# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_cis-1
_database_code_depnum_ccdc_archive 'CCDC 1443144'
_audit_update_record             
;
2015-12-18 deposited with the CCDC.
2016-02-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        cis-dipyridylcalix[4]pyrrole
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C39 H46 N6 O2'
_chemical_formula_weight         630.82

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

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

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

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

_cell_length_a                   9.931(3)
_cell_length_b                   10.822(3)
_cell_length_c                   16.924(5)
_cell_angle_alpha                95.265(5)
_cell_angle_beta                 98.127(4)
_cell_angle_gamma                92.686(5)
_cell_volume                     1789.7(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)

_cell_measurement_reflns_used    2755

_cell_measurement_theta_min      3.0322

_cell_measurement_theta_max      27.4662


_exptl_crystal_description       Chip

_exptl_crystal_colour            Colorless

_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.171
_exptl_crystal_F_000             676
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.074
_shelx_estimated_absorpt_T_min   0.978
_shelx_estimated_absorpt_T_max   0.996
_exptl_absorpt_correction_type   Numerical

_exptl_absorpt_correction_T_min  0.9138

_exptl_absorpt_correction_T_max  0.9714

_exptl_absorpt_process_details   ?

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku AFC7R Mercury CCD'

_diffrn_measurement_method       dtprofit.ref

_diffrn_detector_area_resol_mean 14.6306

_diffrn_reflns_number            14840
_diffrn_reflns_av_unetI/netI     0.0984
_diffrn_reflns_av_R_equivalents  0.0425
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.032
_diffrn_reflns_theta_max         27.485
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             8100
_reflns_number_gt                3528
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.

 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_structure_solution    
;
????
;

_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Yadokari-XG 2009 (Wakita Nemoto et al., 2009)'

_computing_publication_material  
;Yadokari-XG 2009 (Wakita,Nemoto et al., 2009)
;

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    ?

_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8100
_refine_ls_number_parameters     432
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1547
_refine_ls_R_factor_gt           0.0624
_refine_ls_wR_factor_ref         0.2069
_refine_ls_wR_factor_gt          0.1500
_refine_ls_goodness_of_fit_ref   0.891
_refine_ls_restrained_S_all      0.891
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1020(3) 0.0909(2) 0.37133(17) 0.0490(7) Uani 1 1 d . . . . .
C2 C -0.0334(3) 0.1071(2) 0.3684(2) 0.0624(8) Uani 1 1 d . . . . .
H2 H -0.1000 0.0465 0.3741 0.075 Uiso 1 1 calc R U . . .
C3 C -0.0556(3) 0.2325(2) 0.35503(19) 0.0586(8) Uani 1 1 d . . . . .
H3 H -0.1391 0.2688 0.3511 0.070 Uiso 1 1 calc R U . . .
C4 C 0.0661(3) 0.2900(2) 0.34908(17) 0.0458(6) Uani 1 1 d . . . . .
C5 C 0.1027(3) 0.4232(2) 0.33484(17) 0.0465(7) Uani 1 1 d . . . . .
C6 C 0.1435(3) 0.4301(2) 0.25349(17) 0.0474(7) Uani 1 1 d . . . . .
C7 C 0.0805(3) 0.4738(2) 0.1851(2) 0.0613(8) Uani 1 1 d . . . . .
H7 H -0.0044 0.5074 0.1791 0.074 Uiso 1 1 calc R U . . .
C8 C 0.1655(3) 0.4595(2) 0.1259(2) 0.0653(9) Uani 1 1 d . . . . .
H8 H 0.1458 0.4810 0.0738 0.078 Uiso 1 1 calc R U . . .
C9 C 0.2815(3) 0.4088(2) 0.15739(17) 0.0521(7) Uani 1 1 d . . . . .
C10 C 0.4135(3) 0.3912(2) 0.12541(18) 0.0564(8) Uani 1 1 d . . . . .
C11 C 0.4855(3) 0.2800(2) 0.15524(17) 0.0501(7) Uani 1 1 d . . . . .
C12 C 0.6134(3) 0.2695(2) 0.1937(2) 0.0614(8) Uani 1 1 d . . . . .
H12 H 0.6786 0.3345 0.2105 0.074 Uiso 1 1 calc R U . . .
C13 C 0.6305(3) 0.1420(2) 0.2039(2) 0.0594(8) Uani 1 1 d . . . . .
H13 H 0.7084 0.1089 0.2286 0.071 Uiso 1 1 calc R U . . .
C14 C 0.5127(3) 0.0777(2) 0.17103(17) 0.0470(7) Uani 1 1 d . . . . .
C15 C 0.4717(3) -0.0606(2) 0.16233(17) 0.0464(7) Uani 1 1 d . . . . .
C16 C 0.3542(3) -0.0883(2) 0.20684(16) 0.0447(6) Uani 1 1 d . . . . .
C17 C 0.2590(3) -0.1858(2) 0.19528(18) 0.0493(7) Uani 1 1 d . . . . .
H17 H 0.2468 -0.2473 0.1523 0.059 Uiso 1 1 calc R U . . .
C18 C 0.1826(3) -0.1781(2) 0.25909(18) 0.0509(7) Uani 1 1 d . . . . .
H18 H 0.1113 -0.2334 0.2654 0.061 Uiso 1 1 calc R U . . .
C19 C 0.2305(3) -0.0755(2) 0.31040(17) 0.0467(7) Uani 1 1 d . . . . .
C20 C 0.1847(3) -0.0209(2) 0.38692(17) 0.0516(7) Uani 1 1 d . . . . .
N1 N 0.1624(2) 0.20333(16) 0.35899(13) 0.0470(6) Uani 1 1 d . . . . .
H1N H 0.2480 0.2173 0.3577 0.056 Uiso 1 1 calc R U . . .
N2 N 0.2666(2) 0.39053(16) 0.23517(13) 0.0474(6) Uani 1 1 d . . . . .
H2N H 0.3261 0.3586 0.2680 0.057 Uiso 1 1 calc R U . . .
N3 N 0.4238(2) 0.16194(16) 0.14171(13) 0.0474(6) Uani 1 1 d . . . . .
H3N H 0.3417 0.1436 0.1183 0.057 Uiso 1 1 calc R U . . .
N4 N 0.3360(2) -0.02143(17) 0.27802(13) 0.0477(6) Uani 1 1 d . . . . .
H4N H 0.3839 0.0447 0.2991 0.057 Uiso 1 1 calc R U . . .
C21 C 0.2135(3) 0.4847(2) 0.40038(17) 0.0485(7) Uani 1 1 d . . . . .
C22 C 0.2999(3) 0.5827(2) 0.38675(18) 0.0546(7) Uani 1 1 d . . . . .
H22 H 0.2984 0.6067 0.3353 0.066 Uiso 1 1 calc R U . . .
C23 C 0.3878(3) 0.6440(2) 0.4499(2) 0.0634(8) Uani 1 1 d . . . . .
H23 H 0.4440 0.7097 0.4392 0.076 Uiso 1 1 calc R U . . .
N5 N 0.3975(3) 0.6156(2) 0.52509(17) 0.0651(7) Uani 1 1 d . . . . .
C24 C 0.3165(3) 0.5204(3) 0.5379(2) 0.0664(8) Uani 1 1 d . . . . .
H24 H 0.3220 0.4975 0.5899 0.080 Uiso 1 1 calc R U . . .
C25 C 0.2252(3) 0.4537(3) 0.47906(19) 0.0587(8) Uani 1 1 d . . . . .
H25 H 0.1712 0.3880 0.4917 0.070 Uiso 1 1 calc R U . . .
C26 C 0.5962(3) -0.1294(2) 0.19506(19) 0.0513(7) Uani 1 1 d . . . . .
C27 C 0.7051(3) -0.1437(3) 0.1529(2) 0.0723(9) Uani 1 1 d . . . . .
H27 H 0.7041 -0.1104 0.1041 0.087 Uiso 1 1 calc R U . . .
C28 C 0.8139(4) -0.2066(3) 0.1828(3) 0.0935(13) Uani 1 1 d . . . . .
H28 H 0.8854 -0.2143 0.1530 0.112 Uiso 1 1 calc R U . . .
N6 N 0.8243(3) -0.2575(3) 0.2516(3) 0.1008(12) Uani 1 1 d . . . . .
C29 C 0.7209(4) -0.2418(3) 0.2925(3) 0.0969(14) Uani 1 1 d . . . . .
H29 H 0.7258 -0.2749 0.3416 0.116 Uiso 1 1 calc R U . . .
C30 C 0.6063(3) -0.1798(3) 0.2674(2) 0.0741(10) Uani 1 1 d . . . . .
H30 H 0.5370 -0.1722 0.2989 0.089 Uiso 1 1 calc R U . . .
C31 C -0.0242(3) 0.4997(2) 0.3404(2) 0.0621(8) Uani 1 1 d . . . . .
H31 H -0.0515 0.4961 0.3924 0.093 Uiso 1 1 calc R U . . .
H31A H -0.0023 0.5846 0.3325 0.093 Uiso 1 1 calc R U . . .
H31B H -0.0973 0.4657 0.2998 0.093 Uiso 1 1 calc R U . . .
C32 C 0.5088(4) 0.5096(2) 0.1553(2) 0.0781(11) Uani 1 1 d . . . . .
H32 H 0.5943 0.5010 0.1357 0.117 Uiso 1 1 calc R U . . .
H32A H 0.4669 0.5812 0.1357 0.117 Uiso 1 1 calc R U . . .
H32B H 0.5239 0.5195 0.2129 0.117 Uiso 1 1 calc R U . . .
C33 C 0.3883(4) 0.3760(3) 0.03403(19) 0.0779(10) Uani 1 1 d . . . . .
H33 H 0.4731 0.3648 0.0140 0.117 Uiso 1 1 calc R U . . .
H33A H 0.3269 0.3047 0.0157 0.117 Uiso 1 1 calc R U . . .
H33B H 0.3489 0.4489 0.0148 0.117 Uiso 1 1 calc R U . . .
C34 C 0.4274(3) -0.1060(2) 0.07310(18) 0.0569(8) Uani 1 1 d . . . . .
H34 H 0.5009 -0.0893 0.0436 0.085 Uiso 1 1 calc R U . . .
H34A H 0.4043 -0.1938 0.0676 0.085 Uiso 1 1 calc R U . . .
H34B H 0.3496 -0.0631 0.0525 0.085 Uiso 1 1 calc R U . . .
C35 C 0.0939(3) -0.1204(2) 0.4162(2) 0.0696(9) Uani 1 1 d . . . . .
H35 H 0.0636 -0.0877 0.4649 0.104 Uiso 1 1 calc R U . . .
H35A H 0.0164 -0.1438 0.3760 0.104 Uiso 1 1 calc R U . . .
H35B H 0.1450 -0.1920 0.4261 0.104 Uiso 1 1 calc R U . . .
C36 C 0.3069(3) 0.0158(3) 0.4523(2) 0.0692(9) Uani 1 1 d . . . . .
H36 H 0.2752 0.0501 0.5002 0.104 Uiso 1 1 calc R U . . .
H36A H 0.3561 -0.0564 0.4634 0.104 Uiso 1 1 calc R U . . .
H36B H 0.3658 0.0767 0.4342 0.104 Uiso 1 1 calc R U . . .
O1 O 0.4552(2) 0.24879(18) 0.34490(15) 0.0621(6) Uani 1 1 d . . . . .
H1A H 0.498(4) 0.296(3) 0.391(2) 0.093 Uiso 1 1 d . U . . .
H1B H 0.522(4) 0.236(3) 0.313(2) 0.093 Uiso 1 1 d . U . . .
O2 O 0.1529(3) 0.1178(2) 0.04072(16) 0.0853(7) Uani 1 1 d . . . . .
C37 C 0.0504(4) 0.1383(3) 0.0702(2) 0.0721(10) Uani 1 1 d . . . . .
C38 C -0.0634(4) 0.2002(4) 0.0268(3) 0.1255(18) Uani 1 1 d . . . . .
H38 H -0.0353 0.2309 -0.0201 0.188 Uiso 1 1 calc R U . . .
H38A H -0.0883 0.2682 0.0612 0.188 Uiso 1 1 calc R U . . .
H38B H -0.1402 0.1416 0.0112 0.188 Uiso 1 1 calc R U . . .
C39 C 0.0362(5) 0.1034(4) 0.1513(3) 0.1032(13) Uani 1 1 d . . . . .
H39 H 0.1095 0.0533 0.1693 0.155 Uiso 1 1 calc R U . . .
H39A H -0.0492 0.0571 0.1495 0.155 Uiso 1 1 calc R U . . .
H39B H 0.0392 0.1773 0.1878 0.155 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.359(4) . ?
C1 N1 1.377(3) . ?
C1 C20 1.516(3) . ?
C2 C3 1.418(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.355(4) . ?
C3 H3 0.9300 . ?
C4 N1 1.375(3) . ?
C4 C5 1.519(3) . ?
C5 C6 1.496(4) . ?
C5 C21 1.528(4) . ?
C5 C31 1.548(3) . ?
C6 C7 1.370(4) . ?
C6 N2 1.380(3) . ?
C7 C8 1.401(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.361(4) . ?
C8 H8 0.9300 . ?
C9 N2 1.376(3) . ?
C9 C10 1.501(4) . ?
C10 C11 1.519(4) . ?
C10 C33 1.524(4) . ?
C10 C32 1.557(4) . ?
C11 C12 1.357(4) . ?
C11 N3 1.376(3) . ?
C12 C13 1.420(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.353(4) . ?
C13 H13 0.9300 . ?
C14 N3 1.375(3) . ?
C14 C15 1.520(3) . ?
C15 C16 1.509(4) . ?
C15 C26 1.535(3) . ?
C15 C34 1.540(4) . ?
C16 C17 1.365(3) . ?
C16 N4 1.386(3) . ?
C17 C18 1.403(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.368(4) . ?
C18 H18 0.9300 . ?
C19 N4 1.379(3) . ?
C19 C20 1.511(4) . ?
C20 C36 1.533(4) . ?
C20 C35 1.533(4) . ?
N1 H1N 0.8600 . ?
N2 H2N 0.8600 . ?
N3 H3N 0.8600 . ?
N4 H4N 0.8600 . ?
C21 C22 1.389(4) . ?
C21 C25 1.393(4) . ?
C22 C23 1.377(4) . ?
C22 H22 0.9300 . ?
C23 N5 1.328(4) . ?
C23 H23 0.9300 . ?
N5 C24 1.330(4) . ?
C24 C25 1.373(4) . ?
C24 H24 0.9300 . ?
C25 H25 0.9300 . ?
C26 C30 1.378(4) . ?
C26 C27 1.384(4) . ?
C27 C28 1.366(4) . ?
C27 H27 0.9300 . ?
C28 N6 1.326(5) . ?
C28 H28 0.9300 . ?
N6 C29 1.326(5) . ?
C29 C30 1.384(5) . ?
C29 H29 0.9300 . ?
C30 H30 0.9300 . ?
C31 H31 0.9600 . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C32 H32 0.9600 . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C33 H33 0.9600 . ?
C33 H33A 0.9600 . ?
C33 H33B 0.9600 . ?
C34 H34 0.9600 . ?
C34 H34A 0.9600 . ?
C34 H34B 0.9600 . ?
C35 H35 0.9600 . ?
C35 H35A 0.9600 . ?
C35 H35B 0.9600 . ?
C36 H36 0.9600 . ?
C36 H36A 0.9600 . ?
C36 H36B 0.9600 . ?
O1 H1A 0.93(4) . ?
O1 H1B 0.93(4) . ?
O2 C37 1.217(4) . ?
C37 C38 1.480(5) . ?
C37 C39 1.480(5) . ?
C38 H38 0.9600 . ?
C38 H38A 0.9600 . ?
C38 H38B 0.9600 . ?
C39 H39 0.9600 . ?
C39 H39A 0.9600 . ?
C39 H39B 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 N1 106.7(2) . . ?
C2 C1 C20 131.5(2) . . ?
N1 C1 C20 121.8(2) . . ?
C1 C2 C3 108.1(2) . . ?
C1 C2 H2 125.9 . . ?
C3 C2 H2 125.9 . . ?
C4 C3 C2 107.9(2) . . ?
C4 C3 H3 126.0 . . ?
C2 C3 H3 126.0 . . ?
C3 C4 N1 107.1(2) . . ?
C3 C4 C5 130.7(2) . . ?
N1 C4 C5 122.2(2) . . ?
C6 C5 C4 111.3(2) . . ?
C6 C5 C21 111.1(2) . . ?
C4 C5 C21 111.6(2) . . ?
C6 C5 C31 108.5(2) . . ?
C4 C5 C31 108.4(2) . . ?
C21 C5 C31 105.8(2) . . ?
C7 C6 N2 105.6(3) . . ?
C7 C6 C5 132.3(3) . . ?
N2 C6 C5 122.1(2) . . ?
C6 C7 C8 108.6(3) . . ?
C6 C7 H7 125.7 . . ?
C8 C7 H7 125.7 . . ?
C9 C8 C7 108.7(3) . . ?
C9 C8 H8 125.7 . . ?
C7 C8 H8 125.7 . . ?
C8 C9 N2 106.1(3) . . ?
C8 C9 C10 131.1(3) . . ?
N2 C9 C10 122.2(3) . . ?
C9 C10 C11 112.8(2) . . ?
C9 C10 C33 110.0(3) . . ?
C11 C10 C33 109.1(2) . . ?
C9 C10 C32 107.5(2) . . ?
C11 C10 C32 107.8(3) . . ?
C33 C10 C32 109.5(2) . . ?
C12 C11 N3 106.7(2) . . ?
C12 C11 C10 131.6(2) . . ?
N3 C11 C10 121.5(3) . . ?
C11 C12 C13 108.3(2) . . ?
C11 C12 H12 125.9 . . ?
C13 C12 H12 125.9 . . ?
C14 C13 C12 107.5(3) . . ?
C14 C13 H13 126.2 . . ?
C12 C13 H13 126.2 . . ?
C13 C14 N3 107.4(2) . . ?
C13 C14 C15 131.5(2) . . ?
N3 C14 C15 121.1(2) . . ?
C16 C15 C14 111.5(2) . . ?
C16 C15 C26 110.2(2) . . ?
C14 C15 C26 108.1(2) . . ?
C16 C15 C34 108.1(2) . . ?
C14 C15 C34 109.6(2) . . ?
C26 C15 C34 109.3(2) . . ?
C17 C16 N4 105.9(2) . . ?
C17 C16 C15 130.5(2) . . ?
N4 C16 C15 123.1(2) . . ?
C16 C17 C18 108.7(2) . . ?
C16 C17 H17 125.7 . . ?
C18 C17 H17 125.7 . . ?
C19 C18 C17 108.6(2) . . ?
C19 C18 H18 125.7 . . ?
C17 C18 H18 125.7 . . ?
C18 C19 N4 106.1(2) . . ?
C18 C19 C20 131.3(2) . . ?
N4 C19 C20 122.6(2) . . ?
C19 C20 C1 110.4(2) . . ?
C19 C20 C36 111.0(2) . . ?
C1 C20 C36 110.1(2) . . ?
C19 C20 C35 108.0(2) . . ?
C1 C20 C35 108.6(2) . . ?
C36 C20 C35 108.6(2) . . ?
C4 N1 C1 110.2(2) . . ?
C4 N1 H1N 124.9 . . ?
C1 N1 H1N 124.9 . . ?
C9 N2 C6 111.1(2) . . ?
C9 N2 H2N 124.5 . . ?
C6 N2 H2N 124.5 . . ?
C14 N3 C11 110.0(2) . . ?
C14 N3 H3N 125.0 . . ?
C11 N3 H3N 125.0 . . ?
C19 N4 C16 110.8(2) . . ?
C19 N4 H4N 124.6 . . ?
C16 N4 H4N 124.6 . . ?
C22 C21 C25 116.0(3) . . ?
C22 C21 C5 121.8(3) . . ?
C25 C21 C5 121.9(2) . . ?
C23 C22 C21 119.6(3) . . ?
C23 C22 H22 120.2 . . ?
C21 C22 H22 120.2 . . ?
N5 C23 C22 124.3(3) . . ?
N5 C23 H23 117.8 . . ?
C22 C23 H23 117.8 . . ?
C23 N5 C24 116.1(3) . . ?
N5 C24 C25 124.0(3) . . ?
N5 C24 H24 118.0 . . ?
C25 C24 H24 118.0 . . ?
C24 C25 C21 120.0(3) . . ?
C24 C25 H25 120.0 . . ?
C21 C25 H25 120.0 . . ?
C30 C26 C27 116.5(3) . . ?
C30 C26 C15 122.3(3) . . ?
C27 C26 C15 121.2(3) . . ?
C28 C27 C26 120.1(3) . . ?
C28 C27 H27 120.0 . . ?
C26 C27 H27 120.0 . . ?
N6 C28 C27 124.3(4) . . ?
N6 C28 H28 117.8 . . ?
C27 C28 H28 117.8 . . ?
C28 N6 C29 115.4(3) . . ?
N6 C29 C30 124.7(4) . . ?
N6 C29 H29 117.7 . . ?
C30 C29 H29 117.7 . . ?
C26 C30 C29 119.0(4) . . ?
C26 C30 H30 120.5 . . ?
C29 C30 H30 120.5 . . ?
C5 C31 H31 109.5 . . ?
C5 C31 H31A 109.5 . . ?
H31 C31 H31A 109.5 . . ?
C5 C31 H31B 109.5 . . ?
H31 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C10 C32 H32 109.5 . . ?
C10 C32 H32A 109.5 . . ?
H32 C32 H32A 109.5 . . ?
C10 C32 H32B 109.5 . . ?
H32 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C10 C33 H33 109.5 . . ?
C10 C33 H33A 109.5 . . ?
H33 C33 H33A 109.5 . . ?
C10 C33 H33B 109.5 . . ?
H33 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
C15 C34 H34 109.5 . . ?
C15 C34 H34A 109.5 . . ?
H34 C34 H34A 109.5 . . ?
C15 C34 H34B 109.5 . . ?
H34 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
C20 C35 H35 109.5 . . ?
C20 C35 H35A 109.5 . . ?
H35 C35 H35A 109.5 . . ?
C20 C35 H35B 109.5 . . ?
H35 C35 H35B 109.5 . . ?
H35A C35 H35B 109.5 . . ?
C20 C36 H36 109.5 . . ?
C20 C36 H36A 109.5 . . ?
H36 C36 H36A 109.5 . . ?
C20 C36 H36B 109.5 . . ?
H36 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
H1A O1 H1B 106(3) . . ?
O2 C37 C38 121.2(4) . . ?
O2 C37 C39 120.9(3) . . ?
C38 C37 C39 117.9(4) . . ?
C37 C38 H38 109.5 . . ?
C37 C38 H38A 109.5 . . ?
H38 C38 H38A 109.5 . . ?
C37 C38 H38B 109.5 . . ?
H38 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
C37 C39 H39 109.5 . . ?
C37 C39 H39A 109.5 . . ?
H39 C39 H39A 109.5 . . ?
C37 C39 H39B 109.5 . . ?
H39 C39 H39B 109.5 . . ?
H39A C39 H39B 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 -0.8(3) . . . . ?
C20 C1 C2 C3 177.4(3) . . . . ?
C1 C2 C3 C4 0.8(4) . . . . ?
C2 C3 C4 N1 -0.4(3) . . . . ?
C2 C3 C4 C5 179.9(3) . . . . ?
C3 C4 C5 C6 -110.4(3) . . . . ?
N1 C4 C5 C6 69.9(3) . . . . ?
C3 C4 C5 C21 124.9(3) . . . . ?
N1 C4 C5 C21 -54.7(3) . . . . ?
C3 C4 C5 C31 8.9(4) . . . . ?
N1 C4 C5 C31 -170.8(2) . . . . ?
C4 C5 C6 C7 108.7(3) . . . . ?
C21 C5 C6 C7 -126.3(3) . . . . ?
C31 C5 C6 C7 -10.4(4) . . . . ?
C4 C5 C6 N2 -72.8(3) . . . . ?
C21 C5 C6 N2 52.2(3) . . . . ?
C31 C5 C6 N2 168.0(2) . . . . ?
N2 C6 C7 C8 0.4(3) . . . . ?
C5 C6 C7 C8 179.1(3) . . . . ?
C6 C7 C8 C9 -0.9(3) . . . . ?
C7 C8 C9 N2 0.9(3) . . . . ?
C7 C8 C9 C10 -169.8(3) . . . . ?
C8 C9 C10 C11 -151.2(3) . . . . ?
N2 C9 C10 C11 39.4(3) . . . . ?
C8 C9 C10 C33 -29.1(4) . . . . ?
N2 C9 C10 C33 161.5(2) . . . . ?
C8 C9 C10 C32 90.1(4) . . . . ?
N2 C9 C10 C32 -79.3(3) . . . . ?
C9 C10 C11 C12 -125.2(3) . . . . ?
C33 C10 C11 C12 112.2(4) . . . . ?
C32 C10 C11 C12 -6.7(4) . . . . ?
C9 C10 C11 N3 58.2(3) . . . . ?
C33 C10 C11 N3 -64.3(3) . . . . ?
C32 C10 C11 N3 176.8(2) . . . . ?
N3 C11 C12 C13 0.1(3) . . . . ?
C10 C11 C12 C13 -176.9(3) . . . . ?
C11 C12 C13 C14 0.3(4) . . . . ?
C12 C13 C14 N3 -0.5(3) . . . . ?
C12 C13 C14 C15 178.5(3) . . . . ?
C13 C14 C15 C16 118.1(3) . . . . ?
N3 C14 C15 C16 -63.0(3) . . . . ?
C13 C14 C15 C26 -3.2(4) . . . . ?
N3 C14 C15 C26 175.7(2) . . . . ?
C13 C14 C15 C34 -122.3(3) . . . . ?
N3 C14 C15 C34 56.6(3) . . . . ?
C14 C15 C16 C17 155.9(3) . . . . ?
C26 C15 C16 C17 -84.0(3) . . . . ?
C34 C15 C16 C17 35.3(3) . . . . ?
C14 C15 C16 N4 -33.8(3) . . . . ?
C26 C15 C16 N4 86.3(3) . . . . ?
C34 C15 C16 N4 -154.3(2) . . . . ?
N4 C16 C17 C18 0.3(3) . . . . ?
C15 C16 C17 C18 171.9(2) . . . . ?
C16 C17 C18 C19 0.0(3) . . . . ?
C17 C18 C19 N4 -0.2(3) . . . . ?
C17 C18 C19 C20 178.3(3) . . . . ?
C18 C19 C20 C1 -102.3(3) . . . . ?
N4 C19 C20 C1 76.0(3) . . . . ?
C18 C19 C20 C36 135.2(3) . . . . ?
N4 C19 C20 C36 -46.5(3) . . . . ?
C18 C19 C20 C35 16.3(4) . . . . ?
N4 C19 C20 C35 -165.4(2) . . . . ?
C2 C1 C20 C19 107.9(4) . . . . ?
N1 C1 C20 C19 -74.1(3) . . . . ?
C2 C1 C20 C36 -129.2(4) . . . . ?
N1 C1 C20 C36 48.9(3) . . . . ?
C2 C1 C20 C35 -10.4(4) . . . . ?
N1 C1 C20 C35 167.6(3) . . . . ?
C3 C4 N1 C1 -0.1(3) . . . . ?
C5 C4 N1 C1 179.7(2) . . . . ?
C2 C1 N1 C4 0.6(3) . . . . ?
C20 C1 N1 C4 -177.9(2) . . . . ?
C8 C9 N2 C6 -0.6(3) . . . . ?
C10 C9 N2 C6 171.0(2) . . . . ?
C7 C6 N2 C9 0.1(3) . . . . ?
C5 C6 N2 C9 -178.7(2) . . . . ?
C13 C14 N3 C11 0.5(3) . . . . ?
C15 C14 N3 C11 -178.6(2) . . . . ?
C12 C11 N3 C14 -0.4(3) . . . . ?
C10 C11 N3 C14 176.9(2) . . . . ?
C18 C19 N4 C16 0.4(3) . . . . ?
C20 C19 N4 C16 -178.3(2) . . . . ?
C17 C16 N4 C19 -0.4(3) . . . . ?
C15 C16 N4 C19 -172.8(2) . . . . ?
C6 C5 C21 C22 29.8(3) . . . . ?
C4 C5 C21 C22 154.6(2) . . . . ?
C31 C5 C21 C22 -87.8(3) . . . . ?
C6 C5 C21 C25 -156.5(2) . . . . ?
C4 C5 C21 C25 -31.7(3) . . . . ?
C31 C5 C21 C25 86.0(3) . . . . ?
C25 C21 C22 C23 -1.4(4) . . . . ?
C5 C21 C22 C23 172.7(2) . . . . ?
C21 C22 C23 N5 0.5(4) . . . . ?
C22 C23 N5 C24 0.7(5) . . . . ?
C23 N5 C24 C25 -1.0(4) . . . . ?
N5 C24 C25 C21 0.0(5) . . . . ?
C22 C21 C25 C24 1.1(4) . . . . ?
C5 C21 C25 C24 -172.9(2) . . . . ?
C16 C15 C26 C30 -15.7(3) . . . . ?
C14 C15 C26 C30 106.4(3) . . . . ?
C34 C15 C26 C30 -134.3(3) . . . . ?
C16 C15 C26 C27 164.4(2) . . . . ?
C14 C15 C26 C27 -73.4(3) . . . . ?
C34 C15 C26 C27 45.8(3) . . . . ?
C30 C26 C27 C28 0.9(4) . . . . ?
C15 C26 C27 C28 -179.2(3) . . . . ?
C26 C27 C28 N6 0.1(6) . . . . ?
C27 C28 N6 C29 -1.2(6) . . . . ?
C28 N6 C29 C30 1.3(6) . . . . ?
C27 C26 C30 C29 -0.9(5) . . . . ?
C15 C26 C30 C29 179.2(3) . . . . ?
N6 C29 C30 C26 -0.2(6) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1N O1 0.86 2.11 2.972(3) 175.7 .
N2 H2N O1 0.86 2.17 3.019(3) 170.2 .
N3 H3N O2 0.86 2.12 2.969(4) 167.9 .
N4 H4N O1 0.86 2.32 3.150(3) 163.6 .
C30 H30 N4 0.93 2.64 3.269(4) 125.2 .
O1 H1A N5 0.93(4) 1.80(4) 2.726(3) 172(3) 2_666
N1 H1N O1 0.86 2.11 2.972(3) 175.7 .
N2 H2N O1 0.86 2.17 3.019(3) 170.2 .
N3 H3N O2 0.86 2.12 2.969(4) 167.9 .
N4 H4N O1 0.86 2.32 3.150(3) 163.6 .
C30 H30 N4 0.93 2.64 3.269(4) 125.2 .
O1 H1A N5 0.93(4) 1.80(4) 2.726(3) 172(3) 2_666

_refine_diff_density_max         0.303
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.038


_symmetry_cell_setting           ?
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_monochromator  'Graphite Monochromator'
_chemical_absolute_configuration ?

####################################################################### 
# 
# 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_trans-1
_database_code_depnum_ccdc_archive 'CCDC 1443145'
_audit_update_record             
;
2015-12-18 deposited with the CCDC.
2016-02-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        trans-dipyridylcalix[4]pyrrole
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C36 H40 N6 O'
_chemical_formula_weight         572.74

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

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

_cell_length_a                   17.908(10)
_cell_length_b                   12.767(7)
_cell_length_c                   14.894(8)
_cell_angle_alpha                90
_cell_angle_beta                 102.821(10)
_cell_angle_gamma                90
_cell_volume                     3321(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)

_cell_measurement_reflns_used    2884

_cell_measurement_theta_min      3.1912

_cell_measurement_theta_max      27.4276


_exptl_crystal_description       Prism

_exptl_crystal_colour            Orange

_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.146
_exptl_crystal_F_000             1224
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2000

_exptl_crystal_size_mid          0.2000

_exptl_crystal_size_min          0.2000

_exptl_absorpt_coefficient_mu    0.071
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Multi-scan

_exptl_absorpt_correction_T_min  0.7151

_exptl_absorpt_correction_T_max  1.0000

_exptl_absorpt_process_details   ?

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)

_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku AFC7R Mercury CCD'

_diffrn_measurement_method       dtprofit.ref

_diffrn_detector_area_resol_mean 14.6306

_diffrn_reflns_number            13208
_diffrn_reflns_av_unetI/netI     0.0634
_diffrn_reflns_av_R_equivalents  0.0584
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.191
_diffrn_reflns_theta_max         27.481
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3799
_reflns_number_gt                2158
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.

 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_structure_solution    
;
????
;

_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Yadokari-XG 2009 (Wakita Nemoto et al., 2009)'

_computing_publication_material  
;Yadokari-XG 2009 (Wakita,Nemoto et al., 2009)
;

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    ?

_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3799
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1521
_refine_ls_R_factor_gt           0.0861
_refine_ls_wR_factor_ref         0.2344
_refine_ls_wR_factor_gt          0.1972
_refine_ls_goodness_of_fit_ref   1.127
_refine_ls_restrained_S_all      1.127
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.21709(17) 0.0538(2) 0.60280(19) 0.0545(7) Uani 1 1 d . . . . .
C2 C 0.20555(19) 0.0670(2) 0.6898(2) 0.0641(9) Uani 1 1 d . . . . .
H2 H 0.2297 0.0296 0.7417 0.077 Uiso 1 1 calc R U . . .
C3 C 0.1511(2) 0.1465(2) 0.68765(19) 0.0629(8) Uani 1 1 d . . . . .
H3 H 0.1330 0.1708 0.7377 0.076 Uiso 1 1 calc R U . . .
C4 C 0.12949(16) 0.1820(2) 0.59898(18) 0.0504(7) Uani 1 1 d . . . . .
C5 C 0.07432(16) 0.2676(2) 0.55759(18) 0.0520(7) Uani 1 1 d . . . . .
C6 C 0.11682(17) 0.3683(2) 0.55166(18) 0.0518(7) Uani 1 1 d . . . . .
C7 C 0.1234(2) 0.4564(2) 0.6045(2) 0.0726(10) Uani 1 1 d . . . . .
H7 H 0.0998 0.4679 0.6533 0.087 Uiso 1 1 calc R U . . .
C8 C 0.1720(2) 0.5271(2) 0.5725(2) 0.0745(10) Uani 1 1 d . . . . .
H8 H 0.1862 0.5931 0.5967 0.089 Uiso 1 1 calc R U . . .
C9 C 0.19441(17) 0.4828(2) 0.5009(2) 0.0553(7) Uani 1 1 d . . . . .
C10 C 0.24086(19) 0.5283(2) 0.4383(2) 0.0640(9) Uani 1 1 d . . . . .
N1 N 0.17027(13) 0.12505(16) 0.54827(15) 0.0516(6) Uani 1 1 d . . . . .
H1N H 0.1670 0.1329 0.4902 0.062 Uiso 1 1 calc R U . . .
N2 N 0.16055(13) 0.38557(17) 0.48835(14) 0.0508(6) Uani 1 1 d . . . . .
H2N H 0.1661 0.3417 0.4465 0.061 Uiso 1 1 calc R U . . .
C11 C 0.02454(16) 0.2376(2) 0.46362(18) 0.0512(7) Uani 1 1 d . . . . .
C12 C 0.00580(18) 0.1357(2) 0.4372(2) 0.0624(8) Uani 1 1 d . . . . .
H12 H 0.0277 0.0806 0.4748 0.075 Uiso 1 1 calc R U . . .
C13 C -0.0454(2) 0.1153(3) 0.3550(2) 0.0702(9) Uani 1 1 d . . . . .
H13 H -0.0566 0.0457 0.3390 0.084 Uiso 1 1 calc R U . . .
N3 N -0.07950(16) 0.1886(2) 0.29782(17) 0.0679(7) Uani 1 1 d . . . . .
C14 C -0.0614(2) 0.2864(3) 0.3233(2) 0.0727(10) Uani 1 1 d . . . . .
H14 H -0.0845 0.3398 0.2845 0.087 Uiso 1 1 calc R U . . .
C15 C -0.01056(19) 0.3142(2) 0.4033(2) 0.0675(9) Uani 1 1 d . . . . .
H15 H 0.0001 0.3844 0.4168 0.081 Uiso 1 1 calc R U . . .
C16 C 0.0179(2) 0.2848(3) 0.6212(2) 0.0750(10) Uani 1 1 d . . . . .
H16 H 0.0460 0.3029 0.6819 0.113 Uiso 1 1 calc R U . . .
H16A H -0.0106 0.2217 0.6240 0.113 Uiso 1 1 calc R U . . .
H16B H -0.0167 0.3406 0.5972 0.113 Uiso 1 1 calc R U . . .
C17 C 0.1877(3) 0.5895(3) 0.3613(3) 0.1148(17) Uani 1 1 d . . . . .
H17 H 0.2175 0.6235 0.3237 0.172 Uiso 1 1 calc R U . . .
H17A H 0.1602 0.6413 0.3879 0.172 Uiso 1 1 calc R U . . .
H17B H 0.1520 0.5422 0.3243 0.172 Uiso 1 1 calc R U . . .
C18 C 0.3002(3) 0.6056(3) 0.4942(4) 0.1058(15) Uani 1 1 d . . . . .
H18 H 0.3351 0.5680 0.5414 0.159 Uiso 1 1 calc R U . . .
H18A H 0.2741 0.6579 0.5220 0.159 Uiso 1 1 calc R U . . .
H18B H 0.3281 0.6387 0.4539 0.159 Uiso 1 1 calc R U . . .
O1 O 0.18289(14) 0.20096(19) 0.36955(16) 0.0703(7) Uani 1 1 d . . . . .
H1A H 0.143(3) 0.184(3) 0.311(3) 0.105 Uiso 1 1 d . U . . .
H1B H 0.227(3) 0.195(3) 0.364(3) 0.105 Uiso 1 1 d . U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.367(4) . ?
C1 N1 1.374(3) . ?
C1 C10 1.498(4) 7_556 ?
C2 C3 1.402(4) . ?
C3 C4 1.368(4) . ?
C4 N1 1.370(3) . ?
C4 C5 1.511(4) . ?
C5 C6 1.506(4) . ?
C5 C11 1.532(4) . ?
C5 C16 1.546(4) . ?
C6 C7 1.363(4) . ?
C6 N2 1.371(4) . ?
C7 C8 1.409(5) . ?
C8 C9 1.344(4) . ?
C9 N2 1.376(3) . ?
C9 C10 1.498(4) . ?
C10 C1 1.498(4) 7_556 ?
C10 C17 1.532(5) . ?
C10 C18 1.550(5) . ?
C11 C12 1.379(4) . ?
C11 C15 1.381(4) . ?
C12 C13 1.382(4) . ?
C13 N3 1.320(4) . ?
N3 C14 1.324(4) . ?
C14 C15 1.376(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 N1 106.1(3) . . ?
C2 C1 C10 132.0(3) . 7_556 ?
N1 C1 C10 121.2(2) . 7_556 ?
C1 C2 C3 108.6(3) . . ?
C4 C3 C2 107.9(3) . . ?
C3 C4 N1 106.6(3) . . ?
C3 C4 C5 130.8(3) . . ?
N1 C4 C5 122.7(2) . . ?
C6 C5 C4 110.4(2) . . ?
C6 C5 C11 111.0(2) . . ?
C4 C5 C11 112.8(2) . . ?
C6 C5 C16 108.8(2) . . ?
C4 C5 C16 108.1(2) . . ?
C11 C5 C16 105.6(2) . . ?
C7 C6 N2 105.9(3) . . ?
C7 C6 C5 130.6(3) . . ?
N2 C6 C5 123.5(2) . . ?
C6 C7 C8 108.3(3) . . ?
C9 C8 C7 108.3(3) . . ?
C8 C9 N2 106.7(3) . . ?
C8 C9 C10 129.5(3) . . ?
N2 C9 C10 123.7(2) . . ?
C1 C10 C9 112.5(2) 7_556 . ?
C1 C10 C17 109.7(3) 7_556 . ?
C9 C10 C17 108.9(3) . . ?
C1 C10 C18 108.5(3) 7_556 . ?
C9 C10 C18 108.7(3) . . ?
C17 C10 C18 108.4(3) . . ?
C4 N1 C1 110.8(2) . . ?
C6 N2 C9 110.7(2) . . ?
C12 C11 C15 115.8(3) . . ?
C12 C11 C5 123.5(2) . . ?
C15 C11 C5 120.4(3) . . ?
C11 C12 C13 120.1(3) . . ?
N3 C13 C12 124.0(3) . . ?
C13 N3 C14 115.8(3) . . ?
N3 C14 C15 124.3(3) . . ?
C14 C15 C11 119.9(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 0.3(3) . . . . ?
C10 C1 C2 C3 -169.9(3) 7_556 . . . ?
C1 C2 C3 C4 -0.1(4) . . . . ?
C2 C3 C4 N1 -0.1(3) . . . . ?
C2 C3 C4 C5 -178.5(3) . . . . ?
C3 C4 C5 C6 95.9(3) . . . . ?
N1 C4 C5 C6 -82.3(3) . . . . ?
C3 C4 C5 C11 -139.2(3) . . . . ?
N1 C4 C5 C11 42.6(4) . . . . ?
C3 C4 C5 C16 -22.9(4) . . . . ?
N1 C4 C5 C16 158.9(3) . . . . ?
C4 C5 C6 C7 -103.9(4) . . . . ?
C11 C5 C6 C7 130.3(3) . . . . ?
C16 C5 C6 C7 14.5(4) . . . . ?
C4 C5 C6 N2 73.9(3) . . . . ?
C11 C5 C6 N2 -51.9(3) . . . . ?
C16 C5 C6 N2 -167.7(3) . . . . ?
N2 C6 C7 C8 -0.3(4) . . . . ?
C5 C6 C7 C8 177.8(3) . . . . ?
C6 C7 C8 C9 0.3(4) . . . . ?
C7 C8 C9 N2 -0.2(4) . . . . ?
C7 C8 C9 C10 174.6(3) . . . . ?
C8 C9 C10 C1 153.9(3) . . . 7_556 ?
N2 C9 C10 C1 -32.1(4) . . . 7_556 ?
C8 C9 C10 C17 -84.3(4) . . . . ?
N2 C9 C10 C17 89.8(3) . . . . ?
C8 C9 C10 C18 33.7(4) . . . . ?
N2 C9 C10 C18 -152.3(3) . . . . ?
C3 C4 N1 C1 0.3(3) . . . . ?
C5 C4 N1 C1 178.9(2) . . . . ?
C2 C1 N1 C4 -0.4(3) . . . . ?
C10 C1 N1 C4 171.1(3) 7_556 . . . ?
C7 C6 N2 C9 0.1(3) . . . . ?
C5 C6 N2 C9 -178.1(2) . . . . ?
C8 C9 N2 C6 0.1(3) . . . . ?
C10 C9 N2 C6 -175.2(2) . . . . ?
C6 C5 C11 C12 151.6(3) . . . . ?
C4 C5 C11 C12 27.1(4) . . . . ?
C16 C5 C11 C12 -90.7(3) . . . . ?
C6 C5 C11 C15 -34.8(4) . . . . ?
C4 C5 C11 C15 -159.3(3) . . . . ?
C16 C5 C11 C15 82.9(3) . . . . ?
C15 C11 C12 C13 -0.2(4) . . . . ?
C5 C11 C12 C13 173.7(3) . . . . ?
C11 C12 C13 N3 -0.4(5) . . . . ?
C12 C13 N3 C14 0.5(5) . . . . ?
C13 N3 C14 C15 0.1(5) . . . . ?
N3 C14 C15 C11 -0.8(6) . . . . ?
C12 C11 C15 C14 0.8(5) . . . . ?
C5 C11 C15 C14 -173.3(3) . . . . ?

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
N1 H1N O1 0.86 2.07 2.888(3) 158.4 .
N2 H2N O1 0.86 2.19 3.027(3) 165.1 .
O1 H1A N3 1.02(4) 1.76(5) 2.760(4) 165(3) 2
N1 H1N O1 0.86 2.07 2.888(3) 158.4 .
N2 H2N O1 0.86 2.19 3.027(3) 165.1 .
O1 H1A N3 1.02(4) 1.76(5) 2.760(4) 165(3) 2

_refine_diff_density_max         0.169
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.036


_symmetry_cell_setting           ?
_diffrn_radiation_source         'Sealed Tube'
_diffrn_radiation_monochromator  Confocal
_chemical_absolute_configuration ?

