# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C
# This journal is © The Royal Society of Chemistry 2013


#######################################################################
#
#                 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_RTP
_database_code_depnum_ccdc_archive 'CCDC 908562'
#TrackingRef '15079_web_deposit_cif_file_0_zhihuasun_1351673840.dabco p-nitrophenol.cif'
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H22 N4 O6'
_chemical_formula_weight         390.40
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   P21/c
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                   9.984(6)
_cell_length_b                   8.890(5)
_cell_length_c                   10.791(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.593(9)
_cell_angle_gamma                90.00
_cell_volume                     944.4(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2222
_cell_measurement_theta_min      2.9858
_cell_measurement_theta_max      27.4971
_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.29
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.373
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             412
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9574
_exptl_absorpt_correction_T_max  0.9703
_exptl_absorpt_process_details   ?
_exptl_special_details           
;
?
;
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Mercury CCD'
_diffrn_measurement_method       CCD_Profile_fitting
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  120
_diffrn_standards_decay_%        2
_diffrn_reflns_number            5754
_diffrn_reflns_av_R_equivalents  0.0341
_diffrn_reflns_av_sigmaI/netI    0.0314
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         4.04
_diffrn_reflns_theta_max         25.00
_reflns_number_total             1604
_reflns_number_gt                1214
_reflns_threshold_expression     >2sigma(I)
_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0906P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1604
_refine_ls_number_parameters     154
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0569
_refine_ls_R_factor_gt           0.0461
_refine_ls_wR_factor_ref         0.1390
_refine_ls_wR_factor_gt          0.1303
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_restrained_S_all      1.068
_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
O1 O 0.88996(12) 0.01963(14) 0.63701(11) 0.0728(4) Uani 1 1 d . . .
H1A H 0.8835 0.0251 0.7181 0.087 Uiso 1 1 d R . .
O2 O 0.39055(15) -0.19277(18) 0.25307(14) 0.0963(6) Uani 1 1 d . . .
O3 O 0.38101(17) -0.3503(2) 0.40201(16) 0.1156(7) Uani 1 1 d . . .
N1 N 0.43373(16) -0.2439(2) 0.35668(16) 0.0732(5) Uani 1 1 d . . .
N2 N -0.05040(12) -0.49208(12) 0.38254(11) 0.0494(4) Uani 1 1 d . . .
C1 C 0.55494(15) -0.17567(18) 0.42993(14) 0.0534(4) Uani 1 1 d . . .
C2 C 0.59230(17) -0.2183(2) 0.55334(15) 0.0586(5) Uani 1 1 d . . .
H2 H 0.5429 -0.2911 0.5882 0.070 Uiso 1 1 calc R . .
C3 C 0.70366(16) -0.15178(18) 0.62449(14) 0.0550(4) Uani 1 1 d . . .
H3 H 0.7283 -0.1783 0.7086 0.066 Uiso 1 1 calc R . .
C4 C 0.77960(16) -0.04571(17) 0.57236(14) 0.0513(4) Uani 1 1 d . . .
C5 C 0.7403(2) -0.00619(18) 0.44626(16) 0.0627(5) Uani 1 1 d . . .
H5 H 0.7911 0.0637 0.4098 0.075 Uiso 1 1 calc R . .
C6 C 0.62742(18) -0.06970(19) 0.37587(15) 0.0598(5) Uani 1 1 d . . .
H6 H 0.6002 -0.0414 0.2925 0.072 Uiso 1 1 calc R . .
C7 C 0.0997(3) -0.4585(5) 0.3996(3) 0.0675(9) Uani 0.50 1 d P . .
H7A H 0.1138 -0.3591 0.3695 0.081 Uiso 0.50 1 d PR . .
H7B H 0.1435 -0.5291 0.3521 0.081 Uiso 0.50 1 d PR . .
C8 C 0.1601(4) -0.4701(5) 0.5406(3) 0.0692(10) Uani 0.50 1 d P . .
H8A H 0.2028 -0.3767 0.5690 0.083 Uiso 0.50 1 d PR . .
H8B H 0.2198 -0.5673 0.5562 0.083 Uiso 0.50 1 d PR . .
C9 C -0.1165(5) -0.3882(5) 0.4517(3) 0.0800(12) Uani 0.50 1 d P . .
H9A H -0.2114 -0.4123 0.4422 0.096 Uiso 0.50 1 d PR . .
H9B H -0.1079 -0.2887 0.4194 0.096 Uiso 0.50 1 d PR . .
C10 C -0.0547(5) -0.3958(5) 0.5921(3) 0.0802(12) Uani 0.50 1 d P . .
H10A H -0.1244 -0.4153 0.6415 0.096 Uiso 0.50 1 d PR . .
H10B H -0.0152 -0.2997 0.6170 0.096 Uiso 0.50 1 d PR . .
C11 C -0.0640(4) -0.6467(4) 0.4277(3) 0.0688(10) Uani 0.50 1 d P . .
H11A H -0.0148 -0.7150 0.3830 0.083 Uiso 0.50 1 d PR . .
H11B H -0.1579 -0.6757 0.4128 0.083 Uiso 0.50 1 d PR . .
C12 C -0.0068(5) -0.6550(4) 0.5693(3) 0.0745(11) Uani 0.50 1 d P . .
H12A H 0.0857 -0.7202 0.5828 0.089 Uiso 0.50 1 d PR . .
H12B H -0.0777 -0.6847 0.6145 0.089 Uiso 0.50 1 d PR . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0697(9) 0.0947(9) 0.0516(8) -0.0053(6) 0.0026(6) -0.0258(6)
O2 0.0755(10) 0.1412(14) 0.0624(9) -0.0283(9) -0.0174(7) 0.0159(8)
O3 0.0989(13) 0.1460(16) 0.0978(12) -0.0255(11) 0.0049(9) -0.0561(11)
N1 0.0613(10) 0.0985(12) 0.0570(10) -0.0300(9) 0.0015(8) 0.0051(9)
N2 0.0446(8) 0.0504(7) 0.0493(8) 0.0022(5) -0.0037(6) 0.0058(5)
C1 0.0466(9) 0.0641(10) 0.0469(9) -0.0181(7) -0.0001(7) 0.0089(7)
C2 0.0553(10) 0.0717(10) 0.0492(10) -0.0048(8) 0.0095(7) -0.0061(7)
C3 0.0565(10) 0.0691(10) 0.0373(8) 0.0011(7) 0.0016(7) 0.0006(7)
C4 0.0535(9) 0.0560(9) 0.0425(9) -0.0066(7) 0.0023(7) 0.0000(6)
C5 0.0836(13) 0.0557(9) 0.0477(10) 0.0005(7) 0.0075(9) -0.0067(8)
C6 0.0763(11) 0.0596(9) 0.0388(8) -0.0036(7) -0.0037(8) 0.0131(8)
C7 0.055(2) 0.088(3) 0.056(2) 0.0074(18) -0.0033(16) -0.0151(18)
C8 0.054(2) 0.093(3) 0.057(2) 0.0015(18) -0.0032(17) -0.0145(17)
C9 0.090(3) 0.090(3) 0.053(2) -0.0006(19) -0.006(2) 0.048(3)
C10 0.088(3) 0.092(3) 0.055(2) -0.0029(19) -0.0059(19) 0.048(2)
C11 0.075(3) 0.0583(19) 0.064(2) 0.0056(16) -0.0133(18) -0.0144(17)
C12 0.087(3) 0.062(2) 0.065(2) 0.0173(17) -0.013(2) -0.0132(19)
_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
O1 C4 1.335(2) . ?
O1 H1A 0.8893 . ?
O2 N1 1.217(2) . ?
O3 N1 1.224(2) . ?
N1 C1 1.462(2) . ?
N2 C9 1.418(4) . ?
N2 C10 1.440(4) 3_546 ?
N2 C11 1.472(3) . ?
N2 C12 1.486(4) 3_546 ?
N2 C7 1.509(4) . ?
N2 C8 1.518(4) 3_546 ?
C1 C2 1.375(2) . ?
C1 C6 1.376(3) . ?
C2 C3 1.375(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.387(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.397(2) . ?
C5 C6 1.371(2) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C10 1.379(6) 3_546 ?
C7 C12 1.448(6) 3_546 ?
C7 C8 1.544(5) . ?
C7 H7A 0.9599 . ?
C7 H7B 0.9599 . ?
C8 C9 1.340(6) 3_546 ?
C8 C11 1.492(6) 3_546 ?
C8 N2 1.518(4) 3_546 ?
C8 C10 2.019(6) 3_546 ?
C8 H8A 0.9601 . ?
C8 H8B 1.0472 . ?
C9 C8 1.340(6) 3_546 ?
C9 C12 1.345(6) 3_546 ?
C9 C10 1.539(5) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9599 . ?
C10 C11 1.295(6) 3_546 ?
C10 C7 1.379(6) 3_546 ?
C10 N2 1.440(4) 3_546 ?
C10 C12 1.993(6) 3_546 ?
C10 C8 2.019(6) 3_546 ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C11 C10 1.295(6) 3_546 ?
C11 C8 1.492(6) 3_546 ?
C11 C12 1.541(5) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C12 C9 1.345(6) 3_546 ?
C12 C7 1.448(6) 3_546 ?
C12 N2 1.486(4) 3_546 ?
C12 C10 1.993(6) 3_546 ?
C12 H12A 1.0794 . ?
C12 H12B 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
C4 O1 H1A 110.4 . . ?
O2 N1 O3 123.07(18) . . ?
O2 N1 C1 118.45(19) . . ?
O3 N1 C1 118.48(18) . . ?
C9 N2 C10 137.7(2) . 3_546 ?
C9 N2 C11 110.9(3) . . ?
C10 N2 C11 52.8(3) 3_546 . ?
C9 N2 C12 55.1(3) . 3_546 ?
C10 N2 C12 108.5(3) 3_546 3_546 ?
C11 N2 C12 139.2(2) . 3_546 ?
C9 N2 C7 110.3(3) . . ?
C10 N2 C7 55.7(3) 3_546 . ?
C11 N2 C7 106.8(2) . . ?
C12 N2 C7 57.8(2) 3_546 . ?
C9 N2 C8 54.2(3) . 3_546 ?
C10 N2 C8 108.2(3) 3_546 3_546 ?
C11 N2 C8 59.9(3) . 3_546 ?
C12 N2 C8 105.9(3) 3_546 3_546 ?
C7 N2 C8 140.3(2) . 3_546 ?
C2 C1 C6 121.50(15) . . ?
C2 C1 N1 118.41(17) . . ?
C6 C1 N1 120.08(16) . . ?
C3 C2 C1 119.08(16) . . ?
C3 C2 H2 120.5 . . ?
C1 C2 H2 120.5 . . ?
C2 C3 C4 120.78(14) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
O1 C4 C3 122.92(14) . . ?
O1 C4 C5 118.23(15) . . ?
C3 C4 C5 118.85(15) . . ?
C6 C5 C4 120.51(16) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C5 C6 C1 119.26(15) . . ?
C5 C6 H6 120.4 . . ?
C1 C6 H6 120.4 . . ?
C10 C7 C12 114.3(3) 3_546 3_546 ?
C10 C7 N2 59.6(2) 3_546 . ?
C12 C7 N2 60.3(2) 3_546 . ?
C10 C7 C8 87.2(3) 3_546 . ?
C12 C7 C8 88.8(3) 3_546 . ?
N2 C7 C8 108.9(3) . . ?
C10 C7 H7A 162.6 3_546 . ?
C12 C7 H7A 64.6 3_546 . ?
N2 C7 H7A 109.8 . . ?
C8 C7 H7A 109.9 . . ?
C10 C7 H7B 66.6 3_546 . ?
C12 C7 H7B 161.0 3_546 . ?
N2 C7 H7B 109.7 . . ?
C8 C7 H7B 110.1 . . ?
H7A C7 H7B 108.4 . . ?
C9 C8 C11 114.3(3) 3_546 3_546 ?
C9 C8 N2 59.1(2) 3_546 3_546 ?
C11 C8 N2 58.5(2) 3_546 3_546 ?
C9 C8 C7 92.6(3) 3_546 . ?
C11 C8 C7 91.1(3) 3_546 . ?
N2 C8 C7 110.8(2) 3_546 . ?
C9 C8 C10 49.6(2) 3_546 3_546 ?
C11 C8 C10 107.1(2) 3_546 3_546 ?
N2 C8 C10 85.3(2) 3_546 3_546 ?
C7 C8 C10 43.0(2) . 3_546 ?
C9 C8 H8A 157.7 3_546 . ?
C11 C8 H8A 66.0 3_546 . ?
N2 C8 H8A 109.8 3_546 . ?
C7 C8 H8A 109.7 . . ?
C10 C8 H8A 152.7 3_546 . ?
C9 C8 H8B 52.9 3_546 . ?
C11 C8 H8B 155.2 3_546 . ?
N2 C8 H8B 99.9 3_546 . ?
C7 C8 H8B 109.4 . . ?
C10 C8 H8B 80.9 3_546 . ?
H8A C8 H8B 116.9 . . ?
C8 C9 C12 126.6(3) 3_546 3_546 ?
C8 C9 N2 66.7(2) 3_546 . ?
C12 C9 N2 65.0(3) 3_546 . ?
C8 C9 C10 88.8(3) 3_546 . ?
C12 C9 C10 87.2(3) 3_546 . ?
N2 C9 C10 110.2(3) . . ?
C8 C9 H9A 58.1 3_546 . ?
C12 C9 H9A 163.9 3_546 . ?
N2 C9 H9A 109.6 . . ?
C10 C9 H9A 108.8 . . ?
C8 C9 H9B 159.8 3_546 . ?
C12 C9 H9B 62.3 3_546 . ?
N2 C9 H9B 109.3 . . ?
C10 C9 H9B 110.7 . . ?
H9A C9 H9B 108.3 . . ?
C11 C10 C7 127.0(3) 3_546 3_546 ?
C11 C10 N2 64.9(2) 3_546 3_546 ?
C7 C10 N2 64.7(2) 3_546 3_546 ?
C11 C10 C9 93.0(4) 3_546 . ?
C7 C10 C9 91.3(3) 3_546 . ?
N2 C10 C9 112.1(3) 3_546 . ?
C11 C10 C12 50.6(3) 3_546 3_546 ?
C7 C10 C12 114.9(3) 3_546 3_546 ?
N2 C10 C12 90.1(2) 3_546 3_546 ?
C9 C10 C12 42.4(2) . 3_546 ?
C11 C10 C8 116.0(3) 3_546 3_546 ?
C7 C10 C8 49.8(2) 3_546 3_546 ?
N2 C10 C8 90.2(3) 3_546 3_546 ?
C9 C10 C8 41.6(2) . 3_546 ?
C12 C10 C8 73.39(19) 3_546 3_546 ?
C11 C10 H10A 155.8 3_546 . ?
C7 C10 H10A 61.3 3_546 . ?
N2 C10 H10A 110.0 3_546 . ?
C9 C10 H10A 110.2 . . ?
C12 C10 H10A 152.1 3_546 . ?
C8 C10 H10A 86.9 3_546 . ?
C11 C10 H10B 56.1 3_546 . ?
C7 C10 H10B 160.2 3_546 . ?
N2 C10 H10B 108.1 3_546 . ?
C9 C10 H10B 108.4 . . ?
C12 C10 H10B 82.6 3_546 . ?
C8 C10 H10B 149.9 3_546 . ?
H10A C10 H10B 107.9 . . ?
C10 C11 N2 62.4(2) 3_546 . ?
C10 C11 C8 118.5(3) 3_546 3_546 ?
N2 C11 C8 61.6(2) . 3_546 ?
C10 C11 C12 88.9(3) 3_546 . ?
N2 C11 C12 109.5(2) . . ?
C8 C11 C12 87.3(3) 3_546 . ?
C10 C11 H11A 62.8 3_546 . ?
N2 C11 H11A 109.9 . . ?
C8 C11 H11A 163.3 3_546 . ?
C12 C11 H11A 109.4 . . ?
C10 C11 H11B 161.0 3_546 . ?
N2 C11 H11B 109.7 . . ?
C8 C11 H11B 65.0 3_546 . ?
C12 C11 H11B 110.1 . . ?
H11A C11 H11B 108.2 . . ?
C9 C12 C7 118.7(3) 3_546 3_546 ?
C9 C12 N2 59.9(2) 3_546 3_546 ?
C7 C12 N2 61.9(2) 3_546 3_546 ?
C9 C12 C11 90.9(3) 3_546 . ?
C7 C12 C11 92.9(3) 3_546 . ?
N2 C12 C11 111.2(2) 3_546 . ?
C9 C12 C10 50.5(2) 3_546 3_546 ?
C7 C12 C10 110.3(2) 3_546 3_546 ?
N2 C12 C10 87.1(2) 3_546 3_546 ?
C11 C12 C10 40.5(2) . 3_546 ?
C9 C12 H12A 52.4 3_546 . ?
C7 C12 H12A 155.5 3_546 . ?
N2 C12 H12A 98.9 3_546 . ?
C11 C12 H12A 109.0 . . ?
C10 C12 H12A 81.8 3_546 . ?
C9 C12 H12B 159.5 3_546 . ?
C7 C12 H12B 61.3 3_546 . ?
N2 C12 H12B 109.7 3_546 . ?
C11 C12 H12B 109.5 . . ?
C10 C12 H12B 150.0 3_546 . ?
H12A C12 H12B 118.1 . . ?
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 N2 0.89 1.81 2.629(2) 151.7 4_656
_diffrn_measured_fraction_theta_max 0.962
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.962
_refine_diff_density_max         0.168
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.030


data_ITP
_database_code_depnum_ccdc_archive 'CCDC 908563'
#TrackingRef '15079_web_deposit_cif_file_0_zhihuasun_1351673840.dabco p-nitrophenol.cif'
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H22 N4 O6'
_chemical_formula_weight         390.40
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'
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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
_cell_length_a                   9.805(5)
_cell_length_b                   13.762(6)
_cell_length_c                   13.774(7)
_cell_angle_alpha                80.039(13)
_cell_angle_beta                 83.930(9)
_cell_angle_gamma                84.024(11)
_cell_volume                     1813.3(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6040
_cell_measurement_theta_min      2.0969
_cell_measurement_theta_max      27.4932
_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.48
_exptl_crystal_size_min          0.35
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.430
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             824
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.9455
_exptl_absorpt_correction_T_max  0.9628
_exptl_absorpt_process_details   ?
_exptl_special_details           
;
?
;
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       '\w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 120
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            15084
_diffrn_reflns_av_R_equivalents  0.0917
_diffrn_reflns_av_sigmaI/netI    0.0690
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.30
_diffrn_reflns_theta_max         27.39
_reflns_number_total             7628
_reflns_number_gt                6961
_reflns_threshold_expression     >2sigma(I)
_computing_data_collection       'Bruker XSCANS'
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.1085P)^2^+25.1525P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         7628
_refine_ls_number_parameters     506
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1829
_refine_ls_R_factor_gt           0.1768
_refine_ls_wR_factor_ref         0.4191
_refine_ls_wR_factor_gt          0.4157
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_restrained_S_all      1.089
_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
N1 N -0.0506(5) 0.3075(4) 0.8151(4) 0.0178(10) Uani 1 1 d . . .
N2 N 0.0489(5) 0.1930(4) 0.6909(4) 0.0198(11) Uani 1 1 d . . .
C1 C -0.1604(7) 0.2888(6) 0.7540(5) 0.0282(15) Uani 1 1 d . . .
H1A H -0.2005 0.3514 0.7204 0.034 Uiso 1 1 calc R . .
H1B H -0.2328 0.2560 0.7968 0.034 Uiso 1 1 calc R . .
C2 C -0.0978(7) 0.2226(5) 0.6760(5) 0.0257(14) Uani 1 1 d . . .
H2A H -0.1478 0.1641 0.6834 0.031 Uiso 1 1 calc R . .
H2B H -0.1060 0.2591 0.6097 0.031 Uiso 1 1 calc R . .
C3 C 0.0618(8) 0.3512(6) 0.7470(5) 0.0289(15) Uani 1 1 d . . .
H3A H 0.1333 0.3647 0.7852 0.035 Uiso 1 1 calc R . .
H3B H 0.0266 0.4135 0.7099 0.035 Uiso 1 1 calc R . .
C4 C 0.1244(8) 0.2811(6) 0.6740(5) 0.0282(15) Uani 1 1 d . . .
H4A H 0.1187 0.3148 0.6065 0.034 Uiso 1 1 calc R . .
H4B H 0.2207 0.2624 0.6840 0.034 Uiso 1 1 calc R . .
C5 C 0.0051(8) 0.2113(5) 0.8672(5) 0.0268(14) Uani 1 1 d . . .
H5A H -0.0669 0.1807 0.9123 0.032 Uiso 1 1 calc R . .
H5B H 0.0782 0.2214 0.9057 0.032 Uiso 1 1 calc R . .
C6 C 0.0621(7) 0.1419(5) 0.7922(5) 0.0272(15) Uani 1 1 d . . .
H6A H 0.1582 0.1209 0.8009 0.033 Uiso 1 1 calc R . .
H6B H 0.0116 0.0833 0.8043 0.033 Uiso 1 1 calc R . .
O9 O 0.8877(5) 0.4428(4) -0.0722(4) 0.0276(11) Uani 1 1 d . . .
O7 O 0.3676(6) 0.3555(5) 0.2231(4) 0.0391(14) Uani 1 1 d . . .
O8 O 0.3737(6) 0.5125(4) 0.2232(4) 0.0329(12) Uani 1 1 d . . .
N7 N 0.4206(6) 0.4344(5) 0.1963(4) 0.0245(12) Uani 1 1 d . . .
C29 C 0.7035(7) 0.3523(5) 0.0194(6) 0.0270(15) Uani 1 1 d . . .
H29 H 0.7329 0.2963 -0.0091 0.032 Uiso 1 1 calc R . .
C25 C 0.5439(6) 0.4351(5) 0.1292(4) 0.0180(12) Uani 1 1 d . . .
C28 C 0.7759(6) 0.4369(5) -0.0058(5) 0.0180(12) Uani 1 1 d . . .
C27 C 0.7310(8) 0.5211(5) 0.0386(5) 0.0243(14) Uani 1 1 d . . .
H27 H 0.7806 0.5767 0.0242 0.029 Uiso 1 1 calc R . .
C30 C 0.5886(7) 0.3519(5) 0.0866(5) 0.0246(14) Uani 1 1 d . . .
H30 H 0.5408 0.2955 0.1034 0.030 Uiso 1 1 calc R . .
C26 C 0.6131(7) 0.5211(5) 0.1038(4) 0.0225(13) Uani 1 1 d . . .
H26 H 0.5803 0.5777 0.1303 0.027 Uiso 1 1 calc R . .
O12 O 0.1164(5) 1.0706(4) 0.0535(4) 0.0261(11) Uani 1 1 d . . .
O11 O 0.6269(7) 0.7669(5) 0.1435(5) 0.0487(16) Uani 1 1 d . . .
O10 O 0.6341(6) 0.7773(4) -0.0160(5) 0.0384(14) Uani 1 1 d . . .
C35 C 0.2931(7) 0.9742(5) 0.1453(5) 0.0211(13) Uani 1 1 d . . .
H35 H 0.2614 1.0005 0.2022 0.025 Uiso 1 1 calc R . .
C31 C 0.4574(6) 0.8696(5) 0.0614(5) 0.0192(12) Uani 1 1 d . . .
C34 C 0.2263(6) 1.0046(4) 0.0613(5) 0.0182(12) Uani 1 1 d . . .
N8 N 0.5806(6) 0.7978(5) 0.0656(5) 0.0276(13) Uani 1 1 d . . .
C33 C 0.2789(7) 0.9655(5) -0.0250(5) 0.0259(14) Uani 1 1 d . . .
H33 H 0.2346 0.9844 -0.0827 0.031 Uiso 1 1 calc R . .
C32 C 0.3960(7) 0.8989(5) -0.0247(5) 0.0242(14) Uani 1 1 d . . .
H32 H 0.4318 0.8748 -0.0820 0.029 Uiso 1 1 calc R . .
C36 C 0.4075(7) 0.9048(5) 0.1477(5) 0.0216(13) Uani 1 1 d . . .
H36 H 0.4494 0.8828 0.2060 0.026 Uiso 1 1 calc R . .
O5 O 0.5999(5) 0.2834(4) 0.4661(5) 0.0342(13) Uani 1 1 d . . .
O6 O 0.1037(5) 0.5901(4) 0.5510(4) 0.0254(10) Uani 1 1 d . . .
O4 O 0.6113(6) 0.2829(4) 0.6237(5) 0.0376(13) Uani 1 1 d . . .
N6 N 0.5565(6) 0.3125(4) 0.5441(5) 0.0240(12) Uani 1 1 d . . .
C19 C 0.4363(6) 0.3841(5) 0.5456(5) 0.0218(13) Uani 1 1 d . . .
C22 C 0.2138(6) 0.5232(4) 0.5507(5) 0.0181(12) Uani 1 1 d . . .
C23 C 0.2944(6) 0.4985(5) 0.6331(5) 0.0209(13) Uani 1 1 d . . .
H23 H 0.2723 0.5295 0.6883 0.025 Uiso 1 1 calc R . .
C20 C 0.3593(6) 0.4069(5) 0.4656(5) 0.0190(12) Uani 1 1 d . . .
H20 H 0.3831 0.3764 0.4103 0.023 Uiso 1 1 calc R . .
C24 C 0.4050(6) 0.4286(4) 0.6307(5) 0.0182(12) Uani 1 1 d . . .
H24 H 0.4580 0.4111 0.6842 0.022 Uiso 1 1 calc R . .
C21 C 0.2467(6) 0.4754(5) 0.4682(5) 0.0213(13) Uani 1 1 d . . .
H21 H 0.1924 0.4899 0.4153 0.026 Uiso 1 1 calc R . .
O3 O 0.1068(5) 0.0483(4) 0.5879(4) 0.0256(10) Uani 1 1 d . . .
O2 O 0.6068(6) -0.0415(5) 0.2869(4) 0.0382(13) Uani 1 1 d . . .
O1 O 0.6067(6) 0.1180(5) 0.2710(4) 0.0407(14) Uani 1 1 d . . .
N5 N 0.5581(6) 0.0403(5) 0.3087(4) 0.0259(13) Uani 1 1 d . . .
C15 C 0.4390(6) 0.0423(5) 0.3823(4) 0.0171(12) Uani 1 1 d . . .
C14 C 0.4024(7) 0.1288(5) 0.4209(6) 0.0270(14) Uani 1 1 d . . .
H14 H 0.4507 0.1845 0.3998 0.032 Uiso 1 1 calc R . .
C18 C 0.2152(7) 0.0486(5) 0.5206(4) 0.0191(12) Uani 1 1 d . . .
C17 C 0.2534(7) -0.0366(5) 0.4782(4) 0.0211(13) Uani 1 1 d . . .
H17 H 0.2025 -0.0913 0.4964 0.025 Uiso 1 1 calc R . .
C13 C 0.2917(6) 0.1297(5) 0.4920(5) 0.0215(13) Uani 1 1 d . . .
H13 H 0.2681 0.1859 0.5212 0.026 Uiso 1 1 calc R . .
C16 C 0.3659(7) -0.0403(5) 0.4095(5) 0.0217(13) Uani 1 1 d . . .
H16 H 0.3922 -0.0973 0.3820 0.026 Uiso 1 1 calc R . .
N4 N 1.0477(5) 0.1837(4) 0.1891(4) 0.0162(10) Uani 1 1 d . . .
N3 N 0.9467(5) 0.3072(4) 0.3043(4) 0.0188(11) Uani 1 1 d . . .
C7 C 1.0066(8) 0.3612(6) 0.2078(5) 0.0298(15) Uani 1 1 d . . .
H7A H 1.0801 0.3986 0.2195 0.036 Uiso 1 1 calc R . .
H7B H 0.9362 0.4074 0.1767 0.036 Uiso 1 1 calc R . .
C8 C 1.0629(7) 0.2870(5) 0.1396(5) 0.0271(15) Uani 1 1 d . . .
H8A H 1.0139 0.3003 0.0804 0.033 Uiso 1 1 calc R . .
H8B H 1.1594 0.2951 0.1197 0.033 Uiso 1 1 calc R . .
C11 C 0.8373(7) 0.2498(6) 0.2848(6) 0.0272(14) Uani 1 1 d . . .
H11A H 0.7666 0.2939 0.2516 0.033 Uiso 1 1 calc R . .
H11B H 0.7953 0.2163 0.3468 0.033 Uiso 1 1 calc R . .
C10 C 1.1203(8) 0.1683(7) 0.2792(6) 0.0359(18) Uani 1 1 d . . .
H10A H 1.2167 0.1787 0.2613 0.043 Uiso 1 1 calc R . .
H10B H 1.1149 0.1005 0.3126 0.043 Uiso 1 1 calc R . .
C12 C 0.8984(7) 0.1723(6) 0.2188(6) 0.0285(15) Uani 1 1 d . . .
H12A H 0.8874 0.1061 0.2549 0.034 Uiso 1 1 calc R . .
H12B H 0.8489 0.1810 0.1601 0.034 Uiso 1 1 calc R . .
C9 C 1.0577(7) 0.2397(6) 0.3497(5) 0.0293(15) Uani 1 1 d . . .
H9A H 1.0212 0.2021 0.4114 0.035 Uiso 1 1 calc R . .
H9B H 1.1287 0.2778 0.3642 0.035 Uiso 1 1 calc R . .
H6C H 0.0768 0.6139 0.6078 0.035 Uiso 1 1 d R . .
H12C H 0.1150 1.1162 0.0968 0.035 Uiso 1 1 d R . .
H9C H 0.8936 0.3889 -0.1034 0.035 Uiso 1 1 d R . .
H3C H 0.1006 0.0974 0.6253 0.035 Uiso 1 1 d R . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.017(2) 0.014(2) 0.019(2) 0.0012(19) 0.0083(19) -0.0030(19)
N2 0.015(2) 0.019(3) 0.023(3) -0.001(2) 0.004(2) 0.000(2)
C1 0.019(3) 0.036(4) 0.031(4) -0.012(3) -0.003(3) 0.004(3)
C2 0.022(3) 0.022(3) 0.031(3) -0.002(3) -0.004(3) 0.006(3)
C3 0.029(3) 0.028(4) 0.029(4) -0.011(3) 0.009(3) -0.003(3)
C4 0.028(3) 0.030(4) 0.028(3) -0.010(3) 0.005(3) -0.005(3)
C5 0.030(3) 0.025(3) 0.022(3) 0.000(3) -0.003(3) 0.006(3)
C6 0.028(3) 0.028(4) 0.021(3) 0.000(3) 0.000(3) 0.012(3)
O9 0.029(3) 0.022(2) 0.032(3) -0.008(2) 0.007(2) -0.009(2)
O7 0.034(3) 0.046(4) 0.039(3) -0.018(3) 0.011(2) -0.010(3)
O8 0.034(3) 0.035(3) 0.028(3) -0.013(2) 0.003(2) 0.012(2)
N7 0.019(3) 0.033(3) 0.021(3) -0.007(2) 0.002(2) -0.002(2)
C29 0.022(3) 0.017(3) 0.044(4) -0.014(3) 0.004(3) -0.002(2)
C25 0.014(3) 0.020(3) 0.017(3) 0.003(2) 0.002(2) -0.001(2)
C28 0.016(3) 0.017(3) 0.021(3) 0.000(2) -0.002(2) -0.002(2)
C27 0.035(4) 0.015(3) 0.022(3) -0.003(2) 0.000(3) -0.001(3)
C30 0.018(3) 0.025(3) 0.032(3) -0.011(3) 0.004(3) -0.003(2)
C26 0.036(4) 0.016(3) 0.012(3) -0.001(2) 0.002(2) 0.004(3)
O12 0.026(2) 0.025(2) 0.028(2) -0.0096(19) -0.0064(19) 0.0084(19)
O11 0.039(3) 0.040(3) 0.062(4) -0.003(3) -0.013(3) 0.021(3)
O10 0.026(3) 0.035(3) 0.056(4) -0.025(3) 0.012(2) -0.001(2)
C35 0.022(3) 0.020(3) 0.021(3) -0.007(2) 0.003(2) 0.001(2)
C31 0.012(3) 0.014(3) 0.031(3) -0.005(2) 0.003(2) -0.002(2)
C34 0.018(3) 0.013(3) 0.022(3) 0.000(2) 0.003(2) -0.003(2)
N8 0.015(2) 0.024(3) 0.047(4) -0.017(3) 0.001(2) 0.000(2)
C33 0.032(4) 0.028(3) 0.017(3) -0.006(3) -0.003(3) 0.004(3)
C32 0.027(3) 0.013(3) 0.032(4) -0.007(2) 0.010(3) -0.008(2)
C36 0.022(3) 0.018(3) 0.025(3) -0.003(2) -0.001(2) 0.000(2)
O5 0.023(2) 0.026(3) 0.056(4) -0.018(2) 0.001(2) 0.005(2)
O6 0.022(2) 0.025(2) 0.029(2) -0.0104(19) -0.0007(19) 0.0117(19)
O4 0.029(3) 0.032(3) 0.053(4) -0.010(3) -0.011(2) 0.009(2)
N6 0.016(2) 0.016(3) 0.039(3) -0.004(2) 0.000(2) 0.002(2)
C19 0.016(3) 0.013(3) 0.034(3) -0.001(2) 0.003(2) 0.000(2)
C22 0.016(3) 0.014(3) 0.022(3) 0.000(2) 0.002(2) 0.000(2)
C23 0.014(3) 0.018(3) 0.030(3) -0.006(2) 0.003(2) -0.002(2)
C20 0.017(3) 0.017(3) 0.025(3) -0.010(2) 0.004(2) -0.004(2)
C24 0.015(3) 0.012(3) 0.026(3) 0.004(2) -0.001(2) -0.006(2)
C21 0.018(3) 0.020(3) 0.027(3) -0.005(2) -0.003(2) -0.002(2)
O3 0.023(2) 0.021(2) 0.033(3) -0.0087(19) 0.0055(19) -0.0048(18)
O2 0.028(3) 0.050(4) 0.039(3) -0.022(3) 0.001(2) 0.004(2)
O1 0.030(3) 0.052(4) 0.039(3) -0.009(3) 0.014(2) -0.016(3)
N5 0.020(3) 0.038(3) 0.019(3) -0.007(2) 0.001(2) 0.000(2)
C15 0.020(3) 0.019(3) 0.011(2) 0.001(2) 0.005(2) -0.005(2)
C14 0.020(3) 0.025(3) 0.039(4) -0.011(3) -0.002(3) -0.004(3)
C18 0.023(3) 0.016(3) 0.016(3) 0.002(2) 0.001(2) -0.002(2)
C17 0.031(3) 0.020(3) 0.010(3) 0.001(2) 0.000(2) -0.004(3)
C13 0.017(3) 0.023(3) 0.026(3) -0.011(2) 0.001(2) -0.001(2)
C16 0.026(3) 0.022(3) 0.015(3) -0.001(2) 0.001(2) 0.002(2)
N4 0.014(2) 0.010(2) 0.021(2) 0.0012(18) 0.0055(19) -0.0001(18)
N3 0.016(2) 0.023(3) 0.017(2) -0.006(2) 0.0008(19) 0.003(2)
C7 0.026(3) 0.031(4) 0.029(4) -0.004(3) 0.004(3) 0.002(3)
C8 0.027(3) 0.023(3) 0.025(3) 0.005(3) 0.010(3) -0.003(3)
C11 0.017(3) 0.031(4) 0.032(4) -0.008(3) 0.007(3) -0.003(3)
C10 0.025(3) 0.044(5) 0.038(4) -0.014(3) -0.005(3) 0.014(3)
C12 0.019(3) 0.028(4) 0.037(4) -0.006(3) 0.011(3) -0.008(3)
C9 0.027(3) 0.036(4) 0.024(3) -0.007(3) -0.001(3) 0.007(3)
_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 C5 1.473(8) . ?
N1 C3 1.477(8) . ?
N1 C1 1.502(9) . ?
N2 C4 1.459(9) . ?
N2 C6 1.462(8) . ?
N2 C2 1.480(8) . ?
C1 C2 1.562(9) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.549(9) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.549(9) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
O9 C28 1.351(8) . ?
O9 H9C 0.9139 . ?
O7 N7 1.234(9) . ?
O8 N7 1.226(8) . ?
N7 C25 1.442(8) . ?
C29 C30 1.380(9) . ?
C29 C28 1.400(9) . ?
C29 H29 0.9300 . ?
C25 C30 1.386(9) . ?
C25 C26 1.398(9) . ?
C28 C27 1.413(9) . ?
C27 C26 1.387(9) . ?
C27 H27 0.9300 . ?
C30 H30 0.9300 . ?
C26 H26 0.9300 . ?
O12 C34 1.336(8) . ?
O12 H12C 0.9357 . ?
O11 N8 1.200(9) . ?
O10 N8 1.254(8) . ?
C35 C34 1.371(9) . ?
C35 C36 1.394(9) . ?
C35 H35 0.9300 . ?
C31 C32 1.365(10) . ?
C31 C36 1.384(9) . ?
C31 N8 1.479(8) . ?
C34 C33 1.415(9) . ?
C33 C32 1.392(10) . ?
C33 H33 0.9300 . ?
C32 H32 0.9300 . ?
C36 H36 0.9300 . ?
O5 N6 1.230(8) . ?
O6 C22 1.344(7) . ?
O6 H6C 0.9038 . ?
O4 N6 1.257(8) . ?
N6 C19 1.455(8) . ?
C19 C20 1.374(10) . ?
C19 C24 1.406(9) . ?
C22 C21 1.401(9) . ?
C22 C23 1.424(9) . ?
C23 C24 1.374(8) . ?
C23 H23 0.9300 . ?
C20 C21 1.377(9) . ?
C20 H20 0.9300 . ?
C24 H24 0.9300 . ?
C21 H21 0.9300 . ?
O3 C18 1.334(8) . ?
O3 H3C 0.9131 . ?
O2 N5 1.248(8) . ?
O1 N5 1.225(9) . ?
N5 C15 1.465(8) . ?
C15 C16 1.382(9) . ?
C15 C14 1.386(9) . ?
C14 C13 1.383(9) . ?
C14 H14 0.9300 . ?
C18 C13 1.387(9) . ?
C18 C17 1.398(9) . ?
C17 C16 1.377(9) . ?
C17 H17 0.9300 . ?
C13 H13 0.9300 . ?
C16 H16 0.9300 . ?
N4 C10 1.468(9) . ?
N4 C8 1.482(8) . ?
N4 C12 1.494(8) . ?
N3 C11 1.469(9) . ?
N3 C9 1.474(9) . ?
N3 C7 1.498(9) . ?
C7 C8 1.529(10) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C11 C12 1.552(10) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C10 C9 1.537(10) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
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
C5 N1 C3 107.8(5) . . ?
C5 N1 C1 108.1(5) . . ?
C3 N1 C1 108.0(5) . . ?
C4 N2 C6 109.0(6) . . ?
C4 N2 C2 109.3(5) . . ?
C6 N2 C2 110.0(5) . . ?
N1 C1 C2 110.2(5) . . ?
N1 C1 H1A 109.6 . . ?
C2 C1 H1A 109.6 . . ?
N1 C1 H1B 109.6 . . ?
C2 C1 H1B 109.6 . . ?
H1A C1 H1B 108.1 . . ?
N2 C2 C1 109.3(5) . . ?
N2 C2 H2A 109.8 . . ?
C1 C2 H2A 109.8 . . ?
N2 C2 H2B 109.8 . . ?
C1 C2 H2B 109.8 . . ?
H2A C2 H2B 108.3 . . ?
N1 C3 C4 111.6(6) . . ?
N1 C3 H3A 109.3 . . ?
C4 C3 H3A 109.3 . . ?
N1 C3 H3B 109.3 . . ?
C4 C3 H3B 109.3 . . ?
H3A C3 H3B 108.0 . . ?
N2 C4 C3 109.2(6) . . ?
N2 C4 H4A 109.8 . . ?
C3 C4 H4A 109.8 . . ?
N2 C4 H4B 109.8 . . ?
C3 C4 H4B 109.8 . . ?
H4A C4 H4B 108.3 . . ?
N1 C5 C6 110.5(5) . . ?
N1 C5 H5A 109.6 . . ?
C6 C5 H5A 109.6 . . ?
N1 C5 H5B 109.6 . . ?
C6 C5 H5B 109.6 . . ?
H5A C5 H5B 108.1 . . ?
N2 C6 C5 110.3(5) . . ?
N2 C6 H6A 109.6 . . ?
C5 C6 H6A 109.6 . . ?
N2 C6 H6B 109.6 . . ?
C5 C6 H6B 109.6 . . ?
H6A C6 H6B 108.1 . . ?
C28 O9 H9C 107.3 . . ?
O8 N7 O7 123.6(6) . . ?
O8 N7 C25 118.0(6) . . ?
O7 N7 C25 118.4(6) . . ?
C30 C29 C28 120.0(6) . . ?
C30 C29 H29 120.0 . . ?
C28 C29 H29 120.0 . . ?
C30 C25 C26 120.7(6) . . ?
C30 C25 N7 119.3(6) . . ?
C26 C25 N7 119.9(6) . . ?
O9 C28 C29 123.1(6) . . ?
O9 C28 C27 117.5(6) . . ?
C29 C28 C27 119.5(6) . . ?
C26 C27 C28 120.1(6) . . ?
C26 C27 H27 120.0 . . ?
C28 C27 H27 120.0 . . ?
C29 C30 C25 120.3(6) . . ?
C29 C30 H30 119.8 . . ?
C25 C30 H30 119.8 . . ?
C27 C26 C25 119.3(6) . . ?
C27 C26 H26 120.3 . . ?
C25 C26 H26 120.3 . . ?
C34 O12 H12C 111.7 . . ?
C34 C35 C36 121.7(6) . . ?
C34 C35 H35 119.1 . . ?
C36 C35 H35 119.1 . . ?
C32 C31 C36 122.0(6) . . ?
C32 C31 N8 120.7(6) . . ?
C36 C31 N8 117.3(6) . . ?
O12 C34 C35 125.1(6) . . ?
O12 C34 C33 116.9(6) . . ?
C35 C34 C33 118.0(6) . . ?
O11 N8 O10 124.3(6) . . ?
O11 N8 C31 119.8(6) . . ?
O10 N8 C31 115.7(6) . . ?
C32 C33 C34 120.8(6) . . ?
C32 C33 H33 119.6 . . ?
C34 C33 H33 119.6 . . ?
C31 C32 C33 118.8(6) . . ?
C31 C32 H32 120.6 . . ?
C33 C32 H32 120.6 . . ?
C31 C36 C35 118.5(6) . . ?
C31 C36 H36 120.8 . . ?
C35 C36 H36 120.8 . . ?
C22 O6 H6C 117.6 . . ?
O5 N6 O4 122.8(6) . . ?
O5 N6 C19 119.3(6) . . ?
O4 N6 C19 117.9(6) . . ?
C20 C19 C24 122.4(6) . . ?
C20 C19 N6 120.3(6) . . ?
C24 C19 N6 117.3(6) . . ?
O6 C22 C21 118.7(6) . . ?
O6 C22 C23 121.4(6) . . ?
C21 C22 C23 119.9(6) . . ?
C24 C23 C22 119.7(6) . . ?
C24 C23 H23 120.2 . . ?
C22 C23 H23 120.2 . . ?
C19 C20 C21 119.4(6) . . ?
C19 C20 H20 120.3 . . ?
C21 C20 H20 120.3 . . ?
C23 C24 C19 118.6(6) . . ?
C23 C24 H24 120.7 . . ?
C19 C24 H24 120.7 . . ?
C20 C21 C22 120.0(6) . . ?
C20 C21 H21 120.0 . . ?
C22 C21 H21 120.0 . . ?
C18 O3 H3C 114.7 . . ?
O1 N5 O2 122.3(6) . . ?
O1 N5 C15 119.4(6) . . ?
O2 N5 C15 118.3(6) . . ?
C16 C15 C14 122.3(6) . . ?
C16 C15 N5 119.7(6) . . ?
C14 C15 N5 118.0(6) . . ?
C13 C14 C15 117.8(6) . . ?
C13 C14 H14 121.1 . . ?
C15 C14 H14 121.1 . . ?
O3 C18 C13 122.5(6) . . ?
O3 C18 C17 118.5(6) . . ?
C13 C18 C17 119.0(6) . . ?
C16 C17 C18 120.6(6) . . ?
C16 C17 H17 119.7 . . ?
C18 C17 H17 119.7 . . ?
C14 C13 C18 121.4(6) . . ?
C14 C13 H13 119.3 . . ?
C18 C13 H13 119.3 . . ?
C17 C16 C15 118.8(6) . . ?
C17 C16 H16 120.6 . . ?
C15 C16 H16 120.6 . . ?
C10 N4 C8 107.1(6) . . ?
C10 N4 C12 108.4(6) . . ?
C8 N4 C12 108.6(5) . . ?
C11 N3 C9 109.7(6) . . ?
C11 N3 C7 108.8(5) . . ?
C9 N3 C7 107.8(5) . . ?
N3 C7 C8 109.7(6) . . ?
N3 C7 H7A 109.7 . . ?
C8 C7 H7A 109.7 . . ?
N3 C7 H7B 109.7 . . ?
C8 C7 H7B 109.7 . . ?
H7A C7 H7B 108.2 . . ?
N4 C8 C7 111.4(5) . . ?
N4 C8 H8A 109.3 . . ?
C7 C8 H8A 109.3 . . ?
N4 C8 H8B 109.3 . . ?
C7 C8 H8B 109.3 . . ?
H8A C8 H8B 108.0 . . ?
N3 C11 C12 109.8(5) . . ?
N3 C11 H11A 109.7 . . ?
C12 C11 H11A 109.7 . . ?
N3 C11 H11B 109.7 . . ?
C12 C11 H11B 109.7 . . ?
H11A C11 H11B 108.2 . . ?
N4 C10 C9 111.1(6) . . ?
N4 C10 H10A 109.4 . . ?
C9 C10 H10A 109.4 . . ?
N4 C10 H10B 109.4 . . ?
C9 C10 H10B 109.4 . . ?
H10A C10 H10B 108.0 . . ?
N4 C12 C11 110.6(6) . . ?
N4 C12 H12A 109.5 . . ?
C11 C12 H12A 109.5 . . ?
N4 C12 H12B 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 108.1 . . ?
N3 C9 C10 110.2(6) . . ?
N3 C9 H9A 109.6 . . ?
C10 C9 H9A 109.6 . . ?
N3 C9 H9B 109.6 . . ?
C10 C9 H9B 109.6 . . ?
H9A C9 H9B 108.1 . . ?
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 H6C N3 0.90 1.74 2.615(7) 160.9 2_666
O12 H12C N4 0.94 1.74 2.625(7) 156.9 1_465
O9 H9C N1 0.91 1.73 2.610(7) 160.8 1_654
O3 H3C N2 0.91 1.73 2.622(7) 166.6 .
_diffrn_measured_fraction_theta_max 0.925
_diffrn_reflns_theta_full        27.39
_diffrn_measured_fraction_theta_full 0.925
_refine_diff_density_max         1.034
_refine_diff_density_min         -0.665
_refine_diff_density_rms         0.143


data_LTP
_database_code_depnum_ccdc_archive 'CCDC 908564'
#TrackingRef '15079_web_deposit_cif_file_0_zhihuasun_1351673840.dabco p-nitrophenol.cif'
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H22 N4 O6'
_chemical_formula_weight         390.40
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'
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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   p-1
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
_cell_length_a                   9.785(2)
_cell_length_b                   13.7474(18)
_cell_length_c                   13.7474(18)
_cell_angle_alpha                80.157(14)
_cell_angle_beta                 84.13(2)
_cell_angle_gamma                84.13(2)
_cell_volume                     1805.7(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5263
_cell_measurement_theta_min      1.51
_cell_measurement_theta_max      23.99
_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.27
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.436
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             824
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9555
_exptl_absorpt_correction_T_max  0.9710
_exptl_absorpt_process_details   ?
_exptl_special_details           
;
?
;
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       '\w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 120
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            7724
_diffrn_reflns_av_R_equivalents  0.0189
_diffrn_reflns_av_sigmaI/netI    0.0740
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.51
_diffrn_reflns_theta_max         23.99
_reflns_number_total             5263
_reflns_number_gt                4240
_reflns_threshold_expression     >2sigma(I)
_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0000P)^2^+12.8936P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5263
_refine_ls_number_parameters     505
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1193
_refine_ls_R_factor_gt           0.1050
_refine_ls_wR_factor_ref         0.2449
_refine_ls_wR_factor_gt          0.2386
_refine_ls_goodness_of_fit_ref   1.184
_refine_ls_restrained_S_all      1.184
_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
O1 O 0.3877(5) -0.0717(3) 0.9429(3) 0.0253(10) Uani 1 1 d . . .
O92 O -0.1283(5) 0.2246(3) 1.0112(3) 0.0284(11) Uani 1 1 d . . .
O137 O -0.1329(5) 0.2226(4) 0.8543(4) 0.0335(12) Uani 1 1 d . . .
N35 N -0.0809(5) 0.1957(4) 0.9332(4) 0.0232(12) Uani 1 1 d . . .
C4 C 0.2757(6) -0.0058(5) 0.9376(5) 0.0184(13) Uani 1 1 d . . .
C2 C 0.0882(6) 0.0854(5) 0.8513(5) 0.0234(14) Uani 1 1 d . . .
H2 H 0.0387 0.1017 0.7939 0.028 Uiso 1 1 calc R . .
C1 C 0.0442(6) 0.1282(4) 0.9355(5) 0.0183(13) Uani 1 1 d . . .
C6 C 0.1127(7) 0.1040(4) 1.0201(5) 0.0212(14) Uani 1 1 d . . .
H6 H 0.0795 0.1320 1.0775 0.025 Uiso 1 1 calc R . .
C5 C 0.2296(7) 0.0388(4) 1.0212(5) 0.0216(14) Uani 1 1 d . . .
H5 H 0.2791 0.0240 1.0786 0.026 Uiso 1 1 calc R . .
C3 C 0.2041(6) 0.0193(5) 0.8523(5) 0.0226(14) Uani 1 1 d . . .
H3 H 0.2356 -0.0093 0.7950 0.027 Uiso 1 1 calc R . .
O5 O 0.3937(4) 0.4110(3) 0.4531(3) 0.0235(10) Uani 1 1 d . . .
O44 O -0.1066(5) 0.7119(3) 0.5429(4) 0.0341(12) Uani 1 1 d . . .
O78 O -0.1061(5) 0.7303(4) 0.3830(4) 0.0369(13) Uani 1 1 d . . .
N73 N -0.0571(5) 0.6912(4) 0.4610(4) 0.0242(13) Uani 1 1 d . . .
C19 C 0.0618(6) 0.6182(4) 0.4579(5) 0.0207(14) Uani 1 1 d . . .
C22 C 0.2862(6) 0.4787(4) 0.4519(4) 0.0187(13) Uani 1 1 d . . .
C21 C 0.2081(6) 0.5081(5) 0.3713(5) 0.0207(14) Uani 1 1 d . . .
H21 H 0.2309 0.4779 0.3139 0.025 Uiso 1 1 calc R . .
C20 C 0.0977(6) 0.5802(5) 0.3718(5) 0.0217(14) Uani 1 1 d . . .
H20 H 0.0489 0.6025 0.3147 0.026 Uiso 1 1 calc R . .
C23 C 0.2482(7) 0.5208(4) 0.5370(5) 0.0223(14) Uani 1 1 d . . .
H23 H 0.3008 0.5020 0.5926 0.027 Uiso 1 1 calc R . .
C24 C 0.1346(7) 0.5900(4) 0.5419(5) 0.0209(14) Uani 1 1 d . . .
H24 H 0.1073 0.6172 0.6006 0.025 Uiso 1 1 calc R . .
O10 O 0.3953(4) 0.4493(3) -0.0909(3) 0.0225(10) Uani 1 1 d . . .
O62 O -0.0987(4) 0.5329(4) 0.2168(3) 0.0281(11) Uani 1 1 d . . .
O117 O -0.1108(5) 0.3756(4) 0.2174(4) 0.0321(12) Uani 1 1 d . . .
N50 N -0.0554(5) 0.4551(4) 0.1874(4) 0.0218(12) Uani 1 1 d . . .
C18 C 0.0954(6) 0.3694(5) 0.0698(4) 0.0181(13) Uani 1 1 d . . .
H18 H 0.0415 0.3143 0.0874 0.022 Uiso 1 1 calc R . .
C16 C 0.2859(6) 0.4491(4) -0.0239(4) 0.0159(13) Uani 1 1 d . . .
C14 C 0.1409(6) 0.5337(4) 0.0944(4) 0.0169(13) Uani 1 1 d . . .
H14 H 0.1178 0.5896 0.1270 0.020 Uiso 1 1 calc R . .
C13 C 0.0638(6) 0.4535(5) 0.1153(4) 0.0187(13) Uani 1 1 d . . .
C15 C 0.2533(6) 0.5311(5) 0.0246(5) 0.0191(13) Uani 1 1 d . . .
H15 H 0.3087 0.5855 0.0096 0.023 Uiso 1 1 calc R . .
C17 C 0.2049(6) 0.3675(5) -0.0002(5) 0.0203(14) Uani 1 1 d . . .
H17 H 0.2266 0.3115 -0.0328 0.024 Uiso 1 1 calc R . .
O19 O 0.6161(4) 0.0526(3) 0.5695(3) 0.0232(10) Uani 1 1 d . . .
O90 O 1.1268(5) 0.1446(4) 0.2657(4) 0.0453(14) Uani 1 1 d . . .
O95 O 1.1359(5) -0.0158(4) 0.2773(4) 0.0360(13) Uani 1 1 d . . .
N140 N 1.0820(5) 0.0658(4) 0.2978(4) 0.0254(13) Uani 1 1 d . . .
C7 C 0.9575(6) 0.0618(5) 0.3685(4) 0.0174(13) Uani 1 1 d . . .
C9 C 0.7924(6) 0.1461(5) 0.4727(4) 0.0188(13) Uani 1 1 d . . .
H9 H 0.7590 0.2043 0.4993 0.023 Uiso 1 1 calc R . .
C8 C 0.9064(6) 0.1485(5) 0.4030(4) 0.0203(14) Uani 1 1 d . . .
H8 H 0.9482 0.2085 0.3796 0.024 Uiso 1 1 calc R . .
C10 C 0.7272(6) 0.0601(5) 0.5038(4) 0.0190(13) Uani 1 1 d . . .
C12 C 0.8978(7) -0.0256(5) 0.3996(5) 0.0231(14) Uani 1 1 d . . .
H12 H 0.9361 -0.0845 0.3763 0.028 Uiso 1 1 calc R . .
C11 C 0.7813(7) -0.0265(5) 0.4655(5) 0.0235(14) Uani 1 1 d . . .
H11 H 0.7370 -0.0859 0.4853 0.028 Uiso 1 1 calc R . .
N31 N 0.5472(5) 0.1889(4) 0.6833(4) 0.0163(11) Uani 1 1 d . . .
N71 N 0.4470(5) 0.3042(4) 0.8066(4) 0.0177(11) Uani 1 1 d . . .
C28 C 0.3987(6) 0.2183(5) 0.6716(5) 0.0259(15) Uani 1 1 d . . .
H28A H 0.3481 0.1582 0.6802 0.031 Uiso 1 1 calc R . .
H28B H 0.3879 0.2549 0.6039 0.031 Uiso 1 1 calc R . .
C26 C 0.5624(7) 0.1391(5) 0.7872(5) 0.0248(15) Uani 1 1 d . . .
H26A H 0.6611 0.1188 0.7958 0.030 Uiso 1 1 calc R . .
H26B H 0.5120 0.0787 0.8009 0.030 Uiso 1 1 calc R . .
C27 C 0.3364(6) 0.2847(5) 0.7489(5) 0.0241(14) Uani 1 1 d . . .
H27A H 0.2938 0.3480 0.7145 0.029 Uiso 1 1 calc R . .
H27B H 0.2640 0.2508 0.7938 0.029 Uiso 1 1 calc R . .
C30 C 0.6200(7) 0.2796(5) 0.6674(6) 0.0303(16) Uani 1 1 d . . .
H30A H 0.6139 0.3135 0.5982 0.036 Uiso 1 1 calc R . .
H30B H 0.7187 0.2618 0.6777 0.036 Uiso 1 1 calc R . .
C29 C 0.5572(7) 0.3510(5) 0.7394(5) 0.0233(14) Uani 1 1 d . . .
H29A H 0.6298 0.3662 0.7784 0.028 Uiso 1 1 calc R . .
H29B H 0.5193 0.4139 0.7013 0.028 Uiso 1 1 calc R . .
C25 C 0.5057(7) 0.2089(5) 0.8615(5) 0.0247(15) Uani 1 1 d . . .
H25A H 0.4333 0.1777 0.9086 0.030 Uiso 1 1 calc R . .
H25B H 0.5807 0.2213 0.8997 0.030 Uiso 1 1 calc R . .
N52 N 0.4526(5) 0.3087(4) 0.3073(4) 0.0188(11) Uani 1 1 d . . .
N89 N 0.5515(5) 0.1848(4) 0.1925(4) 0.0172(11) Uani 1 1 d . . .
C35 C 0.4372(7) 0.2063(4) 0.3583(5) 0.0223(14) Uani 1 1 d . . .
H35A H 0.3386 0.1980 0.3790 0.027 Uiso 1 1 calc R . .
H35B H 0.4881 0.1932 0.4185 0.027 Uiso 1 1 calc R . .
C36 C 0.4937(7) 0.1320(4) 0.2885(5) 0.0236(14) Uani 1 1 d . . .
H36A H 0.5663 0.0851 0.3198 0.028 Uiso 1 1 calc R . .
H36B H 0.4185 0.0933 0.2771 0.028 Uiso 1 1 calc R . .
C34 C 0.6600(6) 0.2459(5) 0.2113(5) 0.0250(15) Uani 1 1 d . . .
H34A H 0.7006 0.2806 0.1475 0.030 Uiso 1 1 calc R . .
H34B H 0.7344 0.2024 0.2444 0.030 Uiso 1 1 calc R . .
C32 C 0.4374(7) 0.2528(5) 0.1473(5) 0.0269(15) Uani 1 1 d . . .
H32A H 0.3643 0.2134 0.1338 0.032 Uiso 1 1 calc R . .
H32B H 0.4732 0.2906 0.0835 0.032 Uiso 1 1 calc R . .
C33 C 0.5983(6) 0.3226(5) 0.2774(5) 0.0246(15) Uani 1 1 d . . .
H33A H 0.6498 0.3147 0.3370 0.029 Uiso 1 1 calc R . .
H33B H 0.6071 0.3904 0.2404 0.029 Uiso 1 1 calc R . .
C31 C 0.3758(7) 0.3255(5) 0.2180(5) 0.0254(15) Uani 1 1 d . . .
H31A H 0.3817 0.3946 0.1837 0.030 Uiso 1 1 calc R . .
H31B H 0.2774 0.3153 0.2373 0.030 Uiso 1 1 calc R . .
H1 H 0.4082 0.3825 0.4012 0.030 Uiso 1 1 d R . .
H7 H 0.4037 0.3932 -0.1147 0.030 Uiso 1 1 d R . .
H4 H 0.3994 -0.1015 0.8819 0.030 Uiso 1 1 d R . .
H10 H 0.5966 0.1057 0.6204 0.030 Uiso 1 1 d R . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.028(2) 0.024(2) 0.026(3) -0.012(2) -0.010(2) 0.0057(19)
O92 0.030(3) 0.027(3) 0.029(3) -0.015(2) 0.010(2) 0.001(2)
O137 0.030(3) 0.035(3) 0.040(3) -0.017(2) -0.012(2) 0.006(2)
N35 0.016(3) 0.018(3) 0.036(3) -0.006(3) -0.005(3) -0.001(2)
C4 0.012(3) 0.024(3) 0.020(3) -0.003(3) -0.006(2) -0.001(2)
C2 0.019(3) 0.035(4) 0.018(3) -0.009(3) -0.005(3) -0.002(3)
C1 0.012(3) 0.021(3) 0.022(3) -0.002(3) 0.002(2) -0.005(2)
C6 0.034(4) 0.017(3) 0.013(3) -0.006(3) 0.002(3) -0.001(3)
C5 0.032(4) 0.015(3) 0.018(3) -0.002(3) -0.006(3) -0.002(3)
C3 0.024(3) 0.031(4) 0.013(3) -0.011(3) -0.002(3) 0.005(3)
O5 0.019(2) 0.033(3) 0.019(2) -0.009(2) -0.0035(18) 0.0037(19)
O44 0.029(3) 0.031(3) 0.045(3) -0.019(2) 0.002(2) 0.000(2)
O78 0.027(3) 0.032(3) 0.054(4) -0.012(3) -0.016(2) 0.009(2)
N73 0.021(3) 0.016(3) 0.039(4) -0.011(3) -0.007(3) -0.001(2)
C19 0.020(3) 0.011(3) 0.031(4) -0.004(3) -0.002(3) -0.001(2)
C22 0.025(3) 0.014(3) 0.017(3) 0.001(2) 0.001(3) -0.007(3)
C21 0.013(3) 0.030(4) 0.021(3) -0.012(3) 0.000(3) -0.001(3)
C20 0.019(3) 0.028(4) 0.022(3) -0.013(3) -0.006(3) -0.002(3)
C23 0.031(4) 0.015(3) 0.020(3) 0.001(3) -0.006(3) -0.002(3)
C24 0.029(3) 0.016(3) 0.017(3) -0.003(3) 0.002(3) -0.003(3)
O10 0.022(2) 0.026(2) 0.021(2) -0.0131(19) 0.0094(18) -0.0030(18)
O62 0.021(2) 0.041(3) 0.023(3) -0.014(2) 0.0027(19) 0.004(2)
O117 0.028(3) 0.043(3) 0.026(3) -0.010(2) 0.004(2) -0.006(2)
N50 0.021(3) 0.031(3) 0.013(3) -0.001(2) 0.001(2) -0.006(2)
C18 0.011(3) 0.029(3) 0.014(3) 0.001(3) -0.005(2) -0.006(2)
C16 0.014(3) 0.022(3) 0.011(3) -0.002(2) -0.002(2) 0.001(2)
C14 0.014(3) 0.020(3) 0.018(3) -0.009(3) -0.003(2) 0.001(2)
C13 0.015(3) 0.028(3) 0.013(3) -0.004(3) -0.003(2) 0.004(3)
C15 0.016(3) 0.021(3) 0.021(3) -0.004(3) -0.003(3) -0.004(2)
C17 0.018(3) 0.024(3) 0.021(3) -0.009(3) -0.005(3) 0.001(3)
O19 0.023(2) 0.028(2) 0.020(2) -0.0108(19) 0.0053(19) -0.0056(19)
O90 0.037(3) 0.059(4) 0.038(3) -0.008(3) 0.017(3) -0.016(3)
O95 0.022(2) 0.058(3) 0.033(3) -0.028(3) -0.002(2) 0.009(2)
N140 0.014(3) 0.042(4) 0.024(3) -0.018(3) -0.002(2) 0.001(3)
C7 0.013(3) 0.029(3) 0.009(3) -0.006(3) 0.001(2) 0.000(3)
C9 0.019(3) 0.024(3) 0.015(3) -0.009(3) 0.001(2) -0.002(3)
C8 0.023(3) 0.024(3) 0.016(3) -0.008(3) 0.001(3) -0.007(3)
C10 0.019(3) 0.027(3) 0.011(3) -0.004(3) -0.003(2) 0.001(3)
C12 0.028(3) 0.028(4) 0.014(3) -0.009(3) -0.008(3) 0.007(3)
C11 0.032(4) 0.018(3) 0.021(3) -0.004(3) -0.001(3) -0.006(3)
N31 0.013(2) 0.021(3) 0.014(3) -0.002(2) -0.001(2) 0.003(2)
N71 0.017(3) 0.018(3) 0.020(3) -0.006(2) 0.002(2) -0.006(2)
C28 0.021(3) 0.032(4) 0.024(4) -0.007(3) -0.005(3) 0.004(3)
C26 0.021(3) 0.025(3) 0.026(4) 0.000(3) -0.006(3) 0.004(3)
C27 0.017(3) 0.031(4) 0.025(4) -0.007(3) -0.006(3) 0.003(3)
C30 0.027(4) 0.028(4) 0.037(4) -0.011(3) 0.005(3) -0.005(3)
C29 0.023(3) 0.017(3) 0.029(4) -0.005(3) 0.002(3) -0.002(3)
C25 0.025(3) 0.025(3) 0.022(3) -0.002(3) -0.004(3) 0.007(3)
N52 0.018(3) 0.020(3) 0.017(3) -0.002(2) 0.000(2) 0.004(2)
N89 0.016(2) 0.022(3) 0.013(3) -0.003(2) -0.003(2) 0.001(2)
C35 0.023(3) 0.021(3) 0.020(3) 0.001(3) 0.005(3) 0.000(3)
C36 0.025(3) 0.016(3) 0.028(4) -0.001(3) 0.001(3) -0.001(3)
C34 0.016(3) 0.032(4) 0.029(4) -0.009(3) 0.000(3) -0.003(3)
C32 0.030(4) 0.027(4) 0.022(4) -0.006(3) -0.004(3) 0.009(3)
C33 0.020(3) 0.031(4) 0.023(4) -0.007(3) 0.001(3) 0.000(3)
C31 0.025(3) 0.026(4) 0.028(4) -0.013(3) -0.007(3) 0.006(3)
_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
O1 C4 1.348(7) . ?
O1 H4 0.9858 . ?
O92 N35 1.236(7) . ?
O137 N35 1.228(7) . ?
N35 C1 1.458(8) . ?
C4 C3 1.402(9) . ?
C4 C5 1.407(9) . ?
C2 C3 1.379(9) . ?
C2 C1 1.396(9) . ?
C2 H2 0.9500 . ?
C1 C6 1.377(9) . ?
C6 C5 1.378(9) . ?
C6 H6 0.9500 . ?
C5 H5 0.9500 . ?
C3 H3 0.9500 . ?
O5 C22 1.330(7) . ?
O5 H1 0.8638 . ?
O44 N73 1.246(7) . ?
O78 N73 1.234(7) . ?
N73 C19 1.459(8) . ?
C19 C20 1.373(9) . ?
C19 C24 1.396(9) . ?
C22 C21 1.391(9) . ?
C22 C23 1.392(9) . ?
C21 C20 1.390(9) . ?
C21 H21 0.9500 . ?
C20 H20 0.9500 . ?
C23 C24 1.391(9) . ?
C23 H23 0.9500 . ?
C24 H24 0.9500 . ?
O10 C16 1.338(7) . ?
O10 H7 0.8806 . ?
O62 N50 1.227(7) . ?
O117 N50 1.257(7) . ?
N50 C13 1.452(8) . ?
C18 C17 1.366(8) . ?
C18 C13 1.400(9) . ?
C18 H18 0.9500 . ?
C16 C15 1.399(8) . ?
C16 C17 1.414(9) . ?
C14 C13 1.373(9) . ?
C14 C15 1.386(8) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C17 H17 0.9500 . ?
O19 C10 1.341(7) . ?
O19 H10 1.0849 . ?
O90 N140 1.206(8) . ?
O95 N140 1.255(7) . ?
N140 C7 1.478(8) . ?
C7 C12 1.373(9) . ?
C7 C8 1.385(9) . ?
C9 C10 1.384(9) . ?
C9 C8 1.393(8) . ?
C9 H9 0.9500 . ?
C8 H8 0.9500 . ?
C10 C11 1.415(9) . ?
C12 C11 1.381(9) . ?
C12 H12 0.9500 . ?
C11 H11 0.9500 . ?
N31 C30 1.472(8) . ?
N31 C28 1.485(8) . ?
N31 C26 1.491(8) . ?
N71 C29 1.471(8) . ?
N71 C27 1.477(8) . ?
N71 C25 1.487(8) . ?
C28 C27 1.555(9) . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C26 C25 1.544(9) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C30 C29 1.551(9) . ?
C30 H30A 0.9900 . ?
C30 H30B 0.9900 . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
N52 C35 1.476(8) . ?
N52 C33 1.466(8) . ?
N52 C31 1.477(8) . ?
N89 C36 1.481(8) . ?
N89 C34 1.487(8) . ?
N89 C32 1.496(8) . ?
C35 C36 1.544(9) . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?
C36 H36A 0.9900 . ?
C36 H36B 0.9900 . ?
C34 C33 1.545(9) . ?
C34 H34A 0.9900 . ?
C34 H34B 0.9900 . ?
C32 C31 1.548(8) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
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
C4 O1 H4 108.0 . . ?
O137 N35 O92 123.1(5) . . ?
O137 N35 C1 119.0(5) . . ?
O92 N35 C1 117.9(5) . . ?
O1 C4 C3 122.4(5) . . ?
O1 C4 C5 118.4(5) . . ?
C3 C4 C5 119.2(5) . . ?
C3 C2 C1 119.3(6) . . ?
C3 C2 H2 120.3 . . ?
C1 C2 H2 120.3 . . ?
C6 C1 C2 121.2(6) . . ?
C6 C1 N35 120.6(6) . . ?
C2 C1 N35 118.1(6) . . ?
C5 C6 C1 119.7(6) . . ?
C5 C6 H6 120.1 . . ?
C1 C6 H6 120.1 . . ?
C6 C5 C4 120.2(6) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C2 C3 C4 120.3(6) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C22 O5 H1 114.9 . . ?
O78 N73 O44 122.0(5) . . ?
O78 N73 C19 119.4(6) . . ?
O44 N73 C19 118.7(6) . . ?
C20 C19 C24 122.7(6) . . ?
C20 C19 N73 118.3(6) . . ?
C24 C19 N73 119.1(6) . . ?
O5 C22 C21 123.6(5) . . ?
O5 C22 C23 118.1(6) . . ?
C21 C22 C23 118.2(6) . . ?
C22 C21 C20 122.2(6) . . ?
C22 C21 H21 118.9 . . ?
C20 C21 H21 118.9 . . ?
C19 C20 C21 117.6(6) . . ?
C19 C20 H20 121.2 . . ?
C21 C20 H20 121.2 . . ?
C24 C23 C22 121.1(6) . . ?
C24 C23 H23 119.4 . . ?
C22 C23 H23 119.4 . . ?
C23 C24 C19 118.0(6) . . ?
C23 C24 H24 121.0 . . ?
C19 C24 H24 121.0 . . ?
C16 O10 H7 108.9 . . ?
O62 N50 O117 122.3(5) . . ?
O62 N50 C13 119.6(5) . . ?
O117 N50 C13 118.1(5) . . ?
C17 C18 C13 119.1(6) . . ?
C17 C18 H18 120.5 . . ?
C13 C18 H18 120.5 . . ?
O10 C16 C15 118.9(5) . . ?
O10 C16 C17 121.4(5) . . ?
C15 C16 C17 119.7(5) . . ?
C13 C14 C15 118.3(5) . . ?
C13 C14 H14 120.8 . . ?
C15 C14 H14 120.8 . . ?
C14 C13 C18 122.6(5) . . ?
C14 C13 N50 119.3(5) . . ?
C18 C13 N50 118.2(5) . . ?
C14 C15 C16 120.6(5) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 H15 119.7 . . ?
C18 C17 C16 119.8(6) . . ?
C18 C17 H17 120.1 . . ?
C16 C17 H17 120.1 . . ?
C10 O19 H10 118.4 . . ?
O90 N140 O95 124.4(6) . . ?
O90 N140 C7 119.4(5) . . ?
O95 N140 C7 116.1(6) . . ?
C12 C7 C8 122.0(5) . . ?
C12 C7 N140 120.5(5) . . ?
C8 C7 N140 117.5(5) . . ?
C10 C9 C8 120.9(6) . . ?
C10 C9 H9 119.5 . . ?
C8 C9 H9 119.5 . . ?
C7 C8 C9 118.7(6) . . ?
C7 C8 H8 120.6 . . ?
C9 C8 H8 120.6 . . ?
O19 C10 C9 124.2(5) . . ?
O19 C10 C11 117.3(6) . . ?
C9 C10 C11 118.5(6) . . ?
C7 C12 C11 119.0(6) . . ?
C7 C12 H12 120.5 . . ?
C11 C12 H12 120.5 . . ?
C12 C11 C10 120.8(6) . . ?
C12 C11 H11 119.6 . . ?
C10 C11 H11 119.6 . . ?
C30 N31 C28 108.1(5) . . ?
C30 N31 C26 107.5(5) . . ?
C28 N31 C26 108.8(5) . . ?
C29 N71 C27 109.9(5) . . ?
C29 N71 C25 108.9(5) . . ?
C27 N71 C25 109.3(5) . . ?
N31 C28 C27 110.9(5) . . ?
N31 C28 H28A 109.5 . . ?
C27 C28 H28A 109.5 . . ?
N31 C28 H28B 109.5 . . ?
C27 C28 H28B 109.5 . . ?
H28A C28 H28B 108.1 . . ?
N31 C26 C25 110.9(5) . . ?
N31 C26 H26A 109.5 . . ?
C25 C26 H26A 109.5 . . ?
N31 C26 H26B 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 108.1 . . ?
N71 C27 C28 109.2(5) . . ?
N71 C27 H27A 109.8 . . ?
C28 C27 H27A 109.8 . . ?
N71 C27 H27B 109.8 . . ?
C28 C27 H27B 109.8 . . ?
H27A C27 H27B 108.3 . . ?
N31 C30 C29 111.1(5) . . ?
N31 C30 H30A 109.4 . . ?
C29 C30 H30A 109.4 . . ?
N31 C30 H30B 109.4 . . ?
C29 C30 H30B 109.4 . . ?
H30A C30 H30B 108.0 . . ?
N71 C29 C30 109.4(5) . . ?
N71 C29 H29A 109.8 . . ?
C30 C29 H29A 109.8 . . ?
N71 C29 H29B 109.8 . . ?
C30 C29 H29B 109.8 . . ?
H29A C29 H29B 108.2 . . ?
N71 C25 C26 109.4(5) . . ?
N71 C25 H25A 109.8 . . ?
C26 C25 H25A 109.8 . . ?
N71 C25 H25B 109.8 . . ?
C26 C25 H25B 109.8 . . ?
H25A C25 H25B 108.2 . . ?
C35 N52 C33 110.3(5) . . ?
C35 N52 C31 108.2(5) . . ?
C33 N52 C31 109.0(5) . . ?
C36 N89 C34 108.9(5) . . ?
C36 N89 C32 107.4(5) . . ?
C34 N89 C32 108.4(5) . . ?
N52 C35 C36 110.1(5) . . ?
N52 C35 H35A 109.6 . . ?
C36 C35 H35A 109.6 . . ?
N52 C35 H35B 109.6 . . ?
C36 C35 H35B 109.6 . . ?
H35A C35 H35B 108.2 . . ?
N89 C36 C35 110.5(5) . . ?
N89 C36 H36A 109.6 . . ?
C35 C36 H36A 109.6 . . ?
N89 C36 H36B 109.6 . . ?
C35 C36 H36B 109.6 . . ?
H36A C36 H36B 108.1 . . ?
N89 C34 C33 110.4(5) . . ?
N89 C34 H34A 109.6 . . ?
C33 C34 H34A 109.6 . . ?
N89 C34 H34B 109.6 . . ?
C33 C34 H34B 109.6 . . ?
H34A C34 H34B 108.1 . . ?
N89 C32 C31 110.4(5) . . ?
N89 C32 H32A 109.6 . . ?
C31 C32 H32A 109.6 . . ?
N89 C32 H32B 109.6 . . ?
C31 C32 H32B 109.6 . . ?
H32A C32 H32B 108.1 . . ?
N52 C33 C34 110.1(5) . . ?
N52 C33 H33A 109.6 . . ?
C34 C33 H33A 109.6 . . ?
N52 C33 H33B 109.6 . . ?
C34 C33 H33B 109.6 . . ?
H33A C33 H33B 108.2 . . ?
N52 C31 C32 109.7(5) . . ?
N52 C31 H31A 109.7 . . ?
C32 C31 H31A 109.7 . . ?
N52 C31 H31B 109.7 . . ?
C32 C31 H31B 109.7 . . ?
H31A C31 H31B 108.2 . . ?
_diffrn_measured_fraction_theta_max 0.927
_diffrn_reflns_theta_full        23.99
_diffrn_measured_fraction_theta_full 0.927
_refine_diff_density_max         0.474
_refine_diff_density_min         -0.451
_refine_diff_density_rms         0.085