# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 1543798'
_audit_update_record             
;
2017-04-13 deposited with the CCDC.
2017-08-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C36 H28 N4 O6'
_chemical_formula_weight         612.62

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   28.115(4)
_cell_length_b                   4.5482(5)
_cell_length_c                   23.970(4)
_cell_angle_alpha                90
_cell_angle_beta                 93.065(11)
_cell_angle_gamma                90
_cell_volume                     3060.7(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    458
_cell_measurement_theta_min      3.7700
_cell_measurement_theta_max      19.7540

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_F_000             1280
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.090
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.092
_shelx_estimated_absorpt_T_min   0.992
_shelx_estimated_absorpt_T_max   0.998
_exptl_absorpt_correction_T_min  0.25756
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;


_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Micro-Focus (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'OXFORD DIFFRACTION SUPER NOVA'
_diffrn_measurement_method       ω/q-scan
_diffrn_detector_area_resol_mean 15.9948
_diffrn_reflns_number            11501
_diffrn_reflns_av_unetI/netI     0.1354
_diffrn_reflns_av_R_equivalents  0.1370
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         3.285
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        24.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2700
_reflns_number_gt                828
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'CrysAlis CCD, Oxford Diffraction Ltd.,'
_computing_cell_refinement       'CrysAlis RED, Oxford Diffraction Ltd.,'
_computing_data_reduction        'CrysAlis RED, Oxford Diffraction Ltd.,'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    Ortep3
_computing_publication_material  Shelx97

_refine_special_details          ?

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1010P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2700
_refine_ls_number_parameters     211
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2418
_refine_ls_R_factor_gt           0.0898
_refine_ls_wR_factor_ref         0.2885
_refine_ls_wR_factor_gt          0.2037
_refine_ls_goodness_of_fit_ref   0.966
_refine_ls_restrained_S_all      0.966
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
O2 O 0.44861(14) 0.2837(9) 0.2449(2) 0.0923(14) Uani 1 1 d . . . . .
H2 H 0.4365 0.4390 0.2543 0.138 Uiso 1 1 calc R U . . .
O3 O 0.26566(16) 0.9288(12) 0.3360(3) 0.1141(17) Uani 1 1 d . . . . .
H3 H 0.2824 0.8259 0.3170 0.171 Uiso 1 1 calc R U . . .
N1 N 0.34269(18) 0.7441(10) 0.2962(2) 0.0778(15) Uani 1 1 d . . . . .
N2 N 0.37203(17) 0.5588(10) 0.2658(2) 0.0754(14) Uani 1 1 d . . . . .
O1 O 0.49479(18) -0.0650(11) 0.1750(2) 0.1233(18) Uani 1 1 d . . . . .
H1 H 0.5061 0.0596 0.1966 0.185 Uiso 1 1 calc R U . . .
C006 C 0.3661(2) 0.8972(12) 0.3332(3) 0.0658(16) Uani 1 1 d . . . . .
H006 H 0.3991 0.8864 0.3352 0.079 Uiso 1 1 calc R U . . .
C007 C 0.4227(3) 0.1678(13) 0.2008(3) 0.0794(18) Uani 1 1 d . . . . .
C008 C 0.3745(3) 0.2217(12) 0.1901(3) 0.0726(17) Uani 1 1 d . . . . .
C009 C 0.3427(2) 1.0875(13) 0.3723(3) 0.0731(17) Uani 1 1 d . . . . .
C00A C 0.4474(3) -0.0147(14) 0.1654(4) 0.093(2) Uani 1 1 d . . . . .
C00B C 0.3494(2) 0.4212(13) 0.2252(3) 0.0771(18) Uani 1 1 d . . . . .
H00B H 0.3168 0.4506 0.2185 0.092 Uiso 1 1 calc R U . . .
C00C C 0.3695(3) 1.2711(13) 0.4105(3) 0.0773(18) Uani 1 1 d . . . . .
C00D C 0.2933(3) 1.0855(15) 0.3721(3) 0.090(2) Uani 1 1 d . . . . .
C00E C 0.3443(4) 1.4325(16) 0.4511(3) 0.103(2) Uani 1 1 d . . . . .
C00F C 0.4230(3) -0.1505(13) 0.1230(3) 0.095(2) Uani 1 1 d . . . . .
H00F H 0.4392 -0.2789 0.1004 0.114 Uiso 1 1 calc R U . . .
C00G C 0.3745(3) -0.1055(14) 0.1116(3) 0.103(2) Uani 1 1 d . . . . .
H00G H 0.3585 -0.1986 0.0816 0.123 Uiso 1 1 calc R U . . .
C00H C 0.3503(2) 0.0820(14) 0.1463(3) 0.093(2) Uani 1 1 d . . . . .
H00H H 0.3178 0.1127 0.1399 0.112 Uiso 1 1 calc R U . . .
C00I C 0.2935(4) 1.413(2) 0.4489(5) 0.136(4) Uani 1 1 d . . . . .
H00I H 0.2766 1.5241 0.4736 0.163 Uiso 1 1 calc R U . . .
C00J C 0.4189(3) 1.3007(14) 0.4113(3) 0.095(2) Uani 1 1 d . . . . .
H00J H 0.4358 1.1936 0.3860 0.114 Uiso 1 1 calc R U . . .
C00K C 0.2705(4) 1.243(2) 0.4133(5) 0.128(3) Uani 1 1 d . . . . .
H00K H 0.2376 1.2262 0.4151 0.154 Uiso 1 1 calc R U . . .
C00L C 0.3709(5) 1.611(2) 0.4878(4) 0.134(4) Uani 1 1 d . . . . .
H00L H 0.3549 1.7169 0.5141 0.161 Uiso 1 1 calc R U . . .
C00M C 0.4432(3) 1.481(2) 0.4482(4) 0.128(3) Uani 1 1 d . . . . .
H00M H 0.4761 1.5000 0.4472 0.153 Uiso 1 1 calc R U . . .
C00N C 0.4182(6) 1.639(2) 0.4878(5) 0.152(4) Uani 1 1 d . . . . .
H00N H 0.4344 1.7619 0.5134 0.182 Uiso 1 1 calc R U . . .


_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
O2 C007 1.359(7) . ?
O2 H2 0.8200 . ?
O3 C00D 1.337(7) . ?
O3 H3 0.8200 . ?
N1 C006 1.282(6) . ?
N1 N2 1.409(6) . ?
N2 C00B 1.296(7) . ?
O1 C00A 1.359(7) . ?
O1 H1 0.8200 . ?
C006 C009 1.457(8) . ?
C006 H006 0.9300 . ?
C007 C008 1.385(8) . ?
C007 C00A 1.398(8) . ?
C008 C00H 1.374(8) . ?
C008 C00B 1.448(8) . ?
C009 C00D 1.389(8) . ?
C009 C00C 1.423(8) . ?
C00A C00F 1.345(8) . ?
C00B H00B 0.9300 . ?
C00C C00J 1.396(8) . ?
C00C C00E 1.436(9) . ?
C00D C00K 1.404(10) . ?
C00E C00L 1.386(11) . ?
C00E C00I 1.428(10) . ?
C00F C00G 1.392(8) . ?
C00F H00F 0.9300 . ?
C00G C00H 1.393(9) . ?
C00G H00G 0.9300 . ?
C00H H00H 0.9300 . ?
C00I C00K 1.298(11) . ?
C00I H00I 0.9300 . ?
C00J C00M 1.363(9) . ?
C00J H00J 0.9300 . ?
C00K H00K 0.9300 . ?
C00L C00N 1.337(12) . ?
C00L H00L 0.9300 . ?
C00M C00N 1.408(13) . ?
C00M H00M 0.9300 . ?
C00N H00N 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
C007 O2 H2 109.5 . . ?
C00D O3 H3 109.5 . . ?
C006 N1 N2 113.0(5) . . ?
C00B N2 N1 113.6(5) . . ?
C00A O1 H1 109.5 . . ?
N1 C006 C009 122.4(6) . . ?
N1 C006 H006 118.8 . . ?
C009 C006 H006 118.8 . . ?
O2 C007 C008 123.6(6) . . ?
O2 C007 C00A 116.1(7) . . ?
C008 C007 C00A 120.3(7) . . ?
C00H C008 C007 119.9(7) . . ?
C00H C008 C00B 119.7(7) . . ?
C007 C008 C00B 120.4(6) . . ?
C00D C009 C00C 120.0(6) . . ?
C00D C009 C006 118.6(7) . . ?
C00C C009 C006 121.4(6) . . ?
C00F C00A O1 120.4(7) . . ?
C00F C00A C007 118.8(8) . . ?
O1 C00A C007 120.8(8) . . ?
N2 C00B C008 120.2(6) . . ?
N2 C00B H00B 119.9 . . ?
C008 C00B H00B 119.9 . . ?
C00J C00C C009 123.9(7) . . ?
C00J C00C C00E 117.8(7) . . ?
C009 C00C C00E 118.2(7) . . ?
O3 C00D C009 123.5(7) . . ?
O3 C00D C00K 117.1(9) . . ?
C009 C00D C00K 119.3(8) . . ?
C00L C00E C00I 124.4(10) . . ?
C00L C00E C00C 117.4(10) . . ?
C00I C00E C00C 118.1(8) . . ?
C00A C00F C00G 122.3(8) . . ?
C00A C00F H00F 118.8 . . ?
C00G C00F H00F 118.8 . . ?
C00F C00G C00H 118.5(7) . . ?
C00F C00G H00G 120.8 . . ?
C00H C00G H00G 120.8 . . ?
C008 C00H C00G 120.1(7) . . ?
C008 C00H H00H 120.0 . . ?
C00G C00H H00H 120.0 . . ?
C00K C00I C00E 121.6(10) . . ?
C00K C00I H00I 119.2 . . ?
C00E C00I H00I 119.2 . . ?
C00M C00J C00C 122.2(8) . . ?
C00M C00J H00J 118.9 . . ?
C00C C00J H00J 118.9 . . ?
C00I C00K C00D 122.4(10) . . ?
C00I C00K H00K 118.8 . . ?
C00D C00K H00K 118.8 . . ?
C00N C00L C00E 124.1(12) . . ?
C00N C00L H00L 117.9 . . ?
C00E C00L H00L 117.9 . . ?
C00J C00M C00N 119.5(10) . . ?
C00J C00M H00M 120.2 . . ?
C00N C00M H00M 120.2 . . ?
C00L C00N C00M 118.9(12) . . ?
C00L C00N H00N 120.6 . . ?
C00M C00N H00N 120.6 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C006 N1 N2 C00B -174.6(5) . . . . ?
N2 N1 C006 C009 -175.4(4) . . . . ?
O2 C007 C008 C00H -176.2(6) . . . . ?
C00A C007 C008 C00H 3.8(9) . . . . ?
O2 C007 C008 C00B 2.9(9) . . . . ?
C00A C007 C008 C00B -177.1(5) . . . . ?
N1 C006 C009 C00D 5.0(8) . . . . ?
N1 C006 C009 C00C -175.5(5) . . . . ?
O2 C007 C00A C00F 175.9(6) . . . . ?
C008 C007 C00A C00F -4.1(9) . . . . ?
O2 C007 C00A O1 -1.2(9) . . . . ?
C008 C007 C00A O1 178.9(5) . . . . ?
N1 N2 C00B C008 -179.8(4) . . . . ?
C00H C008 C00B N2 -178.5(5) . . . . ?
C007 C008 C00B N2 2.4(8) . . . . ?
C00D C009 C00C C00J -176.0(6) . . . . ?
C006 C009 C00C C00J 4.6(9) . . . . ?
C00D C009 C00C C00E 5.0(8) . . . . ?
C006 C009 C00C C00E -174.4(5) . . . . ?
C00C C009 C00D O3 177.0(6) . . . . ?
C006 C009 C00D O3 -3.5(9) . . . . ?
C00C C009 C00D C00K -6.1(9) . . . . ?
C006 C009 C00D C00K 173.3(6) . . . . ?
C00J C00C C00E C00L 1.1(9) . . . . ?
C009 C00C C00E C00L -179.8(6) . . . . ?
C00J C00C C00E C00I 177.4(6) . . . . ?
C009 C00C C00E C00I -3.5(9) . . . . ?
O1 C00A C00F C00G 180.0(6) . . . . ?
C007 C00A C00F C00G 2.9(10) . . . . ?
C00A C00F C00G C00H -1.4(10) . . . . ?
C007 C008 C00H C00G -2.3(9) . . . . ?
C00B C008 C00H C00G 178.6(6) . . . . ?
C00F C00G C00H C008 1.1(10) . . . . ?
C00L C00E C00I C00K 179.4(8) . . . . ?
C00C C00E C00I C00K 3.4(12) . . . . ?
C009 C00C C00J C00M 179.3(6) . . . . ?
C00E C00C C00J C00M -1.7(10) . . . . ?
C00E C00I C00K C00D -4.7(14) . . . . ?
O3 C00D C00K C00I -176.9(8) . . . . ?
C009 C00D C00K C00I 6.1(12) . . . . ?
C00I C00E C00L C00N -176.5(9) . . . . ?
C00C C00E C00L C00N -0.4(13) . . . . ?
C00C C00J C00M C00N 1.5(12) . . . . ?
C00E C00L C00N C00M 0.2(16) . . . . ?
C00J C00M C00N C00L -0.7(14) . . . . ?

_refine_diff_density_max         0.181
_refine_diff_density_min         -0.161
_refine_diff_density_rms         0.048



####################################################################### 
# 
# 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_L2
_database_code_depnum_ccdc_archive 'CCDC 1565839'
_audit_update_record             
;
2017-07-31 deposited with the CCDC.
2017-08-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H10 Br2 N2'
_chemical_formula_weight         366.06

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   3.8997(4)
_cell_length_b                   7.1770(5)
_cell_length_c                   24.082(3)
_cell_angle_alpha                90
_cell_angle_beta                 90.434(10)
_cell_angle_gamma                90
_cell_volume                     673.99(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    356
_cell_measurement_theta_min      4.4000
_cell_measurement_theta_max      23.3780

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.804
_exptl_crystal_F_000             356
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    5.996
_shelx_estimated_absorpt_T_min   0.339
_shelx_estimated_absorpt_T_max   0.614
_exptl_absorpt_correction_T_min  0.16001
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Micro-Focus (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'OXFORD DIFFRACTION SUPER NOVA'
_diffrn_measurement_method       ω/q-scan
_diffrn_detector_area_resol_mean 15.9948
_diffrn_reflns_number            4630
_diffrn_reflns_av_unetI/netI     0.0707
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         3.305
_diffrn_reflns_theta_max         28.906
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.873
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.873
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.873
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             4630
_reflns_number_gt                2696
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _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.
;

_computing_data_collection       'CrysAlis CCD, Oxford Diffraction Ltd.,'
_computing_cell_refinement       'CrysAlis RED, Oxford Diffraction Ltd.,'
_computing_data_reduction        'CrysAlis RED, Oxford Diffraction Ltd.,'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    Ortep3
_computing_publication_material  Shelx97

_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4630
_refine_ls_number_parameters     84
_refine_ls_number_restraints     60
_refine_ls_R_factor_all          0.1737
_refine_ls_R_factor_gt           0.1250
_refine_ls_wR_factor_ref         0.3734
_refine_ls_wR_factor_gt          0.3152
_refine_ls_goodness_of_fit_ref   1.171
_refine_ls_restrained_S_all      1.170
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.9138(4) 0.1774(2) 0.31299(9) 0.0877(10) Uani 1 1 d . U . . .
N1 N 0.559(2) 0.9120(12) 0.4896(4) 0.039(2) Uani 1 1 d . U . . .
C1 C 0.489(2) 0.8898(13) 0.4389(5) 0.035(2) Uani 1 1 d . U . . .
H1 H 0.3719 0.9829 0.4197 0.042 Uiso 1 1 calc R U . . .
C2 C 0.590(2) 0.7190(12) 0.4096(4) 0.0277(19) Uani 1 1 d . U . . .
C3 C 0.740(2) 0.5680(14) 0.4372(4) 0.032(2) Uani 1 1 d . U . . .
H3 H 0.7780 0.5741 0.4753 0.038 Uiso 1 1 calc R U . . .
C4 C 0.833(2) 0.4087(13) 0.4082(4) 0.031(2) Uani 1 1 d . U . . .
H4 H 0.9321 0.3079 0.4265 0.037 Uiso 1 1 calc R U . . .
C5 C 0.776(2) 0.4031(14) 0.3532(4) 0.032(2) Uani 1 1 d . U . . .
C6 C 0.623(2) 0.5519(14) 0.3235(4) 0.036(2) Uani 1 1 d . U . . .
H6 H 0.5905 0.5450 0.2852 0.043 Uiso 1 1 calc R U . . .
C7 C 0.526(2) 0.7045(14) 0.3523(4) 0.034(2) Uani 1 1 d . U . . .
H7 H 0.4139 0.8012 0.3339 0.041 Uiso 1 1 calc R U . . .


_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 C5 1.963(9) . ?
N1 C1 1.261(14) . ?
N1 N1 1.435(16) 3_676 ?
C1 C2 1.470(13) . ?
C1 H1 0.9300 . ?
C2 C3 1.398(13) . ?
C2 C7 1.403(15) . ?
C3 C4 1.389(13) . ?
C3 H3 0.9300 . ?
C4 C5 1.341(15) . ?
C4 H4 0.9300 . ?
C5 C6 1.415(15) . ?
C6 C7 1.353(14) . ?
C6 H6 0.9300 . ?
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
C1 N1 N1 112.3(11) . 3_676 ?
N1 C1 C2 120.9(9) . . ?
N1 C1 H1 119.5 . . ?
C2 C1 H1 119.5 . . ?
C3 C2 C7 118.8(9) . . ?
C3 C2 C1 122.1(10) . . ?
C7 C2 C1 119.1(9) . . ?
C4 C3 C2 120.5(10) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C5 C4 C3 118.7(9) . . ?
C5 C4 H4 120.7 . . ?
C3 C4 H4 120.7 . . ?
C4 C5 C6 122.8(9) . . ?
C4 C5 Br1 117.9(7) . . ?
C6 C5 Br1 119.3(8) . . ?
C7 C6 C5 118.1(10) . . ?
C7 C6 H6 121.0 . . ?
C5 C6 H6 121.0 . . ?
C6 C7 C2 121.0(10) . . ?
C6 C7 H7 119.5 . . ?
C2 C7 H7 119.5 . . ?

_refine_diff_density_max         2.699
_refine_diff_density_min         -0.808
_refine_diff_density_rms         0.280



####################################################################### 
# 
# 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_L1
_database_code_depnum_ccdc_archive 'CCDC 1565840'
_audit_update_record             
;
2017-07-31 deposited with the CCDC.
2017-08-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H20 Fe2 N2'
_chemical_formula_weight         424.10

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'
Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.5953(15)
_cell_length_b                   10.1025(15)
_cell_length_c                   12.191(3)
_cell_angle_alpha                90
_cell_angle_beta                 105.83(2)
_cell_angle_gamma                90
_cell_volume                     899.9(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1051
_cell_measurement_theta_min      3.7760
_cell_measurement_theta_max      25.6460

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.565
_exptl_crystal_F_000             436
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    1.619
_shelx_estimated_absorpt_T_min   0.707
_shelx_estimated_absorpt_T_max   0.829
_exptl_absorpt_correction_T_min  0.28039
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Micro-Focus (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'OXFORD DIFFRACTION SUPER NOVA'
_diffrn_measurement_method       ω/q-scan
_diffrn_detector_area_resol_mean 15.9948
_diffrn_reflns_number            6135
_diffrn_reflns_av_unetI/netI     0.1183
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.441
_diffrn_reflns_theta_max         28.896
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.894
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.894
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.894
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             6135
_reflns_number_gt                3569
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _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.
;

_computing_data_collection       'CrysAlis CCD, Oxford Diffraction Ltd.,'
_computing_cell_refinement       'CrysAlis RED, Oxford Diffraction Ltd.,'
_computing_data_reduction        'CrysAlis RED, Oxford Diffraction Ltd.,'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    Ortep3
_computing_publication_material  Shelx97

_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6135
_refine_ls_number_parameters     119
_refine_ls_number_restraints     183
_refine_ls_R_factor_all          0.1614
_refine_ls_R_factor_gt           0.1166
_refine_ls_wR_factor_ref         0.3725
_refine_ls_wR_factor_gt          0.3031
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_restrained_S_all      1.088
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
Fe1 Fe 0.71356(18) 0.67986(15) 0.66520(11) 0.0446(6) Uani 1 1 d . U . . .
N1 N 1.0105(14) 0.5286(9) 0.9505(8) 0.061(3) Uani 1 1 d . U . . .
C1 C 0.8890(16) 0.4893(10) 0.8620(9) 0.054(3) Uani 1 1 d . U . . .
H1 H 0.8006 0.4301 0.8716 0.065 Uiso 1 1 calc R U . . .
C2 C 0.8816(14) 0.5322(10) 0.7467(9) 0.049(2) Uani 1 1 d . U . . .
C3 C 0.9838(14) 0.6351(10) 0.7098(9) 0.049(2) Uani 1 1 d . U . . .
H3 H 1.0750 0.6866 0.7572 0.059 Uiso 1 1 calc R U . . .
C4 C 0.9232(15) 0.6449(12) 0.5908(10) 0.055(3) Uani 1 1 d . U . . .
H4 H 0.9672 0.7035 0.5456 0.066 Uiso 1 1 calc R U . . .
C5 C 0.7812(15) 0.5487(11) 0.5507(9) 0.058(3) Uani 1 1 d . U . . .
H5 H 0.7180 0.5327 0.4750 0.069 Uiso 1 1 calc R U . . .
C6 C 0.7549(14) 0.4828(10) 0.6468(9) 0.048(2) Uani 1 1 d . U . . .
H6 H 0.6682 0.4173 0.6452 0.058 Uiso 1 1 calc R U . . .
C7 C 0.5913(18) 0.7533(12) 0.7812(11) 0.069(3) Uani 1 1 d . U . . .
H7 H 0.6111 0.7229 0.8556 0.083 Uiso 1 1 calc R U . . .
C8 C 0.6897(18) 0.8555(12) 0.7410(12) 0.067(3) Uani 1 1 d . U . . .
H8 H 0.7864 0.9045 0.7859 0.080 Uiso 1 1 calc R U . . .
C9 C 0.617(2) 0.8691(13) 0.6243(12) 0.074(3) Uani 1 1 d . U . . .
H9 H 0.6547 0.9295 0.5780 0.089 Uiso 1 1 calc R U . . .
C10 C 0.4763(17) 0.7770(13) 0.5880(11) 0.068(3) Uani 1 1 d . U . . .
H10 H 0.4079 0.7642 0.5129 0.082 Uiso 1 1 calc R U . . .
C11 C 0.4552(16) 0.7080(12) 0.6811(11) 0.063(3) Uani 1 1 d . U . . .
H11 H 0.3677 0.6430 0.6796 0.076 Uiso 1 1 calc R U . . .


_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
Fe1 C3 2.026(10) . ?
Fe1 C8 2.031(12) . ?
Fe1 C7 2.032(12) . ?
Fe1 C6 2.037(10) . ?
Fe1 C2 2.037(10) . ?
Fe1 C10 2.042(11) . ?
Fe1 C11 2.044(11) . ?
Fe1 C9 2.060(12) . ?
Fe1 C4 2.066(11) . ?
Fe1 C5 2.088(10) . ?
N1 C1 1.277(14) . ?
N1 N1 1.386(18) 3_767 ?
C1 C2 1.457(14) . ?
C1 H1 0.9300 . ?
C2 C6 1.421(14) . ?
C2 C3 1.441(14) . ?
C3 C4 1.401(14) . ?
C3 H3 0.9300 . ?
C4 C5 1.435(16) . ?
C4 H4 0.9300 . ?
C5 C6 1.408(16) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C8 1.437(18) . ?
C7 C11 1.442(17) . ?
C7 H7 0.9300 . ?
C8 C9 1.385(17) . ?
C8 H8 0.9300 . ?
C9 C10 1.392(19) . ?
C9 H9 0.9300 . ?
C10 C11 1.379(16) . ?
C10 H10 0.9300 . ?
C11 H11 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
C3 Fe1 C8 106.4(5) . . ?
C3 Fe1 C7 121.1(5) . . ?
C8 Fe1 C7 41.4(5) . . ?
C3 Fe1 C6 68.7(4) . . ?
C8 Fe1 C6 159.9(5) . . ?
C7 Fe1 C6 123.1(5) . . ?
C3 Fe1 C2 41.5(4) . . ?
C8 Fe1 C2 122.6(5) . . ?
C7 Fe1 C2 105.8(5) . . ?
C6 Fe1 C2 40.8(4) . . ?
C3 Fe1 C10 158.9(5) . . ?
C8 Fe1 C10 67.2(5) . . ?
C7 Fe1 C10 68.4(5) . . ?
C6 Fe1 C10 124.2(5) . . ?
C2 Fe1 C10 159.0(5) . . ?
C3 Fe1 C11 159.1(5) . . ?
C8 Fe1 C11 68.2(5) . . ?
C7 Fe1 C11 41.4(5) . . ?
C6 Fe1 C11 109.1(5) . . ?
C2 Fe1 C11 123.1(5) . . ?
C10 Fe1 C11 39.4(5) . . ?
C3 Fe1 C9 122.8(5) . . ?
C8 Fe1 C9 39.6(5) . . ?
C7 Fe1 C9 68.2(5) . . ?
C6 Fe1 C9 159.3(5) . . ?
C2 Fe1 C9 158.8(5) . . ?
C10 Fe1 C9 39.7(5) . . ?
C11 Fe1 C9 66.7(5) . . ?
C3 Fe1 C4 40.0(4) . . ?
C8 Fe1 C4 121.6(5) . . ?
C7 Fe1 C4 157.1(5) . . ?
C6 Fe1 C4 67.9(5) . . ?
C2 Fe1 C4 68.5(4) . . ?
C10 Fe1 C4 124.6(5) . . ?
C11 Fe1 C4 160.1(5) . . ?
C9 Fe1 C4 108.7(5) . . ?
C3 Fe1 C5 67.8(4) . . ?
C8 Fe1 C5 158.0(5) . . ?
C7 Fe1 C5 160.0(5) . . ?
C6 Fe1 C5 39.9(4) . . ?
C2 Fe1 C5 68.0(4) . . ?
C10 Fe1 C5 110.1(5) . . ?
C11 Fe1 C5 124.7(5) . . ?
C9 Fe1 C5 124.3(5) . . ?
C4 Fe1 C5 40.4(4) . . ?
C1 N1 N1 112.2(14) . 3_767 ?
N1 C1 C2 123.5(12) . . ?
N1 C1 H1 118.3 . . ?
C2 C1 H1 118.3 . . ?
C6 C2 C3 106.4(9) . . ?
C6 C2 C1 124.1(10) . . ?
C3 C2 C1 129.3(9) . . ?
C6 C2 Fe1 69.6(5) . . ?
C3 C2 Fe1 68.8(5) . . ?
C1 C2 Fe1 122.9(7) . . ?
C4 C3 C2 108.7(9) . . ?
C4 C3 Fe1 71.5(6) . . ?
C2 C3 Fe1 69.6(6) . . ?
C4 C3 H3 125.6 . . ?
C2 C3 H3 125.6 . . ?
Fe1 C3 H3 124.8 . . ?
C3 C4 C5 108.0(10) . . ?
C3 C4 Fe1 68.4(6) . . ?
C5 C4 Fe1 70.6(6) . . ?
C3 C4 H4 126.0 . . ?
C5 C4 H4 126.0 . . ?
Fe1 C4 H4 126.5 . . ?
C6 C5 C4 107.5(10) . . ?
C6 C5 Fe1 68.1(6) . . ?
C4 C5 Fe1 69.0(6) . . ?
C6 C5 H5 126.3 . . ?
C4 C5 H5 126.3 . . ?
Fe1 C5 H5 128.2 . . ?
C5 C6 C2 109.3(11) . . ?
C5 C6 Fe1 72.0(6) . . ?
C2 C6 Fe1 69.6(6) . . ?
C5 C6 H6 125.3 . . ?
C2 C6 H6 125.3 . . ?
Fe1 C6 H6 124.7 . . ?
C8 C7 C11 105.0(12) . . ?
C8 C7 Fe1 69.3(7) . . ?
C11 C7 Fe1 69.7(7) . . ?
C8 C7 H7 127.5 . . ?
C11 C7 H7 127.5 . . ?
Fe1 C7 H7 125.1 . . ?
C9 C8 C7 108.7(12) . . ?
C9 C8 Fe1 71.3(7) . . ?
C7 C8 Fe1 69.3(7) . . ?
C9 C8 H8 125.6 . . ?
C7 C8 H8 125.6 . . ?
Fe1 C8 H8 125.3 . . ?
C8 C9 C10 108.6(12) . . ?
C8 C9 Fe1 69.1(7) . . ?
C10 C9 Fe1 69.5(7) . . ?
C8 C9 H9 125.7 . . ?
C10 C9 H9 125.7 . . ?
Fe1 C9 H9 127.3 . . ?
C11 C10 C9 109.1(12) . . ?
C11 C10 Fe1 70.3(7) . . ?
C9 C10 Fe1 70.9(7) . . ?
C11 C10 H10 125.5 . . ?
C9 C10 H10 125.5 . . ?
Fe1 C10 H10 124.9 . . ?
C10 C11 C7 108.6(13) . . ?
C10 C11 Fe1 70.2(7) . . ?
C7 C11 Fe1 68.8(7) . . ?
C10 C11 H11 125.7 . . ?
C7 C11 H11 125.7 . . ?
Fe1 C11 H11 126.8 . . ?

_refine_diff_density_max         1.554
_refine_diff_density_min         -0.929
_refine_diff_density_rms         0.220



####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1543797'
_audit_update_record             
;
2017-04-13 deposited with the CCDC.
2017-08-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H14 N2 O3'
_chemical_formula_weight         306.31

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   14.6490(13)
_cell_length_b                   5.0010(4)
_cell_length_c                   21.4358(17)
_cell_angle_alpha                90
_cell_angle_beta                 108.746(9)
_cell_angle_gamma                90
_cell_volume                     1487.1(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2065
_cell_measurement_theta_min      4.0050
_cell_measurement_theta_max      21.4530

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    not-measured
_exptl_crystal_density_diffrn    1.368
_exptl_crystal_F_000             640
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.090
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.095
_shelx_estimated_absorpt_T_min   0.992
_shelx_estimated_absorpt_T_max   0.998
_exptl_absorpt_correction_T_min  0.59787
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Micro-Focus (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'OXFORD DIFFRACTION SUPER NOVA'
_diffrn_measurement_method       ω/q-scan
_diffrn_detector_area_resol_mean 15.9948
_diffrn_reflns_number            13936
_diffrn_reflns_av_unetI/netI     0.0536
_diffrn_reflns_av_R_equivalents  0.0742
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.894
_diffrn_reflns_theta_max         24.996
_diffrn_reflns_theta_full        24.996
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2606
_reflns_number_gt                1297
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'CrysAlis CCD, Oxford Diffraction Ltd.,'
_computing_cell_refinement       'CrysAlis RED, Oxford Diffraction Ltd.,'
_computing_data_reduction        'CrysAlis RED, Oxford Diffraction Ltd.,'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    Ortep3
_computing_publication_material  Shelx97

_refine_special_details          ?

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0876P)²+0.3282P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0016(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2606
_refine_ls_number_parameters     217
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1311
_refine_ls_R_factor_gt           0.0685
_refine_ls_wR_factor_ref         0.2260
_refine_ls_wR_factor_gt          0.1773
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.041
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
O1 O 0.8686(2) 0.2639(7) 0.40585(16) 0.0949(10) Uani 1 1 d D . . . .
O2 O 0.73590(18) 0.8787(5) 0.62932(13) 0.0801(8) Uani 1 1 d . . . . .
H2 H 0.7354 0.7739 0.5998 0.120 Uiso 1 1 calc R U . . .
O3 O 0.7603(2) 1.2327(6) 0.72332(15) 0.0853(10) Uani 1 1 d . . . . .
N1 N 0.7995(2) 0.4920(6) 0.48816(14) 0.0688(9) Uani 1 1 d . . . . .
N2 N 0.7967(2) 0.6659(6) 0.53796(14) 0.0663(9) Uani 1 1 d . . . . .
C1 C 0.7873(3) 0.1126(8) 0.38809(18) 0.0746(12) Uani 1 1 d . . . . .
C2 C 0.7792(4) -0.0765(11) 0.3384(2) 0.0943(15) Uani 1 1 d . . . . .
H2A H 0.8275 -0.0918 0.3191 0.113 Uiso 1 1 calc R U . . .
C3 C 0.7017(4) -0.2350(10) 0.3189(2) 0.0945(16) Uani 1 1 d . . . . .
H3 H 0.6971 -0.3575 0.2853 0.113 Uiso 1 1 calc R U . . .
C4 C 0.6269(3) -0.2251(9) 0.34659(19) 0.0800(13) Uani 1 1 d . . . . .
C5 C 0.5489(4) -0.4019(9) 0.3267(2) 0.0977(16) Uani 1 1 d . . . . .
H5 H 0.5456 -0.5271 0.2939 0.117 Uiso 1 1 calc R U . . .
C6 C 0.4785(4) -0.3922(10) 0.3545(3) 0.1059(17) Uani 1 1 d . . . . .
H6 H 0.4274 -0.5125 0.3416 0.127 Uiso 1 1 calc R U . . .
C7 C 0.4825(4) -0.2047(10) 0.4017(3) 0.1026(15) Uani 1 1 d . . . . .
H7 H 0.4325 -0.1952 0.4196 0.123 Uiso 1 1 calc R U . . .
C8 C 0.5587(3) -0.0296(9) 0.4235(2) 0.0882(13) Uani 1 1 d . . . . .
H8 H 0.5600 0.0931 0.4564 0.106 Uiso 1 1 calc R U . . .
C9 C 0.6340(3) -0.0338(8) 0.39684(17) 0.0695(11) Uani 1 1 d . . . . .
C10 C 0.7161(3) 0.1400(7) 0.41725(16) 0.0655(10) Uani 1 1 d . . . . .
C11 C 0.7254(3) 0.3362(8) 0.46821(17) 0.0649(10) Uani 1 1 d . . . . .
H11 H 0.6768 0.3510 0.4872 0.078 Uiso 1 1 calc R U . . .
C12 C 0.8704(3) 0.8249(8) 0.55705(17) 0.0671(10) Uani 1 1 d . . . . .
H12 H 0.9176 0.8137 0.5367 0.080 Uiso 1 1 calc R U . . .
C13 C 0.8814(2) 1.0183(7) 0.60874(15) 0.0570(9) Uani 1 1 d . . . . .
C14 C 0.8151(3) 1.0398(7) 0.64250(17) 0.0611(10) Uani 1 1 d . . . . .
C15 C 0.8273(3) 1.2289(7) 0.69195(18) 0.0623(10) Uani 1 1 d . . . . .
C16 C 0.9061(3) 1.3974(7) 0.70775(18) 0.0666(10) Uani 1 1 d . . . . .
H16 H 0.9149 1.5235 0.7411 0.080 Uiso 1 1 calc R U . . .
C17 C 0.9722(3) 1.3784(8) 0.67387(19) 0.0710(11) Uani 1 1 d . . . . .
H17 H 1.0249 1.4933 0.6841 0.085 Uiso 1 1 calc R U . . .
C18 C 0.9601(3) 1.1907(8) 0.62547(18) 0.0688(10) Uani 1 1 d . . . . .
H18 H 1.0051 1.1782 0.6034 0.083 Uiso 1 1 calc R U . . .
H103 H 0.766(3) 1.373(9) 0.746(2) 0.091(16) Uiso 1 1 d . . . . .
H101 H 0.868(4) 0.383(8) 0.4381(19) 0.14(2) Uiso 1 1 d D . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.358(5) . ?
O1 H101 0.92(2) . ?
O2 C14 1.365(4) . ?
O2 H2 0.8200 . ?
O3 C15 1.357(4) . ?
O3 H103 0.84(4) . ?
N1 C11 1.292(5) . ?
N1 N2 1.387(4) . ?
N2 C12 1.296(5) . ?
C1 C10 1.384(5) . ?
C1 C2 1.400(6) . ?
C2 C3 1.336(7) . ?
C2 H2A 0.9300 . ?
C3 C4 1.405(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.399(6) . ?
C4 C9 1.419(5) . ?
C5 C6 1.349(7) . ?
C5 H5 0.9300 . ?
C6 C7 1.367(6) . ?
C6 H6 0.9300 . ?
C7 C8 1.377(6) . ?
C7 H7 0.9300 . ?
C8 C9 1.396(6) . ?
C8 H8 0.9300 . ?
C9 C10 1.434(5) . ?
C10 C11 1.442(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.440(5) . ?
C12 H12 0.9300 . ?
C13 C18 1.391(5) . ?
C13 C14 1.390(5) . ?
C14 C15 1.389(5) . ?
C15 C16 1.380(5) . ?
C16 C17 1.389(5) . ?
C16 H16 0.9300 . ?
C17 C18 1.367(5) . ?
C17 H17 0.9300 . ?
C18 H18 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
C1 O1 H101 111(4) . . ?
C14 O2 H2 109.5 . . ?
C15 O3 H103 110(3) . . ?
C11 N1 N2 113.8(3) . . ?
C12 N2 N1 113.6(3) . . ?
O1 C1 C10 122.5(4) . . ?
O1 C1 C2 116.2(4) . . ?
C10 C1 C2 121.2(5) . . ?
C3 C2 C1 119.7(5) . . ?
C3 C2 H2A 120.2 . . ?
C1 C2 H2A 120.2 . . ?
C2 C3 C4 123.0(4) . . ?
C2 C3 H3 118.5 . . ?
C4 C3 H3 118.5 . . ?
C5 C4 C3 121.3(5) . . ?
C5 C4 C9 120.7(5) . . ?
C3 C4 C9 117.9(4) . . ?
C6 C5 C4 120.5(5) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C5 C6 C7 119.7(5) . . ?
C5 C6 H6 120.2 . . ?
C7 C6 H6 120.2 . . ?
C6 C7 C8 121.6(5) . . ?
C6 C7 H7 119.2 . . ?
C8 C7 H7 119.2 . . ?
C7 C8 C9 120.8(5) . . ?
C7 C8 H8 119.6 . . ?
C9 C8 H8 119.6 . . ?
C8 C9 C4 116.5(4) . . ?
C8 C9 C10 124.2(4) . . ?
C4 C9 C10 119.3(4) . . ?
C1 C10 C9 118.8(4) . . ?
C1 C10 C11 120.5(4) . . ?
C9 C10 C11 120.6(4) . . ?
N1 C11 C10 121.7(4) . . ?
N1 C11 H11 119.1 . . ?
C10 C11 H11 119.1 . . ?
N2 C12 C13 122.1(4) . . ?
N2 C12 H12 119.0 . . ?
C13 C12 H12 119.0 . . ?
C18 C13 C14 118.5(3) . . ?
C18 C13 C12 119.6(4) . . ?
C14 C13 C12 121.9(3) . . ?
O2 C14 C15 116.9(3) . . ?
O2 C14 C13 122.4(3) . . ?
C15 C14 C13 120.6(3) . . ?
O3 C15 C16 123.4(4) . . ?
O3 C15 C14 116.8(3) . . ?
C16 C15 C14 119.7(3) . . ?
C15 C16 C17 119.9(4) . . ?
C15 C16 H16 120.0 . . ?
C17 C16 H16 120.0 . . ?
C18 C17 C16 120.1(4) . . ?
C18 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
C17 C18 C13 121.1(4) . . ?
C17 C18 H18 119.4 . . ?
C13 C18 H18 119.4 . . ?

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
C11 N1 N2 C12 -178.9(3) . . . . ?
O1 C1 C2 C3 179.2(4) . . . . ?
C10 C1 C2 C3 -0.4(6) . . . . ?
C1 C2 C3 C4 -1.0(7) . . . . ?
C2 C3 C4 C5 -177.3(4) . . . . ?
C2 C3 C4 C9 1.2(6) . . . . ?
C3 C4 C5 C6 179.0(4) . . . . ?
C9 C4 C5 C6 0.6(6) . . . . ?
C4 C5 C6 C7 1.2(7) . . . . ?
C5 C6 C7 C8 -2.2(7) . . . . ?
C6 C7 C8 C9 1.4(7) . . . . ?
C7 C8 C9 C4 0.4(6) . . . . ?
C7 C8 C9 C10 -179.4(4) . . . . ?
C5 C4 C9 C8 -1.3(5) . . . . ?
C3 C4 C9 C8 -179.8(4) . . . . ?
C5 C4 C9 C10 178.5(3) . . . . ?
C3 C4 C9 C10 0.0(5) . . . . ?
O1 C1 C10 C9 -178.1(3) . . . . ?
C2 C1 C10 C9 1.4(5) . . . . ?
O1 C1 C10 C11 0.6(5) . . . . ?
C2 C1 C10 C11 -179.8(3) . . . . ?
C8 C9 C10 C1 178.6(4) . . . . ?
C4 C9 C10 C1 -1.2(5) . . . . ?
C8 C9 C10 C11 -0.2(6) . . . . ?
C4 C9 C10 C11 -179.9(3) . . . . ?
N2 N1 C11 C10 -179.3(3) . . . . ?
C1 C10 C11 N1 0.2(5) . . . . ?
C9 C10 C11 N1 178.9(3) . . . . ?
N1 N2 C12 C13 -179.4(3) . . . . ?
N2 C12 C13 C18 -177.5(3) . . . . ?
N2 C12 C13 C14 2.0(5) . . . . ?
C18 C13 C14 O2 -179.9(3) . . . . ?
C12 C13 C14 O2 0.5(5) . . . . ?
C18 C13 C14 C15 -0.2(5) . . . . ?
C12 C13 C14 C15 -179.7(3) . . . . ?
O2 C14 C15 O3 1.1(5) . . . . ?
C13 C14 C15 O3 -178.7(3) . . . . ?
O2 C14 C15 C16 179.8(3) . . . . ?
C13 C14 C15 C16 0.0(5) . . . . ?
O3 C15 C16 C17 179.1(3) . . . . ?
C14 C15 C16 C17 0.5(5) . . . . ?
C15 C16 C17 C18 -0.8(5) . . . . ?
C16 C17 C18 C13 0.7(5) . . . . ?
C14 C13 C18 C17 -0.2(5) . . . . ?
C12 C13 C18 C17 179.4(3) . . . . ?

_refine_diff_density_max         0.172
_refine_diff_density_min         -0.146
_refine_diff_density_rms         0.041



