Supplementary Material for Organic & Biomolecular Chemistry
This journal is © The Royal Society of Chemistry 2005

data_global
_journal_name_full               Org.Biomol.Chem.

_journal_coden_Cambridge         0177

_publ_contact_author_name        'Prof Stephen G Davies'
_publ_contact_author_address     
;
department of organic chemistry
university of oxford
mansfield road
oxford
oX1 3TA
UNITED KINGDOM
;

_publ_contact_author_email       STEVE.DAVIES@CHEM.OX.AC.UK
_publ_contact_author_phone       '01865 275 646'
_publ_contact_author_fax         '01865 275 633'

_publ_section_title              
;
Kinetic Resolution and Parallel Kinetic Resolution of
methyl (RS)-5-alkyl-cyclopentene-1-carboxylates for the asymmetric
synthesis of 5-alkyl-cispentacin derivatives
;
loop_
_publ_author_name
'S. Davies'
'A.Christopher Garner'
'Marcus J.C. Long'
'Rachel M. Morrison'
'Paul M. Roberts'
;
E.D.Savory
;
'Miles J. Sweet'
'Jonathan M. Withey'

data_1
_database_code_depnum_ccdc_archive 'CCDC 237685'
_audit_creation_date             03-28-04
_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
;

_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    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                   8.6059(1)
_cell_angle_alpha                90
_cell_length_b                   11.6484(1)
_cell_angle_beta                 90
_cell_length_c                   25.9199(3)
_cell_angle_gamma                90
_cell_volume                     2598.34(5)

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_int_tables_number      19
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
x+1/2,-y+1/2,-z
-x,y+1/2,-z+1/2
-x+1/2,-y,z+1/2

# 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            'C30 H35 N1 O4'
_chemical_formula_moiety         'C30 H35 N1 O4'
_chemical_compound_source        ?
_chemical_formula_weight         473.61

_cell_measurement_reflns_used    3223
_cell_measurement_theta_min      5
_cell_measurement_theta_max      27
_cell_measurement_temperature    190

_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    1.211
_exptl_crystal_density_meas      'not measured'
# Non-dispersive F(000):
_exptl_crystal_F_000             1016.000
_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      190
_diffrn_reflns_number            5889
_reflns_number_total             3316
_diffrn_reflns_av_R_equivalents  0.01
# Number of reflections with Friedels Law is 3316
# Number of reflections without Friedels Law is 0
# Theoretical number of reflections is about 2971

_diffrn_reflns_theta_min         5.112
_diffrn_reflns_theta_max         27.472
_diffrn_measured_fraction_theta_max 0.983

_diffrn_reflns_theta_full        27.334
_diffrn_measured_fraction_theta_full 0.983

_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       33
_reflns_limit_h_min              0
_reflns_limit_h_max              11
_reflns_limit_k_min              0
_reflns_limit_k_max              15
_reflns_limit_l_min              0
_reflns_limit_l_max              33

_refine_diff_density_min         -0.11
_refine_diff_density_max         0.17

_refine_ls_number_reflns         2742
_refine_ls_number_parameters     316

#_refine_ls_R_factor_ref 0.0322
_refine_ls_wR_factor_ref         0.0381
_refine_ls_goodness_of_fit_ref   1.1199

#_reflns_number_all 3316
_refine_ls_R_factor_all          0.0417
_refine_ls_wR_factor_all         0.0470

# 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                2742
_refine_ls_R_factor_gt           0.0322
_refine_ls_wR_factor_gt          0.0381

_refine_ls_shift/su_max          0.000458
_refine_ls_structure_factor_coef F
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
Method = Prince modified Chebychev polynomial, (Watkin, 1994)
W = [weight] * [1-(deltaF/6*sigmaF)^2]^2

0.754 0.129 0.406
;
_diffrn_radiation_probe          ?
_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. (1994),
Acta Cryst, A50, 411-437
Prince, E.
Mathematical Techniques in Crystallography
and Materials Science
Springer-Verlag, New York, 1982.

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
_atom_site_attached_hydrogens
# Replace trailing . with the number of unfound
# hydrogen atoms attaced to relavent atom
C1 C 0.7934(2) 0.46428(15) 0.70359(6) 0.0329 1.0000 Uani .
C2 C 0.6251(2) 0.41602(14) 0.69693(6) 0.0329 1.0000 Uani .
N3 N 0.52698(16) 0.48568(11) 0.66287(5) 0.0304 1.0000 Uani .
C4 C 0.4043(2) 0.41952(15) 0.63578(7) 0.0365 1.0000 Uani .
C5 C 0.4786(2) 0.33278(15) 0.59953(7) 0.0381 1.0000 Uani .
C6 C 0.5956(3) 0.36921(19) 0.56641(8) 0.0491 1.0000 Uani .
C7 C 0.6693(3) 0.2939(3) 0.5331(1) 0.0705 1.0000 Uani .
C8 C 0.6263(4) 0.1806(3) 0.53190(12) 0.0784 1.0000 Uani .
C9 C 0.5088(4) 0.14305(19) 0.56309(11) 0.0744 1.0000 Uani .
C10 C 0.4342(3) 0.21755(17) 0.59717(9) 0.0547 1.0000 Uani .
C11 C 0.2786(3) 0.3685(2) 0.67052(9) 0.0562 1.0000 Uani .
C12 C 0.4689(2) 0.59210(15) 0.68649(6) 0.0349 1.0000 Uani .
C13 C 0.3967(2) 0.67200(14) 0.64748(6) 0.0317 1.0000 Uani .
C14 C 0.4894(2) 0.72206(14) 0.60902(6) 0.0316 1.0000 Uani .
C15 C 0.4266(2) 0.79845(14) 0.57418(6) 0.0308 1.0000 Uani .
C16 C 0.2677(2) 0.82787(14) 0.57733(6) 0.0326 1.0000 Uani .
C17 C 0.1754(2) 0.77696(15) 0.61425(7) 0.0357 1.0000 Uani .
C18 C 0.2405(2) 0.69929(15) 0.64924(6) 0.0346 1.0000 Uani .
O19 O 0.21660(15) 0.90854(12) 0.54252(5) 0.0443 1.0000 Uani .
C20 C 0.0593(3) 0.9431(3) 0.54783(13) 0.0871 1.0000 Uani .
O21 O 0.50706(15) 0.85100(11) 0.53514(5) 0.0399 1.0000 Uani .
C22 C 0.6706(2) 0.83329(19) 0.53391(8) 0.0459 1.0000 Uani .
C23 C 0.5745(2) 0.39847(17) 0.75359(7) 0.0439 1.0000 Uani .
C24 C 0.6591(2) 0.4879(2) 0.78640(7) 0.0458 1.0000 Uani .
C25 C 0.7981(2) 0.53344(15) 0.75434(6) 0.0350 1.0000 Uani .
C26 C 0.9530(2) 0.52698(15) 0.78228(6) 0.0326 1.0000 Uani .
C27 C 1.0288(2) 0.42269(16) 0.79085(6) 0.0367 1.0000 Uani .
C28 C 1.1686(2) 0.41816(18) 0.81777(7) 0.0429 1.0000 Uani .
C29 C 1.2332(2) 0.5175(2) 0.83726(8) 0.0502 1.0000 Uani .
C30 C 1.1586(3) 0.62109(19) 0.83057(9) 0.0555 1.0000 Uani .
C31 C 1.0198(3) 0.62608(16) 0.80251(8) 0.0449 1.0000 Uani .
C32 C 0.8484(2) 0.53041(16) 0.65731(7) 0.0347 1.0000 Uani .
O33 O 0.90478(16) 0.45957(13) 0.62128(5) 0.0464 1.0000 Uani .
C34 C 0.9554(3) 0.5131(2) 0.57354(8) 0.0620 1.0000 Uani .
O35 O 0.84547(17) 0.63336(12) 0.65244(5) 0.0451 1.0000 Uani .
H11 H 0.8694 0.3977 0.7068 0.0404 1.0000 Uiso .
H21 H 0.6148 0.3414 0.6767 0.0416 1.0000 Uiso .
H41 H 0.3415 0.4757 0.6146 0.0459 1.0000 Uiso .
H61 H 0.6316 0.4522 0.5679 0.0602 1.0000 Uiso .
H71 H 0.7563 0.3236 0.5092 0.0857 1.0000 Uiso .
H81 H 0.6833 0.1267 0.5075 0.0991 1.0000 Uiso .
H91 H 0.4726 0.0595 0.5605 0.0902 1.0000 Uiso .
H101 H 0.3484 0.1885 0.6216 0.0690 1.0000 Uiso .
H111 H 0.2006 0.3241 0.6494 0.0679 1.0000 Uiso .
H112 H 0.2245 0.4290 0.6905 0.0679 1.0000 Uiso .
H113 H 0.3286 0.3123 0.6956 0.0679 1.0000 Uiso .
H121 H 0.5561 0.6333 0.7045 0.0447 1.0000 Uiso .
H122 H 0.3876 0.5720 0.7134 0.0447 1.0000 Uiso .
H141 H 0.6032 0.7007 0.6065 0.0381 1.0000 Uiso .
H171 H 0.0618 0.7966 0.6160 0.0428 1.0000 Uiso .
H181 H 0.1726 0.6614 0.6760 0.0425 1.0000 Uiso .
H201 H 0.0308 1.0023 0.5212 0.1056 1.0000 Uiso .
H202 H 0.0386 0.9768 0.5831 0.1056 1.0000 Uiso .
H203 H -0.0130 0.8750 0.5433 0.1056 1.0000 Uiso .
H221 H 0.7175 0.8757 0.5040 0.0574 1.0000 Uiso .
H222 H 0.7194 0.8625 0.5667 0.0574 1.0000 Uiso .
H223 H 0.6945 0.7495 0.5304 0.0574 1.0000 Uiso .
H231 H 0.6047 0.3178 0.7656 0.0519 1.0000 Uiso .
H232 H 0.4594 0.4061 0.7572 0.0519 1.0000 Uiso .
H241 H 0.6975 0.4514 0.8196 0.0581 1.0000 Uiso .
H242 H 0.5848 0.5510 0.7959 0.0581 1.0000 Uiso .
H251 H 0.7882 0.6186 0.7464 0.0423 1.0000 Uiso .
H271 H 0.9812 0.3496 0.7771 0.0451 1.0000 Uiso .
H281 H 1.2227 0.3428 0.8226 0.0544 1.0000 Uiso .
H291 H 1.3326 0.5136 0.8571 0.0626 1.0000 Uiso .
H301 H 1.2054 0.6935 0.8458 0.0676 1.0000 Uiso .
H311 H 0.9675 0.7021 0.7964 0.0546 1.0000 Uiso .
H341 H 0.9964 0.4540 0.5492 0.0779 1.0000 Uiso .
H342 H 1.0411 0.5703 0.5812 0.0779 1.0000 Uiso .
H343 H 0.8671 0.5552 0.5569 0.0779 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
C1 0.0321(8) 0.0357(8) 0.0309(8) -0.0021(7) -0.0015(6) 0.0057(7)
C2 0.0361(8) 0.0306(7) 0.0322(8) 0.0047(7) -0.0029(7) 0.0006(7)
N3 0.0320(6) 0.0286(6) 0.0305(6) 0.0015(5) -0.0029(6) 0.0014(6)
C4 0.0334(8) 0.0363(8) 0.0399(9) 0.0040(7) -0.0050(7) -0.0036(8)
C5 0.042(1) 0.0322(8) 0.0398(9) 0.0006(7) -0.0146(8) -0.0005(8)
C6 0.0546(11) 0.0516(11) 0.041(1) -0.0100(9) -0.0021(9) -0.005(1)
C7 0.0649(15) 0.0908(19) 0.0560(13) -0.0336(14) -0.0043(12) 0.0043(15)
C8 0.081(2) 0.0795(18) 0.0741(17) -0.0406(15) -0.0310(16) 0.0255(16)
C9 0.103(2) 0.036(1) 0.0840(18) -0.0187(11) -0.0522(18) 0.0119(14)
C10 0.0697(15) 0.0350(9) 0.0595(12) 0.0029(9) -0.0279(12) -0.007(1)
C11 0.0424(11) 0.0638(13) 0.0625(12) 0.0062(11) 0.000(1) -0.016(1)
C12 0.0376(8) 0.0362(8) 0.0310(7) 0.0005(7) 0.0010(7) 0.0053(8)
C13 0.0346(8) 0.0296(7) 0.0308(8) -0.0038(6) -0.0029(7) 0.0029(7)
C14 0.0283(8) 0.0322(8) 0.0344(8) -0.0037(6) -0.0006(7) 0.0020(7)
C15 0.0307(8) 0.0305(7) 0.0313(7) -0.0025(6) 0.0004(7) -0.0014(6)
C16 0.0314(8) 0.0323(8) 0.0341(8) -0.0004(6) -0.0049(7) 0.0017(7)
C17 0.0271(8) 0.0393(9) 0.0406(8) -0.0009(7) -0.0003(7) 0.0023(7)
C18 0.0336(8) 0.0359(8) 0.0344(8) 0.0006(7) 0.0035(7) -0.0014(7)
O19 0.0344(6) 0.0479(7) 0.0505(7) 0.0139(6) -0.0009(6) 0.0080(6)
C20 0.0469(13) 0.115(2) 0.100(2) 0.0629(19) 0.0133(13) 0.0373(15)
O21 0.0323(6) 0.0450(7) 0.0426(7) 0.0097(6) 0.0046(5) 0.0031(6)
C22 0.0326(9) 0.0600(12) 0.045(1) 0.0048(9) 0.0075(8) 0.0020(9)
C23 0.046(1) 0.051(1) 0.0347(8) 0.0144(8) -0.0002(8) -0.0024(9)
C24 0.0374(9) 0.0679(13) 0.0320(8) -0.0013(9) 0.0017(8) 0.007(1)
C25 0.0377(9) 0.0376(8) 0.0296(8) -0.0020(7) -0.0020(7) 0.0067(7)
C26 0.0351(8) 0.0375(8) 0.0252(7) 0.0017(7) 0.0028(7) -0.0004(7)
C27 0.0378(9) 0.0393(8) 0.0330(8) -0.0005(7) -0.0004(7) 0.0016(8)
C28 0.0367(9) 0.055(1) 0.0374(9) 0.0047(8) -0.0008(8) 0.0042(9)
C29 0.0362(9) 0.0687(13) 0.046(1) 0.010(1) -0.0062(9) -0.012(1)
C30 0.0559(12) 0.0535(12) 0.0570(12) 0.001(1) -0.0091(11) -0.0231(11)
C31 0.0513(11) 0.0365(9) 0.047(1) 0.0023(8) -0.0029(9) -0.0054(9)
C32 0.0273(7) 0.045(1) 0.0324(8) -0.0037(7) -0.0018(7) 0.0000(7)
O33 0.0474(7) 0.0591(8) 0.0327(6) -0.0097(6) 0.0083(6) -0.0011(7)
C34 0.0632(13) 0.0865(17) 0.0365(9) -0.0107(11) 0.017(1) -0.0192(13)
O35 0.0465(7) 0.0444(7) 0.0443(7) 0.0047(6) 0.0076(6) -0.0040(6)
_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
C1 . C2 . 1.563(2) yes
C1 . C25 . 1.543(2) yes
C1 . C32 . 1.502(2) yes
C1 . H11 . 1.018 no
C2 . N3 . 1.467(2) yes
C2 . C23 . 1.545(2) yes
C2 . H21 . 1.019 no
N3 . C4 . 1.484(2) yes
N3 . C12 . 1.470(2) yes
C4 . C5 . 1.521(3) yes
C4 . C11 . 1.528(3) yes
C4 . H41 . 1.011 no
C5 . C6 . 1.389(3) yes
C5 . C10 . 1.397(3) yes
C6 . C7 . 1.385(3) yes
C6 . H61 . 1.016 no
C7 . C8 . 1.371(4) yes
C7 . H71 . 1.032 no
C8 . C9 . 1.367(5) yes
C8 . H81 . 1.017 no
C9 . C10 . 1.395(4) yes
C9 . H91 . 1.024 no
C10 . H101 . 1.030 no
C11 . H111 . 1.009 no
C11 . H112 . 0.990 no
C11 . H113 . 1.018 no
C12 . C13 . 1.508(2) yes
C12 . H121 . 1.006 no
C12 . H122 . 1.016 no
C13 . C14 . 1.403(2) yes
C13 . C18 . 1.383(3) yes
C14 . C15 . 1.378(2) yes
C14 . H141 . 1.012 no
C15 . C16 . 1.412(2) yes
C15 . O21 . 1.370(2) yes
C16 . C17 . 1.378(2) yes
C16 . O19 . 1.375(2) yes
C17 . C18 . 1.398(2) yes
C17 . H171 . 1.005 no
C18 . H181 . 1.008 no
O19 . C20 . 1.419(3) yes
C20 . H201 . 1.005 no
C20 . H202 . 1.012 no
C20 . H203 . 1.014 no
O21 . C22 . 1.423(2) yes
C22 . H221 . 1.004 no
C22 . H222 . 1.007 no
C22 . H223 . 1.002 no
C23 . C24 . 1.529(3) yes
C23 . H231 . 1.023 no
C23 . H232 . 0.999 no
C24 . C25 . 1.550(3) yes
C24 . H241 . 1.016 no
C24 . H242 . 1.005 no
C25 . C26 . 1.519(2) yes
C25 . H251 . 1.017 no
C26 . C27 . 1.396(2) yes
C26 . C31 . 1.392(3) yes
C27 . C28 . 1.391(3) yes
C27 . H271 . 1.010 no
C28 . C29 . 1.380(3) yes
C28 . H281 . 1.001 no
C29 . C30 . 1.378(3) yes
C29 . H291 . 0.998 no
C30 . C31 . 1.400(3) yes
C30 . H301 . 1.015 no
C31 . H311 . 1.006 no
C32 . O33 . 1.337(2) yes
C32 . O35 . 1.206(2) yes
O33 . C34 . 1.453(2) yes
C34 . H341 . 0.998 no
C34 . H342 . 1.013 no
C34 . H343 . 1.001 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
C2 . C1 . C25 . 107.83(14) yes
C2 . C1 . C32 . 112.83(13) yes
C25 . C1 . C32 . 113.88(14) yes
C2 . C1 . H11 . 109.271 no
C25 . C1 . H11 . 108.152 no
C32 . C1 . H11 . 104.689 no
C1 . C2 . N3 . 113.65(13) yes
C1 . C2 . C23 . 101.75(14) yes
N3 . C2 . C23 . 118.88(15) yes
C1 . C2 . H21 . 116.382 no
N3 . C2 . H21 . 96.429 no
C23 . C2 . H21 . 110.582 no
C2 . N3 . C4 . 114.04(13) yes
C2 . N3 . C12 . 114.31(13) yes
C4 . N3 . C12 . 113.12(13) yes
N3 . C4 . C5 . 109.74(14) yes
N3 . C4 . C11 . 115.28(15) yes
C5 . C4 . C11 . 113.81(16) yes
N3 . C4 . H41 . 107.556 no
C5 . C4 . H41 . 108.560 no
C11 . C4 . H41 . 101.196 no
C4 . C5 . C6 . 118.93(16) yes
C4 . C5 . C10 . 123.40(19) yes
C6 . C5 . C10 . 117.7(2) yes
C5 . C6 . C7 . 121.6(2) yes
C5 . C6 . H61 . 119.171 no
C7 . C6 . H61 . 119.196 no
C6 . C7 . C8 . 120.0(3) yes
C6 . C7 . H71 . 119.560 no
C8 . C7 . H71 . 120.390 no
C7 . C8 . C9 . 119.6(2) yes
C7 . C8 . H81 . 118.544 no
C9 . C8 . H81 . 121.843 no
C8 . C9 . C10 . 121.1(2) yes
C8 . C9 . H91 . 119.408 no
C10 . C9 . H91 . 119.500 no
C5 . C10 . C9 . 120.0(2) yes
C5 . C10 . H101 . 118.952 no
C9 . C10 . H101 . 121.014 no
C4 . C11 . H111 . 110.556 no
C4 . C11 . H112 . 111.310 no
H111 . C11 . H112 . 109.582 no
C4 . C11 . H113 . 109.118 no
H111 . C11 . H113 . 107.363 no
H112 . C11 . H113 . 108.811 no
N3 . C12 . C13 . 112.41(13) yes
N3 . C12 . H121 . 109.985 no
C13 . C12 . H121 . 108.893 no
N3 . C12 . H122 . 109.027 no
C13 . C12 . H122 . 108.658 no
H121 . C12 . H122 . 107.749 no
C12 . C13 . C14 . 119.93(15) yes
C12 . C13 . C18 . 121.35(16) yes
C14 . C13 . C18 . 118.71(16) yes
C13 . C14 . C15 . 120.75(16) yes
C13 . C14 . H141 . 119.547 no
C15 . C14 . H141 . 119.698 no
C14 . C15 . C16 . 119.88(16) yes
C14 . C15 . O21 . 125.07(15) yes
C16 . C15 . O21 . 115.05(15) yes
C15 . C16 . C17 . 119.61(16) yes
C15 . C16 . O19 . 115.97(15) yes
C17 . C16 . O19 . 124.42(15) yes
C16 . C17 . C18 . 119.87(16) yes
C16 . C17 . H171 . 119.681 no
C18 . C17 . H171 . 120.446 no
C13 . C18 . C17 . 121.14(16) yes
C13 . C18 . H181 . 119.055 no
C17 . C18 . H181 . 119.803 no
C16 . O19 . C20 . 115.81(16) yes
O19 . C20 . H201 . 111.148 no
O19 . C20 . H202 . 111.443 no
H201 . C20 . H202 . 108.131 no
O19 . C20 . H203 . 110.619 no
H201 . C20 . H203 . 107.932 no
H202 . C20 . H203 . 107.412 no
C15 . O21 . C22 . 116.83(14) yes
O21 . C22 . H221 . 110.068 no
O21 . C22 . H222 . 110.155 no
H221 . C22 . H222 . 108.569 no
O21 . C22 . H223 . 110.246 no
H221 . C22 . H223 . 109.009 no
H222 . C22 . H223 . 108.754 no
C2 . C23 . C24 . 107.73(15) yes
C2 . C23 . H231 . 109.813 no
C24 . C23 . H231 . 109.620 no
C2 . C23 . H232 . 110.846 no
C24 . C23 . H232 . 111.119 no
H231 . C23 . H232 . 107.717 no
C23 . C24 . C25 . 107.61(14) yes
C23 . C24 . H241 . 109.972 no
C25 . C24 . H241 . 110.310 no
C23 . C24 . H242 . 109.379 no
C25 . C24 . H242 . 111.776 no
H241 . C24 . H242 . 107.795 no
C1 . C25 . C24 . 104.94(14) yes
C1 . C25 . C26 . 113.81(14) yes
C24 . C25 . C26 . 113.88(14) yes
C1 . C25 . H251 . 109.601 no
C24 . C25 . H251 . 112.182 no
C26 . C25 . H251 . 102.589 no
C25 . C26 . C27 . 121.92(16) yes
C25 . C26 . C31 . 120.06(16) yes
C27 . C26 . C31 . 117.94(16) yes
C26 . C27 . C28 . 121.08(17) yes
C26 . C27 . H271 . 119.164 no
C28 . C27 . H271 . 119.752 no
C27 . C28 . C29 . 120.03(19) yes
C27 . C28 . H281 . 119.843 no
C29 . C28 . H281 . 120.125 no
C28 . C29 . C30 . 120.04(17) yes
C28 . C29 . H291 . 119.708 no
C30 . C29 . H291 . 120.232 no
C29 . C30 . C31 . 119.96(19) yes
C29 . C30 . H301 . 119.652 no
C31 . C30 . H301 . 120.390 no
C26 . C31 . C30 . 120.91(19) yes
C26 . C31 . H311 . 119.071 no
C30 . C31 . H311 . 120.016 no
C1 . C32 . O33 . 110.82(15) yes
C1 . C32 . O35 . 125.93(16) yes
O33 . C32 . O35 . 123.24(17) yes
C32 . O33 . C34 . 116.01(17) yes
O33 . C34 . H341 . 110.320 no
O33 . C34 . H342 . 109.543 no
H341 . C34 . H342 . 108.605 no
O33 . C34 . H343 . 110.468 no
H341 . C34 . H343 . 109.542 no
H342 . C34 . H343 . 108.315 no

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

data_2
_database_code_depnum_ccdc_archive 'CCDC 237686'

_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    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                   9.4415(1)
_cell_angle_alpha                90
_cell_length_b                   15.0875(2)
_cell_angle_beta                 90
_cell_length_c                   18.2970(3)
_cell_angle_gamma                90
_cell_volume                     2606.38(6)

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_int_tables_number      19
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
x+1/2,-y+1/2,-z
-x,y+1/2,-z+1/2
-x+1/2,-y,z+1/2

# 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            'C31 H37 N1 O2'
_chemical_formula_moiety         'C31 H37 N1 O2'
_chemical_compound_source        ?
_chemical_formula_weight         455.64

_cell_measurement_reflns_used    3272
_cell_measurement_theta_min      5
_cell_measurement_theta_max      27
_cell_measurement_temperature    190

_exptl_crystal_description       ' plate '
_exptl_crystal_colour            ' colourless '
_exptl_crystal_size_min          0.30
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_max          0.50

_exptl_crystal_density_diffrn    1.161
_exptl_crystal_density_meas      'not measured'
# Non-dispersive F(000):
_exptl_crystal_F_000             984.000
_exptl_absorpt_coefficient_mu    0.071
# Sheldrick geometric definitions 0.97 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  0.97
_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      190
_diffrn_reflns_number            5898
_reflns_number_total             3327
_diffrn_reflns_av_R_equivalents  0.01
# Number of reflections with Friedels Law is 3327
# Number of reflections without Friedels Law is 0
# Theoretical number of reflections is about 2991

_diffrn_reflns_theta_min         5.134
_diffrn_reflns_theta_max         27.494
_diffrn_measured_fraction_theta_max 0.988

_diffrn_reflns_theta_full        27.356
_diffrn_measured_fraction_theta_full 0.988

_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_reflns_limit_h_min              0
_reflns_limit_h_max              12
_reflns_limit_k_min              0
_reflns_limit_k_max              19
_reflns_limit_l_min              0
_reflns_limit_l_max              23

_refine_diff_density_min         -0.16
_refine_diff_density_max         0.17

_refine_ls_number_reflns         2898
_refine_ls_number_parameters     307

#_refine_ls_R_factor_ref 0.0379
_refine_ls_wR_factor_ref         0.0442
_refine_ls_goodness_of_fit_ref   1.1113

#_reflns_number_all 3327
_refine_ls_R_factor_all          0.0444
_refine_ls_wR_factor_all         0.0501

# 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                2898
_refine_ls_R_factor_gt           0.0379
_refine_ls_wR_factor_gt          0.0442

_refine_ls_shift/su_max          0.000312
_refine_ls_structure_factor_coef F
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
Method = Prince modified Chebychev polynomial, (Watkin, 1994)
W = [weight] * [1-(deltaF/6*sigmaF)^2]^2

1.31 0.291 0.755
;
_diffrn_radiation_probe          ?
_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. (1994),
Acta Cryst, A50, 411-437
Prince, E.
Mathematical Techniques in Crystallography
and Materials Science
Springer-Verlag, New York, 1982.

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
_atom_site_attached_hydrogens
# Replace trailing . with the number of unfound
# hydrogen atoms attaced to relavent atom
C1 C 0.13465(17) 0.20114(11) 0.26179(8) 0.0273 1.0000 Uani .
C2 C -0.01058(18) 0.24543(13) 0.25262(9) 0.0312 1.0000 Uani .
C3 C -0.08306(17) 0.24363(12) 0.17814(8) 0.0281 1.0000 Uani .
C4 C -0.13081(19) 0.32398(12) 0.1484(1) 0.0336 1.0000 Uani .
C5 C -0.20501(19) 0.32464(13) 0.0825(1) 0.0368 1.0000 Uani .
C6 C -0.23556(17) 0.24792(14) 0.04490(9) 0.0336 1.0000 Uani .
C7 C -0.18816(19) 0.16895(13) 0.0744(1) 0.0342 1.0000 Uani .
C8 C -0.11195(18) 0.16488(12) 0.1399(1) 0.0319 1.0000 Uani .
C9 C -0.0648(3) 0.07314(14) 0.16319(14) 0.0573 1.0000 Uani .
C10 C -0.3206(2) 0.24900(18) -0.0251(1) 0.0467 1.0000 Uani .
C11 C -0.1053(3) 0.41258(15) 0.18556(14) 0.0599 1.0000 Uani .
C12 C -0.0980(2) 0.20455(18) 0.3149(1) 0.0485 1.0000 Uani .
C13 C 0.0038(2) 0.19914(17) 0.37871(11) 0.0460 1.0000 Uani .
C14 C 0.15633(18) 0.19137(11) 0.34702(9) 0.0288 1.0000 Uani .
N15 N 0.26450(14) 0.25080(9) 0.37768(7) 0.0263 1.0000 Uani .
C16 C 0.33311(18) 0.21465(11) 0.44435(9) 0.0280 1.0000 Uani .
C17 C 0.41909(18) 0.13255(11) 0.4247(1) 0.0310 1.0000 Uani .
C18 C 0.5072(2) 0.13571(14) 0.36381(12) 0.0414 1.0000 Uani .
C19 C 0.5871(2) 0.06285(17) 0.34343(15) 0.0567 1.0000 Uani .
C20 C 0.5816(3) -0.01394(15) 0.38488(19) 0.0648 1.0000 Uani .
C21 C 0.4971(3) -0.01747(15) 0.44553(19) 0.0623 1.0000 Uani .
C22 C 0.4147(2) 0.05513(13) 0.46558(13) 0.0457 1.0000 Uani .
C23 C 0.2321(2) 0.19977(14) 0.50902(9) 0.0388 1.0000 Uani .
C24 C 0.2205(2) 0.34350(12) 0.3872(1) 0.0338 1.0000 Uani .
C25 C 0.3448(2) 0.40505(11) 0.4003(1) 0.0374 1.0000 Uani .
C26 C 0.3601(3) 0.44782(14) 0.46717(12) 0.0502 1.0000 Uani .
C27 C 0.4718(4) 0.50707(15) 0.47798(16) 0.0647 1.0000 Uani .
C28 C 0.5665(4) 0.52405(15) 0.42291(18) 0.0699 1.0000 Uani .
C29 C 0.5523(3) 0.48265(18) 0.35686(17) 0.0690 1.0000 Uani .
C30 C 0.4417(3) 0.42271(16) 0.34555(13) 0.0539 1.0000 Uani .
C31 C 0.25335(17) 0.24955(13) 0.22418(8) 0.0303 1.0000 Uani .
O32 O 0.35845(14) 0.1943(1) 0.20647(7) 0.0409 1.0000 Uani .
C33 C 0.4815(2) 0.23420(19) 0.17244(14) 0.0555 1.0000 Uani .
O34 O 0.25360(15) 0.32749(9) 0.21001(7) 0.0415 1.0000 Uani .
H11 H 0.1360 0.1415 0.2373 0.0356 1.0000 Uiso .
H21 H 0.0019 0.3121 0.2556 0.0413 1.0000 Uiso .
H51 H -0.2376 0.3830 0.0620 0.0482 1.0000 Uiso .
H71 H -0.2072 0.1127 0.0473 0.0447 1.0000 Uiso .
H91 H -0.1015 0.0284 0.1275 0.0729 1.0000 Uiso .
H92 H -0.1061 0.0592 0.2130 0.0729 1.0000 Uiso .
H93 H 0.0395 0.0705 0.1657 0.0729 1.0000 Uiso .
H101 H -0.3313 0.1869 -0.0447 0.0582 1.0000 Uiso .
H102 H -0.4172 0.2739 -0.0155 0.0582 1.0000 Uiso .
H103 H -0.2718 0.2861 -0.0628 0.0582 1.0000 Uiso .
H111 H -0.1509 0.4618 0.1556 0.0757 1.0000 Uiso .
H112 H -0.1517 0.4136 0.2355 0.0757 1.0000 Uiso .
H113 H -0.0032 0.4250 0.1907 0.0757 1.0000 Uiso .
H121 H -0.1826 0.2442 0.3272 0.0633 1.0000 Uiso .
H122 H -0.1345 0.1451 0.3014 0.0633 1.0000 Uiso .
H131 H -0.0027 0.2557 0.4097 0.0628 1.0000 Uiso .
H132 H -0.0192 0.1480 0.4110 0.0628 1.0000 Uiso .
H141 H 0.2000 0.1321 0.3598 0.0374 1.0000 Uiso .
H161 H 0.4000 0.2621 0.4628 0.0377 1.0000 Uiso .
H181 H 0.5121 0.1923 0.3339 0.0524 1.0000 Uiso .
H191 H 0.6486 0.0662 0.2975 0.0703 1.0000 Uiso .
H201 H 0.6361 -0.0684 0.3691 0.0830 1.0000 Uiso .
H211 H 0.4960 -0.0732 0.4773 0.0775 1.0000 Uiso .
H221 H 0.3508 0.0518 0.5104 0.0577 1.0000 Uiso .
H231 H 0.2867 0.1765 0.5522 0.0512 1.0000 Uiso .
H232 H 0.1867 0.2576 0.5235 0.0512 1.0000 Uiso .
H233 H 0.1574 0.1566 0.4953 0.0512 1.0000 Uiso .
H241 H 0.1547 0.3476 0.4301 0.0445 1.0000 Uiso .
H242 H 0.1692 0.3639 0.3421 0.0445 1.0000 Uiso .
H261 H 0.2892 0.4351 0.5087 0.0651 1.0000 Uiso .
H271 H 0.4859 0.5376 0.5269 0.0819 1.0000 Uiso .
H281 H 0.6470 0.5686 0.4307 0.0913 1.0000 Uiso .
H291 H 0.6220 0.4959 0.3152 0.0826 1.0000 Uiso .
H301 H 0.4328 0.3917 0.2963 0.0673 1.0000 Uiso .
H331 H 0.5537 0.1879 0.1607 0.0712 1.0000 Uiso .
H332 H 0.5245 0.2797 0.2056 0.0712 1.0000 Uiso .
H333 H 0.4530 0.2646 0.1252 0.0712 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
C1 0.0257(7) 0.0313(8) 0.0247(7) -0.0029(6) 0.0001(6) -0.0028(7)
C2 0.0259(7) 0.0427(9) 0.0252(7) -0.0035(7) -0.0010(6) -0.0004(8)
C3 0.0238(7) 0.0354(8) 0.0250(7) -0.0028(7) -0.0006(6) -0.0027(7)
C4 0.0333(8) 0.0341(9) 0.0335(8) -0.0047(7) -0.0026(7) 0.0021(7)
C5 0.0314(8) 0.0405(9) 0.0384(9) 0.0053(7) -0.0030(7) 0.0041(8)
C6 0.0230(7) 0.051(1) 0.0269(7) 0.0016(8) 0.0002(6) -0.0031(8)
C7 0.0311(8) 0.0393(9) 0.0320(8) -0.0066(7) -0.0034(7) -0.0059(8)
C8 0.0284(7) 0.0333(8) 0.0340(8) -0.0009(7) -0.0042(7) -0.0052(7)
C9 0.0732(16) 0.033(1) 0.0658(14) 0.000(1) -0.0324(13) -0.007(1)
C10 0.040(1) 0.0694(13) 0.0305(8) 0.002(1) -0.0099(8) -0.0037(11)
C11 0.0759(17) 0.036(1) 0.0683(15) -0.014(1) -0.0231(14) 0.0120(11)
C12 0.0271(8) 0.0878(16) 0.0306(9) 0.002(1) 0.0016(7) -0.008(1)
C13 0.0262(8) 0.0797(15) 0.0320(9) 0.010(1) 0.0029(7) -0.011(1)
C14 0.0264(7) 0.0339(8) 0.0260(7) 0.0045(6) -0.0017(6) -0.0053(6)
N15 0.0259(6) 0.0266(6) 0.0263(6) -0.0003(5) -0.0027(5) 0.0003(6)
C16 0.0290(7) 0.0287(8) 0.0264(7) -0.0004(6) -0.0035(7) -0.0007(6)
C17 0.0258(7) 0.0284(8) 0.0388(8) -0.0019(7) -0.0082(7) -0.0011(7)
C18 0.0340(9) 0.041(1) 0.0494(11) -0.0069(9) 0.0004(8) 0.0020(8)
C19 0.038(1) 0.0601(14) 0.0725(15) -0.0239(12) 0.0018(11) 0.005(1)
C20 0.0409(11) 0.0357(11) 0.118(2) -0.0225(13) -0.0168(15) 0.010(1)
C21 0.0450(12) 0.032(1) 0.110(2) 0.0078(12) -0.0140(15) 0.004(1)
C22 0.0367(9) 0.0363(9) 0.0640(13) 0.011(1) -0.009(1) 0.0005(8)
C23 0.041(1) 0.049(1) 0.0268(8) 0.0019(7) -0.0007(8) -0.0000(9)
C24 0.0355(9) 0.0314(8) 0.0347(8) -0.0015(7) -0.0040(7) 0.0059(7)
C25 0.047(1) 0.0229(7) 0.0420(9) -0.0024(7) -0.0136(9) 0.0060(8)
C26 0.0662(14) 0.0342(9) 0.0502(11) -0.0098(9) -0.0215(11) 0.017(1)
C27 0.0836(19) 0.0349(11) 0.0756(16) -0.0178(11) -0.0453(16) 0.0105(12)
C28 0.0814(19) 0.0354(11) 0.093(2) 0.0044(12) -0.0393(18) -0.0147(12)
C29 0.0745(17) 0.0562(14) 0.0764(17) 0.0119(13) -0.0121(15) -0.0301(14)
C30 0.0644(14) 0.0447(11) 0.0526(12) -0.001(1) -0.0078(11) -0.0181(11)
C31 0.0279(7) 0.0394(9) 0.0236(6) -0.0027(7) 0.0008(6) -0.0049(8)
O32 0.0310(6) 0.0497(8) 0.0420(7) -0.0024(6) 0.0118(6) -0.0009(6)
C33 0.035(1) 0.0749(16) 0.0566(12) -0.0045(12) 0.021(1) -0.008(1)
O34 0.0429(7) 0.0407(7) 0.0407(7) 0.0060(6) 0.0051(6) -0.0087(6)
_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
C1 . C2 . 1.535(2) yes
C1 . C14 . 1.580(2) yes
C1 . C31 . 1.504(2) yes
C1 . H11 . 1.005 no
C2 . C3 . 1.525(2) yes
C2 . C12 . 1.536(3) yes
C2 . H21 . 1.014 no
C3 . C4 . 1.403(3) yes
C3 . C8 . 1.406(2) yes
C4 . C5 . 1.395(3) yes
C4 . C11 . 1.519(3) yes
C5 . C6 . 1.377(3) yes
C5 . H51 . 1.005 no
C6 . C7 . 1.382(3) yes
C6 . C10 . 1.513(2) yes
C7 . C8 . 1.400(2) yes
C7 . H71 . 0.999 no
C8 . C9 . 1.515(3) yes
C9 . H91 . 1.001 no
C9 . H92 . 1.014 no
C9 . H93 . 0.986 no
C10 . H101 . 1.008 no
C10 . H102 . 1.002 no
C10 . H103 . 1.000 no
C11 . H111 . 1.019 no
C11 . H112 . 1.013 no
C11 . H113 . 0.987 no
C12 . C13 . 1.514(3) yes
C12 . H121 . 1.023 no
C12 . H122 . 0.992 no
C13 . C14 . 1.557(2) yes
C13 . H131 . 1.027 no
C13 . H132 . 0.996 no
C14 . N15 . 1.470(2) yes
C14 . H141 . 1.012 no
N15 . C16 . 1.485(2) yes
N15 . C24 . 1.469(2) yes
C16 . C17 . 1.524(2) yes
C16 . C23 . 1.536(2) yes
C16 . H161 . 1.013 no
C17 . C18 . 1.391(3) yes
C17 . C22 . 1.388(3) yes
C18 . C19 . 1.385(3) yes
C18 . H181 . 1.015 no
C19 . C20 . 1.386(4) yes
C19 . H191 . 1.022 no
C20 . C21 . 1.367(4) yes
C20 . H201 . 1.012 no
C21 . C22 . 1.393(3) yes
C21 . H211 . 1.021 no
C22 . H221 . 1.019 no
C23 . H231 . 1.007 no
C23 . H232 . 1.008 no
C23 . H233 . 0.993 no
C24 . C25 . 1.516(3) yes
C24 . H241 . 1.002 no
C24 . H242 . 1.005 no
C25 . C26 . 1.390(3) yes
C25 . C30 . 1.383(3) yes
C26 . C27 . 1.397(4) yes
C26 . H261 . 1.030 no
C27 . C28 . 1.371(4) yes
C27 . H271 . 1.016 no
C28 . C29 . 1.367(4) yes
C28 . H281 . 1.024 no
C29 . C30 . 1.396(3) yes
C29 . H291 . 1.026 no
C30 . H301 . 1.019 no
C31 . O32 . 1.336(2) yes
C31 . O34 . 1.204(2) yes
O32 . C33 . 1.449(2) yes
C33 . H331 . 0.999 no
C33 . H332 . 1.002 no
C33 . H333 . 1.014 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
C2 . C1 . C14 . 105.33(13) yes
C2 . C1 . C31 . 113.84(14) yes
C14 . C1 . C31 . 113.60(13) yes
C2 . C1 . H11 . 110.613 no
C14 . C1 . H11 . 110.806 no
C31 . C1 . H11 . 102.785 no
C1 . C2 . C3 . 119.39(14) yes
C1 . C2 . C12 . 102.95(15) yes
C3 . C2 . C12 . 114.49(14) yes
C1 . C2 . H21 . 108.773 no
C3 . C2 . H21 . 96.774 no
C12 . C2 . H21 . 114.896 no
C2 . C3 . C4 . 118.38(16) yes
C2 . C3 . C8 . 123.15(16) yes
C4 . C3 . C8 . 118.35(14) yes
C3 . C4 . C5 . 120.19(16) yes
C3 . C4 . C11 . 122.38(17) yes
C5 . C4 . C11 . 117.43(17) yes
C4 . C5 . C6 . 122.07(17) yes
C4 . C5 . H51 . 118.836 no
C6 . C5 . H51 . 119.089 no
C5 . C6 . C7 . 117.53(15) yes
C5 . C6 . C10 . 121.68(18) yes
C7 . C6 . C10 . 120.77(17) yes
C6 . C7 . C8 . 122.57(16) yes
C6 . C7 . H71 . 118.744 no
C8 . C7 . H71 . 118.673 no
C3 . C8 . C7 . 119.28(17) yes
C3 . C8 . C9 . 125.11(16) yes
C7 . C8 . C9 . 115.61(17) yes
C8 . C9 . H91 . 109.289 no
C8 . C9 . H92 . 109.210 no
H91 . C9 . H92 . 108.271 no
C8 . C9 . H93 . 110.079 no
H91 . C9 . H93 . 110.491 no
H92 . C9 . H93 . 109.466 no
C6 . C10 . H101 . 110.081 no
C6 . C10 . H102 . 109.756 no
H101 . C10 . H102 . 108.673 no
C6 . C10 . H103 . 110.215 no
H101 . C10 . H103 . 108.811 no
H102 . C10 . H103 . 109.274 no
C4 . C11 . H111 . 109.452 no
C4 . C11 . H112 . 110.378 no
H111 . C11 . H112 . 106.995 no
C4 . C11 . H113 . 111.402 no
H111 . C11 . H113 . 109.030 no
H112 . C11 . H113 . 109.472 no
C2 . C12 . C13 . 104.63(15) yes
C2 . C12 . H121 . 110.340 no
C13 . C12 . H121 . 110.939 no
C2 . C12 . H122 . 111.430 no
C13 . C12 . H122 . 111.266 no
H121 . C12 . H122 . 108.243 no
C12 . C13 . C14 . 107.70(14) yes
C12 . C13 . H131 . 110.058 no
C14 . C13 . H131 . 108.868 no
C12 . C13 . H132 . 111.193 no
C14 . C13 . H132 . 111.337 no
H131 . C13 . H132 . 107.668 no
C1 . C14 . C13 . 103.92(13) yes
C1 . C14 . N15 . 114.20(13) yes
C13 . C14 . N15 . 117.04(15) yes
C1 . C14 . H141 . 111.264 no
C13 . C14 . H141 . 110.944 no
N15 . C14 . H141 . 99.676 no
C14 . N15 . C16 . 113.11(13) yes
C14 . N15 . C24 . 115.43(13) yes
C16 . N15 . C24 . 112.03(13) yes
N15 . C16 . C17 . 109.69(13) yes
N15 . C16 . C23 . 114.56(14) yes
C17 . C16 . C23 . 113.19(14) yes
N15 . C16 . H161 . 106.673 no
C17 . C16 . H161 . 108.714 no
C23 . C16 . H161 . 103.485 no
C16 . C17 . C18 . 118.67(16) yes
C16 . C17 . C22 . 122.74(17) yes
C18 . C17 . C22 . 118.58(18) yes
C17 . C18 . C19 . 121.0(2) yes
C17 . C18 . H181 . 119.196 no
C19 . C18 . H181 . 119.835 no
C18 . C19 . C20 . 119.7(2) yes
C18 . C19 . H191 . 119.408 no
C20 . C19 . H191 . 120.879 no
C19 . C20 . C21 . 119.9(2) yes
C19 . C20 . H201 . 120.258 no
C21 . C20 . H201 . 119.746 no
C20 . C21 . C22 . 120.6(2) yes
C20 . C21 . H211 . 119.982 no
C22 . C21 . H211 . 119.416 no
C17 . C22 . C21 . 120.2(2) yes
C17 . C22 . H221 . 119.526 no
C21 . C22 . H221 . 120.267 no
C16 . C23 . H231 . 109.767 no
C16 . C23 . H232 . 109.886 no
H231 . C23 . H232 . 108.247 no
C16 . C23 . H233 . 110.054 no
H231 . C23 . H233 . 109.479 no
H232 . C23 . H233 . 109.380 no
N15 . C24 . C25 . 112.52(15) yes
N15 . C24 . H241 . 109.112 no
C25 . C24 . H241 . 108.591 no
N15 . C24 . H242 . 109.276 no
C25 . C24 . H242 . 108.368 no
H241 . C24 . H242 . 108.905 no
C24 . C25 . C26 . 120.2(2) yes
C24 . C25 . C30 . 121.07(17) yes
C26 . C25 . C30 . 118.7(2) yes
C25 . C26 . C27 . 120.0(2) yes
C25 . C26 . H261 . 119.698 no
C27 . C26 . H261 . 120.317 no
C26 . C27 . C28 . 120.5(2) yes
C26 . C27 . H271 . 120.914 no
C28 . C27 . H271 . 118.544 no
C27 . C28 . C29 . 120.0(2) yes
C27 . C28 . H281 . 120.271 no
C29 . C28 . H281 . 119.727 no
C28 . C29 . C30 . 120.0(3) yes
C28 . C29 . H291 . 120.260 no
C30 . C29 . H291 . 119.697 no
C25 . C30 . C29 . 120.8(2) yes
C25 . C30 . H301 . 119.869 no
C29 . C30 . H301 . 119.338 no
C1 . C31 . O32 . 111.18(16) yes
C1 . C31 . O34 . 125.04(17) yes
O32 . C31 . O34 . 123.76(16) yes
C31 . O32 . C33 . 116.14(16) yes
O32 . C33 . H331 . 110.390 no
O32 . C33 . H332 . 110.454 no
H331 . C33 . H332 . 109.393 no
O32 . C33 . H333 . 109.952 no
H331 . C33 . H333 . 108.381 no
H332 . C33 . H333 . 108.214 no

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

data_3
_database_code_depnum_ccdc_archive 'CCDC 237689'

_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                   10.0421(2)
_cell_angle_alpha                90
_cell_length_b                   9.1315(2)
_cell_angle_beta                 95.1151(9)
_cell_length_c                   25.1731(8)
_cell_angle_gamma                90
_cell_volume                     2299.2(1)
_symmetry_cell_setting           'Monoclinic '
_symmetry_space_group_name_H-M   'P 1 21/c 1 '
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
-x,y+1/2,-z+1/2
x,-y+1/2,z+1/2
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            ' C28 H31 N1 O2 '
_chemical_formula_moiety         ' C28 H31 N1 O2 '
_chemical_compound_source        
;
?
;
_chemical_formula_weight         413.56
_cell_measurement_reflns_used    4311
_cell_measurement_theta_min      1
_cell_measurement_theta_max      27
_cell_measurement_temperature    190
_cell_formula_units_Z            4
_exptl_crystal_description       ' plate '
_exptl_crystal_colour            ' colourless '
_exptl_crystal_size_min          0.20
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_max          0.60
_exptl_crystal_density_diffrn    1.195
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_F_000             888.357
_exptl_absorpt_coefficient_mu    0.074
# Sheldrick geometric definitions 0.97 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  0.97
_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            8740
_reflns_number_total             5082
_diffrn_reflns_av_R_equivalents  0.03
# Number of reflections with Friedels Law is 5082
# Number of reflections without Friedels Law is 0
# Theoretical number of reflections is about 5257
_diffrn_measured_fraction_theta_max 0.967
_reflns_number_gt                3301
_diffrn_reflns_theta_min         2.76
_diffrn_reflns_theta_max         27.45
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       32
_reflns_limit_h_min              -13
_reflns_limit_h_max              12
_reflns_limit_k_min              0
_reflns_limit_k_max              11
_reflns_limit_l_min              0
_reflns_limit_l_max              32
_refine_diff_density_min         -0.52
_refine_diff_density_max         0.45
_reflns_threshold_expression     >1.00\s(I)
_refine_ls_number_reflns         3301
_refine_ls_number_parameters     280
_refine_ls_R_factor_gt           0.0873
_refine_ls_wR_factor_ref         0.0784
_refine_ls_goodness_of_fit_ref   1.0124
_refine_ls_shift/su_max          0.000523
_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

1.20 0.857 0.712
;
_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 0.6697(2) 0.3295(2) 0.91511(9) 0.0638 1.0000 Uani
C2 C 0.7849(3) 0.3061(3) 0.92904(11) 0.0471 1.0000 Uani
O3 O 0.8637(2) 0.4016(2) 0.95805(9) 0.0644 1.0000 Uani
C4 C 0.8010(5) 0.5399(4) 0.97028(16) 0.0890 1.0000 Uani
C5 C 0.8630(2) 0.1710(3) 0.9174(1) 0.0397 1.0000 Uani
C6 C 0.7792(3) 0.0307(3) 0.9104(1) 0.0408 1.0000 Uani
C7 C 0.7254(3) -0.0325(3) 0.9599(1) 0.0393 1.0000 Uani
C8 C 0.7831(3) -0.0048(3) 1.01124(12) 0.0543 1.0000 Uani
C9 C 0.7335(3) -0.0695(4) 1.05506(12) 0.0604 1.0000 Uani
C10 C 0.6266(3) -0.1644(3) 1.04887(12) 0.0527 1.0000 Uani
C11 C 0.5680(3) -0.1913(3) 0.99872(12) 0.0564 1.0000 Uani
C12 C 0.6174(3) -0.1270(3) 0.95452(11) 0.0498 1.0000 Uani
C13 C 0.8740(3) -0.0720(3) 0.88411(11) 0.0518 1.0000 Uani
C14 C 0.9429(3) 0.0237(3) 0.84509(12) 0.0514 1.0000 Uani
C15 C 0.9436(3) 0.1837(3) 0.8671(1) 0.0420 1.0000 Uani
N16 N 0.89485(19) 0.3004(2) 0.83009(8) 0.0368 1.0000 Uani
C17 C 0.9997(3) 0.3614(3) 0.7983(1) 0.0421 1.0000 Uani
C18 C 1.1010(3) 0.4480(3) 0.83451(11) 0.0427 1.0000 Uani
C19 C 1.0554(3) 0.5556(3) 0.86754(12) 0.0528 1.0000 Uani
C20 C 1.1436(4) 0.6404(4) 0.89956(13) 0.0664 1.0000 Uani
C21 C 1.2789(4) 0.6207(4) 0.89909(15) 0.0701 1.0000 Uani
C22 C 1.3259(3) 0.5156(4) 0.86750(17) 0.0747 1.0000 Uani
C23 C 1.2379(3) 0.4283(4) 0.83514(14) 0.0611 1.0000 Uani
C24 C 1.0636(3) 0.2493(3) 0.76285(12) 0.0559 1.0000 Uani
C25 C 0.7722(3) 0.2648(3) 0.79614(12) 0.0492 1.0000 Uani
C26 C 0.7061(3) 0.3986(3) 0.76996(11) 0.0485 1.0000 Uani
C27 C 0.6714(3) 0.5180(3) 0.79985(13) 0.0585 1.0000 Uani
C28 C 0.6035(3) 0.6357(4) 0.77632(17) 0.0732 1.0000 Uani
C29 C 0.5679(3) 0.6353(5) 0.7225(2) 0.0815 1.0000 Uani
C30 C 0.6019(4) 0.5195(5) 0.69196(15) 0.0799 1.0000 Uani
C31 C 0.6734(3) 0.4000(4) 0.71515(13) 0.0620 1.0000 Uani
H41 H 0.8632 0.6076 0.9914 0.1082 1.0000 Uiso
H42 H 0.7193 0.5242 0.9907 0.1082 1.0000 Uiso
H43 H 0.7670 0.5939 0.9358 0.1082 1.0000 Uiso
H51 H 0.9269 0.1612 0.9518 0.0501 1.0000 Uiso
H61 H 0.6910 0.0491 0.8878 0.0483 1.0000 Uiso
H81 H 0.8632 0.0630 1.0161 0.0643 1.0000 Uiso
H91 H 0.7765 -0.0467 1.0921 0.0711 1.0000 Uiso
H101 H 0.5926 -0.2144 1.0809 0.0665 1.0000 Uiso
H111 H 0.4869 -0.2593 0.9939 0.0687 1.0000 Uiso
H121 H 0.5731 -0.1495 0.9170 0.0619 1.0000 Uiso
H131 H 0.9422 -0.1161 0.9122 0.0642 1.0000 Uiso
H132 H 0.8243 -0.1589 0.8659 0.0642 1.0000 Uiso
H141 H 1.0355 -0.0146 0.8401 0.0641 1.0000 Uiso
H142 H 0.8898 0.0182 0.8082 0.0641 1.0000 Uiso
H151 H 1.0406 0.2180 0.8751 0.0551 1.0000 Uiso
H171 H 0.9549 0.4321 0.7710 0.0530 1.0000 Uiso
H191 H 0.9550 0.5741 0.8675 0.0616 1.0000 Uiso
H201 H 1.1069 0.7162 0.9251 0.0799 1.0000 Uiso
H211 H 1.3435 0.6857 0.9217 0.0851 1.0000 Uiso
H221 H 1.4278 0.5001 0.8673 0.0868 1.0000 Uiso
H231 H 1.2743 0.3494 0.8109 0.0725 1.0000 Uiso
H241 H 1.1330 0.2960 0.7418 0.0698 1.0000 Uiso
H242 H 1.1074 0.1683 0.7852 0.0698 1.0000 Uiso
H243 H 0.9934 0.2031 0.7364 0.0698 1.0000 Uiso
H251 H 0.7071 0.2139 0.8182 0.0598 1.0000 Uiso
H252 H 0.7950 0.1939 0.7672 0.0598 1.0000 Uiso
H271 H 0.6962 0.5181 0.8406 0.0702 1.0000 Uiso
H281 H 0.5835 0.7264 0.7998 0.0881 1.0000 Uiso
H291 H 0.5146 0.7205 0.7064 0.0968 1.0000 Uiso
H301 H 0.5777 0.5217 0.6521 0.0942 1.0000 Uiso
H311 H 0.7007 0.3138 0.6913 0.0762 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 0.0543(13) 0.0578(13) 0.0822(15) 0.0142(11) 0.0217(11) 0.013(1)
C2 0.0595(18) 0.0380(13) 0.0462(15) 0.0072(12) 0.0186(13) 0.0029(12)
O3 0.0908(16) 0.0411(11) 0.0623(13) -0.012(1) 0.0116(11) 0.0012(11)
C4 0.150(4) 0.0402(17) 0.081(2) -0.0127(18) 0.030(2) 0.016(2)
C5 0.0439(14) 0.0337(12) 0.0409(14) -0.0005(11) 0.0015(11) 0.000(1)
C6 0.0430(14) 0.0324(12) 0.0463(14) 0.0013(11) -0.0005(11) -0.004(1)
C7 0.0412(13) 0.0301(11) 0.0459(14) 0.0040(11) 0.0002(11) 0.003(1)
C8 0.0509(17) 0.0628(18) 0.0475(16) 0.0028(14) -0.0045(13) -0.0096(14)
C9 0.0579(18) 0.073(2) 0.0484(17) 0.0089(16) -0.0058(14) -0.0012(16)
C10 0.0603(18) 0.0451(15) 0.0538(17) 0.0131(13) 0.0117(14) 0.0059(13)
C11 0.0597(18) 0.0500(16) 0.0601(18) 0.0013(14) 0.0085(15) -0.0124(14)
C12 0.0563(16) 0.0426(14) 0.0496(16) -0.0003(13) -0.0010(13) -0.0071(13)
C13 0.0691(19) 0.0350(13) 0.0517(16) -0.0006(12) 0.0085(14) 0.0032(13)
C14 0.0625(18) 0.0342(13) 0.0589(17) -0.0006(13) 0.0138(14) 0.0066(12)
C15 0.0424(14) 0.0324(12) 0.0516(15) 0.0019(12) 0.0055(11) 0.0035(11)
N16 0.034(1) 0.034(1) 0.0424(11) 0.0016(9) 0.0020(9) 0.0002(8)
C17 0.0460(14) 0.0381(13) 0.0429(14) 0.0017(11) 0.0082(11) 0.0043(11)
C18 0.0417(14) 0.0355(13) 0.0512(15) 0.0079(12) 0.0046(11) 0.0009(11)
C19 0.0486(16) 0.0523(16) 0.0565(17) -0.0077(14) -0.0007(13) 0.0035(13)
C20 0.075(2) 0.0593(19) 0.0626(19) -0.0107(16) -0.0064(16) -0.0065(17)
C21 0.063(2) 0.064(2) 0.078(2) 0.0100(19) -0.0197(18) -0.0197(17)
C22 0.0395(17) 0.073(2) 0.110(3) 0.019(2) -0.0026(17) -0.0119(16)
C23 0.0421(16) 0.0573(17) 0.085(2) 0.0071(17) 0.0131(15) -0.0011(14)
C24 0.0656(19) 0.0506(16) 0.0539(16) -0.0026(14) 0.0188(14) 0.0076(14)
C25 0.0452(15) 0.0452(15) 0.0558(16) 0.0010(13) -0.0035(12) -0.0014(12)
C26 0.0377(14) 0.0530(16) 0.0538(17) 0.0102(13) -0.0016(12) -0.0041(12)
C27 0.0493(17) 0.0587(18) 0.0681(19) 0.0165(16) 0.0093(14) 0.0112(14)
C28 0.0474(18) 0.070(2) 0.104(3) 0.027(2) 0.0197(18) 0.0166(16)
C29 0.0335(17) 0.083(3) 0.126(4) 0.046(3) -0.0025(19) 0.0013(16)
C30 0.0507(19) 0.109(3) 0.075(2) 0.047(2) -0.0194(17) -0.029(2)
C31 0.0544(18) 0.073(2) 0.0568(18) 0.0150(16) -0.0051(14) -0.0170(16)
_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 . 1.197(3) yes
C2 . O3 . 1.348(4) yes
C2 . C5 . 1.504(4) yes
O3 . C4 . 1.456(4) yes
C4 . H41 . 0.998 no
C4 . H42 . 1.017 no
C4 . H43 . 1.031 no
C5 . C6 . 1.534(3) yes
C5 . C15 . 1.568(4) yes
C5 . H51 . 1.034 no
C6 . C7 . 1.516(4) yes
C6 . C13 . 1.528(4) yes
C6 . H61 . 1.023 no
C7 . C8 . 1.393(4) yes
C7 . C12 . 1.382(4) yes
C8 . C9 . 1.383(4) yes
C8 . H81 . 1.014 no
C9 . C10 . 1.377(4) yes
C9 . H91 . 1.014 no
C10 . C11 . 1.367(4) yes
C10 . H101 . 1.012 no
C11 . C12 . 1.389(4) yes
C11 . H111 . 1.022 no
C12 . H121 . 1.028 no
C13 . C14 . 1.526(4) yes
C13 . H131 . 1.023 no
C13 . H132 . 1.023 no
C14 . C15 . 1.562(4) yes
C14 . H141 . 1.012 no
C14 . H142 . 1.031 no
C15 . N16 . 1.470(3) yes
C15 . H151 . 1.026 no
N16 . C17 . 1.486(3) yes
N16 . C25 . 1.472(3) yes
C17 . C18 . 1.525(4) yes
C17 . C24 . 1.536(4) yes
C17 . H171 . 1.018 no
C18 . C19 . 1.390(4) yes
C18 . C23 . 1.385(4) yes
C19 . C20 . 1.381(4) yes
C19 . H191 . 1.023 no
C20 . C21 . 1.371(5) yes
C20 . H201 . 1.035 no
C21 . C22 . 1.358(5) yes
C21 . H211 . 1.016 no
C22 . C23 . 1.397(5) yes
C22 . H221 . 1.033 no
C23 . H231 . 1.033 no
C24 . H241 . 1.007 no
C24 . H242 . 1.006 no
C24 . H243 . 1.016 no
C25 . C26 . 1.513(4) yes
C25 . H251 . 1.008 no
C25 . H252 . 1.017 no
C26 . C27 . 1.387(4) yes
C26 . C31 . 1.389(4) yes
C27 . C28 . 1.378(4) yes
C27 . H271 . 1.033 no
C28 . C29 . 1.371(6) yes
C28 . H281 . 1.048 no
C29 . C30 . 1.368(6) yes
C29 . H291 . 1.008 no
C30 . C31 . 1.405(5) yes
C30 . H301 . 1.010 no
C31 . H311 . 1.041 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 . O3 . 123.3(3) yes
O1 . C2 . C5 . 126.6(3) yes
O3 . C2 . C5 . 110.1(2) yes
C2 . O3 . C4 . 115.5(3) yes
O3 . C4 . H41 . 112.804 no
O3 . C4 . H42 . 111.652 no
H41 . C4 . H42 . 108.281 no
O3 . C4 . H43 . 110.743 no
H41 . C4 . H43 . 107.207 no
H42 . C4 . H43 . 105.810 no
C2 . C5 . C6 . 114.6(2) yes
C2 . C5 . C15 . 114.4(2) yes
C6 . C5 . C15 . 106.6(2) yes
C2 . C5 . H51 . 101.804 no
C6 . C5 . H51 . 108.477 no
C15 . C5 . H51 . 110.856 no
C5 . C6 . C7 . 117.1(2) yes
C5 . C6 . C13 . 101.9(2) yes
C7 . C6 . C13 . 113.8(2) yes
C5 . C6 . H61 . 111.476 no
C7 . C6 . H61 . 99.483 no
C13 . C6 . H61 . 113.660 no
C6 . C7 . C8 . 123.0(2) yes
C6 . C7 . C12 . 119.5(2) yes
C8 . C7 . C12 . 117.5(2) yes
C7 . C8 . C9 . 120.9(3) yes
C7 . C8 . H81 . 118.926 no
C9 . C8 . H81 . 120.202 no
C8 . C9 . C10 . 120.7(3) yes
C8 . C9 . H91 . 119.441 no
C10 . C9 . H91 . 119.810 no
C9 . C10 . C11 . 119.0(3) yes
C9 . C10 . H101 . 120.571 no
C11 . C10 . H101 . 120.422 no
C10 . C11 . C12 . 120.6(3) yes
C10 . C11 . H111 . 119.440 no
C12 . C11 . H111 . 119.994 no
C7 . C12 . C11 . 121.3(3) yes
C7 . C12 . H121 . 119.051 no
C11 . C12 . H121 . 119.658 no
C6 . C13 . C14 . 105.2(2) yes
C6 . C13 . H131 . 110.295 no
C14 . C13 . H131 . 110.899 no
C6 . C13 . H132 . 111.864 no
C14 . C13 . H132 . 112.752 no
H131 . C13 . H132 . 105.895 no
C13 . C14 . C15 . 107.2(2) yes
C13 . C14 . H141 . 110.940 no
C15 . C14 . H141 . 113.089 no
C13 . C14 . H142 . 108.942 no
C15 . C14 . H142 . 110.522 no
H141 . C14 . H142 . 106.128 no
C5 . C15 . C14 . 103.4(2) yes
C5 . C15 . N16 . 113.5(2) yes
C14 . C15 . N16 . 117.6(2) yes
C5 . C15 . H151 . 114.386 no
C14 . C15 . H151 . 109.254 no
N16 . C15 . H151 . 99.162 no
C15 . N16 . C17 . 113.62(19) yes
C15 . N16 . C25 . 114.93(19) yes
C17 . N16 . C25 . 111.5(2) yes
N16 . C17 . C18 . 109.8(2) yes
N16 . C17 . C24 . 114.6(2) yes
C18 . C17 . C24 . 113.7(2) yes
N16 . C17 . H171 . 108.006 no
C18 . C17 . H171 . 107.771 no
C24 . C17 . H171 . 102.295 no
C17 . C18 . C19 . 119.1(2) yes
C17 . C18 . C23 . 123.2(3) yes
C19 . C18 . C23 . 117.7(3) yes
C18 . C19 . C20 . 121.1(3) yes
C18 . C19 . H191 . 119.540 no
C20 . C19 . H191 . 119.297 no
C19 . C20 . C21 . 120.3(3) yes
C19 . C20 . H201 . 119.537 no
C21 . C20 . H201 . 120.077 no
C20 . C21 . C22 . 119.7(3) yes
C20 . C21 . H211 . 120.177 no
C22 . C21 . H211 . 120.147 no
C21 . C22 . C23 . 120.6(3) yes
C21 . C22 . H221 . 119.766 no
C23 . C22 . H221 . 119.624 no
C18 . C23 . C22 . 120.5(3) yes
C18 . C23 . H231 . 119.184 no
C22 . C23 . H231 . 120.265 no
C17 . C24 . H241 . 111.563 no
C17 . C24 . H242 . 110.498 no
H241 . C24 . H242 . 108.447 no
C17 . C24 . H243 . 110.858 no
H241 . C24 . H243 . 107.636 no
H242 . C24 . H243 . 107.699 no
N16 . C25 . C26 . 112.7(2) yes
N16 . C25 . H251 . 109.388 no
C26 . C25 . H251 . 109.383 no
N16 . C25 . H252 . 109.073 no
C26 . C25 . H252 . 108.656 no
H251 . C25 . H252 . 107.473 no
C25 . C26 . C27 . 121.3(2) yes
C25 . C26 . C31 . 119.7(3) yes
C27 . C26 . C31 . 118.8(3) yes
C26 . C27 . C28 . 121.3(3) yes
C26 . C27 . H271 . 119.265 no
C28 . C27 . H271 . 119.479 no
C27 . C28 . C29 . 119.9(4) yes
C27 . C28 . H281 . 119.096 no
C29 . C28 . H281 . 120.946 no
C28 . C29 . C30 . 120.1(3) yes
C28 . C29 . H291 . 118.519 no
C30 . C29 . H291 . 121.404 no
C29 . C30 . C31 . 120.7(3) yes
C29 . C30 . H301 . 119.464 no
C31 . C30 . H301 . 119.763 no
C26 . C31 . C30 . 119.1(4) yes
C26 . C31 . H311 . 120.895 no
C30 . C31 . H311 . 119.957 no