# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
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data_13srv320
_database_code_depnum_ccdc_archive 'CCDC 1039437'
_audit_update_record             
;
2014-12-15 deposited with the CCDC.
2015-03-06 downloaded from the CCDC.
;
_audit_creation_date             2013-12-12
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2013.12.10 svn.r2850 for OlexSys, GUI svn.r4736)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C12 H9 F3 N2 O3'
_chemical_formula_sum            'C12 H9 F3 N2 O3'
_chemical_formula_weight         286.21
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   12.5161(10)
_cell_length_b                   14.0082(11)
_cell_length_c                   27.051(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4742.7(7)
_cell_formula_units_Z            16
_cell_measurement_reflns_used    9897
_cell_measurement_temperature    120
_cell_measurement_theta_max      28.91
_cell_measurement_theta_min      2.309
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.147
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.6090
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2009/1 (Bruker,2010) was used for absorption correction.
wR2(int) was 0.0900 before and 0.0582 after correction.
The Ratio of minimum to maximum transmission is 0.8164.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.603
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       brick
_exptl_crystal_F_000             2336
_exptl_crystal_size_max          0.63
_exptl_crystal_size_mid          0.46
_exptl_crystal_size_min          0.33
_exptl_special_details           
;
 The data collection nominally covered a full sphere of reciprocal space by
 a combination of 4 sets of ω scans each set at different φ and/or
 2θ angles and each scan (5 s exposure) covering -0.3° in ω.
 The crystal to detector distance was 5.84 cm.
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0371
_diffrn_reflns_av_unetI/netI     0.0214
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            37987
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         1.506
_diffrn_ambient_temperature      120
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 5.6
_diffrn_detector_type            'Bruker SMART CCD 6000 area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART CCD 6000 area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_current           35.0
_diffrn_source_power             1.75
_diffrn_source_target            Mo
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3538
_reflns_number_total             4178
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v7.46A (Bruker, 2008)'
_computing_data_collection       'SMART v5.625 (Bruker, 2001)'
_computing_data_reduction        'SAINT v7.46A (Bruker, 2008)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL-2012 (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.494
_refine_diff_density_min         -0.306
_refine_diff_density_rms         0.067
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.209
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     365
_refine_ls_number_reflns         4178
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0778
_refine_ls_R_factor_gt           0.0665
_refine_ls_restrained_S_all      1.209
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0320P)²+12.3320P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1543
_refine_ls_wR_factor_ref         0.1646
_refine_special_details          
;
 Methyl groups were refined as rigid bodies rotating around C---C bonds, 
 with a common refined U for three H atoms. Other H atoms: riding model.
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Others
 Uiso(H12A)=Uiso(H12B)=Uiso(H12C)=FVAR(1)
 Uiso(H12D)=Uiso(H12E)=Uiso(H12F)=FVAR(2)
3.a Rotating group:
 C12A(H12A,H12B,H12C), C12B(H12D,H12E,H12F)
3.b Secondary CH2 refined with riding coordinates:
 C11A(H11A,H11B), C11B(H11C,H11D)
3.c Aromatic/amide H refined with riding coordinates:
 C4A(H4A), C5A(H5A), C7A(H7A), C10A(H10A), C4B(H4B), C5B(H5B), C7B(H7B),
 C10B(H10B)
;
_atom_sites_solution_hydrogens   mixed
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1A F 0.4761(2) 0.11869(18) 0.79643(8) 0.0514(6) Uani 1 1 d . . . . .
F2A F 0.5055(2) -0.03208(16) 0.79088(8) 0.0494(6) Uani 1 1 d . . . . .
F3A F 0.6223(2) 0.05958(17) 0.82466(7) 0.0474(6) Uani 1 1 d . . . . .
O1A O 0.7041(2) 0.0796(2) 0.73701(9) 0.0391(6) Uani 1 1 d . . . . .
O2A O 0.5641(3) 0.1206(2) 0.46605(10) 0.0545(8) Uani 1 1 d . . . . .
O3A O 0.7330(3) 0.1499(2) 0.48845(9) 0.0501(8) Uani 1 1 d . . . . .
N1A N 0.5754(2) 0.0831(2) 0.64771(10) 0.0313(7) Uani 1 1 d . . . . .
N2A N 0.6956(3) 0.1181(2) 0.58374(11) 0.0380(7) Uani 1 1 d . . . . .
C1A C 0.5519(3) 0.0536(3) 0.78817(13) 0.0373(9) Uani 1 1 d . . . . .
C2A C 0.6073(3) 0.0691(2) 0.73744(12) 0.0310(8) Uani 1 1 d . . . . .
C3A C 0.5379(3) 0.0682(2) 0.69575(12) 0.0309(8) Uani 1 1 d . . . . .
C4A C 0.4281(3) 0.0516(3) 0.69210(14) 0.0387(9) Uani 1 1 d . . . . .
H4A H 0.3813 0.0398 0.7191 0.046 Uiso 1 1 calc R . . . .
C5A C 0.3985(3) 0.0550(3) 0.64270(15) 0.0428(10) Uani 1 1 d . . . . .
H5A H 0.3285 0.0458 0.6300 0.051 Uiso 1 1 calc R . . . .
C6A C 0.4890(3) 0.0743(3) 0.61527(13) 0.0366(9) Uani 1 1 d . . . . .
C7A C 0.5105(3) 0.0877(3) 0.56473(14) 0.0402(9) Uani 1 1 d . . . . .
H7A H 0.4556 0.0809 0.5408 0.048 Uiso 1 1 calc R . . . .
C8A C 0.6109(3) 0.1103(3) 0.55112(13) 0.0399(9) Uani 1 1 d . . . . .
C9A C 0.6328(4) 0.1270(3) 0.49720(14) 0.0426(9) Uani 1 1 d . . . . .
C10A C 0.6758(3) 0.1034(3) 0.63027(13) 0.0343(8) Uani 1 1 d . . . . .
H10A H 0.7332 0.1069 0.6532 0.041 Uiso 1 1 calc R . . . .
C11A C 0.7582(4) 0.1637(4) 0.43596(15) 0.0588(13) Uani 1 1 d . . . . .
H11A H 0.7476 0.1035 0.4175 0.071 Uiso 1 1 calc R . . . .
H11B H 0.7112 0.2133 0.4215 0.071 Uiso 1 1 calc R . . . .
C12A C 0.8677(4) 0.1930(5) 0.43333(18) 0.0725(16) Uani 1 1 d . . . . .
H12A H 0.8866 0.2067 0.3989 0.102(12) Uiso 1 1 d GR . . . .
H12B H 0.9136 0.1419 0.4460 0.102(12) Uiso 1 1 d GR . . . .
H12C H 0.8779 0.2507 0.4533 0.102(12) Uiso 1 1 d GR . . . .
F1B F 0.3427(2) 0.24824(19) 0.20641(8) 0.0560(7) Uani 1 1 d . . . . .
F2B F 0.2697(2) 0.11263(17) 0.19458(8) 0.0537(7) Uani 1 1 d . . . . .
F3B F 0.1820(2) 0.2403(2) 0.18004(8) 0.0563(7) Uani 1 1 d . . . . .
O1B O 0.1101(2) 0.20873(19) 0.26845(9) 0.0385(6) Uani 1 1 d . . . . .
O2B O 0.2624(3) 0.0807(3) 0.52943(10) 0.0650(10) Uani 1 1 d . . . . .
O3B O 0.0924(3) 0.1155(3) 0.51212(10) 0.0598(9) Uani 1 1 d . . . . .
N1B N 0.2458(2) 0.1636(2) 0.35136(10) 0.0291(6) Uani 1 1 d . . . . .
N2B N 0.1275(3) 0.1404(3) 0.41727(11) 0.0423(8) Uani 1 1 d . . . . .
C1B C 0.2522(3) 0.2011(3) 0.21053(13) 0.0373(9) Uani 1 1 d . . . . .
C2B C 0.2067(3) 0.1979(2) 0.26377(12) 0.0306(8) Uani 1 1 d . . . . .
C3B C 0.2806(3) 0.1792(2) 0.30281(12) 0.0298(8) Uani 1 1 d . . . . .
C4B C 0.3922(3) 0.1746(3) 0.30398(13) 0.0351(8) Uani 1 1 d . . . . .
H4B H 0.4378 0.1822 0.2762 0.042 Uiso 1 1 calc R . . . .
C5B C 0.4257(3) 0.1572(3) 0.35190(14) 0.0373(9) Uani 1 1 d . . . . .
H5B H 0.4976 0.1516 0.3627 0.045 Uiso 1 1 calc R . . . .
C6B C 0.3353(3) 0.1494(3) 0.38124(13) 0.0324(8) Uani 1 1 d . . . . .
C7B C 0.3164(3) 0.1313(3) 0.43169(13) 0.0365(9) Uani 1 1 d . . . . .
H7B H 0.3741 0.1224 0.4540 0.044 Uiso 1 1 calc R . . . .
C8B C 0.2148(3) 0.1267(3) 0.44734(13) 0.0395(9) Uani 1 1 d . . . . .
C9B C 0.1940(3) 0.1047(3) 0.50092(15) 0.0466(10) Uani 1 1 d . . . . .
C10B C 0.1449(3) 0.1584(3) 0.37088(13) 0.0357(8) Uani 1 1 d . . . . .
H10B H 0.0854 0.1683 0.3497 0.043 Uiso 1 1 calc R . . . .
C11B C 0.0649(4) 0.0956(5) 0.56381(16) 0.0735(17) Uani 1 1 d . . . . .
H11C H 0.0802 0.0281 0.5719 0.088 Uiso 1 1 calc R . . . .
H11D H 0.1073 0.1368 0.5862 0.088 Uiso 1 1 calc R . . . .
C12B C -0.0448(4) 0.1147(4) 0.56942(17) 0.0695(15) Uani 1 1 d . . . . .
H12D H -0.0858 0.0750 0.5464 0.152(18) Uiso 1 1 d GR . . . .
H12E H -0.0586 0.1822 0.5624 0.152(18) Uiso 1 1 d GR . . . .
H12F H -0.0666 0.1002 0.6034 0.152(18) Uiso 1 1 d GR . . . .

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
F1A 0.0583(15) 0.0551(15) 0.0409(13) -0.0075(11) 0.0139(11) 0.0087(12)
F2A 0.0679(16) 0.0425(13) 0.0377(12) -0.0008(10) 0.0107(11) -0.0170(12)
F3A 0.0628(15) 0.0552(15) 0.0241(10) -0.0049(10) 0.0002(10) -0.0056(12)
O1A 0.0391(15) 0.0504(16) 0.0278(13) 0.0029(11) -0.0032(11) -0.0015(13)
O2A 0.070(2) 0.062(2) 0.0323(15) 0.0015(14) -0.0141(15) 0.0011(16)
O3A 0.067(2) 0.0592(19) 0.0240(13) 0.0030(12) -0.0012(13) -0.0065(16)
N1A 0.0361(17) 0.0302(16) 0.0277(15) -0.0016(12) -0.0028(13) -0.0006(13)
N2A 0.0438(18) 0.0405(18) 0.0296(16) 0.0020(14) -0.0018(14) -0.0050(15)
C1A 0.047(2) 0.035(2) 0.0298(19) -0.0046(16) 0.0041(17) -0.0032(18)
C2A 0.039(2) 0.0263(18) 0.0277(18) -0.0023(14) 0.0017(15) 0.0019(16)
C3A 0.038(2) 0.0263(18) 0.0280(17) -0.0040(14) 0.0036(15) -0.0013(15)
C4A 0.037(2) 0.039(2) 0.040(2) -0.0081(17) 0.0040(17) 0.0012(17)
C5A 0.033(2) 0.050(2) 0.045(2) -0.0088(19) -0.0044(18) 0.0012(18)
C6A 0.040(2) 0.036(2) 0.0346(19) -0.0048(16) -0.0083(16) 0.0021(17)
C7A 0.046(2) 0.043(2) 0.0319(19) -0.0025(17) -0.0092(17) 0.0050(19)
C8A 0.058(3) 0.036(2) 0.0260(18) 0.0003(16) -0.0065(17) 0.0003(19)
C9A 0.054(3) 0.042(2) 0.032(2) 0.0032(17) -0.0022(19) -0.002(2)
C10A 0.041(2) 0.0328(19) 0.0293(18) -0.0008(15) -0.0024(16) -0.0026(16)
C11A 0.075(3) 0.072(3) 0.029(2) 0.009(2) 0.004(2) -0.006(3)
C12A 0.072(4) 0.106(5) 0.039(3) 0.005(3) 0.003(2) -0.011(3)
F1B 0.0657(16) 0.0670(17) 0.0352(12) 0.0036(11) 0.0092(11) -0.0266(14)
F2B 0.0849(19) 0.0410(13) 0.0352(12) -0.0076(10) 0.0092(12) 0.0043(13)
F3B 0.0682(17) 0.0745(18) 0.0261(11) 0.0113(11) -0.0009(11) 0.0183(14)
O1B 0.0391(15) 0.0461(16) 0.0303(13) 0.0082(11) -0.0032(11) -0.0018(12)
O2B 0.068(2) 0.096(3) 0.0308(15) 0.0170(16) -0.0105(15) -0.005(2)
O3B 0.065(2) 0.091(3) 0.0233(14) 0.0078(15) 0.0019(13) 0.0004(19)
N1B 0.0362(16) 0.0275(15) 0.0235(14) -0.0024(12) -0.0020(13) 0.0017(13)
N2B 0.047(2) 0.055(2) 0.0249(15) 0.0023(14) 0.0019(14) -0.0037(16)
C1B 0.047(2) 0.039(2) 0.0260(18) -0.0010(16) 0.0005(17) 0.0028(18)
C2B 0.041(2) 0.0256(17) 0.0251(17) 0.0006(14) 0.0009(15) -0.0023(15)
C3B 0.039(2) 0.0261(18) 0.0239(16) -0.0038(14) 0.0005(14) 0.0009(15)
C4B 0.037(2) 0.035(2) 0.0334(19) -0.0056(16) 0.0032(16) 0.0022(16)
C5B 0.037(2) 0.039(2) 0.036(2) -0.0055(16) -0.0026(16) 0.0048(17)
C6B 0.037(2) 0.0302(18) 0.0298(18) -0.0051(14) -0.0065(15) 0.0021(16)
C7B 0.045(2) 0.035(2) 0.0293(18) -0.0012(15) -0.0079(16) 0.0008(17)
C8B 0.051(2) 0.043(2) 0.0245(18) -0.0003(16) -0.0064(16) 0.0002(19)
C9B 0.046(2) 0.061(3) 0.033(2) 0.0050(19) -0.0016(19) -0.003(2)
C10B 0.040(2) 0.043(2) 0.0246(18) 0.0021(15) -0.0019(15) -0.0044(17)
C11B 0.069(3) 0.125(5) 0.026(2) 0.012(3) 0.009(2) -0.006(3)
C12B 0.074(4) 0.099(4) 0.036(2) 0.010(3) 0.002(2) 0.001(3)

_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
F1A C1A 1.334(4) . ?
F2A C1A 1.336(4) . ?
F3A C1A 1.325(4) . ?
O1A C2A 1.220(4) . ?
O2A C9A 1.208(5) . ?
O3A C9A 1.316(5) . ?
O3A C11A 1.467(5) . ?
N1A C3A 1.397(4) . ?
N1A C6A 1.398(5) . ?
N1A C10A 1.372(5) . ?
N2A C8A 1.384(5) . ?
N2A C10A 1.299(5) . ?
C1A C2A 1.553(5) . ?
C2A C3A 1.424(5) . ?
C3A C4A 1.398(5) . ?
C4A C5A 1.387(5) . ?
C5A C6A 1.381(6) . ?
C6A C7A 1.406(5) . ?
C7A C8A 1.347(6) . ?
C8A C9A 1.502(5) . ?
C11A C12A 1.432(7) . ?
F1B C1B 1.316(5) . ?
F2B C1B 1.330(4) . ?
F3B C1B 1.324(4) . ?
O1B C2B 1.225(4) . ?
O2B C9B 1.200(5) . ?
O3B C9B 1.316(5) . ?
O3B C11B 1.467(5) . ?
N1B C3B 1.401(4) . ?
N1B C6B 1.395(4) . ?
N1B C10B 1.370(5) . ?
N2B C8B 1.376(5) . ?
N2B C10B 1.298(5) . ?
C1B C2B 1.549(5) . ?
C2B C3B 1.428(5) . ?
C3B C4B 1.399(5) . ?
C4B C5B 1.384(5) . ?
C5B C6B 1.387(5) . ?
C6B C7B 1.408(5) . ?
C7B C8B 1.342(6) . ?
C8B C9B 1.505(5) . ?
C11B C12B 1.407(7) . ?

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
C9A O3A C11A 114.3(3) . . ?
C3A N1A C6A 108.1(3) . . ?
C10A N1A C3A 131.2(3) . . ?
C10A N1A C6A 120.7(3) . . ?
C10A N2A C8A 117.3(3) . . ?
F1A C1A F2A 107.2(3) . . ?
F1A C1A C2A 111.7(3) . . ?
F2A C1A C2A 111.6(3) . . ?
F3A C1A F1A 107.7(3) . . ?
F3A C1A F2A 107.7(3) . . ?
F3A C1A C2A 110.6(3) . . ?
O1A C2A C1A 118.0(3) . . ?
O1A C2A C3A 126.8(3) . . ?
C3A C2A C1A 115.2(3) . . ?
N1A C3A C2A 122.0(3) . . ?
N1A C3A C4A 106.8(3) . . ?
C4A C3A C2A 131.1(3) . . ?
C5A C4A C3A 108.9(3) . . ?
C6A C5A C4A 107.8(3) . . ?
N1A C6A C7A 116.8(3) . . ?
C5A C6A N1A 108.3(3) . . ?
C5A C6A C7A 134.9(4) . . ?
C8A C7A C6A 118.4(4) . . ?
N2A C8A C9A 117.8(4) . . ?
C7A C8A N2A 124.0(3) . . ?
C7A C8A C9A 118.2(4) . . ?
O2A C9A O3A 124.9(4) . . ?
O2A C9A C8A 122.4(4) . . ?
O3A C9A C8A 112.7(3) . . ?
N2A C10A N1A 122.7(3) . . ?
C12A C11A O3A 106.9(4) . . ?
C9B O3B C11B 115.1(4) . . ?
C6B N1B C3B 108.4(3) . . ?
C10B N1B C3B 131.0(3) . . ?
C10B N1B C6B 120.6(3) . . ?
C10B N2B C8B 117.8(3) . . ?
F1B C1B F2B 107.3(3) . . ?
F1B C1B F3B 108.1(3) . . ?
F1B C1B C2B 114.2(3) . . ?
F2B C1B C2B 109.6(3) . . ?
F3B C1B F2B 107.1(3) . . ?
F3B C1B C2B 110.3(3) . . ?
O1B C2B C1B 117.1(3) . . ?
O1B C2B C3B 125.8(3) . . ?
C3B C2B C1B 117.1(3) . . ?
N1B C3B C2B 121.4(3) . . ?
C4B C3B N1B 106.4(3) . . ?
C4B C3B C2B 132.2(3) . . ?
C5B C4B C3B 109.4(3) . . ?
C4B C5B C6B 107.6(3) . . ?
N1B C6B C7B 116.9(3) . . ?
C5B C6B N1B 108.2(3) . . ?
C5B C6B C7B 134.9(4) . . ?
C8B C7B C6B 118.2(3) . . ?
N2B C8B C9B 117.4(4) . . ?
C7B C8B N2B 124.0(3) . . ?
C7B C8B C9B 118.5(3) . . ?
O2B C9B O3B 125.0(4) . . ?
O2B C9B C8B 123.6(4) . . ?
O3B C9B C8B 111.4(3) . . ?
N2B C10B N1B 122.5(3) . . ?
C12B C11B O3B 107.2(4) . . ?

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_14srv167
_database_code_depnum_ccdc_archive 'CCDC 1039438'
_audit_update_record             
;
2014-12-15 deposited with the CCDC.
2015-03-06 downloaded from the CCDC.
;
_audit_creation_date             2014-07-15
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2014.06.27 svn.r2953 for OlexSys, GUI svn.r4855)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C11 H10 Cl N3 O2'
_chemical_formula_sum            'C11 H10 Cl N3 O2'
_chemical_formula_weight         251.67
_chemical_absolute_configuration ad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z'

_cell_length_a                   8.0883(3)
_cell_length_b                   7.0136(3)
_cell_length_c                   10.3616(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 107.9650(10)
_cell_angle_gamma                90.00
_cell_volume                     559.14(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3459
_cell_measurement_temperature    120.0
_cell_measurement_theta_max      30.83
_cell_measurement_theta_min      2.81
_exptl_absorpt_coefficient_mu    0.334
_exptl_absorpt_correction_T_max  .
_exptl_absorpt_correction_T_min  .
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.495
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             260
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.14
_exptl_special_details           
;
 The data collection nominally covered a full sphere of reciprocal space by
 a combination of 3 sets of ω scans each set at different φ and/or
 2θ angles and each scan (3 s exposure) covering -0.300° degrees in ω.
 The crystal to detector distance was 4.85 cm.
;
_diffrn_reflns_av_R_equivalents  0.0399
_diffrn_reflns_av_unetI/netI     0.0402
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6930
_diffrn_reflns_theta_full        29.00
_diffrn_reflns_theta_max         29.00
_diffrn_reflns_theta_min         2.07
_diffrn_ambient_temperature      120.0
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 5.6
_diffrn_detector_type            'Bruker SMART CCD 6000 area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'SMART 6K'
_diffrn_measurement_method       ω-scan
_diffrn_radiation_monochromator  Parallel,graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_current           35.0
_diffrn_source_power             1.75
_diffrn_source_target            Mo
_diffrn_source_voltage           50.0
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         0
_reflns_number_gt                2672
_reflns_number_total             2957
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'SAINT v6.45A (Bruker, 2003)'
_computing_data_collection       'SMART v5.625 (Bruker, 2001)'
_computing_data_reduction        'SAINT v6.45A (Bruker, 2003)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.506
_refine_diff_density_min         -0.312
_refine_diff_density_rms         0.059
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.06(6)
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         2957
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0453
_refine_ls_R_factor_gt           0.0404
_refine_ls_restrained_S_all      1.088
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0550P)²+0.1000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1009
_refine_ls_wR_factor_ref         0.1052
_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. 
;
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
Cl1 Cl 0.64472(7) -0.10160(7) 0.26125(6) 0.03148(15) Uani 1 d . . .
O1 O 0.02323(19) 1.1692(2) 0.25794(15) 0.0235(3) Uani 1 d . . .
O2 O 0.1771(2) 1.0287(3) 0.45351(16) 0.0292(3) Uani 1 d . . .
N1 N 0.2551(2) 0.6255(3) 0.19013(16) 0.0198(3) Uani 1 d . . .
N2 N 0.2553(2) 0.7307(3) 0.30004(16) 0.0208(3) Uani 1 d . . .
N3 N 0.0885(2) 0.8720(3) 0.10590(17) 0.0230(4) Uani 1 d . . .
C1 C 0.1539(2) 0.8769(4) 0.24468(19) 0.0211(4) Uani 1 d . . .
C2 C 0.1546(3) 0.7122(3) 0.0760(2) 0.0225(4) Uani 1 d . . .
C3 C 0.3509(3) 0.4514(3) 0.2057(2) 0.0205(4) Uani 1 d . . .
C4 C 0.3332(3) 0.3332(3) 0.0939(2) 0.0245(4) Uani 1 d . . .
C5 C 0.4248(3) 0.1639(3) 0.1107(2) 0.0248(4) Uani 1 d . . .
C6 C 0.5309(3) 0.1129(3) 0.2386(2) 0.0228(4) Uani 1 d . . .
C7 C 0.5497(3) 0.2289(3) 0.3500(2) 0.0230(4) Uani 1 d . . .
C8 C 0.4600(2) 0.4021(4) 0.33337(19) 0.0217(4) Uani 1 d . . .
C9 C 0.1212(3) 1.0308(3) 0.3313(2) 0.0211(4) Uani 1 d . . .
C10 C -0.0132(3) 1.3271(3) 0.3374(2) 0.0241(4) Uani 1 d . . .
C11 C -0.1316(3) 1.4636(4) 0.2397(2) 0.0261(5) Uani 1 d . . .
H2 H 0.128(3) 0.664(4) -0.009(3) 0.019(6) Uiso 1 d . . .
H4 H 0.261(3) 0.381(4) 0.007(3) 0.025(6) Uiso 1 d . . .
H5 H 0.413(4) 0.080(5) 0.034(3) 0.037(8) Uiso 1 d . . .
H7 H 0.624(4) 0.191(5) 0.438(3) 0.034(7) Uiso 1 d . . .
H8 H 0.464(3) 0.476(3) 0.401(2) 0.011(5) Uiso 1 d . . .
H10A H -0.064(3) 1.273(4) 0.401(3) 0.020(6) Uiso 1 d . . .
H10B H 0.099(3) 1.387(4) 0.385(2) 0.016(5) Uiso 1 d . . .
H11A H -0.161(3) 1.566(4) 0.289(3) 0.031(7) Uiso 1 d . . .
H11B H -0.246(3) 1.410(5) 0.193(3) 0.033(7) Uiso 1 d . . .
H11C H -0.080(3) 1.514(4) 0.174(3) 0.021(6) Uiso 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cl1 0.0316(3) 0.0221(2) 0.0394(3) -0.0001(2) 0.0090(2) 0.0049(2)
O1 0.0263(7) 0.0214(7) 0.0219(7) -0.0007(6) 0.0060(6) 0.0028(6)
O2 0.0363(9) 0.0283(8) 0.0205(7) 0.0023(6) 0.0053(6) 0.0081(7)
N1 0.0192(8) 0.0210(8) 0.0175(8) -0.0018(7) 0.0030(6) -0.0005(6)
N2 0.0220(8) 0.0207(8) 0.0184(8) -0.0014(7) 0.0042(6) 0.0009(7)
N3 0.0256(8) 0.0217(9) 0.0184(8) -0.0015(7) 0.0019(6) -0.0029(7)
C1 0.0176(8) 0.0229(11) 0.0200(9) 0.0015(8) 0.0018(7) -0.0015(8)
C2 0.0229(10) 0.0244(10) 0.0167(9) 0.0019(8) 0.0011(7) -0.0022(8)
C3 0.0186(9) 0.0195(9) 0.0235(9) 0.0006(7) 0.0067(8) -0.0008(7)
C4 0.0208(10) 0.0265(10) 0.0233(10) -0.0032(8) 0.0026(8) 0.0011(8)
C5 0.0237(10) 0.0235(10) 0.0254(10) -0.0075(8) 0.0047(8) -0.0019(8)
C6 0.0210(9) 0.0182(9) 0.0288(10) 0.0014(8) 0.0071(8) -0.0003(7)
C7 0.0218(9) 0.0253(10) 0.0213(9) 0.0042(8) 0.0057(8) 0.0027(8)
C8 0.0232(9) 0.0234(9) 0.0187(8) 0.0011(9) 0.0066(7) 0.0033(9)
C9 0.0207(10) 0.0199(9) 0.0226(9) 0.0005(8) 0.0064(8) -0.0012(8)
C10 0.0267(11) 0.0232(10) 0.0228(10) -0.0013(8) 0.0082(8) 0.0025(9)
C11 0.0277(11) 0.0200(9) 0.0307(11) 0.0055(9) 0.0090(9) 0.0075(8)

_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
Cl1 C6 1.741(2) . ?
O1 C9 1.333(3) . ?
O1 C10 1.464(3) . ?
O2 C9 1.206(2) . ?
N1 N2 1.357(2) . ?
N1 C2 1.355(3) . ?
N1 C3 1.429(3) . ?
N2 C1 1.328(3) . ?
N3 C1 1.371(2) . ?
N3 C2 1.319(3) . ?
C1 C9 1.479(3) . ?
C2 H2 0.90(3) . ?
C3 C4 1.396(3) . ?
C3 C8 1.389(3) . ?
C4 C5 1.382(3) . ?
C4 H4 0.97(3) . ?
C5 C6 1.385(3) . ?
C5 H5 0.97(3) . ?
C6 C7 1.382(3) . ?
C7 C8 1.398(3) . ?
C7 H7 0.96(3) . ?
C8 H8 0.87(2) . ?
C10 C11 1.503(3) . ?
C10 H10A 0.96(3) . ?
C10 H10B 0.98(2) . ?
C11 H11A 0.96(3) . ?
C11 H11B 0.98(3) . ?
C11 H11C 0.97(3) . ?

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
C9 O1 C10 114.70(16) . . ?
N2 N1 C3 120.66(16) . . ?
C2 N1 N2 109.50(17) . . ?
C2 N1 C3 129.84(18) . . ?
C1 N2 N1 102.51(15) . . ?
C2 N3 C1 102.38(18) . . ?
N2 C1 N3 114.9(2) . . ?
N2 C1 C9 120.23(17) . . ?
N3 C1 C9 124.9(2) . . ?
N1 C2 H2 125.5(17) . . ?
N3 C2 N1 110.71(18) . . ?
N3 C2 H2 123.6(17) . . ?
C4 C3 N1 120.06(18) . . ?
C8 C3 N1 118.91(19) . . ?
C8 C3 C4 121.0(2) . . ?
C3 C4 H4 116.5(18) . . ?
C5 C4 C3 119.5(2) . . ?
C5 C4 H4 124.0(17) . . ?
C4 C5 C6 119.5(2) . . ?
C4 C5 H5 120.3(18) . . ?
C6 C5 H5 120.1(18) . . ?
C5 C6 Cl1 119.88(17) . . ?
C7 C6 Cl1 118.58(17) . . ?
C7 C6 C5 121.5(2) . . ?
C6 C7 C8 119.29(19) . . ?
C6 C7 H7 120.6(19) . . ?
C8 C7 H7 120.1(19) . . ?
C3 C8 C7 119.1(2) . . ?
C3 C8 H8 118.6(15) . . ?
C7 C8 H8 122.1(15) . . ?
O1 C9 C1 111.79(17) . . ?
O2 C9 O1 124.9(2) . . ?
O2 C9 C1 123.30(19) . . ?
O1 C10 C11 107.45(17) . . ?
O1 C10 H10A 107.0(16) . . ?
O1 C10 H10B 106.7(15) . . ?
C11 C10 H10A 113.4(15) . . ?
C11 C10 H10B 111.3(16) . . ?
H10A C10 H10B 110.6(19) . . ?
C10 C11 H11A 109.3(17) . . ?
C10 C11 H11B 113.3(19) . . ?
C10 C11 H11C 112.3(15) . . ?
H11A C11 H11B 102(2) . . ?
H11A C11 H11C 110(2) . . ?
H11B C11 H11C 110(2) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_14srv235
_database_code_depnum_ccdc_archive 'CCDC 1039439'
_audit_update_record             
;
2014-12-15 deposited with the CCDC.
2015-03-06 downloaded from the CCDC.
;
_audit_creation_date             2014-11-03
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2014.10.30 svn.r3070 for OlexSys, GUI svn.r4932)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C12 H8 Br F3 N2 O3'
_chemical_formula_sum            'C12 H8 Br F3 N2 O3'
_chemical_formula_weight         365.10
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   6.79290(10)
_cell_length_b                   9.5186(2)
_cell_length_c                   10.3220(2)
_cell_angle_alpha                102.643(3)
_cell_angle_beta                 91.759(3)
_cell_angle_gamma                104.107(3)
_cell_volume                     629.09(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    8948
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      31.587
_cell_measurement_theta_min      2.269
_exptl_absorpt_coefficient_mu    3.321
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.4928
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.1521 before and 0.1023 after correction.
The Ratio of minimum to maximum transmission is 0.4928.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.927
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.424
_exptl_crystal_size_mid          0.249
_exptl_crystal_size_min          0.187
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0641
_diffrn_reflns_av_unetI/netI     0.0558
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10397
_diffrn_reflns_theta_full        28.00
_diffrn_reflns_theta_max         28.00
_diffrn_reflns_theta_min         2.27
_diffrn_ambient_temperature      120.0
_diffrn_detector                 'Bruker PHOTON 100 CMOS'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'CMOS sensor'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'Bruker D8 Venture'
_diffrn_measurement_device_type  '3-circle diffractometer'
_diffrn_measurement_method       ω-scan
_diffrn_radiation_monochromator  'focusing mirrors'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'ImuS microsource'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2835
_reflns_number_total             3027
_reflns_threshold_expression     >2sigma(I)
_computing.bruker_data_scaling   'SADABS V2012/1 (Bruker AXS Inc.)'
_computing_cell_refinement       'APEX2 v.2013.4_1 (Bruker, 2013)'
_computing_data_collection       'APEX2 v.2013.4_1 (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         1.843
_refine_diff_density_min         -0.993
_refine_diff_density_rms         0.226
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         3027
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0528
_refine_ls_R_factor_gt           0.0507
_refine_ls_restrained_S_all      1.101
_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)+(0.0900P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1256
_refine_ls_wR_factor_ref         0.1275
_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. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5), C7(H7)
2.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C)
;
_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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
Br1 Br 0.66703(3) -0.27470(2) 0.51455(2) 0.01771(14) Uani 1 d . . .
F1 F 1.0366(3) 0.3073(2) 0.84804(18) 0.0272(4) Uani 1 d . . .
F2 F 0.9376(3) 0.50776(19) 0.86293(18) 0.0259(4) Uani 1 d . . .
F3 F 0.7183(3) 0.3006(2) 0.85934(18) 0.0263(4) Uani 1 d . . .
O1 O 0.8741(3) 0.4391(2) 0.6060(2) 0.0257(5) Uani 1 d . . .
O2 O 0.7823(4) 0.0339(3) -0.0438(2) 0.0307(5) Uani 1 d . . .
O3 O 0.6597(3) -0.1913(2) 0.00061(19) 0.0197(4) Uani 1 d . . .
N1 N 0.8098(4) 0.1659(3) 0.2251(2) 0.0203(5) Uani 1 d . . .
N2 N 0.7932(3) 0.1388(3) 0.4454(2) 0.0150(4) Uani 1 d . . .
C1 C 0.8111(4) 0.1792(3) 0.5843(3) 0.0153(5) Uani 1 d . . .
C2 C 0.7714(4) 0.0484(3) 0.6303(3) 0.0161(5) Uani 1 d . . .
H2 H 0.7741 0.0421 0.7209 0.019 Uiso 1 calc . . R
C3 C 0.7273(4) -0.0712(3) 0.5192(3) 0.0148(5) Uani 1 d . . .
C4 C 0.7413(4) -0.0153(3) 0.4043(3) 0.0147(5) Uani 1 d . . .
C5 C 0.7168(4) -0.0802(3) 0.2669(3) 0.0154(5) Uani 1 d . . .
H5 H 0.6769 -0.1853 0.2343 0.019 Uiso 1 calc . . R
C6 C 0.7523(4) 0.0131(3) 0.1816(3) 0.0173(5) Uani 1 d . . .
C7 C 0.8274(4) 0.2246(3) 0.3517(3) 0.0192(6) Uani 1 d . . .
H7 H 0.8649 0.3301 0.3815 0.023 Uiso 1 calc . . R
C8 C 0.8585(4) 0.3329(3) 0.6563(3) 0.0174(5) Uani 1 d . . .
C9 C 0.8883(4) 0.3629(3) 0.8097(3) 0.0189(5) Uani 1 d . . .
C10 C 0.7345(4) -0.0443(3) 0.0335(3) 0.0185(5) Uani 1 d . . .
C11 C 0.6384(5) -0.2613(3) -0.1408(3) 0.0219(6) Uani 1 d . . .
H11A H 0.7708 -0.2759 -0.1702 0.026 Uiso 1 calc . . R
H11B H 0.5921 -0.1977 -0.1930 0.026 Uiso 1 calc . . R
C12 C 0.4838(5) -0.4091(4) -0.1619(3) 0.0274(7) Uani 1 d . . .
H12A H 0.4678 -0.4600 -0.2565 0.041 Uiso 1 calc . . GR
H12B H 0.3527 -0.3931 -0.1342 0.041 Uiso 1 calc . . GR
H12C H 0.5302 -0.4705 -0.1088 0.041 Uiso 1 calc . . GR

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
Br1 0.02056(19) 0.01479(19) 0.01609(19) 0.00426(12) 0.00269(11) 0.00069(12)
F1 0.0274(9) 0.0303(10) 0.0232(9) 0.0008(7) -0.0046(7) 0.0118(8)
F2 0.0324(9) 0.0173(8) 0.0224(9) -0.0027(7) -0.0006(7) 0.0028(7)
F3 0.0249(9) 0.0299(10) 0.0211(9) 0.0055(7) 0.0082(7) 0.0011(7)
O1 0.0341(12) 0.0174(10) 0.0226(11) 0.0050(8) 0.0037(9) 0.0003(8)
O2 0.0486(14) 0.0243(11) 0.0163(10) 0.0079(9) 0.0032(9) 0.0014(10)
O3 0.0244(10) 0.0206(10) 0.0118(9) 0.0031(7) 0.0024(7) 0.0018(8)
N1 0.0213(11) 0.0196(12) 0.0189(12) 0.0058(9) 0.0024(9) 0.0017(9)
N2 0.0124(10) 0.0165(10) 0.0147(11) 0.0044(8) 0.0011(8) 0.0005(8)
C1 0.0122(11) 0.0176(12) 0.0145(12) 0.0032(10) 0.0023(9) 0.0013(9)
C2 0.0125(11) 0.0184(13) 0.0157(12) 0.0038(10) 0.0019(9) 0.0008(9)
C3 0.0139(11) 0.0143(12) 0.0151(12) 0.0040(9) 0.0025(9) 0.0012(9)
C4 0.0101(11) 0.0165(12) 0.0168(12) 0.0038(10) 0.0026(9) 0.0018(9)
C5 0.0114(11) 0.0170(12) 0.0174(12) 0.0049(10) 0.0006(9) 0.0022(9)
C6 0.0127(11) 0.0205(13) 0.0167(13) 0.0035(10) 0.0012(9) 0.0015(9)
C7 0.0192(12) 0.0172(13) 0.0204(14) 0.0068(11) 0.0019(10) 0.0008(10)
C8 0.0136(11) 0.0173(13) 0.0192(13) 0.0036(10) 0.0035(10) 0.0007(10)
C9 0.0177(12) 0.0202(13) 0.0166(13) 0.0014(10) 0.0007(10) 0.0032(10)
C10 0.0181(12) 0.0236(14) 0.0142(13) 0.0063(10) 0.0016(10) 0.0043(10)
C11 0.0253(14) 0.0255(14) 0.0124(12) 0.0037(10) 0.0030(10) 0.0025(11)
C12 0.0328(16) 0.0221(15) 0.0222(15) 0.0021(12) 0.0013(12) 0.0004(12)

_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
Br1 C3 1.869(3) . ?
F1 C9 1.334(3) . ?
F2 C9 1.322(3) . ?
F3 C9 1.336(3) . ?
O1 C8 1.219(4) . ?
O2 C10 1.206(4) . ?
O3 C10 1.329(4) . ?
O3 C11 1.453(3) . ?
N1 C6 1.376(4) . ?
N1 C7 1.293(4) . ?
N2 C1 1.394(3) . ?
N2 C4 1.386(3) . ?
N2 C7 1.388(4) . ?
C1 C2 1.397(4) . ?
C1 C8 1.441(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.394(4) . ?
C3 C4 1.399(4) . ?
C4 C5 1.404(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.369(4) . ?
C6 C10 1.497(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.543(4) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.504(4) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?

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 O3 C11 116.1(2) . . ?
C7 N1 C6 119.0(2) . . ?
C4 N2 C1 108.9(2) . . ?
C4 N2 C7 119.9(2) . . ?
C7 N2 C1 131.1(2) . . ?
N2 C1 C2 107.7(2) . . ?
N2 C1 C8 121.7(2) . . ?
C2 C1 C8 130.6(2) . . ?
C1 C2 H2 126.2 . . ?
C3 C2 C1 107.6(2) . . ?
C3 C2 H2 126.2 . . ?
C2 C3 Br1 128.3(2) . . ?
C2 C3 C4 108.6(2) . . ?
C4 C3 Br1 123.1(2) . . ?
N2 C4 C3 107.2(2) . . ?
N2 C4 C5 118.3(2) . . ?
C3 C4 C5 134.4(3) . . ?
C4 C5 H5 121.1 . . ?
C6 C5 C4 117.7(2) . . ?
C6 C5 H5 121.1 . . ?
N1 C6 C10 115.1(2) . . ?
C5 C6 N1 122.8(2) . . ?
C5 C6 C10 122.1(3) . . ?
N1 C7 N2 122.2(3) . . ?
N1 C7 H7 118.9 . . ?
N2 C7 H7 118.9 . . ?
O1 C8 C1 125.3(3) . . ?
O1 C8 C9 118.2(3) . . ?
C1 C8 C9 116.5(2) . . ?
F1 C9 F3 107.7(2) . . ?
F1 C9 C8 111.2(2) . . ?
F2 C9 F1 108.1(2) . . ?
F2 C9 F3 108.3(2) . . ?
F2 C9 C8 110.3(2) . . ?
F3 C9 C8 111.2(2) . . ?
O2 C10 O3 125.5(3) . . ?
O2 C10 C6 123.8(3) . . ?
O3 C10 C6 110.7(2) . . ?
O3 C11 H11A 110.2 . . ?
O3 C11 H11B 110.2 . . ?
O3 C11 C12 107.5(2) . . ?
H11A C11 H11B 108.5 . . ?
C12 C11 H11A 110.2 . . ?
C12 C11 H11B 110.2 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C8 C9 F1 -122.8(3) . . . . ?
O1 C8 C9 F2 -3.0(4) . . . . ?
O1 C8 C9 F3 117.2(3) . . . . ?
N1 C6 C10 O2 6.0(4) . . . . ?
N1 C6 C10 O3 -174.0(2) . . . . ?
N2 C1 C8 O1 4.9(4) . . . . ?
C1 C8 C9 F1 58.0(3) . . . . ?
C1 C8 C9 F2 177.9(2) . . . . ?
C1 C8 C9 F3 -62.0(3) . . . . ?
C2 C1 C8 O1 -173.5(3) . . . . ?
C2 C1 C8 C9 5.6(4) . . . . ?
C5 C6 C10 O2 -173.0(3) . . . . ?
C5 C6 C10 O3 7.0(4) . . . . ?
C6 C10 O3 C11 -178.9(2) . . . . ?
C9 C8 C1 N2 -176.0(2) . . . . ?
C11 O3 C10 O2 1.1(4) . . . . ?
C12 C11 O3 C10 -158.6(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_14srv265
_database_code_depnum_ccdc_archive 'CCDC 1039440'
_audit_update_record             
;
2014-12-15 deposited with the CCDC.
2015-03-06 downloaded from the CCDC.
;
_audit_creation_date             2014-12-03
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2014.11.28 svn.r3106 for OlexSys, GUI svn.r4957)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C10 H8 I N3 O4'
_chemical_formula_sum            'C10 H8 I N3 O4'
_chemical_formula_weight         361.09
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   14.7611(3)
_cell_length_b                   4.6408(3)
_cell_length_c                   17.1279(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.424(2)
_cell_angle_gamma                90.00
_cell_volume                     1173.29(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9934
_cell_measurement_temperature    120.0
_cell_measurement_theta_max      31.54
_cell_measurement_theta_min      2.74
_exptl_absorpt_coefficient_mu    2.741
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.5916
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/4 (Bruker,2014/4) was used for absorption correction.
wR2(int) was 0.1660 before and 0.0832 after correction.
The Ratio of minimum to maximum transmission is 0.5916.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    2.044
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plank
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.56
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.07
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0632
_diffrn_reflns_av_unetI/netI     0.0474
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            17049
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         30.00
_diffrn_reflns_theta_min         2.38
_diffrn_ambient_temperature      120.0
_diffrn_detector                 'Bruker PHOTON 100 CMOS'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'CMOS sensor'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'Bruker D8 Venture'
_diffrn_measurement_device_type  D8Venture
_diffrn_measurement_method       ω-scan
_diffrn_radiation_monochromator  'focusing mirrors'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'ImuS microsource'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         0
_reflns_number_gt                3039
_reflns_number_total             3436
_reflns_threshold_expression     >2sigma(I)
_computing.bruker_data_scaling   'SADABS V2012/1 (Bruker AXS Inc.)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX2 v.2013.4_1 (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         2.010
_refine_diff_density_min         -0.660
_refine_diff_density_rms         0.181
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         3436
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0384
_refine_ls_R_factor_gt           0.0320
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0400P)²+0.4000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0742
_refine_ls_wR_factor_ref         0.0774
_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. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5), C7(H7)
2.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C)
;
_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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
I1 I 0.800365(10) 0.16103(3) 0.424289(8) 0.01398(7) Uani 1 d . . .
O1 O 0.93764(12) -0.5247(4) 0.73543(10) 0.0147(3) Uani 1 d . . .
O2 O 1.01070(13) -0.6134(4) 0.62787(11) 0.0172(4) Uani 1 d . . .
O3 O 0.62538(12) 0.5043(4) 0.80143(10) 0.0149(3) Uani 1 d . . .
O4 O 0.61259(13) 0.6868(4) 0.68008(12) 0.0174(4) Uani 1 d . . .
N1 N 0.75622(14) 0.1378(4) 0.75964(12) 0.0108(4) Uani 1 d . . .
N2 N 0.84241(13) -0.0865(4) 0.66205(11) 0.0091(4) Uani 1 d . . .
N3 N 0.95442(13) -0.4776(4) 0.66595(11) 0.0113(4) Uani 1 d . . .
C1 C 0.90584(16) -0.2610(5) 0.62628(14) 0.0110(4) Uani 1 d . . .
C2 C 0.90487(17) -0.2100(5) 0.54680(15) 0.0124(5) Uani 1 d . . .
H2 H 0.9419 -0.3021 0.5092 0.015 Uiso 1 calc . . R
C3 C 0.84005(16) 0.0001(5) 0.53180(13) 0.0123(4) Uani 1 d . . .
C4 C 0.80161(16) 0.0780(5) 0.60298(14) 0.0110(4) Uani 1 d . . .
C5 C 0.73523(16) 0.2790(5) 0.62538(14) 0.0114(4) Uani 1 d . . .
H5 H 0.7053 0.3955 0.5876 0.014 Uiso 1 calc . . R
C6 C 0.71509(16) 0.3018(5) 0.70256(14) 0.0105(4) Uani 1 d . . .
C7 C 0.81813(16) -0.0459(5) 0.73905(13) 0.0108(4) Uani 1 d . . .
H7 H 0.8478 -0.1562 0.7784 0.013 Uiso 1 calc . . R
C8 C 0.64556(15) 0.5197(5) 0.72599(14) 0.0122(4) Uani 1 d . . .
C9 C 0.55953(19) 0.7163(6) 0.82816(17) 0.0198(5) Uani 1 d . . .
H9A H 0.5025 0.6985 0.7977 0.024 Uiso 1 calc . . R
H9B H 0.5836 0.9135 0.8210 0.024 Uiso 1 calc . . R
C10 C 0.5421(3) 0.6614(7) 0.91236(19) 0.0324(8) Uani 1 d . . .
H10A H 0.5207 0.4630 0.9191 0.049 Uiso 1 calc . . GR
H10B H 0.4958 0.7956 0.9310 0.049 Uiso 1 calc . . GR
H10C H 0.5982 0.6893 0.9423 0.049 Uiso 1 calc . . GR

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
I1 0.01814(10) 0.01713(10) 0.00669(9) 0.00119(5) 0.00000(6) 0.00015(6)
O1 0.0179(8) 0.0159(9) 0.0103(8) 0.0019(7) 0.0012(6) 0.0005(7)
O2 0.0161(9) 0.0205(9) 0.0151(9) -0.0012(7) 0.0039(7) 0.0073(7)
O3 0.0154(8) 0.0169(9) 0.0125(8) -0.0007(7) 0.0043(6) 0.0047(7)
O4 0.0179(9) 0.0189(10) 0.0154(9) 0.0017(7) 0.0010(7) 0.0045(7)
N1 0.0122(9) 0.0124(10) 0.0079(9) -0.0006(7) -0.0007(7) -0.0011(7)
N2 0.0093(9) 0.0096(9) 0.0084(9) -0.0001(7) 0.0004(7) -0.0013(7)
N3 0.0099(9) 0.0120(9) 0.0121(9) -0.0012(8) -0.0002(7) -0.0017(7)
C1 0.0131(11) 0.0096(10) 0.0103(11) -0.0014(9) 0.0014(9) -0.0009(9)
C2 0.0139(11) 0.0121(11) 0.0113(11) -0.0017(8) 0.0022(9) -0.0009(9)
C3 0.0156(11) 0.0134(11) 0.0079(10) 0.0003(9) 0.0001(8) -0.0028(9)
C4 0.0129(10) 0.0126(10) 0.0075(10) 0.0006(8) -0.0002(8) -0.0026(9)
C5 0.0107(10) 0.0118(11) 0.0116(11) 0.0012(9) -0.0015(8) -0.0002(9)
C6 0.0093(10) 0.0118(11) 0.0105(11) -0.0013(8) -0.0002(8) -0.0024(8)
C7 0.0124(10) 0.0130(11) 0.0069(10) -0.0005(8) 0.0010(8) -0.0018(9)
C8 0.0093(10) 0.0119(11) 0.0153(11) -0.0014(9) 0.0007(8) -0.0025(9)
C9 0.0201(13) 0.0213(13) 0.0179(13) -0.0017(10) 0.0050(10) 0.0079(11)
C10 0.0354(18) 0.042(2) 0.0199(15) -0.0022(12) 0.0083(13) 0.0182(14)

_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
I1 C3 2.068(2) . ?
O1 N3 1.237(2) . ?
O2 N3 1.233(3) . ?
O3 C8 1.330(3) . ?
O3 C9 1.459(3) . ?
O4 C8 1.205(3) . ?
N1 C6 1.377(3) . ?
N1 C7 1.300(3) . ?
N2 C1 1.384(3) . ?
N2 C4 1.400(3) . ?
N2 C7 1.382(3) . ?
N3 C1 1.407(3) . ?
C1 C2 1.382(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.389(3) . ?
C3 C4 1.396(3) . ?
C4 C5 1.408(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.361(3) . ?
C6 C8 1.498(3) . ?
C7 H7 0.9500 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.489(4) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?

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
C8 O3 C9 115.04(19) . . ?
C7 N1 C6 118.5(2) . . ?
C1 N2 C4 106.73(19) . . ?
C7 N2 C1 133.1(2) . . ?
C7 N2 C4 120.1(2) . . ?
O1 N3 C1 119.08(19) . . ?
O2 N3 O1 124.0(2) . . ?
O2 N3 C1 116.9(2) . . ?
N2 C1 N3 123.2(2) . . ?
C2 C1 N2 109.5(2) . . ?
C2 C1 N3 126.9(2) . . ?
C1 C2 H2 126.1 . . ?
C1 C2 C3 107.7(2) . . ?
C3 C2 H2 126.1 . . ?
C2 C3 I1 127.48(18) . . ?
C2 C3 C4 107.7(2) . . ?
C4 C3 I1 124.74(18) . . ?
N2 C4 C5 117.4(2) . . ?
C3 C4 N2 108.3(2) . . ?
C3 C4 C5 134.2(2) . . ?
C4 C5 H5 120.9 . . ?
C6 C5 C4 118.3(2) . . ?
C6 C5 H5 120.9 . . ?
N1 C6 C8 118.8(2) . . ?
C5 C6 N1 123.3(2) . . ?
C5 C6 C8 117.9(2) . . ?
N1 C7 N2 122.4(2) . . ?
N1 C7 H7 118.8 . . ?
N2 C7 H7 118.8 . . ?
O3 C8 C6 112.5(2) . . ?
O4 C8 O3 125.2(2) . . ?
O4 C8 C6 122.3(2) . . ?
O3 C9 H9A 110.1 . . ?
O3 C9 H9B 110.1 . . ?
O3 C9 C10 108.0(2) . . ?
H9A C9 H9B 108.4 . . ?
C10 C9 H9A 110.1 . . ?
C10 C9 H9B 110.1 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C6 C8 O3 -6.7(3) . . . . ?
N1 C6 C8 O4 173.6(2) . . . . ?
N2 C1 N3 O1 3.1(3) . . . . ?
N2 C1 N3 O2 -178.2(2) . . . . ?
C2 C1 N3 O1 -168.8(2) . . . . ?
C2 C1 N3 O2 9.9(4) . . . . ?
C5 C6 C8 O3 174.1(2) . . . . ?
C5 C6 C8 O4 -5.6(4) . . . . ?
C6 C8 O3 C9 178.6(2) . . . . ?
C9 O3 C8 O4 -1.7(4) . . . . ?
C10 C9 O3 C8 177.7(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_192b
_database_code_depnum_ccdc_archive 'CCDC 1039441'
_audit_update_record             
;
2014-12-15 deposited with the CCDC.
2015-03-06 downloaded from the CCDC.
;
_audit_creation_date             2014-10-08
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C10 H8 Cl N3 O4'
_chemical_formula_sum            'C10 H8 Cl N3 O4'
_chemical_formula_weight         269.64
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   6.3391(12)
_cell_length_b                   7.7064(15)
_cell_length_c                   12.819(2)
_cell_angle_alpha                93.164(6)
_cell_angle_beta                 102.778(6)
_cell_angle_gamma                113.261(6)
_cell_volume                     553.93(18)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3899
_cell_measurement_temperature    120.0
_cell_measurement_theta_max      31.42
_cell_measurement_theta_min      2.91
_exptl_absorpt_coefficient_mu    0.356
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.6785
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.1402 before and 0.1157 after correction.
The Ratio of minimum to maximum transmission is 0.6785.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.617
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             276
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.02
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0929
_diffrn_reflns_av_unetI/netI     0.0912
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            9387
_diffrn_reflns_theta_full        29.00
_diffrn_reflns_theta_max         29.00
_diffrn_reflns_theta_min         3.57
_diffrn_ambient_temperature      120.0
_diffrn_detector                 'Bruker PHOTON 100 CMOS'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'CMOS sensor'
_diffrn_measured_fraction_theta_full 0.912
_diffrn_measured_fraction_theta_max 0.912
_diffrn_measurement_device       'Bruker D8 Venture'
_diffrn_measurement_device_type  D8Venture
_diffrn_measurement_method       ω-scan
_diffrn_radiation_monochromator  'focusing mirrors'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'ImuS microsource'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         0
_reflns_number_gt                1856
_reflns_number_total             2696
_reflns_threshold_expression     >2sigma(I)
_computing.bruker_data_scaling   'SADABS V2012/1 (Bruker AXS Inc.)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX2 v.2013.4_1 (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         1.899
_refine_diff_density_min         -1.315
_refine_diff_density_rms         0.180
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2696
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1213
_refine_ls_R_factor_gt           0.0889
_refine_ls_restrained_S_all      1.024
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1500P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2074
_refine_ls_wR_factor_ref         0.2298
_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. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5), C7(H7)
2.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
Cl1 Cl 0.12739(14) 0.36206(13) 0.37922(7) 0.0256(3) Uani 1 d . . .
O1 O 0.3690(5) 0.4104(4) 0.8764(2) 0.0345(7) Uani 1 d . . .
O2 O 0.1875(5) 0.1263(4) 0.7807(3) 0.0394(7) Uani 1 d . . .
O3 O 0.7192(4) 1.0878(4) 0.8887(2) 0.0274(6) Uani 1 d . . .
O4 O 0.7328(5) 1.2529(4) 0.7488(2) 0.0296(6) Uani 1 d . . .
N1 N 0.5046(5) 0.9178(4) 0.6052(2) 0.0234(6) Uani 1 d . . .
N2 N 0.3254(4) 0.5837(4) 0.5751(2) 0.0186(6) Uani 1 d . . .
N3 N 0.2773(5) 0.3012(4) 0.7904(3) 0.0272(7) Uani 1 d . . .
C1 C 0.2066(6) 0.4000(5) 0.5169(3) 0.0220(7) Uani 1 d . . .
C2 C 0.1742(6) 0.2732(5) 0.5876(3) 0.0256(8) Uani 1 d . . .
H2 H 0.0977 0.1377 0.5698 0.031 Uiso 1 calc . . R
C3 C 0.2754(6) 0.3803(5) 0.6922(3) 0.0229(7) Uani 1 d . . .
C4 C 0.3698(5) 0.5740(5) 0.6860(3) 0.0189(7) Uani 1 d . . .
C5 C 0.4894(5) 0.7470(5) 0.7577(3) 0.0207(7) Uani 1 d . . .
H5 H 0.5263 0.7494 0.8339 0.025 Uiso 1 calc . . R
C6 C 0.5510(5) 0.9114(5) 0.7147(3) 0.0214(7) Uani 1 d . . .
C7 C 0.3954(6) 0.7580(5) 0.5387(3) 0.0214(7) Uani 1 d . . .
H7 H 0.3624 0.7605 0.4630 0.026 Uiso 1 calc . . R
C8 C 0.6771(6) 1.1045(5) 0.7841(3) 0.0228(7) Uani 1 d . . .
C9 C 0.8436(7) 1.2668(5) 0.9648(3) 0.0308(8) Uani 1 d . . .
H9A H 0.7387 1.3339 0.9642 0.037 Uiso 1 calc . . R
H9B H 0.9877 1.3516 0.9446 0.037 Uiso 1 calc . . R
C10 C 0.9108(7) 1.2172(6) 1.0743(3) 0.0349(9) Uani 1 d . . .
H10A H 1.0172 1.1532 1.0741 0.052 Uiso 1 calc . . GR
H10B H 0.7670 1.1314 1.0927 0.052 Uiso 1 calc . . GR
H10C H 0.9924 1.3342 1.1280 0.052 Uiso 1 calc . . GR

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
Cl1 0.0279(4) 0.0308(5) 0.0161(4) -0.0009(3) 0.0019(3) 0.0129(3)
O1 0.0520(16) 0.0273(15) 0.0198(14) 0.0088(12) 0.0055(11) 0.0135(13)
O2 0.0562(17) 0.0236(16) 0.0381(17) 0.0187(13) 0.0142(13) 0.0138(13)
O3 0.0399(13) 0.0182(13) 0.0168(13) 0.0043(10) 0.0025(10) 0.0070(10)
O4 0.0452(14) 0.0167(13) 0.0198(13) 0.0046(11) 0.0042(10) 0.0080(11)
N1 0.0283(14) 0.0214(15) 0.0187(15) 0.0050(12) 0.0040(11) 0.0095(12)
N2 0.0216(12) 0.0201(15) 0.0114(13) 0.0009(11) 0.0013(10) 0.0080(11)
N3 0.0332(15) 0.0202(16) 0.0250(16) 0.0051(13) 0.0058(12) 0.0088(12)
C1 0.0251(15) 0.0206(17) 0.0180(17) 0.0000(14) 0.0014(12) 0.0101(13)
C2 0.0284(16) 0.0214(18) 0.0243(19) 0.0040(14) 0.0059(14) 0.0083(14)
C3 0.0288(16) 0.0214(17) 0.0190(17) 0.0074(14) 0.0061(13) 0.0105(13)
C4 0.0228(14) 0.0189(16) 0.0161(15) 0.0049(12) 0.0045(12) 0.0100(12)
C5 0.0244(15) 0.0197(17) 0.0169(16) 0.0048(13) 0.0043(12) 0.0085(13)
C6 0.0247(15) 0.0200(17) 0.0181(17) 0.0045(13) 0.0049(12) 0.0084(13)
C7 0.0254(15) 0.0222(17) 0.0175(16) 0.0060(13) 0.0050(12) 0.0108(13)
C8 0.0280(15) 0.0205(17) 0.0183(17) 0.0048(14) 0.0041(12) 0.0095(13)
C9 0.047(2) 0.0188(18) 0.0176(18) 0.0011(14) 0.0019(14) 0.0082(15)
C10 0.050(2) 0.024(2) 0.0233(19) 0.0032(16) 0.0020(16) 0.0117(17)

_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
Cl1 C1 1.699(4) . ?
O1 N3 1.221(4) . ?
O2 N3 1.225(4) . ?
O3 C8 1.332(4) . ?
O3 C9 1.459(5) . ?
O4 C8 1.202(4) . ?
N1 C6 1.377(4) . ?
N1 C7 1.293(5) . ?
N2 C1 1.386(4) . ?
N2 C4 1.399(4) . ?
N2 C7 1.382(4) . ?
N3 C3 1.428(4) . ?
C1 C2 1.357(5) . ?
C2 H2 0.9500 . ?
C2 C3 1.403(5) . ?
C3 C4 1.386(5) . ?
C4 C5 1.399(5) . ?
C5 H5 0.9500 . ?
C5 C6 1.357(5) . ?
C6 C8 1.498(5) . ?
C7 H7 0.9500 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.490(5) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?

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
C8 O3 C9 115.9(3) . . ?
C7 N1 C6 118.4(3) . . ?
C1 N2 C4 109.3(3) . . ?
C7 N2 C1 129.8(3) . . ?
C7 N2 C4 120.9(3) . . ?
O1 N3 O2 125.1(3) . . ?
O1 N3 C3 118.5(3) . . ?
O2 N3 C3 116.4(3) . . ?
N2 C1 Cl1 121.0(3) . . ?
C2 C1 Cl1 130.2(3) . . ?
C2 C1 N2 108.7(3) . . ?
C1 C2 H2 126.5 . . ?
C1 C2 C3 107.0(3) . . ?
C3 C2 H2 126.5 . . ?
C2 C3 N3 124.9(3) . . ?
C4 C3 N3 125.2(3) . . ?
C4 C3 C2 109.9(3) . . ?
N2 C4 C5 117.3(3) . . ?
C3 C4 N2 105.1(3) . . ?
C3 C4 C5 137.5(3) . . ?
C4 C5 H5 121.1 . . ?
C6 C5 C4 117.7(3) . . ?
C6 C5 H5 121.1 . . ?
N1 C6 C8 113.8(3) . . ?
C5 C6 N1 124.0(3) . . ?
C5 C6 C8 122.1(3) . . ?
N1 C7 N2 121.7(3) . . ?
N1 C7 H7 119.2 . . ?
N2 C7 H7 119.2 . . ?
O3 C8 C6 110.7(3) . . ?
O4 C8 O3 125.4(3) . . ?
O4 C8 C6 123.9(3) . . ?
O3 C9 H9A 110.3 . . ?
O3 C9 H9B 110.3 . . ?
O3 C9 C10 107.2(3) . . ?
H9A C9 H9B 108.5 . . ?
C10 C9 H9A 110.3 . . ?
C10 C9 H9B 110.3 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?

# start Validation Reply Form
_vrf_PLAT029_192b                
;
PROBLEM: _diffrn_measured_fraction_theta_full Low .......      0.912 Note  
RESPONSE: Twinning in these crystals of extremely poor quality 
resulted in overlapping of the reflections on the OKL layer. 
Finally, all 0KL reflections were omitted from the refinement.
The task of the study - confirmation of the chemical composition of the
sample, has been achieved, but the reported structure can not be used 
in the discussion of fine features of molecular and crystal structures.

;
# end Validation Reply Form
