# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is © The Royal Society of Chemistry 2013


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#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
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# 
#  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. 
# 
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#  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_10_12srv031
_database_code_depnum_ccdc_archive 'CCDC 911245'
#TrackingRef '15470_web_deposit_cif_file_0_DmitryYufit_1353069364.10.cif'
_audit_creation_date             2012-02-03
_audit_creation_method           
;
Olex2 1.1-beta
(compiled 2011.11.01 svn.r2039, GUI svn.r3906)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
tert-Butyl 2,2'-(6-nitro-6-phenyl-1,4-diazepane-1,4-diyl)diacetate
;
_chemical_formula_moiety         'C23 H35 N3 O6'
_chemical_formula_sum            'C23 H35 N3 O6'
_chemical_formula_weight         449.54
_chemical_melting_point          '78-90 C'
_chemical_oxdiff_formula         'C23 H35 N3 O6'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'
_cell_length_a                   21.3378(19)
_cell_length_b                   11.5579(10)
_cell_length_c                   10.3203(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.329(8)
_cell_angle_gamma                90.00
_cell_volume                     2503.9(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    790
_cell_measurement_temperature    120
_cell_measurement_theta_max      32.4600
_cell_measurement_theta_min      2.6160
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.19115
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug 3 2011,13:03:54)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.192
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             968
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.06
_exptl_special_details           
;
?
;
_diffrn_reflns_av_R_equivalents  0.1564
_diffrn_reflns_av_unetI/netI     0.2183
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            15496
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         0.9042
_diffrn_ambient_temperature      120
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 16.1511
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
1 omega -103.00 -74.00 1.0000 25.0000
omega____ theta____ kappa____ phi______ frames
- -26.1867 165.0000 147.0000 29
#__ type_ start__ end____ width___ exp.time_
2 omega -88.00 47.00 1.0000 25.0000
omega____ theta____ kappa____ phi______ frames
- -26.1867 0.0000 90.0000 135
#__ type_ start__ end____ width___ exp.time_
3 omega 57.00 89.00 1.0000 25.0000
omega____ theta____ kappa____ phi______ frames
- 26.9679 179.0000 30.0000 32
#__ type_ start__ end____ width___ exp.time_
4 omega 61.00 103.00 1.0000 25.0000
omega____ theta____ kappa____ phi______ frames
- 26.9679 179.0000 -90.0000 42
#__ type_ start__ end____ width___ exp.time_
5 omega 50.00 103.00 1.0000 25.0000
omega____ theta____ kappa____ phi______ frames
- 26.9679 -165.0000 -55.0000 53
#__ type_ start__ end____ width___ exp.time_
6 omega -96.00 -37.00 1.0000 25.0000
omega____ theta____ kappa____ phi______ frames
- -26.1867 -77.0000 30.0000 59
;
_diffrn_measurement_device       '3-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini ultra'
_diffrn_measurement_method       \w-scan
_diffrn_orient_matrix_UB_11      0.0231851000
_diffrn_orient_matrix_UB_12      -0.0440000000
_diffrn_orient_matrix_UB_13      0.0173170000
_diffrn_orient_matrix_UB_21      -0.0245687000
_diffrn_orient_matrix_UB_22      -0.0418002000
_diffrn_orient_matrix_UB_23      -0.0037504000
_diffrn_orient_matrix_UB_31      0.0010320000
_diffrn_orient_matrix_UB_32      -0.0088930000
_diffrn_orient_matrix_UB_33      -0.0675991000
_diffrn_radiation_collimation    monochromator
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_radiation_xray_symbol    Mo
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_source_current           n/a
_diffrn_source_type              'sealed tube'
_diffrn_source_voltage           n/a
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1948
_reflns_number_total             5463
_reflns_odcompleteness_completeness 99.89
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.44
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug 3 2011,13:03:54)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug 3 2011,13:03:54)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug 3 2011,13:03:54)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.338
_refine_diff_density_min         -0.328
_refine_diff_density_rms         0.065
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.944
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     293
_refine_ls_number_reflns         5463
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2327
_refine_ls_R_factor_gt           0.0899
_refine_ls_restrained_S_all      0.944
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0600P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1741
_refine_ls_wR_factor_ref         0.2425
_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.
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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 0.44314(15) 0.2863(4) 0.2759(3) 0.0581(11) Uani 1 1 d . . .
O2 O 0.49877(14) 0.1918(3) 0.4516(3) 0.0442(9) Uani 1 1 d . . .
O3 O 0.10645(16) 0.1495(3) 0.3792(3) 0.0551(11) Uani 1 1 d . . .
O4 O 0.03621(15) 0.1530(3) 0.1897(3) 0.0515(10) Uani 1 1 d . . .
O5 O 0.31711(16) 0.4949(3) 0.5448(3) 0.0494(10) Uani 1 1 d . . .
O6 O 0.21432(16) 0.5100(3) 0.5180(3) 0.0435(9) Uani 1 1 d . . .
N1 N 0.33189(16) 0.2677(3) 0.3967(3) 0.0344(10) Uani 1 1 d . A .
N2 N 0.20240(16) 0.2435(3) 0.2443(3) 0.0279(9) Uani 1 1 d . B .
N3 N 0.2633(2) 0.4817(3) 0.4790(4) 0.0382(10) Uani 1 1 d . . .
C1 C 0.3119(2) 0.1645(4) 0.3181(5) 0.0362(12) Uani 1 1 d . . .
H1A H 0.3345 0.0978 0.3601 0.043 Uiso 1 1 calc R . .
H1B H 0.3232 0.1732 0.2317 0.043 Uiso 1 1 calc R . .
C2 C 0.2401(2) 0.1434(4) 0.3024(5) 0.0378(12) Uani 1 1 d . . .
H2A H 0.2288 0.0762 0.2468 0.045 Uiso 1 1 calc R . .
H2B H 0.2295 0.1267 0.3881 0.045 Uiso 1 1 calc R . .
C3 C 0.2008(2) 0.3362(4) 0.3402(4) 0.0328(11) Uani 1 1 d . . .
H3A H 0.2048 0.3025 0.4274 0.039 Uiso 1 1 calc R . .
H3B H 0.1599 0.3749 0.3205 0.039 Uiso 1 1 calc R . .
C4 C 0.2544(2) 0.4270(4) 0.3411(4) 0.0323(11) Uani 1 1 d . . .
C5 C 0.3180(2) 0.3741(4) 0.3199(4) 0.0338(11) Uani 1 1 d . . .
H5A H 0.3159 0.3571 0.2271 0.041 Uiso 1 1 calc R . .
H5B H 0.3521 0.4294 0.3462 0.041 Uiso 1 1 calc R . .
C6 C 0.3962(2) 0.2593(5) 0.4692(4) 0.0416(13) Uani 1 1 d . . .
H6A H 0.3986 0.1933 0.5279 0.050 Uiso 1 1 calc R A .
H6B H 0.4053 0.3280 0.5234 0.050 Uiso 1 1 calc R . .
C7 C 0.4472(2) 0.2468(4) 0.3853(5) 0.0395(12) Uani 1 1 d . A .
C8A C 0.5614(6) 0.1866(12) 0.4072(12) 0.029(4) Uiso 0.50 1 d P A 2
C8B C 0.5538(7) 0.1672(14) 0.3799(14) 0.043(5) Uiso 0.50 1 d P A 1
C9A C 0.5872(6) 0.2975(11) 0.3891(13) 0.038(3) Uiso 0.50 1 d P A 2
H9AA H 0.5600 0.3371 0.3189 0.058 Uiso 0.50 1 calc PR A 2
H9AB H 0.6289 0.2887 0.3674 0.058 Uiso 0.50 1 calc PR A 2
H9AC H 0.5903 0.3415 0.4689 0.058 Uiso 0.50 1 calc PR A 2
C9B C 0.5780(9) 0.2881(16) 0.3459(16) 0.083(6) Uiso 0.50 1 d P A 1
H9BA H 0.5484 0.3213 0.2746 0.124 Uiso 0.50 1 calc PR A 1
H9BB H 0.6189 0.2803 0.3203 0.124 Uiso 0.50 1 calc PR A 1
H9BC H 0.5817 0.3375 0.4216 0.124 Uiso 0.50 1 calc PR A 1
C10A C 0.6061(6) 0.1342(11) 0.5165(12) 0.053(4) Uiso 0.50 1 d P A 2
H10A H 0.6134 0.1869 0.5896 0.080 Uiso 0.50 1 calc PR A 2
H10B H 0.6458 0.1181 0.4884 0.080 Uiso 0.50 1 calc PR A 2
H10C H 0.5884 0.0635 0.5429 0.080 Uiso 0.50 1 calc PR A 2
C10B C 0.5949(6) 0.0920(12) 0.4862(12) 0.058(4) Uiso 0.50 1 d P A 1
H10D H 0.5992 0.1300 0.5700 0.087 Uiso 0.50 1 calc PR A 1
H10E H 0.6363 0.0811 0.4638 0.087 Uiso 0.50 1 calc PR A 1
H10F H 0.5748 0.0182 0.4908 0.087 Uiso 0.50 1 calc PR A 1
C11A C 0.5441(6) 0.0893(12) 0.2953(13) 0.065(4) Uiso 0.50 1 d P A 2
H11A H 0.5249 0.0242 0.3308 0.097 Uiso 0.50 1 calc PR A 2
H11B H 0.5823 0.0648 0.2661 0.097 Uiso 0.50 1 calc PR A 2
H11C H 0.5149 0.1207 0.2222 0.097 Uiso 0.50 1 calc PR A 2
C11B C 0.5430(5) 0.1233(10) 0.2520(10) 0.039(3) Uiso 0.50 1 d P A 1
H11D H 0.5187 0.0532 0.2490 0.059 Uiso 0.50 1 calc PR A 1
H11E H 0.5831 0.1073 0.2257 0.059 Uiso 0.50 1 calc PR A 1
H11F H 0.5199 0.1792 0.1931 0.059 Uiso 0.50 1 calc PR A 1
C12 C 0.1394(2) 0.2109(4) 0.1760(4) 0.0347(12) Uani 1 1 d . . .
H12A H 0.1440 0.1508 0.1128 0.042 Uiso 1 1 calc R B .
H12B H 0.1202 0.2774 0.1268 0.042 Uiso 1 1 calc R . .
C13 C 0.0940(2) 0.1679(4) 0.2634(5) 0.0368(12) Uani 1 1 d . B .
C14A C -0.0196(4) 0.1184(9) 0.2643(10) 0.021(2) Uiso 0.50 1 d P B 1
C14B C -0.0179(6) 0.0974(12) 0.2244(13) 0.053(4) Uiso 0.50 1 d P B 2
C15A C -0.0067(7) -0.0101(13) 0.2843(14) 0.049(4) Uiso 0.50 1 d P B 1
H15A H 0.0011 -0.0437 0.2035 0.073 Uiso 0.50 1 calc PR B 1
H15B H -0.0429 -0.0468 0.3099 0.073 Uiso 0.50 1 calc PR B 1
H15C H 0.0300 -0.0211 0.3520 0.073 Uiso 0.50 1 calc PR B 1
C15B C -0.0053(7) -0.0029(13) 0.3208(13) 0.045(4) Uiso 0.50 1 d P B 2
H15D H 0.0122 -0.0667 0.2796 0.067 Uiso 0.50 1 calc PR B 2
H15E H -0.0445 -0.0262 0.3465 0.067 Uiso 0.50 1 calc PR B 2
H15F H 0.0244 0.0210 0.3973 0.067 Uiso 0.50 1 calc PR B 2
C16A C -0.0763(5) 0.1400(10) 0.1525(10) 0.048(3) Uiso 0.50 1 d P B 1
H16A H -0.0782 0.2206 0.1298 0.072 Uiso 0.50 1 calc PR B 1
H16B H -0.1151 0.1178 0.1808 0.072 Uiso 0.50 1 calc PR B 1
H16C H -0.0711 0.0950 0.0769 0.072 Uiso 0.50 1 calc PR B 1
C16B C -0.0650(7) 0.0703(13) 0.1085(12) 0.082(4) Uiso 0.50 1 d P B 2
H16D H -0.0746 0.1388 0.0560 0.123 Uiso 0.50 1 calc PR B 2
H16E H -0.1031 0.0424 0.1351 0.123 Uiso 0.50 1 calc PR B 2
H16F H -0.0485 0.0119 0.0577 0.123 Uiso 0.50 1 calc PR B 2
C17A C -0.0249(4) 0.1912(8) 0.3820(8) 0.030(2) Uiso 0.50 1 d P B 1
H17A H 0.0126 0.1812 0.4480 0.046 Uiso 0.50 1 calc PR B 1
H17B H -0.0617 0.1679 0.4170 0.046 Uiso 0.50 1 calc PR B 1
H17C H -0.0290 0.2711 0.3565 0.046 Uiso 0.50 1 calc PR B 1
C17B C -0.0441(7) 0.1898(14) 0.3009(14) 0.084(4) Uiso 0.50 1 d P B 2
H17D H -0.0107 0.2192 0.3676 0.126 Uiso 0.50 1 calc PR B 2
H17E H -0.0773 0.1580 0.3416 0.126 Uiso 0.50 1 calc PR B 2
H17F H -0.0610 0.2514 0.2427 0.126 Uiso 0.50 1 calc PR B 2
C18 C 0.2372(2) 0.5279(4) 0.2461(4) 0.0297(11) Uani 1 1 d . . .
C19 C 0.2025(2) 0.5045(4) 0.1188(4) 0.0379(12) Uani 1 1 d . . .
H19 H 0.1898 0.4292 0.0956 0.045 Uiso 1 1 calc R . .
C20 C 0.1874(2) 0.5927(5) 0.0290(5) 0.0442(13) Uani 1 1 d . . .
H20 H 0.1638 0.5771 -0.0540 0.053 Uiso 1 1 calc R . .
C21 C 0.2072(2) 0.7052(5) 0.0622(5) 0.0446(14) Uani 1 1 d . . .
H21 H 0.1971 0.7645 0.0011 0.054 Uiso 1 1 calc R . .
C22 C 0.2417(2) 0.7291(4) 0.1856(5) 0.0439(13) Uani 1 1 d . . .
H22 H 0.2550 0.8042 0.2081 0.053 Uiso 1 1 calc R . .
C23 C 0.2564(2) 0.6402(4) 0.2752(5) 0.0369(12) Uani 1 1 d . . .
H23 H 0.2799 0.6567 0.3580 0.044 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 0.036(2) 0.091(3) 0.049(2) 0.017(2) 0.0127(16) 0.021(2)
O2 0.0244(19) 0.053(2) 0.057(2) 0.0080(19) 0.0119(15) 0.0077(18)
O3 0.050(2) 0.081(3) 0.039(2) -0.004(2) 0.0199(17) -0.021(2)
O4 0.027(2) 0.066(3) 0.061(2) 0.023(2) 0.0067(16) -0.0122(19)
O5 0.042(2) 0.048(2) 0.053(2) -0.0073(19) -0.0064(17) -0.006(2)
O6 0.052(2) 0.038(2) 0.046(2) -0.0047(18) 0.0226(17) 0.0017(19)
N1 0.019(2) 0.036(2) 0.047(2) -0.001(2) 0.0043(16) 0.0024(19)
N2 0.021(2) 0.027(2) 0.036(2) -0.0021(18) 0.0059(15) -0.0009(18)
N3 0.044(3) 0.034(2) 0.038(2) 0.000(2) 0.012(2) -0.002(2)
C1 0.029(3) 0.031(3) 0.048(3) 0.003(2) 0.007(2) 0.010(2)
C2 0.040(3) 0.029(3) 0.046(3) 0.002(2) 0.012(2) -0.004(2)
C3 0.032(3) 0.025(3) 0.043(3) -0.004(2) 0.010(2) 0.002(2)
C4 0.030(3) 0.032(3) 0.036(3) 0.004(2) 0.0073(19) 0.004(2)
C5 0.022(3) 0.034(3) 0.047(3) 0.005(2) 0.011(2) 0.006(2)
C6 0.030(3) 0.049(3) 0.049(3) -0.002(3) 0.014(2) 0.001(3)
C7 0.032(3) 0.040(3) 0.047(3) -0.001(3) 0.009(2) 0.005(3)
C12 0.027(3) 0.038(3) 0.040(3) -0.008(2) 0.009(2) -0.008(2)
C13 0.021(3) 0.037(3) 0.053(3) -0.005(3) 0.009(2) -0.006(2)
C18 0.030(3) 0.031(3) 0.032(2) 0.002(2) 0.017(2) 0.004(2)
C19 0.043(3) 0.027(3) 0.047(3) 0.004(3) 0.017(2) 0.003(2)
C20 0.049(3) 0.047(3) 0.038(3) 0.002(3) 0.010(2) 0.000(3)
C21 0.044(3) 0.047(4) 0.045(3) 0.009(3) 0.015(2) 0.003(3)
C22 0.048(3) 0.028(3) 0.062(3) 0.002(3) 0.025(3) -0.006(3)
C23 0.035(3) 0.032(3) 0.045(3) 0.002(3) 0.013(2) -0.004(2)
_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 C7 1.206(5) . ?
O2 C7 1.346(5) . ?
O2 C8A 1.490(13) . ?
O2 C8B 1.523(15) . ?
O3 C13 1.196(5) . ?
O4 C13 1.339(5) . ?
O4 C14A 1.582(10) . ?
O4 C14B 1.423(13) . ?
O5 N3 1.233(4) . ?
O6 N3 1.231(4) . ?
N1 C1 1.462(6) . ?
N1 C5 1.464(6) . ?
N1 C6 1.443(5) . ?
N2 C2 1.473(5) . ?
N2 C3 1.463(5) . ?
N2 C12 1.451(5) . ?
N3 C4 1.538(5) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 C2 1.531(6) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.551(6) . ?
C4 C5 1.540(6) . ?
C4 C18 1.525(6) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C7 1.516(6) . ?
C8A C9A 1.421(18) . ?
C8A C10A 1.471(16) . ?
C8A C11A 1.607(19) . ?
C8B C9B 1.55(2) . ?
C8B C10B 1.543(18) . ?
C8B C11B 1.394(18) . ?
C9A H9AA 0.9600 . ?
C9A H9AB 0.9600 . ?
C9A H9AC 0.9600 . ?
C9B H9BA 0.9600 . ?
C9B H9BB 0.9600 . ?
C9B H9BC 0.9600 . ?
C10A H10A 0.9600 . ?
C10A H10B 0.9600 . ?
C10A H10C 0.9600 . ?
C10B H10D 0.9600 . ?
C10B H10E 0.9600 . ?
C10B H10F 0.9600 . ?
C11A H11A 0.9600 . ?
C11A H11B 0.9600 . ?
C11A H11C 0.9600 . ?
C11B H11D 0.9600 . ?
C11B H11E 0.9600 . ?
C11B H11F 0.9600 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.520(6) . ?
C14A C15A 1.518(18) . ?
C14A C16A 1.535(14) . ?
C14A C17A 1.498(14) . ?
C14B C15B 1.52(2) . ?
C14B C16B 1.451(17) . ?
C14B C17B 1.494(18) . ?
C15A H15A 0.9600 . ?
C15A H15B 0.9600 . ?
C15A H15C 0.9600 . ?
C15B H15D 0.9600 . ?
C15B H15E 0.9600 . ?
C15B H15F 0.9600 . ?
C16A H16A 0.9600 . ?
C16A H16B 0.9600 . ?
C16A H16C 0.9600 . ?
C16B H16D 0.9600 . ?
C16B H16E 0.9600 . ?
C16B H16F 0.9600 . ?
C17A H17A 0.9600 . ?
C17A H17B 0.9600 . ?
C17A H17C 0.9600 . ?
C17B H17D 0.9600 . ?
C17B H17E 0.9600 . ?
C17B H17F 0.9600 . ?
C18 C19 1.414(6) . ?
C18 C23 1.378(6) . ?
C19 H19 0.9300 . ?
C19 C20 1.377(6) . ?
C20 H20 0.9300 . ?
C20 C21 1.391(7) . ?
C21 H21 0.9300 . ?
C21 C22 1.379(7) . ?
C22 H22 0.9300 . ?
C22 C23 1.380(6) . ?
C23 H23 0.9300 . ?
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
C7 O2 C8A 124.0(6) . . ?
C7 O2 C8B 118.2(6) . . ?
C8A O2 C8B 14.2(8) . . ?
C13 O4 C14A 117.0(5) . . ?
C13 O4 C14B 128.5(6) . . ?
C14B O4 C14A 17.6(6) . . ?
C1 N1 C5 112.0(3) . . ?
C6 N1 C1 112.9(4) . . ?
C6 N1 C5 114.7(4) . . ?
C3 N2 C2 112.1(3) . . ?
C12 N2 C2 112.6(4) . . ?
C12 N2 C3 112.8(3) . . ?
O5 N3 C4 120.6(4) . . ?
O6 N3 O5 123.3(4) . . ?
O6 N3 C4 116.1(4) . . ?
N1 C1 H1A 109.2 . . ?
N1 C1 H1B 109.2 . . ?
N1 C1 C2 112.1(4) . . ?
H1A C1 H1B 107.9 . . ?
C2 C1 H1A 109.2 . . ?
C2 C1 H1B 109.2 . . ?
N2 C2 C1 112.3(4) . . ?
N2 C2 H2A 109.1 . . ?
N2 C2 H2B 109.1 . . ?
C1 C2 H2A 109.1 . . ?
C1 C2 H2B 109.1 . . ?
H2A C2 H2B 107.9 . . ?
N2 C3 H3A 108.9 . . ?
N2 C3 H3B 108.9 . . ?
N2 C3 C4 113.2(3) . . ?
H3A C3 H3B 107.8 . . ?
C4 C3 H3A 108.9 . . ?
C4 C3 H3B 108.9 . . ?
N3 C4 C3 104.6(3) . . ?
N3 C4 C5 109.2(4) . . ?
C5 C4 C3 113.4(4) . . ?
C18 C4 N3 104.9(3) . . ?
C18 C4 C3 114.9(4) . . ?
C18 C4 C5 109.2(3) . . ?
N1 C5 C4 110.8(3) . . ?
N1 C5 H5A 109.5 . . ?
N1 C5 H5B 109.5 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 108.1 . . ?
N1 C6 H6A 108.5 . . ?
N1 C6 H6B 108.5 . . ?
N1 C6 C7 115.1(4) . . ?
H6A C6 H6B 107.5 . . ?
C7 C6 H6A 108.5 . . ?
C7 C6 H6B 108.5 . . ?
O1 C7 O2 124.7(4) . . ?
O1 C7 C6 124.0(4) . . ?
O2 C7 C6 111.1(4) . . ?
O2 C8A C11A 98.4(9) . . ?
C9A C8A O2 113.2(10) . . ?
C9A C8A C10A 105.0(11) . . ?
C9A C8A C11A 125.6(11) . . ?
C10A C8A O2 106.0(9) . . ?
C10A C8A C11A 107.3(11) . . ?
O2 C8B C9B 105.0(11) . . ?
O2 C8B C10B 98.6(9) . . ?
C10B C8B C9B 119.8(13) . . ?
C11B C8B O2 121.2(11) . . ?
C11B C8B C9B 96.8(12) . . ?
C11B C8B C10B 116.4(13) . . ?
C8A C9A H9AA 109.5 . . ?
C8A C9A H9AB 109.5 . . ?
C8A C9A H9AC 109.5 . . ?
H9AA C9A H9AB 109.5 . . ?
H9AA C9A H9AC 109.5 . . ?
H9AB C9A H9AC 109.5 . . ?
C8A C10A H10A 109.5 . . ?
C8A C10A H10B 109.5 . . ?
C8A C10A H10C 109.5 . . ?
H10A C10A H10B 109.5 . . ?
H10A C10A H10C 109.5 . . ?
H10B C10A H10C 109.5 . . ?
C8A C11A H11A 109.5 . . ?
C8A C11A H11B 109.5 . . ?
C8A C11A H11C 109.5 . . ?
H11A C11A H11B 109.5 . . ?
H11A C11A H11C 109.5 . . ?
H11B C11A H11C 109.5 . . ?
N2 C12 H12A 108.4 . . ?
N2 C12 H12B 108.4 . . ?
N2 C12 C13 115.4(4) . . ?
H12A C12 H12B 107.5 . . ?
C13 C12 H12A 108.4 . . ?
C13 C12 H12B 108.4 . . ?
O3 C13 O4 124.1(4) . . ?
O3 C13 C12 126.9(4) . . ?
O4 C13 C12 109.0(4) . . ?
C15A C14A O4 100.3(8) . . ?
C15A C14A C16A 111.1(10) . . ?
C16A C14A O4 98.8(7) . . ?
C17A C14A O4 115.2(7) . . ?
C17A C14A C15A 118.5(10) . . ?
C17A C14A C16A 110.8(9) . . ?
O4 C14B C15B 116.9(10) . . ?
O4 C14B C16B 111.3(11) . . ?
O4 C14B C17B 101.9(11) . . ?
C16B C14B C15B 113.0(13) . . ?
C16B C14B C17B 108.7(12) . . ?
C17B C14B C15B 103.8(11) . . ?
C14B C15B H15D 109.5 . . ?
C14B C15B H15E 109.5 . . ?
C14B C15B H15F 109.5 . . ?
H15D C15B H15E 109.5 . . ?
H15D C15B H15F 109.5 . . ?
H15E C15B H15F 109.5 . . ?
C14B C16B H16D 109.5 . . ?
C14B C16B H16E 109.5 . . ?
C14B C16B H16F 109.5 . . ?
H16D C16B H16E 109.5 . . ?
H16D C16B H16F 109.5 . . ?
H16E C16B H16F 109.5 . . ?
C14B C17B H17D 109.5 . . ?
C14B C17B H17E 109.5 . . ?
C14B C17B H17F 109.5 . . ?
H17D C17B H17E 109.5 . . ?
H17D C17B H17F 109.5 . . ?
H17E C17B H17F 109.5 . . ?
C19 C18 C4 118.5(4) . . ?
C23 C18 C4 123.5(4) . . ?
C23 C18 C19 117.9(4) . . ?
C18 C19 H19 119.9 . . ?
C20 C19 C18 120.3(5) . . ?
C20 C19 H19 119.9 . . ?
C19 C20 H20 119.9 . . ?
C19 C20 C21 120.2(5) . . ?
C21 C20 H20 119.9 . . ?
C20 C21 H21 119.9 . . ?
C22 C21 C20 120.2(5) . . ?
C22 C21 H21 119.9 . . ?
C21 C22 H22 120.4 . . ?
C21 C22 C23 119.3(5) . . ?
C23 C22 H22 120.4 . . ?
C18 C23 C22 122.2(5) . . ?
C18 C23 H23 118.9 . . ?
C22 C23 H23 118.9 . . ?

data_23_12srv042
_database_code_depnum_ccdc_archive 'CCDC 911246'
#TrackingRef '15471_web_deposit_cif_file_1_DmitryYufit_1353069364.23.cif'
_audit_creation_date             2012-02-14
_audit_creation_method           
;
Olex2 1.1-beta
(compiled 2011.11.01 svn.r2039, GUI svn.r3906)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
tert-Butyl 2,2'-(6-hydroxy-6-phenyl-1,4-diazepane-1,4-diyl)diacetate
;
_chemical_formula_moiety         'C23 H36 N2 O5'
_chemical_formula_sum            'C23 H36 N2 O5'
_chemical_formula_weight         420.54
_chemical_melting_point          '88-97 C'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'
_cell_length_a                   5.7906(7)
_cell_length_b                   9.5843(11)
_cell_length_c                   20.978(2)
_cell_angle_alpha                81.025(10)
_cell_angle_beta                 87.158(10)
_cell_angle_gamma                85.460(10)
_cell_volume                     1145.6(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2758
_cell_measurement_temperature    120
_cell_measurement_theta_max      29.758
_cell_measurement_theta_min      2.229
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.5924
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2006/1 (Bruker,2006) was used for absorption correction.
R(int) was 0.0429 before and 0.0326 after correction.
The Ratio of minimum to maximum transmission is 0.5924.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.219
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prizm
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_exptl_special_details           
;
The data collection nominally covered a full sphere of reciprocal space by
a combination of 4 sets of \w scans each set at different \f and/or
2\q angles and each scan (20 s exposure) covering -0.300\% degrees in \w.
The crystal to detector distance was 4.424 cm.
;
_diffrn_reflns_av_R_equivalents  0.0595
_diffrn_reflns_av_unetI/netI     0.0959
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            13558
_diffrn_reflns_theta_full        28.50
_diffrn_reflns_theta_max         28.50
_diffrn_reflns_theta_min         1.97
_diffrn_ambient_temperature      120
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'Bruker SMART CCD 1K area detector'
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART CCD 1K area detector'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_current           10.0
_diffrn_source_power             0.3
_diffrn_source_target            Mo
_diffrn_source_voltage           30.0
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                3370
_reflns_number_total             5749
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'SAINT v6.45A (Bruker, 2003)'
_computing_data_collection       'SMART v5.049 (Bruker, 1999)'
_computing_data_reduction        'SAINT v6.45A (Bruker, 2003)'
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    
;
XS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         0.303
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.994
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     415
_refine_ls_number_reflns         5749
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1141
_refine_ls_R_factor_gt           0.0563
_refine_ls_restrained_S_all      0.994
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0600P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1154
_refine_ls_wR_factor_ref         0.1365
_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.
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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 0.1251(3) 0.68172(18) 0.42972(7) 0.0340(4) Uani 1 1 d . . .
O2 O 0.2317(2) 0.82267(15) 0.49845(6) 0.0192(3) Uani 1 1 d . . .
O3 O 0.1717(2) 0.74767(17) 0.09916(7) 0.0260(4) Uani 1 1 d . . .
O4 O 0.4817(2) 0.71717(15) 0.03177(6) 0.0194(3) Uani 1 1 d . . .
O5 O 0.0262(2) 0.92759(17) 0.19281(7) 0.0190(3) Uani 1 1 d . . .
N1 N 0.4126(3) 0.82678(18) 0.32928(8) 0.0170(4) Uani 1 1 d . . .
N2 N 0.4693(3) 0.73857(17) 0.20108(8) 0.0156(4) Uani 1 1 d . . .
C1 C 0.5148(4) 0.6855(2) 0.32124(10) 0.0189(5) Uani 1 1 d . . .
C2 C 0.6231(4) 0.6791(2) 0.25395(10) 0.0180(5) Uani 1 1 d . . .
C3 C 0.4449(3) 0.8947(2) 0.19428(10) 0.0153(4) Uani 1 1 d . . .
C4 C 0.2227(3) 0.9470(2) 0.22844(9) 0.0144(4) Uani 1 1 d . . .
C5 C 0.1923(3) 0.8600(2) 0.29652(10) 0.0168(4) Uani 1 1 d . . .
C6 C 0.4037(4) 0.8562(2) 0.39463(10) 0.0195(5) Uani 1 1 d . . .
C7 C 0.2361(4) 0.7741(2) 0.44169(10) 0.0202(5) Uani 1 1 d . . .
C8 C 0.0922(4) 0.7591(2) 0.55553(9) 0.0189(5) Uani 1 1 d . . .
C9 C 0.1380(4) 0.8520(3) 0.60505(11) 0.0239(5) Uani 1 1 d . . .
C10 C -0.1629(4) 0.7706(3) 0.54045(12) 0.0278(6) Uani 1 1 d . . .
C11 C 0.1861(4) 0.6076(2) 0.57602(12) 0.0257(5) Uani 1 1 d . . .
C12 C 0.5554(4) 0.6909(3) 0.14113(10) 0.0190(5) Uani 1 1 d . . .
C13 C 0.3772(4) 0.7232(2) 0.08946(10) 0.0181(5) Uani 1 1 d . . .
C14 C 0.3506(3) 0.7450(2) -0.02898(9) 0.0174(4) Uani 1 1 d . . .
C15 C 0.5409(4) 0.7312(3) -0.08013(11) 0.0289(6) Uani 1 1 d . . .
C16 C 0.1802(4) 0.6326(3) -0.02788(12) 0.0264(5) Uani 1 1 d . . .
C17 C 0.2345(5) 0.8934(3) -0.03641(13) 0.0287(6) Uani 1 1 d . . .
C18 C 0.2237(3) 1.1040(2) 0.23244(9) 0.0155(4) Uani 1 1 d . . .
C19 C 0.4008(4) 1.1562(2) 0.26260(10) 0.0186(5) Uani 1 1 d . . .
C20 C 0.4005(4) 1.2993(2) 0.26673(10) 0.0223(5) Uani 1 1 d . . .
C21 C 0.2238(4) 1.3939(3) 0.24066(10) 0.0245(5) Uani 1 1 d . . .
C22 C 0.0460(4) 1.3427(2) 0.21162(10) 0.0238(5) Uani 1 1 d . . .
C23 C 0.0449(4) 1.1997(2) 0.20777(10) 0.0203(5) Uani 1 1 d . . .
H1A H 0.641(4) 0.661(2) 0.3520(10) 0.018(5) Uiso 1 1 d . . .
H1B H 0.398(4) 0.614(2) 0.3305(10) 0.017(5) Uiso 1 1 d . . .
H2A H 0.767(4) 0.726(2) 0.2482(9) 0.012(5) Uiso 1 1 d . . .
H2B H 0.668(4) 0.577(2) 0.2501(10) 0.022(6) Uiso 1 1 d . . .
H3A H 0.580(4) 0.935(2) 0.2110(10) 0.017(5) Uiso 1 1 d . . .
H3B H 0.438(4) 0.936(2) 0.1469(11) 0.023(6) Uiso 1 1 d . . .
H5 H 0.067(5) 0.863(3) 0.1688(14) 0.052(9) Uiso 1 1 d . . .
H5A H 0.073(3) 0.918(2) 0.3235(10) 0.014(5) Uiso 1 1 d . . .
H5B H 0.121(3) 0.771(2) 0.2922(9) 0.013(5) Uiso 1 1 d . . .
H6A H 0.359(3) 0.956(2) 0.3954(9) 0.010(5) Uiso 1 1 d . . .
H6B H 0.553(4) 0.839(2) 0.4113(10) 0.026(6) Uiso 1 1 d . . .
H9A H 0.055(4) 0.826(2) 0.6460(12) 0.032(7) Uiso 1 1 d . . .
H9B H 0.299(5) 0.850(3) 0.6133(11) 0.035(7) Uiso 1 1 d . . .
H9C H 0.088(4) 0.950(3) 0.5883(12) 0.037(7) Uiso 1 1 d . . .
H10A H -0.213(4) 0.871(3) 0.5223(12) 0.038(7) Uiso 1 1 d . . .
H10B H -0.196(4) 0.704(3) 0.5078(12) 0.044(7) Uiso 1 1 d . . .
H10C H -0.246(4) 0.746(2) 0.5796(12) 0.027(6) Uiso 1 1 d . . .
H11A H 0.353(4) 0.601(2) 0.5837(11) 0.032(7) Uiso 1 1 d . . .
H11B H 0.108(4) 0.575(2) 0.6185(11) 0.022(6) Uiso 1 1 d . . .
H11C H 0.156(4) 0.542(2) 0.5421(11) 0.029(6) Uiso 1 1 d . . .
H12A H 0.588(4) 0.582(2) 0.1488(10) 0.024(6) Uiso 1 1 d . . .
H12B H 0.704(4) 0.732(2) 0.1242(11) 0.029(6) Uiso 1 1 d . . .
H15A H 0.614(4) 0.637(3) -0.0740(12) 0.039(7) Uiso 1 1 d . . .
H15B H 0.469(4) 0.751(3) -0.1229(13) 0.045(8) Uiso 1 1 d . . .
H15C H 0.648(5) 0.801(3) -0.0771(12) 0.045(8) Uiso 1 1 d . . .
H16A H 0.265(4) 0.539(3) -0.0223(11) 0.038(7) Uiso 1 1 d . . .
H16B H 0.113(4) 0.646(2) -0.0724(11) 0.028(6) Uiso 1 1 d . . .
H16C H 0.059(4) 0.640(2) 0.0046(12) 0.032(7) Uiso 1 1 d . . .
H17A H 0.168(4) 0.914(2) -0.0776(12) 0.027(6) Uiso 1 1 d . . .
H17B H 0.112(5) 0.905(3) -0.0030(14) 0.051(8) Uiso 1 1 d . . .
H17C H 0.345(4) 0.965(3) -0.0306(11) 0.036(7) Uiso 1 1 d . . .
H19 H 0.525(4) 1.091(2) 0.2816(10) 0.019(6) Uiso 1 1 d . . .
H20 H 0.522(4) 1.332(2) 0.2877(10) 0.014(5) Uiso 1 1 d . . .
H21 H 0.226(4) 1.493(3) 0.2441(10) 0.024(6) Uiso 1 1 d . . .
H22 H -0.071(4) 1.406(2) 0.1927(10) 0.022(6) Uiso 1 1 d . . .
H23 H -0.076(4) 1.160(2) 0.1879(10) 0.025(6) Uiso 1 1 d . . .
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 0.0504(11) 0.0349(10) 0.0214(8) -0.0091(7) 0.0040(7) -0.0253(8)
O2 0.0243(8) 0.0196(8) 0.0136(7) -0.0005(6) 0.0003(6) -0.0051(6)
O3 0.0171(8) 0.0437(11) 0.0198(8) -0.0140(7) 0.0001(6) -0.0009(7)
O4 0.0183(7) 0.0258(9) 0.0137(7) -0.0032(6) -0.0009(6) 0.0010(6)
O5 0.0149(7) 0.0245(9) 0.0193(8) -0.0078(7) -0.0044(6) -0.0017(6)
N1 0.0204(9) 0.0187(10) 0.0121(8) -0.0029(7) -0.0017(7) 0.0003(7)
N2 0.0174(9) 0.0157(9) 0.0139(8) -0.0047(7) -0.0017(7) 0.0023(7)
C1 0.0245(11) 0.0157(11) 0.0162(11) -0.0015(9) -0.0052(9) 0.0009(9)
C2 0.0198(11) 0.0164(12) 0.0180(11) -0.0024(9) -0.0042(8) -0.0003(9)
C3 0.0161(10) 0.0179(11) 0.0124(10) -0.0018(8) -0.0009(8) -0.0049(8)
C4 0.0148(10) 0.0153(11) 0.0137(10) -0.0025(8) -0.0037(8) -0.0021(8)
C5 0.0172(10) 0.0180(12) 0.0155(10) -0.0031(9) -0.0003(8) -0.0027(9)
C6 0.0250(12) 0.0183(12) 0.0166(11) -0.0037(9) -0.0025(9) -0.0070(9)
C7 0.0262(11) 0.0211(12) 0.0138(10) -0.0042(9) -0.0016(8) -0.0016(9)
C8 0.0226(11) 0.0197(12) 0.0133(10) 0.0014(8) 0.0000(8) -0.0036(9)
C9 0.0283(13) 0.0284(14) 0.0148(11) -0.0030(10) 0.0007(9) -0.0026(11)
C10 0.0243(12) 0.0363(16) 0.0217(12) 0.0010(11) -0.0012(10) -0.0060(11)
C11 0.0299(14) 0.0222(13) 0.0229(12) 0.0031(10) -0.0010(10) -0.0018(10)
C12 0.0161(10) 0.0247(13) 0.0167(11) -0.0062(9) 0.0006(8) 0.0012(9)
C13 0.0200(11) 0.0174(11) 0.0179(11) -0.0052(9) 0.0012(8) -0.0033(9)
C14 0.0182(10) 0.0232(12) 0.0106(10) -0.0034(8) -0.0034(8) 0.0028(9)
C15 0.0278(13) 0.0412(17) 0.0161(12) -0.0023(11) 0.0006(10) 0.0023(12)
C16 0.0295(13) 0.0293(15) 0.0212(13) -0.0045(10) -0.0033(10) -0.0045(11)
C17 0.0383(15) 0.0216(13) 0.0256(13) -0.0042(10) -0.0073(12) 0.0061(11)
C18 0.0175(10) 0.0188(11) 0.0095(9) -0.0020(8) 0.0035(8) -0.0010(8)
C19 0.0201(11) 0.0189(12) 0.0161(10) -0.0014(9) -0.0007(8) -0.0007(9)
C20 0.0261(12) 0.0227(13) 0.0191(11) -0.0036(9) -0.0034(9) -0.0054(10)
C21 0.0346(13) 0.0163(12) 0.0229(12) -0.0043(10) -0.0001(10) -0.0017(10)
C22 0.0276(12) 0.0218(13) 0.0207(12) -0.0034(10) -0.0019(10) 0.0073(10)
C23 0.0188(11) 0.0270(13) 0.0155(11) -0.0062(9) 0.0011(8) 0.0010(9)
_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 C7 1.198(3) . ?
O2 C7 1.343(2) . ?
O2 C8 1.487(2) . ?
O3 C13 1.208(2) . ?
O4 C13 1.333(2) . ?
O4 C14 1.493(2) . ?
O5 C4 1.431(2) . ?
O5 H5 0.87(3) . ?
N1 C1 1.465(3) . ?
N1 C5 1.468(3) . ?
N1 C6 1.440(3) . ?
N2 C2 1.472(2) . ?
N2 C3 1.477(3) . ?
N2 C12 1.456(3) . ?
C1 C2 1.524(3) . ?
C1 H1A 0.99(2) . ?
C1 H1B 0.99(2) . ?
C2 H2A 0.97(2) . ?
C2 H2B 1.01(2) . ?
C3 C4 1.529(3) . ?
C3 H3A 1.00(2) . ?
C3 H3B 1.01(2) . ?
C4 C5 1.547(3) . ?
C4 C18 1.521(3) . ?
C5 H5A 1.05(2) . ?
C5 H5B 0.99(2) . ?
C6 C7 1.523(3) . ?
C6 H6A 0.97(2) . ?
C6 H6B 0.94(2) . ?
C8 C9 1.516(3) . ?
C8 C10 1.518(3) . ?
C8 C11 1.514(3) . ?
C9 H9A 0.97(2) . ?
C9 H9B 0.95(3) . ?
C9 H9C 0.97(3) . ?
C10 H10A 1.01(3) . ?
C10 H10B 1.04(3) . ?
C10 H10C 0.94(2) . ?
C11 H11A 0.98(2) . ?
C11 H11B 0.99(2) . ?
C11 H11C 1.05(2) . ?
C12 C13 1.514(3) . ?
C12 H12A 1.04(2) . ?
C12 H12B 1.00(2) . ?
C14 C15 1.512(3) . ?
C14 C16 1.515(3) . ?
C14 C17 1.512(3) . ?
C15 H15A 0.96(3) . ?
C15 H15B 0.99(3) . ?
C15 H15C 0.96(3) . ?
C16 H16A 0.99(3) . ?
C16 H16B 1.02(2) . ?
C16 H16C 0.96(3) . ?
C17 H17A 0.95(2) . ?
C17 H17B 0.98(3) . ?
C17 H17C 1.00(3) . ?
C18 C19 1.395(3) . ?
C18 C23 1.391(3) . ?
C19 C20 1.388(3) . ?
C19 H19 0.97(2) . ?
C20 C21 1.386(3) . ?
C20 H20 0.95(2) . ?
C21 C22 1.381(3) . ?
C21 H21 0.96(2) . ?
C22 C23 1.386(3) . ?
C22 H22 0.94(2) . ?
C23 H23 0.96(2) . ?
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
C7 O2 C8 122.02(16) . . ?
C13 O4 C14 121.92(15) . . ?
C4 O5 H5 107.7(18) . . ?
C1 N1 C5 111.59(16) . . ?
C6 N1 C1 114.70(16) . . ?
C6 N1 C5 114.10(17) . . ?
C2 N2 C3 110.66(16) . . ?
C12 N2 C2 110.20(16) . . ?
C12 N2 C3 111.52(16) . . ?
N1 C1 C2 113.08(17) . . ?
N1 C1 H1A 107.6(12) . . ?
N1 C1 H1B 111.2(12) . . ?
C2 C1 H1A 106.9(12) . . ?
C2 C1 H1B 108.6(12) . . ?
H1A C1 H1B 109.3(16) . . ?
N2 C2 C1 114.16(17) . . ?
N2 C2 H2A 109.3(11) . . ?
N2 C2 H2B 108.3(12) . . ?
C1 C2 H2A 110.5(11) . . ?
C1 C2 H2B 108.3(12) . . ?
H2A C2 H2B 105.8(17) . . ?
N2 C3 C4 111.59(16) . . ?
N2 C3 H3A 112.6(12) . . ?
N2 C3 H3B 109.3(12) . . ?
C4 C3 H3A 109.0(12) . . ?
C4 C3 H3B 107.9(12) . . ?
H3A C3 H3B 106.2(17) . . ?
O5 C4 C3 109.70(16) . . ?
O5 C4 C5 107.16(15) . . ?
O5 C4 C18 107.85(15) . . ?
C3 C4 C5 110.59(16) . . ?
C18 C4 C3 110.71(16) . . ?
C18 C4 C5 110.73(16) . . ?
N1 C5 C4 112.44(16) . . ?
N1 C5 H5A 110.8(11) . . ?
N1 C5 H5B 110.2(11) . . ?
C4 C5 H5A 107.9(11) . . ?
C4 C5 H5B 108.4(11) . . ?
H5A C5 H5B 106.9(16) . . ?
N1 C6 C7 116.25(17) . . ?
N1 C6 H6A 110.2(11) . . ?
N1 C6 H6B 109.3(14) . . ?
C7 C6 H6A 106.0(12) . . ?
C7 C6 H6B 108.2(14) . . ?
H6A C6 H6B 106.4(18) . . ?
O1 C7 O2 125.61(19) . . ?
O1 C7 C6 125.34(19) . . ?
O2 C7 C6 109.05(17) . . ?
O2 C8 C9 101.73(16) . . ?
O2 C8 C10 110.39(16) . . ?
O2 C8 C11 108.92(17) . . ?
C9 C8 C10 111.2(2) . . ?
C11 C8 C9 111.38(18) . . ?
C11 C8 C10 112.70(19) . . ?
C8 C9 H9A 112.6(14) . . ?
C8 C9 H9B 112.3(15) . . ?
C8 C9 H9C 108.8(14) . . ?
H9A C9 H9B 107.9(19) . . ?
H9A C9 H9C 108(2) . . ?
H9B C9 H9C 107(2) . . ?
C8 C10 H10A 109.8(14) . . ?
C8 C10 H10B 111.2(14) . . ?
C8 C10 H10C 107.1(13) . . ?
H10A C10 H10B 109.8(19) . . ?
H10A C10 H10C 108(2) . . ?
H10B C10 H10C 111(2) . . ?
C8 C11 H11A 111.9(14) . . ?
C8 C11 H11B 106.2(13) . . ?
C8 C11 H11C 112.2(12) . . ?
H11A C11 H11B 106.0(18) . . ?
H11A C11 H11C 109.2(19) . . ?
H11B C11 H11C 111.2(18) . . ?
N2 C12 C13 111.58(17) . . ?
N2 C12 H12A 109.6(12) . . ?
N2 C12 H12B 113.0(13) . . ?
C13 C12 H12A 106.1(12) . . ?
C13 C12 H12B 109.4(13) . . ?
H12A C12 H12B 106.7(18) . . ?
O3 C13 O4 125.35(18) . . ?
O3 C13 C12 125.25(19) . . ?
O4 C13 C12 109.39(17) . . ?
O4 C14 C15 102.26(16) . . ?
O4 C14 C16 109.43(16) . . ?
O4 C14 C17 109.34(17) . . ?
C15 C14 C16 111.0(2) . . ?
C15 C14 C17 111.5(2) . . ?
C17 C14 C16 112.8(2) . . ?
C14 C15 H15A 110.0(15) . . ?
C14 C15 H15B 107.7(15) . . ?
C14 C15 H15C 107.5(16) . . ?
H15A C15 H15B 109(2) . . ?
H15A C15 H15C 112(2) . . ?
H15B C15 H15C 110(2) . . ?
C14 C16 H16A 109.0(14) . . ?
C14 C16 H16B 106.9(13) . . ?
C14 C16 H16C 111.6(14) . . ?
H16A C16 H16B 106.3(19) . . ?
H16A C16 H16C 112(2) . . ?
H16B C16 H16C 110.3(19) . . ?
C14 C17 H17A 108.7(14) . . ?
C14 C17 H17B 112.9(16) . . ?
C14 C17 H17C 112.0(14) . . ?
H17A C17 H17B 109(2) . . ?
H17A C17 H17C 111.2(19) . . ?
H17B C17 H17C 103(2) . . ?
C19 C18 C4 121.02(17) . . ?
C23 C18 C4 121.12(18) . . ?
C23 C18 C19 117.8(2) . . ?
C18 C19 H19 119.5(12) . . ?
C20 C19 C18 121.0(2) . . ?
C20 C19 H19 119.5(13) . . ?
C19 C20 H20 119.4(12) . . ?
C21 C20 C19 120.5(2) . . ?
C21 C20 H20 120.1(12) . . ?
C20 C21 H21 119.5(13) . . ?
C22 C21 C20 118.8(2) . . ?
C22 C21 H21 121.7(13) . . ?
C21 C22 C23 120.8(2) . . ?
C21 C22 H22 119.3(13) . . ?
C23 C22 H22 119.9(13) . . ?
C18 C23 H23 115.9(14) . . ?
C22 C23 C18 121.0(2) . . ?
C22 C23 H23 123.1(14) . . ?
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
O5 H5 O3 0.87(3) 2.01(3) 2.865(2) 168(3) .