# Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is © The Royal Society of Chemistry 2003

data_global

_journal_coden_Cambridge         177

loop_
_publ_author_name
'Steven D. Bull'
'Elena Bunuel'
'Stephen G. Davies'
'A. Christopher Garner'
'Andrew D. Smith'
'Richard J. Vickers'
;
D.J.Watkin
;
'Edward D. Savory'

_publ_contact_author_name        'Prof Stephen G. Davies'

_publ_contact_author_address     
;                                                                               
Dyson Perrins Laboratory
Oxford University
South Parks Road
Oxford
UNITED KINGDOM                                                                  
;

_publ_contact_author_email       stephen.davies@chem.ox.ac.uk

_publ_requested_journal          'Organic & Biomolecular Chemistry'

_publ_section_title              
;
Asymmetric synthesis of substituted
1-aminocyclopropane-1-carboxylic acids via diketopiperazine methodology.
;

data_es59d_cif
_database_code_CSD               198088
_audit_creation_date             02-18-11
_audit_creation_method           CRYSTALS_ver_12-03-99
_vrf_plat_305_crystals_cif       
;
PROBLEM: _A Isolated Hydrogen Atom (Outside Bond Range ??)      >H91          
RESPONSE: The Alert is possible a bug or misinterpretation by PLATON of 
the disorder.  There are no anomalous bonds to hydrogen.
The short H11-H152 non-bonded contact is an artifact of the H atom 
placement on a disordered atom. The equivalent contact in the second 
molecule is 1.8 A.  The data is not adrquate to enable refinement of the 
H atoms.

see also _publ_section_exptl_refinement
;

_publ_section_exptl_refinement   
# see also _refine_ls_hydrogen for refinement keywords.                         
;                                                                               

In both molecules the cyclopropyl group is disordered 
approximately 50/50 over two sites (C1/C9 and C101/C109).  This leads to a 
splitting of the adjacent carbons (C200/C201, C230/C231, C1100/C1101, 
C1030/C1031) which can be successfully modelled provided ADP similarity 
constraints are applied.  The terminal methyl groups are probably also 
disordered, but cannot successfully be split and modelled. Because of 
this, hydrogen atoms have not been placed on the terminal atoms.
Bond restraints were applied to the cyclopropy and iso-propyl groups.

The refinement using all data with I greater than -3.0Sigma(I), using F^2 
as the coefficient are reported here to avoid contention with referees. 
The refinement against F with a +3Sigma(I) data-threshold fared no better.

All other H atoms placed geometrically and refined as riding on the 
adjacent carbon                                  
;

_publ_section_exptl_prep         
;                                                                               
The crystals were grown from diethylether-pentane, and 
grew as brick-shaped blocks, generally with a line
running down the long length. Several batches 
were examined on the diffractometer - all samples were twinned.  
Eventually a fragment cut from a twin and which did not 
show extraneous diffraction spots was obtained.

;

#==========================================================================     

_chemical_name_systematic        
# IUPAC name, in full                           
;                                                                               
?                                                                               
;

_chemical_melting_point          ?

# choose from 'full, fullcycle, atomblock, userblock, diagonal, sparse'         
_refine_ls_matrix_type           full

# choose from 'heavy, direct, difmap, geom'                                     
_atom_sites_solution_primary     direct

# _atom_sites_solution_secondary            difmap                              
_atom_sites_solution_hydrogens   geom

# choose from 'none, undef, noref, refall, refxyz, refU, constr, mixed'         
_refine_ls_hydrogen_treatment    constr

#****************************************************************************   
# General computing 
#============================================================= 
_computing_structure_refinement  
; 
CRYSTALS (Watkin et al 2001) 
;
_computing_publication_material  
; 
CRYSTALS (Watkin et al 2001) 
;
_computing_molecular_graphics    
; 
CAMERON (Watkin et al 1996) 
;
#============================================================= 

_cell_length_a                   9.2515(1)
_cell_angle_alpha                90
_cell_length_b                   28.6084(4)
_cell_angle_beta                 99.9280(6)
_cell_length_c                   9.4481(1)
_cell_angle_gamma                90
_cell_volume                     2463.19(5)

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 1 21 1 '
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,y+1/2,-z

# choose from: rm (reference molecule of 
# known chirality), ad (anomolous 
# dispersion - ie. Flack param), rmad 
# (both rm and ad), syn (known from 
# synthetic pathway), unk (unknown) 
# or . (not applicable). 

_chemical_absolute_configuration unk

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
'C   ' 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 International_Tables_Vol_IV_Table_2.2B
'H   ' 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 International_Tables_Vol_IV_Table_2.2B
'N   ' 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 International_Tables_Vol_IV_Table_2.2B
'O   ' 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 International_Tables_Vol_IV_Table_2.2B

_cell_formula_units_Z            4
_chemical_formula_sum            ' C27 H20 N2 O4 '
_chemical_formula_moiety         ' C27 H20 N2 O4 '
_chemical_compound_source        
;
?
;
_chemical_formula_weight         436.47

_cell_measurement_reflns_used    5605
_cell_measurement_theta_min      5
_cell_measurement_theta_max      27
_cell_measurement_temperature    150

_exptl_crystal_description       ' block '
_exptl_crystal_colour            ' colourless '
_exptl_crystal_size_min          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_max          0.20

_exptl_crystal_density_diffrn    1.177
_exptl_crystal_density_meas      ?
# Non-dispersive F(000): 
_exptl_crystal_F_000             912.000
_exptl_absorpt_coefficient_mu    0.080
# Sheldrick geometric definitions 0.98 0.98 

_diffrn_measurement_device_type  
; 
Enraf Nonius Kappa CCD 
;
_diffrn_radiation_monochromator  graphite
_computing_data_collection       
; 
COLLECT (Nonius BV, 1997) 
;
_computing_data_reduction        
; 
Denzo/Scalepack (Otwinowski & Minor, 1996) 
;
_computing_cell_refinement       
; 
Denzo/Scalepack (Otwinowski & Minor, 1996) 
;
_computing_structure_solution    
; 
SIR92 (Altomare et al, 1994) 
;
_diffrn_measurement_method       \w
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
; 
Denzo/Scalepack (Otwinowski & Minor, 1996) 
;
_exptl_absorpt_correction_T_min  0.98
_exptl_absorpt_correction_T_max  0.98

_diffrn_standards_interval_time  0
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_diffrn_standards_decay_%        0.00

_diffrn_ambient_temperature      150
_diffrn_reflns_number            10759
_reflns_number_total             5686
_diffrn_reflns_av_R_equivalents  0.01
# Number of reflections with Friedels Law is 5686 
# Number of reflections without Friedels Law is 0 
# Theoretical number of reflections is about 5641 

_diffrn_reflns_theta_min         5.138
_diffrn_reflns_theta_max         27.468
_diffrn_measured_fraction_theta_max 0.989

_diffrn_reflns_theta_full        27.331
_diffrn_measured_fraction_theta_full 0.991

_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -36
_diffrn_reflns_limit_k_max       37
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_reflns_limit_h_min              -12
_reflns_limit_h_max              11
_reflns_limit_k_min              0
_reflns_limit_k_max              36
_reflns_limit_l_min              0
_reflns_limit_l_max              12

_refine_diff_density_min         -0.23
_refine_diff_density_max         0.35

_refine_ls_number_reflns         5686
_refine_ls_number_parameters     615

#_refine_ls_R_factor_ref 0.0657 
_refine_ls_wR_factor_ref         0.1407
_refine_ls_goodness_of_fit_ref   0.9234

#_reflns_number_all 5686 
_refine_ls_R_factor_all          0.0657
_refine_ls_wR_factor_all         0.1407

# The I/u(I) cutoff below was used for refinement as 
# well as the _gt R-factors:
_reflns_threshold_expression     I>-3.00u(I)
_reflns_number_gt                5686
_refine_ls_R_factor_gt           0.0657
_refine_ls_wR_factor_gt          0.1407

_refine_ls_shift/su_max          0.014797
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
Method = SHELXL 97 (Sheldrick, 1997) 
W = q / [Sigma^2(F*)+(P(1)p)^2+P(2)p+P(4)+P(5)Sin(theta) ] 

0.844E-01 0.663 0.00 0.00 0.00 0.333 
;
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073

## -------------------REFERENCES ----------------------## 
## Insert your own references - in alphabetic order 
_publ_section_references         
; 

Altomare, A., Cascarano, G., Giacovazzo G., Guagliardi A., Burla M.C., 
Polidori, G. & Camalli, M. (1994) SIR92 - a program for automatic solution 
of crystal structures by direct methods. J. Appl. Cryst. (27), 435-435 

COLLECT Software, Nonius BV 1997-2001) 

Otwinowski, Z. & Minor, W. (1996), Processing of X-ray 
Diffraction Data Collected in Oscillation Mode. Methods Enzymol. 
276, 1997, 307-326. Ed Carter, C.W. & Sweet, R.M., Academic Press. 

Sheldrick, G.M. (1997). SHELXL-97. Program for the refinement of 
crystal structures. Univ. of Gottingen, Federal Republic of Germany. 

Watkin, D.J., Prout, C.K., Carruthers, J.R., Betteridge, P.W. & Cooper 
R.I. (2001) CRYSTALS 
Issue 11. Chemical Crystallography Laboratory, OXFORD, UK. 

Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996) CAMERON, Chemical 
Crystallography Laboratory, OXFORD, UK. 
;

# Uequiv = arithmetic mean of Ui
# i.e. Ueqiv = (U1+U2+U3)/3

# Replace trailing . with the number of unfound
# hydrogen atoms attaced to relavent atom

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_occupancy
_atom_site_adp_type
_atom_site_attached_hydrogens
C1 C 0.061(1) 0.2371(3) 0.4933(7) 0.0434 0.3528(19) Uani .
C2 C 0.0931(3) 0.26577(11) 0.3759(3) 0.0391 1.0000 Uani .
C4 C -0.1816(4) 0.24628(19) 0.3466(6) 0.0806 1.0000 Uani 3
C5 C -0.0020(5) 0.18601(15) 0.2747(6) 0.0747 1.0000 Uani 3
C6 C 0.2314(3) 0.25807(11) 0.3160(3) 0.0396 1.0000 Uani .
C8 C 0.1378(3) 0.3217(1) 0.1562(3) 0.0349 1.0000 Uani .
C9 C 0.1434(5) 0.35262(17) 0.0336(5) 0.0434 0.6472(19) Uani .
C11 C -0.1252(6) 0.33051(17) 0.0007(6) 0.0873 1.0000 Uani 3
C12 C 0.0629(6) 0.27328(16) -0.0753(4) 0.0723 1.0000 Uani 3
C13 C 0.0772(3) 0.34458(11) 0.2772(3) 0.0365 1.0000 Uani .
C15 C 0.0125(4) 0.33552(15) 0.5137(4) 0.0544 1.0000 Uani .
C16 C 0.1309(3) 0.36181(12) 0.6114(3) 0.0397 1.0000 Uani .
C17 C 0.2698(3) 0.34341(12) 0.6546(3) 0.0416 1.0000 Uani .
C18 C 0.3759(3) 0.36728(12) 0.7472(3) 0.0394 1.0000 Uani .
C19 C 0.3434(3) 0.41130(11) 0.7993(3) 0.0365 1.0000 Uani .
C20 C 0.2059(3) 0.43014(12) 0.7572(3) 0.0405 1.0000 Uani .
C21 C 0.1015(3) 0.40531(13) 0.6620(3) 0.0429 1.0000 Uani .
C23 C 0.4201(4) 0.47443(13) 0.9593(4) 0.0518 1.0000 Uani .
C25 C 0.3950(3) 0.28949(13) 0.1626(4) 0.0443 1.0000 Uani .
C26 C 0.4885(3) 0.32783(11) 0.2406(3) 0.0374 1.0000 Uani .
C27 C 0.5219(4) 0.32854(13) 0.3898(4) 0.0474 1.0000 Uani .
C28 C 0.6078(4) 0.36336(14) 0.4622(4) 0.0490 1.0000 Uani .
C29 C 0.6634(3) 0.39878(12) 0.3863(3) 0.0394 1.0000 Uani .
C30 C 0.8107(4) 0.46796(13) 0.3947(4) 0.0542 1.0000 Uani .
C32 C 0.6342(4) 0.39843(13) 0.2381(4) 0.0462 1.0000 Uani .
C33 C 0.5460(4) 0.36302(14) 0.1665(4) 0.0484 1.0000 Uani .
C101 C 1.2571(6) 0.6883(2) 1.1784(7) 0.0464 0.5129(19) Uani .
C102 C 1.3763(3) 0.65843(11) 1.1534(3) 0.0387 1.0000 Uani .
C104 C 1.4114(6) 0.67885(19) 1.4225(5) 0.0807 1.0000 Uani 3
C105 C 1.4744(7) 0.74044(16) 1.2413(6) 0.0904 1.0000 Uani 3
C106 C 1.4359(4) 0.66597(11) 1.0176(3) 0.0404 1.0000 Uani .
C108 C 1.6077(3) 0.60557(11) 1.1151(3) 0.0371 1.0000 Uani .
C109 C 1.7338(6) 0.5776(2) 1.1101(7) 0.0464 0.4871(19) Uani .
C111 C 1.7792(7) 0.59972(19) 1.3634(6) 0.0964 1.0000 Uani 3
C112 C 1.8363(5) 0.65673(18) 1.1720(6) 0.0827 1.0000 Uani 3
C113 C 1.4888(3) 0.58159(11) 1.1802(3) 0.0375 1.0000 Uani .
C115 C 1.2457(4) 0.58709(14) 1.2387(4) 0.0500 1.0000 Uani .
C116 C 1.1479(3) 0.56052(11) 1.1211(3) 0.0382 1.0000 Uani .
C117 C 1.1139(4) 0.57756(13) 0.9814(4) 0.0486 1.0000 Uani .
C118 C 1.0211(4) 0.55307(13) 0.8756(4) 0.0476 1.0000 Uani .
C119 C 0.9617(3) 0.51109(11) 0.9082(3) 0.0366 1.0000 Uani .
C120 C 0.9943(3) 0.49337(11) 1.0472(3) 0.0388 1.0000 Uani .
C121 C 1.0868(3) 0.51846(12) 1.1518(3) 0.0400 1.0000 Uani .
C123 C 0.7990(5) 0.44867(15) 0.8304(4) 0.0616 1.0000 Uani .
C125 C 1.5945(4) 0.63517(13) 0.8579(4) 0.0458 1.0000 Uani .
C126 C 1.5163(3) 0.59771(12) 0.7625(3) 0.0403 1.0000 Uani .
C127 C 1.3634(4) 0.59900(14) 0.7218(4) 0.0487 1.0000 Uani .
C128 C 1.2889(4) 0.56524(14) 0.6332(4) 0.0497 1.0000 Uani .
C129 C 1.3657(4) 0.52922(11) 0.5806(3) 0.0390 1.0000 Uani .
C131 C 1.3551(5) 0.45935(12) 0.4400(4) 0.0529 1.0000 Uani .
C132 C 1.5167(4) 0.52759(13) 0.6184(3) 0.0455 1.0000 Uani .
C133 C 1.5894(4) 0.56116(13) 0.7093(4) 0.0460 1.0000 Uani .
C200 C 0.0252(13) 0.2977(3) 0.0369(9) 0.0405 0.3529(19) Uani .
C201 C 0.0236(6) 0.31553(18) 0.0170(5) 0.0405 0.6471(19) Uani .
C230 C -0.0379(6) 0.2366(2) 0.2945(6) 0.0436 0.6471(19) Uani .
C231 C -0.035(1) 0.2317(4) 0.3447(9) 0.0436 0.3529(19) Uani .
C1030 C 1.4474(7) 0.6895(3) 1.2799(8) 0.0399 0.4871(19) Uani .
C1031 C 1.4063(6) 0.6952(3) 1.2727(8) 0.0399 0.5129(19) Uani .
C1100 C 1.7261(6) 0.6298(2) 1.2284(7) 0.0388 0.5129(19) Uani .
C1101 C 1.7497(7) 0.6173(2) 1.2199(8) 0.0388 0.4871(19) Uani .
N7 N 0.2497(3) 0.28699(9) 0.2070(3) 0.0378 1.0000 Uani .
N14 N 0.0613(3) 0.3155(1) 0.3864(3) 0.0398 1.0000 Uani .
N107 N 1.5486(3) 0.63747(9) 1.0002(3) 0.0390 1.0000 Uani .
N114 N 1.3725(3) 0.60927(9) 1.1908(3) 0.0396 1.0000 Uani .
O22 O 0.4555(2) 0.43256(8) 0.8893(2) 0.0455 1.0000 Uani .
O24 O 0.0432(3) 0.38595(8) 0.2755(3) 0.0540 1.0000 Uani .
O30 O 0.7454(3) 0.43205(8) 0.4678(2) 0.0480 1.0000 Uani .
O34 O 0.3205(3) 0.22815(9) 0.3653(3) 0.0555 1.0000 Uani .
O122 O 0.8743(2) 0.48911(9) 0.7959(2) 0.0444 1.0000 Uani .
O124 O 1.4986(3) 0.54093(8) 1.2190(2) 0.0483 1.0000 Uani .
O130 O 1.2815(3) 0.49783(9) 0.4938(2) 0.0498 1.0000 Uani .
O134 O 1.3835(3) 0.69518(9) 0.9277(3) 0.0540 1.0000 Uani .
H151 H -0.0699(4) 0.35767(15) 0.4802(4) 0.0663 1.0000 Uiso .
H152 H -0.0233(4) 0.30959(15) 0.5697(4) 0.0663 1.0000 Uiso .
H171 H 0.2941(3) 0.31204(12) 0.6183(3) 0.0504 1.0000 Uiso .
H181 H 0.4755(3) 0.35336(12) 0.7775(3) 0.0462 1.0000 Uiso .
H201 H 0.1814(3) 0.46142(12) 0.7940(3) 0.0488 1.0000 Uiso .
H211 H 0.0021(3) 0.41936(13) 0.6310(3) 0.0503 1.0000 Uiso .
H231 H 0.5103(4) 0.48658(13) 1.0222(4) 0.0617 1.0000 Uiso .
H232 H 0.3822(4) 0.49844(13) 0.8852(4) 0.0617 1.0000 Uiso .
H233 H 0.3434(4) 0.46758(13) 1.0192(4) 0.0617 1.0000 Uiso .
H251 H 0.3808(3) 0.29548(13) 0.0568(4) 0.0600 1.0000 Uiso .
H252 H 0.4461(3) 0.25888(13) 0.1846(4) 0.0600 1.0000 Uiso .
H271 H 0.4826(4) 0.30325(13) 0.4456(4) 0.0559 1.0000 Uiso .
H281 H 0.6302(4) 0.36311(14) 0.5696(4) 0.0583 1.0000 Uiso .
H311 H 0.8670(4) 0.48986(13) 0.4663(4) 0.0663 1.0000 Uiso .
H312 H 0.7317(4) 0.48559(13) 0.3308(4) 0.0663 1.0000 Uiso .
H313 H 0.8786(4) 0.45357(13) 0.3353(4) 0.0663 1.0000 Uiso .
H321 H 0.6751(4) 0.42337(13) 0.1822(4) 0.0531 1.0000 Uiso .
H331 H 0.5246(4) 0.36287(14) 0.0591(4) 0.0566 1.0000 Uiso .
H1151 H 1.1863(4) 0.61195(14) 1.2763(4) 0.0607 1.0000 Uiso .
H1152 H 1.2827(4) 0.56454(14) 1.3175(4) 0.0607 1.0000 Uiso .
H1171 H 1.1578(4) 0.60775(13) 0.9564(4) 0.0585 1.0000 Uiso .
H1181 H 0.9966(4) 0.56624(13) 0.7763(4) 0.0541 1.0000 Uiso .
H1201 H 0.9522(3) 0.46281(11) 1.0716(3) 0.0461 1.0000 Uiso .
H1211 H 1.1099(3) 0.50574(12) 1.2517(3) 0.0467 1.0000 Uiso .
H1231 H 0.7390(5) 0.43574(15) 0.7408(4) 0.0714 1.0000 Uiso .
H1232 H 0.7330(5) 0.45728(15) 0.8997(4) 0.0714 1.0000 Uiso .
H1233 H 0.8711(5) 0.42458(15) 0.8748(4) 0.0714 1.0000 Uiso .
H1251 H 1.5748(4) 0.66610(13) 0.8090(4) 0.0556 1.0000 Uiso .
H1252 H 1.7022(4) 0.62847(13) 0.8729(4) 0.0556 1.0000 Uiso .
H1271 H 1.3068(4) 0.62484(14) 0.7581(4) 0.0577 1.0000 Uiso .
H1281 H 1.1797(4) 0.56694(14) 0.6056(4) 0.0604 1.0000 Uiso .
H1311 H 1.2809(5) 0.43936(12) 0.3783(4) 0.0666 1.0000 Uiso .
H1312 H 1.4275(5) 0.47143(12) 0.3817(4) 0.0666 1.0000 Uiso .
H1313 H 1.4074(5) 0.44038(12) 0.5220(4) 0.0666 1.0000 Uiso .
H1321 H 1.5729(4) 0.50192(13) 0.5808(3) 0.0535 1.0000 Uiso .
H1331 H 1.6986(4) 0.55945(13) 0.7365(4) 0.0553 1.0000 Uiso .
H1011 H 1.2179(6) 0.7126(2) 1.1058(7) 0.0566 0.5110 Uiso .
H1012 H 1.1745(6) 0.6748(2) 1.2210(7) 0.0566 0.5110 Uiso .
H1091 H 1.7848(6) 0.5797(2) 1.0252(7) 0.0566 0.4890 Uiso .
H1092 H 1.7358(6) 0.5445(2) 1.1444(7) 0.0566 0.4890 Uiso .
H91 H 0.1168(5) 0.38635(17) 0.0400(5) 0.0526 0.6430 Uiso .
H92 H 0.2259(5) 0.34957(17) -0.0216(5) 0.0526 0.6430 Uiso .
H11 H 0.012(1) 0.2506(3) 0.5709(7) 0.0526 0.3570 Uiso .
H12 H 0.127(1) 0.2109(3) 0.5334(7) 0.0526 0.3570 Uiso .
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 0.0500(7) 0.0379(7) 0.0447(7) -0.0002(6) 0.0148(5) -0.0047(19)
C2 0.0373(8) 0.0418(8) 0.0367(8) 0.0001(8) 0.0019(6) -0.0056(13)
C4 0.0438(9) 0.0951(9) 0.1081(9) -0.0353(9) 0.0281(6) -0.028(2)
C5 0.0729(9) 0.0400(9) 0.1070(9) -0.0141(9) 0.0033(7) -0.0124(19)
C6 0.0369(8) 0.0331(8) 0.0466(8) 0.0001(8) 0.0008(6) -0.0022(13)
C8 0.0334(8) 0.0315(8) 0.0400(8) -0.0018(8) 0.0067(6) -0.0011(12)
C9 0.0500(7) 0.0379(7) 0.0447(7) -0.0002(6) 0.0148(5) -0.0047(19)
C11 0.0859(9) 0.0603(9) 0.0951(9) -0.0033(9) -0.0422(7) 0.017(2)
C12 0.1094(9) 0.0605(9) 0.0431(9) -0.0163(9) 0.0027(7) -0.004(2)
C13 0.0326(8) 0.0312(8) 0.0458(8) -0.0089(8) 0.0066(6) -0.0024(12)
C15 0.0425(8) 0.0736(9) 0.0508(8) -0.0244(8) 0.0189(6) -0.0132(16)
C16 0.0398(8) 0.0467(8) 0.0353(8) -0.0070(8) 0.0139(6) -0.0038(14)
C17 0.0430(8) 0.0394(8) 0.0450(8) -0.0114(8) 0.0151(6) -0.0009(14)
C18 0.0403(8) 0.0409(8) 0.0385(8) -0.0059(8) 0.0112(6) 0.0062(14)
C19 0.0447(8) 0.0355(8) 0.0294(8) -0.0011(8) 0.0067(6) -0.0023(13)
C20 0.0443(8) 0.0360(8) 0.0420(8) -0.0064(8) 0.0095(6) 0.0064(14)
C21 0.0365(8) 0.0537(9) 0.0386(8) -0.0044(8) 0.0063(6) 0.0059(15)
C23 0.0652(9) 0.0438(9) 0.0446(8) -0.0135(8) 0.0039(6) -0.0035(17)
C25 0.0361(8) 0.0482(9) 0.0517(8) -0.0080(8) 0.0160(6) 0.0026(14)
C26 0.0292(8) 0.0415(8) 0.0432(8) -0.0022(8) 0.0116(6) 0.0031(12)
C27 0.0443(8) 0.0531(9) 0.0459(8) 0.0041(8) 0.0105(6) -0.0086(15)
C28 0.0513(9) 0.0582(9) 0.0386(8) 0.0027(8) 0.0103(6) -0.0106(17)
C29 0.0311(8) 0.0422(8) 0.0450(8) -0.0004(8) 0.0072(6) 0.0031(13)
C30 0.0545(9) 0.0390(8) 0.0683(9) 0.0009(8) 0.0083(6) -0.0059(16)
C32 0.0486(8) 0.0472(9) 0.0423(8) 0.0084(8) 0.0062(6) -0.0078(15)
C33 0.0508(8) 0.0586(9) 0.0358(8) 0.0002(8) 0.0079(6) -0.0034(17)
C101 0.0393(6) 0.0483(7) 0.0545(7) -0.0036(7) 0.0158(5) 0.004(2)
C102 0.0376(8) 0.0393(8) 0.0379(8) -0.0041(8) 0.0030(6) -0.0063(13)
C104 0.1148(9) 0.0838(9) 0.0461(9) -0.0287(9) 0.0207(7) -0.021(3)
C105 0.138(1) 0.0401(9) 0.0865(9) -0.0139(9) 0.0019(7) -0.021(3)
C106 0.0427(8) 0.0378(8) 0.0389(8) -0.0002(8) 0.0020(6) -0.0061(14)
C108 0.0413(8) 0.0332(8) 0.0370(8) -0.0002(8) 0.0076(6) -0.0038(13)
C109 0.0393(6) 0.0483(7) 0.0545(7) -0.0036(7) 0.0158(5) 0.004(2)
C111 0.1058(9) 0.0753(9) 0.0837(9) 0.0227(9) -0.0522(7) -0.025(3)
C112 0.0546(9) 0.0696(9) 0.1174(9) 0.0129(9) -0.0033(7) -0.029(2)
C113 0.0461(8) 0.0368(8) 0.0296(8) -0.0050(8) 0.0068(6) -0.0110(13)
C115 0.0513(8) 0.0611(9) 0.0412(8) -0.0129(8) 0.0178(6) -0.0240(16)
C116 0.0380(8) 0.0412(8) 0.0371(8) -0.0065(8) 0.0112(6) -0.0077(13)
C117 0.0576(9) 0.0465(9) 0.0421(8) 0.0012(8) 0.0093(6) -0.0225(15)
C118 0.0496(8) 0.0552(9) 0.0373(8) 0.0068(8) 0.0054(6) -0.0088(16)
C119 0.0287(8) 0.0396(8) 0.0416(8) -0.0044(8) 0.0065(6) 0.0001(12)
C120 0.0349(8) 0.0386(8) 0.0424(8) 0.0007(8) 0.0049(6) -0.0045(13)
C121 0.0371(8) 0.0459(8) 0.0376(8) -0.0002(8) 0.0084(6) -0.0044(13)
C123 0.0619(9) 0.0663(9) 0.0544(9) -0.0113(9) 0.0039(6) -0.0292(18)
C125 0.0497(8) 0.0506(9) 0.0398(8) 0.0082(8) 0.0155(6) -0.0036(15)
C126 0.0457(8) 0.0440(8) 0.0330(8) 0.0082(8) 0.0123(6) 0.0032(14)
C127 0.0488(8) 0.0547(9) 0.0428(8) -0.0049(8) 0.0083(6) 0.0158(16)
C128 0.0423(8) 0.0628(9) 0.0436(8) -0.0070(8) 0.0066(6) 0.0093(16)
C129 0.0464(8) 0.0407(8) 0.0309(8) 0.0035(8) 0.0097(6) 0.0020(14)
C131 0.0721(9) 0.0407(9) 0.0493(8) -0.0005(8) 0.0201(6) 0.0036(17)
C132 0.0502(8) 0.0504(9) 0.0389(8) 0.0022(8) 0.0157(6) 0.0112(15)
C133 0.0416(8) 0.0544(9) 0.0437(8) 0.0075(8) 0.0116(6) 0.0081(15)
C200 0.0456(6) 0.0418(7) 0.0336(6) 0.0008(7) 0.0059(5) 0.005(3)
C201 0.0456(6) 0.0418(7) 0.0336(6) 0.0008(7) 0.0059(5) 0.005(3)
C230 0.0434(6) 0.0420(7) 0.0464(7) -0.0027(7) 0.0108(5) -0.0130(17)
C231 0.0434(6) 0.0420(7) 0.0464(7) -0.0027(7) 0.0108(5) -0.0130(17)
C1030 0.0290(7) 0.0376(7) 0.0547(6) -0.0151(6) 0.0122(5) 0.002(2)
C1031 0.0290(7) 0.0376(7) 0.0547(6) -0.0151(6) 0.0122(5) 0.002(2)
C1100 0.0258(7) 0.0417(7) 0.0495(6) -0.0052(7) 0.0079(5) 0.010(2)
C1101 0.0258(7) 0.0417(7) 0.0495(6) -0.0052(7) 0.0079(5) 0.010(2)
N7 0.0319(7) 0.0365(8) 0.0458(8) -0.0017(7) 0.0087(6) 0.0014(11)
N14 0.0401(8) 0.0424(8) 0.0390(8) -0.0108(7) 0.0129(6) -0.0076(11)
N107 0.0444(8) 0.0391(8) 0.0348(7) 0.0054(7) 0.0104(6) -0.0006(12)
N114 0.0423(8) 0.0360(8) 0.0425(8) -0.0090(7) 0.0124(6) -0.0128(11)
O22 0.0472(7) 0.0435(8) 0.0436(7) -0.0106(7) 0.0020(6) -0.0012(11)
O24 0.0528(8) 0.0378(8) 0.0698(8) -0.0116(7) 0.0060(6) 0.0052(11)
O30 0.0470(7) 0.0460(8) 0.0508(8) -0.0035(7) 0.0081(6) -0.0086(11)
O34 0.0428(8) 0.0438(8) 0.0765(8) 0.0077(8) 0.0008(6) 0.0052(11)
O122 0.0388(7) 0.0507(8) 0.0420(7) -0.0061(7) 0.0020(5) -0.006(1)
O124 0.0699(8) 0.0329(7) 0.0421(7) 0.0011(7) 0.0097(6) -0.0125(11)
O130 0.0561(8) 0.0522(8) 0.0423(7) -0.0044(7) 0.0118(6) 0.0018(11)
O134 0.0665(8) 0.0444(8) 0.0485(8) 0.0070(7) 0.0030(6) 0.0052(12)
_refine_ls_extinction_coef       369.459
_refine_ls_extinction_method     'Larson 1970 Crystallographic Computing eq 22'
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 . C2 . 1.452(7) yes
C1 . C231 . 1.532(8) yes
C1 . H11 . 1.000 no
C1 . H12 . 1.000 no
C2 . C6 . 1.502(4) yes
C2 . C230 . 1.560(5) yes
C2 . C231 . 1.522(7) yes
C2 . N14 . 1.459(4) yes
C4 . C230 . 1.520(7) yes
C4 . C231 . 1.423(12) yes
C5 . C230 . 1.504(7) yes
C5 . C231 . 1.519(12) yes
C6 . N7 . 1.354(4) yes
C6 . O34 . 1.224(4) yes
C8 . C9 . 1.466(5) yes
C8 . C13 . 1.507(4) yes
C8 . C200 . 1.556(7) yes
C8 . C201 . 1.548(5) yes
C8 . N7 . 1.454(4) yes
C9 . C201 . 1.523(6) yes
C9 . H91 . 1.000 no
C9 . H92 . 1.000 no
C11 . C200 . 1.665(13) yes
C11 . C201 . 1.425(8) yes
C12 . C200 . 1.364(11) yes
C12 . C201 . 1.570(7) yes
C13 . N14 . 1.353(4) yes
C13 . O24 . 1.224(4) yes
C15 . C16 . 1.507(5) yes
C15 . N14 . 1.472(4) yes
C15 . H151 . 1.000 no
C15 . H152 . 1.000 no
C16 . C17 . 1.383(5) yes
C16 . C21 . 1.377(5) yes
C17 . C18 . 1.378(5) yes
C17 . H171 . 1.000 no
C18 . C19 . 1.404(4) yes
C18 . H181 . 1.000 no
C19 . C20 . 1.376(4) yes
C19 . O22 . 1.365(4) yes
C20 . C21 . 1.395(5) yes
C20 . H201 . 1.000 no
C21 . H211 . 1.000 no
C23 . O22 . 1.434(4) yes
C23 . H231 . 1.000 no
C23 . H232 . 1.000 no
C23 . H233 . 1.000 no
C25 . C26 . 1.508(5) yes
C25 . N7 . 1.478(4) yes
C25 . H251 . 1.000 no
C25 . H252 . 1.000 no
C26 . C27 . 1.390(5) yes
C26 . C33 . 1.383(5) yes
C27 . C28 . 1.380(5) yes
C27 . H271 . 1.000 no
C28 . C29 . 1.390(5) yes
C28 . H281 . 1.000 no
C29 . C32 . 1.379(5) yes
C29 . O30 . 1.369(4) yes
C30 . O30 . 1.429(4) yes
C30 . H311 . 1.000 no
C30 . H312 . 1.000 no
C30 . H313 . 1.000 no
C32 . C33 . 1.400(5) yes
C32 . H321 . 1.000 no
C33 . H331 . 1.000 no
C101 . C102 . 1.446(6) yes
C101 . C1031 . 1.521(7) yes
C101 . H1011 . 1.000 no
C101 . H1012 . 1.000 no
C102 . C106 . 1.497(4) yes
C102 . C1030 . 1.543(7) yes
C102 . C1031 . 1.531(6) yes
C102 . N114 . 1.452(4) yes
C104 . C1030 . 1.474(9) yes
C104 . C1031 . 1.48(1) yes
C105 . C1030 . 1.533(11) yes
C105 . C1031 . 1.49(1) yes
C106 . N107 . 1.356(4) yes
C106 . O134 . 1.230(4) yes
C108 . C109 . 1.423(6) yes
C108 . C113 . 1.514(4) yes
C108 . C1100 . 1.556(6) yes
C108 . C1101 . 1.540(6) yes
C108 . N107 . 1.451(4) yes
C109 . C1101 . 1.528(7) yes
C109 . H1091 . 1.000 no
C109 . H1092 . 1.000 no
C111 . C1100 . 1.546(9) yes
C111 . C1101 . 1.427(9) yes
C112 . C1100 . 1.450(9) yes
C112 . C1101 . 1.498(9) yes
C113 . N114 . 1.354(4) yes
C113 . O124 . 1.218(4) yes
C115 . C116 . 1.512(4) yes
C115 . N114 . 1.472(4) yes
C115 . H1151 . 1.000 no
C115 . H1152 . 1.000 no
C116 . C117 . 1.391(5) yes
C116 . C121 . 1.381(5) yes
C117 . C118 . 1.390(5) yes
C117 . H1171 . 1.000 no
C118 . C119 . 1.377(5) yes
C118 . H1181 . 1.000 no
C119 . C120 . 1.391(4) yes
C119 . O122 . 1.370(4) yes
C120 . C121 . 1.390(4) yes
C120 . H1201 . 1.000 no
C121 . H1211 . 1.000 no
C123 . O122 . 1.417(5) yes
C123 . H1231 . 1.000 no
C123 . H1232 . 1.000 no
C123 . H1233 . 1.000 no
C125 . C126 . 1.503(5) yes
C125 . N107 . 1.480(4) yes
C125 . H1251 . 1.000 no
C125 . H1252 . 1.000 no
C126 . C127 . 1.401(5) yes
C126 . C133 . 1.386(5) yes
C127 . C128 . 1.382(5) yes
C127 . H1271 . 1.000 no
C128 . C129 . 1.391(5) yes
C128 . H1281 . 1.000 no
C129 . C132 . 1.382(5) yes
C129 . O130 . 1.366(4) yes
C131 . O130 . 1.433(4) yes
C131 . H1311 . 1.000 no
C131 . H1312 . 1.000 no
C131 . H1313 . 1.000 no
C132 . C133 . 1.383(5) yes
C132 . H1321 . 1.000 no
C133 . H1331 . 1.000 no
C200 . C201 . 0.54(1) yes
C230 . C231 . 0.491(9) yes
C1030 . C1031 . 0.409(9) yes
C1100 . C1101 . 0.434(8) yes
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 . C1 . C231 . 61.3(4) yes
C2 . C1 . H11 . 121.3(4) no
C231 . C1 . H11 . 116.8(6) no
C2 . C1 . H12 . 121.2(4) no
C231 . C1 . H12 . 119.4(6) no
H11 . C1 . H12 . 109.467 no
C1 . C2 . C6 . 120.4(5) yes
C1 . C2 . C230 . 80.2(4) yes
C6 . C2 . C230 . 112.1(3) yes
C1 . C2 . C231 . 61.9(4) yes
C6 . C2 . C231 . 121.2(5) yes
C230 . C2 . C231 . 18.3(3) yes
C1 . C2 . N14 . 115.4(5) yes
C6 . C2 . N14 . 111.3(2) yes
C230 . C2 . N14 . 114.0(3) yes
C231 . C2 . N14 . 118.6(5) yes
C230 . C4 . C231 . 18.8(4) yes
C230 . C5 . C231 . 18.7(4) yes
C2 . C6 . N7 . 115.0(3) yes
C2 . C6 . O34 . 121.4(3) yes
N7 . C6 . O34 . 123.6(3) yes
C9 . C8 . C13 . 113.9(3) yes
C9 . C8 . C200 . 78.7(4) yes
C13 . C8 . C200 . 116.8(5) yes
C9 . C8 . C201 . 60.6(3) yes
C13 . C8 . C201 . 113.9(3) yes
C200 . C8 . C201 . 20.2(4) yes
C9 . C8 . N7 . 123.6(3) yes
C13 . C8 . N7 . 112.5(2) yes
C200 . C8 . N7 . 106.7(5) yes
C201 . C8 . N7 . 123.1(3) yes
C8 . C9 . C201 . 62.3(3) yes
C8 . C9 . H91 . 119.5(2) no
C201 . C9 . H91 . 119.8(3) no
C8 . C9 . H92 . 119.6(2) no
C201 . C9 . H92 . 119.5(3) no
H91 . C9 . H92 . 109.467 no
C200 . C11 . C201 . 18.2(4) yes
C200 . C12 . C201 . 19.8(4) yes
C8 . C13 . N14 . 114.4(3) yes
C8 . C13 . O24 . 122.6(3) yes
N14 . C13 . O24 . 122.9(3) yes
C16 . C15 . N14 . 113.7(3) yes
C16 . C15 . H151 . 108.2(2) no
N14 . C15 . H151 . 108.2(2) no
C16 . C15 . H152 . 108.6(2) no
N14 . C15 . H152 . 108.6(2) no
H151 . C15 . H152 . 109.467 no
C15 . C16 . C17 . 122.1(3) yes
C15 . C16 . C21 . 119.8(3) yes
C17 . C16 . C21 . 118.1(3) yes
C16 . C17 . C18 . 121.5(3) yes
C16 . C17 . H171 . 119.55(18) no
C18 . C17 . H171 . 118.98(19) no
C17 . C18 . C19 . 119.7(3) yes
C17 . C18 . H181 . 120.36(19) no
C19 . C18 . H181 . 119.93(18) no
C18 . C19 . C20 . 119.5(3) yes
C18 . C19 . O22 . 115.6(3) yes
C20 . C19 . O22 . 124.8(3) yes
C19 . C20 . C21 . 119.3(3) yes
C19 . C20 . H201 . 120.25(18) no
C21 . C20 . H201 . 120.42(19) no
C16 . C21 . C20 . 121.8(3) yes
C16 . C21 . H211 . 119.26(19) no
C20 . C21 . H211 . 118.91(19) no
O22 . C23 . H231 . 109.29(18) no
O22 . C23 . H232 . 109.34(18) no
H231 . C23 . H232 . 109.474 no
O22 . C23 . H233 . 109.77(18) no
H231 . C23 . H233 . 109.477 no
H232 . C23 . H233 . 109.475 no
C26 . C25 . N7 . 111.7(3) yes
C26 . C25 . H251 . 109.20(18) no
N7 . C25 . H251 . 108.85(18) no
C26 . C25 . H252 . 108.94(18) no
N7 . C25 . H252 . 108.65(18) no
H251 . C25 . H252 . 109.466 no
C25 . C26 . C27 . 121.0(3) yes
C25 . C26 . C33 . 121.4(3) yes
C27 . C26 . C33 . 117.7(3) yes
C26 . C27 . C28 . 121.5(3) yes
C26 . C27 . H271 . 119.1(2) no
C28 . C27 . H271 . 119.4(2) no
C27 . C28 . C29 . 120.2(3) yes
C27 . C28 . H281 . 120.0(2) no
C29 . C28 . H281 . 119.9(2) no
C28 . C29 . C32 . 119.6(3) yes
C28 . C29 . O30 . 115.8(3) yes
C32 . C29 . O30 . 124.7(3) yes
O30 . C30 . H311 . 109.71(19) no
O30 . C30 . H312 . 109.17(18) no
H311 . C30 . H312 . 109.475 no
O30 . C30 . H313 . 109.51(19) no
H311 . C30 . H313 . 109.475 no
H312 . C30 . H313 . 109.477 no
C29 . C32 . C33 . 119.4(3) yes
C29 . C32 . H321 . 120.3(2) no
C33 . C32 . H321 . 120.24(19) no
C26 . C33 . C32 . 121.7(3) yes
C26 . C33 . H331 . 118.97(19) no
C32 . C33 . H331 . 119.34(19) no
C102 . C101 . C1031 . 62.1(3) yes
C102 . C101 . H1011 . 119.7(3) no
C1031 . C101 . H1011 . 119.8(4) no
C102 . C101 . H1012 . 119.6(3) no
C1031 . C101 . H1012 . 119.6(4) no
H1011 . C101 . H1012 . 109.467 no
C101 . C102 . C106 . 117.3(4) yes
C101 . C102 . C1030 . 76.6(4) yes
C106 . C102 . C1030 . 114.2(4) yes
C101 . C102 . C1031 . 61.4(3) yes
C106 . C102 . C1031 . 119.0(4) yes
C1030 . C102 . C1031 . 15.3(3) yes
C101 . C102 . N114 . 118.8(4) yes
C106 . C102 . N114 . 112.1(3) yes
C1030 . C102 . N114 . 113.2(4) yes
C1031 . C102 . N114 . 119.7(4) yes
C1030 . C104 . C1031 . 15.9(3) yes
C1030 . C105 . C1031 . 15.4(3) yes
C102 . C106 . N107 . 115.0(3) yes
C102 . C106 . O134 . 122.0(3) yes
N107 . C106 . O134 . 123.0(3) yes
C109 . C108 . C113 . 114.6(4) yes
C109 . C108 . C1100 . 77.8(4) yes
C113 . C108 . C1100 . 113.4(3) yes
C109 . C108 . C1101 . 62.0(3) yes
C113 . C108 . C1101 . 115.9(4) yes
C1100 . C108 . C1101 . 16.1(3) yes
C109 . C108 . N107 . 122.3(4) yes
C113 . C108 . N107 . 112.5(2) yes
C1100 . C108 . N107 . 111.4(3) yes
C1101 . C108 . N107 . 120.9(4) yes
C108 . C109 . C1101 . 62.8(3) yes
C108 . C109 . H1091 . 119.6(3) no
C1101 . C109 . H1091 . 119.7(4) no
C108 . C109 . H1092 . 119.5(3) no
C1101 . C109 . H1092 . 119.3(4) no
H1091 . C109 . H1092 . 109.467 no
C1100 . C111 . C1101 . 16.1(3) yes
C1100 . C112 . C1101 . 16.8(3) yes
C108 . C113 . N114 . 114.0(3) yes
C108 . C113 . O124 . 122.3(3) yes
N114 . C113 . O124 . 123.7(3) yes
C116 . C115 . N114 . 113.5(3) yes
C116 . C115 . H1151 . 108.83(19) no
N114 . C115 . H1151 . 108.55(19) no
C116 . C115 . H1152 . 107.9(2) no
N114 . C115 . H1152 . 108.6(2) no
H1151 . C115 . H1152 . 109.467 no
C115 . C116 . C117 . 122.0(3) yes
C115 . C116 . C121 . 119.9(3) yes
C117 . C116 . C121 . 118.1(3) yes
C116 . C117 . C118 . 121.1(3) yes
C116 . C117 . H1171 . 119.50(19) no
C118 . C117 . H1171 . 119.43(19) no
C117 . C118 . C119 . 120.0(3) yes
C117 . C118 . H1181 . 119.79(19) no
C119 . C118 . H1181 . 120.23(19) no
C118 . C119 . C120 . 119.9(3) yes
C118 . C119 . O122 . 115.6(3) yes
C120 . C119 . O122 . 124.5(3) yes
C119 . C120 . C121 . 119.3(3) yes
C119 . C120 . H1201 . 120.49(18) no
C121 . C120 . H1201 . 120.22(19) no
C116 . C121 . C120 . 121.6(3) yes
C116 . C121 . H1211 . 119.11(18) no
C120 . C121 . H1211 . 119.25(19) no
O122 . C123 . H1231 . 109.31(18) no
O122 . C123 . H1232 . 109.2(2) no
H1231 . C123 . H1232 . 109.476 no
O122 . C123 . H1233 . 109.9(2) no
H1231 . C123 . H1233 . 109.476 no
H1232 . C123 . H1233 . 109.477 no
C126 . C125 . N107 . 113.1(3) yes
C126 . C125 . H1251 . 108.87(17) no
N107 . C125 . H1251 . 108.78(18) no
C126 . C125 . H1252 . 108.24(18) no
N107 . C125 . H1252 . 108.32(17) no
H1251 . C125 . H1252 . 109.466 no
C125 . C126 . C127 . 120.3(3) yes
C125 . C126 . C133 . 122.8(3) yes
C127 . C126 . C133 . 117.0(3) yes
C126 . C127 . C128 . 121.5(3) yes
C126 . C127 . H1271 . 119.3(2) no
C128 . C127 . H1271 . 119.2(2) no
C127 . C128 . C129 . 120.1(3) yes
C127 . C128 . H1281 . 120.0(2) no
C129 . C128 . H1281 . 119.9(2) no
C128 . C129 . C132 . 119.2(3) yes
C128 . C129 . O130 . 115.3(3) yes
C132 . C129 . O130 . 125.4(3) yes
O130 . C131 . H1311 . 109.04(19) no
O130 . C131 . H1312 . 109.56(18) no
H1311 . C131 . H1312 . 109.476 no
O130 . C131 . H1313 . 109.79(18) no
H1311 . C131 . H1313 . 109.476 no
H1312 . C131 . H1313 . 109.476 no
C129 . C132 . C133 . 119.9(3) yes
C129 . C132 . H1321 . 119.8(2) no
C133 . C132 . H1321 . 120.23(19) no
C126 . C133 . C132 . 122.2(3) yes
C126 . C133 . H1331 . 118.6(2) no
C132 . C133 . H1331 . 119.18(19) no
C8 . C200 . C11 . 109.3(6) yes
C8 . C200 . C12 . 124.0(9) yes
C11 . C200 . C12 . 116.5(6) yes
C8 . C200 . C201 . 79.1(10) yes
C11 . C200 . C201 . 55.0(16) yes
C12 . C200 . C201 . 102.0(17) yes
C8 . C201 . C9 . 57.0(3) yes
C8 . C201 . C11 . 124.3(5) yes
C9 . C201 . C11 . 118.3(5) yes
C8 . C201 . C12 . 111.7(4) yes
C9 . C201 . C12 . 111.1(5) yes
C11 . C201 . C12 . 118.9(4) yes
C8 . C201 . C200 . 80.8(10) yes
C9 . C201 . C200 . 130.1(16) yes
C11 . C201 . C200 . 106.8(19) yes
C12 . C201 . C200 . 58.2(15) yes
C2 . C230 . C4 . 113.1(4) yes
C2 . C230 . C5 . 114.0(4) yes
C4 . C230 . C5 . 116.1(4) yes
C2 . C230 . C231 . 76.5(11) yes
C4 . C230 . C231 . 69.4(16) yes
C5 . C230 . C231 . 82.3(18) yes
C1 . C231 . C2 . 56.8(4) yes
C1 . C231 . C4 . 111.1(8) yes
C2 . C231 . C4 . 121.4(8) yes
C1 . C231 . C5 . 111.0(8) yes
C2 . C231 . C5 . 115.4(7) yes
C4 . C231 . C5 . 121.4(5) yes
C1 . C231 . C230 . 141.7(13) yes
C2 . C231 . C230 . 85.3(11) yes
C4 . C231 . C230 . 91.8(18) yes
C5 . C231 . C230 . 79.0(17) yes
C102 . C1030 . C104 . 117.1(6) yes
C102 . C1030 . C105 . 115.4(6) yes
C104 . C1030 . C105 . 119.1(5) yes
C102 . C1030 . C1031 . 80.6(14) yes
C104 . C1030 . C1031 . 83.3(20) yes
C105 . C1030 . C1031 . 76.7(23) yes
C101 . C1031 . C102 . 56.6(3) yes
C101 . C1031 . C104 . 113.3(6) yes
C102 . C1031 . C104 . 117.3(6) yes
C101 . C1031 . C105 . 111.6(6) yes
C102 . C1031 . C105 . 118.6(6) yes
C104 . C1031 . C105 . 121.1(5) yes
C101 . C1031 . C1030 . 140.6(17) yes
C102 . C1031 . C1030 . 84.1(15) yes
C104 . C1031 . C1030 . 80.8(21) yes
C105 . C1031 . C1030 . 87.9(22) yes
C108 . C1100 . C111 . 113.9(5) yes
C108 . C1100 . C112 . 116.1(5) yes
C111 . C1100 . C112 . 117.1(5) yes
C108 . C1100 . C1101 . 79.8(12) yes
C111 . C1100 . C1101 . 66.1(17) yes
C112 . C1100 . C1101 . 87.8(17) yes
C108 . C1101 . C109 . 55.3(3) yes
C108 . C1101 . C111 . 122.4(6) yes
C109 . C1101 . C111 . 111.3(6) yes
C108 . C1101 . C112 . 114.3(5) yes
C109 . C1101 . C112 . 110.4(6) yes
C111 . C1101 . C112 . 121.8(5) yes
C108 . C1101 . C1100 . 84.1(13) yes
C109 . C1101 . C1100 . 138.3(15) yes
C111 . C1101 . C1100 . 97.7(18) yes
C112 . C1101 . C1100 . 75.4(17) yes
C6 . N7 . C8 . 119.5(2) yes
C6 . N7 . C25 . 119.0(3) yes
C8 . N7 . C25 . 120.3(3) yes
C2 . N14 . C13 . 119.9(2) yes
C2 . N14 . C15 . 121.9(3) yes
C13 . N14 . C15 . 118.2(3) yes
C106 . N107 . C108 . 119.1(2) yes
C106 . N107 . C125 . 119.0(3) yes
C108 . N107 . C125 . 121.4(3) yes
C102 . N114 . C113 . 119.7(3) yes
C102 . N114 . C115 . 123.1(3) yes
C113 . N114 . C115 . 117.2(3) yes
C19 . O22 . C23 . 116.7(3) yes
C29 . O30 . C30 . 117.8(3) yes
C119 . O122 . C123 . 116.4(3) yes
C129 . O130 . C131 . 117.5(3) yes


data_CRYSTALS_cif
_database_code_CSD               206108
_audit_creation_date             02-27-05
_audit_creation_method           CRYSTALS_ver_12-03-99

_publ_section_exptl_refinement   
# see also _refine_ls_hydrogen for refinement keywords.                         
;                                                                               
H atoms placed geometrically after each cycle                                  
;
_publ_section_exptl_prep         
;                                                                               
?                                                                              
;
#==========================================================================     

_chemical_name_systematic        
# IUPAC name, in full                           
;                                                                               
(1S,3R,6S)-4,7-bis(4-methoxybenzyl)-6-isopropyl-1-phenyl-4,7-diaza-
spiro[2.5]octane-5,8-dione

;
_chemical_melting_point          'not measured'
# choose from 'full, fullcycle, atomblock, userblock, diagonal, sparse'         
_refine_ls_matrix_type           full
# choose from 'heavy, direct, difmap, geom'                                     
_atom_sites_solution_primary     direct
# _atom_sites_solution_secondary            difmap                              
_atom_sites_solution_hydrogens   geom
# choose from 'none, undef, noref, refall, refxyz, refU, constr, mixed'         
_refine_ls_hydrogen_treatment    noref
#****************************************************************************   
# General computing 
#============================================================= 
_computing_structure_refinement  
; 
CRYSTALS (Watkin et al 2001) 
;
_computing_publication_material  
; 
CRYSTALS (Watkin et al 2001) 
;
_computing_molecular_graphics    
; 
CAMERON (Watkin et al 1996) 
;
#============================================================= 
_cell_length_a                   10.4793(2)
_cell_angle_alpha                90
_cell_length_b                   10.5310(3)
_cell_angle_beta                 96.237(1)
_cell_length_c                   12.0380(4)
_cell_angle_gamma                90
_cell_volume                     1320.62(6)
_symmetry_cell_setting           'Monoclinic '
_symmetry_space_group_name_H-M   'P 1 21 1 '

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

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
'C   ' 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 International_Tables_Vol_IV_Table_2.2B
'H   ' 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7997
0.0030 International_Tables_Vol_IV_Table_2.2B
'N   ' 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 International_Tables_Vol_IV_Table_2.2B
'O   ' 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 International_Tables_Vol_IV_Table_2.2B
_chemical_formula_sum            ' C31 H34 N2 O4 '
_chemical_formula_moiety         ' C31 H34 N2 O4 '
_chemical_compound_source        
;
?
;
_chemical_formula_weight         498.62
_cell_measurement_reflns_used    3043
_cell_measurement_theta_min      1
_cell_measurement_theta_max      27
_cell_measurement_temperature    190
_cell_formula_units_Z            2
_exptl_crystal_description       ' plate '
_exptl_crystal_colour            ' colourless '
_exptl_crystal_size_min          0.10
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_max          0.30
_exptl_crystal_density_diffrn    1.254
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_F_000             532.234
_exptl_absorpt_coefficient_mu    0.083
# Sheldrick geometric definitions 0.98 0.99 
_diffrn_measurement_device_type  
; 
Enraf Nonius Kappa CCD 
;
_diffrn_radiation_monochromator  graphite
_computing_data_collection       
; 
COLLECT (Nonius BV, 1997) 
;
_computing_data_reduction        
; 
Denzo/Scalepack (Otwinowski & Minor, 1996) 
;
_computing_cell_refinement       
; 
Denzo/Scalepack (Otwinowski & Minor, 1996) 
;
_computing_structure_solution    
; 
SIR92 (Altomare et al, 1994) 
;
_diffrn_measurement_method       \w
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
; 
Denzo/Scalepack (Otwinowski & Minor, 1996) 
;
_exptl_absorpt_correction_T_min  0.98
_exptl_absorpt_correction_T_max  0.99
_diffrn_standards_interval_time  0
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_diffrn_standards_decay_%        0.00
_diffrn_ambient_temperature      190
_diffrn_reflns_number            5859
_reflns_number_total             3196
_diffrn_reflns_av_R_equivalents  0.02
# Number of reflections with Friedels Law is 3196 
# Number of reflections without Friedels Law is 0 
# Theoretical number of reflections is about 3032 
_diffrn_measured_fraction_theta_max 1.000
_reflns_number_gt                2613
_diffrn_reflns_theta_min         3.34
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_reflns_limit_h_min              -13
_reflns_limit_h_max              13
_reflns_limit_k_min              0
_reflns_limit_k_max              13
_reflns_limit_l_min              0
_reflns_limit_l_max              15
_refine_diff_density_min         -0.33
_refine_diff_density_max         0.29
_reflns_threshold_expression     >1.00\s(I)
_refine_ls_number_reflns         2613
_refine_ls_number_parameters     334
_refine_ls_R_factor_gt           0.0507
_refine_ls_wR_factor_ref         0.0496
_refine_ls_goodness_of_fit_ref   1.0366
_refine_ls_shift/su_max          0.000202
_refine_ls_structure_factor_coef F
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
Method= Tukey and Prince 
W = [weight] * [1-(deltaF/6*sigmaF)^2]^2 

0.505 0.250 0.185 
;
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
## -------------------REFERENCES ----------------------## 
## Insert your own references - in alphabetic order 
_publ_section_references         
; 

Altomare, A., Cascarano, G., Giacovazzo G., Guagliardi A., Burla M.C., 
Polidori, G. & Camalli, M. (1994) SIR92 - a program for automatic solution 
of crystal structures by direct methods. J. Appl. Cryst. (27), 435-435 

COLLECT Software, Nonius BV 1997-2001) 

Otwinowski, Z. & Minor, W. (1996), Processing of X-ray 
Diffraction Data Collected in Oscillation Mode. Methods Enzymol. 
276, 1997, 307-326. Ed Carter, C.W. & Sweet, R.M., Academic Press. 

Watkin, D.J., Prout, C.K., Carruthers, J.R., Betteridge, P.W. & Cooper 
R.I. (2001) CRYSTALS 
Issue 11. Chemical Crystallography Laboratory, OXFORD, UK. 

Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996) CAMERON, Chemical 
Crystallography Laboratory, OXFORD, UK. 
;

# Uequiv = arithmetic mean of Ui
# i.e. Ueqiv = (U1+U2+U3)/3

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_occupancy
_atom_site_adp_type
O1 O 0.40905(18) 0.3874(2) 0.90669(18) 0.0337 1.0000 Uani
C2 C 0.3455(2) 0.3049(3) 0.9465(2) 0.0279 1.0000 Uani
N3 N 0.3979(2) 0.1980(2) 0.9944(2) 0.0307 1.0000 Uani
C4 C 0.5339(3) 0.1708(3) 0.9832(3) 0.0340 1.0000 Uani
C5 C 0.5505(3) 0.1293(3) 0.8649(3) 0.0336 1.0000 Uani
C6 C 0.4966(3) 0.0172(3) 0.8219(3) 0.0399 1.0000 Uani
C7 C 0.5057(3) -0.0202(3) 0.7118(3) 0.0424 1.0000 Uani
C8 C 0.5717(3) 0.0561(4) 0.6442(3) 0.0474 1.0000 Uani
O9 O 0.5851(3) 0.0306(3) 0.5343(2) 0.0671 1.0000 Uani
C10 C 0.5275(5) -0.0816(5) 0.4871(3) 0.0648 1.0000 Uani
C11 C 0.6302(4) 0.1672(4) 0.6867(4) 0.0588 1.0000 Uani
C12 C 0.6183(3) 0.2038(4) 0.7960(3) 0.0492 1.0000 Uani
C13 C 0.3218(3) 0.1090(3) 1.0555(2) 0.0314 1.0000 Uani
C14 C 0.1919(3) 0.0867(3) 0.9894(3) 0.0335 1.0000 Uani
O15 O 0.1445(2) -0.0195(2) 0.9836(2) 0.0439 1.0000 Uani
N16 N 0.1374(2) 0.1907(3) 0.9369(2) 0.0334 1.0000 Uani
C17 C 0.2022(3) 0.3132(3) 0.9492(2) 0.0299 1.0000 Uani
C18 C 0.1611(3) 0.4107(3) 1.0327(2) 0.0348 1.0000 Uani
C19 C 0.1267(3) 0.4294(3) 0.9094(2) 0.0336 1.0000 Uani
C20 C 0.1708(3) 0.5366(3) 0.8413(2) 0.0334 1.0000 Uani
C21 C 0.1595(3) 0.6613(3) 0.8775(3) 0.0400 1.0000 Uani
C22 C 0.1846(3) 0.7621(3) 0.8084(3) 0.0449 1.0000 Uani
C23 C 0.2179(3) 0.7398(3) 0.7022(3) 0.0445 1.0000 Uani
C24 C 0.2301(3) 0.6157(3) 0.6657(3) 0.0425 1.0000 Uani
C25 C 0.2077(3) 0.5145(3) 0.7347(3) 0.0364 1.0000 Uani
C26 C 0.0269(3) 0.1726(4) 0.8510(3) 0.0433 1.0000 Uani
C27 C 0.0611(3) 0.2013(3) 0.7344(3) 0.0386 1.0000 Uani
C28 C -0.0149(3) 0.2809(4) 0.6636(3) 0.0479 1.0000 Uani
C29 C 0.0181(3) 0.3135(4) 0.5579(3) 0.0497 1.0000 Uani
C30 C 0.1308(4) 0.2662(4) 0.5243(3) 0.0469 1.0000 Uani
O31 O 0.1784(3) 0.2981(3) 0.4256(2) 0.0599 1.0000 Uani
C32 C 0.1160(4) 0.4000(5) 0.3614(3) 0.0647 1.0000 Uani
C33 C 0.2074(3) 0.1837(4) 0.5928(3) 0.0481 1.0000 Uani
C34 C 0.1721(3) 0.1520(3) 0.6972(3) 0.0443 1.0000 Uani
C35 C 0.3130(3) 0.1493(3) 1.1782(3) 0.0351 1.0000 Uani
C36 C 0.2177(4) 0.0652(4) 1.2323(3) 0.0497 1.0000 Uani
C37 C 0.4453(3) 0.1423(4) 1.2434(3) 0.0490 1.0000 Uani
H41 H 0.5661 0.1013 1.0379 0.0431 1.0000 Uiso
H42 H 0.5886 0.2488 1.0032 0.0431 1.0000 Uiso
H61 H 0.4492 -0.0411 0.8711 0.0476 1.0000 Uiso
H71 H 0.4662 -0.1042 0.6820 0.0526 1.0000 Uiso
H101 H 0.5432 -0.0909 0.4050 0.0790 1.0000 Uiso
H102 H 0.5636 -0.1604 0.5269 0.0790 1.0000 Uiso
H103 H 0.4312 -0.0825 0.4890 0.0790 1.0000 Uiso
H111 H 0.6782 0.2227 0.6377 0.0718 1.0000 Uiso
H121 H 0.6634 0.2851 0.8280 0.0598 1.0000 Uiso
H131 H 0.3702 0.0242 1.0638 0.0394 1.0000 Uiso
H181 H 0.2275 0.4689 1.0754 0.0411 1.0000 Uiso
H182 H 0.0946 0.3902 1.0837 0.0411 1.0000 Uiso
H191 H 0.0444 0.4420 0.8597 0.0410 1.0000 Uiso
H211 H 0.1337 0.6764 0.9549 0.0488 1.0000 Uiso
H221 H 0.1793 0.8539 0.8370 0.0538 1.0000 Uiso
H231 H 0.2316 0.8155 0.6505 0.0545 1.0000 Uiso
H241 H 0.2576 0.5985 0.5893 0.0499 1.0000 Uiso
H251 H 0.2200 0.4232 0.7088 0.0411 1.0000 Uiso
H261 H -0.0461 0.2296 0.8687 0.0506 1.0000 Uiso
H262 H -0.0038 0.0816 0.8551 0.0506 1.0000 Uiso
H281 H -0.0966 0.3167 0.6893 0.0537 1.0000 Uiso
H291 H -0.0386 0.3732 0.5055 0.0603 1.0000 Uiso
H321 H 0.1557 0.4176 0.2899 0.0734 1.0000 Uiso
H322 H 0.1212 0.4836 0.4056 0.0734 1.0000 Uiso
H323 H 0.0206 0.3840 0.3392 0.0734 1.0000 Uiso
H331 H 0.2902 0.1476 0.5681 0.0568 1.0000 Uiso
H341 H 0.2285 0.0932 0.7478 0.0524 1.0000 Uiso
H351 H 0.2794 0.2383 1.1792 0.0422 1.0000 Uiso
H361 H 0.2138 0.0928 1.3122 0.0634 1.0000 Uiso
H362 H 0.2506 -0.0258 1.2343 0.0634 1.0000 Uiso
H363 H 0.1324 0.0689 1.1905 0.0634 1.0000 Uiso
H371 H 0.4437 0.1685 1.3236 0.0596 1.0000 Uiso
H372 H 0.4805 0.0522 1.2432 0.0596 1.0000 Uiso
H373 H 0.5085 0.1989 1.2090 0.0596 1.0000 Uiso
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 0.029(1) 0.026(1) 0.0462(12) 0.0019(9) 0.0069(8) -0.0012(8)
C2 0.0264(12) 0.0274(13) 0.0300(13) -0.0056(12) 0.004(1) -0.0002(12)
N3 0.0250(11) 0.0280(12) 0.0401(13) 0.001(1) 0.007(1) 0.000(1)
C4 0.0243(12) 0.0302(16) 0.0483(17) 0.0037(14) 0.0076(12) 0.0033(11)
C5 0.0247(12) 0.0310(15) 0.0466(17) 0.0055(13) 0.0105(11) 0.0051(11)
C6 0.0386(16) 0.0370(17) 0.0457(17) 0.0037(14) 0.0125(13) -0.0005(14)
C7 0.0388(17) 0.0400(18) 0.0500(19) 0.0009(15) 0.0123(14) 0.0003(14)
C8 0.0474(18) 0.051(2) 0.0472(19) 0.0061(16) 0.0196(15) 0.0051(16)
O9 0.085(2) 0.0695(19) 0.0509(15) 0.0026(15) 0.0274(14) -0.0059(17)
C10 0.081(3) 0.067(3) 0.048(2) 0.002(2) 0.014(2) 0.005(2)
C11 0.066(2) 0.052(2) 0.064(2) 0.006(2) 0.0334(19) -0.0105(19)
C12 0.0485(18) 0.0365(17) 0.066(2) 0.0017(16) 0.0198(17) -0.0081(16)
C13 0.0318(13) 0.0275(14) 0.0359(15) 0.0014(12) 0.0087(11) -0.0014(12)
C14 0.0342(14) 0.0353(16) 0.0331(15) -0.0049(12) 0.0124(12) -0.0071(13)
O15 0.0447(13) 0.0335(12) 0.0545(14) -0.008(1) 0.0096(11) -0.012(1)
N16 0.0267(11) 0.0385(14) 0.0351(13) -0.0028(11) 0.004(1) -0.0075(11)
C17 0.0270(13) 0.0315(14) 0.0316(14) -0.0021(12) 0.004(1) 0.0018(12)
C18 0.0345(14) 0.0379(17) 0.0327(15) -0.0037(13) 0.0072(11) 0.0079(13)
C19 0.0286(14) 0.0394(16) 0.0327(14) -0.0019(13) 0.0029(11) 0.0057(12)
C20 0.0261(13) 0.0376(16) 0.0356(15) -0.0035(13) -0.0006(11) 0.0053(12)
C21 0.0393(15) 0.0440(18) 0.0358(16) -0.0054(14) 0.0000(12) 0.0107(14)
C22 0.0482(19) 0.0364(18) 0.0485(19) -0.0029(15) -0.0025(15) 0.0059(15)
C23 0.0392(17) 0.046(2) 0.0465(19) 0.0095(16) -0.0033(14) 0.0037(15)
C24 0.0404(16) 0.051(2) 0.0368(17) 0.0010(15) 0.0060(13) 0.0008(15)
C25 0.0346(15) 0.0383(17) 0.0366(15) -0.0047(14) 0.0052(12) -0.0003(13)
C26 0.0309(14) 0.056(2) 0.0427(17) -0.0039(16) -0.0004(12) -0.0146(15)
C27 0.0328(14) 0.0451(18) 0.0374(16) -0.0081(14) 0.0007(12) -0.0134(14)
C28 0.0306(15) 0.072(3) 0.0410(17) -0.0034(18) 0.0020(13) -0.0015(16)
C29 0.0442(18) 0.063(2) 0.0390(17) -0.0007(18) -0.0065(14) -0.0025(18)
C30 0.0539(19) 0.057(2) 0.0306(15) -0.0095(15) 0.0064(13) -0.0057(17)
O31 0.0703(17) 0.0704(19) 0.0409(13) -0.0060(13) 0.0152(12) -0.0031(16)
C32 0.062(2) 0.090(3) 0.0400(19) 0.014(2) -0.0027(17) -0.011(2)
C33 0.0537(19) 0.047(2) 0.0444(19) -0.0111(16) 0.0113(15) 0.0046(17)
C34 0.0499(19) 0.0399(17) 0.0436(18) -0.0047(15) 0.0066(15) 0.0008(15)
C35 0.0420(15) 0.0272(14) 0.0366(15) -0.0018(12) 0.0066(12) -0.0007(12)
C36 0.056(2) 0.052(2) 0.0443(18) -0.0067(16) 0.0200(16) -0.0091(17)
C37 0.0466(18) 0.054(2) 0.0448(18) -0.0011(17) -0.0043(15) 0.0004(17)
_refine_ls_extinction_method     None
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 . C2 . 1.224(3) yes
C2 . N3 . 1.354(4) yes
C2 . C17 . 1.508(4) yes
N3 . C4 . 1.474(3) yes
N3 . C13 . 1.478(4) yes
C4 . C5 . 1.518(4) yes
C4 . H41 . 1.017 no
C4 . H42 . 1.016 no
C5 . C6 . 1.384(5) yes
C5 . C12 . 1.391(4) yes
C6 . C7 . 1.396(5) yes
C6 . H61 . 1.019 no
C7 . C8 . 1.381(5) yes
C7 . H71 . 1.025 no
C8 . O9 . 1.372(4) yes
C8 . C11 . 1.392(6) yes
O9 . C10 . 1.418(6) yes
C10 . H101 . 1.024 no
C10 . H102 . 1.010 no
C10 . H103 . 1.012 no
C11 . C12 . 1.390(6) yes
C11 . H111 . 1.004 no
C12 . H121 . 1.032 no
C13 . C14 . 1.519(4) yes
C13 . C35 . 1.549(4) yes
C13 . H131 . 1.026 no
C14 . O15 . 1.222(4) yes
C14 . N16 . 1.359(4) yes
N16 . C17 . 1.458(4) yes
N16 . C26 . 1.478(4) yes
C17 . C18 . 1.531(4) yes
C17 . C19 . 1.506(4) yes
C18 . C19 . 1.502(4) yes
C18 . H181 . 1.023 no
C18 . H182 . 1.001 no
C19 . C20 . 1.498(4) yes
C19 . H191 . 1.004 no
C20 . C21 . 1.393(5) yes
C20 . C25 . 1.399(4) yes
C21 . C22 . 1.391(5) yes
C21 . H211 . 1.010 no
C22 . C23 . 1.382(5) yes
C22 . H221 . 1.030 no
C23 . C24 . 1.389(5) yes
C23 . H231 . 1.030 no
C24 . C25 . 1.388(5) yes
C24 . H241 . 1.009 no
C25 . H251 . 1.023 no
C26 . C27 . 1.517(4) yes
C26 . H261 . 1.014 no
C26 . H262 . 1.014 no
C27 . C28 . 1.384(5) yes
C27 . C34 . 1.391(5) yes
C28 . C29 . 1.397(5) yes
C28 . H281 . 1.014 no
C29 . C30 . 1.382(5) yes
C29 . H291 . 1.032 no
C30 . O31 . 1.379(4) yes
C30 . C33 . 1.392(5) yes
O31 . C32 . 1.438(5) yes
C32 . H321 . 1.014 no
C32 . H322 . 1.028 no
C32 . H323 . 1.020 no
C33 . C34 . 1.389(5) yes
C33 . H331 . 1.020 no
C34 . H341 . 1.013 no
C35 . C36 . 1.532(5) yes
C35 . C37 . 1.518(5) yes
C35 . H351 . 1.002 no
C36 . H361 . 1.010 no
C36 . H362 . 1.019 no
C36 . H363 . 0.978 no
C37 . H371 . 1.006 no
C37 . H372 . 1.018 no
C37 . H373 . 1.012 no
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 . C2 . N3 . 123.0(2) yes
O1 . C2 . C17 . 123.5(3) yes
N3 . C2 . C17 . 113.5(2) yes
C2 . N3 . C4 . 118.3(2) yes
C2 . N3 . C13 . 121.6(2) yes
C4 . N3 . C13 . 120.1(2) yes
N3 . C4 . C5 . 110.6(2) yes
N3 . C4 . H41 . 109.634 no
C5 . C4 . H41 . 109.642 no
N3 . C4 . H42 . 110.354 no
C5 . C4 . H42 . 109.629 no
H41 . C4 . H42 . 106.866 no
C4 . C5 . C6 . 120.9(3) yes
C4 . C5 . C12 . 121.0(3) yes
C6 . C5 . C12 . 118.2(3) yes
C5 . C6 . C7 . 121.9(3) yes
C5 . C6 . H61 . 120.108 no
C7 . C6 . H61 . 117.977 no
C6 . C7 . C8 . 119.0(3) yes
C6 . C7 . H71 . 120.596 no
C8 . C7 . H71 . 120.368 no
C7 . C8 . O9 . 124.3(3) yes
C7 . C8 . C11 . 120.1(3) yes
O9 . C8 . C11 . 115.6(3) yes
C8 . O9 . C10 . 117.8(3) yes
O9 . C10 . H101 . 111.134 no
O9 . C10 . H102 . 111.927 no
H101 . C10 . H102 . 106.754 no
O9 . C10 . H103 . 112.358 no
H101 . C10 . H103 . 106.634 no
H102 . C10 . H103 . 107.713 no
C8 . C11 . C12 . 120.0(3) yes
C8 . C11 . H111 . 120.144 no
C12 . C11 . H111 . 119.830 no
C5 . C12 . C11 . 120.8(3) yes
C5 . C12 . H121 . 119.241 no
C11 . C12 . H121 . 119.929 no
N3 . C13 . C14 . 109.8(2) yes
N3 . C13 . C35 . 113.1(2) yes
C14 . C13 . C35 . 113.5(2) yes
N3 . C13 . H131 . 108.233 no
C14 . C13 . H131 . 108.758 no
C35 . C13 . H131 . 103.048 no
C13 . C14 . O15 . 120.4(3) yes
C13 . C14 . N16 . 115.2(3) yes
O15 . C14 . N16 . 124.3(3) yes
C14 . N16 . C17 . 119.9(2) yes
C14 . N16 . C26 . 118.6(3) yes
C17 . N16 . C26 . 120.4(3) yes
C2 . C17 . N16 . 113.6(2) yes
C2 . C17 . C18 . 113.9(2) yes
N16 . C17 . C18 . 119.9(2) yes
C2 . C17 . C19 . 122.0(3) yes
N16 . C17 . C19 . 117.6(2) yes
C18 . C17 . C19 . 59.25(19) yes
C17 . C18 . C19 . 59.55(19) yes
C17 . C18 . H181 . 120.482 no
C19 . C18 . H181 . 119.744 no
C17 . C18 . H182 . 121.423 no
C19 . C18 . H182 . 121.704 no
H181 . C18 . H182 . 107.599 no
C17 . C19 . C18 . 61.2(2) yes
C17 . C19 . C20 . 127.1(2) yes
C18 . C19 . C20 . 125.8(3) yes
C17 . C19 . H191 . 133.243 no
C18 . C19 . H191 . 134.859 no
C20 . C19 . H191 . 82.491 no
C19 . C20 . C21 . 119.8(3) yes
C19 . C20 . C25 . 120.6(3) yes
C21 . C20 . C25 . 119.1(3) yes
C20 . C21 . C22 . 120.3(3) yes
C20 . C21 . H211 . 118.540 no
C22 . C21 . H211 . 121.157 no
C21 . C22 . C23 . 120.4(3) yes
C21 . C22 . H221 . 119.770 no
C23 . C22 . H221 . 119.786 no
C22 . C23 . C24 . 119.6(3) yes
C22 . C23 . H231 . 119.517 no
C24 . C23 . H231 . 120.897 no
C23 . C24 . C25 . 120.4(3) yes
C23 . C24 . H241 . 120.109 no
C25 . C24 . H241 . 119.479 no
C20 . C25 . C24 . 120.2(3) yes
C20 . C25 . H251 . 119.530 no
C24 . C25 . H251 . 120.266 no
N16 . C26 . C27 . 112.1(2) yes
N16 . C26 . H261 . 109.194 no
C27 . C26 . H261 . 109.650 no
N16 . C26 . H262 . 108.502 no
C27 . C26 . H262 . 109.961 no
H261 . C26 . H262 . 107.310 no
C26 . C27 . C28 . 120.8(3) yes
C26 . C27 . C34 . 120.9(3) yes
C28 . C27 . C34 . 118.3(3) yes
C27 . C28 . C29 . 121.8(3) yes
C27 . C28 . H281 . 119.110 no
C29 . C28 . H281 . 119.086 no
C28 . C29 . C30 . 118.8(3) yes
C28 . C29 . H291 . 121.618 no
C30 . C29 . H291 . 119.568 no
C29 . C30 . O31 . 124.4(3) yes
C29 . C30 . C33 . 120.5(3) yes
O31 . C30 . C33 . 115.0(3) yes
C30 . O31 . C32 . 117.3(3) yes
O31 . C32 . H321 . 112.857 no
O31 . C32 . H322 . 111.433 no
H321 . C32 . H322 . 106.233 no
O31 . C32 . H323 . 113.178 no
H321 . C32 . H323 . 106.842 no
H322 . C32 . H323 . 105.778 no
C30 . C33 . C34 . 119.6(3) yes
C30 . C33 . H331 . 120.925 no
C34 . C33 . H331 . 119.506 no
C27 . C34 . C33 . 121.0(3) yes
C27 . C34 . H341 . 119.266 no
C33 . C34 . H341 . 119.699 no
C13 . C35 . C36 . 110.8(3) yes
C13 . C35 . C37 . 109.5(3) yes
C36 . C35 . C37 . 110.7(3) yes
C13 . C35 . H351 . 108.951 no
C36 . C35 . H351 . 106.805 no
C37 . C35 . H351 . 110.038 no
C35 . C36 . H361 . 109.479 no
C35 . C36 . H362 . 108.634 no
H361 . C36 . H362 . 107.223 no
C35 . C36 . H363 . 111.163 no
H361 . C36 . H363 . 110.484 no
H362 . C36 . H363 . 109.757 no
C35 . C37 . H371 . 111.900 no
C35 . C37 . H372 . 110.803 no
H371 . C37 . H372 . 107.578 no
C35 . C37 . H373 . 111.170 no
H371 . C37 . H373 . 108.059 no
H372 . C37 . H373 . 107.127 no