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

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

data_Ce(arenediNOx)2
_database_code_depnum_ccdc_archive 'CCDC 1411379'
_audit_update_record             
;
2015-07-07 deposited with the CCDC.
2015-08-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97

_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C60 H76 Ce N4 O6'
_chemical_formula_weight         1089.37

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'
Ce Ce -0.2486 2.6331 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c     '
_symmetry_Int_Tables_number      14

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

_cell_length_a                   15.1376(7)
_cell_length_b                   13.3253(7)
_cell_length_c                   26.6562(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.733(2)
_cell_angle_gamma                90.00
_cell_volume                     5299.5(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(1)
_exptl_crystal_description       prism
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10

_exptl_crystal_density_diffrn    1.365
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2280
_exptl_absorpt_coefficient_mu    0.914
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2007)'
_exptl_absorpt_correction_T_min  0.6858
_exptl_absorpt_correction_T_max  0.7456
_diffrn_ambient_temperature      100(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'CCD Area Detector'
_diffrn_measurement_device_type  'Bruker APEXII'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_reflns_number            70825
_diffrn_reflns_av_R_equivalents  0.0355
_diffrn_reflns_av_sigmaI/netI    0.0270
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_theta_min         1.36
_diffrn_reflns_theta_max         27.63
_reflns_number_total             12139
_reflns_number_gt                10604
_reflns_threshold_expression     >2sigma(I)
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0274P)²+7.2469P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         12139
_refine_ls_number_parameters     653
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0386
_refine_ls_R_factor_gt           0.0307
_refine_ls_wR_factor_ref         0.0717
_refine_ls_wR_factor_gt          0.0688
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_restrained_S_all      1.083
_refine_ls_shift/su_max          0.002
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Ce1 Ce 0.274049(7) 0.656839(9) 0.224278(4) 0.00919(4) Uani 1 1 d . . .
O1 O 0.30286(10) 0.59529(12) 0.15132(6) 0.0140(3) Uani 1 1 d . . .
O2 O 0.26418(10) 0.72470(11) 0.29878(6) 0.0127(3) Uani 1 1 d . . .
O3 O 0.35555(10) 0.78594(12) 0.21088(5) 0.0126(3) Uani 1 1 d . . .
O4 O 0.13721(10) 0.62254(12) 0.20781(6) 0.0130(3) Uani 1 1 d . . .
N1 N 0.32813(12) 0.50578(14) 0.17908(7) 0.0115(4) Uani 1 1 d . . .
N2 N 0.29045(12) 0.63002(14) 0.32194(7) 0.0111(4) Uani 1 1 d . . .
N3 N 0.28531(12) 0.81714(14) 0.17056(7) 0.0108(4) Uani 1 1 d . . .
N4 N 0.04885(11) 0.64318(14) 0.18173(7) 0.0107(4) Uani 1 1 d . . .
C1 C 0.27094(14) 0.34314(18) 0.24549(8) 0.0137(4) Uani 1 1 d . . .
C2 C 0.23419(14) 0.41670(16) 0.27262(8) 0.0112(4) Uani 1 1 d . . .
H2 H 0.2012 0.4685 0.2551 0.015 Uiso 1 1 calc R . .
C3 C 0.24579(14) 0.41433(16) 0.32566(8) 0.0119(4) Uani 1 1 d . . .
C4 C 0.29382(14) 0.33476(17) 0.35152(8) 0.0149(4) Uani 1 1 d . . .
H4 H 0.3007 0.3310 0.3868 0.020 Uiso 1 1 calc R . .
C5 C 0.33112(15) 0.26171(18) 0.32470(9) 0.0164(5) Uani 1 1 d . . .
H5 H 0.3639 0.2098 0.3422 0.022 Uiso 1 1 calc R . .
C6 C 0.32004(15) 0.26519(17) 0.27184(9) 0.0160(5) Uani 1 1 d . . .
H6 H 0.3453 0.2157 0.2541 0.021 Uiso 1 1 calc R . .
C7 C 0.24684(14) 0.34561(18) 0.18873(8) 0.0143(4) Uani 1 1 d . . .
C8 C 0.26605(14) 0.42591(17) 0.15840(8) 0.0126(4) Uani 1 1 d . . .
C9 C 0.22515(15) 0.42988(19) 0.10719(8) 0.0167(5) Uani 1 1 d . . .
H9 H 0.2361 0.4843 0.0873 0.022 Uiso 1 1 calc R . .
C10 C 0.16886(16) 0.3542(2) 0.08594(9) 0.0207(5) Uani 1 1 d . . .
H10 H 0.1411 0.3587 0.0521 0.028 Uiso 1 1 calc R . .
C11 C 0.15345(16) 0.2712(2) 0.11481(9) 0.0218(5) Uani 1 1 d . . .
H11 H 0.1177 0.2187 0.1001 0.029 Uiso 1 1 calc R . .
C12 C 0.19204(15) 0.26761(18) 0.16575(9) 0.0177(5) Uani 1 1 d . . .
H12 H 0.1814 0.2123 0.1852 0.024 Uiso 1 1 calc R . .
C13 C 0.42601(15) 0.48304(18) 0.17493(9) 0.0171(5) Uani 1 1 d . . .
C14 C 0.45923(16) 0.3989(2) 0.21212(11) 0.0269(6) Uani 1 1 d . . .
H14a H 0.4285 0.3378 0.2010 0.040 Uiso 1 1 calc R . .
H14b H 0.4476 0.4161 0.2454 0.040 Uiso 1 1 calc R . .
H14c H 0.5225 0.3899 0.2134 0.040 Uiso 1 1 calc R . .
C15 C 0.43482(18) 0.4537(2) 0.12088(11) 0.0321(7) Uani 1 1 d . . .
H15a H 0.4094 0.5054 0.0978 0.048 Uiso 1 1 calc R . .
H15b H 0.4036 0.3917 0.1121 0.048 Uiso 1 1 calc R . .
H15c H 0.4970 0.4453 0.1186 0.048 Uiso 1 1 calc R . .
C16 C 0.48119(15) 0.57721(18) 0.18976(9) 0.0178(5) Uani 1 1 d . . .
H16a H 0.5434 0.5630 0.1899 0.027 Uiso 1 1 calc R . .
H16b H 0.4731 0.5984 0.2231 0.027 Uiso 1 1 calc R . .
H16c H 0.4618 0.6296 0.1657 0.027 Uiso 1 1 calc R . .
C17 C 0.20188(14) 0.49269(17) 0.35273(8) 0.0118(4) Uani 1 1 d . . .
C18 C 0.21995(14) 0.59544(17) 0.34931(8) 0.0112(4) Uani 1 1 d . . .
C19 C 0.17135(14) 0.66538(17) 0.37223(8) 0.0136(4) Uani 1 1 d . . .
H19 H 0.1826 0.7335 0.3692 0.018 Uiso 1 1 calc R . .
C20 C 0.10598(15) 0.63389(18) 0.39970(8) 0.0160(5) Uani 1 1 d . . .
H20 H 0.0739 0.6811 0.4150 0.021 Uiso 1 1 calc R . .
C21 C 0.08839(15) 0.53310(19) 0.40438(8) 0.0172(5) Uani 1 1 d . . .
H21 H 0.0451 0.5122 0.4230 0.023 Uiso 1 1 calc R . .
C22 C 0.13612(15) 0.46299(18) 0.38094(8) 0.0154(4) Uani 1 1 d . . .
H22 H 0.1241 0.3950 0.3841 0.020 Uiso 1 1 calc R . .
C23 C 0.38136(14) 0.64467(18) 0.35630(8) 0.0150(4) Uani 1 1 d . . .
C24 C 0.38126(17) 0.7379(2) 0.38959(9) 0.0235(5) Uani 1 1 d . . .
H24a H 0.3387 0.7292 0.4122 0.035 Uiso 1 1 calc R . .
H24b H 0.3650 0.7955 0.3684 0.035 Uiso 1 1 calc R . .
H24c H 0.4400 0.7476 0.4092 0.035 Uiso 1 1 calc R . .
C25 C 0.40554(17) 0.5525(2) 0.38926(10) 0.0272(6) Uani 1 1 d . . .
H25a H 0.4024 0.4940 0.3680 0.041 Uiso 1 1 calc R . .
H25b H 0.3642 0.5456 0.4127 0.041 Uiso 1 1 calc R . .
H25c H 0.4653 0.5596 0.4079 0.041 Uiso 1 1 calc R . .
C26 C 0.44966(15) 0.6560(2) 0.32088(9) 0.0216(5) Uani 1 1 d . . .
H26a H 0.5077 0.6692 0.3406 0.032 Uiso 1 1 calc R . .
H26b H 0.4326 0.7108 0.2979 0.032 Uiso 1 1 calc R . .
H26c H 0.4519 0.5953 0.3018 0.032 Uiso 1 1 calc R . .
C27 C 0.16385(14) 0.78031(17) 0.06653(8) 0.0128(4) Uani 1 1 d . . .
C28 C 0.12503(14) 0.69970(17) 0.08767(8) 0.0120(4) Uani 1 1 d . . .
H28 H 0.1611 0.6576 0.1103 0.016 Uiso 1 1 calc R . .
C29 C 0.03312(14) 0.68004(17) 0.07587(8) 0.0120(4) Uani 1 1 d . . .
C30 C -0.02107(14) 0.74432(18) 0.04272(8) 0.0142(4) Uani 1 1 d . . .
H30 H -0.0824 0.7327 0.0348 0.019 Uiso 1 1 calc R . .
C31 C 0.01662(15) 0.82566(17) 0.02161(8) 0.0161(5) Uani 1 1 d . . .
H31 H -0.0198 0.8689 -0.0002 0.021 Uiso 1 1 calc R . .
C32 C 0.10840(15) 0.84310(18) 0.03269(8) 0.0160(4) Uani 1 1 d . . .
H32 H 0.1331 0.8967 0.0176 0.021 Uiso 1 1 calc R . .
C33 C 0.26370(14) 0.79391(17) 0.07533(8) 0.0133(4) Uani 1 1 d . . .
C34 C 0.31977(14) 0.80939(17) 0.12234(8) 0.0117(4) Uani 1 1 d . . .
C35 C 0.41263(15) 0.81667(17) 0.12410(9) 0.0142(4) Uani 1 1 d . . .
H35 H 0.4496 0.8271 0.1552 0.019 Uiso 1 1 calc R . .
C36 C 0.45038(15) 0.80874(19) 0.08048(9) 0.0182(5) Uani 1 1 d . . .
H36 H 0.5122 0.8134 0.0825 0.024 Uiso 1 1 calc R . .
C37 C 0.39585(16) 0.7939(2) 0.03377(9) 0.0208(5) Uani 1 1 d . . .
H37 H 0.4207 0.7885 0.0043 0.028 Uiso 1 1 calc R . .
C38 C 0.30411(15) 0.78715(19) 0.03157(8) 0.0182(5) Uani 1 1 d . . .
H38 H 0.2678 0.7779 0.0001 0.024 Uiso 1 1 calc R . .
C39 C 0.25853(15) 0.92322(17) 0.18337(8) 0.0142(4) Uani 1 1 d . . .
C40 C 0.33459(16) 0.99792(18) 0.18100(9) 0.0205(5) Uani 1 1 d . . .
H40a H 0.3879 0.9755 0.2029 0.031 Uiso 1 1 calc R . .
H40b H 0.3178 1.0628 0.1920 0.031 Uiso 1 1 calc R . .
H40c H 0.3457 1.0023 0.1467 0.031 Uiso 1 1 calc R . .
C41 C 0.17503(16) 0.95419(19) 0.14603(9) 0.0205(5) Uani 1 1 d . . .
H41a H 0.1896 0.9598 0.1125 0.031 Uiso 1 1 calc R . .
H41b H 0.1539 1.0177 0.1562 0.031 Uiso 1 1 calc R . .
H41c H 0.1291 0.9045 0.1460 0.031 Uiso 1 1 calc R . .
C42 C 0.23612(16) 0.92193(18) 0.23713(9) 0.0188(5) Uani 1 1 d . . .
H42a H 0.1898 0.8735 0.2389 0.028 Uiso 1 1 calc R . .
H42b H 0.2158 0.9872 0.2453 0.028 Uiso 1 1 calc R . .
H42c H 0.2887 0.9043 0.2610 0.028 Uiso 1 1 calc R . .
C43 C 0.00026(14) 0.58502(17) 0.09519(8) 0.0117(4) Uani 1 1 d . . .
C44 C 0.01908(13) 0.56136(16) 0.14745(8) 0.0108(4) Uani 1 1 d . . .
C45 C 0.00546(15) 0.46375(17) 0.16330(8) 0.0150(4) Uani 1 1 d . . .
H45 H 0.0230 0.4463 0.1973 0.020 Uiso 1 1 calc R . .
C46 C -0.03392(15) 0.39256(18) 0.12880(9) 0.0175(5) Uani 1 1 d . . .
H46 H -0.0433 0.3278 0.1398 0.023 Uiso 1 1 calc R . .
C47 C -0.05965(15) 0.41752(19) 0.07762(9) 0.0189(5) Uani 1 1 d . . .
H47 H -0.0888 0.3706 0.0548 0.025 Uiso 1 1 calc R . .
C48 C -0.04151(14) 0.51267(18) 0.06110(8) 0.0152(4) Uani 1 1 d . . .
H48 H -0.0573 0.5288 0.0268 0.020 Uiso 1 1 calc R . .
C49 C -0.01097(14) 0.66808(17) 0.21927(8) 0.0129(4) Uani 1 1 d . . .
C50 C -0.10560(15) 0.67988(19) 0.18910(9) 0.0191(5) Uani 1 1 d . . .
H50a H -0.1041 0.7238 0.1607 0.029 Uiso 1 1 calc R . .
H50b H -0.1440 0.7078 0.2107 0.029 Uiso 1 1 calc R . .
H50c H -0.1281 0.6154 0.1769 0.029 Uiso 1 1 calc R . .
C51 C -0.01056(15) 0.59146(19) 0.26239(8) 0.0175(5) Uani 1 1 d . . .
H51a H -0.0429 0.5325 0.2493 0.026 Uiso 1 1 calc R . .
H51b H -0.0386 0.6204 0.2887 0.026 Uiso 1 1 calc R . .
H51c H 0.0501 0.5736 0.2762 0.026 Uiso 1 1 calc R . .
C52 C 0.02100(16) 0.76897(18) 0.24258(9) 0.0188(5) Uani 1 1 d . . .
H52a H 0.0797 0.7614 0.2625 0.028 Uiso 1 1 calc R . .
H52b H -0.0198 0.7921 0.2640 0.028 Uiso 1 1 calc R . .
H52c H 0.0232 0.8169 0.2159 0.028 Uiso 1 1 calc R . .
O5 O 0.40853(12) 0.16144(16) 0.04393(8) 0.0362(5) Uani 1 1 d . . .
C53 C 0.32607(18) 0.1997(2) 0.05444(12) 0.0332(7) Uani 1 1 d . . .
H53a H 0.3203 0.2704 0.0458 0.044 Uiso 1 1 calc R . .
H53b H 0.3229 0.1921 0.0903 0.044 Uiso 1 1 calc R . .
C54 C 0.2517(2) 0.1395(3) 0.02206(15) 0.0479(9) Uani 1 1 d . . .
H54a H 0.2042 0.1238 0.0411 0.064 Uiso 1 1 calc R . .
H54b H 0.2264 0.1761 -0.0085 0.064 Uiso 1 1 calc R . .
C55 C 0.2976(2) 0.0474(2) 0.00936(12) 0.0350(7) Uani 1 1 d . . .
H55a H 0.2686 0.0190 -0.0227 0.047 Uiso 1 1 calc R . .
H55b H 0.2998 -0.0028 0.0359 0.047 Uiso 1 1 calc R . .
C56 C 0.38981(18) 0.0861(2) 0.00580(10) 0.0311(6) Uani 1 1 d . . .
H56a H 0.4336 0.0324 0.0119 0.041 Uiso 1 1 calc R . .
H56b H 0.3910 0.1142 -0.0277 0.041 Uiso 1 1 calc R . .
O6 O 0.65704(16) 0.66888(19) 0.05426(9) 0.0486(6) Uani 1 1 d . . .
C57 C 0.5856(2) 0.6052(3) 0.03108(13) 0.0421(8) Uani 1 1 d . . .
H57a H 0.5655 0.6249 -0.0040 0.056 Uiso 1 1 calc R . .
H57b H 0.5353 0.6097 0.0492 0.056 Uiso 1 1 calc R . .
C58 C 0.6224(2) 0.4985(3) 0.03360(14) 0.0468(8) Uani 1 1 d . . .
H58a H 0.6382 0.4781 0.0013 0.062 Uiso 1 1 calc R . .
H58b H 0.5798 0.4510 0.0434 0.062 Uiso 1 1 calc R . .
C59 C 0.7056(3) 0.5087(3) 0.07495(19) 0.0698(13) Uani 1 1 d . . .
H59a H 0.6904 0.5028 0.1088 0.093 Uiso 1 1 calc R . .
H59b H 0.7506 0.4590 0.0708 0.093 Uiso 1 1 calc R . .
C60 C 0.7359(2) 0.6110(3) 0.06533(15) 0.0527(9) Uani 1 1 d . . .
H60a H 0.7749 0.6370 0.0951 0.070 Uiso 1 1 calc R . .
H60b H 0.7680 0.6113 0.0368 0.070 Uiso 1 1 calc R . .


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ce1 O4 2.0940(15) . ?
Ce1 O3 2.1813(15) . ?
Ce1 O2 2.2100(15) . ?
Ce1 O1 2.2208(15) . ?
Ce1 N1 2.5510(18) . ?
Ce1 N3 2.5931(18) . ?
Ce1 N2 2.5976(18) . ?
O1 N1 1.422(2) . ?
O2 N2 1.431(2) . ?
O3 N3 1.439(2) . ?
O4 N4 1.426(2) . ?
N1 C8 1.465(3) . ?
N1 C13 1.534(3) . ?
N2 C18 1.465(3) . ?
N2 C23 1.531(3) . ?
N3 C34 1.470(3) . ?
N3 C39 1.525(3) . ?
N4 C44 1.445(3) . ?
N4 C49 1.496(3) . ?
C1 C2 1.389(3) . ?
C1 C6 1.396(3) . ?
C1 C7 1.496(3) . ?
C2 C3 1.395(3) . ?
C3 C4 1.399(3) . ?
C3 C17 1.488(3) . ?
C4 C5 1.383(3) . ?
C5 C6 1.391(3) . ?
C7 C8 1.401(3) . ?
C7 C12 1.404(3) . ?
C8 C9 1.401(3) . ?
C9 C10 1.379(3) . ?
C10 C11 1.390(4) . ?
C11 C12 1.385(3) . ?
C13 C15 1.521(3) . ?
C13 C16 1.522(3) . ?
C13 C14 1.524(3) . ?
C17 C22 1.402(3) . ?
C17 C18 1.402(3) . ?
C18 C19 1.391(3) . ?
C19 C20 1.392(3) . ?
C20 C21 1.379(3) . ?
C21 C22 1.392(3) . ?
C23 C25 1.518(3) . ?
C23 C26 1.521(3) . ?
C23 C24 1.527(3) . ?
C27 C28 1.389(3) . ?
C27 C32 1.401(3) . ?
C27 C33 1.501(3) . ?
C28 C29 1.398(3) . ?
C29 C30 1.394(3) . ?
C29 C43 1.484(3) . ?
C30 C31 1.388(3) . ?
C31 C32 1.390(3) . ?
C33 C34 1.405(3) . ?
C33 C38 1.409(3) . ?
C34 C35 1.402(3) . ?
C35 C36 1.384(3) . ?
C36 C37 1.387(3) . ?
C37 C38 1.383(3) . ?
C39 C42 1.528(3) . ?
C39 C41 1.528(3) . ?
C39 C40 1.531(3) . ?
C43 C48 1.400(3) . ?
C43 C44 1.410(3) . ?
C44 C45 1.394(3) . ?
C45 C46 1.384(3) . ?
C46 C47 1.394(3) . ?
C47 C48 1.385(3) . ?
C49 C52 1.525(3) . ?
C49 C50 1.528(3) . ?
C49 C51 1.537(3) . ?
O5 C53 1.419(3) . ?
O5 C56 1.423(3) . ?
C53 C54 1.526(4) . ?
C54 C55 1.478(4) . ?
C55 C56 1.506(4) . ?
O6 C60 1.409(4) . ?
O6 C57 1.430(4) . ?
C57 C58 1.524(5) . ?
C58 C59 1.533(5) . ?
C59 C60 1.475(6) . ?

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
O4 Ce1 O3 134.80(6) . . ?
O4 Ce1 O2 93.61(6) . . ?
O3 Ce1 O2 87.16(6) . . ?
O4 Ce1 O1 93.99(6) . . ?
O3 Ce1 O1 87.00(6) . . ?
O2 Ce1 O1 172.37(6) . . ?
O4 Ce1 N1 96.54(6) . . ?
O3 Ce1 N1 108.02(6) . . ?
O2 Ce1 N1 145.40(6) . . ?
O1 Ce1 N1 33.77(5) . . ?
O4 Ce1 N3 102.66(6) . . ?
O3 Ce1 N3 33.71(5) . . ?
O2 Ce1 N3 100.36(6) . . ?
O1 Ce1 N3 77.27(6) . . ?
N1 Ce1 N3 109.45(6) . . ?
O4 Ce1 N2 95.94(6) . . ?
O3 Ce1 N2 108.17(6) . . ?
O2 Ce1 N2 33.42(5) . . ?
O1 Ce1 N2 145.81(6) . . ?
N1 Ce1 N2 112.38(6) . . ?
N3 Ce1 N2 131.50(6) . . ?
N1 O1 Ce1 85.95(10) . . ?
N2 O2 Ce1 88.33(10) . . ?
N3 O3 Ce1 89.04(10) . . ?
N4 O4 Ce1 150.82(13) . . ?
O1 N1 C8 108.34(15) . . ?
O1 N1 C13 107.83(16) . . ?
C8 N1 C13 113.29(17) . . ?
O1 N1 Ce1 60.28(9) . . ?
C8 N1 Ce1 120.96(13) . . ?
C13 N1 Ce1 125.50(13) . . ?
O2 N2 C18 108.63(16) . . ?
O2 N2 C23 107.56(16) . . ?
C18 N2 C23 113.50(16) . . ?
O2 N2 Ce1 58.26(8) . . ?
C18 N2 Ce1 126.03(12) . . ?
C23 N2 Ce1 120.39(13) . . ?
O3 N3 C34 107.81(15) . . ?
O3 N3 C39 106.94(15) . . ?
C34 N3 C39 114.07(17) . . ?
O3 N3 Ce1 57.25(9) . . ?
C34 N3 Ce1 119.41(13) . . ?
C39 N3 Ce1 126.52(13) . . ?
O4 N4 C44 109.23(16) . . ?
O4 N4 C49 109.91(15) . . ?
C44 N4 C49 115.53(16) . . ?
C2 C1 C6 119.3(2) . . ?
C2 C1 C7 117.4(2) . . ?
C6 C1 C7 122.9(2) . . ?
C1 C2 C3 121.2(2) . . ?
C2 C3 C4 118.8(2) . . ?
C2 C3 C17 119.04(19) . . ?
C4 C3 C17 122.03(19) . . ?
C5 C4 C3 120.1(2) . . ?
C4 C5 C6 120.7(2) . . ?
C5 C6 C1 119.8(2) . . ?
C8 C7 C12 118.6(2) . . ?
C8 C7 C1 124.2(2) . . ?
C12 C7 C1 116.7(2) . . ?
C9 C8 C7 119.4(2) . . ?
C9 C8 N1 119.3(2) . . ?
C7 C8 N1 121.36(19) . . ?
C10 C9 C8 120.9(2) . . ?
C9 C10 C11 120.3(2) . . ?
C12 C11 C10 119.2(2) . . ?
C11 C12 C7 121.5(2) . . ?
C15 C13 C16 109.0(2) . . ?
C15 C13 C14 110.8(2) . . ?
C16 C13 C14 109.3(2) . . ?
C15 C13 N1 111.07(19) . . ?
C16 C13 N1 108.22(18) . . ?
C14 C13 N1 108.35(19) . . ?
C22 C17 C18 118.3(2) . . ?
C22 C17 C3 118.5(2) . . ?
C18 C17 C3 123.06(19) . . ?
C19 C18 C17 120.1(2) . . ?
C19 C18 N2 119.5(2) . . ?
C17 C18 N2 120.39(19) . . ?
C18 C19 C20 120.3(2) . . ?
C21 C20 C19 120.4(2) . . ?
C20 C21 C22 119.4(2) . . ?
C21 C22 C17 121.4(2) . . ?
C25 C23 C26 108.5(2) . . ?
C25 C23 C24 110.2(2) . . ?
C26 C23 C24 110.3(2) . . ?
C25 C23 N2 110.32(18) . . ?
C26 C23 N2 106.13(17) . . ?
C24 C23 N2 111.24(18) . . ?
C28 C27 C32 118.3(2) . . ?
C28 C27 C33 120.92(19) . . ?
C32 C27 C33 120.4(2) . . ?
C27 C28 C29 121.8(2) . . ?
C30 C29 C28 119.0(2) . . ?
C30 C29 C43 123.26(19) . . ?
C28 C29 C43 117.44(19) . . ?
C31 C30 C29 119.9(2) . . ?
C30 C31 C32 120.6(2) . . ?
C31 C32 C27 120.4(2) . . ?
C34 C33 C38 117.8(2) . . ?
C34 C33 C27 126.71(19) . . ?
C38 C33 C27 115.45(19) . . ?
C35 C34 C33 119.4(2) . . ?
C35 C34 N3 117.89(19) . . ?
C33 C34 N3 122.68(19) . . ?
C36 C35 C34 121.4(2) . . ?
C35 C36 C37 119.9(2) . . ?
C38 C37 C36 119.2(2) . . ?
C37 C38 C33 122.3(2) . . ?
N3 C39 C42 108.01(18) . . ?
N3 C39 C41 109.06(17) . . ?
C42 C39 C41 108.89(19) . . ?
N3 C39 C40 111.29(18) . . ?
C42 C39 C40 109.50(19) . . ?
C41 C39 C40 110.03(19) . . ?
C48 C43 C44 118.7(2) . . ?
C48 C43 C29 120.22(19) . . ?
C44 C43 C29 120.68(19) . . ?
C45 C44 C43 119.5(2) . . ?
C45 C44 N4 123.99(19) . . ?
C43 C44 N4 116.45(19) . . ?
C46 C45 C44 120.5(2) . . ?
C45 C46 C47 120.3(2) . . ?
C48 C47 C46 119.5(2) . . ?
C47 C48 C43 121.1(2) . . ?
N4 C49 C52 106.36(18) . . ?
N4 C49 C50 106.88(17) . . ?
C52 C49 C50 109.17(19) . . ?
N4 C49 C51 115.26(18) . . ?
C52 C49 C51 108.67(18) . . ?
C50 C49 C51 110.31(19) . . ?
C53 O5 C56 108.6(2) . . ?
O5 C53 C54 106.8(2) . . ?
C55 C54 C53 103.6(2) . . ?
C54 C55 C56 101.9(3) . . ?
O5 C56 C55 105.8(2) . . ?
C60 O6 C57 108.5(3) . . ?
O6 C57 C58 106.9(3) . . ?
C57 C58 C59 101.5(3) . . ?
C60 C59 C58 101.5(3) . . ?
O6 C60 C59 105.4(3) . . ?

_diffrn_measured_fraction_theta_max 0.985
_diffrn_reflns_theta_full        27.63
_diffrn_measured_fraction_theta_full 0.985
_refine_diff_density_max         1.392
_refine_diff_density_min         -1.033
_refine_diff_density_rms         0.079
####################################################################### 
# 
# 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_H2arenediNOx
_database_code_depnum_ccdc_archive 'CCDC 1411380'
_audit_update_record             
;
2015-07-07 deposited with the CCDC.
2015-08-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97

_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H40 N2 O3'
_chemical_formula_weight         476.64

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c     '
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.0002(4)
_cell_length_b                   9.8745(4)
_cell_length_c                   27.4051(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.384(2)
_cell_angle_gamma                90.00
_cell_volume                     2689.39(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(1)
_exptl_crystal_description       prism
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08

_exptl_crystal_density_diffrn    1.177
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1032
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2007)'
_exptl_absorpt_correction_T_min  0.6944
_exptl_absorpt_correction_T_max  0.7452
_diffrn_ambient_temperature      100(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'CCD Area Detector'
_diffrn_measurement_device_type  'Bruker APEXII'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_reflns_number            55475
_diffrn_reflns_av_R_equivalents  0.0386
_diffrn_reflns_av_sigmaI/netI    0.0193
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         2.05
_diffrn_reflns_theta_max         25.40
_reflns_number_total             4833
_reflns_number_gt                4170
_reflns_threshold_expression     >2sigma(I)
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0221P)²+3.0825P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4833
_refine_ls_number_parameters     325
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0568
_refine_ls_R_factor_gt           0.0479
_refine_ls_wR_factor_ref         0.1104
_refine_ls_wR_factor_gt          0.1068
_refine_ls_goodness_of_fit_ref   1.159
_refine_ls_restrained_S_all      1.159
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.42374(19) 0.38908(19) 0.13798(7) 0.0143(4) Uani 1 1 d . . .
H1 H 0.3625 0.3551 0.1580 0.019 Uiso 1 1 calc R . .
C2 C 0.38122(19) 0.48663(19) 0.10268(7) 0.0144(4) Uani 1 1 d . . .
C3 C 0.4728(2) 0.5319(2) 0.07145(7) 0.0183(4) Uani 1 1 d . . .
H3 H 0.4456 0.5947 0.0471 0.024 Uiso 1 1 calc R . .
C4 C 0.6038(2) 0.4840(2) 0.07646(7) 0.0199(4) Uani 1 1 d . . .
H4 H 0.6639 0.5150 0.0554 0.026 Uiso 1 1 calc R . .
C5 C 0.6461(2) 0.3907(2) 0.11250(7) 0.0184(4) Uani 1 1 d . . .
H5 H 0.7348 0.3606 0.1160 0.024 Uiso 1 1 calc R . .
C6 C 0.55574(19) 0.34151(19) 0.14380(7) 0.0144(4) Uani 1 1 d . . .
C7 C 0.2460(2) 0.5501(2) 0.10182(7) 0.0155(4) Uani 1 1 d . . .
C8 C 0.2402(2) 0.6917(2) 0.10282(7) 0.0192(4) Uani 1 1 d . . .
H8 H 0.3183 0.7412 0.1002 0.026 Uiso 1 1 calc R . .
C9 C 0.1216(2) 0.7598(2) 0.10753(7) 0.0219(5) Uani 1 1 d . . .
H9 H 0.1204 0.8540 0.1084 0.029 Uiso 1 1 calc R . .
C10 C 0.0049(2) 0.6876(2) 0.11090(7) 0.0228(5) Uani 1 1 d . . .
H10 H -0.0747 0.7329 0.1149 0.030 Uiso 1 1 calc R . .
C11 C 0.0065(2) 0.5475(2) 0.10826(7) 0.0191(4) Uani 1 1 d . . .
H11 H -0.0729 0.4994 0.1097 0.025 Uiso 1 1 calc R . .
C12 C 0.12568(19) 0.4776(2) 0.10339(6) 0.0147(4) Uani 1 1 d . . .
C13 C 0.59908(18) 0.2457(2) 0.18454(7) 0.0149(4) Uani 1 1 d . . .
C14 C 0.55615(19) 0.2694(2) 0.23073(7) 0.0180(4) Uani 1 1 d . . .
H14 H 0.4960 0.3395 0.2344 0.024 Uiso 1 1 calc R . .
C15 C 0.6011(2) 0.1907(2) 0.27101(7) 0.0207(4) Uani 1 1 d . . .
H15 H 0.5705 0.2075 0.3013 0.027 Uiso 1 1 calc R . .
C16 C 0.6917(2) 0.0874(2) 0.26622(7) 0.0212(4) Uani 1 1 d . . .
H16 H 0.7257 0.0373 0.2936 0.028 Uiso 1 1 calc R . .
C17 C 0.7317(2) 0.0586(2) 0.22066(7) 0.0190(4) Uani 1 1 d . . .
H17 H 0.7911 -0.0125 0.2174 0.025 Uiso 1 1 calc R . .
C18 C 0.68422(19) 0.1347(2) 0.17947(7) 0.0153(4) Uani 1 1 d . . .
C19 C 0.09276(19) 0.2692(2) 0.05192(7) 0.0157(4) Uani 1 1 d . . .
C20 C 0.1914(2) 0.3242(2) 0.01791(7) 0.0185(4) Uani 1 1 d . . .
H20a H 0.1823 0.4208 0.0154 0.028 Uiso 1 1 calc R . .
H20b H 0.1721 0.2845 -0.0141 0.028 Uiso 1 1 calc R . .
H20c H 0.2817 0.3018 0.0310 0.028 Uiso 1 1 calc R . .
C21 C 0.1138(2) 0.1165(2) 0.05748(7) 0.0190(4) Uani 1 1 d . . .
H21a H 0.2027 0.0989 0.0733 0.028 Uiso 1 1 calc R . .
H21b H 0.1034 0.0747 0.0256 0.028 Uiso 1 1 calc R . .
H21c H 0.0486 0.0798 0.0770 0.028 Uiso 1 1 calc R . .
C22 C -0.0521(2) 0.2998(2) 0.03050(7) 0.0212(4) Uani 1 1 d . . .
H22a H -0.1131 0.2686 0.0528 0.032 Uiso 1 1 calc R . .
H22b H -0.0713 0.2542 -0.0004 0.032 Uiso 1 1 calc R . .
H22c H -0.0629 0.3956 0.0257 0.032 Uiso 1 1 calc R . .
C23 C 0.6401(2) -0.0034(2) 0.10345(7) 0.0208(4) Uani 1 1 d . . .
C24 C 0.6955(2) -0.0179(3) 0.05404(8) 0.0304(5) Uani 1 1 d . . .
H24a H 0.6934 0.0685 0.0379 0.046 Uiso 1 1 calc R . .
H24b H 0.6414 -0.0813 0.0339 0.046 Uiso 1 1 calc R . .
H24c H 0.7866 -0.0501 0.0592 0.046 Uiso 1 1 calc R . .
C25 C 0.6442(2) -0.1392(2) 0.13039(9) 0.0281(5) Uani 1 1 d . . .
H25a H 0.7360 -0.1648 0.1398 0.042 Uiso 1 1 calc R . .
H25b H 0.6008 -0.2071 0.1091 0.042 Uiso 1 1 calc R . .
H25c H 0.5982 -0.1310 0.1592 0.042 Uiso 1 1 calc R . .
C26 C 0.4951(2) 0.0468(2) 0.09461(8) 0.0267(5) Uani 1 1 d . . .
H26a H 0.4598 0.0580 0.1255 0.040 Uiso 1 1 calc R . .
H26b H 0.4415 -0.0181 0.0750 0.040 Uiso 1 1 calc R . .
H26c H 0.4927 0.1320 0.0777 0.040 Uiso 1 1 calc R . .
N1 N 0.12960(16) 0.33107(16) 0.10168(6) 0.0140(3) Uani 1 1 d . . .
N2 N 0.72270(15) 0.10378(17) 0.13141(6) 0.0163(4) Uani 1 1 d . . .
O1 O 0.03106(13) 0.28142(15) 0.13297(5) 0.0183(3) Uani 1 1 d . . .
H1a H 0.0698 0.2583 0.1596 0.027 Uiso 1 1 calc R . .
O2 O 0.86016(13) 0.05252(15) 0.13849(5) 0.0208(3) Uani 1 1 d . . .
H2a H 0.9125 0.1133 0.1331 0.031 Uiso 1 1 calc R . .
O3 O 0.18047(15) 0.19892(16) 0.21599(5) 0.0280(4) Uani 1 1 d . . .
C27 C 0.2357(2) 0.0686(3) 0.20507(9) 0.0311(5) Uani 1 1 d . . .
H27a H 0.3263 0.0586 0.2214 0.041 Uiso 1 1 calc R . .
H27b H 0.2380 0.0580 0.1700 0.041 Uiso 1 1 calc R . .
C28 C 0.1425(2) -0.0338(2) 0.22409(8) 0.0277(5) Uani 1 1 d . . .
H28a H 0.1874 -0.1199 0.2311 0.037 Uiso 1 1 calc R . .
H28b H 0.0628 -0.0480 0.2011 0.037 Uiso 1 1 calc R . .
C29 C 0.1083(2) 0.0350(2) 0.27079(8) 0.0310(5) Uani 1 1 d . . .
H29a H 0.0247 0.0008 0.2808 0.041 Uiso 1 1 calc R . .
H29b H 0.1797 0.0231 0.2975 0.041 Uiso 1 1 calc R . .
C30 C 0.0951(3) 0.1823(2) 0.25501(8) 0.0332(6) Uani 1 1 d . . .
H30a H 0.0024 0.2035 0.2433 0.044 Uiso 1 1 calc R . .
H30b H 0.1242 0.2417 0.2823 0.044 Uiso 1 1 calc R . .


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.393(3) . ?
C1 C2 1.397(3) . ?
C2 C3 1.395(3) . ?
C2 C7 1.489(3) . ?
C3 C4 1.385(3) . ?
C4 C5 1.382(3) . ?
C5 C6 1.400(3) . ?
C6 C13 1.490(3) . ?
C7 C8 1.400(3) . ?
C7 C12 1.405(3) . ?
C8 C9 1.382(3) . ?
C9 C10 1.379(3) . ?
C10 C11 1.385(3) . ?
C11 C12 1.397(3) . ?
C12 N1 1.448(3) . ?
C13 C14 1.401(3) . ?
C13 C18 1.405(3) . ?
C14 C15 1.383(3) . ?
C15 C16 1.380(3) . ?
C16 C17 1.382(3) . ?
C17 C18 1.394(3) . ?
C18 N2 1.445(2) . ?
C19 N1 1.502(2) . ?
C19 C21 1.528(3) . ?
C19 C20 1.530(3) . ?
C19 C22 1.532(3) . ?
C23 N2 1.499(3) . ?
C23 C26 1.526(3) . ?
C23 C24 1.526(3) . ?
C23 C25 1.529(3) . ?
N1 O1 1.4611(19) . ?
N2 O2 1.458(2) . ?
O3 C27 1.445(3) . ?
O3 C30 1.450(3) . ?
C27 C28 1.507(3) . ?
C28 C29 1.521(3) . ?
C29 C30 1.519(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 121.54(17) . . ?
C3 C2 C1 118.39(18) . . ?
C3 C2 C7 120.85(17) . . ?
C1 C2 C7 120.49(17) . . ?
C4 C3 C2 120.55(18) . . ?
C5 C4 C3 120.60(18) . . ?
C4 C5 C6 120.14(18) . . ?
C1 C6 C5 118.71(18) . . ?
C1 C6 C13 119.51(17) . . ?
C5 C6 C13 121.70(17) . . ?
C8 C7 C12 118.15(18) . . ?
C8 C7 C2 117.35(18) . . ?
C12 C7 C2 124.36(17) . . ?
C9 C8 C7 121.7(2) . . ?
C10 C9 C8 119.74(19) . . ?
C9 C10 C11 119.9(2) . . ?
C10 C11 C12 120.9(2) . . ?
C11 C12 C7 119.56(18) . . ?
C11 C12 N1 121.58(18) . . ?
C7 C12 N1 118.82(17) . . ?
C14 C13 C18 118.00(18) . . ?
C14 C13 C6 118.59(17) . . ?
C18 C13 C6 123.39(17) . . ?
C15 C14 C13 121.50(19) . . ?
C16 C15 C14 119.85(18) . . ?
C15 C16 C17 119.79(19) . . ?
C16 C17 C18 120.92(19) . . ?
C17 C18 C13 119.73(18) . . ?
C17 C18 N2 121.54(17) . . ?
C13 C18 N2 118.72(17) . . ?
N1 C19 C21 107.09(15) . . ?
N1 C19 C20 107.40(15) . . ?
C21 C19 C20 108.66(16) . . ?
N1 C19 C22 113.20(15) . . ?
C21 C19 C22 110.28(16) . . ?
C20 C19 C22 110.05(16) . . ?
N2 C23 C26 108.14(16) . . ?
N2 C23 C24 106.64(17) . . ?
C26 C23 C24 108.78(18) . . ?
N2 C23 C25 112.88(17) . . ?
C26 C23 C25 109.57(18) . . ?
C24 C23 C25 110.70(18) . . ?
C12 N1 O1 107.08(14) . . ?
C12 N1 C19 115.53(15) . . ?
O1 N1 C19 106.44(13) . . ?
C18 N2 O2 107.14(14) . . ?
C18 N2 C23 115.31(15) . . ?
O2 N2 C23 106.29(14) . . ?
C27 O3 C30 108.80(17) . . ?
O3 C27 C28 105.13(17) . . ?
C27 C28 C29 101.33(19) . . ?
C30 C29 C28 102.08(18) . . ?
O3 C30 C29 106.15(19) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1a O3 0.82 1.89 2.705(2) 171.7 .
O2 H2a O1 0.82 2.04 2.848(2) 168.0 1_655

_diffrn_measured_fraction_theta_max 0.979
_diffrn_reflns_theta_full        25.40
_diffrn_measured_fraction_theta_full 0.979
_refine_diff_density_max         0.211
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.044
