# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2017

####################################################################### 
# 
# 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_asif35re
_database_code_depnum_ccdc_archive 'CCDC 1435339'
_audit_update_record             
;
2015-11-05 deposited with the CCDC.
2017-05-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
2,2,6,6,13-pentamethyl-3-methylene-2,2a,2a1,3,4,5,5a,6-octahydroindolo[3,2,1-de]pyrano[5,4,3,2-lmn]-phenanthridine
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H29 N O'
_chemical_formula_sum            'C26 H29 N O'
_chemical_formula_weight         371.50

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

_symmetry_cell_setting           MONOCLINIC
_symmetry_space_group_name_H-M   'p 21'
_symmetry_space_group_name_Hall  'P 2yb'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   11.5077(10)
_cell_length_b                   12.2620(7)
_cell_length_c                   15.7286(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 109.805(9)
_cell_angle_gamma                90.00
_cell_volume                     2088.1(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2341
_cell_measurement_theta_min      3.8920
_cell_measurement_theta_max      26.7880

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            WHITE
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      1.18
_exptl_crystal_density_diffrn    1.182
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             800
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.93437
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
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_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'Omega Scan'
_diffrn_detector_area_resol_mean 16.1049
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            7542
_diffrn_reflns_av_R_equivalents  0.0347
_diffrn_reflns_av_sigmaI/netI    0.0591
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.60
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3844
_reflns_number_gt                2582
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0312P)²+0.0000P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.6(17)
_refine_ls_number_reflns         3844
_refine_ls_number_parameters     515
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0820
_refine_ls_R_factor_gt           0.0463
_refine_ls_wR_factor_ref         0.0911
_refine_ls_wR_factor_gt          0.0787
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.039
_refine_ls_shift/su_mean         0.002

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
O2 O 0.3398(2) 0.39568(18) 0.12303(14) 0.0551(6) Uani 1 1 d . . .
N2 N 0.7225(3) 0.3886(2) 0.05854(17) 0.0484(7) Uani 1 1 d . . .
C21 C 0.5220(3) 0.3964(2) 0.08089(19) 0.0397(8) Uani 1 1 d . . .
C22 C 0.4523(3) 0.3525(3) 0.1287(2) 0.0455(9) Uani 1 1 d . . .
C23 C 0.4958(4) 0.2659(3) 0.1896(2) 0.0466(9) Uani 1 1 d . . .
C23A C 0.4160(4) 0.2248(3) 0.2419(2) 0.0707(12) Uani 1 1 d . . .
H23A H 0.4584 0.1674 0.2818 0.106 Uiso 1 1 calc R . .
H23B H 0.3396 0.1975 0.2004 0.106 Uiso 1 1 calc R . .
H23C H 0.3994 0.2835 0.2765 0.106 Uiso 1 1 calc R . .
C24 C 0.6102(4) 0.2224(3) 0.2010(2) 0.0513(10) Uani 1 1 d . . .
H24 H 0.6385 0.1639 0.2402 0.062 Uiso 1 1 calc R . .
C24A C 0.6846(3) 0.2643(2) 0.1551(2) 0.0417(9) Uani 1 1 d . . .
C24B C 0.8060(3) 0.2440(3) 0.1511(2) 0.0480(9) Uani 1 1 d . . .
C25 C 0.8978(4) 0.1692(3) 0.1927(2) 0.0639(11) Uani 1 1 d . . .
H25 H 0.8861 0.1191 0.2334 0.077 Uiso 1 1 calc R . .
C26 C 1.0059(4) 0.1689(4) 0.1739(3) 0.0795(13) Uani 1 1 d . . .
H26 H 1.0680 0.1193 0.2026 0.095 Uiso 1 1 calc R . .
C27 C 1.0221(4) 0.2417(3) 0.1128(3) 0.0753(12) Uani 1 1 d . . .
H27 H 1.0949 0.2392 0.0997 0.090 Uiso 1 1 calc R . .
C28 C 0.9339(4) 0.3188(3) 0.0700(3) 0.0623(11) Uani 1 1 d . . .
H28 H 0.9469 0.3677 0.0289 0.075 Uiso 1 1 calc R . .
C28A C 0.8255(4) 0.3209(3) 0.0901(2) 0.0492(9) Uani 1 1 d . . .
C28B C 0.6381(3) 0.3509(2) 0.0961(2) 0.0417(8) Uani 1 1 d . . .
C22' C 0.2891(3) 0.4807(3) 0.0553(2) 0.0537(10) Uani 1 1 d . . .
C22A C 0.2276(3) 0.4220(3) -0.0337(2) 0.0709(12) Uani 1 1 d . . .
H22A H 0.2861 0.3741 -0.0458 0.106 Uiso 1 1 calc R . .
H22B H 0.1990 0.4746 -0.0816 0.106 Uiso 1 1 calc R . .
H22C H 0.1589 0.3803 -0.0301 0.106 Uiso 1 1 calc R . .
C22B C 0.1907(4) 0.5382(3) 0.0836(3) 0.0795(13) Uani 1 1 d . . .
H22D H 0.1426 0.4850 0.1017 0.119 Uiso 1 1 calc R . .
H22E H 0.1379 0.5796 0.0336 0.119 Uiso 1 1 calc R . .
H22F H 0.2297 0.5863 0.1332 0.119 Uiso 1 1 calc R . .
C23' C 0.3924(3) 0.5582(3) 0.0517(2) 0.0483(9) Uani 1 1 d . . .
H23' H 0.3549 0.6140 0.0061 0.058 Uiso 1 1 calc R . .
C24' C 0.4848(3) 0.4929(2) 0.01974(19) 0.0412(8) Uani 1 1 d . . .
H24' H 0.4409 0.4663 -0.0415 0.049 Uiso 1 1 calc R . .
C25' C 0.5994(3) 0.5556(3) 0.0181(2) 0.0491(9) Uani 1 1 d . . .
H25' H 0.5709 0.6099 -0.0302 0.059 Uiso 1 1 calc R . .
C26' C 0.6600(3) 0.6179(3) 0.1056(2) 0.0582(10) Uani 1 1 d . . .
H26A H 0.7254 0.6640 0.0997 0.070 Uiso 1 1 calc R . .
H26B H 0.6962 0.5671 0.1547 0.070 Uiso 1 1 calc R . .
C27' C 0.5632(4) 0.6877(3) 0.1261(3) 0.0730(13) Uani 1 1 d . . .
H27A H 0.6017 0.7297 0.1807 0.088 Uiso 1 1 calc R . .
H27B H 0.5268 0.7383 0.0768 0.088 Uiso 1 1 calc R . .
C28' C 0.4646(4) 0.6158(3) 0.1382(3) 0.0570(10) Uani 1 1 d . . .
C29' C 0.4592(4) 0.5992(3) 0.2190(3) 0.0837(14) Uani 1 1 d . . .
H29A H 0.5166 0.6321 0.2690 0.100 Uiso 1 1 calc R . .
H29B H 0.3980 0.5546 0.2264 0.100 Uiso 1 1 calc R . .
C30' C 0.6918(3) 0.4803(3) -0.0062(2) 0.0530(10) Uani 1 1 d . . .
C30A C 0.6338(4) 0.4344(3) -0.1016(2) 0.0719(12) Uani 1 1 d . . .
H30A H 0.6898 0.3838 -0.1137 0.108 Uiso 1 1 calc R . .
H30B H 0.6169 0.4930 -0.1446 0.108 Uiso 1 1 calc R . .
H30C H 0.5581 0.3978 -0.1064 0.108 Uiso 1 1 calc R . .
C30B C 0.8073(4) 0.5454(3) -0.0020(3) 0.0757(13) Uani 1 1 d . . .
H30D H 0.8610 0.5513 0.0596 0.114 Uiso 1 1 calc R . .
H30E H 0.7835 0.6170 -0.0264 0.114 Uiso 1 1 calc R . .
H30F H 0.8499 0.5087 -0.0368 0.114 Uiso 1 1 calc R . .
O1 O 0.6688(2) 0.05355(19) 0.47431(16) 0.0651(7) Uani 1 1 d . . .
N1 N 1.0643(3) 0.0260(2) 0.43051(18) 0.0538(8) Uani 1 1 d . . .
C1 C 0.8680(3) 0.0524(3) 0.45647(19) 0.0439(9) Uani 1 1 d . . .
C2 C 0.7470(3) 0.0168(3) 0.4321(2) 0.0471(9) Uani 1 1 d . . .
C3 C 0.6991(3) -0.0619(3) 0.3643(2) 0.0462(9) Uani 1 1 d . . .
C3A C 0.5677(3) -0.0993(3) 0.3438(3) 0.0708(12) Uani 1 1 d . . .
H3A1 H 0.5453 -0.1478 0.2929 0.106 Uiso 1 1 calc R . .
H3A2 H 0.5136 -0.0373 0.3300 0.106 Uiso 1 1 calc R . .
H3A3 H 0.5604 -0.1368 0.3953 0.106 Uiso 1 1 calc R . .
C4 C 0.7726(3) -0.1030(3) 0.3190(2) 0.0489(9) Uani 1 1 d . . .
H4 H 0.7404 -0.1533 0.2727 0.059 Uiso 1 1 calc R . .
C4A C 0.8960(3) -0.0696(2) 0.3424(2) 0.0429(9) Uani 1 1 d . . .
C4B C 0.9966(3) -0.0918(3) 0.3099(2) 0.0474(9) Uani 1 1 d . . .
C5 C 1.0080(4) -0.1527(3) 0.2400(2) 0.0608(11) Uani 1 1 d . . .
H5 H 0.9412 -0.1932 0.2036 0.073 Uiso 1 1 calc R . .
C6 C 1.1178(5) -0.1541(4) 0.2235(3) 0.0785(14) Uani 1 1 d . . .
H6 H 1.1261 -0.1959 0.1766 0.094 Uiso 1 1 calc R . .
C7 C 1.2163(4) -0.0924(4) 0.2777(3) 0.0791(13) Uani 1 1 d . . .
H7 H 1.2897 -0.0932 0.2653 0.095 Uiso 1 1 calc R . .
C8 C 1.2104(4) -0.0303(3) 0.3487(3) 0.0698(12) Uani 1 1 d . . .
H8 H 1.2782 0.0095 0.3843 0.084 Uiso 1 1 calc R . .
C8A C 1.0992(4) -0.0292(3) 0.3656(2) 0.0525(10) Uani 1 1 d . . .
C8B C 0.9399(3) 0.0047(3) 0.4121(2) 0.0449(9) Uani 1 1 d . . .
C2' C 0.7115(4) 0.1459(3) 0.5348(3) 0.0698(12) Uani 1 1 d . . .
C20A C 0.6915(4) 0.2485(3) 0.4757(3) 0.0869(14) Uani 1 1 d . . .
H20A H 0.7290 0.2385 0.4303 0.130 Uiso 1 1 calc R . .
H20B H 0.7284 0.3101 0.5127 0.130 Uiso 1 1 calc R . .
H20C H 0.6046 0.2612 0.4472 0.130 Uiso 1 1 calc R . .
C20B C 0.6254(4) 0.1534(4) 0.5897(3) 0.1062(17) Uani 1 1 d . . .
H20D H 0.5413 0.1484 0.5500 0.159 Uiso 1 1 calc R . .
H20E H 0.6379 0.2218 0.6213 0.159 Uiso 1 1 calc R . .
H20F H 0.6427 0.0947 0.6326 0.159 Uiso 1 1 calc R . .
C3' C 0.8489(4) 0.1314(3) 0.5928(2) 0.0618(11) Uani 1 1 d . . .
H3' H 0.8733 0.1949 0.6328 0.074 Uiso 1 1 calc R . .
C4' C 0.9231(3) 0.1348(3) 0.5282(2) 0.0529(10) Uani 1 1 d . . .
H4' H 0.9107 0.2068 0.4995 0.063 Uiso 1 1 calc R . .
C5' C 1.0633(4) 0.1157(3) 0.5705(2) 0.0602(11) Uani 1 1 d . . .
H5' H 1.0974 0.1793 0.6085 0.072 Uiso 1 1 calc R . .
C6' C 1.0896(4) 0.0168(3) 0.6334(2) 0.0760(13) Uani 1 1 d . . .
H6'1 H 1.0647 -0.0491 0.5977 0.091 Uiso 1 1 calc R . .
H6'2 H 1.1777 0.0122 0.6661 0.091 Uiso 1 1 calc R . .
C7' C 1.0208(5) 0.0249(4) 0.7002(3) 0.0910(15) Uani 1 1 d . . .
H7'1 H 1.0394 -0.0384 0.7395 0.109 Uiso 1 1 calc R . .
H7'2 H 1.0478 0.0893 0.7375 0.109 Uiso 1 1 calc R . .
C8' C 0.8831(5) 0.0312(4) 0.6509(3) 0.0708(12) Uani 1 1 d . . .
C9' C 0.8119(5) -0.0489(4) 0.6580(3) 0.0962(16) Uani 1 1 d . . .
H9'1 H 0.7281 -0.0480 0.6242 0.115 Uiso 1 1 calc R . .
H9'2 H 0.8450 -0.1067 0.6970 0.115 Uiso 1 1 calc R . .
C10' C 1.1260(4) 0.1118(3) 0.4969(2) 0.0639(11) Uani 1 1 d . . .
C11' C 1.1107(4) 0.2215(3) 0.4472(3) 0.0926(16) Uani 1 1 d . . .
H11A H 1.1561 0.2201 0.4060 0.139 Uiso 1 1 calc R . .
H11B H 1.1415 0.2791 0.4903 0.139 Uiso 1 1 calc R . .
H11C H 1.0248 0.2338 0.4141 0.139 Uiso 1 1 calc R . .
C12' C 1.2638(4) 0.0874(4) 0.5414(3) 0.1028(17) Uani 1 1 d . . .
H12A H 1.2744 0.0133 0.5623 0.154 Uiso 1 1 calc R . .
H12B H 1.2985 0.1358 0.5917 0.154 Uiso 1 1 calc R . .
H12C H 1.3050 0.0979 0.4982 0.154 Uiso 1 1 calc R . .


_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
O2 C22 1.373(4) . ?
O2 C22' 1.463(4) . ?
N2 C28B 1.376(4) . ?
N2 C28A 1.394(4) . ?
N2 C30' 1.476(4) . ?
C21 C22 1.381(4) . ?
C21 C28B 1.391(4) . ?
C21 C24' 1.492(4) . ?
C22 C23 1.405(4) . ?
C23 C24 1.374(5) . ?
C23 C23A 1.511(4) . ?
C23A H23A 0.9600 . ?
C23A H23B 0.9600 . ?
C23A H23C 0.9600 . ?
C24 C24A 1.392(4) . ?
C24 H24 0.9300 . ?
C24A C28B 1.392(4) . ?
C24A C24B 1.441(5) . ?
C24B C25 1.384(5) . ?
C24B C28A 1.417(4) . ?
C25 C26 1.373(5) . ?
C25 H25 0.9300 . ?
C26 C27 1.369(5) . ?
C26 H26 0.9300 . ?
C27 C28 1.384(5) . ?
C27 H27 0.9300 . ?
C28 C28A 1.388(5) . ?
C28 H28 0.9300 . ?
C22' C22A 1.519(4) . ?
C22' C22B 1.523(5) . ?
C22' C23' 1.537(5) . ?
C22A H22A 0.9600 . ?
C22A H22B 0.9600 . ?
C22A H22C 0.9600 . ?
C22B H22D 0.9600 . ?
C22B H22E 0.9600 . ?
C22B H22F 0.9600 . ?
C23' C28' 1.508(4) . ?
C23' C24' 1.545(4) . ?
C23' H23' 0.9800 . ?
C24' C25' 1.534(4) . ?
C24' H24' 0.9800 . ?
C25' C26' 1.521(4) . ?
C25' C30' 1.551(5) . ?
C25' H25' 0.9800 . ?
C26' C27' 1.524(5) . ?
C26' H26A 0.9700 . ?
C26' H26B 0.9700 . ?
C27' C28' 1.499(5) . ?
C27' H27A 0.9700 . ?
C27' H27B 0.9700 . ?
C28' C29' 1.308(5) . ?
C29' H29A 0.9300 . ?
C29' H29B 0.9300 . ?
C30' C30A 1.528(4) . ?
C30' C30B 1.533(5) . ?
C30A H30A 0.9600 . ?
C30A H30B 0.9600 . ?
C30A H30C 0.9600 . ?
C30B H30D 0.9600 . ?
C30B H30E 0.9600 . ?
C30B H30F 0.9600 . ?
O1 C2 1.363(4) . ?
O1 C2' 1.454(4) . ?
N1 C8B 1.386(4) . ?
N1 C8A 1.392(4) . ?
N1 C10' 1.483(4) . ?
C1 C8B 1.380(4) . ?
C1 C2 1.384(4) . ?
C1 C4' 1.488(4) . ?
C2 C3 1.405(4) . ?
C3 C4 1.373(4) . ?
C3 C3A 1.507(4) . ?
C3A H3A1 0.9600 . ?
C3A H3A2 0.9600 . ?
C3A H3A3 0.9600 . ?
C4 C4A 1.402(5) . ?
C4 H4 0.9300 . ?
C4A C8B 1.383(4) . ?
C4A C4B 1.441(5) . ?
C4B C5 1.372(5) . ?
C4B C8A 1.432(5) . ?
C5 C6 1.373(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.388(6) . ?
C6 H6 0.9300 . ?
C7 C8 1.373(5) . ?
C7 H7 0.9300 . ?
C8 C8A 1.392(5) . ?
C8 H8 0.9300 . ?
C2' C20B 1.522(5) . ?
C2' C20A 1.535(5) . ?
C2' C3' 1.545(5) . ?
C20A H20A 0.9600 . ?
C20A H20B 0.9600 . ?
C20A H20C 0.9600 . ?
C20B H20D 0.9600 . ?
C20B H20E 0.9600 . ?
C20B H20F 0.9600 . ?
C3' C8' 1.502(6) . ?
C3' C4' 1.532(5) . ?
C3' H3' 0.9800 . ?
C4' C5' 1.540(5) . ?
C4' H4' 0.9800 . ?
C5' C6' 1.529(5) . ?
C5' C10' 1.559(5) . ?
C5' H5' 0.9800 . ?
C6' C7' 1.520(5) . ?
C6' H6'1 0.9700 . ?
C6' H6'2 0.9700 . ?
C7' C8' 1.512(6) . ?
C7' H7'1 0.9700 . ?
C7' H7'2 0.9700 . ?
C8' C9' 1.308(5) . ?
C9' H9'1 0.9300 . ?
C9' H9'2 0.9300 . ?
C10' C12' 1.530(5) . ?
C10' C11' 1.535(5) . ?
C11' H11A 0.9600 . ?
C11' H11B 0.9600 . ?
C11' H11C 0.9600 . ?
C12' H12A 0.9600 . ?
C12' H12B 0.9600 . ?
C12' H12C 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
C22 O2 C22' 117.1(3) . . ?
C28B N2 C28A 106.6(3) . . ?
C28B N2 C30' 120.9(3) . . ?
C28A N2 C30' 132.4(3) . . ?
C22 C21 C28B 116.8(3) . . ?
C22 C21 C24' 124.5(3) . . ?
C28B C21 C24' 118.5(3) . . ?
O2 C22 C21 121.6(3) . . ?
O2 C22 C23 116.5(3) . . ?
C21 C22 C23 121.8(3) . . ?
C24 C23 C22 119.1(3) . . ?
C24 C23 C23A 122.1(3) . . ?
C22 C23 C23A 118.8(4) . . ?
C23 C23A H23A 109.5 . . ?
C23 C23A H23B 109.5 . . ?
H23A C23A H23B 109.5 . . ?
C23 C23A H23C 109.5 . . ?
H23A C23A H23C 109.5 . . ?
H23B C23A H23C 109.5 . . ?
C23 C24 C24A 121.3(3) . . ?
C23 C24 H24 119.4 . . ?
C24A C24 H24 119.4 . . ?
C28B C24A C24 117.5(3) . . ?
C28B C24A C24B 105.2(3) . . ?
C24 C24A C24B 137.2(3) . . ?
C25 C24B C28A 119.4(4) . . ?
C25 C24B C24A 133.6(3) . . ?
C28A C24B C24A 107.0(3) . . ?
C26 C25 C24B 120.2(4) . . ?
C26 C25 H25 119.9 . . ?
C24B C25 H25 119.9 . . ?
C27 C26 C25 119.8(4) . . ?
C27 C26 H26 120.1 . . ?
C25 C26 H26 120.1 . . ?
C26 C27 C28 122.4(4) . . ?
C26 C27 H27 118.8 . . ?
C28 C27 H27 118.8 . . ?
C27 C28 C28A 118.0(4) . . ?
C27 C28 H28 121.0 . . ?
C28A C28 H28 121.0 . . ?
C28 C28A N2 130.7(3) . . ?
C28 C28A C24B 120.2(3) . . ?
N2 C28A C24B 109.1(3) . . ?
N2 C28B C21 124.6(3) . . ?
N2 C28B C24A 112.0(3) . . ?
C21 C28B C24A 123.4(3) . . ?
O2 C22' C22A 106.2(3) . . ?
O2 C22' C22B 105.6(3) . . ?
C22A C22' C22B 109.2(3) . . ?
O2 C22' C23' 110.2(3) . . ?
C22A C22' C23' 112.6(3) . . ?
C22B C22' C23' 112.7(3) . . ?
C22' C22A H22A 109.5 . . ?
C22' C22A H22B 109.5 . . ?
H22A C22A H22B 109.5 . . ?
C22' C22A H22C 109.5 . . ?
H22A C22A H22C 109.5 . . ?
H22B C22A H22C 109.5 . . ?
C22' C22B H22D 109.5 . . ?
C22' C22B H22E 109.5 . . ?
H22D C22B H22E 109.5 . . ?
C22' C22B H22F 109.5 . . ?
H22D C22B H22F 109.5 . . ?
H22E C22B H22F 109.5 . . ?
C28' C23' C22' 117.0(3) . . ?
C28' C23' C24' 107.9(3) . . ?
C22' C23' C24' 108.5(3) . . ?
C28' C23' H23' 107.7 . . ?
C22' C23' H23' 107.7 . . ?
C24' C23' H23' 107.7 . . ?
C21 C24' C25' 110.3(3) . . ?
C21 C24' C23' 106.2(3) . . ?
C25' C24' C23' 115.8(3) . . ?
C21 C24' H24' 108.1 . . ?
C25' C24' H24' 108.1 . . ?
C23' C24' H24' 108.1 . . ?
C26' C25' C24' 111.7(3) . . ?
C26' C25' C30' 112.3(3) . . ?
C24' C25' C30' 111.7(3) . . ?
C26' C25' H25' 106.9 . . ?
C24' C25' H25' 106.9 . . ?
C30' C25' H25' 106.9 . . ?
C25' C26' C27' 109.2(3) . . ?
C25' C26' H26A 109.8 . . ?
C27' C26' H26A 109.8 . . ?
C25' C26' H26B 109.8 . . ?
C27' C26' H26B 109.8 . . ?
H26A C26' H26B 108.3 . . ?
C28' C27' C26' 109.6(3) . . ?
C28' C27' H27A 109.7 . . ?
C26' C27' H27A 109.7 . . ?
C28' C27' H27B 109.7 . . ?
C26' C27' H27B 109.7 . . ?
H27A C27' H27B 108.2 . . ?
C29' C28' C27' 120.1(4) . . ?
C29' C28' C23' 127.6(4) . . ?
C27' C28' C23' 111.7(3) . . ?
C28' C29' H29A 120.0 . . ?
C28' C29' H29B 120.0 . . ?
H29A C29' H29B 120.0 . . ?
N2 C30' C30A 108.7(3) . . ?
N2 C30' C30B 111.5(3) . . ?
C30A C30' C30B 108.5(3) . . ?
N2 C30' C25' 107.9(3) . . ?
C30A C30' C25' 110.7(3) . . ?
C30B C30' C25' 109.7(3) . . ?
C30' C30A H30A 109.5 . . ?
C30' C30A H30B 109.5 . . ?
H30A C30A H30B 109.5 . . ?
C30' C30A H30C 109.5 . . ?
H30A C30A H30C 109.5 . . ?
H30B C30A H30C 109.5 . . ?
C30' C30B H30D 109.5 . . ?
C30' C30B H30E 109.5 . . ?
H30D C30B H30E 109.5 . . ?
C30' C30B H30F 109.5 . . ?
H30D C30B H30F 109.5 . . ?
H30E C30B H30F 109.5 . . ?
C2 O1 C2' 116.3(3) . . ?
C8B N1 C8A 106.9(3) . . ?
C8B N1 C10' 119.7(3) . . ?
C8A N1 C10' 132.2(3) . . ?
C8B C1 C2 116.4(3) . . ?
C8B C1 C4' 119.8(3) . . ?
C2 C1 C4' 123.7(3) . . ?
O1 C2 C1 122.0(3) . . ?
O1 C2 C3 116.2(3) . . ?
C1 C2 C3 121.8(3) . . ?
C4 C3 C2 119.6(3) . . ?
C4 C3 C3A 121.8(3) . . ?
C2 C3 C3A 118.6(3) . . ?
C3 C3A H3A1 109.5 . . ?
C3 C3A H3A2 109.5 . . ?
H3A1 C3A H3A2 109.5 . . ?
C3 C3A H3A3 109.5 . . ?
H3A1 C3A H3A3 109.5 . . ?
H3A2 C3A H3A3 109.5 . . ?
C3 C4 C4A 120.3(3) . . ?
C3 C4 H4 119.9 . . ?
C4A C4 H4 119.9 . . ?
C8B C4A C4 117.7(3) . . ?
C8B C4A C4B 106.5(3) . . ?
C4 C4A C4B 135.7(3) . . ?
C5 C4B C8A 120.0(4) . . ?
C5 C4B C4A 133.9(4) . . ?
C8A C4B C4A 106.1(3) . . ?
C4B C5 C6 120.1(4) . . ?
C4B C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C5 C6 C7 119.3(4) . . ?
C5 C6 H6 120.3 . . ?
C7 C6 H6 120.3 . . ?
C8 C7 C6 123.1(4) . . ?
C8 C7 H7 118.4 . . ?
C6 C7 H7 118.5 . . ?
C7 C8 C8A 117.6(4) . . ?
C7 C8 H8 121.2 . . ?
C8A C8 H8 121.2 . . ?
C8 C8A N1 131.1(4) . . ?
C8 C8A C4B 119.9(3) . . ?
N1 C8A C4B 109.0(3) . . ?
C1 C8B C4A 124.1(3) . . ?
C1 C8B N1 124.6(3) . . ?
C4A C8B N1 111.3(3) . . ?
O1 C2' C20B 106.1(3) . . ?
O1 C2' C20A 107.1(3) . . ?
C20B C2' C20A 107.6(4) . . ?
O1 C2' C3' 110.3(3) . . ?
C20B C2' C3' 113.9(3) . . ?
C20A C2' C3' 111.4(4) . . ?
C2' C20A H20A 109.5 . . ?
C2' C20A H20B 109.5 . . ?
H20A C20A H20B 109.5 . . ?
C2' C20A H20C 109.5 . . ?
H20A C20A H20C 109.5 . . ?
H20B C20A H20C 109.5 . . ?
C2' C20B H20D 109.5 . . ?
C2' C20B H20E 109.5 . . ?
H20D C20B H20E 109.5 . . ?
C2' C20B H20F 109.5 . . ?
H20D C20B H20F 109.5 . . ?
H20E C20B H20F 109.5 . . ?
C8' C3' C4' 109.7(3) . . ?
C8' C3' C2' 117.2(4) . . ?
C4' C3' C2' 107.1(3) . . ?
C8' C3' H3' 107.5 . . ?
C4' C3' H3' 107.5 . . ?
C2' C3' H3' 107.5 . . ?
C1 C4' C3' 107.1(3) . . ?
C1 C4' C5' 109.8(3) . . ?
C3' C4' C5' 116.5(3) . . ?
C1 C4' H4' 107.7 . . ?
C3' C4' H4' 107.7 . . ?
C5' C4' H4' 107.7 . . ?
C6' C5' C4' 110.5(3) . . ?
C6' C5' C10' 114.6(3) . . ?
C4' C5' C10' 111.4(3) . . ?
C6' C5' H5' 106.6 . . ?
C4' C5' H5' 106.6 . . ?
C10' C5' H5' 106.6 . . ?
C7' C6' C5' 111.1(4) . . ?
C7' C6' H6'1 109.4 . . ?
C5' C6' H6'1 109.4 . . ?
C7' C6' H6'2 109.4 . . ?
C5' C6' H6'2 109.4 . . ?
H6'1 C6' H6'2 108.0 . . ?
C8' C7' C6' 110.5(3) . . ?
C8' C7' H7'1 109.6 . . ?
C6' C7' H7'1 109.6 . . ?
C8' C7' H7'2 109.6 . . ?
C6' C7' H7'2 109.6 . . ?
H7'1 C7' H7'2 108.1 . . ?
C9' C8' C3' 128.6(5) . . ?
C9' C8' C7' 119.7(5) . . ?
C3' C8' C7' 111.5(4) . . ?
C8' C9' H9'1 120.0 . . ?
C8' C9' H9'2 120.0 . . ?
H9'1 C9' H9'2 120.0 . . ?
N1 C10' C12' 111.0(3) . . ?
N1 C10' C11' 108.5(3) . . ?
C12' C10' C11' 109.1(4) . . ?
N1 C10' C5' 108.2(3) . . ?
C12' C10' C5' 109.6(3) . . ?
C11' C10' C5' 110.5(3) . . ?
C10' C11' H11A 109.5 . . ?
C10' C11' H11B 109.5 . . ?
H11A C11' H11B 109.5 . . ?
C10' C11' H11C 109.5 . . ?
H11A C11' H11C 109.5 . . ?
H11B C11' H11C 109.5 . . ?
C10' C12' H12A 109.5 . . ?
C10' C12' H12B 109.5 . . ?
H12A C12' H12B 109.5 . . ?
C10' C12' H12C 109.5 . . ?
H12A C12' H12C 109.5 . . ?
H12B C12' H12C 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
C22' O2 C22 C21 8.0(4) . . . . ?
C22' O2 C22 C23 -175.8(3) . . . . ?
C28B C21 C22 O2 175.9(3) . . . . ?
C24' C21 C22 O2 0.2(5) . . . . ?
C28B C21 C22 C23 -0.2(4) . . . . ?
C24' C21 C22 C23 -175.9(3) . . . . ?
O2 C22 C23 C24 -177.3(3) . . . . ?
C21 C22 C23 C24 -1.0(5) . . . . ?
O2 C22 C23 C23A 1.6(4) . . . . ?
C21 C22 C23 C23A 177.9(3) . . . . ?
C22 C23 C24 C24A 1.5(5) . . . . ?
C23A C23 C24 C24A -177.3(3) . . . . ?
C23 C24 C24A C28B -0.9(5) . . . . ?
C23 C24 C24A C24B 177.9(3) . . . . ?
C28B C24A C24B C25 -179.3(3) . . . . ?
C24 C24A C24B C25 1.8(7) . . . . ?
C28B C24A C24B C28A 0.5(3) . . . . ?
C24 C24A C24B C28A -178.4(4) . . . . ?
C28A C24B C25 C26 -0.8(5) . . . . ?
C24A C24B C25 C26 179.0(4) . . . . ?
C24B C25 C26 C27 -1.0(6) . . . . ?
C25 C26 C27 C28 1.6(6) . . . . ?
C26 C27 C28 C28A -0.3(6) . . . . ?
C27 C28 C28A N2 179.5(3) . . . . ?
C27 C28 C28A C24B -1.5(5) . . . . ?
C28B N2 C28A C28 176.3(3) . . . . ?
C30' N2 C28A C28 0.1(6) . . . . ?
C28B N2 C28A C24B -2.8(4) . . . . ?
C30' N2 C28A C24B -178.9(3) . . . . ?
C25 C24B C28A C28 2.1(5) . . . . ?
C24A C24B C28A C28 -177.7(3) . . . . ?
C25 C24B C28A N2 -178.7(3) . . . . ?
C24A C24B C28A N2 1.4(4) . . . . ?
C28A N2 C28B C21 -179.7(3) . . . . ?
C30' N2 C28B C21 -3.0(4) . . . . ?
C28A N2 C28B C24A 3.2(3) . . . . ?
C30' N2 C28B C24A 179.9(3) . . . . ?
C22 C21 C28B N2 -175.9(3) . . . . ?
C24' C21 C28B N2 0.1(4) . . . . ?
C22 C21 C28B C24A 0.8(4) . . . . ?
C24' C21 C28B C24A 176.8(3) . . . . ?
C24 C24A C28B N2 176.8(3) . . . . ?
C24B C24A C28B N2 -2.3(3) . . . . ?
C24 C24A C28B C21 -0.3(4) . . . . ?
C24B C24A C28B C21 -179.4(3) . . . . ?
C22 O2 C22' C22A 82.2(3) . . . . ?
C22 O2 C22' C22B -161.9(3) . . . . ?
C22 O2 C22' C23' -40.0(4) . . . . ?
O2 C22' C23' C28' -58.2(4) . . . . ?
C22A C22' C23' C28' -176.6(3) . . . . ?
C22B C22' C23' C28' 59.5(4) . . . . ?
O2 C22' C23' C24' 64.0(3) . . . . ?
C22A C22' C23' C24' -54.3(4) . . . . ?
C22B C22' C23' C24' -178.3(3) . . . . ?
C22 C21 C24' C25' 150.0(3) . . . . ?
C28B C21 C24' C25' -25.7(4) . . . . ?
C22 C21 C24' C23' 23.7(4) . . . . ?
C28B C21 C24' C23' -152.0(3) . . . . ?
C28' C23' C24' C21 74.4(3) . . . . ?
C22' C23' C24' C21 -53.2(3) . . . . ?
C28' C23' C24' C25' -48.5(4) . . . . ?
C22' C23' C24' C25' -176.1(2) . . . . ?
C21 C24' C25' C26' -72.8(3) . . . . ?
C23' C24' C25' C26' 47.9(4) . . . . ?
C21 C24' C25' C30' 53.9(3) . . . . ?
C23' C24' C25' C30' 174.6(2) . . . . ?
C24' C25' C26' C27' -52.1(4) . . . . ?
C30' C25' C26' C27' -178.6(3) . . . . ?
C25' C26' C27' C28' 61.4(4) . . . . ?
C26' C27' C28' C29' 106.3(4) . . . . ?
C26' C27' C28' C23' -65.7(4) . . . . ?
C22' C23' C28' C29' 8.1(6) . . . . ?
C24' C23' C28' C29' -114.5(4) . . . . ?
C22' C23' C28' C27' 179.4(3) . . . . ?
C24' C23' C28' C27' 56.8(4) . . . . ?
C28B N2 C30' C30A -89.7(4) . . . . ?
C28A N2 C30' C30A 85.9(4) . . . . ?
C28B N2 C30' C30B 150.7(3) . . . . ?
C28A N2 C30' C30B -33.6(5) . . . . ?
C28B N2 C30' C25' 30.3(4) . . . . ?
C28A N2 C30' C25' -154.0(3) . . . . ?
C26' C25' C30' N2 71.0(3) . . . . ?
C24' C25' C30' N2 -55.5(3) . . . . ?
C26' C25' C30' C30A -170.3(3) . . . . ?
C24' C25' C30' C30A 63.3(3) . . . . ?
C26' C25' C30' C30B -50.6(4) . . . . ?
C24' C25' C30' C30B -177.0(3) . . . . ?
C2' O1 C2 C1 10.6(5) . . . . ?
C2' O1 C2 C3 -171.3(3) . . . . ?
C8B C1 C2 O1 176.5(3) . . . . ?
C4' C1 C2 O1 -1.5(5) . . . . ?
C8B C1 C2 C3 -1.5(5) . . . . ?
C4' C1 C2 C3 -179.6(3) . . . . ?
O1 C2 C3 C4 -179.8(3) . . . . ?
C1 C2 C3 C4 -1.6(5) . . . . ?
O1 C2 C3 C3A -0.2(4) . . . . ?
C1 C2 C3 C3A 177.9(3) . . . . ?
C2 C3 C4 C4A 2.1(5) . . . . ?
C3A C3 C4 C4A -177.4(3) . . . . ?
C3 C4 C4A C8B 0.5(5) . . . . ?
C3 C4 C4A C4B -178.1(3) . . . . ?
C8B C4A C4B C5 -175.7(3) . . . . ?
C4 C4A C4B C5 2.9(6) . . . . ?
C8B C4A C4B C8A 1.4(3) . . . . ?
C4 C4A C4B C8A -180.0(3) . . . . ?
C8A C4B C5 C6 0.3(5) . . . . ?
C4A C4B C5 C6 177.1(3) . . . . ?
C4B C5 C6 C7 -0.7(5) . . . . ?
C5 C6 C7 C8 0.9(6) . . . . ?
C6 C7 C8 C8A -0.7(6) . . . . ?
C7 C8 C8A N1 -178.9(3) . . . . ?
C7 C8 C8A C4B 0.3(5) . . . . ?
C8B N1 C8A C8 175.2(3) . . . . ?
C10' N1 C8A C8 8.3(6) . . . . ?
C8B N1 C8A C4B -4.1(4) . . . . ?
C10' N1 C8A C4B -171.0(3) . . . . ?
C5 C4B C8A C8 -0.1(5) . . . . ?
C4A C4B C8A C8 -177.7(3) . . . . ?
C5 C4B C8A N1 179.3(3) . . . . ?
C4A C4B C8A N1 1.7(3) . . . . ?
C2 C1 C8B C4A 4.3(5) . . . . ?
C4' C1 C8B C4A -177.5(3) . . . . ?
C2 C1 C8B N1 -176.7(3) . . . . ?
C4' C1 C8B N1 1.4(5) . . . . ?
C4 C4A C8B C1 -3.9(5) . . . . ?
C4B C4A C8B C1 175.1(3) . . . . ?
C4 C4A C8B N1 177.0(3) . . . . ?
C4B C4A C8B N1 -4.0(3) . . . . ?
C8A N1 C8B C1 -174.0(3) . . . . ?
C10' N1 C8B C1 -5.2(5) . . . . ?
C8A N1 C8B C4A 5.1(4) . . . . ?
C10' N1 C8B C4A 173.9(3) . . . . ?
C2 O1 C2' C20B -166.5(3) . . . . ?
C2 O1 C2' C20A 78.8(4) . . . . ?
C2 O1 C2' C3' -42.6(4) . . . . ?
O1 C2' C3' C8' -58.3(4) . . . . ?
C20B C2' C3' C8' 60.9(5) . . . . ?
C20A C2' C3' C8' -177.2(3) . . . . ?
O1 C2' C3' C4' 65.3(4) . . . . ?
C20B C2' C3' C4' -175.4(3) . . . . ?
C20A C2' C3' C4' -53.5(4) . . . . ?
C8B C1 C4' C3' -153.3(3) . . . . ?
C2 C1 C4' C3' 24.7(4) . . . . ?
C8B C1 C4' C5' -25.9(4) . . . . ?
C2 C1 C4' C5' 152.1(3) . . . . ?
C8' C3' C4' C1 74.8(4) . . . . ?
C2' C3' C4' C1 -53.5(4) . . . . ?
C8' C3' C4' C5' -48.6(4) . . . . ?
C2' C3' C4' C5' -176.8(3) . . . . ?
C1 C4' C5' C6' -75.1(4) . . . . ?
C3' C4' C5' C6' 46.8(4) . . . . ?
C1 C4' C5' C10' 53.4(4) . . . . ?
C3' C4' C5' C10' 175.3(3) . . . . ?
C4' C5' C6' C7' -50.8(4) . . . . ?
C10' C5' C6' C7' -177.6(3) . . . . ?
C5' C6' C7' C8' 59.6(5) . . . . ?
C4' C3' C8' C9' -120.5(5) . . . . ?
C2' C3' C8' C9' 1.9(6) . . . . ?
C4' C3' C8' C7' 54.9(4) . . . . ?
C2' C3' C8' C7' 177.3(3) . . . . ?
C6' C7' C8' C9' 113.6(4) . . . . ?
C6' C7' C8' C3' -62.2(5) . . . . ?
C8B N1 C10' C12' 152.3(3) . . . . ?
C8A N1 C10' C12' -42.2(5) . . . . ?
C8B N1 C10' C11' -87.9(4) . . . . ?
C8A N1 C10' C11' 77.7(5) . . . . ?
C8B N1 C10' C5' 32.0(4) . . . . ?
C8A N1 C10' C5' -162.4(3) . . . . ?
C6' C5' C10' N1 70.1(4) . . . . ?
C4' C5' C10' N1 -56.2(4) . . . . ?
C6' C5' C10' C12' -51.1(4) . . . . ?
C4' C5' C10' C12' -177.4(3) . . . . ?
C6' C5' C10' C11' -171.3(3) . . . . ?
C4' C5' C10' C11' 62.4(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.136
_refine_diff_density_min         -0.142
_refine_diff_density_rms         0.029
####################################################################### 
# 
# 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_5
_audit_block_doi                 10.5517/ccdc.csd.cc14hz2p
_database_code_depnum_ccdc_archive 'CCDC 1058032'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/C6RA16531A 2016
_audit_update_record             
;
2015-04-06 deposited with the CCDC.
2017-05-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 5,7-dimethyl-2-(propan-2-ylidene)-1,2,3,4,5,13-hexahydro-1,5-
 methanooxocino[3,2-a]carbazole 
;
_chemical_name_common            MK-POCL3-R
_chemical_melting_point          ?
_chemical_formula_moiety         'C46 H50 N2 O2'
_chemical_formula_sum            'C46 H50 N2 O2'
_chemical_formula_weight         662.88

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/c

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                   8.4284(6)
_cell_length_b                   18.5039(14)
_cell_length_c                   23.3119(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.851(5)
_cell_angle_gamma                90.00
_cell_volume                     3627.5(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3356
_cell_measurement_theta_min      3.7750
_cell_measurement_theta_max      28.6210

_exptl_crystal_description       rod
_exptl_crystal_colour            'color less'
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.214
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1424
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.83843
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   'Crysalis PRO (Oxford Diffraction, 2010)'

_exptl_special_details           
; 
 CrysAlis PRO, Oxford Diffraction Ltd., Version 1.171.34.40 (release
27--08-2010 CrysAlis171. NET) (compiled Aug 27 2010,11:50:40) 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_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, sapphire3'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean 16.1049
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            14007
_diffrn_reflns_av_R_equivalents  0.0704
_diffrn_reflns_av_sigmaI/netI    0.1404
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         3.43
_diffrn_reflns_theta_max         26.00
_reflns_number_total             7064
_reflns_number_gt                2884
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlis Pro  (Oxford Diffraction, 2010)'
_computing_cell_refinement       'CrysAlis Pro  (Oxford Diffraction, 2010)'
_computing_data_reduction        'CrysAlis Pro  (Oxford Diffraction, 2010)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'ORTEP3 (Farrugia, 2012)'
_computing_publication_material  'PLATON (Spek, 2009)'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0758P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0023(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         7064
_refine_ls_number_parameters     452
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1760
_refine_ls_R_factor_gt           0.0791
_refine_ls_wR_factor_ref         0.2269
_refine_ls_wR_factor_gt          0.1726
_refine_ls_goodness_of_fit_ref   0.989
_refine_ls_restrained_S_all      0.989
_refine_ls_shift/su_max          0.011
_refine_ls_shift/su_mean         0.002

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
N1 N 0.3032(3) 0.38494(15) 0.52985(12) 0.0500(8) Uani 1 1 d . . .
H1 H 0.2273 0.4137 0.5184 0.060 Uiso 1 1 calc R . .
C1 C 0.4503(4) 0.40571(19) 0.55442(15) 0.0469(9) Uani 1 1 d . . .
C2 C 0.5080(4) 0.4742(2) 0.56501(15) 0.0545(10) Uani 1 1 d . . .
H2 H 0.4464 0.5147 0.5556 0.065 Uiso 1 1 calc R . .
C3 C 0.6617(5) 0.4809(2) 0.59035(17) 0.0647(11) Uani 1 1 d . . .
H3 H 0.7029 0.5266 0.5987 0.078 Uiso 1 1 calc R . .
C4 C 0.7542(4) 0.4202(2) 0.60329(16) 0.0610(11) Uani 1 1 d . . .
H4 H 0.8570 0.4258 0.6198 0.073 Uiso 1 1 calc R . .
C5 C 0.6953(4) 0.3519(2) 0.59188(15) 0.0545(10) Uani 1 1 d . . .
H5 H 0.7578 0.3116 0.6010 0.065 Uiso 1 1 calc R . .
C6 C 0.5428(4) 0.3434(2) 0.56679(14) 0.0471(9) Uani 1 1 d . . .
C7 C 0.4447(4) 0.28217(19) 0.54958(14) 0.0437(9) Uani 1 1 d . . .
C8 C 0.4700(4) 0.20798(19) 0.54916(15) 0.0497(9) Uani 1 1 d . . .
H8 H 0.5669 0.1894 0.5638 0.060 Uiso 1 1 calc R . .
C9 C 0.3531(4) 0.1614(2) 0.52726(16) 0.0511(9) Uani 1 1 d . . .
C10 C 0.2067(4) 0.1922(2) 0.50599(15) 0.0498(9) Uani 1 1 d . . .
C11 C 0.1741(4) 0.2653(2) 0.50584(15) 0.0469(9) Uani 1 1 d . . .
C12 C 0.2986(4) 0.30936(19) 0.52676(14) 0.0460(9) Uani 1 1 d . . .
C13 C 0.3800(5) 0.0820(2) 0.5230(2) 0.0765(13) Uani 1 1 d . . .
H13A H 0.2853 0.0593 0.5063 0.115 Uiso 1 1 calc R . .
H13B H 0.4054 0.0626 0.5606 0.115 Uiso 1 1 calc R . .
H13C H 0.4664 0.0731 0.4991 0.115 Uiso 1 1 calc R . .
O1 O 0.0964(3) 0.14175(13) 0.48452(11) 0.0609(7) Uani 1 1 d . . .
C14 C -0.0597(4) 0.1670(2) 0.46159(17) 0.0569(10) Uani 1 1 d . . .
C15 C -0.0510(5) 0.1828(2) 0.39755(17) 0.0683(12) Uani 1 1 d . . .
H15A H -0.1575 0.1926 0.3810 0.082 Uiso 1 1 calc R . .
H15B H -0.0124 0.1400 0.3789 0.082 Uiso 1 1 calc R . .
C16 C 0.0563(4) 0.2465(2) 0.38472(16) 0.0633(11) Uani 1 1 d . . .
H16A H 0.1665 0.2332 0.3935 0.076 Uiso 1 1 calc R . .
H16B H 0.0430 0.2583 0.3441 0.076 Uiso 1 1 calc R . .
C17 C 0.0165(4) 0.3118(2) 0.41982(16) 0.0516(10) Uani 1 1 d . . .
C18 C 0.0149(4) 0.2937(2) 0.48334(15) 0.0504(9) Uani 1 1 d . . .
H18 H -0.0117 0.3370 0.5049 0.060 Uiso 1 1 calc R . .
C19 C -0.1059(4) 0.2344(2) 0.49272(16) 0.0560(10) Uani 1 1 d . . .
H19A H -0.1089 0.2245 0.5335 0.067 Uiso 1 1 calc R . .
H19B H -0.2110 0.2501 0.4783 0.067 Uiso 1 1 calc R . .
C20 C -0.1701(5) 0.1037(2) 0.4711(2) 0.0842(14) Uani 1 1 d . . .
H20A H -0.1367 0.0625 0.4500 0.126 Uiso 1 1 calc R . .
H20B H -0.2769 0.1164 0.4581 0.126 Uiso 1 1 calc R . .
H20C H -0.1663 0.0921 0.5114 0.126 Uiso 1 1 calc R . .
C21 C -0.0134(4) 0.3776(2) 0.39641(18) 0.0584(10) Uani 1 1 d . . .
C22 C -0.0703(5) 0.4393(2) 0.4310(2) 0.0804(13) Uani 1 1 d . . .
H22A H -0.0847 0.4812 0.4069 0.121 Uiso 1 1 calc R . .
H22B H 0.0069 0.4496 0.4621 0.121 Uiso 1 1 calc R . .
H22C H -0.1697 0.4267 0.4462 0.121 Uiso 1 1 calc R . .
C23 C 0.0090(5) 0.3928(2) 0.33417(18) 0.0855(14) Uani 1 1 d . . .
H23A H -0.0186 0.4422 0.3256 0.128 Uiso 1 1 calc R . .
H23B H -0.0582 0.3613 0.3105 0.128 Uiso 1 1 calc R . .
H23C H 0.1181 0.3846 0.3265 0.128 Uiso 1 1 calc R . .
N2 N 0.2039(3) 0.71475(16) 0.26890(13) 0.0589(9) Uani 1 1 d . . .
H2A H 0.2743 0.6958 0.2485 0.071 Uiso 1 1 calc R . .
C24 C 0.0611(4) 0.6826(2) 0.28099(17) 0.0558(10) Uani 1 1 d . . .
C25 C -0.0004(5) 0.6172(2) 0.26339(17) 0.0686(12) Uani 1 1 d . . .
H25 H 0.0533 0.5876 0.2390 0.082 Uiso 1 1 calc R . .
C26 C -0.1452(5) 0.5966(2) 0.28302(19) 0.0741(13) Uani 1 1 d . . .
H26 H -0.1890 0.5522 0.2719 0.089 Uiso 1 1 calc R . .
C27 C -0.2256(5) 0.6412(3) 0.31901(19) 0.0724(12) Uani 1 1 d . . .
H27 H -0.3221 0.6261 0.3321 0.087 Uiso 1 1 calc R . .
C28 C -0.1653(4) 0.7069(2) 0.33551(17) 0.0629(12) Uani 1 1 d . . .
H28 H -0.2201 0.7362 0.3599 0.075 Uiso 1 1 calc R . .
C29 C -0.0209(4) 0.7301(2) 0.31570(15) 0.0523(10) Uani 1 1 d . . .
C30 C 0.0760(4) 0.7939(2) 0.32405(15) 0.0495(9) Uani 1 1 d . . .
C31 C 0.0607(4) 0.8602(2) 0.35122(15) 0.0558(10) Uani 1 1 d . . .
H31 H -0.0293 0.8691 0.3711 0.067 Uiso 1 1 calc R . .
C32 C 0.1748(4) 0.9128(2) 0.34940(15) 0.0535(10) Uani 1 1 d . . .
C33 C 0.3142(4) 0.8976(2) 0.32030(15) 0.0541(10) Uani 1 1 d . . .
C34 C 0.3389(4) 0.8324(2) 0.29499(15) 0.0500(9) Uani 1 1 d . . .
C35 C 0.2153(4) 0.7825(2) 0.29499(15) 0.0519(10) Uani 1 1 d . . .
C36 C 0.1599(5) 0.9867(2) 0.37530(19) 0.0816(14) Uani 1 1 d . . .
H36A H 0.2530 1.0146 0.3688 0.122 Uiso 1 1 calc R . .
H36B H 0.1493 0.9823 0.4159 0.122 Uiso 1 1 calc R . .
H36C H 0.0677 1.0105 0.3578 0.122 Uiso 1 1 calc R . .
O2 O 0.4205(3) 0.95376(14) 0.31953(11) 0.0664(8) Uani 1 1 d . . .
C37 C 0.5706(4) 0.9437(2) 0.29202(18) 0.0643(11) Uani 1 1 d . . .
C38 C 0.5487(5) 0.9632(2) 0.22933(19) 0.0736(12) Uani 1 1 d . . .
H38A H 0.6522 0.9648 0.2135 0.088 Uiso 1 1 calc R . .
H38B H 0.5031 1.0113 0.2259 0.088 Uiso 1 1 calc R . .
C39 C 0.4421(5) 0.9108(2) 0.19340(16) 0.0675(12) Uani 1 1 d . . .
H39A H 0.3323 0.9191 0.2017 0.081 Uiso 1 1 calc R . .
H39B H 0.4514 0.9211 0.1530 0.081 Uiso 1 1 calc R . .
C40 C 0.4819(4) 0.8320(2) 0.20433(16) 0.0547(10) Uani 1 1 d . . .
C41 C 0.4942(4) 0.8166(2) 0.26788(14) 0.0515(10) Uani 1 1 d . . .
H41 H 0.5224 0.7657 0.2742 0.062 Uiso 1 1 calc R . .
C42 C 0.6219(4) 0.8648(2) 0.29922(17) 0.0628(11) Uani 1 1 d . . .
H42A H 0.6330 0.8523 0.3397 0.075 Uiso 1 1 calc R . .
H42B H 0.7237 0.8574 0.2830 0.075 Uiso 1 1 calc R . .
C43 C 0.6867(5) 0.9946(2) 0.3234(2) 0.0911(15) Uani 1 1 d . . .
H43A H 0.6994 0.9811 0.3633 0.137 Uiso 1 1 calc R . .
H43B H 0.6469 1.0431 0.3203 0.137 Uiso 1 1 calc R . .
H43C H 0.7877 0.9918 0.3068 0.137 Uiso 1 1 calc R . .
C44 C 0.5061(4) 0.7835(2) 0.16427(17) 0.0622(11) Uani 1 1 d . . .
C45 C 0.5445(5) 0.7049(2) 0.1761(2) 0.0826(14) Uani 1 1 d . . .
H45A H 0.5577 0.6803 0.1405 0.124 Uiso 1 1 calc R . .
H45B H 0.4593 0.6829 0.1952 0.124 Uiso 1 1 calc R . .
H45C H 0.6412 0.7015 0.2002 0.124 Uiso 1 1 calc R . .
C46 C 0.4935(5) 0.8021(3) 0.10045(17) 0.0890(15) Uani 1 1 d . . .
H46A H 0.5152 0.7598 0.0785 0.134 Uiso 1 1 calc R . .
H46B H 0.5693 0.8391 0.0931 0.134 Uiso 1 1 calc R . .
H46C H 0.3882 0.8192 0.0896 0.134 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.385(4) . ?
N1 C12 1.401(4) . ?
C1 C2 1.373(5) . ?
C1 C6 1.411(5) . ?
C2 C3 1.393(5) . ?
C3 C4 1.389(5) . ?
C4 C5 1.377(5) . ?
C5 C6 1.385(4) . ?
C6 C7 1.443(5) . ?
C7 C8 1.389(4) . ?
C7 C12 1.401(4) . ?
C8 C9 1.380(5) . ?
C9 C10 1.418(5) . ?
C9 C13 1.492(5) . ?
C10 C11 1.380(5) . ?
C10 O1 1.388(4) . ?
C11 C12 1.391(4) . ?
C11 C18 1.503(4) . ?
O1 C14 1.463(4) . ?
C14 C19 1.508(5) . ?
C14 C15 1.528(5) . ?
C14 C20 1.522(5) . ?
C15 C16 1.528(5) . ?
C16 C17 1.509(5) . ?
C17 C21 1.352(5) . ?
C17 C18 1.519(5) . ?
C18 C19 1.523(4) . ?
C21 C22 1.495(5) . ?
C21 C23 1.502(5) . ?
N2 C24 1.388(4) . ?
N2 C35 1.394(4) . ?
C24 C25 1.369(5) . ?
C24 C29 1.407(5) . ?
C25 C26 1.385(5) . ?
C26 C27 1.386(5) . ?
C27 C28 1.363(5) . ?
C28 C29 1.398(5) . ?
C29 C30 1.442(5) . ?
C30 C31 1.390(5) . ?
C30 C35 1.411(4) . ?
C31 C32 1.371(5) . ?
C32 C33 1.424(4) . ?
C32 C36 1.504(5) . ?
C33 C34 1.366(5) . ?
C33 O2 1.372(4) . ?
C34 C35 1.391(5) . ?
C34 C41 1.520(4) . ?
O2 C37 1.468(4) . ?
C37 C38 1.504(5) . ?
C37 C43 1.512(5) . ?
C37 C42 1.530(5) . ?
C38 C39 1.533(5) . ?
C39 C40 1.512(5) . ?
C40 C44 1.322(5) . ?
C40 C41 1.506(5) . ?
C41 C42 1.544(5) . ?
C44 C45 1.511(5) . ?
C44 C46 1.524(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
C1 N1 C12 108.6(3) . . ?
C2 C1 N1 128.8(3) . . ?
C2 C1 C6 122.2(3) . . ?
N1 C1 C6 109.0(3) . . ?
C1 C2 C3 117.8(4) . . ?
C4 C3 C2 120.8(4) . . ?
C5 C4 C3 120.7(3) . . ?
C4 C5 C6 119.9(4) . . ?
C5 C6 C1 118.5(3) . . ?
C5 C6 C7 134.8(3) . . ?
C1 C6 C7 106.6(3) . . ?
C8 C7 C12 118.9(3) . . ?
C8 C7 C6 133.8(3) . . ?
C12 C7 C6 107.2(3) . . ?
C9 C8 C7 120.9(3) . . ?
C8 C9 C10 117.5(3) . . ?
C8 C9 C13 122.1(3) . . ?
C10 C9 C13 120.3(3) . . ?
C11 C10 O1 122.0(3) . . ?
C11 C10 C9 124.3(3) . . ?
O1 C10 C9 113.7(3) . . ?
C10 C11 C12 115.3(3) . . ?
C10 C11 C18 121.1(3) . . ?
C12 C11 C18 123.5(3) . . ?
C11 C12 N1 128.4(3) . . ?
C11 C12 C7 123.1(3) . . ?
N1 C12 C7 108.6(3) . . ?
C10 O1 C14 118.8(3) . . ?
O1 C14 C19 110.1(3) . . ?
O1 C14 C15 108.5(3) . . ?
C19 C14 C15 110.1(3) . . ?
O1 C14 C20 104.1(3) . . ?
C19 C14 C20 112.7(3) . . ?
C15 C14 C20 111.1(3) . . ?
C14 C15 C16 114.0(3) . . ?
C17 C16 C15 110.8(3) . . ?
C21 C17 C16 123.0(4) . . ?
C21 C17 C18 125.3(3) . . ?
C16 C17 C18 111.7(3) . . ?
C11 C18 C17 110.6(3) . . ?
C11 C18 C19 106.7(3) . . ?
C17 C18 C19 110.4(3) . . ?
C14 C19 C18 109.3(3) . . ?
C17 C21 C22 121.9(4) . . ?
C17 C21 C23 121.8(4) . . ?
C22 C21 C23 116.4(4) . . ?
C24 N2 C35 109.4(3) . . ?
C25 C24 N2 129.4(4) . . ?
C25 C24 C29 122.2(4) . . ?
N2 C24 C29 108.4(3) . . ?
C24 C25 C26 118.0(4) . . ?
C27 C26 C25 120.9(4) . . ?
C28 C27 C26 120.9(4) . . ?
C27 C28 C29 119.8(4) . . ?
C28 C29 C24 118.1(4) . . ?
C28 C29 C30 134.8(4) . . ?
C24 C29 C30 107.0(3) . . ?
C31 C30 C35 117.2(3) . . ?
C31 C30 C29 135.7(3) . . ?
C35 C30 C29 107.2(3) . . ?
C32 C31 C30 121.7(3) . . ?
C31 C32 C33 118.5(3) . . ?
C31 C32 C36 123.8(3) . . ?
C33 C32 C36 117.7(3) . . ?
C34 C33 O2 123.0(3) . . ?
C34 C33 C32 122.3(4) . . ?
O2 C33 C32 114.7(3) . . ?
C33 C34 C35 116.8(3) . . ?
C33 C34 C41 120.7(3) . . ?
C35 C34 C41 122.6(3) . . ?
C34 C35 N2 128.8(3) . . ?
C34 C35 C30 123.3(3) . . ?
N2 C35 C30 108.0(3) . . ?
C33 O2 C37 119.5(3) . . ?
O2 C37 C38 109.9(3) . . ?
O2 C37 C43 105.0(3) . . ?
C38 C37 C43 110.8(4) . . ?
O2 C37 C42 108.6(3) . . ?
C38 C37 C42 110.5(4) . . ?
C43 C37 C42 111.9(3) . . ?
C37 C38 C39 114.1(3) . . ?
C40 C39 C38 113.7(3) . . ?
C44 C40 C41 124.2(4) . . ?
C44 C40 C39 125.4(4) . . ?
C41 C40 C39 110.4(3) . . ?
C40 C41 C34 111.6(3) . . ?
C40 C41 C42 110.8(3) . . ?
C34 C41 C42 106.5(3) . . ?
C37 C42 C41 108.5(3) . . ?
C40 C44 C45 124.5(4) . . ?
C40 C44 C46 122.1(4) . . ?
C45 C44 C46 113.3(4) . . ?

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.286
_refine_diff_density_min         -0.271
_refine_diff_density_rms         0.047
