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

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#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
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#  except for the purpose of generating routine backup copies
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#  data retrieval see:
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data_r210

_chemical_name_systematic        
; 
 3β--hydroxy--16β--(4--phenyl--1H--1,2,3--triazol--1--yl)--
17α--hydroxy--17β--methyl--D--homoandrost--5--en--17a--one 
;
_chemical_name_common            ?
_chemical_melting_point_gt       564
_chemical_melting_point_lt       566
_chemical_formula_moiety         'C29 H37 N3 O3'
_chemical_formula_sum            'C29 H37 N3 O3'
_chemical_formula_weight         475.62
_chemical_absolute_configuration unk

_exptl_crystal_preparation       CH₂Cl₂--CH₃OH
_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.135

_cell_length_a                   5.91340(10)
_cell_length_b                   19.9075(4)
_cell_length_c                   23.6392(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2782.83(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'

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

_diffrn_ambient_temperature      295(2)

_refine_ls_R_factor_all          0.0835
_refine_ls_R_factor_gt           0.0465
_refine_ls_wR_factor_ref         0.1158
_refine_ls_wR_factor_gt          0.1038

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.0065(7) 0.84829(18) 0.39199(13) 0.0611(10) Uani 1 1 d . . .
H1 H 0.1015 0.8084 0.3972 0.073 Uiso 1 1 calc R . .
O1 O -0.0812(5) 0.85069(13) 0.33543(10) 0.0765(8) Uani 1 1 d . . .
H1A H -0.1062 0.8124 0.3243 0.115 Uiso 1 1 calc R . .
C2 C 0.1442(7) 0.9129(2) 0.40296(14) 0.0679(11) Uani 1 1 d . . .
H2A H 0.2785 0.9125 0.3794 0.082 Uiso 1 1 calc R . .
H2B H 0.0542 0.9516 0.3923 0.082 Uiso 1 1 calc R . .
C3 C 0.2132(7) 0.9194(2) 0.46386(14) 0.0656(11) Uani 1 1 d . . .
H3A H 0.2970 0.9609 0.4687 0.079 Uiso 1 1 calc R . .
H3B H 0.3133 0.8825 0.4735 0.079 Uiso 1 1 calc R . .
C4 C 0.0114(6) 0.91917(16) 0.50465(14) 0.0514(8) Uani 1 1 d . . .
C41 C -0.1391(7) 0.98059(16) 0.49489(16) 0.0640(10) Uani 1 1 d . . .
H41A H -0.2227 0.9902 0.5287 0.096 Uiso 1 1 calc R . .
H41B H -0.2424 0.9716 0.4645 0.096 Uiso 1 1 calc R . .
H41C H -0.0466 1.0185 0.4853 0.096 Uiso 1 1 calc R . .
C5 C 0.1063(6) 0.91682(17) 0.56691(13) 0.0518(9) Uani 1 1 d . . .
H5 H 0.2234 0.8820 0.5675 0.062 Uiso 1 1 calc R . .
C6 C 0.2223(7) 0.98264(19) 0.58248(13) 0.0619(10) Uani 1 1 d . . .
H6A H 0.1170 1.0194 0.5767 0.074 Uiso 1 1 calc R . .
H6B H 0.3499 0.9896 0.5574 0.074 Uiso 1 1 calc R . .
C7 C 0.3065(6) 0.98419(19) 0.64418(14) 0.0615(10) Uani 1 1 d . . .
H7A H 0.4275 0.9517 0.6488 0.074 Uiso 1 1 calc R . .
H7B H 0.3673 1.0283 0.6525 0.074 Uiso 1 1 calc R . .
C8 C 0.1177(6) 0.96821(16) 0.68570(14) 0.0527(8) Uani 1 1 d . . .
C81 C -0.0674(7) 1.02378(17) 0.68453(16) 0.0629(10) Uani 1 1 d . . .
H81A H -0.1332 1.0260 0.6475 0.094 Uiso 1 1 calc R . .
H81B H -0.0005 1.0663 0.6937 0.094 Uiso 1 1 calc R . .
H81C H -0.1827 1.0133 0.7117 0.094 Uiso 1 1 calc R . .
C9 C 0.2126(6) 0.96518(18) 0.74540(15) 0.0546(9) Uani 1 1 d . . .
O9 O 0.3929(5) 0.99031(16) 0.75640(11) 0.0821(9) Uani 1 1 d . . .
C10 C 0.0839(6) 0.93075(17) 0.79479(14) 0.0552(9) Uani 1 1 d . . .
C101 C -0.1028(7) 0.97533(18) 0.81900(15) 0.0614(9) Uani 1 1 d . . .
H10A H -0.0603 1.0216 0.8151 0.092 Uiso 1 1 calc R . .
H10B H -0.1243 0.9649 0.8583 0.092 Uiso 1 1 calc R . .
H10C H -0.2410 0.9674 0.7988 0.092 Uiso 1 1 calc R . .
O101 O 0.2290(4) 0.91981(13) 0.83999(10) 0.0685(7) Uani 1 1 d . . .
H101 H 0.3344 0.8960 0.8297 0.103 Uiso 1 1 calc R . .
C11 C -0.0062(6) 0.86296(17) 0.77234(14) 0.0545(9) Uani 1 1 d . . .
H11 H 0.1270 0.8352 0.7644 0.065 Uiso 1 1 calc R . .
C12 C -0.1339(6) 0.87015(18) 0.71584(13) 0.0551(9) Uani 1 1 d . . .
H12A H -0.1908 0.8266 0.7041 0.066 Uiso 1 1 calc R . .
H12B H -0.2622 0.8999 0.7209 0.066 Uiso 1 1 calc R . .
C13 C 0.0226(6) 0.89846(16) 0.66965(13) 0.0496(8) Uani 1 1 d . . .
H13 H 0.1541 0.8685 0.6692 0.060 Uiso 1 1 calc R . .
C14 C -0.0743(6) 0.89530(16) 0.60927(14) 0.0511(9) Uani 1 1 d . . .
H14 H -0.2006 0.9270 0.6068 0.061 Uiso 1 1 calc R . .
C15 C -0.1624(7) 0.82587(16) 0.59532(14) 0.0604(10) Uani 1 1 d . . .
H15A H -0.0554 0.7926 0.6089 0.073 Uiso 1 1 calc R . .
H15B H -0.3043 0.8188 0.6150 0.073 Uiso 1 1 calc R . .
C16 C -0.1986(8) 0.81585(18) 0.53364(15) 0.0670(12) Uani 1 1 d . . .
H16 H -0.2792 0.7779 0.5227 0.080 Uiso 1 1 calc R . .
C17 C -0.1268(6) 0.85598(16) 0.49301(14) 0.0527(9) Uani 1 1 d . . .
C18 C -0.1941(8) 0.8466(2) 0.43227(15) 0.0721(12) Uani 1 1 d . . .
H18A H -0.2996 0.8818 0.4218 0.087 Uiso 1 1 calc R . .
H18B H -0.2713 0.8039 0.4283 0.087 Uiso 1 1 calc R . .
N19 N -0.1395(5) 0.82625(14) 0.81440(12) 0.0548(7) Uani 1 1 d . . .
N20 N -0.3682(5) 0.82910(16) 0.81331(13) 0.0603(8) Uani 1 1 d . . .
N21 N -0.4361(5) 0.78935(15) 0.85280(13) 0.0593(8) Uani 1 1 d . . .
C22 C -0.2618(7) 0.75949(16) 0.87977(13) 0.0535(9) Uani 1 1 d . . .
C23 C -0.0663(3) 0.78505(7) 0.85369(6) 0.0572(9) Uani 1 1 d . . .
H23 H 0.0833 0.7749 0.8624 0.069 Uiso 1 1 calc R . .
C24 C -0.2897(3) 0.71154(7) 0.92593(6) 0.0511(9) Uani 1 1 d R . .
C25 C -0.4916(3) 0.67605(7) 0.92949(6) 0.0662(10) Uani 1 1 d R . .
H25 H -0.6021 0.6817 0.9019 0.079 Uiso 1 1 calc R . .
C26 C -0.5282(3) 0.63214(7) 0.97426(6) 0.0688(11) Uani 1 1 d R . .
H26 H -0.6633 0.6084 0.9766 0.083 Uiso 1 1 calc R . .
C27 C -0.3630(3) 0.62373(7) 1.01548(6) 0.0780(13) Uani 1 1 d R . .
H27 H -0.3876 0.5943 1.0454 0.094 Uiso 1 1 calc R . .
C28 C -0.1611(3) 0.65922(7) 1.01192(6) 0.0661(11) Uani 1 1 d R . .
H28 H -0.0506 0.6536 1.0395 0.079 Uiso 1 1 calc R . .
C29 C -0.1245(3) 0.70312(7) 0.96715(6) 0.0646(10) Uani 1 1 d R . .
H29 H 0.0106 0.7269 0.9648 0.078 Uiso 1 1 calc R . .


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.435(4) . ?
C1 C18 1.522(5) . ?
C1 C2 1.544(5) . ?
C1 H1 0.9800 . ?
O1 H1A 0.8200 . ?
C2 C3 1.502(5) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.534(5) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C17 1.525(5) . ?
C4 C41 1.530(4) . ?
C4 C5 1.576(5) . ?
C41 H41A 0.9600 . ?
C41 H41B 0.9600 . ?
C41 H41C 0.9600 . ?
C5 C6 1.524(5) . ?
C5 C14 1.525(5) . ?
C5 H5 0.9800 . ?
C6 C7 1.542(5) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.520(5) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.520(5) . ?
C8 C13 1.546(4) . ?
C8 C81 1.557(5) . ?
C81 H81A 0.9600 . ?
C81 H81B 0.9600 . ?
C81 H81C 0.9600 . ?
C9 O9 1.206(4) . ?
C9 C10 1.553(5) . ?
C10 O101 1.388(4) . ?
C10 C101 1.527(5) . ?
C10 C11 1.545(5) . ?
C101 H10A 0.9600 . ?
C101 H10B 0.9600 . ?
C101 H10C 0.9600 . ?
O101 H101 0.8200 . ?
C11 N19 1.464(4) . ?
C11 C12 1.541(5) . ?
C11 H11 0.9800 . ?
C12 C13 1.538(4) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.539(5) . ?
C13 H13 0.9800 . ?
C14 C15 1.514(4) . ?
C14 H14 0.9800 . ?
C15 C16 1.487(5) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.319(5) . ?
C16 H16 0.9300 . ?
C17 C18 1.502(5) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
N19 C23 1.312(3) . ?
N19 N20 1.354(4) . ?
N20 N21 1.288(4) . ?
N21 C22 1.350(5) . ?
C22 C23 1.406(4) . ?
C22 C24 1.459(4) . ?
C23 H23 0.9300 . ?
C24 C25 1.3898 . ?
C24 C29 1.3900 . ?
C25 C26 1.3897 . ?
C25 H25 0.9300 . ?
C26 C27 1.3899 . ?
C26 H26 0.9300 . ?
C27 C28 1.3898 . ?
C27 H27 0.9300 . ?
C28 C29 1.3897 . ?
C28 H28 0.9300 . ?
C29 H29 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 C18 107.6(3) . . ?
O1 C1 C2 108.6(3) . . ?
C18 C1 C2 108.9(3) . . ?
O1 C1 H1 110.5 . . ?
C18 C1 H1 110.5 . . ?
C2 C1 H1 110.5 . . ?
C1 O1 H1A 109.5 . . ?
C3 C2 C1 112.1(3) . . ?
C3 C2 H2A 109.2 . . ?
C1 C2 H2A 109.2 . . ?
C3 C2 H2B 109.2 . . ?
C1 C2 H2B 109.2 . . ?
H2A C2 H2B 107.9 . . ?
C2 C3 C4 113.0(3) . . ?
C2 C3 H3A 109.0 . . ?
C4 C3 H3A 109.0 . . ?
C2 C3 H3B 109.0 . . ?
C4 C3 H3B 109.0 . . ?
H3A C3 H3B 107.8 . . ?
C17 C4 C41 108.7(3) . . ?
C17 C4 C3 107.8(3) . . ?
C41 C4 C3 110.8(3) . . ?
C17 C4 C5 109.6(3) . . ?
C41 C4 C5 111.8(3) . . ?
C3 C4 C5 108.1(3) . . ?
C4 C41 H41A 109.5 . . ?
C4 C41 H41B 109.5 . . ?
H41A C41 H41B 109.5 . . ?
C4 C41 H41C 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 109.5 . . ?
C6 C5 C14 113.5(3) . . ?
C6 C5 C4 111.1(3) . . ?
C14 C5 C4 111.9(3) . . ?
C6 C5 H5 106.6 . . ?
C14 C5 H5 106.6 . . ?
C4 C5 H5 106.6 . . ?
C5 C6 C7 113.0(3) . . ?
C5 C6 H6A 109.0 . . ?
C7 C6 H6A 109.0 . . ?
C5 C6 H6B 109.0 . . ?
C7 C6 H6B 109.0 . . ?
H6A C6 H6B 107.8 . . ?
C8 C7 C6 111.7(3) . . ?
C8 C7 H7A 109.3 . . ?
C6 C7 H7A 109.3 . . ?
C8 C7 H7B 109.3 . . ?
C6 C7 H7B 109.3 . . ?
H7A C7 H7B 107.9 . . ?
C7 C8 C9 109.7(3) . . ?
C7 C8 C13 107.3(3) . . ?
C9 C8 C13 109.1(3) . . ?
C7 C8 C81 110.9(3) . . ?
C9 C8 C81 107.7(3) . . ?
C13 C8 C81 112.2(3) . . ?
C8 C81 H81A 109.5 . . ?
C8 C81 H81B 109.5 . . ?
H81A C81 H81B 109.5 . . ?
C8 C81 H81C 109.5 . . ?
H81A C81 H81C 109.5 . . ?
H81B C81 H81C 109.5 . . ?
O9 C9 C8 120.7(3) . . ?
O9 C9 C10 117.0(3) . . ?
C8 C9 C10 122.3(3) . . ?
O101 C10 C101 104.4(3) . . ?
O101 C10 C11 109.9(3) . . ?
C101 C10 C11 112.8(3) . . ?
O101 C10 C9 110.2(3) . . ?
C101 C10 C9 112.3(3) . . ?
C11 C10 C9 107.2(3) . . ?
C10 C101 H10A 109.5 . . ?
C10 C101 H10B 109.5 . . ?
H10A C101 H10B 109.5 . . ?
C10 C101 H10C 109.5 . . ?
H10A C101 H10C 109.5 . . ?
H10B C101 H10C 109.5 . . ?
C10 O101 H101 109.5 . . ?
N19 C11 C12 111.8(3) . . ?
N19 C11 C10 112.9(3) . . ?
C12 C11 C10 112.7(3) . . ?
N19 C11 H11 106.3 . . ?
C12 C11 H11 106.3 . . ?
C10 C11 H11 106.3 . . ?
C13 C12 C11 110.7(3) . . ?
C13 C12 H12A 109.5 . . ?
C11 C12 H12A 109.5 . . ?
C13 C12 H12B 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 108.1 . . ?
C12 C13 C14 114.8(3) . . ?
C12 C13 C8 112.0(3) . . ?
C14 C13 C8 113.6(3) . . ?
C12 C13 H13 105.1 . . ?
C14 C13 H13 105.1 . . ?
C8 C13 H13 105.1 . . ?
C15 C14 C5 110.8(3) . . ?
C15 C14 C13 111.6(3) . . ?
C5 C14 C13 109.7(3) . . ?
C15 C14 H14 108.2 . . ?
C5 C14 H14 108.2 . . ?
C13 C14 H14 108.2 . . ?
C16 C15 C14 112.7(3) . . ?
C16 C15 H15A 109.1 . . ?
C14 C15 H15A 109.1 . . ?
C16 C15 H15B 109.1 . . ?
C14 C15 H15B 109.1 . . ?
H15A C15 H15B 107.8 . . ?
C17 C16 C15 125.9(3) . . ?
C17 C16 H16 117.1 . . ?
C15 C16 H16 117.1 . . ?
C16 C17 C18 122.4(3) . . ?
C16 C17 C4 122.7(3) . . ?
C18 C17 C4 114.6(3) . . ?
C17 C18 C1 112.9(3) . . ?
C17 C18 H18A 109.0 . . ?
C1 C18 H18A 109.0 . . ?
C17 C18 H18B 109.0 . . ?
C1 C18 H18B 109.0 . . ?
H18A C18 H18B 107.8 . . ?
C23 N19 N20 111.7(3) . . ?
C23 N19 C11 127.9(3) . . ?
N20 N19 C11 120.3(3) . . ?
N21 N20 N19 105.8(3) . . ?
N20 N21 C22 112.0(3) . . ?
N21 C22 C23 105.2(3) . . ?
N21 C22 C24 123.7(3) . . ?
C23 C22 C24 131.1(3) . . ?
N19 C23 C22 105.4(2) . . ?
N19 C23 H23 127.3 . . ?
C22 C23 H23 127.3 . . ?
C25 C24 C29 120.0 . . ?
C25 C24 C22 118.35(17) . . ?
C29 C24 C22 121.58(17) . . ?
C26 C25 C24 120.0 . . ?
C26 C25 H25 120.0 . . ?
C24 C25 H25 120.0 . . ?
C25 C26 C27 120.0 . . ?
C25 C26 H26 120.0 . . ?
C27 C26 H26 120.0 . . ?
C28 C27 C26 120.0 . . ?
C28 C27 H27 120.0 . . ?
C26 C27 H27 120.0 . . ?
C29 C28 C27 120.0 . . ?
C29 C28 H28 120.0 . . ?
C27 C28 H28 120.0 . . ?
C28 C29 C24 120.0 . . ?
C28 C29 H29 120.0 . . ?
C24 C29 H29 120.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 171.5(3) . . . . ?
C18 C1 C2 C3 54.6(4) . . . . ?
C1 C2 C3 C4 -57.8(5) . . . . ?
C2 C3 C4 C17 54.5(4) . . . . ?
C2 C3 C4 C41 -64.3(4) . . . . ?
C2 C3 C4 C5 172.8(3) . . . . ?
C17 C4 C5 C6 -173.4(3) . . . . ?
C41 C4 C5 C6 -52.9(4) . . . . ?
C3 C4 C5 C6 69.4(4) . . . . ?
C17 C4 C5 C14 -45.5(4) . . . . ?
C41 C4 C5 C14 75.1(3) . . . . ?
C3 C4 C5 C14 -162.7(3) . . . . ?
C14 C5 C6 C7 49.8(4) . . . . ?
C4 C5 C6 C7 176.8(3) . . . . ?
C5 C6 C7 C8 -54.3(4) . . . . ?
C6 C7 C8 C9 175.8(3) . . . . ?
C6 C7 C8 C13 57.5(4) . . . . ?
C6 C7 C8 C81 -65.4(4) . . . . ?
C7 C8 C9 O9 18.4(5) . . . . ?
C13 C8 C9 O9 135.6(4) . . . . ?
C81 C8 C9 O9 -102.4(4) . . . . ?
C7 C8 C9 C10 -162.2(3) . . . . ?
C13 C8 C9 C10 -45.0(4) . . . . ?
C81 C8 C9 C10 77.0(4) . . . . ?
O9 C9 C10 O101 -15.9(4) . . . . ?
C8 C9 C10 O101 164.7(3) . . . . ?
O9 C9 C10 C101 100.1(4) . . . . ?
C8 C9 C10 C101 -79.3(4) . . . . ?
O9 C9 C10 C11 -135.5(4) . . . . ?
C8 C9 C10 C11 45.1(4) . . . . ?
O101 C10 C11 N19 62.5(4) . . . . ?
C101 C10 C11 N19 -53.6(4) . . . . ?
C9 C10 C11 N19 -177.8(3) . . . . ?
O101 C10 C11 C12 -169.8(3) . . . . ?
C101 C10 C11 C12 74.1(4) . . . . ?
C9 C10 C11 C12 -50.0(4) . . . . ?
N19 C11 C12 C13 -170.8(3) . . . . ?
C10 C11 C12 C13 60.9(4) . . . . ?
C11 C12 C13 C14 169.1(3) . . . . ?
C11 C12 C13 C8 -59.5(4) . . . . ?
C7 C8 C13 C12 167.8(3) . . . . ?
C9 C8 C13 C12 49.1(4) . . . . ?
C81 C8 C13 C12 -70.1(4) . . . . ?
C7 C8 C13 C14 -60.2(4) . . . . ?
C9 C8 C13 C14 -178.9(3) . . . . ?
C81 C8 C13 C14 61.8(4) . . . . ?
C6 C5 C14 C15 -173.1(3) . . . . ?
C4 C5 C14 C15 60.2(4) . . . . ?
C6 C5 C14 C13 -49.5(4) . . . . ?
C4 C5 C14 C13 -176.2(3) . . . . ?
C12 C13 C14 C15 -50.2(4) . . . . ?
C8 C13 C14 C15 179.3(3) . . . . ?
C12 C13 C14 C5 -173.3(3) . . . . ?
C8 C13 C14 C5 56.2(4) . . . . ?
C5 C14 C15 C16 -41.9(5) . . . . ?
C13 C14 C15 C16 -164.4(3) . . . . ?
C14 C15 C16 C17 12.0(6) . . . . ?
C15 C16 C17 C18 -172.5(4) . . . . ?
C15 C16 C17 C4 1.3(6) . . . . ?
C41 C4 C17 C16 -107.0(4) . . . . ?
C3 C4 C17 C16 132.8(4) . . . . ?
C5 C4 C17 C16 15.4(5) . . . . ?
C41 C4 C17 C18 67.3(4) . . . . ?
C3 C4 C17 C18 -52.9(4) . . . . ?
C5 C4 C17 C18 -170.3(3) . . . . ?
C16 C17 C18 C1 -131.1(4) . . . . ?
C4 C17 C18 C1 54.6(4) . . . . ?
O1 C1 C18 C17 -170.1(3) . . . . ?
C2 C1 C18 C17 -52.6(4) . . . . ?
C12 C11 N19 C23 145.7(3) . . . . ?
C10 C11 N19 C23 -86.1(4) . . . . ?
C12 C11 N19 N20 -29.7(4) . . . . ?
C10 C11 N19 N20 98.6(4) . . . . ?
C23 N19 N20 N21 0.4(4) . . . . ?
C11 N19 N20 N21 176.5(3) . . . . ?
N19 N20 N21 C22 -0.7(4) . . . . ?
N20 N21 C22 C23 0.7(4) . . . . ?
N20 N21 C22 C24 -179.4(3) . . . . ?
N20 N19 C23 C22 0.0(3) . . . . ?
C11 N19 C23 C22 -175.7(3) . . . . ?
N21 C22 C23 N19 -0.4(3) . . . . ?
C24 C22 C23 N19 179.7(3) . . . . ?
N21 C22 C24 C25 24.3(3) . . . . ?
C23 C22 C24 C25 -155.8(2) . . . . ?
N21 C22 C24 C29 -152.8(2) . . . . ?
C23 C22 C24 C29 27.0(4) . . . . ?
C29 C24 C25 C26 0.0 . . . . ?
C22 C24 C25 C26 -177.17(16) . . . . ?
C24 C25 C26 C27 0.0 . . . . ?
C25 C26 C27 C28 0.0 . . . . ?
C26 C27 C28 C29 0.0 . . . . ?
C27 C28 C29 C24 0.0 . . . . ?
C25 C24 C29 C28 0.0 . . . . ?
C22 C24 C29 C28 177.08(16) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O101 H101 N20 0.82 2.24 3.055(4) 172.8 1_655
O101 H101 N21 0.82 2.58 3.280(4) 144.5 1_655

_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0


#########################################################################

_audit_creation_method           SHELXL97

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

_cell_measurement_reflns_used    14050
_cell_measurement_theta_min      4.35
_cell_measurement_theta_max      69.66

_exptl_crystal_size_max          .2
_exptl_crystal_size_mid          .2
_exptl_crystal_size_min          .2
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1024
_exptl_absorpt_coefficient_mu    0.584
_exptl_absorpt_correction_type   refdelf
_exptl_absorpt_factor_muR        0.063
_exptl_absorpt_process_details   
;
 Walker, N. & Stuart, D (1983) Acta. Cryst. A39, 158-166
;
_exptl_absorpt_correction_T_min  0.9392
_exptl_absorpt_correction_T_max  1.2541
_exptl_special_details           ?

_diffrn_radiation_wavelength     1.5418
_diffrn_detector                 Pilatus100K
_diffrn_detector_type            STOE
_diffrn_detector_area_resol_mean 5.81
_diffrn_source                   'Cu GeniX 3D'
_diffrn_source_voltage           50
_diffrn_source_current           0.600
_diffrn_source_power             0.030
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_monochromator  none
_diffrn_radiation_polarisn_norm  0
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_measurement_method       'rotation method'
_diffrn_measurement_details      '3497 frames, detector distance = 60 mm'
_diffrn_measurement_device_type  'Stoe STADI VARI'
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3036
_diffrn_reflns_av_R_equivalents  0.0000 #0.0417 before absorption coorection
_diffrn_reflns_av_sigmaI/netI    0.0875
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         4.44
_diffrn_reflns_theta_max         70.10
_reflns_number_total             3036
_reflns_number_gt                1835
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'X--AREA  (STOE & CIE, 2012)'
_computing_cell_refinement       'X--AREA  (STOE & CIE, 2012)'
_computing_data_reduction        'X--AREA  (STOE & CIE, 2012)'
_computing_structure_solution    'SHELXS97 (Sheldrick,  2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick,  2008)'
_computing_molecular_graphics    'Ortep--3 (Farrugia,   1997)'
_computing_publication_material  'WinGX    (Farrugia,   1999)'

_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 > 2σ(F²) is used only for calculating R--factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement. R--factors based 
 on F² are statistically about twice as large as those based on F, and 
 R--factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0534P)²P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3036
_refine_ls_number_parameters     301
_refine_ls_number_restraints     0
_refine_ls_goodness_of_fit_ref   0.869
_refine_ls_restrained_S_all      0.869
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        70.10
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.356
_refine_diff_density_min         -0.131
_refine_diff_density_rms         0.035
#######################################################################
_database_code_depnum_ccdc_archive 'CCDC 994279'
