# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_ms2100s
_database_code_depnum_ccdc_archive 'CCDC 2083073'
loop_
_audit_author_name
_audit_author_address
'Arkady Ellern'
;Chemistry Department, Iowa State University, Osborn Drive, Ames, Iowa
United States of America
;
_audit_update_record             
;
2021-05-11 deposited with the CCDC.	2022-09-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H19 N1 O2'
_chemical_formula_weight         305.38

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

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.187(3)
_cell_length_b                   9.949(3)
_cell_length_c                   10.504(3)
_cell_angle_alpha                76.646(6)
_cell_angle_beta                 82.523(6)
_cell_angle_gamma                75.163(6)
_cell_volume                     802.4(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    570(2)
_cell_measurement_reflns_used    1036
_cell_measurement_theta_min      2.63
_cell_measurement_theta_max      23.83

_exptl_crystal_description       cube
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_crystal_density_meas      1.264
_exptl_crystal_density_diffrn    1.264
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             185
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.9898
_exptl_absorpt_correction_T_max  0.9974
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      570(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4083
_diffrn_reflns_av_R_equivalents  0.0281
_diffrn_reflns_av_sigmaI/netI    0.0563
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.00
_diffrn_reflns_theta_max         25.08
_reflns_number_total             2802
_reflns_number_gt                1637
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0783P)²+0.3121P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.004(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2802
_refine_ls_number_parameters     241
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1044
_refine_ls_R_factor_gt           0.0580
_refine_ls_wR_factor_ref         0.1853
_refine_ls_wR_factor_gt          0.1590
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.063
_refine_ls_shift/su_max          0.013
_refine_ls_shift/su_mean         0.001

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2849(4) 0.0160(3) 0.1790(3) 0.0461(7) Uani 1 1 d . . .
N1 N 0.1950(4) -0.2802(3) 0.5243(2) 0.0614(8) Uani 1 1 d . . .
O2 O 0.2545(3) 0.3586(3) -0.1585(2) 0.0776(8) Uani 1 1 d . . .
O1 O 0.6721(3) 0.1146(3) 0.1375(2) 0.0768(8) Uani 1 1 d . . .
C2 C 0.5276(4) 0.3896(3) -0.1261(3) 0.0493(8) Uani 1 1 d . . .
C3 C 0.6475(4) 0.3156(3) -0.0398(3) 0.0482(8) Uani 1 1 d . . .
C4 C 0.1375(4) -0.0343(3) 0.1973(3) 0.0531(8) Uani 1 1 d . . .
C5 C 0.3987(4) -0.0379(4) 0.2739(3) 0.0596(9) Uani 1 1 d . . .
C6 C 0.3820(4) 0.3214(3) -0.0993(3) 0.0510(8) Uani 1 1 d . . .
C7 C 0.3689(4) -0.1355(4) 0.3860(3) 0.0607(9) Uani 1 1 d . . .
C8 C 0.2199(4) -0.1828(3) 0.4043(3) 0.0512(8) Uani 1 1 d . . .
C9 C 0.1032(4) -0.1329(3) 0.3086(3) 0.0547(8) Uani 1 1 d . . .
C10 C 0.5887(4) 0.1969(3) 0.0511(3) 0.0498(8) Uani 1 1 d . . .
C11 C 0.5508(5) 0.5094(4) -0.2165(3) 0.0629(10) Uani 1 1 d . . .
C12 C 0.4195(4) 0.2012(3) 0.0152(3) 0.0458(7) Uani 1 1 d . . .
C13 C 0.3013(4) 0.1265(3) 0.0638(3) 0.0480(8) Uani 1 1 d . . .
C14 C 0.7977(4) 0.3581(4) -0.0415(3) 0.0618(9) Uani 1 1 d . . .
C15 C 0.6966(5) 0.5526(4) -0.2192(3) 0.0670(10) Uani 1 1 d . . .
C16 C 0.8202(5) 0.4773(4) -0.1342(4) 0.0669(10) Uani 1 1 d . . .
C17 C -0.0633(5) -0.1759(5) 0.3217(4) 0.0864(13) Uani 1 1 d . . .
H8 H -0.1298 -0.1202 0.2506 0.130 Uiso 1 1 calc R . .
H10 H -0.1237 -0.1600 0.4036 0.130 Uiso 1 1 calc R . .
H9 H -0.0420 -0.2748 0.3192 0.130 Uiso 1 1 calc R . .
C18 C 0.4978(5) -0.1911(5) 0.4871(4) 0.1028(16) Uani 1 1 d . . .
H11 H 0.5822 -0.1362 0.4671 0.154 Uiso 1 1 calc R . .
H12 H 0.5508 -0.2888 0.4861 0.154 Uiso 1 1 calc R . .
H13 H 0.4425 -0.1836 0.5724 0.154 Uiso 1 1 calc R . .
C19 C 0.1732(9) -0.4144(5) 0.5236(4) 0.133(2) Uani 1 1 d . . .
H16 H 0.2073 -0.4783 0.6043 0.199 Uiso 1 1 calc R . .
H18 H 0.2411 -0.4492 0.4512 0.199 Uiso 1 1 calc R . .
H17 H 0.0560 -0.4083 0.5150 0.199 Uiso 1 1 calc R . .
C20 C 0.1084(7) -0.2238(5) 0.6325(4) 0.129(2) Uani 1 1 d . . .
H19 H -0.0112 -0.1972 0.6222 0.193 Uiso 1 1 calc R . .
H14 H 0.1466 -0.1417 0.6372 0.193 Uiso 1 1 calc R . .
H15 H 0.1308 -0.2942 0.7117 0.193 Uiso 1 1 calc R . .
H7 H 0.045(4) 0.004(3) 0.130(3) 0.054(8) Uiso 1 1 d . . .
H5 H 0.196(4) 0.162(3) 0.013(3) 0.060(9) Uiso 1 1 d . . .
H4 H 0.892(5) 0.296(4) 0.023(4) 0.091(12) Uiso 1 1 d . . .
H3 H 0.939(5) 0.511(4) -0.129(4) 0.095(12) Uiso 1 1 d . . .
H6 H 0.493(4) -0.003(3) 0.266(3) 0.057(9) Uiso 1 1 d . . .
H1 H 0.701(4) 0.649(4) -0.279(4) 0.086(11) Uiso 1 1 d . . .
H2 H 0.474(5) 0.557(4) -0.272(4) 0.086(13) 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
C1 C5 1.374(4) . ?
C1 C4 1.396(4) . ?
C1 C13 1.452(4) . ?
N1 C19 1.394(5) . ?
N1 C20 1.411(5) . ?
N1 C8 1.427(4) . ?
O2 C6 1.216(4) . ?
O1 C10 1.222(3) . ?
C2 C3 1.371(4) . ?
C2 C11 1.380(4) . ?
C2 C6 1.483(4) . ?
C3 C14 1.396(4) . ?
C3 C10 1.479(4) . ?
C4 C9 1.391(4) . ?
C4 H7 1.04(3) . ?
C5 C7 1.381(4) . ?
C5 H6 0.91(3) . ?
C6 C12 1.488(4) . ?
C7 C8 1.392(4) . ?
C7 C18 1.506(5) . ?
C8 C9 1.395(4) . ?
C9 C17 1.510(5) . ?
C10 C12 1.470(4) . ?
C11 C15 1.363(5) . ?
C11 H2 0.88(4) . ?
C12 C13 1.347(4) . ?
C13 H5 1.02(3) . ?
C14 C16 1.386(5) . ?
C14 H4 1.07(4) . ?
C15 C16 1.386(5) . ?
C15 H1 1.03(4) . ?
C16 H3 1.12(4) . ?
C17 H8 0.9600 . ?
C17 H10 0.9600 . ?
C17 H9 0.9600 . ?
C18 H11 0.9600 . ?
C18 H12 0.9600 . ?
C18 H13 0.9600 . ?
C19 H16 0.9600 . ?
C19 H18 0.9600 . ?
C19 H17 0.9600 . ?
C20 H19 0.9600 . ?
C20 H14 0.9600 . ?
C20 H15 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
C5 C1 C4 117.6(3) . . ?
C5 C1 C13 125.3(3) . . ?
C4 C1 C13 117.0(3) . . ?
C19 N1 C20 113.7(4) . . ?
C19 N1 C8 120.8(3) . . ?
C20 N1 C8 117.9(3) . . ?
C3 C2 C11 121.1(3) . . ?
C3 C2 C6 108.8(3) . . ?
C11 C2 C6 130.1(3) . . ?
C2 C3 C14 121.1(3) . . ?
C2 C3 C10 110.6(3) . . ?
C14 C3 C10 128.3(3) . . ?
C9 C4 C1 121.9(3) . . ?
C9 C4 H7 116.8(16) . . ?
C1 C4 H7 121.2(16) . . ?
C1 C5 C7 122.2(3) . . ?
C1 C5 H6 118.9(19) . . ?
C7 C5 H6 119(2) . . ?
O2 C6 C2 126.3(3) . . ?
O2 C6 C12 126.5(3) . . ?
C2 C6 C12 107.2(2) . . ?
C5 C7 C8 119.6(3) . . ?
C5 C7 C18 120.0(3) . . ?
C8 C7 C18 120.3(3) . . ?
C7 C8 C9 119.8(3) . . ?
C7 C8 N1 116.6(3) . . ?
C9 C8 N1 123.6(3) . . ?
C4 C9 C8 118.9(3) . . ?
C4 C9 C17 117.7(3) . . ?
C8 C9 C17 123.3(3) . . ?
O1 C10 C12 129.5(3) . . ?
O1 C10 C3 123.6(3) . . ?
C12 C10 C3 106.9(2) . . ?
C15 C11 C2 118.6(3) . . ?
C15 C11 H2 120(3) . . ?
C2 C11 H2 122(3) . . ?
C13 C12 C10 134.8(3) . . ?
C13 C12 C6 118.8(3) . . ?
C10 C12 C6 106.4(2) . . ?
C12 C13 C1 134.2(3) . . ?
C12 C13 H5 112.1(17) . . ?
C1 C13 H5 113.4(17) . . ?
C16 C14 C3 117.1(3) . . ?
C16 C14 H4 123(2) . . ?
C3 C14 H4 120(2) . . ?
C11 C15 C16 120.9(3) . . ?
C11 C15 H1 116(2) . . ?
C16 C15 H1 123(2) . . ?
C15 C16 C14 121.2(3) . . ?
C15 C16 H3 124(2) . . ?
C14 C16 H3 115(2) . . ?
C9 C17 H8 109.5 . . ?
C9 C17 H10 109.5 . . ?
H8 C17 H10 109.5 . . ?
C9 C17 H9 109.5 . . ?
H8 C17 H9 109.5 . . ?
H10 C17 H9 109.5 . . ?
C7 C18 H11 109.5 . . ?
C7 C18 H12 109.5 . . ?
H11 C18 H12 109.5 . . ?
C7 C18 H13 109.5 . . ?
H11 C18 H13 109.5 . . ?
H12 C18 H13 109.5 . . ?
N1 C19 H16 109.5 . . ?
N1 C19 H18 109.5 . . ?
H16 C19 H18 109.5 . . ?
N1 C19 H17 109.5 . . ?
H16 C19 H17 109.5 . . ?
H18 C19 H17 109.5 . . ?
N1 C20 H19 109.5 . . ?
N1 C20 H14 109.5 . . ?
H19 C20 H14 109.5 . . ?
N1 C20 H15 109.5 . . ?
H19 C20 H15 109.5 . . ?
H14 C20 H15 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.982
_diffrn_reflns_theta_full        25.08
_diffrn_measured_fraction_theta_full 0.982
_refine_diff_density_max         0.234
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.045
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_IDLET
_database_code_depnum_ccdc_archive 'CCDC 2083072'
_audit_update_record             
;
2022-07-28 deposited with the CCDC.	2022-09-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H21 N O2'
_chemical_formula_weight         331.40

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

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

_cell_length_a                   21.496(8)
_cell_length_b                   7.800(3)
_cell_length_c                   21.007(7)
_cell_angle_alpha                90
_cell_angle_beta                 95.13(3)
_cell_angle_gamma                90
_cell_volume                     3508(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    193(2)
_cell_measurement_reflns_used    38
_cell_measurement_theta_min      3.45
_cell_measurement_theta_max      20.36

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.255
_exptl_crystal_F_000             1408
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_absorpt_coefficient_mu    0.080
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;

Crystal suitable for X--ray structure determination was selected under the
polarizing microscope, covered with Paratone oil and mounted on a goniometer
head. Experiment was performed at the low temperature. Data
were collected till resolution of 0.74 Α and were truncated with XPREP till
actual observed resolution.
;


_diffrn_ambient_temperature      193(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Syntax P1'
_diffrn_measurement_method       '2-theta/omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3182
_diffrn_reflns_av_unetI/netI     0.2408
_diffrn_reflns_av_R_equivalents  0.1093
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.598
_diffrn_reflns_theta_max         25.052
_diffrn_reflns_theta_full        25.052
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             3094
_reflns_number_gt                1313
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         ?
_reflns_Friedel_fraction_max     ?
_reflns_Friedel_fraction_full    ?



_computing_data_collection       'Syntax P-1 Suite'
_computing_cell_refinement       'Syntax P-1 Suite'
_computing_data_reduction        'Syntax P-1 Suite'
_computing_structure_solution    'Syntax P-1 Suite'
_computing_molecular_graphics    'XSHELL, Bruker'
_computing_publication_material  "'XSHELL, Bruker"
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'

_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)+(0.0548P)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         3094
_refine_ls_number_parameters     228
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2539
_refine_ls_R_factor_gt           0.0687
_refine_ls_wR_factor_ref         0.1388
_refine_ls_wR_factor_gt          0.1021
_refine_ls_goodness_of_fit_ref   0.953
_refine_ls_restrained_S_all      0.953
_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
O1 O 0.66991(12) 0.4326(3) -0.10881(11) 0.0487(7) Uani 1 1 d . . . . .
O2 O 0.59580(12) 0.7696(3) 0.05609(11) 0.0450(7) Uani 1 1 d . . . . .
N1 N 0.38020(12) -0.0349(3) 0.24814(12) 0.0331(7) Uani 1 1 d . . . . .
C1 C 0.66090(15) 0.5497(4) -0.07169(16) 0.0327(9) Uani 1 1 d . . . . .
C2 C 0.62044(15) 0.5481(4) -0.01886(15) 0.0288(8) Uani 1 1 d . . . . .
C3 C 0.62326(15) 0.7184(4) 0.01067(17) 0.0316(9) Uani 1 1 d . . . . .
C4 C 0.66639(15) 0.8224(4) -0.02501(16) 0.0293(8) Uani 1 1 d . . . . .
C5 C 0.68579(16) 0.9915(4) -0.01659(17) 0.0397(10) Uani 1 1 d . . . . .
H5 H 0.670903 1.060770 0.016012 0.048 Uiso 1 1 calc R U . . .
C6 C 0.72752(17) 1.0561(5) -0.05721(18) 0.0456(10) Uani 1 1 d . . . . .
H6 H 0.740615 1.172151 -0.052645 0.055 Uiso 1 1 calc R U . . .
C7 C 0.75058(18) 0.9564(5) -0.10415(18) 0.0467(10) Uani 1 1 d . . . . .
H7 H 0.779653 1.003466 -0.130843 0.056 Uiso 1 1 calc R U . . .
C8 C 0.73130(17) 0.7881(4) -0.11221(17) 0.0410(10) Uani 1 1 d . . . . .
H8 H 0.747015 0.718305 -0.144186 0.049 Uiso 1 1 calc R U . . .
C9 C 0.68897(15) 0.7237(4) -0.07312(15) 0.0284(9) Uani 1 1 d . . . . .
C10 C 0.59116(15) 0.4032(4) -0.00106(15) 0.0321(9) Uani 1 1 d . . . . .
H10 H 0.597352 0.305169 -0.026577 0.038 Uiso 1 1 calc R U . . .
C11 C 0.55276(16) 0.3756(4) 0.04973(16) 0.0357(9) Uani 1 1 d . . . . .
H11 H 0.542892 0.468842 0.076150 0.043 Uiso 1 1 calc R U . . .
C12 C 0.53019(15) 0.2171(4) 0.06064(15) 0.0337(9) Uani 1 1 d . . . . .
H12 H 0.542274 0.130239 0.032534 0.040 Uiso 1 1 calc R U . . .
C13 C 0.49077(15) 0.1603(4) 0.10825(15) 0.0276(8) Uani 1 1 d . . . . .
C14 C 0.47535(16) -0.0141(4) 0.11134(16) 0.0353(9) Uani 1 1 d . . . . .
H14 H 0.490820 -0.090469 0.081269 0.042 Uiso 1 1 calc R U . . .
C15 C 0.43885(15) -0.0788(4) 0.15598(15) 0.0337(9) Uani 1 1 d . . . . .
H15 H 0.429293 -0.197689 0.155724 0.040 Uiso 1 1 calc R U . . .
C16 C 0.41527(15) 0.0286(4) 0.20231(16) 0.0286(8) Uani 1 1 d . . . . .
C17 C 0.42978(15) 0.2049(4) 0.19915(16) 0.0331(9) Uani 1 1 d . . . . .
H17 H 0.414140 0.281687 0.228988 0.040 Uiso 1 1 calc R U . . .
C18 C 0.46611(15) 0.2676(4) 0.15373(16) 0.0336(9) Uani 1 1 d . . . . .
H18 H 0.474835 0.386929 0.153022 0.040 Uiso 1 1 calc R U . . .
C19 C 0.35842(18) -0.2126(4) 0.24646(17) 0.0470(11) Uani 1 1 d . . . . .
H19A H 0.350453 -0.249256 0.201356 0.056 Uiso 1 1 calc R U . . .
H19B H 0.318368 -0.218750 0.266234 0.056 Uiso 1 1 calc R U . . .
C20 C 0.4047(2) -0.3358(5) 0.28109(19) 0.0685(13) Uani 1 1 d . . . . .
H20A H 0.442778 -0.340561 0.258747 0.103 Uiso 1 1 calc R U . . .
H20B H 0.386071 -0.450386 0.281843 0.103 Uiso 1 1 calc R U . . .
H20C H 0.415074 -0.295924 0.324998 0.103 Uiso 1 1 calc R U . . .
C21 C 0.36598(16) 0.0636(4) 0.30383(15) 0.0369(9) Uani 1 1 d . . . . .
H21A H 0.398621 0.151983 0.312853 0.044 Uiso 1 1 calc R U . . .
H21B H 0.367126 -0.013758 0.341288 0.044 Uiso 1 1 calc R U . . .
C22 C 0.30308(18) 0.1497(5) 0.2952(2) 0.0604(12) Uani 1 1 d . . . . .
H22A H 0.303884 0.240135 0.262906 0.091 Uiso 1 1 calc R U . . .
H22B H 0.293333 0.199992 0.335871 0.091 Uiso 1 1 calc R U . . .
H22C H 0.271103 0.064880 0.281174 0.091 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
O1 C1 1.228(3) . ?
O2 C3 1.233(4) . ?
N1 C16 1.368(4) . ?
N1 C21 1.454(4) . ?
N1 C19 1.462(4) . ?
C1 C2 1.470(4) . ?
C1 C9 1.487(4) . ?
C2 C10 1.362(4) . ?
C2 C3 1.465(4) . ?
C3 C4 1.484(4) . ?
C4 C9 1.392(4) . ?
C4 C5 1.390(4) . ?
C5 C6 1.387(5) . ?
C5 H5 0.9500 . ?
C6 C7 1.382(5) . ?
C6 H6 0.9500 . ?
C7 C8 1.382(5) . ?
C7 H7 0.9500 . ?
C8 C9 1.374(5) . ?
C8 H8 0.9500 . ?
C10 C11 1.423(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.355(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.437(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.403(4) . ?
C13 C18 1.409(4) . ?
C14 C15 1.372(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.412(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.413(4) . ?
C17 C18 1.376(4) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 C20 1.521(5) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 C22 1.506(5) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 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
C16 N1 C21 122.9(3) . . ?
C16 N1 C19 121.4(3) . . ?
C21 N1 C19 115.5(3) . . ?
O1 C1 C2 127.7(3) . . ?
O1 C1 C9 125.4(3) . . ?
C2 C1 C9 106.9(3) . . ?
C10 C2 C3 129.7(3) . . ?
C10 C2 C1 122.2(3) . . ?
C3 C2 C1 107.9(3) . . ?
O2 C3 C2 128.1(3) . . ?
O2 C3 C4 125.3(3) . . ?
C2 C3 C4 106.6(3) . . ?
C9 C4 C5 119.8(3) . . ?
C9 C4 C3 109.8(3) . . ?
C5 C4 C3 130.4(3) . . ?
C6 C5 C4 118.0(4) . . ?
C6 C5 H5 121.0 . . ?
C4 C5 H5 121.0 . . ?
C7 C6 C5 121.8(4) . . ?
C7 C6 H6 119.1 . . ?
C5 C6 H6 119.1 . . ?
C6 C7 C8 119.9(4) . . ?
C6 C7 H7 120.0 . . ?
C8 C7 H7 120.0 . . ?
C9 C8 C7 118.8(4) . . ?
C9 C8 H8 120.6 . . ?
C7 C8 H8 120.6 . . ?
C8 C9 C4 121.6(3) . . ?
C8 C9 C1 129.6(3) . . ?
C4 C9 C1 108.8(3) . . ?
C2 C10 C11 130.1(3) . . ?
C2 C10 H10 114.9 . . ?
C11 C10 H10 114.9 . . ?
C12 C11 C10 120.3(3) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C11 C12 C13 129.9(3) . . ?
C11 C12 H12 115.1 . . ?
C13 C12 H12 115.1 . . ?
C14 C13 C18 116.1(3) . . ?
C14 C13 C12 119.2(3) . . ?
C18 C13 C12 124.8(3) . . ?
C15 C14 C13 122.7(3) . . ?
C15 C14 H14 118.6 . . ?
C13 C14 H14 118.6 . . ?
C14 C15 C16 121.0(3) . . ?
C14 C15 H15 119.5 . . ?
C16 C15 H15 119.5 . . ?
N1 C16 C15 121.7(3) . . ?
N1 C16 C17 121.6(3) . . ?
C15 C16 C17 116.8(3) . . ?
C18 C17 C16 121.3(3) . . ?
C18 C17 H17 119.3 . . ?
C16 C17 H17 119.3 . . ?
C17 C18 C13 122.1(3) . . ?
C17 C18 H18 119.0 . . ?
C13 C18 H18 119.0 . . ?
N1 C19 C20 113.2(3) . . ?
N1 C19 H19A 108.9 . . ?
C20 C19 H19A 108.9 . . ?
N1 C19 H19B 108.9 . . ?
C20 C19 H19B 108.9 . . ?
H19A C19 H19B 107.8 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N1 C21 C22 112.9(3) . . ?
N1 C21 H21A 109.0 . . ?
C22 C21 H21A 109.0 . . ?
N1 C21 H21B 109.0 . . ?
C22 C21 H21B 109.0 . . ?
H21A C21 H21B 107.8 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?

_refine_diff_density_max         0.179
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.045

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

data_RV1
_database_code_depnum_ccdc_archive 'CCDC 2083076'
loop_
_audit_author_name
_audit_author_address
'Arkady Ellern'
;Chemistry Department, Iowa State University, Osborn Drive, Ames, Iowa
United States of America
;
_audit_update_record             
;
2021-05-11 deposited with the CCDC.	2022-09-21 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_THETM01_RV1                 
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.550
RESPONSE: No reflections observed at higher resolution
;
# end Validation Reply Form
_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H21 N5'
_chemical_formula_weight         427.50

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'

_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                   8.190(4)
_cell_length_b                   11.379(5)
_cell_length_c                   12.636(6)
_cell_angle_alpha                104.04(4)
_cell_angle_beta                 91.86(4)
_cell_angle_gamma                97.94(4)
_cell_volume                     1128.8(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    420
_cell_measurement_theta_min      2.18
_cell_measurement_theta_max      22.25

_exptl_crystal_description       block
_exptl_crystal_colour            black
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.258
_exptl_crystal_F_000             448
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.077
_shelx_estimated_absorpt_T_min   0.970
_shelx_estimated_absorpt_T_max   0.985
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9700
_exptl_absorpt_correction_T_max  0.9848
_exptl_absorpt_process_details   'Bruker, SADABS'
_exptl_absorpt_special_details   'phi scan'
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Syntax P-1'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            2846
_diffrn_reflns_av_unetI/netI     0.0353
_diffrn_reflns_av_R_equivalents  0.0448
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.169
_diffrn_reflns_theta_max         21.721
_diffrn_reflns_theta_full        21.721
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measured_fraction_theta_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_point_group_measured_fraction_full 0.977
_reflns_number_total             2619
_reflns_number_gt                2000
_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       'Syntax P-1 Suite'
_computing_cell_refinement       'Syntax P-1 Suite'
_computing_data_reduction        'Syntax P-1 Suite'
_computing_structure_solution    'Syntax P-1 Suite'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'XSHELL, Bruker'
_computing_publication_material  "'XSHELL, Bruker"

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_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     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.024(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2619
_refine_ls_number_parameters     301
_refine_ls_number_restraints     15
_refine_ls_R_factor_all          0.1070
_refine_ls_R_factor_gt           0.0731
_refine_ls_wR_factor_ref         0.2512
_refine_ls_wR_factor_gt          0.1994
_refine_ls_goodness_of_fit_ref   1.119
_refine_ls_restrained_S_all      1.118
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.8161(5) 0.6854(4) 0.6501(3) 0.0720(13) Uani 1 1 d . . . . .
N2 N 0.5214(6) 0.5524(4) 0.8742(4) 0.0767(13) Uani 1 1 d . . . . .
N3 N 0.6635(5) 1.2194(4) 0.4821(3) 0.0702(12) Uani 1 1 d . . . . .
N4 N 1.5366(5) 0.8910(4) 0.8630(4) 0.0687(12) Uani 1 1 d . . . . .
N5 N 1.5727(5) 0.8070(4) 1.1670(4) 0.0687(12) Uani 1 1 d . . . . .
C1 C 0.9271(5) 0.7172(3) 0.9301(3) 0.0376(10) Uani 1 1 d . . . . .
C2 C 1.0821(5) 0.7937(3) 0.9211(3) 0.0381(10) Uani 1 1 d . . . . .
C3 C 1.2032(5) 0.7740(3) 0.9994(3) 0.0371(10) Uani 1 1 d . . . . .
C4 C 1.1131(5) 0.7038(3) 1.0694(3) 0.0343(10) Uani 1 1 d . . . . .
C5 C 1.1671(5) 0.6637(3) 1.1568(3) 0.0404(10) Uani 1 1 d . . . . .
H5 H 1.2804 0.6806 1.1822 0.049 Uiso 1 1 calc R U . . .
C6 C 1.0522(5) 0.5982(4) 1.2068(3) 0.0464(11) Uani 1 1 d . . . . .
H6 H 1.0869 0.5724 1.2688 0.056 Uiso 1 1 calc R U . . .
C7 C 0.8899(5) 0.5700(4) 1.1688(3) 0.0476(11) Uani 1 1 d . . . . .
H7 H 0.8143 0.5241 1.2046 0.057 Uiso 1 1 calc R U . . .
C8 C 0.8339(5) 0.6062(4) 1.0806(3) 0.0457(11) Uani 1 1 d . . . . .
H8 H 0.7208 0.5857 1.0547 0.055 Uiso 1 1 calc R U . . .
C9 C 0.9463(4) 0.6741(3) 1.0291(3) 0.0368(10) Uani 1 1 d . . . . .
C10 C 0.7982(5) 0.6768(3) 0.8514(3) 0.0418(10) Uani 1 1 d . . . . .
C11 C 0.8099(5) 0.6861(4) 0.7412(4) 0.0482(12) Uani 1 1 d . . . . .
C12 C 0.6462(6) 0.6067(4) 0.8675(3) 0.0491(12) Uani 1 1 d . . . . .
C13 C 1.1048(5) 0.8853(3) 0.8656(3) 0.0427(11) Uani 1 1 d . . . . .
H13 H 1.2166 0.9200 0.8635 0.051 Uiso 1 1 calc R U . . .
C14 C 0.9905(5) 0.9342(3) 0.8128(3) 0.0445(11) Uani 1 1 d . . . . .
H14 H 0.8760 0.9129 0.8207 0.053 Uiso 1 1 calc R U . . .
C15 C 1.0398(5) 1.0128(3) 0.7494(3) 0.0448(11) Uani 1 1 d . . . . .
H15 H 1.1557 1.0366 0.7498 0.054 Uiso 1 1 calc R U . . .
C16 C 0.9406(5) 1.0635(3) 0.6830(3) 0.0387(10) Uani 1 1 d . . . . .
C17 C 1.0162(5) 1.1294(4) 0.6123(3) 0.0509(12) Uani 1 1 d . . . . .
H17 H 1.1331 1.1391 0.6107 0.061 Uiso 1 1 calc R U . . .
C18 C 0.9293(6) 1.1797(4) 0.5464(3) 0.0565(13) Uani 1 1 d . . . . .
H18 H 0.9859 1.2224 0.4992 0.068 Uiso 1 1 calc R U . . .
C19 C 0.7539(6) 1.1695(4) 0.5469(3) 0.0521(12) Uani 1 1 d . . . . .
C20 C 0.6778(5) 1.1036(4) 0.6174(3) 0.0501(12) Uani 1 1 d . . . . .
H20 H 0.5612 1.0957 0.6209 0.060 Uiso 1 1 calc R U . . .
C21 C 0.7680(5) 1.0506(3) 0.6812(3) 0.0442(11) Uani 1 1 d . . . . .
H21 H 0.7118 1.0038 0.7255 0.053 Uiso 1 1 calc R U . . .
C22 C 0.4900(7) 1.2300(5) 0.4979(4) 0.0791(17) Uani 1 1 d . U . . .
H22A H 0.4325 1.1506 0.5063 0.095 Uiso 1 1 calc R U . . .
H22B H 0.4397 1.2457 0.4314 0.095 Uiso 1 1 calc R U . . .
C23 C 0.4611(8) 1.3287(5) 0.5945(5) 0.0864(18) Uani 1 1 d . U . . .
H23A H 0.5126 1.3154 0.6609 0.130 Uiso 1 1 calc R U . . .
H23B H 0.3420 1.3269 0.6016 0.130 Uiso 1 1 calc R U . . .
H23C H 0.5097 1.4086 0.5844 0.130 Uiso 1 1 calc R U . . .
C24 C 0.7362(10) 1.2669(7) 0.3934(5) 0.115(2) Uani 1 1 d D U . . .
H24A H 0.6532 1.2512 0.3310 0.138 Uiso 1 1 calc R U . . .
H24B H 0.8311 1.2248 0.3679 0.138 Uiso 1 1 calc R U . . .
C25 C 0.7943(12) 1.4054(7) 0.4357(9) 0.178(4) Uani 1 1 d D U . . .
H25A H 0.7049 1.4446 0.4723 0.266 Uiso 1 1 calc R U . . .
H25B H 0.8243 1.4404 0.3741 0.266 Uiso 1 1 calc R U . . .
H25C H 0.8907 1.4196 0.4877 0.266 Uiso 1 1 calc R U . . .
C26 C 1.3713(5) 0.8109(3) 1.0076(3) 0.0415(11) Uani 1 1 d . . . . .
C27 C 1.4584(5) 0.8562(4) 0.9263(4) 0.0473(11) Uani 1 1 d . . . . .
C28 C 1.4793(5) 0.8052(4) 1.0964(4) 0.0471(11) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C11 1.151(5) . ?
N2 C12 1.136(5) . ?
N3 C19 1.357(6) . ?
N3 C22 1.459(7) . ?
N3 C24 1.466(8) . ?
N4 C27 1.150(5) . ?
N5 C28 1.150(5) . ?
C1 C10 1.375(6) . ?
C1 C2 1.461(5) . ?
C1 C9 1.463(5) . ?
C2 C13 1.387(5) . ?
C2 C3 1.455(5) . ?
C3 C26 1.376(5) . ?
C3 C4 1.479(5) . ?
C4 C5 1.375(5) . ?
C4 C9 1.408(5) . ?
C5 C6 1.383(6) . ?
C5 H5 0.9500 . ?
C6 C7 1.366(6) . ?
C6 H6 0.9500 . ?
C7 C8 1.366(6) . ?
C7 H7 0.9500 . ?
C8 C9 1.397(5) . ?
C8 H8 0.9500 . ?
C10 C11 1.428(7) . ?
C10 C12 1.431(7) . ?
C13 C14 1.384(5) . ?
C13 H13 0.9500 . ?
C14 C15 1.369(5) . ?
C14 H14 0.9500 . ?
C15 C16 1.420(5) . ?
C15 H15 0.9500 . ?
C16 C21 1.399(6) . ?
C16 C17 1.406(5) . ?
C17 C18 1.353(6) . ?
C17 H17 0.9500 . ?
C18 C19 1.425(6) . ?
C18 H18 0.9500 . ?
C19 C20 1.405(6) . ?
C20 C21 1.372(6) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
C22 C23 1.495(7) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 C25 1.538(2) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 C28 1.425(6) . ?
C26 C27 1.427(6) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C19 N3 C22 121.8(4) . . ?
C19 N3 C24 121.6(5) . . ?
C22 N3 C24 116.6(4) . . ?
C10 C1 C2 126.2(3) . . ?
C10 C1 C9 125.8(3) . . ?
C2 C1 C9 107.2(3) . . ?
C13 C2 C3 124.8(3) . . ?
C13 C2 C1 127.1(3) . . ?
C3 C2 C1 107.0(3) . . ?
C26 C3 C2 127.4(4) . . ?
C26 C3 C4 125.2(4) . . ?
C2 C3 C4 107.4(3) . . ?
C5 C4 C9 120.7(3) . . ?
C5 C4 C3 131.3(3) . . ?
C9 C4 C3 108.0(3) . . ?
C4 C5 C6 118.2(4) . . ?
C4 C5 H5 120.9 . . ?
C6 C5 H5 120.9 . . ?
C7 C6 C5 121.4(4) . . ?
C7 C6 H6 119.3 . . ?
C5 C6 H6 119.3 . . ?
C6 C7 C8 121.4(4) . . ?
C6 C7 H7 119.3 . . ?
C8 C7 H7 119.3 . . ?
C7 C8 C9 118.7(4) . . ?
C7 C8 H8 120.7 . . ?
C9 C8 H8 120.7 . . ?
C8 C9 C4 119.5(3) . . ?
C8 C9 C1 131.3(4) . . ?
C4 C9 C1 109.0(3) . . ?
C1 C10 C11 123.4(4) . . ?
C1 C10 C12 123.3(4) . . ?
C11 C10 C12 112.7(4) . . ?
N1 C11 C10 175.5(5) . . ?
N2 C12 C10 175.5(4) . . ?
C14 C13 C2 130.3(4) . . ?
C14 C13 H13 114.8 . . ?
C2 C13 H13 114.8 . . ?
C15 C14 C13 121.0(4) . . ?
C15 C14 H14 119.5 . . ?
C13 C14 H14 119.5 . . ?
C14 C15 C16 128.6(4) . . ?
C14 C15 H15 115.7 . . ?
C16 C15 H15 115.7 . . ?
C21 C16 C17 116.4(4) . . ?
C21 C16 C15 124.0(3) . . ?
C17 C16 C15 119.5(4) . . ?
C18 C17 C16 122.7(4) . . ?
C18 C17 H17 118.6 . . ?
C16 C17 H17 118.6 . . ?
C17 C18 C19 120.9(4) . . ?
C17 C18 H18 119.6 . . ?
C19 C18 H18 119.6 . . ?
N3 C19 C20 121.2(5) . . ?
N3 C19 C18 122.2(4) . . ?
C20 C19 C18 116.6(4) . . ?
C21 C20 C19 121.5(4) . . ?
C21 C20 H20 119.2 . . ?
C19 C20 H20 119.2 . . ?
C20 C21 C16 121.9(4) . . ?
C20 C21 H21 119.1 . . ?
C16 C21 H21 119.1 . . ?
N3 C22 C23 114.6(4) . . ?
N3 C22 H22A 108.6 . . ?
C23 C22 H22A 108.6 . . ?
N3 C22 H22B 108.6 . . ?
C23 C22 H22B 108.6 . . ?
H22A C22 H22B 107.6 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
N3 C24 C25 109.1(5) . . ?
N3 C24 H24A 109.9 . . ?
C25 C24 H24A 109.9 . . ?
N3 C24 H24B 109.9 . . ?
C25 C24 H24B 109.9 . . ?
H24A C24 H24B 108.3 . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C3 C26 C28 124.2(4) . . ?
C3 C26 C27 123.7(4) . . ?
C28 C26 C27 112.1(3) . . ?
N4 C27 C26 176.1(4) . . ?
N5 C28 C26 175.6(4) . . ?

_refine_diff_density_max         0.439
_refine_diff_density_min         -0.361
_refine_diff_density_rms         0.101

####################################################################### 
# 
# 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_ROI5
_database_code_depnum_ccdc_archive 'CCDC 2193391'
_audit_update_record             
;
2022-07-28 deposited with the CCDC.	2022-09-21 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_THETM01_ROI5                
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.550
RESPONSE: Very weak crystal with poor resolution. 
;
# end Validation Reply Form 
_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H21 N3 O'
_chemical_formula_weight         379.45

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                   14.660(3)
_cell_length_b                   8.7900(18)
_cell_length_c                   16.190(3)
_cell_angle_alpha                90
_cell_angle_beta                 99.29(3)
_cell_angle_gamma                90
_cell_volume                     2058.9(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    112
_cell_measurement_theta_min      2.15
_cell_measurement_theta_max      22.37

_exptl_crystal_description       block
_exptl_crystal_colour            'dark green'
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.224
_exptl_crystal_F_000             800
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_absorpt_coefficient_mu    0.076
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_special_details           
;

Crystal suitable for X--ray structure determination was selected under the
polarizing microscope, covered with Paratone oil and mounted on a goniometer
head. Experiment was performed at the low temperature. Data
were collected till resolution of 0.74 Α and were truncated with XPREP till
actual observed resolution.
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_measurement_device_type  'Syntax P-1'
_diffrn_measurement_method       'phi scan'

_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            2141
_diffrn_reflns_av_unetI/netI     0.1211
_diffrn_reflns_av_R_equivalents  0.1471
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.092
_diffrn_reflns_theta_max         20.811
_diffrn_reflns_theta_full        20.811
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             2141
_reflns_number_gt                1015
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
The systematic absences in the diffraction data were consistent for the
stated space group. The position of almost all non-hydrogen atoms
were found by direct methods. The remaining atoms were located in an
alternating series of least-squares cycles on difference Fourier map.

All non-hydrogen atoms were refined in full-matrix anisotropic approximation.
All hydrogen atoms were placed in the structure factor calculation at
idealized positions and were allowed to ride on the neighboring atoms with
relative isotropic displacement coefficients.

DFIX, SIMU ande DELU restraints were used to improve geometry of the moieties
 and obtain resonable thermal parameters. 

Final results were tested with CHECKCIF routine and all A-warnings (if any)
were addressed on the very top of this file.
 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0568P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0053(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2141
_refine_ls_number_parameters     263
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1270
_refine_ls_R_factor_gt           0.0508
_refine_ls_wR_factor_ref         0.1280
_refine_ls_wR_factor_gt          0.1079
_refine_ls_goodness_of_fit_ref   0.853
_refine_ls_restrained_S_all      0.853
_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 0.3449(3) 0.0945(4) 0.9495(3) 0.0530(13) Uani 1 1 d . . . . .
C2 C 0.4075(3) 0.0963(5) 0.8867(3) 0.0592(14) Uani 1 1 d . . . . .
C3 C 0.4466(3) -0.0586(5) 0.8861(3) 0.0536(13) Uani 1 1 d . . . . .
C4 C 0.5044(3) -0.1170(5) 0.8349(3) 0.0727(16) Uani 1 1 d . . . . .
H4A H 0.524286 -0.054254 0.792582 0.080 Uiso 1 1 d R U . . .
C5 C 0.5298(3) -0.2694(6) 0.8437(3) 0.0768(16) Uani 1 1 d . . . . .
H5A H 0.571307 -0.313458 0.810189 0.080 Uiso 1 1 d R U . . .
C6 C 0.4972(4) -0.3567(5) 0.9036(4) 0.0774(17) Uani 1 1 d . . . . .
H6A H 0.515761 -0.461355 0.909948 0.080 Uiso 1 1 d R U . . .
C7 C 0.4402(3) -0.2982(5) 0.9553(3) 0.0681(15) Uani 1 1 d . . . . .
H7A H 0.416823 -0.360659 0.995794 0.080 Uiso 1 1 d R U . . .
C8 C 0.4148(3) -0.1460(4) 0.9469(3) 0.0479(13) Uani 1 1 d . . . . .
C9 C 0.3518(3) -0.0544(4) 0.9889(3) 0.0498(13) Uani 1 1 d . . . . .
C10 C 0.3108(3) -0.1030(4) 1.0531(3) 0.0589(14) Uani 1 1 d . . . . .
C11 C 0.3263(3) -0.2491(5) 1.0925(3) 0.0679(16) Uani 1 1 d . . . . .
C12 C 0.2465(5) -0.0173(5) 1.0898(4) 0.093(2) Uani 1 1 d . . . . .
C13 C 0.2904(3) 0.2143(4) 0.9634(3) 0.0600(14) Uani 1 1 d . . . . .
H13A H 0.253945 0.203230 1.007307 0.080 Uiso 1 1 d R U . . .
C14 C 0.2798(3) 0.3566(4) 0.9204(3) 0.0588(14) Uani 1 1 d . . . . .
H14A H 0.317480 0.379022 0.878693 0.080 Uiso 1 1 d R U . . .
C15 C 0.2171(3) 0.4595(5) 0.9401(3) 0.0621(15) Uani 1 1 d . . . . .
H15A H 0.185578 0.429360 0.985028 0.080 Uiso 1 1 d R U . . .
C16 C 0.1910(3) 0.6043(4) 0.9022(3) 0.0544(13) Uani 1 1 d . . . . .
C17 C 0.1203(3) 0.6883(5) 0.9298(3) 0.0639(14) Uani 1 1 d . . . . .
H17A H 0.092172 0.647312 0.974610 0.080 Uiso 1 1 d R U . . .
C18 C 0.0910(3) 0.8249(4) 0.8956(3) 0.0612(14) Uani 1 1 d . . . . .
H18A H 0.041674 0.879115 0.915023 0.080 Uiso 1 1 d R U . . .
C19 C 0.1312(3) 0.8900(5) 0.8312(3) 0.0563(13) Uani 1 1 d . . . . .
C20 C 0.2039(3) 0.8076(5) 0.8046(3) 0.0588(14) Uani 1 1 d . . . . .
H20A H 0.234150 0.851989 0.762133 0.080 Uiso 1 1 d R U . . .
C21 C 0.2315(3) 0.6687(4) 0.8380(3) 0.0575(13) Uani 1 1 d . . . . .
H21A H 0.279600 0.613875 0.817160 0.080 Uiso 1 1 d R U . . .
C22 C 0.0114(4) 1.0885(5) 0.8074(3) 0.0838(18) Uani 1 1 d . . . . .
H22A H -0.015294 1.140814 0.757240 0.080 Uiso 1 1 d R U . . .
H22B H -0.029364 1.007374 0.817130 0.080 Uiso 1 1 d R U . . .
C23 C 0.0191(4) 1.1957(5) 0.8778(4) 0.123(2) Uani 1 1 d . . . . .
H23A H -0.039760 1.237076 0.884764 0.080 Uiso 1 1 d R U . . .
H23B H 0.045450 1.142445 0.927724 0.080 Uiso 1 1 d R U . . .
H23C H 0.059610 1.276806 0.867424 0.080 Uiso 1 1 d R U . . .
C24 C 0.1580(4) 1.1150(5) 0.7445(4) 0.101(2) Uani 1 1 d . . . . .
H24A H 0.150278 1.222467 0.751405 0.080 Uiso 1 1 d R U . . .
H24B H 0.222048 1.090377 0.761605 0.080 Uiso 1 1 d R U . . .
C25 C 0.1317(4) 1.0719(5) 0.6587(4) 0.112(2) Uani 1 1 d . . . . .
H25A H 0.168027 1.125731 0.623919 0.080 Uiso 1 1 d R U . . .
H25B H 0.139897 0.964421 0.652529 0.080 Uiso 1 1 d R U . . .
H25C H 0.067687 1.097321 0.642269 0.080 Uiso 1 1 d R U . . .
N1 N 0.3346(3) -0.3628(4) 1.1280(3) 0.0858(15) Uani 1 1 d . . . . .
N2 N 0.1933(4) 0.0480(5) 1.1218(4) 0.152(3) Uani 1 1 d . . . . .
N3 N 0.1012(3) 1.0240(4) 0.7967(3) 0.0784(14) Uani 1 1 d . . . . .
O1 O 0.4242(2) 0.2029(3) 0.8425(2) 0.0863(12) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C13 1.363(5) . ?
C1 C9 1.453(5) . ?
C1 C2 1.476(5) . ?
C2 O1 1.227(4) . ?
C2 C3 1.478(5) . ?
C3 C4 1.378(5) . ?
C3 C8 1.387(5) . ?
C4 C5 1.392(5) . ?
C4 H4A 0.9597 . ?
C5 C6 1.381(6) . ?
C5 H5A 0.9596 . ?
C6 C7 1.375(6) . ?
C6 H6A 0.9598 . ?
C7 C8 1.390(5) . ?
C7 H7A 0.9597 . ?
C8 C9 1.473(5) . ?
C9 C10 1.350(5) . ?
C10 C12 1.410(6) . ?
C10 C11 1.436(6) . ?
C11 N1 1.150(5) . ?
C12 N2 1.156(6) . ?
C13 C14 1.428(5) . ?
C13 H13A 0.9596 . ?
C14 C15 1.364(5) . ?
C14 H14A 0.9597 . ?
C15 C16 1.437(5) . ?
C15 H15A 0.9596 . ?
C16 C21 1.397(5) . ?
C16 C17 1.404(5) . ?
C17 C18 1.363(5) . ?
C17 H17A 0.9596 . ?
C18 C19 1.401(5) . ?
C18 H18A 0.9596 . ?
C19 N3 1.347(5) . ?
C19 C20 1.411(5) . ?
C20 C21 1.369(5) . ?
C20 H20A 0.9597 . ?
C21 H21A 0.9596 . ?
C22 N3 1.469(5) . ?
C22 C23 1.469(6) . ?
C22 H22A 0.9597 . ?
C22 H22B 0.9598 . ?
C23 H23A 0.9595 . ?
C23 H23B 0.9597 . ?
C23 H23C 0.9597 . ?
C24 C25 1.432(6) . ?
C24 N3 1.508(6) . ?
C24 H24A 0.9598 . ?
C24 H24B 0.9596 . ?
C25 H25A 0.9597 . ?
C25 H25B 0.9599 . ?
C25 H25C 0.9596 . ?

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
C13 C1 C9 128.6(4) . . ?
C13 C1 C2 123.6(4) . . ?
C9 C1 C2 107.8(4) . . ?
O1 C2 C1 127.9(4) . . ?
O1 C2 C3 125.9(5) . . ?
C1 C2 C3 106.2(4) . . ?
C4 C3 C8 122.1(4) . . ?
C4 C3 C2 128.6(5) . . ?
C8 C3 C2 109.3(4) . . ?
C3 C4 C5 118.5(4) . . ?
C3 C4 H4A 120.2 . . ?
C5 C4 H4A 121.3 . . ?
C6 C5 C4 119.4(5) . . ?
C6 C5 H5A 119.7 . . ?
C4 C5 H5A 120.9 . . ?
C7 C6 C5 122.2(4) . . ?
C7 C6 H6A 118.9 . . ?
C5 C6 H6A 118.9 . . ?
C6 C7 C8 118.7(5) . . ?
C6 C7 H7A 121.4 . . ?
C8 C7 H7A 119.9 . . ?
C3 C8 C7 119.2(4) . . ?
C3 C8 C9 109.4(4) . . ?
C7 C8 C9 131.2(4) . . ?
C10 C9 C1 127.9(4) . . ?
C10 C9 C8 125.0(4) . . ?
C1 C9 C8 107.1(4) . . ?
C9 C10 C12 124.5(4) . . ?
C9 C10 C11 124.5(4) . . ?
C12 C10 C11 111.0(4) . . ?
N1 C11 C10 175.1(5) . . ?
N2 C12 C10 177.3(5) . . ?
C1 C13 C14 128.0(4) . . ?
C1 C13 H13A 117.1 . . ?
C14 C13 H13A 114.8 . . ?
C15 C14 C13 119.4(4) . . ?
C15 C14 H14A 121.0 . . ?
C13 C14 H14A 119.6 . . ?
C14 C15 C16 129.1(4) . . ?
C14 C15 H15A 114.7 . . ?
C16 C15 H15A 116.2 . . ?
C21 C16 C17 116.6(4) . . ?
C21 C16 C15 124.1(4) . . ?
C17 C16 C15 119.2(4) . . ?
C18 C17 C16 122.3(4) . . ?
C18 C17 H17A 119.5 . . ?
C16 C17 H17A 118.2 . . ?
C17 C18 C19 121.3(4) . . ?
C17 C18 H18A 120.6 . . ?
C19 C18 H18A 118.1 . . ?
N3 C19 C18 121.1(4) . . ?
N3 C19 C20 122.3(4) . . ?
C18 C19 C20 116.5(4) . . ?
C21 C20 C19 121.8(4) . . ?
C21 C20 H20A 120.3 . . ?
C19 C20 H20A 117.9 . . ?
C20 C21 C16 121.4(4) . . ?
C20 C21 H21A 119.7 . . ?
C16 C21 H21A 118.9 . . ?
N3 C22 C23 112.4(5) . . ?
N3 C22 H22A 109.6 . . ?
C23 C22 H22A 108.6 . . ?
N3 C22 H22B 109.0 . . ?
C23 C22 H22B 108.7 . . ?
H22A C22 H22B 108.4 . . ?
C22 C23 H23A 112.1 . . ?
C22 C23 H23B 108.1 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 108.2 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C25 C24 N3 108.4(5) . . ?
C25 C24 H24A 110.8 . . ?
N3 C24 H24A 111.7 . . ?
C25 C24 H24B 108.5 . . ?
N3 C24 H24B 108.8 . . ?
H24A C24 H24B 108.5 . . ?
C24 C25 H25A 110.5 . . ?
C24 C25 H25B 110.1 . . ?
H25A C25 H25B 109.5 . . ?
C24 C25 H25C 107.8 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C19 N3 C22 121.9(4) . . ?
C19 N3 C24 121.5(4) . . ?
C22 N3 C24 116.6(4) . . ?

_refine_diff_density_max         0.183
_refine_diff_density_min         -0.172
_refine_diff_density_rms         0.036

####################################################################### 
# 
# 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_ROI32
_database_code_depnum_ccdc_archive 'CCDC 2083075'
_audit_update_record             
;
2022-07-28 deposited with the CCDC.	2022-09-21 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_THETM01_ROI32               
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.550
RESPONSE: Poor diffraction. 
;
# end Validation Reply Form
_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H23 N O2'
_chemical_formula_weight         357.43

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

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

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

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

_cell_length_a                   11.278(3)
_cell_length_b                   17.731(3)
_cell_length_c                   20.405(5)
_cell_angle_alpha                90
_cell_angle_beta                 103.26(3)
_cell_angle_gamma                90
_cell_volume                     3971.6(17)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    57
_cell_measurement_theta_min      3.34
_cell_measurement_theta_max      24.43

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.196
_exptl_crystal_F_000             1520
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_absorpt_coefficient_mu    0.076
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?



_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Syntax P1'
_diffrn_measurement_method       '2Theta-omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4576
_diffrn_reflns_av_unetI/netI     0.0378
_diffrn_reflns_av_R_equivalents  0.0242
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.540
_diffrn_reflns_theta_max         20.044
_diffrn_reflns_theta_full        20.044
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.521
_diffrn_reflns_point_group_measured_fraction_full 0.521
_reflns_number_total             3882
_reflns_number_gt                2837
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     0.000
_reflns_Friedel_fraction_full    0.000

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0639P)²+1.2838P] 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     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0055(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
No quotients, so Flack parameter determined by classical intensity fit
;
_refine_ls_abs_structure_Flack   -1(2)

_refine_special_details          
;
 
The systematic absences in the diffraction data were consistent for the
stated space group. The position of almost all non-hydrogen atoms
were found by direct methods. The remaining atoms were located in an
alternating series of least-squares cycles on difference Fourier map.

All non-hydrogen atoms were refined in full-matrix anisotropic approximation.
All hydrogen atoms were placed in the structure factor calculation at
idealized positions and were allowed to ride on the neighboring atoms with
relative isotropic displacement coefficients.

Final results were tested with CHECKCIF routine and all A-warnings (if any)
were addressed on the very top of this file.
 
;




_chemical_absolute_configuration ?
_refine_ls_number_reflns         3882
_refine_ls_number_parameters     878
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0845
_refine_ls_R_factor_gt           0.0458
_refine_ls_wR_factor_ref         0.1208
_refine_ls_wR_factor_gt          0.1070
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.053
_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 0.0225(9) 0.6121(5) 0.3456(4) 0.083(2) Uani 1 1 d . . . . .
C2 C 0.0168(7) 0.6143(3) 0.2730(3) 0.082(2) Uani 1 1 d G . . . .
C3 C -0.0794(5) 0.5976(3) 0.2190(5) 0.114(3) Uani 1 1 d G . . . .
H3 H -0.154815 0.584116 0.226523 0.137 Uiso 1 1 calc R U . . .
C4 C -0.0628(7) 0.6010(4) 0.1536(4) 0.133(4) Uani 1 1 d G . . . .
H4 H -0.127116 0.589790 0.117425 0.159 Uiso 1 1 calc R U . . .
C5 C 0.0500(9) 0.6211(4) 0.1423(3) 0.132(4) Uani 1 1 d G . . . .
H5 H 0.061077 0.623375 0.098560 0.158 Uiso 1 1 calc R U . . .
C6 C 0.1461(6) 0.6378(4) 0.1964(4) 0.114(3) Uani 1 1 d G . . . .
H6 H 0.221573 0.651285 0.188792 0.137 Uiso 1 1 calc R U . . .
C7 C 0.1295(6) 0.6344(3) 0.2617(3) 0.089(3) Uani 1 1 d G . . . .
C8 C 0.2160(9) 0.6418(5) 0.3269(4) 0.089(3) Uani 1 1 d . . . . .
C9 C 0.1506(8) 0.6246(5) 0.3793(4) 0.078(2) Uani 1 1 d . . . . .
C10 C 0.2062(8) 0.6118(5) 0.4442(5) 0.091(3) Uani 1 1 d . . . . .
H10 H 0.290219 0.618758 0.454736 0.109 Uiso 1 1 calc R U . . .
C11 C 0.1571(8) 0.5899(5) 0.4979(4) 0.085(2) Uani 1 1 d . . . . .
H11 H 0.072771 0.587970 0.491411 0.102 Uiso 1 1 calc R U . . .
C12 C 0.2269(8) 0.5712(5) 0.5593(4) 0.086(2) Uani 1 1 d . . . . .
H12 H 0.310722 0.574074 0.563795 0.103 Uiso 1 1 calc R U . . .
C13 C 0.1873(8) 0.5479(5) 0.6173(4) 0.082(2) Uani 1 1 d . . . . .
H13 H 0.104228 0.543095 0.614538 0.099 Uiso 1 1 calc R U . . .
C14 C 0.2660(7) 0.5325(4) 0.6765(4) 0.081(2) Uani 1 1 d . . . . .
H14 H 0.348099 0.531821 0.675810 0.098 Uiso 1 1 calc R U . . .
C15 C 0.2375(6) 0.5167(3) 0.7415(2) 0.073(2) Uani 1 1 d G . . . .
C16 C 0.1204(4) 0.5254(3) 0.7515(2) 0.072(2) Uani 1 1 d G . . . .
H16 H 0.056112 0.536389 0.715314 0.087 Uiso 1 1 calc R U . . .
C17 C 0.0995(4) 0.5176(3) 0.8157(3) 0.074(2) Uani 1 1 d G . . . .
H17 H 0.021230 0.523341 0.822455 0.089 Uiso 1 1 calc R U . . .
C18 C 0.1957(6) 0.5011(3) 0.8699(2) 0.072(2) Uani 1 1 d G . . . .
C19 C 0.3127(5) 0.4925(3) 0.8598(2) 0.083(2) Uani 1 1 d G . . . .
H19 H 0.377063 0.481467 0.896068 0.100 Uiso 1 1 calc R U . . .
C20 C 0.3336(4) 0.5003(3) 0.7956(3) 0.080(2) Uani 1 1 d G . . . .
H20 H 0.411948 0.494514 0.788927 0.096 Uiso 1 1 calc R U . . .
C21 C 0.0551(8) 0.5021(5) 0.9478(4) 0.092(3) Uani 1 1 d . . . . .
H21A H 0.055551 0.477458 0.990276 0.110 Uiso 1 1 calc R U . . .
H21B H -0.002259 0.475431 0.912783 0.110 Uiso 1 1 calc R U . . .
C22 C 0.0120(9) 0.5820(6) 0.9509(5) 0.124(3) Uani 1 1 d . . . . .
H22A H -0.067981 0.581851 0.959799 0.186 Uiso 1 1 calc R U . . .
H22B H 0.067091 0.608518 0.986162 0.186 Uiso 1 1 calc R U . . .
H22C H 0.009236 0.606489 0.908608 0.186 Uiso 1 1 calc R U . . .
C23 C 0.2770(8) 0.4979(6) 0.9942(4) 0.098(3) Uani 1 1 d . . . . .
H23A H 0.249593 0.521806 1.030879 0.118 Uiso 1 1 calc R U . . .
H23B H 0.342692 0.528225 0.984693 0.118 Uiso 1 1 calc R U . . .
C24 C 0.3256(8) 0.4194(6) 1.0164(5) 0.121(3) Uani 1 1 d . . . . .
H24A H 0.391233 0.423525 1.055541 0.181 Uiso 1 1 calc R U . . .
H24B H 0.261432 0.389466 1.026819 0.181 Uiso 1 1 calc R U . . .
H24C H 0.354533 0.395886 0.980633 0.181 Uiso 1 1 calc R U . . .
N1 N 0.1761(6) 0.4963(4) 0.9344(4) 0.088(2) Uani 1 1 d . . . . .
O1 O -0.0637(5) 0.5997(4) 0.3710(3) 0.105(2) Uani 1 1 d . . . . .
O2 O 0.3262(7) 0.6538(4) 0.3354(3) 0.126(2) Uani 1 1 d . . . . .
C1B C 0.1782(7) 0.2769(4) 0.8133(4) 0.070(2) Uani 1 1 d . . . . .
C2B C 0.1675(5) 0.2685(3) 0.8835(2) 0.067(2) Uani 1 1 d G . . . .
C3B C 0.2411(4) 0.2288(3) 0.9363(3) 0.081(2) Uani 1 1 d G . . . .
H3B H 0.312704 0.206509 0.930639 0.097 Uiso 1 1 calc R U . . .
C4B C 0.2076(5) 0.2225(3) 0.9975(3) 0.085(2) Uani 1 1 d G . . . .
H4B H 0.256802 0.195925 1.032813 0.102 Uiso 1 1 calc R U . . .
C5B C 0.1005(6) 0.2558(3) 1.0060(2) 0.083(2) Uani 1 1 d G . . . .
H5B H 0.078127 0.251542 1.046930 0.100 Uiso 1 1 calc R U . . .
C6B C 0.0270(4) 0.2954(3) 0.9532(3) 0.072(2) Uani 1 1 d G . . . .
H6B H -0.044648 0.317744 0.958872 0.087 Uiso 1 1 calc R U . . .
C7B C 0.0605(4) 0.3018(3) 0.8920(2) 0.066(2) Uani 1 1 d G . . . .
C8B C -0.0036(7) 0.3361(4) 0.8287(4) 0.060(2) Uani 1 1 d . . . . .
C9B C 0.0701(7) 0.3193(4) 0.7794(4) 0.064(2) Uani 1 1 d . . . . .
C10B C 0.0381(7) 0.3419(4) 0.7148(4) 0.074(2) Uani 1 1 d . . . . .
H10B H -0.030046 0.372871 0.703234 0.088 Uiso 1 1 calc R U . . .
C11B C 0.0969(7) 0.3235(5) 0.6620(4) 0.078(2) Uani 1 1 d . . . . .
H11B H 0.161073 0.289279 0.670439 0.094 Uiso 1 1 calc R U . . .
C12B C 0.0618(7) 0.3546(5) 0.6001(4) 0.075(2) Uani 1 1 d . . . . .
H12B H -0.000616 0.389984 0.594280 0.090 Uiso 1 1 calc R U . . .
C13B C 0.1101(7) 0.3390(5) 0.5423(4) 0.074(2) Uani 1 1 d . . . . .
H13B H 0.169750 0.302153 0.545637 0.089 Uiso 1 1 calc R U . . .
C14B C 0.0725(6) 0.3756(5) 0.4838(4) 0.081(2) Uani 1 1 d . . . . .
H14B H 0.015130 0.413322 0.483864 0.097 Uiso 1 1 calc R U . . .
C15B C 0.1080(5) 0.3651(3) 0.4202(2) 0.073(2) Uani 1 1 d G . . . .
C16B C 0.1809(5) 0.3057(3) 0.4085(3) 0.074(2) Uani 1 1 d G . . . .
H16B H 0.206258 0.269161 0.441404 0.089 Uiso 1 1 calc R U . . .
C17B C 0.2159(5) 0.3010(3) 0.3476(3) 0.085(2) Uani 1 1 d G . . . .
H17B H 0.264660 0.261252 0.339754 0.101 Uiso 1 1 calc R U . . .
C18B C 0.1780(5) 0.3556(4) 0.2984(2) 0.093(3) Uani 1 1 d G . . . .
C19B C 0.1051(5) 0.4150(3) 0.3101(3) 0.103(3) Uani 1 1 d G . . . .
H19B H 0.079737 0.451594 0.277224 0.124 Uiso 1 1 calc R U . . .
C20B C 0.0701(5) 0.4198(3) 0.3710(3) 0.094(3) Uani 1 1 d G . . . .
H20B H 0.021333 0.459504 0.378874 0.113 Uiso 1 1 calc R U . . .
C21B C 0.3106(17) 0.2965(7) 0.2247(6) 0.194(8) Uani 1 1 d . . . . .
H21C H 0.352841 0.315287 0.191586 0.233 Uiso 1 1 calc R U . . .
H21D H 0.369787 0.283442 0.265556 0.233 Uiso 1 1 calc R U . . .
C22B C 0.2373(14) 0.2361(10) 0.2001(6) 0.195(7) Uani 1 1 d . . . . .
H22D H 0.286495 0.195747 0.189505 0.293 Uiso 1 1 calc R U . . .
H22E H 0.195597 0.219396 0.233560 0.293 Uiso 1 1 calc R U . . .
H22F H 0.178799 0.250962 0.160237 0.293 Uiso 1 1 calc R U . . .
C23B C 0.1914(13) 0.4164(7) 0.1883(6) 0.148(5) Uani 1 1 d . . . . .
H23C H 0.196413 0.464478 0.211409 0.177 Uiso 1 1 calc R U . . .
H23D H 0.252011 0.416187 0.161333 0.177 Uiso 1 1 calc R U . . .
C24B C 0.0690(14) 0.4077(6) 0.1438(6) 0.177(6) Uani 1 1 d . . . . .
H24D H 0.054083 0.448273 0.111813 0.266 Uiso 1 1 calc R U . . .
H24E H 0.064451 0.360485 0.120350 0.266 Uiso 1 1 calc R U . . .
H24F H 0.008929 0.408710 0.170357 0.266 Uiso 1 1 calc R U . . .
N1B N 0.2179(9) 0.3544(5) 0.2386(4) 0.138(3) Uani 1 1 d . . . . .
O1B O 0.2622(5) 0.2535(3) 0.7903(3) 0.0932(17) Uani 1 1 d . . . . .
O2B O -0.0991(5) 0.3710(3) 0.8191(3) 0.0816(16) Uani 1 1 d . . . . .
C1C C 0.7806(8) 0.2419(5) 1.0921(4) 0.077(2) Uani 1 1 d . . . . .
C2C C 0.7919(6) 0.2337(3) 1.1657(2) 0.072(2) Uani 1 1 d G . . . .
C3C C 0.8906(4) 0.2440(3) 1.2199(4) 0.102(3) Uani 1 1 d G . . . .
H3C H 0.966481 0.256464 1.212432 0.122 Uiso 1 1 calc R U . . .
C4C C 0.8758(6) 0.2358(4) 1.2853(3) 0.119(3) Uani 1 1 d G . . . .
H4C H 0.941831 0.242741 1.321597 0.142 Uiso 1 1 calc R U . . .
C5C C 0.7623(8) 0.2173(4) 1.2965(2) 0.107(3) Uani 1 1 d G . . . .
H5C H 0.752431 0.211766 1.340256 0.128 Uiso 1 1 calc R U . . .
C6C C 0.6636(5) 0.2069(3) 1.2423(4) 0.086(2) Uani 1 1 d G . . . .
H6C H 0.587681 0.194514 1.249750 0.103 Uiso 1 1 calc R U . . .
C7C C 0.6784(5) 0.2152(3) 1.1769(3) 0.069(2) Uani 1 1 d G . . . .
C8C C 0.5899(8) 0.2102(5) 1.1122(4) 0.077(2) Uani 1 1 d . . . . .
C9C C 0.6535(7) 0.2287(4) 1.0597(4) 0.072(2) Uani 1 1 d . . . . .
C10C C 0.5949(7) 0.2416(5) 0.9942(4) 0.081(2) Uani 1 1 d . . . . .
H10C H 0.510936 0.234577 0.984277 0.097 Uiso 1 1 calc R U . . .
C11C C 0.6444(8) 0.2643(5) 0.9390(4) 0.083(2) Uani 1 1 d . . . . .
H11C H 0.728486 0.266569 0.944245 0.100 Uiso 1 1 calc R U . . .
C12C C 0.5702(8) 0.2827(5) 0.8790(4) 0.082(2) Uani 1 1 d . . . . .
H12C H 0.486880 0.280284 0.876402 0.098 Uiso 1 1 calc R U . . .
C13C C 0.6060(7) 0.3050(5) 0.8204(4) 0.079(2) Uani 1 1 d . . . . .
H13C H 0.688671 0.306265 0.821016 0.095 Uiso 1 1 calc R U . . .
C14C C 0.5270(7) 0.3245(4) 0.7640(4) 0.076(2) Uani 1 1 d . . . . .
H14C H 0.445891 0.324416 0.766838 0.091 Uiso 1 1 calc R U . . .
C15C C 0.5470(5) 0.3460(3) 0.6977(2) 0.070(2) Uani 1 1 d G . . . .
C16C C 0.6610(4) 0.3385(3) 0.6833(2) 0.073(2) Uani 1 1 d G . . . .
H16C H 0.727171 0.322613 0.716539 0.087 Uiso 1 1 calc R U . . .
C17C C 0.6761(4) 0.3547(3) 0.6190(3) 0.076(2) Uani 1 1 d G . . . .
H17C H 0.752349 0.349699 0.609324 0.091 Uiso 1 1 calc R U . . .
C18C C 0.5772(5) 0.3785(3) 0.5693(2) 0.075(2) Uani 1 1 d G . . . .
C19C C 0.4632(4) 0.3860(3) 0.5838(3) 0.076(2) Uani 1 1 d G . . . .
H19C H 0.397035 0.401844 0.550486 0.091 Uiso 1 1 calc R U . . .
C20C C 0.4481(4) 0.3697(3) 0.6480(3) 0.078(2) Uani 1 1 d G . . . .
H20C H 0.371855 0.374758 0.657700 0.093 Uiso 1 1 calc R U . . .
C21C C 0.7104(8) 0.3856(5) 0.4863(4) 0.091(3) Uani 1 1 d . . . . .
H21E H 0.773143 0.404522 0.523425 0.109 Uiso 1 1 calc R U . . .
H21F H 0.709602 0.417254 0.447405 0.109 Uiso 1 1 calc R U . . .
C22C C 0.7410(8) 0.3048(6) 0.4705(4) 0.112(3) Uani 1 1 d . . . . .
H22G H 0.818987 0.303777 0.459102 0.168 Uiso 1 1 calc R U . . .
H22H H 0.743357 0.273538 0.509152 0.168 Uiso 1 1 calc R U . . .
H22I H 0.679856 0.286262 0.433181 0.168 Uiso 1 1 calc R U . . .
C23C C 0.4872(9) 0.3980(6) 0.4457(5) 0.108(3) Uani 1 1 d . . . . .
H23E H 0.506683 0.374038 0.406705 0.129 Uiso 1 1 calc R U . . .
H23F H 0.418184 0.371567 0.455720 0.129 Uiso 1 1 calc R U . . .
C24C C 0.4531(10) 0.4757(7) 0.4292(5) 0.150(4) Uani 1 1 d . . . . .
H24G H 0.384466 0.477160 0.391408 0.224 Uiso 1 1 calc R U . . .
H24H H 0.431849 0.499514 0.467240 0.224 Uiso 1 1 calc R U . . .
H24I H 0.520371 0.501986 0.418212 0.224 Uiso 1 1 calc R U . . .
N1C N 0.5931(6) 0.3907(4) 0.5039(3) 0.092(2) Uani 1 1 d . . . . .
O1C O 0.8651(5) 0.2587(4) 1.0663(3) 0.1036(19) Uani 1 1 d . . . . .
O2C O 0.4833(6) 0.1931(4) 1.1051(3) 0.112(2) Uani 1 1 d . . . . .
C1A C 0.7768(7) 0.5487(5) 0.6064(4) 0.071(2) Uani 1 1 d . . . . .
C2A C 0.7241(5) 0.5946(3) 0.5467(3) 0.067(2) Uani 1 1 d G . . . .
C3A C 0.7597(4) 0.6016(3) 0.4861(3) 0.082(2) Uani 1 1 d G . . . .
H3A H 0.827835 0.575732 0.479632 0.098 Uiso 1 1 calc R U . . .
C4A C 0.6934(6) 0.6471(4) 0.4353(2) 0.091(3) Uani 1 1 d G . . . .
H4A H 0.717247 0.651743 0.394725 0.109 Uiso 1 1 calc R U . . .
C5A C 0.5915(6) 0.6857(3) 0.4450(3) 0.091(3) Uani 1 1 d G . . . .
H5A H 0.547208 0.716166 0.410921 0.109 Uiso 1 1 calc R U . . .
C6A C 0.5559(4) 0.6788(3) 0.5055(4) 0.086(2) Uani 1 1 d G . . . .
H6A H 0.487754 0.704579 0.512024 0.103 Uiso 1 1 calc R U . . .
C7A C 0.6222(5) 0.6332(3) 0.5564(2) 0.066(2) Uani 1 1 d G . . . .
C8A C 0.6077(7) 0.6177(5) 0.6246(4) 0.070(2) Uani 1 1 d . . . . .
C9A C 0.7024(6) 0.5630(4) 0.6559(4) 0.067(2) Uani 1 1 d . . . . .
C10A C 0.7247(7) 0.5306(4) 0.7175(4) 0.072(2) Uani 1 1 d . . . . .
H10A H 0.786407 0.494608 0.725818 0.086 Uiso 1 1 calc R U . . .
C11A C 0.6676(7) 0.5438(5) 0.7703(4) 0.074(2) Uani 1 1 d . . . . .
H11A H 0.604802 0.578880 0.764567 0.089 Uiso 1 1 calc R U . . .
C12A C 0.7012(7) 0.5070(5) 0.8293(4) 0.073(2) Uani 1 1 d . . . . .
H12A H 0.757276 0.468174 0.830970 0.087 Uiso 1 1 calc R U . . .
C13A C 0.6610(7) 0.5204(5) 0.8893(4) 0.073(2) Uani 1 1 d . . . . .
H13A H 0.604390 0.558514 0.889177 0.088 Uiso 1 1 calc R U . . .
C14A C 0.7008(7) 0.4807(4) 0.9465(4) 0.076(2) Uani 1 1 d . . . . .
H14A H 0.755209 0.442104 0.943406 0.091 Uiso 1 1 calc R U . . .
C15A C 0.6723(5) 0.4885(3) 1.0122(2) 0.068(2) Uani 1 1 d G . . . .
C16A C 0.7177(5) 0.4334(3) 1.0599(3) 0.091(3) Uani 1 1 d G . . . .
H16A H 0.764548 0.394118 1.049196 0.110 Uiso 1 1 calc R U . . .
C17A C 0.6931(5) 0.4371(3) 1.1235(3) 0.100(3) Uani 1 1 d G . . . .
H17A H 0.723477 0.400266 1.155391 0.121 Uiso 1 1 calc R U . . .
C18A C 0.6231(6) 0.4958(4) 1.1395(2) 0.094(3) Uani 1 1 d G . . . .
C19A C 0.5777(5) 0.5509(3) 1.0918(3) 0.082(2) Uani 1 1 d G . . . .
H19A H 0.530916 0.590201 1.102518 0.098 Uiso 1 1 calc R U . . .
C20A C 0.6023(4) 0.5472(3) 1.0282(3) 0.069(2) Uani 1 1 d G . . . .
H20A H 0.571986 0.584054 0.996323 0.082 Uiso 1 1 calc R U . . .
C21A C 0.6170(14) 0.4339(8) 1.2503(6) 0.154(5) Uani 1 1 d . . . . .
H21G H 0.557170 0.433758 1.277747 0.184 Uiso 1 1 calc R U . . .
H21H H 0.610502 0.386455 1.226082 0.184 Uiso 1 1 calc R U . . .
C22A C 0.7353(14) 0.4409(8) 1.2923(6) 0.191(6) Uani 1 1 d . . . . .
H22J H 0.750450 0.399617 1.323466 0.287 Uiso 1 1 calc R U . . .
H22K H 0.794388 0.440398 1.265098 0.287 Uiso 1 1 calc R U . . .
H22L H 0.741164 0.487606 1.316659 0.287 Uiso 1 1 calc R U . . .
C23A C 0.4808(13) 0.5583(8) 1.2179(6) 0.154(5) Uani 1 1 d . . . . .
H23G H 0.423079 0.575522 1.177857 0.185 Uiso 1 1 calc R U . . .
H23H H 0.438994 0.538790 1.250897 0.185 Uiso 1 1 calc R U . . .
C24A C 0.5670(11) 0.6086(10) 1.2429(6) 0.194(7) Uani 1 1 d . . . . .
H24J H 0.530367 0.652395 1.257720 0.290 Uiso 1 1 calc R U . . .
H24K H 0.624142 0.586858 1.280302 0.290 Uiso 1 1 calc R U . . .
H24L H 0.608532 0.622883 1.208666 0.290 Uiso 1 1 calc R U . . .
N1A N 0.5916(9) 0.4980(5) 1.2012(4) 0.147(4) Uani 1 1 d . . . . .
O1A O 0.8663(5) 0.5079(3) 0.6130(2) 0.0859(16) Uani 1 1 d . . . . .
O2A O 0.5280(5) 0.6442(3) 0.6495(3) 0.0968(18) 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(9) . ?
C1 C9 1.467(11) . ?
C1 C2 1.468(10) . ?
C2 C3 1.3900 . ?
C2 C7 1.3900 . ?
C3 C4 1.3900 . ?
C3 H3 0.9300 . ?
C4 C5 1.3900 . ?
C4 H4 0.9300 . ?
C5 C6 1.3900 . ?
C5 H5 0.9300 . ?
C6 C7 1.3900 . ?
C6 H6 0.9300 . ?
C7 C8 1.463(10) . ?
C8 O2 1.234(9) . ?
C8 C9 1.464(11) . ?
C9 C10 1.349(10) . ?
C10 C11 1.391(11) . ?
C10 H10 0.9300 . ?
C11 C12 1.359(10) . ?
C11 H11 0.9300 . ?
C12 C13 1.420(10) . ?
C12 H12 0.9300 . ?
C13 C14 1.353(10) . ?
C13 H13 0.9300 . ?
C14 C15 1.460(9) . ?
C14 H14 0.9300 . ?
C15 C16 1.3900 . ?
C15 C20 1.3900 . ?
C16 C17 1.3900 . ?
C16 H16 0.9300 . ?
C17 C18 1.3900 . ?
C17 H17 0.9300 . ?
C18 N1 1.387(7) . ?
C18 C19 1.3900 . ?
C19 C20 1.3900 . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C21 N1 1.456(10) . ?
C21 C22 1.503(12) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 N1 1.466(9) . ?
C23 C24 1.525(13) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C1B O1B 1.222(8) . ?
C1B C9B 1.464(10) . ?
C1B C2B 1.473(8) . ?
C2B C3B 1.3900 . ?
C2B C7B 1.3900 . ?
C3B C4B 1.3900 . ?
C3B H3B 0.9300 . ?
C4B C5B 1.3900 . ?
C4B H4B 0.9300 . ?
C5B C6B 1.3900 . ?
C5B H5B 0.9300 . ?
C6B C7B 1.3900 . ?
C6B H6B 0.9300 . ?
C7B C8B 1.460(8) . ?
C8B O2B 1.219(8) . ?
C8B C9B 1.474(9) . ?
C9B C10B 1.346(9) . ?
C10B C11B 1.425(9) . ?
C10B H10B 0.9300 . ?
C11B C12B 1.352(10) . ?
C11B H11B 0.9300 . ?
C12B C13B 1.433(10) . ?
C12B H12B 0.9300 . ?
C13B C14B 1.339(10) . ?
C13B H13B 0.9300 . ?
C14B C15B 1.456(8) . ?
C14B H14B 0.9300 . ?
C15B C16B 1.3900 . ?
C15B C20B 1.3900 . ?
C16B C17B 1.3900 . ?
C16B H16B 0.9300 . ?
C17B C18B 1.3900 . ?
C17B H17B 0.9300 . ?
C18B C19B 1.3900 . ?
C18B N1B 1.394(9) . ?
C19B C20B 1.3900 . ?
C19B H19B 0.9300 . ?
C20B H20B 0.9300 . ?
C21B C22B 1.375(19) . ?
C21B N1B 1.537(16) . ?
C21B H21C 0.9700 . ?
C21B H21D 0.9700 . ?
C22B H22D 0.9600 . ?
C22B H22E 0.9600 . ?
C22B H22F 0.9600 . ?
C23B C24B 1.476(15) . ?
C23B N1B 1.487(13) . ?
C23B H23C 0.9700 . ?
C23B H23D 0.9700 . ?
C24B H24D 0.9600 . ?
C24B H24E 0.9600 . ?
C24B H24F 0.9600 . ?
C1C O1C 1.226(8) . ?
C1C C9C 1.454(10) . ?
C1C C2C 1.484(9) . ?
C2C C3C 1.3900 . ?
C2C C7C 1.3900 . ?
C3C C4C 1.3900 . ?
C3C H3C 0.9300 . ?
C4C C5C 1.3900 . ?
C4C H4C 0.9300 . ?
C5C C6C 1.3900 . ?
C5C H5C 0.9300 . ?
C6C C7C 1.3900 . ?
C6C H6C 0.9300 . ?
C7C C8C 1.463(9) . ?
C8C O2C 1.216(8) . ?
C8C C9C 1.456(10) . ?
C9C C10C 1.368(10) . ?
C10C C11C 1.425(10) . ?
C10C H10C 0.9300 . ?
C11C C12C 1.355(10) . ?
C11C H11C 0.9300 . ?
C12C C13C 1.405(10) . ?
C12C H12C 0.9300 . ?
C13C C14C 1.329(10) . ?
C13C H13C 0.9300 . ?
C14C C15C 1.470(8) . ?
C14C H14C 0.9300 . ?
C15C C16C 1.3900 . ?
C15C C20C 1.3900 . ?
C16C C17C 1.3900 . ?
C16C H16C 0.9300 . ?
C17C C18C 1.3900 . ?
C17C H17C 0.9300 . ?
C18C C19C 1.3900 . ?
C18C N1C 1.403(7) . ?
C19C C20C 1.3900 . ?
C19C H19C 0.9300 . ?
C20C H20C 0.9300 . ?
C21C N1C 1.451(9) . ?
C21C C22C 1.526(12) . ?
C21C H21E 0.9700 . ?
C21C H21F 0.9700 . ?
C22C H22G 0.9600 . ?
C22C H22H 0.9600 . ?
C22C H22I 0.9600 . ?
C23C C24C 1.449(13) . ?
C23C N1C 1.484(10) . ?
C23C H23E 0.9700 . ?
C23C H23F 0.9700 . ?
C24C H24G 0.9600 . ?
C24C H24H 0.9600 . ?
C24C H24I 0.9600 . ?
C1A O1A 1.224(8) . ?
C1A C2A 1.473(9) . ?
C1A C9A 1.475(10) . ?
C2A C3A 1.3900 . ?
C2A C7A 1.3900 . ?
C3A C4A 1.3900 . ?
C3A H3A 0.9300 . ?
C4A C5A 1.3900 . ?
C4A H4A 0.9300 . ?
C5A C6A 1.3900 . ?
C5A H5A 0.9300 . ?
C6A C7A 1.3900 . ?
C6A H6A 0.9300 . ?
C7A C8A 1.464(9) . ?
C8A O2A 1.222(8) . ?
C8A C9A 1.475(11) . ?
C9A C10A 1.352(10) . ?
C10A C11A 1.396(9) . ?
C10A H10A 0.9300 . ?
C11A C12A 1.345(10) . ?
C11A H11A 0.9300 . ?
C12A C13A 1.419(9) . ?
C12A H12A 0.9300 . ?
C13A C14A 1.348(10) . ?
C13A H13A 0.9300 . ?
C14A C15A 1.457(9) . ?
C14A H14A 0.9300 . ?
C15A C16A 1.3900 . ?
C15A C20A 1.3900 . ?
C16A C17A 1.3900 . ?
C16A H16A 0.9300 . ?
C17A C18A 1.3900 . ?
C17A H17A 0.9300 . ?
C18A N1A 1.386(9) . ?
C18A C19A 1.3900 . ?
C19A C20A 1.3900 . ?
C19A H19A 0.9300 . ?
C20A H20A 0.9300 . ?
C21A C22A 1.415(15) . ?
C21A N1A 1.499(14) . ?
C21A H21G 0.9700 . ?
C21A H21H 0.9700 . ?
C22A H22J 0.9600 . ?
C22A H22K 0.9600 . ?
C22A H22L 0.9600 . ?
C23A C24A 1.331(15) . ?
C23A N1A 1.737(15) . ?
C23A H23G 0.9700 . ?
C23A H23H 0.9700 . ?
C24A H24J 0.9600 . ?
C24A H24K 0.9600 . ?
C24A H24L 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 C9 128.4(8) . . ?
O1 C1 C2 125.3(9) . . ?
C9 C1 C2 106.2(8) . . ?
C3 C2 C7 120.0 . . ?
C3 C2 C1 129.8(7) . . ?
C7 C2 C1 110.1(7) . . ?
C2 C3 C4 120.0 . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C5 C4 C3 120.0 . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C4 C5 C6 120.0 . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C7 C6 C5 120.0 . . ?
C7 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
C6 C7 C2 120.0 . . ?
C6 C7 C8 131.3(7) . . ?
C2 C7 C8 108.4(7) . . ?
O2 C8 C7 125.7(8) . . ?
O2 C8 C9 126.4(8) . . ?
C7 C8 C9 107.6(8) . . ?
C10 C9 C8 123.6(8) . . ?
C10 C9 C1 128.4(8) . . ?
C8 C9 C1 107.2(8) . . ?
C9 C10 C11 129.8(8) . . ?
C9 C10 H10 115.1 . . ?
C11 C10 H10 115.1 . . ?
C12 C11 C10 122.8(8) . . ?
C12 C11 H11 118.6 . . ?
C10 C11 H11 118.6 . . ?
C11 C12 C13 127.9(8) . . ?
C11 C12 H12 116.1 . . ?
C13 C12 H12 116.1 . . ?
C14 C13 C12 122.5(8) . . ?
C14 C13 H13 118.7 . . ?
C12 C13 H13 118.7 . . ?
C13 C14 C15 127.9(8) . . ?
C13 C14 H14 116.1 . . ?
C15 C14 H14 116.1 . . ?
C16 C15 C20 120.0 . . ?
C16 C15 C14 121.8(5) . . ?
C20 C15 C14 117.9(5) . . ?
C17 C16 C15 120.0 . . ?
C17 C16 H16 120.0 . . ?
C15 C16 H16 120.0 . . ?
C16 C17 C18 120.0 . . ?
C16 C17 H17 120.0 . . ?
C18 C17 H17 120.0 . . ?
N1 C18 C17 120.2(5) . . ?
N1 C18 C19 119.8(5) . . ?
C17 C18 C19 120.0 . . ?
C20 C19 C18 120.0 . . ?
C20 C19 H19 120.0 . . ?
C18 C19 H19 120.0 . . ?
C19 C20 C15 120.0 . . ?
C19 C20 H20 120.0 . . ?
C15 C20 H20 120.0 . . ?
N1 C21 C22 113.6(8) . . ?
N1 C21 H21A 108.8 . . ?
C22 C21 H21A 108.8 . . ?
N1 C21 H21B 108.8 . . ?
C22 C21 H21B 108.8 . . ?
H21A C21 H21B 107.7 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
N1 C23 C24 112.7(8) . . ?
N1 C23 H23A 109.0 . . ?
C24 C23 H23A 109.0 . . ?
N1 C23 H23B 109.0 . . ?
C24 C23 H23B 109.0 . . ?
H23A C23 H23B 107.8 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C18 N1 C21 122.3(6) . . ?
C18 N1 C23 121.8(7) . . ?
C21 N1 C23 115.1(7) . . ?
O1B C1B C9B 128.9(7) . . ?
O1B C1B C2B 125.6(7) . . ?
C9B C1B C2B 105.4(6) . . ?
C3B C2B C7B 120.0 . . ?
C3B C2B C1B 129.6(5) . . ?
C7B C2B C1B 110.2(5) . . ?
C2B C3B C4B 120.0 . . ?
C2B C3B H3B 120.0 . . ?
C4B C3B H3B 120.0 . . ?
C5B C4B C3B 120.0 . . ?
C5B C4B H4B 120.0 . . ?
C3B C4B H4B 120.0 . . ?
C4B C5B C6B 120.0 . . ?
C4B C5B H5B 120.0 . . ?
C6B C5B H5B 120.0 . . ?
C7B C6B C5B 120.0 . . ?
C7B C6B H6B 120.0 . . ?
C5B C6B H6B 120.0 . . ?
C6B C7B C2B 120.0 . . ?
C6B C7B C8B 130.3(5) . . ?
C2B C7B C8B 109.6(5) . . ?
O2B C8B C7B 126.4(7) . . ?
O2B C8B C9B 127.5(7) . . ?
C7B C8B C9B 106.1(6) . . ?
C10B C9B C1B 128.5(7) . . ?
C10B C9B C8B 122.8(7) . . ?
C1B C9B C8B 108.7(7) . . ?
C9B C10B C11B 127.3(7) . . ?
C9B C10B H10B 116.4 . . ?
C11B C10B H10B 116.4 . . ?
C12B C11B C10B 121.7(8) . . ?
C12B C11B H11B 119.1 . . ?
C10B C11B H11B 119.1 . . ?
C11B C12B C13B 127.2(8) . . ?
C11B C12B H12B 116.4 . . ?
C13B C12B H12B 116.4 . . ?
C14B C13B C12B 122.5(7) . . ?
C14B C13B H13B 118.8 . . ?
C12B C13B H13B 118.8 . . ?
C13B C14B C15B 129.6(7) . . ?
C13B C14B H14B 115.2 . . ?
C15B C14B H14B 115.2 . . ?
C16B C15B C20B 120.0 . . ?
C16B C15B C14B 123.0(5) . . ?
C20B C15B C14B 116.9(5) . . ?
C15B C16B C17B 120.0 . . ?
C15B C16B H16B 120.0 . . ?
C17B C16B H16B 120.0 . . ?
C18B C17B C16B 120.0 . . ?
C18B C17B H17B 120.0 . . ?
C16B C17B H17B 120.0 . . ?
C17B C18B C19B 120.0 . . ?
C17B C18B N1B 120.9(6) . . ?
C19B C18B N1B 119.0(6) . . ?
C20B C19B C18B 120.0 . . ?
C20B C19B H19B 120.0 . . ?
C18B C19B H19B 120.0 . . ?
C19B C20B C15B 120.0 . . ?
C19B C20B H20B 120.0 . . ?
C15B C20B H20B 120.0 . . ?
C22B C21B N1B 102.2(15) . . ?
C22B C21B H21C 111.3 . . ?
N1B C21B H21C 111.3 . . ?
C22B C21B H21D 111.3 . . ?
N1B C21B H21D 111.3 . . ?
H21C C21B H21D 109.2 . . ?
C21B C22B H22D 109.5 . . ?
C21B C22B H22E 109.5 . . ?
H22D C22B H22E 109.5 . . ?
C21B C22B H22F 109.5 . . ?
H22D C22B H22F 109.5 . . ?
H22E C22B H22F 109.5 . . ?
C24B C23B N1B 111.0(12) . . ?
C24B C23B H23C 109.4 . . ?
N1B C23B H23C 109.4 . . ?
C24B C23B H23D 109.4 . . ?
N1B C23B H23D 109.4 . . ?
H23C C23B H23D 108.0 . . ?
C23B C24B H24D 109.5 . . ?
C23B C24B H24E 109.5 . . ?
H24D C24B H24E 109.5 . . ?
C23B C24B H24F 109.5 . . ?
H24D C24B H24F 109.5 . . ?
H24E C24B H24F 109.5 . . ?
C18B N1B C23B 122.7(8) . . ?
C18B N1B C21B 122.8(8) . . ?
C23B N1B C21B 113.7(9) . . ?
O1C C1C C9C 128.8(8) . . ?
O1C C1C C2C 124.3(8) . . ?
C9C C1C C2C 106.9(6) . . ?
C3C C2C C7C 120.0 . . ?
C3C C2C C1C 131.2(6) . . ?
C7C C2C C1C 108.7(6) . . ?
C4C C3C C2C 120.0 . . ?
C4C C3C H3C 120.0 . . ?
C2C C3C H3C 120.0 . . ?
C3C C4C C5C 120.0 . . ?
C3C C4C H4C 120.0 . . ?
C5C C4C H4C 120.0 . . ?
C4C C5C C6C 120.0 . . ?
C4C C5C H5C 120.0 . . ?
C6C C5C H5C 120.0 . . ?
C7C C6C C5C 120.0 . . ?
C7C C6C H6C 120.0 . . ?
C5C C6C H6C 120.0 . . ?
C6C C7C C2C 120.0 . . ?
C6C C7C C8C 130.7(6) . . ?
C2C C7C C8C 109.2(6) . . ?
O2C C8C C9C 127.5(8) . . ?
O2C C8C C7C 125.0(7) . . ?
C9C C8C C7C 107.5(7) . . ?
C10C C9C C1C 128.5(7) . . ?
C10C C9C C8C 123.2(7) . . ?
C1C C9C C8C 107.6(7) . . ?
C9C C10C C11C 129.1(8) . . ?
C9C C10C H10C 115.5 . . ?
C11C C10C H10C 115.5 . . ?
C12C C11C C10C 120.6(8) . . ?
C12C C11C H11C 119.7 . . ?
C10C C11C H11C 119.7 . . ?
C11C C12C C13C 126.8(8) . . ?
C11C C12C H12C 116.6 . . ?
C13C C12C H12C 116.6 . . ?
C14C C13C C12C 123.0(8) . . ?
C14C C13C H13C 118.5 . . ?
C12C C13C H13C 118.5 . . ?
C13C C14C C15C 130.5(7) . . ?
C13C C14C H14C 114.8 . . ?
C15C C14C H14C 114.8 . . ?
C16C C15C C20C 120.0 . . ?
C16C C15C C14C 121.0(5) . . ?
C20C C15C C14C 118.9(5) . . ?
C17C C16C C15C 120.0 . . ?
C17C C16C H16C 120.0 . . ?
C15C C16C H16C 120.0 . . ?
C16C C17C C18C 120.0 . . ?
C16C C17C H17C 120.0 . . ?
C18C C17C H17C 120.0 . . ?
C19C C18C C17C 120.0 . . ?
C19C C18C N1C 120.9(5) . . ?
C17C C18C N1C 119.0(5) . . ?
C18C C19C C20C 120.0 . . ?
C18C C19C H19C 120.0 . . ?
C20C C19C H19C 120.0 . . ?
C19C C20C C15C 120.0 . . ?
C19C C20C H20C 120.0 . . ?
C15C C20C H20C 120.0 . . ?
N1C C21C C22C 111.9(8) . . ?
N1C C21C H21E 109.2 . . ?
C22C C21C H21E 109.2 . . ?
N1C C21C H21F 109.2 . . ?
C22C C21C H21F 109.2 . . ?
H21E C21C H21F 107.9 . . ?
C21C C22C H22G 109.5 . . ?
C21C C22C H22H 109.5 . . ?
H22G C22C H22H 109.5 . . ?
C21C C22C H22I 109.5 . . ?
H22G C22C H22I 109.5 . . ?
H22H C22C H22I 109.5 . . ?
C24C C23C N1C 113.0(9) . . ?
C24C C23C H23E 109.0 . . ?
N1C C23C H23E 109.0 . . ?
C24C C23C H23F 109.0 . . ?
N1C C23C H23F 109.0 . . ?
H23E C23C H23F 107.8 . . ?
C23C C24C H24G 109.5 . . ?
C23C C24C H24H 109.5 . . ?
H24G C24C H24H 109.5 . . ?
C23C C24C H24I 109.5 . . ?
H24G C24C H24I 109.5 . . ?
H24H C24C H24I 109.5 . . ?
C18C N1C C21C 123.2(6) . . ?
C18C N1C C23C 121.3(7) . . ?
C21C N1C C23C 114.8(7) . . ?
O1A C1A C2A 125.7(7) . . ?
O1A C1A C9A 127.7(7) . . ?
C2A C1A C9A 106.6(7) . . ?
C3A C2A C7A 120.0 . . ?
C3A C2A C1A 129.8(6) . . ?
C7A C2A C1A 110.1(6) . . ?
C4A C3A C2A 120.0 . . ?
C4A C3A H3A 120.0 . . ?
C2A C3A H3A 120.0 . . ?
C3A C4A C5A 120.0 . . ?
C3A C4A H4A 120.0 . . ?
C5A C4A H4A 120.0 . . ?
C6A C5A C4A 120.0 . . ?
C6A C5A H5A 120.0 . . ?
C4A C5A H5A 120.0 . . ?
C5A C6A C7A 120.0 . . ?
C5A C6A H6A 120.0 . . ?
C7A C6A H6A 120.0 . . ?
C6A C7A C2A 120.0 . . ?
C6A C7A C8A 131.4(6) . . ?
C2A C7A C8A 108.6(6) . . ?
O2A C8A C7A 125.1(7) . . ?
O2A C8A C9A 126.9(8) . . ?
C7A C8A C9A 107.9(7) . . ?
C10A C9A C1A 123.3(7) . . ?
C10A C9A C8A 130.1(7) . . ?
C1A C9A C8A 106.6(7) . . ?
C9A C10A C11A 128.7(7) . . ?
C9A C10A H10A 115.6 . . ?
C11A C10A H10A 115.6 . . ?
C12A C11A C10A 121.6(8) . . ?
C12A C11A H11A 119.2 . . ?
C10A C11A H11A 119.2 . . ?
C11A C12A C13A 127.6(8) . . ?
C11A C12A H12A 116.2 . . ?
C13A C12A H12A 116.2 . . ?
C14A C13A C12A 123.4(8) . . ?
C14A C13A H13A 118.3 . . ?
C12A C13A H13A 118.3 . . ?
C13A C14A C15A 130.4(7) . . ?
C13A C14A H14A 114.8 . . ?
C15A C14A H14A 114.8 . . ?
C16A C15A C20A 120.0 . . ?
C16A C15A C14A 117.0(6) . . ?
C20A C15A C14A 123.0(6) . . ?
C15A C16A C17A 120.0 . . ?
C15A C16A H16A 120.0 . . ?
C17A C16A H16A 120.0 . . ?
C18A C17A C16A 120.0 . . ?
C18A C17A H17A 120.0 . . ?
C16A C17A H17A 120.0 . . ?
N1A C18A C17A 120.8(6) . . ?
N1A C18A C19A 119.1(6) . . ?
C17A C18A C19A 120.0 . . ?
C20A C19A C18A 120.0 . . ?
C20A C19A H19A 120.0 . . ?
C18A C19A H19A 120.0 . . ?
C19A C20A C15A 120.0 . . ?
C19A C20A H20A 120.0 . . ?
C15A C20A H20A 120.0 . . ?
C22A C21A N1A 110.2(13) . . ?
C22A C21A H21G 109.6 . . ?
N1A C21A H21G 109.6 . . ?
C22A C21A H21H 109.6 . . ?
N1A C21A H21H 109.6 . . ?
H21G C21A H21H 108.1 . . ?
C21A C22A H22J 109.5 . . ?
C21A C22A H22K 109.5 . . ?
H22J C22A H22K 109.5 . . ?
C21A C22A H22L 109.5 . . ?
H22J C22A H22L 109.5 . . ?
H22K C22A H22L 109.5 . . ?
C24A C23A N1A 89.6(12) . . ?
C24A C23A H23G 113.7 . . ?
N1A C23A H23G 113.7 . . ?
C24A C23A H23H 113.7 . . ?
N1A C23A H23H 113.7 . . ?
H23G C23A H23H 111.0 . . ?
C23A C24A H24J 109.5 . . ?
C23A C24A H24K 109.5 . . ?
H24J C24A H24K 109.5 . . ?
C23A C24A H24L 109.5 . . ?
H24J C24A H24L 109.5 . . ?
H24K C24A H24L 109.5 . . ?
C18A N1A C21A 122.5(8) . . ?
C18A N1A C23A 122.8(7) . . ?
C21A N1A C23A 111.8(9) . . ?

_refine_diff_density_max         0.132
_refine_diff_density_min         -0.120
_refine_diff_density_rms         0.025

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

data_DIDLET
_database_code_depnum_ccdc_archive 'CCDC 2083071'
_audit_update_record             
;
2022-07-28 deposited with the CCDC.	2022-09-21 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_THETM01_DIDLET              
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.550
RESPONSE: Data were collected to resolution of 0.74 \A and were truncated
to statistically relevant resolution.

;
# end Validation Reply Form


_audit_creation_method           SHELXL-2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H21 N3 O'
_chemical_formula_weight         379.45

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

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

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

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

_cell_length_a                   11.991(3)
_cell_length_b                   12.429(3)
_cell_length_c                   14.575(3)
_cell_angle_alpha                103.172(16)
_cell_angle_beta                 107.987(18)
_cell_angle_gamma                93.834(19)
_cell_volume                     1989.5(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    193(2)
_cell_measurement_reflns_used    53
_cell_measurement_theta_min      2.18
_cell_measurement_theta_max      16.56

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.14
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.267
_exptl_crystal_F_000             800
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?

_exptl_absorpt_coefficient_mu    0.079
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_special_details           
;

Crystal suitable for X--ray structure determination was selected under the
polarizing microscope, covered with Paratone oil and mounted on a goniometer
head. Experiment was performed at the low temperature. Data
were collected till resolution of 0.74 Α and were truncated with XPREP till
actual observed resolution.
;

_diffrn_ambient_temperature      193(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Syntax P-1'
_diffrn_measurement_method       '2-theta/omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5521
_diffrn_reflns_av_unetI/netI     0.0442
_diffrn_reflns_av_R_equivalents  0.0508
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.290
_diffrn_reflns_theta_max         22.974
_diffrn_reflns_theta_full        22.974
_diffrn_measured_fraction_theta_max 0.942
_diffrn_measured_fraction_theta_full 0.942
_diffrn_reflns_Laue_measured_fraction_max 0.942
_diffrn_reflns_Laue_measured_fraction_full 0.942
_diffrn_reflns_point_group_measured_fraction_max 0.942
_diffrn_reflns_point_group_measured_fraction_full 0.942
_reflns_number_total             5205
_reflns_number_gt                3840
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         ?
_reflns_Friedel_fraction_max     ?
_reflns_Friedel_fraction_full    ?



_computing_data_collection       'Syntax P-1 Suite'
_computing_cell_refinement       'Syntax P-1 Suite'
_computing_data_reduction        'Syntax P-1 Suite'
_computing_structure_solution    'Syntax P-1 Suite'
_computing_molecular_graphics    'XSHELL, Bruker'
_computing_publication_material  "'XSHELL, Bruker"
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'

_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)+(0.1159P)²+2.7047P] 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         5205
_refine_ls_number_parameters     527
_refine_ls_number_restraints     9
_refine_ls_R_factor_all          0.0995
_refine_ls_R_factor_gt           0.0719
_refine_ls_wR_factor_ref         0.2067
_refine_ls_wR_factor_gt          0.1842
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.033
_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
O1 O 0.7025(3) 0.2103(2) 0.1869(2) 0.0391(8) Uani 1 1 d . . . . .
N1 N 1.3107(3) -0.0857(3) 0.1286(2) 0.0304(8) Uani 1 1 d . . . . .
N2 N 0.6088(4) 0.7208(3) 0.0585(3) 0.0418(10) Uani 1 1 d . . . . .
N3 N 0.9001(5) 0.5794(4) 0.0237(4) 0.0770(17) Uani 1 1 d . . . . .
C1 C 0.6832(4) 0.3004(3) 0.1690(3) 0.0292(10) Uani 1 1 d . . . . .
C2 C 0.7501(3) 0.3693(3) 0.1278(3) 0.0260(9) Uani 1 1 d . . . . .
C3 C 0.6912(3) 0.4669(3) 0.1181(3) 0.0256(9) Uani 1 1 d . . . . .
C3A C 0.5895(3) 0.4582(3) 0.1551(3) 0.0258(9) Uani 1 1 d . . . . .
C4 C 0.5059(4) 0.5283(3) 0.1645(3) 0.0316(10) Uani 1 1 d . . . . .
H4 H 0.508094 0.596931 0.146376 0.038 Uiso 1 1 calc R U . . .
C5 C 0.4193(4) 0.4951(4) 0.2009(3) 0.0391(11) Uani 1 1 d . . . . .
H5 H 0.360108 0.541019 0.205888 0.047 Uiso 1 1 calc R U . . .
C6 C 0.4163(4) 0.3974(4) 0.2302(4) 0.0420(11) Uani 1 1 d . . . . .
H6 H 0.355992 0.377664 0.255655 0.050 Uiso 1 1 calc R U . . .
C7 C 0.5001(4) 0.3277(3) 0.2230(3) 0.0342(10) Uani 1 1 d . . . . .
H7 H 0.499151 0.260575 0.243621 0.041 Uiso 1 1 calc R U . . .
C7A C 0.5847(4) 0.3591(3) 0.1850(3) 0.0280(9) Uani 1 1 d . . . . .
C8 C 0.8472(4) 0.3410(3) 0.1018(3) 0.0300(10) Uani 1 1 d . . . . .
H8 H 0.879299 0.390387 0.072252 0.036 Uiso 1 1 calc R U . . .
C9 C 0.9049(4) 0.2474(3) 0.1138(3) 0.0295(10) Uani 1 1 d . . . . .
H9 H 0.877536 0.194918 0.143220 0.035 Uiso 1 1 calc R U . . .
C10 C 1.0002(4) 0.2329(3) 0.0828(3) 0.0297(10) Uani 1 1 d . . . . .
H10 H 1.020573 0.286708 0.051359 0.036 Uiso 1 1 calc R U . . .
C11 C 1.0736(3) 0.1473(3) 0.0914(3) 0.0247(9) Uani 1 1 d . . . . .
C12 C 1.0583(3) 0.0622(3) 0.1374(3) 0.0250(9) Uani 1 1 d . . . . .
H12 H 0.993606 0.058190 0.161701 0.030 Uiso 1 1 calc R U . . .
C13 C 1.1341(3) -0.0148(3) 0.1482(3) 0.0244(9) Uani 1 1 d . . . . .
H13 H 1.121661 -0.070659 0.180443 0.029 Uiso 1 1 calc R U . . .
C14 C 1.2312(3) -0.0128(3) 0.1120(3) 0.0254(9) Uani 1 1 d . . . . .
C15 C 1.2440(4) 0.0691(3) 0.0611(3) 0.0296(9) Uani 1 1 d . . . . .
H15 H 1.305685 0.070960 0.033077 0.035 Uiso 1 1 calc R U . . .
C16 C 1.1667(4) 0.1459(3) 0.0525(3) 0.0304(10) Uani 1 1 d . . . . .
H16 H 1.176916 0.200601 0.018490 0.037 Uiso 1 1 calc R U . . .
C17 C 1.3155(4) -0.1512(3) 0.2011(3) 0.0339(10) Uani 1 1 d . . . . .
H17A H 1.285195 -0.110540 0.253005 0.041 Uiso 1 1 calc R U . . .
H17B H 1.399221 -0.158091 0.234387 0.041 Uiso 1 1 calc R U . . .
C18 C 1.2443(5) -0.2674(4) 0.1549(4) 0.0467(12) Uani 1 1 d . . . . .
H18A H 1.160665 -0.261414 0.123988 0.070 Uiso 1 1 calc R U . . .
H18B H 1.252016 -0.307049 0.206939 0.070 Uiso 1 1 calc R U . . .
H18C H 1.274269 -0.308671 0.103911 0.070 Uiso 1 1 calc R U . . .
C19 C 1.4000(4) -0.0986(3) 0.0790(3) 0.0332(10) Uani 1 1 d . . . . .
H19A H 1.366265 -0.087889 0.011135 0.040 Uiso 1 1 calc R U . . .
H19B H 1.418907 -0.175744 0.071700 0.040 Uiso 1 1 calc R U . . .
C20 C 1.5132(4) -0.0173(4) 0.1349(4) 0.0442(12) Uani 1 1 d . . . . .
H20A H 1.495808 0.059304 0.139678 0.066 Uiso 1 1 calc R U . . .
H20B H 1.569926 -0.031181 0.099019 0.066 Uiso 1 1 calc R U . . .
H20C H 1.547215 -0.027384 0.202213 0.066 Uiso 1 1 calc R U . . .
C21 C 0.7210(4) 0.5537(3) 0.0821(3) 0.0293(10) Uani 1 1 d . . . . .
C22 C 0.6560(4) 0.6450(3) 0.0713(3) 0.0296(10) Uani 1 1 d . . . . .
C23 C 0.8217(5) 0.5641(4) 0.0500(4) 0.0454(12) Uani 1 1 d . . . . .
O1' O 0.1641(3) 0.7844(2) 0.3481(2) 0.0373(7) Uani 1 1 d . . . . .
N1' N 0.8016(3) 0.5231(3) 0.5637(3) 0.0491(11) Uani 1 1 d D . . . .
N2' N 0.0796(4) 1.3209(3) 0.5764(3) 0.0505(11) Uani 1 1 d . . . . .
N3' N 0.4019(4) 1.2085(3) 0.7008(3) 0.0420(9) Uani 1 1 d . . . . .
C1' C 0.1457(4) 0.8778(3) 0.3828(3) 0.0281(9) Uani 1 1 d . . . . .
C2' C 0.2269(3) 0.9659(3) 0.4684(3) 0.0248(9) Uani 1 1 d . . . . .
C3' C 0.1635(3) 1.0614(3) 0.4834(3) 0.0246(9) Uani 1 1 d . . . . .
C3'A C 0.0452(3) 1.0332(3) 0.4039(3) 0.0250(9) Uani 1 1 d . . . . .
C4' C -0.0496(4) 1.0926(3) 0.3797(3) 0.0321(10) Uani 1 1 d . . . . .
H4' H -0.045227 1.166827 0.417630 0.039 Uiso 1 1 calc R U . . .
C5' C -0.1501(4) 1.0417(4) 0.2994(3) 0.0357(11) Uani 1 1 d . . . . .
H5' H -0.214724 1.082004 0.282525 0.043 Uiso 1 1 calc R U . . .
C6' C -0.1592(4) 0.9339(4) 0.2431(3) 0.0352(10) Uani 1 1 d . . . . .
H6' H -0.229865 0.900845 0.188840 0.042 Uiso 1 1 calc R U . . .
C7' C -0.0656(4) 0.8737(4) 0.2653(3) 0.0339(10) Uani 1 1 d . . . . .
H7' H -0.070522 0.799653 0.226759 0.041 Uiso 1 1 calc R U . . .
C7'A C 0.0353(3) 0.9247(3) 0.3456(3) 0.0268(9) Uani 1 1 d . . . . .
C8' C 0.3404(3) 0.9554(3) 0.5215(3) 0.0272(9) Uani 1 1 d . . . . .
H8' H 0.383252 1.017024 0.576212 0.033 Uiso 1 1 calc R U . . .
C9' C 0.4001(3) 0.8635(3) 0.5037(3) 0.0277(9) Uani 1 1 d . . . . .
H9' H 0.362999 0.801751 0.447361 0.033 Uiso 1 1 calc R U . . .
C10' C 0.5114(4) 0.8621(3) 0.5666(3) 0.0301(10) Uani 1 1 d . . . . .
H10' H 0.544452 0.926613 0.621024 0.036 Uiso 1 1 calc R U . . .
C11' C 0.5839(3) 0.7762(3) 0.5610(3) 0.0242(9) Uani 1 1 d . . . . .
C12' C 0.5542(4) 0.6772(3) 0.4828(3) 0.0286(9) Uani 1 1 d . . . . .
H12' H 0.481879 0.666492 0.428914 0.034 Uiso 1 1 calc R U . . .
C13' C 0.6259(4) 0.5964(3) 0.4820(3) 0.0327(10) Uani 1 1 d . . . . .
H13' H 0.603206 0.531756 0.427111 0.039 Uiso 1 1 calc R U . . .
C14' C 0.7339(4) 0.6073(3) 0.5617(3) 0.0310(10) Uani 1 1 d . . . . .
C15' C 0.7658(3) 0.7076(3) 0.6380(3) 0.0256(9) Uani 1 1 d . . . . .
H15' H 0.838863 0.719403 0.691173 0.031 Uiso 1 1 calc R U . . .
C16' C 0.6942(4) 0.7880(3) 0.6372(3) 0.0275(9) Uani 1 1 d . . . . .
H16' H 0.719411 0.854675 0.689907 0.033 Uiso 1 1 calc R U . . .
C17' C 0.7588(5) 0.4119(3) 0.5017(4) 0.082(2) Uani 1 1 d D U . . .
H17C H 0.671259 0.399557 0.472420 0.099 Uiso 1 1 calc R U . . .
H17D H 0.783769 0.356220 0.540028 0.099 Uiso 1 1 calc R U . . .
C19' C 0.9087(4) 0.5304(3) 0.6488(3) 0.0365(11) Uani 1 1 d . . . . .
H19C H 0.951714 0.607691 0.672753 0.044 Uiso 1 1 calc R U . . .
H19D H 0.961592 0.480017 0.627189 0.044 Uiso 1 1 calc R U . . .
C20' C 0.8783(4) 0.4984(4) 0.7335(4) 0.0501(13) Uani 1 1 d . . . . .
H20D H 0.833847 0.553459 0.760212 0.075 Uiso 1 1 calc R U . . .
H20E H 0.951463 0.496466 0.786491 0.075 Uiso 1 1 calc R U . . .
H20F H 0.829815 0.424396 0.708380 0.075 Uiso 1 1 calc R U . . .
C21' C 0.2011(3) 1.1597(3) 0.5573(3) 0.0259(9) Uani 1 1 d . . . . .
C22' C 0.1318(4) 1.2484(4) 0.5656(3) 0.0328(10) Uani 1 1 d . . . . .
C23' C 0.3137(4) 1.1840(3) 0.6354(3) 0.0298(10) Uani 1 1 d . . . . .
C18' C 0.8163(5) 0.4048(7) 0.4204(4) 0.096(2) Uani 1 1 d D U . . .
H18D H 0.788627 0.459237 0.382537 0.144 Uiso 1 1 calc R U . . .
H18E H 0.794149 0.329365 0.375152 0.144 Uiso 1 1 calc R U . . .
H18F H 0.902669 0.421091 0.451550 0.144 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
O1 C1 1.228(5) . ?
N1 C14 1.364(5) . ?
N1 C19 1.463(5) . ?
N1 C17 1.465(5) . ?
N2 C22 1.151(5) . ?
N3 C23 1.140(6) . ?
C1 C2 1.476(5) . ?
C1 C7A 1.480(6) . ?
C2 C8 1.374(6) . ?
C2 C3 1.457(5) . ?
C3 C21 1.374(5) . ?
C3 C3A 1.485(6) . ?
C3A C4 1.389(6) . ?
C3A C7A 1.399(5) . ?
C4 C5 1.383(6) . ?
C4 H4 0.9500 . ?
C5 C6 1.378(6) . ?
C5 H5 0.9500 . ?
C6 C7 1.382(6) . ?
C6 H6 0.9500 . ?
C7 C7A 1.371(6) . ?
C7 H7 0.9500 . ?
C8 C9 1.410(6) . ?
C8 H8 0.9500 . ?
C9 C10 1.361(6) . ?
C9 H9 0.9500 . ?
C10 C11 1.429(5) . ?
C10 H10 0.9500 . ?
C11 C16 1.399(6) . ?
C11 C12 1.406(5) . ?
C12 C13 1.365(5) . ?
C12 H12 0.9500 . ?
C13 C14 1.420(6) . ?
C13 H13 0.9500 . ?
C14 C15 1.415(5) . ?
C15 C16 1.374(6) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 C18 1.517(6) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 C20 1.512(6) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 C23 1.431(7) . ?
C21 C22 1.431(6) . ?
O1' C1' 1.221(5) . ?
N1' C14' 1.366(5) . ?
N1' C17' 1.428(2) . ?
N1' C19' 1.464(5) . ?
N2' C22' 1.140(5) . ?
N3' C23' 1.150(5) . ?
C1' C2' 1.480(6) . ?
C1' C7'A 1.480(6) . ?
C2' C8' 1.374(5) . ?
C2' C3' 1.463(5) . ?
C3' C21' 1.373(5) . ?
C3' C3'A 1.487(6) . ?
C3'A C4' 1.394(5) . ?
C3'A C7'A 1.397(6) . ?
C4' C5' 1.383(6) . ?
C4' H4' 0.9500 . ?
C5' C6' 1.380(6) . ?
C5' H5' 0.9500 . ?
C6' C7' 1.387(6) . ?
C6' H6' 0.9500 . ?
C7' C7'A 1.385(6) . ?
C7' H7' 0.9500 . ?
C8' C9' 1.405(5) . ?
C8' H8' 0.9500 . ?
C9' C10' 1.370(6) . ?
C9' H9' 0.9500 . ?
C10' C11' 1.425(5) . ?
C10' H10' 0.9500 . ?
C11' C12' 1.411(5) . ?
C11' C16' 1.413(5) . ?
C12' C13' 1.366(5) . ?
C12' H12' 0.9500 . ?
C13' C14' 1.422(6) . ?
C13' H13' 0.9500 . ?
C14' C15' 1.406(5) . ?
C15' C16' 1.359(5) . ?
C15' H15' 0.9500 . ?
C16' H16' 0.9500 . ?
C17' C18' 1.534(2) . ?
C17' H17C 0.9900 . ?
C17' H17D 0.9900 . ?
C19' C20' 1.515(7) . ?
C19' H19C 0.9900 . ?
C19' H19D 0.9900 . ?
C20' H20D 0.9800 . ?
C20' H20E 0.9800 . ?
C20' H20F 0.9800 . ?
C21' C22' 1.430(6) . ?
C21' C23' 1.431(6) . ?
C18' H18D 0.9800 . ?
C18' H18E 0.9800 . ?
C18' H18F 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
C14 N1 C19 122.1(3) . . ?
C14 N1 C17 121.7(3) . . ?
C19 N1 C17 116.1(3) . . ?
O1 C1 C2 127.8(4) . . ?
O1 C1 C7A 124.7(4) . . ?
C2 C1 C7A 107.5(3) . . ?
C8 C2 C3 128.5(4) . . ?
C8 C2 C1 124.4(3) . . ?
C3 C2 C1 107.0(3) . . ?
C21 C3 C2 127.9(4) . . ?
C21 C3 C3A 124.3(3) . . ?
C2 C3 C3A 107.8(3) . . ?
C4 C3A C7A 119.1(4) . . ?
C4 C3A C3 132.0(4) . . ?
C7A C3A C3 108.9(3) . . ?
C5 C4 C3A 118.0(4) . . ?
C5 C4 H4 121.0 . . ?
C3A C4 H4 121.0 . . ?
C6 C5 C4 122.0(4) . . ?
C6 C5 H5 119.0 . . ?
C4 C5 H5 119.0 . . ?
C5 C6 C7 120.6(4) . . ?
C5 C6 H6 119.7 . . ?
C7 C6 H6 119.7 . . ?
C7A C7 C6 117.6(4) . . ?
C7A C7 H7 121.2 . . ?
C6 C7 H7 121.2 . . ?
C7 C7A C3A 122.6(4) . . ?
C7 C7A C1 128.6(4) . . ?
C3A C7A C1 108.8(3) . . ?
C2 C8 C9 127.8(4) . . ?
C2 C8 H8 116.1 . . ?
C9 C8 H8 116.1 . . ?
C10 C9 C8 119.3(4) . . ?
C10 C9 H9 120.3 . . ?
C8 C9 H9 120.3 . . ?
C9 C10 C11 128.3(4) . . ?
C9 C10 H10 115.8 . . ?
C11 C10 H10 115.8 . . ?
C16 C11 C12 116.8(4) . . ?
C16 C11 C10 119.5(4) . . ?
C12 C11 C10 123.8(4) . . ?
C13 C12 C11 121.7(4) . . ?
C13 C12 H12 119.1 . . ?
C11 C12 H12 119.1 . . ?
C12 C13 C14 121.0(4) . . ?
C12 C13 H13 119.5 . . ?
C14 C13 H13 119.5 . . ?
N1 C14 C15 121.6(4) . . ?
N1 C14 C13 120.6(3) . . ?
C15 C14 C13 117.7(3) . . ?
C16 C15 C14 119.6(4) . . ?
C16 C15 H15 120.2 . . ?
C14 C15 H15 120.2 . . ?
C15 C16 C11 123.1(4) . . ?
C15 C16 H16 118.5 . . ?
C11 C16 H16 118.5 . . ?
N1 C17 C18 113.5(4) . . ?
N1 C17 H17A 108.9 . . ?
C18 C17 H17A 108.9 . . ?
N1 C17 H17B 108.9 . . ?
C18 C17 H17B 108.9 . . ?
H17A C17 H17B 107.7 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N1 C19 C20 113.3(4) . . ?
N1 C19 H19A 108.9 . . ?
C20 C19 H19A 108.9 . . ?
N1 C19 H19B 108.9 . . ?
C20 C19 H19B 108.9 . . ?
H19A C19 H19B 107.7 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C3 C21 C23 124.2(4) . . ?
C3 C21 C22 124.8(4) . . ?
C23 C21 C22 111.0(3) . . ?
N2 C22 C21 174.7(4) . . ?
N3 C23 C21 175.4(5) . . ?
C14' N1' C17' 123.1(4) . . ?
C14' N1' C19' 121.4(3) . . ?
C17' N1' C19' 113.1(4) . . ?
O1' C1' C2' 127.7(4) . . ?
O1' C1' C7'A 125.7(4) . . ?
C2' C1' C7'A 106.6(3) . . ?
C8' C2' C3' 128.4(4) . . ?
C8' C2' C1' 124.3(4) . . ?
C3' C2' C1' 107.3(3) . . ?
C21' C3' C2' 128.1(4) . . ?
C21' C3' C3'A 124.2(3) . . ?
C2' C3' C3'A 107.7(3) . . ?
C4' C3'A C7'A 118.7(4) . . ?
C4' C3'A C3' 133.0(4) . . ?
C7'A C3'A C3' 108.4(3) . . ?
C5' C4' C3'A 118.9(4) . . ?
C5' C4' H4' 120.6 . . ?
C3'A C4' H4' 120.6 . . ?
C6' C5' C4' 121.9(4) . . ?
C6' C5' H5' 119.1 . . ?
C4' C5' H5' 119.1 . . ?
C5' C6' C7' 120.2(4) . . ?
C5' C6' H6' 119.9 . . ?
C7' C6' H6' 119.9 . . ?
C6' C7' C7'A 118.0(4) . . ?
C6' C7' H7' 121.0 . . ?
C7'A C7' H7' 121.0 . . ?
C7' C7'A C3'A 122.4(4) . . ?
C7' C7'A C1' 127.7(4) . . ?
C3'A C7'A C1' 109.9(3) . . ?
C2' C8' C9' 127.1(4) . . ?
C2' C8' H8' 116.4 . . ?
C9' C8' H8' 116.4 . . ?
C10' C9' C8' 120.7(4) . . ?
C10' C9' H9' 119.7 . . ?
C8' C9' H9' 119.7 . . ?
C9' C10' C11' 128.3(4) . . ?
C9' C10' H10' 115.8 . . ?
C11' C10' H10' 115.8 . . ?
C12' C11' C16' 115.8(3) . . ?
C12' C11' C10' 124.5(4) . . ?
C16' C11' C10' 119.7(3) . . ?
C13' C12' C11' 122.2(4) . . ?
C13' C12' H12' 118.9 . . ?
C11' C12' H12' 118.9 . . ?
C12' C13' C14' 121.2(4) . . ?
C12' C13' H13' 119.4 . . ?
C14' C13' H13' 119.4 . . ?
N1' C14' C15' 122.3(4) . . ?
N1' C14' C13' 121.0(4) . . ?
C15' C14' C13' 116.7(4) . . ?
C16' C15' C14' 121.4(4) . . ?
C16' C15' H15' 119.3 . . ?
C14' C15' H15' 119.3 . . ?
C15' C16' C11' 122.6(4) . . ?
C15' C16' H16' 118.7 . . ?
C11' C16' H16' 118.7 . . ?
N1' C17' C18' 103.6(5) . . ?
N1' C17' H17C 111.0 . . ?
C18' C17' H17C 111.0 . . ?
N1' C17' H17D 111.0 . . ?
C18' C17' H17D 111.0 . . ?
H17C C17' H17D 109.0 . . ?
N1' C19' C20' 111.1(4) . . ?
N1' C19' H19C 109.4 . . ?
C20' C19' H19C 109.4 . . ?
N1' C19' H19D 109.4 . . ?
C20' C19' H19D 109.4 . . ?
H19C C19' H19D 108.0 . . ?
C19' C20' H20D 109.5 . . ?
C19' C20' H20E 109.5 . . ?
H20D C20' H20E 109.5 . . ?
C19' C20' H20F 109.5 . . ?
H20D C20' H20F 109.5 . . ?
H20E C20' H20F 109.5 . . ?
C3' C21' C22' 123.8(4) . . ?
C3' C21' C23' 123.5(3) . . ?
C22' C21' C23' 112.6(3) . . ?
N2' C22' C21' 177.0(5) . . ?
N3' C23' C21' 176.2(4) . . ?
C17' C18' H18D 109.5 . . ?
C17' C18' H18E 109.5 . . ?
H18D C18' H18E 109.5 . . ?
C17' C18' H18F 109.5 . . ?
H18D C18' H18F 109.5 . . ?
H18E C18' H18F 109.5 . . ?

_refine_diff_density_max         1.221
_refine_diff_density_min         -0.859
_refine_diff_density_rms         0.067

