# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2015

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

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 1417823'
_audit_update_record             
;
2015-08-09 deposited with the CCDC.
2015-09-10 downloaded from the CCDC.
;

_audit_creation_date             2015-08-09T14:20:31-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

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

# CHEMICAL DATA

_chemical_name_systematic        
;
13,17-diethyl-12,18-dimethyldibenzo[b,g]-21,22-dicarbaporphyrin
;
_chemical_formula_moiety         'C36 H32 N2'
_chemical_formula_sum            'C36 H32 N2'
_chemical_formula_weight         492.63

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

# CRYSTAL DATA

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.9415(4)
_cell_length_b                   15.4054(7)
_cell_length_c                   21.5716(9)
_cell_angle_alpha                102.614(3)
_cell_angle_beta                 95.363(3)
_cell_angle_gamma                97.396(3)
_cell_volume                     2533.8(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5840
_cell_measurement_theta_min      2.67
_cell_measurement_theta_max      22.47
_cell_measurement_temperature    100(2)
_exptl_crystal_description       plate
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.116
_exptl_crystal_size_mid          0.065
_exptl_crystal_size_min          0.021
_exptl_crystal_density_diffrn    1.291
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1048
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.70
_exptl_absorpt_correction_T_max  0.75
_exptl_absorpt_process_details   
;
TWINABS; (Bruker, 2014)
;

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

# EXPERIMENTAL DATA

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_reflns_number            9949
_diffrn_reflns_theta_min         0.975
_diffrn_reflns_theta_max         26.022
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       26
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        0

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

# STRUCTURE SOLUTION

_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed

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

# REFINEMENT DATA

_refine_special_details          Twin
_reflns_number_total             9949
_reflns_number_gt                5143
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.1647
_refine_ls_R_factor_gt           0.0727
_refine_ls_wR_factor_ref         0.194
_refine_ls_goodness_of_fit_ref   1.01
_refine_ls_restrained_S_all      1.01
_refine_ls_number_reflns         9949
_refine_ls_number_parameters     700
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0879P)²+0.3501P] where P=(Fo²+2Fc²)/3'
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.413
_refine_diff_density_min         -0.641
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
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 0 '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'

_computing_data_collection       'APEX2 (Bruker, 2014)'
_computing_cell_refinement       'APEX2 & SAINT (Bruker, 2013)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SUPERFLIP (Palatinus & Chapuis, 2007)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    
;
ORTEP-3 for Windows (Farrugia, 2012) and 
Mercury CSD (Macrae et al., 2008)
;
_computing_publication_material  
;
WinGX (Farrugia, 1999)
;

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

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
N23 0.1510(4) 0.9944(2) 0.11478(15) 0.0210(7) Uani d 1 . . N
N24 0.3122(4) 0.8544(2) 0.02981(14) 0.0219(7) Uani d 1 . . N
C1 0.3955(5) 0.8941(2) -0.09852(16) 0.0206(8) Uani d 1 . . C
C2 0.4146(4) 0.9037(2) -0.16425(16) 0.0191(8) Uani d 1 . . C
C2A 0.4621(5) 0.8465(2) -0.21648(16) 0.0226(8) Uani d 1 . . C
H2A 0.4903 0.7894 -0.2134 0.027 Uiso calc 1 . . H
C2B 0.4679(5) 0.8741(3) -0.27345(17) 0.0262(9) Uani d 1 . . C
H2B 0.4987 0.8352 -0.3098 0.031 Uiso calc 1 . . H
C3 0.3727(4) 0.9884(2) -0.16890(15) 0.0189(8) Uani d 1 . . C
C3A 0.3813(5) 1.0157(2) -0.22603(16) 0.0215(8) Uani d 1 . . C
H3A 0.3548 1.073 -0.2294 0.026 Uiso calc 1 . . H
C3B 0.4291(5) 0.9582(2) -0.27780(16) 0.0229(8) Uani d 1 . . C
H3B 0.4355 0.9764 -0.3169 0.027 Uiso calc 1 . . H
C4 0.3231(5) 1.0327(2) -0.10699(16) 0.0194(8) Uani d 1 . . C
C5 0.2622(4) 1.1148(2) -0.09255(15) 0.0205(8) Uani d 1 . . C
H5 0.2688 1.1507 -0.1231 0.025 Uiso calc 1 . . H
C6 0.1918(5) 1.1486(2) -0.03645(16) 0.0201(8) Uani d 1 . . C
C7 0.1532(4) 1.2399(2) -0.01515(16) 0.0194(8) Uani d 1 . . C
C7A 0.1680(5) 1.3131(2) -0.04334(17) 0.0226(9) Uani d 1 . . C
H7A 0.2055 1.3075 -0.0844 0.027 Uiso calc 1 . . H
C7B 0.1277(5) 1.3940(2) -0.01095(16) 0.0253(9) Uani d 1 . . C
H7B 0.1375 1.4444 -0.0299 0.03 Uiso calc 1 . . H
C8 0.0959(4) 1.2486(2) 0.04565(16) 0.0194(8) Uani d 1 . . C
C8A 0.0554(5) 1.3301(2) 0.07766(17) 0.0234(9) Uani d 1 . . C
H8A 0.0164 1.3362 0.1185 0.028 Uiso calc 1 . . H
C8B 0.0728(5) 1.4024(2) 0.04913(16) 0.0258(9) Uani d 1 . . C
H8B 0.0469 1.4588 0.071 0.031 Uiso calc 1 . . H
C9 0.0965(5) 1.1617(2) 0.06369(16) 0.0202(8) Uani d 1 . . C
C10 0.0635(4) 1.1445(2) 0.12286(16) 0.0211(8) Uani d 1 . . C
H10 0.0154 1.1894 0.1501 0.025 Uiso calc 1 . . H
C11 0.0920(5) 1.0699(2) 0.14713(16) 0.0212(8) Uani d 1 . . C
C12 0.0833(5) 1.0598(2) 0.21105(16) 0.0216(8) Uani d 1 . . C
C12A 0.0324(5) 1.1279(3) 0.26455(17) 0.0279(9) Uani d 1 . . C
H12A 0.0016 1.1792 0.2483 0.042 Uiso calc 0.5 . . H
H12B -0.066 1.1001 0.2814 0.042 Uiso calc 0.5 . . H
H12C 0.1286 1.1488 0.2988 0.042 Uiso calc 0.5 . . H
H12D 0.0412 1.1062 0.304 0.042 Uiso calc 0.5 . . H
H12E 0.1088 1.1853 0.271 0.042 Uiso calc 0.5 . . H
H12F -0.0858 1.1366 0.2535 0.042 Uiso calc 0.5 . . H
C13 0.1346(5) 0.9790(3) 0.21558(17) 0.0226(9) Uani d 1 . . C
C13A 0.1539(5) 0.9420(3) 0.27456(17) 0.0281(9) Uani d 1 . . C
H13A 0.2432 0.9025 0.2704 0.034 Uiso calc 1 . . H
H13B 0.1936 0.9926 0.3122 0.034 Uiso calc 1 . . H
C13B -0.0084(5) 0.8894(3) 0.2862(2) 0.0478(6) Uani d 1 . . C
H13C 0.0132 0.8673 0.3251 0.072 Uiso calc 1 . . H
H13D -0.0968 0.9283 0.2915 0.072 Uiso calc 1 . . H
H13E -0.0472 0.8382 0.2496 0.072 Uiso calc 1 . . H
C14 0.1730(5) 0.9353(2) 0.15422(16) 0.0216(8) Uani d 1 . . C
C15 0.2247(5) 0.8518(2) 0.13609(16) 0.0224(8) Uani d 1 . . C
H15 0.2202 0.8165 0.1671 0.027 Uiso calc 1 . . H
C16 0.2823(5) 0.8119(2) 0.07931(16) 0.0203(8) Uani d 1 . . C
C17 0.3179(5) 0.7233(2) 0.05920(16) 0.0212(8) Uani d 1 . . C
C17A 0.2984(5) 0.6549(2) 0.09949(17) 0.0264(9) Uani d 1 . . C
H17A 0.2889 0.5938 0.0716 0.032 Uiso calc 1 . . H
H17B 0.1912 0.6587 0.1193 0.032 Uiso calc 1 . . H
C17B 0.4491(6) 0.6691(3) 0.1522(2) 0.0478(6) Uani d 1 . . C
H17C 0.4309 0.6233 0.1771 0.072 Uiso calc 1 . . H
H17D 0.5552 0.6642 0.1328 0.072 Uiso calc 1 . . H
H17E 0.4576 0.7291 0.1806 0.072 Uiso calc 1 . . H
C18 0.3710(5) 0.7128(2) -0.00097(16) 0.0220(8) Uani d 1 . . C
C18A 0.4138(5) 0.6303(2) -0.04237(17) 0.0280(9) Uani d 1 . . C
H18A 0.4473 0.6435 -0.0823 0.042 Uiso calc 0.5 . . H
H18B 0.5087 0.6098 -0.02 0.042 Uiso calc 0.5 . . H
H18C 0.3136 0.583 -0.0521 0.042 Uiso calc 0.5 . . H
H18D 0.3991 0.5806 -0.0207 0.042 Uiso calc 0.5 . . H
H18E 0.3377 0.6144 -0.0829 0.042 Uiso calc 0.5 . . H
H18F 0.5328 0.6412 -0.0509 0.042 Uiso calc 0.5 . . H
C19 0.3706(5) 0.7966(2) -0.01925(16) 0.0218(8) Uani d 1 . . C
C20 0.4119(5) 0.8155(2) -0.07656(16) 0.0207(8) Uani d 1 . . C
H20 0.4566 0.7698 -0.1044 0.025 Uiso calc 1 . . H
C21 0.3465(5) 0.9732(2) -0.06677(17) 0.0209(8) Uani d 1 . . C
C22 0.1501(5) 1.1041(2) 0.01190(16) 0.0206(8) Uani d 1 . . C
H23 0.125(6) 0.967(3) 0.076(2) 0.051(15) Uiso d 1 . . H
H24 0.349(5) 0.915(3) 0.0400(18) 0.030(11) Uiso d 1 . . H
H21 0.335(5) 0.995(2) -0.0192(18) 0.027(10) Uiso d 1 . . H
H22 0.159(4) 1.039(2) 0.0064(16) 0.025(10) Uiso d 1 . . H
N73 0.3698(4) 0.6416(2) 0.46862(14) 0.0212(7) Uani d 1 . . N
N74 0.0981(4) 0.5015(2) 0.38450(14) 0.0190(7) Uani d 1 . . N
C51 -0.0165(5) 0.3355(2) 0.43651(16) 0.0214(8) Uani d 1 . . C
C52 -0.0532(5) 0.2491(2) 0.45509(16) 0.0192(8) Uani d 1 . . C
C52A -0.1486(5) 0.1670(2) 0.42330(17) 0.0244(9) Uani d 1 . . C
H52A -0.2062 0.1596 0.3814 0.029 Uiso calc 1 . . H
C52B -0.1593(5) 0.0954(2) 0.45325(17) 0.0260(9) Uani d 1 . . C
H52B -0.223 0.0387 0.4314 0.031 Uiso calc 1 . . H
C53 0.0342(5) 0.2591(2) 0.51747(16) 0.0191(8) Uani d 1 . . C
C53A 0.0201(5) 0.1876(2) 0.54694(17) 0.0225(9) Uani d 1 . . C
H53A 0.0769 0.1945 0.5889 0.027 Uiso calc 1 . . H
C53B -0.0771(5) 0.1062(2) 0.51522(17) 0.0251(9) Uani d 1 . . C
H53B -0.0879 0.0574 0.5357 0.03 Uiso calc 1 . . H
C54 0.1292(5) 0.3504(2) 0.53782(16) 0.0190(8) Uani d 1 . . C
C55 0.2431(5) 0.3857(2) 0.59422(15) 0.0216(8) Uani d 1 . . C
H55 0.2446 0.351 0.6256 0.026 Uiso calc 1 . . H
C56 0.3540(5) 0.4670(2) 0.60816(16) 0.0188(8) Uani d 1 . . C
C57 0.4548(4) 0.5124(2) 0.67005(16) 0.0194(8) Uani d 1 . . C
C57A 0.4728(5) 0.4884(2) 0.72829(16) 0.0223(9) Uani d 1 . . C
H57A 0.4175 0.4319 0.7325 0.027 Uiso calc 1 . . H
C57B 0.5722(5) 0.5478(2) 0.78042(17) 0.0255(9) Uani d 1 . . C
H57B 0.5843 0.5318 0.8205 0.031 Uiso calc 1 . . H
C58 0.5400(5) 0.5961(2) 0.66423(16) 0.0203(8) Uani d 1 . . C
C58A 0.6384(5) 0.6546(2) 0.71637(17) 0.0246(9) Uani d 1 . . C
H58A 0.6949 0.711 0.7125 0.03 Uiso calc 1 . . H
C58B 0.6541(5) 0.6301(3) 0.77479(17) 0.0256(9) Uani d 1 . . C
H58B 0.7214 0.6702 0.811 0.031 Uiso calc 1 . . H
C59 0.4965(5) 0.6036(2) 0.59757(16) 0.0216(8) Uani d 1 . . C
C60 0.5444(5) 0.6808(2) 0.57459(16) 0.0225(9) Uani d 1 . . C
H60 0.6288 0.7258 0.6017 0.027 Uiso calc 1 . . H
C61 0.4836(5) 0.6993(2) 0.51717(16) 0.0218(8) Uani d 1 . . C
C62 0.5162(5) 0.7832(2) 0.49790(17) 0.0213(8) Uani d 1 . . C
C62A 0.6232(5) 0.8661(2) 0.53924(18) 0.0271(9) Uani d 1 . . C
H62A 0.6701 0.8529 0.5792 0.041 Uiso calc 0.5 . . H
H62B 0.7172 0.8859 0.5167 0.041 Uiso calc 0.5 . . H
H62C 0.5524 0.9138 0.5489 0.041 Uiso calc 0.5 . . H
H62D 0.623 0.9155 0.5173 0.041 Uiso calc 0.5 . . H
H62E 0.576 0.8825 0.5798 0.041 Uiso calc 0.5 . . H
H62F 0.7407 0.8546 0.5477 0.041 Uiso calc 0.5 . . H
C63 0.4280(5) 0.7724(2) 0.43840(16) 0.0221(8) Uani d 1 . . C
C63A 0.4229(5) 0.8404(2) 0.39783(17) 0.0259(9) Uani d 1 . . C
H63A 0.4552 0.9017 0.4257 0.031 Uiso calc 1 . . H
H63B 0.3047 0.8354 0.3768 0.031 Uiso calc 1 . . H
C63B 0.5432(6) 0.8267(3) 0.3470(2) 0.0478(6) Uani d 1 . . C
H63C 0.5363 0.8721 0.3217 0.072 Uiso calc 1 . . H
H63D 0.6608 0.8328 0.3677 0.072 Uiso calc 1 . . H
H63E 0.5103 0.7665 0.3189 0.072 Uiso calc 1 . . H
C64 0.3365(5) 0.6828(2) 0.41841(16) 0.0212(8) Uani d 1 . . C
C65 0.2312(5) 0.6422(2) 0.36139(16) 0.0232(9) Uani d 1 . . C
H65 0.2295 0.6768 0.3299 0.028 Uiso calc 1 . . H
C66 0.1284(5) 0.5586(2) 0.34387(16) 0.0207(8) Uani d 1 . . C
C67 0.0381(5) 0.5147(2) 0.28283(16) 0.0203(8) Uani d 1 . . C
C67A 0.0499(5) 0.5505(2) 0.22337(15) 0.0256(9) Uani d 1 . . C
H67A 0.1627 0.5886 0.2277 0.031 Uiso calc 1 . . H
H67B 0.0446 0.4991 0.1862 0.031 Uiso calc 1 . . H
C67B -0.0880(6) 0.6047(3) 0.2100(2) 0.0478(6) Uani d 1 . . C
H67C -0.0717 0.6255 0.1709 0.072 Uiso calc 1 . . H
H67D -0.2002 0.5671 0.2045 0.072 Uiso calc 1 . . H
H67E -0.082 0.6568 0.2461 0.072 Uiso calc 1 . . H
C68 -0.0502(5) 0.4338(2) 0.28762(16) 0.0210(8) Uani d 1 . . C
C68A -0.1620(5) 0.3642(3) 0.23636(16) 0.0261(9) Uani d 1 . . C
H68A -0.2074 0.3139 0.2541 0.039 Uiso calc 0.5 . . H
H68B -0.2571 0.3905 0.2194 0.039 Uiso calc 0.5 . . H
H68C -0.0952 0.3423 0.2018 0.039 Uiso calc 0.5 . . H
H68D -0.1657 0.3839 0.1961 0.039 Uiso calc 0.5 . . H
H68E -0.116 0.3073 0.2309 0.039 Uiso calc 0.5 . . H
H68F -0.2779 0.3555 0.2484 0.039 Uiso calc 0.5 . . H
C69 -0.0140(5) 0.4255(2) 0.35223(16) 0.0205(8) Uani d 1 . . C
C70 -0.0681(5) 0.3510(2) 0.37651(16) 0.0207(8) Uani d 1 . . C
H70 -0.1502 0.3052 0.3489 0.025 Uiso calc 1 . . H
C71 0.0885(5) 0.3935(3) 0.48846(16) 0.0214(8) Uani d 1 . . C
C72 0.3911(5) 0.5239(2) 0.56658(17) 0.0218(8) Uani d 1 . . C
H73 0.367(5) 0.582(3) 0.4585(18) 0.030(11) Uiso d 1 . . H
H74 0.096(5) 0.529(2) 0.4252(18) 0.026(10) Uiso d 1 . . H
H71 0.133(4) 0.460(2) 0.4944(16) 0.025(10) Uiso d 1 . . H
H72 0.341(4) 0.504(2) 0.5192(17) 0.021(9) Uiso d 1 . . H



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

# MOLECULAR GEOMETRY

_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N23 C11 . 1.381(5) ?
N23 C14 . 1.391(4) ?
N23 H23 . 0.84(4) ?
N24 C19 . 1.384(5) ?
N24 C16 . 1.392(4) ?
N24 H24 . 0.92(4) ?
C1 C21 . 1.383(5) ?
C1 C20 . 1.409(5) ?
C1 C2 . 1.477(5) ?
C2 C2A . 1.385(5) ?
C2 C3 . 1.411(5) ?
C2A C2B . 1.388(5) ?
C2A H2A . 0.95 ?
C2B C3B . 1.391(5) ?
C2B H2B . 0.95 ?
C3 C3A . 1.391(4) ?
C3 C4 . 1.474(5) ?
C3A C3B . 1.382(5) ?
C3A H3A . 0.95 ?
C3B H3B . 0.95 ?
C4 C5 . 1.393(5) ?
C4 C21 . 1.411(5) ?
C5 C6 . 1.405(5) ?
C5 H5 . 0.95 ?
C6 C22 . 1.410(5) ?
C6 C7 . 1.462(5) ?
C7 C7A . 1.390(5) ?
C7 C8 . 1.413(5) ?
C7A C7B . 1.382(5) ?
C7A H7A . 0.95 ?
C7B C8B . 1.390(5) ?
C7B H7B . 0.95 ?
C8 C8A . 1.388(5) ?
C8 C9 . 1.474(5) ?
C8A C8B . 1.384(5) ?
C8A H8A . 0.95 ?
C8B H8B . 0.95 ?
C9 C10 . 1.400(5) ?
C9 C22 . 1.403(5) ?
C10 C11 . 1.397(5) ?
C10 H10 . 0.95 ?
C11 C12 . 1.428(5) ?
C12 C13 . 1.378(5) ?
C12 C12A . 1.505(5) ?
C12A H12A . 0.98 ?
C12A H12B . 0.98 ?
C12A H12C . 0.98 ?
C12A H12D . 0.98 ?
C12A H12E . 0.98 ?
C12A H12F . 0.98 ?
C13 C14 . 1.428(5) ?
C13 C13A . 1.507(5) ?
C13A C13B . 1.504(5) ?
C13A H13A . 0.99 ?
C13A H13B . 0.99 ?
C13B H13C . 0.98 ?
C13B H13D . 0.98 ?
C13B H13E . 0.98 ?
C14 C15 . 1.387(5) ?
C15 C16 . 1.391(5) ?
C15 H15 . 0.95 ?
C16 C17 . 1.412(5) ?
C17 C18 . 1.384(5) ?
C17 C17A . 1.508(5) ?
C17A C17B . 1.531(5) ?
C17A H17A . 0.99 ?
C17A H17B . 0.99 ?
C17B H17C . 0.98 ?
C17B H17D . 0.98 ?
C17B H17E . 0.98 ?
C18 C19 . 1.430(5) ?
C18 C18A . 1.484(5) ?
C18A H18A . 0.98 ?
C18A H18B . 0.98 ?
C18A H18C . 0.98 ?
C18A H18D . 0.98 ?
C18A H18E . 0.98 ?
C18A H18F . 0.98 ?
C19 C20 . 1.389(5) ?
C20 H20 . 0.95 ?
C21 H21 . 1.02(4) ?
C22 H22 . 1.00(4) ?
N73 C61 . 1.383(5) ?
N73 C64 . 1.392(4) ?
N73 H73 . 0.89(4) ?
N74 C69 . 1.381(5) ?
N74 C66 . 1.386(4) ?
N74 H74 . 0.89(4) ?
C51 C71 . 1.395(5) ?
C51 C70 . 1.400(5) ?
C51 C52 . 1.475(5) ?
C52 C52A . 1.386(5) ?
C52 C53 . 1.423(5) ?
C52A C52B . 1.392(5) ?
C52A H52A . 0.95 ?
C52B C53B . 1.397(5) ?
C52B H52B . 0.95 ?
C53 C53A . 1.384(5) ?
C53 C54 . 1.461(5) ?
C53A C53B . 1.384(5) ?
C53A H53A . 0.95 ?
C53B H53B . 0.95 ?
C54 C55 . 1.405(5) ?
C54 C71 . 1.407(5) ?
C55 C56 . 1.391(5) ?
C55 H55 . 0.95 ?
C56 C72 . 1.410(5) ?
C56 C57 . 1.470(5) ?
C57 C57A . 1.385(5) ?
C57 C58 . 1.414(5) ?
C57A C57B . 1.387(5) ?
C57A H57A . 0.95 ?
C57B C58B . 1.384(5) ?
C57B H57B . 0.95 ?
C58 C58A . 1.378(5) ?
C58 C59 . 1.480(5) ?
C58A C58B . 1.391(5) ?
C58A H58A . 0.95 ?
C58B H58B . 0.95 ?
C59 C72 . 1.388(5) ?
C59 C60 . 1.408(5) ?
C60 C61 . 1.388(5) ?
C60 H60 . 0.95 ?
C61 C62 . 1.441(5) ?
C62 C63 . 1.369(5) ?
C62 C62A . 1.493(5) ?
C62A H62A . 0.98 ?
C62A H62B . 0.98 ?
C62A H62C . 0.98 ?
C62A H62D . 0.98 ?
C62A H62E . 0.98 ?
C62A H62F . 0.98 ?
C63 C64 . 1.429(5) ?
C63 C63A . 1.507(5) ?
C63A C63B . 1.518(5) ?
C63A H63A . 0.99 ?
C63A H63B . 0.99 ?
C63B H63C . 0.98 ?
C63B H63D . 0.98 ?
C63B H63E . 0.98 ?
C64 C65 . 1.393(5) ?
C65 C66 . 1.389(5) ?
C65 H65 . 0.95 ?
C66 C67 . 1.420(5) ?
C67 C68 . 1.378(5) ?
C67 C67A . 1.509(4) ?
C67A C67B . 1.504(5) ?
C67A H67A . 0.99 ?
C67A H67B . 0.99 ?
C67B H67C . 0.98 ?
C67B H67D . 0.98 ?
C67B H67E . 0.98 ?
C68 C69 . 1.433(5) ?
C68 C68A . 1.489(5) ?
C68A H68A . 0.98 ?
C68A H68B . 0.98 ?
C68A H68C . 0.98 ?
C68A H68D . 0.98 ?
C68A H68E . 0.98 ?
C68A H68F . 0.98 ?
C69 C70 . 1.397(5) ?
C70 H70 . 0.95 ?
C71 H71 . 1.02(4) ?
C72 H72 . 1.03(3) ?

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
C11 N23 C14 110.7(3) . . ?
C11 N23 H23 128(3) . . ?
C14 N23 H23 112(3) . . ?
C19 N24 C16 110.0(3) . . ?
C19 N24 H24 122(2) . . ?
C16 N24 H24 118(2) . . ?
C21 C1 C20 128.7(3) . . ?
C21 C1 C2 106.3(3) . . ?
C20 C1 C2 124.8(3) . . ?
C2A C2 C3 120.5(3) . . ?
C2A C2 C1 131.9(3) . . ?
C3 C2 C1 107.6(3) . . ?
C2 C2A C2B 118.9(3) . . ?
C2 C2A H2A 120.6 . . ?
C2B C2A H2A 120.6 . . ?
C2A C2B C3B 120.6(3) . . ?
C2A C2B H2B 119.7 . . ?
C3B C2B H2B 119.7 . . ?
C3A C3 C2 119.9(3) . . ?
C3A C3 C4 131.7(3) . . ?
C2 C3 C4 108.4(3) . . ?
C3B C3A C3 119.1(3) . . ?
C3B C3A H3A 120.5 . . ?
C3 C3A H3A 120.5 . . ?
C3A C3B C2B 121.0(3) . . ?
C3A C3B H3B 119.5 . . ?
C2B C3B H3B 119.5 . . ?
C5 C4 C21 128.0(3) . . ?
C5 C4 C3 126.9(3) . . ?
C21 C4 C3 105.1(3) . . ?
C4 C5 C6 125.3(3) . . ?
C4 C5 H5 117.4 . . ?
C6 C5 H5 117.4 . . ?
C5 C6 C22 127.9(3) . . ?
C5 C6 C7 126.3(3) . . ?
C22 C6 C7 105.7(3) . . ?
C7A C7 C8 120.0(3) . . ?
C7A C7 C6 131.4(3) . . ?
C8 C7 C6 108.6(3) . . ?
C7B C7A C7 119.2(3) . . ?
C7B C7A H7A 120.4 . . ?
C7 C7A H7A 120.4 . . ?
C7A C7B C8B 120.5(3) . . ?
C7A C7B H7B 119.7 . . ?
C8B C7B H7B 119.7 . . ?
C8A C8 C7 120.2(3) . . ?
C8A C8 C9 131.9(3) . . ?
C7 C8 C9 107.9(3) . . ?
C8B C8A C8 118.9(3) . . ?
C8B C8A H8A 120.6 . . ?
C8 C8A H8A 120.6 . . ?
C8A C8B C7B 121.1(3) . . ?
C8A C8B H8B 119.5 . . ?
C7B C8B H8B 119.5 . . ?
C10 C9 C22 128.1(3) . . ?
C10 C9 C8 125.9(3) . . ?
C22 C9 C8 105.8(3) . . ?
C11 C10 C9 128.5(3) . . ?
C11 C10 H10 115.7 . . ?
C9 C10 H10 115.7 . . ?
N23 C11 C10 125.9(3) . . ?
N23 C11 C12 106.3(3) . . ?
C10 C11 C12 127.6(3) . . ?
C13 C12 C11 108.5(3) . . ?
C13 C12 C12A 126.3(3) . . ?
C11 C12 C12A 125.2(3) . . ?
C12 C12A H12A 109.5 . . ?
C12 C12A H12B 109.5 . . ?
H12A C12A H12B 109.5 . . ?
C12 C12A H12C 109.5 . . ?
H12A C12A H12C 109.5 . . ?
H12B C12A H12C 109.5 . . ?
C12 C12A H12D 109.5 . . ?
H12A C12A H12D 141.1 . . ?
H12B C12A H12D 56.3 . . ?
H12C C12A H12D 56.3 . . ?
C12 C12A H12E 109.5 . . ?
H12A C12A H12E 56.3 . . ?
H12B C12A H12E 141.1 . . ?
H12C C12A H12E 56.3 . . ?
H12D C12A H12E 109.5 . . ?
C12 C12A H12F 109.5 . . ?
H12A C12A H12F 56.3 . . ?
H12B C12A H12F 56.3 . . ?
H12C C12A H12F 141.1 . . ?
H12D C12A H12F 109.5 . . ?
H12E C12A H12F 109.5 . . ?
C12 C13 C14 108.4(3) . . ?
C12 C13 C13A 127.3(3) . . ?
C14 C13 C13A 124.3(3) . . ?
C13B C13A C13 113.7(3) . . ?
C13B C13A H13A 108.8 . . ?
C13 C13A H13A 108.8 . . ?
C13B C13A H13B 108.8 . . ?
C13 C13A H13B 108.8 . . ?
H13A C13A H13B 107.7 . . ?
C13A C13B H13C 109.5 . . ?
C13A C13B H13D 109.5 . . ?
H13C C13B H13D 109.5 . . ?
C13A C13B H13E 109.5 . . ?
H13C C13B H13E 109.5 . . ?
H13D C13B H13E 109.5 . . ?
C15 C14 N23 125.6(3) . . ?
C15 C14 C13 128.4(3) . . ?
N23 C14 C13 106.1(3) . . ?
C14 C15 C16 129.7(3) . . ?
C14 C15 H15 115.2 . . ?
C16 C15 H15 115.2 . . ?
C15 C16 N24 124.6(3) . . ?
C15 C16 C17 128.7(3) . . ?
N24 C16 C17 106.6(3) . . ?
C18 C17 C16 108.9(3) . . ?
C18 C17 C17A 128.1(3) . . ?
C16 C17 C17A 123.0(3) . . ?
C17 C17A C17B 112.3(3) . . ?
C17 C17A H17A 109.1 . . ?
C17B C17A H17A 109.1 . . ?
C17 C17A H17B 109.1 . . ?
C17B C17A H17B 109.1 . . ?
H17A C17A H17B 107.9 . . ?
C17A C17B H17C 109.5 . . ?
C17A C17B H17D 109.5 . . ?
H17C C17B H17D 109.5 . . ?
C17A C17B H17E 109.5 . . ?
H17C C17B H17E 109.5 . . ?
H17D C17B H17E 109.5 . . ?
C17 C18 C19 107.6(3) . . ?
C17 C18 C18A 128.2(3) . . ?
C19 C18 C18A 124.2(3) . . ?
C18 C18A H18A 109.5 . . ?
C18 C18A H18B 109.5 . . ?
H18A C18A H18B 109.5 . . ?
C18 C18A H18C 109.5 . . ?
H18A C18A H18C 109.5 . . ?
H18B C18A H18C 109.5 . . ?
C18 C18A H18D 109.5 . . ?
H18A C18A H18D 141.1 . . ?
H18B C18A H18D 56.3 . . ?
H18C C18A H18D 56.3 . . ?
C18 C18A H18E 109.5 . . ?
H18A C18A H18E 56.3 . . ?
H18B C18A H18E 141.1 . . ?
H18C C18A H18E 56.3 . . ?
H18D C18A H18E 109.5 . . ?
C18 C18A H18F 109.5 . . ?
H18A C18A H18F 56.3 . . ?
H18B C18A H18F 56.3 . . ?
H18C C18A H18F 141.1 . . ?
H18D C18A H18F 109.5 . . ?
H18E C18A H18F 109.5 . . ?
N24 C19 C20 126.2(3) . . ?
N24 C19 C18 106.8(3) . . ?
C20 C19 C18 127.0(3) . . ?
C19 C20 C1 128.1(3) . . ?
C19 C20 H20 116 . . ?
C1 C20 H20 116 . . ?
C1 C21 C4 112.4(3) . . ?
C1 C21 H21 129(2) . . ?
C4 C21 H21 118(2) . . ?
C9 C22 C6 111.9(3) . . ?
C9 C22 H22 128(2) . . ?
C6 C22 H22 120(2) . . ?
C61 N73 C64 110.3(3) . . ?
C61 N73 H73 124(2) . . ?
C64 N73 H73 117(2) . . ?
C69 N74 C66 109.7(3) . . ?
C69 N74 H74 123(2) . . ?
C66 N74 H74 115(2) . . ?
C71 C51 C70 128.6(3) . . ?
C71 C51 C52 105.8(3) . . ?
C70 C51 C52 125.4(3) . . ?
C52A C52 C53 119.9(3) . . ?
C52A C52 C51 132.2(3) . . ?
C53 C52 C51 107.9(3) . . ?
C52 C52A C52B 119.4(3) . . ?
C52 C52A H52A 120.3 . . ?
C52B C52A H52A 120.3 . . ?
C52A C52B C53B 120.6(4) . . ?
C52A C52B H52B 119.7 . . ?
C53B C52B H52B 119.7 . . ?
C53A C53 C52 120.0(3) . . ?
C53A C53 C54 132.1(3) . . ?
C52 C53 C54 107.9(3) . . ?
C53B C53A C53 119.9(3) . . ?
C53B C53A H53A 120.1 . . ?
C53 C53A H53A 120.1 . . ?
C53A C53B C52B 120.3(3) . . ?
C53A C53B H53B 119.9 . . ?
C52B C53B H53B 119.9 . . ?
C55 C54 C71 127.5(3) . . ?
C55 C54 C53 126.4(3) . . ?
C71 C54 C53 106.1(3) . . ?
C56 C55 C54 125.8(3) . . ?
C56 C55 H55 117.1 . . ?
C54 C55 H55 117.1 . . ?
C55 C56 C72 127.5(3) . . ?
C55 C56 C57 127.0(3) . . ?
C72 C56 C57 105.5(3) . . ?
C57A C57 C58 119.7(3) . . ?
C57A C57 C56 132.0(3) . . ?
C58 C57 C56 108.2(3) . . ?
C57 C57A C57B 119.3(3) . . ?
C57 C57A H57A 120.3 . . ?
C57B C57A H57A 120.3 . . ?
C58B C57B C57A 120.9(3) . . ?
C58B C57B H57B 119.6 . . ?
C57A C57B H57B 119.6 . . ?
C58A C58 C57 120.5(3) . . ?
C58A C58 C59 131.7(3) . . ?
C57 C58 C59 107.8(3) . . ?
C58 C58A C58B 119.3(3) . . ?
C58 C58A H58A 120.4 . . ?
C58B C58A H58A 120.4 . . ?
C57B C58B C58A 120.3(4) . . ?
C57B C58B H58B 119.8 . . ?
C58A C58B H58B 119.8 . . ?
C72 C59 C60 129.1(3) . . ?
C72 C59 C58 105.9(3) . . ?
C60 C59 C58 124.7(3) . . ?
C61 C60 C59 128.0(4) . . ?
C61 C60 H60 116 . . ?
C59 C60 H60 116 . . ?
N73 C61 C60 126.0(3) . . ?
N73 C61 C62 106.4(3) . . ?
C60 C61 C62 127.4(4) . . ?
C63 C62 C61 108.0(3) . . ?
C63 C62 C62A 128.3(3) . . ?
C61 C62 C62A 123.6(3) . . ?
C62 C62A H62A 109.5 . . ?
C62 C62A H62B 109.5 . . ?
H62A C62A H62B 109.5 . . ?
C62 C62A H62C 109.5 . . ?
H62A C62A H62C 109.5 . . ?
H62B C62A H62C 109.5 . . ?
C62 C62A H62D 109.5 . . ?
H62A C62A H62D 141.1 . . ?
H62B C62A H62D 56.3 . . ?
H62C C62A H62D 56.3 . . ?
C62 C62A H62E 109.5 . . ?
H62A C62A H62E 56.3 . . ?
H62B C62A H62E 141.1 . . ?
H62C C62A H62E 56.3 . . ?
H62D C62A H62E 109.5 . . ?
C62 C62A H62F 109.5 . . ?
H62A C62A H62F 56.3 . . ?
H62B C62A H62F 56.3 . . ?
H62C C62A H62F 141.1 . . ?
H62D C62A H62F 109.5 . . ?
H62E C62A H62F 109.5 . . ?
C62 C63 C64 108.9(3) . . ?
C62 C63 C63A 128.0(3) . . ?
C64 C63 C63A 123.1(3) . . ?
C63 C63A C63B 111.9(3) . . ?
C63 C63A H63A 109.2 . . ?
C63B C63A H63A 109.2 . . ?
C63 C63A H63B 109.2 . . ?
C63B C63A H63B 109.2 . . ?
H63A C63A H63B 107.9 . . ?
C63A C63B H63C 109.5 . . ?
C63A C63B H63D 109.5 . . ?
H63C C63B H63D 109.5 . . ?
C63A C63B H63E 109.5 . . ?
H63C C63B H63E 109.5 . . ?
H63D C63B H63E 109.5 . . ?
N73 C64 C65 125.0(3) . . ?
N73 C64 C63 106.2(3) . . ?
C65 C64 C63 128.8(3) . . ?
C66 C65 C64 129.4(3) . . ?
C66 C65 H65 115.3 . . ?
C64 C65 H65 115.3 . . ?
N74 C66 C65 124.8(3) . . ?
N74 C66 C67 107.2(3) . . ?
C65 C66 C67 127.9(3) . . ?
C68 C67 C66 108.2(3) . . ?
C68 C67 C67A 127.6(3) . . ?
C66 C67 C67A 124.1(3) . . ?
C67B C67A C67 114.3(3) . . ?
C67B C67A H67A 108.7 . . ?
C67 C67A H67A 108.7 . . ?
C67B C67A H67B 108.7 . . ?
C67 C67A H67B 108.7 . . ?
H67A C67A H67B 107.6 . . ?
C67A C67B H67C 109.5 . . ?
C67A C67B H67D 109.5 . . ?
H67C C67B H67D 109.5 . . ?
C67A C67B H67E 109.5 . . ?
H67C C67B H67E 109.5 . . ?
H67D C67B H67E 109.5 . . ?
C67 C68 C69 107.9(3) . . ?
C67 C68 C68A 128.1(3) . . ?
C69 C68 C68A 124.0(3) . . ?
C68 C68A H68A 109.5 . . ?
C68 C68A H68B 109.5 . . ?
H68A C68A H68B 109.5 . . ?
C68 C68A H68C 109.5 . . ?
H68A C68A H68C 109.5 . . ?
H68B C68A H68C 109.5 . . ?
C68 C68A H68D 109.5 . . ?
H68A C68A H68D 141.1 . . ?
H68B C68A H68D 56.3 . . ?
H68C C68A H68D 56.3 . . ?
C68 C68A H68E 109.5 . . ?
H68A C68A H68E 56.3 . . ?
H68B C68A H68E 141.1 . . ?
H68C C68A H68E 56.3 . . ?
H68D C68A H68E 109.5 . . ?
C68 C68A H68F 109.5 . . ?
H68A C68A H68F 56.3 . . ?
H68B C68A H68F 56.3 . . ?
H68C C68A H68F 141.1 . . ?
H68D C68A H68F 109.5 . . ?
H68E C68A H68F 109.5 . . ?
N74 C69 C70 126.2(3) . . ?
N74 C69 C68 106.9(3) . . ?
C70 C69 C68 126.7(3) . . ?
C69 C70 C51 128.1(4) . . ?
C69 C70 H70 116 . . ?
C51 C70 H70 116 . . ?
C51 C71 C54 112.2(3) . . ?
C51 C71 H71 128(2) . . ?
C54 C71 H71 119(2) . . ?
C59 C72 C56 112.4(3) . . ?
C59 C72 H72 127.9(19) . . ?
C56 C72 H72 119.7(19) . . ?

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
C21 C1 C2 C2A 179.4(4) . . . . ?
C20 C1 C2 C2A -5.2(6) . . . . ?
C21 C1 C2 C3 -1.0(4) . . . . ?
C20 C1 C2 C3 174.4(3) . . . . ?
C3 C2 C2A C2B 0.0(5) . . . . ?
C1 C2 C2A C2B 179.6(4) . . . . ?
C2 C2A C2B C3B 0.9(6) . . . . ?
C2A C2 C3 C3A -0.9(5) . . . . ?
C1 C2 C3 C3A 179.4(3) . . . . ?
C2A C2 C3 C4 178.5(3) . . . . ?
C1 C2 C3 C4 -1.2(4) . . . . ?
C2 C3 C3A C3B 0.8(5) . . . . ?
C4 C3 C3A C3B -178.4(4) . . . . ?
C3 C3A C3B C2B 0.1(6) . . . . ?
C2A C2B C3B C3A -1.0(6) . . . . ?
C3A C3 C4 C5 3.7(6) . . . . ?
C2 C3 C4 C5 -175.6(3) . . . . ?
C3A C3 C4 C21 -177.8(4) . . . . ?
C2 C3 C4 C21 2.9(4) . . . . ?
C21 C4 C5 C6 -8.4(6) . . . . ?
C3 C4 C5 C6 169.8(3) . . . . ?
C4 C5 C6 C22 -8.1(6) . . . . ?
C4 C5 C6 C7 169.2(4) . . . . ?
C5 C6 C7 C7A 2.5(6) . . . . ?
C22 C6 C7 C7A -179.7(4) . . . . ?
C5 C6 C7 C8 -175.7(3) . . . . ?
C22 C6 C7 C8 2.0(4) . . . . ?
C8 C7 C7A C7B 0.6(5) . . . . ?
C6 C7 C7A C7B -177.5(4) . . . . ?
C7 C7A C7B C8B 0.0(6) . . . . ?
C7A C7 C8 C8A -0.5(5) . . . . ?
C6 C7 C8 C8A 178.1(3) . . . . ?
C7A C7 C8 C9 -178.8(3) . . . . ?
C6 C7 C8 C9 -0.3(4) . . . . ?
C7 C8 C8A C8B -0.3(5) . . . . ?
C9 C8 C8A C8B 177.7(4) . . . . ?
C8 C8A C8B C7B 0.8(6) . . . . ?
C7A C7B C8B C8A -0.7(6) . . . . ?
C8A C8 C9 C10 -4.3(6) . . . . ?
C7 C8 C9 C10 173.8(3) . . . . ?
C8A C8 C9 C22 -179.7(4) . . . . ?
C7 C8 C9 C22 -1.5(4) . . . . ?
C22 C9 C10 C11 7.1(7) . . . . ?
C8 C9 C10 C11 -167.1(4) . . . . ?
C14 N23 C11 C10 176.9(3) . . . . ?
C14 N23 C11 C12 2.5(4) . . . . ?
C9 C10 C11 N23 -4.1(6) . . . . ?
C9 C10 C11 C12 169.2(4) . . . . ?
N23 C11 C12 C13 -0.6(4) . . . . ?
C10 C11 C12 C13 -175.0(4) . . . . ?
N23 C11 C12 C12A 177.3(3) . . . . ?
C10 C11 C12 C12A 3.0(6) . . . . ?
C11 C12 C13 C14 -1.4(4) . . . . ?
C12A C12 C13 C14 -179.3(4) . . . . ?
C11 C12 C13 C13A 176.9(4) . . . . ?
C12A C12 C13 C13A -1.1(6) . . . . ?
C12 C13 C13A C13B 87.2(5) . . . . ?
C14 C13 C13A C13B -94.9(5) . . . . ?
C11 N23 C14 C15 177.6(4) . . . . ?
C11 N23 C14 C13 -3.3(4) . . . . ?
C12 C13 C14 C15 -178.1(4) . . . . ?
C13A C13 C14 C15 3.6(6) . . . . ?
C12 C13 C14 N23 2.8(4) . . . . ?
C13A C13 C14 N23 -175.5(3) . . . . ?
N23 C14 C15 C16 7.4(6) . . . . ?
C13 C14 C15 C16 -171.5(4) . . . . ?
C14 C15 C16 N24 5.5(6) . . . . ?
C14 C15 C16 C17 -172.9(4) . . . . ?
C19 N24 C16 C15 179.2(3) . . . . ?
C19 N24 C16 C17 -2.1(4) . . . . ?
C15 C16 C17 C18 179.6(4) . . . . ?
N24 C16 C17 C18 0.9(4) . . . . ?
C15 C16 C17 C17A -0.4(6) . . . . ?
N24 C16 C17 C17A -179.1(3) . . . . ?
C18 C17 C17A C17B 101.0(5) . . . . ?
C16 C17 C17A C17B -79.0(5) . . . . ?
C16 C17 C18 C19 0.6(4) . . . . ?
C17A C17 C18 C19 -179.4(3) . . . . ?
C16 C17 C18 C18A -176.7(4) . . . . ?
C17A C17 C18 C18A 3.3(6) . . . . ?
C16 N24 C19 C20 179.2(3) . . . . ?
C16 N24 C19 C18 2.4(4) . . . . ?
C17 C18 C19 N24 -1.8(4) . . . . ?
C18A C18 C19 N24 175.6(3) . . . . ?
C17 C18 C19 C20 -178.6(4) . . . . ?
C18A C18 C19 C20 -1.2(6) . . . . ?
N24 C19 C20 C1 -3.5(6) . . . . ?
C18 C19 C20 C1 172.7(4) . . . . ?
C21 C1 C20 C19 5.1(7) . . . . ?
C2 C1 C20 C19 -169.3(4) . . . . ?
C20 C1 C21 C4 -172.2(4) . . . . ?
C2 C1 C21 C4 3.0(4) . . . . ?
C5 C4 C21 C1 174.8(4) . . . . ?
C3 C4 C21 C1 -3.7(4) . . . . ?
C10 C9 C22 C6 -172.2(4) . . . . ?
C8 C9 C22 C6 2.9(4) . . . . ?
C5 C6 C22 C9 174.6(4) . . . . ?
C7 C6 C22 C9 -3.1(4) . . . . ?
C71 C51 C52 C52A -179.6(4) . . . . ?
C70 C51 C52 C52A -4.0(6) . . . . ?
C71 C51 C52 C53 -0.8(4) . . . . ?
C70 C51 C52 C53 174.8(3) . . . . ?
C53 C52 C52A C52B 0.7(5) . . . . ?
C51 C52 C52A C52B 179.4(4) . . . . ?
C52 C52A C52B C53B 1.0(6) . . . . ?
C52A C52 C53 C53A -1.7(5) . . . . ?
C51 C52 C53 C53A 179.3(3) . . . . ?
C52A C52 C53 C54 177.6(3) . . . . ?
C51 C52 C53 C54 -1.4(4) . . . . ?
C52 C53 C53A C53B 1.0(5) . . . . ?
C54 C53 C53A C53B -178.1(4) . . . . ?
C53 C53A C53B C52B 0.8(5) . . . . ?
C52A C52B C53B C53A -1.8(6) . . . . ?
C53A C53 C54 C55 4.5(6) . . . . ?
C52 C53 C54 C55 -174.6(3) . . . . ?
C53A C53 C54 C71 -177.8(4) . . . . ?
C52 C53 C54 C71 3.0(4) . . . . ?
C71 C54 C55 C56 -8.6(6) . . . . ?
C53 C54 C55 C56 168.6(3) . . . . ?
C54 C55 C56 C72 -8.9(6) . . . . ?
C54 C55 C56 C57 169.8(3) . . . . ?
C55 C56 C57 C57A 2.2(6) . . . . ?
C72 C56 C57 C57A -178.9(4) . . . . ?
C55 C56 C57 C58 -175.8(3) . . . . ?
C72 C56 C57 C58 3.2(4) . . . . ?
C58 C57 C57A C57B 1.0(5) . . . . ?
C56 C57 C57A C57B -176.8(4) . . . . ?
C57 C57A C57B C58B -0.4(5) . . . . ?
C57A C57 C58 C58A -1.1(5) . . . . ?
C56 C57 C58 C58A 177.2(3) . . . . ?
C57A C57 C58 C59 -179.5(3) . . . . ?
C56 C57 C58 C59 -1.3(4) . . . . ?
C57 C58 C58A C58B 0.4(5) . . . . ?
C59 C58 C58A C58B 178.5(4) . . . . ?
C57A C57B C58B C58A -0.3(6) . . . . ?
C58 C58A C58B C57B 0.2(6) . . . . ?
C58A C58 C59 C72 -179.4(4) . . . . ?
C57 C58 C59 C72 -1.1(4) . . . . ?
C58A C58 C59 C60 -4.2(6) . . . . ?
C57 C58 C59 C60 174.0(3) . . . . ?
C72 C59 C60 C61 7.1(7) . . . . ?
C58 C59 C60 C61 -166.9(4) . . . . ?
C64 N73 C61 C60 179.6(4) . . . . ?
C64 N73 C61 C62 3.2(4) . . . . ?
C59 C60 C61 N73 -4.6(6) . . . . ?
C59 C60 C61 C62 171.0(4) . . . . ?
N73 C61 C62 C63 -2.3(4) . . . . ?
C60 C61 C62 C63 -178.5(4) . . . . ?
N73 C61 C62 C62A 175.4(3) . . . . ?
C60 C61 C62 C62A -0.9(6) . . . . ?
C61 C62 C63 C64 0.5(4) . . . . ?
C62A C62 C63 C64 -177.1(4) . . . . ?
C61 C62 C63 C63A -179.2(4) . . . . ?
C62A C62 C63 C63A 3.2(6) . . . . ?
C62 C63 C63A C63B 99.1(5) . . . . ?
C64 C63 C63A C63B -80.6(5) . . . . ?
C61 N73 C64 C65 178.1(3) . . . . ?
C61 N73 C64 C63 -2.9(4) . . . . ?
C62 C63 C64 N73 1.5(4) . . . . ?
C63A C63 C64 N73 -178.8(3) . . . . ?
C62 C63 C64 C65 -179.6(4) . . . . ?
C63A C63 C64 C65 0.1(6) . . . . ?
N73 C64 C65 C66 5.8(6) . . . . ?
C63 C64 C65 C66 -172.9(4) . . . . ?
C69 N74 C66 C65 178.1(3) . . . . ?
C69 N74 C66 C67 -2.9(4) . . . . ?
C64 C65 C66 N74 7.0(6) . . . . ?
C64 C65 C66 C67 -171.9(4) . . . . ?
N74 C66 C67 C68 2.2(4) . . . . ?
C65 C66 C67 C68 -178.7(4) . . . . ?
N74 C66 C67 C67A -174.3(3) . . . . ?
C65 C66 C67 C67A 4.8(6) . . . . ?
C68 C67 C67A C67B 89.5(5) . . . . ?
C66 C67 C67A C67B -94.7(5) . . . . ?
C66 C67 C68 C69 -0.8(4) . . . . ?
C67A C67 C68 C69 175.5(3) . . . . ?
C66 C67 C68 C68A -179.6(3) . . . . ?
C67A C67 C68 C68A -3.3(6) . . . . ?
C66 N74 C69 C70 176.8(3) . . . . ?
C66 N74 C69 C68 2.4(4) . . . . ?
C67 C68 C69 N74 -0.9(4) . . . . ?
C68A C68 C69 N74 177.9(3) . . . . ?
C67 C68 C69 C70 -175.3(3) . . . . ?
C68A C68 C69 C70 3.6(6) . . . . ?
N74 C69 C70 C51 -2.9(6) . . . . ?
C68 C69 C70 C51 170.4(4) . . . . ?
C71 C51 C70 C69 6.5(7) . . . . ?
C52 C51 C70 C69 -168.0(4) . . . . ?
C70 C51 C71 C54 -172.5(4) . . . . ?
C52 C51 C71 C54 2.8(4) . . . . ?
C55 C54 C71 C51 173.9(3) . . . . ?
C53 C54 C71 C51 -3.7(4) . . . . ?
C60 C59 C72 C56 -171.6(4) . . . . ?
C58 C59 C72 C56 3.3(4) . . . . ?
C55 C56 C72 C59 174.9(3) . . . . ?
C57 C56 C72 C59 -4.1(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
N23 H23 N24 0.84(4) 2.53(4) 3.012(5) 117(4) .
N73 H73 N74 0.89(4) 2.54(4) 2.994(5) 112(3) .
N74 H74 N73 0.89(4) 2.57(4) 2.994(5) 110(3) .



# start Validation Reply Form
_vrf_PLAT410_shelx               
;
PROBLEM: Short Intra H...H Contact  H21    ..  H22     ..       1.71 Ang.  
PROBLEM: Short Intra H...H Contact  H71    ..  H72     ..       1.69 Ang.  
RESPONSE: Indeed the four H atoms in the internal porphyrinoid
cavity are very crowded.
;
# end Validation Reply Form

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

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

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 1417925'
_audit_update_record             
;
2015-08-10 deposited with the CCDC.
2015-09-10 downloaded from the CCDC.
;

_audit_creation_date             2015-08-10T08:36:20-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

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

# CHEMICAL DATA

_chemical_name_systematic        
;
13,17-diethyl-12,18-dimethyl-2,3-dihydro-21,22-dicarbaporphyrin
;
_chemical_formula_moiety         'C28 H30 N2'
_chemical_formula_sum            'C28 H30 N2'
_chemical_formula_weight         394.54

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

# CRYSTAL DATA

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.6391(4)
_cell_length_b                   11.5516(4)
_cell_length_c                   19.4951(7)
_cell_angle_alpha                80.562(2)
_cell_angle_beta                 85.708(3)
_cell_angle_gamma                85.426(2)
_cell_volume                     2130.30(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9947
_cell_measurement_theta_min      2.22
_cell_measurement_theta_max      28.7
_cell_measurement_temperature    100(2)
_exptl_crystal_description       needle
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.395
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.085
_exptl_crystal_density_diffrn    1.23
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             848
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6914
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_process_details   
;
Apex2 v2014.7-1 (Bruker, 2014)
;

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

# EXPERIMENTAL DATA

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_reflns_number            71618
_diffrn_reflns_av_R_equivalents  0.0488
_diffrn_reflns_theta_min         1.791
_diffrn_reflns_theta_max         28.784
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 1
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        0

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

# STRUCTURE SOLUTION

_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed

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

# REFINEMENT DATA
_refine_special_details          disorder

_reflns_number_total             11056
_reflns_number_gt                7944
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0845
_refine_ls_R_factor_gt           0.055
_refine_ls_wR_factor_ref         0.1484
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_refine_ls_number_reflns         11056
_refine_ls_number_parameters     600
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0617P)²+1.1801P] where P=(Fo²+2Fc²)/3'
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.497
_refine_diff_density_min         -0.367
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
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 0 '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'

_computing_data_collection       'APEX2 (Bruker, 2014)'
_computing_cell_refinement       'APEX2 & SAINT (Bruker, 2013)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SUPERFLIP (Palatinus & Chapuis, 2007)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    
;
ORTEP-3 for Windows (Farrugia, 2012) and 
Mercury CSD (Macrae et al., 2008)
;
_computing_publication_material  
;
WinGX (Farrugia, 1999)
;

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

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
N23 0.17758(13) 0.39499(10) 0.33319(6) 0.0194(3) Uani d 1 . . N
N24 0.03973(13) 0.47558(10) 0.20469(7) 0.0190(3) Uani d 1 . . N
C1 0.09614(16) 0.72733(13) 0.13441(8) 0.0206(3) Uani d 1 . . C
C2 0.11884(18) 0.84633(14) 0.10504(9) 0.0274(3) Uani d 1 . . C
H2 0.077 0.8885 0.0649 0.033 Uiso calc 1 . . H
C3 0.21131(17) 0.89188(14) 0.14372(9) 0.0266(3) Uani d 1 . . C
H3 0.2426 0.9691 0.1334 0.032 Uiso calc 1 . . H
C4 0.25205(16) 0.80557(13) 0.20096(8) 0.0224(3) Uani d 1 . . C
C5 0.33882(16) 0.81784(13) 0.25245(9) 0.0243(3) Uani d 1 . . C
H5 0.3808 0.8905 0.2486 0.029 Uiso calc 1 . . H
C6 0.36979(16) 0.73134(14) 0.30994(9) 0.0241(3) Uani d 1 . . C
C7 0.45809(17) 0.74870(15) 0.36742(9) 0.0287(4) Uani d 1 . . C
H7A 0.4173 0.8146 0.3908 0.034 Uiso calc 1 . . H
H7B 0.5538 0.7661 0.3487 0.034 Uiso calc 1 . . H
C8 0.46003(18) 0.63264(15) 0.41864(9) 0.0289(4) Uani d 1 . . C
H8A 0.5562 0.596 0.4222 0.035 Uiso calc 1 . . H
H8B 0.4221 0.6458 0.4656 0.035 Uiso calc 1 . . H
C9 0.36893(16) 0.55600(13) 0.38835(8) 0.0218(3) Uani d 1 . . C
C10 0.33482(16) 0.44418(14) 0.41782(8) 0.0229(3) Uani d 1 . . C
H10 0.3749 0.4128 0.4606 0.027 Uiso calc 1 . . H
C11 0.24745(16) 0.37039(12) 0.39212(8) 0.0200(3) Uani d 1 . . C
C12 0.22017(17) 0.25319(13) 0.43016(8) 0.0227(3) Uani d 1 . . C
C12A 0.28343(19) 0.19596(15) 0.49612(9) 0.0299(4) Uani d 1 . . C
H12A 0.2403 0.1219 0.5136 0.045 Uiso calc 1 . . H
H12B 0.2675 0.2485 0.531 0.045 Uiso calc 1 . . H
H12C 0.3839 0.18 0.487 0.045 Uiso calc 1 . . H
C13 0.13069(17) 0.20821(13) 0.39261(8) 0.0230(3) Uani d 1 . . C
C13A 0.07169(19) 0.08954(14) 0.40944(9) 0.0298(4) Uani d 1 . . C
H13A -0.0181 0.0929 0.3874 0.036 Uiso calc 1 . . H
H13B 0.0526 0.0702 0.4605 0.036 Uiso calc 1 . . H
C13B 0.1689(2) -0.00727(15) 0.38472(12) 0.0427(5) Uani d 1 . . C
H13C 0.1257 -0.0825 0.3969 0.064 Uiso calc 1 . . H
H13D 0.1866 0.0105 0.3341 0.064 Uiso calc 1 . . H
H13E 0.2573 -0.0123 0.4072 0.064 Uiso calc 1 . . H
C14 0.10525(16) 0.29706(12) 0.33170(8) 0.0202(3) Uani d 1 . . C
C15 0.01990(16) 0.28481(12) 0.27948(8) 0.0203(3) Uani d 1 . . C
H15 -0.0227 0.2123 0.2847 0.024 Uiso calc 1 . . H
C16 -0.01128(15) 0.36586(12) 0.22013(8) 0.0193(3) Uani d 1 . . C
C17 -0.09825(16) 0.35460(13) 0.16584(8) 0.0213(3) Uani d 1 . . C
C17A -0.17098(17) 0.24694(14) 0.16003(9) 0.0260(3) Uani d 1 . . C
H17A -0.2574 0.271 0.1355 0.031 Uiso calc 1 . . H
H17B -0.1979 0.2065 0.2074 0.031 Uiso calc 1 . . H
C17B -0.0808(2) 0.16108(18) 0.12112(13) 0.0478(5) Uani d 1 . . C
H17C -0.1331 0.0926 0.1188 0.072 Uiso calc 1 . . H
H17D -0.0555 0.2 0.0738 0.072 Uiso calc 1 . . H
H17E 0.004 0.1355 0.1457 0.072 Uiso calc 1 . . H
C18 -0.09842(16) 0.45900(13) 0.11910(8) 0.0207(3) Uani d 1 . . C
C18A -0.17711(17) 0.48908(15) 0.05451(9) 0.0266(3) Uani d 1 . . C
H18A -0.158 0.5686 0.0314 0.04 Uiso calc 0.5 . . H
H18B -0.1476 0.4327 0.0229 0.04 Uiso calc 0.5 . . H
H18C -0.2773 0.4856 0.0669 0.04 Uiso calc 0.5 . . H
H18D -0.2306 0.4226 0.0494 0.04 Uiso calc 0.5 . . H
H18E -0.241 0.5586 0.0579 0.04 Uiso calc 0.5 . . H
H18F -0.1113 0.5057 0.0139 0.04 Uiso calc 0.5 . . H
C19 -0.01155(15) 0.53525(12) 0.14363(7) 0.0185(3) Uani d 1 . . C
C20 0.01358(16) 0.65128(13) 0.11186(8) 0.0206(3) Uani d 1 . . C
H20 -0.0317 0.68 0.0702 0.025 Uiso calc 1 . . H
C21 0.17989(17) 0.69771(13) 0.19678(9) 0.0232(3) Uani d 1 . . C
C22 0.32306(18) 0.61779(14) 0.32493(9) 0.0262(3) Uani d 1 . . C
H21A 0.2452(18) 0.6281(16) 0.1955(9) 0.023(4) Uiso d 1 . . H
H21B 0.113(2) 0.6751(17) 0.2430(10) 0.036(5) Uiso d 1 . . H
H22 0.270(2) 0.5856(19) 0.2981(11) 0.041(6) Uiso d 1 . . H
H24 0.102(2) 0.4998(19) 0.2360(11) 0.044(6) Uiso d 1 . . H
C42A 0.40576(19) 0.73169(18) 0.00535(10) 0.0374(4) Uani d 1 . . C
H42A 0.4233 0.812 -0.017 0.056 Uiso calc 1 . . H
H42B 0.3058 0.7266 0.0178 0.056 Uiso calc 1 . . H
H42C 0.4362 0.6766 -0.0269 0.056 Uiso calc 1 . . H
C43A 0.59700(19) 0.89486(14) 0.07148(9) 0.0310(4) Uani d 1 . . C
H43A 0.5986 0.9364 0.1119 0.037 Uiso calc 1 . . H
H43B 0.5203 0.933 0.0429 0.037 Uiso calc 1 . . H
C43B 0.7329(2) 0.90846(17) 0.02869(11) 0.0417(5) Uani d 1 . . C
H43C 0.746 0.9922 0.0134 0.063 Uiso calc 1 . . H
H43D 0.8098 0.8727 0.0569 0.063 Uiso calc 1 . . H
H43E 0.7314 0.8693 -0.0122 0.063 Uiso calc 1 . . H
C47A 0.91754(18) 0.83709(15) 0.28917(9) 0.0278(3) Uani d 1 . . C
H47A 0.9456 0.8542 0.2388 0.033 Uiso calc 1 . . H
H47B 1.0022 0.8354 0.3152 0.033 Uiso calc 1 . . H
C47B 0.8142(2) 0.93621(15) 0.30827(10) 0.0349(4) Uani d 1 . . C
H47C 0.858 1.0113 0.2969 0.052 Uiso calc 1 . . H
H47D 0.731 0.9398 0.2819 0.052 Uiso calc 1 . . H
H47E 0.7876 0.921 0.3583 0.052 Uiso calc 1 . . H
C48A 0.9773(2) 0.62608(19) 0.41814(9) 0.0398(5) Uani d 1 . . C
H48A 1.0533 0.5652 0.4151 0.06 Uiso calc 1 . . H
H48B 0.9241 0.6089 0.463 0.06 Uiso calc 1 . . H
H48C 1.0162 0.7029 0.4142 0.06 Uiso calc 1 . . H
C31 0.7190(3) 0.32903(19) 0.38796(13) 0.0275(6) Uani d 0.8357(16) A 1 C
C32 0.7108(3) 0.21734(19) 0.43050(12) 0.0361(5) Uani d 0.8357(16) A 1 C
H32 0.756 0.1937 0.4727 0.043 Uiso calc 0.8357(16) A 1 H
C33 0.6272(3) 0.14734(18) 0.40174(13) 0.0381(6) Uani d 0.8357(16) A 1 C
H33 0.6078 0.0692 0.4217 0.046 Uiso calc 0.8357(16) A 1 H
C34 0.5754(3) 0.20782(19) 0.33915(14) 0.0338(6) Uani d 0.8357(16) A 1 C
C35 0.4895(2) 0.1686(2) 0.29505(15) 0.0364(6) Uani d 0.8357(16) A 1 C
H35 0.4622 0.0903 0.3076 0.044 Uiso calc 0.8357(16) A 1 H
C36 0.4390(2) 0.23408(19) 0.23336(14) 0.0343(5) Uani d 0.8357(16) A 1 C
C37 0.3467(2) 0.18599(19) 0.18627(15) 0.0402(6) Uani d 0.8357(16) A 1 C
H37A 0.261 0.1574 0.2126 0.048 Uiso calc 0.8357(16) A 1 H
H37B 0.3969 0.1204 0.1658 0.048 Uiso calc 0.8357(16) A 1 H
C38 0.3108(2) 0.29076(19) 0.12898(13) 0.0350(5) Uani d 0.8357(16) A 1 C
H38A 0.3369 0.2703 0.0821 0.042 Uiso calc 0.8357(16) A 1 H
H38B 0.2099 0.3148 0.1321 0.042 Uiso calc 0.8357(16) A 1 H
C39 0.3964(2) 0.38809(19) 0.14323(15) 0.0288(5) Uani d 0.8357(16) A 1 C
C40 0.4062(2) 0.49762(19) 0.10256(12) 0.0251(4) Uani d 0.8357(16) A 1 C
H40 0.3555 0.5134 0.0617 0.03 Uiso calc 0.8357(16) A 1 H
C50 0.7934(2) 0.42168(18) 0.39660(11) 0.0256(4) Uani d 0.8357(16) A 1 C
H50 0.8447 0.4105 0.4372 0.031 Uiso calc 0.8357(16) A 1 H
C51 0.6316(2) 0.32821(16) 0.32759(12) 0.0275(4) Uani d 0.8357(16) A 1 C
H51A 0.6888 0.3415 0.283 0.033 Uiso calc 0.8357(16) A 1 H
H51B 0.5544 0.3903 0.3266 0.033 Uiso calc 0.8357(16) A 1 H
C52 0.4629(3) 0.3486(2) 0.20421(15) 0.0301(5) Uani d 0.8357(16) A 1 C
H52 0.5198 0.396 0.2242 0.036 Uiso calc 0.8357(16) A 1 H
N53 0.56753(14) 0.58959(11) 0.17070(7) 0.0265(4) Uani d 0.8357(16) A 1 N
N54 0.73408(15) 0.56644(11) 0.29286(7) 0.0262(4) Uani d 0.8357(16) A 1 N
H54 0.6776 0.523 0.2764 0.031 Uiso calc 0.8357(16) A 1 H
N54B 0.56753(14) 0.58959(11) 0.17070(7) 0.0262(4) Uani d 0.1643(16) A 2 N
H54B 0.5835 0.5322 0.2055 0.031 Uiso calc 0.1643(16) A 2 H
N53B 0.73408(15) 0.56644(11) 0.29286(7) 0.0265(4) Uani d 0.1643(16) A 2 N
C39B 0.7692(12) 0.3524(11) 0.4124(7) 0.0288(5) Uani d 0.1643(16) A 2 C
C38B 0.7840(11) 0.2401(9) 0.4685(7) 0.0350(5) Uani d 0.1643(16) A 2 C
H38C 0.8816 0.2062 0.4697 0.042 Uiso calc 0.1643(16) A 2 H
H38D 0.7505 0.2564 0.5155 0.042 Uiso calc 0.1643(16) A 2 H
C37B 0.6876(13) 0.1584(12) 0.4409(8) 0.0402(6) Uani d 0.1643(16) A 2 C
H37C 0.7424 0.0862 0.4311 0.048 Uiso calc 0.1643(16) A 2 H
H37D 0.6126 0.1352 0.4769 0.048 Uiso calc 0.1643(16) A 2 H
C36B 0.6267(12) 0.2185(10) 0.3780(8) 0.0343(5) Uani d 0.1643(16) A 2 C
C35B 0.5360(16) 0.1750(12) 0.3375(10) 0.0364(6) Uani d 0.1643(16) A 2 C
H35B 0.5101 0.0974 0.3546 0.044 Uiso calc 0.1643(16) A 2 H
C34B 0.4789(13) 0.2264(11) 0.2772(8) 0.0338(6) Uani d 0.1643(16) A 2 C
C33B 0.3892(15) 0.1864(11) 0.2328(8) 0.0381(6) Uani d 0.1643(16) A 2 C
H33B 0.354 0.1105 0.2415 0.046 Uiso calc 0.1643(16) A 2 H
C32B 0.3593(13) 0.2681(9) 0.1767(7) 0.0361(5) Uani d 0.1643(16) A 2 C
H32B 0.3013 0.256 0.1416 0.043 Uiso calc 0.1643(16) A 2 H
C31B 0.4256(16) 0.3751(11) 0.1766(9) 0.0275(6) Uani d 0.1643(16) A 2 C
C50B 0.4247(13) 0.4702(10) 0.1296(6) 0.0256(4) Uani d 0.1643(16) A 2 C
H50B 0.3691 0.4623 0.0927 0.031 Uiso calc 0.1643(16) A 2 H
C40B 0.8373(12) 0.4503(10) 0.4105(6) 0.0251(4) Uani d 0.1643(16) A 2 C
H40B 0.8995 0.4617 0.444 0.03 Uiso calc 0.1643(16) A 2 H
C52B 0.6780(15) 0.3305(12) 0.3664(10) 0.0301(5) Uani d 0.1643(16) A 2 C
H52B 0.6509 0.3883 0.3284 0.036 Uiso calc 0.1643(16) A 2 H
C51B 0.5053(12) 0.3518(8) 0.2418(6) 0.0275(4) Uani d 0.1643(16) A 2 C
H51C 0.4723 0.4089 0.2733 0.033 Uiso calc 0.1643(16) A 2 H
H51D 0.6062 0.3593 0.2299 0.033 Uiso calc 0.1643(16) A 2 H
C41 0.48582(17) 0.58841(15) 0.11680(9) 0.0281(4) Uani d 1 . . C
C42 0.48501(17) 0.70096(15) 0.06970(9) 0.0289(4) Uani d 1 . . C
C43 0.56727(17) 0.76938(14) 0.09736(9) 0.0250(3) Uani d 1 . . C
C44 0.62000(17) 0.69896(13) 0.15963(8) 0.0239(3) Uani d 1 . . C
C45 0.71035(17) 0.73769(13) 0.20166(8) 0.0231(3) Uani d 1 . . C
H45 0.7385 0.8153 0.1869 0.028 Uiso calc 1 . . H
C46 0.76535(17) 0.67785(13) 0.26270(8) 0.0226(3) Uani d 1 . . C
C47 0.85960(17) 0.71808(14) 0.30479(8) 0.0253(3) Uani d 1 . . C
C48 0.88302(19) 0.62798(15) 0.36019(8) 0.0308(4) Uani d 1 . . C
C49 0.80363(19) 0.53269(15) 0.35238(9) 0.0302(4) Uani d 1 . . C



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

# MOLECULAR GEOMETRY

_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N23 C11 . 1.354(2) ?
N23 C14 . 1.3807(19) ?
N24 C16 . 1.3751(18) ?
N24 C19 . 1.3788(19) ?
N24 H24 . 0.97(2) ?
C1 C20 . 1.374(2) ?
C1 C2 . 1.427(2) ?
C1 C21 . 1.488(2) ?
C2 C3 . 1.395(2) ?
C2 H2 . 0.95 ?
C3 C4 . 1.426(2) ?
C3 H3 . 0.95 ?
C4 C5 . 1.385(2) ?
C4 C21 . 1.491(2) ?
C5 C6 . 1.407(2) ?
C5 H5 . 0.95 ?
C6 C22 . 1.399(2) ?
C6 C7 . 1.505(2) ?
C7 C8 . 1.534(2) ?
C7 H7A . 0.99 ?
C7 H7B . 0.99 ?
C8 C9 . 1.509(2) ?
C8 H8A . 0.99 ?
C8 H8B . 0.99 ?
C9 C10 . 1.379(2) ?
C9 C22 . 1.405(2) ?
C10 C11 . 1.416(2) ?
C10 H10 . 0.95 ?
C11 C12 . 1.466(2) ?
C12 C13 . 1.357(2) ?
C12 C12A . 1.496(2) ?
C12A H12A . 0.98 ?
C12A H12B . 0.98 ?
C12A H12C . 0.98 ?
C13 C14 . 1.458(2) ?
C13 C13A . 1.503(2) ?
C13A C13B . 1.518(3) ?
C13A H13A . 0.99 ?
C13A H13B . 0.99 ?
C13B H13C . 0.98 ?
C13B H13D . 0.98 ?
C13B H13E . 0.98 ?
C14 C15 . 1.387(2) ?
C15 C16 . 1.399(2) ?
C15 H15 . 0.95 ?
C16 C17 . 1.427(2) ?
C17 C18 . 1.387(2) ?
C17 C17A . 1.499(2) ?
C17A C17B . 1.525(2) ?
C17A H17A . 0.99 ?
C17A H17B . 0.99 ?
C17B H17C . 0.98 ?
C17B H17D . 0.98 ?
C17B H17E . 0.98 ?
C18 C19 . 1.422(2) ?
C18 C18A . 1.496(2) ?
C18A H18A . 0.98 ?
C18A H18B . 0.98 ?
C18A H18C . 0.98 ?
C18A H18D . 0.98 ?
C18A H18E . 0.98 ?
C18A H18F . 0.98 ?
C19 C20 . 1.413(2) ?
C20 H20 . 0.95 ?
C21 H21A . 0.984(18) ?
C21 H21B . 1.08(2) ?
C22 H22 . 0.90(2) ?
C42A C42 . 1.496(3) ?
C42A H42A . 0.98 ?
C42A H42B . 0.98 ?
C42A H42C . 0.98 ?
C43A C43 . 1.498(2) ?
C43A C43B . 1.504(3) ?
C43A H43A . 0.99 ?
C43A H43B . 0.99 ?
C43B H43C . 0.98 ?
C43B H43D . 0.98 ?
C43B H43E . 0.98 ?
C47A C47 . 1.501(2) ?
C47A C47B . 1.531(2) ?
C47A H47A . 0.99 ?
C47A H47B . 0.99 ?
C47B H47C . 0.98 ?
C47B H47D . 0.98 ?
C47B H47E . 0.98 ?
C48A C48 . 1.498(3) ?
C48A H48A . 0.98 ?
C48A H48B . 0.98 ?
C48A H48C . 0.98 ?
C31 C50 . 1.374(4) ?
C31 C32 . 1.419(3) ?
C31 C51 . 1.499(3) ?
C32 C33 . 1.392(4) ?
C32 H32 . 0.95 ?
C33 C34 . 1.408(4) ?
C33 H33 . 0.95 ?
C34 C35 . 1.387(4) ?
C34 C51 . 1.509(3) ?
C35 C36 . 1.409(4) ?
C35 H35 . 0.95 ?
C36 C52 . 1.381(3) ?
C36 C37 . 1.521(4) ?
C37 C38 . 1.542(4) ?
C37 H37A . 0.99 ?
C37 H37B . 0.99 ?
C38 C39 . 1.519(3) ?
C38 H38A . 0.99 ?
C38 H38B . 0.99 ?
C39 C40 . 1.385(3) ?
C39 C52 . 1.386(3) ?
C40 C41 . 1.422(3) ?
C40 H40 . 0.95 ?
C50 C49 . 1.429(3) ?
C50 H50 . 0.95 ?
C51 H51A . 0.99 ?
C51 H51B . 0.99 ?
C52 H52 . 0.95 ?
N53 C41 . 1.362(2) ?
N53 C44 . 1.3766(19) ?
N54 C49 . 1.369(2) ?
N54 C46 . 1.3711(19) ?
N54 H54 . 0.88 ?
N54B C41 . 1.362(2) ?
N54B C44 . 1.3766(19) ?
N54B H54B . 0.88 ?
N53B C49 . 1.369(2) ?
N53B C46 . 1.3711(19) ?
C39B C40B . 1.345(15) ?
C39B C52B . 1.369(19) ?
C39B C38B . 1.558(18) ?
C38B C37B . 1.556(16) ?
C38B H38C . 0.99 ?
C38B H38D . 0.99 ?
C37B C36B . 1.45(2) ?
C37B H37C . 0.99 ?
C37B H37D . 0.99 ?
C36B C35B . 1.39(2) ?
C36B C52B . 1.399(17) ?
C35B C34B . 1.36(2) ?
C35B H35B . 0.95 ?
C34B C33B . 1.42(2) ?
C34B C51B . 1.531(15) ?
C33B C32B . 1.355(17) ?
C33B H33B . 0.95 ?
C32B C31B . 1.436(19) ?
C32B H32B . 0.95 ?
C31B C50B . 1.310(17) ?
C31B C51B . 1.51(2) ?
C50B C41 . 1.506(13) ?
C50B H50B . 0.95 ?
C40B C49 . 1.396(12) ?
C40B H40B . 0.95 ?
C52B H52B . 0.95 ?
C51B H51C . 0.99 ?
C51B H51D . 0.99 ?
C41 C42 . 1.463(3) ?
C42 C43 . 1.359(2) ?
C43 C44 . 1.448(2) ?
C44 C45 . 1.385(2) ?
C45 C46 . 1.393(2) ?
C45 H45 . 0.95 ?
C46 C47 . 1.421(2) ?
C47 C48 . 1.390(2) ?
C48 C49 . 1.424(3) ?

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
C11 N23 C14 105.50(12) . . ?
C16 N24 C19 110.11(12) . . ?
C16 N24 H24 119.5(13) . . ?
C19 N24 H24 130.4(13) . . ?
C20 C1 C2 128.56(15) . . ?
C20 C1 C21 124.58(13) . . ?
C2 C1 C21 106.86(13) . . ?
C3 C2 C1 110.24(15) . . ?
C3 C2 H2 124.9 . . ?
C1 C2 H2 124.9 . . ?
C2 C3 C4 110.06(14) . . ?
C2 C3 H3 125 . . ?
C4 C3 H3 125 . . ?
C5 C4 C3 127.67(14) . . ?
C5 C4 C21 125.38(14) . . ?
C3 C4 C21 106.94(14) . . ?
C4 C5 C6 125.23(14) . . ?
C4 C5 H5 117.4 . . ?
C6 C5 H5 117.4 . . ?
C22 C6 C5 127.13(15) . . ?
C22 C6 C7 108.44(15) . . ?
C5 C6 C7 124.41(14) . . ?
C6 C7 C8 105.75(13) . . ?
C6 C7 H7A 110.6 . . ?
C8 C7 H7A 110.6 . . ?
C6 C7 H7B 110.6 . . ?
C8 C7 H7B 110.6 . . ?
H7A C7 H7B 108.7 . . ?
C9 C8 C7 104.81(14) . . ?
C9 C8 H8A 110.8 . . ?
C7 C8 H8A 110.8 . . ?
C9 C8 H8B 110.8 . . ?
C7 C8 H8B 110.8 . . ?
H8A C8 H8B 108.9 . . ?
C10 C9 C22 125.27(15) . . ?
C10 C9 C8 126.05(15) . . ?
C22 C9 C8 108.67(14) . . ?
C9 C10 C11 127.95(15) . . ?
C9 C10 H10 116 . . ?
C11 C10 H10 116 . . ?
N23 C11 C10 127.33(14) . . ?
N23 C11 C12 111.21(13) . . ?
C10 C11 C12 121.45(14) . . ?
C13 C12 C11 106.26(13) . . ?
C13 C12 C12A 128.04(15) . . ?
C11 C12 C12A 125.68(15) . . ?
C12 C12A H12A 109.5 . . ?
C12 C12A H12B 109.5 . . ?
H12A C12A H12B 109.5 . . ?
C12 C12A H12C 109.5 . . ?
H12A C12A H12C 109.5 . . ?
H12B C12A H12C 109.5 . . ?
C12 C13 C14 106.29(13) . . ?
C12 C13 C13A 126.99(15) . . ?
C14 C13 C13A 126.71(15) . . ?
C13 C13A C13B 112.74(15) . . ?
C13 C13A H13A 109 . . ?
C13B C13A H13A 109 . . ?
C13 C13A H13B 109 . . ?
C13B C13A H13B 109 . . ?
H13A C13A H13B 107.8 . . ?
C13A C13B H13C 109.5 . . ?
C13A C13B H13D 109.5 . . ?
H13C C13B H13D 109.5 . . ?
C13A C13B H13E 109.5 . . ?
H13C C13B H13E 109.5 . . ?
H13D C13B H13E 109.5 . . ?
N23 C14 C15 124.67(13) . . ?
N23 C14 C13 110.73(13) . . ?
C15 C14 C13 124.60(14) . . ?
C14 C15 C16 128.17(13) . . ?
C14 C15 H15 115.9 . . ?
C16 C15 H15 115.9 . . ?
N24 C16 C15 123.83(14) . . ?
N24 C16 C17 107.26(13) . . ?
C15 C16 C17 128.92(14) . . ?
C18 C17 C16 107.51(13) . . ?
C18 C17 C17A 127.00(14) . . ?
C16 C17 C17A 125.45(14) . . ?
C17 C17A C17B 112.77(14) . . ?
C17 C17A H17A 109 . . ?
C17B C17A H17A 109 . . ?
C17 C17A H17B 109 . . ?
C17B C17A H17B 109 . . ?
H17A C17A H17B 107.8 . . ?
C17A C17B H17C 109.5 . . ?
C17A C17B H17D 109.5 . . ?
H17C C17B H17D 109.5 . . ?
C17A C17B H17E 109.5 . . ?
H17C C17B H17E 109.5 . . ?
H17D C17B H17E 109.5 . . ?
C17 C18 C19 108.07(13) . . ?
C17 C18 C18A 126.87(14) . . ?
C19 C18 C18A 125.05(14) . . ?
C18 C18A H18A 109.5 . . ?
C18 C18A H18B 109.5 . . ?
H18A C18A H18B 109.5 . . ?
C18 C18A H18C 109.5 . . ?
H18A C18A H18C 109.5 . . ?
H18B C18A H18C 109.5 . . ?
C18 C18A H18D 109.5 . . ?
H18A C18A H18D 141.1 . . ?
H18B C18A H18D 56.3 . . ?
H18C C18A H18D 56.3 . . ?
C18 C18A H18E 109.5 . . ?
H18A C18A H18E 56.3 . . ?
H18B C18A H18E 141.1 . . ?
H18C C18A H18E 56.3 . . ?
H18D C18A H18E 109.5 . . ?
C18 C18A H18F 109.5 . . ?
H18A C18A H18F 56.3 . . ?
H18B C18A H18F 56.3 . . ?
H18C C18A H18F 141.1 . . ?
H18D C18A H18F 109.5 . . ?
H18E C18A H18F 109.5 . . ?
N24 C19 C20 126.97(13) . . ?
N24 C19 C18 107.05(12) . . ?
C20 C19 C18 125.96(14) . . ?
C1 C20 C19 127.38(14) . . ?
C1 C20 H20 116.3 . . ?
C19 C20 H20 116.3 . . ?
C1 C21 C4 105.90(13) . . ?
C1 C21 H21A 113.4(10) . . ?
C4 C21 H21A 112.5(10) . . ?
C1 C21 H21B 110.4(11) . . ?
C4 C21 H21B 110.2(11) . . ?
H21A C21 H21B 104.4(15) . . ?
C6 C22 C9 112.28(15) . . ?
C6 C22 H22 125.7(14) . . ?
C9 C22 H22 122.1(14) . . ?
C42 C42A H42A 109.5 . . ?
C42 C42A H42B 109.5 . . ?
H42A C42A H42B 109.5 . . ?
C42 C42A H42C 109.5 . . ?
H42A C42A H42C 109.5 . . ?
H42B C42A H42C 109.5 . . ?
C43 C43A C43B 113.56(15) . . ?
C43 C43A H43A 108.9 . . ?
C43B C43A H43A 108.9 . . ?
C43 C43A H43B 108.9 . . ?
C43B C43A H43B 108.9 . . ?
H43A C43A H43B 107.7 . . ?
C43A C43B H43C 109.5 . . ?
C43A C43B H43D 109.5 . . ?
H43C C43B H43D 109.5 . . ?
C43A C43B H43E 109.5 . . ?
H43C C43B H43E 109.5 . . ?
H43D C43B H43E 109.5 . . ?
C47 C47A C47B 113.36(14) . . ?
C47 C47A H47A 108.9 . . ?
C47B C47A H47A 108.9 . . ?
C47 C47A H47B 108.9 . . ?
C47B C47A H47B 108.9 . . ?
H47A C47A H47B 107.7 . . ?
C47A C47B H47C 109.5 . . ?
C47A C47B H47D 109.5 . . ?
H47C C47B H47D 109.5 . . ?
C47A C47B H47E 109.5 . . ?
H47C C47B H47E 109.5 . . ?
H47D C47B H47E 109.5 . . ?
C48 C48A H48A 109.5 . . ?
C48 C48A H48B 109.5 . . ?
H48A C48A H48B 109.5 . . ?
C48 C48A H48C 109.5 . . ?
H48A C48A H48C 109.5 . . ?
H48B C48A H48C 109.5 . . ?
C50 C31 C32 128.9(3) . . ?
C50 C31 C51 124.46(19) . . ?
C32 C31 C51 106.6(2) . . ?
C33 C32 C31 110.5(2) . . ?
C33 C32 H32 124.7 . . ?
C31 C32 H32 124.7 . . ?
C32 C33 C34 110.9(2) . . ?
C32 C33 H33 124.5 . . ?
C34 C33 H33 124.5 . . ?
C35 C34 C33 128.6(2) . . ?
C35 C34 C51 124.9(2) . . ?
C33 C34 C51 106.6(2) . . ?
C34 C35 C36 126.0(2) . . ?
C34 C35 H35 117 . . ?
C36 C35 H35 117 . . ?
C52 C36 C35 128.2(3) . . ?
C52 C36 C37 108.0(2) . . ?
C35 C36 C37 123.9(2) . . ?
C36 C37 C38 105.01(17) . . ?
C36 C37 H37A 110.7 . . ?
C38 C37 H37A 110.7 . . ?
C36 C37 H37B 110.7 . . ?
C38 C37 H37B 110.7 . . ?
H37A C37 H37B 108.8 . . ?
C39 C38 C37 104.5(2) . . ?
C39 C38 H38A 110.8 . . ?
C37 C38 H38A 110.8 . . ?
C39 C38 H38B 110.8 . . ?
C37 C38 H38B 110.8 . . ?
H38A C38 H38B 108.9 . . ?
C40 C39 C52 125.8(2) . . ?
C40 C39 C38 126.0(2) . . ?
C52 C39 C38 108.2(2) . . ?
C39 C40 C41 125.5(2) . . ?
C39 C40 H40 117.3 . . ?
C41 C40 H40 117.3 . . ?
C31 C50 C49 128.4(2) . . ?
C31 C50 H50 115.8 . . ?
C49 C50 H50 115.8 . . ?
C31 C51 C34 105.37(19) . . ?
C31 C51 H51A 110.7 . . ?
C34 C51 H51A 110.7 . . ?
C31 C51 H51B 110.7 . . ?
C34 C51 H51B 110.7 . . ?
H51A C51 H51B 108.8 . . ?
C36 C52 C39 114.0(2) . . ?
C36 C52 H52 123 . . ?
C39 C52 H52 123 . . ?
C41 N53 C44 105.89(14) . . ?
C49 N54 C46 110.05(15) . . ?
C49 N54 H54 125 . . ?
C46 N54 H54 125 . . ?
C41 N54B C44 105.89(14) . . ?
C41 N54B H54B 127.1 . . ?
C44 N54B H54B 127.1 . . ?
C49 N53B C46 110.05(15) . . ?
C40B C39B C52B 127.8(14) . . ?
C40B C39B C38B 125.1(12) . . ?
C52B C39B C38B 107.1(12) . . ?
C37B C38B C39B 100.8(11) . . ?
C37B C38B H38C 111.6 . . ?
C39B C38B H38C 111.6 . . ?
C37B C38B H38D 111.6 . . ?
C39B C38B H38D 111.6 . . ?
H38C C38B H38D 109.4 . . ?
C36B C37B C38B 110.3(11) . . ?
C36B C37B H37C 109.6 . . ?
C38B C37B H37C 109.6 . . ?
C36B C37B H37D 109.6 . . ?
C38B C37B H37D 109.6 . . ?
H37C C37B H37D 108.1 . . ?
C35B C36B C52B 127.1(15) . . ?
C35B C36B C37B 127.7(12) . . ?
C52B C36B C37B 105.2(13) . . ?
C34B C35B C36B 130.0(13) . . ?
C34B C35B H35B 115 . . ?
C36B C35B H35B 115 . . ?
C35B C34B C33B 132.8(13) . . ?
C35B C34B C51B 123.1(13) . . ?
C33B C34B C51B 104.0(13) . . ?
C32B C33B C34B 112.7(14) . . ?
C32B C33B H33B 123.6 . . ?
C34B C33B H33B 123.6 . . ?
C33B C32B C31B 112.1(15) . . ?
C33B C32B H32B 124 . . ?
C31B C32B H32B 124 . . ?
C50B C31B C32B 128.9(18) . . ?
C50B C31B C51B 126.8(14) . . ?
C32B C31B C51B 104.3(11) . . ?
C31B C50B C41 138.8(14) . . ?
C31B C50B H50B 110.6 . . ?
C41 C50B H50B 110.6 . . ?
C39B C40B C49 110.4(10) . . ?
C39B C40B H40B 124.8 . . ?
C49 C40B H40B 124.8 . . ?
C39B C52B C36B 116.6(16) . . ?
C39B C52B H52B 121.7 . . ?
C36B C52B H52B 121.7 . . ?
C31B C51B C34B 106.9(11) . . ?
C31B C51B H51C 110.3 . . ?
C34B C51B H51C 110.3 . . ?
C31B C51B H51D 110.3 . . ?
C34B C51B H51D 110.3 . . ?
H51C C51B H51D 108.6 . . ?
N53 C41 C40 129.62(18) . . ?
N54B C41 C42 110.69(14) . . ?
N53 C41 C42 110.69(14) . . ?
C40 C41 C42 119.68(18) . . ?
N54B C41 C50B 106.2(5) . . ?
C42 C41 C50B 143.0(5) . . ?
C43 C42 C41 106.03(15) . . ?
C43 C42 C42A 128.43(17) . . ?
C41 C42 C42A 125.54(15) . . ?
C42 C43 C44 106.94(15) . . ?
C42 C43 C43A 128.06(16) . . ?
C44 C43 C43A 124.98(15) . . ?
N54B C44 C45 125.44(15) . . ?
N53 C44 C45 125.44(15) . . ?
N54B C44 C43 110.44(14) . . ?
N53 C44 C43 110.44(14) . . ?
C45 C44 C43 124.12(14) . . ?
C44 C45 C46 128.55(14) . . ?
C44 C45 H45 115.7 . . ?
C46 C45 H45 115.7 . . ?
N53B C46 C45 124.08(15) . . ?
N54 C46 C45 124.08(15) . . ?
N53B C46 C47 107.96(14) . . ?
N54 C46 C47 107.96(14) . . ?
C45 C46 C47 127.95(14) . . ?
C48 C47 C46 106.78(15) . . ?
C48 C47 C47A 129.24(16) . . ?
C46 C47 C47A 123.98(14) . . ?
C47 C48 C49 108.22(16) . . ?
C47 C48 C48A 127.52(18) . . ?
C49 C48 C48A 124.24(16) . . ?
N53B C49 C40B 151.2(5) . . ?
N53B C49 C48 106.99(14) . . ?
N54 C49 C48 106.99(14) . . ?
C40B C49 C48 101.8(5) . . ?
N54 C49 C50 124.36(19) . . ?
C48 C49 C50 128.65(18) . . ?

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
C20 C1 C2 C3 -179.54(16) . . . . ?
C21 C1 C2 C3 0.82(18) . . . . ?
C1 C2 C3 C4 -0.90(19) . . . . ?
C2 C3 C4 C5 -177.84(16) . . . . ?
C2 C3 C4 C21 0.59(18) . . . . ?
C3 C4 C5 C6 176.48(16) . . . . ?
C21 C4 C5 C6 -1.7(3) . . . . ?
C4 C5 C6 C22 1.8(3) . . . . ?
C4 C5 C6 C7 -176.50(15) . . . . ?
C22 C6 C7 C8 0.27(18) . . . . ?
C5 C6 C7 C8 178.84(15) . . . . ?
C6 C7 C8 C9 -1.48(17) . . . . ?
C7 C8 C9 C10 -177.33(15) . . . . ?
C7 C8 C9 C22 2.21(18) . . . . ?
C22 C9 C10 C11 -1.0(3) . . . . ?
C8 C9 C10 C11 178.42(15) . . . . ?
C14 N23 C11 C10 -178.73(15) . . . . ?
C14 N23 C11 C12 0.05(16) . . . . ?
C9 C10 C11 N23 -0.8(3) . . . . ?
C9 C10 C11 C12 -179.42(15) . . . . ?
N23 C11 C12 C13 -0.49(17) . . . . ?
C10 C11 C12 C13 178.37(14) . . . . ?
N23 C11 C12 C12A 177.97(14) . . . . ?
C10 C11 C12 C12A -3.2(2) . . . . ?
C11 C12 C13 C14 0.69(16) . . . . ?
C12A C12 C13 C14 -177.73(15) . . . . ?
C11 C12 C13 C13A 179.52(15) . . . . ?
C12A C12 C13 C13A 1.1(3) . . . . ?
C12 C13 C13A C13B -83.9(2) . . . . ?
C14 C13 C13A C13B 94.7(2) . . . . ?
C11 N23 C14 C15 -179.67(14) . . . . ?
C11 N23 C14 C13 0.39(16) . . . . ?
C12 C13 C14 N23 -0.71(17) . . . . ?
C13A C13 C14 N23 -179.54(14) . . . . ?
C12 C13 C14 C15 179.36(14) . . . . ?
C13A C13 C14 C15 0.5(2) . . . . ?
N23 C14 C15 C16 -0.8(2) . . . . ?
C13 C14 C15 C16 179.13(15) . . . . ?
C19 N24 C16 C15 -178.95(14) . . . . ?
C19 N24 C16 C17 0.61(16) . . . . ?
C14 C15 C16 N24 -0.8(2) . . . . ?
C14 C15 C16 C17 179.74(15) . . . . ?
N24 C16 C17 C18 -0.55(16) . . . . ?
C15 C16 C17 C18 178.98(15) . . . . ?
N24 C16 C17 C17A 177.39(14) . . . . ?
C15 C16 C17 C17A -3.1(3) . . . . ?
C18 C17 C17A C17B 89.7(2) . . . . ?
C16 C17 C17A C17B -87.9(2) . . . . ?
C16 C17 C18 C19 0.29(17) . . . . ?
C17A C17 C18 C19 -177.61(14) . . . . ?
C16 C17 C18 C18A -178.77(14) . . . . ?
C17A C17 C18 C18A 3.3(3) . . . . ?
C16 N24 C19 C20 178.02(14) . . . . ?
C16 N24 C19 C18 -0.43(16) . . . . ?
C17 C18 C19 N24 0.08(17) . . . . ?
C18A C18 C19 N24 179.16(14) . . . . ?
C17 C18 C19 C20 -178.40(14) . . . . ?
C18A C18 C19 C20 0.7(2) . . . . ?
C2 C1 C20 C19 -177.16(16) . . . . ?
C21 C1 C20 C19 2.4(3) . . . . ?
N24 C19 C20 C1 1.4(3) . . . . ?
C18 C19 C20 C1 179.60(15) . . . . ?
C20 C1 C21 C4 179.91(14) . . . . ?
C2 C1 C21 C4 -0.44(17) . . . . ?
C5 C4 C21 C1 178.40(15) . . . . ?
C3 C4 C21 C1 -0.08(17) . . . . ?
C5 C6 C22 C9 -177.33(15) . . . . ?
C7 C6 C22 C9 1.19(19) . . . . ?
C10 C9 C22 C6 177.36(15) . . . . ?
C8 C9 C22 C6 -2.19(19) . . . . ?
C50 C31 C32 C33 -177.9(2) . . . . ?
C51 C31 C32 C33 0.4(2) . . . . ?
C31 C32 C33 C34 -0.1(3) . . . . ?
C32 C33 C34 C35 179.8(2) . . . . ?
C32 C33 C34 C51 -0.3(2) . . . . ?
C33 C34 C35 C36 178.9(2) . . . . ?
C51 C34 C35 C36 -1.0(4) . . . . ?
C34 C35 C36 C52 -0.3(4) . . . . ?
C34 C35 C36 C37 179.0(2) . . . . ?
C52 C36 C37 C38 -4.2(2) . . . . ?
C35 C36 C37 C38 176.34(19) . . . . ?
C36 C37 C38 C39 5.3(2) . . . . ?
C37 C38 C39 C40 175.5(2) . . . . ?
C37 C38 C39 C52 -4.7(2) . . . . ?
C52 C39 C40 C41 -0.4(3) . . . . ?
C38 C39 C40 C41 179.41(18) . . . . ?
C32 C31 C50 C49 178.2(2) . . . . ?
C51 C31 C50 C49 0.1(3) . . . . ?
C50 C31 C51 C34 177.9(2) . . . . ?
C32 C31 C51 C34 -0.6(2) . . . . ?
C35 C34 C51 C31 -179.5(2) . . . . ?
C33 C34 C51 C31 0.5(2) . . . . ?
C35 C36 C52 C39 -179.3(2) . . . . ?
C37 C36 C52 C39 1.3(3) . . . . ?
C40 C39 C52 C36 -177.9(2) . . . . ?
C38 C39 C52 C36 2.3(3) . . . . ?
C40B C39B C38B C37B -177.3(11) . . . . ?
C52B C39B C38B C37B 1.4(13) . . . . ?
C39B C38B C37B C36B -0.4(12) . . . . ?
C38B C37B C36B C35B 179.4(12) . . . . ?
C38B C37B C36B C52B -0.7(13) . . . . ?
C52B C36B C35B C34B 2(2) . . . . ?
C37B C36B C35B C34B -178.1(13) . . . . ?
C36B C35B C34B C33B 178.2(13) . . . . ?
C36B C35B C34B C51B -1(2) . . . . ?
C35B C34B C33B C32B -179.1(13) . . . . ?
C51B C34B C33B C32B 0.4(13) . . . . ?
C34B C33B C32B C31B -0.3(14) . . . . ?
C33B C32B C31B C50B 177.0(13) . . . . ?
C33B C32B C31B C51B 0.1(13) . . . . ?
C32B C31B C50B C41 -178.3(11) . . . . ?
C51B C31B C50B C41 -2(2) . . . . ?
C52B C39B C40B C49 -0.3(18) . . . . ?
C38B C39B C40B C49 178.1(8) . . . . ?
C40B C39B C52B C36B 176.6(11) . . . . ?
C38B C39B C52B C36B -2.1(16) . . . . ?
C35B C36B C52B C39B -178.3(13) . . . . ?
C37B C36B C52B C39B 1.8(16) . . . . ?
C50B C31B C51B C34B -176.9(12) . . . . ?
C32B C31B C51B C34B 0.1(12) . . . . ?
C35B C34B C51B C31B 179.3(12) . . . . ?
C33B C34B C51B C31B -0.3(12) . . . . ?
C44 N54B C41 C42 -0.34(17) . . . . ?
C44 N54B C41 C50B -178.4(5) . . . . ?
C44 N53 C41 C40 -179.70(17) . . . . ?
C44 N53 C41 C42 -0.34(17) . . . . ?
C39 C40 C41 N53 0.2(3) . . . . ?
C39 C40 C41 C42 -179.07(18) . . . . ?
C31B C50B C41 N54B 2.3(17) . . . . ?
C31B C50B C41 C42 -174.7(11) . . . . ?
N54B C41 C42 C43 -0.56(18) . . . . ?
N53 C41 C42 C43 -0.56(18) . . . . ?
C40 C41 C42 C43 178.88(16) . . . . ?
C50B C41 C42 C43 176.4(7) . . . . ?
N54B C41 C42 C42A -179.45(15) . . . . ?
N53 C41 C42 C42A -179.45(15) . . . . ?
C40 C41 C42 C42A 0.0(3) . . . . ?
C50B C41 C42 C42A -2.5(8) . . . . ?
C41 C42 C43 C44 1.17(18) . . . . ?
C42A C42 C43 C44 -179.98(16) . . . . ?
C41 C42 C43 C43A -177.08(16) . . . . ?
C42A C42 C43 C43A 1.8(3) . . . . ?
C43B C43A C43 C42 -98.2(2) . . . . ?
C43B C43A C43 C44 83.8(2) . . . . ?
C41 N54B C44 C45 -179.03(15) . . . . ?
C41 N54B C44 C43 1.08(17) . . . . ?
C41 N53 C44 C45 -179.03(15) . . . . ?
C41 N53 C44 C43 1.08(17) . . . . ?
C42 C43 C44 N54B -1.46(18) . . . . ?
C43A C43 C44 N54B 176.85(15) . . . . ?
C42 C43 C44 N53 -1.46(18) . . . . ?
C43A C43 C44 N53 176.85(15) . . . . ?
C42 C43 C44 C45 178.65(15) . . . . ?
C43A C43 C44 C45 -3.0(3) . . . . ?
N54B C44 C45 C46 -0.8(3) . . . . ?
N53 C44 C45 C46 -0.8(3) . . . . ?
C43 C44 C45 C46 179.08(15) . . . . ?
C49 N53B C46 C45 -179.51(14) . . . . ?
C49 N53B C46 C47 -0.04(17) . . . . ?
C49 N54 C46 C45 -179.51(14) . . . . ?
C49 N54 C46 C47 -0.04(17) . . . . ?
C44 C45 C46 N53B -1.6(3) . . . . ?
C44 C45 C46 N54 -1.6(3) . . . . ?
C44 C45 C46 C47 179.01(16) . . . . ?
N53B C46 C47 C48 0.04(17) . . . . ?
N54 C46 C47 C48 0.04(17) . . . . ?
C45 C46 C47 C48 179.49(15) . . . . ?
N53B C46 C47 C47A -179.54(14) . . . . ?
N54 C46 C47 C47A -179.54(14) . . . . ?
C45 C46 C47 C47A -0.1(3) . . . . ?
C47B C47A C47 C48 -101.9(2) . . . . ?
C47B C47A C47 C46 77.6(2) . . . . ?
C46 C47 C48 C49 -0.03(18) . . . . ?
C47A C47 C48 C49 179.53(15) . . . . ?
C46 C47 C48 C48A 178.42(15) . . . . ?
C47A C47 C48 C48A -2.0(3) . . . . ?
C46 N53B C49 C40B -179.6(9) . . . . ?
C46 N53B C49 C48 0.02(17) . . . . ?
C46 N54 C49 C48 0.02(17) . . . . ?
C46 N54 C49 C50 179.57(16) . . . . ?
C39B C40B C49 N53B -1.0(16) . . . . ?
C39B C40B C49 C48 179.3(8) . . . . ?
C47 C48 C49 N53B 0.00(18) . . . . ?
C48A C48 C49 N53B -178.50(15) . . . . ?
C47 C48 C49 N54 0.00(18) . . . . ?
C48A C48 C49 N54 -178.50(15) . . . . ?
C47 C48 C49 C40B 179.8(5) . . . . ?
C48A C48 C49 C40B 1.3(5) . . . . ?
C47 C48 C49 C50 -179.52(17) . . . . ?
C48A C48 C49 C50 2.0(3) . . . . ?
C31 C50 C49 N54 2.1(3) . . . . ?
C31 C50 C49 C48 -178.41(19) . . . . ?

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
N24 H24 N23 0.97(2) 2.22(2) 2.9058(18) 127.1(17) .
N54 H54 N53 0.88 2.37 2.935(2) 121.8 .
N54B H54B N53B 0.88 2.42 2.935(2) 117.9 .

# start Validation Reply Form
_vrf_PLAT411_shelx               
;
PROBLEM: Short Inter H...H Contact  H8B   ..  H38D    ..       2.12 Ang.  Short Inter H...H Contact  H43B   ..  H43B    
..       2.12 Ang.  
RESPONSE: These are most likely artifacts of imperfect modeling
 of disorder.  The model is the best possible for the available
 data. H38D is part of the minor (less than 15 percent)
PART of the disordered residue.  H43B is in the region of the
 disordered main residue that was best treated as ordered.  
;
# end Validation Reply Form



# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
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# END of CIF
_chemical_name_common            
13,17-diethyl-12,18-dimethyl-21,22-dicarbachlorin
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: '
