# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2014

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#                                CCDC 
# 
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# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
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data_is_1h003
_audit_creation_method           SHELXL-97

#==============================================================================

# CHEMICAL DATA

_chemical_name_systematic        
;
5-(4-(tert-Butyl)phenyl)-10-methyl-5,10-dihydroindolo[3,2-b]indole
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H24 N2'
_chemical_formula_sum            'C25 H24 N2'
_chemical_formula_weight         352.46

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'

#==============================================================================

# CRYSTAL DATA

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14

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

_cell_length_a                   9.8957(3)
_cell_length_b                   23.4982(7)
_cell_length_c                   8.5844(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.811(2)
_cell_angle_gamma                90.00
_cell_volume                     1938.43(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    4520
_cell_measurement_theta_min      5.477
_cell_measurement_theta_max      59.975

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.208
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             752
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9737
_exptl_absorpt_correction_T_max  0.9902
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2004)'

#==============================================================================

# EXPERIMENTAL DATA

_exptl_special_details           ?

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker-Nonius Apex X8-CCD-diffractometer'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            27546
_diffrn_reflns_av_R_equivalents  0.0494
_diffrn_reflns_av_sigmaI/netI    0.0539
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.96
_diffrn_reflns_theta_max         30.08
_reflns_number_total             5629
_reflns_number_gt                3510
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'Bruker Apex V7.51A'
_computing_cell_refinement       'Bruker Apex V7.51A'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP-3v2.01 (Farrugia, 1997)'
_computing_publication_material  SHELXL-97

#==============================================================================

# REFINEMENT DATA 

_refine_special_details          
;
 All H atoms were positioned geometrically and refined using a riding model, 
 with C---H = 0.98 (methyl groups), 0.99Å (methylene groups), 
 1.00Å (methine groups) or 0.95 Å (aryl CH) and with Uiso(H) = 
 1.5 times Ueq(C) (methyl groups) or with Uiso(H) = 1.2 times 
 Ueq(C) (methylene  groups, aryl CH, methine groups). Torsion angles 
 of all methyl groups (except C15b/C23b/C24b/C25b) were allowed to refine.
 The geometry of the minor part of the disordered molecule was restrained to be 
 equal to the major part within an esd of 0.01. The Uij of all atoms were 
 restrained to be equal in both parts.
 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0536P)²+0.3631P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_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         5629
_refine_ls_number_parameters     294
_refine_ls_number_restraints     80
_refine_ls_R_factor_all          0.0971
_refine_ls_R_factor_gt           0.0507
_refine_ls_wR_factor_ref         0.1326
_refine_ls_wR_factor_gt          0.1115
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.029
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

#==============================================================================

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1A N -0.19372(14) 0.19473(5) 1.20516(15) 0.0275(3) Uani 0.9524(12) 1 d PD A 1
C1A C -0.05532(16) 0.18287(6) 1.21211(17) 0.0244(3) Uani 0.9524(12) 1 d PD A 1
C2A C -0.04612(16) 0.15133(6) 1.08019(17) 0.0238(3) Uani 0.9524(12) 1 d PD A 1
N2A N 0.09126(13) 0.13735(5) 1.08984(13) 0.0247(3) Uani 0.9524(12) 1 d PD A 1
C3A C -0.18216(16) 0.14174(8) 0.9832(2) 0.0255(3) Uani 0.9524(12) 1 d PD A 1
C4A C -0.27195(17) 0.16959(8) 1.0666(2) 0.0277(4) Uani 0.9524(12) 1 d PD A 1
C5A C -0.41544(18) 0.16992(8) 1.0064(2) 0.0353(4) Uani 0.9524(12) 1 d PD A 1
H5A H -0.4749 0.1883 1.0628 0.042 Uiso 0.9524(12) 1 calc PR A 1
C6A C -0.46892(19) 0.14280(8) 0.8625(2) 0.0404(4) Uani 0.9524(12) 1 d PD A 1
H6A H -0.5668 0.1425 0.8197 0.048 Uiso 0.9524(12) 1 calc PR A 1
C7A C -0.3826(2) 0.11577(8) 0.7783(2) 0.0396(4) Uani 0.9524(12) 1 d PD A 1
H7A H -0.4228 0.0978 0.6789 0.048 Uiso 0.9524(12) 1 calc PR A 1
C8A C -0.24060(17) 0.11470(8) 0.83673(19) 0.0315(4) Uani 0.9524(12) 1 d PD A 1
H8A H -0.1829 0.0960 0.7789 0.038 Uiso 0.9524(12) 1 calc PR A 1
C9A C 0.08090(16) 0.19023(6) 1.31296(17) 0.0243(3) Uani 0.9524(12) 1 d PD A 1
C10A C 0.16986(17) 0.16069(6) 1.23223(16) 0.0234(3) Uani 0.9524(12) 1 d PD A 1
C11A C 0.31305(17) 0.15902(7) 1.29303(18) 0.0284(3) Uani 0.9524(12) 1 d PD A 1
H11A H 0.3717 0.1394 1.2381 0.034 Uiso 0.9524(12) 1 calc PR A 1
C12A C 0.36749(19) 0.18689(8) 1.4363(2) 0.0345(4) Uani 0.9524(12) 1 d PD A 1
H12A H 0.4652 0.1863 1.4803 0.041 Uiso 0.9524(12) 1 calc PR A 1
C13A C 0.2818(2) 0.21599(8) 1.5178(2) 0.0360(4) Uani 0.9524(12) 1 d PD A 1
H13A H 0.3221 0.2346 1.6163 0.043 Uiso 0.9524(12) 1 calc PR A 1
C14A C 0.14029(19) 0.21810(7) 1.45775(18) 0.0308(4) Uani 0.9524(12) 1 d PD A 1
H14A H 0.0831 0.2382 1.5136 0.037 Uiso 0.9524(12) 1 calc PR A 1
C15A C -0.2485(2) 0.22296(8) 1.3267(2) 0.0432(5) Uani 0.9524(12) 1 d PD A 1
H15A H -0.2982 0.1953 1.3779 0.065 Uiso 0.9524(12) 1 calc PR A 1
H15B H -0.3127 0.2532 1.2770 0.065 Uiso 0.9524(12) 1 calc PR A 1
H15C H -0.1717 0.2396 1.4077 0.065 Uiso 0.9524(12) 1 calc PR A 1
C16A C 0.14038(15) 0.10229(6) 0.97965(16) 0.0234(3) Uani 0.9524(12) 1 d PD A 1
C17A C 0.12844(17) 0.12000(6) 0.82382(17) 0.0262(3) Uani 0.9524(12) 1 d PD A 1
H17A H 0.0912 0.1565 0.7908 0.031 Uiso 0.9524(12) 1 calc PR A 1
C18A C 0.1708(2) 0.08451(7) 0.7149(2) 0.0252(4) Uani 0.9524(12) 1 d PD A 1
H18A H 0.1608 0.0971 0.6076 0.030 Uiso 0.9524(12) 1 calc PR A 1
C19A C 0.22713(15) 0.03119(7) 0.75890(18) 0.0221(4) Uani 0.9524(12) 1 d PD A 1
C20A C 0.2400(2) 0.01474(7) 0.91773(18) 0.0395(5) Uani 0.9524(12) 1 d PD A 1
H20A H 0.2794 -0.0213 0.9522 0.047 Uiso 0.9524(12) 1 calc PR A 1
C21A C 0.1969(2) 0.04956(7) 1.02655(18) 0.0403(5) Uani 0.9524(12) 1 d PD A 1
H21A H 0.2064 0.0371 1.1339 0.048 Uiso 0.9524(12) 1 calc PR A 1
C22A C 0.2711(2) -0.00984(9) 0.6417(2) 0.0247(3) Uani 0.9524(12) 1 d PD A 1
C23A C 0.1667(3) -0.05924(12) 0.6066(4) 0.0389(5) Uani 0.9524(12) 1 d PD A 1
H23A H 0.1622 -0.0778 0.7075 0.058 Uiso 0.9524(12) 1 calc PR A 1
H23B H 0.1968 -0.0869 0.5364 0.058 Uiso 0.9524(12) 1 calc PR A 1
H23C H 0.0745 -0.0446 0.5536 0.058 Uiso 0.9524(12) 1 calc PR A 1
C24A C 0.2744(3) 0.01923(12) 0.4832(2) 0.0360(6) Uani 0.9524(12) 1 d PD A 1
H24A H 0.1807 0.0325 0.4306 0.054 Uiso 0.9524(12) 1 calc PR A 1
H24B H 0.3064 -0.0079 0.4132 0.054 Uiso 0.9524(12) 1 calc PR A 1
H24C H 0.3381 0.0518 0.5043 0.054 Uiso 0.9524(12) 1 calc PR A 1
C25A C 0.4160(2) -0.03362(9) 0.7166(2) 0.0403(5) Uani 0.9524(12) 1 d PD A 1
H25A H 0.4823 -0.0021 0.7447 0.060 Uiso 0.9524(12) 1 calc PR A 1
H25B H 0.4451 -0.0588 0.6396 0.060 Uiso 0.9524(12) 1 calc PR A 1
H25C H 0.4133 -0.0552 0.8136 0.060 Uiso 0.9524(12) 1 calc PR A 1
N1B N -0.0675(15) 0.1997(7) 1.3432(16) 0.0247(3) Uani 0.0476(12) 1 d PD A 2
C1B C -0.1176(15) 0.1791(13) 1.189(2) 0.0238(3) Uani 0.0476(12) 1 d PD A 2
C2B C -0.0092(16) 0.1547(13) 1.139(2) 0.0244(3) Uani 0.0476(12) 1 d PD A 2
N2B N -0.0523(15) 0.1301(8) 0.9890(18) 0.0275(3) Uani 0.0476(12) 1 d PD A 2
C3B C 0.1172(15) 0.1706(10) 1.250(2) 0.0277(4) Uani 0.0476(12) 1 d PGD A 2
C4B C 0.0768(15) 0.1982(10) 1.375(2) 0.0255(3) Uani 0.0476(12) 1 d PGD A 2
C5B C 0.177(2) 0.2164(13) 1.508(2) 0.0315(4) Uani 0.0476(12) 1 d PGD A 2
H5B H 0.1490 0.2353 1.5934 0.038 Uiso 0.0476(12) 1 calc PR A 2
C6B C 0.3169(19) 0.2071(16) 1.517(3) 0.0396(4) Uani 0.0476(12) 1 d PGD A 2
H6B H 0.3852 0.2196 1.6080 0.048 Uiso 0.0476(12) 1 calc PR A 2
C7B C 0.3574(14) 0.1795(16) 1.392(3) 0.0404(4) Uani 0.0476(12) 1 d PGD A 2
H7B H 0.4533 0.1731 1.3981 0.048 Uiso 0.0476(12) 1 calc PR A 2
C8B C 0.2575(16) 0.1612(13) 1.259(3) 0.0353(4) Uani 0.0476(12) 1 d PGD A 2
H8B H 0.2852 0.1423 1.1735 0.042 Uiso 0.0476(12) 1 calc PR A 2
C9B C -0.2416(15) 0.1631(16) 1.072(3) 0.0234(3) Uani 0.0476(12) 1 d PGD A 2
C10B C -0.1971(15) 0.1332(16) 0.953(3) 0.0243(3) Uani 0.0476(12) 1 d PGD A 2
C11B C -0.294(2) 0.1133(14) 0.819(3) 0.0308(4) Uani 0.0476(12) 1 d PGD A 2
H11B H -0.2631 0.0929 0.7384 0.037 Uiso 0.0476(12) 1 calc PR A 2
C12B C -0.4347(18) 0.1232(13) 0.804(3) 0.0360(4) Uani 0.0476(12) 1 d PGD A 2
H12B H -0.5007 0.1096 0.7119 0.043 Uiso 0.0476(12) 1 calc PR A 2
C13B C -0.4793(14) 0.1530(13) 0.922(3) 0.0345(4) Uani 0.0476(12) 1 d PGD A 2
H13B H -0.5757 0.1598 0.9112 0.041 Uiso 0.0476(12) 1 calc PR A 2
C14B C -0.3827(16) 0.1730(13) 1.056(3) 0.0284(3) Uani 0.0476(12) 1 d PGD A 2
H14B H -0.4132 0.1934 1.1369 0.034 Uiso 0.0476(12) 1 calc PR A 2
C15B C -0.156(3) 0.2178(14) 1.446(3) 0.0432(5) Uani 0.0476(12) 1 d PD A 2
H15D H -0.0982 0.2344 1.5448 0.065 Uiso 0.0476(12) 1 calc PR A 2
H15E H -0.2066 0.1850 1.4736 0.065 Uiso 0.0476(12) 1 calc PR A 2
H15F H -0.2221 0.2463 1.3904 0.065 Uiso 0.0476(12) 1 calc PR A 2
C16B C 0.032(2) 0.0974(6) 0.9093(19) 0.0234(3) Uani 0.0476(12) 1 d PGD A 2
C17B C 0.069(3) 0.0423(7) 0.961(2) 0.0403(5) Uani 0.0476(12) 1 d PGD A 2
H17B H 0.0402 0.0273 1.0510 0.048 Uiso 0.0476(12) 1 calc PR A 2
C18B C 0.147(3) 0.0090(8) 0.881(3) 0.0395(5) Uani 0.0476(12) 1 d PGD A 2
H18B H 0.1719 -0.0287 0.9168 0.047 Uiso 0.0476(12) 1 calc PR A 2
C19B C 0.189(3) 0.0308(10) 0.750(3) 0.0221(4) Uani 0.0476(12) 1 d PGD A 2
C20B C 0.152(4) 0.0860(10) 0.698(3) 0.0252(4) Uani 0.0476(12) 1 d PGD A 2
H20B H 0.1805 0.1009 0.6080 0.030 Uiso 0.0476(12) 1 calc PR A 2
C21B C 0.074(3) 0.1193(7) 0.778(2) 0.0262(3) Uani 0.0476(12) 1 d PGD A 2
H21B H 0.0489 0.1570 0.7422 0.031 Uiso 0.0476(12) 1 calc PR A 2
C22B C 0.270(3) -0.0067(14) 0.658(3) 0.0247(3) Uani 0.0476(12) 1 d PD A 2
C23B C 0.183(6) -0.060(2) 0.601(9) 0.0389(5) Uani 0.0476(12) 1 d PD A 2
H23D H 0.1604 -0.0792 0.6933 0.058 Uiso 0.0476(12) 1 calc PR A 2
H23E H 0.2359 -0.0862 0.5490 0.058 Uiso 0.0476(12) 1 calc PR A 2
H23F H 0.0964 -0.0493 0.5243 0.058 Uiso 0.0476(12) 1 calc PR A 2
C24B C 0.299(6) 0.023(3) 0.511(5) 0.0360(6) Uani 0.0476(12) 1 d PD A 2
H24D H 0.3541 -0.0016 0.4594 0.054 Uiso 0.0476(12) 1 calc PR A 2
H24E H 0.3498 0.0587 0.5450 0.054 Uiso 0.0476(12) 1 calc PR A 2
H24F H 0.2101 0.0322 0.4356 0.054 Uiso 0.0476(12) 1 calc PR A 2
C25B C 0.408(4) -0.025(2) 0.770(5) 0.0403(5) Uani 0.0476(12) 1 d PD A 2
H25D H 0.3897 -0.0452 0.8622 0.060 Uiso 0.0476(12) 1 calc PR A 2
H25E H 0.4651 0.0087 0.8065 0.060 Uiso 0.0476(12) 1 calc PR A 2
H25F H 0.4579 -0.0502 0.7114 0.060 Uiso 0.0476(12) 1 calc PR A 2


#==============================================================================

# MOLECULAR GEOMETRY

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
N1A C1A 1.385(2) . ?
N1A C4A 1.387(2) . ?
N1A C15A 1.4469(19) . ?
C1A C2A 1.3745(19) . ?
C1A C9A 1.428(2) . ?
C2A N2A 1.3817(19) . ?
C2A C3A 1.422(2) . ?
N2A C10A 1.3949(18) . ?
N2A C16A 1.4244(17) . ?
C3A C8A 1.405(2) . ?
C3A C4A 1.426(2) . ?
C4A C5A 1.390(2) . ?
C5A C6A 1.378(3) . ?
C5A H5A 0.9500 . ?
C6A C7A 1.396(3) . ?
C6A H6A 0.9500 . ?
C7A C8A 1.375(2) . ?
C7A H7A 0.9500 . ?
C8A H8A 0.9500 . ?
C9A C14A 1.404(2) . ?
C9A C10A 1.424(2) . ?
C10A C11A 1.389(2) . ?
C11A C12A 1.384(2) . ?
C11A H11A 0.9500 . ?
C12A C13A 1.400(2) . ?
C12A H12A 0.9500 . ?
C13A C14A 1.372(2) . ?
C13A H13A 0.9500 . ?
C14A H14A 0.9500 . ?
C15A H15A 0.9800 . ?
C15A H15B 0.9800 . ?
C15A H15C 0.9800 . ?
C16A C17A 1.3789(19) . ?
C16A C21A 1.380(2) . ?
C17A C18A 1.3902(19) . ?
C17A H17A 0.9500 . ?
C18A C19A 1.3869(19) . ?
C18A H18A 0.9500 . ?
C19A C20A 1.393(2) . ?
C19A C22A 1.5297(19) . ?
C20A C21A 1.383(2) . ?
C20A H20A 0.9500 . ?
C21A H21A 0.9500 . ?
C22A C24A 1.5295(19) . ?
C22A C25A 1.530(2) . ?
C22A C23A 1.535(2) . ?
C23A H23A 0.9800 . ?
C23A H23B 0.9800 . ?
C23A H23C 0.9800 . ?
C24A H24A 0.9800 . ?
C24A H24B 0.9800 . ?
C24A H24C 0.9800 . ?
C25A H25A 0.9800 . ?
C25A H25B 0.9800 . ?
C25A H25C 0.9800 . ?
N1B C1B 1.387(9) . ?
N1B C4B 1.389(8) . ?
N1B C15B 1.448(9) . ?
C1B C2B 1.370(9) . ?
C1B C9B 1.438(8) . ?
C2B N2B 1.385(8) . ?
C2B C3B 1.428(8) . ?
N2B C10B 1.393(8) . ?
N2B C16B 1.426(8) . ?
C3B C4B 1.3900 . ?
C3B C8B 1.3900 . ?
C4B C5B 1.3900 . ?
C5B C6B 1.3900 . ?
C5B H5B 0.9500 . ?
C6B C7B 1.3900 . ?
C6B H6B 0.9500 . ?
C7B C8B 1.3900 . ?
C7B H7B 0.9500 . ?
C8B H8B 0.9500 . ?
C9B C10B 1.3900 . ?
C9B C14B 1.3900 . ?
C10B C11B 1.3900 . ?
C11B C12B 1.3900 . ?
C11B H11B 0.9500 . ?
C12B C13B 1.3900 . ?
C12B H12B 0.9500 . ?
C13B C14B 1.3900 . ?
C13B H13B 0.9500 . ?
C14B H14B 0.9500 . ?
C15B H15D 0.9800 . ?
C15B H15E 0.9800 . ?
C15B H15F 0.9800 . ?
C16B C17B 1.3900 . ?
C16B C21B 1.3900 . ?
C17B C18B 1.3900 . ?
C17B H17B 0.9500 . ?
C18B C19B 1.3900 . ?
C18B H18B 0.9500 . ?
C19B C20B 1.3900 . ?
C19B C22B 1.533(8) . ?
C20B C21B 1.3900 . ?
C20B H20B 0.9500 . ?
C21B H21B 0.9500 . ?
C22B C24B 1.527(9) . ?
C22B C25B 1.531(10) . ?
C22B C23B 1.538(9) . ?
C23B H23D 0.9800 . ?
C23B H23E 0.9800 . ?
C23B H23F 0.9800 . ?
C24B H24D 0.9800 . ?
C24B H24E 0.9800 . ?
C24B H24F 0.9800 . ?
C25B H25D 0.9800 . ?
C25B H25E 0.9800 . ?
C25B H25F 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1A N1A C4A 107.17(12) . . ?
C1A N1A C15A 126.75(14) . . ?
C4A N1A C15A 125.82(14) . . ?
C2A C1A N1A 109.41(13) . . ?
C2A C1A C9A 109.04(13) . . ?
N1A C1A C9A 141.48(13) . . ?
C1A C2A N2A 109.67(13) . . ?
C1A C2A C3A 109.16(13) . . ?
N2A C2A C3A 141.08(13) . . ?
C2A N2A C10A 107.09(11) . . ?
C2A N2A C16A 125.77(12) . . ?
C10A N2A C16A 127.01(12) . . ?
C8A C3A C2A 136.55(15) . . ?
C8A C3A C4A 118.98(14) . . ?
C2A C3A C4A 104.46(13) . . ?
N1A C4A C5A 128.91(15) . . ?
N1A C4A C3A 109.81(14) . . ?
C5A C4A C3A 121.28(15) . . ?
C6A C5A C4A 118.05(16) . . ?
C6A C5A H5A 121.0 . . ?
C4A C5A H5A 121.0 . . ?
C5A C6A C7A 121.52(17) . . ?
C5A C6A H6A 119.2 . . ?
C7A C6A H6A 119.2 . . ?
C8A C7A C6A 121.19(16) . . ?
C8A C7A H7A 119.4 . . ?
C6A C7A H7A 119.4 . . ?
C7A C8A C3A 118.98(15) . . ?
C7A C8A H8A 120.5 . . ?
C3A C8A H8A 120.5 . . ?
C14A C9A C10A 118.78(14) . . ?
C14A C9A C1A 136.76(15) . . ?
C10A C9A C1A 104.45(13) . . ?
C11A C10A N2A 128.58(14) . . ?
C11A C10A C9A 121.64(13) . . ?
N2A C10A C9A 109.75(13) . . ?
C12A C11A C10A 117.80(15) . . ?
C12A C11A H11A 121.1 . . ?
C10A C11A H11A 121.1 . . ?
C11A C12A C13A 121.44(16) . . ?
C11A C12A H12A 119.3 . . ?
C13A C12A H12A 119.3 . . ?
C14A C13A C12A 121.00(15) . . ?
C14A C13A H13A 119.5 . . ?
C12A C13A H13A 119.5 . . ?
C13A C14A C9A 119.34(15) . . ?
C13A C14A H14A 120.3 . . ?
C9A C14A H14A 120.3 . . ?
C17A C16A C21A 119.28(13) . . ?
C17A C16A N2A 120.39(13) . . ?
C21A C16A N2A 120.31(12) . . ?
C16A C17A C18A 120.12(14) . . ?
C16A C17A H17A 119.9 . . ?
C18A C17A H17A 119.9 . . ?
C19A C18A C17A 121.66(13) . . ?
C19A C18A H18A 119.2 . . ?
C17A C18A H18A 119.2 . . ?
C18A C19A C20A 117.01(13) . . ?
C18A C19A C22A 123.32(13) . . ?
C20A C19A C22A 119.65(13) . . ?
C21A C20A C19A 121.71(14) . . ?
C21A C20A H20A 119.1 . . ?
C19A C20A H20A 119.1 . . ?
C16A C21A C20A 120.21(13) . . ?
C16A C21A H21A 119.9 . . ?
C20A C21A H21A 119.9 . . ?
C24A C22A C25A 108.70(14) . . ?
C24A C22A C19A 111.91(12) . . ?
C25A C22A C19A 109.82(14) . . ?
C24A C22A C23A 108.60(14) . . ?
C25A C22A C23A 108.99(15) . . ?
C19A C22A C23A 108.76(13) . . ?
C1B N1B C4B 107.1(8) . . ?
C1B N1B C15B 123.8(12) . . ?
C4B N1B C15B 129.1(12) . . ?
C2B C1B N1B 108.3(8) . . ?
C2B C1B C9B 106.0(8) . . ?
N1B C1B C9B 144.1(12) . . ?
C1B C2B N2B 111.9(8) . . ?
C1B C2B C3B 108.2(8) . . ?
N2B C2B C3B 139.0(10) . . ?
C2B N2B C10B 104.8(8) . . ?
C2B N2B C16B 125.9(11) . . ?
C10B N2B C16B 127.8(11) . . ?
C4B C3B C8B 120.0 . . ?
C4B C3B C2B 105.4(8) . . ?
C8B C3B C2B 134.4(8) . . ?
N1B C4B C3B 109.5(8) . . ?
N1B C4B C5B 130.4(8) . . ?
C3B C4B C5B 120.0 . . ?
C6B C5B C4B 120.0 . . ?
C6B C5B H5B 120.0 . . ?
C4B C5B H5B 120.0 . . ?
C5B C6B C7B 120.0 . . ?
C5B C6B H6B 120.0 . . ?
C7B C6B H6B 120.0 . . ?
C8B C7B C6B 120.0 . . ?
C8B C7B H7B 120.0 . . ?
C6B C7B H7B 120.0 . . ?
C7B C8B C3B 120.0 . . ?
C7B C8B H8B 120.0 . . ?
C3B C8B H8B 120.0 . . ?
C10B C9B C14B 120.0 . . ?
C10B C9B C1B 106.0(7) . . ?
C14B C9B C1B 133.9(8) . . ?
C9B C10B C11B 120.0 . . ?
C9B C10B N2B 110.8(8) . . ?
C11B C10B N2B 129.2(8) . . ?
C12B C11B C10B 120.0 . . ?
C12B C11B H11B 120.0 . . ?
C10B C11B H11B 120.0 . . ?
C13B C12B C11B 120.0 . . ?
C13B C12B H12B 120.0 . . ?
C11B C12B H12B 120.0 . . ?
C14B C13B C12B 120.0 . . ?
C14B C13B H13B 120.0 . . ?
C12B C13B H13B 120.0 . . ?
C13B C14B C9B 120.0 . . ?
C13B C14B H14B 120.0 . . ?
C9B C14B H14B 120.0 . . ?
N1B C15B H15D 109.5 . . ?
N1B C15B H15E 109.5 . . ?
H15D C15B H15E 109.5 . . ?
N1B C15B H15F 109.5 . . ?
H15D C15B H15F 109.5 . . ?
H15E C15B H15F 109.5 . . ?
C17B C16B C21B 120.0 . . ?
C17B C16B N2B 119.1(9) . . ?
C21B C16B N2B 120.8(9) . . ?
C16B C17B C18B 120.0 . . ?
C16B C17B H17B 120.0 . . ?
C18B C17B H17B 120.0 . . ?
C19B C18B C17B 120.0 . . ?
C19B C18B H18B 120.0 . . ?
C17B C18B H18B 120.0 . . ?
C18B C19B C20B 120.0 . . ?
C18B C19B C22B 120.0(10) . . ?
C20B C19B C22B 120.0(10) . . ?
C21B C20B C19B 120.0 . . ?
C21B C20B H20B 120.0 . . ?
C19B C20B H20B 120.0 . . ?
C20B C21B C16B 120.0 . . ?
C20B C21B H21B 120.0 . . ?
C16B C21B H21B 120.0 . . ?
C24B C22B C25B 109.4(13) . . ?
C24B C22B C19B 112.4(13) . . ?
C25B C22B C19B 109.9(12) . . ?
C24B C22B C23B 108.4(13) . . ?
C25B C22B C23B 108.6(13) . . ?
C19B C22B C23B 108.0(12) . . ?
C22B C23B H23D 109.5 . . ?
C22B C23B H23E 109.5 . . ?
H23D C23B H23E 109.5 . . ?
C22B C23B H23F 109.5 . . ?
H23D C23B H23F 109.5 . . ?
H23E C23B H23F 109.5 . . ?
C22B C24B H24D 109.5 . . ?
C22B C24B H24E 109.5 . . ?
H24D C24B H24E 109.5 . . ?
C22B C24B H24F 109.5 . . ?
H24D C24B H24F 109.5 . . ?
H24E C24B H24F 109.5 . . ?
C22B C25B H25D 109.5 . . ?
C22B C25B H25E 109.5 . . ?
H25D C25B H25E 109.5 . . ?
C22B C25B H25F 109.5 . . ?
H25D C25B H25F 109.5 . . ?
H25E C25B H25F 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
C4A N1A C1A C2A 0.50(17) . . . . ?
C15A N1A C1A C2A 174.77(15) . . . . ?
C4A N1A C1A C9A -175.9(2) . . . . ?
C15A N1A C1A C9A -1.7(3) . . . . ?
N1A C1A C2A N2A -177.53(12) . . . . ?
C9A C1A C2A N2A 0.12(17) . . . . ?
N1A C1A C2A C3A -0.26(18) . . . . ?
C9A C1A C2A C3A 177.39(14) . . . . ?
C1A C2A N2A C10A 0.23(17) . . . . ?
C3A C2A N2A C10A -175.7(2) . . . . ?
C1A C2A N2A C16A 176.25(13) . . . . ?
C3A C2A N2A C16A 0.4(3) . . . . ?
C1A C2A C3A C8A 178.3(2) . . . . ?
N2A C2A C3A C8A -5.8(4) . . . . ?
C1A C2A C3A C4A -0.08(18) . . . . ?
N2A C2A C3A C4A 175.8(2) . . . . ?
C1A N1A C4A C5A -179.40(18) . . . . ?
C15A N1A C4A C5A 6.3(3) . . . . ?
C1A N1A C4A C3A -0.55(17) . . . . ?
C15A N1A C4A C3A -174.89(15) . . . . ?
C8A C3A C4A N1A -178.34(17) . . . . ?
C2A C3A C4A N1A 0.39(17) . . . . ?
C8A C3A C4A C5A 0.6(2) . . . . ?
C2A C3A C4A C5A 179.34(18) . . . . ?
N1A C4A C5A C6A 178.3(2) . . . . ?
C3A C4A C5A C6A -0.4(2) . . . . ?
C4A C5A C6A C7A -0.2(2) . . . . ?
C5A C6A C7A C8A 0.7(3) . . . . ?
C6A C7A C8A C3A -0.5(2) . . . . ?
C2A C3A C8A C7A -178.4(2) . . . . ?
C4A C3A C8A C7A -0.2(2) . . . . ?
C2A C1A C9A C14A 178.37(17) . . . . ?
N1A C1A C9A C14A -5.2(3) . . . . ?
C2A C1A C9A C10A -0.41(16) . . . . ?
N1A C1A C9A C10A 176.03(19) . . . . ?
C2A N2A C10A C11A -178.66(14) . . . . ?
C16A N2A C10A C11A 5.4(2) . . . . ?
C2A N2A C10A C9A -0.50(16) . . . . ?
C16A N2A C10A C9A -176.45(13) . . . . ?
C14A C9A C10A C11A -0.2(2) . . . . ?
C1A C9A C10A C11A 178.87(13) . . . . ?
C14A C9A C10A N2A -178.49(13) . . . . ?
C1A C9A C10A N2A 0.55(15) . . . . ?
N2A C10A C11A C12A 178.33(15) . . . . ?
C9A C10A C11A C12A 0.4(2) . . . . ?
C10A C11A C12A C13A -0.1(2) . . . . ?
C11A C12A C13A C14A -0.3(2) . . . . ?
C12A C13A C14A C9A 0.5(2) . . . . ?
C10A C9A C14A C13A -0.3(2) . . . . ?
C1A C9A C14A C13A -178.91(18) . . . . ?
C2A N2A C16A C17A 66.4(2) . . . . ?
C10A N2A C16A C17A -118.41(17) . . . . ?
C2A N2A C16A C21A -111.86(18) . . . . ?
C10A N2A C16A C21A 63.4(2) . . . . ?
C21A C16A C17A C18A 1.2(3) . . . . ?
N2A C16A C17A C18A -177.08(16) . . . . ?
C16A C17A C18A C19A -0.8(3) . . . . ?
C17A C18A C19A C20A -0.2(3) . . . . ?
C17A C18A C19A C22A 178.20(17) . . . . ?
C18A C19A C20A C21A 0.8(3) . . . . ?
C22A C19A C20A C21A -177.64(18) . . . . ?
C17A C16A C21A C20A -0.6(3) . . . . ?
N2A C16A C21A C20A 177.68(16) . . . . ?
C19A C20A C21A C16A -0.5(3) . . . . ?
C18A C19A C22A C24A 12.0(2) . . . . ?
C20A C19A C22A C24A -169.67(18) . . . . ?
C18A C19A C22A C25A 132.77(18) . . . . ?
C20A C19A C22A C25A -48.9(2) . . . . ?
C18A C19A C22A C23A -108.0(2) . . . . ?
C20A C19A C22A C23A 70.3(2) . . . . ?
C4B N1B C1B C2B 12(3) . . . . ?
C15B N1B C1B C2B -167(3) . . . . ?
C4B N1B C1B C9B 174(5) . . . . ?
C15B N1B C1B C9B -5(5) . . . . ?
N1B C1B C2B N2B 177(2) . . . . ?
C9B C1B C2B N2B 8(4) . . . . ?
N1B C1B C2B C3B -12(3) . . . . ?
C9B C1B C2B C3B 179(3) . . . . ?
C1B C2B N2B C10B -8(4) . . . . ?
C3B C2B N2B C10B -175(4) . . . . ?
C1B C2B N2B C16B -175(2) . . . . ?
C3B C2B N2B C16B 18(6) . . . . ?
C1B C2B C3B C4B 8(3) . . . . ?
N2B C2B C3B C4B 175(4) . . . . ?
C1B C2B C3B C8B -177(3) . . . . ?
N2B C2B C3B C8B -9(6) . . . . ?
C1B N1B C4B C3B -7.2(18) . . . . ?
C15B N1B C4B C3B 171.9(18) . . . . ?
C1B N1B C4B C5B 177(2) . . . . ?
C15B N1B C4B C5B -4(2) . . . . ?
C8B C3B C4B N1B -177(2) . . . . ?
C2B C3B C4B N1B 0(2) . . . . ?
C8B C3B C4B C5B 0.0 . . . . ?
C2B C3B C4B C5B 176(3) . . . . ?
N1B C4B C5B C6B 176(2) . . . . ?
C3B C4B C5B C6B 0.0 . . . . ?
C4B C5B C6B C7B 0.0 . . . . ?
C5B C6B C7B C8B 0.0 . . . . ?
C6B C7B C8B C3B 0.0 . . . . ?
C4B C3B C8B C7B 0.0 . . . . ?
C2B C3B C8B C7B -175(3) . . . . ?
C2B C1B C9B C10B -4(3) . . . . ?
N1B C1B C9B C10B -166(4) . . . . ?
C2B C1B C9B C14B 178(3) . . . . ?
N1B C1B C9B C14B 16(7) . . . . ?
C14B C9B C10B C11B 0.0 . . . . ?
C1B C9B C10B C11B -178(3) . . . . ?
C14B C9B C10B N2B 177(3) . . . . ?
C1B C9B C10B N2B -1(3) . . . . ?
C2B N2B C10B C9B 5(3) . . . . ?
C16B N2B C10B C9B 171.4(18) . . . . ?
C2B N2B C10B C11B -178(3) . . . . ?
C16B N2B C10B C11B -11(5) . . . . ?
C9B C10B C11B C12B 0.0 . . . . ?
N2B C10B C11B C12B -177(4) . . . . ?
C10B C11B C12B C13B 0.0 . . . . ?
C11B C12B C13B C14B 0.0 . . . . ?
C12B C13B C14B C9B 0.0 . . . . ?
C10B C9B C14B C13B 0.0 . . . . ?
C1B C9B C14B C13B 177(4) . . . . ?
C2B N2B C16B C17B 74(3) . . . . ?
C10B N2B C16B C17B -90(3) . . . . ?
C2B N2B C16B C21B -108(3) . . . . ?
C10B N2B C16B C21B 88(3) . . . . ?
C21B C16B C17B C18B 0.0 . . . . ?
N2B C16B C17B C18B 177.7(18) . . . . ?
C16B C17B C18B C19B 0.0 . . . . ?
C17B C18B C19B C20B 0.0 . . . . ?
C17B C18B C19B C22B -178(2) . . . . ?
C18B C19B C20B C21B 0.0 . . . . ?
C22B C19B C20B C21B 178(2) . . . . ?
C19B C20B C21B C16B 0.0 . . . . ?
C17B C16B C21B C20B 0.0 . . . . ?
N2B C16B C21B C20B -177.7(19) . . . . ?
C18B C19B C22B C24B 176(3) . . . . ?
C20B C19B C22B C24B -1(3) . . . . ?
C18B C19B C22B C25B -61(3) . . . . ?
C20B C19B C22B C25B 121(3) . . . . ?
C18B C19B C22B C23B 57(3) . . . . ?
C20B C19B C22B C23B -121(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        30.08
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.244
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.042

#=====================  End of is_1h003 =================================

#=====================  End of CIF submission =================================

_database_code_depnum_ccdc_archive 'CCDC 1018402'
