# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2024

####################################################################### 
# 
# 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_cmpd_5a_SP401
_database_code_depnum_ccdc_archive 'CCDC 2310238'
loop_
_audit_author_name
_audit_author_address
'Pascal Retailleau'
;ICSN CNRS University Paris Saclay
France
;
_audit_update_record             
;
2023-11-24 deposited with the CCDC.	2024-02-08 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT910_cmpd_5a_SP401       
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min). 17 Note  
RESPONSE: Beam stop was set up too close to the sample, hiding some 
 low resolution reflections which could not be measured in further runs.
 (theta min started from 4 degrees)
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2019/3
_chemical_name_systematic        
6,12-dimethyl-6-phenyl-5,6-dihydroindolo[1,2-c]quinazoline
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H20 N2'
_chemical_formula_sum            'C23 H20 N2'
_chemical_formula_weight         324.41

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      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'I 2/a'
_space_group_name_Hall           '-I 2ya'

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

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

_cell_length_a                   17.1017(11)
_cell_length_b                   10.1324(6)
_cell_length_c                   21.8754(15)
_cell_angle_alpha                90
_cell_angle_beta                 111.523(8)
_cell_angle_gamma                90
_cell_volume                     3526.3(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6949
_cell_measurement_theta_min      3.7420
_cell_measurement_theta_max      29.1500

_exptl_crystal_description       tab
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.222
_exptl_crystal_F_000             1376
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 -5 -1 0.1756
-1 5 1 0.3881
1 0 -5 0.1589
-1 0 5 0.1454
5 0 -1 0.0775
-5 0 1 0.0466
-4 -2 30 0.1311
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.072
_shelx_estimated_absorpt_T_min   0.958
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_T_min  0.351
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.96a (Rigaku Oxford Diffraction, 2023)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      293(2)
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_reflns_number            21551
_diffrn_reflns_av_unetI/netI     0.0327
_diffrn_reflns_av_R_equivalents  0.0533
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         4.239
_diffrn_reflns_theta_max         25.344
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             3225
_reflns_number_gt                2827
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'CrysAlisPro system (CCD 39.46)'
_computing_cell_refinement       'CrysAlisPro 1.171.43.96a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.43.96a (Rigaku OD, 2023)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0591P)²+1.4118P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     other
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3208
_refine_ls_number_parameters     231
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0467
_refine_ls_R_factor_gt           0.0413
_refine_ls_wR_factor_ref         0.1136
_refine_ls_wR_factor_gt          0.1091
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_restrained_S_all      1.011
_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
C6 C 0.36825(7) 0.40042(12) 0.29982(6) 0.0398(3) Uani 1 1 d . . . . .
C7 C 0.37539(9) 0.38568(14) 0.36508(7) 0.0493(3) Uani 1 1 d . . . . .
H7 H 0.411924 0.323988 0.392441 0.059 Uiso 1 1 calc R U . . .
C8 C 0.32671(9) 0.46522(16) 0.38760(7) 0.0564(4) Uani 1 1 d . . . . .
H8 H 0.330489 0.456729 0.430924 0.068 Uiso 1 1 calc R U . . .
C9 C 0.27181(9) 0.55830(15) 0.34729(8) 0.0559(4) Uani 1 1 d . . . . .
H9 H 0.240781 0.612033 0.364434 0.067 Uiso 1 1 calc R U . . .
C10 C 0.26289(8) 0.57181(14) 0.28279(7) 0.0500(3) Uani 1 1 d . . . . .
H10 H 0.225858 0.633760 0.256090 0.060 Uiso 1 1 calc R U . . .
C11 C 0.40081(8) 0.32058(12) 0.14963(6) 0.0407(3) Uani 1 1 d . . . . .
C12 C 0.47618(8) 0.24877(12) 0.17299(6) 0.0407(3) Uani 1 1 d . . . . .
C13 C 0.50929(9) 0.19687(14) 0.12900(7) 0.0528(3) Uani 1 1 d . . . . .
H13 H 0.560228 0.151891 0.144638 0.063 Uiso 1 1 calc R U . . .
C14 C 0.46730(11) 0.21147(16) 0.06237(7) 0.0620(4) Uani 1 1 d . . . . .
H14 H 0.490288 0.177090 0.033260 0.074 Uiso 1 1 calc R U . . .
C15 C 0.39139(11) 0.27676(16) 0.03858(7) 0.0631(4) Uani 1 1 d . . . . .
H15 H 0.362439 0.284402 -0.006491 0.076 Uiso 1 1 calc R U . . .
C16 C 0.35855(9) 0.33066(15) 0.08178(6) 0.0544(4) Uani 1 1 d . . . . .
H16 H 0.307265 0.374583 0.065457 0.065 Uiso 1 1 calc R U . . .
C17 C 0.25970(10) 0.55497(17) 0.13457(7) 0.0649(4) Uani 1 1 d . . . . .
H17A H 0.213691 0.501466 0.107509 0.097 Uiso 1 1 calc R U . . .
H17B H 0.293110 0.581610 0.109755 0.097 Uiso 1 1 calc R U . . .
H17C H 0.238222 0.631788 0.148803 0.097 Uiso 1 1 calc R U . . .
C18 C 0.52566(8) 0.23570(12) 0.35304(6) 0.0406(3) Uani 1 1 d . . . . .
C19 C 0.53489(10) 0.13569(15) 0.39828(7) 0.0552(4) Uani 1 1 d . . . . .
H19 H 0.504826 0.057553 0.385242 0.066 Uiso 1 1 calc R U . . .
C20 C 0.58884(12) 0.15173(18) 0.46299(7) 0.0693(5) Uani 1 1 d . . . . .
H20 H 0.594419 0.084388 0.493188 0.083 Uiso 1 1 calc R U . . .
C21 C 0.63396(10) 0.26575(19) 0.48279(7) 0.0675(5) Uani 1 1 d . . . . .
H21 H 0.670179 0.275659 0.526232 0.081 Uiso 1 1 calc R U . . .
C22 C 0.62559(9) 0.36552(17) 0.43834(7) 0.0592(4) Uani 1 1 d . . . . .
H22 H 0.655922 0.443312 0.451760 0.071 Uiso 1 1 calc R U . . .
C23 C 0.57209(8) 0.35048(14) 0.37361(6) 0.0482(3) Uani 1 1 d . . . . .
H23 H 0.567222 0.417971 0.343623 0.058 Uiso 1 1 calc R U . . .
N1 N 0.40845(6) 0.33878(10) 0.26314(5) 0.0385(3) Uani 1 1 d . . . . .
C1 C 0.46610(7) 0.22439(12) 0.28157(6) 0.0385(3) Uani 1 1 d . . . . .
N2 N 0.51760(7) 0.23669(11) 0.24093(5) 0.0433(3) Uani 1 1 d . . . . .
H2N H 0.5590(9) 0.1793(15) 0.2521(7) 0.052 Uiso 1 1 d . U . . .
C2 C 0.41317(9) 0.09914(14) 0.26640(7) 0.0546(4) Uani 1 1 d . . . . .
H2A H 0.377795 0.098082 0.220704 0.082 Uiso 1 1 calc R U . . .
H2B H 0.378912 0.096944 0.292682 0.082 Uiso 1 1 calc R U . . .
H2C H 0.449455 0.023440 0.276247 0.082 Uiso 1 1 calc R U . . .
C3 C 0.37185(7) 0.38097(12) 0.19796(6) 0.0392(3) Uani 1 1 d . . . . .
C4 C 0.31296(8) 0.47688(13) 0.19341(6) 0.0441(3) Uani 1 1 d . . . . .
C5 C 0.31050(7) 0.49071(12) 0.25758(6) 0.0416(3) 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
C6 N1 1.3825(15) . ?
C6 C7 1.3956(18) . ?
C6 C5 1.4130(18) . ?
C7 C8 1.373(2) . ?
C7 H7 0.9300 . ?
C8 C9 1.393(2) . ?
C8 H8 0.9300 . ?
C9 C10 1.369(2) . ?
C9 H9 0.9300 . ?
C10 C5 1.4043(18) . ?
C10 H10 0.9300 . ?
C11 C16 1.3959(17) . ?
C11 C12 1.4031(18) . ?
C11 C3 1.4565(17) . ?
C12 C13 1.3867(18) . ?
C12 N2 1.3976(16) . ?
C13 C14 1.376(2) . ?
C13 H13 0.9300 . ?
C14 C15 1.378(2) . ?
C14 H14 0.9300 . ?
C15 C16 1.377(2) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 C4 1.5008(18) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 C19 1.3845(19) . ?
C18 C23 1.3868(19) . ?
C18 C1 1.5252(16) . ?
C19 C20 1.387(2) . ?
C19 H19 0.9300 . ?
C20 C21 1.368(3) . ?
C20 H20 0.9300 . ?
C21 C22 1.373(2) . ?
C21 H21 0.9300 . ?
C22 C23 1.3837(18) . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?
N1 C3 1.3973(15) . ?
N1 C1 1.4787(15) . ?
C1 N2 1.4683(16) . ?
C1 C2 1.5230(17) . ?
N2 H2N 0.878(15) . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C3 C4 1.3766(17) . ?
C4 C5 1.4266(18) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C6 C7 132.06(12) . . ?
N1 C6 C5 106.86(10) . . ?
C7 C6 C5 121.07(12) . . ?
C8 C7 C6 117.84(13) . . ?
C8 C7 H7 121.1 . . ?
C6 C7 H7 121.1 . . ?
C7 C8 C9 121.78(14) . . ?
C7 C8 H8 119.1 . . ?
C9 C8 H8 119.1 . . ?
C10 C9 C8 120.96(13) . . ?
C10 C9 H9 119.5 . . ?
C8 C9 H9 119.5 . . ?
C9 C10 C5 119.00(13) . . ?
C9 C10 H10 120.5 . . ?
C5 C10 H10 120.5 . . ?
C16 C11 C12 118.25(12) . . ?
C16 C11 C3 124.04(12) . . ?
C12 C11 C3 117.72(11) . . ?
C13 C12 N2 121.87(12) . . ?
C13 C12 C11 119.90(12) . . ?
N2 C12 C11 118.18(11) . . ?
C14 C13 C12 120.46(13) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C13 C14 C15 120.32(14) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 H14 119.8 . . ?
C16 C15 C14 119.75(14) . . ?
C16 C15 H15 120.1 . . ?
C14 C15 H15 120.1 . . ?
C15 C16 C11 121.22(13) . . ?
C15 C16 H16 119.4 . . ?
C11 C16 H16 119.4 . . ?
C4 C17 H17A 109.5 . . ?
C4 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C4 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C19 C18 C23 118.70(12) . . ?
C19 C18 C1 122.40(12) . . ?
C23 C18 C1 118.90(11) . . ?
C18 C19 C20 120.17(15) . . ?
C18 C19 H19 119.9 . . ?
C20 C19 H19 119.9 . . ?
C21 C20 C19 120.58(15) . . ?
C21 C20 H20 119.7 . . ?
C19 C20 H20 119.7 . . ?
C20 C21 C22 119.81(14) . . ?
C20 C21 H21 120.1 . . ?
C22 C21 H21 120.1 . . ?
C21 C22 C23 120.10(15) . . ?
C21 C22 H22 119.9 . . ?
C23 C22 H22 119.9 . . ?
C22 C23 C18 120.62(14) . . ?
C22 C23 H23 119.7 . . ?
C18 C23 H23 119.7 . . ?
C6 N1 C3 108.79(10) . . ?
C6 N1 C1 128.29(10) . . ?
C3 N1 C1 121.48(10) . . ?
N2 C1 N1 104.86(9) . . ?
N2 C1 C2 112.29(11) . . ?
N1 C1 C2 108.07(10) . . ?
N2 C1 C18 106.91(10) . . ?
N1 C1 C18 110.38(9) . . ?
C2 C1 C18 113.95(10) . . ?
C12 N2 C1 117.95(10) . . ?
C12 N2 H2N 113.3(10) . . ?
C1 N2 H2N 112.1(10) . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C4 C3 N1 109.37(11) . . ?
C4 C3 C11 132.74(11) . . ?
N1 C3 C11 117.89(10) . . ?
C3 C4 C5 106.44(11) . . ?
C3 C4 C17 129.19(12) . . ?
C5 C4 C17 124.36(12) . . ?
C10 C5 C6 119.27(12) . . ?
C10 C5 C4 132.43(12) . . ?
C6 C5 C4 108.30(11) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C6 C7 C8 178.75(13) . . . . ?
C5 C6 C7 C8 -2.36(19) . . . . ?
C6 C7 C8 C9 -0.1(2) . . . . ?
C7 C8 C9 C10 1.6(2) . . . . ?
C8 C9 C10 C5 -0.4(2) . . . . ?
C16 C11 C12 C13 3.84(19) . . . . ?
C3 C11 C12 C13 -175.70(12) . . . . ?
C16 C11 C12 N2 -178.83(12) . . . . ?
C3 C11 C12 N2 1.63(18) . . . . ?
N2 C12 C13 C14 -179.41(13) . . . . ?
C11 C12 C13 C14 -2.2(2) . . . . ?
C12 C13 C14 C15 -0.6(2) . . . . ?
C13 C14 C15 C16 1.7(3) . . . . ?
C14 C15 C16 C11 0.0(2) . . . . ?
C12 C11 C16 C15 -2.8(2) . . . . ?
C3 C11 C16 C15 176.71(14) . . . . ?
C23 C18 C19 C20 0.8(2) . . . . ?
C1 C18 C19 C20 -178.91(13) . . . . ?
C18 C19 C20 C21 -0.5(2) . . . . ?
C19 C20 C21 C22 0.2(3) . . . . ?
C20 C21 C22 C23 -0.4(2) . . . . ?
C21 C22 C23 C18 0.8(2) . . . . ?
C19 C18 C23 C22 -1.0(2) . . . . ?
C1 C18 C23 C22 178.76(12) . . . . ?
C7 C6 N1 C3 174.10(13) . . . . ?
C5 C6 N1 C3 -4.91(13) . . . . ?
C7 C6 N1 C1 7.8(2) . . . . ?
C5 C6 N1 C1 -171.19(11) . . . . ?
C6 N1 C1 N2 -155.55(11) . . . . ?
C3 N1 C1 N2 39.72(14) . . . . ?
C6 N1 C1 C2 84.49(14) . . . . ?
C3 N1 C1 C2 -80.25(14) . . . . ?
C6 N1 C1 C18 -40.74(16) . . . . ?
C3 N1 C1 C18 154.52(10) . . . . ?
C19 C18 C1 N2 -119.90(13) . . . . ?
C23 C18 C1 N2 60.35(14) . . . . ?
C19 C18 C1 N1 126.59(13) . . . . ?
C23 C18 C1 N1 -53.16(15) . . . . ?
C19 C18 C1 C2 4.77(18) . . . . ?
C23 C18 C1 C2 -174.98(12) . . . . ?
C13 C12 N2 C1 -146.95(13) . . . . ?
C11 C12 N2 C1 35.78(16) . . . . ?
N1 C1 N2 C12 -53.66(13) . . . . ?
C2 C1 N2 C12 63.44(14) . . . . ?
C18 C1 N2 C12 -170.88(10) . . . . ?
C6 N1 C3 C4 4.67(14) . . . . ?
C1 N1 C3 C4 172.06(10) . . . . ?
C6 N1 C3 C11 -175.61(10) . . . . ?
C1 N1 C3 C11 -8.22(16) . . . . ?
C16 C11 C3 C4 -14.9(2) . . . . ?
C12 C11 C3 C4 164.57(13) . . . . ?
C16 C11 C3 N1 165.42(12) . . . . ?
C12 C11 C3 N1 -15.07(17) . . . . ?
N1 C3 C4 C5 -2.44(14) . . . . ?
C11 C3 C4 C5 177.90(13) . . . . ?
N1 C3 C4 C17 177.67(13) . . . . ?
C11 C3 C4 C17 -2.0(2) . . . . ?
C9 C10 C5 C6 -2.03(19) . . . . ?
C9 C10 C5 C4 176.95(13) . . . . ?
N1 C6 C5 C10 -177.39(11) . . . . ?
C7 C6 C5 C10 3.48(18) . . . . ?
N1 C6 C5 C4 3.41(13) . . . . ?
C7 C6 C5 C4 -175.73(11) . . . . ?
C3 C4 C5 C10 -179.67(13) . . . . ?
C17 C4 C5 C10 0.2(2) . . . . ?
C3 C4 C5 C6 -0.60(14) . . . . ?
C17 C4 C5 C6 179.30(13) . . . . ?

_refine_diff_density_max         0.194
_refine_diff_density_min         -0.165
_refine_diff_density_rms         0.032




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

data_cmpd_6c_SP584
_database_code_depnum_ccdc_archive 'CCDC 2310241'
loop_
_audit_author_name
_audit_author_address
'Pascal Retailleau'
;ICSN CNRS University Paris Saclay
France
;
_audit_update_record             
;
2023-11-24 deposited with the CCDC.	2024-02-08 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_THETM01_cmpd_6c_SP584       
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.550
RESPONSE: poorly diffracting needle-like crystal despite copper rotating anode
radiation. 
;
_vrf_PLAT088_cmpd_6c_SP584       
;
PROBLEM: Poor Data / Parameter Ratio ....................       7.46 Note  
RESPONSE: see above
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2018/3
_chemical_name_systematic        
;'5-(1-(2-methoxyphenyl)vinyl)-5,10-dihydroindolo[3,2-b]indole'
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H18 N2 O'
_chemical_formula_sum            'C23 H18 N2 O'
_chemical_formula_weight         338.39

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

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

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

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

_cell_length_a                   12.7466(12)
_cell_length_b                   17.1840(13)
_cell_length_c                   7.9788(7)
_cell_angle_alpha                90
_cell_angle_beta                 93.746(7)
_cell_angle_gamma                90
_cell_volume                     1743.9(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4073
_cell_measurement_theta_min      2.6
_cell_measurement_theta_max      66.5

_exptl_crystal_description       needle
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_F_000             712
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.04
_exptl_absorpt_coefficient_mu    0.626
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.607
_exptl_absorpt_process_details   'Abscor (Higashi-Rigaku)'
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54187
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Rotating Anode'
_diffrn_radiation_monochromator  'Confocal CMF Osmic'
_diffrn_measurement_specimen_support Fiber
_diffrn_detector                 'RX Rapid2 curved IP'
_diffrn_measurement_device       
;
Crystal Goniometer chi-partial
;
_diffrn_measurement_device_type  
;
Rigaku RAXIS conversion
;
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_reflns_number            10256
_diffrn_reflns_av_unetI/netI     0.0539
_diffrn_reflns_av_R_equivalents  0.0533
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         3.475
_diffrn_reflns_theta_max         49.733
_diffrn_reflns_theta_full        49.733
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             1760
_reflns_number_gt                1163
_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       
;
CrystalClear-SM Expert 2.0 r16 (Rigaku, 2014)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 r16 (Rigaku, 2014)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r16 (Rigaku, 2014)
;
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1130P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     other
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1760
_refine_ls_number_parameters     236
_refine_ls_number_restraints     392
_refine_ls_R_factor_all          0.0888
_refine_ls_R_factor_gt           0.0656
_refine_ls_wR_factor_ref         0.1880
_refine_ls_wR_factor_gt          0.1721
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      0.955
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.7061(2) 0.57000(15) 0.5451(3) 0.0914(9) Uani 1 1 d . . . . .
N1 N 0.6058(3) 0.5825(2) 0.2093(4) 0.0895(10) Uani 1 1 d . U . . .
C1 C 0.6760(4) 0.6302(3) 0.1413(5) 0.0873(12) Uani 1 1 d . U . . .
C2 C 0.6247(4) 0.6976(3) 0.0810(5) 0.0869(12) Uani 1 1 d . U . . .
N2 N 0.6940(3) 0.7465(2) 0.0112(4) 0.1097(12) Uani 1 1 d . U . . .
H2 H 0.678962 0.790878 -0.033929 0.132 Uiso 1 1 calc R U . . .
C5 C 0.4113(4) 0.5995(2) 0.2553(5) 0.0907(12) Uani 1 1 d . U . . .
H5 H 0.406299 0.553094 0.314362 0.109 Uiso 1 1 calc R U . . .
C4 C 0.5047(4) 0.6222(3) 0.1959(5) 0.0867(12) Uani 1 1 d . U . . .
C6 C 0.3252(4) 0.6464(3) 0.2262(5) 0.1057(14) Uani 1 1 d . U . . .
H6 H 0.260893 0.630841 0.263723 0.127 Uiso 1 1 calc R U . . .
C8 C 0.4268(4) 0.7415(2) 0.0857(5) 0.1029(14) Uani 1 1 d . U . . .
H8 H 0.431937 0.788771 0.030090 0.123 Uiso 1 1 calc R U . . .
C7 C 0.3316(4) 0.7169(3) 0.1417(6) 0.1153(15) Uani 1 1 d . U . . .
H7 H 0.271930 0.747565 0.122802 0.138 Uiso 1 1 calc R U . . .
C9 C 0.7854(4) 0.6380(2) 0.1034(4) 0.0832(11) Uani 1 1 d . U . . .
C3 C 0.5146(4) 0.6938(3) 0.1147(5) 0.0942(12) Uani 1 1 d . U . . .
C10 C 0.7917(4) 0.7126(3) 0.0251(5) 0.0907(12) Uani 1 1 d . U . . .
C11 C 0.6208(4) 0.5014(3) 0.2459(4) 0.0845(12) Uani 1 1 d . U . . .
C12 C 0.8840(5) 0.7423(3) -0.0260(5) 0.1080(15) Uani 1 1 d . U . . .
H12 H 0.885882 0.791454 -0.074573 0.130 Uiso 1 1 calc R U . . .
C13 C 0.9719(4) 0.6993(3) -0.0047(5) 0.1170(15) Uani 1 1 d . U . . .
H13 H 1.035326 0.718453 -0.038995 0.140 Uiso 1 1 calc R U . . .
C14 C 0.9677(4) 0.6257(3) 0.0691(5) 0.1103(14) Uani 1 1 d . U . . .
H14 H 1.029184 0.596495 0.081146 0.132 Uiso 1 1 calc R U . . .
C15 C 0.8776(4) 0.5947(2) 0.1244(4) 0.0887(12) Uani 1 1 d . U . . .
H15 H 0.877849 0.545947 0.174782 0.106 Uiso 1 1 calc R U . . .
C16 C 0.5479(3) 0.4503(2) 0.2021(5) 0.1021(14) Uani 1 1 d . . . . .
H16A H 0.485294 0.466390 0.146446 0.123 Uiso 1 1 calc R U . . .
H16B H 0.558771 0.397894 0.226751 0.123 Uiso 1 1 calc R U . . .
C17 C 0.7229(3) 0.4779(2) 0.3317(5) 0.0790(11) Uani 1 1 d . . . . .
C18 C 0.7638(4) 0.5111(2) 0.4822(6) 0.0830(12) Uani 1 1 d . . . . .
C19 C 0.8561(4) 0.4845(3) 0.5624(5) 0.0996(13) Uani 1 1 d . . . . .
H19 H 0.883018 0.508012 0.660994 0.119 Uiso 1 1 calc R U . . .
C20 C 0.9086(4) 0.4222(3) 0.4947(7) 0.1154(16) Uani 1 1 d . . . . .
H20 H 0.970863 0.404218 0.548474 0.138 Uiso 1 1 calc R U . . .
C21 C 0.8697(4) 0.3872(3) 0.3499(7) 0.1079(15) Uani 1 1 d . . . . .
H21 H 0.904355 0.345042 0.305587 0.130 Uiso 1 1 calc R U . . .
C22 C 0.7770(4) 0.4159(2) 0.2699(5) 0.0960(13) Uani 1 1 d . . . . .
H22 H 0.750739 0.392211 0.171029 0.115 Uiso 1 1 calc R U . . .
C23 C 0.7326(3) 0.5935(2) 0.7169(5) 0.1133(15) Uani 1 1 d . . . . .
H23A H 0.680022 0.628706 0.752634 0.170 Uiso 1 1 calc R U . . .
H23B H 0.799786 0.618968 0.723740 0.170 Uiso 1 1 calc R U . . .
H23C H 0.735566 0.548441 0.788110 0.170 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 C18 1.365(4) . ?
O1 C23 1.447(4) . ?
N1 C1 1.352(5) . ?
N1 C11 1.435(5) . ?
N1 C4 1.455(5) . ?
C1 C2 1.399(5) . ?
C1 C9 1.452(5) . ?
C2 N2 1.364(4) . ?
C2 C3 1.448(5) . ?
N2 C10 1.373(4) . ?
C5 C4 1.368(5) . ?
C5 C6 1.370(5) . ?
C4 C3 1.400(5) . ?
C6 C7 1.390(5) . ?
C8 C7 1.386(5) . ?
C8 C3 1.394(5) . ?
C9 C15 1.391(5) . ?
C9 C10 1.431(5) . ?
C10 C12 1.369(5) . ?
C11 C16 1.309(5) . ?
C11 C17 1.486(5) . ?
C12 C13 1.344(6) . ?
C13 C14 1.398(5) . ?
C14 C15 1.365(5) . ?
C17 C22 1.379(5) . ?
C17 C18 1.399(5) . ?
C18 C19 1.381(5) . ?
C19 C20 1.389(5) . ?
C20 C21 1.367(5) . ?
C21 C22 1.396(5) . ?

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
C18 O1 C23 117.2(3) . . ?
C1 N1 C11 126.0(4) . . ?
C1 N1 C4 107.0(4) . . ?
C11 N1 C4 125.1(4) . . ?
N1 C1 C2 109.4(4) . . ?
N1 C1 C9 143.9(4) . . ?
C2 C1 C9 106.6(4) . . ?
N2 C2 C1 110.5(4) . . ?
N2 C2 C3 139.9(5) . . ?
C1 C2 C3 109.6(4) . . ?
C2 N2 C10 108.3(4) . . ?
C4 C5 C6 118.6(5) . . ?
C5 C4 C3 121.2(5) . . ?
C5 C4 N1 128.9(4) . . ?
C3 C4 N1 109.9(4) . . ?
C5 C6 C7 121.5(5) . . ?
C7 C8 C3 118.5(5) . . ?
C8 C7 C6 120.2(5) . . ?
C15 C9 C10 117.4(4) . . ?
C15 C9 C1 137.8(4) . . ?
C10 C9 C1 104.8(4) . . ?
C8 C3 C4 119.9(5) . . ?
C8 C3 C2 136.1(5) . . ?
C4 C3 C2 104.0(4) . . ?
C12 C10 N2 127.7(5) . . ?
C12 C10 C9 122.5(5) . . ?
N2 C10 C9 109.8(4) . . ?
C16 C11 N1 121.0(4) . . ?
C16 C11 C17 121.7(4) . . ?
N1 C11 C17 117.3(4) . . ?
C13 C12 C10 118.9(5) . . ?
C12 C13 C14 119.8(5) . . ?
C15 C14 C13 123.0(5) . . ?
C14 C15 C9 118.4(4) . . ?
C22 C17 C18 117.1(4) . . ?
C22 C17 C11 119.2(4) . . ?
C18 C17 C11 123.4(4) . . ?
O1 C18 C19 122.6(4) . . ?
O1 C18 C17 116.0(4) . . ?
C19 C18 C17 121.4(4) . . ?
C18 C19 C20 119.5(5) . . ?
C21 C20 C19 120.7(5) . . ?
C20 C21 C22 118.7(5) . . ?
C17 C22 C21 122.5(4) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C11 N1 C1 C2 163.5(3) . . . . ?
C4 N1 C1 C2 -1.5(4) . . . . ?
C11 N1 C1 C9 -14.8(7) . . . . ?
C4 N1 C1 C9 -179.9(4) . . . . ?
N1 C1 C2 N2 -179.7(3) . . . . ?
C9 C1 C2 N2 -0.8(4) . . . . ?
N1 C1 C2 C3 1.0(4) . . . . ?
C9 C1 C2 C3 -180.0(3) . . . . ?
C1 C2 N2 C10 -0.4(4) . . . . ?
C3 C2 N2 C10 178.5(4) . . . . ?
C6 C5 C4 C3 3.5(5) . . . . ?
C6 C5 C4 N1 -179.4(3) . . . . ?
C1 N1 C4 C5 -175.9(3) . . . . ?
C11 N1 C4 C5 19.0(6) . . . . ?
C1 N1 C4 C3 1.5(4) . . . . ?
C11 N1 C4 C3 -163.7(3) . . . . ?
C4 C5 C6 C7 -1.6(6) . . . . ?
C3 C8 C7 C6 0.6(6) . . . . ?
C5 C6 C7 C8 -0.5(6) . . . . ?
N1 C1 C9 C15 -0.9(8) . . . . ?
C2 C1 C9 C15 -179.2(4) . . . . ?
N1 C1 C9 C10 179.9(5) . . . . ?
C2 C1 C9 C10 1.6(4) . . . . ?
C7 C8 C3 C4 1.2(6) . . . . ?
C7 C8 C3 C2 -178.9(4) . . . . ?
C5 C4 C3 C8 -3.3(6) . . . . ?
N1 C4 C3 C8 179.0(3) . . . . ?
C5 C4 C3 C2 176.8(3) . . . . ?
N1 C4 C3 C2 -0.8(4) . . . . ?
N2 C2 C3 C8 1.2(8) . . . . ?
C1 C2 C3 C8 -179.9(4) . . . . ?
N2 C2 C3 C4 -179.0(4) . . . . ?
C1 C2 C3 C4 -0.1(4) . . . . ?
C2 N2 C10 C12 -178.8(4) . . . . ?
C2 N2 C10 C9 1.4(4) . . . . ?
C15 C9 C10 C12 -1.0(6) . . . . ?
C1 C9 C10 C12 178.4(3) . . . . ?
C15 C9 C10 N2 178.7(3) . . . . ?
C1 C9 C10 N2 -1.9(4) . . . . ?
C1 N1 C11 C16 -133.0(4) . . . . ?
C4 N1 C11 C16 29.3(5) . . . . ?
C1 N1 C11 C17 45.7(5) . . . . ?
C4 N1 C11 C17 -152.0(4) . . . . ?
N2 C10 C12 C13 -178.5(4) . . . . ?
C9 C10 C12 C13 1.2(6) . . . . ?
C10 C12 C13 C14 -0.2(7) . . . . ?
C12 C13 C14 C15 -1.0(7) . . . . ?
C13 C14 C15 C9 1.2(6) . . . . ?
C10 C9 C15 C14 -0.2(5) . . . . ?
C1 C9 C15 C14 -179.3(4) . . . . ?
C16 C11 C17 C22 46.8(5) . . . . ?
N1 C11 C17 C22 -131.9(3) . . . . ?
C16 C11 C17 C18 -127.4(4) . . . . ?
N1 C11 C17 C18 53.9(5) . . . . ?
C23 O1 C18 C19 -12.6(5) . . . . ?
C23 O1 C18 C17 166.4(3) . . . . ?
C22 C17 C18 O1 -176.9(3) . . . . ?
C11 C17 C18 O1 -2.6(5) . . . . ?
C22 C17 C18 C19 2.0(5) . . . . ?
C11 C17 C18 C19 176.3(3) . . . . ?
O1 C18 C19 C20 177.4(3) . . . . ?
C17 C18 C19 C20 -1.5(6) . . . . ?
C18 C19 C20 C21 -0.1(6) . . . . ?
C19 C20 C21 C22 0.9(6) . . . . ?
C18 C17 C22 C21 -1.1(5) . . . . ?
C11 C17 C22 C21 -175.7(4) . . . . ?
C20 C21 C22 C17 -0.3(6) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N2 H2 O1 0.86 2.49 3.169(5) 136.3 4_575 yes

_refine_diff_density_max         0.412
_refine_diff_density_min         -0.144
_refine_diff_density_rms         0.042






####################################################################### 
# 
# 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_cmpd_5f-SP582-1
_database_code_depnum_ccdc_archive 'CCDC 2310239'
loop_
_audit_author_name
_audit_author_address
'Pascal Retailleau'
;ICSN CNRS University Paris Saclay
France
;
_audit_update_record             
;
2023-11-24 deposited with the CCDC.	2024-02-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_chemical_name_systematic        
;'6,12-dimethyl-6-(m-tolyl)-5,6-dihydroindolo[1,2-c]quinazoline'
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H22 N2'
_chemical_formula_sum            'C24 H22 N2'
_chemical_formula_weight         338.43

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'

_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                   8.1403(4)
_cell_length_b                   17.9909(9)
_cell_length_c                   13.1138(7)
_cell_angle_alpha                90
_cell_angle_beta                 97.700(5)
_cell_angle_gamma                90
_cell_volume                     1903.22(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6626
_cell_measurement_theta_min      2.7550
_cell_measurement_theta_max      25.2360

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.181
_exptl_crystal_F_000             720
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.130
_shelx_estimated_absorpt_T_min   0.986
_shelx_estimated_absorpt_T_max   0.991
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 5 0 0.0640
1 -5 -5 0.0697
-2 -5 0 0.0563
-4 -5 5 0.0565
-2 2 5 0.0874
-5 4 -2 0.0554
-4 5 4 0.0663
0 2 5 0.0916
5 -2 5 0.0689
5 -5 -2 0.0778
2 -4 -5 0.0721
0 -2 -5 0.0840
-1 -5 2 0.0669
0 -5 -2 0.0664
_exptl_absorpt_coefficient_mu    0.069
_exptl_absorpt_correction_T_min  0.495
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.122a (Rigaku Oxford Diffraction, 2021)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku microsource mm003'
_diffrn_radiation_monochromator  'Rigaku MaxFlux double bounce layer optic'
_diffrn_measurement_specimen_support Fiber
_diffrn_detector                 'HPAD Dectris PILATUS3R 200K-A'
_diffrn_measurement_device       
;
 κ-geometry diffractometer
;
_diffrn_measurement_device_type  
;
Rigaku XtaLabPro AFC12 (Right) goniometer
;
_diffrn_reflns_number            23102
_diffrn_reflns_av_unetI/netI     0.0243
_diffrn_reflns_av_R_equivalents  0.0391
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.264
_diffrn_reflns_theta_max         25.345
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3487
_reflns_number_gt                2876
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0485P)²+0.3383P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     other
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3485
_refine_ls_number_parameters     282
_refine_ls_number_restraints     261
_refine_ls_R_factor_all          0.0558
_refine_ls_R_factor_gt           0.0464
_refine_ls_wR_factor_ref         0.1268
_refine_ls_wR_factor_gt          0.1198
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_restrained_S_all      1.089
_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 0.6264(2) 0.36352(9) 0.44779(13) 0.0667(4) Uani 1 1 d . . . . .
N1 N 0.48311(16) 0.32332(7) 0.46019(10) 0.0647(3) Uani 1 1 d . . . . .
C2 C 0.6602(2) 0.41240(9) 0.52852(15) 0.0772(5) Uani 1 1 d . . . . .
N2 N 0.53417(17) 0.24100(8) 0.33065(11) 0.0704(4) Uani 1 1 d D . . . .
HN2 H 0.497(2) 0.2073(9) 0.2862(13) 0.084 Uiso 1 1 d D U . . .
C3 C 0.5295(3) 0.40553(9) 0.58924(13) 0.0765(5) Uani 1 1 d . . . . .
C4 C 0.4174(2) 0.35088(9) 0.54409(12) 0.0672(4) Uani 1 1 d . . . . .
C5 C 0.2709(3) 0.33549(10) 0.58366(14) 0.0803(5) Uani 1 1 d . . . . .
H5 H 0.196333 0.300462 0.552633 0.096 Uiso 1 1 calc R U . . .
C6 C 0.2392(3) 0.37352(12) 0.67001(15) 0.0950(6) Uani 1 1 d . . . . .
H6 H 0.141299 0.364285 0.697092 0.114 Uiso 1 1 calc R U . . .
C7 C 0.3506(4) 0.42542(12) 0.71753(16) 0.1050(8) Uani 1 1 d . . . . .
H7 H 0.327370 0.449345 0.776814 0.126 Uiso 1 1 calc R U . . .
C8 C 0.4936(4) 0.44184(11) 0.67855(16) 0.0976(7) Uani 1 1 d . . . . .
H8 H 0.566828 0.476863 0.710912 0.117 Uiso 1 1 calc R U . . .
C9 C 0.70333(19) 0.35000(9) 0.35604(13) 0.0680(4) Uani 1 1 d . . . . .
C10 C 0.65278(19) 0.28710(10) 0.29637(13) 0.0678(4) Uani 1 1 d . . . . .
C11 C 0.39970(19) 0.27558(9) 0.37730(12) 0.0631(4) Uani 1 1 d D U . . .
C12 C 0.8060(3) 0.46386(12) 0.55261(19) 0.1078(8) Uani 1 1 d . . . . .
H12A H 0.818348 0.477062 0.624152 0.162 Uiso 1 1 calc R U . . .
H12B H 0.788004 0.507962 0.511423 0.162 Uiso 1 1 calc R U . . .
H12C H 0.904792 0.439358 0.537601 0.162 Uiso 1 1 calc R U . . .
C13 C 0.8208(2) 0.39692(11) 0.32070(17) 0.0839(5) Uani 1 1 d . . . . .
H13 H 0.854182 0.439652 0.357707 0.101 Uiso 1 1 calc R U . . .
C14 C 0.8876(2) 0.38110(14) 0.23267(19) 0.0977(7) Uani 1 1 d . . . . .
H14 H 0.964380 0.413369 0.210044 0.117 Uiso 1 1 calc R U . . .
C15 C 0.8416(2) 0.31766(14) 0.17768(17) 0.0945(6) Uani 1 1 d . . . . .
H15 H 0.889997 0.306340 0.119240 0.113 Uiso 1 1 calc R U . . .
C16 C 0.7241(2) 0.27083(12) 0.20878(15) 0.0819(5) Uani 1 1 d . . . . .
H16 H 0.692579 0.228235 0.170969 0.098 Uiso 1 1 calc R U . . .
C17 C 0.2917(2) 0.32500(11) 0.30182(14) 0.0802(5) Uani 1 1 d . . . . .
H17A H 0.239158 0.295401 0.245805 0.120 Uiso 1 1 calc R U . . .
H17B H 0.359130 0.362392 0.275726 0.120 Uiso 1 1 calc R U . . .
H17C H 0.208488 0.348408 0.336242 0.120 Uiso 1 1 calc R U . . .
C18 C 0.3064(6) 0.2114(3) 0.4275(6) 0.0627(16) Uani 0.590(5) 1 d DG U P A 1
C19 C 0.1390(6) 0.1959(3) 0.3998(4) 0.0623(10) Uani 0.590(5) 1 d G U P A 1
H19 H 0.073987 0.227049 0.354408 0.075 Uiso 0.590(5) 1 calc R U P A 1
C20 C 0.0689(5) 0.1339(3) 0.4402(5) 0.0721(12) Uani 0.590(5) 1 d DG U P A 1
C21 C 0.1662(7) 0.0873(3) 0.5081(6) 0.0842(15) Uani 0.590(5) 1 d G U P A 1
H21 H 0.119259 0.045786 0.535032 0.101 Uiso 0.590(5) 1 calc R U P A 1
C22 C 0.3335(7) 0.1028(4) 0.5357(8) 0.0809(16) Uani 0.590(5) 1 d G U P A 1
H22 H 0.398543 0.071661 0.581121 0.097 Uiso 0.590(5) 1 calc R U P A 1
C23 C 0.4036(6) 0.1649(5) 0.4954(8) 0.0715(16) Uani 0.590(5) 1 d G U P A 1
H23 H 0.515551 0.175230 0.513854 0.086 Uiso 0.590(5) 1 calc R U P A 1
C24 C -0.1124(4) 0.1199(2) 0.4044(3) 0.1089(15) Uani 0.590(5) 1 d D U P A 1
H24A H -0.155215 0.085793 0.450657 0.163 Uiso 0.590(5) 1 calc R U P A 1
H24B H -0.125176 0.099010 0.336449 0.163 Uiso 0.590(5) 1 calc R U P A 1
H24C H -0.172164 0.165923 0.403452 0.163 Uiso 0.590(5) 1 calc R U P A 1
C18B C 0.3080(11) 0.2143(5) 0.4139(10) 0.069(2) Uani 0.410(5) 1 d DG U P A 2
C19B C 0.3868(9) 0.1610(7) 0.4800(12) 0.076(2) Uani 0.410(5) 1 d G U P A 2
H19B H 0.501116 0.162645 0.498176 0.091 Uiso 0.410(5) 1 calc R U P A 2
C20B C 0.2946(12) 0.1052(6) 0.5187(11) 0.087(2) Uani 0.410(5) 1 d DG U P A 2
C21B C 0.1237(11) 0.1027(5) 0.4915(9) 0.092(3) Uani 0.410(5) 1 d G U P A 2
H21B H 0.062047 0.065314 0.517464 0.110 Uiso 0.410(5) 1 calc R U P A 2
C22B C 0.0449(9) 0.1560(5) 0.4255(8) 0.099(3) Uani 0.410(5) 1 d G U P A 2
H22B H -0.069419 0.154312 0.407282 0.119 Uiso 0.410(5) 1 calc R U P A 2
C23B C 0.1371(11) 0.2118(4) 0.3867(8) 0.098(3) Uani 0.410(5) 1 d G U P A 2
H23B H 0.084381 0.247478 0.342546 0.117 Uiso 0.410(5) 1 calc R U P A 2
C24B C 0.3965(10) 0.0497(3) 0.5845(5) 0.134(3) Uani 0.410(5) 1 d D U P A 2
H24D H 0.330517 0.027692 0.631869 0.201 Uiso 0.410(5) 1 calc R U P A 2
H24E H 0.490544 0.074183 0.622106 0.201 Uiso 0.410(5) 1 calc R U P A 2
H24F H 0.433968 0.011709 0.541679 0.201 Uiso 0.410(5) 1 calc R U P A 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.375(2) . ?
C1 N1 1.401(2) . ?
C1 C9 1.449(2) . ?
N1 C4 1.379(2) . ?
N1 C11 1.4773(19) . ?
C2 C3 1.417(3) . ?
C2 C12 1.505(3) . ?
N2 C10 1.392(2) . ?
N2 C11 1.463(2) . ?
C3 C8 1.406(3) . ?
C3 C4 1.416(2) . ?
C4 C5 1.391(2) . ?
C5 C6 1.377(3) . ?
C6 C7 1.390(3) . ?
C7 C8 1.365(3) . ?
C9 C13 1.400(2) . ?
C9 C10 1.406(2) . ?
C10 C16 1.386(2) . ?
C11 C18B 1.449(7) . ?
C11 C17 1.520(2) . ?
C11 C18 1.574(5) . ?
C13 C14 1.370(3) . ?
C14 C15 1.375(3) . ?
C15 C16 1.377(3) . ?
C18 C19 1.3900 . ?
C18 C23 1.3900 . ?
C19 C20 1.3900 . ?
C20 C21 1.3900 . ?
C20 C24 1.509(5) . ?
C21 C22 1.3900 . ?
C22 C23 1.3900 . ?
C18B C19B 1.3900 . ?
C18B C23B 1.3900 . ?
C19B C20B 1.3900 . ?
C20B C21B 1.3900 . ?
C20B C24B 1.495(7) . ?
C21B C22B 1.3900 . ?
C22B C23B 1.3900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 N1 108.93(16) . . ?
C2 C1 C9 133.03(16) . . ?
N1 C1 C9 117.96(14) . . ?
C4 N1 C1 108.99(13) . . ?
C4 N1 C11 127.38(13) . . ?
C1 N1 C11 121.51(13) . . ?
C1 C2 C3 106.82(15) . . ?
C1 C2 C12 128.7(2) . . ?
C3 C2 C12 124.48(18) . . ?
C10 N2 C11 118.16(14) . . ?
C8 C3 C4 118.5(2) . . ?
C8 C3 C2 133.1(2) . . ?
C4 C3 C2 108.41(16) . . ?
N1 C4 C5 132.08(16) . . ?
N1 C4 C3 106.62(15) . . ?
C5 C4 C3 121.27(17) . . ?
C6 C5 C4 118.2(2) . . ?
C5 C6 C7 121.3(2) . . ?
C8 C7 C6 121.0(2) . . ?
C7 C8 C3 119.6(2) . . ?
C13 C9 C10 117.58(17) . . ?
C13 C9 C1 124.31(17) . . ?
C10 C9 C1 118.06(14) . . ?
C16 C10 N2 121.83(17) . . ?
C16 C10 C9 120.50(16) . . ?
N2 C10 C9 117.63(15) . . ?
C18B C11 N2 105.2(4) . . ?
C18B C11 N1 113.9(5) . . ?
N2 C11 N1 105.02(12) . . ?
C18B C11 C17 112.5(5) . . ?
N2 C11 C17 112.12(13) . . ?
N1 C11 C17 107.94(13) . . ?
N2 C11 C18 107.0(3) . . ?
N1 C11 C18 108.6(3) . . ?
C17 C11 C18 115.6(3) . . ?
C14 C13 C9 121.3(2) . . ?
C13 C14 C15 120.21(19) . . ?
C14 C15 C16 120.3(2) . . ?
C15 C16 C10 120.1(2) . . ?
C19 C18 C23 120.0 . . ?
C19 C18 C11 123.3(4) . . ?
C23 C18 C11 116.4(4) . . ?
C18 C19 C20 120.0 . . ?
C21 C20 C19 120.0 . . ?
C21 C20 C24 123.2(3) . . ?
C19 C20 C24 116.8(3) . . ?
C20 C21 C22 120.0 . . ?
C21 C22 C23 120.0 . . ?
C22 C23 C18 120.0 . . ?
C19B C18B C23B 120.0 . . ?
C19B C18B C11 121.1(7) . . ?
C23B C18B C11 118.8(7) . . ?
C20B C19B C18B 120.0 . . ?
C19B C20B C21B 120.0 . . ?
C19B C20B C24B 114.1(7) . . ?
C21B C20B C24B 125.9(7) . . ?
C20B C21B C22B 120.0 . . ?
C23B C22B C21B 120.0 . . ?
C22B C23B C18B 120.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 C1 N1 C4 5.04(18) . . . . ?
C9 C1 N1 C4 -172.15(13) . . . . ?
C2 C1 N1 C11 169.61(13) . . . . ?
C9 C1 N1 C11 -7.6(2) . . . . ?
N1 C1 C2 C3 -3.43(18) . . . . ?
C9 C1 C2 C3 173.17(17) . . . . ?
N1 C1 C2 C12 175.86(17) . . . . ?
C9 C1 C2 C12 -7.5(3) . . . . ?
C1 C2 C3 C8 -178.05(18) . . . . ?
C12 C2 C3 C8 2.6(3) . . . . ?
C1 C2 C3 C4 0.67(18) . . . . ?
C12 C2 C3 C4 -178.66(17) . . . . ?
C1 N1 C4 C5 173.58(17) . . . . ?
C11 N1 C4 C5 10.2(3) . . . . ?
C1 N1 C4 C3 -4.48(17) . . . . ?
C11 N1 C4 C3 -167.90(14) . . . . ?
C8 C3 C4 N1 -178.70(15) . . . . ?
C2 C3 C4 N1 2.36(18) . . . . ?
C8 C3 C4 C5 3.0(2) . . . . ?
C2 C3 C4 C5 -175.95(15) . . . . ?
N1 C4 C5 C6 -179.50(16) . . . . ?
C3 C4 C5 C6 -1.7(3) . . . . ?
C4 C5 C6 C7 -0.7(3) . . . . ?
C5 C6 C7 C8 1.7(3) . . . . ?
C6 C7 C8 C3 -0.3(3) . . . . ?
C4 C3 C8 C7 -2.0(3) . . . . ?
C2 C3 C8 C7 176.67(19) . . . . ?
C2 C1 C9 C13 -12.2(3) . . . . ?
N1 C1 C9 C13 164.19(15) . . . . ?
C2 C1 C9 C10 170.17(17) . . . . ?
N1 C1 C9 C10 -13.5(2) . . . . ?
C11 N2 C10 C16 -144.23(16) . . . . ?
C11 N2 C10 C9 38.1(2) . . . . ?
C13 C9 C10 C16 3.2(2) . . . . ?
C1 C9 C10 C16 -178.95(15) . . . . ?
C13 C9 C10 N2 -179.08(15) . . . . ?
C1 C9 C10 N2 -1.3(2) . . . . ?
C10 N2 C11 C18B -174.4(5) . . . . ?
C10 N2 C11 N1 -53.94(17) . . . . ?
C10 N2 C11 C17 63.01(18) . . . . ?
C10 N2 C11 C18 -169.3(3) . . . . ?
C4 N1 C11 C18B -45.5(5) . . . . ?
C1 N1 C11 C18B 152.9(5) . . . . ?
C4 N1 C11 N2 -160.14(14) . . . . ?
C1 N1 C11 N2 38.31(18) . . . . ?
C4 N1 C11 C17 80.09(18) . . . . ?
C1 N1 C11 C17 -81.47(17) . . . . ?
C4 N1 C11 C18 -45.9(3) . . . . ?
C1 N1 C11 C18 152.5(3) . . . . ?
C10 C9 C13 C14 -1.8(3) . . . . ?
C1 C9 C13 C14 -179.42(17) . . . . ?
C9 C13 C14 C15 -0.9(3) . . . . ?
C13 C14 C15 C16 2.1(3) . . . . ?
C14 C15 C16 C10 -0.6(3) . . . . ?
N2 C10 C16 C15 -179.69(16) . . . . ?
C9 C10 C16 C15 -2.1(3) . . . . ?
N2 C11 C18 C19 -120.6(5) . . . . ?
N1 C11 C18 C19 126.5(5) . . . . ?
C17 C11 C18 C19 5.1(6) . . . . ?
N2 C11 C18 C23 53.3(4) . . . . ?
N1 C11 C18 C23 -59.6(4) . . . . ?
C17 C11 C18 C23 178.9(3) . . . . ?
C23 C18 C19 C20 0.0 . . . . ?
C11 C18 C19 C20 173.7(6) . . . . ?
C18 C19 C20 C21 0.0 . . . . ?
C18 C19 C20 C24 -178.6(6) . . . . ?
C19 C20 C21 C22 0.0 . . . . ?
C24 C20 C21 C22 178.5(6) . . . . ?
C20 C21 C22 C23 0.0 . . . . ?
C21 C22 C23 C18 0.0 . . . . ?
C19 C18 C23 C22 0.0 . . . . ?
C11 C18 C23 C22 -174.1(6) . . . . ?
N2 C11 C18B C19B 54.7(7) . . . . ?
N1 C11 C18B C19B -59.8(7) . . . . ?
C17 C11 C18B C19B 177.0(5) . . . . ?
N2 C11 C18B C23B -129.0(7) . . . . ?
N1 C11 C18B C23B 116.6(7) . . . . ?
C17 C11 C18B C23B -6.6(9) . . . . ?
C23B C18B C19B C20B 0.0 . . . . ?
C11 C18B C19B C20B 176.3(9) . . . . ?
C18B C19B C20B C21B 0.0 . . . . ?
C18B C19B C20B C24B 177.2(11) . . . . ?
C19B C20B C21B C22B 0.0 . . . . ?
C24B C20B C21B C22B -176.8(12) . . . . ?
C20B C21B C22B C23B 0.0 . . . . ?
C21B C22B C23B C18B 0.0 . . . . ?
C19B C18B C23B C22B 0.0 . . . . ?
C11 C18B C23B C22B -176.4(9) . . . . ?

_refine_diff_density_max         0.116
_refine_diff_density_min         -0.110
_refine_diff_density_rms         0.026




####################################################################### 
# 
# 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_cmpd_6a-SP673_sq
_database_code_depnum_ccdc_archive 'CCDC 2310240'
loop_
_audit_author_name
_audit_author_address
'Pascal Retailleau'
;ICSN CNRS University Paris Saclay
France
;
_audit_update_record             
;
2023-11-24 deposited with the CCDC.	2024-02-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_chemical_name_systematic        
;
'5-(1-(3,4,5-trimethoxyphenyl)vinyl)-5,10-dihydroindolo[3,2-b]indole solvate'
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H22 N2 O3 [+ solvent]'
_chemical_formula_sum            'C25 H22 N2 O3 [+ solvent]'
_chemical_formula_weight         398.44

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

_space_group_crystal_system      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                   8.4557(5)
_cell_length_b                   11.5977(7)
_cell_length_c                   12.3663(9)
_cell_angle_alpha                79.089(6)
_cell_angle_beta                 84.728(6)
_cell_angle_gamma                72.178(5)
_cell_volume                     1132.91(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    825
_cell_measurement_theta_min      5.5
_cell_measurement_theta_max      68.2

_exptl_crystal_description       block
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.168
_exptl_crystal_F_000             420
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.58
_exptl_crystal_size_mid          0.55
_exptl_crystal_size_min          0.28
_exptl_absorpt_coefficient_mu    0.621
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.856
_exptl_absorpt_process_details   'Abscor (Higashi-Rigaku, 1998)'

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54187
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Rotating Anode'
_diffrn_radiation_monochromator  'Confocal CMF Osmic'
_diffrn_measurement_specimen_support Fiber
_diffrn_detector                 'RX Rapid2 curved IP'
_diffrn_measurement_device       
;
Crystal Goniometer chi-partial
;
_diffrn_measurement_device_type  
;
Rigaku RAXIS conversion
;
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_reflns_number            14682
_diffrn_reflns_av_unetI/netI     0.0437
_diffrn_reflns_av_R_equivalents  0.0494
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.643
_diffrn_reflns_theta_max         66.699
_diffrn_reflns_theta_full        66.699
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measured_fraction_theta_full 0.973
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_Laue_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_point_group_measured_fraction_full 0.973
_reflns_number_total             3919
_reflns_number_gt                2395
_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.
 
 Structure factors included contributions from the .fab file.
 
 _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       
;
CrystalClear-SM Expert 2.0 r16 (Rigaku, 2014)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 r16 (Rigaku, 2014)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r16 (Rigaku, 2014)
;
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL-2019/2  (Sheldrick, 2015b)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          SQUEEZE
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0946P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     other
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3903
_refine_ls_number_parameters     317
_refine_ls_number_restraints     120
_refine_ls_R_factor_all          0.0732
_refine_ls_R_factor_gt           0.0499
_refine_ls_wR_factor_ref         0.1498
_refine_ls_wR_factor_gt          0.1303
_refine_ls_goodness_of_fit_ref   0.931
_refine_ls_restrained_S_all      0.949
_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 0.04940(15) 0.77951(11) 0.14442(10) 0.0684(4) Uani 1 1 d . . . . .
C1 C 0.5935(2) 0.14508(16) 0.18912(14) 0.0578(5) Uani 1 1 d . . . . .
N1 N 0.55577(19) 0.27218(13) 0.17819(12) 0.0621(4) Uani 1 1 d . . . . .
O2 O 0.0460(5) 0.7420(3) 0.3586(3) 0.0707(11) Uani 0.838(5) 1 d D U P A 1
C24 C 0.1357(4) 0.7927(2) 0.4243(2) 0.0907(11) Uani 0.838(5) 1 d D U P A 1
H24A H 0.061692 0.865889 0.446825 0.136 Uiso 0.838(5) 1 calc R U P A 1
H24B H 0.227071 0.812245 0.380877 0.136 Uiso 0.838(5) 1 calc R U P A 1
H24C H 0.177103 0.733208 0.488343 0.136 Uiso 0.838(5) 1 calc R U P A 1
O2B O 0.093(3) 0.7536(14) 0.3542(17) 0.062(4) Uani 0.162(5) 1 d D U P A 2
C24B C 0.010(3) 0.7388(19) 0.4667(15) 0.161(9) Uani 0.162(5) 1 d D U P A 2
H24D H -0.042712 0.818243 0.486359 0.241 Uiso 0.162(5) 1 calc R U P A 2
H24E H 0.091822 0.691496 0.519623 0.241 Uiso 0.162(5) 1 calc R U P A 2
H24F H -0.071700 0.697068 0.465778 0.241 Uiso 0.162(5) 1 calc R U P A 2
C2 C 0.7507(2) 0.09073(17) 0.22727(14) 0.0597(5) Uani 1 1 d . . . . .
N2 N 0.7845(2) -0.03494(15) 0.24413(13) 0.0690(5) Uani 1 1 d . . . . .
HN2 H 0.889(3) -0.0939(17) 0.2636(16) 0.083 Uiso 1 1 d . U . . .
C3 C 0.8214(2) 0.18375(17) 0.24079(14) 0.0613(5) Uani 1 1 d . . . . .
C4 C 0.6976(2) 0.29574(17) 0.20775(15) 0.0614(5) Uani 1 1 d . . . . .
C5 C 0.7280(3) 0.40838(19) 0.20177(17) 0.0765(6) Uani 1 1 d . . . . .
H5 H 0.647040 0.481850 0.178266 0.092 Uiso 1 1 calc R U . . .
C6 C 0.8803(3) 0.4079(2) 0.2314(2) 0.0897(7) Uani 1 1 d . . . . .
H6 H 0.903071 0.482145 0.227331 0.108 Uiso 1 1 calc R U . . .
C7 C 1.0016(3) 0.2984(2) 0.26766(19) 0.0936(8) Uani 1 1 d . . . . .
H7 H 1.102679 0.301216 0.289231 0.112 Uiso 1 1 calc R U . . .
C8 C 0.9753(3) 0.1852(2) 0.27233(17) 0.0784(6) Uani 1 1 d . . . . .
H8 H 1.057527 0.112460 0.295742 0.094 Uiso 1 1 calc R U . . .
C9 C 0.5212(2) 0.05127(16) 0.17965(14) 0.0575(5) Uani 1 1 d . . . . .
C10 C 0.6459(3) -0.05981(18) 0.21377(15) 0.0629(5) Uani 1 1 d . . . . .
C11 C 0.4103(2) 0.35948(16) 0.13167(15) 0.0611(5) Uani 1 1 d . . . . .
C12 C 0.3490(3) 0.34195(18) 0.04326(16) 0.0832(7) Uani 1 1 d . . . . .
H12A H 0.401237 0.272508 0.011758 0.100 Uiso 1 1 calc R U . . .
H12B H 0.253705 0.399095 0.012751 0.100 Uiso 1 1 calc R U . . .
C13 C 0.6238(3) -0.17425(18) 0.21692(17) 0.0791(6) Uani 1 1 d . . . . .
H13 H 0.708276 -0.246326 0.238373 0.095 Uiso 1 1 calc R U . . .
C14 C 0.4732(3) -0.1771(2) 0.18732(19) 0.0856(7) Uani 1 1 d . . . . .
H14 H 0.454535 -0.252490 0.189490 0.103 Uiso 1 1 calc R U . . .
C15 C 0.3478(3) -0.0694(2) 0.15410(19) 0.0864(7) Uani 1 1 d . . . . .
H15 H 0.246646 -0.074469 0.134865 0.104 Uiso 1 1 calc R U . . .
C16 C 0.3689(3) 0.04487(19) 0.14882(17) 0.0736(6) Uani 1 1 d . . . . .
H16 H 0.284175 0.116054 0.125342 0.088 Uiso 1 1 calc R U . . .
C17 C 0.3266(2) 0.46227(16) 0.19228(15) 0.0565(5) Uani 1 1 d . . . . .
C18 C 0.2339(2) 0.57391(16) 0.13488(14) 0.0556(5) Uani 1 1 d . . . . .
H18 H 0.231202 0.586591 0.058439 0.067 Uiso 1 1 calc R U . . .
C19 C 0.1454(2) 0.66614(16) 0.19274(15) 0.0539(4) Uani 1 1 d . . . . .
C20 C 0.1494(2) 0.64882(16) 0.30630(15) 0.0580(5) Uani 1 1 d D U . . .
C21 C 0.2417(3) 0.53780(18) 0.36269(15) 0.0678(5) Uani 1 1 d D U . . .
C22 C 0.3316(2) 0.44453(17) 0.30568(15) 0.0649(5) Uani 1 1 d . . . . .
H22 H 0.395115 0.370146 0.343910 0.078 Uiso 1 1 calc R U . . .
C23 C 0.0343(3) 0.80319(19) 0.02901(17) 0.0926(7) Uani 1 1 d . . . . .
H23A H -0.044787 0.882134 0.007641 0.139 Uiso 1 1 calc R U . . .
H23B H -0.002833 0.740837 0.007324 0.139 Uiso 1 1 calc R U . . .
H23C H 0.140358 0.802710 -0.006437 0.139 Uiso 1 1 calc R U . . .
O3 O 0.2684(15) 0.5331(8) 0.4723(5) 0.0866(18) Uani 0.404(13) 1 d D U P B 1
C25 C 0.262(2) 0.4101(8) 0.5393(8) 0.101(3) Uani 0.404(13) 1 d D U P B 1
H25A H 0.231835 0.419097 0.614661 0.152 Uiso 0.404(13) 1 calc R U P B 1
H25B H 0.368897 0.350464 0.535472 0.152 Uiso 0.404(13) 1 calc R U P B 1
H25C H 0.180546 0.383200 0.509903 0.152 Uiso 0.404(13) 1 calc R U P B 1
O3B O 0.2176(9) 0.5235(6) 0.4762(3) 0.0832(15) Uani 0.596(13) 1 d D U P B 2
C25B C 0.3569(13) 0.4174(6) 0.5353(6) 0.107(2) Uani 0.596(13) 1 d D U P B 2
H25D H 0.358798 0.427356 0.610448 0.161 Uiso 0.596(13) 1 calc R U P B 2
H25E H 0.461930 0.418024 0.498750 0.161 Uiso 0.596(13) 1 calc R U P B 2
H25F H 0.337025 0.340606 0.533570 0.161 Uiso 0.596(13) 1 calc R U P B 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C19 1.372(2) . ?
O1 C23 1.411(2) . ?
C1 C2 1.370(3) . ?
C1 N1 1.392(2) . ?
C1 C9 1.428(2) . ?
N1 C4 1.402(2) . ?
N1 C11 1.420(2) . ?
O2 C20 1.390(3) . ?
O2 C24 1.466(4) . ?
O2B C20 1.386(8) . ?
O2B C24B 1.504(9) . ?
C2 N2 1.375(2) . ?
C2 C3 1.425(2) . ?
N2 C10 1.388(2) . ?
C3 C8 1.398(3) . ?
C3 C4 1.412(3) . ?
C4 C5 1.394(2) . ?
C5 C6 1.369(3) . ?
C6 C7 1.392(3) . ?
C7 C8 1.387(3) . ?
C9 C16 1.403(3) . ?
C9 C10 1.412(3) . ?
C10 C13 1.389(3) . ?
C11 C12 1.326(3) . ?
C11 C17 1.486(2) . ?
C13 C14 1.368(3) . ?
C14 C15 1.389(3) . ?
C15 C16 1.379(3) . ?
C17 C22 1.381(2) . ?
C17 C18 1.389(2) . ?
C18 C19 1.385(2) . ?
C19 C20 1.382(2) . ?
C20 C21 1.378(3) . ?
C21 O3 1.383(6) . ?
C21 O3B 1.386(4) . ?
C21 C22 1.390(2) . ?
O3 C25 1.522(7) . ?
O3B C25B 1.539(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 O1 C23 118.53(14) . . ?
C2 C1 N1 109.54(17) . . ?
C2 C1 C9 108.80(17) . . ?
N1 C1 C9 141.55(19) . . ?
C1 N1 C4 106.52(16) . . ?
C1 N1 C11 125.73(16) . . ?
C4 N1 C11 127.23(15) . . ?
C20 O2 C24 113.4(3) . . ?
C20 O2B C24B 116.0(13) . . ?
C1 C2 N2 109.60(17) . . ?
C1 C2 C3 109.14(18) . . ?
N2 C2 C3 141.2(2) . . ?
C2 N2 C10 107.21(16) . . ?
C8 C3 C4 119.72(18) . . ?
C8 C3 C2 135.3(2) . . ?
C4 C3 C2 104.92(17) . . ?
C5 C4 N1 128.8(2) . . ?
C5 C4 C3 121.21(18) . . ?
N1 C4 C3 109.84(16) . . ?
C6 C5 C4 118.2(2) . . ?
C5 C6 C7 121.3(2) . . ?
C8 C7 C6 121.5(2) . . ?
C7 C8 C3 118.0(2) . . ?
C16 C9 C10 118.29(17) . . ?
C16 C9 C1 137.22(19) . . ?
C10 C9 C1 104.49(17) . . ?
N2 C10 C13 127.5(2) . . ?
N2 C10 C9 109.89(16) . . ?
C13 C10 C9 122.6(2) . . ?
C12 C11 N1 119.96(17) . . ?
C12 C11 C17 123.24(18) . . ?
N1 C11 C17 116.60(16) . . ?
C14 C13 C10 117.6(2) . . ?
C13 C14 C15 121.2(2) . . ?
C16 C15 C14 121.9(2) . . ?
C15 C16 C9 118.5(2) . . ?
C22 C17 C18 120.09(16) . . ?
C22 C17 C11 120.29(17) . . ?
C18 C17 C11 119.48(16) . . ?
C19 C18 C17 119.25(17) . . ?
O1 C19 C20 114.99(15) . . ?
O1 C19 C18 124.05(16) . . ?
C20 C19 C18 120.95(17) . . ?
C21 C20 C19 119.47(16) . . ?
C21 C20 O2B 122.1(10) . . ?
C19 C20 O2B 116.5(10) . . ?
C21 C20 O2 123.1(2) . . ?
C19 C20 O2 117.2(3) . . ?
C20 C21 O3 117.0(4) . . ?
C20 C21 O3B 114.7(3) . . ?
C20 C21 C22 120.21(17) . . ?
O3 C21 C22 121.4(5) . . ?
O3B C21 C22 124.5(3) . . ?
C17 C22 C21 120.03(18) . . ?
C21 O3 C25 110.2(8) . . ?
C21 O3B C25B 111.9(5) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 C1 N1 C4 1.80(19) . . . . ?
C9 C1 N1 C4 177.3(2) . . . . ?
C2 C1 N1 C11 174.01(15) . . . . ?
C9 C1 N1 C11 -10.5(3) . . . . ?
N1 C1 C2 N2 176.56(13) . . . . ?
C9 C1 C2 N2 -0.5(2) . . . . ?
N1 C1 C2 C3 -0.9(2) . . . . ?
C9 C1 C2 C3 -177.89(13) . . . . ?
C1 C2 N2 C10 1.11(19) . . . . ?
C3 C2 N2 C10 177.2(2) . . . . ?
C1 C2 C3 C8 -177.29(19) . . . . ?
N2 C2 C3 C8 6.6(4) . . . . ?
C1 C2 C3 C4 -0.41(19) . . . . ?
N2 C2 C3 C4 -176.5(2) . . . . ?
C1 N1 C4 C5 174.05(18) . . . . ?
C11 N1 C4 C5 2.0(3) . . . . ?
C1 N1 C4 C3 -2.07(19) . . . . ?
C11 N1 C4 C3 -174.13(16) . . . . ?
C8 C3 C4 C5 2.5(3) . . . . ?
C2 C3 C4 C5 -174.93(16) . . . . ?
C8 C3 C4 N1 179.01(15) . . . . ?
C2 C3 C4 N1 1.53(19) . . . . ?
N1 C4 C5 C6 -177.30(17) . . . . ?
C3 C4 C5 C6 -1.6(3) . . . . ?
C4 C5 C6 C7 -0.6(3) . . . . ?
C5 C6 C7 C8 1.8(3) . . . . ?
C6 C7 C8 C3 -0.8(3) . . . . ?
C4 C3 C8 C7 -1.3(3) . . . . ?
C2 C3 C8 C7 175.23(18) . . . . ?
C2 C1 C9 C16 178.6(2) . . . . ?
N1 C1 C9 C16 3.1(4) . . . . ?
C2 C1 C9 C10 -0.36(18) . . . . ?
N1 C1 C9 C10 -175.8(2) . . . . ?
C2 N2 C10 C13 -179.97(18) . . . . ?
C2 N2 C10 C9 -1.36(19) . . . . ?
C16 C9 C10 N2 -178.11(15) . . . . ?
C1 C9 C10 N2 1.06(18) . . . . ?
C16 C9 C10 C13 0.6(3) . . . . ?
C1 C9 C10 C13 179.74(17) . . . . ?
C1 N1 C11 C12 -39.6(3) . . . . ?
C4 N1 C11 C12 131.0(2) . . . . ?
C1 N1 C11 C17 135.48(17) . . . . ?
C4 N1 C11 C17 -53.9(2) . . . . ?
N2 C10 C13 C14 177.25(17) . . . . ?
C9 C10 C13 C14 -1.2(3) . . . . ?
C10 C13 C14 C15 0.7(3) . . . . ?
C13 C14 C15 C16 0.3(3) . . . . ?
C14 C15 C16 C9 -1.0(3) . . . . ?
C10 C9 C16 C15 0.5(3) . . . . ?
C1 C9 C16 C15 -178.31(19) . . . . ?
C12 C11 C17 C22 143.2(2) . . . . ?
N1 C11 C17 C22 -31.7(2) . . . . ?
C12 C11 C17 C18 -32.4(3) . . . . ?
N1 C11 C17 C18 152.69(16) . . . . ?
C22 C17 C18 C19 -0.8(3) . . . . ?
C11 C17 C18 C19 174.90(15) . . . . ?
C23 O1 C19 C20 -177.94(16) . . . . ?
C23 O1 C19 C18 2.3(3) . . . . ?
C17 C18 C19 O1 -179.73(14) . . . . ?
C17 C18 C19 C20 0.5(3) . . . . ?
O1 C19 C20 C21 179.73(15) . . . . ?
C18 C19 C20 C21 -0.5(3) . . . . ?
O1 C19 C20 O2B -15.6(10) . . . . ?
C18 C19 C20 O2B 164.2(10) . . . . ?
O1 C19 C20 O2 5.6(3) . . . . ?
C18 C19 C20 O2 -174.6(2) . . . . ?
C24B O2B C20 C21 -48(2) . . . . ?
C24B O2B C20 C19 147.7(17) . . . . ?
C24 O2 C20 C21 64.5(4) . . . . ?
C24 O2 C20 C19 -121.6(3) . . . . ?
C19 C20 C21 O3 167.5(5) . . . . ?
O2 C20 C21 O3 -18.7(6) . . . . ?
C19 C20 C21 O3B -170.7(4) . . . . ?
O2B C20 C21 O3B 25.5(11) . . . . ?
C19 C20 C21 C22 0.7(3) . . . . ?
O2B C20 C21 C22 -163.1(9) . . . . ?
O2 C20 C21 C22 174.5(2) . . . . ?
C18 C17 C22 C21 1.0(3) . . . . ?
C11 C17 C22 C21 -174.66(17) . . . . ?
C20 C21 C22 C17 -0.9(3) . . . . ?
O3 C21 C22 C17 -167.2(5) . . . . ?
O3B C21 C22 C17 169.6(5) . . . . ?
C20 C21 O3 C25 142.3(10) . . . . ?
C22 C21 O3 C25 -51.0(13) . . . . ?
C20 C21 O3B C25B -163.4(8) . . . . ?
C22 C21 O3B C25B 25.5(12) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C24^a H24C^a O3^a 0.96 2.25 2.838(9) 118.5 . yes
C24B^b H24E^b O3B^b 0.96 2.06 2.563(18) 110.9 . yes
N2 HN2 O1 0.95(2) 2.325(19) 2.952(2) 122.8(15) 1_645 yes
N2 HN2 O2^a 0.95(2) 2.16(2) 3.045(5) 154.0(16) 1_645 yes
N2 HN2 O2B^b 0.95(2) 2.26(3) 3.19(2) 163.6(17) 1_645 yes

_refine_diff_density_max         0.162
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.043




loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.500 0.000 0.500 123 33 '0.39 (diethyl ether (?) solvent molecule) per asu '
_platon_squeeze_void_probe_radius 1.20
_platon_squeeze_details          ?

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: diethyl ether'
####################################################################### 
# 
# 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_cmpd_6c_SP659F2_sq
_database_code_depnum_ccdc_archive 'CCDC 2310242'
loop_
_audit_author_name
_audit_author_address
'Pascal Retailleau'
;ICSN CNRS University Paris Saclay
France
;
_audit_update_record             
;
2023-11-24 deposited with the CCDC.	2024-02-08 downloaded from the CCDC.
;

# start Validation Reply Form

_vrf_PLAT309_cmpd_6c_SP659F2_sq  
;
PROBLEM: Single Bonded Oxygen (C-O > 1.3 Ang) ...........         O3 Check 
RESPONSE: slight disorder of the trimethoxy phenyl substituent has been
treated as static disorder (occ : 0.84-0.16)and two methoxy groups have 
occupancy sites correlated by packing symmetry (O2-C24 and O3-C25). 
Regarding the latter one,
the major site has been split in two sites (occ: 0.54-0.30)leading to 
three putative positions that should avoid bad contacts between different asus.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        
2-fluoro-10-(1-(3,4,5-trimethoxyphenyl)vinyl)-5,10-dihydroindolo[3,2-b]indole
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H21 F N2 O3 [+ solvent]'
_chemical_formula_sum            'C25 H21 F N2 O3 [+ solvent]'
_chemical_formula_weight         416.44

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

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

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

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

_cell_length_a                   8.6051(3)
_cell_length_b                   11.7265(6)
_cell_length_c                   12.2507(6)
_cell_angle_alpha                79.867(4)
_cell_angle_beta                 86.096(4)
_cell_angle_gamma                70.779(4)
_cell_volume                     1149.00(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    10086
_cell_measurement_theta_min      2.6010
_cell_measurement_theta_max      28.9580

_exptl_crystal_description       prism
_exptl_crystal_colour            'pale orange'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             436
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 -1 0.0497
-1 -5 3 0.0555
0 -1 5 0.0935
5 3 2 0.0919
-1 -5 0 0.0751
-4 -5 -1 0.1135
-5 0 -2 0.1216
0 5 2 0.0901
-1 -1 5 0.0695
-1 -5 1 0.0677
0 -1 0 0.0806
-2 14 0 0.0796
0 -1 -5 0.0540
_exptl_absorpt_coefficient_mu    0.085
_exptl_crystal_size_max          0.251
_exptl_crystal_size_mid          0.182
_exptl_crystal_size_min          0.148
_exptl_crystal_density_diffrn    1.204
_exptl_absorpt_correction_T_min  0.374
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.122a (Rigaku Oxford Diffraction, 2021)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      293(2)
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku mm003 (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'Double bounce MaxFlux multilayer optic'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku XtaLAB Pro: Kappa single'
_diffrn_detector                 'Dectris Pilatus200K 3R'
_diffrn_reflns_number            22443
_diffrn_reflns_av_unetI/netI     0.0261
_diffrn_reflns_av_R_equivalents  0.0399
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.507
_diffrn_reflns_theta_max         25.348
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -33.00  97.00   0.50   30.00    --    7.40  57.00 -60.00  260
  2  ω    -33.00  97.00   0.50   30.00    --    7.40  57.00 -90.00  260
  3  ω    -33.00  87.00   0.50   30.00    --    7.40  57.00  30.00  240
  4  ω     14.00  96.00   0.50   30.00    --    7.40  57.00 150.00  164
  5  ω     21.00  60.00   0.50   30.00    --   -7.70  57.00 -30.00   78
  6  ω    -48.00  82.00   0.50   30.00    --   -7.70  57.00  90.00  260
  7  ω    -58.00  81.00   0.50   30.00    --   -7.70  38.00  30.00  278
;
_reflns_number_total             4211
_reflns_number_gt                3419
_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.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          SQUEEZE
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1333P)²+0.1238P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     other
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4208
_refine_ls_number_parameters     416
_refine_ls_number_restraints     569
_refine_ls_R_factor_all          0.0655
_refine_ls_R_factor_gt           0.0572
_refine_ls_wR_factor_ref         0.1850
_refine_ls_wR_factor_gt          0.1746
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.005
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.89121(18) 0.51450(13) 0.21795(15) 0.0975(5) Uani 1 1 d . . . . .
C1 C 0.7476(2) 0.09178(14) 0.22591(14) 0.0480(4) Uani 1 1 d . . . . .
N1 N 0.78573(19) -0.03397(13) 0.24366(13) 0.0573(4) Uani 1 1 d D . . . .
H1N H 0.878(2) -0.0905(18) 0.2617(18) 0.069 Uiso 1 1 d D U . . .
C2 C 0.59010(19) 0.14439(14) 0.18854(13) 0.0457(4) Uani 1 1 d . . . . .
N2 N 0.54824(16) 0.27193(11) 0.17728(12) 0.0486(4) Uani 1 1 d . . . . .
C3 C 0.5213(2) 0.05127(14) 0.18047(14) 0.0489(4) Uani 1 1 d . . . . .
C4 C 0.6500(2) -0.05946(15) 0.21542(15) 0.0528(4) Uani 1 1 d . . . . .
C5 C 0.6305(3) -0.17324(16) 0.21802(18) 0.0679(6) Uani 1 1 d . . . . .
H5 H 0.716827 -0.245259 0.238268 0.081 Uiso 1 1 calc R U . . .
C6 C 0.4813(3) -0.17597(19) 0.1901(2) 0.0762(6) Uani 1 1 d . . . . .
H6 H 0.464697 -0.250951 0.193203 0.091 Uiso 1 1 calc R U . . .
C7 C 0.3527(3) -0.0677(2) 0.1567(2) 0.0744(6) Uani 1 1 d . . . . .
H7 H 0.252359 -0.072424 0.137767 0.089 Uiso 1 1 calc R U . . .
C8 C 0.3704(2) 0.04500(18) 0.15107(17) 0.0613(5) Uani 1 1 d . . . . .
H8 H 0.283773 0.116001 0.128176 0.074 Uiso 1 1 calc R U . . .
C9 C 0.8147(2) 0.18435(15) 0.23852(14) 0.0494(4) Uani 1 1 d . . . . .
C10 C 0.68705(19) 0.29627(14) 0.20475(14) 0.0483(4) Uani 1 1 d . . . . .
C12 C 0.9664(2) 0.18814(19) 0.26760(17) 0.0618(5) Uani 1 1 d . . . . .
H12 H 1.050810 0.115866 0.290904 0.074 Uiso 1 1 calc R U . . .
C13 C 0.9909(3) 0.2989(2) 0.26173(19) 0.0711(6) Uani 1 1 d . . . . .
H13 H 1.091299 0.302511 0.281736 0.085 Uiso 1 1 calc R U . . .
C14 C 0.8636(3) 0.40585(19) 0.22551(19) 0.0675(5) Uani 1 1 d . . . . .
C15 C 0.7115(2) 0.40881(16) 0.19745(17) 0.0585(5) Uani 1 1 d . . . . .
H15 H 0.628638 0.482147 0.174657 0.070 Uiso 1 1 calc R U . . .
C16 C 0.3347(3) 0.34297(16) 0.04397(16) 0.0635(5) Uani 1 1 d . . . . .
H16A H 0.385090 0.273514 0.011716 0.076 Uiso 1 1 calc R U . . .
H16B H 0.238025 0.400645 0.014447 0.076 Uiso 1 1 calc R U . . .
C11 C 0.40046(19) 0.35970(13) 0.13169(14) 0.0467(4) Uani 1 1 d D U . . .
C17 C 0.3205(10) 0.4657(3) 0.1903(3) 0.0385(10) Uani 0.84 1 d D U P A 1
C18 C 0.2305(6) 0.5798(3) 0.1337(4) 0.0389(9) Uani 0.84 1 d D U P A 1
H18 H 0.223918 0.594144 0.056811 0.047 Uiso 0.84 1 calc R U P A 1
C19 C 0.1501(8) 0.6724(5) 0.1958(4) 0.0383(9) Uani 0.84 1 d D U P A 1
O1 O 0.0618(8) 0.7874(5) 0.1465(4) 0.0518(11) Uani 0.84 1 d D U P A 1
C23 C 0.0419(7) 0.8070(4) 0.0310(4) 0.0786(15) Uani 0.84 1 d D U P A 1
H23A H -0.031174 0.888357 0.007356 0.118 Uiso 0.84 1 calc R U P A 1
H23B H -0.003512 0.748625 0.011889 0.118 Uiso 0.84 1 calc R U P A 1
H23C H 0.146911 0.797521 -0.005228 0.118 Uiso 0.84 1 calc R U P A 1
C20 C 0.1552(9) 0.6512(4) 0.3113(3) 0.0451(9) Uani 0.84 1 d D U P A 1
O2 O 0.0576(5) 0.7467(5) 0.3635(3) 0.0617(9) Uani 0.84 1 d D U P A 1
C24 C 0.1477(4) 0.7947(2) 0.4265(2) 0.0823(8) Uani 0.84 1 d D U P A 1
H24A H 0.079127 0.873316 0.441972 0.124 Uiso 0.84 1 calc R U P A 1
H24B H 0.243095 0.803176 0.385034 0.124 Uiso 0.84 1 calc R U P A 1
H24C H 0.181410 0.739919 0.495018 0.124 Uiso 0.84 1 calc R U P A 1
C21 C 0.2469(11) 0.5354(4) 0.3666(5) 0.0549(10) Uani 0.84 1 d D U P A 1
C22 C 0.3319(7) 0.4445(4) 0.3060(3) 0.0455(9) Uani 0.84 1 d D U P A 1
H22 H 0.396917 0.368906 0.342260 0.055 Uiso 0.84 1 calc R U P A 1
O3 O 0.246(2) 0.5275(11) 0.4848(12) 0.073(3) Uani 0.54 1 d D U P B 3
C25 C 0.3395(14) 0.4146(8) 0.5438(10) 0.100(5) Uani 0.54 1 d D U P B 3
H25A H 0.292990 0.352704 0.535229 0.150 Uiso 0.54 1 calc R U P B 3
H25B H 0.339286 0.420663 0.620968 0.150 Uiso 0.54 1 calc R U P B 3
H25C H 0.450464 0.393155 0.515699 0.150 Uiso 0.54 1 calc R U P B 3
O3C O 0.213(4) 0.5223(19) 0.471(2) 0.082(5) Uani 0.3 1 d D U P C 4
C25C C 0.2412(19) 0.4074(14) 0.5386(13) 0.105(5) Uani 0.3 1 d D U P C 4
H25G H 0.194733 0.418706 0.610995 0.157 Uiso 0.3 1 calc R U P C 4
H25H H 0.357574 0.365864 0.544696 0.157 Uiso 0.3 1 calc R U P C 4
H25I H 0.190876 0.359429 0.506485 0.157 Uiso 0.3 1 calc R U P C 4
C17B C 0.331(5) 0.446(2) 0.2114(18) 0.041(4) Uani 0.16 1 d D U P A 2
C18B C 0.260(3) 0.557(2) 0.146(2) 0.040(4) Uani 0.16 1 d D U P A 2
H18B H 0.291578 0.562753 0.072002 0.048 Uiso 0.16 1 calc R U P A 2
C19B C 0.148(5) 0.660(3) 0.178(2) 0.044(4) Uani 0.16 1 d D U P A 2
O1B O 0.038(5) 0.773(3) 0.138(3) 0.055(5) Uani 0.16 1 d D U P A 2
C23B C -0.010(4) 0.814(3) 0.027(3) 0.090(8) Uani 0.16 1 d D U P A 2
H23D H -0.008425 0.896172 0.004495 0.134 Uiso 0.16 1 calc R U P A 2
H23E H -0.119146 0.811686 0.018858 0.134 Uiso 0.16 1 calc R U P A 2
H23F H 0.064915 0.761584 -0.019490 0.134 Uiso 0.16 1 calc R U P A 2
C20B C 0.155(6) 0.664(2) 0.288(2) 0.049(4) Uani 0.16 1 d D U P A 2
O2B O 0.097(3) 0.758(3) 0.3482(18) 0.068(5) Uani 0.16 1 d D U P A 2
C24B C 0.022(3) 0.752(2) 0.4541(16) 0.132(7) Uani 0.16 1 d D U P A 2
H24D H -0.073996 0.727570 0.451063 0.199 Uiso 0.16 1 calc R U P A 2
H24E H -0.010449 0.830772 0.476880 0.199 Uiso 0.16 1 calc R U P A 2
H24F H 0.097958 0.693047 0.506346 0.199 Uiso 0.16 1 calc R U P A 2
C21B C 0.234(6) 0.560(2) 0.359(2) 0.054(4) Uani 0.16 1 d D U P A 2
O3B O 0.289(3) 0.543(2) 0.4660(18) 0.068(5) Uani 0.16 1 d D U P A 2
C25B C 0.393(5) 0.434(3) 0.527(3) 0.090(9) Uani 0.16 1 d D U P A 2
H25D H 0.503470 0.418940 0.498810 0.135 Uiso 0.16 1 calc R U P A 2
H25E H 0.355787 0.367214 0.520044 0.135 Uiso 0.16 1 calc R U P A 2
H25F H 0.390005 0.442943 0.603649 0.135 Uiso 0.16 1 calc R U P A 2
C22B C 0.302(4) 0.449(3) 0.323(2) 0.068(10) Uani 0.16 1 d D U P A 2
H22B H 0.327309 0.376184 0.373690 0.082 Uiso 0.16 1 calc R U P A 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C14 1.358(2) . ?
C1 C2 1.365(2) . ?
C1 N1 1.381(2) . ?
C1 C9 1.421(2) . ?
N1 C4 1.377(3) . ?
N1 H1N 0.865(16) . ?
C2 N2 1.4018(19) . ?
C2 C3 1.423(2) . ?
N2 C10 1.391(2) . ?
N2 C11 1.422(2) . ?
C3 C8 1.399(3) . ?
C3 C4 1.421(2) . ?
C4 C5 1.393(3) . ?
C5 C6 1.363(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.399(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.369(3) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
C9 C12 1.393(3) . ?
C9 C10 1.422(2) . ?
C10 C15 1.390(2) . ?
C12 C13 1.372(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.391(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.364(3) . ?
C15 H15 0.9300 . ?
C16 C11 1.320(3) . ?
C16 H16A 0.9300 . ?
C16 H16B 0.9300 . ?
C11 C17B 1.487(9) . ?
C11 C17 1.489(3) . ?
C17 C18 1.391(4) . ?
C17 C22 1.399(4) . ?
C18 C19 1.401(4) . ?
C18 H18 0.9300 . ?
C19 O1 1.364(4) . ?
C19 C20 1.394(4) . ?
O1 C23 1.406(4) . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C20 O2 1.388(4) . ?
C20 C21 1.403(4) . ?
O2 C24 1.427(5) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C21 C22 1.384(5) . ?
C22 H22 0.9300 . ?
O3 C25 1.403(6) . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
O3C C25C 1.408(8) . ?
C25C H25G 0.9600 . ?
C25C H25H 0.9600 . ?
C25C H25I 0.9600 . ?
C17B C18B 1.366(14) . ?
C17B C22B 1.379(14) . ?
C18B C19B 1.375(14) . ?
C18B H18B 0.9300 . ?
C19B C20B 1.363(14) . ?
C19B O1B 1.376(16) . ?
O1B C23B 1.410(8) . ?
C23B H23D 0.9600 . ?
C23B H23E 0.9600 . ?
C23B H23F 0.9600 . ?
C20B C21B 1.369(14) . ?
C20B O2B 1.377(15) . ?
O2B C24B 1.411(8) . ?
C24B H24D 0.9600 . ?
C24B H24E 0.9600 . ?
C24B H24F 0.9600 . ?
C21B C22B 1.379(15) . ?
C21B O3B 1.377(16) . ?
O3B C25B 1.408(8) . ?
C25B H25D 0.9600 . ?
C25B H25E 0.9600 . ?
C25B H25F 0.9600 . ?
C22B H22B 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 N1 109.10(16) . . ?
C2 C1 C9 109.70(14) . . ?
N1 C1 C9 141.11(16) . . ?
C4 N1 C1 107.47(14) . . ?
C4 N1 H1N 122.6(14) . . ?
C1 N1 H1N 129.6(15) . . ?
C1 C2 N2 108.98(15) . . ?
C1 C2 C3 109.44(14) . . ?
N2 C2 C3 141.44(15) . . ?
C10 N2 C2 106.89(13) . . ?
C10 N2 C11 126.27(13) . . ?
C2 N2 C11 126.30(14) . . ?
C8 C3 C4 118.78(16) . . ?
C8 C3 C2 137.17(15) . . ?
C4 C3 C2 104.03(15) . . ?
N1 C4 C5 128.51(17) . . ?
N1 C4 C3 109.94(15) . . ?
C5 C4 C3 121.54(18) . . ?
C6 C5 C4 118.09(19) . . ?
C6 C5 H5 121.0 . . ?
C4 C5 H5 121.0 . . ?
C5 C6 C7 121.02(18) . . ?
C5 C6 H6 119.5 . . ?
C7 C6 H6 119.5 . . ?
C8 C7 C6 121.8(2) . . ?
C8 C7 H7 119.1 . . ?
C6 C7 H7 119.1 . . ?
C7 C8 C3 118.70(19) . . ?
C7 C8 H8 120.7 . . ?
C3 C8 H8 120.7 . . ?
C12 C9 C1 136.21(16) . . ?
C12 C9 C10 118.98(16) . . ?
C1 C9 C10 104.69(14) . . ?
C15 C10 N2 128.66(15) . . ?
C15 C10 C9 121.58(16) . . ?
N2 C10 C9 109.68(14) . . ?
C13 C12 C9 119.73(18) . . ?
C13 C12 H12 120.1 . . ?
C9 C12 H12 120.1 . . ?
C12 C13 C14 119.19(18) . . ?
C12 C13 H13 120.4 . . ?
C14 C13 H13 120.4 . . ?
F1 C14 C15 117.54(19) . . ?
F1 C14 C13 118.36(18) . . ?
C15 C14 C13 124.10(18) . . ?
C14 C15 C10 116.38(17) . . ?
C14 C15 H15 121.8 . . ?
C10 C15 H15 121.8 . . ?
C11 C16 H16A 120.0 . . ?
C11 C16 H16B 120.0 . . ?
H16A C16 H16B 120.0 . . ?
C16 C11 N2 120.32(15) . . ?
C16 C11 C17B 130.6(16) . . ?
N2 C11 C17B 107.9(15) . . ?
C16 C11 C17 122.3(3) . . ?
N2 C11 C17 117.3(3) . . ?
C18 C17 C22 120.9(3) . . ?
C18 C17 C11 121.7(3) . . ?
C22 C17 C11 117.2(3) . . ?
C17 C18 C19 118.2(4) . . ?
C17 C18 H18 120.9 . . ?
C19 C18 H18 120.9 . . ?
O1 C19 C20 116.7(3) . . ?
O1 C19 C18 121.8(4) . . ?
C20 C19 C18 121.5(4) . . ?
C19 O1 C23 117.4(5) . . ?
O1 C23 H23A 109.5 . . ?
O1 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
O1 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
O2 C20 C19 115.9(4) . . ?
O2 C20 C21 124.7(4) . . ?
C19 C20 C21 119.3(4) . . ?
C20 O2 C24 114.1(5) . . ?
O2 C24 H24A 109.5 . . ?
O2 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
O2 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C22 C21 C20 119.7(5) . . ?
C21 C22 C17 120.3(4) . . ?
C21 C22 H22 119.9 . . ?
C17 C22 H22 119.9 . . ?
O3 C25 H25A 109.5 . . ?
O3 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
O3 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
O3C C25C H25G 109.5 . . ?
O3C C25C H25H 109.5 . . ?
H25G C25C H25H 109.5 . . ?
O3C C25C H25I 109.5 . . ?
H25G C25C H25I 109.5 . . ?
H25H C25C H25I 109.5 . . ?
C18B C17B C22B 113.5(19) . . ?
C18B C17B C11 104.6(17) . . ?
C22B C17B C11 141(2) . . ?
C17B C18B C19B 128(2) . . ?
C17B C18B H18B 116.2 . . ?
C19B C18B H18B 116.2 . . ?
C20B C19B C18B 113(2) . . ?
C20B C19B O1B 103(2) . . ?
C18B C19B O1B 143(3) . . ?
C19B O1B C23B 125(3) . . ?
O1B C23B H23D 109.5 . . ?
O1B C23B H23E 109.5 . . ?
H23D C23B H23E 109.5 . . ?
O1B C23B H23F 109.5 . . ?
H23D C23B H23F 109.5 . . ?
H23E C23B H23F 109.5 . . ?
C19B C20B C21B 120(2) . . ?
C19B C20B O2B 132(2) . . ?
C21B C20B O2B 108(2) . . ?
C20B O2B C24B 126(3) . . ?
O2B C24B H24D 109.5 . . ?
O2B C24B H24E 109.5 . . ?
H24D C24B H24E 109.5 . . ?
O2B C24B H24F 109.5 . . ?
H24D C24B H24F 109.5 . . ?
H24E C24B H24F 109.5 . . ?
C20B C21B C22B 121(2) . . ?
C20B C21B O3B 132(2) . . ?
C22B C21B O3B 106(2) . . ?
C21B O3B C25B 127(3) . . ?
O3B C25B H25D 109.5 . . ?
O3B C25B H25E 109.5 . . ?
H25D C25B H25E 109.5 . . ?
O3B C25B H25F 109.5 . . ?
H25D C25B H25F 109.5 . . ?
H25E C25B H25F 109.5 . . ?
C17B C22B C21B 119(2) . . ?
C17B C22B H22B 120.3 . . ?
C21B C22B H22B 120.3 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 C1 N1 C4 0.75(19) . . . . ?
C9 C1 N1 C4 176.7(2) . . . . ?
N1 C1 C2 N2 176.31(13) . . . . ?
C9 C1 C2 N2 -0.96(19) . . . . ?
N1 C1 C2 C3 -0.34(19) . . . . ?
C9 C1 C2 C3 -177.61(13) . . . . ?
C1 C2 N2 C10 2.27(18) . . . . ?
C3 C2 N2 C10 177.2(2) . . . . ?
C1 C2 N2 C11 174.26(16) . . . . ?
C3 C2 N2 C11 -10.8(3) . . . . ?
C1 C2 C3 C8 178.4(2) . . . . ?
N2 C2 C3 C8 3.4(4) . . . . ?
C1 C2 C3 C4 -0.19(18) . . . . ?
N2 C2 C3 C4 -175.1(2) . . . . ?
C1 N1 C4 C5 179.11(18) . . . . ?
C1 N1 C4 C3 -0.89(19) . . . . ?
C8 C3 C4 N1 -178.21(16) . . . . ?
C2 C3 C4 N1 0.66(18) . . . . ?
C8 C3 C4 C5 1.8(3) . . . . ?
C2 C3 C4 C5 -179.33(16) . . . . ?
N1 C4 C5 C6 177.49(19) . . . . ?
C3 C4 C5 C6 -2.5(3) . . . . ?
C4 C5 C6 C7 1.8(3) . . . . ?
C5 C6 C7 C8 -0.3(4) . . . . ?
C6 C7 C8 C3 -0.5(3) . . . . ?
C4 C3 C8 C7 -0.3(3) . . . . ?
C2 C3 C8 C7 -178.66(19) . . . . ?
C2 C1 C9 C12 -176.4(2) . . . . ?
N1 C1 C9 C12 7.7(4) . . . . ?
C2 C1 C9 C10 -0.70(18) . . . . ?
N1 C1 C9 C10 -176.6(2) . . . . ?
C2 N2 C10 C15 174.05(17) . . . . ?
C11 N2 C10 C15 2.1(3) . . . . ?
C2 N2 C10 C9 -2.73(18) . . . . ?
C11 N2 C10 C9 -174.73(15) . . . . ?
C12 C9 C10 C15 1.7(3) . . . . ?
C1 C9 C10 C15 -174.92(16) . . . . ?
C12 C9 C10 N2 178.71(15) . . . . ?
C1 C9 C10 N2 2.13(18) . . . . ?
C1 C9 C12 C13 174.29(19) . . . . ?
C10 C9 C12 C13 -0.9(3) . . . . ?
C9 C12 C13 C14 -0.7(3) . . . . ?
C12 C13 C14 F1 -178.60(19) . . . . ?
C12 C13 C14 C15 1.8(3) . . . . ?
F1 C14 C15 C10 179.32(17) . . . . ?
C13 C14 C15 C10 -1.1(3) . . . . ?
N2 C10 C15 C14 -177.12(18) . . . . ?
C9 C10 C15 C14 -0.7(3) . . . . ?
C10 N2 C11 C16 131.16(19) . . . . ?
C2 N2 C11 C16 -39.3(3) . . . . ?
C10 N2 C11 C17B -60.0(17) . . . . ?
C2 N2 C11 C17B 129.5(17) . . . . ?
C10 N2 C11 C17 -52.0(4) . . . . ?
C2 N2 C11 C17 137.5(4) . . . . ?
C16 C11 C17 C18 -34.2(9) . . . . ?
N2 C11 C17 C18 149.1(6) . . . . ?
C16 C11 C17 C22 142.5(5) . . . . ?
N2 C11 C17 C22 -34.3(8) . . . . ?
C22 C17 C18 C19 -0.7(11) . . . . ?
C11 C17 C18 C19 175.8(6) . . . . ?
C17 C18 C19 O1 178.8(7) . . . . ?
C17 C18 C19 C20 -1.8(11) . . . . ?
C20 C19 O1 C23 -173.9(7) . . . . ?
C18 C19 O1 C23 5.5(10) . . . . ?
O1 C19 C20 O2 5.5(11) . . . . ?
C18 C19 C20 O2 -173.9(7) . . . . ?
O1 C19 C20 C21 -178.7(8) . . . . ?
C18 C19 C20 C21 1.9(12) . . . . ?
C19 C20 O2 C24 -117.7(7) . . . . ?
C21 C20 O2 C24 66.7(9) . . . . ?
O2 C20 C21 C22 176.0(7) . . . . ?
C19 C20 C21 C22 0.6(13) . . . . ?
C20 C21 C22 C17 -3.0(12) . . . . ?
C18 C17 C22 C21 3.1(11) . . . . ?
C11 C17 C22 C21 -173.5(7) . . . . ?
C16 C11 C17B C18B -47(4) . . . . ?
N2 C11 C17B C18B 145(3) . . . . ?
C16 C11 C17B C22B 124(5) . . . . ?
N2 C11 C17B C22B -43(7) . . . . ?
C22B C17B C18B C19B -11(7) . . . . ?
C11 C17B C18B C19B 164(4) . . . . ?
C17B C18B C19B C20B 24(7) . . . . ?
C17B C18B C19B O1B -167(6) . . . . ?
C20B C19B O1B C23B 180(4) . . . . ?
C18B C19B O1B C23B 10(10) . . . . ?
C18B C19B C20B C21B -16(7) . . . . ?
O1B C19B C20B C21B 171(5) . . . . ?
C18B C19B C20B O2B 162(5) . . . . ?
O1B C19B C20B O2B -11(7) . . . . ?
C19B C20B O2B C24B 139(5) . . . . ?
C21B C20B O2B C24B -42(6) . . . . ?
C19B C20B C21B C22B -3(8) . . . . ?
O2B C20B C21B C22B 178(4) . . . . ?
C19B C20B C21B O3B 164(5) . . . . ?
O2B C20B C21B O3B -14(7) . . . . ?
C20B C21B O3B C25B -169(5) . . . . ?
C22B C21B O3B C25B 0(6) . . . . ?
C18B C17B C22B C21B -11(6) . . . . ?
C11 C17B C22B C21B 178(5) . . . . ?
C20B C21B C22B C17B 18(7) . . . . ?
O3B C21B C22B C17B -152(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1N O1 0.865(16) 2.34(2) 2.944(6) 127.6(18) 1_645 yes
N1 H1N O2 0.865(16) 2.251(18) 3.069(5) 158(2) 1_645 yes
N1 H1N O1B 0.865(16) 2.42(4) 2.99(4) 123.5(19) 1_645 yes
N1 H1N O2B 0.865(16) 2.28(3) 3.13(3) 167(2) 1_645 yes
C25C H25G F1 0.96 2.35 3.292(17) 165.9 2_666 yes
C24B H24F O3B 0.96 2.08 2.74(3) 124.6 . yes
C25B H25D O3B 0.96 2.07 2.84(6) 136.9 2_666 yes

_refine_diff_density_max         0.290
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.066











_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: diethyl ether'
####################################################################### 
# 
# 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_cmpd_8a_SP596
_database_code_depnum_ccdc_archive 'CCDC 2310243'
loop_
_audit_author_name
_audit_author_address
'Pascal Retailleau'
;ICSN CNRS University Paris Saclay
France
;
_audit_update_record             
;
2023-11-24 deposited with the CCDC.	2024-02-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_chemical_name_systematic        
;
'5-(1-(4-methoxyphenyl)vinyl)-5,6-dihydroindolo[2,3-b]indole'
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H18 N2 O'
_chemical_formula_sum            'C23 H18 N2 O'
_chemical_formula_weight         338.39

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

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

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

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

_cell_length_a                   11.2201(4)
_cell_length_b                   19.8758(7)
_cell_length_c                   16.7325(6)
_cell_angle_alpha                90
_cell_angle_beta                 107.865(4)
_cell_angle_gamma                90
_cell_volume                     3551.6(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    13903
_cell_measurement_theta_min      2.7500
_cell_measurement_theta_max      29.2030

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.266
_exptl_crystal_F_000             1424
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.227
_exptl_crystal_size_mid          0.188
_exptl_crystal_size_min          0.124
_exptl_absorpt_coefficient_mu    0.078
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 5 3 0.0751
-4 5 -3 0.1045
-5 -3 1 0.0618
-3 -5 3 0.0639
2 -5 3 0.0646
2 5 -3 0.0667
5 3 -1 0.0620
-2 0 -5 0.0738
0 -1 -1 0.0898
9 -6 14 0.0719
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.417
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.122a (Rigaku Oxford Diffraction, 2021)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku microsource mm003'
_diffrn_radiation_monochromator  'Rigaku MaxFlux double bounce layer optic'
_diffrn_measurement_specimen_support Fiber
_diffrn_detector                 'HPAD Dectris PILATUS3R 200K-A'
_diffrn_measurement_device       
;
 κ-geometry diffractometer
;
_diffrn_measurement_device_type  
;
Rigaku XtaLabPro AFC12 (Right) goniometer
;
_diffrn_reflns_number            43740
_diffrn_reflns_av_unetI/netI     0.0216
_diffrn_reflns_av_R_equivalents  0.0338
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.558
_diffrn_reflns_theta_max         25.350
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6510
_reflns_number_gt                5191
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2015b)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0333P)²+1.3869P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     other
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6508
_refine_ls_number_parameters     489
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0602
_refine_ls_R_factor_gt           0.0462
_refine_ls_wR_factor_ref         0.1113
_refine_ls_wR_factor_gt          0.1038
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_restrained_S_all      1.076
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.71631(15) 0.36972(9) 0.64385(10) 0.0443(4) Uani 1 1 d . . . . .
N1 N 0.78860(14) 0.35569(8) 0.59388(10) 0.0513(4) Uani 1 1 d . . . . .
H1N H 0.7682(18) 0.3302(10) 0.5483(13) 0.062 Uiso 1 1 d . U . . .
O1 O 0.05898(11) 0.32101(7) 0.41382(8) 0.0613(4) Uani 1 1 d . . . . .
C2 C 0.77512(15) 0.41073(9) 0.71036(10) 0.0443(4) Uani 1 1 d . . . . .
N2 N 0.59480(12) 0.35583(7) 0.63951(9) 0.0457(3) Uani 1 1 d . . . . .
C3 C 0.89657(15) 0.42481(9) 0.70211(10) 0.0451(4) Uani 1 1 d . . . . .
C4 C 0.90163(16) 0.39026(9) 0.62906(11) 0.0488(4) Uani 1 1 d . . . . .
C5 C 1.00403(18) 0.39431(11) 0.60003(13) 0.0619(5) Uani 1 1 d . . . . .
H5 H 1.005636 0.371454 0.551876 0.074 Uiso 1 1 calc R U . . .
C6 C 1.10393(18) 0.43335(12) 0.64473(14) 0.0691(6) Uani 1 1 d . . . . .
H6 H 1.174169 0.436714 0.626566 0.083 Uiso 1 1 calc R U . . .
C7 C 1.10126(18) 0.46761(11) 0.71623(14) 0.0651(6) Uani 1 1 d . . . . .
H7 H 1.169958 0.493487 0.745263 0.078 Uiso 1 1 calc R U . . .
C8 C 0.99881(17) 0.46419(10) 0.74538(12) 0.0544(5) Uani 1 1 d . . . . .
H8 H 0.998041 0.487827 0.793191 0.065 Uiso 1 1 calc R U . . .
C9 C 0.68471(15) 0.42369(8) 0.75360(10) 0.0414(4) Uani 1 1 d . . . . .
C10 C 0.57382(15) 0.38910(8) 0.70839(10) 0.0427(4) Uani 1 1 d . . . . .
C11 C 0.50635(15) 0.31876(8) 0.57511(10) 0.0426(4) Uani 1 1 d . . . . .
C12 C 0.68351(18) 0.45999(9) 0.82469(11) 0.0504(4) Uani 1 1 d . . . . .
H12 H 0.754524 0.483167 0.855955 0.060 Uiso 1 1 calc R U . . .
C13 C 0.57608(18) 0.46117(10) 0.84811(12) 0.0570(5) Uani 1 1 d . . . . .
H13 H 0.575199 0.485814 0.895178 0.068 Uiso 1 1 calc R U . . .
C14 C 0.46912(18) 0.42652(10) 0.80326(12) 0.0574(5) Uani 1 1 d . . . . .
H14 H 0.398225 0.428018 0.820901 0.069 Uiso 1 1 calc R U . . .
C15 C 0.46678(16) 0.38974(9) 0.73252(11) 0.0503(4) Uani 1 1 d . . . . .
H15 H 0.395488 0.366269 0.702306 0.060 Uiso 1 1 calc R U . . .
C16 C 0.53577(19) 0.25771(10) 0.55682(14) 0.0555(5) Uani 1 1 d . . . . .
H16A H 0.6128(19) 0.2347(10) 0.5905(12) 0.067 Uiso 1 1 d . U . . .
H16B H 0.4771(19) 0.2335(10) 0.5092(13) 0.067 Uiso 1 1 d . U . . .
C17 C 0.39028(15) 0.35507(8) 0.52913(10) 0.0421(4) Uani 1 1 d . . . . .
C18 C 0.39156(17) 0.42365(9) 0.51555(11) 0.0494(4) Uani 1 1 d . . . . .
H18 H 0.464828 0.448075 0.538404 0.059 Uiso 1 1 calc R U . . .
C19 C 0.28391(19) 0.45597(10) 0.46799(12) 0.0573(5) Uani 1 1 d . . . . .
H19 H 0.285594 0.502038 0.458656 0.069 Uiso 1 1 calc R U . . .
C20 C 0.17466(18) 0.42078(10) 0.43445(12) 0.0553(5) Uani 1 1 d . . . . .
H20 H 0.102742 0.442748 0.402284 0.066 Uiso 1 1 calc R U . . .
C21 C 0.17257(16) 0.35263(9) 0.44889(10) 0.0476(4) Uani 1 1 d . . . . .
C22 C 0.27919(15) 0.31939(9) 0.49627(10) 0.0451(4) Uani 1 1 d . . . . .
H22 H 0.276661 0.273440 0.506125 0.054 Uiso 1 1 calc R U . . .
C23 C 0.0479(2) 0.25274(12) 0.43584(18) 0.0879(8) Uani 1 1 d . . . . .
H23A H -0.035470 0.237070 0.407939 0.132 Uiso 1 1 calc R U . . .
H23B H 0.064638 0.249271 0.495508 0.132 Uiso 1 1 calc R U . . .
H23C H 0.106963 0.225772 0.418956 0.132 Uiso 1 1 calc R U . . .
C1B C 0.05432(16) 0.34085(10) 0.18111(11) 0.0520(4) Uani 1 1 d . . . . .
N1B N -0.01798(14) 0.32883(9) 0.23156(10) 0.0583(4) Uani 1 1 d . . . . .
H1NB H 0.0087(19) 0.3178(10) 0.2871(14) 0.070 Uiso 1 1 d . U . . .
O1B O 0.71072(11) 0.28365(6) 0.41948(8) 0.0571(3) Uani 1 1 d . . . . .
C2B C -0.00766(16) 0.37472(9) 0.10884(10) 0.0483(4) Uani 1 1 d . . . . .
N2B N 0.17750(13) 0.32845(8) 0.18768(9) 0.0538(4) Uani 1 1 d . . . . .
C3B C -0.13210(15) 0.38659(9) 0.11421(10) 0.0454(4) Uani 1 1 d . . . . .
C4B C -0.13393(16) 0.35849(9) 0.19123(11) 0.0499(4) Uani 1 1 d . . . . .
C5B C -0.23795(17) 0.36215(10) 0.21886(12) 0.0575(5) Uani 1 1 d . . . . .
H5B H -0.237485 0.343096 0.269717 0.069 Uiso 1 1 calc R U . . .
C6B C -0.34252(17) 0.39500(10) 0.16851(13) 0.0599(5) Uani 1 1 d . . . . .
H6B H -0.413396 0.398770 0.185910 0.072 Uiso 1 1 calc R U . . .
C7B C -0.34286(17) 0.42237(10) 0.09243(13) 0.0591(5) Uani 1 1 d . . . . .
H7B H -0.414652 0.443877 0.059288 0.071 Uiso 1 1 calc R U . . .
C8B C -0.23955(16) 0.41862(9) 0.06442(12) 0.0517(4) Uani 1 1 d . . . . .
H8B H -0.241658 0.437217 0.012998 0.062 Uiso 1 1 calc R U . . .
C9B C 0.08126(16) 0.38491(9) 0.06430(10) 0.0457(4) Uani 1 1 d . . . . .
C10B C 0.19560(16) 0.35552(9) 0.11447(10) 0.0465(4) Uani 1 1 d . . . . .
C11B C 0.26440(16) 0.29073(10) 0.25306(11) 0.0504(4) Uani 1 1 d . . . . .
C12B C 0.07886(18) 0.41383(9) -0.01179(11) 0.0535(5) Uani 1 1 d . . . . .
H12B H 0.005839 0.433676 -0.045824 0.064 Uiso 1 1 calc R U . . .
C13B C 0.18528(19) 0.41296(10) -0.03664(12) 0.0586(5) Uani 1 1 d . . . . .
H13B H 0.183415 0.432448 -0.087538 0.070 Uiso 1 1 calc R U . . .
C14B C 0.29517(18) 0.38343(10) 0.01320(12) 0.0568(5) Uani 1 1 d . . . . .
H14B H 0.365494 0.383198 -0.005113 0.068 Uiso 1 1 calc R U . . .
C15B C 0.30190(16) 0.35442(10) 0.08937(11) 0.0520(4) Uani 1 1 d . . . . .
H15B H 0.375620 0.334781 0.122726 0.062 Uiso 1 1 calc R U . . .
C16B C 0.2301(2) 0.23185(12) 0.27446(16) 0.0702(6) Uani 1 1 d . . . . .
H16C H 0.149(2) 0.2108(12) 0.2452(14) 0.084 Uiso 1 1 d . U . . .
H16D H 0.287(2) 0.2078(12) 0.3233(15) 0.084 Uiso 1 1 d . U . . .
C17B C 0.38538(16) 0.32449(9) 0.29493(10) 0.0447(4) Uani 1 1 d . . . . .
C18B C 0.39380(18) 0.39376(9) 0.29844(11) 0.0519(4) Uani 1 1 d . . . . .
H18B H 0.323597 0.419803 0.272832 0.062 Uiso 1 1 calc R U . . .
C19B C 0.50603(19) 0.42449(9) 0.33982(11) 0.0560(5) Uani 1 1 d . . . . .
H19B H 0.511297 0.471198 0.340963 0.067 Uiso 1 1 calc R U . . .
C20B C 0.61015(18) 0.38682(9) 0.37938(11) 0.0519(4) Uani 1 1 d . . . . .
H20B H 0.685289 0.407861 0.407673 0.062 Uiso 1 1 calc R U . . .
C21B C 0.60226(15) 0.31724(9) 0.37678(10) 0.0447(4) Uani 1 1 d . . . . .
C22B C 0.49169(16) 0.28593(9) 0.33350(10) 0.0458(4) Uani 1 1 d . . . . .
H22B H 0.487817 0.239247 0.329965 0.055 Uiso 1 1 calc R U . . .
C23B C 0.71094(19) 0.21224(10) 0.41202(16) 0.0726(6) Uani 1 1 d . . . . .
H23D H 0.698664 0.200169 0.354493 0.109 Uiso 1 1 calc R U . . .
H23E H 0.644538 0.193654 0.430104 0.109 Uiso 1 1 calc R U . . .
H23F H 0.789775 0.194795 0.446419 0.109 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.360(2) . ?
C1 N2 1.371(2) . ?
C1 C2 1.374(2) . ?
N1 C4 1.403(2) . ?
N1 H1N 0.89(2) . ?
O1 C21 1.380(2) . ?
O1 C23 1.422(3) . ?
C2 C9 1.438(2) . ?
C2 C3 1.439(2) . ?
N2 C10 1.410(2) . ?
N2 C11 1.426(2) . ?
C3 C8 1.394(2) . ?
C3 C4 1.418(2) . ?
C4 C5 1.380(3) . ?
C5 C6 1.380(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.385(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.381(3) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
C9 C12 1.395(2) . ?
C9 C10 1.420(2) . ?
C10 C15 1.380(2) . ?
C11 C16 1.318(3) . ?
C11 C17 1.481(2) . ?
C12 C13 1.377(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.387(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.385(3) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 H16A 0.99(2) . ?
C16 H16B 0.99(2) . ?
C17 C18 1.383(2) . ?
C17 C22 1.392(2) . ?
C18 C19 1.384(2) . ?
C18 H18 0.9300 . ?
C19 C20 1.373(3) . ?
C19 H19 0.9300 . ?
C20 C21 1.377(3) . ?
C20 H20 0.9300 . ?
C21 C22 1.383(2) . ?
C22 H22 0.9300 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C1B N1B 1.359(2) . ?
C1B C2B 1.372(2) . ?
C1B N2B 1.375(2) . ?
N1B C4B 1.399(2) . ?
N1B H1NB 0.91(2) . ?
O1B C21B 1.3798(19) . ?
O1B C23B 1.425(2) . ?
C2B C9B 1.431(2) . ?
C2B C3B 1.446(2) . ?
N2B C10B 1.408(2) . ?
N2B C11B 1.434(2) . ?
C3B C8B 1.392(2) . ?
C3B C4B 1.411(2) . ?
C4B C5B 1.383(2) . ?
C5B C6B 1.381(3) . ?
C5B H5B 0.9300 . ?
C6B C7B 1.383(3) . ?
C6B H6B 0.9300 . ?
C7B C8B 1.379(3) . ?
C7B H7B 0.9300 . ?
C8B H8B 0.9300 . ?
C9B C12B 1.390(2) . ?
C9B C10B 1.425(2) . ?
C10B C15B 1.381(2) . ?
C11B C16B 1.315(3) . ?
C11B C17B 1.483(2) . ?
C12B C13B 1.380(3) . ?
C12B H12B 0.9300 . ?
C13B C14B 1.389(3) . ?
C13B H13B 0.9300 . ?
C14B C15B 1.380(3) . ?
C14B H14B 0.9300 . ?
C15B H15B 0.9300 . ?
C16B H16C 0.98(2) . ?
C16B H16D 0.99(2) . ?
C17B C18B 1.380(2) . ?
C17B C22B 1.398(2) . ?
C18B C19B 1.380(3) . ?
C18B H18B 0.9300 . ?
C19B C20B 1.374(3) . ?
C19B H19B 0.9300 . ?
C20B C21B 1.386(2) . ?
C20B H20B 0.9300 . ?
C21B C22B 1.378(2) . ?
C22B H22B 0.9300 . ?
C23B H23D 0.9600 . ?
C23B H23E 0.9600 . ?
C23B H23F 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
N1 C1 N2 134.17(15) . . ?
N1 C1 C2 112.99(15) . . ?
N2 C1 C2 112.65(15) . . ?
C1 N1 C4 105.93(15) . . ?
C1 N1 H1N 126.9(13) . . ?
C4 N1 H1N 127.1(13) . . ?
C21 O1 C23 117.86(14) . . ?
C1 C2 C9 106.02(14) . . ?
C1 C2 C3 105.74(15) . . ?
C9 C2 C3 148.03(16) . . ?
C1 N2 C10 105.96(13) . . ?
C1 N2 C11 126.48(14) . . ?
C10 N2 C11 127.46(14) . . ?
C8 C3 C4 118.39(17) . . ?
C8 C3 C2 135.40(17) . . ?
C4 C3 C2 106.15(14) . . ?
C5 C4 N1 128.60(17) . . ?
C5 C4 C3 122.19(17) . . ?
N1 C4 C3 109.18(15) . . ?
C6 C5 C4 117.88(19) . . ?
C6 C5 H5 121.1 . . ?
C4 C5 H5 121.1 . . ?
C5 C6 C7 121.03(19) . . ?
C5 C6 H6 119.5 . . ?
C7 C6 H6 119.5 . . ?
C8 C7 C6 121.45(19) . . ?
C8 C7 H7 119.3 . . ?
C6 C7 H7 119.3 . . ?
C7 C8 C3 119.05(19) . . ?
C7 C8 H8 120.5 . . ?
C3 C8 H8 120.5 . . ?
C12 C9 C10 117.95(16) . . ?
C12 C9 C2 135.59(16) . . ?
C10 C9 C2 106.46(14) . . ?
C15 C10 N2 128.48(16) . . ?
C15 C10 C9 122.61(16) . . ?
N2 C10 C9 108.90(14) . . ?
C16 C11 N2 119.04(16) . . ?
C16 C11 C17 124.81(16) . . ?
N2 C11 C17 115.98(14) . . ?
C13 C12 C9 119.32(17) . . ?
C13 C12 H12 120.3 . . ?
C9 C12 H12 120.3 . . ?
C12 C13 C14 121.66(18) . . ?
C12 C13 H13 119.2 . . ?
C14 C13 H13 119.2 . . ?
C15 C14 C13 120.73(18) . . ?
C15 C14 H14 119.6 . . ?
C13 C14 H14 119.6 . . ?
C10 C15 C14 117.72(17) . . ?
C10 C15 H15 121.1 . . ?
C14 C15 H15 121.1 . . ?
C11 C16 H16A 122.1(12) . . ?
C11 C16 H16B 118.9(12) . . ?
H16A C16 H16B 119.0(16) . . ?
C18 C17 C22 119.37(16) . . ?
C18 C17 C11 120.92(15) . . ?
C22 C17 C11 119.66(15) . . ?
C17 C18 C19 120.06(17) . . ?
C17 C18 H18 120.0 . . ?
C19 C18 H18 120.0 . . ?
C20 C19 C18 120.72(17) . . ?
C20 C19 H19 119.6 . . ?
C18 C19 H19 119.6 . . ?
C19 C20 C21 119.36(17) . . ?
C19 C20 H20 120.3 . . ?
C21 C20 H20 120.3 . . ?
C20 C21 O1 115.87(15) . . ?
C20 C21 C22 120.79(17) . . ?
O1 C21 C22 123.34(16) . . ?
C21 C22 C17 119.67(16) . . ?
C21 C22 H22 120.2 . . ?
C17 C22 H22 120.2 . . ?
O1 C23 H23A 109.5 . . ?
O1 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
O1 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
N1B C1B C2B 113.32(16) . . ?
N1B C1B N2B 134.09(17) . . ?
C2B C1B N2B 112.56(17) . . ?
C1B N1B C4B 105.68(15) . . ?
C1B N1B H1NB 127.1(13) . . ?
C4B N1B H1NB 124.0(13) . . ?
C21B O1B C23B 117.49(14) . . ?
C1B C2B C9B 106.42(15) . . ?
C1B C2B C3B 105.26(16) . . ?
C9B C2B C3B 148.22(16) . . ?
C1B N2B C10B 105.76(14) . . ?
C1B N2B C11B 125.91(16) . . ?
C10B N2B C11B 128.14(15) . . ?
C8B C3B C4B 118.39(16) . . ?
C8B C3B C2B 135.50(17) . . ?
C4B C3B C2B 106.09(15) . . ?
C5B C4B N1B 128.05(18) . . ?
C5B C4B C3B 122.34(17) . . ?
N1B C4B C3B 109.61(15) . . ?
C6B C5B C4B 117.86(19) . . ?
C6B C5B H5B 121.1 . . ?
C4B C5B H5B 121.1 . . ?
C5B C6B C7B 120.63(18) . . ?
C5B C6B H6B 119.7 . . ?
C7B C6B H6B 119.7 . . ?
C8B C7B C6B 121.74(18) . . ?
C8B C7B H7B 119.1 . . ?
C6B C7B H7B 119.1 . . ?
C7B C8B C3B 119.03(18) . . ?
C7B C8B H8B 120.5 . . ?
C3B C8B H8B 120.5 . . ?
C12B C9B C10B 118.05(16) . . ?
C12B C9B C2B 135.65(16) . . ?
C10B C9B C2B 106.29(15) . . ?
C15B C10B N2B 128.83(16) . . ?
C15B C10B C9B 122.18(17) . . ?
N2B C10B C9B 108.97(15) . . ?
C16B C11B N2B 119.07(18) . . ?
C16B C11B C17B 125.13(17) . . ?
N2B C11B C17B 115.70(16) . . ?
C13B C12B C9B 119.71(17) . . ?
C13B C12B H12B 120.1 . . ?
C9B C12B H12B 120.1 . . ?
C12B C13B C14B 121.02(18) . . ?
C12B C13B H13B 119.5 . . ?
C14B C13B H13B 119.5 . . ?
C15B C14B C13B 121.21(18) . . ?
C15B C14B H14B 119.4 . . ?
C13B C14B H14B 119.4 . . ?
C14B C15B C10B 117.83(17) . . ?
C14B C15B H15B 121.1 . . ?
C10B C15B H15B 121.1 . . ?
C11B C16B H16C 123.1(13) . . ?
C11B C16B H16D 119.0(13) . . ?
H16C C16B H16D 117.8(19) . . ?
C18B C17B C22B 119.32(16) . . ?
C18B C17B C11B 120.81(16) . . ?
C22B C17B C11B 119.85(15) . . ?
C19B C18B C17B 120.20(17) . . ?
C19B C18B H18B 119.9 . . ?
C17B C18B H18B 119.9 . . ?
C20B C19B C18B 120.70(17) . . ?
C20B C19B H19B 119.6 . . ?
C18B C19B H19B 119.6 . . ?
C19B C20B C21B 119.47(17) . . ?
C19B C20B H20B 120.3 . . ?
C21B C20B H20B 120.3 . . ?
C22B C21B O1B 124.22(15) . . ?
C22B C21B C20B 120.38(16) . . ?
O1B C21B C20B 115.40(15) . . ?
C21B C22B C17B 119.87(16) . . ?
C21B C22B H22B 120.1 . . ?
C17B C22B H22B 120.1 . . ?
O1B C23B H23D 109.5 . . ?
O1B C23B H23E 109.5 . . ?
H23D C23B H23E 109.5 . . ?
O1B C23B H23F 109.5 . . ?
H23D C23B H23F 109.5 . . ?
H23E C23B H23F 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N2 C1 N1 C4 173.91(19) . . . . ?
C2 C1 N1 C4 -0.7(2) . . . . ?
N1 C1 C2 C9 176.80(14) . . . . ?
N2 C1 C2 C9 0.97(19) . . . . ?
N1 C1 C2 C3 0.4(2) . . . . ?
N2 C1 C2 C3 -175.43(14) . . . . ?
N1 C1 N2 C10 -175.61(19) . . . . ?
C2 C1 N2 C10 -0.96(19) . . . . ?
N1 C1 N2 C11 0.8(3) . . . . ?
C2 C1 N2 C11 175.49(15) . . . . ?
C1 C2 C3 C8 177.02(19) . . . . ?
C9 C2 C3 C8 3.6(4) . . . . ?
C1 C2 C3 C4 0.09(18) . . . . ?
C9 C2 C3 C4 -173.4(2) . . . . ?
C1 N1 C4 C5 -177.39(19) . . . . ?
C1 N1 C4 C3 0.76(19) . . . . ?
C8 C3 C4 C5 0.2(3) . . . . ?
C2 C3 C4 C5 177.76(17) . . . . ?
C8 C3 C4 N1 -178.08(15) . . . . ?
C2 C3 C4 N1 -0.53(19) . . . . ?
N1 C4 C5 C6 178.19(19) . . . . ?
C3 C4 C5 C6 0.2(3) . . . . ?
C4 C5 C6 C7 -0.3(3) . . . . ?
C5 C6 C7 C8 -0.2(3) . . . . ?
C6 C7 C8 C3 0.6(3) . . . . ?
C4 C3 C8 C7 -0.6(3) . . . . ?
C2 C3 C8 C7 -177.29(19) . . . . ?
C1 C2 C9 C12 179.34(18) . . . . ?
C3 C2 C9 C12 -7.2(4) . . . . ?
C1 C2 C9 C10 -0.57(18) . . . . ?
C3 C2 C9 C10 172.9(3) . . . . ?
C1 N2 C10 C15 -178.76(17) . . . . ?
C11 N2 C10 C15 4.8(3) . . . . ?
C1 N2 C10 C9 0.55(18) . . . . ?
C11 N2 C10 C9 -175.85(15) . . . . ?
C12 C9 C10 C15 -0.6(2) . . . . ?
C2 C9 C10 C15 179.37(15) . . . . ?
C12 C9 C10 N2 -179.91(14) . . . . ?
C2 C9 C10 N2 0.02(18) . . . . ?
C1 N2 C11 C16 54.7(2) . . . . ?
C10 N2 C11 C16 -129.66(19) . . . . ?
C1 N2 C11 C17 -120.85(18) . . . . ?
C10 N2 C11 C17 54.8(2) . . . . ?
C10 C9 C12 C13 -0.2(2) . . . . ?
C2 C9 C12 C13 179.91(18) . . . . ?
C9 C12 C13 C14 0.7(3) . . . . ?
C12 C13 C14 C15 -0.5(3) . . . . ?
N2 C10 C15 C14 179.99(16) . . . . ?
C9 C10 C15 C14 0.8(3) . . . . ?
C13 C14 C15 C10 -0.2(3) . . . . ?
C16 C11 C17 C18 -142.69(19) . . . . ?
N2 C11 C17 C18 32.5(2) . . . . ?
C16 C11 C17 C22 34.8(3) . . . . ?
N2 C11 C17 C22 -149.96(15) . . . . ?
C22 C17 C18 C19 -1.6(3) . . . . ?
C11 C17 C18 C19 175.98(16) . . . . ?
C17 C18 C19 C20 0.6(3) . . . . ?
C18 C19 C20 C21 0.4(3) . . . . ?
C19 C20 C21 O1 179.33(17) . . . . ?
C19 C20 C21 C22 -0.4(3) . . . . ?
C23 O1 C21 C20 -172.1(2) . . . . ?
C23 O1 C21 C22 7.6(3) . . . . ?
C20 C21 C22 C17 -0.6(3) . . . . ?
O1 C21 C22 C17 179.74(16) . . . . ?
C18 C17 C22 C21 1.6(3) . . . . ?
C11 C17 C22 C21 -176.01(15) . . . . ?
C2B C1B N1B C4B -1.9(2) . . . . ?
N2B C1B N1B C4B 175.6(2) . . . . ?
N1B C1B C2B C9B 178.48(16) . . . . ?
N2B C1B C2B C9B 0.4(2) . . . . ?
N1B C1B C2B C3B 1.0(2) . . . . ?
N2B C1B C2B C3B -177.04(15) . . . . ?
N1B C1B N2B C10B -178.1(2) . . . . ?
C2B C1B N2B C10B -0.6(2) . . . . ?
N1B C1B N2B C11B 6.5(3) . . . . ?
C2B C1B N2B C11B -176.03(17) . . . . ?
C1B C2B C3B C8B 178.5(2) . . . . ?
C9B C2B C3B C8B 3.1(4) . . . . ?
C1B C2B C3B C4B 0.31(19) . . . . ?
C9B C2B C3B C4B -175.1(3) . . . . ?
C1B N1B C4B C5B -177.49(19) . . . . ?
C1B N1B C4B C3B 2.0(2) . . . . ?
C8B C3B C4B C5B -0.5(3) . . . . ?
C2B C3B C4B C5B 178.09(17) . . . . ?
C8B C3B C4B N1B 179.98(16) . . . . ?
C2B C3B C4B N1B -1.5(2) . . . . ?
N1B C4B C5B C6B 179.13(18) . . . . ?
C3B C4B C5B C6B -0.3(3) . . . . ?
C4B C5B C6B C7B 0.9(3) . . . . ?
C5B C6B C7B C8B -0.7(3) . . . . ?
C6B C7B C8B C3B -0.2(3) . . . . ?
C4B C3B C8B C7B 0.7(3) . . . . ?
C2B C3B C8B C7B -177.31(19) . . . . ?
C1B C2B C9B C12B 178.5(2) . . . . ?
C3B C2B C9B C12B -6.1(5) . . . . ?
C1B C2B C9B C10B -0.07(19) . . . . ?
C3B C2B C9B C10B 175.3(3) . . . . ?
C1B N2B C10B C15B -177.80(18) . . . . ?
C11B N2B C10B C15B -2.5(3) . . . . ?
C1B N2B C10B C9B 0.54(19) . . . . ?
C11B N2B C10B C9B 175.83(17) . . . . ?
C12B C9B C10B C15B -0.7(3) . . . . ?
C2B C9B C10B C15B 178.18(16) . . . . ?
C12B C9B C10B N2B -179.16(16) . . . . ?
C2B C9B C10B N2B -0.29(19) . . . . ?
C1B N2B C11B C16B 47.9(3) . . . . ?
C10B N2B C11B C16B -126.5(2) . . . . ?
C1B N2B C11B C17B -128.50(19) . . . . ?
C10B N2B C11B C17B 57.1(2) . . . . ?
C10B C9B C12B C13B 0.4(3) . . . . ?
C2B C9B C12B C13B -178.05(19) . . . . ?
C9B C12B C13B C14B 0.2(3) . . . . ?
C12B C13B C14B C15B -0.5(3) . . . . ?
C13B C14B C15B C10B 0.2(3) . . . . ?
N2B C10B C15B C14B 178.54(18) . . . . ?
C9B C10B C15B C14B 0.4(3) . . . . ?
C16B C11B C17B C18B -149.2(2) . . . . ?
N2B C11B C17B C18B 27.0(2) . . . . ?
C16B C11B C17B C22B 29.0(3) . . . . ?
N2B C11B C17B C22B -154.85(16) . . . . ?
C22B C17B C18B C19B -0.2(3) . . . . ?
C11B C17B C18B C19B 178.00(16) . . . . ?
C17B C18B C19B C20B -1.2(3) . . . . ?
C18B C19B C20B C21B 0.7(3) . . . . ?
C23B O1B C21B C22B 5.7(3) . . . . ?
C23B O1B C21B C20B -174.13(18) . . . . ?
C19B C20B C21B C22B 1.3(3) . . . . ?
C19B C20B C21B O1B -178.87(16) . . . . ?
O1B C21B C22B C17B 177.49(16) . . . . ?
C20B C21B C22B C17B -2.7(3) . . . . ?
C18B C17B C22B C21B 2.1(3) . . . . ?
C11B C17B C22B C21B -176.07(16) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1N O1B 0.89(2) 2.25(2) 3.125(2) 169.3(18) . yes
N1B H1NB O1 0.91(2) 2.02(2) 2.908(2) 163.9(19) . yes

_refine_diff_density_max         0.149
_refine_diff_density_min         -0.144
_refine_diff_density_rms         0.029





