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

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

data_3g
_database_code_depnum_ccdc_archive 'CCDC 2294775'
loop_
_audit_author_name
_audit_author_address
'Constantinos Stoumpos'
;University of Crete
Greece
;
_audit_update_record             
;
2023-09-13 deposited with the CCDC.	2023-11-13 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT230_3g                  
;
PROBLEM: Hirshfeld Test Diff for    S002     --C00F     .       14.0 s.u.
RESPONSE: There is an intermolecular between C00F and O005 of the neighboring that influences the C-S carbon bond test. The other C-S bond of the thiophene ring, which is not in close contact with the neighboring molecules does not produce any disagreements with the rigid-bond test. 
;
# Added during the CSD deposition process: Wednesday 13 September 2023 11:48 AM
# end Validation Reply Form


_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H12 Cl N3 O2 S'
_chemical_formula_sum            'C15 H12 Cl N3 O2 S'
_chemical_formula_weight         333.79

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   7.2004(5)
_cell_length_b                   11.4906(8)
_cell_length_c                   18.0070(13)
_cell_angle_alpha                90
_cell_angle_beta                 99.310(3)
_cell_angle_gamma                90
_cell_volume                     1470.22(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    126
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      21.49
_cell_measurement_theta_min      2.92

_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.481
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       'rectangular plate'
_exptl_crystal_F_000             664
_exptl_transmission_factor_min   0.3845
_exptl_transmission_factor_max   0.4885
_exptl_crystal_size_max          0.138
_exptl_crystal_size_mid          0.119
_exptl_crystal_size_min          0.074
_exptl_absorpt_coefficient_mu    0.412
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_max  0.7449
_exptl_absorpt_correction_T_min  0.7057
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            59753
_diffrn_reflns_av_unetI/netI     0.0329
_diffrn_reflns_av_R_equivalents  0.1053
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.111
_diffrn_reflns_theta_max         25.998
_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             2886
_reflns_number_gt                1963
_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 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
There is an intermolecular between C00F and O005 of the
 neighboring that influences the C-S carbon bond test. 
The other C-S bond of the thiophene ring, which is not 
in close contact with the neighboring molecules does not
 produce any disagreements with the rigid-bond test.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0804P)²+1.3591P] 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         2886
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0892
_refine_ls_R_factor_gt           0.0578
_refine_ls_wR_factor_ref         0.1729
_refine_ls_wR_factor_gt          0.1489
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl01 Cl 0.40238(16) 0.81885(10) 0.75064(6) 0.0739(4) Uani 1 1 d . . . . .
S002 S 0.39499(18) 0.58451(12) 0.21925(6) 0.0802(4) Uani 1 1 d . . . . .
N003 N 0.3769(3) 0.6942(2) 0.54673(14) 0.0420(6) Uani 1 1 d . . . . .
N004 N 0.5620(4) 0.7831(2) 0.46080(15) 0.0470(7) Uani 1 1 d . . . . .
O005 O 0.3274(5) 0.9135(3) 0.42779(17) 0.0774(9) Uani 1 1 d . . . . .
N006 N 0.2339(4) 0.5481(3) 0.47656(16) 0.0514(7) Uani 1 1 d . . . . .
O7 O 0.6096(5) 0.9611(2) 0.40807(16) 0.0790(9) Uani 1 1 d . . . . .
C008 C 0.4320(4) 0.7006(3) 0.47686(18) 0.0434(7) Uani 1 1 d . . . . .
C009 C 0.3421(4) 0.6110(3) 0.43482(18) 0.0455(7) Uani 1 1 d . . . . .
C00A C 0.4212(4) 0.7625(3) 0.60917(18) 0.0464(8) Uani 1 1 d . . . . .
H00G H 0.501841 0.825736 0.609315 0.056 Uiso 1 1 calc R U . . .
C00B C 0.2543(4) 0.5996(3) 0.54355(19) 0.0481(8) Uani 1 1 d . . . . .
C00C C 0.4915(6) 0.8873(3) 0.43266(18) 0.0554(9) Uani 1 1 d . . . . .
C00D C 0.3507(4) 0.5799(3) 0.35710(19) 0.0489(8) Uani 1 1 d . . . . .
C00E C 0.3445(5) 0.7356(3) 0.67083(19) 0.0495(8) Uani 1 1 d . . . . .
C00F C 0.2972(5) 0.4615(3) 0.2483(2) 0.0555(9) Uani 1 1 d . . . . .
H00H H 0.259916 0.397031 0.218378 0.067 Uiso 1 1 calc R U . . .
C00G C 0.1752(5) 0.5744(3) 0.6080(2) 0.0544(9) Uani 1 1 d . . . . .
H00I H 0.092409 0.512209 0.607747 0.065 Uiso 1 1 calc R U . . .
C00H C 0.2818(5) 0.4728(3) 0.3242(2) 0.0580(9) Uani 1 1 d . . . . .
H00J H 0.230766 0.415028 0.350973 0.070 Uiso 1 1 calc R U . . .
C00I C 0.2195(5) 0.6406(3) 0.6708(2) 0.0578(9) Uani 1 1 d . . . . .
H00K H 0.167778 0.623616 0.713678 0.069 Uiso 1 1 calc R U . . .
C00J C 0.4170(5) 0.6481(4) 0.3049(2) 0.0614(10) Uani 1 1 d . . . . .
H00L H 0.468611 0.721651 0.315450 0.074 Uiso 1 1 calc R U . . .
C00K C 0.7618(5) 0.7501(4) 0.4709(3) 0.0770(13) Uani 1 1 d . . . . .
H00A H 0.798115 0.715619 0.520235 0.092 Uiso 1 1 calc R U . . .
H00B H 0.780134 0.692224 0.433502 0.092 Uiso 1 1 calc R U . . .
C00L C 0.8058(9) 0.9339(5) 0.4135(3) 0.109(2) Uani 1 1 d . . . . .
H00C H 0.828655 0.911276 0.363924 0.130 Uiso 1 1 calc R U . . .
H00D H 0.876755 1.004621 0.427129 0.130 Uiso 1 1 calc R U . . .
C00M C 0.8780(8) 0.8478(5) 0.4637(5) 0.128(3) Uani 1 1 d . . . . .
H00E H 0.910797 0.883121 0.512992 0.153 Uiso 1 1 calc R U . . .
H00F H 0.993804 0.819769 0.448977 0.153 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
Cl01 C00E 1.721(3) . ?
S002 C00J 1.692(4) . ?
S002 C00F 1.699(4) . ?
N003 C00A 1.366(4) . ?
N003 C008 1.381(4) . ?
N003 C00B 1.396(4) . ?
N004 C00C 1.366(5) . ?
N004 C008 1.395(4) . ?
N004 C00K 1.470(5) . ?
O005 C00C 1.209(5) . ?
N006 C00B 1.330(4) . ?
N006 C009 1.373(4) . ?
O7 C00C 1.327(4) . ?
O7 C00L 1.434(7) . ?
C008 C009 1.376(4) . ?
C009 C00D 1.455(5) . ?
C00A C00E 1.353(5) . ?
C00A H00G 0.9300 . ?
C00B C00G 1.404(5) . ?
C00D C00J 1.367(5) . ?
C00D C00H 1.421(5) . ?
C00E C00I 1.415(5) . ?
C00F C00H 1.395(5) . ?
C00F H00H 0.9300 . ?
C00G C00I 1.357(5) . ?
C00G H00I 0.9300 . ?
C00H H00J 0.9300 . ?
C00I H00K 0.9300 . ?
C00J H00L 0.9300 . ?
C00K C00M 1.418(6) . ?
C00K H00A 0.9700 . ?
C00K H00B 0.9700 . ?
C00L C00M 1.383(8) . ?
C00L H00C 0.9700 . ?
C00L H00D 0.9700 . ?
C00M H00E 0.9700 . ?
C00M H00F 0.9700 . ?

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
C00J S002 C00F 93.49(19) . . ?
C00A N003 C008 131.0(3) . . ?
C00A N003 C00B 122.9(3) . . ?
C008 N003 C00B 106.1(3) . . ?
C00C N004 C008 116.8(3) . . ?
C00C N004 C00K 124.7(3) . . ?
C008 N004 C00K 118.4(3) . . ?
C00B N006 C009 105.9(3) . . ?
C00C O7 C00L 121.0(3) . . ?
C009 C008 N003 106.4(3) . . ?
C009 C008 N004 131.7(3) . . ?
N003 C008 N004 121.8(3) . . ?
N006 C009 C008 110.5(3) . . ?
N006 C009 C00D 120.9(3) . . ?
C008 C009 C00D 128.6(3) . . ?
C00E C00A N003 118.2(3) . . ?
C00E C00A H00G 120.9 . . ?
N003 C00A H00G 120.9 . . ?
N006 C00B N003 111.1(3) . . ?
N006 C00B C00G 131.2(3) . . ?
N003 C00B C00G 117.7(3) . . ?
O005 C00C O7 119.2(4) . . ?
O005 C00C N004 123.1(3) . . ?
O7 C00C N004 117.7(4) . . ?
C00J C00D C00H 110.3(3) . . ?
C00J C00D C009 126.4(3) . . ?
C00H C00D C009 123.2(3) . . ?
C00A C00E C00I 121.4(3) . . ?
C00A C00E Cl01 118.8(3) . . ?
C00I C00E Cl01 119.8(3) . . ?
C00H C00F S002 109.1(3) . . ?
C00H C00F H00H 125.4 . . ?
S002 C00F H00H 125.4 . . ?
C00I C00G C00B 120.1(3) . . ?
C00I C00G H00I 119.9 . . ?
C00B C00G H00I 119.9 . . ?
C00F C00H C00D 114.3(4) . . ?
C00F C00H H00J 122.9 . . ?
C00D C00H H00J 122.9 . . ?
C00G C00I C00E 119.7(3) . . ?
C00G C00I H00K 120.1 . . ?
C00E C00I H00K 120.1 . . ?
C00D C00J S002 112.8(3) . . ?
C00D C00J H00L 123.6 . . ?
S002 C00J H00L 123.6 . . ?
C00M C00K N004 111.4(4) . . ?
C00M C00K H00A 109.3 . . ?
N004 C00K H00A 109.3 . . ?
C00M C00K H00B 109.3 . . ?
N004 C00K H00B 109.3 . . ?
H00A C00K H00B 108.0 . . ?
C00M C00L O7 117.6(4) . . ?
C00M C00L H00C 107.9 . . ?
O7 C00L H00C 107.9 . . ?
C00M C00L H00D 107.9 . . ?
O7 C00L H00D 107.9 . . ?
H00C C00L H00D 107.2 . . ?
C00L C00M C00K 117.4(5) . . ?
C00L C00M H00E 107.9 . . ?
C00K C00M H00E 107.9 . . ?
C00L C00M H00F 107.9 . . ?
C00K C00M H00F 107.9 . . ?
H00E C00M H00F 107.2 . . ?

_refine_diff_density_max         0.317
_refine_diff_density_min         -0.420
_refine_diff_density_rms         0.061



####################################################################### 
# 
# 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_4
_database_code_depnum_ccdc_archive 'CCDC 2294777'
loop_
_audit_author_name
_audit_author_address
'Constantinos Stoumpos'
;University of Crete
Greece
;
_audit_update_record             
;
2023-09-13 deposited with the CCDC.	2023-11-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H16 Cl N3 O'
_chemical_formula_sum            'C16 H16 Cl N3 O'
_chemical_formula_weight         301.77

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   7.804(3)
_cell_length_b                   9.955(4)
_cell_length_c                   19.163(7)
_cell_angle_alpha                96.538(13)
_cell_angle_beta                 96.978(11)
_cell_angle_gamma                90.269(13)
_cell_volume                     1467.8(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    123
_cell_measurement_theta_min      4.304
_cell_measurement_theta_max      24.58

_exptl_crystal_description       'elongated needle'
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.366
_exptl_crystal_F_000             632
_exptl_transmission_factor_min   0.9480
_exptl_transmission_factor_max   0.9920
_exptl_crystal_size_max          0.205
_exptl_crystal_size_mid          0.081
_exptl_crystal_size_min          0.029
_exptl_absorpt_coefficient_mu    0.263
_shelx_estimated_absorpt_T_min   0.948
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.4945
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            63756
_diffrn_reflns_av_unetI/netI     0.1814
_diffrn_reflns_av_R_equivalents  0.3286
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.060
_diffrn_reflns_theta_max         26.000
_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             5791
_reflns_number_gt                2157
_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 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;Crystal and refinement statistics are 
 poor due to an unresolved twinning
 along 010 (rec) with a ( -1 0 0 0.048 1 0.12 0 0 -1)
 matrix. The same matrix
 was obtained for three independent
 crystal collections at approximately the same 
 fraction (0.25). The data in this file 
 are the highest intensity dataset obtained.
 The crystals are weakly diffracting at high 2 theta 
 angles.,Twin
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2000P)²] 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         5791
_refine_ls_number_parameters     381
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2790
_refine_ls_R_factor_gt           0.1487
_refine_ls_wR_factor_ref         0.4528
_refine_ls_wR_factor_gt          0.3815
_refine_ls_goodness_of_fit_ref   1.172
_refine_ls_restrained_S_all      1.172
_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
Cl01 Cl 0.6089(4) 0.5176(3) 0.32356(15) 0.1078(12) Uani 1 1 d . . . . .
Cl02 Cl 0.2954(5) -0.0372(4) 0.79146(15) 0.1188(13) Uani 1 1 d . . . . .
O003 O 0.1818(8) -0.1397(6) 0.0621(4) 0.0721(17) Uani 1 1 d . . . . .
H003 H 0.224732 -0.198608 0.036472 0.108 Uiso 1 1 calc R U . . .
N004 N 0.2115(10) 0.0658(8) 0.3726(4) 0.070(2) Uani 1 1 d . . . . .
N005 N 0.1389(10) 0.4352(8) -0.0836(4) 0.071(2) Uani 1 1 d . . . . .
N006 N 0.1690(9) 0.2506(7) -0.0086(4) 0.068(2) Uani 1 1 d . . . . .
H006 H 0.082011 0.224190 0.010184 0.082 Uiso 1 1 calc R U . . .
N007 N 0.2771(10) -0.1075(7) 0.4348(4) 0.072(2) Uani 1 1 d . . . . .
N008 N 0.2665(10) 0.6100(7) -0.0100(4) 0.070(2) Uani 1 1 d . . . . .
N009 N 0.1543(10) 0.2486(7) 0.4588(4) 0.068(2) Uani 1 1 d . . . . .
H009 H 0.049442 0.274066 0.459950 0.081 Uiso 1 1 calc R U . . .
C00A C 0.2397(11) 0.0049(9) 0.4797(5) 0.063(2) Uani 1 1 d . . . . .
C00B C 0.2697(11) 0.4936(9) 0.0241(5) 0.064(2) Uani 1 1 d . . . . .
C00C C 0.2513(12) -0.0037(9) 0.5568(5) 0.066(2) Uani 1 1 d . . . . .
O0 O 0.0769(11) 0.6537(7) 0.4208(5) 0.109(3) Uani 1 1 d . . . . .
H0 H 0.118389 0.695087 0.458593 0.164 Uiso 1 1 calc R U . . .
C00D C 0.3539(12) 0.4964(9) 0.0984(5) 0.064(2) Uani 1 1 d . . . . .
C00F C 0.1895(12) 0.5725(10) -0.0750(5) 0.073(3) Uani 1 1 d . . . . .
C00G C 0.1931(11) 0.3854(9) -0.0210(5) 0.063(2) Uani 1 1 d . . . . .
C00H C 0.5106(13) 0.5118(11) 0.2352(5) 0.077(3) Uani 1 1 d . . . . .
C00I C 0.1980(12) 0.1153(9) 0.4425(5) 0.066(2) Uani 1 1 d . . . . .
C00J C 0.4407(12) 0.6132(10) 0.1320(6) 0.075(3) Uani 1 1 d . . . . .
H00J H 0.445913 0.688206 0.107451 0.089 Uiso 1 1 calc R U . . .
C00K C 0.2560(14) -0.0703(10) 0.3696(5) 0.076(3) Uani 1 1 d . . . . .
C00L C 0.5173(12) 0.6197(10) 0.1992(5) 0.075(3) Uani 1 1 d . . . . .
H00L H 0.574730 0.698608 0.220688 0.090 Uiso 1 1 calc R U . . .
C00M C 0.1989(13) 0.0998(10) 0.6032(5) 0.076(3) Uani 1 1 d . . . . .
H00M H 0.154884 0.177743 0.585708 0.091 Uiso 1 1 calc R U . . .
C00N C 0.2549(12) 0.0132(9) -0.0218(5) 0.069(2) Uani 1 1 d . . . . .
H00A H 0.141731 -0.008212 -0.047806 0.083 Uiso 1 1 calc R U . . .
H00B H 0.336620 -0.047535 -0.042585 0.083 Uiso 1 1 calc R U . . .
C00O C 0.2770(14) -0.0241(12) 0.7010(5) 0.080(3) Uani 1 1 d . . . . .
C00P C 0.3044(12) 0.1578(9) -0.0304(5) 0.073(3) Uani 1 1 d . . . . .
H00C H 0.413268 0.182927 -0.001605 0.088 Uiso 1 1 calc R U . . .
H00D H 0.319030 0.164596 -0.079429 0.088 Uiso 1 1 calc R U . . .
C00Q C 0.0252(13) 0.4465(12) -0.2013(6) 0.086(3) Uani 1 1 d . . . . .
H00Q H -0.031519 0.406360 -0.244117 0.103 Uiso 1 1 calc R U . . .
C00R C 0.0604(12) 0.3702(11) -0.1472(5) 0.076(3) Uani 1 1 d . . . . .
H00R H 0.032987 0.278290 -0.152655 0.092 Uiso 1 1 calc R U . . .
C00S C 0.2105(13) 0.0902(11) 0.6759(5) 0.082(3) Uani 1 1 d . . . . .
H00S H 0.173632 0.160345 0.706557 0.098 Uiso 1 1 calc R U . . .
C00T C 0.2513(12) -0.0115(10) 0.0536(5) 0.074(3) Uani 1 1 d . . . . .
H00E H 0.368140 -0.003225 0.077742 0.088 Uiso 1 1 calc R U . . .
H00F H 0.183602 0.058208 0.076294 0.088 Uiso 1 1 calc R U . . .
C00U C 0.4264(14) 0.3955(11) 0.2048(5) 0.083(3) Uani 1 1 d . . . . .
H00U H 0.422021 0.322020 0.230468 0.100 Uiso 1 1 calc R U . . .
C00V C 0.2767(14) -0.1388(10) 0.3057(6) 0.083(3) Uani 1 1 d . . . . .
H00V H 0.312956 -0.227924 0.303214 0.099 Uiso 1 1 calc R U . . .
C00W C 0.3056(12) 0.3443(9) 0.4744(6) 0.079(3) Uani 1 1 d . . . . .
H00G H 0.378485 0.330630 0.436759 0.094 Uiso 1 1 calc R U . . .
H00H H 0.373427 0.327613 0.518321 0.094 Uiso 1 1 calc R U . . .
C00X C 0.1790(14) 0.1299(11) 0.3139(5) 0.084(3) Uani 1 1 d . . . . .
H00X H 0.147691 0.220266 0.317064 0.101 Uiso 1 1 calc R U . . .
C00Y C 0.3174(15) -0.1162(10) 0.5846(5) 0.088(3) Uani 1 1 d . . . . .
H00Y H 0.357943 -0.185962 0.554822 0.106 Uiso 1 1 calc R U . . .
C00Z C 0.0694(15) 0.5778(12) -0.1950(6) 0.088(3) Uani 1 1 d . . . . .
H00Z H 0.045282 0.624899 -0.234188 0.106 Uiso 1 1 calc R U . . .
C010 C 0.3479(13) 0.3866(10) 0.1360(6) 0.078(3) Uani 1 1 d . . . . .
H010 H 0.291280 0.307015 0.115068 0.093 Uiso 1 1 calc R U . . .
C011 C 0.1478(13) 0.6447(10) -0.1340(6) 0.079(3) Uani 1 1 d . . . . .
H011 H 0.173703 0.736648 -0.130845 0.095 Uiso 1 1 calc R U . . .
C012 C 0.1935(14) 0.0581(12) 0.2497(5) 0.087(3) Uani 1 1 d . . . . .
H012 H 0.169053 0.099927 0.208723 0.105 Uiso 1 1 calc R U . . .
C013 C 0.1504(15) 0.5252(10) 0.4128(6) 0.090(3) Uani 1 1 d . . . . .
H01A H 0.231169 0.523875 0.378068 0.108 Uiso 1 1 calc R U . . .
H01B H 0.060134 0.458396 0.395067 0.108 Uiso 1 1 calc R U . . .
C014 C 0.2424(12) 0.4877(10) 0.4805(6) 0.084(3) Uani 1 1 d . . . . .
H01C H 0.165059 0.498758 0.516644 0.100 Uiso 1 1 calc R U . . .
H01D H 0.340258 0.548992 0.495566 0.100 Uiso 1 1 calc R U . . .
C015 C 0.2442(17) -0.0771(12) 0.2442(6) 0.098(4) Uani 1 1 d . . . . .
H015 H 0.255926 -0.124399 0.200359 0.118 Uiso 1 1 calc R U . . .
C016 C 0.3250(16) -0.1282(12) 0.6565(6) 0.101(4) Uani 1 1 d . . . . .
H016 H 0.363003 -0.207764 0.673901 0.122 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
Cl01 C00H 1.766(10) . ?
Cl02 C00O 1.742(10) . ?
O003 C00T 1.418(10) . ?
O003 H003 0.8200 . ?
N004 C00X 1.355(11) . ?
N004 C00I 1.390(11) . ?
N004 C00K 1.397(12) . ?
N005 C00G 1.372(11) . ?
N005 C00R 1.384(12) . ?
N005 C00F 1.407(12) . ?
N006 C00G 1.404(11) . ?
N006 C00P 1.474(11) . ?
N006 H006 0.8600 . ?
N007 C00K 1.334(11) . ?
N007 C00A 1.387(11) . ?
N008 C00F 1.328(12) . ?
N008 C00B 1.392(11) . ?
N009 C00I 1.382(11) . ?
N009 C00W 1.493(12) . ?
N009 H009 0.8600 . ?
C00A C00I 1.396(12) . ?
C00A C00C 1.482(12) . ?
C00B C00G 1.386(12) . ?
C00B C00D 1.492(13) . ?
C00C C00Y 1.370(12) . ?
C00C C00M 1.379(13) . ?
O0 C013 1.404(11) . ?
O0 H0 0.8200 . ?
C00D C010 1.380(13) . ?
C00D C00J 1.393(13) . ?
C00F C011 1.413(13) . ?
C00H C00L 1.346(13) . ?
C00H C00U 1.363(14) . ?
C00J C00L 1.348(13) . ?
C00J H00J 0.9300 . ?
C00K C00V 1.360(14) . ?
C00L H00L 0.9300 . ?
C00M C00S 1.400(13) . ?
C00M H00M 0.9300 . ?
C00N C00T 1.496(12) . ?
C00N C00P 1.521(12) . ?
C00N H00A 0.9700 . ?
C00N H00B 0.9700 . ?
C00O C016 1.349(15) . ?
C00O C00S 1.365(14) . ?
C00P H00C 0.9700 . ?
C00P H00D 0.9700 . ?
C00Q C00Z 1.338(15) . ?
C00Q C00R 1.356(14) . ?
C00Q H00Q 0.9300 . ?
C00R H00R 0.9300 . ?
C00S H00S 0.9300 . ?
C00T H00E 0.9700 . ?
C00T H00F 0.9700 . ?
C00U C010 1.377(14) . ?
C00U H00U 0.9300 . ?
C00V C015 1.387(14) . ?
C00V H00V 0.9300 . ?
C00W C014 1.509(12) . ?
C00W H00G 0.9700 . ?
C00W H00H 0.9700 . ?
C00X C012 1.368(14) . ?
C00X H00X 0.9300 . ?
C00Y C016 1.390(14) . ?
C00Y H00Y 0.9300 . ?
C00Z C011 1.354(14) . ?
C00Z H00Z 0.9300 . ?
C010 H010 0.9300 . ?
C011 H011 0.9300 . ?
C012 C015 1.401(15) . ?
C012 H012 0.9300 . ?
C013 C014 1.491(14) . ?
C013 H01A 0.9700 . ?
C013 H01B 0.9700 . ?
C014 H01C 0.9700 . ?
C014 H01D 0.9700 . ?
C015 H015 0.9300 . ?
C016 H016 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
C00T O003 H003 109.5 . . ?
C00X N004 C00I 128.5(8) . . ?
C00X N004 C00K 122.4(9) . . ?
C00I N004 C00K 109.0(7) . . ?
C00G N005 C00R 130.4(9) . . ?
C00G N005 C00F 106.8(8) . . ?
C00R N005 C00F 122.6(8) . . ?
C00G N006 C00P 114.8(7) . . ?
C00G N006 H006 122.6 . . ?
C00P N006 H006 122.6 . . ?
C00K N007 C00A 106.2(7) . . ?
C00F N008 C00B 105.2(8) . . ?
C00I N009 C00W 114.0(7) . . ?
C00I N009 H009 123.0 . . ?
C00W N009 H009 123.0 . . ?
N007 C00A C00I 111.4(8) . . ?
N007 C00A C00C 119.5(8) . . ?
C00I C00A C00C 129.1(8) . . ?
C00G C00B N008 110.8(8) . . ?
C00G C00B C00D 128.9(8) . . ?
N008 C00B C00D 120.3(8) . . ?
C00Y C00C C00M 117.6(9) . . ?
C00Y C00C C00A 120.4(8) . . ?
C00M C00C C00A 122.0(8) . . ?
C013 O0 H0 109.5 . . ?
C010 C00D C00J 118.1(9) . . ?
C010 C00D C00B 122.1(9) . . ?
C00J C00D C00B 119.7(8) . . ?
N008 C00F N005 111.2(8) . . ?
N008 C00F C011 132.1(10) . . ?
N005 C00F C011 116.7(9) . . ?
N005 C00G C00B 106.0(8) . . ?
N005 C00G N006 124.3(8) . . ?
C00B C00G N006 129.7(8) . . ?
C00L C00H C00U 120.9(9) . . ?
C00L C00H Cl01 120.9(9) . . ?
C00U C00H Cl01 118.2(8) . . ?
N009 C00I N004 119.7(8) . . ?
N009 C00I C00A 136.6(8) . . ?
N004 C00I C00A 103.7(7) . . ?
C00L C00J C00D 121.4(9) . . ?
C00L C00J H00J 119.3 . . ?
C00D C00J H00J 119.3 . . ?
N007 C00K C00V 131.6(10) . . ?
N007 C00K N004 109.7(8) . . ?
C00V C00K N004 118.7(9) . . ?
C00H C00L C00J 119.8(10) . . ?
C00H C00L H00L 120.1 . . ?
C00J C00L H00L 120.1 . . ?
C00C C00M C00S 121.4(9) . . ?
C00C C00M H00M 119.3 . . ?
C00S C00M H00M 119.3 . . ?
C00T C00N C00P 113.6(8) . . ?
C00T C00N H00A 108.8 . . ?
C00P C00N H00A 108.8 . . ?
C00T C00N H00B 108.8 . . ?
C00P C00N H00B 108.8 . . ?
H00A C00N H00B 107.7 . . ?
C016 C00O C00S 120.9(10) . . ?
C016 C00O Cl02 119.6(8) . . ?
C00S C00O Cl02 119.5(8) . . ?
N006 C00P C00N 110.0(7) . . ?
N006 C00P H00C 109.7 . . ?
C00N C00P H00C 109.7 . . ?
N006 C00P H00D 109.7 . . ?
C00N C00P H00D 109.7 . . ?
H00C C00P H00D 108.2 . . ?
C00Z C00Q C00R 122.2(11) . . ?
C00Z C00Q H00Q 118.9 . . ?
C00R C00Q H00Q 118.9 . . ?
C00Q C00R N005 117.0(10) . . ?
C00Q C00R H00R 121.5 . . ?
N005 C00R H00R 121.5 . . ?
C00O C00S C00M 118.7(10) . . ?
C00O C00S H00S 120.6 . . ?
C00M C00S H00S 120.6 . . ?
O003 C00T C00N 114.3(8) . . ?
O003 C00T H00E 108.7 . . ?
C00N C00T H00E 108.7 . . ?
O003 C00T H00F 108.7 . . ?
C00N C00T H00F 108.7 . . ?
H00E C00T H00F 107.6 . . ?
C00H C00U C010 120.2(9) . . ?
C00H C00U H00U 119.9 . . ?
C010 C00U H00U 119.9 . . ?
C00K C00V C015 120.6(10) . . ?
C00K C00V H00V 119.7 . . ?
C015 C00V H00V 119.7 . . ?
N009 C00W C014 109.4(7) . . ?
N009 C00W H00G 109.8 . . ?
C014 C00W H00G 109.8 . . ?
N009 C00W H00H 109.8 . . ?
C014 C00W H00H 109.8 . . ?
H00G C00W H00H 108.2 . . ?
N004 C00X C012 118.1(10) . . ?
N004 C00X H00X 121.0 . . ?
C012 C00X H00X 121.0 . . ?
C00C C00Y C016 121.4(9) . . ?
C00C C00Y H00Y 119.3 . . ?
C016 C00Y H00Y 119.3 . . ?
C00Q C00Z C011 122.6(10) . . ?
C00Q C00Z H00Z 118.7 . . ?
C011 C00Z H00Z 118.7 . . ?
C00D C010 C00U 119.6(10) . . ?
C00D C010 H010 120.2 . . ?
C00U C010 H010 120.2 . . ?
C00Z C011 C00F 118.9(10) . . ?
C00Z C011 H011 120.6 . . ?
C00F C011 H011 120.6 . . ?
C00X C012 C015 121.5(10) . . ?
C00X C012 H012 119.2 . . ?
C015 C012 H012 119.2 . . ?
O0 C013 C014 112.5(10) . . ?
O0 C013 H01A 109.1 . . ?
C014 C013 H01A 109.1 . . ?
O0 C013 H01B 109.1 . . ?
C014 C013 H01B 109.1 . . ?
H01A C013 H01B 107.8 . . ?
C013 C014 C00W 113.0(9) . . ?
C013 C014 H01C 109.0 . . ?
C00W C014 H01C 109.0 . . ?
C013 C014 H01D 109.0 . . ?
C00W C014 H01D 109.0 . . ?
H01C C014 H01D 107.8 . . ?
C00V C015 C012 118.5(10) . . ?
C00V C015 H015 120.8 . . ?
C012 C015 H015 120.8 . . ?
C00O C016 C00Y 119.8(9) . . ?
C00O C016 H016 120.1 . . ?
C00Y C016 H016 120.1 . . ?

_refine_diff_density_max         0.518
_refine_diff_density_min         -0.452
_refine_diff_density_rms         0.105



####################################################################### 
# 
# 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_3a
_database_code_depnum_ccdc_archive 'CCDC 2294778'
loop_
_audit_author_name
_audit_author_address
'Constantinos Stoumpos'
;University of Crete
Greece
;
_audit_update_record             
;
2023-09-13 deposited with the CCDC.	2023-11-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H14 Cl N3 O2'
_chemical_formula_sum            'C17 H14 Cl N3 O2'
_chemical_formula_weight         327.76

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   11.1476(9)
_cell_length_b                   7.1242(6)
_cell_length_c                   18.6955(15)
_cell_angle_alpha                90
_cell_angle_beta                 101.839(3)
_cell_angle_gamma                90
_cell_volume                     1453.2(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7694
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      21.98
_cell_measurement_theta_min      2.23

_exptl_crystal_description       'rectangular plate'
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.498
_exptl_crystal_F_000             680
_exptl_transmission_factor_min   0.602
_exptl_transmission_factor_max   0.701
_exptl_crystal_size_max          0.089
_exptl_crystal_size_mid          0.087
_exptl_crystal_size_min          0.077
_exptl_absorpt_coefficient_mu    0.277
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_max  0.7448
_exptl_absorpt_correction_T_min  0.6613
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            71443
_diffrn_reflns_av_unetI/netI     0.0318
_diffrn_reflns_av_R_equivalents  0.1210
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.226
_diffrn_reflns_theta_max         25.999
_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             2856
_reflns_number_gt                2043
_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 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0438P)²+0.7417P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0104(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2856
_refine_ls_number_parameters     265
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0672
_refine_ls_R_factor_gt           0.0417
_refine_ls_wR_factor_ref         0.1098
_refine_ls_wR_factor_gt          0.0953
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_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
Cl01 Cl -0.09585(6) 0.34608(10) 0.41037(4) 0.0570(2) Uani 1 1 d . . . . .
O002 O 0.63211(14) 0.4248(2) 0.47190(8) 0.0478(4) Uani 1 1 d . . . . .
O003 O 0.57513(16) 0.6097(3) 0.37680(9) 0.0523(5) Uani 1 1 d . . . . .
N004 N 0.52384(16) 0.3015(3) 0.36269(9) 0.0374(4) Uani 1 1 d . . . . .
N005 N 0.51336(16) 0.3318(3) 0.23278(9) 0.0394(4) Uani 1 1 d . . . . .
N006 N 0.31118(16) 0.3509(3) 0.18752(9) 0.0406(4) Uani 1 1 d . . . . .
C007 C 0.57610(19) 0.4537(3) 0.40149(12) 0.0388(5) Uani 1 1 d . . . . .
C008 C 0.3323(2) 0.3409(3) 0.26249(11) 0.0374(5) Uani 1 1 d . . . . .
C009 C 0.45562(19) 0.3305(3) 0.29142(11) 0.0375(5) Uani 1 1 d . . . . .
C00A C 0.22911(19) 0.3408(3) 0.30034(11) 0.0363(5) Uani 1 1 d . . . . .
C00B C 0.4210(2) 0.3464(3) 0.17064(12) 0.0402(5) Uani 1 1 d . . . . .
C00C C 0.6341(2) 0.0905(4) 0.45644(14) 0.0480(6) Uani 1 1 d . . . . .
H11 H 0.628(2) -0.031(4) 0.4782(14) 0.057(8) Uiso 1 1 d . . . . .
H10 H 0.717(3) 0.099(4) 0.4468(14) 0.064(8) Uiso 1 1 d . . . . .
C00D C 0.2443(2) 0.3756(4) 0.37507(13) 0.0458(6) Uani 1 1 d . . . . .
H0 H 0.326(3) 0.404(4) 0.4060(14) 0.063(8) Uiso 1 1 d . . . . .
C00E C 0.1114(2) 0.3060(3) 0.26099(13) 0.0407(5) Uani 1 1 d . . . . .
H3 H 0.100(2) 0.276(3) 0.2108(14) 0.045(6) Uiso 1 1 d . . . . .
C00F C 0.0295(2) 0.3430(3) 0.36809(12) 0.0416(5) Uani 1 1 d . . . . .
C00G C 0.1450(2) 0.3764(4) 0.40897(13) 0.0467(6) Uani 1 1 d . . . . .
H1 H 0.153(2) 0.403(4) 0.4609(15) 0.064(8) Uiso 1 1 d . . . . .
C00H C 0.0122(2) 0.3070(4) 0.29422(13) 0.0451(6) Uani 1 1 d . . . . .
H2 H -0.067(2) 0.285(3) 0.2675(13) 0.048(7) Uiso 1 1 d . . . . .
C00I C 0.4564(2) 0.3516(4) 0.10220(13) 0.0474(6) Uani 1 1 d . . . . .
H4 H 0.393(2) 0.362(4) 0.0581(15) 0.061(8) Uiso 1 1 d . . . . .
C00J C 0.5376(3) 0.1047(4) 0.38759(14) 0.0481(6) Uani 1 1 d . . . . .
H9 H 0.559(2) 0.027(4) 0.3496(15) 0.059(8) Uiso 1 1 d . . . . .
H8 H 0.457(2) 0.063(4) 0.3975(13) 0.055(7) Uiso 1 1 d . . . . .
C00K C 0.6353(2) 0.3203(4) 0.22975(14) 0.0500(6) Uani 1 1 d . . . . .
H7 H 0.686(3) 0.312(4) 0.2725(15) 0.062(8) Uiso 1 1 d . . . . .
C00L C 0.6170(3) 0.2463(4) 0.50645(14) 0.0499(6) Uani 1 1 d . . . . .
H13 H 0.677(3) 0.250(4) 0.5533(16) 0.065(8) Uiso 1 1 d . . . . .
H12 H 0.532(2) 0.248(3) 0.5174(13) 0.055(7) Uiso 1 1 d . . . . .
C00M C 0.5760(3) 0.3389(4) 0.09948(14) 0.0539(7) Uani 1 1 d . . . . .
H5 H 0.602(3) 0.343(4) 0.0530(15) 0.066(8) Uiso 1 1 d . . . . .
C00N C 0.6669(3) 0.3227(4) 0.16381(15) 0.0568(7) Uani 1 1 d . . . . .
H6 H 0.749(3) 0.313(4) 0.1609(15) 0.067(8) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl01 C00F 1.741(2) . ?
O002 C007 1.352(3) . ?
O002 C00L 1.452(3) . ?
O003 C007 1.203(3) . ?
N004 C007 1.366(3) . ?
N004 C009 1.407(3) . ?
N004 C00J 1.475(3) . ?
N005 C00K 1.374(3) . ?
N005 C009 1.380(3) . ?
N005 C00B 1.389(3) . ?
N006 C00B 1.326(3) . ?
N006 C008 1.375(3) . ?
C008 C009 1.372(3) . ?
C008 C00A 1.469(3) . ?
C00A C00E 1.389(3) . ?
C00A C00D 1.395(3) . ?
C00B C00I 1.415(3) . ?
C00C C00L 1.488(4) . ?
C00C C00J 1.502(3) . ?
C00C H11 0.97(3) . ?
C00C H10 0.98(3) . ?
C00D C00G 1.384(3) . ?
C00D H0 0.99(3) . ?
C00E C00H 1.374(3) . ?
C00E H3 0.94(2) . ?
C00F C00G 1.376(3) . ?
C00F C00H 1.379(3) . ?
C00G H1 0.98(3) . ?
C00H H2 0.93(3) . ?
C00I C00M 1.348(4) . ?
C00I H4 0.97(3) . ?
C00J H9 0.97(3) . ?
C00J H8 0.99(3) . ?
C00K C00N 1.350(4) . ?
C00K H7 0.88(3) . ?
C00L H13 0.99(3) . ?
C00L H12 1.01(3) . ?
C00M C00N 1.409(4) . ?
C00M H5 0.97(3) . ?
C00N H6 0.94(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C007 O002 C00L 119.59(19) . . ?
C007 N004 C009 118.36(19) . . ?
C007 N004 C00J 125.52(18) . . ?
C009 N004 C00J 116.04(18) . . ?
C00K N005 C009 131.2(2) . . ?
C00K N005 C00B 122.65(19) . . ?
C009 N005 C00B 106.15(17) . . ?
C00B N006 C008 105.53(18) . . ?
O003 C007 O002 118.7(2) . . ?
O003 C007 N004 124.1(2) . . ?
O002 C007 N004 117.2(2) . . ?
C009 C008 N006 110.69(19) . . ?
C009 C008 C00A 129.08(19) . . ?
N006 C008 C00A 120.23(18) . . ?
C008 C009 N005 106.21(18) . . ?
C008 C009 N004 133.2(2) . . ?
N005 C009 N004 120.23(19) . . ?
C00E C00A C00D 118.0(2) . . ?
C00E C00A C008 119.57(19) . . ?
C00D C00A C008 122.43(19) . . ?
N006 C00B N005 111.41(18) . . ?
N006 C00B C00I 131.1(2) . . ?
N005 C00B C00I 117.5(2) . . ?
C00L C00C C00J 109.1(2) . . ?
C00L C00C H11 112.0(15) . . ?
C00J C00C H11 108.7(15) . . ?
C00L C00C H10 108.5(16) . . ?
C00J C00C H10 112.1(16) . . ?
H11 C00C H10 106(2) . . ?
C00G C00D C00A 121.0(2) . . ?
C00G C00D H0 117.0(15) . . ?
C00A C00D H0 122.0(15) . . ?
C00H C00E C00A 121.3(2) . . ?
C00H C00E H3 119.7(14) . . ?
C00A C00E H3 119.0(14) . . ?
C00G C00F C00H 120.7(2) . . ?
C00G C00F Cl01 119.48(18) . . ?
C00H C00F Cl01 119.82(18) . . ?
C00F C00G C00D 119.4(2) . . ?
C00F C00G H1 118.4(16) . . ?
C00D C00G H1 122.3(16) . . ?
C00E C00H C00F 119.6(2) . . ?
C00E C00H H2 121.1(15) . . ?
C00F C00H H2 119.3(15) . . ?
C00M C00I C00B 119.6(2) . . ?
C00M C00I H4 121.6(15) . . ?
C00B C00I H4 118.7(16) . . ?
N004 C00J C00C 110.1(2) . . ?
N004 C00J H9 109.8(16) . . ?
C00C C00J H9 110.3(16) . . ?
N004 C00J H8 107.6(15) . . ?
C00C C00J H8 109.5(14) . . ?
H9 C00J H8 109(2) . . ?
C00N C00K N005 118.9(2) . . ?
C00N C00K H7 126.0(18) . . ?
N005 C00K H7 115.1(18) . . ?
O002 C00L C00C 109.4(2) . . ?
O002 C00L H13 104.7(16) . . ?
C00C C00L H13 115.4(16) . . ?
O002 C00L H12 106.2(14) . . ?
C00C C00L H12 112.5(14) . . ?
H13 C00L H12 108(2) . . ?
C00I C00M C00N 121.1(2) . . ?
C00I C00M H5 120.8(17) . . ?
C00N C00M H5 118.1(17) . . ?
C00K C00N C00M 120.3(3) . . ?
C00K C00N H6 119.8(17) . . ?
C00M C00N H6 120.0(17) . . ?

_refine_diff_density_max         0.192
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.048



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

data_3n
_database_code_depnum_ccdc_archive 'CCDC 2294776'
loop_
_audit_author_name
_audit_author_address
'Constantinos Stoumpos'
;University of Crete
Greece
;
_audit_update_record             
;
2023-09-13 deposited with the CCDC.	2023-11-13 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_RINTA01_3n                  
;
PROBLEM: The value of Rint is greater than 0.18
RESPONSE: The crystals are weakly diffracting at high 2 theta angles.
;
# Added during the CSD deposition process: Wednesday 13 September 2023 11:48 AM
# end Validation Reply Form


_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H17 N3 O4'
_chemical_formula_sum            'C18 H17 N3 O4'
_chemical_formula_weight         337.361

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                   11.7816(13)
_cell_length_b                   7.4720(7)
_cell_length_c                   18.3634(18)
_cell_angle_alpha                90
_cell_angle_beta                 99.553(4)
_cell_angle_gamma                90
_cell_volume                     1594.2(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1200
_cell_measurement_theta_max      22.51
_cell_measurement_theta_min      2.25

_exptl_crystal_description       'rectangular needle'
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.414
_exptl_crystal_F_000             712
_exptl_transmission_factor_min   0.2858
_exptl_transmission_factor_max   0.5584
_exptl_crystal_size_max          0.206
_exptl_crystal_size_mid          0.049
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_T_max  0.7449
_exptl_absorpt_correction_T_min  0.6696
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            79029
_diffrn_reflns_av_unetI/netI     0.0552
_diffrn_reflns_av_R_equivalents  0.2120
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.249
_diffrn_reflns_theta_max         25.999
_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             3141
_reflns_number_gt                1700
_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 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
The crystals are weakly diffracting at high 2 theta angles. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0856P)²+0.0679P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.039(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3141
_refine_ls_number_parameters     295
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1188
_refine_ls_R_factor_gt           0.0587
_refine_ls_wR_factor_ref         0.1684
_refine_ls_wR_factor_gt          0.1322
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_restrained_S_all      1.018
_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
O001 O 0.90174(19) 0.2567(3) 0.70473(11) 0.0618(6) Uani 1 1 d . . . . .
O002 O 0.5405(2) 0.3739(3) 0.33801(12) 0.0660(7) Uani 1 1 d . . . . .
H2 H 0.503(4) 0.309(6) 0.380(3) 0.118(15) Uiso 1 1 d . . . . .
O3 O 0.2269(2) 0.0409(3) 0.61028(12) 0.0692(7) Uani 1 1 d . . . . .
N004 N 0.5447(2) 0.2269(3) 0.58758(12) 0.0466(6) Uani 1 1 d . . . . .
N005 N 0.7388(2) 0.3404(3) 0.62259(12) 0.0491(6) Uani 1 1 d . . . . .
O006 O 0.8136(2) 0.0605(3) 0.62597(13) 0.0765(8) Uani 1 1 d . . . . .
N007 N 0.5108(2) 0.2626(3) 0.46606(12) 0.0477(6) Uani 1 1 d . . . . .
C008 C 0.4653(3) 0.2093(4) 0.52377(14) 0.0446(7) Uani 1 1 d . . . . .
C009 C 0.6453(3) 0.2929(4) 0.56790(14) 0.0474(7) Uani 1 1 d . . . . .
C00A C 0.8165(3) 0.2109(5) 0.64979(15) 0.0525(8) Uani 1 1 d . . . . .
C00B C 0.6226(3) 0.3145(4) 0.49266(15) 0.0473(7) Uani 1 1 d . . . . .
C00C C 0.3545(3) 0.1434(4) 0.52844(16) 0.0494(8) Uani 1 1 d . . . . .
H0 H 0.295(3) 0.129(4) 0.4820(17) 0.057(8) Uiso 1 1 d . . . . .
C00D C 0.6961(3) 0.3829(4) 0.44166(15) 0.0483(7) Uani 1 1 d . . . . .
C00E C 0.6512(3) 0.4123(4) 0.36710(16) 0.0498(8) Uani 1 1 d . . . . .
C00F C 0.3298(3) 0.1020(4) 0.59607(16) 0.0533(8) Uani 1 1 d . . . . .
C00G C 0.5192(3) 0.1830(4) 0.65598(16) 0.0565(8) Uani 1 1 d . . . . .
H6 H 0.576(3) 0.207(4) 0.6981(16) 0.050(8) Uiso 1 1 d . . . . .
C00H C 0.7208(3) 0.4833(5) 0.32038(19) 0.0603(9) Uani 1 1 d . . . . .
H14 H 0.686(3) 0.509(5) 0.269(2) 0.086(12) Uiso 1 1 d . . . . .
C00I C 0.4139(3) 0.1215(5) 0.66037(18) 0.0596(9) Uani 1 1 d . . . . .
H5 H 0.399(3) 0.088(5) 0.706(2) 0.087(12) Uiso 1 1 d . . . . .
C00J C 0.8345(3) 0.5217(5) 0.34521(19) 0.0655(9) Uani 1 1 d . . . . .
H15 H 0.884(3) 0.578(4) 0.3120(19) 0.074(10) Uiso 1 1 d . . . . .
C00K C 0.8122(3) 0.4221(5) 0.46548(19) 0.0651(10) Uani 1 1 d . . . . .
H13 H 0.847(3) 0.405(4) 0.517(2) 0.079(11) Uiso 1 1 d . . . . .
C00L C 0.7418(3) 0.5277(5) 0.6487(2) 0.0632(9) Uani 1 1 d . . . . .
H12 H 0.673(4) 0.543(6) 0.679(2) 0.107(14) Uiso 1 1 d . . . . .
H11 H 0.723(4) 0.597(5) 0.603(2) 0.106(15) Uiso 1 1 d . . . . .
C00M C 0.8912(4) 0.4184(5) 0.7463(2) 0.0694(10) Uani 1 1 d . . . . .
H10 H 0.837(4) 0.395(5) 0.782(2) 0.091(13) Uiso 1 1 d . . . . .
H9 H 0.980(4) 0.427(5) 0.777(2) 0.098(13) Uiso 1 1 d . . . . .
C00N C 0.8560(4) 0.5700(5) 0.6949(2) 0.0732(11) Uani 1 1 d . . . . .
H8 H 0.846(4) 0.689(6) 0.721(2) 0.105(13) Uiso 1 1 d . . . . .
H7 H 0.917(4) 0.590(5) 0.662(2) 0.096(14) Uiso 1 1 d . . . . .
C00O C 0.8805(3) 0.4881(6) 0.4182(2) 0.0729(11) Uani 1 1 d . . . . .
H16 H 0.959(3) 0.518(5) 0.435(2) 0.085(11) Uiso 1 1 d . . . . .
C00P C 0.1333(4) 0.0350(7) 0.5495(2) 0.0761(11) Uani 1 1 d . . . . .
H4 H 0.073(4) -0.011(6) 0.569(2) 0.095(14) Uiso 1 1 d . . . . .
H3 H 0.120(3) 0.159(5) 0.529(2) 0.080(12) Uiso 1 1 d . . . . .
H1 H 0.157(4) -0.059(5) 0.507(2) 0.104(14) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O001 C00A 1.344(3) . ?
O001 C00M 1.445(4) . ?
O002 C00E 1.356(4) . ?
O002 H2 1.06(5) . ?
O3 C00F 1.361(4) . ?
O3 C00P 1.433(4) . ?
N004 C00G 1.379(4) . ?
N004 C008 1.379(3) . ?
N004 C009 1.386(4) . ?
N005 C00A 1.368(4) . ?
N005 C009 1.407(3) . ?
N005 C00L 1.478(4) . ?
O006 C00A 1.204(4) . ?
N007 C008 1.325(4) . ?
N007 C00B 1.382(4) . ?
C008 C00C 1.412(4) . ?
C009 C00B 1.373(4) . ?
C00B C00D 1.469(4) . ?
C00C C00F 1.357(4) . ?
C00C H0 1.02(3) . ?
C00D C00K 1.396(5) . ?
C00D C00E 1.401(4) . ?
C00E C00H 1.387(5) . ?
C00F C00I 1.417(4) . ?
C00G C00I 1.338(5) . ?
C00G H6 0.95(3) . ?
C00H C00J 1.371(5) . ?
C00H H14 0.98(4) . ?
C00I H5 0.92(4) . ?
C00J C00O 1.382(5) . ?
C00J H15 1.00(4) . ?
C00K C00O 1.371(5) . ?
C00K H13 0.97(3) . ?
C00L C00N 1.501(5) . ?
C00L H12 1.06(5) . ?
C00L H11 0.98(4) . ?
C00M C00N 1.488(6) . ?
C00M H10 1.01(4) . ?
C00M H9 1.11(4) . ?
C00N H8 1.03(4) . ?
C00N H7 1.03(4) . ?
C00O H16 0.95(4) . ?
C00P H4 0.92(4) . ?
C00P H3 1.00(4) . ?
C00P H1 1.11(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C00A O001 C00M 119.4(3) . . ?
C00E O002 H2 108(2) . . ?
C00F O3 C00P 117.1(3) . . ?
C00G N004 C008 122.1(3) . . ?
C00G N004 C009 130.3(2) . . ?
C008 N004 C009 107.5(2) . . ?
C00A N005 C009 118.7(2) . . ?
C00A N005 C00L 124.9(3) . . ?
C009 N005 C00L 116.4(2) . . ?
C008 N007 C00B 106.8(2) . . ?
N007 C008 N004 110.1(3) . . ?
N007 C008 C00C 130.8(3) . . ?
N004 C008 C00C 119.0(3) . . ?
C00B C009 N004 105.8(2) . . ?
C00B C009 N005 133.5(3) . . ?
N004 C009 N005 120.4(2) . . ?
O006 C00A O001 118.9(3) . . ?
O006 C00A N005 123.4(3) . . ?
O001 C00A N005 117.7(3) . . ?
C009 C00B N007 109.8(3) . . ?
C009 C00B C00D 130.2(3) . . ?
N007 C00B C00D 120.0(2) . . ?
C00F C00C C008 118.4(3) . . ?
C00F C00C H0 121.5(18) . . ?
C008 C00C H0 120.1(17) . . ?
C00K C00D C00E 117.7(3) . . ?
C00K C00D C00B 121.6(3) . . ?
C00E C00D C00B 120.7(3) . . ?
O002 C00E C00H 117.8(3) . . ?
O002 C00E C00D 122.3(3) . . ?
C00H C00E C00D 119.9(3) . . ?
C00C C00F O3 125.8(3) . . ?
C00C C00F C00I 120.9(3) . . ?
O3 C00F C00I 113.4(3) . . ?
C00I C00G N004 118.8(3) . . ?
C00I C00G H6 123.5(17) . . ?
N004 C00G H6 117.6(18) . . ?
C00J C00H C00E 121.3(3) . . ?
C00J C00H H14 120(2) . . ?
C00E C00H H14 118(2) . . ?
C00G C00I C00F 120.8(3) . . ?
C00G C00I H5 118(2) . . ?
C00F C00I H5 121(3) . . ?
C00H C00J C00O 119.3(3) . . ?
C00H C00J H15 121.1(19) . . ?
C00O C00J H15 120(2) . . ?
C00O C00K C00D 121.6(3) . . ?
C00O C00K H13 118(2) . . ?
C00D C00K H13 120(2) . . ?
N005 C00L C00N 110.7(3) . . ?
N005 C00L H12 107(2) . . ?
C00N C00L H12 112(2) . . ?
N005 C00L H11 103(2) . . ?
C00N C00L H11 115(3) . . ?
H12 C00L H11 108(3) . . ?
O001 C00M C00N 109.9(3) . . ?
O001 C00M H10 108(2) . . ?
C00N C00M H10 114(2) . . ?
O001 C00M H9 99(2) . . ?
C00N C00M H9 115(2) . . ?
H10 C00M H9 110(3) . . ?
C00M C00N C00L 109.1(4) . . ?
C00M C00N H8 114(2) . . ?
C00L C00N H8 107(2) . . ?
C00M C00N H7 110(2) . . ?
C00L C00N H7 110(2) . . ?
H8 C00N H7 107(3) . . ?
C00K C00O C00J 120.2(4) . . ?
C00K C00O H16 121(2) . . ?
C00J C00O H16 118(2) . . ?
O3 C00P H4 105(2) . . ?
O3 C00P H3 108(2) . . ?
H4 C00P H3 115(3) . . ?
O3 C00P H1 108(2) . . ?
H4 C00P H1 110(3) . . ?
H3 C00P H1 111(3) . . ?

_refine_diff_density_max         0.235
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.059



