# Electronic Supplementary Material (ESI) for Chemical Science.
# 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_p-1
_audit_creation_date             2014-02-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2013.12.10 svn.r2853 for OlexSys, GUI svn.r4736)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C10 H2 I2 N2 O4, 2(C12 H12 O2)'
_chemical_formula_sum            'C34 H26 I2 N2 O8'
_chemical_formula_weight         844.37
_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 0.0181 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'
I I -0.3257 6.8362 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   6.6274(3)
_cell_length_b                   9.4654(3)
_cell_length_c                   12.3549(4)
_cell_angle_alpha                82.120(2)
_cell_angle_beta                 80.651(3)
_cell_angle_gamma                79.408(2)
_cell_volume                     747.10(5)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    3436
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      62.311
_cell_measurement_theta_min      3.648
_shelx_estimated_absorpt_T_max   0.638
_shelx_estimated_absorpt_T_min   0.072
_exptl_absorpt_coefficient_mu    17.033
_exptl_absorpt_correction_T_max  0.7522
_exptl_absorpt_correction_T_min  0.6269
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0432 before and 0.0222 after correction.
The Ratio of minimum to maximum transmission is 0.8334.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.877
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       Needle
_exptl_crystal_F_000             414
_exptl_crystal_size_max          0.327
_exptl_crystal_size_mid          0.039
_exptl_crystal_size_min          0.029
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0149
_diffrn_reflns_av_unetI/netI     0.0220
_diffrn_reflns_Laue_measured_fraction_full 0.823
_diffrn_reflns_Laue_measured_fraction_max 0.934
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4204
_diffrn_reflns_point_group_measured_fraction_full 0.823
_diffrn_reflns_point_group_measured_fraction_max 0.934
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         62.312
_diffrn_reflns_theta_min         3.648
_diffrn_ambient_temperature      100.02
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.823
_diffrn_measured_fraction_theta_max 0.934
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2108
_reflns_number_total             2217
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.513
_refine_diff_density_min         -0.344
_refine_diff_density_rms         0.090
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         2217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0226
_refine_ls_R_factor_gt           0.0209
_refine_ls_restrained_S_all      1.081
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0339P)²+0.7294P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0547
_refine_ls_wR_factor_ref         0.0557
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C14(H14), C16(H16), C17(H17), C7(H7), C9(H9), C11(H11)
2.b Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C6(H6A,H6B,H6C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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
I1 I 0.39792(3) 0.87949(2) 0.78287(2) 0.01481(9) Uani 1 1 d . . . . .
O1 O 0.6692(4) 0.7692(2) 0.26226(19) 0.0218(6) Uani 1 1 d . . . . .
O2 O 0.5434(4) 0.6082(2) 0.62837(19) 0.0189(5) Uani 1 1 d . . . . .
N1 N 0.6188(5) 0.6563(3) 0.4397(2) 0.0145(6) Uani 1 1 d . . . . .
H1 H 0.6510 0.5663 0.4239 0.017 Uiso 1 1 calc R . . . .
C1 C 0.6227(5) 0.7747(3) 0.3598(3) 0.0132(7) Uani 1 1 d . . . . .
C2 C 0.5601(5) 0.6924(3) 0.5457(3) 0.0127(7) Uani 1 1 d . . . . .
C3 C 0.5611(5) 0.9046(3) 0.4231(3) 0.0095(6) Uani 1 1 d . . . . .
C4 C 0.5228(5) 0.8551(3) 0.5350(3) 0.0095(6) Uani 1 1 d . . . . .
C5 C 0.4615(5) 0.9497(3) 0.6156(3) 0.0091(6) Uani 1 1 d . . . . .
O5 O 0.2554(4) 0.6004(3) 0.07027(19) 0.0207(5) Uani 1 1 d . . . . .
C12 C 0.4300(6) 0.5913(4) 0.1254(3) 0.0260(9) Uani 1 1 d . . . . .
H12A H 0.5312 0.6455 0.0793 0.039 Uiso 1 1 calc GR . . . .
H12B H 0.4935 0.4897 0.1394 0.039 Uiso 1 1 calc GR . . . .
H12C H 0.3857 0.6324 0.1958 0.039 Uiso 1 1 calc GR . . . .
C13 C 0.1508(6) 0.7361(4) 0.0426(3) 0.0178(8) Uani 1 1 d . . . . .
C14 C 0.2108(6) 0.8632(4) 0.0574(3) 0.0175(7) Uani 1 1 d . . . . .
H14 H 0.3327 0.8607 0.0894 0.021 Uiso 1 1 calc R . . . .
C15 C 0.0898(6) 0.9980(4) 0.0247(3) 0.0159(7) Uani 1 1 d . . . . .
C16 C 0.1461(6) 1.1322(4) 0.0376(3) 0.0182(8) Uani 1 1 d . . . . .
H16 H 0.2678 1.1323 0.0688 0.022 Uiso 1 1 calc R . . . .
C17 C 0.0287(6) 1.2602(4) 0.0058(3) 0.0178(8) Uani 1 1 d . . . . .
H17 H 0.0683 1.3483 0.0164 0.021 Uiso 1 1 calc R . . . .
O3 O 0.0662(4) 0.5925(2) 0.61255(18) 0.0149(5) Uani 1 1 d . . . . .
C6 C 0.0175(6) 0.5732(4) 0.7310(3) 0.0202(8) Uani 1 1 d . . . . .
H6A H -0.1270 0.6165 0.7528 0.030 Uiso 1 1 calc GR . . . .
H6B H 0.1092 0.6203 0.7637 0.030 Uiso 1 1 calc GR . . . .
H6C H 0.0373 0.4697 0.7570 0.030 Uiso 1 1 calc GR . . . .
C7 C 0.0916(5) 0.7457(3) 0.4466(3) 0.0124(7) Uani 1 1 d . . . . .
H7 H 0.1306 0.6613 0.4094 0.015 Uiso 1 1 calc R . . . .
C8 C 0.0460(5) 0.7327(3) 0.5629(3) 0.0109(7) Uani 1 1 d . . . . .
C9 C -0.0116(5) 0.8526(3) 0.6185(3) 0.0101(6) Uani 1 1 d . . . . .
H9 H -0.0432 0.8425 0.6967 0.012 Uiso 1 1 calc R . . . .
C10 C -0.0238(5) 0.9929(3) 0.5580(3) 0.0099(6) Uani 1 1 d . . . . .
C11 C -0.0798(5) 1.1203(3) 0.6125(3) 0.0119(7) Uani 1 1 d . . . . .
H11 H -0.1093 1.1123 0.6907 0.014 Uiso 1 1 calc R . . . .


_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 C5 2.082(3) . ?
O1 C1 1.201(4) . ?
O2 C2 1.210(4) . ?
N1 H1 0.8800 . ?
N1 C1 1.389(4) . ?
N1 C2 1.375(4) . ?
C1 C3 1.505(4) . ?
C2 C4 1.505(4) . ?
C3 C4 1.396(4) . ?
C3 C5 1.385(4) 2_676 ?
C4 C5 1.392(4) . ?
C5 C3 1.385(4) 2_676 ?
O5 C12 1.419(5) . ?
O5 C13 1.370(4) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.378(5) . ?
C13 C17 1.408(6) 2_575 ?
C14 H14 0.9500 . ?
C14 C15 1.422(5) . ?
C15 C15 1.416(8) 2_575 ?
C15 C16 1.423(5) . ?
C16 H16 0.9500 . ?
C16 C17 1.360(5) . ?
C17 C13 1.408(6) 2_575 ?
C17 H17 0.9500 . ?
O3 C6 1.440(4) . ?
O3 C8 1.375(4) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7 0.9500 . ?
C7 C8 1.412(5) . ?
C7 C11 1.371(5) 2_576 ?
C8 C9 1.370(4) . ?
C9 H9 0.9500 . ?
C9 C10 1.427(4) . ?
C10 C10 1.410(6) 2_576 ?
C10 C11 1.422(4) . ?
C11 C7 1.371(5) 2_576 ?
C11 H11 0.9500 . ?

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
C1 N1 H1 123.0 . . ?
C2 N1 H1 123.0 . . ?
C2 N1 C1 114.0(3) . . ?
O1 C1 N1 125.6(3) . . ?
O1 C1 C3 129.5(3) . . ?
N1 C1 C3 105.0(3) . . ?
O2 C2 N1 125.9(3) . . ?
O2 C2 C4 128.7(3) . . ?
N1 C2 C4 105.4(3) . . ?
C4 C3 C1 107.9(3) . . ?
C5 C3 C1 129.5(3) 2_676 . ?
C5 C3 C4 122.6(3) 2_676 . ?
C3 C4 C2 107.8(3) . . ?
C5 C4 C2 130.3(3) . . ?
C5 C4 C3 121.9(3) . . ?
C3 C5 I1 121.7(2) 2_676 . ?
C3 C5 C4 115.5(3) 2_676 . ?
C4 C5 I1 122.9(2) . . ?
C13 O5 C12 116.9(3) . . ?
O5 C12 H12A 109.5 . . ?
O5 C12 H12B 109.5 . . ?
O5 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O5 C13 C14 124.9(3) . . ?
O5 C13 C17 115.0(3) . 2_575 ?
C14 C13 C17 120.1(3) . 2_575 ?
C13 C14 H14 120.1 . . ?
C13 C14 C15 119.8(3) . . ?
C15 C14 H14 120.1 . . ?
C14 C15 C16 121.9(3) . . ?
C15 C15 C14 120.2(4) 2_575 . ?
C15 C15 C16 117.9(4) 2_575 . ?
C15 C16 H16 119.4 . . ?
C17 C16 C15 121.2(3) . . ?
C17 C16 H16 119.4 . . ?
C13 C17 H17 119.6 2_575 . ?
C16 C17 C13 120.8(3) . 2_575 ?
C16 C17 H17 119.6 . . ?
C8 O3 C6 116.7(2) . . ?
O3 C6 H6A 109.5 . . ?
O3 C6 H6B 109.5 . . ?
O3 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C8 C7 H7 120.0 . . ?
C11 C7 H7 120.0 2_576 . ?
C11 C7 C8 120.1(3) 2_576 . ?
O3 C8 C7 114.5(3) . . ?
C9 C8 O3 124.5(3) . . ?
C9 C8 C7 121.0(3) . . ?
C8 C9 H9 120.3 . . ?
C8 C9 C10 119.5(3) . . ?
C10 C9 H9 120.3 . . ?
C10 C10 C9 120.0(3) 2_576 . ?
C10 C10 C11 118.7(4) 2_576 . ?
C11 C10 C9 121.3(3) . . ?
C7 C11 C10 120.7(3) 2_576 . ?
C7 C11 H11 119.6 2_576 . ?
C10 C11 H11 119.6 . . ?

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 C1 C3 C4 -179.7(4) . . . . ?
O1 C1 C3 C5 1.4(6) . . . 2_676 ?
O2 C2 C4 C3 -179.7(3) . . . . ?
O2 C2 C4 C5 0.3(6) . . . . ?
N1 C1 C3 C4 -0.7(4) . . . . ?
N1 C1 C3 C5 -179.5(3) . . . 2_676 ?
N1 C2 C4 C3 0.3(4) . . . . ?
N1 C2 C4 C5 -179.7(3) . . . . ?
C1 N1 C2 O2 179.2(3) . . . . ?
C1 N1 C2 C4 -0.8(4) . . . . ?
C1 C3 C4 C2 0.2(4) . . . . ?
C1 C3 C4 C5 -179.7(3) . . . . ?
C2 N1 C1 O1 180.0(3) . . . . ?
C2 N1 C1 C3 0.9(4) . . . . ?
C2 C4 C5 I1 -1.1(5) . . . . ?
C2 C4 C5 C3 -179.2(3) . . . 2_676 ?
C3 C4 C5 I1 178.8(2) . . . . ?
C3 C4 C5 C3 0.7(5) . . . 2_676 ?
C5 C3 C4 C2 179.2(3) 2_676 . . . ?
C5 C3 C4 C5 -0.8(5) 2_676 . . . ?
O5 C13 C14 C15 179.6(3) . . . . ?
C12 O5 C13 C14 4.7(5) . . . . ?
C12 O5 C13 C17 -176.2(3) . . . 2_575 ?
C13 C14 C15 C15 -1.1(6) . . . 2_575 ?
C13 C14 C15 C16 -179.5(3) . . . . ?
C14 C15 C16 C17 180.0(3) . . . . ?
C15 C15 C16 C17 1.5(6) 2_575 . . . ?
C15 C16 C17 C13 -1.1(5) . . . 2_575 ?
C17 C13 C14 C15 0.6(5) 2_575 . . . ?
O3 C8 C9 C10 178.9(3) . . . . ?
C6 O3 C8 C7 -178.8(3) . . . . ?
C6 O3 C8 C9 1.7(5) . . . . ?
C7 C8 C9 C10 -0.6(5) . . . . ?
C8 C9 C10 C10 -0.1(6) . . . 2_576 ?
C8 C9 C10 C11 -179.0(3) . . . . ?
C9 C10 C11 C7 -179.8(3) . . . 2_576 ?
C10 C10 C11 C7 1.4(6) 2_576 . . 2_576 ?
C11 C7 C8 O3 -179.2(3) 2_576 . . . ?
C11 C7 C8 C9 0.4(5) 2_576 . . . ?


_database_code_depnum_ccdc_archive 'CCDC 995177'
#######################################################################
#
#                 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_p21c
_audit_creation_date             2013-12-03
_audit_creation_method           
;
Olex2 1.2
(compiled 2013.11.15 svn.r2839 for OlexSys, GUI svn.r4720)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         '2(C18 H26 N2 O4), 2(C10 H2 Br2 N2 O4)'
_chemical_formula_sum            'C56 H56 Br4 N8 O16'
_chemical_formula_weight         1416.72
_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 0.0181 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'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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      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_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   6.7598(4)
_cell_length_b                   22.6656(13)
_cell_length_c                   9.1153(5)
_cell_angle_alpha                90
_cell_angle_beta                 101.623(2)
_cell_angle_gamma                90
_cell_volume                     1367.96(14)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    9985
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      68.085
_cell_measurement_theta_min      5.325
_shelx_estimated_absorpt_T_max   0.768
_shelx_estimated_absorpt_T_min   0.434
_exptl_absorpt_coefficient_mu    4.278
_exptl_absorpt_correction_T_max  0.7530
_exptl_absorpt_correction_T_min  0.5418
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0853 before and 0.0363 after correction.
The Ratio of minimum to maximum transmission is 0.7195.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.720
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       Needle
_exptl_crystal_F_000             716
_exptl_crystal_size_max          0.234
_exptl_crystal_size_mid          0.066
_exptl_crystal_size_min          0.065
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0249
_diffrn_reflns_av_unetI/netI     0.0169
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            13777
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.079
_diffrn_reflns_theta_min         5.325
_diffrn_ambient_temperature      99.99
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2444
_reflns_number_total             2462
_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       ?
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.27A (Bruker, 2012)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.611
_refine_diff_density_min         -0.585
_refine_diff_density_rms         0.061
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2462
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0227
_refine_ls_R_factor_gt           0.0226
_refine_ls_restrained_S_all      1.081
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0275P)²+1.3166P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0576
_refine_ls_wR_factor_ref         0.0576
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C12(H12A,H12B), C13(H13A,H13B), C14(H14A,H14B)
2.b Aromatic/amide H refined with riding coordinates:
 N2(H2), C6(H6), C7(H7), C10(H10), N1(H1)
2.c Idealised tetrahedral OH refined as rotating group:
 O4(H4)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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
N2 N 0.9638(2) 0.61258(7) 0.31134(17) 0.0199(3) Uani 1 1 d . . . . .
H2 H 0.9678 0.6364 0.3882 0.024 Uiso 1 1 calc R . . . .
O3 O 1.1337(2) 0.71944(6) 0.28192(15) 0.0231(3) Uani 1 1 d . . . . .
O4 O 1.5323(2) 0.76506(6) 0.36935(16) 0.0262(3) Uani 1 1 d . . . . .
H4 H 1.5637 0.7848 0.2995 0.039 Uiso 1 1 calc GR . . . .
C6 C 1.0545(3) 0.54842(8) 0.7540(2) 0.0185(4) Uani 1 1 d . . . . .
H6 H 1.0735 0.5752 0.8359 0.022 Uiso 1 1 calc R . . . .
C7 C 1.0252(3) 0.57013(8) 0.6110(2) 0.0172(4) Uani 1 1 d . . . . .
H7 H 1.0221 0.6115 0.5947 0.021 Uiso 1 1 calc R . . . .
C8 C 0.9994(3) 0.53097(8) 0.4871(2) 0.0155(4) Uani 1 1 d . . . . .
C9 C 0.9705(3) 0.55232(8) 0.3355(2) 0.0163(4) Uani 1 1 d . . . . .
C10 C 0.9431(3) 0.51238(8) 0.2180(2) 0.0180(4) Uani 1 1 d . . . . .
H10 H 0.9226 0.5263 0.1178 0.022 Uiso 1 1 calc R . . . .
C11 C 0.9503(3) 0.63798(9) 0.1631(2) 0.0214(4) Uani 1 1 d . . . . .
H11A H 0.8235 0.6252 0.0962 0.026 Uiso 1 1 calc R . . . .
H11B H 1.0653 0.6244 0.1197 0.026 Uiso 1 1 calc R . . . .
C12 C 0.9543(3) 0.70457(9) 0.1773(2) 0.0232(4) Uani 1 1 d . . . . .
H12A H 0.9550 0.7230 0.0790 0.028 Uiso 1 1 calc R . . . .
H12B H 0.8339 0.7186 0.2134 0.028 Uiso 1 1 calc R . . . .
C13 C 1.1697(3) 0.78111(8) 0.2965(2) 0.0245(4) Uani 1 1 d . . . . .
H13A H 1.0543 0.8009 0.3278 0.029 Uiso 1 1 calc R . . . .
H13B H 1.1852 0.7979 0.1993 0.029 Uiso 1 1 calc R . . . .
C14 C 1.3590(3) 0.79081(8) 0.4119(2) 0.0271(4) Uani 1 1 d . . . . .
H14A H 1.3815 0.8337 0.4272 0.033 Uiso 1 1 calc R . . . .
H14B H 1.3418 0.7735 0.5083 0.033 Uiso 1 1 calc R . . . .
Br1 Br 0.42675(3) 0.45733(2) 0.14584(2) 0.01589(8) Uani 1 1 d . . . . .
O1 O 0.5760(2) 0.65687(6) 0.64717(15) 0.0245(3) Uani 1 1 d . . . . .
O2 O 0.4619(2) 0.59910(6) 0.15811(14) 0.0219(3) Uani 1 1 d . . . . .
N1 N 0.5162(2) 0.64170(7) 0.39291(18) 0.0190(3) Uani 1 1 d . . . . .
H1 H 0.5181 0.6788 0.3651 0.023 Uiso 1 1 calc R . . . .
C1 C 0.4650(2) 0.48147(8) 0.34611(19) 0.0128(3) Uani 1 1 d . . . . .
C2 C 0.4894(3) 0.54049(7) 0.3873(2) 0.0128(3) Uani 1 1 d . . . . .
C3 C 0.5234(2) 0.55839(8) 0.53685(19) 0.0129(3) Uani 1 1 d . . . . .
C4 C 0.5429(3) 0.62422(8) 0.5396(2) 0.0168(4) Uani 1 1 d . . . . .
C5 C 0.4859(3) 0.59492(8) 0.2928(2) 0.0162(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
N2 H2 0.8800 . ?
N2 C9 1.383(2) . ?
N2 C11 1.454(2) . ?
O3 C12 1.424(2) . ?
O3 C13 1.420(2) . ?
O4 H4 0.8400 . ?
O4 C14 1.431(3) . ?
C6 H6 0.9500 . ?
C6 C7 1.370(3) . ?
C6 C10 1.401(3) 3_766 ?
C7 H7 0.9500 . ?
C7 C8 1.419(3) . ?
C8 C8 1.423(4) 3_766 ?
C8 C9 1.439(3) . ?
C9 C10 1.386(3) . ?
C10 C6 1.401(3) 3_766 ?
C10 H10 0.9500 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.515(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.500(3) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
Br1 C1 1.8731(17) . ?
O1 C4 1.213(2) . ?
O2 C5 1.209(2) . ?
N1 H1 0.8800 . ?
N1 C4 1.371(2) . ?
N1 C5 1.387(2) . ?
C1 C2 1.390(2) . ?
C1 C3 1.388(2) 3_666 ?
C2 C3 1.396(3) . ?
C2 C5 1.502(2) . ?
C3 C1 1.388(2) 3_666 ?
C3 C4 1.498(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
C9 N2 H2 118.9 . . ?
C9 N2 C11 122.22(16) . . ?
C11 N2 H2 118.9 . . ?
C13 O3 C12 113.74(15) . . ?
C14 O4 H4 109.5 . . ?
C7 C6 H6 119.3 . . ?
C7 C6 C10 121.36(17) . 3_766 ?
C10 C6 H6 119.3 3_766 . ?
C6 C7 H7 119.9 . . ?
C6 C7 C8 120.26(17) . . ?
C8 C7 H7 119.9 . . ?
C7 C8 C8 119.3(2) . 3_766 ?
C7 C8 C9 121.65(17) . . ?
C8 C8 C9 119.1(2) 3_766 . ?
N2 C9 C8 118.61(16) . . ?
N2 C9 C10 121.79(17) . . ?
C10 C9 C8 119.56(17) . . ?
C6 C10 H10 119.8 3_766 . ?
C9 C10 C6 120.47(18) . 3_766 ?
C9 C10 H10 119.8 . . ?
N2 C11 H11A 110.0 . . ?
N2 C11 H11B 110.0 . . ?
N2 C11 C12 108.58(15) . . ?
H11A C11 H11B 108.4 . . ?
C12 C11 H11A 110.0 . . ?
C12 C11 H11B 110.0 . . ?
O3 C12 C11 106.92(15) . . ?
O3 C12 H12A 110.3 . . ?
O3 C12 H12B 110.3 . . ?
C11 C12 H12A 110.3 . . ?
C11 C12 H12B 110.3 . . ?
H12A C12 H12B 108.6 . . ?
O3 C13 H13A 110.0 . . ?
O3 C13 H13B 110.0 . . ?
O3 C13 C14 108.42(16) . . ?
H13A C13 H13B 108.4 . . ?
C14 C13 H13A 110.0 . . ?
C14 C13 H13B 110.0 . . ?
O4 C14 C13 112.32(16) . . ?
O4 C14 H14A 109.1 . . ?
O4 C14 H14B 109.1 . . ?
C13 C14 H14A 109.1 . . ?
C13 C14 H14B 109.1 . . ?
H14A C14 H14B 107.9 . . ?
C4 N1 H1 123.4 . . ?
C4 N1 C5 113.20(15) . . ?
C5 N1 H1 123.4 . . ?
C2 C1 Br1 121.99(13) . . ?
C3 C1 Br1 122.29(13) 3_666 . ?
C3 C1 C2 115.69(16) 3_666 . ?
C1 C2 C3 122.03(16) . . ?
C1 C2 C5 130.40(16) . . ?
C3 C2 C5 107.56(15) . . ?
C1 C3 C2 122.27(16) 3_666 . ?
C1 C3 C4 130.11(16) 3_666 . ?
C2 C3 C4 107.61(15) . . ?
O1 C4 N1 125.36(17) . . ?
O1 C4 C3 128.53(17) . . ?
N1 C4 C3 106.11(15) . . ?
O2 C5 N1 125.46(17) . . ?
O2 C5 C2 129.05(17) . . ?
N1 C5 C2 105.50(14) . . ?

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
N2 C9 C10 C6 -178.34(17) . . . 3_766 ?
N2 C11 C12 O3 56.03(19) . . . . ?
O3 C13 C14 O4 62.0(2) . . . . ?
C6 C7 C8 C8 1.1(3) . . . 3_766 ?
C6 C7 C8 C9 -179.32(17) . . . . ?
C7 C8 C9 N2 -1.4(3) . . . . ?
C7 C8 C9 C10 -179.11(16) . . . . ?
C8 C8 C9 N2 178.2(2) 3_766 . . . ?
C8 C8 C9 C10 0.5(3) 3_766 . . . ?
C8 C9 C10 C6 -0.7(3) . . . 3_766 ?
C9 N2 C11 C12 -177.81(16) . . . . ?
C10 C6 C7 C8 -0.9(3) 3_766 . . . ?
C11 N2 C9 C8 175.30(16) . . . . ?
C11 N2 C9 C10 -7.0(3) . . . . ?
C12 O3 C13 C14 178.65(15) . . . . ?
C13 O3 C12 C11 174.14(16) . . . . ?
Br1 C1 C2 C3 -178.25(13) . . . . ?
Br1 C1 C2 C5 1.9(3) . . . . ?
C1 C2 C3 C1 0.0(3) . . . 3_666 ?
C1 C2 C3 C4 179.82(16) . . . . ?
C1 C2 C5 O2 -0.5(3) . . . . ?
C1 C2 C5 N1 179.33(18) . . . . ?
C1 C3 C4 O1 1.0(3) 3_666 . . . ?
C1 C3 C4 N1 -179.18(17) 3_666 . . . ?
C2 C3 C4 O1 -178.80(18) . . . . ?
C2 C3 C4 N1 1.02(19) . . . . ?
C3 C1 C2 C3 0.0(3) 3_666 . . . ?
C3 C1 C2 C5 -179.88(17) 3_666 . . . ?
C3 C2 C5 O2 179.62(18) . . . . ?
C3 C2 C5 N1 -0.56(19) . . . . ?
C4 N1 C5 O2 -178.89(17) . . . . ?
C4 N1 C5 C2 1.3(2) . . . . ?
C5 N1 C4 O1 178.37(18) . . . . ?
C5 N1 C4 C3 -1.5(2) . . . . ?
C5 C2 C3 C1 179.91(15) . . . 3_666 ?
C5 C2 C3 C4 -0.27(19) . . . . ?

_database_code_depnum_ccdc_archive 'CCDC 995178'
#######################################################################
#
#                 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.
# 
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#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
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#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_p21c
_audit_creation_date             2013-12-03
_audit_creation_method           
;
Olex2 1.2
(compiled 2013.11.15 svn.r2839 for OlexSys, GUI svn.r4720)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         '2(C18 H26 N2 O4), 2(C10 H2 Cl2 N2 O4)'
_chemical_formula_sum            'C56 H56 Cl4 N8 O16'
_chemical_formula_weight         1238.88
_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 0.0181 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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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      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_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   6.6819(3)
_cell_length_b                   22.9780(11)
_cell_length_c                   8.8554(4)
_cell_angle_alpha                90
_cell_angle_beta                 101.576(2)
_cell_angle_gamma                90
_cell_volume                     1331.97(11)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    4971
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      67.249
_cell_measurement_theta_min      5.450
_shelx_estimated_absorpt_T_max   0.878
_shelx_estimated_absorpt_T_min   0.260
_exptl_absorpt_coefficient_mu    2.724
_exptl_absorpt_correction_T_max  0.7529
_exptl_absorpt_correction_T_min  0.6031
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.1059 before and 0.0298 after correction.
The Ratio of minimum to maximum transmission is 0.8010.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.544
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       Needle
_exptl_crystal_F_000             644
_exptl_crystal_size_max          0.676
_exptl_crystal_size_mid          0.113
_exptl_crystal_size_min          0.049
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0192
_diffrn_reflns_av_unetI/netI     0.0217
_diffrn_reflns_Laue_measured_fraction_full 0.957
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            6929
_diffrn_reflns_point_group_measured_fraction_full 0.957
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         67.483
_diffrn_reflns_theta_min         5.450
_diffrn_ambient_temperature      99.95
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.957
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2174
_reflns_number_total             2301
_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       ?
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.27A (Bruker, 2012)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.547
_refine_diff_density_min         -0.519
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2301
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0329
_refine_ls_R_factor_gt           0.0315
_refine_ls_restrained_S_all      1.053
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0402P)²+0.9517P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0827
_refine_ls_wR_factor_ref         0.0837
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C12(H12A,H12B), C13(H13A,H13B), C14(H14A,H14B)
2.b Aromatic/amide H refined with riding coordinates:
 N2(H2), C6(H6), C7(H7), C10(H10), N1(H1)
2.c Idealised tetrahedral OH refined as rotating group:
 O4(H4)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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
O3 O 0.41416(18) 0.28022(5) 0.22034(13) 0.0228(3) Uani 1 1 d . . . . .
O4 O 0.01314(18) 0.23686(5) 0.13421(14) 0.0259(3) Uani 1 1 d . . . . .
H4 H -0.0242 0.2189 0.2065 0.039 Uiso 1 1 calc GR . . . .
N2 N 0.5694(2) 0.38786(6) 0.19035(15) 0.0189(3) Uani 1 1 d . . . . .
H2 H 0.5702 0.3651 0.1105 0.023 Uiso 1 1 calc R . . . .
C6 C 0.4399(2) 0.45377(7) -0.26370(18) 0.0175(3) Uani 1 1 d . . . . .
H6 H 0.4208 0.4279 -0.3492 0.021 Uiso 1 1 calc R . . . .
C7 C 0.4801(2) 0.43160(7) -0.11719(18) 0.0165(3) Uani 1 1 d . . . . .
H7 H 0.4902 0.3907 -0.1020 0.020 Uiso 1 1 calc R . . . .
C8 C 0.5067(2) 0.46935(7) 0.01191(18) 0.0146(3) Uani 1 1 d . . . . .
C9 C 0.5483(2) 0.44753(7) 0.16765(18) 0.0160(3) Uani 1 1 d . . . . .
C10 C 0.5733(2) 0.48614(7) 0.28955(18) 0.0174(3) Uani 1 1 d . . . . .
H10 H 0.5998 0.4717 0.3922 0.021 Uiso 1 1 calc R . . . .
C11 C 0.5901(2) 0.36199(7) 0.34260(18) 0.0201(4) Uani 1 1 d . . . . .
H11A H 0.4737 0.3737 0.3895 0.024 Uiso 1 1 calc R . . . .
H11B H 0.7178 0.3757 0.4102 0.024 Uiso 1 1 calc R . . . .
C12 C 0.5948(2) 0.29657(7) 0.3271(2) 0.0218(4) Uani 1 1 d . . . . .
H12A H 0.7176 0.2843 0.2887 0.026 Uiso 1 1 calc R . . . .
H12B H 0.5980 0.2779 0.4282 0.026 Uiso 1 1 calc R . . . .
C13 C 0.3780(3) 0.21945(7) 0.2142(2) 0.0229(4) Uani 1 1 d . . . . .
H13A H 0.3613 0.2051 0.3163 0.027 Uiso 1 1 calc R . . . .
H13B H 0.4950 0.1989 0.1854 0.027 Uiso 1 1 calc R . . . .
C14 C 0.1867(3) 0.20820(7) 0.0959(2) 0.0254(4) Uani 1 1 d . . . . .
H14A H 0.2064 0.2220 -0.0059 0.030 Uiso 1 1 calc R . . . .
H14B H 0.1607 0.1658 0.0883 0.030 Uiso 1 1 calc R . . . .
Cl1 Cl 0.07704(6) 0.53675(2) 0.34898(4) 0.01983(14) Uani 1 1 d . . . . .
O1 O -0.05639(19) 0.34667(5) -0.16115(15) 0.0278(3) Uani 1 1 d . . . . .
O2 O 0.08017(18) 0.39885(6) 0.34646(13) 0.0259(3) Uani 1 1 d . . . . .
N1 N 0.0237(2) 0.35884(6) 0.10213(17) 0.0218(3) Uani 1 1 d . . . . .
H1 H 0.0349 0.3219 0.1287 0.026 Uiso 1 1 calc R . . . .
C1 C 0.0381(2) 0.51673(7) 0.15922(17) 0.0143(3) Uani 1 1 d . . . . .
C2 C 0.0254(2) 0.45867(7) 0.11372(18) 0.0143(3) Uani 1 1 d . . . . .
C3 C -0.0125(2) 0.44263(7) -0.04114(18) 0.0142(3) Uani 1 1 d . . . . .
C4 C -0.0190(2) 0.37749(7) -0.04798(19) 0.0190(3) Uani 1 1 d . . . . .
C5 C 0.0473(2) 0.40408(7) 0.20774(19) 0.0190(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
O3 C12 1.426(2) . ?
O3 C13 1.4162(19) . ?
O4 H4 0.8400 . ?
O4 C14 1.432(2) . ?
N2 H2 0.8800 . ?
N2 C9 1.389(2) . ?
N2 C11 1.454(2) . ?
C6 H6 0.9500 . ?
C6 C7 1.369(2) . ?
C6 C10 1.400(2) 3_665 ?
C7 H7 0.9500 . ?
C7 C8 1.418(2) . ?
C8 C8 1.424(3) 3_665 ?
C8 C9 1.441(2) . ?
C9 C10 1.381(2) . ?
C10 C6 1.400(2) 3_665 ?
C10 H10 0.9500 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.510(2) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.503(3) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
Cl1 C1 1.7110(15) . ?
O1 C4 1.212(2) . ?
O2 C5 1.210(2) . ?
N1 H1 0.8800 . ?
N1 C4 1.371(2) . ?
N1 C5 1.386(2) . ?
C1 C2 1.391(2) . ?
C1 C3 1.387(2) 3_565 ?
C2 C3 1.393(2) . ?
C2 C5 1.497(2) . ?
C3 C1 1.387(2) 3_565 ?
C3 C4 1.498(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
C13 O3 C12 113.62(13) . . ?
C14 O4 H4 109.5 . . ?
C9 N2 H2 119.1 . . ?
C9 N2 C11 121.72(13) . . ?
C11 N2 H2 119.1 . . ?
C7 C6 H6 119.5 . . ?
C7 C6 C10 121.05(15) . 3_665 ?
C10 C6 H6 119.5 3_665 . ?
C6 C7 H7 119.8 . . ?
C6 C7 C8 120.37(15) . . ?
C8 C7 H7 119.8 . . ?
C7 C8 C8 119.45(18) . 3_665 ?
C7 C8 C9 121.85(14) . . ?
C8 C8 C9 118.70(18) 3_665 . ?
N2 C9 C8 118.46(14) . . ?
C10 C9 N2 121.88(15) . . ?
C10 C9 C8 119.61(15) . . ?
C6 C10 H10 119.6 3_665 . ?
C9 C10 C6 120.81(15) . 3_665 ?
C9 C10 H10 119.6 . . ?
N2 C11 H11A 109.9 . . ?
N2 C11 H11B 109.9 . . ?
N2 C11 C12 108.81(13) . . ?
H11A C11 H11B 108.3 . . ?
C12 C11 H11A 109.9 . . ?
C12 C11 H11B 109.9 . . ?
O3 C12 C11 107.01(13) . . ?
O3 C12 H12A 110.3 . . ?
O3 C12 H12B 110.3 . . ?
C11 C12 H12A 110.3 . . ?
C11 C12 H12B 110.3 . . ?
H12A C12 H12B 108.6 . . ?
O3 C13 H13A 110.1 . . ?
O3 C13 H13B 110.1 . . ?
O3 C13 C14 108.13(13) . . ?
H13A C13 H13B 108.4 . . ?
C14 C13 H13A 110.1 . . ?
C14 C13 H13B 110.1 . . ?
O4 C14 C13 111.82(14) . . ?
O4 C14 H14A 109.3 . . ?
O4 C14 H14B 109.3 . . ?
C13 C14 H14A 109.3 . . ?
C13 C14 H14B 109.3 . . ?
H14A C14 H14B 107.9 . . ?
C4 N1 H1 123.4 . . ?
C4 N1 C5 113.16(13) . . ?
C5 N1 H1 123.4 . . ?
C2 C1 Cl1 122.05(12) . . ?
C3 C1 Cl1 122.07(12) 3_565 . ?
C3 C1 C2 115.87(14) 3_565 . ?
C1 C2 C3 121.82(14) . . ?
C1 C2 C5 130.49(14) . . ?
C3 C2 C5 107.69(14) . . ?
C1 C3 C2 122.31(14) 3_565 . ?
C1 C3 C4 130.10(14) 3_565 . ?
C2 C3 C4 107.59(13) . . ?
O1 C4 N1 125.98(15) . . ?
O1 C4 C3 128.09(15) . . ?
N1 C4 C3 105.92(13) . . ?
O2 C5 N1 125.71(15) . . ?
O2 C5 C2 128.74(16) . . ?
N1 C5 C2 105.55(13) . . ?

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
O3 C13 C14 O4 -60.23(17) . . . . ?
N2 C9 C10 C6 177.20(14) . . . 3_665 ?
N2 C11 C12 O3 -55.58(17) . . . . ?
C6 C7 C8 C8 -0.6(3) . . . 3_665 ?
C6 C7 C8 C9 179.74(14) . . . . ?
C7 C8 C9 N2 2.2(2) . . . . ?
C7 C8 C9 C10 179.89(14) . . . . ?
C8 C8 C9 N2 -177.44(17) 3_665 . . . ?
C8 C8 C9 C10 0.3(2) 3_665 . . . ?
C8 C9 C10 C6 -0.4(2) . . . 3_665 ?
C9 N2 C11 C12 175.99(14) . . . . ?
C10 C6 C7 C8 0.8(2) 3_665 . . . ?
C11 N2 C9 C8 -173.47(13) . . . . ?
C11 N2 C9 C10 8.9(2) . . . . ?
C12 O3 C13 C14 -178.92(13) . . . . ?
C13 O3 C12 C11 -169.35(13) . . . . ?
Cl1 C1 C2 C3 178.01(11) . . . . ?
Cl1 C1 C2 C5 -2.2(2) . . . . ?
C1 C2 C3 C1 0.6(2) . . . 3_565 ?
C1 C2 C3 C4 -179.20(14) . . . . ?
C1 C2 C5 O2 0.6(3) . . . . ?
C1 C2 C5 N1 -178.97(15) . . . . ?
C1 C3 C4 O1 -3.1(3) 3_565 . . . ?
C1 C3 C4 N1 177.76(15) 3_565 . . . ?
C2 C3 C4 O1 176.69(16) . . . . ?
C2 C3 C4 N1 -2.47(16) . . . . ?
C3 C1 C2 C3 -0.6(2) 3_565 . . . ?
C3 C1 C2 C5 179.19(14) 3_565 . . . ?
C3 C2 C5 O2 -179.67(16) . . . . ?
C3 C2 C5 N1 0.81(16) . . . . ?
C4 N1 C5 O2 177.93(15) . . . . ?
C4 N1 C5 C2 -2.53(17) . . . . ?
C5 N1 C4 O1 -176.05(15) . . . . ?
C5 N1 C4 C3 3.13(17) . . . . ?
C5 C2 C3 C1 -179.21(13) . . . 3_565 ?
C5 C2 C3 C4 1.00(16) . . . . ?

_database_code_depnum_ccdc_archive 'CCDC 995179'
#######################################################################
#
#                 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_p-1
_audit_creation_date             2014-01-02
_audit_creation_method           
;
Olex2 1.2
(compiled 2013.12.10 svn.r2853 for OlexSys, GUI svn.r4736)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C10 H2 I2 N2 O4, C5 H9 N O, H2 O'
_chemical_formula_sum            'C15 H13 I2 N3 O6'
_chemical_formula_weight         585.08
_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 0.0181 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'
I I -0.3257 6.8362 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   7.2221(5)
_cell_length_b                   9.4868(7)
_cell_length_c                   13.2822(9)
_cell_angle_alpha                93.245(3)
_cell_angle_beta                 102.205(3)
_cell_angle_gamma                99.769(3)
_cell_volume                     872.51(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4019
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      67.970
_cell_measurement_theta_min      3.421
_shelx_estimated_absorpt_T_max   0.571
_shelx_estimated_absorpt_T_min   0.148
_exptl_absorpt_coefficient_mu    28.676
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
 TWINABS-2012/1 (Bruker,2012) was used for absorption correction.
 
For component 1:
 wR2(int) was 0.0905 before and 0.0436 after correction.
 The Ratio of minimum to maximum transmission not present.
 The λ/2 correction factor is Not present
 
For component 2:
 wR2(int) was 0.1174 before and 0.0503 after correction.
 The Ratio of minimum to maximum transmission is 0.56.
 The λ/2 correction factor is Not present

Final HKLF 4 output contains 14075 reflections, Rint = 0.0463
 (10782 with I > 3sig(I), Rint = 0.0448)
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    2.227
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             556
_exptl_crystal_size_max          0.108
_exptl_crystal_size_mid          0.049
_exptl_crystal_size_min          0.022
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   0.753015
_exptl_transmission_factor_min   0.418991
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.0340
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            14244
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.010
_diffrn_reflns_theta_min         3.420
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2863
_reflns_number_total             3131
_reflns_special_details          
;
 Data were apparently pre-merged, so _diffrn_reflns_number
 etc. will have to be added later.
 
 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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXD (Sheldrick, 2008)'
_refine_diff_density_max         1.742
_refine_diff_density_min         -1.095
_refine_diff_density_rms         0.204
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     252
_refine_ls_number_reflns         3131
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0436
_refine_ls_R_factor_gt           0.0383
_refine_ls_restrained_S_all      1.097
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0556P)²+7.2499P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1057
_refine_ls_wR_factor_ref         0.1098
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C3S(H3SA,H3SB), C4S(H4SA,H4SB), C1S(H1SA,H1SB)
2.b Idealised Me refined as rotating group:
 C5S(H5SA,H5SB,H5SC)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
I1 I 0.80674(6) 0.49956(4) 0.65167(3) 0.01455(15) Uani 1 1 d . . . . .
I2 I 0.73072(5) 1.16297(4) 0.44514(3) 0.01347(15) Uani 1 1 d . . . . .
O1 O 0.9055(7) 0.7716(5) 0.8327(3) 0.0205(10) Uani 1 1 d . . . . .
O2 O 0.8479(8) 1.1977(5) 0.6991(4) 0.0267(11) Uani 1 1 d . . . . .
O3 O 0.7114(7) 0.4665(5) 0.3996(4) 0.0188(10) Uani 1 1 d . . . . .
O4 O 0.7064(7) 0.8993(5) 0.2656(4) 0.0208(10) Uani 1 1 d . . . . .
N1 N 0.8847(8) 1.0006(6) 0.7900(4) 0.0154(11) Uani 1 1 d . . . . .
N2 N 0.7030(8) 0.6662(6) 0.3088(4) 0.0153(11) Uani 1 1 d . . . . .
C1 C 0.8714(9) 0.8560(7) 0.7685(5) 0.0174(14) Uani 1 1 d . . . . .
C2 C 0.8433(10) 1.0698(7) 0.7011(5) 0.0173(14) Uani 1 1 d . . . . .
C3 C 0.8114(8) 0.8240(7) 0.6535(5) 0.0106(12) Uani 1 1 d . . . . .
C4 C 0.7980(9) 0.9564(7) 0.6119(5) 0.0139(13) Uani 1 1 d . . . . .
C5 C 0.7799(9) 0.6954(7) 0.5913(5) 0.0132(13) Uani 1 1 d . . . . .
C6 C 0.7561(9) 0.9655(7) 0.5058(5) 0.0127(12) Uani 1 1 d . . . . .
C7 C 0.7417(9) 0.7071(7) 0.4856(5) 0.0132(13) Uani 1 1 d . . . . .
C8 C 0.7336(9) 0.8378(7) 0.4438(5) 0.0134(12) Uani 1 1 d . . . . .
C9 C 0.7189(10) 0.5935(7) 0.3970(5) 0.0154(13) Uani 1 1 d . . . . .
C10 C 0.7138(9) 0.8114(7) 0.3293(5) 0.0185(14) Uani 1 1 d . . . . .
O1S O 0.2682(7) 0.4431(5) 0.8869(4) 0.0228(10) Uani 1 1 d . . . . .
C2S C 0.3106(10) 0.5763(8) 0.9101(5) 0.0219(14) Uani 1 1 d . . . . .
C3S C 0.3841(12) 0.6858(8) 0.8402(6) 0.0293(17) Uani 1 1 d . . . . .
H3SA H 0.5057 0.6666 0.8240 0.035 Uiso 1 1 calc R . . . .
H3SB H 0.2873 0.6822 0.7746 0.035 Uiso 1 1 calc R . . . .
C4S C 0.4170(12) 0.8299(8) 0.9018(6) 0.0280(16) Uani 1 1 d . . . . .
H4SA H 0.3311 0.8913 0.8660 0.034 Uiso 1 1 calc R . . . .
H4SB H 0.5524 0.8795 0.9108 0.034 Uiso 1 1 calc R . . . .
C5S C 0.2472(11) 0.5761(8) 1.0830(6) 0.0261(16) Uani 1 1 d . . . . .
H5SA H 0.3588 0.5910 1.1417 0.039 Uiso 1 1 calc GR . . . .
H5SB H 0.2029 0.4729 1.0628 0.039 Uiso 1 1 calc GR . . . .
H5SC H 0.1430 0.6172 1.1030 0.039 Uiso 1 1 calc GR . . . .
N1S N 0.3012(8) 0.6456(6) 0.9971(4) 0.0214(12) Uani 1 1 d . . . . .
C1S C 0.3719(11) 0.7998(8) 1.0072(6) 0.0253(15) Uani 1 1 d . . . . .
H1SA H 0.4893 0.8274 1.0634 0.030 Uiso 1 1 calc R . . . .
H1SB H 0.2725 0.8532 1.0217 0.030 Uiso 1 1 calc R . . . .
O2S O 0.8928(8) 0.8196(6) 0.0436(4) 0.0267(12) Uani 1 1 d . . . . .
H2 H 0.707(12) 0.629(9) 0.235(7) 0.03(2) Uiso 1 1 d . . . . .
H2SA H 0.840(15) 0.741(12) 0.061(8) 0.05(3) Uiso 1 1 d . . . . .
H1 H 0.916(15) 1.047(11) 0.856(8) 0.05(3) Uiso 1 1 d . . . . .
H2SB H 0.902(16) 0.800(12) -0.016(10) 0.06(3) Uiso 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
I1 C5 2.087(6) . ?
I2 C6 2.102(6) . ?
O1 C1 1.218(8) . ?
O2 C2 1.210(8) . ?
O3 C9 1.199(8) . ?
O4 C10 1.221(8) . ?
N1 C1 1.368(9) . ?
N1 C2 1.387(9) . ?
N1 H1 0.92(11) . ?
N2 C9 1.387(9) . ?
N2 C10 1.374(9) . ?
N2 H2 1.03(9) . ?
C1 C3 1.495(9) . ?
C2 C4 1.497(9) . ?
C3 C4 1.411(9) . ?
C3 C5 1.391(9) . ?
C4 C6 1.389(9) . ?
C5 C7 1.387(9) . ?
C6 C8 1.390(9) . ?
C7 C8 1.392(9) . ?
C7 C9 1.513(9) . ?
C8 C10 1.500(9) . ?
O1S C2S 1.253(9) . ?
C2S C3S 1.534(10) . ?
C2S N1S 1.317(9) . ?
C3S H3SA 0.9900 . ?
C3S H3SB 0.9900 . ?
C3S C4S 1.508(10) . ?
C4S H4SA 0.9900 . ?
C4S H4SB 0.9900 . ?
C4S C1S 1.533(10) . ?
C5S H5SA 0.9800 . ?
C5S H5SB 0.9800 . ?
C5S H5SC 0.9800 . ?
C5S N1S 1.440(9) . ?
N1S C1S 1.455(9) . ?
C1S H1SA 0.9900 . ?
C1S H1SB 0.9900 . ?
O2S H2SA 0.85(11) . ?
O2S H2SB 0.82(12) . ?

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
C1 N1 C2 112.2(5) . . ?
C1 N1 H1 125(7) . . ?
C2 N1 H1 123(7) . . ?
C9 N2 H2 128(5) . . ?
C10 N2 C9 113.1(5) . . ?
C10 N2 H2 118(5) . . ?
O1 C1 N1 125.2(6) . . ?
O1 C1 C3 127.5(6) . . ?
N1 C1 C3 107.3(5) . . ?
O2 C2 N1 125.1(6) . . ?
O2 C2 C4 128.4(6) . . ?
N1 C2 C4 106.4(5) . . ?
C4 C3 C1 106.8(5) . . ?
C5 C3 C1 130.8(6) . . ?
C5 C3 C4 122.3(6) . . ?
C3 C4 C2 107.2(5) . . ?
C6 C4 C2 131.3(6) . . ?
C6 C4 C3 121.4(6) . . ?
C3 C5 I1 122.7(5) . . ?
C7 C5 I1 121.8(5) . . ?
C7 C5 C3 115.4(6) . . ?
C4 C6 I2 120.9(5) . . ?
C4 C6 C8 116.1(6) . . ?
C8 C6 I2 123.0(5) . . ?
C5 C7 C8 122.7(6) . . ?
C5 C7 C9 129.5(6) . . ?
C8 C7 C9 107.6(6) . . ?
C6 C8 C7 121.9(6) . . ?
C6 C8 C10 130.3(6) . . ?
C7 C8 C10 107.6(6) . . ?
O3 C9 N2 126.0(6) . . ?
O3 C9 C7 128.7(6) . . ?
N2 C9 C7 105.4(6) . . ?
O4 C10 N2 126.0(6) . . ?
O4 C10 C8 127.8(6) . . ?
N2 C10 C8 106.3(5) . . ?
O1S C2S C3S 124.8(6) . . ?
O1S C2S N1S 126.5(7) . . ?
N1S C2S C3S 108.7(6) . . ?
C2S C3S H3SA 110.7 . . ?
C2S C3S H3SB 110.7 . . ?
H3SA C3S H3SB 108.8 . . ?
C4S C3S C2S 105.0(6) . . ?
C4S C3S H3SA 110.7 . . ?
C4S C3S H3SB 110.7 . . ?
C3S C4S H4SA 110.4 . . ?
C3S C4S H4SB 110.4 . . ?
C3S C4S C1S 106.5(6) . . ?
H4SA C4S H4SB 108.6 . . ?
C1S C4S H4SA 110.4 . . ?
C1S C4S H4SB 110.4 . . ?
H5SA C5S H5SB 109.5 . . ?
H5SA C5S H5SC 109.5 . . ?
H5SB C5S H5SC 109.5 . . ?
N1S C5S H5SA 109.5 . . ?
N1S C5S H5SB 109.5 . . ?
N1S C5S H5SC 109.5 . . ?
C2S N1S C5S 124.0(6) . . ?
C2S N1S C1S 115.3(6) . . ?
C5S N1S C1S 120.3(6) . . ?
C4S C1S H1SA 110.9 . . ?
C4S C1S H1SB 110.9 . . ?
N1S C1S C4S 104.2(6) . . ?
N1S C1S H1SA 110.9 . . ?
N1S C1S H1SB 110.9 . . ?
H1SA C1S H1SB 108.9 . . ?
H2SA O2S H2SB 104(10) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2 O1S 1.03(9) 1.77(9) 2.806(7) 175(7) 2_666
O2S H2SA O1S 0.85(11) 2.01(11) 2.854(7) 175(10) 2_666
N1 H1 O2S 0.92(11) 1.93(11) 2.741(8) 146(9) 2_776
O2S H2SB O1 0.82(12) 2.02(13) 2.836(7) 173(11) 1_554

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
I1 C5 C7 C8 -176.4(5) . . . . ?
I1 C5 C7 C9 -2.0(10) . . . . ?
I2 C6 C8 C7 -176.8(5) . . . . ?
I2 C6 C8 C10 8.6(9) . . . . ?
O1 C1 C3 C4 -177.2(7) . . . . ?
O1 C1 C3 C5 -0.1(11) . . . . ?
O2 C2 C4 C3 179.9(7) . . . . ?
O2 C2 C4 C6 2.2(13) . . . . ?
N1 C1 C3 C4 1.9(7) . . . . ?
N1 C1 C3 C5 179.0(6) . . . . ?
N1 C2 C4 C3 1.2(7) . . . . ?
N1 C2 C4 C6 -176.5(7) . . . . ?
C1 N1 C2 O2 -178.8(7) . . . . ?
C1 N1 C2 C4 0.0(8) . . . . ?
C1 C3 C4 C2 -1.8(7) . . . . ?
C1 C3 C4 C6 176.1(6) . . . . ?
C1 C3 C5 I1 1.5(9) . . . . ?
C1 C3 C5 C7 -174.4(6) . . . . ?
C2 N1 C1 O1 178.0(6) . . . . ?
C2 N1 C1 C3 -1.1(7) . . . . ?
C2 C4 C6 I2 -3.9(10) . . . . ?
C2 C4 C6 C8 175.7(7) . . . . ?
C3 C4 C6 I2 178.7(4) . . . . ?
C3 C4 C6 C8 -1.7(9) . . . . ?
C3 C5 C7 C8 -0.6(9) . . . . ?
C3 C5 C7 C9 173.8(6) . . . . ?
C4 C3 C5 I1 178.2(5) . . . . ?
C4 C3 C5 C7 2.4(9) . . . . ?
C4 C6 C8 C7 3.5(9) . . . . ?
C4 C6 C8 C10 -171.1(6) . . . . ?
C5 C3 C4 C2 -179.3(6) . . . . ?
C5 C3 C4 C6 -1.3(10) . . . . ?
C5 C7 C8 C6 -2.5(10) . . . . ?
C5 C7 C8 C10 173.2(6) . . . . ?
C5 C7 C9 O3 7.7(13) . . . . ?
C5 C7 C9 N2 -173.8(6) . . . . ?
C6 C8 C10 O4 -3.0(11) . . . . ?
C6 C8 C10 N2 177.7(6) . . . . ?
C7 C8 C10 O4 -178.2(7) . . . . ?
C7 C8 C10 N2 2.5(7) . . . . ?
C8 C7 C9 O3 -177.2(6) . . . . ?
C8 C7 C9 N2 1.2(7) . . . . ?
C9 N2 C10 O4 178.9(6) . . . . ?
C9 N2 C10 C8 -1.8(7) . . . . ?
C9 C7 C8 C6 -178.0(6) . . . . ?
C9 C7 C8 C10 -2.3(7) . . . . ?
C10 N2 C9 O3 178.9(7) . . . . ?
C10 N2 C9 C7 0.4(8) . . . . ?
O1S C2S C3S C4S -179.2(7) . . . . ?
O1S C2S N1S C5S 2.9(12) . . . . ?
O1S C2S N1S C1S 175.8(7) . . . . ?
C2S C3S C4S C1S 2.8(8) . . . . ?
C2S N1S C1S C4S 5.5(9) . . . . ?
C3S C2S N1S C5S -176.8(7) . . . . ?
C3S C2S N1S C1S -3.8(9) . . . . ?
C3S C4S C1S N1S -4.7(8) . . . . ?
C5S N1S C1S C4S 178.7(6) . . . . ?
N1S C2S C3S C4S 0.4(8) . . . . ?

_database_code_depnum_ccdc_archive 'CCDC 995180'
#######################################################################
#
#                 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_p21-c
_audit_creation_date             2013-12-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2013.12.10 svn.r2853 for OlexSys, GUI svn.r4736)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C10 H2 Br2 N2 O4'
_chemical_formula_sum            'C10 H2 Br2 N2 O4'
_chemical_formula_weight         373.96
_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'
Br Br -0.2901 2.4595 '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      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_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.3668(2)
_cell_length_b                   5.4181(2)
_cell_length_c                   12.5250(4)
_cell_angle_alpha                90
_cell_angle_beta                 92.257(2)
_cell_angle_gamma                90
_cell_volume                     499.54(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9958
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.490
_cell_measurement_theta_min      3.256
_shelx_estimated_absorpt_T_max   0.668
_shelx_estimated_absorpt_T_min   0.260
_exptl_absorpt_coefficient_mu    8.122
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.5562
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.1010 before and 0.0724 after correction.
The Ratio of minimum to maximum transmission is 0.7455.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    2.486
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             356
_exptl_crystal_size_max          0.227
_exptl_crystal_size_mid          0.139
_exptl_crystal_size_min          0.054
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0610
_diffrn_reflns_av_unetI/netI     0.0232
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            17489
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         30.540
_diffrn_reflns_theta_min         2.767
_diffrn_ambient_temperature      99.9
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1422
_reflns_number_total             1527
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.601
_refine_diff_density_min         -0.535
_refine_diff_density_rms         0.104
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.124
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     82
_refine_ls_number_reflns         1527
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0241
_refine_ls_R_factor_gt           0.0216
_refine_ls_restrained_S_all      1.124
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0239P)²+0.6474P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0550
_refine_ls_wR_factor_ref         0.0568
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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
Br1 Br 0.79294(2) 0.07105(4) 0.43300(2) 0.01288(7) Uani 1 1 d . . . . .
O1 O 0.4206(2) -0.0073(3) 0.29383(13) 0.0170(3) Uani 1 1 d . . . . .
O2 O 0.03946(19) 0.6343(3) 0.36386(12) 0.0162(3) Uani 1 1 d . . . . .
N1 N 0.1995(2) 0.2903(3) 0.31154(13) 0.0139(3) Uani 1 1 d . . . . .
H1 H 0.1198 0.2331 0.2636 0.017 Uiso 1 1 calc R . . . .
C1 C 0.6652(2) 0.4786(4) 0.55396(14) 0.0100(3) Uani 1 1 d . . . . .
C2 C 0.6258(2) 0.3114(3) 0.47208(14) 0.0100(3) Uani 1 1 d . . . . .
C3 C 0.4570(2) 0.3363(3) 0.41959(14) 0.0097(3) Uani 1 1 d . . . . .
C4 C 0.3671(2) 0.1802(4) 0.33402(15) 0.0125(3) Uani 1 1 d . . . . .
C5 C 0.1709(2) 0.4979(4) 0.37199(15) 0.0123(3) 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
Br1 C2 1.8707(18) . ?
O1 C4 1.207(3) . ?
O2 C5 1.219(2) . ?
N1 C4 1.390(2) . ?
N1 C5 1.377(3) . ?
C1 C2 1.390(3) . ?
C1 C3 1.397(2) 3_666 ?
C1 C5 1.498(3) 3_666 ?
C2 C3 1.390(2) . ?
C3 C1 1.397(2) 3_666 ?
C3 C4 1.499(3) . ?
C5 C1 1.498(3) 3_666 ?

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
C5 N1 C4 113.16(15) . . ?
C2 C1 C3 121.66(16) . 3_666 ?
C2 C1 C5 130.68(17) . 3_666 ?
C3 C1 C5 107.65(16) 3_666 3_666 ?
C1 C2 Br1 121.72(13) . . ?
C3 C2 Br1 121.98(14) . . ?
C3 C2 C1 116.29(16) . . ?
C1 C3 C4 107.72(15) 3_666 . ?
C2 C3 C1 122.04(16) . 3_666 ?
C2 C3 C4 130.17(17) . . ?
O1 C4 N1 125.36(18) . . ?
O1 C4 C3 129.14(17) . . ?
N1 C4 C3 105.45(16) . . ?
O2 C5 N1 125.99(18) . . ?
O2 C5 C1 128.17(19) . 3_666 ?
N1 C5 C1 105.83(16) . 3_666 ?

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
Br1 C2 C3 C1 -177.56(14) . . . 3_666 ?
Br1 C2 C3 C4 5.7(3) . . . . ?
C1 C2 C3 C1 1.1(3) . . . 3_666 ?
C1 C2 C3 C4 -175.57(18) . . . . ?
C1 C3 C4 O1 -174.7(2) 3_666 . . . ?
C1 C3 C4 N1 2.7(2) 3_666 . . . ?
C2 C3 C4 O1 2.4(3) . . . . ?
C2 C3 C4 N1 179.78(19) . . . . ?
C3 C1 C2 Br1 177.57(14) 3_666 . . . ?
C3 C1 C2 C3 -1.1(3) 3_666 . . . ?
C4 N1 C5 O2 176.1(2) . . . . ?
C4 N1 C5 C1 -2.7(2) . . . 3_666 ?
C5 N1 C4 O1 177.6(2) . . . . ?
C5 N1 C4 C3 0.1(2) . . . . ?
C5 C1 C2 Br1 -3.0(3) 3_666 . . . ?
C5 C1 C2 C3 178.33(18) 3_666 . . . ?

_database_code_depnum_ccdc_archive 'CCDC 995181'
#######################################################################
#
#                 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_p21-c
_audit_creation_date             2013-12-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2013.12.10 svn.r2853 for OlexSys, GUI svn.r4736)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C10 H2 Cl2 N2 O4'
_chemical_formula_sum            'C10 H2 Cl2 N2 O4'
_chemical_formula_weight         285.04
_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 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 '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      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_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.1051(12)
_cell_length_b                   5.4752(10)
_cell_length_c                   12.252(2)
_cell_angle_alpha                90
_cell_angle_beta                 90.693(15)
_cell_angle_gamma                90
_cell_volume                     476.57(14)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1838
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      64.872
_cell_measurement_theta_min      6.229
_shelx_estimated_absorpt_T_max   0.957
_shelx_estimated_absorpt_T_min   0.559
_exptl_absorpt_coefficient_mu    6.271
_exptl_absorpt_correction_T_max  0.7526
_exptl_absorpt_correction_T_min  0.6576
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0480 before and 0.0331 after correction.
The Ratio of minimum to maximum transmission is 0.8738.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.986
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             284
_exptl_crystal_size_max          0.105
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.007
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0234
_diffrn_reflns_av_unetI/netI     0.0227
_diffrn_reflns_Laue_measured_fraction_full 0.932
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            2930
_diffrn_reflns_point_group_measured_fraction_full 0.932
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         64.867
_diffrn_reflns_theta_min         6.229
_diffrn_ambient_temperature      99.99
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.932
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                723
_reflns_number_total             807
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.348
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.072
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     82
_refine_ls_number_reflns         807
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0365
_refine_ls_R_factor_gt           0.0313
_refine_ls_restrained_S_all      1.099
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0443P)²+0.5603P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0813
_refine_ls_wR_factor_ref         0.0844
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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
Cl1 Cl 0.78766(8) 0.08424(11) 0.06287(5) 0.0160(2) Uani 1 1 d . . . . .
O1 O 0.0302(2) 0.6324(3) 0.13317(14) 0.0176(4) Uani 1 1 d . . . . .
O2 O 0.4226(3) -0.0134(3) 0.20328(14) 0.0189(4) Uani 1 1 d . . . . .
N1 N 0.1978(3) 0.2887(4) 0.18740(16) 0.0145(5) Uani 1 1 d . . . . .
H1 H 0.1189 0.2333 0.2364 0.017 Uiso 1 1 calc R . . . .
C1 C 0.6304(3) 0.3096(5) 0.02757(19) 0.0133(5) Uani 1 1 d . . . . .
C2 C 0.4570(3) 0.3330(5) 0.07881(19) 0.0114(5) Uani 1 1 d . . . . .
C3 C 0.3672(4) 0.1762(5) 0.1640(2) 0.0161(6) Uani 1 1 d . . . . .
C4 C 0.1650(4) 0.4966(5) 0.1261(2) 0.0148(6) Uani 1 1 d . . . . .
C5 C 0.3312(3) 0.5193(5) 0.05238(19) 0.0129(5) 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
Cl1 C1 1.717(3) . ?
O1 C4 1.217(3) . ?
O2 C3 1.208(3) . ?
N1 C3 1.385(3) . ?
N1 C4 1.381(3) . ?
C1 C2 1.395(4) . ?
C1 C5 1.385(4) 3_665 ?
C2 C3 1.500(4) . ?
C2 C5 1.392(4) . ?
C4 C5 1.501(3) . ?
C5 C1 1.385(4) 3_665 ?

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
C4 N1 C3 113.3(2) . . ?
C2 C1 Cl1 121.9(2) . . ?
C5 C1 Cl1 122.1(2) 3_665 . ?
C5 C1 C2 116.0(2) 3_665 . ?
C1 C2 C3 130.2(2) . . ?
C5 C2 C1 122.0(2) . . ?
C5 C2 C3 107.7(2) . . ?
O2 C3 N1 125.4(2) . . ?
O2 C3 C2 129.0(2) . . ?
N1 C3 C2 105.5(2) . . ?
O1 C4 N1 126.3(2) . . ?
O1 C4 C5 128.2(2) . . ?
N1 C4 C5 105.5(2) . . ?
C1 C5 C2 121.9(2) 3_665 . ?
C1 C5 C4 130.2(2) 3_665 . ?
C2 C5 C4 107.9(2) . . ?

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
Cl1 C1 C2 C3 -3.8(4) . . . . ?
Cl1 C1 C2 C5 178.29(19) . . . . ?
O1 C4 C5 C1 -2.8(5) . . . 3_665 ?
O1 C4 C5 C2 175.4(2) . . . . ?
N1 C4 C5 C1 178.3(2) . . . 3_665 ?
N1 C4 C5 C2 -3.5(3) . . . . ?
C1 C2 C3 O2 -4.0(4) . . . . ?
C1 C2 C3 N1 178.3(2) . . . . ?
C1 C2 C5 C1 1.0(4) . . . 3_665 ?
C1 C2 C5 C4 -177.4(2) . . . . ?
C3 N1 C4 O1 -177.6(2) . . . . ?
C3 N1 C4 C5 1.3(3) . . . . ?
C3 C2 C5 C1 -177.4(2) . . . 3_665 ?
C3 C2 C5 C4 4.3(3) . . . . ?
C4 N1 C3 O2 -176.5(2) . . . . ?
C4 N1 C3 C2 1.3(3) . . . . ?
C5 C1 C2 C3 177.0(2) 3_665 . . . ?
C5 C1 C2 C5 -0.9(4) 3_665 . . . ?
C5 C2 C3 O2 174.1(3) . . . . ?
C5 C2 C3 N1 -3.5(3) . . . . ?

_database_code_depnum_ccdc_archive 'CCDC 995182'
