#------------------------------------------------------------------------------
#$Date: 2016-03-26 17:11:47 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180380 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/49/7204983.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7204983
loop_
_publ_author_name
'Linder, Michael R.'
'Frey, Wolfgang U.'
'Podlech, Joachim'
_publ_contact_author             'Joachim Podlech'
_publ_section_title
;
 Diazoketones as precursors in Î²-lactam synthesis. New
 insights into the mechanism of the photochemically induced Staudinger
 reaction
;
_journal_issue                   20
_journal_name_full
'Journal of the Chemical Society, Perkin Transactions 1'
_journal_page_first              2566
_journal_paper_doi               10.1039/b105748k
_journal_year                    2001
_chemical_formula_sum            'C24 H24 N2 O3 S'
_chemical_formula_weight         420.51
_chemical_melting_point          378.5(5)
_chemical_name_systematic
; 
(3S,4R,1'S)-1-Benzyl-3-[1-(benzyloxycarbonylamino)ethyl]-4-(2-thienyl)-
azetidin-2-one 
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 90.117(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.2101(5)
_cell_length_b                   20.7429(10)
_cell_length_c                   11.5524(6)
_cell_measurement_reflns_used    50
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      50
_cell_measurement_theta_min      22.5
_cell_volume                     2207.0(2)
_computing_cell_refinement       'SIEMENS XSCANS'
_computing_data_collection       'Siemens XSCANS'
_computing_data_reduction        'Siemens XSCANS and XEMP'
_computing_molecular_graphics    'SHELXTL - XP'
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_device       'Siemens P4'
_diffrn_measurement_method       'Omega Scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0388
_diffrn_reflns_av_sigmaI/netI    0.0375
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7539
_diffrn_reflns_theta_max         68.00
_diffrn_reflns_theta_min         3.83
_diffrn_standards_interval_count 100
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    1.523
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_correction_T_min  0.526
_exptl_absorpt_correction_type   psi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.266
_exptl_crystal_description       plates
_exptl_crystal_F_000             888
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.248
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.05(4)
_refine_ls_extinction_coef       0.0075(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_all   1.169
_refine_ls_goodness_of_fit_obs   1.206
_refine_ls_matrix_type           full
_refine_ls_number_parameters     616
_refine_ls_number_reflns         6660
_refine_ls_number_restraints     317
_refine_ls_restrained_S_all      1.263
_refine_ls_restrained_S_obs      1.192
_refine_ls_R_factor_all          0.0944
_refine_ls_R_factor_obs          0.0790
_refine_ls_shift/esd_max         -0.033
_refine_ls_shift/esd_mean        0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1483P)²+0.5129P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.2715
_refine_ls_wR_factor_obs         0.2244
_reflns_number_observed          5301
_reflns_number_total             6870
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            b105748k.txt
_cod_data_source_block           s549rc2
_cod_depositor_comments
;
The following automatic conversions were performed:
'_exptl_absorpt_correction_type' value 'Psi- Scan' changed to 'psi-scan'
according to '/home/adriana/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1555 2011-01-17 13:19:09Z saulius 

The following automatic conversions were performed:

'_chemical_melting_point' value '378 - 379 K' was changed to
'378.5(5)' - the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1569 2011-02-09 13:29:24Z adriana 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.1483P)^2^+0.5129P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to
'w=1/[\s^2^(Fo^2^)+(0.1483P)^2^+0.5129P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_sg_symbol_H-M      P2(1)
_cod_database_code               7204983
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
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_thermal_displace_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_group
N1A N 0.8360(2) 0.32185(8) 0.34684(15) 0.0713(5) Uani 1 d . .
O1A O 1.0367(2) 0.33680(8) 0.46688(13) 0.0860(5) Uani 1 d . .
C1A C 0.9426(2) 0.30421(10) 0.4213(2) 0.0653(6) Uani 1 d . .
N2A N 0.7679(2) 0.24932(8) 0.60906(13) 0.0631(4) Uani 1 d . .
H2A H 0.6779 0.25633 0.59328 0.076 Uiso 1 calc R .
O2A O 0.95584(14) 0.27701(8) 0.72729(13) 0.0799(5) Uani 1 d . .
C2A C 0.8926(2) 0.23421(9) 0.4230(2) 0.0594(5) Uani 1 d . .
H2A1 H 0.9619 0.20690 0.3814 0.071 Uiso 1 calc R .
O3A O 0.73313(15) 0.32020(7) 0.74778(12) 0.0760(4) Uani 1 d . .
C3A C 0.7700(2) 0.25656(9) 0.3405(2) 0.0647(5) Uani 1 d . .
H3A H 0.6748 0.25520 0.3782 0.078 Uiso 1 calc R .
C4A C 0.8506(2) 0.20302(9) 0.5383(2) 0.0608(5) Uani 1 d . .
H4A H 0.9402 0.19237 0.5801 0.073 Uiso 1 calc R .
C5A C 0.7647(2) 0.14176(10) 0.5228(2) 0.0767(7) Uani 1 d . .
H5A1 H 0.7411 0.12416 0.5973 0.115 Uiso 1 calc R .
H5A2 H 0.8214 0.11112 0.4801 0.115 Uiso 1 calc R .
H5A3 H 0.6768 0.15099 0.4812 0.115 Uiso 1 calc R .
C6A C 0.8299(2) 0.28048(10) 0.6969(2) 0.0636(5) Uani 1 d . .
C7A C 0.7893(3) 0.36150(13) 0.8386(2) 0.0978(8) Uani 1 d . .
H7A1 H 0.8743 0.38455 0.8115 0.117 Uiso 1 calc R .
H7A2 H 0.8167 0.33594 0.9054 0.117 Uiso 1 calc R .
C8A C 0.6727(3) 0.40773(12) 0.8700(2) 0.0850(7) Uani 1 d . .
C9A C 0.6001(3) 0.4024(2) 0.9721(2) 0.1188(10) Uani 1 d . .
H9A H 0.6252 0.3703 1.0247 0.143 Uiso 1 calc R .
C10A C 0.4867(4) 0.4456(2) 0.9975(3) 0.1495(11) Uani 1 d U .
H10A H 0.4338 0.4408 1.0654 0.179 Uiso 1 calc R .
C11A C 0.4553(4) 0.4931(2) 0.9250(4) 0.1730(14) Uani 1 d . .
H11A H 0.3830 0.5227 0.9437 0.208 Uiso 1 calc R .
C12A C 0.5271(4) 0.4988(2) 0.8249(5) 0.152(2) Uani 1 d . .
H12A H 0.5017 0.5314 0.7733 0.182 Uiso 1 calc R .
C13A C 0.6381(4) 0.45712(14) 0.7970(3) 0.1115(11) Uani 1 d . .
H13A H 0.6895 0.46265 0.7285 0.134 Uiso 1 calc R .
C14A C 0.8012(3) 0.38198(11) 0.2939(2) 0.0832(7) Uani 1 d . .
H14A H 0.7850 0.37440 0.2120 0.100 Uiso 1 calc R .
H14B H 0.8851 0.40999 0.3007 0.100 Uiso 1 calc R .
C15A C 0.6716(3) 0.41740(9) 0.3408(2) 0.0725(6) Uani 1 d . .
C16A C 0.6062(4) 0.39827(14) 0.4389(3) 0.1316(11) Uani 1 d . .
H16A H 0.6360 0.36072 0.4760 0.158 Uiso 1 calc R .
C17A C 0.4936(5) 0.4351(2) 0.4846(3) 0.1589(12) Uani 1 d . .
H17A H 0.4583 0.4262 0.5583 0.191 Uiso 1 calc R .
C18A C 0.4331(4) 0.48580(14) 0.4191(3) 0.1381(12) Uani 1 d . .
H18A H 0.3439 0.50362 0.4388 0.166 Uiso 1 calc R .
C19A C 0.5065(4) 0.50734(13) 0.3289(3) 0.1066(10) Uani 1 d . .
H19A H 0.4796 0.54582 0.2935 0.128 Uiso 1 calc R .
C20A C 0.6239(3) 0.47237(11) 0.2869(2) 0.0872(8) Uani 1 d . .
H20A H 0.6713 0.48661 0.2206 0.105 Uiso 1 calc R .
C21A C 0.76528(4) 0.22809(3) 0.22308(5) 0.0743(6) Uani 1 d D .
S1A S 0.65119(6) 0.16787(3) 0.18247(5) 0.1093(3) Uani 0.6870(13) d PDU 1
C22A C 0.84633(9) 0.24493(3) 0.12745(5) 0.0962(11) Uani 0.6870(13) d PDU 1
H22A H 0.89869 0.28326 0.12612 0.115 Uiso 0.6870(13) calc PR 1
C23A C 0.84801(8) 0.20363(3) 0.03378(5) 0.120(2) Uani 0.6870(13) d PDU 1
H23A H 0.91455 0.20273 -0.02664 0.144 Uiso 0.6870(13) calc PR 1
C24A C 0.72938(8) 0.16395(4) 0.04937(5) 0.0996(12) Uani 0.6870(13) d PDU 1
H24A H 0.69465 0.13699 -0.00874 0.120 Uiso 0.6870(13) calc PR 1
S1C S 0.89743(6) 0.23819(4) 0.12244(6) 0.1029(8) Uani 0.3130(13) d PDU 2
C22C C 0.65015(7) 0.19761(4) 0.16933(5) 0.066(2) Uani 0.3130(13) d PDU 2
H22C H 0.55856 0.19719 0.20306 0.079 Uiso 0.3130(13) calc PR 2
C23C C 0.67438(7) 0.16778(5) 0.06429(5) 0.101(2) Uani 0.3130(13) d PDU 2
H23C H 0.61761 0.13638 0.02878 0.121 Uiso 0.3130(13) calc PR 2
C24C C 0.80136(7) 0.19479(5) 0.02357(5) 0.084(2) Uani 0.3130(13) d PDU 2
H24C H 0.83219 0.18964 -0.05248 0.101 Uiso 0.3130(13) calc PR 2
N1B N 0.3410(2) 0.18771(8) -0.0980(2) 0.0715(5) Uani 1 d . .
C1B C 0.4463(2) 0.20491(10) -0.1737(2) 0.0654(5) Uani 1 d . .
O1B O 0.5413(2) 0.17397(8) -0.21790(14) 0.0825(5) Uani 1 d . .
N2B N 0.26916(15) 0.25662(7) -0.36354(13) 0.0599(4) Uani 1 d . .
H2B H 0.17885 0.25025 -0.34862 0.072 Uiso 1 calc R .
O2B O 0.45680(14) 0.22830(8) -0.48140(13) 0.0759(4) Uani 1 d . .
C2B C 0.3912(2) 0.27453(9) -0.1768(2) 0.0588(5) Uani 1 d . .
H2B1 H 0.4572 0.30330 -0.1348 0.071 Uiso 1 calc R .
O3B O 0.23507(14) 0.18261(7) -0.49929(12) 0.0736(4) Uani 1 d . .
C3B C 0.2678(2) 0.25048(10) -0.0970(2) 0.0648(5) Uani 1 d . .
H3B H 0.1742 0.24897 -0.1375 0.078 Uiso 1 calc R .
C4B C 0.3505(2) 0.30297(9) -0.2952(2) 0.0576(5) Uani 1 d . .
H4B H 0.4403 0.31335 -0.3366 0.069 Uiso 1 calc R .
C5B C 0.2633(2) 0.36483(9) -0.2804(2) 0.0710(6) Uani 1 d . .
H5B1 H 0.2388 0.38194 -0.3552 0.107 Uiso 1 calc R .
H5B2 H 0.3202 0.39583 -0.2385 0.107 Uiso 1 calc R .
H5B3 H 0.1759 0.35571 -0.2383 0.107 Uiso 1 calc R .
C6B C 0.3322(2) 0.22364(10) -0.4493(2) 0.0632(5) Uani 1 d . .
C7B C 0.2961(3) 0.13994(13) -0.5840(2) 0.0969(8) Uani 1 d . .
H7B1 H 0.3785 0.11703 -0.5515 0.116 Uiso 1 calc R .
H7B2 H 0.3287 0.16415 -0.6508 0.116 Uiso 1 calc R .
C8B C 0.1793(2) 0.09331(11) -0.6184(2) 0.0718(6) Uani 1 d . .
C9B C 0.1484(3) 0.03827(14) -0.5526(3) 0.1021(9) Uani 1 d . .
H9B H 0.2020 0.02892 -0.4864 0.122 Uiso 1 calc R .
C10B C 0.0329(4) -0.00339(13) -0.5889(3) 0.1171(11) Uani 1 d . .
H10B H 0.0109 -0.04066 -0.5477 0.141 Uiso 1 calc R .
C11B C -0.0424(4) 0.01283(15) -0.6835(3) 0.1108(10) Uani 1 d . .
H11B H -0.1185 -0.01381 -0.7061 0.133 Uiso 1 calc R .
C12B C -0.0150(3) 0.0645(2) -0.7470(3) 0.1066(10) Uani 1 d . .
H12B H -0.0712 0.0740 -0.8118 0.128 Uiso 1 calc R .
C13B C 0.0967(3) 0.10350(11) -0.7155(2) 0.0771(7) Uani 1 d . .
H13B H 0.1182 0.13881 -0.7620 0.093 Uiso 1 calc R .
C14B C 0.3086(3) 0.12463(11) -0.0492(2) 0.0862(8) Uani 1 d . .
H14C H 0.2991 0.12912 0.0340 0.103 Uiso 1 calc R .
H14D H 0.3905 0.09635 -0.0636 0.103 Uiso 1 calc R .
C15B C 0.1729(3) 0.09275(10) -0.0956(2) 0.0724(6) Uani 1 d . .
C16B C 0.1206(3) 0.10644(13) -0.2029(3) 0.1026(9) Uani 1 d . .
H16B H 0.1669 0.13740 -0.2478 0.123 Uiso 1 calc R .
C17B C -0.0015(4) 0.0749(2) -0.2468(3) 0.1356(12) Uani 1 d . .
H17B H -0.0351 0.0836 -0.3212 0.163 Uiso 1 calc R .
C18B C -0.0720(4) 0.0299(2) -0.1767(4) 0.1339(13) Uani 1 d . .
H18B H -0.1580 0.0108 -0.2014 0.161 Uiso 1 calc R .
C19B C -0.0126(4) 0.0137(2) -0.0692(3) 0.1209(11) Uani 1 d . .
H19B H -0.0546 -0.0185 -0.0242 0.145 Uiso 1 calc R .
C20B C 0.1084(3) 0.04564(12) -0.0309(2) 0.0964(9) Uani 1 d . .
H20B H 0.1477 0.03504 0.0408 0.116 Uiso 1 calc R .
C21B C 0.25464(5) 0.28096(2) 0.02016(5) 0.0737(6) Uani 1 d D .
S1B S 0.15229(7) 0.34807(3) 0.04088(4) 0.0959(3) Uani 0.6781(14) d PDU 3
C22B C 0.31030(11) 0.26210(3) 0.12478(4) 0.0973(12) Uani 0.6781(14) d PDU 3
H22B H 0.36193 0.22375 0.13148 0.117 Uiso 0.6781(14) calc PR 3
C23B C 0.28870(10) 0.30064(3) 0.21935(5) 0.132(2) Uani 0.6781(14) d PDU 3
H23B H 0.32519 0.29433 0.29361 0.159 Uiso 0.6781(14) calc PR 3
C24B C 0.20253(10) 0.35035(3) 0.18252(5) 0.1105(12) Uani 0.6781(14) d PDU 3
H24B H 0.17330 0.38330 0.23185 0.133 Uiso 0.6781(14) calc PR 3
S1D S 0.37380(7) 0.26809(4) 0.13014(6) 0.1207(9) Uani 0.3219(14) d PDU 4
C22D C 0.15355(8) 0.32497(4) 0.05597(5) 0.119(3) Uani 0.3219(14) d PDU 4
H22D H 0.07465 0.33527 0.00913 0.142 Uiso 0.3219(14) calc PR 4
C23D C 0.17056(8) 0.35358(4) 0.16191(5) 0.117(3) Uani 0.3219(14) d PDU 4
H23D H 0.11518 0.38690 0.19267 0.141 Uiso 0.3219(14) calc PR 4
C24D C 0.28569(8) 0.32314(4) 0.21337(5) 0.097(2) Uani 0.3219(14) d PDU 4
H24D H 0.31392 0.33201 0.28905 0.117 Uiso 0.3219(14) calc PR 4
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1A N1A C14A 132.2(2) . . ?
C1A N1A C3A 94.62(15) . . ?
C14A N1A C3A 133.2(2) . . ?
O1A C1A N1A 129.7(2) . . ?
O1A C1A C2A 137.6(2) . . ?
N1A C1A C2A 92.69(15) . . ?
C6A N2A C4A 121.16(15) . . ?
C6A N2A H2A 119.42 . . ?
C4A N2A H2A 119.42 . . ?
C1A C2A C4A 119.4(2) . . ?
C1A C2A C3A 85.80(14) . . ?
C4A C2A C3A 118.5(2) . . ?
C1A C2A H2A1 110.34 . . ?
C4A C2A H2A1 110.34 . . ?
C3A C2A H2A1 110.34 . . ?
C6A O3A C7A 116.2(2) . . ?
C21A C3A N1A 114.82(15) . . ?
C21A C3A C2A 117.71(14) . . ?
N1A C3A C2A 86.86(14) . . ?
C21A C3A H3A 111.75 . . ?
N1A C3A H3A 111.75 . . ?
C2A C3A H3A 111.75 . . ?
N2A C4A C5A 110.1(2) . . ?
N2A C4A C2A 109.80(15) . . ?
C5A C4A C2A 112.7(2) . . ?
N2A C4A H4A 108.04 . . ?
C5A C4A H4A 108.04 . . ?
C2A C4A H4A 108.04 . . ?
C4A C5A H5A1 109.47 . . ?
C4A C5A H5A2 109.47 . . ?
H5A1 C5A H5A2 109.5 . . ?
C4A C5A H5A3 109.47 . . ?
H5A1 C5A H5A3 109.5 . . ?
H5A2 C5A H5A3 109.5 . . ?
O2A C6A N2A 126.9(2) . . ?
O2A C6A O3A 122.8(2) . . ?
N2A C6A O3A 110.2(2) . . ?
O3A C7A C8A 107.6(2) . . ?
O3A C7A H7A1 110.20 . . ?
C8A C7A H7A1 110.20 . . ?
O3A C7A H7A2 110.20 . . ?
C8A C7A H7A2 110.20 . . ?
H7A1 C7A H7A2 108.5 . . ?
C9A C8A C13A 118.8(3) . . ?
C9A C8A C7A 121.1(3) . . ?
C13A C8A C7A 120.1(2) . . ?
C8A C9A C10A 119.6(3) . . ?
C8A C9A H9A 120.2 . . ?
C10A C9A H9A 120.2 . . ?
C11A C10A C9A 120.2(3) . . ?
C11A C10A H10A 119.9 . . ?
C9A C10A H10A 119.9 . . ?
C10A C11A C12A 120.2(4) . . ?
C10A C11A H11A 119.9 . . ?
C12A C11A H11A 119.9 . . ?
C11A C12A C13A 121.0(4) . . ?
C11A C12A H12A 119.5 . . ?
C13A C12A H12A 119.5 . . ?
C8A C13A C12A 120.0(3) . . ?
C8A C13A H13A 120.0 . . ?
C12A C13A H13A 120.0 . . ?
N1A C14A C15A 116.8(2) . . ?
N1A C14A H14A 108.10 . . ?
C15A C14A H14A 108.10 . . ?
N1A C14A H14B 108.10 . . ?
C15A C14A H14B 108.10 . . ?
H14A C14A H14B 107.3 . . ?
C16A C15A C20A 119.0(2) . . ?
C16A C15A C14A 121.1(2) . . ?
C20A C15A C14A 119.7(2) . . ?
C15A C16A C17A 119.5(3) . . ?
C15A C16A H16A 120.2 . . ?
C17A C16A H16A 120.2 . . ?
C16A C17A C18A 120.0(3) . . ?
C16A C17A H17A 120.0 . . ?
C18A C17A H17A 120.0 . . ?
C19A C18A C17A 118.3(3) . . ?
C19A C18A H18A 120.9 . . ?
C17A C18A H18A 120.9 . . ?
C18A C19A C20A 119.9(3) . . ?
C18A C19A H19A 120.1 . . ?
C20A C19A H19A 120.1 . . ?
C15A C20A C19A 121.6(2) . . ?
C15A C20A H20A 119.20 . . ?
C19A C20A H20A 119.2 . . ?
C22A C21A C3A 128.17(9) . . ?
C22C C21A C3A 128.02(8) . . ?
C22A C21A S1A 107.49(5) . . ?
C3A C21A S1A 124.32(8) . . ?
C22C C21A S1C 107.42(5) . . ?
C3A C21A S1C 123.96(8) . . ?
C21A S1A C24A 91.26(4) . . ?
C21A C22A C23A 118.53(6) . . ?
C21A C22A H22A 120.74 . . ?
C23A C22A H22A 120.74 . . ?
C24A C23A C22A 104.94(6) . . ?
C24A C23A H23A 127.53 . . ?
C22A C23A H23A 127.53 . . ?
C23A C24A S1A 115.23(5) . . ?
C23A C24A H24A 122.39 . . ?
S1A C24A H24A 122.39 . . ?
C21A S1C C24C 91.26(4) . . ?
C23C C22C C21A 118.37(6) . . ?
C23C C22C H22C 120.82 . . ?
C21A C22C H22C 120.82 . . ?
C24C C23C C22C 104.84(6) . . ?
C24C C23C H23C 127.58 . . ?
C22C C23C H23C 127.58 . . ?
C23C C24C S1C 115.20(5) . . ?
C23C C24C H24C 122.40 . . ?
S1C C24C H24C 122.40 . . ?
C1B N1B C14B 129.4(2) . . ?
C1B N1B C3B 95.8(2) . . ?
C14B N1B C3B 134.4(2) . . ?
O1B C1B N1B 131.1(2) . . ?
O1B C1B C2B 137.4(2) . . ?
N1B C1B C2B 91.48(15) . . ?
C6B N2B C4B 121.17(15) . . ?
C6B N2B H2B 119.41 . . ?
C4B N2B H2B 119.41 . . ?
C1B C2B C4B 117.6(2) . . ?
C1B C2B C3B 85.74(14) . . ?
C4B C2B C3B 118.5(2) . . ?
C1B C2B H2B1 110.93 . . ?
C4B C2B H2B1 110.93 . . ?
C3B C2B H2B1 110.93 . . ?
C6B O3B C7B 114.6(2) . . ?
N1B C3B C21B 114.80(15) . . ?
N1B C3B C2B 86.73(14) . . ?
C21B C3B C2B 117.55(14) . . ?
N1B C3B H3B 111.84 . . ?
C21B C3B H3B 111.84 . . ?
C2B C3B H3B 111.84 . . ?
N2B C4B C5B 110.31(15) . . ?
N2B C4B C2B 110.79(15) . . ?
C5B C4B C2B 110.6(2) . . ?
N2B C4B H4B 108.36 . . ?
C5B C4B H4B 108.36 . . ?
C2B C4B H4B 108.36 . . ?
C4B C5B H5B1 109.47 . . ?
C4B C5B H5B2 109.47 . . ?
H5B1 C5B H5B2 109.5 . . ?
C4B C5B H5B3 109.47 . . ?
H5B1 C5B H5B3 109.5 . . ?
H5B2 C5B H5B3 109.5 . . ?
O2B C6B N2B 126.8(2) . . ?
O2B C6B O3B 122.9(2) . . ?
N2B C6B O3B 110.4(2) . . ?
O3B C7B C8B 107.3(2) . . ?
O3B C7B H7B1 110.26 . . ?
C8B C7B H7B1 110.26 . . ?
O3B C7B H7B2 110.26 . . ?
C8B C7B H7B2 110.26 . . ?
H7B1 C7B H7B2 108.5 . . ?
C13B C8B C9B 117.1(2) . . ?
C13B C8B C7B 120.9(2) . . ?
C9B C8B C7B 121.9(2) . . ?
C8B C9B C10B 119.0(3) . . ?
C8B C9B H9B 120.5 . . ?
C10B C9B H9B 120.5 . . ?
C11B C10B C9B 118.1(3) . . ?
C11B C10B H10B 121.0 . . ?
C9B C10B H10B 121.0 . . ?
C12B C11B C10B 123.9(3) . . ?
C12B C11B H11B 118.0 . . ?
C10B C11B H11B 118.0 . . ?
C11B C12B C13B 118.6(3) . . ?
C11B C12B H12B 120.7 . . ?
C13B C12B H12B 120.7 . . ?
C12B C13B C8B 123.2(2) . . ?
C12B C13B H13B 118.4 . . ?
C8B C13B H13B 118.42 . . ?
N1B C14B C15B 115.2(2) . . ?
N1B C14B H14C 108.47 . . ?
C15B C14B H14C 108.47 . . ?
N1B C14B H14D 108.47 . . ?
C15B C14B H14D 108.47 . . ?
H14C C14B H14D 107.5 . . ?
C16B C15B C20B 119.6(2) . . ?
C16B C15B C14B 121.6(2) . . ?
C20B C15B C14B 118.6(2) . . ?
C15B C16B C17B 121.2(3) . . ?
C15B C16B H16B 119.4 . . ?
C17B C16B H16B 119.4 . . ?
C16B C17B C18B 118.5(3) . . ?
C16B C17B H17B 120.7 . . ?
C18B C17B H17B 120.7 . . ?
C19B C18B C17B 119.6(3) . . ?
C19B C18B H18B 120.2 . . ?
C17B C18B H18B 120.2 . . ?
C20B C19B C18B 119.2(3) . . ?
C20B C19B H19B 120.4 . . ?
C18B C19B H19B 120.4 . . ?
C15B C20B C19B 121.6(3) . . ?
C15B C20B H20B 119.2 . . ?
C19B C20B H20B 119.2 . . ?
C22D C21B C3B 127.62(9) . . ?
C22B C21B C3B 130.24(9) . . ?
C22D C21B S1D 108.53(5) . . ?
C3B C21B S1D 123.78(8) . . ?
C22B C21B S1B 108.47(5) . . ?
C3B C21B S1B 121.25(8) . . ?
C21B S1B C24B 90.48(4) . . ?
C23B C22B C21B 118.89(6) . . ?
C23B C22B H22B 120.56 . . ?
C21B C22B H22B 120.56 . . ?
C24B C23B C22B 106.08(5) . . ?
C24B C23B H23B 126.96 . . ?
C22B C23B H23B 126.96 . . ?
C23B C24B S1B 115.77(5) . . ?
C23B C24B H24B 122.11 . . ?
S1B C24B H24B 122.11 . . ?
C21B S1D C24D 90.52(4) . . ?
C21B C22D C23D 118.86(6) . . ?
C21B C22D H22D 120.57 . . ?
C23D C22D H22D 120.57 . . ?
C22D C23D C24D 105.99(6) . . ?
C22D C23D H23D 127.01 . . ?
C24D C23D H23D 127.01 . . ?
C23D C24D S1D 115.75(5) . . ?
C23D C24D H24D 122.13 . . ?
S1D C24D H24D 122.13 . . ?
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
N1A C1A 1.354(3) . ?
N1A C14A 1.425(3) . ?
N1A C3A 1.486(3) . ?
O1A C1A 1.218(3) . ?
C1A C2A 1.523(3) . ?
N2A C6A 1.331(2) . ?
N2A C4A 1.474(2) . ?
N2A H2A 0.86 . ?
O2A C6A 1.213(2) . ?
C2A C4A 1.532(3) . ?
C2A C3A 1.546(3) . ?
C2A H2A1 0.98 . ?
O3A C6A 1.349(2) . ?
O3A C7A 1.449(3) . ?
C3A C21A 1.480(2) . ?
C3A H3A 0.98 . ?
C4A C5A 1.507(3) . ?
C4A H4A 0.98 . ?
C5A H5A1 0.96 . ?
C5A H5A2 0.96 . ?
C5A H5A3 0.96 . ?
C7A C8A 1.485(4) . ?
C7A H7A1 0.97 . ?
C7A H7A2 0.97 . ?
C8A C9A 1.361(4) . ?
C8A C13A 1.364(4) . ?
C9A C10A 1.408(5) . ?
C9A H9A 0.93 . ?
C10A C11A 1.325(6) . ?
C10A H10A 0.93 . ?
C11A C12A 1.339(7) . ?
C11A H11A 0.93 . ?
C12A C13A 1.378(5) . ?
C12A H12A 0.93 . ?
C13A H13A 0.93 . ?
C14A C15A 1.504(3) . ?
C14A H14A 0.97 . ?
C14A H14B 0.97 . ?
C15A C16A 1.344(4) . ?
C15A C20A 1.371(3) . ?
C16A C17A 1.393(5) . ?
C16A H16A 0.93 . ?
C17A C18A 1.410(5) . ?
C17A H17A 0.93 . ?
C18A C19A 1.321(5) . ?
C18A H18A 0.93 . ?
C19A C20A 1.391(4) . ?
C19A H19A 0.93 . ?
C20A H20A 0.93 . ?
C21A C22A 1.3796(8) . ?
C21A C22C 1.3809(8) . ?
C21A S1A 1.6978(7) . ?
C21A S1C 1.6979(7) . ?
S1A C24A 1.7012(7) . ?
C22A C23A 1.3803(8) . ?
C22A H22A 0.93 . ?
C23A C24A 1.3800(9) . ?
C23A H23A 0.93 . ?
C24A H24A 0.93 . ?
S1C C24C 1.7011(9) . ?
C22C C23C 1.3807(9) . ?
C22C H22C 0.93 . ?
C23C C24C 1.3804(9) . ?
C23C H23C 0.93 . ?
C24C H24C 0.93 . ?
N1B C1B 1.355(3) . ?
N1B C14B 1.456(3) . ?
N1B C3B 1.466(3) . ?
C1B O1B 1.200(2) . ?
C1B C2B 1.531(3) . ?
N2B C6B 1.338(2) . ?
N2B C4B 1.451(2) . ?
N2B H2B 0.86 . ?
O2B C6B 1.211(2) . ?
C2B C4B 1.535(3) . ?
C2B C3B 1.548(3) . ?
C2B H2B1 0.98 . ?
O3B C6B 1.362(2) . ?
O3B C7B 1.434(3) . ?
C3B C21B 1.499(2) . ?
C3B H3B 0.98 . ?
C4B C5B 1.524(3) . ?
C4B H4B 0.98 . ?
C5B H5B1 0.96 . ?
C5B H5B2 0.96 . ?
C5B H5B3 0.96 . ?
C7B C8B 1.499(3) . ?
C7B H7B1 0.97 . ?
C7B H7B2 0.97 . ?
C8B C13B 1.371(3) . ?
C8B C9B 1.401(4) . ?
C9B C10B 1.433(4) . ?
C9B H9B 0.93 . ?
C10B C11B 1.336(5) . ?
C10B H10B 0.93 . ?
C11B C12B 1.324(4) . ?
C11B H11B 0.93 . ?
C12B C13B 1.357(4) . ?
C12B H12B 0.93 . ?
C13B H13B 0.93 . ?
C14B C15B 1.511(3) . ?
C14B H14C 0.97 . ?
C14B H14D 0.97 . ?
C15B C16B 1.359(4) . ?
C15B C20B 1.366(3) . ?
C16B C17B 1.396(5) . ?
C16B H16B 0.93 . ?
C17B C18B 1.398(5) . ?
C17B H17B 0.93 . ?
C18B C19B 1.397(5) . ?
C18B H18B 0.93 . ?
C19B C20B 1.369(5) . ?
C19B H19B 0.93 . ?
C20B H20B 0.93 . ?
C21B C22D 1.3686(8) . ?
C21B C22B 1.3690(7) . ?
C21B S1D 1.6983(7) . ?
C21B S1B 1.6984(7) . ?
S1B C24B 1.7002(7) . ?
C22B C23B 1.3686(8) . ?
C22B H22B 0.93 . ?
C23B C24B 1.3685(9) . ?
C23B H23B 0.93 . ?
C24B H24B 0.93 . ?
S1D C24D 1.7001(9) . ?
C22D C23D 1.3689(8) . ?
C22D H22D 0.93 . ?
C23D C24D 1.3689(9) . ?
C23D H23D 0.93 . ?
C24D H24D 0.93 . ?
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
C14A N1A C1A O1A 2.9(4) . . . . ?
C3A N1A C1A O1A -177.3(2) . . . . ?
C14A N1A C1A C2A -178.4(2) . . . . ?
C3A N1A C1A C2A 1.4(2) . . . . ?
O1A C1A C2A C4A 56.6(3) . . . . ?
N1A C1A C2A C4A -121.9(2) . . . . ?
O1A C1A C2A C3A 177.2(3) . . . . ?
N1A C1A C2A C3A -1.37(15) . . . . ?
C1A N1A C3A C21A -120.6(2) . . . . ?
C14A N1A C3A C21A 59.2(3) . . . . ?
C1A N1A C3A C2A -1.4(2) . . . . ?
C14A N1A C3A C2A 178.4(2) . . . . ?
C1A C2A C3A C21A 117.7(2) . . . . ?
C4A C2A C3A C21A -120.9(2) . . . . ?
C1A C2A C3A N1A 1.25(13) . . . . ?
C4A C2A C3A N1A 122.6(2) . . . . ?
C6A N2A C4A C5A 132.9(2) . . . . ?
C6A N2A C4A C2A -102.5(2) . . . . ?
C1A C2A C4A N2A 40.5(2) . . . . ?
C3A C2A C4A N2A -61.6(2) . . . . ?
C1A C2A C4A C5A 163.6(2) . . . . ?
C3A C2A C4A C5A 61.5(2) . . . . ?
C4A N2A C6A O2A 2.2(3) . . . . ?
C4A N2A C6A O3A 179.7(2) . . . . ?
C7A O3A C6A O2A 2.8(3) . . . . ?
C7A O3A C6A N2A -174.7(2) . . . . ?
C6A O3A C7A C8A 171.5(2) . . . . ?
O3A C7A C8A C9A 107.6(3) . . . . ?
O3A C7A C8A C13A -73.3(3) . . . . ?
C13A C8A C9A C10A 3.1(4) . . . . ?
C7A C8A C9A C10A -177.8(3) . . . . ?
C8A C9A C10A C11A -3.1(5) . . . . ?
C9A C10A C11A C12A 2.7(6) . . . . ?
C10A C11A C12A C13A -2.4(6) . . . . ?
C9A C8A C13A C12A -2.8(5) . . . . ?
C7A C8A C13A C12A 178.1(3) . . . . ?
C11A C12A C13A C8A 2.4(6) . . . . ?
C1A N1A C14A C15A -105.4(3) . . . . ?
C3A N1A C14A C15A 74.8(3) . . . . ?
N1A C14A C15A C16A 10.0(4) . . . . ?
N1A C14A C15A C20A -173.8(2) . . . . ?
C20A C15A C16A C17A -1.1(5) . . . . ?
C14A C15A C16A C17A 175.1(3) . . . . ?
C15A C16A C17A C18A 10.3(5) . . . . ?
C16A C17A C18A C19A -16.2(6) . . . . ?
C17A C18A C19A C20A 12.8(5) . . . . ?
C16A C15A C20A C19A -2.4(4) . . . . ?
C14A C15A C20A C19A -178.6(2) . . . . ?
C18A C19A C20A C15A -3.7(5) . . . . ?
N1A C3A C21A C22A 19.5(2) . . . . ?
C2A C3A C21A C22A -80.6(2) . . . . ?
N1A C3A C21A C22C -133.72(13) . . . . ?
C2A C3A C21A C22C 126.21(14) . . . . ?
N1A C3A C21A S1A -159.06(11) . . . . ?
C2A C3A C21A S1A 100.87(15) . . . . ?
N1A C3A C21A S1C 36.3(2) . . . . ?
C2A C3A C21A S1C -63.8(2) . . . . ?
C22A C21A S1A C24A 5.51(6) . . . . ?
C22C C21A S1A C24A 76.65(9) . . . . ?
C3A C21A S1A C24A -175.70(10) . . . . ?
S1C C21A S1A C24A -9.22(6) . . . . ?
C22C C21A C22A C23A -34.99(9) . . . . ?
C3A C21A C22A C23A 166.15(11) . . . . ?
S1A C21A C22A C23A -15.12(8) . . . . ?
S1C C21A C22A C23A 88.3(2) . . . . ?
C21A C22A C23A C24A 17.75(9) . . . . ?
C22A C23A C24A S1A -12.45(8) . . . . ?
C21A S1A C24A C23A 4.32(7) . . . . ?
C22A C21A S1C C24C -65.70(15) . . . . ?
C22C C21A S1C C24C -6.02(7) . . . . ?
C3A C21A S1C C24C -177.78(10) . . . . ?
S1A C21A S1C C24C 15.68(6) . . . . ?
C22A C21A C22C C23C 28.64(10) . . . . ?
C3A C21A C22C C23C -172.46(11) . . . . ?
S1A C21A C22C C23C -84.98(12) . . . . ?
S1C C21A C22C C23C 16.22(10) . . . . ?
C21A C22C C23C C24C -18.92(11) . . . . ?
C22C C23C C24C S1C 13.17(10) . . . . ?
C21A S1C C24C C23C -4.45(9) . . . . ?
C14B N1B C1B O1B -2.0(4) . . . . ?
C3B N1B C1B O1B -175.5(2) . . . . ?
C14B N1B C1B C2B 177.4(2) . . . . ?
C3B N1B C1B C2B 3.8(2) . . . . ?
O1B C1B C2B C4B 55.6(3) . . . . ?
N1B C1B C2B C4B -123.6(2) . . . . ?
O1B C1B C2B C3B 175.6(3) . . . . ?
N1B C1B C2B C3B -3.60(15) . . . . ?
C1B N1B C3B C21B -122.7(2) . . . . ?
C14B N1B C3B C21B 64.3(3) . . . . ?
C1B N1B C3B C2B -3.8(2) . . . . ?
C14B N1B C3B C2B -176.8(2) . . . . ?
C1B C2B C3B N1B 3.33(14) . . . . ?
C4B C2B C3B N1B 122.6(2) . . . . ?
C1B C2B C3B C21B 119.7(2) . . . . ?
C4B C2B C3B C21B -121.0(2) . . . . ?
C6B N2B C4B C5B 134.6(2) . . . . ?
C6B N2B C4B C2B -102.6(2) . . . . ?
C1B C2B C4B N2B 43.0(2) . . . . ?
C3B C2B C4B N2B -57.8(2) . . . . ?
C1B C2B C4B C5B 165.6(2) . . . . ?
C3B C2B C4B C5B 64.8(2) . . . . ?
C4B N2B C6B O2B -1.4(3) . . . . ?
C4B N2B C6B O3B 179.0(2) . . . . ?
C7B O3B C6B O2B 6.9(3) . . . . ?
C7B O3B C6B N2B -173.5(2) . . . . ?
C6B O3B C7B C8B 173.0(2) . . . . ?
O3B C7B C8B C13B 96.5(2) . . . . ?
O3B C7B C8B C9B -82.6(3) . . . . ?
C13B C8B C9B C10B -0.7(4) . . . . ?
C7B C8B C9B C10B 178.4(3) . . . . ?
C8B C9B C10B C11B -1.1(4) . . . . ?
C9B C10B C11B C12B 1.2(5) . . . . ?
C10B C11B C12B C13B 0.6(5) . . . . ?
C11B C12B C13B C8B -2.6(4) . . . . ?
C9B C8B C13B C12B 2.6(4) . . . . ?
C7B C8B C13B C12B -176.5(2) . . . . ?
C1B N1B C14B C15B -107.4(3) . . . . ?
C3B N1B C14B C15B 63.6(3) . . . . ?
N1B C14B C15B C16B 26.2(3) . . . . ?
N1B C14B C15B C20B -158.7(2) . . . . ?
C20B C15B C16B C17B 2.4(4) . . . . ?
C14B C15B C16B C17B 177.4(3) . . . . ?
C15B C16B C17B C18B 1.8(5) . . . . ?
C16B C17B C18B C19B -5.3(5) . . . . ?
C17B C18B C19B C20B 4.6(5) . . . . ?
C16B C15B C20B C19B -3.1(4) . . . . ?
C14B C15B C20B C19B -178.3(3) . . . . ?
C18B C19B C20B C15B -0.4(5) . . . . ?
N1B C3B C21B C22D -155.04(12) . . . . ?
C2B C3B C21B C22D 105.2(2) . . . . ?
N1B C3B C21B C22B 6.0(2) . . . . ?
C2B C3B C21B C22B -93.8(2) . . . . ?
N1B C3B C21B S1D 28.4(2) . . . . ?
C2B C3B C21B S1D -71.4(2) . . . . ?
N1B C3B C21B S1B -171.08(11) . . . . ?
C2B C3B C21B S1B 89.1(2) . . . . ?
C22D C21B S1B C24B 62.37(13) . . . . ?
C22B C21B S1B C24B 4.85(6) . . . . ?
C3B C21B S1B C24B -177.51(10) . . . . ?
S1D C21B S1B C24B -14.97(6) . . . . ?
C22D C21B C22B C23B -18.58(10) . . . . ?
C3B C21B C22B C23B 176.59(12) . . . . ?
S1D C21B C22B C23B 99.36(14) . . . . ?
S1B C21B C22B C23B -6.05(10) . . . . ?
C21B C22B C23B C24B 3.70(12) . . . . ?
C22B C23B C24B S1B 0.44(10) . . . . ?
C21B S1B C24B C23B -3.20(8) . . . . ?
C22D C21B S1D C24D -1.74(6) . . . . ?
C22B C21B S1D C24D -68.23(11) . . . . ?
C3B C21B S1D C24D 175.37(10) . . . . ?
S1B C21B S1D C24D 13.35(6) . . . . ?
C22B C21B C22D C23D 23.03(9) . . . . ?
C3B C21B C22D C23D -171.58(11) . . . . ?
S1D C21B C22D C23D 5.39(9) . . . . ?
S1B C21B C22D C23D -102.6(2) . . . . ?
C21B C22D C23D C24D -6.63(10) . . . . ?
C22D C23D C24D S1D 4.94(10) . . . . ?
C21B S1D C24D C23D -1.98(8) . . . . ?
