# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 2056005'
loop_
_audit_author_name
_audit_author_address
'Narcis Avarvari'
;CNRS University of Angers
France
;
_audit_update_record             
;
2021-05-07 deposited with the CCDC.	2021-06-01 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         'C32 H24 N2 O2 S2, 2(C H Cl3)'
_chemical_formula_sum            'C34 H26 Cl6 N2 O2 S2'
_chemical_formula_weight         771.39

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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                   6.5241(2)
_cell_length_b                   9.3333(3)
_cell_length_c                   27.7177(9)
_cell_angle_alpha                90
_cell_angle_beta                 90.516(3)
_cell_angle_gamma                90
_cell_volume                     1687.70(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    150.00(10)
_cell_measurement_reflns_used    3608
_cell_measurement_theta_min      3.1600
_cell_measurement_theta_max      76.0390

_exptl_crystal_description       needle
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.518
_exptl_crystal_F_000             788
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.403
_exptl_crystal_size_mid          0.076
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    6.092
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.81728
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.45a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150.0(1)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'SuperNova(Cu)micro-focus sealed X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Single source at offset, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 5.1990
_diffrn_reflns_number            7224
_diffrn_reflns_av_unetI/netI     0.0362
_diffrn_reflns_av_R_equivalents  0.0279
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         3.189
_diffrn_reflns_theta_max         76.293
_diffrn_reflns_theta_full        74.000
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measured_fraction_theta_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_point_group_measured_fraction_full 0.985
_reflns_number_total             3435
_reflns_number_gt                3050
_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       'CrysAlisPro 1.171.40.45a (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.45a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.45a (Rigaku OD, 2019)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'DIAMOND 3.2k (Crystal Impact GbR, 2014)'
_computing_publication_material  'WinGX publication routines (Farrugia, V2018)'
_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)+(0.0569P)²+0.8928P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3435
_refine_ls_number_parameters     236
_refine_ls_number_restraints     18
_refine_ls_R_factor_all          0.0489
_refine_ls_R_factor_gt           0.0439
_refine_ls_wR_factor_ref         0.1180
_refine_ls_wR_factor_gt          0.1130
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.060
_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 1.1946(3) 0.7519(2) 0.42407(9) 0.0372(5) Uani 1 1 d . . . . .
H1 H 1.320360 0.792548 0.416444 0.045 Uiso 1 1 calc R U . . .
C2 C 1.0714(3) 0.6844(2) 0.39171(8) 0.0376(5) Uani 1 1 d . . . . .
H2 H 1.104266 0.674113 0.359312 0.045 Uiso 1 1 calc R U . . .
C3 C 0.8882(3) 0.6310(2) 0.41180(7) 0.0298(4) Uani 1 1 d . . . . .
H3 H 0.787788 0.582213 0.394363 0.036 Uiso 1 1 calc R U . . .
C4 C 0.8768(3) 0.66092(19) 0.46136(6) 0.0243(4) Uani 1 1 d . . . . .
C5 C 0.7108(3) 0.61332(18) 0.49153(6) 0.0221(3) Uani 1 1 d . . . . .
C6 C 0.5633(3) 0.51241(18) 0.47973(6) 0.0223(3) Uani 1 1 d . . . . .
C7 C 0.4925(3) 0.42118(19) 0.44103(6) 0.0243(4) Uani 1 1 d . . . . .
C8 C 0.7719(3) 0.7727(2) 0.56636(7) 0.0267(4) Uani 1 1 d . . . . .
H8 H 0.860001 0.826749 0.544421 0.032 Uiso 1 1 calc R U . . .
C9 C 0.6181(3) 0.87524(19) 0.58796(7) 0.0264(4) Uani 1 1 d . . . . .
C10 C 0.4447(3) 0.9322(2) 0.56643(7) 0.0320(4) Uani 1 1 d . . . . .
H10 H 0.410125 0.909299 0.534732 0.038 Uiso 1 1 calc R U . . .
C11 C 0.3227(3) 1.0248(2) 0.59321(9) 0.0378(5) Uani 1 1 d . . . . .
H11 H 0.204113 1.062972 0.579488 0.045 Uiso 1 1 calc R U . . .
C12 C 0.3769(3) 1.0601(2) 0.64011(9) 0.0395(5) Uani 1 1 d . . . . .
H12 H 0.294267 1.121954 0.657673 0.047 Uiso 1 1 calc R U . . .
C13 C 0.5534(3) 1.0042(2) 0.66119(7) 0.0355(4) Uani 1 1 d . . . . .
H13 H 0.590063 1.029005 0.692600 0.043 Uiso 1 1 calc R U . . .
C14 C 0.6751(3) 0.9105(2) 0.63479(7) 0.0280(4) Uani 1 1 d . . . . .
C15 C 0.8714(3) 0.8373(2) 0.64933(7) 0.0350(4) Uani 1 1 d . . . . .
H15A H 0.859033 0.793054 0.680843 0.042 Uiso 1 1 calc R U . . .
H15B H 0.984515 0.904723 0.650150 0.042 Uiso 1 1 calc R U . . .
C16 C 0.9034(3) 0.7235(2) 0.61003(7) 0.0326(4) Uani 1 1 d . . . . .
H16A H 0.858911 0.630123 0.621208 0.039 Uiso 1 1 calc R U . . .
H16B H 1.046816 0.717694 0.601350 0.039 Uiso 1 1 calc R U . . .
C17 C 0.4364(4) 0.5865(3) 0.70858(8) 0.0416(5) Uani 1 1 d . . . . .
H17A H 0.469098 0.634569 0.678170 0.050 Uiso 0.797(6) 1 calc R U P A 1
H17B H 0.442072 0.626572 0.675936 0.050 Uiso 0.203(6) 1 calc R U P A 2
Cl1A Cl 0.5459(4) 0.4135(2) 0.70828(7) 0.0826(6) Uani 0.797(6) 1 d . U P A 1
Cl1B Cl 0.6250(12) 0.4706(11) 0.7155(2) 0.0716(18) Uani 0.203(6) 1 d . U P A 2
Cl2A Cl 0.5395(4) 0.6863(3) 0.75646(6) 0.0835(7) Uani 0.797(6) 1 d . U P A 1
Cl2B Cl 0.4519(17) 0.7264(7) 0.7503(3) 0.073(2) Uani 0.203(6) 1 d . U P A 2
Cl3A Cl 0.1708(2) 0.5718(3) 0.71321(5) 0.0654(4) Uani 0.797(6) 1 d . U P A 1
Cl3B Cl 0.2031(11) 0.5023(12) 0.7160(2) 0.0756(15) Uani 0.203(6) 1 d . U P A 2
N1 N 0.6756(2) 0.65516(16) 0.53904(5) 0.0247(3) Uani 1 1 d . . . . .
O1 O 0.5482(2) 0.40509(15) 0.39923(5) 0.0315(3) Uani 1 1 d . . . . .
S1 S 1.09237(7) 0.75344(6) 0.48026(2) 0.03445(15) 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
C1 C2 1.354(3) . ?
C1 S1 1.700(2) . ?
C1 H1 0.9300 . ?
C2 C3 1.414(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.404(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.444(2) . ?
C4 S1 1.7279(18) . ?
C5 C6 1.384(3) . ?
C5 N1 1.395(2) . ?
C6 C6 1.419(3) 3_666 ?
C6 C7 1.442(2) . ?
C7 O1 1.227(2) . ?
C7 N1 1.424(2) 3_666 ?
C8 N1 1.471(2) . ?
C8 C9 1.514(3) . ?
C8 C16 1.547(3) . ?
C8 H8 0.9800 . ?
C9 C10 1.381(3) . ?
C9 C14 1.386(3) . ?
C10 C11 1.393(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.384(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.389(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.393(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.504(3) . ?
C15 C16 1.537(3) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 Cl1B 1.648(7) . ?
C17 Cl3B 1.727(6) . ?
C17 Cl3A 1.744(3) . ?
C17 Cl2B 1.747(7) . ?
C17 Cl2A 1.750(3) . ?
C17 Cl1A 1.766(3) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 S1 112.05(15) . . ?
C2 C1 H1 124.0 . . ?
S1 C1 H1 124.0 . . ?
C1 C2 C3 113.69(19) . . ?
C1 C2 H2 123.2 . . ?
C3 C2 H2 123.2 . . ?
C4 C3 C2 111.59(18) . . ?
C4 C3 H3 124.2 . . ?
C2 C3 H3 124.2 . . ?
C3 C4 C5 123.52(17) . . ?
C3 C4 S1 110.21(13) . . ?
C5 C4 S1 126.21(14) . . ?
C6 C5 N1 107.07(15) . . ?
C6 C5 C4 126.59(16) . . ?
N1 C5 C4 126.26(16) . . ?
C5 C6 C6 109.41(19) . 3_666 ?
C5 C6 C7 142.65(16) . . ?
C6 C6 C7 107.94(19) 3_666 . ?
O1 C7 N1 122.73(16) . 3_666 ?
O1 C7 C6 132.79(17) . . ?
N1 C7 C6 104.46(14) 3_666 . ?
N1 C8 C9 113.17(15) . . ?
N1 C8 C16 114.36(16) . . ?
C9 C8 C16 104.06(15) . . ?
N1 C8 H8 108.3 . . ?
C9 C8 H8 108.3 . . ?
C16 C8 H8 108.3 . . ?
C10 C9 C14 121.67(18) . . ?
C10 C9 C8 128.01(17) . . ?
C14 C9 C8 110.32(17) . . ?
C9 C10 C11 118.57(19) . . ?
C9 C10 H10 120.7 . . ?
C11 C10 H10 120.7 . . ?
C12 C11 C10 120.4(2) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C11 C12 C13 120.61(19) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
C12 C13 C14 119.3(2) . . ?
C12 C13 H13 120.4 . . ?
C14 C13 H13 120.4 . . ?
C9 C14 C13 119.44(19) . . ?
C9 C14 C15 111.33(16) . . ?
C13 C14 C15 129.23(18) . . ?
C14 C15 C16 104.16(16) . . ?
C14 C15 H15A 110.9 . . ?
C16 C15 H15A 110.9 . . ?
C14 C15 H15B 110.9 . . ?
C16 C15 H15B 110.9 . . ?
H15A C15 H15B 108.9 . . ?
C15 C16 C8 105.76(16) . . ?
C15 C16 H16A 110.6 . . ?
C8 C16 H16A 110.6 . . ?
C15 C16 H16B 110.6 . . ?
C8 C16 H16B 110.6 . . ?
H16A C16 H16B 108.7 . . ?
Cl1B C17 Cl3B 110.2(4) . . ?
Cl1B C17 Cl2B 112.0(4) . . ?
Cl3B C17 Cl2B 107.9(3) . . ?
Cl3A C17 Cl2A 111.17(15) . . ?
Cl3A C17 Cl1A 109.33(16) . . ?
Cl2A C17 Cl1A 109.70(16) . . ?
Cl3A C17 H17A 108.9 . . ?
Cl2A C17 H17A 108.9 . . ?
Cl1A C17 H17A 108.9 . . ?
Cl1B C17 H17B 108.9 . . ?
Cl3B C17 H17B 108.9 . . ?
Cl2B C17 H17B 108.9 . . ?
C5 N1 C7 111.11(14) . 3_666 ?
C5 N1 C8 128.44(15) . . ?
C7 N1 C8 120.05(14) 3_666 . ?
C1 S1 C4 92.47(10) . . ?

_refine_diff_density_max         0.396
_refine_diff_density_min         -0.434
_refine_diff_density_rms         0.059



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

data_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2056004'
loop_
_audit_author_name
_audit_author_address
'Narcis Avarvari'
;CNRS University of Angers
France
;
_audit_update_record             
;
2021-05-07 deposited with the CCDC.	2021-06-01 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         'C24 H28 N2 O2 S2'
_chemical_formula_sum            'C24 H28 N2 O2 S2'
_chemical_formula_weight         440.60

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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                   13.0653(11)
_cell_length_b                   5.5363(3)
_cell_length_c                   16.2264(10)
_cell_angle_alpha                90
_cell_angle_beta                 109.093(8)
_cell_angle_gamma                90
_cell_volume                     1109.14(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    150.00(10)
_cell_measurement_reflns_used    1875
_cell_measurement_theta_min      5.7170
_cell_measurement_theta_max      71.5970

_exptl_crystal_description       prism
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_F_000             468
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.01
_exptl_absorpt_coefficient_mu    2.357
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.57383
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.45a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150.0(1)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'SuperNova(Cu)micro-focus sealed X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Single source at offset, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 5.1990
_diffrn_reflns_number            4034
_diffrn_reflns_av_unetI/netI     0.0289
_diffrn_reflns_av_R_equivalents  0.0227
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.580
_diffrn_reflns_theta_max         72.219
_diffrn_reflns_theta_full        71.000
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measured_fraction_theta_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_point_group_measured_fraction_full 0.985
_reflns_number_total             2123
_reflns_number_gt                1807
_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       'CrysAlisPro 1.171.40.45a (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.45a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.45a (Rigaku OD, 2019)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'DIAMOND 3.2k (Crystal Impact GbR, 2014)'
_computing_publication_material  'WinGX publication routines (Farrugia, V2018)'
_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)+(0.0735P)²+0.2070P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2123
_refine_ls_number_parameters     168
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.0526
_refine_ls_R_factor_gt           0.0455
_refine_ls_wR_factor_ref         0.1312
_refine_ls_wR_factor_gt          0.1224
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.055
_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 0.6617(2) 1.1343(4) 0.77553(15) 0.0690(7) Uani 1 1 d . . . . .
H1 H 0.694624 1.218695 0.826954 0.083 Uiso 1 1 calc R U . . .
C2 C 0.5676(2) 1.1972(4) 0.71643(14) 0.0612(6) Uani 1 1 d . . . . .
H2 H 0.528383 1.332955 0.721878 0.073 Uiso 1 1 calc R U . . .
C3 C 0.53353(19) 1.0373(3) 0.64481(12) 0.0520(5) Uani 1 1 d . . . . .
H3 H 0.468913 1.054683 0.598939 0.062 Uiso 1 1 calc R U . . .
C4 C 0.60598(17) 0.8535(3) 0.65011(11) 0.0484(4) Uani 1 1 d . . . . .
C5 C 0.58864(16) 0.6608(3) 0.58672(10) 0.0434(4) Uani 1 1 d . . . . .
C6 C 0.49154(16) 0.5990(3) 0.52470(10) 0.0428(4) Uani 1 1 d . . . . .
C7 C 0.62166(16) 0.3374(3) 0.50791(11) 0.0452(4) Uani 1 1 d . . . . .
C8 C 0.78271(17) 0.5065(4) 0.62236(12) 0.0528(5) Uani 1 1 d . . . . .
H8A H 0.812253 0.350602 0.614624 0.063 Uiso 1 1 calc R U . . .
H8B H 0.795100 0.527653 0.684208 0.063 Uiso 1 1 calc R U . . .
C9 C 0.84379(18) 0.7030(4) 0.59197(14) 0.0595(5) Uani 1 1 d . . . . .
H9A H 0.809584 0.856287 0.598247 0.071 Uiso 0.474(8) 1 calc R U P A 1
H9B H 0.819378 0.861527 0.604928 0.071 Uiso 0.526(8) 1 calc R U P A 2
C10A C 0.8287(14) 0.676(3) 0.4913(11) 0.089(5) Uani 0.474(8) 1 d . U P A 1
H10A H 0.857504 0.521613 0.481386 0.106 Uiso 0.474(8) 1 calc R U P A 1
H10B H 0.752020 0.678800 0.458099 0.106 Uiso 0.474(8) 1 calc R U P A 1
C10B C 0.9675(16) 0.675(3) 0.6425(11) 0.072(2) Uani 0.526(8) 1 d . U P A 2
H10C H 0.992850 0.523948 0.626090 0.087 Uiso 0.526(8) 1 calc R U P A 2
H10D H 0.978740 0.669300 0.704622 0.087 Uiso 0.526(8) 1 calc R U P A 2
C11A C 0.8850(7) 0.8759(17) 0.4587(6) 0.116(3) Uani 0.474(8) 1 d . . P A 1
H11A H 0.862454 1.029853 0.473833 0.175 Uiso 0.474(8) 1 calc R U P A 1
H11B H 0.866182 0.864536 0.396429 0.175 Uiso 0.474(8) 1 calc R U P A 1
H11C H 0.961975 0.859588 0.485049 0.175 Uiso 0.474(8) 1 calc R U P A 1
C11B C 1.0327(4) 0.8787(11) 0.6243(4) 0.0850(19) Uani 0.526(8) 1 d . . P A 2
H11D H 1.030355 0.871095 0.564635 0.127 Uiso 0.526(8) 1 calc R U P A 2
H11E H 1.106401 0.865441 0.662008 0.127 Uiso 0.526(8) 1 calc R U P A 2
H11F H 1.003060 1.029964 0.634676 0.127 Uiso 0.526(8) 1 calc R U P A 2
C12A C 0.9587(18) 0.713(4) 0.6555(13) 0.091(4) Uani 0.474(8) 1 d . U P A 1
H12A H 0.956814 0.725599 0.713958 0.136 Uiso 0.474(8) 1 calc R U P A 1
H12B H 0.995155 0.851792 0.642637 0.136 Uiso 0.474(8) 1 calc R U P A 1
H12C H 0.996892 0.569366 0.649931 0.136 Uiso 0.474(8) 1 calc R U P A 1
C12B C 0.8265(8) 0.686(2) 0.4970(9) 0.058(3) Uani 0.526(8) 1 d . U P A 2
H12D H 0.851601 0.831809 0.477738 0.087 Uiso 0.526(8) 1 calc R U P A 2
H12E H 0.750706 0.665425 0.465915 0.087 Uiso 0.526(8) 1 calc R U P A 2
H12F H 0.866013 0.550778 0.485980 0.087 Uiso 0.526(8) 1 calc R U P A 2
N1 N 0.66695(13) 0.5045(3) 0.57689(9) 0.0461(4) Uani 1 1 d . . . . .
O1 O 0.67577(12) 0.1816(2) 0.48760(8) 0.0530(4) Uani 1 1 d . . . . .
S1 S 0.71465(5) 0.87918(12) 0.74528(4) 0.0716(2) 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
C1 C2 1.335(4) . ?
C1 S1 1.713(2) . ?
C1 H1 0.9300 . ?
C2 C3 1.412(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.373(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.447(2) . ?
C4 S1 1.728(2) . ?
C5 C6 1.380(3) . ?
C5 N1 1.389(2) . ?
C6 C6 1.418(3) 3_666 ?
C6 C7 1.442(3) 3_666 ?
C7 O1 1.227(2) . ?
C7 N1 1.423(2) . ?
C8 N1 1.450(3) . ?
C8 C9 1.524(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C12B 1.485(14) . ?
C9 C10B 1.563(19) . ?
C9 C12A 1.52(2) . ?
C9 C10A 1.588(18) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C10A C11A 1.51(2) . ?
C10A H10A 0.9700 . ?
C10A H10B 0.9700 . ?
C10B C11B 1.50(2) . ?
C10B H10C 0.9700 . ?
C10B H10D 0.9700 . ?
C11A H11A 0.9600 . ?
C11A H11B 0.9600 . ?
C11A H11C 0.9600 . ?
C11B H11D 0.9600 . ?
C11B H11E 0.9600 . ?
C11B H11F 0.9600 . ?
C12A H12A 0.9600 . ?
C12A H12B 0.9600 . ?
C12A H12C 0.9600 . ?
C12B H12D 0.9600 . ?
C12B H12E 0.9600 . ?
C12B H12F 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 S1 111.88(16) . . ?
C2 C1 H1 124.1 . . ?
S1 C1 H1 124.1 . . ?
C1 C2 C3 113.3(2) . . ?
C1 C2 H2 123.3 . . ?
C3 C2 H2 123.3 . . ?
C4 C3 C2 112.8(2) . . ?
C4 C3 H3 123.6 . . ?
C2 C3 H3 123.6 . . ?
C3 C4 C5 123.86(19) . . ?
C3 C4 S1 110.06(14) . . ?
C5 C4 S1 125.98(15) . . ?
C6 C5 N1 107.33(15) . . ?
C6 C5 C4 126.44(17) . . ?
N1 C5 C4 126.23(18) . . ?
C5 C6 C6 109.1(2) . 3_666 ?
C5 C6 C7 142.66(16) . 3_666 ?
C6 C6 C7 108.2(2) 3_666 3_666 ?
O1 C7 N1 122.72(18) . . ?
O1 C7 C6 133.25(18) . 3_666 ?
N1 C7 C6 104.04(14) . 3_666 ?
N1 C8 C9 114.22(15) . . ?
N1 C8 H8A 108.7 . . ?
C9 C8 H8A 108.7 . . ?
N1 C8 H8B 108.7 . . ?
C9 C8 H8B 108.7 . . ?
H8A C8 H8B 107.6 . . ?
C12B C9 C10B 108.6(7) . . ?
C12B C9 C8 111.9(5) . . ?
C10B C9 C8 108.8(7) . . ?
C8 C9 C12A 108.3(9) . . ?
C8 C9 C10A 111.4(7) . . ?
C12A C9 C10A 117.6(10) . . ?
C8 C9 H9A 106.3 . . ?
C12A C9 H9A 106.3 . . ?
C10A C9 H9A 106.3 . . ?
C12B C9 H9B 109.2 . . ?
C10B C9 H9B 109.2 . . ?
C8 C9 H9B 109.2 . . ?
C11A C10A C9 112.4(13) . . ?
C11A C10A H10A 109.1 . . ?
C9 C10A H10A 109.1 . . ?
C11A C10A H10B 109.1 . . ?
C9 C10A H10B 109.1 . . ?
H10A C10A H10B 107.9 . . ?
C9 C10B C11B 112.3(10) . . ?
C9 C10B H10C 109.1 . . ?
C11B C10B H10C 109.1 . . ?
C9 C10B H10D 109.1 . . ?
C11B C10B H10D 109.1 . . ?
H10C C10B H10D 107.9 . . ?
C10A C11A H11A 109.5 . . ?
C10A C11A H11B 109.5 . . ?
H11A C11A H11B 109.5 . . ?
C10A C11A H11C 109.5 . . ?
H11A C11A H11C 109.5 . . ?
H11B C11A H11C 109.5 . . ?
C10B C11B H11D 109.5 . . ?
C10B C11B H11E 109.5 . . ?
H11D C11B H11E 109.5 . . ?
C10B C11B H11F 109.5 . . ?
H11D C11B H11F 109.5 . . ?
H11E C11B H11F 109.5 . . ?
C9 C12A H12A 109.5 . . ?
C9 C12A H12B 109.5 . . ?
H12A C12A H12B 109.5 . . ?
C9 C12A H12C 109.5 . . ?
H12A C12A H12C 109.5 . . ?
H12B C12A H12C 109.5 . . ?
C9 C12B H12D 109.5 . . ?
C9 C12B H12E 109.5 . . ?
H12D C12B H12E 109.5 . . ?
C9 C12B H12F 109.5 . . ?
H12D C12B H12F 109.5 . . ?
H12E C12B H12F 109.5 . . ?
C5 N1 C7 111.29(16) . . ?
C5 N1 C8 128.48(16) . . ?
C7 N1 C8 120.07(15) . . ?
C1 S1 C4 91.90(11) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 C1 C2 C3 1.2(2) . . . . ?
C1 C2 C3 C4 -1.5(2) . . . . ?
C2 C3 C4 C5 177.74(16) . . . . ?
C2 C3 C4 S1 1.0(2) . . . . ?
C3 C4 C5 C6 -15.6(3) . . . . ?
S1 C4 C5 C6 160.53(14) . . . . ?
C3 C4 C5 N1 164.06(16) . . . . ?
S1 C4 C5 N1 -19.8(2) . . . . ?
N1 C5 C6 C6 0.2(2) . . . 3_666 ?
C4 C5 C6 C6 179.97(17) . . . 3_666 ?
N1 C5 C6 C7 179.8(2) . . . 3_666 ?
C4 C5 C6 C7 -0.5(3) . . . 3_666 ?
N1 C8 C9 C12B -57.0(4) . . . . ?
N1 C8 C9 C10B -177.0(6) . . . . ?
N1 C8 C9 C12A 169.7(8) . . . . ?
N1 C8 C9 C10A -59.4(7) . . . . ?
C8 C9 C10A C11A 177.7(8) . . . . ?
C12A C9 C10A C11A -56.5(15) . . . . ?
C12B C9 C10B C11B 64.6(11) . . . . ?
C8 C9 C10B C11B -173.3(7) . . . . ?
C6 C5 N1 C7 -0.06(18) . . . . ?
C4 C5 N1 C7 -179.81(15) . . . . ?
C6 C5 N1 C8 175.31(16) . . . . ?
C4 C5 N1 C8 -4.4(3) . . . . ?
O1 C7 N1 C5 -179.78(15) . . . . ?
C6 C7 N1 C5 -0.12(17) 3_666 . . . ?
O1 C7 N1 C8 4.4(2) . . . . ?
C6 C7 N1 C8 -175.93(14) 3_666 . . . ?
C9 C8 N1 C5 -75.4(2) . . . . ?
C9 C8 N1 C7 99.6(2) . . . . ?
C2 C1 S1 C4 -0.54(18) . . . . ?
C3 C4 S1 C1 -0.30(15) . . . . ?
C5 C4 S1 C1 -176.92(17) . . . . ?

_refine_diff_density_max         0.436
_refine_diff_density_min         -0.264
_refine_diff_density_rms         0.049



####################################################################### 
# 
# 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_shelx_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 2082406'
loop_
_audit_author_name
_audit_author_address
'Narcis Avarvari'
;CNRS University of Angers
France
;
_audit_update_record             
;
2021-05-07 deposited with the CCDC.	2021-06-01 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         'C24 H26 N4 O2'
_chemical_formula_sum            'C24 H26 N4 O2'
_chemical_formula_weight         402.49

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   11.5078(9)
_cell_length_b                   5.6097(4)
_cell_length_c                   16.8043(11)
_cell_angle_alpha                90
_cell_angle_beta                 106.234(8)
_cell_angle_gamma                90
_cell_volume                     1041.55(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    200.4(6)
_cell_measurement_reflns_used    1666
_cell_measurement_theta_min      4.1730
_cell_measurement_theta_max      73.0350

_exptl_crystal_description       prism
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_F_000             428
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.116
_exptl_crystal_size_mid          0.066
_exptl_crystal_size_min          0.0156
_exptl_absorpt_coefficient_mu    0.667
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.87824
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.45a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200.4(6)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'SuperNova(Cu)micro-focus sealed X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Single source at offset, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 5.1990
_diffrn_reflns_number            4206
_diffrn_reflns_av_unetI/netI     0.0262
_diffrn_reflns_av_R_equivalents  0.0204
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         4.170
_diffrn_reflns_theta_max         76.057
_diffrn_reflns_theta_full        74.000
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measured_fraction_theta_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_point_group_measured_fraction_full 0.983
_reflns_number_total             2096
_reflns_number_gt                1789
_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       'CrysAlisPro 1.171.40.45a (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.45a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.45a (Rigaku OD, 2019)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'DIAMOND 3.2k (Crystal Impact GbR, 2014)'
_computing_publication_material  'WinGX publication routines (Farrugia, V2018)'
_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)+(0.0577P)²+0.4053P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0044(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2096
_refine_ls_number_parameters     178
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0622
_refine_ls_R_factor_gt           0.0548
_refine_ls_wR_factor_ref         0.1430
_refine_ls_wR_factor_gt          0.1372
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_restrained_S_all      1.088
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.42664(18) 0.3547(4) 0.06805(12) 0.0520(5) Uani 1 1 d . . . . .
C2 C 0.52181(16) 0.4105(3) 0.03066(11) 0.0467(5) Uani 1 1 d . . . . .
C3 C 0.63914(17) 0.3567(3) 0.03288(11) 0.0466(5) Uani 1 1 d . . . . .
C4 C 0.72133(17) 0.1920(3) 0.09096(11) 0.0448(4) Uani 1 1 d . . . . .
C5 C 0.67414(18) -0.0095(3) 0.11764(11) 0.0472(5) Uani 1 1 d . . . . .
H5 H 0.591972 -0.043971 0.098490 0.057 Uiso 1 1 calc R U . . .
C6 C 0.7522(2) -0.1594(4) 0.17367(12) 0.0530(5) Uani 1 1 d . . . . .
H6 H 0.723357 -0.297913 0.191940 0.064 Uiso 1 1 calc R U . . .
C7 C 0.8725(2) -0.1002(4) 0.20173(12) 0.0557(5) Uani 1 1 d . . . . .
H7 H 0.926634 -0.197319 0.239386 0.067 Uiso 1 1 calc R U . . .
C8 C 0.91111(19) 0.1055(4) 0.17296(13) 0.0586(6) Uani 1 1 d . . . . .
H8 H 0.992553 0.145323 0.192897 0.070 Uiso 1 1 calc R U . . .
C9A C 0.2145(5) 0.5197(15) 0.0495(6) 0.0511(16) Uani 0.611(7) 1 d D . P A 1
H9A H 0.164425 0.646355 0.016940 0.061 Uiso 0.611(7) 1 calc R U P A 1
C9B C 0.2323(10) 0.570(3) 0.0676(8) 0.076(5) Uani 0.389(7) 1 d D . P A 2
H9B H 0.178239 0.677682 0.028085 0.091 Uiso 0.389(7) 1 calc R U P A 2
C10A C 0.1468(4) 0.2921(9) 0.0318(3) 0.0557(11) Uani 0.611(7) 1 d D . P A 1
H10A H 0.071296 0.307853 0.045140 0.084 Uiso 0.611(7) 1 calc R U P A 1
H10B H 0.193726 0.167124 0.064581 0.084 Uiso 0.611(7) 1 calc R U P A 1
H18C H 0.131324 0.254026 -0.025966 0.084 Uiso 0.611(7) 1 calc R U P A 1
C10B C 0.2689(9) 0.719(2) 0.1533(6) 0.074(2) Uani 0.389(7) 1 d D . P A 2
H10D H 0.313599 0.618462 0.197433 0.111 Uiso 0.389(7) 1 calc R U P A 2
H10E H 0.196799 0.774545 0.165561 0.111 Uiso 0.389(7) 1 calc R U P A 2
H10F H 0.317854 0.853414 0.147815 0.111 Uiso 0.389(7) 1 calc R U P A 2
C11A C 0.2557(6) 0.5981(12) 0.1399(3) 0.0694(15) Uani 0.611(7) 1 d . . P A 1
H11A H 0.297709 0.467742 0.173937 0.083 Uiso 0.611(7) 1 calc R U P A 1
H11B H 0.311601 0.730649 0.145760 0.083 Uiso 0.611(7) 1 calc R U P A 1
C11B C 0.1499(6) 0.3704(15) 0.0797(6) 0.073(2) Uani 0.389(7) 1 d . . P A 2
H11C H 0.191899 0.273772 0.126906 0.088 Uiso 0.389(7) 1 calc R U P A 2
H11D H 0.078538 0.437403 0.091118 0.088 Uiso 0.389(7) 1 calc R U P A 2
C12A C 0.1478(4) 0.6726(9) 0.1690(3) 0.0749(15) Uani 0.611(7) 1 d . . P A 1
H12A H 0.095840 0.537761 0.167355 0.112 Uiso 0.611(7) 1 calc R U P A 1
H12B H 0.103904 0.795739 0.133426 0.112 Uiso 0.611(7) 1 calc R U P A 1
H12C H 0.175415 0.731544 0.224789 0.112 Uiso 0.611(7) 1 calc R U P A 1
C12B C 0.1133(9) 0.2189(19) 0.0043(6) 0.077(3) Uani 0.389(7) 1 d . . P A 2
H12D H 0.182934 0.137667 -0.003106 0.116 Uiso 0.389(7) 1 calc R U P A 2
H12E H 0.078611 0.317242 -0.043190 0.116 Uiso 0.389(7) 1 calc R U P A 2
H12F H 0.054529 0.103978 0.010371 0.116 Uiso 0.389(7) 1 calc R U P A 2
N1 N 0.32866(14) 0.5057(3) 0.02593(10) 0.0520(4) Uani 1 1 d D . . . .
N2 N 0.83883(15) 0.2529(3) 0.11788(10) 0.0536(5) Uani 1 1 d . . . . .
O1 O 0.42133(13) 0.2128(3) 0.12197(10) 0.0659(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
C1 O1 1.221(2) . ?
C1 N1 1.429(2) . ?
C1 C2 1.441(3) . ?
C2 C3 1.374(3) . ?
C2 C2 1.426(3) 3_665 ?
C3 N1 1.384(3) 3_665 ?
C3 C4 1.478(2) . ?
C4 N2 1.345(2) . ?
C4 C5 1.382(3) . ?
C5 C6 1.388(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.373(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.372(3) . ?
C7 H7 0.9300 . ?
C8 N2 1.343(2) . ?
C8 H8 0.9300 . ?
C9A N1 1.476(6) . ?
C9A C10A 1.482(9) . ?
C9A C11A 1.524(9) . ?
C9A H9A 0.9800 . ?
C9B N1 1.511(9) . ?
C9B C11B 1.519(16) . ?
C9B C10B 1.616(11) . ?
C9B H9B 0.9800 . ?
C10A H10A 0.9600 . ?
C10A H10B 0.9600 . ?
C10A H18C 0.9600 . ?
C10B H10D 0.9600 . ?
C10B H10E 0.9600 . ?
C10B H10F 0.9600 . ?
C11A C12A 1.515(7) . ?
C11A H11A 0.9700 . ?
C11A H11B 0.9700 . ?
C11B C12B 1.486(12) . ?
C11B H11C 0.9700 . ?
C11B H11D 0.9700 . ?
C12A H12A 0.9600 . ?
C12A H12B 0.9600 . ?
C12A H12C 0.9600 . ?
C12B H12D 0.9600 . ?
C12B H12E 0.9600 . ?
C12B H12F 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 N1 123.90(19) . . ?
O1 C1 C2 131.85(18) . . ?
N1 C1 C2 104.25(16) . . ?
C3 C2 C2 108.6(2) . 3_665 ?
C3 C2 C1 143.27(17) . . ?
C2 C2 C1 108.1(2) 3_665 . ?
C2 C3 N1 108.38(16) . 3_665 ?
C2 C3 C4 126.71(18) . . ?
N1 C3 C4 124.80(18) 3_665 . ?
N2 C4 C5 123.23(17) . . ?
N2 C4 C3 117.46(17) . . ?
C5 C4 C3 119.25(17) . . ?
C4 C5 C6 118.50(18) . . ?
C4 C5 H5 120.7 . . ?
C6 C5 H5 120.7 . . ?
C7 C6 C5 119.04(19) . . ?
C7 C6 H6 120.5 . . ?
C5 C6 H6 120.5 . . ?
C8 C7 C6 118.51(18) . . ?
C8 C7 H7 120.7 . . ?
C6 C7 H7 120.7 . . ?
N2 C8 C7 124.2(2) . . ?
N2 C8 H8 117.9 . . ?
C7 C8 H8 117.9 . . ?
N1 C9A C10A 111.0(5) . . ?
N1 C9A C11A 103.3(5) . . ?
C10A C9A C11A 116.7(7) . . ?
N1 C9A H9A 108.5 . . ?
C10A C9A H9A 108.5 . . ?
C11A C9A H9A 108.5 . . ?
N1 C9B C11B 116.9(10) . . ?
N1 C9B C10B 119.7(8) . . ?
C11B C9B C10B 106.2(9) . . ?
N1 C9B H9B 104.1 . . ?
C11B C9B H9B 104.1 . . ?
C10B C9B H9B 104.1 . . ?
C9A C10A H10A 109.5 . . ?
C9A C10A H10B 109.5 . . ?
H10A C10A H10B 109.5 . . ?
C9A C10A H18C 109.5 . . ?
H10A C10A H18C 109.5 . . ?
H10B C10A H18C 109.5 . . ?
C9B C10B H10D 109.5 . . ?
C9B C10B H10E 109.5 . . ?
H10D C10B H10E 109.5 . . ?
C9B C10B H10F 109.5 . . ?
H10D C10B H10F 109.5 . . ?
H10E C10B H10F 109.5 . . ?
C12A C11A C9A 110.3(5) . . ?
C12A C11A H11A 109.6 . . ?
C9A C11A H11A 109.6 . . ?
C12A C11A H11B 109.6 . . ?
C9A C11A H11B 109.6 . . ?
H11A C11A H11B 108.1 . . ?
C12B C11B C9B 110.3(8) . . ?
C12B C11B H11C 109.6 . . ?
C9B C11B H11C 109.6 . . ?
C12B C11B H11D 109.6 . . ?
C9B C11B H11D 109.6 . . ?
H11C C11B H11D 108.1 . . ?
C11A C12A H12A 109.5 . . ?
C11A C12A H12B 109.5 . . ?
H12A C12A H12B 109.5 . . ?
C11A C12A H12C 109.5 . . ?
H12A C12A H12C 109.5 . . ?
H12B C12A H12C 109.5 . . ?
C11B C12B H12D 109.5 . . ?
C11B C12B H12E 109.5 . . ?
H12D C12B H12E 109.5 . . ?
C11B C12B H12F 109.5 . . ?
H12D C12B H12F 109.5 . . ?
H12E C12B H12F 109.5 . . ?
C3 N1 C1 110.64(16) 3_665 . ?
C3 N1 C9A 126.7(4) 3_665 . ?
C1 N1 C9A 122.5(4) . . ?
C3 N1 C9B 125.1(7) 3_665 . ?
C1 N1 C9B 119.5(6) . . ?
C8 N2 C4 116.51(18) . . ?

_refine_diff_density_max         0.236
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.038



