# Electronic Supplementary Material (ESI) for Chemical Communications
# 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 
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#  except for the purpose of generating routine backup copies 
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#  data retrieval see:
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data_trail1
_database_code_depnum_ccdc_archive 'CCDC 922310'
#TrackingRef 'web_deposit_cif_file_0_DnyaneshwarShivajiKand_1359376329.04 Talukdar Chemical Communications 14a-R.cif'
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         C42H60N4O10
_chemical_formula_sum            'C42 H60 N4 O10'
_chemical_formula_weight         780.94
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
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
_cell_length_a                   5.155(3)
_cell_length_b                   36.609(18)
_cell_length_c                   11.688(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.638(9)
_cell_angle_gamma                90.00
_cell_volume                     2152(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?
_exptl_crystal_description       Needles
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.224
_exptl_crystal_size_mid          0.148
_exptl_crystal_size_min          0.022
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.205
_exptl_crystal_density_method    calcd
_exptl_crystal_F_000             840
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.985
_exptl_absorpt_correction_T_max  0.998
_exptl_absorpt_process_details   ?
_exptl_special_details           
;
?
;
_diffrn_ambient_temperature      200(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            25243
_diffrn_reflns_av_R_equivalents  0.0843
_diffrn_reflns_av_sigmaI/netI    0.1159
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       2
_diffrn_reflns_limit_k_min       -44
_diffrn_reflns_limit_k_max       45
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.11
_diffrn_reflns_theta_max         26.43
_reflns_number_total             8384
_reflns_number_gt                4811
_reflns_threshold_expression     >2sigma(I)
_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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^)+(0.0475P)^2^+0.8129P] 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     SHELXL
_refine_ls_extinction_coef       0.0065(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.2(14)
_refine_ls_number_reflns         8384
_refine_ls_number_parameters     516
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1369
_refine_ls_R_factor_gt           0.0632
_refine_ls_wR_factor_ref         0.1503
_refine_ls_wR_factor_gt          0.1200
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_restrained_S_all      0.999
_refine_ls_shift/su_max          0.001
_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 0.4837(14) 0.91480(17) 0.2093(5) 0.0667(17) Uani 1 1 d . . .
H1 H 0.4803 0.9381 0.1770 0.080 Uiso 1 1 calc R . .
N1 N 0.6138(6) 0.80681(10) 0.4838(3) 0.0351(8) Uani 1 1 d . . .
H1A H 0.7832 0.8055 0.5092 0.042 Uiso 1 1 calc R . .
O1 O 0.2119(5) 0.80891(8) 0.5335(2) 0.0357(7) Uani 1 1 d . . .
C2 C 0.2713(13) 0.8921(2) 0.1761(5) 0.0763(19) Uani 1 1 d . . .
H2 H 0.1229 0.8998 0.1208 0.092 Uiso 1 1 calc R . .
N2 N 0.6323(6) 0.77457(9) 0.9639(3) 0.0324(8) Uani 1 1 d . . .
H2A H 0.4841 0.7681 0.9803 0.039 Uiso 1 1 calc R . .
O2 O 1.0668(6) 0.75940(9) 0.9830(3) 0.0510(9) Uani 1 1 d . . .
C3 C 0.2768(10) 0.85749(16) 0.2248(4) 0.0584(15) Uani 1 1 d . . .
H3 H 0.1310 0.8421 0.2019 0.070 Uiso 1 1 calc R . .
N3 N 0.4832(6) 0.57983(10) 0.2245(3) 0.0369(9) Uani 1 1 d . . .
H3A H 0.6291 0.5817 0.2007 0.044 Uiso 1 1 calc R . .
O3 O 0.7742(5) 0.72206(8) 1.0453(3) 0.0442(8) Uani 1 1 d . . .
C4 C 0.4968(8) 0.84545(13) 0.3071(4) 0.0361(11) Uani 1 1 d . . .
N4 N 0.0265(6) 0.60649(9) -0.2584(3) 0.0303(8) Uani 1 1 d . . .
H4 H -0.1385 0.6125 -0.2779 0.036 Uiso 1 1 calc R . .
O4 O 0.0911(8) 0.86891(12) 0.8103(4) 0.0856(14) Uani 1 1 d . . .
C5 C 0.7087(10) 0.86895(14) 0.3374(4) 0.0497(13) Uani 1 1 d . . .
H5 H 0.8601 0.8614 0.3910 0.060 Uiso 1 1 calc R . .
O5 O 0.3547(11) 0.89943(12) 0.7204(4) 0.1047(16) Uani 1 1 d . . .
C6 C 0.7016(12) 0.90342(14) 0.2900(5) 0.0591(15) Uani 1 1 d . . .
H6 H 0.8459 0.9190 0.3131 0.071 Uiso 1 1 calc R . .
O6 O 0.0349(5) 0.57618(8) 0.1717(2) 0.0371(7) Uani 1 1 d . . .
C7 C 0.5085(8) 0.80703(12) 0.3572(3) 0.0343(10) Uani 1 1 d . . .
H7 H 0.3273 0.7972 0.3418 0.041 Uiso 1 1 calc R . .
O7 O 0.4424(6) 0.62145(8) -0.2775(3) 0.0485(9) Uani 1 1 d . . .
C8 C 0.6768(9) 0.78221(13) 0.2984(4) 0.0442(12) Uani 1 1 d . . .
H8A H 0.6783 0.7580 0.3302 0.066 Uiso 1 1 calc R . .
H8B H 0.8552 0.7915 0.3122 0.066 Uiso 1 1 calc R . .
H8C H 0.6030 0.7815 0.2155 0.066 Uiso 1 1 calc R . .
O8 O 0.0885(5) 0.65925(8) -0.3359(3) 0.0420(8) Uani 1 1 d . . .
C9 C 0.4599(8) 0.80857(11) 0.5625(3) 0.0276(9) Uani 1 1 d . . .
O9 O -0.3290(7) 0.51099(9) -0.0779(3) 0.0583(10) Uani 1 1 d . . .
C10 C 0.6078(7) 0.81015(11) 0.6856(3) 0.0279(9) Uani 1 1 d . . .
H10 H 0.7896 0.8146 0.7000 0.033 Uiso 1 1 calc R . .
O10 O 0.0336(8) 0.47764(9) -0.0103(3) 0.0632(10) Uani 1 1 d . . .
C11 C 0.4976(7) 0.80562(11) 0.7766(3) 0.0269(9) Uani 1 1 d . . .
H11 H 0.3174 0.8000 0.7618 0.032 Uiso 1 1 calc R . .
C12 C 0.6439(8) 0.80892(11) 0.9026(3) 0.0282(9) Uani 1 1 d . . .
H12 H 0.8310 0.8139 0.9033 0.034 Uiso 1 1 calc R . .
C13 C 0.8438(8) 0.75255(12) 0.9959(4) 0.0308(10) Uani 1 1 d . . .
C14 C 0.9712(8) 0.69330(12) 1.0892(5) 0.0472(13) Uani 1 1 d . . .
C15 C 0.8053(13) 0.66511(18) 1.1351(9) 0.141(4) Uani 1 1 d . . .
H15A H 0.6768 0.6550 1.0709 0.212 Uiso 1 1 calc R . .
H15B H 0.7153 0.6764 1.1896 0.212 Uiso 1 1 calc R . .
H15C H 0.9186 0.6460 1.1740 0.212 Uiso 1 1 calc R . .
C16 C 1.0851(11) 0.67788(15) 0.9907(5) 0.0627(16) Uani 1 1 d . . .
H16A H 1.1989 0.6957 0.9667 0.094 Uiso 1 1 calc R . .
H16B H 0.9428 0.6719 0.9255 0.094 Uiso 1 1 calc R . .
H16C H 1.1858 0.6563 1.0173 0.094 Uiso 1 1 calc R . .
C17 C 1.1833(11) 0.70811(15) 1.1878(5) 0.0634(16) Uani 1 1 d . . .
H17A H 1.1017 0.7214 1.2414 0.095 Uiso 1 1 calc R . .
H17B H 1.2980 0.7241 1.1566 0.095 Uiso 1 1 calc R . .
H17C H 1.2856 0.6883 1.2284 0.095 Uiso 1 1 calc R . .
C18 C 0.5408(9) 0.83998(11) 0.9673(4) 0.0397(11) Uani 1 1 d . . .
H18A H 0.3607 0.8343 0.9737 0.048 Uiso 1 1 calc R . .
H18B H 0.6496 0.8415 1.0462 0.048 Uiso 1 1 calc R . .
C19 C 0.5411(9) 0.87650(12) 0.9095(4) 0.0427(12) Uani 1 1 d . . .
H19A H 0.7029 0.8791 0.8807 0.051 Uiso 1 1 calc R . .
H19B H 0.5394 0.8956 0.9669 0.051 Uiso 1 1 calc R . .
C20 C 0.3027(14) 0.88113(14) 0.8083(5) 0.0581(15) Uani 1 1 d . . .
C21 C 0.540(2) 0.51314(19) 0.3449(8) 0.173(5) Uani 1 1 d . . .
H21 H 0.5930 0.5155 0.2742 0.207 Uiso 1 1 calc R . .
C22 C 0.529(3) 0.4787(2) 0.3947(9) 0.224(8) Uani 1 1 d . . .
H22 H 0.5813 0.4585 0.3568 0.269 Uiso 1 1 calc R . .
C23 C 0.4492(16) 0.47331(17) 0.4934(6) 0.083(2) Uani 1 1 d . . .
H23 H 0.4475 0.4501 0.5257 0.100 Uiso 1 1 calc R . .
C24 C 0.3718(12) 0.50226(19) 0.5437(6) 0.0729(18) Uani 1 1 d . . .
H24 H 0.3065 0.4994 0.6113 0.087 Uiso 1 1 calc R . .
C25 C 0.3860(11) 0.53735(15) 0.4974(5) 0.0638(16) Uani 1 1 d . . .
H25 H 0.3336 0.5574 0.5359 0.077 Uiso 1 1 calc R . .
C26 C 0.4740(9) 0.54262(13) 0.3984(4) 0.0390(11) Uani 1 1 d . . .
C27 C 0.4942(8) 0.58078(12) 0.3506(3) 0.0334(10) Uani 1 1 d . . .
H27 H 0.3430 0.5951 0.3639 0.040 Uiso 1 1 calc R . .
C28 C 0.7481(9) 0.59982(14) 0.4115(4) 0.0489(13) Uani 1 1 d . . .
H28A H 0.7469 0.6245 0.3837 0.073 Uiso 1 1 calc R . .
H28B H 0.8983 0.5871 0.3946 0.073 Uiso 1 1 calc R . .
H28C H 0.7600 0.5999 0.4946 0.073 Uiso 1 1 calc R . .
C29 C 0.2553(8) 0.57622(11) 0.1449(3) 0.0301(9) Uani 1 1 d . . .
C30 C 0.2831(8) 0.57259(11) 0.0216(3) 0.0290(9) Uani 1 1 d . . .
H30 H 0.4498 0.5671 0.0077 0.035 Uiso 1 1 calc R . .
C31 C 0.0813(7) 0.57675(11) -0.0698(3) 0.0271(9) Uani 1 1 d . . .
H31 H -0.0836 0.5828 -0.0550 0.032 Uiso 1 1 calc R . .
C32 C 0.1004(8) 0.57242(11) -0.1936(3) 0.0301(10) Uani 1 1 d . . .
H32 H 0.2855 0.5668 -0.1951 0.036 Uiso 1 1 calc R . .
C33 C 0.2085(8) 0.62841(12) -0.2880(4) 0.0318(10) Uani 1 1 d . . .
C34 C 0.2447(8) 0.68820(13) -0.3780(4) 0.0443(12) Uani 1 1 d . . .
C35 C 0.4591(12) 0.70252(15) -0.2786(5) 0.0662(17) Uani 1 1 d . . .
H35A H 0.6027 0.6853 -0.2614 0.099 Uiso 1 1 calc R . .
H35B H 0.3869 0.7060 -0.2103 0.099 Uiso 1 1 calc R . .
H35C H 0.5240 0.7254 -0.3009 0.099 Uiso 1 1 calc R . .
C36 C 0.0337(11) 0.71694(18) -0.4221(8) 0.124(4) Uani 1 1 d . . .
H36A H -0.0269 0.7271 -0.3569 0.186 Uiso 1 1 calc R . .
H36B H -0.1134 0.7059 -0.4755 0.186 Uiso 1 1 calc R . .
H36C H 0.1079 0.7359 -0.4616 0.186 Uiso 1 1 calc R . .
C37 C 0.3591(12) 0.67380(16) -0.4781(4) 0.0663(17) Uani 1 1 d . . .
H37A H 0.2235 0.6609 -0.5326 0.100 Uiso 1 1 calc R . .
H37B H 0.5037 0.6575 -0.4478 0.100 Uiso 1 1 calc R . .
H37C H 0.4225 0.6938 -0.5173 0.100 Uiso 1 1 calc R . .
C38 C -0.0756(9) 0.54133(11) -0.2551(4) 0.0369(11) Uani 1 1 d . . .
H38A H -0.2599 0.5469 -0.2557 0.044 Uiso 1 1 calc R . .
H38B H -0.0578 0.5398 -0.3358 0.044 Uiso 1 1 calc R . .
C39 C -0.0041(9) 0.50437(11) -0.1956(4) 0.0379(11) Uani 1 1 d . . .
H39A H -0.0685 0.4851 -0.2514 0.046 Uiso 1 1 calc R . .
H39B H 0.1878 0.5023 -0.1727 0.046 Uiso 1 1 calc R . .
C40 C -0.1194(10) 0.49911(12) -0.0887(5) 0.0433(12) Uani 1 1 d . . .
C41 C -0.0666(16) 0.47179(19) 0.0954(6) 0.098(2) Uani 1 1 d . . .
H41A H -0.2487 0.4640 0.0743 0.148 Uiso 1 1 calc R . .
H41B H -0.0551 0.4942 0.1391 0.148 Uiso 1 1 calc R . .
H41C H 0.0378 0.4533 0.1427 0.148 Uiso 1 1 calc R . .
C42 C 0.0828(19) 0.8997(2) 0.6268(7) 0.165(5) Uani 1 1 d . . .
H42A H 0.0210 0.9244 0.6130 0.247 Uiso 1 1 calc R . .
H42B H -0.0466 0.8856 0.6556 0.247 Uiso 1 1 calc R . .
H42C H 0.1084 0.8892 0.5548 0.247 Uiso 1 1 calc 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
C1 0.082(4) 0.059(4) 0.066(4) 0.011(3) 0.030(4) 0.032(3)
N1 0.0247(17) 0.058(2) 0.0212(18) 0.0030(18) 0.0009(15) 0.0015(17)
O1 0.0264(15) 0.0492(19) 0.0309(16) -0.0027(15) 0.0050(13) -0.0015(15)
C2 0.069(4) 0.099(5) 0.061(4) 0.030(4) 0.014(4) 0.045(4)
N2 0.0284(19) 0.036(2) 0.035(2) 0.0112(17) 0.0105(17) 0.0028(16)
O2 0.0252(16) 0.050(2) 0.080(2) 0.0221(18) 0.0157(17) 0.0020(15)
C3 0.040(3) 0.091(5) 0.045(3) 0.017(3) 0.008(3) 0.014(3)
N3 0.0243(18) 0.062(3) 0.0238(18) -0.0004(18) 0.0042(16) -0.0025(18)
O3 0.0302(15) 0.0375(18) 0.067(2) 0.0200(16) 0.0156(16) 0.0042(14)
C4 0.035(2) 0.052(3) 0.025(2) 0.003(2) 0.013(2) 0.012(2)
N4 0.0187(16) 0.034(2) 0.037(2) 0.0070(17) 0.0026(16) 0.0018(15)
O4 0.048(2) 0.087(3) 0.111(4) -0.018(3) -0.005(3) 0.015(2)
C5 0.059(3) 0.049(3) 0.040(3) 0.003(2) 0.007(3) 0.006(3)
O5 0.152(5) 0.081(3) 0.080(3) 0.043(3) 0.024(3) 0.019(3)
C6 0.078(4) 0.044(3) 0.058(4) -0.001(3) 0.021(3) 0.009(3)
O6 0.0276(15) 0.0544(19) 0.0310(16) 0.0001(15) 0.0098(13) 0.0010(14)
C7 0.028(2) 0.051(3) 0.023(2) -0.002(2) 0.0047(18) -0.007(2)
O7 0.0283(17) 0.044(2) 0.075(2) 0.0140(17) 0.0155(17) 0.0052(14)
C8 0.047(3) 0.049(3) 0.038(3) -0.001(2) 0.012(2) -0.001(2)
O8 0.0264(15) 0.0313(17) 0.070(2) 0.0155(16) 0.0134(15) -0.0024(14)
C9 0.029(2) 0.028(2) 0.027(2) 0.0003(19) 0.0082(19) -0.0032(19)
O9 0.042(2) 0.057(2) 0.081(3) -0.003(2) 0.025(2) -0.0060(17)
C10 0.0243(19) 0.035(2) 0.024(2) 0.0050(19) 0.0043(18) -0.0020(19)
O10 0.081(3) 0.050(2) 0.061(3) 0.0204(19) 0.020(2) 0.003(2)
C11 0.027(2) 0.026(2) 0.028(2) -0.0010(19) 0.0078(18) -0.0012(18)
C12 0.032(2) 0.030(2) 0.021(2) 0.0058(19) 0.0020(18) -0.0042(19)
C13 0.029(2) 0.032(2) 0.032(2) 0.0019(19) 0.009(2) -0.0016(19)
C14 0.031(2) 0.033(3) 0.079(4) 0.017(3) 0.015(3) 0.016(2)
C15 0.063(4) 0.071(5) 0.303(12) 0.113(6) 0.071(6) 0.022(4)
C16 0.057(3) 0.052(3) 0.070(4) -0.016(3) -0.005(3) 0.020(3)
C17 0.076(4) 0.069(4) 0.043(3) 0.008(3) 0.009(3) 0.031(3)
C18 0.054(3) 0.037(3) 0.028(3) 0.002(2) 0.010(2) 0.001(2)
C19 0.045(3) 0.032(3) 0.053(3) -0.003(2) 0.016(3) -0.001(2)
C20 0.090(5) 0.042(3) 0.046(3) 0.002(3) 0.022(4) 0.026(3)
C21 0.381(16) 0.056(5) 0.147(8) 0.022(5) 0.199(10) 0.061(7)
C22 0.53(2) 0.041(5) 0.170(9) 0.020(5) 0.230(14) 0.070(8)
C23 0.147(7) 0.043(4) 0.059(4) 0.002(3) 0.021(4) -0.013(4)
C24 0.073(4) 0.084(5) 0.068(4) 0.039(4) 0.032(3) 0.011(4)
C25 0.072(4) 0.065(4) 0.062(4) 0.023(3) 0.033(3) 0.025(3)
C26 0.042(3) 0.047(3) 0.029(3) -0.004(2) 0.011(2) -0.001(2)
C27 0.031(2) 0.045(3) 0.023(2) -0.005(2) 0.0043(18) 0.003(2)
C28 0.046(3) 0.064(3) 0.033(3) -0.003(2) 0.001(2) -0.013(3)
C29 0.032(2) 0.027(2) 0.032(2) 0.002(2) 0.009(2) 0.0033(19)
C30 0.028(2) 0.031(2) 0.031(2) -0.0019(19) 0.0111(19) 0.0024(18)
C31 0.026(2) 0.025(2) 0.029(2) 0.003(2) 0.0052(19) 0.0018(18)
C32 0.027(2) 0.035(3) 0.026(2) 0.001(2) 0.0011(18) 0.0049(19)
C33 0.028(2) 0.036(3) 0.030(2) -0.001(2) 0.003(2) 0.001(2)
C34 0.030(2) 0.039(3) 0.064(3) 0.010(3) 0.010(2) -0.002(2)
C35 0.082(4) 0.061(4) 0.063(4) -0.024(3) 0.031(3) -0.026(3)
C36 0.046(3) 0.070(4) 0.259(11) 0.095(6) 0.042(5) 0.019(3)
C37 0.072(4) 0.080(4) 0.045(3) -0.001(3) 0.007(3) -0.032(3)
C38 0.040(2) 0.031(2) 0.035(3) -0.005(2) -0.003(2) -0.002(2)
C39 0.041(3) 0.027(2) 0.047(3) -0.002(2) 0.011(2) 0.000(2)
C40 0.046(3) 0.026(3) 0.058(3) -0.004(2) 0.011(3) -0.008(2)
C41 0.149(7) 0.080(5) 0.077(5) 0.034(4) 0.049(5) 0.013(5)
C42 0.177(9) 0.124(7) 0.122(7) 0.011(6) -0.124(7) 0.011(7)
_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.362(9) . ?
C1 C6 1.364(8) . ?
C1 H1 0.9300 . ?
N1 C9 1.341(5) . ?
N1 C7 1.460(5) . ?
N1 H1A 0.8600 . ?
O1 C9 1.249(4) . ?
C2 C3 1.387(8) . ?
C2 H2 0.9300 . ?
N2 C13 1.342(5) . ?
N2 C12 1.455(5) . ?
N2 H2A 0.8600 . ?
O2 C13 1.217(5) . ?
C3 C4 1.389(6) . ?
C3 H3 0.9300 . ?
N3 C29 1.336(5) . ?
N3 C27 1.464(5) . ?
N3 H3A 0.8600 . ?
O3 C13 1.341(5) . ?
O3 C14 1.475(5) . ?
C4 C5 1.375(7) . ?
C4 C7 1.520(6) . ?
N4 C33 1.337(5) . ?
N4 C32 1.466(5) . ?
N4 H4 0.8600 . ?
O4 C20 1.184(7) . ?
C5 C6 1.375(7) . ?
C5 H5 0.9300 . ?
O5 C20 1.303(6) . ?
O5 C42 1.578(8) . ?
C6 H6 0.9300 . ?
O6 C29 1.243(5) . ?
C7 C8 1.521(6) . ?
C7 H7 0.9800 . ?
O7 C33 1.212(5) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
O8 C33 1.349(5) . ?
O8 C34 1.479(5) . ?
C9 C10 1.474(5) . ?
O9 C40 1.197(5) . ?
C10 C11 1.322(5) . ?
C10 H10 0.9300 . ?
O10 C40 1.328(6) . ?
O10 C41 1.456(7) . ?
C11 C12 1.505(5) . ?
C11 H11 0.9300 . ?
C12 C18 1.525(6) . ?
C12 H12 0.9800 . ?
C14 C17 1.506(7) . ?
C14 C15 1.511(7) . ?
C14 C16 1.512(7) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 C19 1.498(6) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 C20 1.517(8) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C21 C26 1.328(8) . ?
C21 C22 1.395(10) . ?
C21 H21 0.9300 . ?
C22 C23 1.322(10) . ?
C22 H22 0.9300 . ?
C23 C24 1.316(8) . ?
C23 H23 0.9300 . ?
C24 C25 1.402(8) . ?
C24 H24 0.9300 . ?
C25 C26 1.346(6) . ?
C25 H25 0.9300 . ?
C26 C27 1.517(6) . ?
C27 C28 1.516(6) . ?
C27 H27 0.9800 . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C29 C30 1.485(5) . ?
C30 C31 1.327(5) . ?
C30 H30 0.9300 . ?
C31 C32 1.481(5) . ?
C31 H31 0.9300 . ?
C32 C38 1.533(5) . ?
C32 H32 0.9800 . ?
C34 C35 1.512(7) . ?
C34 C37 1.515(7) . ?
C34 C36 1.520(7) . ?
C35 H35A 0.9600 . ?
C35 H35B 0.9600 . ?
C35 H35C 0.9600 . ?
C36 H36A 0.9600 . ?
C36 H36B 0.9600 . ?
C36 H36C 0.9600 . ?
C37 H37A 0.9600 . ?
C37 H37B 0.9600 . ?
C37 H37C 0.9600 . ?
C38 C39 1.529(6) . ?
C38 H38A 0.9700 . ?
C38 H38B 0.9700 . ?
C39 C40 1.508(6) . ?
C39 H39A 0.9700 . ?
C39 H39B 0.9700 . ?
C41 H41A 0.9600 . ?
C41 H41B 0.9600 . ?
C41 H41C 0.9600 . ?
C42 H42A 0.9600 . ?
C42 H42B 0.9600 . ?
C42 H42C 0.9600 . ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 120.0(6) . . ?
C2 C1 H1 120.0 . . ?
C6 C1 H1 120.0 . . ?
C9 N1 C7 123.4(3) . . ?
C9 N1 H1A 118.3 . . ?
C7 N1 H1A 118.3 . . ?
C1 C2 C3 119.8(6) . . ?
C1 C2 H2 120.1 . . ?
C3 C2 H2 120.1 . . ?
C13 N2 C12 122.5(3) . . ?
C13 N2 H2A 118.7 . . ?
C12 N2 H2A 118.7 . . ?
C2 C3 C4 121.0(5) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C29 N3 C27 122.6(3) . . ?
C29 N3 H3A 118.7 . . ?
C27 N3 H3A 118.7 . . ?
C13 O3 C14 121.0(3) . . ?
C5 C4 C3 117.5(4) . . ?
C5 C4 C7 121.2(4) . . ?
C3 C4 C7 121.2(4) . . ?
C33 N4 C32 121.8(3) . . ?
C33 N4 H4 119.1 . . ?
C32 N4 H4 119.1 . . ?
C4 C5 C6 121.4(5) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
C20 O5 C42 104.2(6) . . ?
C1 C6 C5 120.3(6) . . ?
C1 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
N1 C7 C4 111.7(4) . . ?
N1 C7 C8 109.4(3) . . ?
C4 C7 C8 110.9(3) . . ?
N1 C7 H7 108.2 . . ?
C4 C7 H7 108.2 . . ?
C8 C7 H7 108.2 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C33 O8 C34 120.3(3) . . ?
O1 C9 N1 122.6(3) . . ?
O1 C9 C10 123.0(4) . . ?
N1 C9 C10 114.5(3) . . ?
C11 C10 C9 124.0(3) . . ?
C11 C10 H10 118.0 . . ?
C9 C10 H10 118.0 . . ?
C40 O10 C41 113.9(5) . . ?
C10 C11 C12 124.4(3) . . ?
C10 C11 H11 117.8 . . ?
C12 C11 H11 117.8 . . ?
N2 C12 C11 110.3(3) . . ?
N2 C12 C18 110.1(3) . . ?
C11 C12 C18 113.0(3) . . ?
N2 C12 H12 107.8 . . ?
C11 C12 H12 107.8 . . ?
C18 C12 H12 107.8 . . ?
O2 C13 O3 125.0(4) . . ?
O2 C13 N2 125.0(4) . . ?
O3 C13 N2 110.0(3) . . ?
O3 C14 C17 109.8(4) . . ?
O3 C14 C15 102.2(4) . . ?
C17 C14 C15 110.3(6) . . ?
O3 C14 C16 110.7(4) . . ?
C17 C14 C16 112.3(4) . . ?
C15 C14 C16 111.1(5) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C14 C17 H17A 109.5 . . ?
C14 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C14 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C19 C18 C12 114.0(4) . . ?
C19 C18 H18A 108.8 . . ?
C12 C18 H18A 108.8 . . ?
C19 C18 H18B 108.8 . . ?
C12 C18 H18B 108.8 . . ?
H18A C18 H18B 107.7 . . ?
C18 C19 C20 111.8(4) . . ?
C18 C19 H19A 109.3 . . ?
C20 C19 H19A 109.3 . . ?
C18 C19 H19B 109.3 . . ?
C20 C19 H19B 109.3 . . ?
H19A C19 H19B 107.9 . . ?
O4 C20 O5 124.0(6) . . ?
O4 C20 C19 122.3(5) . . ?
O5 C20 C19 113.6(6) . . ?
C26 C21 C22 120.0(6) . . ?
C26 C21 H21 120.0 . . ?
C22 C21 H21 120.0 . . ?
C23 C22 C21 123.2(7) . . ?
C23 C22 H22 118.4 . . ?
C21 C22 H22 118.4 . . ?
C24 C23 C22 116.9(6) . . ?
C24 C23 H23 121.5 . . ?
C22 C23 H23 121.5 . . ?
C23 C24 C25 121.3(6) . . ?
C23 C24 H24 119.4 . . ?
C25 C24 H24 119.4 . . ?
C26 C25 C24 121.3(5) . . ?
C26 C25 H25 119.4 . . ?
C24 C25 H25 119.4 . . ?
C21 C26 C25 117.2(5) . . ?
C21 C26 C27 122.0(5) . . ?
C25 C26 C27 120.8(4) . . ?
N3 C27 C28 108.8(3) . . ?
N3 C27 C26 111.0(3) . . ?
C28 C27 C26 111.9(4) . . ?
N3 C27 H27 108.3 . . ?
C28 C27 H27 108.3 . . ?
C26 C27 H27 108.3 . . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
O6 C29 N3 122.5(4) . . ?
O6 C29 C30 122.2(4) . . ?
N3 C29 C30 115.3(3) . . ?
C31 C30 C29 123.0(4) . . ?
C31 C30 H30 118.5 . . ?
C29 C30 H30 118.5 . . ?
C30 C31 C32 124.5(4) . . ?
C30 C31 H31 117.8 . . ?
C32 C31 H31 117.8 . . ?
N4 C32 C31 110.4(3) . . ?
N4 C32 C38 109.2(3) . . ?
C31 C32 C38 112.2(3) . . ?
N4 C32 H32 108.3 . . ?
C31 C32 H32 108.3 . . ?
C38 C32 H32 108.3 . . ?
O7 C33 N4 125.9(4) . . ?
O7 C33 O8 125.0(4) . . ?
N4 C33 O8 109.0(3) . . ?
O8 C34 C35 110.6(4) . . ?
O8 C34 C37 109.9(4) . . ?
C35 C34 C37 111.8(4) . . ?
O8 C34 C36 102.0(4) . . ?
C35 C34 C36 111.7(5) . . ?
C37 C34 C36 110.5(5) . . ?
C34 C35 H35A 109.5 . . ?
C34 C35 H35B 109.5 . . ?
H35A C35 H35B 109.5 . . ?
C34 C35 H35C 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
C34 C36 H36A 109.5 . . ?
C34 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
C34 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
C34 C37 H37A 109.5 . . ?
C34 C37 H37B 109.5 . . ?
H37A C37 H37B 109.5 . . ?
C34 C37 H37C 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
C39 C38 C32 112.6(3) . . ?
C39 C38 H38A 109.1 . . ?
C32 C38 H38A 109.1 . . ?
C39 C38 H38B 109.1 . . ?
C32 C38 H38B 109.1 . . ?
H38A C38 H38B 107.8 . . ?
C40 C39 C38 113.0(4) . . ?
C40 C39 H39A 109.0 . . ?
C38 C39 H39A 109.0 . . ?
C40 C39 H39B 109.0 . . ?
C38 C39 H39B 109.0 . . ?
H39A C39 H39B 107.8 . . ?
O9 C40 O10 123.8(5) . . ?
O9 C40 C39 124.7(5) . . ?
O10 C40 C39 111.4(4) . . ?
O10 C41 H41A 109.5 . . ?
O10 C41 H41B 109.5 . . ?
H41A C41 H41B 109.5 . . ?
O10 C41 H41C 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 109.5 . . ?
O5 C42 H42A 109.5 . . ?
O5 C42 H42B 109.5 . . ?
H42A C42 H42B 109.5 . . ?
O5 C42 H42C 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 109.5 . . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 0.2(8) . . . . ?
C1 C2 C3 C4 -0.2(8) . . . . ?
C2 C3 C4 C5 -0.6(7) . . . . ?
C2 C3 C4 C7 -177.6(5) . . . . ?
C3 C4 C5 C6 1.4(7) . . . . ?
C7 C4 C5 C6 178.4(4) . . . . ?
C2 C1 C6 C5 0.5(8) . . . . ?
C4 C5 C6 C1 -1.4(8) . . . . ?
C9 N1 C7 C4 92.7(5) . . . . ?
C9 N1 C7 C8 -144.0(4) . . . . ?
C5 C4 C7 N1 46.5(5) . . . . ?
C3 C4 C7 N1 -136.7(4) . . . . ?
C5 C4 C7 C8 -75.9(5) . . . . ?
C3 C4 C7 C8 100.9(5) . . . . ?
C7 N1 C9 O1 3.2(6) . . . . ?
C7 N1 C9 C10 -176.6(4) . . . . ?
O1 C9 C10 C11 12.4(6) . . . . ?
N1 C9 C10 C11 -167.7(4) . . . . ?
C9 C10 C11 C12 -177.0(4) . . . . ?
C13 N2 C12 C11 107.7(4) . . . . ?
C13 N2 C12 C18 -126.9(4) . . . . ?
C10 C11 C12 N2 -119.5(4) . . . . ?
C10 C11 C12 C18 116.8(4) . . . . ?
C14 O3 C13 O2 -0.3(7) . . . . ?
C14 O3 C13 N2 -179.5(4) . . . . ?
C12 N2 C13 O2 3.8(7) . . . . ?
C12 N2 C13 O3 -176.9(3) . . . . ?
C13 O3 C14 C17 63.3(5) . . . . ?
C13 O3 C14 C15 -179.7(5) . . . . ?
C13 O3 C14 C16 -61.3(6) . . . . ?
N2 C12 C18 C19 -179.1(4) . . . . ?
C11 C12 C18 C19 -55.3(5) . . . . ?
C12 C18 C19 C20 80.3(5) . . . . ?
C42 O5 C20 O4 -1.0(8) . . . . ?
C42 O5 C20 C19 178.6(5) . . . . ?
C18 C19 C20 O4 35.8(7) . . . . ?
C18 C19 C20 O5 -143.8(5) . . . . ?
C26 C21 C22 C23 2(2) . . . . ?
C21 C22 C23 C24 1.4(19) . . . . ?
C22 C23 C24 C25 -2.9(12) . . . . ?
C23 C24 C25 C26 1.4(10) . . . . ?
C22 C21 C26 C25 -3.3(15) . . . . ?
C22 C21 C26 C27 177.1(10) . . . . ?
C24 C25 C26 C21 1.8(10) . . . . ?
C24 C25 C26 C27 -178.6(5) . . . . ?
C29 N3 C27 C28 -157.3(4) . . . . ?
C29 N3 C27 C26 79.1(5) . . . . ?
C21 C26 C27 N3 23.5(8) . . . . ?
C25 C26 C27 N3 -156.1(4) . . . . ?
C21 C26 C27 C28 -98.3(8) . . . . ?
C25 C26 C27 C28 82.1(5) . . . . ?
C27 N3 C29 O6 5.6(7) . . . . ?
C27 N3 C29 C30 -175.0(4) . . . . ?
O6 C29 C30 C31 14.6(6) . . . . ?
N3 C29 C30 C31 -164.8(4) . . . . ?
C29 C30 C31 C32 -178.4(4) . . . . ?
C33 N4 C32 C31 105.0(4) . . . . ?
C33 N4 C32 C38 -131.2(4) . . . . ?
C30 C31 C32 N4 -120.0(4) . . . . ?
C30 C31 C32 C38 117.9(4) . . . . ?
C32 N4 C33 O7 8.5(7) . . . . ?
C32 N4 C33 O8 -173.9(3) . . . . ?
C34 O8 C33 O7 -1.6(7) . . . . ?
C34 O8 C33 N4 -179.3(4) . . . . ?
C33 O8 C34 C35 -60.4(5) . . . . ?
C33 O8 C34 C37 63.5(5) . . . . ?
C33 O8 C34 C36 -179.3(5) . . . . ?
N4 C32 C38 C39 177.8(3) . . . . ?
C31 C32 C38 C39 -59.4(5) . . . . ?
C32 C38 C39 C40 80.3(5) . . . . ?
C41 O10 C40 O9 -4.3(7) . . . . ?
C41 O10 C40 C39 179.5(4) . . . . ?
C38 C39 C40 O9 33.8(6) . . . . ?
C38 C39 C40 O10 -150.1(4) . . . . ?
_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full        26.43
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         0.416
_refine_diff_density_min         -0.328
_refine_diff_density_rms         0.048


data_tr2
_database_code_depnum_ccdc_archive 'CCDC 922311'
#TrackingRef '17263_web_deposit_cif_file_1_DnyaneshwarShivajiKand_1359376329.06 Talukdar Chemical Communications 14a-S.cif'
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         C21H30N2O5
_chemical_formula_sum            'C21 H30 N2 O5'
_chemical_formula_weight         390.47
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           Orthorhombic
_symmetry_space_group_name_H-M   P_21_21_2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x+1/2, y+1/2, -z'
'-x, -y, z'
_cell_length_a                   19.851(4)
_cell_length_b                   20.966(5)
_cell_length_c                   5.1137(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2128.3(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?
_exptl_crystal_description       needles
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.185
_exptl_crystal_size_mid          0.161
_exptl_crystal_size_min          0.058
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.222
_exptl_crystal_density_method    calcd
_exptl_crystal_F_000             844
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.984
_exptl_absorpt_correction_T_max  0.995
_exptl_absorpt_process_details   ?
_exptl_special_details           
;
?
;
_diffrn_ambient_temperature      296(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            25233
_diffrn_reflns_av_R_equivalents  0.0590
_diffrn_reflns_av_sigmaI/netI    0.0450
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_theta_min         1.41
_diffrn_reflns_theta_max         27.38
_reflns_number_total             4839
_reflns_number_gt                4159
_reflns_threshold_expression     >2sigma(I)
_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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^)+(0.0365P)^2^+0.5819P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.2(8)
_refine_ls_number_reflns         4839
_refine_ls_number_parameters     258
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0473
_refine_ls_R_factor_gt           0.0361
_refine_ls_wR_factor_ref         0.0820
_refine_ls_wR_factor_gt          0.0774
_refine_ls_goodness_of_fit_ref   0.935
_refine_ls_restrained_S_all      0.935
_refine_ls_shift/su_max          1.309
_refine_ls_shift/su_mean         0.132
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 1.27162(5) 0.28909(5) 0.9629(3) 0.0267(3) Uani 1 1 d . . .
O2 O 1.23781(6) 0.21437(6) 1.2460(2) 0.0326(3) Uani 1 1 d . . .
O3 O 0.99916(6) 0.27013(5) 0.39391(19) 0.0219(3) Uani 1 1 d . . .
O4 O 0.91025(5) 0.04811(5) 1.0634(2) 0.0178(2) Uani 1 1 d . . .
N1 N 0.89724(6) 0.01959(6) 0.6379(2) 0.0147(3) Uani 1 1 d . . .
H29 H 0.9145 0.0206 0.4836 0.018 Uiso 1 1 calc R . .
N2 N 1.01689(6) 0.25813(5) 0.8300(2) 0.0131(3) Uani 1 1 d . . .
H8 H 1.0145 0.2768 0.9795 0.016 Uiso 1 1 calc R . .
C1 C 0.66007(8) 0.10147(8) 0.6869(4) 0.0252(4) Uani 1 1 d . . .
H1 H 0.6224 0.1278 0.6887 0.030 Uiso 1 1 calc R . .
C2 C 0.66774(8) 0.05452(8) 0.8749(3) 0.0242(4) Uani 1 1 d . . .
H23 H 0.6347 0.0487 1.0016 0.029 Uiso 1 1 calc R . .
C3 C 0.72470(8) 0.01603(7) 0.8749(3) 0.0203(3) Uani 1 1 d . . .
H24 H 0.7297 -0.0152 1.0027 0.024 Uiso 1 1 calc R . .
C4 C 0.77423(7) 0.02361(7) 0.6864(3) 0.0152(3) Uani 1 1 d . . .
C5 C 0.83678(7) -0.01860(7) 0.6849(3) 0.0144(3) Uani 1 1 d . . .
H28 H 0.8409 -0.0389 0.8568 0.017 Uiso 1 1 calc R . .
C6 C 0.92650(7) 0.05325(7) 0.8314(3) 0.0139(3) Uani 1 1 d . . .
C7 C 0.97890(7) 0.09914(7) 0.7401(3) 0.0142(3) Uani 1 1 d . . .
H30 H 0.9953 0.0957 0.5703 0.017 Uiso 1 1 calc R . .
C8 C 1.00265(7) 0.14446(7) 0.8942(3) 0.0143(3) Uani 1 1 d . . .
H20 H 0.9886 0.1444 1.0676 0.017 Uiso 1 1 calc R . .
C9 C 1.05055(7) 0.19606(6) 0.8117(3) 0.0123(3) Uani 1 1 d . . .
H19 H 1.0634 0.1887 0.6291 0.015 Uiso 1 1 calc R . .
C10 C 1.11439(7) 0.19553(7) 0.9801(3) 0.0141(3) Uani 1 1 d . . .
H6 H 1.1026 0.2057 1.1593 0.017 Uiso 1 1 calc R . .
H7 H 1.1338 0.1531 0.9782 0.017 Uiso 1 1 calc R . .
C11 C 1.16642(7) 0.24297(7) 0.8832(3) 0.0173(3) Uani 1 1 d . . .
H5 H 1.1798 0.2314 0.7071 0.021 Uiso 1 1 calc R . .
H4 H 1.1461 0.2850 0.8758 0.021 Uiso 1 1 calc R . .
C12 C 1.22818(8) 0.24588(7) 1.0535(3) 0.0182(3) Uani 1 1 d . . .
C13 C 1.33255(9) 0.29791(8) 1.1136(4) 0.0326(4) Uani 1 1 d . . .
H31 H 1.3211 0.3105 1.2885 0.049 Uiso 1 1 calc R . .
H2 H 1.3596 0.3305 1.0339 0.049 Uiso 1 1 calc R . .
H3 H 1.3574 0.2586 1.1184 0.049 Uiso 1 1 calc R . .
C14 C 0.98955(7) 0.28681(7) 0.6192(3) 0.0145(3) Uani 1 1 d . . .
O5 O 0.95148(6) 0.33637(5) 0.6950(2) 0.0231(3) Uani 1 1 d . . .
C16 C 0.91822(9) 0.37846(8) 0.5001(3) 0.0247(4) Uani 1 1 d . . .
C17 C 0.88147(13) 0.42557(11) 0.6735(4) 0.0561(7) Uani 1 1 d . . .
H10 H 0.8506 0.4030 0.7847 0.084 Uiso 1 1 calc R . .
H11 H 0.8570 0.4552 0.5666 0.084 Uiso 1 1 calc R . .
H12 H 0.9135 0.4483 0.7789 0.084 Uiso 1 1 calc R . .
C18 C 0.86851(9) 0.34098(9) 0.3378(4) 0.0288(4) Uani 1 1 d . . .
H13 H 0.8925 0.3128 0.2229 0.043 Uiso 1 1 calc R . .
H14 H 0.8416 0.3698 0.2364 0.043 Uiso 1 1 calc R . .
H15 H 0.8399 0.3165 0.4511 0.043 Uiso 1 1 calc R . .
C19 C 0.97121(9) 0.41222(8) 0.3374(4) 0.0278(4) Uani 1 1 d . . .
H18 H 1.0057 0.4288 0.4502 0.042 Uiso 1 1 calc R . .
H16 H 0.9507 0.4467 0.2427 0.042 Uiso 1 1 calc R . .
H17 H 0.9908 0.3826 0.2162 0.042 Uiso 1 1 calc R . .
C20 C 0.70890(9) 0.10887(8) 0.4964(4) 0.0264(4) Uani 1 1 d . . .
H22 H 0.7037 0.1399 0.3680 0.032 Uiso 1 1 calc R . .
C21 C 0.76559(8) 0.07015(7) 0.4959(3) 0.0206(3) Uani 1 1 d . . .
H21 H 0.7981 0.0754 0.3668 0.025 Uiso 1 1 calc R . .
C22 C 0.83194(8) -0.07071(7) 0.4784(3) 0.0191(3) Uani 1 1 d . . .
H26 H 0.8296 -0.0516 0.3080 0.029 Uiso 1 1 calc R . .
H27 H 0.7922 -0.0957 0.5084 0.029 Uiso 1 1 calc R . .
H25 H 0.8710 -0.0976 0.4887 0.029 Uiso 1 1 calc 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 0.0168(6) 0.0236(5) 0.0397(7) 0.0062(5) -0.0081(5) -0.0062(5)
O2 0.0246(7) 0.0439(7) 0.0293(7) 0.0144(6) -0.0113(5) -0.0075(6)
O3 0.0317(6) 0.0245(6) 0.0094(5) -0.0006(4) 0.0009(5) 0.0108(5)
O4 0.0219(6) 0.0194(5) 0.0120(5) -0.0004(4) 0.0015(4) -0.0039(4)
N1 0.0164(6) 0.0169(6) 0.0108(6) -0.0003(5) 0.0003(5) -0.0023(5)
N2 0.0175(6) 0.0135(5) 0.0082(6) -0.0021(5) -0.0008(5) 0.0030(5)
C1 0.0187(8) 0.0222(8) 0.0346(9) -0.0049(7) -0.0031(8) 0.0028(7)
C2 0.0173(8) 0.0300(8) 0.0255(9) -0.0024(7) 0.0029(7) -0.0041(7)
C3 0.0211(8) 0.0219(7) 0.0178(7) 0.0021(6) -0.0003(6) -0.0058(6)
C4 0.0164(7) 0.0144(6) 0.0147(7) -0.0019(6) -0.0040(6) -0.0028(6)
C5 0.0163(7) 0.0131(6) 0.0138(7) 0.0022(6) -0.0026(6) -0.0032(6)
C6 0.0141(7) 0.0115(6) 0.0159(7) 0.0003(6) -0.0010(6) 0.0020(6)
C7 0.0136(7) 0.0150(7) 0.0138(7) 0.0011(6) 0.0014(6) 0.0024(6)
C8 0.0134(7) 0.0166(7) 0.0129(7) 0.0030(6) 0.0011(6) 0.0010(6)
C9 0.0139(7) 0.0125(6) 0.0106(7) -0.0001(5) 0.0009(6) 0.0018(5)
C10 0.0148(7) 0.0146(7) 0.0129(7) 0.0014(6) -0.0010(6) 0.0011(6)
C11 0.0149(7) 0.0193(7) 0.0177(7) 0.0025(6) -0.0016(6) -0.0025(6)
C12 0.0161(7) 0.0173(7) 0.0212(8) -0.0013(6) 0.0007(6) 0.0005(6)
C13 0.0191(9) 0.0281(9) 0.0508(12) -0.0035(9) -0.0116(9) -0.0036(7)
C14 0.0142(7) 0.0155(7) 0.0138(7) -0.0012(6) 0.0014(6) 0.0008(6)
O5 0.0331(7) 0.0256(6) 0.0105(5) 0.0011(5) -0.0017(5) 0.0178(5)
C16 0.0335(10) 0.0259(8) 0.0146(8) 0.0032(7) -0.0028(7) 0.0178(7)
C17 0.0894(18) 0.0615(14) 0.0173(9) 0.0002(10) -0.0008(11) 0.0608(14)
C18 0.0209(9) 0.0408(10) 0.0247(9) 0.0136(8) 0.0005(7) 0.0033(7)
C19 0.0344(9) 0.0199(8) 0.0292(9) 0.0043(7) -0.0119(8) 0.0010(7)
C20 0.0288(9) 0.0215(8) 0.0290(9) 0.0071(8) -0.0040(8) 0.0033(7)
C21 0.0217(8) 0.0214(7) 0.0189(8) 0.0043(6) 0.0027(7) 0.0002(6)
C22 0.0226(8) 0.0155(7) 0.0192(8) -0.0012(6) -0.0043(7) 0.0000(6)
_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 C12 1.3339(18) . ?
O1 C13 1.446(2) . ?
O2 C12 1.2005(19) . ?
O3 C14 1.2191(17) . ?
O4 C6 1.2340(18) . ?
N1 C6 1.3470(19) . ?
N1 C5 1.4627(19) . ?
N1 H29 0.8600 . ?
N2 C14 1.3482(18) . ?
N2 C9 1.4658(18) . ?
N2 H8 0.8600 . ?
C1 C20 1.383(3) . ?
C1 C2 1.384(2) . ?
C1 H1 0.9300 . ?
C2 C3 1.389(2) . ?
C2 H23 0.9300 . ?
C3 C4 1.386(2) . ?
C3 H24 0.9300 . ?
C4 C21 1.390(2) . ?
C4 C5 1.525(2) . ?
C5 C22 1.522(2) . ?
C5 H28 0.9800 . ?
C6 C7 1.492(2) . ?
C7 C8 1.321(2) . ?
C7 H30 0.9300 . ?
C8 C9 1.501(2) . ?
C8 H20 0.9300 . ?
C9 C10 1.532(2) . ?
C9 H19 0.9800 . ?
C10 C11 1.517(2) . ?
C10 H6 0.9700 . ?
C10 H7 0.9700 . ?
C11 C12 1.505(2) . ?
C11 H5 0.9700 . ?
C11 H4 0.9700 . ?
C13 H31 0.9600 . ?
C13 H2 0.9600 . ?
C13 H3 0.9600 . ?
C14 O5 1.3420(18) . ?
O5 C16 1.4860(18) . ?
C16 C18 1.510(3) . ?
C16 C17 1.515(2) . ?
C16 C19 1.516(3) . ?
C17 H10 0.9600 . ?
C17 H11 0.9600 . ?
C17 H12 0.9600 . ?
C18 H13 0.9600 . ?
C18 H14 0.9600 . ?
C18 H15 0.9600 . ?
C19 H18 0.9600 . ?
C19 H16 0.9600 . ?
C19 H17 0.9600 . ?
C20 C21 1.388(2) . ?
C20 H22 0.9300 . ?
C21 H21 0.9300 . ?
C22 H26 0.9600 . ?
C22 H27 0.9600 . ?
C22 H25 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
C12 O1 C13 116.26(13) . . ?
C6 N1 C5 121.33(13) . . ?
C6 N1 H29 119.3 . . ?
C5 N1 H29 119.3 . . ?
C14 N2 C9 121.90(12) . . ?
C14 N2 H8 119.0 . . ?
C9 N2 H8 119.1 . . ?
C20 C1 C2 119.47(15) . . ?
C20 C1 H1 120.3 . . ?
C2 C1 H1 120.3 . . ?
C1 C2 C3 120.16(15) . . ?
C1 C2 H23 119.9 . . ?
C3 C2 H23 119.9 . . ?
C4 C3 C2 120.74(14) . . ?
C4 C3 H24 119.6 . . ?
C2 C3 H24 119.6 . . ?
C3 C4 C21 118.71(14) . . ?
C3 C4 C5 120.98(13) . . ?
C21 C4 C5 120.31(13) . . ?
N1 C5 C22 109.31(12) . . ?
N1 C5 C4 110.57(11) . . ?
C22 C5 C4 111.62(12) . . ?
N1 C5 H28 108.4 . . ?
C22 C5 H28 108.4 . . ?
C4 C5 H28 108.4 . . ?
O4 C6 N1 123.21(14) . . ?
O4 C6 C7 122.64(13) . . ?
N1 C6 C7 114.12(13) . . ?
C8 C7 C6 121.74(14) . . ?
C8 C7 H30 119.1 . . ?
C6 C7 H30 119.1 . . ?
C7 C8 C9 125.22(13) . . ?
C7 C8 H20 117.4 . . ?
C9 C8 H20 117.4 . . ?
N2 C9 C8 109.46(11) . . ?
N2 C9 C10 110.35(11) . . ?
C8 C9 C10 111.14(12) . . ?
N2 C9 H19 108.6 . . ?
C8 C9 H19 108.6 . . ?
C10 C9 H19 108.6 . . ?
C11 C10 C9 112.02(12) . . ?
C11 C10 H6 109.2 . . ?
C9 C10 H6 109.2 . . ?
C11 C10 H7 109.2 . . ?
C9 C10 H7 109.2 . . ?
H6 C10 H7 107.9 . . ?
C12 C11 C10 113.10(12) . . ?
C12 C11 H5 109.0 . . ?
C10 C11 H5 109.0 . . ?
C12 C11 H4 109.0 . . ?
C10 C11 H4 109.0 . . ?
H5 C11 H4 107.8 . . ?
O2 C12 O1 123.76(14) . . ?
O2 C12 C11 125.57(14) . . ?
O1 C12 C11 110.67(12) . . ?
O1 C13 H31 109.4 . . ?
O1 C13 H2 109.5 . . ?
H31 C13 H2 109.5 . . ?
O1 C13 H3 109.5 . . ?
H31 C13 H3 109.5 . . ?
H2 C13 H3 109.5 . . ?
O3 C14 O5 125.66(13) . . ?
O3 C14 N2 124.38(13) . . ?
O5 C14 N2 109.95(12) . . ?
C14 O5 C16 121.09(12) . . ?
O5 C16 C18 110.48(13) . . ?
O5 C16 C17 102.03(13) . . ?
C18 C16 C17 110.26(17) . . ?
O5 C16 C19 109.69(13) . . ?
C18 C16 C19 113.26(14) . . ?
C17 C16 C19 110.54(16) . . ?
C16 C17 H10 109.4 . . ?
C16 C17 H11 109.5 . . ?
H10 C17 H11 109.5 . . ?
C16 C17 H12 109.5 . . ?
H10 C17 H12 109.5 . . ?
H11 C17 H12 109.5 . . ?
C16 C18 H13 109.4 . . ?
C16 C18 H14 109.5 . . ?
H13 C18 H14 109.5 . . ?
C16 C18 H15 109.5 . . ?
H13 C18 H15 109.5 . . ?
H14 C18 H15 109.5 . . ?
C16 C19 H18 109.5 . . ?
C16 C19 H16 109.5 . . ?
H18 C19 H16 109.5 . . ?
C16 C19 H17 109.4 . . ?
H18 C19 H17 109.5 . . ?
H16 C19 H17 109.5 . . ?
C1 C20 C21 120.26(15) . . ?
C1 C20 H22 119.9 . . ?
C21 C20 H22 119.9 . . ?
C20 C21 C4 120.65(15) . . ?
C20 C21 H21 119.7 . . ?
C4 C21 H21 119.7 . . ?
C5 C22 H26 109.5 . . ?
C5 C22 H27 109.5 . . ?
H26 C22 H27 109.5 . . ?
C5 C22 H25 109.5 . . ?
H26 C22 H25 109.5 . . ?
H27 C22 H25 109.5 . . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C20 C1 C2 C3 1.3(2) . . . . ?
C1 C2 C3 C4 -0.5(2) . . . . ?
C2 C3 C4 C21 -0.5(2) . . . . ?
C2 C3 C4 C5 -179.85(13) . . . . ?
C6 N1 C5 C22 -156.75(13) . . . . ?
C6 N1 C5 C4 79.98(16) . . . . ?
C3 C4 C5 N1 -136.09(14) . . . . ?
C21 C4 C5 N1 44.58(18) . . . . ?
C3 C4 C5 C22 101.99(16) . . . . ?
C21 C4 C5 C22 -77.34(16) . . . . ?
C5 N1 C6 O4 9.5(2) . . . . ?
C5 N1 C6 C7 -168.56(12) . . . . ?
O4 C6 C7 C8 -11.9(2) . . . . ?
N1 C6 C7 C8 166.14(13) . . . . ?
C6 C7 C8 C9 -174.19(13) . . . . ?
C14 N2 C9 C8 -98.28(15) . . . . ?
C14 N2 C9 C10 139.10(13) . . . . ?
C7 C8 C9 N2 114.69(16) . . . . ?
C7 C8 C9 C10 -123.16(16) . . . . ?
N2 C9 C10 C11 -63.99(15) . . . . ?
C8 C9 C10 C11 174.39(12) . . . . ?
C9 C10 C11 C12 176.97(12) . . . . ?
C13 O1 C12 O2 -1.3(2) . . . . ?
C13 O1 C12 C11 178.33(14) . . . . ?
C10 C11 C12 O2 0.8(2) . . . . ?
C10 C11 C12 O1 -178.80(12) . . . . ?
C9 N2 C14 O3 -12.3(2) . . . . ?
C9 N2 C14 O5 168.58(12) . . . . ?
O3 C14 O5 C16 -2.3(2) . . . . ?
N2 C14 O5 C16 176.82(13) . . . . ?
C14 O5 C16 C18 62.20(18) . . . . ?
C14 O5 C16 C17 179.43(16) . . . . ?
C14 O5 C16 C19 -63.35(18) . . . . ?
C2 C1 C20 C21 -0.9(3) . . . . ?
C1 C20 C21 C4 -0.1(2) . . . . ?
C3 C4 C21 C20 0.8(2) . . . . ?
C5 C4 C21 C20 -179.82(14) . . . . ?
_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        27.38
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.180
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.039