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

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

data_tba-coo
_database_code_depnum_ccdc_archive 'CCDC 1976318'
loop_
_audit_author_name
_audit_author_address
'Nikoletta B. Bathori'
;Cape Peninsula University of Technology
South Africa
;
_audit_update_record             
;
2020-01-09 deposited with the CCDC.	2020-02-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/4
_shelx_SHELXL_version_number     2016/4
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          378.81
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H24 N2 O3'
_chemical_formula_weight         208.30

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'
O O 0.0106 0.0060 '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'

_space_group_crystal_system      trigonal
_space_group_IT_number           167
_space_group_name_H-M_alt        'R -3 c :H'
_space_group_name_Hall           '-R 3 2"c'

_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'
'-y, x-y, z'
'-x+y, -x, z'
'x-y, -y, -z+1/2'
'-x, -x+y, -z+1/2'
'y, x, -z+1/2'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x-y+2/3, -y+1/3, -z+5/6'
'-x+2/3, -x+y+1/3, -z+5/6'
'y+2/3, x+1/3, -z+5/6'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'x-y+1/3, -y+2/3, -z+7/6'
'-x+1/3, -x+y+2/3, -z+7/6'
'y+1/3, x+2/3, -z+7/6'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+y, y, z-1/2'
'x, x-y, z-1/2'
'-y, -x, z-1/2'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+y+2/3, y+1/3, z-1/6'
'x+2/3, x-y+1/3, z-1/6'
'-y+2/3, -x+1/3, z-1/6'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'
'-x+y+1/3, y+2/3, z+1/6'
'x+1/3, x-y+2/3, z+1/6'
'-y+1/3, -x+2/3, z+1/6'

_cell_length_a                   6.3212(9)
_cell_length_b                   6.3212(9)
_cell_length_c                   53.448(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     1849.5(6)
_cell_formula_units_Z            6
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    1594
_cell_measurement_theta_min      2.28
_cell_measurement_theta_max      27.96

_exptl_crystal_description       chunk
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.122
_exptl_crystal_F_000             696
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.380
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    0.083
_shelx_estimated_absorpt_T_min   0.968
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.897
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  Bruker
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4739
_diffrn_reflns_av_unetI/netI     0.0144
_diffrn_reflns_av_R_equivalents  0.0280
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -70
_diffrn_reflns_limit_l_max       70
_diffrn_reflns_theta_min         2.286
_diffrn_reflns_theta_max         28.417
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             528
_reflns_number_gt                484
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0553P)²+0.6075P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    noref
_refine_ls_extinction_method     'SHELXL-2016/4 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.0051(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         528
_refine_ls_number_parameters     26
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0359
_refine_ls_R_factor_gt           0.0331
_refine_ls_wR_factor_ref         0.0946
_refine_ls_wR_factor_gt          0.0922
_refine_ls_goodness_of_fit_ref   1.118
_refine_ls_restrained_S_all      1.118
_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 0.333333 0.666667 0.04077(2) 0.0197(3) Uani 1 3 d S T P . .
H1 H 0.394800 0.566000 0.074707 0.031(3) Uiso 1 1 d R . . . .
C2 C 0.58787(17) 0.73058(18) 0.03206(2) 0.0296(3) Uani 1 1 d . . . . .
H2B H 0.707730 0.892043 0.038487 0.044 Uiso 1 1 calc R U . . .
H2C H 0.593121 0.732575 0.013734 0.044 Uiso 1 1 calc R U . . .
H2A H 0.626595 0.608255 0.038360 0.044 Uiso 1 1 calc R U . . .
N3 N 0.333333 0.666667 0.06888(2) 0.0178(3) Uani 1 3 d S T P . .
C4 C 0.666667 0.333333 0.083333 0.0159(4) Uani 1 6 d S T P . .
O5 O 0.46368(13) 0.333333 0.083333 0.0258(3) Uani 1 2 d S T 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
C1 N3 1.5027(16) . ?
C1 C2 1.5227(10) 2_665 ?
C1 C2 1.5227(10) 3_565 ?
C1 C2 1.5227(10) . ?
C4 O5 1.2831(8) 2_655 ?
C4 O5 1.2831(8) 3_665 ?
C4 O5 1.2831(8) . ?

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
N3 C1 C2 107.80(6) . 2_665 ?
N3 C1 C2 107.80(6) . 3_565 ?
C2 C1 C2 111.09(5) 2_665 3_565 ?
N3 C1 C2 107.79(6) . . ?
C2 C1 C2 111.09(5) 2_665 . ?
C2 C1 C2 111.09(5) 3_565 . ?
O5 C4 O5 120.0 2_655 3_665 ?
O5 C4 O5 120.000(1) 2_655 . ?
O5 C4 O5 120.0 3_665 . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N3 H1 O5 0.95 1.79 2.7297(7) 170.0 .

_refine_diff_density_max         0.287
_refine_diff_density_min         -0.135
_refine_diff_density_rms         0.036

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: tert-butylamine'
####################################################################### 
# 
# 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_racpsa-pyr
_database_code_depnum_ccdc_archive 'CCDC 1976321'
loop_
_audit_author_name
_audit_author_address
'Nikoletta B. Bathori'
;Cape Peninsula University of Technology
South Africa
;
_audit_update_record             
;
2020-01-09 deposited with the CCDC.	2020-02-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/4
_shelx_SHELXL_version_number     2016/4
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          335.32
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H20 N2 O4'
_chemical_formula_weight         352.38

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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                   5.6697(4)
_cell_length_b                   10.5672(6)
_cell_length_c                   15.5754(10)
_cell_angle_alpha                109.3480(10)
_cell_angle_beta                 96.6060(10)
_cell_angle_gamma                91.6070(10)
_cell_volume                     872.44(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    3681
_cell_measurement_theta_min      1.398
_cell_measurement_theta_max      27.532

_exptl_crystal_description       plates
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.341
_exptl_crystal_F_000             372
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.010
_exptl_crystal_size_mid          0.010
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    0.094
_shelx_estimated_absorpt_T_min   0.999
_shelx_estimated_absorpt_T_max   0.999
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7224
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  Bruker
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23333
_diffrn_reflns_av_unetI/netI     0.0149
_diffrn_reflns_av_R_equivalents  0.0223
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.398
_diffrn_reflns_theta_max         27.532
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             4011
_reflns_number_gt                3681
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0321P)²+0.5154P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    noref
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4011
_refine_ls_number_parameters     243
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0389
_refine_ls_R_factor_gt           0.0359
_refine_ls_wR_factor_ref         0.0907
_refine_ls_wR_factor_gt          0.0885
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4373(2) 0.88430(11) 0.32479(8) 0.0149(2) Uani 1 1 d . . . . .
H1 H 0.316645 0.906392 0.368637 0.018 Uiso 1 1 calc R U . . .
C2 C 0.4099(2) 0.97244(11) 0.26450(7) 0.0146(2) Uani 1 1 d . . . . .
C3 C 0.2248(2) 1.05761(11) 0.27054(8) 0.0169(2) Uani 1 1 d . . . . .
H3 H 0.117105 1.062770 0.313808 0.020 Uiso 1 1 calc R U . . .
C4 C 0.1964(2) 1.13528(12) 0.21373(8) 0.0200(2) Uani 1 1 d . . . . .
H4 H 0.069992 1.193401 0.218681 0.024 Uiso 1 1 calc R U . . .
C5 C 0.3517(2) 1.12818(12) 0.14992(8) 0.0210(2) Uani 1 1 d . . . . .
H5 H 0.330772 1.180445 0.110720 0.025 Uiso 1 1 calc R U . . .
C6 C 0.5383(2) 1.04410(12) 0.14362(8) 0.0201(2) Uani 1 1 d . . . . .
H6 H 0.645845 1.039275 0.100315 0.024 Uiso 1 1 calc R U . . .
C7 C 0.5672(2) 0.96716(11) 0.20080(8) 0.0174(2) Uani 1 1 d . . . . .
H7 H 0.695452 0.910350 0.196505 0.021 Uiso 1 1 calc R U . . .
C8 C 0.6856(2) 0.90642(12) 0.37906(8) 0.0182(2) Uani 1 1 d . . . . .
H8B H 0.804132 0.879902 0.335506 0.022 Uiso 1 1 calc R U . . .
H8A H 0.718600 1.003415 0.414355 0.022 Uiso 1 1 calc R U . . .
C9 C 0.7158(2) 0.82794(11) 0.44465(8) 0.0171(2) Uani 1 1 d . . . . .
O10 O 0.55424(16) 0.76373(10) 0.45962(7) 0.0263(2) Uani 1 1 d . . . . .
O11 O 0.93804(16) 0.83775(9) 0.48262(6) 0.0225(2) Uani 1 1 d . . . . .
H11 H 0.957(3) 0.784(2) 0.5211(14) 0.048(5) Uiso 1 1 d . . . . .
C12 C 0.3862(2) 0.73879(11) 0.26083(7) 0.0148(2) Uani 1 1 d . . . . .
O13 O 0.53807(15) 0.66812(9) 0.22579(6) 0.02176(19) Uani 1 1 d . . . . .
O14 O 0.15628(15) 0.70190(9) 0.24410(6) 0.01877(18) Uani 1 1 d . . . . .
H14 H 0.134(3) 0.617(2) 0.2031(14) 0.044(5) Uiso 1 1 d . . . . .
N15 N 1.01657(18) 0.68594(10) 0.58506(7) 0.0166(2) Uani 1 1 d . . . . .
C16 C 0.8462(2) 0.59269(12) 0.58077(8) 0.0168(2) Uani 1 1 d . . . . .
H16 H 0.692393 0.595305 0.550196 0.020 Uiso 1 1 calc R U . . .
C17 C 0.8847(2) 0.49247(12) 0.61906(8) 0.0177(2) Uani 1 1 d . . . . .
H17 H 0.760402 0.427487 0.614510 0.021 Uiso 1 1 calc R U . . .
C18 C 1.1094(2) 0.48948(12) 0.66417(8) 0.0175(2) Uani 1 1 d . . . . .
H18 H 1.141998 0.421755 0.690681 0.021 Uiso 1 1 calc R U . . .
C19 C 1.2855(2) 0.58687(12) 0.66994(8) 0.0181(2) Uani 1 1 d . . . . .
H19 H 1.439833 0.587720 0.701293 0.022 Uiso 1 1 calc R U . . .
C20 C 1.2328(2) 0.68279(12) 0.62927(8) 0.0178(2) Uani 1 1 d . . . . .
H20 H 1.354149 0.748835 0.632798 0.021 Uiso 1 1 calc R U . . .
N21 N 0.07390(18) 0.45568(10) 0.11469(7) 0.0188(2) Uani 1 1 d . . . . .
C22 C 0.2261(2) 0.42888(12) 0.05231(8) 0.0190(2) Uani 1 1 d . . . . .
H22 H 0.367080 0.486155 0.064756 0.023 Uiso 1 1 calc R U . . .
C23 C 0.1879(2) 0.32150(12) -0.02964(8) 0.0213(2) Uani 1 1 d . . . . .
H23 H 0.298361 0.306889 -0.072861 0.026 Uiso 1 1 calc R U . . .
C24 C -0.0154(2) 0.23599(12) -0.04697(8) 0.0206(2) Uani 1 1 d . . . . .
H24 H -0.045872 0.160823 -0.101998 0.025 Uiso 1 1 calc R U . . .
C25 C -0.1727(2) 0.26227(12) 0.01742(8) 0.0214(3) Uani 1 1 d . . . . .
H25 H -0.312869 0.205135 0.007421 0.026 Uiso 1 1 calc R U . . .
C26 C -0.1229(2) 0.37318(13) 0.09671(8) 0.0217(3) Uani 1 1 d . . . . .
H26 H -0.233036 0.391493 0.140167 0.026 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
C1 C8 1.5253(16) . ?
C1 C2 1.5256(15) . ?
C1 C12 1.5279(15) . ?
C2 C3 1.3925(16) . ?
C2 C7 1.3975(16) . ?
C3 C4 1.3923(16) . ?
C4 C5 1.3872(18) . ?
C5 C6 1.3920(18) . ?
C6 C7 1.3910(17) . ?
C8 C9 1.5133(16) . ?
C9 O10 1.2136(15) . ?
C9 O11 1.3149(14) . ?
C12 O13 1.2130(15) . ?
C12 O14 1.3209(14) . ?
N15 C16 1.3405(15) . ?
N15 C20 1.3421(15) . ?
C16 C17 1.3879(17) . ?
C17 C18 1.3886(17) . ?
C18 C19 1.3874(17) . ?
C19 C20 1.3845(17) . ?
N21 C22 1.3390(16) . ?
N21 C26 1.3400(16) . ?
C22 C23 1.3880(17) . ?
C23 C24 1.3879(18) . ?
C24 C25 1.3835(18) . ?
C25 C26 1.3858(17) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 C1 C2 111.47(9) . . ?
C8 C1 C12 111.39(9) . . ?
C2 C1 C12 106.73(9) . . ?
C3 C2 C7 118.73(10) . . ?
C3 C2 C1 120.67(10) . . ?
C7 C2 C1 120.58(10) . . ?
C4 C3 C2 120.58(11) . . ?
C5 C4 C3 120.30(11) . . ?
C4 C5 C6 119.69(11) . . ?
C7 C6 C5 119.91(11) . . ?
C6 C7 C2 120.79(11) . . ?
C9 C8 C1 113.32(9) . . ?
O10 C9 O11 124.62(11) . . ?
O10 C9 C8 123.84(11) . . ?
O11 C9 C8 111.54(10) . . ?
O13 C12 O14 124.09(11) . . ?
O13 C12 C1 123.73(10) . . ?
O14 C12 C1 112.07(10) . . ?
C16 N15 C20 118.35(10) . . ?
N15 C16 C17 122.86(11) . . ?
C16 C17 C18 118.39(11) . . ?
C19 C18 C17 119.01(11) . . ?
C20 C19 C18 118.95(11) . . ?
N15 C20 C19 122.44(11) . . ?
C22 N21 C26 117.75(10) . . ?
N21 C22 C23 123.22(11) . . ?
C24 C23 C22 118.44(11) . . ?
C25 C24 C23 118.74(11) . . ?
C24 C25 C26 119.03(11) . . ?
N21 C26 C25 122.80(12) . . ?

_refine_diff_density_max         0.375
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.043

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: pyridine'
####################################################################### 
# 
# 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_racpsa-pca
_database_code_depnum_ccdc_archive 'CCDC 1976328'
loop_
_audit_author_name
_audit_author_address
'Nikoletta B. Bathori'
;Cape Peninsula University of Technology
South Africa
;
_audit_update_record             
;
2020-01-09 deposited with the CCDC.	2020-02-14 downloaded from the CCDC.
;


_audit_creation_method           SHELXL-2016/4
_shelx_SHELXL_version_number     2016/4
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          398.42
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H15 N3 O5'
_chemical_formula_weight         317.30

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      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                   5.7726(12)
_cell_length_b                   7.9815(16)
_cell_length_c                   16.594(3)
_cell_angle_alpha                99.36(3)
_cell_angle_beta                 99.28(3)
_cell_angle_gamma                97.44(3)
_cell_volume                     734.9(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    3777
_cell_measurement_theta_min      2.62
_cell_measurement_theta_max      26.05

_exptl_crystal_description       plates
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.434
_exptl_crystal_F_000             332
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.900
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.110
_shelx_estimated_absorpt_T_min   0.908
_shelx_estimated_absorpt_T_max   0.996
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.933
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  Bruker
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19165
_diffrn_reflns_av_unetI/netI     0.0331
_diffrn_reflns_av_R_equivalents  0.0416
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.266
_diffrn_reflns_theta_max         28.353
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3666
_reflns_number_gt                2858
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0396P)²+0.1576P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    noref
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3666
_refine_ls_number_parameters     224
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0553
_refine_ls_R_factor_gt           0.0403
_refine_ls_wR_factor_ref         0.0971
_refine_ls_wR_factor_gt          0.0898
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1262(2) 0.67014(15) 0.63332(7) 0.0207(3) Uani 1 1 d . . . . .
H1 H -0.002608 0.727821 0.607403 0.025 Uiso 1 1 calc R U . . .
C2 C 0.0094(2) 0.50247(16) 0.65370(7) 0.0197(3) Uani 1 1 d . . . . .
C3 C -0.1824(2) 0.50422(17) 0.69526(8) 0.0237(3) Uani 1 1 d . . . . .
H3 H -0.239233 0.609152 0.710586 0.028 Uiso 1 1 calc R U . . .
C4 C -0.2909(2) 0.35345(18) 0.71438(8) 0.0283(3) Uani 1 1 d . . . . .
H4 H -0.421276 0.356250 0.742696 0.034 Uiso 1 1 calc R U . . .
C5 C -0.2107(2) 0.19946(18) 0.69252(8) 0.0293(3) Uani 1 1 d . . . . .
H5 H -0.285543 0.096705 0.705583 0.035 Uiso 1 1 calc R U . . .
C6 C -0.0209(3) 0.19648(17) 0.65155(8) 0.0294(3) Uani 1 1 d . . . . .
H6 H 0.034959 0.091071 0.636365 0.035 Uiso 1 1 calc R U . . .
H17A H 0.667(3) 0.975(2) 0.8419(12) 0.052(5) Uiso 1 1 d . . . . .
H17B H 0.856(3) 1.096(2) 0.9090(11) 0.040(5) Uiso 1 1 d . . . . .
H14 H 0.209(4) 0.932(3) 0.8053(14) 0.070(6) Uiso 1 1 d . . . . .
H11 H 0.621(3) 0.889(3) 0.4920(12) 0.061(6) Uiso 1 1 d . . . . .
C7 C 0.0896(2) 0.34693(16) 0.63230(8) 0.0241(3) Uani 1 1 d . . . . .
H7 H 0.220624 0.343364 0.604349 0.029 Uiso 1 1 calc R U . . .
C8 C 0.2966(2) 0.64285(16) 0.57276(7) 0.0218(3) Uani 1 1 d . . . . .
H8B H 0.432648 0.595044 0.599535 0.026 Uiso 1 1 calc R U . . .
H8A H 0.213482 0.557175 0.523153 0.026 Uiso 1 1 calc R U . . .
C9 C 0.3891(2) 0.80482(17) 0.54553(7) 0.0235(3) Uani 1 1 d . . . . .
O10 O 0.29614(17) 0.93381(12) 0.55230(6) 0.0309(2) Uani 1 1 d . . . . .
O11 O 0.57920(18) 0.79189(13) 0.51182(7) 0.0347(3) Uani 1 1 d . . . . .
C12 C 0.2585(2) 0.79005(16) 0.71335(8) 0.0216(3) Uani 1 1 d . . . . .
O13 O 0.47324(16) 0.81582(13) 0.73354(6) 0.0308(2) Uani 1 1 d . . . . .
O14 O 0.11545(17) 0.86115(13) 0.75810(6) 0.0323(2) Uani 1 1 d . . . . .
O15 O 0.32625(17) 1.06973(13) 0.89657(6) 0.0351(2) Uani 1 1 d . . . . .
C16 C 0.5428(2) 1.11766(17) 0.92318(8) 0.0261(3) Uani 1 1 d . . . . .
N17 N 0.7115(2) 1.05603(18) 0.88766(8) 0.0339(3) Uani 1 1 d . . . . .
C18 C 0.6230(2) 1.25278(16) 1.00031(7) 0.0230(3) Uani 1 1 d . . . . .
N19 N 0.8565(2) 1.30599(15) 1.02564(7) 0.0280(3) Uani 1 1 d . . . . .
C20 C 0.9204(2) 1.42966(19) 1.09330(8) 0.0302(3) Uani 1 1 d . . . . .
H20 H 1.084552 1.471253 1.113926 0.036 Uiso 1 1 calc R U . . .
C21 C 0.7539(2) 1.49889(18) 1.13419(8) 0.0276(3) Uani 1 1 d . . . . .
H21 H 0.807655 1.588100 1.181521 0.033 Uiso 1 1 calc R U . . .
N22 N 0.5209(2) 1.44503(15) 1.10962(7) 0.0290(3) Uani 1 1 d . . . . .
C23 C 0.4569(2) 1.31972(17) 1.04216(8) 0.0261(3) Uani 1 1 d . . . . .
H23 H 0.293005 1.275653 1.022539 0.031 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
C1 C8 1.5255(17) . ?
C1 C12 1.5274(19) . ?
C1 C2 1.5322(17) . ?
C2 C7 1.3930(17) . ?
C2 C3 1.3958(17) . ?
C3 C4 1.3907(19) . ?
C4 C5 1.383(2) . ?
C5 C6 1.380(2) . ?
C6 C7 1.3938(19) . ?
C8 C9 1.5000(17) . ?
C9 O10 1.2189(15) . ?
C9 O11 1.3176(15) . ?
C12 O13 1.2121(16) . ?
C12 O14 1.3180(16) . ?
O15 C16 1.2438(17) . ?
C16 N17 1.3239(18) . ?
C16 C18 1.4988(19) . ?
C18 N19 1.3361(17) . ?
C18 C23 1.3830(18) . ?
N19 C20 1.3351(19) . ?
C20 C21 1.3840(19) . ?
C21 N22 1.3329(18) . ?
N22 C23 1.3405(18) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 C1 C12 109.46(10) . . ?
C8 C1 C2 113.45(10) . . ?
C12 C1 C2 109.77(10) . . ?
C7 C2 C3 118.53(12) . . ?
C7 C2 C1 121.90(11) . . ?
C3 C2 C1 119.57(11) . . ?
C4 C3 C2 120.48(12) . . ?
C5 C4 C3 120.57(13) . . ?
C6 C5 C4 119.38(12) . . ?
C5 C6 C7 120.51(13) . . ?
C2 C7 C6 120.53(12) . . ?
C9 C8 C1 113.21(10) . . ?
O10 C9 O11 123.41(12) . . ?
O10 C9 C8 123.73(12) . . ?
O11 C9 C8 112.84(11) . . ?
O13 C12 O14 123.72(12) . . ?
O13 C12 C1 123.10(12) . . ?
O14 C12 C1 113.19(11) . . ?
O15 C16 N17 124.04(13) . . ?
O15 C16 C18 119.25(12) . . ?
N17 C16 C18 116.71(12) . . ?
N19 C18 C23 122.18(12) . . ?
N19 C18 C16 117.82(12) . . ?
C23 C18 C16 119.99(12) . . ?
C20 N19 C18 115.99(12) . . ?
N19 C20 C21 121.78(13) . . ?
N22 C21 C20 122.43(13) . . ?
C21 N22 C23 115.76(12) . . ?
N22 C23 C18 121.84(12) . . ?

_refine_diff_density_max         0.274
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.045


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methanol'
####################################################################### 
# 
# 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_spsa-ani
_database_code_depnum_ccdc_archive 'CCDC 1976320'
loop_
_audit_author_name
_audit_author_address
'Nikoletta B. Bathori'
;Cape Peninsula University of Technology
South Africa
;
_audit_update_record             
;
2020-01-09 deposited with the CCDC.	2020-02-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/4
_shelx_SHELXL_version_number     2016/4
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          334.15
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H31 N3 O4'
_chemical_formula_weight         473.56

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           18
_space_group_name_H-M_alt        'P 21 21 2'
_space_group_name_Hall           'P 2 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, -y, z'
'x+1/2, -y+1/2, -z'
'-x+1/2, y+1/2, -z'

_cell_length_a                   25.731(5)
_cell_length_b                   8.2594(17)
_cell_length_c                   12.118(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2575.3(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    5209
_cell_measurement_theta_min      1.583
_cell_measurement_theta_max      27.175

_exptl_crystal_description       plates
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.221
_exptl_crystal_F_000             1008
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.334
_exptl_crystal_size_mid          0.328
_exptl_crystal_size_min          0.093
_exptl_absorpt_coefficient_mu    0.082
_shelx_estimated_absorpt_T_min   0.973
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6916
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_process_details   SADABS-2016/2
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  Bruker
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            28838
_diffrn_reflns_av_unetI/netI     0.0286
_diffrn_reflns_av_R_equivalents  0.0375
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_h_max       32
_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         1.583
_diffrn_reflns_theta_max         27.175
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             5734
_reflns_number_gt                5209
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.760
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0405P)²+0.8358P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    noref
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 2013 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   ?
_chemical_absolute_configuration ?
_refine_ls_number_reflns         5734
_refine_ls_number_parameters     394
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0473
_refine_ls_R_factor_gt           0.0415
_refine_ls_wR_factor_ref         0.1028
_refine_ls_wR_factor_gt          0.0996
_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
C4 C 0.42113(12) 0.6459(4) 0.3946(3) 0.0452(7) Uani 1 1 d . . . . .
H4 H 0.436645 0.588830 0.454137 0.054 Uiso 1 1 calc R U . A 1
C5 C 0.45345(11) 0.6967(4) 0.3110(3) 0.0489(8) Uani 1 1 d . . . . .
H5 H 0.489922 0.681286 0.317002 0.059 Uiso 1 1 calc R U . . .
C6 C 0.43310(13) 0.7695(4) 0.2193(3) 0.0554(9) Uani 1 1 d . . . . .
H6 H 0.454037 0.804264 0.159269 0.067 Uiso 1 1 calc R U . B 1
C9 C 0.27139(10) 0.5484(3) 0.17291(18) 0.0226(5) Uani 1 1 d . . . . .
O10 O 0.26440(7) 0.51242(19) 0.07216(12) 0.0238(4) Uani 1 1 d . . . . .
O11 O 0.27765(7) 0.44728(18) 0.24672(12) 0.0248(4) Uani 1 1 d . . . . .
C12 C 0.27488(10) 0.9563(3) 0.33102(18) 0.0251(5) Uani 1 1 d . . . . .
O13 O 0.29003(6) 1.05297(18) 0.26057(12) 0.0226(4) Uani 1 1 d . . . . .
O14 O 0.25754(7) 0.99769(19) 0.42483(13) 0.0283(4) Uani 1 1 d . . . . .
N15 N 0.29917(7) 1.2993(2) 0.44416(15) 0.0178(4) Uani 1 1 d . . . . .
C16 C 0.35073(9) 1.2639(3) 0.48712(19) 0.0217(5) Uani 1 1 d . . . . .
C17 C 0.38335(9) 1.1632(3) 0.4270(2) 0.0286(5) Uani 1 1 d . . . . .
H17 H 0.372729 1.121519 0.357485 0.034 Uiso 1 1 calc R U . . .
C18 C 0.43145(11) 1.1247(4) 0.4699(3) 0.0416(7) Uani 1 1 d . . . . .
H18 H 0.454197 1.056187 0.429458 0.050 Uiso 1 1 calc R U . . .
C19 C 0.44671(12) 1.1846(4) 0.5705(3) 0.0531(9) Uani 1 1 d . . . . .
H19 H 0.479808 1.156471 0.599470 0.064 Uiso 1 1 calc R U . . .
C20 C 0.41440(13) 1.2853(4) 0.6297(3) 0.0527(9) Uani 1 1 d . . . . .
H20 H 0.425341 1.326647 0.699112 0.063 Uiso 1 1 calc R U . . .
C21 C 0.36578(11) 1.3265(3) 0.5882(2) 0.0343(6) Uani 1 1 d . . . . .
H21 H 0.343336 1.396239 0.628350 0.041 Uiso 1 1 calc R U . . .
N22 N 0.29632(7) 1.1967(2) 0.06237(15) 0.0175(4) Uani 1 1 d . . . . .
C23 C 0.35143(9) 1.1940(3) 0.03616(17) 0.0201(5) Uani 1 1 d . . . . .
C24 C 0.36937(11) 1.0975(3) -0.0492(2) 0.0311(6) Uani 1 1 d . . . . .
H24 H 0.345978 1.033834 -0.091514 0.037 Uiso 1 1 calc R U . . .
C25 C 0.42248(11) 1.0959(4) -0.0716(2) 0.0416(7) Uani 1 1 d . . . . .
H25 H 0.435456 1.031088 -0.130187 0.050 Uiso 1 1 calc R U . . .
C26 C 0.45622(11) 1.1872(4) -0.0097(2) 0.0413(7) Uani 1 1 d . . . . .
H26 H 0.492422 1.183969 -0.024953 0.050 Uiso 1 1 calc R U . . .
C27 C 0.43762(10) 1.2842(3) 0.0750(2) 0.0354(6) Uani 1 1 d . . . . .
H27 H 0.461043 1.348135 0.117062 0.042 Uiso 1 1 calc R U . . .
C28 C 0.38508(9) 1.2878(3) 0.09827(19) 0.0252(5) Uani 1 1 d . . . . .
H28 H 0.372187 1.353969 0.156260 0.030 Uiso 1 1 calc R U . . .
N29 N 0.17236(12) 0.3645(4) 0.3553(3) 0.0552(8) Uani 1 1 d . . . . .
C30 C 0.14041(10) 0.2812(3) 0.2834(2) 0.0284(5) Uani 1 1 d . . . . .
C31 C 0.08737(10) 0.2673(4) 0.3029(2) 0.0335(6) Uani 1 1 d . . . . .
H31 H 0.072467 0.319358 0.365279 0.040 Uiso 1 1 calc R U . . .
C32 C 0.05629(11) 0.1793(4) 0.2332(2) 0.0416(7) Uani 1 1 d . . . . .
H32 H 0.020189 0.170248 0.248417 0.050 Uiso 1 1 calc R U . . .
C33 C 0.07660(12) 0.1037(4) 0.1411(3) 0.0420(7) Uani 1 1 d . . . . .
H33 H 0.054773 0.045282 0.091987 0.050 Uiso 1 1 calc R U . . .
C34 C 0.12938(11) 0.1149(3) 0.1222(2) 0.0366(6) Uani 1 1 d . . . . .
H34 H 0.144089 0.061793 0.060085 0.044 Uiso 1 1 calc R U . . .
C35 C 0.16100(10) 0.2018(3) 0.1920(2) 0.0329(6) Uani 1 1 d . . . . .
H35 H 0.197250 0.207693 0.177634 0.039 Uiso 1 1 calc R U . . .
C1A C 0.28803(17) 0.7747(4) 0.3099(3) 0.0181(9) Uani 0.694(8) 1 d . . P C 1
H1A H 0.272415 0.709083 0.370857 0.022 Uiso 0.694(8) 1 calc R U P C 1
C2A C 0.34630(14) 0.7430(4) 0.3082(5) 0.0201(9) Uani 0.694(8) 1 d . . P C 1
C3A C 0.37012(17) 0.6695(5) 0.3992(5) 0.0253(10) Uani 0.694(8) 1 d . . P C 1
H3A H 0.350509 0.637781 0.461952 0.030 Uiso 0.694(8) 1 calc R U P C 1
C7A C 0.3770(2) 0.7897(7) 0.2208(5) 0.0341(12) Uani 0.694(8) 1 d . . P C 1
H7A H 0.360760 0.837440 0.158366 0.041 Uiso 0.694(8) 1 calc R U P C 1
C8A C 0.2617(2) 0.7265(4) 0.2019(3) 0.0214(9) Uani 0.694(8) 1 d . . P C 1
H8B H 0.274955 0.795798 0.141508 0.026 Uiso 0.694(8) 1 calc R U P C 1
H8A H 0.223782 0.745269 0.208301 0.026 Uiso 0.694(8) 1 calc R U P C 1
H15A H 0.2787(12) 1.205(4) 0.438(2) 0.042(8) Uiso 1 1 d . . . . .
H15B H 0.3000(10) 1.347(4) 0.375(2) 0.030(7) Uiso 1 1 d . . . . .
H22C H 0.2845(12) 1.306(4) 0.061(2) 0.040(8) Uiso 1 1 d . . . . .
H22A H 0.2933(10) 1.154(3) 0.131(2) 0.026(7) Uiso 1 1 d . . . . .
H22B H 0.2750(11) 1.137(4) 0.013(3) 0.040(8) Uiso 1 1 d . . . . .
H29A H 0.2019(14) 0.393(4) 0.326(3) 0.044(9) Uiso 1 1 d . . . . .
H15C H 0.2799(12) 1.365(4) 0.492(3) 0.047(9) Uiso 1 1 d . . . . .
H29B H 0.1578(15) 0.423(5) 0.403(3) 0.071(13) Uiso 1 1 d . . . . .
C1B C 0.2943(4) 0.7221(8) 0.2055(6) 0.0146(19) Uani 0.306(8) 1 d . . P C 2
H1B H 0.291534 0.793045 0.138880 0.018 Uiso 0.306(8) 1 calc R U P C 2
C2B C 0.3493(4) 0.7258(10) 0.2427(9) 0.0183(19) Uani 0.306(8) 1 d . . P C 2
C3B C 0.3636(4) 0.6662(13) 0.3451(11) 0.028(2) Uani 0.306(8) 1 d . . P C 2
H3B H 0.335966 0.633258 0.391959 0.034 Uiso 0.306(8) 1 calc R U P C 2
C7B C 0.3881(5) 0.7845(15) 0.1757(11) 0.032(3) Uani 0.306(8) 1 d . . P C 2
H7B H 0.382155 0.830916 0.105079 0.038 Uiso 0.306(8) 1 calc R U P C 2
C8B C 0.2544(4) 0.7842(9) 0.2910(6) 0.019(2) Uani 0.306(8) 1 d . . P C 2
H8D H 0.251980 0.708423 0.354115 0.022 Uiso 0.306(8) 1 calc R U P C 2
H8C H 0.219576 0.794493 0.256933 0.022 Uiso 0.306(8) 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
C4 C3A 1.328(5) . ?
C4 C5 1.376(4) . ?
C4 C3B 1.605(13) . ?
C4 H4 0.9500 . ?
C5 C6 1.367(5) . ?
C5 H5 0.9500 . ?
C6 C7B 1.279(13) . ?
C6 C7A 1.452(7) . ?
C6 H6 0.9500 . ?
C9 O11 1.235(3) . ?
C9 O10 1.269(3) . ?
C9 C8A 1.532(4) . ?
C9 C1B 1.600(7) . ?
C12 O13 1.232(3) . ?
C12 O14 1.268(3) . ?
C12 C1A 1.559(4) . ?
C12 C8B 1.592(8) . ?
N15 C16 1.455(3) . ?
N15 H15A 0.94(3) . ?
N15 H15B 0.93(3) . ?
N15 H15C 0.94(3) . ?
C16 C21 1.385(3) . ?
C16 C17 1.388(3) . ?
C17 C18 1.379(4) . ?
C17 H17 0.9500 . ?
C18 C19 1.373(4) . ?
C18 H18 0.9500 . ?
C19 C20 1.378(5) . ?
C19 H19 0.9500 . ?
C20 C21 1.391(4) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
N22 C23 1.453(3) . ?
N22 H22C 0.95(3) . ?
N22 H22A 0.91(3) . ?
N22 H22B 0.95(3) . ?
C23 C28 1.384(3) . ?
C23 C24 1.384(3) . ?
C24 C25 1.393(4) . ?
C24 H24 0.9500 . ?
C25 C26 1.373(4) . ?
C25 H25 0.9500 . ?
C26 C27 1.387(4) . ?
C26 H26 0.9500 . ?
C27 C28 1.381(4) . ?
C27 H27 0.9500 . ?
C28 H28 0.9500 . ?
N29 C30 1.381(4) . ?
N29 H29A 0.87(3) . ?
N29 H29B 0.84(4) . ?
C30 C31 1.390(4) . ?
C30 C35 1.392(4) . ?
C31 C32 1.372(4) . ?
C31 H31 0.9500 . ?
C32 C33 1.381(4) . ?
C32 H32 0.9500 . ?
C33 C34 1.380(4) . ?
C33 H33 0.9500 . ?
C34 C35 1.375(4) . ?
C34 H34 0.9500 . ?
C35 H35 0.9500 . ?
C1Aa C2A 1.522(6) . ?
C1Aa C8A 1.527(5) . ?
C1Aa H1A 1.0000 . ?
C2Aa C7A 1.377(7) . ?
C2Aa C3A 1.400(5) . ?
C3Aa H3A 0.9500 . ?
C7Aa H7A 0.9500 . ?
C8Aa H8B 0.9900 . ?
C8Aa H8A 0.9900 . ?
C1Bb C2B 1.487(14) . ?
C1Bb C8B 1.546(12) . ?
C1Bb H1B 1.0000 . ?
C2Bb C7B 1.375(12) . ?
C2Bb C3B 1.385(13) . ?
C3Bb H3B 0.9500 . ?
C7Bb H7B 0.9500 . ?
C8Bb H8D 0.9900 . ?
C8Bb H8C 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3Aa C4 C5 125.7(4) . . ?
C5 C4 C3B 104.5(5) . . ?
C3Aa C4 H4 117.2 . . ?
C5 C4 H4 117.2 . . ?
C6 C5 C4 120.0(3) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C7Bb C6 C5 136.5(7) . . ?
C5 C6 C7A 114.9(4) . . ?
C5 C6 H6 122.5 . . ?
C7Aa C6 H6 122.5 . . ?
O11 C9 O10 123.8(2) . . ?
O11 C9 C8A 120.3(2) . . ?
O10 C9 C8A 115.0(2) . . ?
O11 C9 C1B 112.3(3) . . ?
O10 C9 C1B 120.0(3) . . ?
O13 C12 O14 123.9(2) . . ?
O13 C12 C1A 116.2(2) . . ?
O14 C12 C1A 118.9(2) . . ?
O13 C12 C8B 118.2(3) . . ?
O14 C12 C8B 113.4(3) . . ?
C16 N15 H15A 111.8(19) . . ?
C16 N15 H15B 112.8(17) . . ?
H15A N15 H15B 107(2) . . ?
C16 N15 H15C 112.1(19) . . ?
H15A N15 H15C 103(3) . . ?
H15B N15 H15C 109(3) . . ?
C21 C16 C17 121.2(2) . . ?
C21 C16 N15 119.8(2) . . ?
C17 C16 N15 118.9(2) . . ?
C18 C17 C16 118.9(3) . . ?
C18 C17 H17 120.6 . . ?
C16 C17 H17 120.6 . . ?
C19 C18 C17 120.5(3) . . ?
C19 C18 H18 119.7 . . ?
C17 C18 H18 119.7 . . ?
C18 C19 C20 120.5(3) . . ?
C18 C19 H19 119.7 . . ?
C20 C19 H19 119.7 . . ?
C19 C20 C21 120.1(3) . . ?
C19 C20 H20 119.9 . . ?
C21 C20 H20 119.9 . . ?
C16 C21 C20 118.7(3) . . ?
C16 C21 H21 120.6 . . ?
C20 C21 H21 120.6 . . ?
C23 N22 H22C 108.7(18) . . ?
C23 N22 H22A 106.1(17) . . ?
H22C N22 H22A 111(2) . . ?
C23 N22 H22B 114.9(18) . . ?
H22C N22 H22B 107(3) . . ?
H22A N22 H22B 109(2) . . ?
C28 C23 C24 121.3(2) . . ?
C28 C23 N22 118.9(2) . . ?
C24 C23 N22 119.8(2) . . ?
C23 C24 C25 118.6(3) . . ?
C23 C24 H24 120.7 . . ?
C25 C24 H24 120.7 . . ?
C26 C25 C24 120.6(3) . . ?
C26 C25 H25 119.7 . . ?
C24 C25 H25 119.7 . . ?
C25 C26 C27 120.2(3) . . ?
C25 C26 H26 119.9 . . ?
C27 C26 H26 119.9 . . ?
C28 C27 C26 120.1(3) . . ?
C28 C27 H27 119.9 . . ?
C26 C27 H27 119.9 . . ?
C27 C28 C23 119.3(2) . . ?
C27 C28 H28 120.4 . . ?
C23 C28 H28 120.4 . . ?
C30 N29 H29A 114(2) . . ?
C30 N29 H29B 117(3) . . ?
H29A N29 H29B 121(4) . . ?
N29 C30 C31 121.2(3) . . ?
N29 C30 C35 120.7(3) . . ?
C31 C30 C35 118.0(2) . . ?
C32 C31 C30 120.7(2) . . ?
C32 C31 H31 119.6 . . ?
C30 C31 H31 119.6 . . ?
C31 C32 C33 121.1(3) . . ?
C31 C32 H32 119.4 . . ?
C33 C32 H32 119.4 . . ?
C34 C33 C32 118.4(3) . . ?
C34 C33 H33 120.8 . . ?
C32 C33 H33 120.8 . . ?
C35 C34 C33 121.0(3) . . ?
C35 C34 H34 119.5 . . ?
C33 C34 H34 119.5 . . ?
C34 C35 C30 120.7(2) . . ?
C34 C35 H35 119.7 . . ?
C30 C35 H35 119.7 . . ?
C2Aa C1Aa C8A 112.4(4) . . ?
C2Aa C1Aa C12 112.4(3) . . ?
C8Aa C1Aa C12 107.1(3) . . ?
C2Aa C1Aa H1A 108.2 . . ?
C8Aa C1Aa H1A 108.2 . . ?
C12 C1Aa H1A 108.2 . . ?
C7Aa C2Aa C3A 118.4(4) . . ?
C7Aa C2Aa C1A 121.9(4) . . ?
C3Aa C2Aa C1A 119.7(4) . . ?
C4 C3Aa C2A 117.6(4) . . ?
C4 C3Aa H3A 121.2 . . ?
C2Aa C3Aa H3A 121.2 . . ?
C2Aa C7Aa C6 123.2(4) . . ?
C2Aa C7Aa H7A 118.4 . . ?
C6 C7Aa H7A 118.4 . . ?
C1Aa C8Aa C9 112.0(3) . . ?
C1Aa C8Aa H8B 109.2 . . ?
C9 C8Aa H8B 109.2 . . ?
C1Aa C8Aa H8A 109.2 . . ?
C9 C8Aa H8A 109.2 . . ?
H8Ba C8Aa H8A 107.9 . . ?
C2Bb C1Bb C8B 115.0(8) . . ?
C2Bb C1Bb C9 116.3(6) . . ?
C8Bb C1Bb C9 102.6(6) . . ?
C2Bb C1Bb H1B 107.5 . . ?
C8Bb C1Bb H1B 107.5 . . ?
C9 C1Bb H1B 107.5 . . ?
C7Bb C2Bb C3B 117.5(9) . . ?
C7Bb C2Bb C1B 121.3(9) . . ?
C3Bb C2Bb C1B 121.2(9) . . ?
C2Bb C3Bb C4 128.1(8) . . ?
C2Bb C3Bb H3B 116.0 . . ?
C4 C3Bb H3B 116.0 . . ?
C6 C7Bb C2B 112.2(11) . . ?
C6 C7Bb H7B 123.9 . . ?
C2Bb C7Bb H7B 123.9 . . ?
C1Bb C8Bb C12 106.3(6) . . ?
C1Bb C8Bb H8D 110.5 . . ?
C12 C8Bb H8D 110.5 . . ?
C1Bb C8Bb H8C 110.5 . . ?
C12 C8Bb H8C 110.5 . . ?
H8Db C8Bb H8C 108.7 . . ?

_refine_diff_density_max         0.177
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.039

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: aniline'
####################################################################### 
# 
# 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_spsa-34lut
_database_code_depnum_ccdc_archive 'CCDC 1976325'
loop_
_audit_author_name
_audit_author_address
'Nikoletta B. Bathori'
;Cape Peninsula University of Technology
South Africa
;
_audit_update_record             
;
2020-01-09 deposited with the CCDC.	2020-02-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/4
_shelx_SHELXL_version_number     2016/4
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          328.61
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H28 N2 O4'
_chemical_formula_weight         408.48

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           1
_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'

_cell_length_a                   7.1918(14)
_cell_length_b                   8.7570(18)
_cell_length_c                   18.766(4)
_cell_angle_alpha                89.75(3)
_cell_angle_beta                 79.83(3)
_cell_angle_gamma                72.07(3)
_cell_volume                     1105.2(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    5940
_cell_measurement_theta_min      4.015
_cell_measurement_theta_max      26.707

_exptl_crystal_description       chunk
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.227
_exptl_crystal_F_000             436
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.084
_shelx_estimated_absorpt_T_min   0.992
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  Bruker
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9225
_diffrn_reflns_av_unetI/netI     0.0613
_diffrn_reflns_av_R_equivalents  0.075
_diffrn_reflns_limit_h_min       ?
_diffrn_reflns_limit_h_max       ?
_diffrn_reflns_limit_k_min       ?
_diffrn_reflns_limit_k_max       ?
_diffrn_reflns_limit_l_min       ?
_diffrn_reflns_limit_l_max       ?
_diffrn_reflns_theta_min         4.015
_diffrn_reflns_theta_max         26.707
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             9225
_reflns_number_gt                5940
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.986
_reflns_Friedel_fraction_max     0.980
_reflns_Friedel_fraction_full    0.986

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0844P)²+0.3894P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 2262 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   ?
_chemical_absolute_configuration ?
_refine_ls_number_reflns         9225
_refine_ls_number_parameters     546
_refine_ls_number_restraints     8
_refine_ls_R_factor_all          0.1152
_refine_ls_R_factor_gt           0.0647
_refine_ls_wR_factor_ref         0.1786
_refine_ls_wR_factor_gt          0.1511
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.024
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1A C 0.4004(9) 0.5378(6) 0.1165(3) 0.0460(13) Uani 1 1 d . . . . .
H1A H 0.296878 0.624618 0.097603 0.055 Uiso 1 1 calc R U . . .
C2A C 0.3220(8) 0.3960(6) 0.1297(3) 0.0402(12) Uani 1 1 d . . . . .
C3A C 0.4433(8) 0.2381(7) 0.1210(3) 0.0452(13) Uani 1 1 d . . . . .
H3A H 0.582461 0.214816 0.104860 0.054 Uiso 1 1 calc R U . . .
C4A C 0.3638(9) 0.1130(7) 0.1355(3) 0.0505(14) Uani 1 1 d . . . . .
H4A H 0.448378 0.004856 0.128823 0.061 Uiso 1 1 calc R U . . .
C5A C 0.1616(10) 0.1458(8) 0.1597(3) 0.0517(14) Uani 1 1 d . . . . .
H5A H 0.106965 0.060497 0.170099 0.062 Uiso 1 1 calc R U . . .
C6A C 0.0409(9) 0.3019(8) 0.1685(4) 0.0576(15) Uani 1 1 d . . . . .
H6A H -0.098029 0.325303 0.185246 0.069 Uiso 1 1 calc R U . . .
C7A C 0.1203(9) 0.4252(7) 0.1533(3) 0.0522(14) Uani 1 1 d . . . . .
H7A H 0.034493 0.532984 0.159180 0.063 Uiso 1 1 calc R U . . .
C8A C 0.5933(10) 0.5015(7) 0.0606(3) 0.0591(15) Uani 1 1 d . . . . .
H8A H 0.704720 0.433572 0.082244 0.071 Uiso 1 1 calc R U . . .
H8B H 0.582333 0.440060 0.018265 0.071 Uiso 1 1 calc R U . . .
C9A C 0.6379(11) 0.6500(8) 0.0359(4) 0.0616(17) Uani 1 1 d . . . . .
O10A O 0.607(3) 0.7079(17) -0.0191(9) 0.072(5) Uiso 0.40(2) 1 d . . P A 1
O11A O 0.740(2) 0.6961(17) 0.0767(11) 0.079(5) Uiso 0.40(2) 1 d . . P A 1
H11A H 0.787129 0.759445 0.051536 0.095 Uiso 0.40(2) 1 d R U P A 1
O10K O 0.5160(19) 0.7547(13) 0.0054(6) 0.077(4) Uiso 0.60(2) 1 d . . P A 2
O11K O 0.8063(17) 0.6641(12) 0.0417(7) 0.080(4) Uiso 0.60(2) 1 d D . P A 2
H11K H 0.796109 0.761911 0.046350 0.096 Uiso 0.60(2) 1 d DR U P A 2
C12A C 0.4267(8) 0.6032(6) 0.1887(3) 0.0404(12) Uani 1 1 d . . . . .
O13A O 0.5470(8) 0.5266(6) 0.2228(3) 0.0807(15) Uani 1 1 d . . . . .
O14A O 0.3062(6) 0.7446(5) 0.2080(3) 0.0588(11) Uani 1 1 d . . . . .
H14A H 0.326924 0.775575 0.247331 0.071 Uiso 1 1 calc R U . . .
N15A N 0.3122(6) 0.8684(5) 0.3315(3) 0.0455(11) Uani 1 1 d . . . . .
C16A C 0.2468(8) 1.0278(7) 0.3404(3) 0.0466(13) Uani 1 1 d . . . . .
H16A H 0.213842 1.086922 0.299372 0.056 Uiso 1 1 calc R U . . .
C17A C 0.2233(7) 1.1128(6) 0.4036(3) 0.0382(12) Uani 1 1 d . . . . .
C18A C 0.2718(7) 1.0278(6) 0.4648(3) 0.0348(11) Uani 1 1 d . . . . .
C19A C 0.3425(7) 0.8603(6) 0.4562(3) 0.0416(12) Uani 1 1 d . . . . .
H19A H 0.379700 0.797657 0.495803 0.050 Uiso 1 1 calc R U . . .
C20A C 0.3583(8) 0.7856(6) 0.3886(3) 0.0492(14) Uani 1 1 d . . . . .
H20A H 0.403526 0.671491 0.383506 0.059 Uiso 1 1 calc R U . . .
C21A C 0.1436(9) 1.2953(7) 0.4074(3) 0.0497(13) Uani 1 1 d . . . . .
H21A H 0.122637 1.332645 0.359285 0.075 Uiso 1 1 calc R U . . .
H21C H 0.239626 1.339533 0.423642 0.075 Uiso 1 1 calc R U . . .
H21B H 0.017057 1.331342 0.441737 0.075 Uiso 1 1 calc R U . . .
C22A C 0.2491(9) 1.1120(7) 0.5362(3) 0.0487(13) Uani 1 1 d . . . . .
H22C H 0.107454 1.160797 0.556340 0.073 Uiso 1 1 calc R U . . .
H22A H 0.313548 1.196028 0.529618 0.073 Uiso 1 1 calc R U . . .
H22B H 0.311314 1.034579 0.569549 0.073 Uiso 1 1 calc R U . . .
N23A N 0.943(3) 0.922(2) 0.0051(10) 0.080(6) Uiso 0.421(15) 1 d . . P B 3
C24A C 1.074(3) 1.027(2) 0.0017(11) 0.071(6) Uiso 0.421(15) 1 d . . P B 3
H24A H 1.184634 1.007139 0.025241 0.086 Uiso 0.421(15) 1 calc R U P B 3
C25A C 1.008(3) 1.162(3) -0.0425(12) 0.043(7) Uiso 0.421(15) 1 d . . P B 3
C26A C 0.867(4) 1.175(3) -0.0763(13) 0.055(8) Uiso 0.421(15) 1 d . . P B 3
C27A C 0.767(3) 1.064(2) -0.0696(10) 0.055(4) Uiso 0.421(15) 1 d . . P B 3
H27A H 0.665830 1.076732 -0.097421 0.067 Uiso 0.421(15) 1 calc R U P B 3
C28A C 0.799(3) 0.9482(19) -0.0298(10) 0.041(4) Uiso 0.421(15) 1 d . . P B 3
H28A H 0.717177 0.880194 -0.025292 0.049 Uiso 0.421(15) 1 calc R U P B 3
C29A C 1.138(3) 1.277(3) -0.0446(10) 0.066(5) Uiso 0.421(15) 1 d . . P B 3
H29G H 1.197550 1.266343 -0.000980 0.099 Uiso 0.421(15) 1 calc R U P B 3
H29H H 1.054540 1.388462 -0.046619 0.099 Uiso 0.421(15) 1 calc R U P B 3
H29I H 1.243906 1.248471 -0.087674 0.099 Uiso 0.421(15) 1 calc R U P B 3
C30A C 0.803(3) 1.312(2) -0.1265(9) 0.065(5) Uiso 0.421(15) 1 d . . P B 3
H30G H 0.762379 1.415184 -0.098816 0.098 Uiso 0.421(15) 1 calc R U P B 3
H30I H 0.691606 1.301045 -0.147043 0.098 Uiso 0.421(15) 1 calc R U P B 3
H30H H 0.915032 1.307117 -0.165717 0.098 Uiso 0.421(15) 1 calc R U P B 3
N23C N 0.8527(19) 0.9358(10) -0.0091(6) 0.040(3) Uiso 0.579(15) 1 d . . P B 4
C24C C 1.0038(19) 1.0004(15) -0.0053(6) 0.052(3) Uiso 0.579(15) 1 d . . P B 4
H24C H 1.097024 0.948693 0.024138 0.062 Uiso 0.579(15) 1 calc R U P B 4
C25C C 1.032(2) 1.1328(18) -0.0402(8) 0.037(5) Uiso 0.579(15) 1 d . . P B 4
C26C C 0.876(2) 1.2057(18) -0.0831(8) 0.040(4) Uiso 0.579(15) 1 d . . P B 4
C27C C 0.7287(16) 1.1441(15) -0.0865(6) 0.050(3) Uiso 0.579(15) 1 d . . P B 4
H27C H 0.631303 1.191912 -0.114968 0.060 Uiso 0.579(15) 1 calc R U P B 4
C28C C 0.7194(19) 1.0118(16) -0.0486(6) 0.051(3) Uiso 0.579(15) 1 d . . P B 4
H28C H 0.611392 0.972134 -0.050745 0.061 Uiso 0.579(15) 1 calc R U P B 4
C29C C 1.1889(17) 1.2010(17) -0.0353(6) 0.057(3) Uiso 0.579(15) 1 d . . P B 4
H29F H 1.245975 1.224666 -0.083821 0.086 Uiso 0.579(15) 1 calc R U P B 4
H29D H 1.292754 1.124228 -0.014117 0.086 Uiso 0.579(15) 1 calc R U P B 4
H29E H 1.134300 1.300509 -0.004478 0.086 Uiso 0.579(15) 1 calc R U P B 4
C30C C 0.8914(19) 1.3504(13) -0.1249(6) 0.055(3) Uiso 0.579(15) 1 d . . P B 4
H30D H 0.875580 1.440081 -0.090884 0.083 Uiso 0.579(15) 1 calc R U P B 4
H30F H 0.786591 1.380967 -0.154070 0.083 Uiso 0.579(15) 1 calc R U P B 4
H30E H 1.021704 1.324050 -0.156789 0.083 Uiso 0.579(15) 1 calc R U P B 4
C1B C 0.5675(7) 0.4967(6) 0.6287(3) 0.0369(11) Uani 1 1 d . . . . .
H1B H 0.424355 0.563325 0.640148 0.044 Uiso 1 1 calc R U . . .
C2B C 0.6889(7) 0.6110(6) 0.6152(3) 0.0335(11) Uani 1 1 d . . . . .
C3B C 0.8943(8) 0.5554(6) 0.5925(3) 0.0453(13) Uani 1 1 d . . . . .
H3B H 0.961083 0.443036 0.586373 0.054 Uiso 1 1 calc R U . . .
C4B C 1.0024(9) 0.6622(7) 0.5786(3) 0.0499(14) Uani 1 1 d . . . . .
H4B H 1.142155 0.622922 0.562082 0.060 Uiso 1 1 calc R U . . .
C5B C 0.9076(9) 0.8250(7) 0.5887(3) 0.0470(13) Uani 1 1 d . . . . .
H5B H 0.981298 0.898510 0.579100 0.056 Uiso 1 1 calc R U . . .
C6B C 0.7054(9) 0.8806(6) 0.6129(3) 0.0458(13) Uani 1 1 d . . . . .
H6B H 0.639774 0.992925 0.620673 0.055 Uiso 1 1 calc R U . . .
C7B C 0.5974(8) 0.7749(6) 0.6258(3) 0.0390(12) Uani 1 1 d . . . . .
H7B H 0.457695 0.815290 0.642267 0.047 Uiso 1 1 calc R U . . .
C8B C 0.6113(8) 0.3955(7) 0.6932(3) 0.0457(12) Uani 1 1 d . . . . .
H8C H 0.749317 0.321758 0.681586 0.055 Uiso 1 1 calc R U . . .
H8D H 0.602392 0.467178 0.735163 0.055 Uiso 1 1 calc R U . . .
C9B C 0.4721(8) 0.2981(7) 0.7142(3) 0.0440(12) Uani 1 1 d . . . . .
O10B O 0.3231(7) 0.3183(5) 0.6895(3) 0.0657(12) Uani 1 1 d . . . . .
O11B O 0.5299(6) 0.1910(5) 0.7612(2) 0.0557(10) Uani 1 1 d . . . . .
H11B H 0.457449 0.131133 0.766331 0.067 Uiso 1 1 calc R U . . .
C12B C 0.5972(10) 0.3961(8) 0.5588(4) 0.0564(16) Uani 1 1 d . . . . .
O13B O 0.5126(8) 0.4588(6) 0.5090(3) 0.0722(13) Uani 1 1 d . . . . .
O14B O 0.7152(7) 0.2530(5) 0.5550(3) 0.0654(12) Uani 1 1 d . . . . .
H14B H 0.717178 0.206677 0.515001 2(2) Uiso 1 1 d R . . . .
N15B N 0.7187(8) 0.1364(7) 0.4211(3) 0.088(2) Uani 1 1 d D . . . .
C16B C 0.7848(9) -0.0255(7) 0.4154(3) 0.080(2) Uani 1 1 d D . . . .
H16B H 0.815781 -0.083646 0.456919 0.096 Uiso 1 1 calc R U . . .
C17B C 0.8080(8) -0.1076(7) 0.3510(3) 0.0523(15) Uani 1 1 d D . . . .
C18B C 0.7633(7) -0.0262(7) 0.2909(3) 0.0406(12) Uani 1 1 d . . . . .
C19B C 0.6958(8) 0.1395(7) 0.2962(3) 0.0562(15) Uani 1 1 d D . . . .
H19B H 0.664779 0.198842 0.255051 0.067 Uiso 1 1 calc R U . . .
C20B C 0.6743(8) 0.2175(6) 0.3618(3) 0.083(3) Uani 1 1 d D . . . .
H20B H 0.626711 0.331595 0.365684 0.100 Uiso 1 1 calc R U . . .
C21B C 0.8845(12) -0.2879(10) 0.3507(6) 0.098(3) Uani 1 1 d . . . . .
H21D H 0.879856 -0.321363 0.400746 0.146 Uiso 1 1 calc R U . . .
H21F H 1.022011 -0.326073 0.324308 0.146 Uiso 1 1 calc R U . . .
H21E H 0.801488 -0.333880 0.326979 0.146 Uiso 1 1 calc R U . . .
C22B C 0.7933(10) -0.1179(9) 0.2205(4) 0.0677(19) Uani 1 1 d . . . . .
H22D H 0.709594 -0.188389 0.225826 0.101 Uiso 1 1 calc R U . . .
H22F H 0.933201 -0.182863 0.206715 0.101 Uiso 1 1 calc R U . . .
H22E H 0.756654 -0.042395 0.182824 0.101 Uiso 1 1 calc R U . . .
N23B N 0.3024(7) 0.0051(5) 0.7833(3) 0.0429(10) Uani 1 1 d . . . . .
C24B C 0.3327(8) -0.1259(7) 0.8222(3) 0.0450(13) Uani 1 1 d . . . . .
H24B H 0.439195 -0.149301 0.848277 0.054 Uiso 1 1 calc R U . . .
C25B C 0.2193(8) -0.2301(6) 0.8273(3) 0.0414(12) Uani 1 1 d . . . . .
C26B C 0.0635(8) -0.1957(7) 0.7884(3) 0.0445(13) Uani 1 1 d . . . . .
C27B C 0.0322(8) -0.0583(7) 0.7478(3) 0.0461(13) Uani 1 1 d . . . . .
H27B H -0.072205 -0.031624 0.720707 0.055 Uiso 1 1 calc R U . . .
C28B C 0.1505(8) 0.0373(7) 0.7469(3) 0.0452(13) Uani 1 1 d . . . . .
H28B H 0.124703 0.130511 0.719476 0.054 Uiso 1 1 calc R U . . .
C29B C 0.2634(10) -0.3721(7) 0.8734(4) 0.0592(16) Uani 1 1 d . . . . .
H29A H 0.375932 -0.374121 0.896555 0.089 Uiso 1 1 calc R U . . .
H29B H 0.296645 -0.470999 0.843039 0.089 Uiso 1 1 calc R U . . .
H29C H 0.146319 -0.364085 0.910725 0.089 Uiso 1 1 calc R U . . .
C30B C -0.0647(10) -0.3018(9) 0.7892(4) 0.0661(18) Uani 1 1 d . . . . .
H30A H 0.016373 -0.408045 0.767172 0.099 Uiso 1 1 calc R U . . .
H30B H -0.170254 -0.254280 0.761620 0.099 Uiso 1 1 calc R U . . .
H30C H -0.124204 -0.312767 0.839377 0.099 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
C1A C2A 1.517(7) . ?
C1A C8A 1.530(8) . ?
C1A C12A 1.538(8) . ?
C2A C3A 1.382(7) . ?
C2A C7A 1.382(8) . ?
C3A C4A 1.388(8) . ?
C4A C5A 1.384(9) . ?
C5A C6A 1.368(8) . ?
C6A C7A 1.375(9) . ?
C8A C9A 1.486(8) . ?
C9A O10A 1.173(14) . ?
C9A O10K 1.270(12) . ?
C9A O11K 1.279(11) . ?
C9A O11A 1.292(16) . ?
C12A O13A 1.201(7) . ?
C12A O14A 1.284(6) . ?
N15A C20A 1.324(7) . ?
N15A C16A 1.329(7) . ?
C16A C17A 1.360(7) . ?
C17A C18A 1.403(7) . ?
C17A C21A 1.520(7) . ?
C18A C19A 1.396(7) . ?
C18A C22A 1.491(8) . ?
C19A C20A 1.400(8) . ?
N23Ac C28A 1.28(2) . ?
N23Ac C24A 1.50(3) . ?
C24Ac C25A 1.45(3) . ?
C25Ac C26A 1.26(3) . ?
C25Ac C29A 1.57(3) . ?
C26Ac C27A 1.37(3) . ?
C26Ac C30A 1.53(3) . ?
C27Ac C28A 1.25(3) . ?
N23Cd C28C 1.329(16) . ?
N23Cd C24C 1.383(18) . ?
C24Cd C25C 1.38(2) . ?
C25Cd C29C 1.444(18) . ?
C25Cd C26C 1.48(2) . ?
C26Cd C27C 1.342(18) . ?
C26Cd C30C 1.509(19) . ?
C27Cd C28C 1.369(18) . ?
C1B C2B 1.512(7) . ?
C1B C8B 1.516(7) . ?
C1B C12B 1.530(8) . ?
C2B C7B 1.381(6) . ?
C2B C3B 1.392(7) . ?
C3B C4B 1.386(8) . ?
C4B C5B 1.376(8) . ?
C5B C6B 1.375(8) . ?
C6B C7B 1.376(7) . ?
C8B C9B 1.506(7) . ?
C9B O10B 1.205(6) . ?
C9B O11B 1.309(6) . ?
C12B O13B 1.238(8) . ?
C12B O14B 1.273(7) . ?
N15B C16B 1.3482(15) . ?
N15B C20B 1.3501(15) . ?
C16B C17B 1.3679(15) . ?
C17B C18B 1.365(8) . ?
C17B C21B 1.503(10) . ?
C18B C19B 1.380(8) . ?
C18B C22B 1.496(8) . ?
C19B C20B 1.3716(15) . ?
N23B C24B 1.338(7) . ?
N23B C28B 1.345(7) . ?
C24B C25B 1.392(7) . ?
C25B C26B 1.399(8) . ?
C25B C29B 1.497(8) . ?
C26B C27B 1.402(8) . ?
C26B C30B 1.496(8) . ?
C27B C28B 1.363(8) . ?

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
C2A C1A C8A 114.2(4) . . ?
C2A C1A C12A 109.7(4) . . ?
C8A C1A C12A 110.4(5) . . ?
C3A C2A C7A 118.0(5) . . ?
C3A C2A C1A 123.1(5) . . ?
C7A C2A C1A 118.8(4) . . ?
C2A C3A C4A 120.6(5) . . ?
C5A C4A C3A 120.1(5) . . ?
C6A C5A C4A 119.5(5) . . ?
C5A C6A C7A 120.1(6) . . ?
C6A C7A C2A 121.6(5) . . ?
C9A C8A C1A 112.3(5) . . ?
O10Kb C9A O11K 121.2(8) . . ?
O10Aa C9A O11A 122.9(11) . . ?
O10Aa C9A C8A 124.3(8) . . ?
O10Kb C9A C8A 120.3(7) . . ?
O11Kb C9A C8A 118.4(7) . . ?
O11Aa C9A C8A 112.2(9) . . ?
O13A C12A O14A 124.8(5) . . ?
O13A C12A C1A 122.3(5) . . ?
O14A C12A C1A 112.9(5) . . ?
C20A N15A C16A 117.6(5) . . ?
N15A C16A C17A 125.1(5) . . ?
C16A C17A C18A 118.4(4) . . ?
C16A C17A C21A 120.3(5) . . ?
C18A C17A C21A 121.3(5) . . ?
C19A C18A C17A 117.2(5) . . ?
C19A C18A C22A 121.1(5) . . ?
C17A C18A C22A 121.7(4) . . ?
C18A C19A C20A 119.4(5) . . ?
N15A C20A C19A 122.3(5) . . ?
C28Ac N23Ac C24A 123.0(16) . . ?
C25Ac C24Ac N23A 110.8(18) . . ?
C26Ac C25Ac C24A 121(2) . . ?
C26Ac C25Ac C29A 127(2) . . ?
C24Ac C25Ac C29A 111.7(18) . . ?
C25Ac C26Ac C27A 120(2) . . ?
C25Ac C26Ac C30A 122(2) . . ?
C27Ac C26Ac C30A 117.5(19) . . ?
C28Ac C27Ac C26A 125.2(19) . . ?
C27Ac C28Ac N23A 119.1(16) . . ?
C28Cd N23Cd C24C 116.5(10) . . ?
C25Cd C24Cd N23C 126.3(12) . . ?
C24Cd C25Cd C29C 126.1(13) . . ?
C24Cd C25Cd C26C 112.2(12) . . ?
C29Cd C25Cd C26C 121.7(13) . . ?
C27Cd C26Cd C25C 121.6(13) . . ?
C27Cd C26Cd C30C 120.7(12) . . ?
C25Cd C26Cd C30C 117.7(12) . . ?
C26Cd C27Cd C28C 119.6(13) . . ?
N23Cd C28Cd C27C 123.7(12) . . ?
C2B C1B C8B 112.6(4) . . ?
C2B C1B C12B 108.9(4) . . ?
C8B C1B C12B 113.1(4) . . ?
C7B C2B C3B 118.1(5) . . ?
C7B C2B C1B 120.3(4) . . ?
C3B C2B C1B 121.6(4) . . ?
C4B C3B C2B 120.7(5) . . ?
C5B C4B C3B 120.1(5) . . ?
C6B C5B C4B 119.5(5) . . ?
C5B C6B C7B 120.5(5) . . ?
C6B C7B C2B 121.0(5) . . ?
C9B C8B C1B 113.5(4) . . ?
O10B C9B O11B 124.2(5) . . ?
O10B C9B C8B 122.5(5) . . ?
O11B C9B C8B 113.3(5) . . ?
O13B C12B O14B 124.3(6) . . ?
O13B C12B C1B 119.0(5) . . ?
O14B C12B C1B 116.7(6) . . ?
C16B N15B C20B 118.8(6) . . ?
N15B C16B C17B 121.1(6) . . ?
C18B C17B C16B 120.3(6) . . ?
C18B C17B C21B 123.1(6) . . ?
C16B C17B C21B 116.6(6) . . ?
C17B C18B C19B 118.9(5) . . ?
C17B C18B C22B 119.6(5) . . ?
C19B C18B C22B 121.5(5) . . ?
C20B C19B C18B 119.0(5) . . ?
N15B C20B C19B 121.8(6) . . ?
C24B N23B C28B 117.1(4) . . ?
N23B C24B C25B 124.7(5) . . ?
C24B C25B C26B 117.5(5) . . ?
C24B C25B C29B 120.5(5) . . ?
C26B C25B C29B 122.0(5) . . ?
C25B C26B C27B 117.6(5) . . ?
C25B C26B C30B 121.6(5) . . ?
C27B C26B C30B 120.7(5) . . ?
C28B C27B C26B 120.4(5) . . ?
N23B C28B C27B 122.7(5) . . ?

_refine_diff_density_max         0.425
_refine_diff_density_min         -0.338
_refine_diff_density_rms         0.048

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: 3,4-lutidine'
####################################################################### 
# 
# 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_racpsa-ani
_database_code_depnum_ccdc_archive 'CCDC 1976319'
loop_
_audit_author_name
_audit_author_address
'Nikoletta B. Bathori'
;Cape Peninsula University of Technology
South Africa
;
_audit_update_record             
;
2020-01-09 deposited with the CCDC.	2020-02-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/4
_shelx_SHELXL_version_number     2016/4
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          408.43
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H17 N O4'
_chemical_formula_weight         287.30

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_H-M_alt        'P n'
_space_group_name_Hall           'P -2yac'

_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'

_cell_length_a                   9.5310(19)
_cell_length_b                   8.3030(17)
_cell_length_c                   9.885(2)
_cell_angle_alpha                90
_cell_angle_beta                 111.82(3)
_cell_angle_gamma                90
_cell_volume                     726.2(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    2428
_cell_measurement_theta_min      2.45
_cell_measurement_theta_max      26.77

_exptl_crystal_description       chunk
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_F_000             304
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.095
_shelx_estimated_absorpt_T_min   0.972
_shelx_estimated_absorpt_T_max   0.996
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.953
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  Bruker
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10213
_diffrn_reflns_av_unetI/netI     0.0381
_diffrn_reflns_av_R_equivalents  0.0316
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.453
_diffrn_reflns_theta_max         28.389
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             3608
_reflns_number_gt                3039
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.973
_reflns_Friedel_fraction_max     0.978
_reflns_Friedel_fraction_full    0.989

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0443P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    noref
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1218 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   ?
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3608
_refine_ls_number_parameters     206
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0500
_refine_ls_R_factor_gt           0.0392
_refine_ls_wR_factor_ref         0.0862
_refine_ls_wR_factor_gt          0.0810
_refine_ls_goodness_of_fit_ref   0.992
_refine_ls_restrained_S_all      0.992
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.5469(2) 0.4384(3) 0.3316(2) 0.0219(5) Uani 1 1 d . . . . .
H1 H 0.623998 0.485024 0.418615 0.026 Uiso 1 1 calc R U . . .
C2 C 0.5565(2) 0.2562(3) 0.3490(3) 0.0232(5) Uani 1 1 d . . . . .
C3 C 0.6162(3) 0.1889(3) 0.4869(3) 0.0335(6) Uani 1 1 d . . . . .
H3 H 0.654506 0.255166 0.568245 0.040 Uiso 1 1 calc R U . . .
C4 C 0.6190(3) 0.0226(4) 0.5043(3) 0.0422(7) Uani 1 1 d . . . . .
H4 H 0.658193 -0.021627 0.597281 0.051 Uiso 1 1 calc R U . . .
C5 C 0.5644(3) -0.0765(3) 0.3851(3) 0.0414(7) Uani 1 1 d . . . . .
H5 H 0.567799 -0.187659 0.397173 0.050 Uiso 1 1 calc R U . . .
C6 C 0.5045(3) -0.0108(3) 0.2474(4) 0.0394(7) Uani 1 1 d . . . . .
H6 H 0.467441 -0.077640 0.166280 0.047 Uiso 1 1 calc R U . . .
H15A H 0.495(3) 0.660(3) 0.729(3) 0.031(7) Uiso 1 1 d . . . . .
H15B H 0.449(3) 0.666(3) 0.862(3) 0.035(7) Uiso 1 1 d . . . . .
H15C H 0.611(3) 0.647(4) 0.891(3) 0.046(9) Uiso 1 1 d . . . . .
H14 H 0.740(4) 0.495(4) 0.138(4) 0.058(10) Uiso 1 1 d . . . . .
C7 C 0.4994(3) 0.1547(3) 0.2299(3) 0.0316(6) Uani 1 1 d . . . . .
H7 H 0.457053 0.198323 0.136794 0.038 Uiso 1 1 calc R U . . .
C8 C 0.3935(3) 0.5010(3) 0.3244(2) 0.0242(5) Uani 1 1 d . . . . .
H8A H 0.373583 0.604700 0.275707 0.029 Uiso 1 1 calc R U . . .
H8B H 0.314828 0.427019 0.267682 0.029 Uiso 1 1 calc R U . . .
C9 C 0.3892(2) 0.5185(3) 0.4752(2) 0.0212(5) Uani 1 1 d . . . . .
O10 O 0.49142(18) 0.5946(2) 0.56826(18) 0.0315(4) Uani 1 1 d . . . . .
O11 O 0.27742(17) 0.4581(2) 0.49702(18) 0.0304(4) Uani 1 1 d . . . . .
C12 C 0.5827(3) 0.4914(3) 0.2014(3) 0.0242(5) Uani 1 1 d . . . . .
O13 O 0.4939(2) 0.5586(2) 0.0957(2) 0.0415(5) Uani 1 1 d . . . . .
O14 O 0.72273(18) 0.4576(2) 0.21765(19) 0.0342(4) Uani 1 1 d . . . . .
N15 N 0.5204(2) 0.6986(2) 0.8334(2) 0.0248(4) Uani 1 1 d . . . . .
C16 C 0.5298(2) 0.8742(3) 0.8428(2) 0.0233(5) Uani 1 1 d . . . . .
C17 C 0.6698(3) 0.9466(3) 0.8990(3) 0.0336(6) Uani 1 1 d . . . . .
H17 H 0.757479 0.884923 0.932428 0.040 Uiso 1 1 calc R U . . .
C18 C 0.6770(3) 1.1124(3) 0.9045(3) 0.0418(7) Uani 1 1 d . . . . .
H18 H 0.770589 1.163127 0.942721 0.050 Uiso 1 1 calc R U . . .
C19 C 0.5472(3) 1.2038(3) 0.8539(3) 0.0432(7) Uani 1 1 d . . . . .
H19 H 0.553236 1.315614 0.856919 0.052 Uiso 1 1 calc R U . . .
C20 C 0.4084(3) 1.1290(3) 0.7988(3) 0.0445(7) Uani 1 1 d . . . . .
H20 H 0.320722 1.190643 0.765175 0.053 Uiso 1 1 calc R U . . .
C21 C 0.3986(3) 0.9630(3) 0.7933(3) 0.0350(6) Uani 1 1 d . . . . .
H21 H 0.304944 0.912241 0.756748 0.042 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
C1 C12 1.514(3) . ?
C1 C2 1.522(3) . ?
C1 C8 1.528(3) . ?
C1 H1 0.9800 . ?
C2 C3 1.385(3) . ?
C2 C7 1.385(3) . ?
C3 C4 1.390(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.371(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.378(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.383(4) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 C9 1.513(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 O10 1.237(3) . ?
C9 O11 1.266(3) . ?
C12 O13 1.208(3) . ?
C12 O14 1.314(3) . ?
O14 H14 0.91(4) . ?
N15 C16 1.462(3) . ?
N15 H15A 1.02(3) . ?
N15 H15B 0.87(3) . ?
N15 H15C 0.94(3) . ?
C16 C21 1.376(3) . ?
C16 C17 1.378(3) . ?
C17 C18 1.379(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.377(4) . ?
C18 H18 0.9300 . ?
C19 C20 1.377(4) . ?
C19 H19 0.9300 . ?
C20 C21 1.381(4) . ?
C20 H20 0.9300 . ?
C21 H21 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
C12 C1 C2 111.24(19) . . ?
C12 C1 C8 112.08(19) . . ?
C2 C1 C8 111.07(19) . . ?
C12 C1 H1 107.4 . . ?
C2 C1 H1 107.4 . . ?
C8 C1 H1 107.4 . . ?
C3 C2 C7 118.6(2) . . ?
C3 C2 C1 119.9(2) . . ?
C7 C2 C1 121.4(2) . . ?
C2 C3 C4 120.3(3) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C5 C4 C3 120.4(3) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C4 C5 C6 119.8(3) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
C5 C6 C7 119.9(3) . . ?
C5 C6 H6 120.0 . . ?
C7 C6 H6 120.0 . . ?
C6 C7 C2 120.9(2) . . ?
C6 C7 H7 119.5 . . ?
C2 C7 H7 119.5 . . ?
C9 C8 C1 111.27(19) . . ?
C9 C8 H8A 109.4 . . ?
C1 C8 H8A 109.4 . . ?
C9 C8 H8B 109.4 . . ?
C1 C8 H8B 109.4 . . ?
H8A C8 H8B 108.0 . . ?
O10 C9 O11 123.8(2) . . ?
O10 C9 C8 118.6(2) . . ?
O11 C9 C8 117.55(19) . . ?
O13 C12 O14 123.9(2) . . ?
O13 C12 C1 124.2(2) . . ?
O14 C12 C1 111.9(2) . . ?
C12 O14 H14 109(2) . . ?
C16 N15 H15A 111.3(15) . . ?
C16 N15 H15B 109.3(18) . . ?
H15A N15 H15B 108(2) . . ?
C16 N15 H15C 113.1(19) . . ?
H15A N15 H15C 107(2) . . ?
H15B N15 H15C 108(2) . . ?
C21 C16 C17 121.7(2) . . ?
C21 C16 N15 119.1(2) . . ?
C17 C16 N15 119.2(2) . . ?
C16 C17 C18 118.6(2) . . ?
C16 C17 H17 120.7 . . ?
C18 C17 H17 120.7 . . ?
C19 C18 C17 120.7(3) . . ?
C19 C18 H18 119.6 . . ?
C17 C18 H18 119.6 . . ?
C18 C19 C20 119.7(3) . . ?
C18 C19 H19 120.1 . . ?
C20 C19 H19 120.1 . . ?
C19 C20 C21 120.5(3) . . ?
C19 C20 H20 119.8 . . ?
C21 C20 H20 119.8 . . ?
C16 C21 C20 118.8(2) . . ?
C16 C21 H21 120.6 . . ?
C20 C21 H21 120.6 . . ?

_refine_diff_density_max         0.152
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.035

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: aniline'
####################################################################### 
# 
# 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_spsa-35lut
_database_code_depnum_ccdc_archive 'CCDC 1976327'
loop_
_audit_author_name
_audit_author_address
'Nikoletta B. Bathori'
;Cape Peninsula University of Technology
South Africa
;
_audit_update_record             
;
2020-01-09 deposited with the CCDC.	2020-02-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/4
_shelx_SHELXL_version_number     2016/4
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          370.27
_chemical_formula_moiety         ?
_chemical_formula_sum            'C88 H96 N4 O24'
_chemical_formula_weight         1593.68

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           1
_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'

_cell_length_a                   8.3469(17)
_cell_length_b                   12.268(3)
_cell_length_c                   20.595(4)
_cell_angle_alpha                84.66(3)
_cell_angle_beta                 86.58(3)
_cell_angle_gamma                76.63(3)
_cell_volume                     2041.2(8)
_cell_formula_units_Z            1
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9885
_cell_measurement_theta_min      2.51
_cell_measurement_theta_max      27.37

_exptl_crystal_description       chunk
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_F_000             844
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.095
_shelx_estimated_absorpt_T_min   0.954
_shelx_estimated_absorpt_T_max   0.981
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.946
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  BRUKER
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            46913
_diffrn_reflns_av_unetI/netI     0.0392
_diffrn_reflns_av_R_equivalents  0.0269
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         1.712
_diffrn_reflns_theta_max         28.361
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_point_group_measured_fraction_full 0.977
_reflns_number_total             19773
_reflns_number_gt                14901
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.945
_reflns_Friedel_fraction_max     0.940
_reflns_Friedel_fraction_full    0.955

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.1122P)²+1.3745P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 5564 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.2(3)
_chemical_absolute_configuration rm
_refine_ls_number_reflns         19773
_refine_ls_number_parameters     1062
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.1012
_refine_ls_R_factor_gt           0.0768
_refine_ls_wR_factor_ref         0.2177
_refine_ls_wR_factor_gt          0.1977
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_restrained_S_all      1.019
_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
C1A C 0.1934(7) 0.3859(5) 0.2798(3) 0.0439(12) Uani 1 1 d . . . . .
H1A H 0.213508 0.455178 0.254160 0.053 Uiso 1 1 calc R U . . .
C2A C 0.0059(6) 0.4009(5) 0.2902(2) 0.0388(11) Uani 1 1 d . . . . .
C3A C -0.0915(7) 0.5062(5) 0.2788(3) 0.0446(12) Uani 1 1 d . . . . .
H3A H -0.043065 0.566030 0.261243 0.054 Uiso 1 1 calc R U . . .
C4A C -0.2588(8) 0.5269(6) 0.2922(3) 0.0534(15) Uani 1 1 d . . . . .
H4A H -0.324986 0.600473 0.283610 0.064 Uiso 1 1 calc R U . . .
C5A C -0.3311(7) 0.4407(6) 0.3182(3) 0.0541(16) Uani 1 1 d . . . . .
H5A H -0.446058 0.455611 0.328692 0.065 Uiso 1 1 calc R U . . .
C6A C -0.2371(7) 0.3348(6) 0.3287(3) 0.0502(14) Uani 1 1 d . . . . .
H6A H -0.286660 0.275495 0.346182 0.060 Uiso 1 1 calc R U . . .
C7A C -0.0682(7) 0.3131(5) 0.3140(3) 0.0445(12) Uani 1 1 d . . . . .
H7A H -0.003305 0.238573 0.320063 0.053 Uiso 1 1 calc R U . . .
C8A C 0.2655(8) 0.2873(5) 0.2398(3) 0.0514(14) Uani 1 1 d . . . . .
H8A H 0.386662 0.277828 0.236003 0.062 Uiso 1 1 calc R U . . .
H8B H 0.242320 0.218294 0.263449 0.062 Uiso 1 1 calc R U . . .
C9A C 0.2001(7) 0.2991(4) 0.1720(3) 0.0412(12) Uani 1 1 d . . . . .
O10A O 0.1727(8) 0.2150(4) 0.1509(2) 0.0751(16) Uani 1 1 d . . . . .
O11A O 0.1786(5) 0.3927(3) 0.13855(18) 0.0435(9) Uani 1 1 d . . . . .
C12A C 0.2709(6) 0.3787(4) 0.3467(3) 0.0364(10) Uani 1 1 d . . . . .
O13A O 0.3372(5) 0.2841(3) 0.3742(2) 0.0466(9) Uani 1 1 d . . . . .
O14A O 0.2570(5) 0.4672(3) 0.3727(2) 0.0436(9) Uani 1 1 d . . . . .
N15A N 0.4561(5) 0.3114(4) 0.4888(2) 0.0388(10) Uani 1 1 d . . . . .
H15A H 0.409761 0.302436 0.453001 0.047 Uiso 1 1 calc R U . . .
C16A C 0.5158(6) 0.2206(5) 0.5289(3) 0.0386(11) Uani 1 1 d . . . . .
H16A H 0.504230 0.148737 0.519113 0.046 Uiso 1 1 calc R U . . .
C17A C 0.5939(6) 0.2309(4) 0.5844(3) 0.0358(10) Uani 1 1 d . . . . .
C18A C 0.6012(6) 0.3387(4) 0.5977(2) 0.0360(10) Uani 1 1 d . . . . .
H18A H 0.651048 0.348470 0.636419 0.043 Uiso 1 1 calc R U . . .
C19A C 0.5375(7) 0.4325(4) 0.5561(3) 0.0380(11) Uani 1 1 d . . . . .
C20A C 0.4641(7) 0.4153(5) 0.5011(3) 0.0404(11) Uani 1 1 d . . . . .
H20A H 0.418854 0.477554 0.471595 0.048 Uiso 1 1 calc R U . . .
C21A C 0.6678(9) 0.1298(5) 0.6286(3) 0.0537(15) Uani 1 1 d . . . . .
H21B H 0.689872 0.062544 0.604307 0.081 Uiso 1 1 calc R U . . .
H21C H 0.590603 0.121267 0.665482 0.081 Uiso 1 1 calc R U . . .
H21A H 0.771091 0.139504 0.644916 0.081 Uiso 1 1 calc R U . . .
C22A C 0.5437(9) 0.5493(5) 0.5711(3) 0.0540(15) Uani 1 1 d . . . . .
H22C H 0.451852 0.578208 0.601397 0.081 Uiso 1 1 calc R U . . .
H22B H 0.535091 0.598730 0.530645 0.081 Uiso 1 1 calc R U . . .
H22A H 0.648206 0.547013 0.591111 0.081 Uiso 1 1 calc R U . . .
N23A N 0.0375(6) 0.3816(4) 0.0245(2) 0.0431(10) Uani 1 1 d . . . . .
H23A H 0.093224 0.386461 0.058692 0.052 Uiso 1 1 calc R U . . .
C24A C 0.0195(9) 0.2807(5) 0.0116(3) 0.0509(14) Uani 1 1 d . . . . .
H24A H 0.067669 0.216154 0.038957 0.061 Uiso 1 1 calc R U . . .
C25A C -0.0677(9) 0.2692(5) -0.0405(3) 0.0540(15) Uani 1 1 d . . . . .
C26A C -0.1398(7) 0.3673(5) -0.0780(3) 0.0456(13) Uani 1 1 d . . . . .
H26A H -0.205250 0.362324 -0.113363 0.055 Uiso 1 1 calc R U . . .
C27A C -0.1178(7) 0.4718(5) -0.0649(3) 0.0477(13) Uani 1 1 d . . . . .
C28A C -0.0252(7) 0.4750(5) -0.0121(3) 0.0489(14) Uani 1 1 d . . . . .
H28A H -0.006152 0.544728 -0.001783 0.059 Uiso 1 1 calc R U . . .
C29A C -0.0906(13) 0.1578(7) -0.0554(4) 0.082(3) Uani 1 1 d . . . . .
H29C H -0.179182 0.137466 -0.026911 0.122 Uiso 1 1 calc R U . . .
H29A H 0.012022 0.101047 -0.048135 0.122 Uiso 1 1 calc R U . . .
H29B H -0.119617 0.161227 -0.101116 0.122 Uiso 1 1 calc R U . . .
C30A C -0.1920(11) 0.5762(6) -0.1059(4) 0.077(3) Uani 1 1 d . . . . .
H30C H -0.105195 0.601852 -0.132994 0.116 Uiso 1 1 calc R U . . .
H30A H -0.246316 0.634932 -0.077540 0.116 Uiso 1 1 calc R U . . .
H30B H -0.273223 0.560403 -0.133974 0.116 Uiso 1 1 calc R U . . .
C1B C 0.3287(16) 0.4596(6) 0.7782(3) 0.111(5) Uani 1 1 d . . . . .
H1B H 0.306268 0.541294 0.785436 0.134 Uiso 1 1 calc R U . . .
C2B C 0.5439(7) 0.3965(8) 0.7760(4) 0.081(3) Uani 1 1 d . . . . .
C3B C 0.6246(9) 0.2865(7) 0.7836(3) 0.066(2) Uani 1 1 d . . . . .
H3B H 0.565831 0.231455 0.800169 0.079 Uiso 1 1 calc R U . . .
C4B C 0.7900(8) 0.2539(6) 0.7676(3) 0.0559(16) Uani 1 1 d . . . . .
H4B H 0.846411 0.177269 0.773702 0.067 Uiso 1 1 calc R U . . .
C5B C 0.8731(7) 0.3354(7) 0.7424(3) 0.0594(18) Uani 1 1 d . . . . .
H5B H 0.986500 0.314706 0.729566 0.071 Uiso 1 1 calc R U . . .
C6B C 0.7930(8) 0.4420(6) 0.7365(3) 0.0573(16) Uani 1 1 d . . . . .
H6B H 0.851578 0.497523 0.720634 0.069 Uiso 1 1 calc R U . . .
C7B C 0.6298(8) 0.4746(7) 0.7522(4) 0.069(2) Uani 1 1 d . . . . .
H7B H 0.575310 0.551714 0.746691 0.082 Uiso 1 1 calc R U . . .
C8B C 0.3101(18) 0.3984(6) 0.8316(4) 0.123(5) Uani 1 1 d . . . . .
H8D H 0.369673 0.320609 0.824122 0.148 Uiso 1 1 calc R U . . .
H8C H 0.191540 0.397702 0.836257 0.148 Uiso 1 1 calc R U . . .
C9B C 0.3594(7) 0.4218(4) 0.8972(2) 0.0381(11) Uani 1 1 d . . . . .
O10B O 0.3876(6) 0.5133(3) 0.90513(17) 0.0469(9) Uani 1 1 d . . . . .
O11B O 0.3689(5) 0.3428(3) 0.94213(16) 0.0395(8) Uani 1 1 d . . . . .
C12B C 0.2570(6) 0.4395(4) 0.7151(2) 0.0328(10) Uani 1 1 d . . . . .
O13B O 0.1952(5) 0.5260(3) 0.67851(17) 0.0401(8) Uani 1 1 d . . . . .
O14B O 0.2709(4) 0.3426(3) 0.70099(17) 0.0337(7) Uani 1 1 d . . . . .
N15B N 0.0788(5) 0.4823(3) 0.5703(2) 0.0331(9) Uani 1 1 d . . . . .
H15B H 0.141534 0.505126 0.610538 0.06(2) Uiso 1 1 d R . . . .
C16B C 0.0162(6) 0.5699(4) 0.5291(3) 0.0360(11) Uani 1 1 d . . . . .
H16B H 0.028191 0.642679 0.536763 0.043 Uiso 1 1 calc R U . . .
C17B C -0.0663(7) 0.5559(4) 0.4750(2) 0.0388(11) Uani 1 1 d . . . . .
C18B C -0.0731(6) 0.4468(4) 0.4651(2) 0.0368(11) Uani 1 1 d . . . . .
H18B H -0.128404 0.434443 0.428402 0.044 Uiso 1 1 calc R U . . .
C19B C -0.0034(6) 0.3562(4) 0.5062(2) 0.0320(10) Uani 1 1 d . . . . .
C20B C 0.0712(6) 0.3774(4) 0.5605(2) 0.0329(10) Uani 1 1 d . . . . .
H20B H 0.117206 0.317061 0.591078 0.039 Uiso 1 1 calc R U . . .
C21B C -0.1456(11) 0.6555(5) 0.4304(3) 0.065(2) Uani 1 1 d . . . . .
H21E H -0.260876 0.653833 0.425006 0.098 Uiso 1 1 calc R U . . .
H21F H -0.086652 0.652542 0.387788 0.098 Uiso 1 1 calc R U . . .
H21D H -0.141051 0.725034 0.449391 0.098 Uiso 1 1 calc R U . . .
C22B C -0.0063(8) 0.2378(5) 0.4940(3) 0.0449(13) Uani 1 1 d . . . . .
H22F H 0.072546 0.212941 0.458185 0.067 Uiso 1 1 calc R U . . .
H22D H -0.117296 0.235152 0.482168 0.067 Uiso 1 1 calc R U . . .
H22E H 0.023828 0.188217 0.533559 0.067 Uiso 1 1 calc R U . . .
N23B N 0.5210(5) 0.3804(4) 1.0452(2) 0.0397(10) Uani 1 1 d . . . . .
H23B H 0.474400 0.376209 1.015594 0.040(16) Uiso 1 1 d R . . . .
C24B C 0.5496(7) 0.4815(5) 1.0522(3) 0.0423(12) Uani 1 1 d . . . . .
H24B H 0.504038 0.543955 1.022907 0.051 Uiso 1 1 calc R U . . .
C25B C 0.6451(7) 0.4951(5) 1.1019(3) 0.0407(11) Uani 1 1 d . . . . .
C26B C 0.7091(7) 0.4023(5) 1.1424(3) 0.0458(13) Uani 1 1 d . . . . .
H26B H 0.778356 0.409363 1.175987 0.055 Uiso 1 1 calc R U . . .
C27B C 0.6758(7) 0.2983(4) 1.1359(3) 0.0408(12) Uani 1 1 d . . . . .
C28B C 0.5807(7) 0.2901(5) 1.0849(3) 0.0437(12) Uani 1 1 d . . . . .
H28B H 0.557674 0.219781 1.078064 0.052 Uiso 1 1 calc R U . . .
C29B C 0.6794(10) 0.6078(6) 1.1089(3) 0.0611(17) Uani 1 1 d . . . . .
H29E H 0.647534 0.657321 1.069432 0.092 Uiso 1 1 calc R U . . .
H29F H 0.797234 0.599213 1.115185 0.092 Uiso 1 1 calc R U . . .
H29D H 0.615818 0.640545 1.146737 0.092 Uiso 1 1 calc R U . . .
C30B C 0.7459(11) 0.1968(6) 1.1812(4) 0.073(2) Uani 1 1 d . . . . .
H30D H 0.702818 0.209831 1.225786 0.109 Uiso 1 1 calc R U . . .
H30E H 0.866371 0.183953 1.179839 0.109 Uiso 1 1 calc R U . . .
H30F H 0.714140 0.130739 1.167330 0.109 Uiso 1 1 calc R U . . .
C1W C 0.4991(8) 0.9451(5) 0.9527(3) 0.0505(14) Uani 1 1 d . . . . .
H1W H 0.511318 0.903600 0.996892 0.061 Uiso 1 1 calc R U . . .
C2W C 0.6638(9) 0.9135(5) 0.9171(3) 0.0516(15) Uani 1 1 d . . . . .
C3W C 0.6814(10) 0.9514(6) 0.8502(3) 0.0635(18) Uani 1 1 d . . . . .
H3W H 0.588754 0.994741 0.827683 0.076 Uiso 1 1 calc R U . . .
C4W C 0.8324(11) 0.9251(7) 0.8186(3) 0.071(2) Uani 1 1 d . . . . .
H4W H 0.845350 0.951659 0.774210 0.085 Uiso 1 1 calc R U . . .
C5W C 0.9664(12) 0.8599(8) 0.8511(4) 0.078(2) Uani 1 1 d . . . . .
H5W H 1.070794 0.841113 0.828798 0.093 Uiso 1 1 calc R U . . .
C6W C 0.9491(10) 0.8217(6) 0.9165(4) 0.0631(18) Uani 1 1 d . . . . .
H6W H 1.040977 0.777177 0.938983 0.076 Uiso 1 1 calc R U . . .
C7W C 0.7965(10) 0.8495(5) 0.9480(3) 0.0577(16) Uani 1 1 d . . . . .
H7W H 0.784116 0.823136 0.992424 0.069 Uiso 1 1 calc R U . . .
C8W C 0.3661(8) 0.9062(4) 0.9204(3) 0.0475(13) Uani 1 1 d . . . . .
H8W1 H 0.256941 0.940930 0.939757 0.057 Uiso 1 1 calc R U . . .
H8W2 H 0.367217 0.930984 0.873237 0.057 Uiso 1 1 calc R U . . .
C9W C 0.3928(7) 0.7795(4) 0.9291(3) 0.0379(11) Uani 1 1 d . . . . .
O10W O 0.4385(7) 0.7274(3) 0.9783(2) 0.0601(12) Uani 1 1 d . . . . .
O11W O 0.3615(6) 0.7323(3) 0.87726(19) 0.0489(10) Uani 1 1 d . . . . .
H11W H 0.366729 0.663647 0.887124 0.059 Uiso 1 1 calc R U . . .
C12W C 0.4644(9) 1.0695(5) 0.9632(3) 0.0537(15) Uani 1 1 d . . . . .
O13W O 0.5284(8) 1.1031(4) 1.0056(3) 0.0823(18) Uani 1 1 d . . . . .
O14W O 0.3689(6) 1.1325(4) 0.9212(2) 0.0550(11) Uani 1 1 d . . . . .
H14W H 0.369028 1.200182 0.924725 0.066 Uiso 1 1 calc R U . . .
C1X C 0.0807(9) -0.1331(5) 0.1060(3) 0.0526(14) Uani 1 1 d . . . . .
H1X H 0.063818 -0.142740 0.059364 0.063 Uiso 1 1 calc R U . . .
C2X C -0.0859(8) -0.1300(5) 0.1439(3) 0.0531(15) Uani 1 1 d . . . . .
C3X C -0.1033(10) -0.1766(6) 0.2070(4) 0.0646(18) Uani 1 1 d . . . . .
H3X H -0.008149 -0.216147 0.229335 0.078 Uiso 1 1 calc R U . . .
C4X C -0.2568(11) -0.1668(7) 0.2380(4) 0.072(2) Uani 1 1 d . . . . .
H4X H -0.267614 -0.198234 0.281470 0.086 Uiso 1 1 calc R U . . .
C5X C -0.3940(10) -0.1104(7) 0.2045(4) 0.070(2) Uani 1 1 d . . . . .
H5X H -0.500528 -0.103628 0.224932 0.083 Uiso 1 1 calc R U . . .
C6X C -0.3777(10) -0.0652(6) 0.1436(4) 0.0653(18) Uani 1 1 d . . . . .
H6X H -0.473199 -0.026288 0.121170 0.078 Uiso 1 1 calc R U . . .
C7X C -0.2266(9) -0.0739(6) 0.1131(3) 0.0592(16) Uani 1 1 d . . . . .
H7X H -0.218153 -0.040722 0.069881 0.071 Uiso 1 1 calc R U . . .
C8X C 0.2125(9) -0.2301(5) 0.1298(4) 0.0579(16) Uani 1 1 d . . . . .
H8X2 H 0.224500 -0.227178 0.177119 0.070 Uiso 1 1 calc R U . . .
H8X1 H 0.318650 -0.224572 0.107117 0.070 Uiso 1 1 calc R U . . .
C9X C 0.1738(8) -0.3412(5) 0.1181(3) 0.0493(14) Uani 1 1 d . . . . .
O10X O 0.0915(6) -0.3527(4) 0.0744(2) 0.0594(12) Uani 1 1 d . . . . .
O11X O 0.2461(6) -0.4206(3) 0.1590(2) 0.0562(11) Uani 1 1 d . . . . .
H11X H 0.217952 -0.480369 0.153327 0.067 Uiso 1 1 calc R U . . .
C12X C 0.1444(9) -0.0257(5) 0.1070(3) 0.0522(14) Uani 1 1 d . . . . .
O13X O 0.1842(8) 0.0244(4) 0.0589(3) 0.0778(16) Uani 1 1 d . . . . .
O14X O 0.1500(7) 0.0052(3) 0.1655(2) 0.0598(12) Uani 1 1 d . . . . .
H14X H 0.168284 0.070090 0.162602 0.072 Uiso 1 1 d R U . . .
C1Y C 0.2817(9) 0.8344(5) 0.4174(3) 0.0555(15) Uani 1 1 d . . . . .
H1Y H 0.286100 0.830572 0.458236 0.067 Uiso 1 1 calc R U . . .
C2Y C 0.1117(6) 0.9075(5) 0.3996(3) 0.0426(12) Uani 1 1 d . . . . .
C3Y C 0.0035(14) 0.9287(6) 0.4527(4) 0.087(3) Uani 1 1 d . . . . .
H3Y H 0.031266 0.907717 0.491167 0.104 Uiso 1 1 calc R U . . .
C4Y C -0.1707(10) 0.9934(6) 0.4361(6) 0.080(3) Uani 1 1 d . . . . .
H4Y H -0.246884 1.009122 0.464529 0.096 Uiso 1 1 calc R U . . .
C5Y C -0.1919(10) 1.0232(7) 0.3718(6) 0.086(3) Uani 1 1 d . . . . .
H5Y H -0.286739 1.057885 0.360913 0.103 Uiso 1 1 calc R U . . .
C6Y C -0.0803(14) 1.0033(7) 0.3255(6) 0.095(3) Uani 1 1 d . . . . .
H6Y H -0.102120 1.029003 0.287006 0.114 Uiso 1 1 calc R U . . .
C7Y C 0.0627(12) 0.9447(7) 0.3384(4) 0.074(2) Uani 1 1 d . . . . .
H7Y H 0.130677 0.928172 0.307159 0.089 Uiso 1 1 calc R U . . .
C8Y C 0.4191(8) 0.8868(5) 0.3894(4) 0.0605(17) Uani 1 1 d . . . . .
H8Y1 H 0.429283 0.880561 0.349040 0.073 Uiso 1 1 calc R U . . .
H8Y2 H 0.507772 0.852065 0.406157 0.073 Uiso 1 1 calc R U . . .
C9Y C 0.3886(7) 1.0091(4) 0.4016(3) 0.0451(13) Uani 1 1 d . . . . .
O10Y O 0.3880(6) 1.0372(3) 0.4546(2) 0.0588(12) Uani 1 1 d . . . . .
O11Y O 0.3756(6) 1.0782(4) 0.3486(2) 0.0569(11) Uani 1 1 d . . . . .
H11Y H 0.358609 1.144649 0.358901 0.068 Uiso 1 1 calc R U . . .
C12Y C 0.3197(8) 0.7123(5) 0.3974(5) 0.067(2) Uani 1 1 d . . . . .
O13Y O 0.4419(7) 0.6496(4) 0.4121(4) 0.0893(19) Uani 1 1 d . . . . .
O14Y O 0.2028(9) 0.6817(5) 0.3731(5) 0.117(3) Uani 1 1 d . . . . .
H14Y H 0.221781 0.611192 0.375773 0.141 Uiso 1 1 calc R U . . .
C1Z C 0.2494(6) -0.0476(4) 0.6904(2) 0.0312(9) Uani 1 1 d . . . . .
H1Z H 0.232777 -0.067898 0.729868 0.037 Uiso 1 1 calc R U . . .
C2Z C 0.4231(6) -0.1065(4) 0.6697(3) 0.0354(10) Uani 1 1 d . . . . .
C3Z C 0.4738(10) -0.1047(6) 0.6044(3) 0.0622(19) Uani 1 1 d . . . . .
H3Z H 0.410652 -0.068223 0.575752 0.075 Uiso 1 1 calc R U . . .
C4Z C 0.6331(14) -0.1651(9) 0.5870(5) 0.102(4) Uani 1 1 d . . . . .
H4Z H 0.663144 -0.167613 0.547386 0.122 Uiso 1 1 calc R U . . .
C5Z C 0.7393(11) -0.2196(10) 0.6337(9) 0.126(6) Uani 1 1 d . . . . .
H5Z H 0.836445 -0.251290 0.622969 0.151 Uiso 1 1 calc R U . . .
C6Z C 0.6874(9) -0.2226(7) 0.6977(6) 0.098(4) Uani 1 1 d . . . . .
H6Z H 0.750796 -0.258975 0.726302 0.118 Uiso 1 1 calc R U . . .
C7Z C 0.5316(8) -0.1660(5) 0.7153(4) 0.0589(17) Uani 1 1 d . . . . .
H7Z H 0.501391 -0.167543 0.754906 0.071 Uiso 1 1 calc R U . . .
C8Z C 0.1209(7) -0.0782(4) 0.6509(3) 0.0436(13) Uani 1 1 d . . . . .
H8Z2 H 0.027501 -0.055952 0.668925 0.052 Uiso 1 1 calc R U . . .
H8Z1 H 0.120712 -0.044240 0.613577 0.052 Uiso 1 1 calc R U . . .
C9Z C 0.1495(6) -0.2031(4) 0.6439(3) 0.0368(11) Uani 1 1 d . . . . .
O10Z O 0.1487(5) -0.2413(3) 0.5923(2) 0.0439(9) Uani 1 1 d . . . . .
O11Z O 0.1668(5) -0.2639(3) 0.70013(19) 0.0444(9) Uani 1 1 d . . . . .
H11Z H 0.193420 -0.332380 0.693523 0.053 Uiso 1 1 calc R U . . .
C12Z C 0.2290(6) 0.0806(4) 0.6839(3) 0.0346(10) Uani 1 1 d . . . . .
O13Z O 0.1552(10) 0.1391(4) 0.6419(3) 0.111(3) Uani 1 1 d . . . . .
O14Z O 0.3058(5) 0.1180(3) 0.7270(2) 0.0475(9) Uani 1 1 d . . . . .
H14Z H 0.285468 0.188519 0.722182 0.057 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
C1A C8A 1.514(8) . ?
C1A C2A 1.537(8) . ?
C1A C12A 1.544(7) . ?
C2A C3A 1.366(8) . ?
C2A C7A 1.399(8) . ?
C3A C4A 1.377(8) . ?
C4A C5A 1.385(10) . ?
C5A C6A 1.359(10) . ?
C6A C7A 1.393(8) . ?
C8A C9A 1.512(8) . ?
C9A O10A 1.229(6) . ?
C9A O11A 1.264(6) . ?
C12A O14A 1.234(6) . ?
C12A O13A 1.262(6) . ?
N15A C16A 1.338(7) . ?
N15A C20A 1.340(7) . ?
C16A C17A 1.378(7) . ?
C17A C18A 1.391(7) . ?
C17A C21A 1.501(8) . ?
C18A C19A 1.389(7) . ?
C19A C20A 1.374(7) . ?
C19A C22A 1.508(8) . ?
N23A C28A 1.329(8) . ?
N23A C24A 1.332(7) . ?
C24A C25A 1.369(9) . ?
C25A C26A 1.398(9) . ?
C25A C29A 1.485(9) . ?
C26A C27A 1.389(8) . ?
C27A C28A 1.381(8) . ?
C27A C30A 1.494(9) . ?
C1B C8B 1.295(9) . ?
C1B C12B 1.526(8) . ?
C1B C2B 1.784(14) . ?
C2B C3B 1.361(12) . ?
C2B C7B 1.364(13) . ?
C3B C4B 1.374(10) . ?
C4B C5B 1.389(11) . ?
C5B C6B 1.322(10) . ?
C6B C7B 1.357(10) . ?
C8B C9B 1.506(8) . ?
C9B O10B 1.227(6) . ?
C9B O11B 1.268(6) . ?
C12B O14B 1.228(6) . ?
C12B O13B 1.266(6) . ?
N15B C16B 1.330(7) . ?
N15B C20B 1.337(6) . ?
C16B C17B 1.387(7) . ?
C17B C18B 1.387(7) . ?
C17B C21B 1.505(7) . ?
C18B C19B 1.369(7) . ?
C19B C20B 1.386(7) . ?
C19B C22B 1.502(7) . ?
N23B C28B 1.329(7) . ?
N23B C24B 1.338(7) . ?
C24B C25B 1.378(8) . ?
C25B C26B 1.369(8) . ?
C25B C29B 1.496(9) . ?
C26B C27B 1.387(8) . ?
C27B C28B 1.378(7) . ?
C27B C30B 1.508(9) . ?
C1W C2W 1.505(9) . ?
C1W C8W 1.514(9) . ?
C1W C12W 1.521(8) . ?
C2W C7W 1.355(10) . ?
C2W C3W 1.422(9) . ?
C3W C4W 1.368(11) . ?
C4W C5W 1.384(13) . ?
C5W C6W 1.394(11) . ?
C6W C7W 1.378(10) . ?
C8W C9W 1.513(7) . ?
C9W O10W 1.181(7) . ?
C9W O11W 1.326(6) . ?
C12W O13W 1.200(8) . ?
C12W O14W 1.286(8) . ?
C1X C8X 1.490(9) . ?
C1X C12X 1.533(8) . ?
C1X C2X 1.548(9) . ?
C2X C7X 1.374(10) . ?
C2X C3X 1.382(10) . ?
C3X C4X 1.381(11) . ?
C4X C5X 1.380(12) . ?
C5X C6X 1.336(11) . ?
C6X C7X 1.361(11) . ?
C8X C9X 1.514(8) . ?
C9X O10X 1.202(8) . ?
C9X O11X 1.289(8) . ?
C12X O13X 1.188(8) . ?
C12X O14X 1.303(7) . ?
C1Y C8Y 1.501(10) . ?
C1Y C2Y 1.539(8) . ?
C1Y C12Y 1.547(8) . ?
C2Y C7Y 1.352(9) . ?
C2Y C3Y 1.380(10) . ?
C3Y C4Y 1.528(14) . ?
C4Y C5Y 1.350(15) . ?
C5Y C6Y 1.292(15) . ?
C6Y C7Y 1.272(13) . ?
C8Y C9Y 1.505(8) . ?
C9Y O10Y 1.175(8) . ?
C9Y O11Y 1.312(8) . ?
C12Y O13Y 1.164(8) . ?
C12Y O14Y 1.267(9) . ?
C1Z C8Z 1.517(7) . ?
C1Z C2Z 1.518(7) . ?
C1Z C12Z 1.536(6) . ?
C2Z C7Z 1.379(8) . ?
C2Z C3Z 1.385(8) . ?
C3Z C4Z 1.408(13) . ?
C4Z C5Z 1.367(19) . ?
C5Z C6Z 1.362(19) . ?
C6Z C7Z 1.370(10) . ?
C8Z C9Z 1.514(7) . ?
C9Z O10Z 1.202(7) . ?
C9Z O11Z 1.314(6) . ?
C12Z O13Z 1.177(7) . ?
C12Z O14Z 1.299(6) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8A C1A C2A 110.9(5) . . ?
C8A C1A C12A 114.3(5) . . ?
C2A C1A C12A 108.9(4) . . ?
C3A C2A C7A 118.8(5) . . ?
C3A C2A C1A 118.1(5) . . ?
C7A C2A C1A 123.0(5) . . ?
C2A C3A C4A 120.9(6) . . ?
C3A C4A C5A 120.2(6) . . ?
C6A C5A C4A 119.9(5) . . ?
C5A C6A C7A 120.1(6) . . ?
C6A C7A C2A 120.1(6) . . ?
C9A C8A C1A 114.3(5) . . ?
O10A C9A O11A 122.2(5) . . ?
O10A C9A C8A 117.8(5) . . ?
O11A C9A C8A 119.9(5) . . ?
O14A C12A O13A 122.5(5) . . ?
O14A C12A C1A 117.5(5) . . ?
O13A C12A C1A 119.9(4) . . ?
C16A N15A C20A 122.5(5) . . ?
N15A C16A C17A 120.3(5) . . ?
C16A C17A C18A 117.4(5) . . ?
C16A C17A C21A 121.3(5) . . ?
C18A C17A C21A 121.4(5) . . ?
C19A C18A C17A 121.8(5) . . ?
C20A C19A C18A 117.5(5) . . ?
C20A C19A C22A 120.8(5) . . ?
C18A C19A C22A 121.7(5) . . ?
N15A C20A C19A 120.4(5) . . ?
C28A N23A C24A 122.7(5) . . ?
N23A C24A C25A 120.7(6) . . ?
C24A C25A C26A 117.3(6) . . ?
C24A C25A C29A 121.6(6) . . ?
C26A C25A C29A 121.1(6) . . ?
C27A C26A C25A 121.6(5) . . ?
C28A C27A C26A 117.1(6) . . ?
C28A C27A C30A 121.4(6) . . ?
C26A C27A C30A 121.5(5) . . ?
N23A C28A C27A 120.6(5) . . ?
C8B C1B C12B 120.4(7) . . ?
C8B C1B C2B 89.7(9) . . ?
C12B C1B C2B 108.5(7) . . ?
C3B C2B C7B 119.0(6) . . ?
C3B C2B C1B 130.5(7) . . ?
C7B C2B C1B 109.6(7) . . ?
C2B C3B C4B 120.8(7) . . ?
C3B C4B C5B 118.7(7) . . ?
C6B C5B C4B 119.5(6) . . ?
C5B C6B C7B 122.0(7) . . ?
C6B C7B C2B 120.0(7) . . ?
C1B C8B C9B 123.4(6) . . ?
O10B C9B O11B 123.3(4) . . ?
O10B C9B C8B 120.3(5) . . ?
O11B C9B C8B 116.4(4) . . ?
O14B C12B O13B 124.2(4) . . ?
O14B C12B C1B 119.1(5) . . ?
O13B C12B C1B 116.6(4) . . ?
C16B N15B C20B 122.2(4) . . ?
N15B C16B C17B 120.7(5) . . ?
C16B C17B C18B 116.7(5) . . ?
C16B C17B C21B 120.9(5) . . ?
C18B C17B C21B 122.4(5) . . ?
C19B C18B C17B 122.6(4) . . ?
C18B C19B C20B 117.3(4) . . ?
C18B C19B C22B 122.3(5) . . ?
C20B C19B C22B 120.4(5) . . ?
N15B C20B C19B 120.5(4) . . ?
C28B N23B C24B 122.7(5) . . ?
N23B C24B C25B 120.1(5) . . ?
C26B C25B C24B 117.7(5) . . ?
C26B C25B C29B 122.3(5) . . ?
C24B C25B C29B 120.0(5) . . ?
C25B C26B C27B 122.0(5) . . ?
C28B C27B C26B 117.4(5) . . ?
C28B C27B C30B 121.0(5) . . ?
C26B C27B C30B 121.5(5) . . ?
N23B C28B C27B 120.1(5) . . ?
C2W C1W C8W 112.1(5) . . ?
C2W C1W C12W 108.3(5) . . ?
C8W C1W C12W 116.3(5) . . ?
C7W C2W C3W 119.3(7) . . ?
C7W C2W C1W 120.9(6) . . ?
C3W C2W C1W 119.8(7) . . ?
C4W C3W C2W 119.6(8) . . ?
C3W C4W C5W 120.1(7) . . ?
C4W C5W C6W 120.4(8) . . ?
C7W C6W C5W 119.0(8) . . ?
C2W C7W C6W 121.7(7) . . ?
C9W C8W C1W 110.9(5) . . ?
O10W C9W O11W 123.1(5) . . ?
O10W C9W C8W 122.1(5) . . ?
O11W C9W C8W 114.8(5) . . ?
O13W C12W O14W 124.9(6) . . ?
O13W C12W C1W 121.4(6) . . ?
O14W C12W C1W 113.7(5) . . ?
C8X C1X C12X 108.1(6) . . ?
C8X C1X C2X 112.2(6) . . ?
C12X C1X C2X 114.2(5) . . ?
C7X C2X C3X 117.7(6) . . ?
C7X C2X C1X 117.3(6) . . ?
C3X C2X C1X 125.0(7) . . ?
C4X C3X C2X 121.1(7) . . ?
C5X C4X C3X 118.7(7) . . ?
C6X C5X C4X 120.3(7) . . ?
C5X C6X C7X 121.0(8) . . ?
C6X C7X C2X 121.1(7) . . ?
C1X C8X C9X 111.5(5) . . ?
O10X C9X O11X 125.4(5) . . ?
O10X C9X C8X 123.5(6) . . ?
O11X C9X C8X 111.0(5) . . ?
O13X C12X O14X 123.5(6) . . ?
O13X C12X C1X 123.0(6) . . ?
O14X C12X C1X 113.5(5) . . ?
C8Y C1Y C2Y 111.8(5) . . ?
C8Y C1Y C12Y 107.4(6) . . ?
C2Y C1Y C12Y 115.9(5) . . ?
C7Y C2Y C3Y 120.6(7) . . ?
C7Y C2Y C1Y 125.7(6) . . ?
C3Y C2Y C1Y 113.6(6) . . ?
C2Y C3Y C4Y 114.9(8) . . ?
C5Y C4Y C3Y 114.4(7) . . ?
C6Y C5Y C4Y 126.2(9) . . ?
C7Y C6Y C5Y 119.8(11) . . ?
C6Y C7Y C2Y 123.8(10) . . ?
C1Y C8Y C9Y 112.1(5) . . ?
O10Y C9Y O11Y 124.1(5) . . ?
O10Y C9Y C8Y 121.2(6) . . ?
O11Y C9Y C8Y 114.5(6) . . ?
O13Y C12Y O14Y 122.6(6) . . ?
O13Y C12Y C1Y 120.3(6) . . ?
O14Y C12Y C1Y 116.3(6) . . ?
C8Z C1Z C2Z 111.8(4) . . ?
C8Z C1Z C12Z 109.4(4) . . ?
C2Z C1Z C12Z 110.9(4) . . ?
C7Z C2Z C3Z 118.7(6) . . ?
C7Z C2Z C1Z 120.7(5) . . ?
C3Z C2Z C1Z 120.6(5) . . ?
C2Z C3Z C4Z 118.8(9) . . ?
C5Z C4Z C3Z 120.8(9) . . ?
C6Z C5Z C4Z 119.9(8) . . ?
C5Z C6Z C7Z 119.8(10) . . ?
C6Z C7Z C2Z 121.9(8) . . ?
C9Z C8Z C1Z 113.5(4) . . ?
O10Z C9Z O11Z 124.0(4) . . ?
O10Z C9Z C8Z 122.9(5) . . ?
O11Z C9Z C8Z 113.0(5) . . ?
O13Z C12Z O14Z 123.2(5) . . ?
O13Z C12Z C1Z 122.6(5) . . ?
O14Z C12Z C1Z 114.2(4) . . ?

_refine_diff_density_max         0.725
_refine_diff_density_min         -0.503
_refine_diff_density_rms         0.061

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: 3,5-lutidine'
####################################################################### 
# 
# 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_racpsa-24lut
_database_code_depnum_ccdc_archive 'CCDC 1976323'
loop_
_audit_author_name
_audit_author_address
'Nikoletta B. Bathori'
;Cape Peninsula University of Technology
South Africa
;
_audit_update_record             
;
2020-01-09 deposited with the CCDC.	2020-02-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/4
_shelx_SHELXL_version_number     2016/4
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H28 N2 O4'
_chemical_formula_weight         408.48

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                   11.773(2)
_cell_length_b                   8.4930(17)
_cell_length_c                   22.318(5)
_cell_angle_alpha                90
_cell_angle_beta                 96.22(3)
_cell_angle_gamma                90
_cell_volume                     2218.4(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    7402
_cell_measurement_theta_min      2.56
_cell_measurement_theta_max      27.78

_exptl_crystal_description       plates
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.223
_exptl_crystal_F_000             872
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.570
_exptl_crystal_size_mid          0.380
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.083
_shelx_estimated_absorpt_T_min   0.954
_shelx_estimated_absorpt_T_max   0.985
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.879
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  Bruker
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            25976
_diffrn_reflns_av_unetI/netI     0.0219
_diffrn_reflns_av_R_equivalents  0.0242
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         1.740
_diffrn_reflns_theta_max         28.452
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             5492
_reflns_number_gt                3832
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0527P)²+1.0017P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    noref
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5492
_refine_ls_number_parameters     353
_refine_ls_number_restraints     8
_refine_ls_R_factor_all          0.0822
_refine_ls_R_factor_gt           0.0545
_refine_ls_wR_factor_ref         0.1464
_refine_ls_wR_factor_gt          0.1303
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_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
C9 C 1.13824(15) 0.4464(2) 0.61402(9) 0.0483(4) Uani 1 1 d . . . . .
O10 O 1.20224(12) 0.3868(2) 0.58289(8) 0.0805(5) Uani 1 1 d . . . . .
O11 O 1.17022(11) 0.5301(2) 0.66112(6) 0.0636(4) Uani 1 1 d D . . . .
H11 H 1.2578(15) 0.541(3) 0.6652(12) 0.096(8) Uiso 1 1 d D . . . .
C12 C 0.83826(15) 0.3163(2) 0.54517(9) 0.0507(5) Uani 1 1 d . . . . .
O13 O 0.77327(11) 0.38427(19) 0.57448(6) 0.0640(4) Uani 1 1 d . . . . .
O14 O 0.80905(11) 0.2344(2) 0.49745(7) 0.0668(4) Uani 1 1 d D . . . .
H14 H 0.7220(15) 0.231(3) 0.4860(12) 0.107(9) Uiso 1 1 d D . . . .
N15 N 0.59041(12) 0.20823(17) 0.47100(6) 0.0423(3) Uani 1 1 d . . . . .
C16 C 0.54384(16) 0.1074(2) 0.42921(8) 0.0456(4) Uani 1 1 d . . . . .
C17 C 0.42631(16) 0.0888(2) 0.42004(8) 0.0494(4) Uani 1 1 d . . . . .
H17 H 0.394560 0.014951 0.390946 0.059 Uiso 1 1 calc R U . . .
C18 C 0.35481(15) 0.1747(2) 0.45202(8) 0.0464(4) Uani 1 1 d . . . . .
C19 C 0.40471(15) 0.2793(2) 0.49455(8) 0.0469(4) Uani 1 1 d . . . . .
H19 H 0.358804 0.341912 0.517704 0.056 Uiso 1 1 calc R U . . .
C20 C 0.52186(14) 0.2910(2) 0.50276(8) 0.0444(4) Uani 1 1 d . . . . .
H20 H 0.555523 0.361733 0.532548 0.053 Uiso 1 1 calc R U . . .
C21 C 0.6236(2) 0.0211(3) 0.39326(10) 0.0663(6) Uani 1 1 d . . . . .
H21A H 0.579783 -0.048641 0.364384 0.099 Uiso 0.5 1 calc R U P . .
H21C H 0.666542 0.096897 0.371435 0.099 Uiso 0.5 1 calc R U P . .
H21E H 0.676892 -0.041602 0.420342 0.099 Uiso 0.5 1 calc R U P . .
H21D H 0.702362 0.053077 0.406390 0.099 Uiso 0.5 1 calc R U P . .
H21F H 0.615602 -0.092461 0.399339 0.099 Uiso 0.5 1 calc R U P . .
H21B H 0.605253 0.046038 0.350432 0.099 Uiso 0.5 1 calc R U P . .
C22 C 0.22721(17) 0.1593(3) 0.44182(11) 0.0708(6) Uani 1 1 d . . . A 4
H22D H 0.192233 0.230524 0.469111 0.106 Uiso 0.5 1 calc R U P A 4
H22B H 0.200764 0.186865 0.399987 0.106 Uiso 0.5 1 calc R U P A 4
H22F H 0.205299 0.050585 0.449709 0.106 Uiso 0.5 1 calc R U P A 4
H22A H 0.206632 0.081459 0.410094 0.106 Uiso 0.5 1 calc R U P A 4
H22E H 0.198100 0.125118 0.479217 0.106 Uiso 0.5 1 calc R U P A 4
H22C H 0.193565 0.261398 0.429496 0.106 Uiso 0.5 1 calc R U P A 4
N23 N 1.38958(12) 0.57954(17) 0.68321(7) 0.0431(3) Uani 1 1 d . . . . .
C24 C 1.42497(15) 0.6558(2) 0.73446(8) 0.0453(4) Uani 1 1 d . . . B 4
C25 C 1.53944(16) 0.6897(2) 0.74923(9) 0.0513(5) Uani 1 1 d . . . B 4
H25 H 1.562799 0.745860 0.785285 0.062 Uiso 1 1 calc R U . B 4
C26 C 1.62014(16) 0.6435(2) 0.71255(9) 0.0520(5) Uani 1 1 d . . . B 4
C27 C 1.58195(17) 0.5647(2) 0.65996(9) 0.0528(5) Uani 1 1 d . . . B 4
H27 H 1.634363 0.530883 0.633113 0.063 Uiso 1 1 calc R U . B 4
C28 C 1.46697(16) 0.5361(2) 0.64716(8) 0.0488(4) Uani 1 1 d . . . B 4
H28 H 1.441453 0.482740 0.610775 0.059 Uiso 1 1 calc R U . B 4
C29 C 1.33445(19) 0.6995(3) 0.77367(11) 0.0659(6) Uani 1 1 d . . . B 4
H29A H 1.282561 0.776734 0.752711 0.099 Uiso 1 1 calc R U . B 4
H29B H 1.370248 0.745126 0.811410 0.099 Uiso 1 1 calc R U . B 4
H29C H 1.291290 0.605223 0.782550 0.099 Uiso 1 1 calc R U . B 4
C30 C 1.74527(19) 0.6768(3) 0.72927(14) 0.0833(8) Uani 1 1 d . . . B 4
H30A H 1.789211 0.635321 0.697890 0.125 Uiso 0.5 1 calc R U P B 4
H30C H 1.757194 0.790694 0.732992 0.125 Uiso 0.5 1 calc R U P B 4
H30E H 1.770796 0.625900 0.767800 0.125 Uiso 0.5 1 calc R U P B 4
H30D H 1.755590 0.732622 0.767898 0.125 Uiso 0.5 1 calc R U P B 4
H30F H 1.787607 0.577249 0.732796 0.125 Uiso 0.5 1 calc R U P B 4
H30B H 1.774005 0.742044 0.697988 0.125 Uiso 0.5 1 calc R U P B 4
C1A C 0.96722(18) 0.3003(3) 0.56831(13) 0.0369(8) Uani 0.754(8) 1 d . . P C 1
H1A H 1.010196 0.286224 0.532412 0.044 Uiso 0.754(8) 1 calc R U P C 1
C2A C 0.9879(3) 0.1547(4) 0.60792(16) 0.0342(6) Uani 0.754(8) 1 d . . P C 1
C3A C 0.9478(6) 0.1462(7) 0.6637(2) 0.0432(11) Uani 0.754(8) 1 d . . P C 1
H3A H 0.907316 0.232341 0.678228 0.052 Uiso 0.754(8) 1 calc R U P C 1
C4A C 0.9666(7) 0.0130(9) 0.6980(4) 0.059(2) Uani 0.754(8) 1 d . . P C 1
H4A H 0.940154 0.011434 0.736731 0.071 Uiso 0.754(8) 1 calc R U P C 1
C5A C 1.0212(7) -0.1177(12) 0.6798(4) 0.0450(15) Uani 0.754(8) 1 d . . P C 1
H5A H 1.029227 -0.211701 0.702962 0.054 Uiso 0.754(8) 1 calc R U P C 1
C6A C 1.0629(8) -0.1019(7) 0.6259(4) 0.0480(19) Uani 0.754(8) 1 d . . P C 1
H6A H 1.107256 -0.186048 0.612804 0.058 Uiso 0.754(8) 1 calc R U P C 1
C7A C 1.0457(4) 0.0282(6) 0.5885(2) 0.0400(9) Uani 0.754(8) 1 d . . P C 1
H7A H 1.073528 0.029386 0.550080 0.048 Uiso 0.754(8) 1 calc R U P C 1
C8A C 1.0096(2) 0.4506(5) 0.59996(14) 0.0453(8) Uani 0.754(8) 1 d . . P C 1
H8B H 0.987318 0.542203 0.573885 0.054 Uiso 0.754(8) 1 calc R U P C 1
H8A H 0.973699 0.462525 0.637828 0.054 Uiso 0.754(8) 1 calc R U P C 1
C1B C 1.0105(7) 0.3632(15) 0.6060(4) 0.045(2) Uani 0.246(8) 1 d . . P C 2
H1B H 0.960723 0.426058 0.630584 0.054 Uiso 0.246(8) 1 calc R U P C 2
C2B C 1.0124(7) 0.1937(11) 0.6304(5) 0.033(2) Uani 0.246(8) 1 d D . P C 2
C3B C 0.9610(17) 0.1661(19) 0.6812(6) 0.039(3) Uani 0.246(8) 1 d D . P C 2
H3B H 0.926002 0.250856 0.700018 0.046 Uiso 0.246(8) 1 calc R U P C 2
C4B C 0.9588(17) 0.0154(15) 0.7061(10) 0.025(3) Uani 0.246(8) 1 d D . P C 2
H4B H 0.920783 -0.010819 0.740182 0.030 Uiso 0.246(8) 1 calc R U P C 2
C5B C 1.020(3) -0.093(4) 0.6741(15) 0.060(8) Uani 0.246(8) 1 d D . P C 2
H5B H 1.033867 -0.190245 0.694651 0.073 Uiso 0.246(8) 1 calc R U P C 2
C6B C 1.067(3) -0.089(3) 0.6181(14) 0.067(8) Uani 0.246(8) 1 d D . P C 2
H6B H 1.092347 -0.175073 0.596114 0.081 Uiso 0.246(8) 1 calc R U P C 2
C7B C 1.0664(12) 0.0711(19) 0.6023(7) 0.050(4) Uani 0.246(8) 1 d D . P C 2
H7B H 1.106799 0.099146 0.569230 0.060 Uiso 0.246(8) 1 calc R U P C 2
C8B C 0.9606(7) 0.3762(15) 0.5422(5) 0.058(3) Uani 0.246(8) 1 d . . P C 2
H8C H 1.002240 0.309498 0.515535 0.070 Uiso 0.246(8) 1 calc R U P C 2
H8D H 0.960937 0.486603 0.527992 0.070 Uiso 0.246(8) 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
C9 O10 1.192(2) . ?
C9 O11 1.291(2) . ?
C9 C8A 1.514(3) . ?
C9 C1B 1.654(8) . ?
C12 O13 1.206(2) . ?
C12 O14 1.287(2) . ?
C12 C8B 1.536(10) . ?
C12 C1A 1.556(3) . ?
N15 C20 1.331(2) . ?
N15 C16 1.339(2) . ?
C16 C17 1.386(3) . ?
C16 C21 1.492(3) . ?
C17 C18 1.371(3) . ?
C18 C19 1.384(2) . ?
C18 C22 1.500(3) . ?
C19 C20 1.375(2) . ?
N23 C28 1.331(2) . ?
N23 C24 1.341(2) . ?
C24d C25 1.383(3) . ?
C24d C29 1.497(3) . ?
C25d C26 1.377(3) . ?
C26d C27 1.383(3) . ?
C26d C30 1.507(3) . ?
C27d C28 1.374(3) . ?
C1Aa C8A 1.516(4) . ?
C1Aa C2A 1.524(5) . ?
C2Aa C7A 1.368(6) . ?
C2Aa C3A 1.379(6) . ?
C3Aa C4A 1.371(8) . ?
C4Aa C5A 1.366(9) . ?
C5Aa C6A 1.354(8) . ?
C6Aa C7A 1.387(8) . ?
C1Bb C8B 1.483(14) . ?
C1Bb C2B 1.538(16) . ?
C2Bb C3B 1.361(15) . ?
C2Bb C7B 1.404(15) . ?
C3Bb C4B 1.396(16) . ?
C4Bb C5B 1.413(19) . ?
C5Bb C6B 1.416(19) . ?
C6Bb C7B 1.402(18) . ?

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
O10 C9 O11 124.17(17) . . ?
O10 C9 C8A 124.8(2) . . ?
O11 C9 C8A 110.68(18) . . ?
O10 C9 C1B 112.3(4) . . ?
O11 C9 C1B 120.3(4) . . ?
O13 C12 O14 125.38(17) . . ?
O13 C12 C8B 121.2(4) . . ?
O14 C12 C8B 108.2(4) . . ?
O13 C12 C1A 121.02(18) . . ?
O14 C12 C1A 113.02(16) . . ?
C20 N15 C16 118.85(15) . . ?
N15 C16 C17 120.17(17) . . ?
N15 C16 C21 117.04(17) . . ?
C17 C16 C21 122.78(17) . . ?
C18 C17 C16 121.48(17) . . ?
C17 C18 C19 117.36(16) . . ?
C17 C18 C22 122.41(18) . . ?
C19 C18 C22 120.23(18) . . ?
C20 C19 C18 118.89(17) . . ?
N15 C20 C19 123.22(16) . . ?
C28d N23 C24 118.66(16) . . ?
N23 C24d C25 120.58(17) . . ?
N23 C24d C29 116.31(17) . . ?
C25d C24d C29 123.11(18) . . ?
C26d C25d C24 121.10(18) . . ?
C25d C26d C27 117.43(18) . . ?
C25d C26d C30 121.2(2) . . ?
C27d C26d C30 121.3(2) . . ?
C28d C27d C26 118.96(19) . . ?
N23 C28d C27 123.27(18) . . ?
C8Aa C1Aa C2A 112.9(4) . . ?
C8Aa C1Aa C12 109.9(2) . . ?
C2Aa C1Aa C12 110.61(19) . . ?
C7Aa C2Aa C3A 118.4(4) . . ?
C7Aa C2Aa C1A 120.5(3) . . ?
C3Aa C2Aa C1A 121.2(4) . . ?
C4Aa C3Aa C2A 119.8(6) . . ?
C5Aa C4Aa C3A 123.8(8) . . ?
C6Aa C5Aa C4A 114.3(9) . . ?
C5Aa C6Aa C7A 124.8(7) . . ?
C2Aa C7Aa C6A 118.7(5) . . ?
C9 C8Aa C1A 110.4(2) . . ?
C8Bb C1Bb C2B 113.6(13) . . ?
C8Bb C1Bb C9 109.5(7) . . ?
C2Bb C1Bb C9 112.5(6) . . ?
C3Bb C2Bb C7B 120.5(11) . . ?
C3Bb C2Bb C1B 117.8(11) . . ?
C7Bb C2Bb C1B 121.7(10) . . ?
C2Bb C3Bb C4B 121.2(16) . . ?
C3Bb C4Bb C5B 111(2) . . ?
C4Bb C5Bb C6B 134(3) . . ?
C7Bb C6Bb C5B 105(2) . . ?
C6Bb C7Bb C2B 126.5(16) . . ?
C1Bb C8Bb C12 102.1(8) . . ?

_refine_diff_density_max         0.256
_refine_diff_density_min         -0.270
_refine_diff_density_rms         0.035

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: 2,4-lutidine'
####################################################################### 
# 
# 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_racpsa-4pic
_database_code_depnum_ccdc_archive 'CCDC 1976322'
loop_
_audit_author_name
_audit_author_address
'Nikoletta B. Bathori'
;Cape Peninsula University of Technology
South Africa
;
_audit_update_record             
;
2020-01-09 deposited with the CCDC.	2020-02-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/4
_shelx_SHELXL_version_number     2016/4
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          338.87
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H24 N2 O4'
_chemical_formula_weight         380.43

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                   22.906(5)
_cell_length_b                   5.7441(11)
_cell_length_c                   15.376(3)
_cell_angle_alpha                90
_cell_angle_beta                 100.98(3)
_cell_angle_gamma                90
_cell_volume                     1986.1(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    1785
_cell_measurement_theta_min      2.678
_cell_measurement_theta_max      23.42

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.272
_exptl_crystal_F_000             808
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.088
_shelx_estimated_absorpt_T_min   0.982
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.892
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  Bruker
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11159
_diffrn_reflns_av_unetI/netI     0.0438
_diffrn_reflns_av_R_equivalents  0.0316
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       3
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.811
_diffrn_reflns_theta_max         27.131
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4367
_reflns_number_gt                2529
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0919P)²+1.9566P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_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         4367
_refine_ls_number_parameters     278
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1345
_refine_ls_R_factor_gt           0.0782
_refine_ls_wR_factor_ref         0.2287
_refine_ls_wR_factor_gt          0.1955
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_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
C2 C 0.23821(14) 0.5420(6) 0.2490(2) 0.0436(8) Uani 1 1 d . . . . .
C3 C 0.26177(14) 0.3494(6) 0.2115(2) 0.0475(8) Uani 1 1 d . . . . .
H3 H 0.277042 0.238535 0.243599 0.057 Uiso 1 1 calc R U . . .
C4 C 0.25952(15) 0.3442(7) 0.1210(2) 0.0509(9) Uani 1 1 d . . . . .
H4 H 0.273186 0.229007 0.097809 0.061 Uiso 1 1 calc R U . . .
C5 C 0.23528(15) 0.5250(7) 0.0694(2) 0.0528(9) Uani 1 1 d . . . . .
H5 H 0.233849 0.520337 0.014406 0.063 Uiso 1 1 calc R U . . .
C6 C 0.21330(14) 0.7133(7) 0.1061(2) 0.0516(9) Uani 1 1 d . . . . .
H6 H 0.198278 0.823966 0.073735 0.062 Uiso 1 1 calc R U . . .
C7 C 0.21554(14) 0.7233(6) 0.1952(2) 0.0477(8) Uani 1 1 d . . . . .
H7 H 0.202853 0.842182 0.217440 0.057 Uiso 1 1 calc R U . . .
C9 C 0.34025(14) 0.6707(6) 0.3965(2) 0.0411(7) Uani 1 1 d . . . . .
C12 C 0.18578(13) 0.3874(6) 0.3659(2) 0.0420(7) Uani 1 1 d . . . . .
N15 N 0.05007(14) 0.1552(7) 0.3625(2) 0.0653(9) Uani 1 1 d . . . . .
C16 C -0.00538(16) 0.2096(7) 0.3306(3) 0.0598(10) Uani 1 1 d . . . . .
H16 H -0.012376 0.337658 0.304348 0.072 Uiso 1 1 calc R U . . .
C17 C -0.05220(14) 0.0709(6) 0.3377(2) 0.0485(8) Uani 1 1 d . . . . .
H17 H -0.086929 0.115229 0.316464 0.058 Uiso 1 1 calc R U . . .
C18 C -0.04332(13) -0.1422(6) 0.3795(2) 0.0438(8) Uani 1 1 d . . . . .
C19 C 0.01495(15) -0.2036(7) 0.4129(2) 0.0538(9) Uani 1 1 d . . . . .
H19 H 0.023096 -0.331148 0.439142 0.065 Uiso 1 1 calc R U . . .
C20 C 0.06031(15) -0.0474(8) 0.4020(3) 0.0655(12) Uani 1 1 d . . . . .
H20 H 0.095743 -0.085580 0.421848 0.079 Uiso 1 1 calc R U . . .
C21 C -0.09487(16) -0.2933(7) 0.3880(3) 0.0634(11) Uani 1 1 d . . . . .
H21B H -0.113122 -0.331486 0.337321 0.095 Uiso 1 1 calc R U . . .
H21A H -0.117951 -0.220016 0.414538 0.095 Uiso 1 1 calc R U . . .
H21C H -0.082567 -0.413469 0.416878 0.095 Uiso 1 1 calc R U . . .
N22 N 0.47731(11) 0.8749(5) 0.39980(18) 0.0436(7) Uani 1 1 d . . . . .
C23 C 0.46473(13) 1.0772(6) 0.3604(2) 0.0472(9) Uani 1 1 d . . . . .
H23 H 0.428918 1.117812 0.346852 0.057 Uiso 1 1 calc R U . . .
C24 C 0.50861(14) 1.2287(6) 0.3399(2) 0.0433(8) Uani 1 1 d . . . . .
H24 H 0.499096 1.355613 0.313874 0.052 Uiso 1 1 calc R U . . .
C25 C 0.56765(12) 1.1639(5) 0.3635(2) 0.0369(7) Uani 1 1 d . . . . .
C26 C 0.57895(14) 0.9536(6) 0.4069(2) 0.0430(8) Uani 1 1 d . . . . .
H26 H 0.614281 0.909717 0.423751 0.052 Uiso 1 1 calc R U . . .
C27 C 0.53387(14) 0.8166(6) 0.4228(2) 0.0459(8) Uani 1 1 d . . . . .
H27 H 0.542373 0.688631 0.448592 0.055 Uiso 1 1 calc R U . . .
C28 C 0.61696(14) 1.3139(6) 0.3445(2) 0.0513(9) Uani 1 1 d . . . . .
H28A H 0.604186 1.449473 0.332439 0.077 Uiso 1 1 calc R U . . .
H28C H 0.629873 1.259106 0.301109 0.077 Uiso 1 1 calc R U . . .
H28B H 0.644565 1.317484 0.389079 0.077 Uiso 1 1 calc R U . . .
C1A C 0.23344(17) 0.5596(8) 0.3465(3) 0.0399(9) Uani 0.815(4) 1 d . . P A 1
H1A H 0.223797 0.695907 0.357713 0.048 Uiso 0.815(4) 1 calc R U P A 1
C8A C 0.29246(16) 0.4978(8) 0.4056(3) 0.0457(10) Uani 0.815(4) 1 d . . P A 1
H8B H 0.288131 0.493884 0.458590 0.055 Uiso 0.815(4) 1 calc R U P A 1
H8A H 0.303002 0.364598 0.392086 0.055 Uiso 0.815(4) 1 calc R U P A 1
O10A O 0.32970(13) 0.8666(8) 0.3707(3) 0.0557(10) Uani 0.815(4) 1 d . . P A 1
O11A O 0.39359(14) 0.5889(6) 0.4221(3) 0.0530(10) Uani 0.815(4) 1 d . . P A 1
H11A H 0.418517 0.695284 0.420534 0.064 Uiso 0.815(4) 1 calc R U P A 1
O13A O 0.19159(16) 0.1743(6) 0.3634(3) 0.0679(10) Uani 0.815(4) 1 d . . P A 1
O14A O 0.13583(16) 0.4803(6) 0.3658(4) 0.0887(15) Uani 0.815(4) 1 d . . P A 1
H14A H 0.109887 0.376056 0.363800 0.106 Uiso 0.815(4) 1 calc R U P A 1
C1B C 0.2486(8) 0.451(4) 0.3611(13) 0.0399(9) Uani 0.185(4) 1 d . . P A 2
H1B H 0.271453 0.335285 0.370852 0.048 Uiso 0.185(4) 1 calc R U P A 2
C8B C 0.2732(7) 0.645(4) 0.4064(13) 0.0457(10) Uani 0.185(4) 1 d . . P A 2
H8C H 0.271241 0.632807 0.460210 0.055 Uiso 0.185(4) 1 calc R U P A 2
H8D H 0.254005 0.763998 0.386070 0.055 Uiso 0.185(4) 1 calc R U P A 2
O10B O 0.3783(8) 0.530(3) 0.4152(15) 0.0557(10) Uani 0.185(4) 1 d . . P A 2
O11B O 0.3473(8) 0.888(4) 0.3813(18) 0.0530(10) Uani 0.185(4) 1 d . . P A 2
H11B H 0.374562 0.904262 0.352196 0.064 Uiso 0.185(4) 1 calc R U P A 2
O13B O 0.1601(8) 0.232(3) 0.3297(13) 0.0679(10) Uani 0.185(4) 1 d . . P A 2
O14B O 0.1664(8) 0.496(3) 0.4293(18) 0.0887(15) Uani 0.185(4) 1 d . . P A 2
H14B H 0.157643 0.397962 0.465445 0.106 Uiso 0.185(4) 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
C2 C7 1.369(5) . ?
C2 C3 1.402(5) . ?
C2 C1A 1.527(5) . ?
C2 C1B 1.77(2) . ?
C3 C4 1.383(5) . ?
C4 C5 1.359(5) . ?
C5 C6 1.361(5) . ?
C6 C7 1.362(5) . ?
C9 O10B 1.18(2) . ?
C9 O10A 1.203(5) . ?
C9 O11B 1.29(2) . ?
C9 O11A 1.298(5) . ?
C9 C8A 1.504(5) . ?
C9 C8B 1.579(17) . ?
C12 O13B 1.154(18) . ?
C12 O13A 1.233(5) . ?
C12 O14A 1.262(5) . ?
C12 O14B 1.30(2) . ?
C12 C1B 1.501(19) . ?
C12 C1A 1.544(5) . ?
N15 C16 1.309(5) . ?
N15 C20 1.313(5) . ?
C16 C17 1.357(5) . ?
C17 C18 1.379(5) . ?
C18 C19 1.382(4) . ?
C18 C21 1.491(5) . ?
C19 C20 1.407(5) . ?
N22 C23 1.317(4) . ?
N22 C27 1.320(4) . ?
C23 C24 1.410(5) . ?
C24 C25 1.383(4) . ?
C25 C26 1.380(4) . ?
C25 C28 1.494(4) . ?
C26 C27 1.357(4) . ?
C1Aa C8A 1.520(6) . ?
C1Bb C8B 1.38(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
C7 C2 C3 118.9(3) . . ?
C7 C2 C1A 116.9(3) . . ?
C3 C2 C1A 124.1(3) . . ?
C7 C2 C1B 141.0(7) . . ?
C3 C2 C1B 100.1(7) . . ?
C4 C3 C2 119.1(3) . . ?
C5 C4 C3 120.3(3) . . ?
C4 C5 C6 120.5(3) . . ?
C5 C6 C7 120.3(3) . . ?
C6 C7 C2 120.8(3) . . ?
O10Bb C9 O11B 126.7(12) . . ?
O10Aa C9 O11A 123.9(3) . . ?
O10Aa C9 C8A 123.0(3) . . ?
O11Aa C9 C8A 113.1(3) . . ?
O10Bb C9 C8B 126.6(12) . . ?
O11Bb C9 C8B 105.4(12) . . ?
O13Aa C12 O14A 121.5(3) . . ?
O13Bb C12 O14B 121.0(11) . . ?
O13Bb C12 C1B 124.7(11) . . ?
O14Bb C12 C1B 112.8(11) . . ?
O13Aa C12 C1A 123.1(3) . . ?
O14Aa C12 C1A 113.8(3) . . ?
C16 N15 C20 117.4(3) . . ?
N15 C16 C17 123.7(4) . . ?
C16 C17 C18 120.6(3) . . ?
C17 C18 C19 116.5(3) . . ?
C17 C18 C21 120.6(3) . . ?
C19 C18 C21 122.9(3) . . ?
C18 C19 C20 118.4(4) . . ?
N15 C20 C19 123.3(3) . . ?
C23 N22 C27 117.7(3) . . ?
N22 C23 C24 123.0(3) . . ?
C25 C24 C23 118.6(3) . . ?
C26 C25 C24 116.5(3) . . ?
C26 C25 C28 121.4(3) . . ?
C24 C25 C28 122.1(3) . . ?
C27 C26 C25 121.0(3) . . ?
N22 C27 C26 123.1(3) . . ?
C8Aa C1Aa C2 110.4(3) . . ?
C8Aa C1Aa C12 108.4(3) . . ?
C2 C1Aa C12 109.4(3) . . ?
C9 C8Aa C1A 111.7(3) . . ?
C8Bb C1Bb C12 118.3(16) . . ?
C8Bb C1Bb C2 102.6(15) . . ?
C12 C1Bb C2 99.6(11) . . ?
C1Bb C8Bb C9 109.8(16) . . ?

_refine_diff_density_max         0.473
_refine_diff_density_min         -0.283
_refine_diff_density_rms         0.052

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: 4-picoline'
####################################################################### 
# 
# 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_racpsa-34lut
_database_code_depnum_ccdc_archive 'CCDC 1976324'
loop_
_audit_author_name
_audit_author_address
'Nikoletta B. Bathori'
;Cape Peninsula University of Technology
South Africa
;
_audit_update_record             
;
2020-01-09 deposited with the CCDC.	2020-02-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/4
_shelx_SHELXL_version_number     2016/4
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          358.14
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H28 N2 O4'
_chemical_formula_weight         408.48

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                   7.0626(14)
_cell_length_b                   8.7704(18)
_cell_length_c                   18.630(4)
_cell_angle_alpha                90.98(3)
_cell_angle_beta                 100.42(3)
_cell_angle_gamma                107.25(3)
_cell_volume                     1080.8(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    3364
_cell_measurement_theta_min      2.60
_cell_measurement_theta_max      28.34

_exptl_crystal_description       rod
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.255
_exptl_crystal_F_000             436
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.480
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.140
_exptl_absorpt_coefficient_mu    0.086
_shelx_estimated_absorpt_T_min   0.960
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.929
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  Bruker
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12233
_diffrn_reflns_av_unetI/netI     0.0359
_diffrn_reflns_av_R_equivalents  0.0265
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.229
_diffrn_reflns_theta_max         28.450
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5423
_reflns_number_gt                4166
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0484P)²+0.4285P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    noref
_refine_ls_extinction_method     'SHELXL-2016/4 (Sheldrick 2016)'
_refine_ls_extinction_coef       ?
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5423
_refine_ls_number_parameters     284
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0683
_refine_ls_R_factor_gt           0.0513
_refine_ls_wR_factor_ref         0.1313
_refine_ls_wR_factor_gt          0.1213
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.057
_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 1.0208(2) 0.49025(18) 0.74694(8) 0.0282(3) Uani 1 1 d . . . . .
H1 H 0.875567 0.424986 0.732239 0.034 Uiso 1 1 calc R U . . .
C2 C 1.1431(2) 0.37437(17) 0.76011(8) 0.0255(3) Uani 1 1 d . . . . .
C3 C 1.3511(2) 0.42662(19) 0.78492(9) 0.0344(4) Uani 1 1 d . . . . .
H3 H 1.419929 0.538204 0.792685 0.041 Uiso 1 1 calc R U . . .
C4 C 1.4592(3) 0.3192(2) 0.79844(9) 0.0371(4) Uani 1 1 d . . . . .
H4 H 1.601198 0.356759 0.815972 0.045 Uiso 1 1 calc R U . . .
C5 C 1.3606(3) 0.1569(2) 0.78644(9) 0.0360(4) Uani 1 1 d . . . . .
H5 H 1.434607 0.082436 0.795793 0.043 Uiso 1 1 calc R U . . .
C6 C 1.1546(3) 0.10297(19) 0.76085(9) 0.0352(4) Uani 1 1 d . . . . .
H6 H 1.086646 -0.008647 0.752172 0.042 Uiso 1 1 calc R U . . .
C7 C 1.0469(2) 0.21131(18) 0.74782(8) 0.0287(3) Uani 1 1 d . . . . .
H7 H 0.905022 0.173369 0.730201 0.034 Uiso 1 1 calc R U . . .
C8 C 1.0741(3) 0.5928(2) 0.68453(9) 0.0341(4) Uani 1 1 d . . . . .
H8A H 1.211897 0.668556 0.699914 0.041 Uiso 1 1 calc R U . . .
H8B H 1.074915 0.523223 0.642250 0.041 Uiso 1 1 calc R U . . .
C9 C 0.9280(3) 0.68595(19) 0.66102(9) 0.0326(3) Uani 1 1 d . . . . .
O10 O 0.7760(2) 0.66934(16) 0.68470(8) 0.0508(4) Uani 1 1 d . . . . .
O11 O 0.9841(2) 0.78696(15) 0.61220(7) 0.0415(3) Uani 1 1 d . . . . .
H11 H 0.888(4) 0.855(3) 0.6013(15) 0.083(8) Uiso 1 1 d . . . . .
C12 C 1.0435(2) 0.58534(19) 0.81963(9) 0.0327(3) Uani 1 1 d . . . . .
O13 O 0.9546(2) 0.52353(16) 0.86668(7) 0.0472(3) Uani 1 1 d . . . . .
O14 O 1.16602(19) 0.73007(14) 0.82647(7) 0.0394(3) Uani 1 1 d D . . . .
H14 H 1.173(5) 0.782(3) 0.8768(7) 0.125(12) Uiso 1 1 d D . . . .
N15 N 1.2009(2) 0.86970(18) 0.95320(8) 0.0361(3) Uani 1 1 d . . . . .
C16 C 1.2640(2) 1.0283(2) 0.96104(9) 0.0352(4) Uani 1 1 d . . . . .
H16 H 1.288078 1.084844 0.918917 0.042 Uiso 1 1 calc R U . . .
C17 C 1.2968(2) 1.11558(19) 1.02636(9) 0.0304(3) Uani 1 1 d . . . . .
C18 C 1.2595(2) 1.03217(18) 1.08808(8) 0.0264(3) Uani 1 1 d . . . . .
C19 C 1.1915(2) 0.86640(19) 1.08022(9) 0.0314(3) Uani 1 1 d . . . . .
H19 H 1.163496 0.806603 1.121163 0.038 Uiso 1 1 calc R U . . .
C20 C 1.1645(2) 0.78843(19) 1.01187(10) 0.0367(4) Uani 1 1 d . . . . .
H20 H 1.119236 0.674721 1.006691 0.044 Uiso 1 1 calc R U . . .
C21 C 1.3719(3) 1.2958(2) 1.03025(11) 0.0431(4) Uani 1 1 d . . . . .
H21A H 1.377362 1.331368 0.980887 0.065 Uiso 1 1 calc R U . . .
H21C H 1.507369 1.333810 1.060966 0.065 Uiso 1 1 calc R U . . .
H21B H 1.279777 1.339351 1.051448 0.065 Uiso 1 1 calc R U . . .
C22 C 1.2953(3) 1.1213(2) 1.16132(9) 0.0377(4) Uani 1 1 d . . . . .
H22B H 1.250973 1.045198 1.197333 0.057 Uiso 1 1 calc R U . . .
H22A H 1.218509 1.198277 1.157492 0.057 Uiso 1 1 calc R U . . .
H22C H 1.439702 1.178396 1.176908 0.057 Uiso 1 1 calc R U . . .
N23 N 0.7497(2) 0.97212(16) 0.59015(7) 0.0325(3) Uani 1 1 d . . . . .
C24 C 0.7843(2) 1.1037(2) 0.55285(8) 0.0336(4) Uani 1 1 d . . . . .
H24 H 0.891501 1.124937 0.526515 0.040 Uiso 1 1 calc R U . . .
C25 C 0.6731(2) 1.21077(18) 0.55035(8) 0.0305(3) Uani 1 1 d . . . . .
C26 C 0.5149(2) 1.17803(19) 0.58864(8) 0.0316(3) Uani 1 1 d . . . . .
C27 C 0.4782(3) 1.0401(2) 0.62594(9) 0.0343(4) Uani 1 1 d . . . . .
H27 H 0.369694 1.013203 0.651676 0.041 Uiso 1 1 calc R U . . .
C28 C 0.5977(3) 0.94254(19) 0.62586(8) 0.0330(3) Uani 1 1 d . . . . .
H28 H 0.570685 0.849649 0.652512 0.040 Uiso 1 1 calc R U . . .
C29 C 0.7208(3) 1.3536(2) 0.50623(10) 0.0436(4) Uani 1 1 d . . . . .
H29A H 0.836545 1.355280 0.483751 0.065 Uiso 1 1 calc R U . . .
H29C H 0.753810 1.451494 0.538224 0.065 Uiso 1 1 calc R U . . .
H29B H 0.603338 1.347462 0.467842 0.065 Uiso 1 1 calc R U . . .
C30 C 0.3867(3) 1.2869(2) 0.58917(11) 0.0460(4) Uani 1 1 d . . . . .
H30A H 0.320212 1.294136 0.538967 0.069 Uiso 1 1 calc R U . . .
H30B H 0.471993 1.393645 0.610158 0.069 Uiso 1 1 calc R U . . .
H30C H 0.284058 1.243967 0.618751 0.069 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
C1 C2 1.514(2) . ?
C1 C8 1.515(2) . ?
C1 C12 1.536(2) . ?
C2 C7 1.384(2) . ?
C2 C3 1.389(2) . ?
C3 C4 1.378(2) . ?
C4 C5 1.381(3) . ?
C5 C6 1.379(3) . ?
C6 C7 1.382(2) . ?
C8 C9 1.507(2) . ?
C9 O10 1.204(2) . ?
C9 O11 1.311(2) . ?
C12 O13 1.212(2) . ?
C12 O14 1.296(2) . ?
N15 C16 1.325(2) . ?
N15 C20 1.337(2) . ?
C16 C17 1.372(2) . ?
C17 C18 1.397(2) . ?
C17 C21 1.506(2) . ?
C18 C19 1.385(2) . ?
C18 C22 1.503(2) . ?
C19 C20 1.390(2) . ?
N23 C28 1.327(2) . ?
N23 C24 1.340(2) . ?
C24 C25 1.388(2) . ?
C25 C26 1.394(2) . ?
C25 C29 1.498(2) . ?
C26 C27 1.386(2) . ?
C26 C30 1.499(2) . ?
C27 C28 1.369(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C8 111.78(13) . . ?
C2 C1 C12 108.58(12) . . ?
C8 C1 C12 114.44(13) . . ?
C7 C2 C3 118.36(14) . . ?
C7 C2 C1 119.75(13) . . ?
C3 C2 C1 121.88(13) . . ?
C4 C3 C2 121.07(15) . . ?
C3 C4 C5 119.82(16) . . ?
C6 C5 C4 119.87(15) . . ?
C5 C6 C7 120.00(15) . . ?
C6 C7 C2 120.87(15) . . ?
C9 C8 C1 112.56(14) . . ?
O10 C9 O11 123.63(16) . . ?
O10 C9 C8 123.48(15) . . ?
O11 C9 C8 112.90(14) . . ?
O13 C12 O14 124.27(15) . . ?
O13 C12 C1 120.47(15) . . ?
O14 C12 C1 115.24(15) . . ?
C16 N15 C20 118.72(14) . . ?
N15 C16 C17 123.91(16) . . ?
C16 C17 C18 117.95(15) . . ?
C16 C17 C21 120.18(16) . . ?
C18 C17 C21 121.87(15) . . ?
C19 C18 C17 118.52(14) . . ?
C19 C18 C22 121.11(15) . . ?
C17 C18 C22 120.36(14) . . ?
C18 C19 C20 119.35(16) . . ?
N15 C20 C19 121.54(15) . . ?
C28 N23 C24 117.41(14) . . ?
N23 C24 C25 124.00(15) . . ?
C24 C25 C26 117.67(15) . . ?
C24 C25 C29 120.28(16) . . ?
C26 C25 C29 122.03(15) . . ?
C27 C26 C25 117.81(15) . . ?
C27 C26 C30 120.71(16) . . ?
C25 C26 C30 121.47(15) . . ?
C28 C27 C26 120.27(16) . . ?
N23 C28 C27 122.82(15) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O11 H11 N23 1.02(3) 1.61(3) 2.6307(19) 175(2) .
O14 H14 N15 1.0232(11) 1.557(3) 2.5782(19) 175(3) .
N15 H14 O13 1.557(3) 2.32(3) 3.245(2) 112.3(14) .
C28 H28 O10 0.95 2.46 3.148(2) 129.4 .

_refine_diff_density_max         0.535
_refine_diff_density_min         -0.277
_refine_diff_density_rms         0.043

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: 3,4-lutidine'
####################################################################### 
# 
# 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_racpsa-35lut
_database_code_depnum_ccdc_archive 'CCDC 1976326'
loop_
_audit_author_name
_audit_author_address
'Nikoletta B. Bathori'
;Cape Peninsula University of Technology
South Africa
;
_audit_update_record             
;
2020-01-09 deposited with the CCDC.	2020-02-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/4
_shelx_SHELXL_version_number     2016/4
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          407.91
_chemical_formula_moiety         ?
_chemical_formula_sum            'C44 H48 N2 O12'
_chemical_formula_weight         796.84

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                   12.222(2)
_cell_length_b                   14.926(3)
_cell_length_c                   22.984(5)
_cell_angle_alpha                90
_cell_angle_beta                 103.42(3)
_cell_angle_gamma                90
_cell_volume                     4078.4(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    5893
_cell_measurement_theta_min      2.21
_cell_measurement_theta_max      26.66

_exptl_crystal_description       rods
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_F_000             1688
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.095
_shelx_estimated_absorpt_T_min   0.978
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.881
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  Bruker
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            51410
_diffrn_reflns_av_unetI/netI     0.0382
_diffrn_reflns_av_R_equivalents  0.0506
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         1.640
_diffrn_reflns_theta_max         27.610
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             9432
_reflns_number_gt                6132
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0699P)²+4.2608P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         9432
_refine_ls_number_parameters     609
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1101
_refine_ls_R_factor_gt           0.0696
_refine_ls_wR_factor_ref         0.1906
_refine_ls_wR_factor_gt          0.1655
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_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
C9 C 0.0539(2) 0.38202(19) 0.39626(11) 0.0354(6) Uani 1 1 d . . . . .
O10 O -0.03250(16) 0.38107(17) 0.41422(9) 0.0535(6) Uani 1 1 d . . . . .
O11 O 0.15021(14) 0.38700(14) 0.43105(8) 0.0392(5) Uani 1 1 d . . . . .
C12 C 0.1070(2) 0.34278(19) 0.23693(10) 0.0340(6) Uani 1 1 d . . . . .
O13 O 0.19314(15) 0.34255(17) 0.21903(8) 0.0527(6) Uani 1 1 d . . . . .
O14 O 0.01001(14) 0.34131(13) 0.20226(7) 0.0358(4) Uani 1 1 d . . . . .
N15 N 0.12226(18) 0.39113(14) 0.54659(9) 0.0311(5) Uani 1 1 d . . . . .
H15 H 0.131(2) 0.3926(19) 0.5078(14) 0.043(8) Uiso 1 1 d . . . . .
C16 C 0.0182(2) 0.38272(17) 0.55498(11) 0.0315(5) Uani 1 1 d . . . . .
H16 H -0.044258 0.379708 0.521546 0.038 Uiso 1 1 calc R U . . .
C17 C 0.0012(2) 0.37839(17) 0.61272(11) 0.0317(5) Uani 1 1 d . . . . .
C18 C 0.0952(2) 0.38443(18) 0.65964(11) 0.0337(6) Uani 1 1 d . . . . .
H18 H 0.085805 0.381457 0.699485 0.040 Uiso 1 1 calc R U . . .
C19 C 0.2036(2) 0.39478(18) 0.65022(11) 0.0336(6) Uani 1 1 d . . . . .
C20 C 0.2136(2) 0.39712(18) 0.59172(11) 0.0339(6) Uani 1 1 d . . . . .
H20 H 0.285788 0.403033 0.583367 0.041 Uiso 1 1 calc R U . . .
C21 C -0.1150(2) 0.3660(2) 0.62256(13) 0.0430(7) Uani 1 1 d . . . . .
H21A H -0.112709 0.371068 0.665335 0.065 Uiso 1 1 calc R U . . .
H21C H -0.143316 0.306598 0.608225 0.065 Uiso 1 1 calc R U . . .
H21B H -0.164991 0.412134 0.600529 0.065 Uiso 1 1 calc R U . . .
C22 C 0.3049(2) 0.4047(2) 0.70102(13) 0.0517(8) Uani 1 1 d . . . . .
H22C H 0.373133 0.394653 0.686461 0.077 Uiso 1 1 calc R U . . .
H22B H 0.301207 0.360742 0.732168 0.077 Uiso 1 1 calc R U . . .
H22A H 0.306456 0.465302 0.717652 0.077 Uiso 1 1 calc R U . . .
N23 N 0.03189(19) 0.34688(15) 0.08714(9) 0.0338(5) Uani 1 1 d . . . . .
H23 H 0.025(2) 0.345(2) 0.1262(14) 0.047(8) Uiso 1 1 d . . . . .
C24 C -0.0587(2) 0.35131(19) 0.04174(12) 0.0386(6) Uani 1 1 d . . . . .
H24 H -0.131405 0.355384 0.049737 0.046 Uiso 1 1 calc R U . . .
C25 C -0.0478(2) 0.3500(2) -0.01651(11) 0.0407(7) Uani 1 1 d . . . . .
C26 C 0.0605(2) 0.3429(2) -0.02540(11) 0.0405(7) Uani 1 1 d . . . . .
H26 H 0.070387 0.340440 -0.065174 0.049 Uiso 1 1 calc R U . . .
C27 C 0.1547(2) 0.33918(18) 0.02170(11) 0.0341(6) Uani 1 1 d . . . . .
C28 C 0.1366(2) 0.34145(17) 0.07896(11) 0.0326(6) Uani 1 1 d . . . . .
H28 H 0.198767 0.339144 0.112568 0.039 Uiso 1 1 calc R U . . .
C29 C -0.1494(3) 0.3545(3) -0.06799(14) 0.0661(11) Uani 1 1 d . . . . .
H29C H -0.217226 0.341719 -0.053559 0.099 Uiso 1 1 calc R U . . .
H29A H -0.142062 0.310210 -0.098303 0.099 Uiso 1 1 calc R U . . .
H29B H -0.155222 0.414620 -0.085635 0.099 Uiso 1 1 calc R U . . .
C30 C 0.2715(2) 0.3304(2) 0.01219(13) 0.0501(8) Uani 1 1 d . . . . .
H30C H 0.290915 0.384602 -0.007230 0.075 Uiso 1 1 calc R U . . .
H30B H 0.275110 0.278314 -0.013286 0.075 Uiso 1 1 calc R U . . .
H30A H 0.324788 0.322389 0.050881 0.075 Uiso 1 1 calc R U . . .
C1A C 0.1199(3) 0.3285(3) 0.30529(14) 0.0268(12) Uani 0.706(10) 1 d . . P A 1
H1A H 0.198204 0.346177 0.325904 0.032 Uiso 0.706(10) 1 calc R U P A 1
C2A C 0.1058(6) 0.2304(3) 0.3181(2) 0.0251(10) Uani 0.706(10) 1 d . . P A 1
C3A C 0.2005(6) 0.1799(5) 0.3429(3) 0.0288(13) Uani 0.706(10) 1 d . . P A 1
H3A H 0.271507 0.208947 0.353394 0.035 Uiso 0.706(10) 1 calc R U P A 1
C4A C 0.1953(9) 0.0898(8) 0.3528(6) 0.0325(17) Uani 0.706(10) 1 d . . P A 1
H4A H 0.260871 0.058204 0.372691 0.039 Uiso 0.706(10) 1 calc R U P A 1
C5A C 0.0935(14) 0.0443(10) 0.3337(9) 0.0409(17) Uani 0.706(10) 1 d . . P A 1
H5A H 0.092003 -0.019239 0.335803 0.049 Uiso 0.706(10) 1 calc R U P A 1
C6A C -0.0094(3) 0.0930(2) 0.31084(12) 0.0416(7) Uani 1 1 d . . . . .
H6A H -0.080528 0.063986 0.300786 0.050 Uiso 1 1 calc R U . A 1
C7A C 0.0020(7) 0.1881(6) 0.3042(4) 0.0309(16) Uani 0.706(10) 1 d . . P A 1
H7A H -0.063694 0.223013 0.289804 0.037 Uiso 0.706(10) 1 calc R U P A 1
C8A C 0.0393(3) 0.3887(4) 0.32869(15) 0.0313(12) Uani 0.706(10) 1 d . . P A 1
H8A1 H -0.038944 0.372182 0.308839 0.038 Uiso 0.706(10) 1 calc R U P A 1
H8A2 H 0.051395 0.451554 0.317994 0.038 Uiso 0.706(10) 1 calc R U P A 1
C1B C 0.0411(9) 0.3339(10) 0.3265(7) 0.069(5) Uani 0.294(10) 1 d . . P A 2
H1B H -0.036790 0.347197 0.302987 0.082 Uiso 0.294(10) 1 calc R U P A 2
C2B C 0.0563(15) 0.2322(10) 0.3246(6) 0.034(3) Uani 0.294(10) 1 d . . P A 2
C3B C 0.1625(16) 0.1997(12) 0.3424(8) 0.032(4) Uani 0.294(10) 1 d . . P A 2
H3B H 0.226011 0.237952 0.353936 0.039 Uiso 0.294(10) 1 calc R U P A 2
C4B C 0.173(3) 0.105(3) 0.3428(15) 0.043(6) Uani 0.294(10) 1 d . . P A 2
H4B H 0.243799 0.076097 0.347585 0.052 Uiso 0.294(10) 1 calc R U P A 2
C5B C 0.076(4) 0.057(3) 0.336(2) 0.0409(17) Uani 0.294(10) 1 d . . P A 2
H5B H 0.076170 -0.002997 0.350242 0.049 Uiso 0.294(10) 1 calc R U P A 2
C7B C -0.0339(16) 0.1739(19) 0.3036(12) 0.040(5) Uani 0.294(10) 1 d . . P A 2
H7B H -0.107524 0.194254 0.285432 0.048 Uiso 0.294(10) 1 calc R U P A 2
C8B C 0.1164(10) 0.3894(11) 0.3023(6) 0.058(4) Uani 0.294(10) 1 d . . P A 2
H8B1 H 0.194190 0.386808 0.327132 0.069 Uiso 0.294(10) 1 calc R U P A 2
H8B2 H 0.090842 0.452554 0.298280 0.069 Uiso 0.294(10) 1 calc R U P A 2
C1X C -0.4245(2) 0.32330(19) 0.21741(11) 0.0332(6) Uani 1 1 d . . . . .
H1X H -0.386682 0.342992 0.258779 0.040 Uiso 1 1 calc R U . . .
C2X C -0.40217(19) 0.22294(17) 0.21102(11) 0.0312(5) Uani 1 1 d . . . . .
C3X C -0.3547(2) 0.1725(2) 0.26084(13) 0.0426(7) Uani 1 1 d . . . . .
H3X H -0.335295 0.200101 0.299087 0.051 Uiso 1 1 calc R U . . .
C4X C -0.3352(3) 0.0814(2) 0.25532(16) 0.0547(8) Uani 1 1 d . . . . .
H4X H -0.304682 0.046743 0.289957 0.066 Uiso 1 1 calc R U . . .
C5X C -0.3600(3) 0.0411(2) 0.19965(17) 0.0539(8) Uani 1 1 d . . . . .
H5X H -0.345513 -0.020895 0.195769 0.065 Uiso 1 1 calc R U . . .
H14Y H 0.287(3) 0.385(2) 0.4236(16) 0.068(11) Uiso 1 1 d . . . . .
H14X H -0.667(3) 0.329(3) 0.2432(17) 0.078(12) Uiso 1 1 d . . . . .
H11Y H 0.823(3) 0.380(3) 0.3868(17) 0.076(12) Uiso 1 1 d . . . . .
H11X H -0.115(4) 0.343(3) 0.2148(18) 0.091(13) Uiso 1 1 d . . . . .
C6X C -0.4058(3) 0.0915(2) 0.15000(15) 0.0506(8) Uani 1 1 d . . . . .
H6X H -0.422582 0.064238 0.111617 0.061 Uiso 1 1 calc R U . . .
C7X C -0.4278(2) 0.1813(2) 0.15531(12) 0.0419(7) Uani 1 1 d . . . . .
H7X H -0.460714 0.215052 0.120633 0.050 Uiso 1 1 calc R U . . .
C8X C -0.3815(2) 0.38013(19) 0.17258(12) 0.0356(6) Uani 1 1 d . . . . .
H8XB H -0.431551 0.370932 0.132505 0.043 Uiso 1 1 calc R U . . .
H8XA H -0.386853 0.443998 0.183201 0.043 Uiso 1 1 calc R U . . .
C9X C -0.2626(2) 0.36095(17) 0.16886(11) 0.0306(5) Uani 1 1 d . . . . .
O10X O -0.23465(15) 0.35965(14) 0.12198(8) 0.0427(5) Uani 1 1 d . . . . .
O11X O -0.19149(15) 0.35071(15) 0.22092(8) 0.0427(5) Uani 1 1 d . . . . .
C12X C -0.5511(2) 0.33923(18) 0.20750(11) 0.0324(6) Uani 1 1 d . . . . .
O13X O -0.60821(16) 0.3651(2) 0.16092(9) 0.0663(8) Uani 1 1 d . . . . .
O14X O -0.59108(16) 0.32059(15) 0.25419(8) 0.0410(5) Uani 1 1 d . . . . .
C1Y C 0.5432(2) 0.3442(3) 0.46297(14) 0.0557(9) Uani 1 1 d . . . . .
H1Y H 0.595978 0.354689 0.502668 0.067 Uiso 1 1 calc R U . . .
C2Y C 0.5481(2) 0.2417(2) 0.44810(15) 0.0487(8) Uani 1 1 d . . . . .
C3Y C 0.5097(2) 0.2049(2) 0.39095(14) 0.0490(8) Uani 1 1 d . . . . .
H3Y H 0.481600 0.243147 0.357804 0.059 Uiso 1 1 calc R U . . .
C4Y C 0.5127(2) 0.1133(2) 0.38250(13) 0.0444(7) Uani 1 1 d . . . . .
H4Y H 0.486757 0.088360 0.343709 0.053 Uiso 1 1 calc R U . . .
C5Y C 0.5534(2) 0.0586(2) 0.43079(14) 0.0463(7) Uani 1 1 d . . . . .
H5Y H 0.554968 -0.004490 0.425519 0.056 Uiso 1 1 calc R U . . .
C6Y C 0.5918(2) 0.0952(2) 0.48671(13) 0.0474(7) Uani 1 1 d . . . . .
H6Y H 0.619858 0.057098 0.519950 0.057 Uiso 1 1 calc R U . . .
C7Y C 0.5900(2) 0.1856(2) 0.49486(13) 0.0470(7) Uani 1 1 d . . . . .
H7Y H 0.618298 0.209961 0.533631 0.056 Uiso 1 1 calc R U . . .
C8Y C 0.5883(2) 0.3910(3) 0.41803(14) 0.0586(9) Uani 1 1 d . . . . .
H8YA H 0.572847 0.455912 0.419973 0.070 Uiso 1 1 calc R U . . .
H8YB H 0.549813 0.369319 0.377785 0.070 Uiso 1 1 calc R U . . .
C9Y C 0.7127(2) 0.37686(19) 0.42704(12) 0.0366(6) Uani 1 1 d . . . . .
O10Y O 0.77254(17) 0.3662(2) 0.47463(10) 0.0802(9) Uani 1 1 d . . . . .
O11Y O 0.74873(18) 0.38394(18) 0.37752(9) 0.0560(6) Uani 1 1 d . . . . .
C12Y C 0.4258(2) 0.3743(2) 0.46804(13) 0.0411(7) Uani 1 1 d . . . . .
O13Y O 0.40137(17) 0.38649(18) 0.51516(9) 0.0607(7) Uani 1 1 d . . . . .
O14Y O 0.35320(16) 0.37683(15) 0.41619(8) 0.0449(5) 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
C9 O10 1.220(3) . ?
C9 O11 1.262(3) . ?
C9 C8A 1.525(4) . ?
C9 C1B 1.730(18) . ?
C12 O13 1.216(3) . ?
C12 O14 1.266(3) . ?
C12 C1A 1.557(4) . ?
C12 C8B 1.635(14) . ?
N15 C16 1.336(3) . ?
N15 C20 1.339(3) . ?
C16 C17 1.391(3) . ?
C17 C18 1.384(4) . ?
C17 C21 1.501(4) . ?
C18 C19 1.400(4) . ?
C19 C20 1.378(3) . ?
C19 C22 1.499(4) . ?
N23 C24 1.335(3) . ?
N23 C28 1.339(3) . ?
C24 C25 1.376(4) . ?
C25 C26 1.390(4) . ?
C25 C29 1.505(4) . ?
C26 C27 1.386(4) . ?
C27 C28 1.385(3) . ?
C27 C30 1.499(4) . ?
C1Aa C2A 1.511(7) . ?
C1Aa C8A 1.521(6) . ?
C2Aa C7A 1.386(7) . ?
C2Aa C3A 1.389(6) . ?
C3Aa C4A 1.368(14) . ?
C4Aa C5A 1.40(2) . ?
C5Aa C6A 1.443(15) . ?
C6A C5B 1.20(4) . ?
C6A C7B 1.25(3) . ?
C6A C7A 1.437(9) . ?
C1Bb C8B 1.44(2) . ?
C1Bb C2B 1.53(2) . ?
C2Bb C3B 1.357(16) . ?
C2Bb C7B 1.400(15) . ?
C3Bb C4B 1.42(4) . ?
C4Bb C5B 1.36(6) . ?
C1X C8X 1.519(4) . ?
C1X C12X 1.529(3) . ?
C1X C2X 1.536(4) . ?
C2X C3X 1.381(4) . ?
C2X C7X 1.392(4) . ?
C3X C4X 1.391(4) . ?
C4X C5X 1.382(5) . ?
C5X C6X 1.373(5) . ?
C6X C7X 1.377(4) . ?
C8X C9X 1.503(3) . ?
C9X O10X 1.203(3) . ?
C9X O11X 1.314(3) . ?
C12X O13X 1.198(3) . ?
C12X O14X 1.308(3) . ?
C1Y C8Y 1.457(5) . ?
C1Y C12Y 1.534(4) . ?
C1Y C2Y 1.573(5) . ?
C2Y C7Y 1.364(4) . ?
C2Y C3Y 1.400(4) . ?
C3Y C4Y 1.384(4) . ?
C4Y C5Y 1.374(4) . ?
C5Y C6Y 1.375(4) . ?
C6Y C7Y 1.364(4) . ?
C8Y C9Y 1.501(4) . ?
C9Y O10Y 1.177(3) . ?
C9Y O11Y 1.316(3) . ?
C12Y O13Y 1.202(3) . ?
C12Y O14Y 1.311(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
O10 C9 O11 122.7(2) . . ?
O10 C9 C8A 116.1(2) . . ?
O11 C9 C8A 120.9(3) . . ?
O10 C9 C1B 114.2(4) . . ?
O11 C9 C1B 118.8(4) . . ?
O13 C12 O14 123.0(2) . . ?
O13 C12 C1A 116.6(2) . . ?
O14 C12 C1A 119.6(2) . . ?
O13 C12 C8B 115.5(4) . . ?
O14 C12 C8B 116.2(5) . . ?
C16 N15 C20 123.0(2) . . ?
N15 C16 C17 120.0(2) . . ?
C18 C17 C16 117.4(2) . . ?
C18 C17 C21 122.3(2) . . ?
C16 C17 C21 120.3(2) . . ?
C17 C18 C19 122.0(2) . . ?
C20 C19 C18 117.1(2) . . ?
C20 C19 C22 120.9(2) . . ?
C18 C19 C22 122.0(2) . . ?
N15 C20 C19 120.5(2) . . ?
C24 N23 C28 122.7(2) . . ?
N23 C24 C25 120.6(2) . . ?
C24 C25 C26 117.0(2) . . ?
C24 C25 C29 121.0(3) . . ?
C26 C25 C29 121.9(2) . . ?
C27 C26 C25 122.3(2) . . ?
C28 C27 C26 117.0(2) . . ?
C28 C27 C30 120.5(2) . . ?
C26 C27 C30 122.4(2) . . ?
N23 C28 C27 120.3(2) . . ?
C2Aa C1Aa C8A 113.0(5) . . ?
C2Aa C1Aa C12 109.8(3) . . ?
C8Aa C1Aa C12 110.7(3) . . ?
C7Aa C2Aa C3A 118.6(7) . . ?
C7Aa C2Aa C1A 122.4(6) . . ?
C3Aa C2Aa C1A 118.9(6) . . ?
C4Aa C3Aa C2A 122.4(7) . . ?
C3Aa C4Aa C5A 119.9(9) . . ?
C4Aa C5Aa C6A 120.5(11) . . ?
C5Bb C6A C7B 131(2) . . ?
C7Aa C6A C5A 116.0(8) . . ?
C2Aa C7Aa C6A 122.1(7) . . ?
C1Aa C8Aa C9 112.9(3) . . ?
C8Bb C1Bb C2B 117.8(16) . . ?
C8Bb C1Bb C9 101.0(11) . . ?
C2Bb C1Bb C9 117.0(10) . . ?
C3Bb C2Bb C7B 120.2(18) . . ?
C3Bb C2Bb C1B 117.4(15) . . ?
C7Bb C2Bb C1B 122.4(18) . . ?
C2Bb C3Bb C4B 115.8(18) . . ?
C5Bb C4Bb C3B 117(2) . . ?
C6A C5Bb C4B 117(4) . . ?
C6A C7Bb C2B 114.3(18) . . ?
C1Bb C8Bb C12 101.2(12) . . ?
C8X C1X C12X 108.0(2) . . ?
C8X C1X C2X 112.5(2) . . ?
C12X C1X C2X 109.5(2) . . ?
C3X C2X C7X 118.7(3) . . ?
C3X C2X C1X 120.2(2) . . ?
C7X C2X C1X 121.1(2) . . ?
C2X C3X C4X 120.4(3) . . ?
C5X C4X C3X 120.3(3) . . ?
C6X C5X C4X 119.3(3) . . ?
C5X C6X C7X 120.7(3) . . ?
C6X C7X C2X 120.6(3) . . ?
C9X C8X C1X 115.1(2) . . ?
O10X C9X O11X 123.3(2) . . ?
O10X C9X C8X 122.2(2) . . ?
O11X C9X C8X 114.4(2) . . ?
O13X C12X O14X 123.4(2) . . ?
O13X C12X C1X 122.9(2) . . ?
O14X C12X C1X 113.7(2) . . ?
C8Y C1Y C12Y 115.3(3) . . ?
C8Y C1Y C2Y 105.8(3) . . ?
C12Y C1Y C2Y 112.6(3) . . ?
C7Y C2Y C3Y 118.8(3) . . ?
C7Y C2Y C1Y 116.8(3) . . ?
C3Y C2Y C1Y 124.3(3) . . ?
C4Y C3Y C2Y 120.3(3) . . ?
C5Y C4Y C3Y 119.4(3) . . ?
C4Y C5Y C6Y 120.0(3) . . ?
C7Y C6Y C5Y 120.6(3) . . ?
C2Y C7Y C6Y 120.9(3) . . ?
C1Y C8Y C9Y 111.9(3) . . ?
O10Y C9Y O11Y 123.6(2) . . ?
O10Y C9Y C8Y 122.6(3) . . ?
O11Y C9Y C8Y 113.6(2) . . ?
O13Y C12Y O14Y 123.9(3) . . ?
O13Y C12Y C1Y 123.0(3) . . ?
O14Y C12Y C1Y 112.8(2) . . ?

_refine_diff_density_max         0.933
_refine_diff_density_min         -0.432
_refine_diff_density_rms         0.053

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: 3,5-lutidine'
