# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_mcg1451lt
_database_code_depnum_ccdc_archive 'CCDC 1059604'
_audit_update_record             
;
2015-04-14 deposited with the CCDC.
2016-08-23 downloaded from the CCDC.
;
_audit_creation_date             2015-04-14
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C6 H4 Cl2 O2, C10 H8 N4'
_chemical_formula_sum            'C16 H12 Cl2 N4 O2'
_chemical_formula_weight         363.20
_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'

_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                   8.9957(11)
_cell_length_b                   10.0831(13)
_cell_length_c                   10.4133(14)
_cell_angle_alpha                89.154(5)
_cell_angle_beta                 71.747(5)
_cell_angle_gamma                64.264(5)
_cell_volume                     799.87(18)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4515
_cell_measurement_temperature    190(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      2.608
_exptl_absorpt_coefficient_mu    0.423
_exptl_absorpt_correction_T_max  0.942
_exptl_absorpt_correction_T_min  0.923
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2002)'
_exptl_crystal_colour            red-orange
_exptl_crystal_density_diffrn    1.508
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       'Irregular Prism'
_exptl_crystal_F_000             372
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.14
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0220
_diffrn_reflns_av_unetI/netI     0.0267
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10633
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.504
_diffrn_reflns_theta_min         2.080
_diffrn_ambient_temperature      190(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       'CCD rotation images, phi scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3060
_reflns_number_total             3664
_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       'HKL Scalepack (Otwinowski and Minor, 1997)'
_computing_data_collection       'Collect (Hooft, 1998)'
_computing_data_reduction        'Denzo (Otwinowski and Minor, 1997)'
_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    'ShelXT (Sheldrick, 2008)'
_refine_diff_density_max         0.282
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         3664
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0410
_refine_ls_R_factor_gt           0.0312
_refine_ls_restrained_S_all      1.055
_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)+(0.0362P)²+0.3247P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0783
_refine_ls_wR_factor_ref         0.0842
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C15(H15), C12(H12), C3(H3), C2(H2), C7(H7), C4(H4), C9(H9), C8(H8), C1(H1),
 C10(H10)
2.b Idealised tetrahedral OH refined as rotating group:
 O2(H2A), O1(H1A)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
Cl2 Cl 0.75620(5) -0.11814(4) -0.71381(4) 0.02703(11) Uani 1 1 d . . . . .
Cl1 Cl 0.29514(6) -0.10223(5) -0.95138(4) 0.03213(12) Uani 1 1 d . . . . .
O2 O 0.54700(14) -0.20787(13) -0.48405(11) 0.0272(3) Uani 1 1 d . . . . .
H2A H 0.4794 -0.2237 -0.4195 0.041 Uiso 1 1 calc GR . . . .
O1 O 0.13240(16) -0.18634(16) -0.69517(13) 0.0369(3) Uani 1 1 d . . . . .
H1A H 0.0966 -0.2184 -0.6254 0.055 Uiso 1 1 calc GR . . . .
C15 C 0.51452(19) -0.11686(16) -0.81685(15) 0.0218(3) Uani 1 1 d . . . . .
H15 H 0.5751 -0.0912 -0.8950 0.026 Uiso 1 1 calc R . . . .
C12 C 0.3357(2) -0.19526(17) -0.58548(16) 0.0234(3) Uani 1 1 d . . . . .
H12 H 0.2751 -0.2208 -0.5073 0.028 Uiso 1 1 calc R . . . .
N1 N -0.01449(18) 0.29732(15) 0.46457(14) 0.0253(3) Uani 1 1 d . . . . .
N2 N 0.20946(18) 0.45283(15) 0.11611(14) 0.0289(3) Uani 1 1 d . . . . .
C13 C 0.48443(19) -0.18183(16) -0.58905(15) 0.0211(3) Uani 1 1 d . . . . .
N4 N 0.34543(19) 0.71341(16) -0.26731(14) 0.0302(3) Uani 1 1 d . . . . .
C14 C 0.57228(19) -0.14027(16) -0.70634(16) 0.0211(3) Uani 1 1 d . . . . .
C11 C 0.2748(2) -0.17160(17) -0.69543(16) 0.0235(3) Uani 1 1 d . . . . .
C16 C 0.3667(2) -0.13152(17) -0.81141(15) 0.0221(3) Uani 1 1 d . . . . .
N3 N 0.10599(18) 0.55379(15) 0.07159(13) 0.0259(3) Uani 1 1 d . . . . .
C5 C 0.1244(2) 0.40505(17) 0.23451(16) 0.0231(3) Uani 1 1 d . . . . .
C3 C 0.1539(2) 0.22304(18) 0.38628(17) 0.0264(3) Uani 1 1 d . . . . .
H3 H 0.2239 0.1340 0.4101 0.032 Uiso 1 1 calc R . . . .
C2 C -0.0514(2) 0.48416(18) 0.31546(17) 0.0265(3) Uani 1 1 d . . . . .
H2 H -0.1245 0.5735 0.2940 0.032 Uiso 1 1 calc R . . . .
C7 C 0.0922(2) 0.73360(18) -0.08415(17) 0.0267(3) Uani 1 1 d . . . . .
H7 H -0.0278 0.7857 -0.0371 0.032 Uiso 1 1 calc R . . . .
C4 C 0.2292(2) 0.27298(18) 0.27076(17) 0.0271(3) Uani 1 1 d . . . . .
H4 H 0.3473 0.2190 0.2188 0.033 Uiso 1 1 calc R . . . .
C9 C 0.3725(2) 0.52610(19) -0.11887(17) 0.0324(4) Uani 1 1 d . . . . .
H9 H 0.4435 0.4374 -0.0952 0.039 Uiso 1 1 calc R . . . .
C8 C 0.1736(2) 0.78537(19) -0.19516(17) 0.0295(4) Uani 1 1 d . . . . .
H8 H 0.1056 0.8742 -0.2206 0.035 Uiso 1 1 calc R . . . .
C1 C -0.1132(2) 0.42570(18) 0.42821(17) 0.0279(4) Uani 1 1 d . . . . .
H1 H -0.2306 0.4782 0.4827 0.034 Uiso 1 1 calc R . . . .
C10 C 0.4410(2) 0.5859(2) -0.22812(18) 0.0346(4) Uani 1 1 d . . . . .
H10 H 0.5604 0.5349 -0.2776 0.041 Uiso 1 1 calc R . . . .
C6 C 0.1942(2) 0.60243(17) -0.04519(16) 0.0246(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
Cl2 C14 1.7413(15) . ?
Cl1 C16 1.7422(15) . ?
O2 H2A 0.8200 . ?
O2 C13 1.3527(18) . ?
O1 H1A 0.8200 . ?
O1 C11 1.3518(18) . ?
C15 H15 0.9300 . ?
C15 C14 1.382(2) . ?
C15 C16 1.385(2) . ?
C12 H12 0.9300 . ?
C12 C13 1.391(2) . ?
C12 C11 1.392(2) . ?
N1 C3 1.334(2) . ?
N1 C1 1.344(2) . ?
N2 N3 1.2454(19) . ?
N2 C5 1.4317(19) . ?
C13 C14 1.400(2) . ?
N4 C8 1.340(2) . ?
N4 C10 1.343(2) . ?
C11 C16 1.398(2) . ?
N3 C6 1.4368(19) . ?
C5 C2 1.392(2) . ?
C5 C4 1.386(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.388(2) . ?
C2 H2 0.9300 . ?
C2 C1 1.375(2) . ?
C7 H7 0.9300 . ?
C7 C8 1.389(2) . ?
C7 C6 1.385(2) . ?
C4 H4 0.9300 . ?
C9 H9 0.9300 . ?
C9 C10 1.379(2) . ?
C9 C6 1.389(2) . ?
C8 H8 0.9300 . ?
C1 H1 0.9300 . ?
C10 H10 0.9300 . ?

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 O2 H2A 109.5 . . ?
C11 O1 H1A 109.5 . . ?
C14 C15 H15 119.9 . . ?
C14 C15 C16 120.14(13) . . ?
C16 C15 H15 119.9 . . ?
C13 C12 H12 119.0 . . ?
C13 C12 C11 122.01(14) . . ?
C11 C12 H12 119.0 . . ?
C3 N1 C1 117.59(13) . . ?
N3 N2 C5 113.81(13) . . ?
O2 C13 C12 122.50(13) . . ?
O2 C13 C14 119.11(13) . . ?
C12 C13 C14 118.38(14) . . ?
C8 N4 C10 117.34(14) . . ?
C15 C14 Cl2 119.52(11) . . ?
C15 C14 C13 120.53(14) . . ?
C13 C14 Cl2 119.95(12) . . ?
O1 C11 C12 123.07(14) . . ?
O1 C11 C16 118.85(14) . . ?
C12 C11 C16 118.08(14) . . ?
C15 C16 Cl1 119.82(11) . . ?
C15 C16 C11 120.84(14) . . ?
C11 C16 Cl1 119.34(12) . . ?
N2 N3 C6 112.84(13) . . ?
C2 C5 N2 124.44(14) . . ?
C4 C5 N2 116.24(14) . . ?
C4 C5 C2 119.29(14) . . ?
N1 C3 H3 118.6 . . ?
N1 C3 C4 122.83(15) . . ?
C4 C3 H3 118.6 . . ?
C5 C2 H2 121.2 . . ?
C1 C2 C5 117.69(14) . . ?
C1 C2 H2 121.2 . . ?
C8 C7 H7 120.8 . . ?
C6 C7 H7 120.8 . . ?
C6 C7 C8 118.36(15) . . ?
C5 C4 C3 118.57(15) . . ?
C5 C4 H4 120.7 . . ?
C3 C4 H4 120.7 . . ?
C10 C9 H9 121.0 . . ?
C10 C9 C6 117.98(16) . . ?
C6 C9 H9 121.0 . . ?
N4 C8 C7 123.09(15) . . ?
N4 C8 H8 118.5 . . ?
C7 C8 H8 118.5 . . ?
N1 C1 C2 124.02(15) . . ?
N1 C1 H1 118.0 . . ?
C2 C1 H1 118.0 . . ?
N4 C10 C9 123.83(16) . . ?
N4 C10 H10 118.1 . . ?
C9 C10 H10 118.1 . . ?
C7 C6 N3 116.77(14) . . ?
C7 C6 C9 119.39(14) . . ?
C9 C6 N3 123.85(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
O2 C13 C14 Cl2 -1.6(2) . . . . ?
O2 C13 C14 C15 178.21(14) . . . . ?
O1 C11 C16 Cl1 -0.1(2) . . . . ?
O1 C11 C16 C15 -179.23(15) . . . . ?
C12 C13 C14 Cl2 178.60(12) . . . . ?
C12 C13 C14 C15 -1.6(2) . . . . ?
C12 C11 C16 Cl1 179.58(12) . . . . ?
C12 C11 C16 C15 0.4(2) . . . . ?
N1 C3 C4 C5 -0.6(3) . . . . ?
N2 N3 C6 C7 -166.96(15) . . . . ?
N2 N3 C6 C9 12.9(2) . . . . ?
N2 C5 C2 C1 -178.32(15) . . . . ?
N2 C5 C4 C3 178.82(15) . . . . ?
C13 C12 C11 O1 178.90(15) . . . . ?
C13 C12 C11 C16 -0.8(2) . . . . ?
C14 C15 C16 Cl1 -179.85(11) . . . . ?
C14 C15 C16 C11 -0.7(2) . . . . ?
C11 C12 C13 O2 -178.45(14) . . . . ?
C11 C12 C13 C14 1.3(2) . . . . ?
C16 C15 C14 Cl2 -178.87(12) . . . . ?
C16 C15 C14 C13 1.3(2) . . . . ?
N3 N2 C5 C2 -15.8(2) . . . . ?
N3 N2 C5 C4 166.37(15) . . . . ?
C5 N2 N3 C6 178.59(13) . . . . ?
C5 C2 C1 N1 -0.1(3) . . . . ?
C3 N1 C1 C2 0.3(2) . . . . ?
C2 C5 C4 C3 0.8(2) . . . . ?
C4 C5 C2 C1 -0.5(2) . . . . ?
C8 N4 C10 C9 -0.1(3) . . . . ?
C8 C7 C6 N3 178.91(14) . . . . ?
C8 C7 C6 C9 -1.0(2) . . . . ?
C1 N1 C3 C4 0.0(2) . . . . ?
C10 N4 C8 C7 -0.3(3) . . . . ?
C10 C9 C6 N3 -179.33(16) . . . . ?
C10 C9 C6 C7 0.6(3) . . . . ?
C6 C7 C8 N4 0.9(3) . . . . ?
C6 C9 C10 N4 0.0(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_mcg1451rt
_database_code_depnum_ccdc_archive 'CCDC 1059605'
_audit_update_record             
;
2015-04-14 deposited with the CCDC.
2016-08-23 downloaded from the CCDC.
;
_audit_creation_date             2015-04-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_shelxl_version_number           2013-3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C6 H4 Cl2 O2, C10 H8 N4'
_chemical_formula_sum            'C16 H12 Cl2 N4 O2'
_chemical_formula_weight         363.20
_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'

_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                   9.0188(9)
_cell_length_b                   10.1722(10)
_cell_length_c                   10.4719(10)
_cell_angle_alpha                88.254(5)
_cell_angle_beta                 71.579(5)
_cell_angle_gamma                64.025(5)
_cell_volume                     812.82(14)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2423
_cell_measurement_temperature    290(2)
_cell_measurement_theta_max      25.35
_cell_measurement_theta_min      1.00
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.416
_exptl_absorpt_correction_T_max  0.943
_exptl_absorpt_correction_T_min  0.924
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2002)'
_exptl_crystal_colour            red-orange
_exptl_crystal_density_diffrn    1.484
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       'Irregular Prism'
_exptl_crystal_F_000             372
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.14
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0320
_diffrn_reflns_av_unetI/netI     0.0612
_diffrn_reflns_Laue_measured_fraction_full 0.923
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4930
_diffrn_reflns_point_group_measured_fraction_full 0.923
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         25.332
_diffrn_reflns_theta_min         2.066
_diffrn_ambient_temperature      290(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.923
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       'CCD rotation images, phi scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1809
_reflns_number_total             2949
_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       'HKL Scalepack (Otwinowski and Minor, 1997)'
_computing_data_collection       'Collect (Hooft, 1998)'
_computing_data_reduction        'Denzo (Otwinowski and Minor, 1997)'
_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    'ShelXT (Sheldrick, 2008)'
_refine_diff_density_max         0.213
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         2949
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0948
_refine_ls_R_factor_gt           0.0445
_refine_ls_restrained_S_all      1.026
_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)+(0.0557P)²+0.1222P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0977
_refine_ls_wR_factor_ref         0.1201
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C15(H15), C12(H12), C9(H9), C8(H8), C7(H7), C4(H4), C2(H2), C3(H3), C10(H10),
 C1(H1)
2.b Idealised tetrahedral OH refined as rotating group:
 O1(H1A), O2(H2A)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 0.24541(9) 0.61826(8) -0.28537(8) 0.0577(3) Uani 1 1 d . . . . .
Cl2 Cl 0.70470(11) 0.60237(10) -0.05080(8) 0.0658(3) Uani 1 1 d . . . . .
O1 O 0.4531(3) 0.7077(2) -0.5148(2) 0.0560(5) Uani 1 1 d . . . . .
H1A H 0.5135 0.7338 -0.5758 0.084 Uiso 1 1 calc GR . . . .
C15 C 0.4868(3) 0.6166(3) -0.1842(3) 0.0463(7) Uani 1 1 d . . . . .
H15 H 0.4272 0.5901 -0.1062 0.056 Uiso 1 1 calc R . . . .
C12 C 0.6635(4) 0.6955(3) -0.4145(3) 0.0488(7) Uani 1 1 d . . . . .
H12 H 0.7239 0.7210 -0.4928 0.059 Uiso 1 1 calc R . . . .
O2 O 0.8666(3) 0.6866(3) -0.3062(2) 0.0714(7) Uani 1 1 d . . . . .
H2A H 0.8912 0.7328 -0.3681 0.107 Uiso 1 1 calc GR . . . .
C13 C 0.7240(4) 0.6722(3) -0.3057(3) 0.0498(7) Uani 1 1 d . . . . .
N3 N 0.2096(3) 0.9513(3) 0.1140(2) 0.0578(7) Uani 1 1 d . . . . .
C9 C -0.0491(4) 0.9831(3) 0.3133(3) 0.0535(8) Uani 1 1 d . . . . .
H9 H -0.1216 1.0720 0.2911 0.064 Uiso 1 1 calc R . . . .
C11 C 0.5156(3) 0.6821(3) -0.4105(3) 0.0435(7) Uani 1 1 d . . . . .
C6 C 0.1237(4) 0.9042(3) 0.2338(3) 0.0468(7) Uani 1 1 d . . . . .
N4 N -0.0148(3) 0.7987(3) 0.4633(2) 0.0518(6) Uani 1 1 d . . . . .
N2 N 0.1088(3) 1.0539(3) 0.0716(2) 0.0533(6) Uani 1 1 d . . . . .
N1 N 0.3478(4) 1.2107(3) -0.2681(2) 0.0598(7) Uani 1 1 d . . . . .
C8 C 0.1503(4) 0.7256(3) 0.3866(3) 0.0543(8) Uani 1 1 d . . . . .
H8 H 0.2199 0.6369 0.4110 0.065 Uiso 1 1 calc R . . . .
C14 C 0.6336(4) 0.6318(3) -0.1901(3) 0.0465(7) Uani 1 1 d . . . . .
C7 C 0.2250(4) 0.7748(3) 0.2709(3) 0.0576(8) Uani 1 1 d . . . . .
H7 H 0.3426 0.7205 0.2192 0.069 Uiso 1 1 calc R . . . .
C4 C 0.0974(4) 1.2316(3) -0.0846(3) 0.0547(8) Uani 1 1 d . . . . .
H4 H -0.0219 1.2840 -0.0372 0.066 Uiso 1 1 calc R . . . .
C16 C 0.4285(3) 0.6406(3) -0.2935(3) 0.0435(7) Uani 1 1 d . . . . .
C2 C 0.3732(4) 1.0250(3) -0.1192(3) 0.0645(9) Uani 1 1 d . . . . .
H2 H 0.4436 0.9362 -0.0954 0.077 Uiso 1 1 calc R . . . .
C3 C 0.1773(4) 1.2831(3) -0.1951(3) 0.0598(8) Uani 1 1 d . . . . .
H3 H 0.1097 1.3724 -0.2200 0.072 Uiso 1 1 calc R . . . .
C10 C -0.1106(4) 0.9257(3) 0.4264(3) 0.0568(8) Uani 1 1 d . . . . .
H10 H -0.2271 0.9791 0.4809 0.068 Uiso 1 1 calc R . . . .
C1 C 0.4412(4) 1.0841(4) -0.2286(3) 0.0662(9) Uani 1 1 d . . . . .
H1 H 0.5600 1.0325 -0.2783 0.079 Uiso 1 1 calc R . . . .
C5 C 0.1973(4) 1.1014(3) -0.0459(3) 0.0490(7) 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 C16 1.739(3) . ?
Cl2 C14 1.739(3) . ?
O1 H1A 0.8200 . ?
O1 C11 1.350(3) . ?
C15 H15 0.9300 . ?
C15 C14 1.382(4) . ?
C15 C16 1.378(4) . ?
C12 H12 0.9300 . ?
C12 C13 1.384(4) . ?
C12 C11 1.387(4) . ?
O2 H2A 0.8200 . ?
O2 C13 1.355(3) . ?
C13 C14 1.392(4) . ?
N3 C6 1.442(3) . ?
N3 N2 1.228(3) . ?
C9 H9 0.9300 . ?
C9 C6 1.375(4) . ?
C9 C10 1.370(4) . ?
C11 C16 1.394(4) . ?
C6 C7 1.362(4) . ?
N4 C8 1.314(4) . ?
N4 C10 1.330(3) . ?
N2 C5 1.438(3) . ?
N1 C3 1.338(4) . ?
N1 C1 1.333(4) . ?
C8 H8 0.9300 . ?
C8 C7 1.384(4) . ?
C7 H7 0.9300 . ?
C4 H4 0.9300 . ?
C4 C3 1.378(4) . ?
C4 C5 1.372(4) . ?
C2 H2 0.9300 . ?
C2 C1 1.374(4) . ?
C2 C5 1.377(4) . ?
C3 H3 0.9300 . ?
C10 H10 0.9300 . ?
C1 H1 0.9300 . ?

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
C11 O1 H1A 109.5 . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
C16 C15 C14 120.1(2) . . ?
C13 C12 H12 119.0 . . ?
C13 C12 C11 122.1(2) . . ?
C11 C12 H12 119.0 . . ?
C13 O2 H2A 109.5 . . ?
C12 C13 C14 118.2(2) . . ?
O2 C13 C12 123.3(2) . . ?
O2 C13 C14 118.5(3) . . ?
N2 N3 C6 114.0(2) . . ?
C6 C9 H9 121.3 . . ?
C10 C9 H9 121.3 . . ?
C10 C9 C6 117.5(3) . . ?
O1 C11 C12 122.6(2) . . ?
O1 C11 C16 119.0(2) . . ?
C12 C11 C16 118.3(2) . . ?
C9 C6 N3 124.4(3) . . ?
C7 C6 N3 116.5(2) . . ?
C7 C6 C9 119.1(3) . . ?
C8 N4 C10 117.2(2) . . ?
N3 N2 C5 113.1(2) . . ?
C1 N1 C3 116.9(3) . . ?
N4 C8 H8 118.6 . . ?
N4 C8 C7 122.8(3) . . ?
C7 C8 H8 118.6 . . ?
C15 C14 Cl2 119.6(2) . . ?
C15 C14 C13 120.8(3) . . ?
C13 C14 Cl2 119.6(2) . . ?
C6 C7 C8 119.0(3) . . ?
C6 C7 H7 120.5 . . ?
C8 C7 H7 120.5 . . ?
C3 C4 H4 120.6 . . ?
C5 C4 H4 120.6 . . ?
C5 C4 C3 118.7(3) . . ?
C15 C16 Cl1 119.6(2) . . ?
C15 C16 C11 120.5(2) . . ?
C11 C16 Cl1 120.0(2) . . ?
C1 C2 H2 121.1 . . ?
C1 C2 C5 117.9(3) . . ?
C5 C2 H2 121.1 . . ?
N1 C3 C4 123.0(3) . . ?
N1 C3 H3 118.5 . . ?
C4 C3 H3 118.5 . . ?
C9 C10 H10 117.8 . . ?
N4 C10 C9 124.4(3) . . ?
N4 C10 H10 117.8 . . ?
N1 C1 C2 124.1(3) . . ?
N1 C1 H1 117.9 . . ?
C2 C1 H1 117.9 . . ?
C4 C5 N2 116.6(2) . . ?
C4 C5 C2 119.4(3) . . ?
C2 C5 N2 124.0(3) . . ?

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 C11 C16 Cl1 1.6(4) . . . . ?
O1 C11 C16 C15 -178.7(2) . . . . ?
C12 C13 C14 Cl2 -179.7(2) . . . . ?
C12 C13 C14 C15 -0.4(4) . . . . ?
C12 C11 C16 Cl1 -178.5(2) . . . . ?
C12 C11 C16 C15 1.2(4) . . . . ?
O2 C13 C14 Cl2 0.3(4) . . . . ?
O2 C13 C14 C15 179.6(3) . . . . ?
C13 C12 C11 O1 178.5(3) . . . . ?
C13 C12 C11 C16 -1.4(4) . . . . ?
N3 C6 C7 C8 178.8(3) . . . . ?
N3 N2 C5 C4 -168.5(3) . . . . ?
N3 N2 C5 C2 11.2(4) . . . . ?
C9 C6 C7 C8 0.9(4) . . . . ?
C11 C12 C13 O2 -179.0(3) . . . . ?
C11 C12 C13 C14 1.0(4) . . . . ?
C6 N3 N2 C5 178.6(2) . . . . ?
C6 C9 C10 N4 -0.6(5) . . . . ?
N4 C8 C7 C6 -0.4(5) . . . . ?
N2 N3 C6 C9 -13.8(4) . . . . ?
N2 N3 C6 C7 168.4(3) . . . . ?
C8 N4 C10 C9 1.1(4) . . . . ?
C14 C15 C16 Cl1 179.0(2) . . . . ?
C14 C15 C16 C11 -0.7(4) . . . . ?
C16 C15 C14 Cl2 179.6(2) . . . . ?
C16 C15 C14 C13 0.3(4) . . . . ?
C3 N1 C1 C2 0.1(5) . . . . ?
C3 C4 C5 N2 178.7(2) . . . . ?
C3 C4 C5 C2 -1.0(4) . . . . ?
C10 C9 C6 N3 -178.1(3) . . . . ?
C10 C9 C6 C7 -0.4(4) . . . . ?
C10 N4 C8 C7 -0.6(4) . . . . ?
C1 N1 C3 C4 -0.8(5) . . . . ?
C1 C2 C5 N2 -179.3(3) . . . . ?
C1 C2 C5 C4 0.4(5) . . . . ?
C5 C4 C3 N1 1.2(5) . . . . ?
C5 C2 C1 N1 0.1(5) . . . . ?

_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_mcg1475lt
_database_code_depnum_ccdc_archive 'CCDC 1059606'
_audit_update_record             
;
2015-04-14 deposited with the CCDC.
2016-08-23 downloaded from the CCDC.
;
_audit_creation_date             2015-04-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_shelxl_version_number           2013-3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C6 H4 Br2 O2, C10 H8 N4'
_chemical_formula_sum            'C16 H12 Br2 N4 O2'
_chemical_formula_weight         452.12
_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      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                   9.0278(9)
_cell_length_b                   10.2654(10)
_cell_length_c                   10.6009(11)
_cell_angle_alpha                75.203(5)
_cell_angle_beta                 70.936(5)
_cell_angle_gamma                64.122(5)
_cell_volume                     828.05(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    190(2)
_exptl_absorpt_coefficient_mu    4.912
_exptl_absorpt_correction_T_max  0.555
_exptl_absorpt_correction_T_min  0.161
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2002)'
_exptl_crystal_colour            'yellowish orange'
_exptl_crystal_colour_modifier   yellow
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.813
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             444
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.12
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0206
_diffrn_reflns_av_unetI/netI     0.0233
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            13131
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         29.102
_diffrn_reflns_theta_min         3.220
_diffrn_ambient_temperature      190(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       'CCD rotation images, phi scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3772
_reflns_number_total             4414
_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       'Collect (Hooft, 1998)'
_computing_data_collection       'HKL Scalepack (Otwinowski and Minor, 1997)'
_computing_data_reduction        'Denzo (Otwinowski and Minor, 1997)'
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.473
_refine_diff_density_min         -0.352
_refine_diff_density_rms         0.065
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         4414
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0287
_refine_ls_R_factor_gt           0.0210
_refine_ls_restrained_S_all      1.049
_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)+(0.0247P)²+0.1964P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0493
_refine_ls_wR_factor_ref         0.0517
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C15(H15), C12(H12), C1(H1), C9(H9), C4(H4), C3(H3), C10(H10), C2(H2), C7(H7),
 C8(H8)
2.b Idealised tetrahedral OH refined as rotating group:
 O2(H2A), O1(H1A)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
Br2 Br 1.15424(2) 0.11623(2) 0.28157(2) 0.02464(5) Uani 1 1 d . . . . .
Br1 Br 0.68150(2) 0.09717(2) 0.04976(2) 0.02846(5) Uani 1 1 d . . . . .
O2 O 0.83843(15) 0.21448(14) 0.51139(11) 0.0263(3) Uani 1 1 d . . . . .
H2A H 0.7535 0.2365 0.5740 0.039 Uiso 1 1 calc GR . . . .
O1 O 0.44207(15) 0.19108(17) 0.31429(13) 0.0365(3) Uani 1 1 d . . . . .
H1A H 0.3750 0.2270 0.3819 0.055 Uiso 1 1 calc GR . . . .
N1 N 0.21280(17) 0.29886(16) 0.53980(14) 0.0251(3) Uani 1 1 d . . . . .
N4 N -0.55721(19) 0.69633(17) 1.27415(14) 0.0297(3) Uani 1 1 d . . . . .
N3 N -0.16076(18) 0.54284(16) 0.93446(14) 0.0264(3) Uani 1 1 d . . . . .
N2 N -0.16501(19) 0.44452(17) 0.88935(15) 0.0301(3) Uani 1 1 d . . . . .
C13 C 0.8011(2) 0.18584(17) 0.41022(15) 0.0198(3) Uani 1 1 d . . . . .
C11 C 0.5996(2) 0.17414(18) 0.31140(16) 0.0229(3) Uani 1 1 d . . . . .
C14 C 0.92922(19) 0.14140(17) 0.29429(16) 0.0194(3) Uani 1 1 d . . . . .
C16 C 0.7302(2) 0.13122(17) 0.19643(15) 0.0200(3) Uani 1 1 d . . . . .
C6 C -0.2970(2) 0.58889(18) 1.05201(16) 0.0241(3) Uani 1 1 d . . . . .
C15 C 0.89301(19) 0.11573(16) 0.18759(15) 0.0200(3) Uani 1 1 d . . . . .
H15 H 0.9784 0.0881 0.1100 0.024 Uiso 1 1 calc R . . . .
C12 C 0.6382(2) 0.20040(19) 0.41724(16) 0.0237(3) Uani 1 1 d . . . . .
H12 H 0.5526 0.2284 0.4946 0.028 Uiso 1 1 calc R . . . .
C1 C 0.1204(2) 0.22290(19) 0.61813(17) 0.0264(4) Uani 1 1 d . . . . .
H1 H 0.1407 0.1344 0.5942 0.032 Uiso 1 1 calc R . . . .
C5 C -0.0334(2) 0.40006(18) 0.76983(16) 0.0238(3) Uani 1 1 d . . . . .
C9 C -0.3203(2) 0.71500(19) 1.09407(17) 0.0263(3) Uani 1 1 d . . . . .
H9 H -0.2492 0.7650 1.0492 0.032 Uiso 1 1 calc R . . . .
C4 C 0.0601(2) 0.48176(19) 0.68960(17) 0.0275(4) Uani 1 1 d . . . . .
H4 H 0.0424 0.5705 0.7115 0.033 Uiso 1 1 calc R . . . .
C3 C 0.1803(2) 0.4267(2) 0.57621(17) 0.0291(4) Uani 1 1 d . . . . .
H3 H 0.2426 0.4814 0.5216 0.035 Uiso 1 1 calc R . . . .
C10 C -0.4524(2) 0.7650(2) 1.20496(17) 0.0282(4) Uani 1 1 d . . . . .
H10 H -0.4690 0.8504 1.2326 0.034 Uiso 1 1 calc R . . . .
C2 C -0.0043(2) 0.26937(19) 0.73322(18) 0.0280(4) Uani 1 1 d . . . . .
H2 H -0.0671 0.2139 0.7848 0.034 Uiso 1 1 calc R . . . .
C7 C -0.4033(2) 0.51577(19) 1.12180(18) 0.0317(4) Uani 1 1 d . . . . .
H7 H -0.3896 0.4305 1.0956 0.038 Uiso 1 1 calc R . . . .
C8 C -0.5308(2) 0.5734(2) 1.23183(18) 0.0329(4) Uani 1 1 d . . . . .
H8 H -0.6022 0.5242 1.2792 0.039 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
Br2 C14 1.8953(15) . ?
Br1 C16 1.8952(15) . ?
O2 H2A 0.8200 . ?
O2 C13 1.3541(18) . ?
O1 H1A 0.8200 . ?
O1 C11 1.3463(19) . ?
N1 C1 1.334(2) . ?
N1 C3 1.344(2) . ?
N4 C10 1.340(2) . ?
N4 C8 1.345(2) . ?
N3 N2 1.241(2) . ?
N3 C6 1.442(2) . ?
N2 C5 1.437(2) . ?
C13 C14 1.398(2) . ?
C13 C12 1.391(2) . ?
C11 C16 1.397(2) . ?
C11 C12 1.394(2) . ?
C14 C15 1.387(2) . ?
C16 C15 1.381(2) . ?
C6 C9 1.384(2) . ?
C6 C7 1.383(2) . ?
C15 H15 0.9300 . ?
C12 H12 0.9300 . ?
C1 H1 0.9300 . ?
C1 C2 1.384(2) . ?
C5 C4 1.387(2) . ?
C5 C2 1.383(2) . ?
C9 H9 0.9300 . ?
C9 C10 1.388(2) . ?
C4 H4 0.9300 . ?
C4 C3 1.379(2) . ?
C3 H3 0.9300 . ?
C10 H10 0.9300 . ?
C2 H2 0.9300 . ?
C7 H7 0.9300 . ?
C7 C8 1.384(2) . ?
C8 H8 0.9300 . ?

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 O2 H2A 109.5 . . ?
C11 O1 H1A 109.5 . . ?
C1 N1 C3 117.20(14) . . ?
C10 N4 C8 117.19(15) . . ?
N2 N3 C6 112.82(14) . . ?
N3 N2 C5 113.72(14) . . ?
O2 C13 C14 119.39(14) . . ?
O2 C13 C12 122.04(14) . . ?
C12 C13 C14 118.56(14) . . ?
O1 C11 C16 118.84(14) . . ?
O1 C11 C12 122.94(14) . . ?
C12 C11 C16 118.20(14) . . ?
C13 C14 Br2 120.10(12) . . ?
C15 C14 Br2 119.44(11) . . ?
C15 C14 C13 120.46(14) . . ?
C11 C16 Br1 119.29(12) . . ?
C15 C16 Br1 119.78(11) . . ?
C15 C16 C11 120.92(14) . . ?
C9 C6 N3 116.45(15) . . ?
C7 C6 N3 123.97(15) . . ?
C7 C6 C9 119.58(15) . . ?
C14 C15 H15 120.0 . . ?
C16 C15 C14 120.05(14) . . ?
C16 C15 H15 120.0 . . ?
C13 C12 C11 121.78(14) . . ?
C13 C12 H12 119.1 . . ?
C11 C12 H12 119.1 . . ?
N1 C1 H1 118.4 . . ?
N1 C1 C2 123.19(16) . . ?
C2 C1 H1 118.4 . . ?
C4 C5 N2 123.96(15) . . ?
C2 C5 N2 116.55(15) . . ?
C2 C5 C4 119.46(15) . . ?
C6 C9 H9 120.8 . . ?
C6 C9 C10 118.33(16) . . ?
C10 C9 H9 120.8 . . ?
C5 C4 H4 121.2 . . ?
C3 C4 C5 117.58(16) . . ?
C3 C4 H4 121.2 . . ?
N1 C3 C4 124.04(16) . . ?
N1 C3 H3 118.0 . . ?
C4 C3 H3 118.0 . . ?
N4 C10 C9 123.25(16) . . ?
N4 C10 H10 118.4 . . ?
C9 C10 H10 118.4 . . ?
C1 C2 H2 120.7 . . ?
C5 C2 C1 118.52(16) . . ?
C5 C2 H2 120.7 . . ?
C6 C7 H7 121.0 . . ?
C6 C7 C8 117.95(16) . . ?
C8 C7 H7 121.0 . . ?
N4 C8 C7 123.70(17) . . ?
N4 C8 H8 118.1 . . ?
C7 C8 H8 118.1 . . ?

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
Br2 C14 C15 C16 178.89(12) . . . . ?
Br1 C16 C15 C14 179.60(12) . . . . ?
O2 C13 C14 Br2 1.8(2) . . . . ?
O2 C13 C14 C15 -178.02(14) . . . . ?
O2 C13 C12 C11 178.43(15) . . . . ?
O1 C11 C16 Br1 -0.4(2) . . . . ?
O1 C11 C16 C15 178.48(16) . . . . ?
O1 C11 C12 C13 -178.24(16) . . . . ?
N1 C1 C2 C5 -0.8(3) . . . . ?
N3 N2 C5 C4 -17.2(3) . . . . ?
N3 N2 C5 C2 164.66(16) . . . . ?
N3 C6 C9 C10 178.55(15) . . . . ?
N3 C6 C7 C8 -178.99(17) . . . . ?
N2 N3 C6 C9 -168.63(16) . . . . ?
N2 N3 C6 C7 10.7(2) . . . . ?
N2 C5 C4 C3 -178.71(17) . . . . ?
N2 C5 C2 C1 179.47(16) . . . . ?
C13 C14 C15 C16 -1.3(2) . . . . ?
C11 C16 C15 C14 0.7(2) . . . . ?
C14 C13 C12 C11 -1.0(2) . . . . ?
C16 C11 C12 C13 0.4(3) . . . . ?
C6 N3 N2 C5 178.23(14) . . . . ?
C6 C9 C10 N4 0.8(3) . . . . ?
C6 C7 C8 N4 0.2(3) . . . . ?
C12 C13 C14 Br2 -178.73(12) . . . . ?
C12 C13 C14 C15 1.4(2) . . . . ?
C12 C11 C16 Br1 -179.17(13) . . . . ?
C12 C11 C16 C15 -0.2(2) . . . . ?
C1 N1 C3 C4 1.0(3) . . . . ?
C5 C4 C3 N1 -0.6(3) . . . . ?
C9 C6 C7 C8 0.4(3) . . . . ?
C4 C5 C2 C1 1.2(3) . . . . ?
C3 N1 C1 C2 -0.3(3) . . . . ?
C10 N4 C8 C7 -0.3(3) . . . . ?
C2 C5 C4 C3 -0.6(3) . . . . ?
C7 C6 C9 C10 -0.8(3) . . . . ?
C8 N4 C10 C9 -0.2(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_mcg1475rt
_database_code_depnum_ccdc_archive 'CCDC 1059607'
_audit_update_record             
;
2015-04-14 deposited with the CCDC.
2016-08-23 downloaded from the CCDC.
;
_audit_creation_date             2015-04-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_shelxl_version_number           2013-3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C6 H4 Br2 O2, C10 H8 N4'
_chemical_formula_sum            'C16 H12 Br2 N4 O2'
_chemical_formula_weight         452.12
_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'
Br Br -0.2901 2.4595 '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      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                   9.0497(9)
_cell_length_b                   10.3158(10)
_cell_length_c                   10.6690(11)
_cell_angle_alpha                76.068(5)
_cell_angle_beta                 70.779(5)
_cell_angle_gamma                64.511(5)
_cell_volume                     843.19(15)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4558
_cell_measurement_temperature    290(2)
_cell_measurement_theta_max      27.56
_cell_measurement_theta_min      2.58
_exptl_absorpt_coefficient_mu    4.823
_exptl_absorpt_correction_T_max  0.561
_exptl_absorpt_correction_T_min  0.167
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2002)'
_exptl_crystal_colour            'yellowish orange'
_exptl_crystal_colour_modifier   yellow
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.781
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             444
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.12
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0190
_diffrn_reflns_av_unetI/netI     0.0238
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            9881
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.590
_diffrn_reflns_theta_min         2.820
_diffrn_ambient_temperature      290(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       'CCD rotation images, phi scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3157
_reflns_number_total             3870
_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       'Collect (Hooft, 1998)'
_computing_data_collection       'HKL Scalepack (Otwinowski and Minor, 1997)'
_computing_data_reduction        'Denzo (Otwinowski and Minor, 1997)'
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.618
_refine_diff_density_min         -0.385
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         3870
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0353
_refine_ls_R_factor_gt           0.0239
_refine_ls_restrained_S_all      1.020
_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)+(0.0268P)²+0.3254P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0558
_refine_ls_wR_factor_ref         0.0603
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C12(H12), C15(H15), C8(H8), C7(H7), C9(H9), C10(H10), C3(H3), C4(H4), C1(H1),
 C2(H2)
2.b Idealised tetrahedral OH refined as rotating group:
 O1(H1A), O2(H2A)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 0.65233(3) 0.11680(3) 1.28107(2) 0.04291(8) Uani 1 1 d . . . . .
Br2 Br 0.18125(3) 0.09674(3) 1.05218(2) 0.04970(8) Uani 1 1 d . . . . .
O1 O 0.33792(19) 0.21472(19) 1.51048(15) 0.0451(4) Uani 1 1 d . . . . .
H1A H 0.2528 0.2381 1.5727 0.068 Uiso 1 1 calc GR . . . .
O2 O -0.05759(19) 0.1907(2) 1.31621(17) 0.0614(5) Uani 1 1 d . . . . .
H2A H -0.1250 0.2290 1.3826 0.092 Uiso 1 1 calc GR . . . .
N2 N 0.3367(2) 0.5425(2) 0.93504(18) 0.0449(5) Uani 1 1 d . . . . .
C12 C 0.1382(3) 0.2003(3) 1.4172(2) 0.0401(5) Uani 1 1 d . . . . .
H12 H 0.0527 0.2285 1.4945 0.048 Uiso 1 1 calc R . . . .
N4 N 0.7121(2) 0.2990(2) 0.54199(18) 0.0428(4) Uani 1 1 d . . . . .
C15 C 0.3917(2) 0.1156(2) 1.18915(19) 0.0341(4) Uani 1 1 d . . . . .
H15 H 0.4772 0.0874 1.1118 0.041 Uiso 1 1 calc R . . . .
C16 C 0.4278(2) 0.1415(2) 1.29428(19) 0.0322(4) Uani 1 1 d . . . . .
C11 C 0.3003(2) 0.1861(2) 1.41030(19) 0.0336(4) Uani 1 1 d . . . . .
C8 C 0.6213(3) 0.2238(3) 0.6195(2) 0.0457(5) Uani 1 1 d . . . . .
H8 H 0.6420 0.1356 0.5951 0.055 Uiso 1 1 calc R . . . .
C14 C 0.2296(3) 0.1311(2) 1.19799(19) 0.0342(4) Uani 1 1 d . . . . .
N3 N 0.3363(3) 0.4428(2) 0.89152(19) 0.0495(5) Uani 1 1 d . . . . .
C13 C 0.0995(2) 0.1741(3) 1.3127(2) 0.0382(5) Uani 1 1 d . . . . .
C6 C 0.4676(3) 0.3987(2) 0.7715(2) 0.0391(5) Uani 1 1 d . . . . .
C7 C 0.4972(3) 0.2698(3) 0.7346(2) 0.0483(6) Uani 1 1 d . . . . .
H7 H 0.4352 0.2143 0.7858 0.058 Uiso 1 1 calc R . . . .
C5 C 0.2011(3) 0.5885(2) 1.0524(2) 0.0400(5) Uani 1 1 d . . . . .
C9 C 0.5595(3) 0.4806(3) 0.6919(2) 0.0469(6) Uani 1 1 d . . . . .
H9 H 0.5412 0.5690 0.7142 0.056 Uiso 1 1 calc R . . . .
C10 C 0.6789(3) 0.4255(3) 0.5786(2) 0.0501(6) Uani 1 1 d . . . . .
H10 H 0.7404 0.4801 0.5240 0.060 Uiso 1 1 calc R . . . .
C3 C 0.0455(3) 0.7639(3) 1.2050(2) 0.0478(6) Uani 1 1 d . . . . .
H3 H 0.0282 0.8495 1.2324 0.057 Uiso 1 1 calc R . . . .
C4 C 0.1766(3) 0.7140(3) 1.0937(2) 0.0452(5) Uani 1 1 d . . . . .
H4 H 0.2463 0.7645 1.0481 0.054 Uiso 1 1 calc R . . . .
C1 C -0.0297(3) 0.5724(3) 1.2334(2) 0.0544(6) Uani 1 1 d . . . . .
H1 H -0.1001 0.5231 1.2814 0.065 Uiso 1 1 calc R . . . .
C2 C 0.0970(3) 0.5144(3) 1.1233(2) 0.0519(6) Uani 1 1 d . . . . .
H2 H 0.1118 0.4286 1.0979 0.062 Uiso 1 1 calc R . . . .
N1 N -0.0568(2) 0.6948(2) 1.27456(18) 0.0485(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
Br1 C16 1.8965(19) . ?
Br2 C14 1.8934(19) . ?
O1 H1A 0.8200 . ?
O1 C11 1.350(2) . ?
O2 H2A 0.8200 . ?
O2 C13 1.346(2) . ?
N2 N3 1.228(3) . ?
N2 C5 1.440(2) . ?
C12 H12 0.9300 . ?
C12 C11 1.389(3) . ?
C12 C13 1.387(3) . ?
N4 C8 1.324(3) . ?
N4 C10 1.333(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.377(3) . ?
C15 C14 1.378(3) . ?
C16 C11 1.397(3) . ?
C8 H8 0.9300 . ?
C8 C7 1.381(3) . ?
C14 C13 1.394(3) . ?
N3 C6 1.440(2) . ?
C6 C7 1.368(3) . ?
C6 C9 1.385(3) . ?
C7 H7 0.9300 . ?
C5 C4 1.373(3) . ?
C5 C2 1.384(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.377(3) . ?
C10 H10 0.9300 . ?
C3 H3 0.9300 . ?
C3 C4 1.386(3) . ?
C3 N1 1.333(3) . ?
C4 H4 0.9300 . ?
C1 H1 0.9300 . ?
C1 C2 1.383(3) . ?
C1 N1 1.333(3) . ?
C2 H2 0.9300 . ?

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
C11 O1 H1A 109.5 . . ?
C13 O2 H2A 109.5 . . ?
N3 N2 C5 113.28(19) . . ?
C11 C12 H12 118.9 . . ?
C13 C12 H12 118.9 . . ?
C13 C12 C11 122.20(17) . . ?
C8 N4 C10 117.12(18) . . ?
C16 C15 H15 119.8 . . ?
C16 C15 C14 120.33(17) . . ?
C14 C15 H15 119.8 . . ?
C15 C16 Br1 119.65(14) . . ?
C15 C16 C11 120.53(18) . . ?
C11 C16 Br1 119.82(15) . . ?
O1 C11 C12 122.47(17) . . ?
O1 C11 C16 119.40(18) . . ?
C12 C11 C16 118.13(18) . . ?
N4 C8 H8 118.3 . . ?
N4 C8 C7 123.3(2) . . ?
C7 C8 H8 118.3 . . ?
C15 C14 Br2 119.92(14) . . ?
C15 C14 C13 120.74(18) . . ?
C13 C14 Br2 119.34(15) . . ?
N2 N3 C6 114.04(18) . . ?
O2 C13 C12 123.10(17) . . ?
O2 C13 C14 118.83(18) . . ?
C12 C13 C14 118.06(18) . . ?
C7 C6 N3 116.55(19) . . ?
C7 C6 C9 119.61(19) . . ?
C9 C6 N3 123.8(2) . . ?
C8 C7 H7 120.7 . . ?
C6 C7 C8 118.5(2) . . ?
C6 C7 H7 120.7 . . ?
C4 C5 N2 116.4(2) . . ?
C4 C5 C2 119.56(19) . . ?
C2 C5 N2 124.0(2) . . ?
C6 C9 H9 121.4 . . ?
C10 C9 C6 117.2(2) . . ?
C10 C9 H9 121.4 . . ?
N4 C10 C9 124.2(2) . . ?
N4 C10 H10 117.9 . . ?
C9 C10 H10 117.9 . . ?
C4 C3 H3 118.5 . . ?
N1 C3 H3 118.5 . . ?
N1 C3 C4 123.1(2) . . ?
C5 C4 C3 118.5(2) . . ?
C5 C4 H4 120.8 . . ?
C3 C4 H4 120.8 . . ?
C2 C1 H1 118.1 . . ?
N1 C1 H1 118.1 . . ?
N1 C1 C2 123.8(2) . . ?
C5 C2 H2 121.2 . . ?
C1 C2 C5 117.7(2) . . ?
C1 C2 H2 121.2 . . ?
C3 N1 C1 117.41(19) . . ?

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 C16 C11 O1 1.8(3) . . . . ?
Br1 C16 C11 C12 -178.81(17) . . . . ?
Br2 C14 C13 O2 -0.3(3) . . . . ?
Br2 C14 C13 C12 -179.16(18) . . . . ?
N2 N3 C6 C7 166.2(2) . . . . ?
N2 N3 C6 C9 -15.6(4) . . . . ?
N2 C5 C4 C3 178.9(2) . . . . ?
N2 C5 C2 C1 -179.2(2) . . . . ?
N4 C8 C7 C6 -0.7(4) . . . . ?
C15 C16 C11 O1 -178.2(2) . . . . ?
C15 C16 C11 C12 1.2(3) . . . . ?
C15 C14 C13 O2 178.7(2) . . . . ?
C15 C14 C13 C12 -0.1(3) . . . . ?
C16 C15 C14 Br2 179.43(16) . . . . ?
C16 C15 C14 C13 0.4(3) . . . . ?
C11 C12 C13 O2 -178.4(2) . . . . ?
C11 C12 C13 C14 0.4(4) . . . . ?
C8 N4 C10 C9 1.2(4) . . . . ?
C14 C15 C16 Br1 179.08(16) . . . . ?
C14 C15 C16 C11 -1.0(3) . . . . ?
N3 N2 C5 C4 -169.6(2) . . . . ?
N3 N2 C5 C2 10.2(3) . . . . ?
N3 C6 C7 C8 179.5(2) . . . . ?
N3 C6 C9 C10 -178.7(2) . . . . ?
C13 C12 C11 O1 178.4(2) . . . . ?
C13 C12 C11 C16 -1.0(4) . . . . ?
C6 C9 C10 N4 -0.7(4) . . . . ?
C7 C6 C9 C10 -0.6(4) . . . . ?
C5 N2 N3 C6 178.00(19) . . . . ?
C9 C6 C7 C8 1.3(4) . . . . ?
C10 N4 C8 C7 -0.5(4) . . . . ?
C4 C5 C2 C1 0.6(4) . . . . ?
C4 C3 N1 C1 -0.1(4) . . . . ?
C2 C5 C4 C3 -1.0(4) . . . . ?
C2 C1 N1 C3 -0.2(4) . . . . ?
N1 C3 C4 C5 0.7(4) . . . . ?
N1 C1 C2 C5 0.0(4) . . . . ?

_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_mcg1476lt
_database_code_depnum_ccdc_archive 'CCDC 1059608'
_audit_update_record             
;
2015-04-14 deposited with the CCDC.
2016-08-23 downloaded from the CCDC.
;
_audit_creation_date             2015-04-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_shelxl_version_number           2013-3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         '0.5(C6 H4 I2 O2), 0.5(C10 H8 N4)'
_chemical_formula_sum            'C8 H6 I N2 O'
_chemical_formula_weight         273.05
_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'

_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                   9.2387(9)
_cell_length_b                   10.4970(10)
_cell_length_c                   10.8284(11)
_cell_angle_alpha                88.215(5)
_cell_angle_beta                 69.551(5)
_cell_angle_gamma                64.302(5)
_cell_volume                     877.58(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9020
_cell_measurement_temperature    190(2)
_cell_measurement_theta_max      29.01
_cell_measurement_theta_min      2.551
_exptl_absorpt_coefficient_mu    3.600
_exptl_absorpt_correction_T_max  0.750
_exptl_absorpt_correction_T_min  0.552
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2002)'
_exptl_crystal_colour            orange-yellow
_exptl_crystal_density_diffrn    2.067
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       lath-like
_exptl_crystal_F_000             516
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.08
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0182
_diffrn_reflns_av_unetI/netI     0.0186
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            12709
_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         29.008
_diffrn_reflns_theta_min         3.179
_diffrn_ambient_temperature      190(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       'CCD rotation images, phi scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4310
_reflns_number_total             4671
_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       'HKL Scalepack (Otwinowski and Minor, 1997)'
_computing_data_collection       'Collect (Hooft, 1998)'
_computing_data_reduction        'Denzo (Otwinowski and Minor, 1997)'
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.999
_refine_diff_density_min         -0.754
_refine_diff_density_rms         0.079
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         4671
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0198
_refine_ls_R_factor_gt           0.0175
_refine_ls_restrained_S_all      1.072
_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)+(0.0145P)²+0.6891P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0408
_refine_ls_wR_factor_ref         0.0421
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C8(H8), C12(H12), C9(H9), C15(H15), C3(H3), C10(H10), C7(H7), C2(H2), C4(H4),
 C1(H1)
2.b Idealised tetrahedral OH refined as rotating group:
 O2(H2A), O1(H1A)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
I2 I -0.28288(2) 0.11480(2) 0.72076(2) 0.02351(4) Uani 1 1 d . . . . .
I1 I 0.24332(2) 0.08375(2) 0.94216(2) 0.02674(4) Uani 1 1 d . . . . .
O2 O -0.05887(18) 0.22925(17) 0.49509(13) 0.0270(3) Uani 1 1 d . . . . .
H2A H 0.0049 0.2475 0.4307 0.041 Uiso 1 1 calc GR . . . .
O1 O 0.3628(2) 0.1985(2) 0.67307(15) 0.0376(4) Uani 1 1 d . . . . .
H1A H 0.3944 0.2324 0.6055 0.056 Uiso 1 1 calc GR . . . .
N3 N 0.6386(2) 0.52624(19) 0.05875(16) 0.0281(4) Uani 1 1 d . . . . .
N1 N 0.4938(2) 0.30156(19) 0.45401(16) 0.0259(3) Uani 1 1 d . . . . .
N4 N 0.8807(2) 0.6733(2) -0.28092(16) 0.0291(4) Uani 1 1 d . . . . .
N2 N 0.7366(2) 0.4342(2) 0.10529(18) 0.0322(4) Uani 1 1 d . . . . .
C14 C -0.0666(2) 0.14449(19) 0.70206(17) 0.0188(3) Uani 1 1 d . . . . .
C16 C 0.1448(2) 0.1304(2) 0.79059(17) 0.0199(3) Uani 1 1 d . . . . .
C11 C 0.2253(2) 0.1798(2) 0.67857(18) 0.0231(4) Uani 1 1 d . . . . .
C6 C 0.7290(3) 0.5698(2) -0.05839(18) 0.0253(4) Uani 1 1 d . . . . .
C8 C 0.9764(3) 0.5593(2) -0.2359(2) 0.0321(4) Uani 1 1 d . . . . .
H8 H 1.0957 0.5148 -0.2815 0.039 Uiso 1 1 calc R . . . .
C12 C 0.1568(2) 0.2114(2) 0.57914(18) 0.0239(4) Uani 1 1 d . . . . .
H12 H 0.2097 0.2437 0.5040 0.029 Uiso 1 1 calc R . . . .
C13 C 0.0109(2) 0.1958(2) 0.58952(17) 0.0198(3) Uani 1 1 d . . . . .
C9 C 0.6271(3) 0.6870(2) -0.10368(19) 0.0275(4) Uani 1 1 d . . . . .
H9 H 0.5072 0.7322 -0.0610 0.033 Uiso 1 1 calc R . . . .
C5 C 0.6468(3) 0.3938(2) 0.22459(18) 0.0252(4) Uani 1 1 d . . . . .
C15 C 0.0000(2) 0.11387(19) 0.80225(17) 0.0196(3) Uani 1 1 d . . . . .
H15 H -0.0530 0.0820 0.8777 0.024 Uiso 1 1 calc R . . . .
C3 C 0.4039(3) 0.4252(2) 0.4175(2) 0.0302(4) Uani 1 1 d . . . . .
H3 H 0.2883 0.4800 0.4715 0.036 Uiso 1 1 calc R . . . .
C10 C 0.7092(3) 0.7352(2) -0.2147(2) 0.0297(4) Uani 1 1 d . . . . .
H10 H 0.6413 0.8147 -0.2446 0.036 Uiso 1 1 calc R . . . .
C7 C 0.9076(3) 0.5039(2) -0.1252(2) 0.0307(4) Uani 1 1 d . . . . .
H7 H 0.9787 0.4252 -0.0967 0.037 Uiso 1 1 calc R . . . .
C2 C 0.7431(3) 0.2677(2) 0.2624(2) 0.0310(4) Uani 1 1 d . . . . .
H2 H 0.8601 0.2129 0.2122 0.037 Uiso 1 1 calc R . . . .
C4 C 0.4735(3) 0.4759(2) 0.3036(2) 0.0289(4) Uani 1 1 d . . . . .
H4 H 0.4066 0.5619 0.2809 0.035 Uiso 1 1 calc R . . . .
C1 C 0.6606(3) 0.2246(2) 0.3776(2) 0.0294(4) Uani 1 1 d . . . . .
H1 H 0.7243 0.1387 0.4023 0.035 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
I2 C14 2.0934(17) . ?
I1 C16 2.0906(17) . ?
O2 H2A 0.8200 . ?
O2 C13 1.352(2) . ?
O1 H1A 0.8200 . ?
O1 C11 1.349(2) . ?
N3 N2 1.240(3) . ?
N3 C6 1.439(2) . ?
N1 C3 1.339(3) . ?
N1 C1 1.335(3) . ?
N4 C8 1.341(3) . ?
N4 C10 1.337(3) . ?
N2 C5 1.435(2) . ?
C14 C13 1.404(2) . ?
C14 C15 1.390(2) . ?
C16 C11 1.399(2) . ?
C16 C15 1.384(2) . ?
C11 C12 1.394(3) . ?
C6 C9 1.387(3) . ?
C6 C7 1.390(3) . ?
C8 H8 0.9300 . ?
C8 C7 1.387(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.393(2) . ?
C9 H9 0.9300 . ?
C9 C10 1.391(3) . ?
C5 C2 1.383(3) . ?
C5 C4 1.389(3) . ?
C15 H15 0.9300 . ?
C3 H3 0.9300 . ?
C3 C4 1.386(3) . ?
C10 H10 0.9300 . ?
C7 H7 0.9300 . ?
C2 H2 0.9300 . ?
C2 C1 1.393(3) . ?
C4 H4 0.9300 . ?
C1 H1 0.9300 . ?

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 O2 H2A 109.5 . . ?
C11 O1 H1A 109.5 . . ?
N2 N3 C6 113.23(17) . . ?
C1 N1 C3 118.02(17) . . ?
C10 N4 C8 117.28(17) . . ?
N3 N2 C5 113.41(17) . . ?
C13 C14 I2 120.52(12) . . ?
C15 C14 I2 119.69(12) . . ?
C15 C14 C13 119.78(15) . . ?
C11 C16 I1 119.37(13) . . ?
C15 C16 I1 120.00(12) . . ?
C15 C16 C11 120.62(16) . . ?
O1 C11 C16 118.68(16) . . ?
O1 C11 C12 122.81(16) . . ?
C12 C11 C16 118.48(16) . . ?
C9 C6 N3 116.04(18) . . ?
C9 C6 C7 119.50(17) . . ?
C7 C6 N3 124.45(18) . . ?
N4 C8 H8 118.1 . . ?
N4 C8 C7 123.8(2) . . ?
C7 C8 H8 118.1 . . ?
C11 C12 H12 119.2 . . ?
C13 C12 C11 121.61(16) . . ?
C13 C12 H12 119.2 . . ?
O2 C13 C14 118.98(15) . . ?
O2 C13 C12 122.07(16) . . ?
C12 C13 C14 118.95(16) . . ?
C6 C9 H9 121.0 . . ?
C6 C9 C10 118.08(19) . . ?
C10 C9 H9 121.0 . . ?
C2 C5 N2 116.62(18) . . ?
C2 C5 C4 119.68(17) . . ?
C4 C5 N2 123.67(18) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 C14 120.53(16) . . ?
C16 C15 H15 119.7 . . ?
N1 C3 H3 118.2 . . ?
N1 C3 C4 123.61(19) . . ?
C4 C3 H3 118.2 . . ?
N4 C10 C9 123.5(2) . . ?
N4 C10 H10 118.2 . . ?
C9 C10 H10 118.2 . . ?
C6 C7 H7 121.1 . . ?
C8 C7 C6 117.8(2) . . ?
C8 C7 H7 121.1 . . ?
C5 C2 H2 120.8 . . ?
C5 C2 C1 118.42(19) . . ?
C1 C2 H2 120.8 . . ?
C5 C4 H4 121.2 . . ?
C3 C4 C5 117.59(19) . . ?
C3 C4 H4 121.2 . . ?
N1 C1 C2 122.65(19) . . ?
N1 C1 H1 118.7 . . ?
C2 C1 H1 118.7 . . ?

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
I2 C14 C13 O2 1.7(2) . . . . ?
I2 C14 C13 C12 -178.68(14) . . . . ?
I2 C14 C15 C16 178.86(14) . . . . ?
I1 C16 C11 O1 -1.3(3) . . . . ?
I1 C16 C11 C12 -179.49(15) . . . . ?
I1 C16 C15 C14 -179.96(14) . . . . ?
O1 C11 C12 C13 -177.7(2) . . . . ?
N3 N2 C5 C2 163.2(2) . . . . ?
N3 N2 C5 C4 -18.8(3) . . . . ?
N3 C6 C9 C10 178.44(18) . . . . ?
N3 C6 C7 C8 -179.1(2) . . . . ?
N1 C3 C4 C5 -0.7(3) . . . . ?
N4 C8 C7 C6 0.8(3) . . . . ?
N2 N3 C6 C9 -170.67(19) . . . . ?
N2 N3 C6 C7 8.4(3) . . . . ?
N2 C5 C2 C1 -179.9(2) . . . . ?
N2 C5 C4 C3 -178.9(2) . . . . ?
C16 C11 C12 C13 0.4(3) . . . . ?
C11 C16 C15 C14 0.7(3) . . . . ?
C11 C12 C13 O2 178.46(19) . . . . ?
C11 C12 C13 C14 -1.1(3) . . . . ?
C6 N3 N2 C5 178.10(17) . . . . ?
C6 C9 C10 N4 0.9(3) . . . . ?
C8 N4 C10 C9 -0.3(3) . . . . ?
C13 C14 C15 C16 -1.5(3) . . . . ?
C9 C6 C7 C8 -0.1(3) . . . . ?
C5 C2 C1 N1 -1.4(3) . . . . ?
C15 C14 C13 O2 -177.94(17) . . . . ?
C15 C14 C13 C12 1.7(3) . . . . ?
C15 C16 C11 O1 178.03(19) . . . . ?
C15 C16 C11 C12 -0.2(3) . . . . ?
C3 N1 C1 C2 -0.2(3) . . . . ?
C10 N4 C8 C7 -0.6(3) . . . . ?
C7 C6 C9 C10 -0.6(3) . . . . ?
C2 C5 C4 C3 -1.0(3) . . . . ?
C4 C5 C2 C1 2.0(3) . . . . ?
C1 N1 C3 C4 1.3(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_mcg1476rt
_database_code_depnum_ccdc_archive 'CCDC 1059609'
_audit_update_record             
;
2015-04-14 deposited with the CCDC.
2016-08-23 downloaded from the CCDC.
;
_audit_creation_date             2015-04-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_shelxl_version_number           2013-3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C6 H4 I2 O2, C10 H8 N4'
_chemical_formula_sum            'C16 H12 I2 N4 O2'
_chemical_formula_weight         546.10
_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'
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'

_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                   9.2547(9)
_cell_length_b                   10.6163(11)
_cell_length_c                   10.8929(11)
_cell_angle_alpha                74.976(5)
_cell_angle_beta                 69.459(5)
_cell_angle_gamma                64.157(5)
_cell_volume                     894.76(16)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    8082
_cell_measurement_temperature    290(2)
_cell_measurement_theta_max      29.04
_cell_measurement_theta_min      2.542
_exptl_absorpt_coefficient_mu    3.531
_exptl_absorpt_correction_T_max  0.754
_exptl_absorpt_correction_T_min  0.558
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2002)'
_exptl_crystal_colour            orange-yellow
_exptl_crystal_density_diffrn    2.027
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       lath-like
_exptl_crystal_F_000             516
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.08
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0194
_diffrn_reflns_av_unetI/netI     0.0187
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            14106
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         29.063
_diffrn_reflns_theta_min         2.629
_diffrn_ambient_temperature      290(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       'CCD rotation images, phi scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4178
_reflns_number_total             4772
_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       'HKL Scalepack (Otwinowski and Minor, 1997)'
_computing_data_collection       'Collect (Hooft, 1998)'
_computing_data_reduction        'Denzo (Otwinowski and Minor, 1997)'
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.423
_refine_diff_density_min         -1.132
_refine_diff_density_rms         0.078
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         4772
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0288
_refine_ls_R_factor_gt           0.0235
_refine_ls_restrained_S_all      1.046
_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)+(0.0153P)²+1.1347P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0509
_refine_ls_wR_factor_ref         0.0540
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C12(H12), C15(H15), C3(H3), C9(H9), C10(H10), C4(H4), C1(H1), C2(H2), C8(H8),
 C7(H7)
2.b Idealised tetrahedral OH refined as rotating group:
 O2(H2A), O1(H1A)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
I2 I 1.16634(2) 0.11576(2) 0.27973(2) 0.04033(5) Uani 1 1 d . . . . .
I1 I 0.67293(2) 0.08348(2) 0.05994(2) 0.04651(6) Uani 1 1 d . . . . .
O2 O 0.8298(2) 0.2290(2) 0.50519(18) 0.0453(5) Uani 1 1 d . . . . .
H2A H 0.7482 0.2470 0.5697 0.068 Uiso 1 1 calc GR . . . .
O1 O 0.4399(2) 0.1972(3) 0.3292(2) 0.0619(7) Uani 1 1 d . . . . .
H1A H 0.3752 0.2283 0.3982 0.093 Uiso 1 1 calc GR . . . .
N1 N 0.2054(3) 0.3012(3) 0.5485(2) 0.0446(5) Uani 1 1 d . . . . .
N4 N -0.5539(3) 0.6722(3) 1.2807(2) 0.0491(6) Uani 1 1 d . . . . .
N3 N -0.1668(3) 0.5267(3) 0.9416(2) 0.0484(6) Uani 1 1 d . . . . .
N2 N -0.1688(3) 0.4329(3) 0.8972(3) 0.0533(6) Uani 1 1 d . . . . .
C16 C 0.7245(3) 0.1299(3) 0.2113(2) 0.0319(5) Uani 1 1 d . . . . .
C13 C 0.7931(3) 0.1954(3) 0.4115(2) 0.0326(5) Uani 1 1 d . . . . .
C14 C 0.9212(3) 0.1448(3) 0.2987(2) 0.0305(5) Uani 1 1 d . . . . .
C11 C 0.5954(3) 0.1791(3) 0.3231(2) 0.0377(6) Uani 1 1 d . . . . .
C12 C 0.6325(3) 0.2108(3) 0.4216(2) 0.0396(6) Uani 1 1 d . . . . .
H12 H 0.5473 0.2433 0.4966 0.048 Uiso 1 1 calc R . . . .
C5 C -0.0387(3) 0.3932(3) 0.7769(3) 0.0423(6) Uani 1 1 d . . . . .
C15 C 0.8849(3) 0.1140(3) 0.1995(2) 0.0326(5) Uani 1 1 d . . . . .
H15 H 0.9696 0.0822 0.1240 0.039 Uiso 1 1 calc R . . . .
C6 C -0.3005(3) 0.5698(3) 1.0585(3) 0.0432(6) Uani 1 1 d . . . . .
C3 C 0.1705(4) 0.4239(3) 0.5849(3) 0.0523(8) Uani 1 1 d . . . . .
H3 H 0.2300 0.4789 0.5308 0.063 Uiso 1 1 calc R . . . .
C9 C -0.3179(4) 0.6876(3) 1.1025(3) 0.0473(7) Uani 1 1 d . . . . .
H9 H -0.2450 0.7339 1.0591 0.057 Uiso 1 1 calc R . . . .
C10 C -0.4477(4) 0.7353(3) 1.2138(3) 0.0492(7) Uani 1 1 d . . . . .
H10 H -0.4608 0.8156 1.2429 0.059 Uiso 1 1 calc R . . . .
C4 C 0.0508(4) 0.4744(3) 0.6986(3) 0.0495(7) Uani 1 1 d . . . . .
H4 H 0.0313 0.5602 0.7214 0.059 Uiso 1 1 calc R . . . .
C1 C 0.1170(4) 0.2253(3) 0.6248(3) 0.0501(7) Uani 1 1 d . . . . .
H1 H 0.1397 0.1395 0.6002 0.060 Uiso 1 1 calc R . . . .
C2 C -0.0079(4) 0.2680(3) 0.7396(3) 0.0529(8) Uani 1 1 d . . . . .
H2 H -0.0690 0.2131 0.7900 0.063 Uiso 1 1 calc R . . . .
C8 C -0.5347(4) 0.5580(4) 1.2367(3) 0.0548(8) Uani 1 1 d . . . . .
H8 H -0.6089 0.5134 1.2825 0.066 Uiso 1 1 calc R . . . .
C7 C -0.4103(4) 0.5024(3) 1.1263(3) 0.0526(8) Uani 1 1 d . . . . .
H7 H -0.4008 0.4226 1.0988 0.063 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
I2 C14 2.093(2) . ?
I1 C16 2.090(2) . ?
O2 H2A 0.8200 . ?
O2 C13 1.349(3) . ?
O1 H1A 0.8200 . ?
O1 C11 1.346(3) . ?
N1 C3 1.330(4) . ?
N1 C1 1.328(4) . ?
N4 C10 1.328(4) . ?
N4 C8 1.336(4) . ?
N3 N2 1.224(4) . ?
N3 C6 1.436(3) . ?
N2 C5 1.442(3) . ?
C16 C11 1.396(3) . ?
C16 C15 1.380(3) . ?
C13 C14 1.403(3) . ?
C13 C12 1.390(3) . ?
C14 C15 1.386(3) . ?
C11 C12 1.389(4) . ?
C12 H12 0.9300 . ?
C5 C4 1.380(4) . ?
C5 C2 1.372(4) . ?
C15 H15 0.9300 . ?
C6 C9 1.379(4) . ?
C6 C7 1.387(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.382(4) . ?
C9 H9 0.9300 . ?
C9 C10 1.391(4) . ?
C10 H10 0.9300 . ?
C4 H4 0.9300 . ?
C1 H1 0.9300 . ?
C1 C2 1.389(4) . ?
C2 H2 0.9300 . ?
C8 H8 0.9300 . ?
C8 C7 1.387(4) . ?
C7 H7 0.9300 . ?

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 O2 H2A 109.5 . . ?
C11 O1 H1A 109.5 . . ?
C1 N1 C3 117.6(2) . . ?
C10 N4 C8 117.6(2) . . ?
N2 N3 C6 113.5(3) . . ?
N3 N2 C5 113.6(3) . . ?
C11 C16 I1 119.55(18) . . ?
C15 C16 I1 120.04(16) . . ?
C15 C16 C11 120.4(2) . . ?
O2 C13 C14 119.0(2) . . ?
O2 C13 C12 122.4(2) . . ?
C12 C13 C14 118.6(2) . . ?
C13 C14 I2 120.27(17) . . ?
C15 C14 I2 119.98(16) . . ?
C15 C14 C13 119.8(2) . . ?
O1 C11 C16 118.6(2) . . ?
O1 C11 C12 122.9(2) . . ?
C12 C11 C16 118.5(2) . . ?
C13 C12 H12 119.0 . . ?
C11 C12 C13 121.9(2) . . ?
C11 C12 H12 119.0 . . ?
C4 C5 N2 124.0(3) . . ?
C2 C5 N2 116.4(3) . . ?
C2 C5 C4 119.6(2) . . ?
C16 C15 C14 120.8(2) . . ?
C16 C15 H15 119.6 . . ?
C14 C15 H15 119.6 . . ?
C9 C6 N3 115.9(3) . . ?
C9 C6 C7 119.5(2) . . ?
C7 C6 N3 124.6(3) . . ?
N1 C3 H3 118.1 . . ?
N1 C3 C4 123.8(3) . . ?
C4 C3 H3 118.1 . . ?
C6 C9 H9 120.9 . . ?
C6 C9 C10 118.1(3) . . ?
C10 C9 H9 120.9 . . ?
N4 C10 C9 123.4(3) . . ?
N4 C10 H10 118.3 . . ?
C9 C10 H10 118.3 . . ?
C5 C4 C3 117.7(3) . . ?
C5 C4 H4 121.2 . . ?
C3 C4 H4 121.2 . . ?
N1 C1 H1 118.5 . . ?
N1 C1 C2 123.0(3) . . ?
C2 C1 H1 118.5 . . ?
C5 C2 C1 118.3(3) . . ?
C5 C2 H2 120.8 . . ?
C1 C2 H2 120.8 . . ?
N4 C8 H8 118.2 . . ?
N4 C8 C7 123.6(3) . . ?
C7 C8 H8 118.2 . . ?
C6 C7 H7 121.1 . . ?
C8 C7 C6 117.8(3) . . ?
C8 C7 H7 121.1 . . ?

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
I2 C14 C15 C16 178.76(19) . . . . ?
I1 C16 C11 O1 -0.9(4) . . . . ?
I1 C16 C11 C12 -179.3(2) . . . . ?
I1 C16 C15 C14 179.76(19) . . . . ?
O2 C13 C14 I2 2.0(3) . . . . ?
O2 C13 C14 C15 -178.0(2) . . . . ?
O2 C13 C12 C11 178.4(3) . . . . ?
O1 C11 C12 C13 -178.0(3) . . . . ?
N1 C3 C4 C5 -1.1(5) . . . . ?
N1 C1 C2 C5 -1.3(5) . . . . ?
N4 C8 C7 C6 -0.1(5) . . . . ?
N3 N2 C5 C4 -16.9(5) . . . . ?
N3 N2 C5 C2 164.6(3) . . . . ?
N3 C6 C9 C10 178.7(3) . . . . ?
N3 C6 C7 C8 -179.1(3) . . . . ?
N2 N3 C6 C9 -171.5(3) . . . . ?
N2 N3 C6 C7 7.8(4) . . . . ?
N2 C5 C4 C3 -179.1(3) . . . . ?
N2 C5 C2 C1 -179.7(3) . . . . ?
C16 C11 C12 C13 0.2(4) . . . . ?
C13 C14 C15 C16 -1.2(4) . . . . ?
C14 C13 C12 C11 -0.7(4) . . . . ?
C11 C16 C15 C14 0.8(4) . . . . ?
C12 C13 C14 I2 -178.8(2) . . . . ?
C12 C13 C14 C15 1.2(4) . . . . ?
C15 C16 C11 O1 178.1(3) . . . . ?
C15 C16 C11 C12 -0.3(4) . . . . ?
C6 N3 N2 C5 177.7(2) . . . . ?
C6 C9 C10 N4 1.0(5) . . . . ?
C3 N1 C1 C2 -0.4(5) . . . . ?
C9 C6 C7 C8 0.3(5) . . . . ?
C10 N4 C8 C7 0.4(5) . . . . ?
C4 C5 C2 C1 1.7(5) . . . . ?
C1 N1 C3 C4 1.6(5) . . . . ?
C2 C5 C4 C3 -0.6(5) . . . . ?
C8 N4 C10 C9 -0.8(5) . . . . ?
C7 C6 C9 C10 -0.7(5) . . . . ?

_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_mcg1522lt
_database_code_depnum_ccdc_archive 'CCDC 1059610'
_audit_update_record             
;
2015-04-14 deposited with the CCDC.
2016-08-23 downloaded from the CCDC.
;
_audit_creation_date             2015-04-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_shelxl_version_number           2013-3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C10 H8 N4'
_chemical_formula_sum            'C10 H8 N4'
_chemical_formula_weight         184.20
_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'

_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                   3.7762(4)
_cell_length_b                   5.8688(7)
_cell_length_c                   10.3157(12)
_cell_angle_alpha                90.165(5)
_cell_angle_beta                 95.411(5)
_cell_angle_gamma                99.256(5)
_cell_volume                     224.59(4)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    3245
_cell_measurement_temperature    190(2)
_cell_measurement_theta_max      25.32
_cell_measurement_theta_min      1.00
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.996
_exptl_absorpt_correction_T_min  0.989
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2002)'
_exptl_crystal_colour            yellow-orange
_exptl_crystal_density_diffrn    1.362
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate-like
_exptl_crystal_F_000             96
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.04
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0251
_diffrn_reflns_av_unetI/netI     0.0261
_diffrn_reflns_Laue_measured_fraction_full 0.933
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -2
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            3229
_diffrn_reflns_point_group_measured_fraction_full 0.933
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         25.392
_diffrn_reflns_theta_min         1.983
_diffrn_ambient_temperature      190(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.933
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       'CCD rotation images, phi scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                668
_reflns_number_total             827
_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       'HKL Scalepack (Otwinowski and Minor, 1997)'
_computing_data_collection       'Collect (Hooft, 1998)'
_computing_data_reduction        'Denzo (Otwinowski and Minor, 1997)'
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.171
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       0.030(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     81
_refine_ls_number_reflns         827
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0477
_refine_ls_R_factor_gt           0.0366
_refine_ls_restrained_S_all      1.059
_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)+(0.0517P)²+0.0345P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0897
_refine_ls_wR_factor_ref         0.1012
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     ?
_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 0.5041(3) 0.60320(19) 0.51595(11) 0.0273(4) Uani 1 1 d . . . . .
N1 N 0.3097(3) 0.7249(2) 0.90400(12) 0.0317(4) Uani 1 1 d . . . . .
C5 C 0.4301(4) 0.6340(2) 0.64833(13) 0.0229(4) Uani 1 1 d . . . . .
C4 C 0.2659(4) 0.4600(3) 0.72351(14) 0.0262(4) Uani 1 1 d . . . . .
H4 H 0.189(4) 0.309(3) 0.6909(15) 0.032(4) Uiso 1 1 d . . . . .
C2 C 0.5258(4) 0.8547(3) 0.70117(15) 0.0294(4) Uani 1 1 d . . . . .
H2 H 0.644(4) 0.984(3) 0.6467(14) 0.033(4) Uiso 1 1 d . . . . .
C3 C 0.2109(4) 0.5144(3) 0.84944(15) 0.0301(4) Uani 1 1 d . . . . .
H3 H 0.100(5) 0.398(3) 0.9037(15) 0.037(4) Uiso 1 1 d . . . . .
C1 C 0.4651(4) 0.8903(3) 0.82959(15) 0.0325(4) Uani 1 1 d . . . . .
H1 H 0.537(4) 1.044(3) 0.8712(16) 0.041(5) 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
N2 N2 1.249(2) 2_666 ?
N2 C5 1.4361(18) . ?
N1 C3 1.338(2) . ?
N1 C1 1.335(2) . ?
C5 C4 1.386(2) . ?
C5 C2 1.383(2) . ?
C4 H4 0.939(16) . ?
C4 C3 1.379(2) . ?
C2 H2 1.015(15) . ?
C2 C1 1.386(2) . ?
C3 H3 0.953(17) . ?
C1 H1 0.983(18) . ?

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
N2 N2 C5 113.43(15) 2_666 . ?
C1 N1 C3 116.91(13) . . ?
C4 C5 N2 124.37(13) . . ?
C2 C5 N2 116.55(13) . . ?
C2 C5 C4 119.07(13) . . ?
C5 C4 H4 122.2(10) . . ?
C3 C4 C5 118.17(14) . . ?
C3 C4 H4 119.7(10) . . ?
C5 C2 H2 119.8(9) . . ?
C5 C2 C1 118.22(14) . . ?
C1 C2 H2 122.0(9) . . ?
N1 C3 C4 123.92(15) . . ?
N1 C3 H3 116.0(9) . . ?
C4 C3 H3 120.0(9) . . ?
N1 C1 C2 123.67(14) . . ?
N1 C1 H1 115.9(9) . . ?
C2 C1 H1 120.4(9) . . ?

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 N2 C5 C4 -17.8(2) 2_666 . . . ?
N2 N2 C5 C2 163.46(15) 2_666 . . . ?
N2 C5 C4 C3 -179.91(12) . . . . ?
N2 C5 C2 C1 -178.74(12) . . . . ?
C5 C4 C3 N1 -0.7(2) . . . . ?
C5 C2 C1 N1 -2.0(2) . . . . ?
C4 C5 C2 C1 2.4(2) . . . . ?
C2 C5 C4 C3 -1.2(2) . . . . ?
C3 N1 C1 C2 0.3(2) . . . . ?
C1 N1 C3 C4 1.1(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_mcg1522
_database_code_depnum_ccdc_archive 'CCDC 1059611'
_audit_update_record             
;
2015-04-14 deposited with the CCDC.
2016-08-23 downloaded from the CCDC.
;
_audit_creation_date             2015-04-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_shelxl_version_number           2013-3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C10 H8 N4'
_chemical_formula_sum            'C10 H8 N4'
_chemical_formula_weight         184.20
_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'

_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                   3.8373(6)
_cell_length_b                   5.9282(7)
_cell_length_c                   10.3247(14)
_cell_angle_alpha                90.671(7)
_cell_angle_beta                 95.227(8)
_cell_angle_gamma                100.693(8)
_cell_volume                     229.73(6)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    753
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      25.35
_cell_measurement_theta_min      1.00
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  0.997
_exptl_absorpt_correction_T_min  0.976
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2002)'
_exptl_crystal_colour            yellow-orange
_exptl_crystal_density_diffrn    1.331
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate-like
_exptl_crystal_F_000             96
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.04
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0386
_diffrn_reflns_av_unetI/netI     0.0548
_diffrn_reflns_Laue_measured_fraction_full 0.914
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            1410
_diffrn_reflns_point_group_measured_fraction_full 0.914
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         25.409
_diffrn_reflns_theta_min         1.982
_diffrn_ambient_temperature      298(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.914
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       'CCD rotation images, phi scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                523
_reflns_number_total             827
_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       'HKL Scalepack (Otwinowski and Minor, 1997)'
_computing_data_collection       'Collect (Hooft, 1998)'
_computing_data_reduction        'Denzo (Otwinowski and Minor, 1997)'
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.212
_refine_diff_density_min         -0.145
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       2.5(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     81
_refine_ls_number_reflns         827
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0953
_refine_ls_R_factor_gt           0.0582
_refine_ls_restrained_S_all      1.073
_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)+(0.0940P)²+0.0106P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1378
_refine_ls_wR_factor_ref         0.1709
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     ?
_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 0.5105(5) 0.6015(3) 0.51695(17) 0.0572(7) Uani 1 1 d . . . . .
N1 N 0.3125(6) 0.7245(4) 0.90306(18) 0.0670(8) Uani 1 1 d . . . . .
C5 C 0.4343(6) 0.6330(4) 0.6486(2) 0.0521(7) Uani 1 1 d . . . . .
C4 C 0.2715(7) 0.4606(4) 0.7241(2) 0.0578(8) Uani 1 1 d . . . . .
H4 H 0.202(7) 0.311(4) 0.694(2) 0.066(7) Uiso 1 1 d . . . . .
C3 C 0.2150(7) 0.5145(4) 0.8493(2) 0.0632(8) Uani 1 1 d . . . . .
H3 H 0.111(8) 0.399(5) 0.907(3) 0.086(9) Uiso 1 1 d . . . . .
C2 C 0.5290(8) 0.8522(4) 0.7016(2) 0.0630(8) Uani 1 1 d . . . . .
H2 H 0.640(7) 0.977(4) 0.650(2) 0.077(8) Uiso 1 1 d . . . . .
C1 C 0.4675(8) 0.8886(5) 0.8290(2) 0.0703(9) Uani 1 1 d . . . . .
H1 H 0.549(8) 1.044(5) 0.873(3) 0.094(9) 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
N2 N2 1.235(3) 2_666 ?
N2 C5 1.433(3) . ?
N1 C3 1.331(3) . ?
N1 C1 1.331(3) . ?
C5 C4 1.384(3) . ?
C5 C2 1.375(3) . ?
C4 H4 0.92(3) . ?
C4 C3 1.373(3) . ?
C3 H3 0.96(3) . ?
C2 H2 0.97(3) . ?
C2 C1 1.379(3) . ?
C1 H1 1.01(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
N2 N2 C5 114.0(2) 2_666 . ?
C1 N1 C3 117.0(2) . . ?
C4 C5 N2 124.8(2) . . ?
C2 C5 N2 116.7(2) . . ?
C2 C5 C4 118.5(2) . . ?
C5 C4 H4 122.3(16) . . ?
C3 C4 C5 118.8(2) . . ?
C3 C4 H4 118.9(16) . . ?
N1 C3 C4 123.5(2) . . ?
N1 C3 H3 114.6(16) . . ?
C4 C3 H3 121.9(16) . . ?
C5 C2 H2 120.2(15) . . ?
C5 C2 C1 118.5(2) . . ?
C1 C2 H2 121.3(16) . . ?
N1 C1 C2 123.7(2) . . ?
N1 C1 H1 115.5(15) . . ?
C2 C1 H1 120.7(16) . . ?

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 N2 C5 C4 -14.7(4) 2_666 . . . ?
N2 N2 C5 C2 165.8(3) 2_666 . . . ?
N2 C5 C4 C3 179.8(2) . . . . ?
N2 C5 C2 C1 -178.5(2) . . . . ?
C5 C4 C3 N1 -0.8(4) . . . . ?
C5 C2 C1 N1 -1.8(4) . . . . ?
C4 C5 C2 C1 2.0(4) . . . . ?
C3 N1 C1 C2 0.3(4) . . . . ?
C2 C5 C4 C3 -0.8(4) . . . . ?
C1 N1 C3 C4 1.0(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
