C5 C6 C7 118.7(7) . . ?
C5 C6 C8 118.4(10) . . ?
C7 C6 C8 122.9(10) . . ?
C2 C7 C6 118.9(7) . . ?
C2 C7 H7 120.5 . . ?
C6 C7 H7 120.5 . . ?
C3B C2B C7B 121.7(8) . . ?
C3B C2B Cl1B 119.5(8) . . ?
C7B C2B Cl1B 118.6(8) . . ?
C4B C3B C2B 119.3(8) . . ?
C4B C3B H3B 120.4 . . ?
C2B C3B H3B 120.4 . . ?
C3B C4B C5B 120.4(9) . . ?
C3B C4B H4B 119.8 . . ?
C5B C4B H4B 119.8 . . ?
C6B C5B C4B 120.2(8) . . ?
C6B C5B H5B 119.9 . . ?
C4B C5B H5B 119.9 . . ?
C5B C6B C7B 119.6(8) . . ?
C5B C6B C8 122.3(12) . . ?
C7B C6B C8 118.1(11) . . ?
C2B C7B C6B 118.6(9) . . ?
C2B C7B H7B 120.7 . . ?
C6B C7B H7B 120.7 . . ?
O9 C8 C10 106.5(3) . . ?
O9 C8 C6B 115.5(12) . . ?
C10 C8 C6B 112.0(17) . . ?
O9 C8 C6 109.6(9) . . ?
C10 C8 C6 111.4(13) . . ?
O9 C8 H8 109.8 . . ?
C10 C8 H8 109.8 . . ?
C6 C8 H8 109.8 . . ?
C8 O9 H9 109.5 . . ?
O11 C10 O12 124.9(4) . . ?
O11 C10 C8 123.9(4) . . ?
O12 C10 C8 111.2(4) . . ?
C10 O12 H12 109.5 . . ?
C23 C22 C27 120.1(4) . . ?
C23 C22 Cl21 121.0(4) . . ?
C27 C22 Cl21 118.9(4) . . ?
C24 C23 C22 120.0(4) . . ?
C24 C23 H23 120.0 . . ?
C22 C23 H23 120.0 . . ?
C23 C24 C25 120.4(4) . . ?
C23 C24 H24 119.8 . . ?
C25 C24 H24 119.8 . . ?
C26 C25 C24 120.7(4) . . ?
C26 C25 H25 119.6 . . ?
C24 C25 H25 119.6 . . ?
C25 C26 C27 118.8(4) . . ?
C25 C26 C28 120.9(4) . . ?
C27 C26 C28 120.3(3) . . ?
C26 C27 C22 119.9(4) . . ?
C26 C27 H27 120.0 . . ?
C22 C27 H27 120.0 . . ?
O29 C28 C26 109.9(3) . . ?
O29 C28 C30 108.6(3) . . ?
C26 C28 C30 109.6(3) . . ?
O29 C28 H28 109.6 . . ?
C26 C28 H28 109.6 . . ?
C30 C28 H28 109.6 . . ?
C28 O29 H29 109.5 . . ?
O31 C30 O32 124.9(4) . . ?
O31 C30 C28 123.8(4) . . ?
O32 C30 C28 111.3(3) . . ?
C30 O32 H32 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 C2 C3 C4 1(5) . . . . ?
Cl1 C2 C3 C4 180(2) . . . . ?
C2 C3 C4 C5 -1(5) . . . . ?
C3 C4 C5 C6 -1(5) . . . . ?
C4 C5 C6 C7 4(5) . . . . ?
C4 C5 C6 C8 -179(3) . . . . ?
C3 C2 C7 C6 1(5) . . . . ?
Cl1 C2 C7 C6 -178(3) . . . . ?
C5 C6 C7 C2 -3(5) . . . . ?
C8 C6 C7 C2 179(3) . . . . ?
C7B C2B C3B C4B -1(6) . . . . ?
Cl1B C2B C3B C4B -177(3) . . . . ?
C2B C3B C4B C5B 2(6) . . . . ?
C3B C4B C5B C6B 0(7) . . . . ?
C4B C5B C6B C7B -3(7) . . . . ?
C4B C5B C6B C8 178(4) . . . . ?
C3B C2B C7B C6B -2(6) . . . . ?
Cl1B C2B C7B C6B 174(3) . . . . ?
C5B C6B C7B C2B 4(6) . . . . ?
C8 C6B C7B C2B -178(3) . . . . ?
C5B C6B C8 O9 -143(4) . . . . ?
C7B C6B C8 O9 38(4) . . . . ?
C5B C6B C8 C10 95(4) . . . . ?
C7B C6B C8 C10 -84(3) . . . . ?
C5 C6 C8 O9 -151(3) . . . . ?
C7 C6 C8 O9 27(3) . . . . ?
C5 C6 C8 C10 91(3) . . . . ?
C7 C6 C8 C10 -91(3) . . . . ?
O9 C8 C10 O11 -16.4(5) . . . . ?
C6B C8 C10 O11 110.8(9) . . . . ?
C6 C8 C10 O11 103.0(8) . . . . ?
O9 C8 C10 O12 163.5(3) . . . . ?
C6B C8 C10 O12 -69.3(9) . . . . ?
C6 C8 C10 O12 -77.1(8) . . . . ?
C27 C22 C23 C24 -0.6(7) . . . . ?
Cl21 C22 C23 C24 -178.6(4) . . . . ?
C22 C23 C24 C25 0.3(9) . . . . ?
C23 C24 C25 C26 1.1(9) . . . . ?
C24 C25 C26 C27 -2.0(7) . . . . ?
C24 C25 C26 C28 174.6(4) . . . . ?
C25 C26 C27 C22 1.7(6) . . . . ?
C28 C26 C27 C22 -175.0(4) . . . . ?
C23 C22 C27 C26 -0.4(6) . . . . ?
Cl21 C22 C27 C26 177.6(3) . . . . ?
C25 C26 C28 O29 134.5(4) . . . . ?
C27 C26 C28 O29 -48.9(5) . . . . ?
C25 C26 C28 C30 -106.3(4) . . . . ?
C27 C26 C28 C30 70.3(5) . . . . ?
O29 C28 C30 O31 22.1(5) . . . . ?
C26 C28 C30 O31 -98.0(4) . . . . ?
O29 C28 C30 O32 -161.1(3) . . . . ?
C26 C28 C30 O32 78.8(4) . . . . ?

_refine_diff_density_max         0.255
_refine_diff_density_min         -0.569
_refine_diff_density_rms         0.063

####################################################################### 
# 
# 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_alex_fl174
_database_code_depnum_ccdc_archive 'CCDC 2247569'
loop_
_audit_author_name
_audit_author_address
'Koen Robeyns'
;Universite catholique de Louvain
Belgium
;
_audit_update_record             
;
2023-03-09 deposited with the CCDC.	2023-04-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '0.5(C16 H13 F2 O6), 0.5(C10 H19 N2 O4)'
_chemical_formula_sum            'C13 H16 F N O5'
_chemical_formula_weight         285.27

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   12.591(2)
_cell_length_b                   8.7414(12)
_cell_length_c                   12.6758(14)
_cell_angle_alpha                90
_cell_angle_beta                 104.824(14)
_cell_angle_gamma                90
_cell_volume                     1348.7(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    2173
_cell_measurement_theta_min      3.0730
_cell_measurement_theta_max      24.9200

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.405
_exptl_crystal_F_000             600
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.08
_exptl_absorpt_coefficient_mu    0.117
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.32646
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?


_diffrn_ambient_temperature      297(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Incoatec microfocus source'
_diffrn_measurement_device_type  'MAR345 image plate'
_diffrn_measurement_method       
;
'60 images, ΔΦ 3.0° '
;
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8414
_diffrn_reflns_av_unetI/netI     0.0281
_diffrn_reflns_av_R_equivalents  0.0333
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.094
_diffrn_reflns_theta_max         25.260
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             2434
_reflns_number_gt                1893
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       MAR
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_atom_sites_solution_primary     'dual space'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'MERCURY (Macrae et al., 2008)'
_computing_publication_material  
;
'MERCURY (Macrae et al., 2008), Platon (Spek, 2009)'
;






_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0400P)²+0.7478P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2434
_refine_ls_number_parameters     184
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0700
_refine_ls_R_factor_gt           0.0526
_refine_ls_wR_factor_ref         0.1267
_refine_ls_wR_factor_gt          0.1190
_refine_ls_goodness_of_fit_ref   1.131
_refine_ls_restrained_S_all      1.131
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.39913(16) 0.2673(2) 0.28032(14) 0.0405(5) Uani 1 1 d . . . . .
H1A H 0.4481(9) 0.2022(12) 0.3189(7) 0.049 Uiso 1 1 calc R U . . .
H1B H 0.4183(4) 0.3614(17) 0.3043(5) 0.049 Uiso 1 1 calc R U . . .
C2 C 0.2879(2) 0.2308(3) 0.2937(2) 0.0547(7) Uani 1 1 d . . . . .
H2A H 0.249963 0.323144 0.305741 0.066 Uiso 1 1 calc R U . . .
H2B H 0.292720 0.161930 0.354724 0.066 Uiso 1 1 calc R U . . .
C3 C 0.2299(3) 0.1563(4) 0.1892(2) 0.0736(9) Uani 1 1 d . . . . .
H3A H 0.151185 0.172482 0.174011 0.088 Uiso 1 1 calc R U . . .
H3B H 0.244454 0.047274 0.191500 0.088 Uiso 1 1 calc R U . . .
C4 C 0.2762(2) 0.2333(4) 0.1053(2) 0.0616(8) Uani 1 1 d . . . . .
H4A H 0.240489 0.330824 0.083790 0.074 Uiso 1 1 calc R U . . .
H4B H 0.267370 0.169470 0.040972 0.074 Uiso 1 1 calc R U . . .
C5 C 0.39653(19) 0.2554(2) 0.16176(17) 0.0383(5) Uani 1 1 d . . . . .
H5 H 0.437642 0.164362 0.150261 0.046 Uiso 1 1 calc R U . . .
C6 C 0.44687(18) 0.3943(2) 0.12470(17) 0.0359(5) Uani 1 1 d . . . . .
O7 O 0.4720(2) 0.5030(2) 0.18453(14) 0.0778(7) Uani 1 1 d . . . . .
O8 O 0.45742(15) 0.38548(18) 0.02802(13) 0.0502(5) Uani 1 1 d . . . . .
H8 H 0.500000 0.500000 0.000000 0.075 Uiso 1 2 d S U P . .
F11 F 0.86416(14) 0.4328(2) 0.52499(14) 0.0798(6) Uani 1 1 d . . . . .
C12 C 0.8797(2) 0.4263(3) 0.6341(2) 0.0502(6) Uani 1 1 d . . . . .
C13 C 0.9653(2) 0.5062(4) 0.6986(3) 0.0702(9) Uani 1 1 d . . . . .
H13 H 1.011153 0.565202 0.667870 0.084 Uiso 1 1 calc R U . . .
C14 C 0.9820(3) 0.4974(4) 0.8097(3) 0.0845(11) Uani 1 1 d . . . . .
H14 H 1.040717 0.549274 0.855054 0.101 Uiso 1 1 calc R U . . .
C15 C 0.9135(3) 0.4135(4) 0.8539(3) 0.0826(10) Uani 1 1 d . . . . .
H15 H 0.925131 0.408925 0.929308 0.099 Uiso 1 1 calc R U . . .
C16 C 0.8262(2) 0.3347(3) 0.7872(2) 0.0600(7) Uani 1 1 d . . . . .
H16 H 0.779524 0.277892 0.818208 0.072 Uiso 1 1 calc R U . . .
C17 C 0.80798(18) 0.3398(3) 0.67454(19) 0.0420(6) Uani 1 1 d . . . . .
C18 C 0.71458(19) 0.2518(3) 0.60236(19) 0.0452(6) Uani 1 1 d . . . . .
H18 H 0.674050 0.202704 0.649655 0.054 Uiso 1 1 calc R U . . .
O19 O 0.75511(17) 0.1348(2) 0.54677(18) 0.0729(7) Uani 1 1 d . . . . .
H19 H 0.728(3) 0.142(3) 0.483(3) 0.109 Uiso 1 1 calc R U . . .
C20 C 0.63331(18) 0.3528(3) 0.52120(19) 0.0427(6) Uani 1 1 d . . . . .
O21 O 0.61743(15) 0.3289(2) 0.42364(14) 0.0618(5) Uani 1 1 d . . . . .
O22 O 0.58504(13) 0.45455(19) 0.56505(12) 0.0478(4) Uani 1 1 d . . . . .
H22 H 0.500000 0.500000 0.500000 0.072 Uiso 1 2 d S U P . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C2 1.488(3) . ?
N1 C5 1.498(3) . ?
N1 H1A 0.889(16) . ?
N1 H1B 0.889(16) . ?
C2 C3 1.488(4) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.498(4) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.513(4) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.500(3) . ?
C5 H5 0.9800 . ?
C6 O7 1.206(3) . ?
C6 O8 1.268(3) . ?
O8 H8 1.2301(15) . ?
F11 C12 1.347(3) . ?
C12 C13 1.367(4) . ?
C12 C17 1.374(3) . ?
C13 C14 1.372(5) . ?
C13 H13 0.9300 . ?
C14 C15 1.358(5) . ?
C14 H14 0.9300 . ?
C15 C16 1.386(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.388(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.504(3) . ?
C18 O19 1.409(3) . ?
C18 C20 1.532(3) . ?
C18 H18 0.9800 . ?
O19 H19 0.79(4) . ?
C20 O21 1.219(3) . ?
C20 O22 1.282(3) . ?
O22 H22 1.2379(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
C2 N1 C5 108.63(17) . . ?
C2 N1 H1A 110.0 . . ?
C5 N1 H1A 110.0 . . ?
C2 N1 H1B 110.0 . . ?
C5 N1 H1B 110.0 . . ?
H1A N1 H1B 108.3 . . ?
N1 C2 C3 104.8(2) . . ?
N1 C2 H2A 110.8 . . ?
C3 C2 H2A 110.8 . . ?
N1 C2 H2B 110.8 . . ?
C3 C2 H2B 110.8 . . ?
H2A C2 H2B 108.9 . . ?
C2 C3 C4 104.1(2) . . ?
C2 C3 H3A 110.9 . . ?
C4 C3 H3A 110.9 . . ?
C2 C3 H3B 110.9 . . ?
C4 C3 H3B 110.9 . . ?
H3A C3 H3B 108.9 . . ?
C3 C4 C5 104.2(2) . . ?
C3 C4 H4A 110.9 . . ?
C5 C4 H4A 110.9 . . ?
C3 C4 H4B 110.9 . . ?
C5 C4 H4B 110.9 . . ?
H4A C4 H4B 108.9 . . ?
N1 C5 C6 110.81(17) . . ?
N1 C5 C4 104.24(18) . . ?
C6 C5 C4 114.02(19) . . ?
N1 C5 H5 109.2 . . ?
C6 C5 H5 109.2 . . ?
C4 C5 H5 109.2 . . ?
O7 C6 O8 125.4(2) . . ?
O7 C6 C5 120.31(19) . . ?
O8 C6 C5 114.26(19) . . ?
C6 O8 H8 113.01(16) . . ?
F11 C12 C13 118.5(3) . . ?
F11 C12 C17 118.0(2) . . ?
C13 C12 C17 123.4(3) . . ?
C12 C13 C14 118.4(3) . . ?
C12 C13 H13 120.8 . . ?
C14 C13 H13 120.8 . . ?
C15 C14 C13 120.5(3) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C14 C15 C16 120.3(3) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 H15 119.8 . . ?
C15 C16 C17 120.5(3) . . ?
C15 C16 H16 119.7 . . ?
C17 C16 H16 119.7 . . ?
C12 C17 C16 116.8(2) . . ?
C12 C17 C18 122.7(2) . . ?
C16 C17 C18 120.5(2) . . ?
O19 C18 C17 110.4(2) . . ?
O19 C18 C20 110.3(2) . . ?
C17 C18 C20 113.43(19) . . ?
O19 C18 H18 107.5 . . ?
C17 C18 H18 107.5 . . ?
C20 C18 H18 107.5 . . ?
C18 O19 H19 109.5 . . ?
O21 C20 O22 125.9(2) . . ?
O21 C20 C18 119.4(2) . . ?
O22 C20 C18 114.7(2) . . ?
C20 O22 H22 111.05(15) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C2 C3 15.3(3) . . . . ?
N1 C2 C3 C4 -32.8(3) . . . . ?
C2 C3 C4 C5 38.0(3) . . . . ?
C2 N1 C5 C6 131.0(2) . . . . ?
C2 N1 C5 C4 8.0(2) . . . . ?
C3 C4 C5 N1 -28.0(3) . . . . ?
C3 C4 C5 C6 -149.0(2) . . . . ?
N1 C5 C6 O7 -7.8(3) . . . . ?
C4 C5 C6 O7 109.4(3) . . . . ?
N1 C5 C6 O8 173.36(18) . . . . ?
C4 C5 C6 O8 -69.4(3) . . . . ?
F11 C12 C13 C14 -179.0(3) . . . . ?
C17 C12 C13 C14 1.4(4) . . . . ?
C12 C13 C14 C15 -1.3(5) . . . . ?
C13 C14 C15 C16 0.5(5) . . . . ?
C14 C15 C16 C17 0.3(5) . . . . ?
F11 C12 C17 C16 179.7(2) . . . . ?
C13 C12 C17 C16 -0.6(4) . . . . ?
F11 C12 C17 C18 0.7(4) . . . . ?
C13 C12 C17 C18 -179.6(2) . . . . ?
C15 C16 C17 C12 -0.2(4) . . . . ?
C15 C16 C17 C18 178.8(3) . . . . ?
C12 C17 C18 O19 65.0(3) . . . . ?
C16 C17 C18 O19 -114.0(3) . . . . ?
C12 C17 C18 C20 -59.4(3) . . . . ?
C16 C17 C18 C20 121.6(3) . . . . ?
O19 C18 C20 O21 -3.6(3) . . . . ?
C17 C18 C20 O21 120.8(2) . . . . ?
O19 C18 C20 O22 174.4(2) . . . . ?
C17 C18 C20 O22 -61.2(3) . . . . ?

_refine_diff_density_max         0.176
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.037

