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

#######################################################################
#
#                 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
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_mcg466
_audit_creation_date             2014-09-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.08.28 svn.r2986 for OlexSys, GUI svn.r4874)
;
_shelxl_version_number           2014/6
_chemical_name_common            "catechol, 2,2'-bpe"
_chemical_name_systematic        
;
 1,2-dihydroxybenzene, 1,2-bis(2-pyridyl)ethylene
;
_chemical_formula_moiety         'C12 H10 N2, 2(C6 H6 O2)'
_chemical_formula_sum            'C24 H22 N2 O4'
_chemical_formula_weight         402.43
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.3687(7)
_cell_length_b                   19.169(2)
_cell_length_c                   14.7014(15)
_cell_angle_alpha                90
_cell_angle_beta                 102.277(5)
_cell_angle_gamma                90
_cell_volume                     2029.1(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8707
_cell_measurement_temperature    190(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      1.00
_shelx_estimated_absorpt_T_max   0.991
_shelx_estimated_absorpt_T_min   0.966
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'HKL Scalepack (Otwinowski & Minor, 1997)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0357
_diffrn_reflns_av_unetI/netI     0.0370
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            16490
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.241
_diffrn_reflns_theta_max         27.483
_diffrn_reflns_theta_min         1.771
_diffrn_ambient_temperature      190.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'CCD phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3329
_reflns_number_total             4648
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor, 1997)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_data_reduction        
;
 HKL Denzo, Scalepack (Otwinowski & Minor, 1997)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.332
_refine_diff_density_min         -0.320
_refine_diff_density_rms         0.118
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     287
_refine_ls_number_reflns         4648
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0739
_refine_ls_R_factor_gt           0.0425
_refine_ls_restrained_S_all      1.101
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0897P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1164
_refine_ls_wR_factor_ref         0.1485
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Others
 Fixed Uiso: H1(0.044) H2(0.049) H3(0.049) H4(0.042) H6(0.035) H7(0.034)
 H9(0.036) H10(0.041) H11(0.043) H12(0.042) H15(0.042) H16(0.049) H17(0.049)
 H18(0.046) H21(0.041) H22(0.048) H23(0.048) H24(0.042)
 Fixed X: H1(0.2926) H2(0.3399) H3(0.3575) H4(0.3181) H6(0.2244) H7(0.2802)
 H9(0.1669) H10(0.1176) H11(0.1432) H12(0.2221) H15(-0.0517) H16(-0.0502)
 H17(0.2329) H18(0.5095) H21(0.9222) H22(1.0142) H23(0.8159) H24(0.5296)
 Fixed Y: H1(0.1963) H2(0.1333) H3(0.0113) H4(-0.0441) H6(0.0494) H7(-0.0831)
 H9(0.0164) H10(-0.0322) H11(-0.1539) H12(-0.2214) H15(0.1877) H16(0.1499)
 H17(0.122) H18(0.1308) H21(0.2815) H22(0.3983) H23(0.484) H24(0.4525)
 Fixed Z: H1(0.8131) H2(0.6853) H3(0.6955) H4(0.8313) H6(1.0327) H7(0.9697)
 H9(1.1606) H10(1.2988) H11(1.3205) H12(1.2043) H15(1.1053) H16(1.2561)
 H17(1.3564) H18(1.3047) H21(0.959) H22(0.9671) H23(1.0034) H24(1.0345)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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 0.2972(2) 0.14681(9) 0.81665(11) 0.0363(4) Uani 1 1 d . . . . .
H1 H 0.2926 0.1963 0.8131 0.044 Uiso 1 1 calc R . . . .
C2 C 0.3264(2) 0.10991(10) 0.74041(11) 0.0410(4) Uani 1 1 d . . . . .
H2 H 0.3399 0.1333 0.6853 0.049 Uiso 1 1 calc R . . . .
C3 C 0.3355(2) 0.03809(10) 0.74644(11) 0.0405(4) Uani 1 1 d . . . . .
H3 H 0.3575 0.0113 0.6955 0.049 Uiso 1 1 calc R . . . .
C4 C 0.31250(19) 0.00534(9) 0.82654(11) 0.0347(4) Uani 1 1 d . . . . .
H4 H 0.3181 -0.0441 0.8313 0.042 Uiso 1 1 calc R . . . .
C5 C 0.28089(19) 0.04571(8) 0.90053(10) 0.0277(3) Uani 1 1 d . . . . .
C6 C 0.25008(19) 0.01673(8) 0.98844(10) 0.0296(3) Uani 1 1 d . . . . .
H6 H 0.2244 0.0494 1.0327 0.035 Uiso 1 1 calc R . . . .
C7 C 0.25413(19) -0.04978(8) 1.01297(10) 0.0287(3) Uani 1 1 d . . . . .
H7 H 0.2802 -0.0831 0.9697 0.034 Uiso 1 1 calc R . . . .
C8 C 0.22151(18) -0.07602(8) 1.10193(10) 0.0267(3) Uani 1 1 d . . . . .
C9 C 0.17705(19) -0.03260(9) 1.17031(10) 0.0304(4) Uani 1 1 d . . . . .
H9 H 0.1669 0.0164 1.1606 0.036 Uiso 1 1 calc R . . . .
C10 C 0.1481(2) -0.06125(9) 1.25186(11) 0.0343(4) Uani 1 1 d . . . . .
H10 H 0.1176 -0.0322 1.2988 0.041 Uiso 1 1 calc R . . . .
C11 C 0.1636(2) -0.13292(9) 1.26506(11) 0.0356(4) Uani 1 1 d . . . . .
H11 H 0.1432 -0.1539 1.3205 0.043 Uiso 1 1 calc R . . . .
C12 C 0.2095(2) -0.17241(9) 1.19528(11) 0.0347(4) Uani 1 1 d . . . . .
H12 H 0.2221 -0.2214 1.2043 0.042 Uiso 1 1 calc R . . . .
C14 C 0.2261(2) 0.18153(8) 1.11404(10) 0.0294(3) Uani 1 1 d . . . . .
C15 C 0.0628(2) 0.17603(8) 1.14575(11) 0.0350(4) Uani 1 1 d . . . . .
H15 H -0.0517 0.1877 1.1053 0.042 Uiso 1 1 calc R . . . .
C16 C 0.0630(2) 0.15378(10) 1.23538(12) 0.0409(4) Uani 1 1 d . . . . .
H16 H -0.0502 0.1499 1.2561 0.049 Uiso 1 1 calc R . . . .
C17 C 0.2310(2) 0.13712(9) 1.29467(12) 0.0410(4) Uani 1 1 d . . . . .
H17 H 0.2329 0.1220 1.3564 0.049 Uiso 1 1 calc R . . . .
C18 C 0.3954(2) 0.14259(9) 1.26395(11) 0.0382(4) Uani 1 1 d . . . . .
H18 H 0.5095 0.1308 1.3047 0.046 Uiso 1 1 calc R . . . .
C13 C 0.3949(2) 0.16499(8) 1.17459(11) 0.0312(4) Uani 1 1 d . . . . .
C20 C 0.6690(2) 0.29780(8) 0.98930(10) 0.0277(3) Uani 1 1 d . . . . .
C21 C 0.8413(2) 0.31641(9) 0.97344(11) 0.0338(4) Uani 1 1 d . . . . .
H21 H 0.9222 0.2815 0.9590 0.041 Uiso 1 1 calc R . . . .
C22 C 0.8963(2) 0.38568(9) 0.97860(12) 0.0399(4) Uani 1 1 d . . . . .
H22 H 1.0142 0.3983 0.9671 0.048 Uiso 1 1 calc R . . . .
C23 C 0.7793(2) 0.43639(9) 1.00048(12) 0.0403(4) Uani 1 1 d . . . . .
H23 H 0.8159 0.4840 1.0034 0.048 Uiso 1 1 calc R . . . .
C24 C 0.6085(2) 0.41766(8) 1.01810(11) 0.0349(4) Uani 1 1 d . . . . .
H24 H 0.5296 0.4525 1.0345 0.042 Uiso 1 1 calc R . . . .
C19 C 0.55188(19) 0.34907(8) 1.01216(10) 0.0274(3) Uani 1 1 d . . . . .
N1 N 0.27502(17) 0.11614(7) 0.89544(9) 0.0315(3) Uani 1 1 d . . . . .
N2 N 0.23763(16) -0.14559(7) 1.11508(9) 0.0303(3) Uani 1 1 d . . . . .
O1 O 0.22548(14) 0.20600(6) 1.02567(7) 0.0330(3) Uani 1 1 d . . . . .
O2 O 0.56089(14) 0.17018(7) 1.14762(9) 0.0422(3) Uani 1 1 d . . . . .
O3 O 0.60584(15) 0.23043(6) 0.98543(8) 0.0347(3) Uani 1 1 d D . . . .
O4 O 0.38203(15) 0.33370(6) 1.02964(8) 0.0347(3) Uani 1 1 d . . . . .
H2A H 0.555(3) 0.1879(11) 1.0910(16) 0.063(7) Uiso 1 1 d . . . . .
H1A H 0.244(3) 0.1675(12) 0.9840(16) 0.070(7) Uiso 1 1 d . . . . .
H4A H 0.353(3) 0.2873(14) 1.0203(16) 0.073(7) Uiso 1 1 d . . . . .
H3A H 0.670(3) 0.2023(11) 0.9532(15) 0.074(7) Uiso 1 1 d D . . . .


_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 1.381(2) . ?
C1 N1 1.340(2) . ?
C2 C3 1.380(3) . ?
C3 C4 1.376(2) . ?
C4 C5 1.394(2) . ?
C5 C6 1.468(2) . ?
C5 N1 1.3524(19) . ?
C6 C7 1.324(2) . ?
C7 C8 1.468(2) . ?
C8 C9 1.397(2) . ?
C8 N2 1.3492(19) . ?
C9 C10 1.376(2) . ?
C10 C11 1.389(2) . ?
C11 C12 1.374(2) . ?
C12 N2 1.342(2) . ?
C14 C15 1.384(2) . ?
C14 C13 1.403(2) . ?
C14 O1 1.3804(18) . ?
C15 C16 1.385(2) . ?
C16 C17 1.391(2) . ?
C17 C18 1.383(2) . ?
C18 C13 1.381(2) . ?
C13 O2 1.3675(18) . ?
C20 C21 1.386(2) . ?
C20 C19 1.395(2) . ?
C20 O3 1.3697(18) . ?
C21 C22 1.386(2) . ?
C22 C23 1.382(2) . ?
C23 C24 1.385(2) . ?
C24 C19 1.376(2) . ?
C19 O4 1.3624(18) . ?

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
N1 C1 C2 123.08(17) . . ?
C3 C2 C1 118.21(15) . . ?
C4 C3 C2 119.80(16) . . ?
C3 C4 C5 119.06(17) . . ?
C4 C5 C6 124.03(15) . . ?
N1 C5 C4 121.30(14) . . ?
N1 C5 C6 114.67(13) . . ?
C7 C6 C5 127.27(14) . . ?
C6 C7 C8 125.06(14) . . ?
C9 C8 C7 123.02(14) . . ?
N2 C8 C7 116.12(13) . . ?
N2 C8 C9 120.86(14) . . ?
C10 C9 C8 119.53(15) . . ?
C9 C10 C11 119.54(15) . . ?
C12 C11 C10 117.83(15) . . ?
N2 C12 C11 123.60(15) . . ?
C15 C14 C13 119.08(14) . . ?
O1 C14 C15 120.91(13) . . ?
O1 C14 C13 119.95(13) . . ?
C14 C15 C16 121.24(15) . . ?
C15 C16 C17 119.20(15) . . ?
C18 C17 C16 120.15(15) . . ?
C13 C18 C17 120.57(15) . . ?
C18 C13 C14 119.76(14) . . ?
O2 C13 C14 121.76(14) . . ?
O2 C13 C18 118.48(14) . . ?
C21 C20 C19 119.66(14) . . ?
O3 C20 C21 123.44(13) . . ?
O3 C20 C19 116.89(13) . . ?
C22 C21 C20 120.36(14) . . ?
C23 C22 C21 119.79(15) . . ?
C22 C23 C24 119.87(16) . . ?
C19 C24 C23 120.72(15) . . ?
C24 C19 C20 119.57(14) . . ?
O4 C19 C20 122.21(14) . . ?
O4 C19 C24 118.22(13) . . ?
C1 N1 C5 118.54(14) . . ?
C12 N2 C8 118.63(13) . . ?

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
O2 H2A O3 0.89(2) 1.86(2) 2.7320(17) 165(2) .
O1 H1A N1 0.99(2) 1.69(2) 2.6576(17) 167(2) .
O4 H4A O1 0.92(3) 1.83(3) 2.7014(17) 158(2) .
O3 H3A N2 0.912(16) 1.717(16) 2.6236(16) 173(2) 3_657

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Acetonitrile'
_database_code_depnum_ccdc_archive 'CCDC 1025307'
#######################################################################
#
#                 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
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_mcg146
_audit_creation_date             2014-09-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.08.28 svn.r2986 for OlexSys, GUI svn.r4874)
;
_shelxl_version_number           2014/6
_chemical_name_common            
;
 catechol, 2,2'-bpe, rctt-2,2'-tpcb
;
_chemical_name_systematic        
'1,2-dihydroxybenzene, 1,2-bis(2-pyridyl)ethylene,  rctt-tetrakis(2-pyridyl)cyclobutane'
_chemical_formula_moiety         'C12 H10 N2, 2(C6 H6 O2)'
_chemical_formula_sum            'C24 H22 N2 O4'
_chemical_formula_weight         402.43
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.4665(8)
_cell_length_b                   19.1328(19)
_cell_length_c                   14.8336(15)
_cell_angle_alpha                90
_cell_angle_beta                 102.249(5)
_cell_angle_gamma                90
_cell_volume                     2070.8(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7072
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      25.35
_cell_measurement_theta_min      1.00
_shelx_estimated_absorpt_T_max   0.982
_shelx_estimated_absorpt_T_min   0.974
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'HKL Scalepack (Otwinowski & Minor, 1997)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.291
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0324
_diffrn_reflns_av_unetI/netI     0.0301
_diffrn_reflns_Laue_measured_fraction_full 0.973
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            10870
_diffrn_reflns_point_group_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         2.551
_diffrn_ambient_temperature      298.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'CCD phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2685
_reflns_number_total             3631
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor, 1997)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_data_reduction        
;
 HKL Denzo, Scalepack (Otwinowski & Minor, 1997)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.163
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.034
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.152
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     310
_refine_ls_number_reflns         3631
_refine_ls_number_restraints     28
_refine_ls_R_factor_all          0.0827
_refine_ls_R_factor_gt           0.0589
_refine_ls_restrained_S_all      1.148
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0468P)²+1.0750P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1442
_refine_ls_wR_factor_ref         0.1548
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 

 Several low angle reflections were omitted due to beam-stop shadowing 
 effects.

 The cyclobutane product is modeled as a disorder of the unreacted olefin.
 The primary component is designated as the olefin and is labeled 'A' while
 the cyclobutane is labeled 'B' as the minor component.  The relative 
 occupancies were refined to 0.906(4) and 0.094(4) for the olefin and 
 cyclobutane, respectively. The atoms that comprise the cyclobutane, as well 
 as the atoms attached directly to the cyclobutane ring were restrained to 
 the same distance.
;
_olex2_refinement_description    
;
1. Others
 Fixed Uiso: H12A(0.085) H11A(0.092) H10A(0.095) H9A(0.079) H7A(0.065)
 H6A(0.064) H4A(0.069) H1A(0.085) H3A(0.081) H2A(0.086) H12B(0.083) H11B(0.089)
 H10B(0.082) H9B(0.075) H7B(0.076) H6B(0.069) H4B(0.09) H3B(0.091) H2B(0.099)
 H1B(0.091) H1(0.081) H2(0.098) H18(0.082) H15(0.089) H17(0.095) H16(0.095)
 H4(0.084) H3(0.086) H21(0.088) H24(0.08) H23(0.098) H22(0.101)
 Fixed X: H12A(0.2076) H11A(0.1657) H10A(0.1503) H9A(0.1879) H7A(0.2721)
 H6A(0.2209) H3A(0.3764) H2A(0.3471) H12B(0.3217) H11B(0.3415) H10B(0.252)
 H9B(0.1428) H7B(0.1338) H6B(0.1681) H4B(0.2753) H3B(0.3907) H2B(0.3759)
 H1B(0.2456) H1(0.2512) H2(-0.0464) H18(0.5388) H15(-0.008) H17(0.5385)
 H16(0.2655) H4(-0.1277) H3(0.1605) H21(0.041) H24(0.4214) H23(0.5125)
 H22(0.3198)
 Fixed Y: H12A(0.6992) H11A(0.6395) H10A(0.5192) H9A(0.4608) H7A(0.5479)
 H6A(0.4183) H3A(0.4611) H2A(0.3415) H12B(0.7269) H11B(0.675) H10B(0.5596)
 H9B(0.4961) H7B(0.5669) H6B(0.4403) H4B(0.5296) H3B(0.4816) H2B(0.3618)
 H1B(0.2901) H1(0.6755) H2(0.6856) H18(0.6858) H15(0.6279) H17(0.6454)
 H16(0.6173) H4(0.2943) H3(0.2081) H21(0.4539) H24(0.282) H23(0.3969)
 H22(0.4834)
 Fixed Z: H12A(0.6788) H11A(0.8068) H10A(0.8014) H9A(0.6697) H7A(0.4668)
 H6A(0.5321) H3A(0.2062) H2A(0.1878) H12B(0.6761) H11B(0.8192) H10B(0.8287)
 H9B(0.6951) H7B(0.4633) H6B(0.5573) H4B(0.3743) H3B(0.2547) H2B(0.2298)
 H1B(0.3245) H1(0.4991) H2(0.397) H18(0.388) H15(0.1915) H17(0.241) H16(0.1433)
 H4(0.0319) H3(-0.0376) H21(0.038) H24(-0.0307) H23(-0.0258) H22(0.008)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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
N2A N 0.2268(4) 0.61822(17) 0.59993(17) 0.0585(8) Uani 0.906(4) 1 d . . P A 1
C12A C 0.2047(5) 0.6506(2) 0.6772(2) 0.0706(9) Uani 0.906(4) 1 d . . P A 1
H12A H 0.2076 0.6992 0.6788 0.085 Uiso 0.906(4) 1 calc R . P A 1
C11A C 0.1781(5) 0.6154(2) 0.7540(2) 0.0763(11) Uani 0.906(4) 1 d . . P A 1
H11A H 0.1657 0.6395 0.8068 0.092 Uiso 0.906(4) 1 calc R . P A 1
C10A C 0.1703(5) 0.5442(2) 0.7508(2) 0.0789(11) Uani 0.906(4) 1 d . . P A 1
H10A H 0.1503 0.5192 0.8014 0.095 Uiso 0.906(4) 1 calc R . P A 1
C9A C 0.1920(4) 0.5094(2) 0.6724(2) 0.0656(9) Uani 0.906(4) 1 d . . P A 1
H9A H 0.1879 0.4608 0.6697 0.079 Uiso 0.906(4) 1 calc R . P A 1
C8A C 0.2202(4) 0.54840(17) 0.59766(19) 0.0524(7) Uani 0.906(4) 1 d . . P A 1
C7A C 0.2487(4) 0.51683(15) 0.51120(19) 0.0544(7) Uani 0.906(4) 1 d . . P A 1
H7A H 0.2721 0.5479 0.4668 0.065 Uiso 0.906(4) 1 calc R . P A 1
C6A C 0.2453(4) 0.45025(15) 0.48899(19) 0.0537(7) Uani 0.906(4) 1 d . . P A 1
H6A H 0.2209 0.4183 0.5321 0.064 Uiso 0.906(4) 1 calc R . P A 1
N1A N 0.2599(4) 0.35265(13) 0.39095(17) 0.0576(7) Uani 0.906(4) 1 d . . P A 1
C5A C 0.2771(4) 0.42233(15) 0.40177(18) 0.0489(7) Uani 0.906(4) 1 d . . P A 1
C4A C 0.3209(5) 0.46412(18) 0.3326(2) 0.0576(8) Uani 0.906(4) 1 d . . P A 1
H4A H 0.337(4) 0.5152(17) 0.342(2) 0.069 Uiso 0.906(4) 1 d R . P A 1
C1A C 0.2866(5) 0.3246(2) 0.3117(3) 0.0710(10) Uani 0.906(4) 1 d . . P A 1
H1A H 0.277(5) 0.275(2) 0.310(2) 0.085 Uiso 0.906(4) 1 d R . P A 1
C3A C 0.3470(5) 0.4336(2) 0.2528(2) 0.0672(9) Uani 0.906(4) 1 d . . P A 1
H3A H 0.3764 0.4611 0.2062 0.081 Uiso 0.906(4) 1 calc R . P A 1
C2A C 0.3298(5) 0.3629(2) 0.2416(2) 0.0720(10) Uani 0.906(4) 1 d . . P A 1
H2A H 0.3471 0.3415 0.1878 0.086 Uiso 0.906(4) 1 calc R . P A 1
N2B N 0.220(3) 0.6426(14) 0.5999(11) 0.066(8) Uiso 0.094(4) 1 d . . P A 2
C12B C 0.286(4) 0.6806(10) 0.6799(16) 0.069(7) Uiso 0.094(4) 1 d G . P A 2
H12B H 0.3217 0.7269 0.6761 0.083 Uiso 0.094(4) 1 calc R . P A 2
C11B C 0.298(3) 0.6495(12) 0.7657(12) 0.074(7) Uiso 0.094(4) 1 d G . P A 2
H11B H 0.3415 0.6750 0.8192 0.089 Uiso 0.094(4) 1 calc R . P A 2
C10B C 0.244(3) 0.5804(12) 0.7714(13) 0.068(7) Uiso 0.094(4) 1 d G . P A 2
H10B H 0.2520 0.5596 0.8287 0.082 Uiso 0.094(4) 1 calc R . P A 2
C9B C 0.179(3) 0.5423(10) 0.6913(18) 0.063(7) Uiso 0.094(4) 1 d G . P A 2
H9B H 0.1428 0.4961 0.6951 0.075 Uiso 0.094(4) 1 calc R . P A 2
C8B C 0.167(2) 0.5735(13) 0.6056(13) 0.064(7) Uiso 0.094(4) 1 d DG . P A 2
C7B C 0.097(3) 0.5406(11) 0.5130(14) 0.063(6) Uiso 0.094(4) 1 d D . P A 2
H7B H 0.1338 0.5669 0.4633 0.076 Uiso 0.094(4) 1 calc R . P A 2
C6B C 0.108(3) 0.4630(11) 0.4995(15) 0.058(6) Uiso 0.094(4) 1 d D . P A 2
H6B H 0.1681 0.4403 0.5573 0.069 Uiso 0.094(4) 1 calc R . P A 2
N1B N 0.182(3) 0.3669(11) 0.4061(17) 0.073(7) Uiso 0.094(4) 1 d . . P A 2
C5B C 0.191(2) 0.4386(12) 0.4210(12) 0.066(6) Uiso 0.094(4) 1 d DG . P A 2
C4B C 0.269(4) 0.4816(10) 0.3643(18) 0.075(8) Uiso 0.094(4) 1 d G . P A 2
H4B H 0.2753 0.5296 0.3743 0.090 Uiso 0.094(4) 1 calc R . P A 2
C3B C 0.338(4) 0.4528(16) 0.2927(18) 0.076(9) Uiso 0.094(4) 1 d G . P A 2
H3B H 0.3907 0.4816 0.2547 0.091 Uiso 0.094(4) 1 calc R . P A 2
C2B C 0.330(4) 0.3811(17) 0.2777(16) 0.082(9) Uiso 0.094(4) 1 d G . P A 2
H2B H 0.3759 0.3618 0.2298 0.099 Uiso 0.094(4) 1 calc R . P A 2
C1B C 0.252(4) 0.3381(11) 0.334(2) 0.076(9) Uiso 0.094(4) 1 d G . P A 2
H1B H 0.2456 0.2901 0.3245 0.091 Uiso 0.094(4) 1 calc R . P A 2
O1 O 0.2658(3) 0.70738(10) 0.46436(13) 0.0673(5) Uani 1 1 d . . . . .
H1 H 0.2512 0.6755 0.4991 0.081 Uiso 1 1 calc R . . . .
O2 O -0.0623(3) 0.66969(12) 0.34458(15) 0.0819(6) Uani 1 1 d . . . . .
H2 H -0.0464 0.6856 0.3970 0.098 Uiso 1 1 calc R . . . .
C13 C 0.2668(4) 0.68058(14) 0.37813(18) 0.0574(7) Uani 1 1 d . . . . .
C14 C 0.1024(4) 0.66391(14) 0.31923(19) 0.0609(7) Uani 1 1 d . . . . .
C18 C 0.4287(4) 0.67403(16) 0.3486(2) 0.0683(8) Uani 1 1 d . . . . .
H18 H 0.5388 0.6858 0.3880 0.082 Uiso 1 1 calc R . . . .
C15 C 0.1018(5) 0.63970(17) 0.2311(2) 0.0741(8) Uani 1 1 d . . . . .
H15 H -0.0080 0.6279 0.1915 0.089 Uiso 1 1 calc R . . . .
C17 C 0.4288(5) 0.65008(18) 0.2606(2) 0.0788(9) Uani 1 1 d . . . . .
H17 H 0.5385 0.6454 0.2410 0.095 Uiso 1 1 calc R . . . .
C16 C 0.2658(5) 0.63324(18) 0.2025(2) 0.0790(9) Uani 1 1 d . . . . .
H16 H 0.2655 0.6173 0.1433 0.095 Uiso 1 1 calc R . . . .
O4 O -0.1098(3) 0.33658(10) 0.03513(14) 0.0698(6) Uani 1 1 d . . . . .
H4 H -0.1277 0.2943 0.0319 0.084 Uiso 1 1 calc R . . . .
O3 O 0.1100(3) 0.23207(9) -0.00447(14) 0.0713(6) Uani 1 1 d . . . . .
H3 H 0.1605 0.2081 -0.0376 0.086 Uiso 1 1 calc R . . . .
C19 C 0.1740(4) 0.29925(13) -0.00259(17) 0.0539(6) Uani 1 1 d . . . . .
C20 C 0.0581(4) 0.35085(14) 0.01843(18) 0.0565(7) Uani 1 1 d . . . . .
C21 C 0.1165(5) 0.41909(15) 0.0230(2) 0.0734(8) Uani 1 1 d . . . . .
H21 H 0.0410 0.4539 0.0380 0.088 Uiso 1 1 calc R . . . .
C24 C 0.3435(4) 0.31678(15) -0.0179(2) 0.0667(8) Uani 1 1 d . . . . .
H24 H 0.4214 0.2820 -0.0307 0.080 Uiso 1 1 calc R . . . .
C23 C 0.3984(5) 0.38518(17) -0.0145(2) 0.0813(9) Uani 1 1 d . . . . .
H23 H 0.5125 0.3969 -0.0258 0.098 Uiso 1 1 calc R . . . .
C22 C 0.2836(5) 0.43679(17) 0.0059(2) 0.0845(10) Uani 1 1 d . . . . .
H22 H 0.3198 0.4834 0.0080 0.101 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N2A C12A 1.344(4) . ?
N2A C8A 1.337(4) . ?
C12A C11A 1.374(5) . ?
C11A C10A 1.363(5) . ?
C10A C9A 1.379(5) . ?
C9A C8A 1.389(4) . ?
C8A C7A 1.473(4) . ?
C7A C6A 1.315(4) . ?
C6A C5A 1.465(4) . ?
N1A C5A 1.346(4) . ?
N1A C1A 1.346(4) . ?
C5A C4A 1.393(4) . ?
C4A C3A 1.371(5) . ?
C1A C2A 1.366(5) . ?
C3A C2A 1.366(5) . ?
N2B C12B 1.3900 . ?
N2B C8B 1.3900 . ?
C12B C11B 1.3900 . ?
C11B C10B 1.3900 . ?
C10B C9B 1.3900 . ?
C9B C8B 1.3900 . ?
C8B C7B 1.500(10) . ?
C7B C6B 1.502(7) 3_566 ?
C7B C6B 1.503(10) . ?
C6B C7B 1.502(7) 3_566 ?
C6B C5B 1.505(10) . ?
N1B C5B 1.3900 . ?
N1B C1B 1.3900 . ?
C5B C4B 1.3900 . ?
C4B C3B 1.3900 . ?
C3B C2B 1.3900 . ?
C2B C1B 1.3900 . ?
O1 C13 1.380(3) . ?
O2 C14 1.365(3) . ?
C13 C14 1.384(4) . ?
C13 C18 1.376(4) . ?
C14 C15 1.386(4) . ?
C18 C17 1.383(4) . ?
C15 C16 1.384(4) . ?
C17 C16 1.372(5) . ?
O4 C20 1.357(3) . ?
O3 C19 1.369(3) . ?
C19 C20 1.391(4) . ?
C19 C24 1.373(4) . ?
C20 C21 1.374(4) . ?
C21 C22 1.367(4) . ?
C24 C23 1.369(4) . ?
C23 C22 1.383(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8A N2A C12A 118.2(3) . . ?
N2A C12A C11A 123.1(3) . . ?
C10A C11A C12A 118.3(3) . . ?
C11A C10A C9A 120.1(3) . . ?
C10A C9A C8A 118.5(3) . . ?
N2A C8A C9A 121.9(3) . . ?
N2A C8A C7A 114.8(3) . . ?
C9A C8A C7A 123.3(3) . . ?
C6A C7A C8A 128.1(3) . . ?
C7A C6A C5A 125.2(3) . . ?
C5A N1A C1A 118.2(3) . . ?
N1A C5A C6A 115.9(2) . . ?
N1A C5A C4A 120.8(3) . . ?
C4A C5A C6A 123.3(3) . . ?
C3A C4A C5A 119.4(3) . . ?
N1A C1A C2A 123.6(3) . . ?
C2A C3A C4A 119.9(3) . . ?
C1A C2A C3A 118.1(3) . . ?
C12B N2B C8B 120.0 . . ?
C11B C12B N2B 120.0 . . ?
C10B C11B C12B 120.0 . . ?
C11B C10B C9B 120.0 . . ?
C8B C9B C10B 120.0 . . ?
N2B C8B C7B 113(2) . . ?
C9B C8B N2B 120.0 . . ?
C9B C8B C7B 127(2) . . ?
C8B C7B C6B 121.1(19) . . ?
C8B C7B C6B 106.4(14) . 3_566 ?
C6B C7B C6B 91(2) 3_566 . ?
C7B C6B C7B 89(2) 3_566 . ?
C7B C6B C5B 117.7(15) 3_566 . ?
C7B C6B C5B 117.0(19) . . ?
C5B N1B C1B 120.0 . . ?
N1B C5B C6B 114.6(18) . . ?
C4B C5B C6B 125.4(18) . . ?
C4B C5B N1B 120.0 . . ?
C5B C4B C3B 120.0 . . ?
C2B C3B C4B 120.0 . . ?
C3B C2B C1B 120.0 . . ?
C2B C1B N1B 120.0 . . ?
O1 C13 C14 119.5(2) . . ?
C18 C13 O1 120.5(3) . . ?
C18 C13 C14 119.9(3) . . ?
O2 C14 C13 122.5(3) . . ?
O2 C14 C15 117.7(3) . . ?
C13 C14 C15 119.8(3) . . ?
C13 C18 C17 120.5(3) . . ?
C16 C15 C14 119.5(3) . . ?
C16 C17 C18 119.5(3) . . ?
C17 C16 C15 120.8(3) . . ?
O3 C19 C20 116.1(2) . . ?
O3 C19 C24 123.8(2) . . ?
C24 C19 C20 120.2(2) . . ?
O4 C20 C19 122.8(2) . . ?
O4 C20 C21 118.6(3) . . ?
C21 C20 C19 118.6(3) . . ?
C22 C21 C20 121.3(3) . . ?
C23 C24 C19 120.4(3) . . ?
C24 C23 C22 119.7(3) . . ?
C21 C22 C23 119.7(3) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Acetonitrile'
_database_code_depnum_ccdc_archive 'CCDC 1025308'
#######################################################################
#
#                 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
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
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#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_mcg1323
_audit_creation_date             2014-09-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.08.28 svn.r2986 for OlexSys, GUI svn.r4874)
;
_shelxl_version_number           2014/6
_chemical_name_common            "catechol, 2,2'-tpcb"
_chemical_name_systematic        
;
 1,2-dihydroxybenzene, rctt-tetrakis(2-pyridyl)cyclobutane
;

_chemical_formula_moiety         '2(C12 H10 N2), 3(C6 H6 O2)'
_chemical_formula_sum            'C42 H38 N4 O6'
_chemical_formula_weight         694.76
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   11.9841(12)
_cell_length_b                   12.6106(13)
_cell_length_c                   13.7902(14)
_cell_angle_alpha                109.918(5)
_cell_angle_beta                 103.137(5)
_cell_angle_gamma                102.958(5)
_cell_volume                     1801.6(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5559
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.11
_cell_measurement_theta_min      1.00
_shelx_estimated_absorpt_T_max   0.990
_shelx_estimated_absorpt_T_min   0.972
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'HKL Scalepack (Otwinowski & Minor, 1997)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             732
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0192
_diffrn_reflns_av_unetI/netI     0.0337
_diffrn_reflns_Laue_measured_fraction_full 0.874
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9665
_diffrn_reflns_point_group_measured_fraction_full 0.874
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         24.096
_diffrn_reflns_theta_min         1.665
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.874
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'CCD phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4235
_reflns_number_total             5711
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor, 1997)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_data_reduction        
;
 HKL Denzo, Scalepack (Otwinowski & Minor, 1997)
;

_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.294
_refine_diff_density_min         -0.425
_refine_diff_density_rms         0.100
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.139
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     493
_refine_ls_number_reflns         5711
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0779
_refine_ls_R_factor_gt           0.0512
_refine_ls_restrained_S_all      1.139
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1084P)²+0.0953P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1451
_refine_ls_wR_factor_ref         0.1776
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 

 Data above 48 degrees 2theta was omitted due to poor diffraction at high 
 angles.
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 O1-H1A
 0.84 with sigma of 0.02
 O2-H2A
 0.84 with sigma of 0.02
 O3-H3A
 0.84 with sigma of 0.02
 O4-H4A
 0.84 with sigma of 0.02
 O5-H5
 0.84 with sigma of 0.02
 O6-H6A
 0.84 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C18(H18), C19(H19), C7(H7), C6(H6)
3.b Aromatic/amide H refined with riding coordinates:
 C16(H16), C21(H21), C4(H4), C9(H9), C27(H27), C30(H30), C28(H28), C29(H29),
 C15(H15), C14(H14), C13(H13), C42(H42), C24(H24), C39(H39), C23(H23), C22(H22),
  C41(H41), C40(H40), C36(H36), C35(H35), C12(H12), C11(H11), C10(H10), C3(H3),
 C1(H1), C2(H2), C34(H34), C33(H33)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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
N1 N 1.50990(16) 0.80656(16) 0.13000(14) 0.0493(5) Uani 1 1 d . . . . .
N2 N 1.42774(16) 1.07386(17) 0.22587(14) 0.0548(5) Uani 1 1 d . . . . .
C16 C 1.3264(2) 0.7992(2) 0.01210(18) 0.0508(5) Uani 1 1 d . . . . .
H16 H 1.2873 0.8281 -0.0345 0.061 Uiso 1 1 calc R . . . .
C21 C 1.2922(2) 1.0867(2) 0.0791(2) 0.0623(7) Uani 1 1 d . . . . .
H21 H 1.2758 1.0907 0.0115 0.075 Uiso 1 1 calc R . . . .
N4 N 1.36731(18) 0.30528(18) 0.53146(16) 0.0594(5) Uani 1 1 d . . . . .
C4 C 1.3764(3) 0.4154(2) 0.2385(2) 0.0684(7) Uani 1 1 d . . . . .
H4 H 1.3083 0.4151 0.2600 0.082 Uiso 1 1 calc R . . . .
N3 N 1.58253(19) 0.42490(18) 0.28178(16) 0.0622(5) Uani 1 1 d . . . . .
C9 C 1.1921(2) 0.3518(2) 0.46256(19) 0.0609(6) Uani 1 1 d . . . . .
H9 H 1.1588 0.3997 0.4349 0.073 Uiso 1 1 calc R . . . .
H6A H 0.890(3) 1.016(3) 0.177(3) 0.106(11) Uiso 1 1 d D . . . .
H5 H 0.6753(17) 0.868(3) 0.197(3) 0.096(11) Uiso 1 1 d D . . . .
H2A H 0.811(3) 0.018(3) 0.3730(18) 0.112(13) Uiso 1 1 d D . . . .
H1A H 0.5831(18) 0.079(3) 0.305(2) 0.092(10) Uiso 1 1 d D . . . .
H4A H 0.721(3) 0.377(3) 0.341(3) 0.105(12) Uiso 1 1 d D . . . .
H3A H 0.779(3) 0.158(3) 0.271(2) 0.100(11) Uiso 1 1 d D . . . .
O1 O 0.65625(15) 0.08078(15) 0.32941(12) 0.0599(4) Uani 1 1 d D . . . .
O2 O 0.85948(16) 0.05323(18) 0.43537(16) 0.0724(5) Uani 1 1 d D . . . .
C25 C 0.7945(2) 0.1076(2) 0.49290(18) 0.0544(6) Uani 1 1 d . . . . .
C26 C 0.6907(2) 0.1240(2) 0.44107(18) 0.0530(6) Uani 1 1 d . . . . .
C27 C 0.6298(3) 0.1828(3) 0.5021(2) 0.0766(8) Uani 1 1 d . . . . .
H27 H 0.5611 0.1956 0.4675 0.092 Uiso 1 1 calc R . . . .
C30 C 0.8345(3) 0.1479(3) 0.6050(2) 0.0742(8) Uani 1 1 d . . . . .
H30 H 0.9041 0.1369 0.6402 0.089 Uiso 1 1 calc R . . . .
C28 C 0.6699(3) 0.2226(3) 0.6137(2) 0.0947(10) Uani 1 1 d . . . . .
H28 H 0.6281 0.2620 0.6546 0.114 Uiso 1 1 calc R . . . .
C29 C 0.7713(3) 0.2044(3) 0.6647(2) 0.0909(10) Uani 1 1 d . . . . .
H29 H 0.7976 0.2305 0.7403 0.109 Uiso 1 1 calc R . . . .
O5 O 0.75253(16) 0.89770(15) 0.21705(14) 0.0623(5) Uani 1 1 d D . . . .
C20 C 1.40179(19) 1.07779(18) 0.12751(17) 0.0452(5) Uani 1 1 d . . . . .
C18 C 1.52778(19) 0.94632(18) 0.04487(16) 0.0427(5) Uani 1 1 d . . . . .
H18 H 1.6143 0.9618 0.0793 0.051 Uiso 1 1 calc R . . . .
O6 O 0.93540(16) 0.97570(16) 0.14961(17) 0.0717(5) Uani 1 1 d D . . . .
C17 C 1.45176(19) 0.84716(18) 0.06258(16) 0.0432(5) Uani 1 1 d . . . . .
C19 C 1.49863(18) 1.06732(18) 0.07522(16) 0.0426(5) Uani 1 1 d . . . . .
H19 H 1.5736 1.1342 0.1219 0.051 Uiso 1 1 calc R . . . .
C37 C 0.9040(2) 0.8619(2) 0.14185(18) 0.0543(6) Uani 1 1 d . . . . .
C38 C 0.8094(2) 0.8184(2) 0.17518(17) 0.0512(6) Uani 1 1 d . . . . .
C15 C 1.2606(2) 0.7088(2) 0.0313(2) 0.0601(6) Uani 1 1 d . . . . .
H15 H 1.1769 0.6756 -0.0023 0.072 Uiso 1 1 calc R . . . .
C14 C 1.3206(3) 0.6685(2) 0.1010(2) 0.0656(7) Uani 1 1 d . . . . .
H14 H 1.2783 0.6080 0.1160 0.079 Uiso 1 1 calc R . . . .
C13 C 1.4438(2) 0.7190(2) 0.1478(2) 0.0606(6) Uani 1 1 d . . . . .
H13 H 1.4838 0.6909 0.1947 0.073 Uiso 1 1 calc R . . . .
C42 C 0.9669(2) 0.7880(3) 0.0998(2) 0.0691(7) Uani 1 1 d . . . . .
H42 H 1.0298 0.8162 0.0766 0.083 Uiso 1 1 calc R . . . .
C24 C 1.3432(2) 1.0763(2) 0.2746(2) 0.0660(7) Uani 1 1 d . . . . .
H24 H 1.3607 1.0727 0.3424 0.079 Uiso 1 1 calc R . . . .
C39 C 0.7807(2) 0.7040(2) 0.16868(19) 0.0616(6) Uani 1 1 d . . . . .
H39 H 0.7184 0.6754 0.1923 0.074 Uiso 1 1 calc R . . . .
C23 C 1.2323(2) 1.0839(3) 0.2301(2) 0.0734(8) Uani 1 1 d . . . . .
H23 H 1.1759 1.0851 0.2666 0.088 Uiso 1 1 calc R . . . .
C22 C 1.2072(2) 1.0895(3) 0.1313(2) 0.0748(8) Uani 1 1 d . . . . .
H22 H 1.1330 1.0952 0.0991 0.090 Uiso 1 1 calc R . . . .
C41 C 0.9362(3) 0.6730(3) 0.0924(2) 0.0727(8) Uani 1 1 d . . . . .
H41 H 0.9783 0.6235 0.0637 0.087 Uiso 1 1 calc R . . . .
C40 C 0.8444(3) 0.6312(2) 0.1270(2) 0.0699(7) Uani 1 1 d . . . . .
H40 H 0.8247 0.5536 0.1225 0.084 Uiso 1 1 calc R . . . .
O3 O 0.82418(16) 0.14882(15) 0.22896(15) 0.0657(5) Uani 1 1 d D . . . .
C8 C 1.3160(2) 0.3716(2) 0.49071(17) 0.0491(5) Uani 1 1 d . . . . .
C5 C 1.4835(2) 0.42596(19) 0.31062(18) 0.0509(6) Uani 1 1 d . . . . .
C7 C 1.39921(19) 0.4684(2) 0.47548(17) 0.0478(5) Uani 1 1 d . . . . .
H7 H 1.3525 0.5037 0.4352 0.057 Uiso 1 1 calc R . . . .
C31 C 0.8848(2) 0.2620(2) 0.24315(18) 0.0527(6) Uani 1 1 d . . . . .
C6 C 1.49353(19) 0.43161(19) 0.42269(17) 0.0474(5) Uani 1 1 d . . . . .
H6 H 1.4943 0.3539 0.4223 0.057 Uiso 1 1 calc R . . . .
O4 O 0.7621(2) 0.3320(2) 0.3400(2) 0.0985(8) Uani 1 1 d D . . . .
C36 C 0.9736(2) 0.2781(3) 0.1969(2) 0.0691(7) Uani 1 1 d . . . . .
H36 H 0.9929 0.2129 0.1575 0.083 Uiso 1 1 calc R . . . .
C32 C 0.8534(2) 0.3573(2) 0.2991(2) 0.0666(7) Uani 1 1 d . . . . .
C35 C 1.0341(2) 0.3908(3) 0.2087(3) 0.0807(9) Uani 1 1 d . . . . .
H35 H 1.0944 0.4017 0.1774 0.097 Uiso 1 1 calc R . . . .
C12 C 1.2933(3) 0.2171(2) 0.5435(2) 0.0707(7) Uani 1 1 d . . . . .
H12 H 1.3276 0.1697 0.5711 0.085 Uiso 1 1 calc R . . . .
C11 C 1.1702(3) 0.1927(3) 0.5175(2) 0.0775(8) Uani 1 1 d . . . . .
H11 H 1.1229 0.1310 0.5281 0.093 Uiso 1 1 calc R . . . .
C10 C 1.1188(2) 0.2606(3) 0.4760(2) 0.0747(8) Uani 1 1 d . . . . .
H10 H 1.0355 0.2456 0.4569 0.090 Uiso 1 1 calc R . . . .
C3 C 1.3706(3) 0.4053(3) 0.1351(2) 0.0814(8) Uani 1 1 d . . . . .
H3 H 1.2983 0.3965 0.0857 0.098 Uiso 1 1 calc R . . . .
C1 C 1.5744(3) 0.4173(2) 0.1802(3) 0.0784(8) Uani 1 1 d . . . . .
H1 H 1.6432 0.4183 0.1596 0.094 Uiso 1 1 calc R . . . .
C2 C 1.4716(4) 0.4082(3) 0.1059(2) 0.0835(9) Uani 1 1 d . . . . .
H2 H 1.4708 0.4042 0.0371 0.100 Uiso 1 1 calc R . . . .
C34 C 1.0054(3) 0.4861(3) 0.2662(3) 0.0902(9) Uani 1 1 d . . . . .
H34 H 1.0473 0.5626 0.2759 0.108 Uiso 1 1 calc R . . . .
C33 C 0.9143(3) 0.4689(3) 0.3100(3) 0.0933(10) Uani 1 1 d . . . . .
H33 H 0.8936 0.5340 0.3477 0.112 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C17 1.342(3) . ?
N1 C13 1.338(3) . ?
N2 C20 1.342(3) . ?
N2 C24 1.337(3) . ?
C16 C17 1.392(3) . ?
C16 C15 1.374(3) . ?
C21 C20 1.379(3) . ?
C21 C22 1.374(4) . ?
N4 C8 1.338(3) . ?
N4 C12 1.342(3) . ?
C4 C5 1.381(3) . ?
C4 C3 1.371(4) . ?
N3 C5 1.336(3) . ?
N3 C1 1.350(4) . ?
C9 C8 1.387(3) . ?
C9 C10 1.376(4) . ?
O1 C26 1.370(3) . ?
O2 C25 1.362(3) . ?
C25 C26 1.383(3) . ?
C25 C30 1.377(3) . ?
C26 C27 1.374(3) . ?
C27 C28 1.371(4) . ?
C30 C29 1.373(4) . ?
C28 C29 1.368(4) . ?
O5 C38 1.375(3) . ?
C20 C19 1.506(3) . ?
C18 C17 1.501(3) . ?
C18 C19 1.554(3) 2_875 ?
C18 C19 1.580(3) . ?
O6 C37 1.359(3) . ?
C19 C18 1.554(3) 2_875 ?
C37 C38 1.388(3) . ?
C37 C42 1.384(3) . ?
C38 C39 1.373(3) . ?
C15 C14 1.372(4) . ?
C14 C13 1.366(4) . ?
C42 C41 1.375(4) . ?
C24 C23 1.370(4) . ?
C39 C40 1.382(4) . ?
C23 C22 1.357(4) . ?
C41 C40 1.366(4) . ?
O3 C31 1.373(3) . ?
C8 C7 1.500(3) . ?
C5 C6 1.498(3) . ?
C7 C6 1.550(3) . ?
C7 C6 1.569(3) 2_866 ?
C31 C36 1.371(3) . ?
C31 C32 1.372(3) . ?
C6 C7 1.569(3) 2_866 ?
O4 C32 1.365(3) . ?
C36 C35 1.378(4) . ?
C32 C33 1.372(4) . ?
C35 C34 1.360(4) . ?
C12 C11 1.371(4) . ?
C11 C10 1.361(4) . ?
C3 C2 1.357(4) . ?
C1 C2 1.366(4) . ?
C34 C33 1.374(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
C13 N1 C17 118.0(2) . . ?
C24 N2 C20 118.0(2) . . ?
C15 C16 C17 119.7(2) . . ?
C22 C21 C20 119.7(2) . . ?
C8 N4 C12 117.0(2) . . ?
C3 C4 C5 120.0(3) . . ?
C5 N3 C1 117.0(2) . . ?
C10 C9 C8 119.4(3) . . ?
O2 C25 C26 121.3(2) . . ?
O2 C25 C30 118.9(2) . . ?
C30 C25 C26 119.8(2) . . ?
O1 C26 C25 116.4(2) . . ?
O1 C26 C27 123.9(2) . . ?
C27 C26 C25 119.7(2) . . ?
C28 C27 C26 120.3(3) . . ?
C29 C30 C25 119.8(3) . . ?
C29 C28 C27 120.0(3) . . ?
C28 C29 C30 120.4(3) . . ?
N2 C20 C21 120.97(19) . . ?
N2 C20 C19 114.76(18) . . ?
C21 C20 C19 124.2(2) . . ?
C17 C18 C19 118.09(16) . . ?
C17 C18 C19 116.52(16) . 2_875 ?
C19 C18 C19 89.21(14) 2_875 . ?
N1 C17 C16 121.1(2) . . ?
N1 C17 C18 117.04(18) . . ?
C16 C17 C18 121.90(19) . . ?
C20 C19 C18 119.51(17) . 2_875 ?
C20 C19 C18 117.27(17) . . ?
C18 C19 C18 90.79(14) 2_875 . ?
O6 C37 C38 120.9(2) . . ?
O6 C37 C42 119.7(2) . . ?
C42 C37 C38 119.4(2) . . ?
O5 C38 C37 115.9(2) . . ?
C39 C38 O5 124.1(2) . . ?
C39 C38 C37 120.0(2) . . ?
C14 C15 C16 118.8(2) . . ?
C13 C14 C15 118.7(2) . . ?
N1 C13 C14 123.7(2) . . ?
C41 C42 C37 120.0(3) . . ?
N2 C24 C23 123.6(2) . . ?
C38 C39 C40 120.0(3) . . ?
C22 C23 C24 118.1(2) . . ?
C23 C22 C21 119.6(3) . . ?
C40 C41 C42 120.4(2) . . ?
C41 C40 C39 120.1(3) . . ?
N4 C8 C9 122.1(2) . . ?
N4 C8 C7 116.56(19) . . ?
C9 C8 C7 121.3(2) . . ?
C4 C5 C6 122.3(2) . . ?
N3 C5 C4 121.5(2) . . ?
N3 C5 C6 116.1(2) . . ?
C8 C7 C6 119.03(17) . 2_866 ?
C8 C7 C6 115.43(18) . . ?
C6 C7 C6 88.90(15) . 2_866 ?
C36 C31 O3 119.2(2) . . ?
C36 C31 C32 120.4(2) . . ?
C32 C31 O3 120.3(2) . . ?
C5 C6 C7 119.91(18) . 2_866 ?
C5 C6 C7 119.51(18) . . ?
C7 C6 C7 91.10(15) . 2_866 ?
C31 C36 C35 120.1(3) . . ?
O4 C32 C31 116.1(2) . . ?
O4 C32 C33 125.0(3) . . ?
C33 C32 C31 118.8(3) . . ?
C34 C35 C36 119.8(3) . . ?
N4 C12 C11 123.9(3) . . ?
C10 C11 C12 118.6(3) . . ?
C11 C10 C9 119.0(3) . . ?
C2 C3 C4 119.2(3) . . ?
N3 C1 C2 124.1(3) . . ?
C3 C2 C1 118.2(3) . . ?
C35 C34 C33 119.8(3) . . ?
C32 C33 C34 121.1(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
O6 H6A O3 0.878(18) 2.00(2) 2.843(2) 161(3) 1_565
O2 H2A O5 0.819(18) 2.01(2) 2.766(3) 153(3) 1_545
O1 H1A N2 0.858(18) 1.906(19) 2.752(2) 169(3) 1_445
O4 H4A N3 0.830(18) 1.99(2) 2.763(3) 155(3) 1_455
O3 H3A O1 0.884(18) 2.04(2) 2.830(2) 149(3) .

_olex2_submission_special_instructions 'No special instructions were received'

#END=====
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Nitromethane'
_database_code_depnum_ccdc_archive 'CCDC 1025309'
