# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_exp_559_chendong
_audit_creation_date             2013-04-30
_audit_creation_method           
;
  Olex2 1.2
  (compiled Apr 23 2013 17:54:37, GUI svn.r4466)
;
_chemical_formula_moiety         '0.92(C15 H15 Cl4 N O4)'
_chemical_formula_sum            'C13.846 H13.846 Cl3.692 N0.923 O3.692'
_chemical_formula_weight         383.17
_chemical_absolute_configuration unk
_chemical_oxdiff_formula         C15H15Cl4NO4
_chemical_oxdiff_usercomment     jiangsheng
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.01920 0.00962 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Cl 0.36843 0.69943 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.05239 0.03377 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.03256 0.01839 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 x+1/2,-y+1/2,-z
3 -x,y+1/2,-z+1/2
4 -x+1/2,-y,z+1/2

_cell_length_a                   10.26770(14)
_cell_length_b                   22.1493(3)
_cell_length_c                   23.3892(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     5319.23(13)
_cell_formula_units_Z            13
_cell_measurement_reflns_used    19069
_cell_measurement_temperature    108.6(6)
_cell_measurement_theta_max      66.5540
_cell_measurement_theta_min      3.7770
_exptl_absorpt_coefficient_mu    6.251
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.30900
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.5549
_exptl_crystal_F_000             2568.0934
_diffrn_reflns_av_R_equivalents  0.0623
_diffrn_reflns_av_unetI/netI     0.0430
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            42381
_diffrn_reflns_theta_full        66.5455
_diffrn_reflns_theta_max         66.55
_diffrn_reflns_theta_min         2.75
_diffrn_ambient_temperature      108.6(6)
_diffrn_detector_area_resol_mean 10.4015
_diffrn_measured_fraction_theta_full 0.9853
_diffrn_measured_fraction_theta_max 0.9968
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -34.00   65.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.8640  -38.0000  -60.0000 99

#__ type_ start__ end____ width___ exp.time_
  2 omega   52.00  115.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.8640   57.0000   90.0000 63

#__ type_ start__ end____ width___ exp.time_
  3 omega   28.00   75.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.8640 -125.0000 -180.0000 47

#__ type_ start__ end____ width___ exp.time_
  4 omega   21.00   76.00   1.0000    1.8400
omega____ theta____ kappa____ phi______ frames
    -       92.5000  -45.0000  120.0000 55

#__ type_ start__ end____ width___ exp.time_
  5 omega   19.00   53.00   1.0000    1.8400
omega____ theta____ kappa____ phi______ frames
    -       92.5000 -125.0000 -150.0000 34

#__ type_ start__ end____ width___ exp.time_
  6 omega   67.00   92.00   1.0000    1.8400
omega____ theta____ kappa____ phi______ frames
    -       92.5000 -125.0000 -150.0000 25

#__ type_ start__ end____ width___ exp.time_
  7 omega   56.00   83.00   1.0000    1.8400
omega____ theta____ kappa____ phi______ frames
    -       92.5000  -94.0000  120.0000 27

#__ type_ start__ end____ width___ exp.time_
  8 omega   34.00   70.00   1.0000    1.8400
omega____ theta____ kappa____ phi______ frames
    -       92.5000  -45.0000   90.0000 36

#__ type_ start__ end____ width___ exp.time_
  9 omega   21.00   47.00   1.0000    1.8400
omega____ theta____ kappa____ phi______ frames
    -       92.5000  -94.0000 -150.0000 26

#__ type_ start__ end____ width___ exp.time_
 10 omega   50.00   76.00   1.0000    1.8400
omega____ theta____ kappa____ phi______ frames
    -       92.5000 -101.0000 -112.0000 26

#__ type_ start__ end____ width___ exp.time_
 11 omega   39.00   74.00   1.0000    1.8400
omega____ theta____ kappa____ phi______ frames
    -       92.5000  -45.0000  -90.0000 35

#__ type_ start__ end____ width___ exp.time_
 12 omega   20.00   48.00   1.0000    1.8400
omega____ theta____ kappa____ phi______ frames
    -       92.5000  -94.0000   90.0000 28

#__ type_ start__ end____ width___ exp.time_
 13 omega   54.00   80.00   1.0000    1.8400
omega____ theta____ kappa____ phi______ frames
    -       92.5000  -94.0000   90.0000 26

#__ type_ start__ end____ width___ exp.time_
 14 omega   26.00   82.00   1.0000    1.8400
omega____ theta____ kappa____ phi______ frames
    -       92.5000  -94.0000  150.0000 56

#__ type_ start__ end____ width___ exp.time_
 15 omega   24.00   69.00   1.0000    1.8400
omega____ theta____ kappa____ phi______ frames
    -       92.5000  -45.0000    0.0000 45

#__ type_ start__ end____ width___ exp.time_
 16 omega  103.00  129.00   1.0000    1.8400
omega____ theta____ kappa____ phi______ frames
    -       92.5000  125.0000 -150.0000 26

#__ type_ start__ end____ width___ exp.time_
 17 omega   18.00   64.00   1.0000    1.8400
omega____ theta____ kappa____ phi______ frames
    -       92.5000  -45.0000   60.0000 46

#__ type_ start__ end____ width___ exp.time_
 18 omega   35.00   61.00   1.0000    1.8400
omega____ theta____ kappa____ phi______ frames
    -       92.5000   15.0000  150.0000 26

#__ type_ start__ end____ width___ exp.time_
 19 omega   80.00  106.00   1.0000    1.8400
omega____ theta____ kappa____ phi______ frames
    -       92.5000   15.0000  150.0000 26

#__ type_ start__ end____ width___ exp.time_
 20 omega   14.00   40.00   1.0000    1.8400
omega____ theta____ kappa____ phi______ frames
    -       92.5000 -101.0000 -112.0000 26

#__ type_ start__ end____ width___ exp.time_
 21 omega   62.00  129.00   1.0000    1.8400
omega____ theta____ kappa____ phi______ frames
    -       92.5000   61.0000  120.0000 67

#__ type_ start__ end____ width___ exp.time_
 22 omega   58.00  104.00   1.0000    1.8400
omega____ theta____ kappa____ phi______ frames
    -       92.5000  -61.0000  120.0000 46

#__ type_ start__ end____ width___ exp.time_
 23 omega   19.00   49.00   1.0000    1.8400
omega____ theta____ kappa____ phi______ frames
    -       92.5000  -30.0000 -180.0000 30

#__ type_ start__ end____ width___ exp.time_
 24 omega   69.00   95.00   1.0000    1.8400
omega____ theta____ kappa____ phi______ frames
    -       92.5000   61.0000  -30.0000 26

#__ type_ start__ end____ width___ exp.time_
 25 omega  108.00  134.00   1.0000    1.8400
omega____ theta____ kappa____ phi______ frames
    -       92.5000   61.0000  -30.0000 26

#__ type_ start__ end____ width___ exp.time_
 26 omega   18.00   89.00   1.0000    1.8400
omega____ theta____ kappa____ phi______ frames
    -       92.5000  -61.0000  -30.0000 71

#__ type_ start__ end____ width___ exp.time_
 27 omega   50.00   81.00   1.0000    1.8400
omega____ theta____ kappa____ phi______ frames
    -       92.5000  -94.0000   30.0000 31

#__ type_ start__ end____ width___ exp.time_
 28 omega   16.00   41.00   1.0000    1.8400
omega____ theta____ kappa____ phi______ frames
    -       92.5000  -30.0000   60.0000 25

#__ type_ start__ end____ width___ exp.time_
 29 omega   46.00   71.00   1.0000    1.8400
omega____ theta____ kappa____ phi______ frames
    -       92.5000  -45.0000 -150.0000 25

#__ type_ start__ end____ width___ exp.time_
 30 omega   13.00   39.00   1.0000    1.8400
omega____ theta____ kappa____ phi______ frames
    -       92.5000  -94.0000    0.0000 26

#__ type_ start__ end____ width___ exp.time_
 31 omega   50.00   75.00   1.0000    1.8400
omega____ theta____ kappa____ phi______ frames
    -       92.5000  -45.0000 -180.0000 25

#__ type_ start__ end____ width___ exp.time_
 32 omega  138.00  176.00   1.0000    1.8400
omega____ theta____ kappa____ phi______ frames
    -       92.5000   15.0000  -60.0000 38

#__ type_ start__ end____ width___ exp.time_
 33 omega   65.00   90.00   1.0000    1.8400
omega____ theta____ kappa____ phi______ frames
    -       92.5000   15.0000  -60.0000 25
;
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.1161759000
_diffrn_orient_matrix_UB_12      -0.0290039000
_diffrn_orient_matrix_UB_13      -0.0313926000
_diffrn_orient_matrix_UB_21      -0.0831540000
_diffrn_orient_matrix_UB_22      0.0056947000
_diffrn_orient_matrix_UB_23      0.0545339000
_diffrn_orient_matrix_UB_31      -0.0459133000
_diffrn_orient_matrix_UB_32      0.0629824000
_diffrn_orient_matrix_UB_33      -0.0193665000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_source                   'Enhance Ultra (Cu) X-ray Source'
_reflns_Friedel_coverage         0.996
_reflns_limit_h_max              12
_reflns_limit_h_min              -12
_reflns_limit_k_max              26
_reflns_limit_k_min              -26
_reflns_limit_l_max              27
_reflns_limit_l_min              -27
_reflns_number_gt                8627
_reflns_number_total             9352
_reflns_odcompleteness_completeness 98.53
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
olex2.refine (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard,
H. Puschmann, in preparation, 2011)
;
_computing_structure_solution    
;
olex2.solve (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard,
H. Puschmann, in preparation, 2011)
;
_refine_diff_density_max         0.3737
_refine_diff_density_min         -0.3341
_refine_diff_density_rms         0.0656
_refine_ls_abs_structure_details 
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   -0.017(9)
_refine_ls_d_res_high            0.8404
_refine_ls_d_res_low             16.0824
_refine_ls_goodness_of_fit_ref   1.0444
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    75
_refine_ls_number_parameters     648
_refine_ls_number_reflns         9352
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0408
_refine_ls_R_factor_gt           0.0357
_refine_ls_restrained_S_all      1.0444
_refine_ls_shift/su_max          0.0001
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0457P)²+1.5168P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0887
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C42(H42), C45(H45), C47(H47), C52(H52), C55(H55), C65(H65)
2.b Secondary CH2 refined with riding coordinates:
 C28(H28a,H28b), C30(H30a,H30b), C32(H32a,H32b), C33(H33a,H33b), C38(H38a,
 H38b), C40(H40a,H40b), C41(H41a,H41b), C44(H44a,H44b), C51(H51a,H51b),
 C53(H53a,H53b), C54(H54a,H54b), C58(H58a,H58b), C60(H60a,H60b), C62(H62a,H62b),
  C71(H71a,H71b)
2.c Aromatic/amide H refined with riding coordinates:
 C36(H36), C37(H37), C43(H43), C46(H46), C57(H57), C59(H59), C64(H64),
 C68(H68), C70(H70)
;
_atom_sites_solution_primary     iterative
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_refinement_flags_posn
Cl1 Cl 0.97620(8) 0.32661(3) 0.36500(4) 0.03024(17) Uani 1.000000 .
Cl2 Cl 0.56343(8) -0.01439(3) 0.28433(3) 0.02785(17) Uani 1.000000 .
Cl3 Cl 0.58878(8) 0.30812(3) 0.30697(4) 0.03142(18) Uani 1.000000 .
Cl4 Cl 1.18478(7) 0.54318(4) 0.29436(4) 0.03416(19) Uani 1.000000 .
Cl5 Cl 0.93068(8) 0.58598(4) 0.26195(4) 0.03417(19) Uani 1.000000 .
Cl6 Cl 1.12319(8) 0.21591(4) 0.37399(4) 0.0385(2) Uani 1.000000 .
Cl7 Cl 1.11245(8) 0.27943(4) 0.26626(4) 0.03472(19) Uani 1.000000 .
Cl8 Cl 0.61004(8) 0.54519(4) 0.60080(4) 0.03532(19) Uani 1.000000 .
Cl9 Cl 0.14057(10) 0.83591(4) 0.70115(4) 0.0426(2) Uani 1.000000 .
Cl10 Cl 1.05161(10) 0.63364(4) 0.36274(4) 0.0424(2) Uani 1.000000 .
Cl11 Cl 0.54386(10) 0.66734(4) 0.63017(4) 0.0439(2) Uani 1.000000 .
Cl12 Cl 0.65958(9) 0.58745(5) 0.71535(4) 0.0485(2) Uani 1.000000 .
O13 O 0.3280(2) 0.57858(9) 0.63134(10) 0.0271(5) Uani 1.000000 .
O14 O 0.8579(2) 0.53656(9) 0.38397(9) 0.0225(4) Uani 1.000000 .
O15 O 0.50150(19) 0.09814(9) 0.47223(9) 0.0206(4) Uani 1.000000 .
O16 O 0.0483(2) 0.71353(9) 0.52079(9) 0.0250(5) Uani 1.000000 .
O17 O 0.7385(2) 0.47874(10) 0.32255(10) 0.0272(5) Uani 1.000000 .
O18 O 0.6831(2) 0.16693(9) 0.30385(9) 0.0241(5) Uani 1.000000 .
O19 O 0.8315(2) 0.21274(9) 0.36067(9) 0.0242(5) Uani 1.000000 .
O20 O 0.2154(2) 0.64611(9) 0.68655(9) 0.0248(5) Uani 1.000000 .
O21 O 0.4946(2) 0.44962(9) 0.47636(8) 0.0222(4) Uani 1.000000 .
N22 N 0.6464(2) 0.52340(10) 0.40050(11) 0.0189(5) Uani 1.000000 .
O23 O 0.3872(2) 0.08104(10) 0.55258(9) 0.0279(5) Uani 1.000000 .
O24 O -0.0565(3) 0.73025(11) 0.43813(10) 0.0442(7) Uani 1.000000 .
N25 N 0.1479(2) 0.62167(11) 0.59680(11) 0.0216(5) Uani 1.000000 .
O26 O 0.3663(3) 0.44482(12) 0.55444(10) 0.0390(6) Uani 1.000000 .
N27 N 0.6405(2) 0.18578(11) 0.39844(11) 0.0198(5) Uani 1.000000 .
C28 C 0.5531(3) 0.05795(13) 0.37761(12) 0.0196(6) Uani 1.000000 .
C29 C 0.0166(3) 0.71543(13) 0.58116(12) 0.0204(6) Uani 1.000000 .
C30 C 0.4378(3) 0.21801(14) 0.43365(13) 0.0237(6) Uani 1.000000 .
C31 C 0.2285(3) 0.61805(14) 0.64204(14) 0.0235(7) Uani 1.000000 .
C32 C 0.9748(3) 0.51716(14) 0.35642(14) 0.0243(7) Uani 1.000000 .
C33 C 0.4333(3) 0.55970(14) 0.40948(13) 0.0237(6) Uani 1.000000 .
C34 C 0.7448(3) 0.51023(13) 0.36507(14) 0.0216(6) Uani 1.000000 .
C35 C 0.3369(3) 0.42625(13) 0.40853(14) 0.0238(7) Uani 1.000000 .
C36 C 0.2818(3) 0.08129(14) 0.45943(13) 0.0235(7) Uani 1.000000 .
C37 C 0.2797(3) 0.07478(14) 0.35098(13) 0.0220(6) Uani 1.000000 .
C38 C 0.9049(3) 0.22471(15) 0.30995(13) 0.0256(7) Uani 1.000000 .
C39 C 0.7141(3) 0.18672(13) 0.35057(14) 0.0226(7) Uani 1.000000 .
C40 C 0.5606(3) 0.39153(13) 0.39207(13) 0.0204(6) Uani 1.000000 .
C41 C -0.0687(3) 0.60572(14) 0.57020(14) 0.0247(7) Uani 1.000000 .
C42 C 0.5009(3) 0.17080(13) 0.39442(13) 0.0200(6) Uani 1.000000 .
C43 C -0.1659(3) 0.76443(14) 0.63723(16) 0.0303(7) Uani 1.000000 .
C44 C 0.1111(3) 0.75743(14) 0.61276(13) 0.0240(7) Uani 1.000000 .
C45 C 0.0185(3) 0.64929(13) 0.60321(13) 0.0204(6) Uani 1.000000 .
C46 C 0.2779(3) 0.42789(15) 0.45937(14) 0.0293(7) Uani 1.000000 .
C47 C 0.0615(3) 0.76845(14) 0.67375(14) 0.0273(7) Uani 1.000000 .
C48 C -0.0591(4) 0.73109(14) 0.48935(15) 0.0306(8) Uani 1.000000 .
C49 C 0.4739(3) 0.10438(13) 0.41189(12) 0.0191(6) Uani 1.000000 .
C50 C 0.4785(3) 0.44376(13) 0.41528(13) 0.0197(6) Uani 1.000000 .
C51 C 0.5111(3) 0.58433(14) 0.46000(14) 0.0253(7) Uani 1.000000 .
C52 C 0.5046(3) 0.05574(13) 0.31591(13) 0.0207(6) Uani 1.000000 .
C53 C 0.6539(3) 0.57001(14) 0.44544(13) 0.0234(7) Uani 1.000000 .
C54 C 0.6710(3) 0.22394(15) 0.44846(13) 0.0263(7) Uani 1.000000 .
C55 C 0.5119(3) 0.50556(13) 0.38731(13) 0.0205(6) Uani 1.000000 .
C56 C 0.3872(3) 0.08664(13) 0.50144(13) 0.0220(6) Uani 1.000000 .
C57 C -0.0828(3) 0.77701(14) 0.67910(15) 0.0305(7) Uani 1.000000 .
C58 C 0.4203(3) 0.57161(15) 0.67682(14) 0.0285(7) Uani 1.000000 .
C59 C 0.2957(3) 0.40399(14) 0.35330(14) 0.0255(7) Uani 1.000000 .
C60 C 0.5415(3) 0.23256(14) 0.47911(13) 0.0251(7) Uani 1.000000 .
C61 C 1.0319(3) 0.56843(13) 0.32104(13) 0.0231(7) Uani 1.000000 .
C62 C 0.0182(3) 0.57989(14) 0.52240(14) 0.0278(7) Uani 1.000000 .
C63 C 0.3753(3) 0.44171(14) 0.50336(14) 0.0287(7) Uani 1.000000 .
C64 C 0.3833(3) 0.38242(13) 0.31624(14) 0.0246(7) Uani 1.000000 .
C65 C 0.5264(3) 0.38139(13) 0.32911(13) 0.0217(6) Uani 1.000000 .
C66 C -0.1165(3) 0.74340(13) 0.58223(14) 0.0248(7) Uani 1.000000 .
C67 C 0.3324(3) 0.08769(13) 0.40714(13) 0.0203(6) Uani 1.000000 .
C68 C 0.3604(3) 0.05790(13) 0.30860(13) 0.0221(6) Uani 1.000000 .
C69 C 0.5526(3) 0.59272(15) 0.65640(14) 0.0288(7) Uani 1.000000 .
C70 C -0.1611(4) 0.74947(15) 0.52944(16) 0.0317(8) Uani 1.000000 .
C71 C 0.1575(3) 0.58345(15) 0.54493(13) 0.0256(7) Uani 1.000000 .
C72 C 1.0237(3) 0.26021(14) 0.32836(14) 0.0246(7) Uani 1.000000 .
H28a H 0.6445(3) 0.06897(13) 0.37818(12) 0.0236(7) Uiso 1.000000 R
H28b H 0.5443(3) 0.01840(13) 0.39499(12) 0.0236(7) Uiso 1.000000 R
H30a H 0.4149(3) 0.25397(14) 0.41223(13) 0.0284(8) Uiso 1.000000 R
H30b H 0.3598(3) 0.20190(14) 0.45138(13) 0.0284(8) Uiso 1.000000 R
H32a H 1.0375(3) 0.50436(14) 0.38494(14) 0.0292(8) Uiso 1.000000 R
H32b H 0.9560(3) 0.48299(14) 0.33182(14) 0.0292(8) Uiso 1.000000 R
H33a H 0.3472(3) 0.54707(14) 0.42164(13) 0.0285(8) Uiso 1.000000 R
H33b H 0.4243(3) 0.59015(14) 0.37994(13) 0.0285(8) Uiso 1.000000 R
H36 H 0.1945(3) 0.07458(14) 0.46778(13) 0.0282(8) Uiso 1.000000 R
H37 H 0.1907(3) 0.07813(14) 0.34429(13) 0.0264(8) Uiso 1.000000 R
H38a H 0.9308(3) 0.18721(15) 0.29180(13) 0.0308(8) Uiso 1.000000 R
H38b H 0.8534(3) 0.24793(15) 0.28303(13) 0.0308(8) Uiso 1.000000 R
H40a H 0.6525(3) 0.40104(13) 0.39574(13) 0.0245(7) Uiso 1.000000 R
H40b H 0.5432(3) 0.35513(13) 0.41382(13) 0.0245(7) Uiso 1.000000 R
H41a H -0.1000(3) 0.57372(14) 0.59498(14) 0.0297(8) Uiso 1.000000 R
H41b H -0.1431(3) 0.62676(14) 0.55416(14) 0.0297(8) Uiso 1.000000 R
H42 H 0.4711(3) 0.17727(13) 0.35508(13) 0.0240(7) Uiso 1.000000 R
H43 H -0.2550(3) 0.76899(14) 0.64294(16) 0.0364(9) Uiso 1.000000 R
H44a H 0.1970(3) 0.73921(14) 0.61409(13) 0.0288(8) Uiso 1.000000 R
H44b H 0.1179(3) 0.79554(14) 0.59255(13) 0.0288(8) Uiso 1.000000 R
H45 H -0.0063(3) 0.64877(13) 0.64367(13) 0.0245(7) Uiso 1.000000 R
H46 H 0.1897(3) 0.42136(15) 0.46582(14) 0.0351(9) Uiso 1.000000 R
H47 H 0.0872(3) 0.73410(14) 0.69763(14) 0.0327(8) Uiso 1.000000 R
H51a H 0.4981(3) 0.62750(14) 0.46400(14) 0.0303(8) Uiso 1.000000 R
H51b H 0.4853(3) 0.56465(14) 0.49528(14) 0.0303(8) Uiso 1.000000 R
H52 H 0.5430(3) 0.08966(13) 0.29493(13) 0.0248(8) Uiso 1.000000 R
H53a H 0.6997(3) 0.55485(14) 0.47876(13) 0.0281(8) Uiso 1.000000 R
H53b H 0.6984(3) 0.60571(14) 0.43150(13) 0.0281(8) Uiso 1.000000 R
H54a H 0.7336(3) 0.20409(15) 0.47321(13) 0.0315(8) Uiso 1.000000 R
H54b H 0.7066(3) 0.26248(15) 0.43645(13) 0.0315(8) Uiso 1.000000 R
H55 H 0.5013(3) 0.50248(13) 0.34577(13) 0.0246(8) Uiso 1.000000 R
H57 H -0.1157(3) 0.79184(14) 0.71338(15) 0.0366(9) Uiso 1.000000 R
H58a H 0.3933(3) 0.59524(15) 0.70965(14) 0.0342(9) Uiso 1.000000 R
H58b H 0.4249(3) 0.52956(15) 0.68824(14) 0.0342(9) Uiso 1.000000 R
H59 H 0.2080(3) 0.40468(14) 0.34352(14) 0.0306(8) Uiso 1.000000 R
H60a H 0.5324(3) 0.27375(14) 0.49262(13) 0.0301(8) Uiso 1.000000 R
H60b H 0.5343(3) 0.20533(14) 0.51143(13) 0.0301(8) Uiso 1.000000 R
H62a H -0.0054(3) 0.53838(14) 0.51416(14) 0.0334(9) Uiso 1.000000 R
H62b H 0.0091(3) 0.60350(14) 0.48770(14) 0.0334(9) Uiso 1.000000 R
H64 H 0.3544(3) 0.36754(13) 0.28127(14) 0.0296(8) Uiso 1.000000 R
H65 H 0.5691(3) 0.41273(13) 0.30625(13) 0.0261(8) Uiso 1.000000 R
H68 H 0.3250(3) 0.04719(13) 0.27344(13) 0.0265(8) Uiso 1.000000 R
H70 H -0.2436(4) 0.76317(15) 0.51947(16) 0.0381(9) Uiso 1.000000 R
H71a H 0.2148(3) 0.60172(15) 0.51686(13) 0.0308(8) Uiso 1.000000 R
H71b H 0.1902(3) 0.54359(15) 0.55439(13) 0.0308(8) Uiso 1.000000 R


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl1 C72 1.771(3) .
Cl2 C52 1.823(3) .
Cl3 C65 1.820(3) .
Cl4 C61 1.780(3) .
Cl5 C61 1.772(3) .
Cl6 C72 1.774(3) .
Cl7 C72 1.767(3) .
Cl8 C69 1.774(3) .
Cl9 C47 1.817(3) .
Cl10 C61 1.755(3) .
Cl11 C69 1.765(3) .
Cl12 C69 1.766(3) .
O13 C31 1.367(4) .
O13 C58 1.433(4) .
O14 C32 1.428(4) .
O14 C34 1.373(4) .
O15 C49 1.446(4) .
O15 C56 1.382(4) .
O16 C29 1.450(4) .
O16 C48 1.382(4) .
O17 C34 1.216(4) .
O18 C39 1.220(4) .
O19 C38 1.431(4) .
O19 C39 1.356(4) .
O20 C31 1.220(4) .
O21 C50 1.444(4) .
O21 C63 1.389(4) .
N22 C34 1.339(4) .
N22 C53 1.475(4) .
N22 C55 1.469(4) .
O23 C56 1.203(4) .
O24 C48 1.198(4) .
N25 C31 1.346(4) .
N25 C45 1.470(4) .
N25 C71 1.483(4) .
O26 C63 1.200(4) .
N27 C39 1.351(4) .
N27 C42 1.474(4) .
N27 C54 1.477(4) .
C28 C49 1.537(4) .
C28 C52 1.527(4) .
C29 C44 1.534(4) .
C29 C45 1.553(4) .
C29 C66 1.501(4) .
C30 C42 1.535(4) .
C30 C60 1.538(4) .
C32 C61 1.523(4) .
C33 C51 1.527(4) .
C33 C55 1.535(4) .
C35 C46 1.335(5) .
C35 C50 1.512(4) .
C35 C59 1.446(5) .
C36 C56 1.466(4) .
C36 C67 1.336(4) .
C37 C67 1.449(4) .
C37 C68 1.345(4) .
C38 C72 1.513(4) .
C40 C50 1.531(4) .
C40 C65 1.530(4) .
C41 C45 1.526(4) .
C41 C62 1.541(5) .
C42 C49 1.552(4) .
C43 C57 1.329(5) .
C43 C66 1.459(5) .
C44 C47 1.534(5) .
C46 C63 1.467(5) .
C47 C57 1.498(5) .
C48 C70 1.463(5) .
C49 C67 1.504(4) .
C50 C55 1.556(4) .
C51 C53 1.538(4) .
C52 C68 1.491(4) .
C54 C60 1.523(4) .
C58 C69 1.514(5) .
C59 C64 1.337(5) .
C62 C71 1.526(5) .
C64 C65 1.500(4) .
C66 C70 1.324(5) .

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C58 O13 C31 115.3(2) . .
C34 O14 C32 116.0(2) . .
C56 O15 C49 109.5(2) . .
C48 O16 C29 109.3(2) . .
C39 O19 C38 113.8(2) . .
C63 O21 C50 109.7(2) . .
C53 N22 C34 123.6(2) . .
C55 N22 C34 121.4(2) . .
C55 N22 C53 112.8(2) . .
C45 N25 C31 120.0(3) . .
C71 N25 C31 124.6(3) . .
C71 N25 C45 112.4(2) . .
C42 N27 C39 119.6(3) . .
C54 N27 C39 121.9(2) . .
C54 N27 C42 112.7(2) . .
C52 C28 C49 110.0(2) . .
C44 C29 O16 110.2(2) . .
C45 C29 O16 107.1(2) . .
C45 C29 C44 113.8(2) . .
C66 C29 O16 103.5(2) . .
C66 C29 C44 108.5(2) . .
C66 C29 C45 113.3(2) . .
C60 C30 C42 105.3(3) . .
O20 C31 O13 124.3(3) . .
N25 C31 O13 110.7(3) . .
N25 C31 O20 124.9(3) . .
C61 C32 O14 110.2(2) . .
C55 C33 C51 105.4(2) . .
O17 C34 O14 123.5(3) . .
N22 C34 O14 110.3(3) . .
N22 C34 O17 126.2(3) . .
C50 C35 C46 109.6(3) . .
C59 C35 C46 132.2(3) . .
C59 C35 C50 117.5(3) . .
C67 C36 C56 108.6(3) . .
C68 C37 C67 119.6(3) . .
C72 C38 O19 106.6(2) . .
O19 C39 O18 122.7(3) . .
N27 C39 O18 126.2(3) . .
N27 C39 O19 111.1(3) . .
C65 C40 C50 109.0(2) . .
C62 C41 C45 105.2(3) . .
C30 C42 N27 102.6(2) . .
C49 C42 N27 111.7(2) . .
C49 C42 C30 114.4(2) . .
C66 C43 C57 119.5(3) . .
C47 C44 C29 109.5(3) . .
C29 C45 N25 111.7(2) . .
C41 C45 N25 102.4(2) . .
C41 C45 C29 114.9(2) . .
C63 C46 C35 108.7(3) . .
C44 C47 Cl9 108.1(2) . .
C57 C47 Cl9 107.9(2) . .
C57 C47 C44 115.2(3) . .
O24 C48 O16 120.6(3) . .
C70 C48 O16 108.0(3) . .
C70 C48 O24 131.4(3) . .
C28 C49 O15 110.0(2) . .
C42 C49 O15 108.2(2) . .
C42 C49 C28 113.7(2) . .
C67 C49 O15 103.8(2) . .
C67 C49 C28 108.0(2) . .
C67 C49 C42 112.7(2) . .
C35 C50 O21 103.7(2) . .
C40 C50 O21 110.8(2) . .
C40 C50 C35 107.4(2) . .
C55 C50 O21 108.2(2) . .
C55 C50 C35 113.2(2) . .
C55 C50 C40 113.2(2) . .
C53 C51 C33 104.7(3) . .
C28 C52 Cl2 107.6(2) . .
C68 C52 Cl2 108.1(2) . .
C68 C52 C28 115.5(3) . .
C51 C53 N22 104.6(2) . .
C60 C54 N27 105.0(2) . .
C33 C55 N22 102.3(2) . .
C50 C55 N22 110.8(2) . .
C50 C55 C33 115.4(2) . .
O23 C56 O15 120.7(3) . .
C36 C56 O15 108.1(2) . .
C36 C56 O23 131.2(3) . .
C47 C57 C43 123.2(3) . .
C69 C58 O13 109.1(3) . .
C64 C59 C35 120.3(3) . .
C54 C60 C30 104.6(2) . .
Cl5 C61 Cl4 108.22(17) . .
Cl10 C61 Cl4 110.59(16) . .
Cl10 C61 Cl5 108.70(17) . .
C32 C61 Cl4 107.2(2) . .
C32 C61 Cl5 111.2(2) . .
C32 C61 Cl10 110.9(2) . .
C71 C62 C41 105.9(3) . .
O26 C63 O21 120.9(3) . .
C46 C63 O21 108.0(3) . .
C46 C63 O26 131.1(3) . .
C65 C64 C59 122.2(3) . .
C40 C65 Cl3 108.9(2) . .
C64 C65 Cl3 107.5(2) . .
C64 C65 C40 114.6(3) . .
C43 C66 C29 117.6(3) . .
C70 C66 C29 110.0(3) . .
C70 C66 C43 132.0(3) . .
C37 C67 C36 131.6(3) . .
C49 C67 C36 109.5(3) . .
C49 C67 C37 118.4(3) . .
C52 C68 C37 122.4(3) . .
Cl11 C69 Cl8 108.52(18) . .
Cl12 C69 Cl8 109.06(18) . .
Cl12 C69 Cl11 111.40(19) . .
C58 C69 Cl8 110.2(2) . .
C58 C69 Cl11 110.7(2) . .
C58 C69 Cl12 106.9(2) . .
C66 C70 C48 108.8(3) . .
C62 C71 N25 104.5(2) . .
Cl6 C72 Cl1 109.08(18) . .
Cl7 C72 Cl1 109.87(17) . .
Cl7 C72 Cl6 109.30(17) . .
C38 C72 Cl1 110.3(2) . .
C38 C72 Cl6 110.4(2) . .
C38 C72 Cl7 107.9(2) . .

_database_code_depnum_ccdc_archive 'CCDC 971441'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_wuzhenlong_0413fu
_audit_creation_date             2013-04-22
_audit_creation_method           
;
  Olex2 1.1
  (compiled Nov  1 2011 20:42:30, GUI svn.r3906)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C12 H15 N O3'
_chemical_formula_sum            'C12 H15 N O3'
_chemical_formula_weight         221.25
_chemical_absolute_configuration unk
_chemical_melting_point          ?
_chemical_oxdiff_formula         CHNO
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, -y, z+1/2'
3 'x+1/2, -y+1/2, -z'
4 '-x, y+1/2, -z+1/2'

_cell_length_a                   5.80812(19)
_cell_length_b                   8.2156(3)
_cell_length_c                   21.4801(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1024.97(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3558
_cell_measurement_temperature    173.01(10)
_cell_measurement_theta_max      62.5510
_cell_measurement_theta_min      4.0990
_exptl_absorpt_coefficient_mu    0.848
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67421
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.434
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             472
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0400
_diffrn_reflns_av_unetI/netI     0.0257
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            8205
_diffrn_reflns_theta_full        62.78
_diffrn_reflns_theta_max         62.78
_diffrn_reflns_theta_min         4.12
_diffrn_ambient_temperature      173.01(10)
_diffrn_detector_area_resol_mean 16.0288
_diffrn_measured_fraction_theta_full 0.9980
_diffrn_measured_fraction_theta_max 0.9940
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -90.00  -61.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.1184 -178.0000  -90.0000 29

#__ type_ start__ end____ width___ exp.time_
  2 omega    3.00  106.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       33.1184   19.0000 -120.0000 103

#__ type_ start__ end____ width___ exp.time_
  3 omega   38.00   84.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       33.1184  178.0000   30.0000 46

#__ type_ start__ end____ width___ exp.time_
  4 omega   38.00   72.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -45.0000  150.0000 34

#__ type_ start__ end____ width___ exp.time_
  5 omega   22.00   66.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -30.0000 -180.0000 44

#__ type_ start__ end____ width___ exp.time_
  6 omega  137.00  163.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  111.0000  150.0000 26

#__ type_ start__ end____ width___ exp.time_
  7 omega   19.00   72.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -45.0000   60.0000 53

#__ type_ start__ end____ width___ exp.time_
  8 omega  118.00  145.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000   45.0000  -30.0000 27

#__ type_ start__ end____ width___ exp.time_
  9 omega   75.00  116.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000   45.0000  -30.0000 41

#__ type_ start__ end____ width___ exp.time_
 10 omega   34.00   76.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -45.0000  -30.0000 42

#__ type_ start__ end____ width___ exp.time_
 11 omega   29.00   64.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -30.0000   90.0000 35

#__ type_ start__ end____ width___ exp.time_
 12 omega   19.00   53.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -30.0000  -60.0000 34

#__ type_ start__ end____ width___ exp.time_
 13 omega   30.00  112.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -61.0000 -120.0000 82

#__ type_ start__ end____ width___ exp.time_
 14 omega -110.00  -53.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.1184  178.0000   30.0000 57

#__ type_ start__ end____ width___ exp.time_
 15 omega    8.00  106.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       33.1184   38.0000  -30.0000 98

#__ type_ start__ end____ width___ exp.time_
 16 omega    3.00  103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       33.1184   77.0000   60.0000 100

#__ type_ start__ end____ width___ exp.time_
 17 omega   18.00   90.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000 -111.0000 -150.0000 72

#__ type_ start__ end____ width___ exp.time_
 18 omega   61.00  163.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000   30.0000 -120.0000 102

#__ type_ start__ end____ width___ exp.time_
 19 omega   67.00  162.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000   45.0000   30.0000 95

#__ type_ start__ end____ width___ exp.time_
 20 omega   60.00  161.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000   77.0000  150.0000 101

#__ type_ start__ end____ width___ exp.time_
 21 omega   18.00   90.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000 -111.0000   90.0000 72

#__ type_ start__ end____ width___ exp.time_
 22 omega   61.00  163.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000   30.0000  120.0000 102

#__ type_ start__ end____ width___ exp.time_
 23 omega -110.00  -53.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.1184  178.0000  150.0000 57

#__ type_ start__ end____ width___ exp.time_
 24 omega   13.00  102.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       33.1184   57.0000    0.0000 89

#__ type_ start__ end____ width___ exp.time_
 25 omega    3.00  103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       33.1184   77.0000 -180.0000 100

#__ type_ start__ end____ width___ exp.time_
 26 omega   18.00   63.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000 -111.0000  -30.0000 45

#__ type_ start__ end____ width___ exp.time_
 27 omega   60.00  161.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000   77.0000  -90.0000 101
;
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.1259962000
_diffrn_orient_matrix_UB_12      -0.1608467000
_diffrn_orient_matrix_UB_13      -0.0139673000
_diffrn_orient_matrix_UB_21      0.0280395000
_diffrn_orient_matrix_UB_22      0.0516200000
_diffrn_orient_matrix_UB_23      -0.0685414000
_diffrn_orient_matrix_UB_31      0.2317410000
_diffrn_orient_matrix_UB_32      0.0813235000
_diffrn_orient_matrix_UB_33      0.0158703000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_source                   'Enhance Ultra (Cu) X-ray Source'
_diffrn_source_current           n/a
_diffrn_source_voltage           n/a
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1553
_reflns_number_total             1647
_reflns_odcompleteness_completeness 99.80
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     61.08
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELXL, G.M. Sheldrick, Acta Cryst.
2008). A64, 112-122
;
_computing_structure_solution    
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         0.130
_refine_diff_density_min         -0.121
_refine_diff_density_rms         0.030
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.0(3)
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.107
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         1647
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0316
_refine_ls_R_factor_gt           0.0286
_refine_ls_restrained_S_all      1.107
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0291P)²+0.1886P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0672
_refine_ls_wR_factor_ref         0.0691
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.2371(2) 0.59131(15) 0.05987(5) 0.0327(3) Uani 1 1 d . . .
H1 H 0.0987 0.5980 0.0670 0.049 Uiso 1 1 calc R . .
N2 N 0.7529(3) 0.57192(15) 0.07763(6) 0.0244(3) Uani 1 1 d . . .
O3 O 0.6524(2) 0.52302(14) 0.24697(5) 0.0295(3) Uani 1 1 d . . .
C4 C 0.3686(3) 0.6161(2) 0.16863(8) 0.0282(4) Uani 1 1 d . . .
H4A H 0.2993 0.6899 0.1985 0.034 Uiso 1 1 calc R . .
H4B H 0.2841 0.5143 0.1695 0.034 Uiso 1 1 calc R . .
O5 O 0.8474(2) 0.59836(17) 0.33263(6) 0.0444(4) Uani 1 1 d . . .
C6 C 0.8440(3) 0.7674(2) 0.23972(8) 0.0321(4) Uani 1 1 d . . .
H6 H 0.9343 0.8563 0.2508 0.039 Uiso 1 1 calc R . .
C7 C 0.7221(3) 0.83738(19) 0.12513(8) 0.0300(4) Uani 1 1 d . . .
H7A H 0.8728 0.8698 0.1101 0.036 Uiso 1 1 calc R . .
H7B H 0.6286 0.9342 0.1306 0.036 Uiso 1 1 calc R . .
C8 C 0.7400(3) 0.47838(18) 0.13717(7) 0.0238(4) Uani 1 1 d . . .
H8 H 0.8980 0.4602 0.1516 0.029 Uiso 1 1 calc R . .
C9 C 0.3596(3) 0.6912(2) 0.10239(7) 0.0277(4) Uani 1 1 d . . .
H9 H 0.2817 0.7967 0.1049 0.033 Uiso 1 1 calc R . .
C10 C 0.6071(3) 0.7195(2) 0.07909(8) 0.0266(4) Uani 1 1 d . . .
H10 H 0.6029 0.7689 0.0376 0.032 Uiso 1 1 calc R . .
C11 C 0.7914(3) 0.6285(2) 0.28004(9) 0.0327(4) Uani 1 1 d . . .
C12 C 0.7395(4) 0.2886(2) 0.05602(8) 0.0339(4) Uani 1 1 d . . .
H12A H 0.6558 0.2056 0.0332 0.041 Uiso 1 1 calc R . .
H12B H 0.9006 0.2582 0.0583 0.041 Uiso 1 1 calc R . .
C13 C 0.6384(4) 0.3133(2) 0.12062(8) 0.0324(4) Uani 1 1 d . . .
H13A H 0.6885 0.2293 0.1493 0.039 Uiso 1 1 calc R . .
H13B H 0.4715 0.3164 0.1196 0.039 Uiso 1 1 calc R . .
C14 C 0.7100(3) 0.4551(2) 0.02593(8) 0.0296(4) Uani 1 1 d . . .
H14A H 0.8202 0.4705 -0.0075 0.036 Uiso 1 1 calc R . .
H14B H 0.5557 0.4680 0.0094 0.036 Uiso 1 1 calc R . .
C15 C 0.6203(3) 0.5866(2) 0.18513(7) 0.0241(4) Uani 1 1 d . . .
C16 C 0.7431(3) 0.74659(18) 0.18516(8) 0.0268(4) Uani 1 1 d . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C9 1.419(2) . ?
N2 C8 1.4938(19) . ?
N2 C10 1.479(2) . ?
N2 C14 1.489(2) . ?
O3 C11 1.381(2) . ?
O3 C15 1.4396(19) . ?
C4 C9 1.552(2) . ?
C4 C15 1.524(2) . ?
O5 C11 1.201(2) . ?
C6 C11 1.465(3) . ?
C6 C16 1.322(2) . ?
C7 C10 1.537(2) . ?
C7 C16 1.495(2) . ?
C8 C13 1.521(2) . ?
C8 C15 1.528(2) . ?
C9 C10 1.540(2) . ?
C12 C13 1.520(2) . ?
C12 C14 1.522(2) . ?
C15 C16 1.495(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 N2 C8 111.99(12) . . ?
C10 N2 C14 116.63(13) . . ?
C14 N2 C8 107.36(12) . . ?
C11 O3 C15 108.81(13) . . ?
C15 C4 C9 107.98(14) . . ?
C16 C6 C11 109.32(16) . . ?
C16 C7 C10 106.02(13) . . ?
N2 C8 C13 106.15(12) . . ?
N2 C8 C15 107.50(12) . . ?
C13 C8 C15 120.01(15) . . ?
O1 C9 C4 112.17(15) . . ?
O1 C9 C10 110.26(14) . . ?
C10 C9 C4 109.07(14) . . ?
N2 C10 C7 106.33(13) . . ?
N2 C10 C9 114.69(14) . . ?
C7 C10 C9 106.97(14) . . ?
O3 C11 C6 107.87(15) . . ?
O5 C11 O3 120.84(18) . . ?
O5 C11 C6 131.29(18) . . ?
C13 C12 C14 102.95(14) . . ?
C12 C13 C8 100.53(14) . . ?
N2 C14 C12 104.11(13) . . ?
O3 C15 C4 113.35(13) . . ?
O3 C15 C8 110.62(13) . . ?
O3 C15 C16 104.89(13) . . ?
C4 C15 C8 111.84(13) . . ?
C16 C15 C4 108.53(14) . . ?
C16 C15 C8 107.16(13) . . ?
C6 C16 C7 137.44(16) . . ?
C6 C16 C15 109.01(15) . . ?
C7 C16 C15 113.54(14) . . ?

_database_code_depnum_ccdc_archive 'CCDC 971455'
