# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_ic18907
_database_code_depnum_ccdc_archive 'CCDC 1816891'
_audit_update_record             
;
2018-01-15 deposited with the CCDC.
2018-05-15 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            'C23 H19 N3 O'
_chemical_formula_weight         353.41

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

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

_cell_length_a                   10.21340(10)
_cell_length_b                   18.2798(2)
_cell_length_c                   19.5856(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3656.61(8)
_cell_formula_units_Z            8
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    9984
_cell_measurement_theta_min      5.45
_cell_measurement_theta_max      75.05

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.284
_exptl_crystal_F_000             1488
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.244
_exptl_crystal_size_mid          0.244
_exptl_crystal_size_min          0.045
_exptl_absorpt_coefficient_mu    0.635
_shelx_estimated_absorpt_T_min   0.860
_shelx_estimated_absorpt_T_max   0.972
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6382
_exptl_absorpt_correction_T_max  0.7539
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19042
_diffrn_reflns_av_unetI/netI     0.0166
_diffrn_reflns_av_R_equivalents  0.0212
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         4.515
_diffrn_reflns_theta_max         74.989
_diffrn_reflns_theta_full        67.679
_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             3764
_reflns_number_gt                3440
_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       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0368P)²+1.1706P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3764
_refine_ls_number_parameters     252
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0386
_refine_ls_R_factor_gt           0.0352
_refine_ls_wR_factor_ref         0.0891
_refine_ls_wR_factor_gt          0.0845
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.001
_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 0.33228(7) 1.03647(4) 0.50950(4) 0.03319(18) Uani 1 1 d . . . . .
N1 N 0.44409(9) 0.95543(5) 0.57420(4) 0.02850(19) Uani 1 1 d . . . . .
H1 H 0.5093(16) 0.9557(8) 0.5456(8) 0.043(4) Uiso 1 1 d . . . . .
N2 N 0.28474(8) 0.98479(5) 0.68164(4) 0.0300(2) Uani 1 1 d . . . . .
N3 N -0.08295(10) 0.91451(6) 0.55841(5) 0.0370(2) Uani 1 1 d . . . . .
H3 H -0.1616(18) 0.9205(9) 0.5410(9) 0.058(5) Uiso 1 1 d . . . . .
C1 C 0.34017(10) 0.99764(6) 0.56140(5) 0.0261(2) Uani 1 1 d . . . . .
C2 C 0.22958(9) 0.99580(6) 0.61331(5) 0.0261(2) Uani 1 1 d . . . . .
H2 H 0.1909 1.0461 0.6135 0.031 Uiso 1 1 calc R U . . .
C3 C -0.00183(10) 0.97061(7) 0.57675(6) 0.0325(2) Uani 1 1 d . . . . .
H3A H -0.0270 1.0206 0.5788 0.039 Uiso 1 1 calc R U . . .
C4 C 0.12043(10) 0.94490(6) 0.59182(5) 0.0264(2) Uani 1 1 d . . . . .
C5 C 0.11616(10) 0.86669(6) 0.58185(5) 0.0282(2) Uani 1 1 d . . . . .
C6 C 0.20439(11) 0.80855(6) 0.58967(6) 0.0361(3) Uani 1 1 d . . . . .
H6 H 0.2919 0.8176 0.6037 0.043 Uiso 1 1 calc R U . . .
C7 C 0.16295(14) 0.73787(7) 0.57685(8) 0.0470(3) Uani 1 1 d . . . . .
H7 H 0.2229 0.6985 0.5820 0.056 Uiso 1 1 calc R U . . .
C8 C 0.03388(15) 0.72323(8) 0.55634(8) 0.0504(3) Uani 1 1 d . . . . .
H8 H 0.0080 0.6741 0.5479 0.060 Uiso 1 1 calc R U . . .
C9 C -0.05541(13) 0.77860(8) 0.54831(7) 0.0441(3) Uani 1 1 d . . . . .
H9 H -0.1429 0.7687 0.5346 0.053 Uiso 1 1 calc R U . . .
C10 C -0.01357(11) 0.85005(7) 0.56088(5) 0.0329(2) Uani 1 1 d . . . . .
C11 C 0.46117(10) 0.91501(6) 0.63497(5) 0.0270(2) Uani 1 1 d . . . . .
C12 C 0.37832(10) 0.93044(6) 0.69036(5) 0.0275(2) Uani 1 1 d . . . . .
C13 C 0.39940(11) 0.89210(6) 0.75118(6) 0.0338(2) Uani 1 1 d . . . . .
H13 H 0.3462 0.9020 0.7899 0.041 Uiso 1 1 calc R U . . .
C14 C 0.49749(13) 0.83974(6) 0.75533(6) 0.0378(3) Uani 1 1 d . . . . .
H14 H 0.5095 0.8134 0.7967 0.045 Uiso 1 1 calc R U . . .
C15 C 0.57807(12) 0.82523(6) 0.70020(6) 0.0370(3) Uani 1 1 d . . . . .
H15 H 0.6456 0.7897 0.7039 0.044 Uiso 1 1 calc R U . . .
C16 C 0.55943(11) 0.86308(6) 0.63938(6) 0.0322(2) Uani 1 1 d . . . . .
H16 H 0.6138 0.8533 0.6011 0.039 Uiso 1 1 calc R U . . .
C17 C 0.20166(11) 1.00622(7) 0.73856(5) 0.0342(2) Uani 1 1 d . . . . .
H17A H 0.1733 0.9617 0.7632 0.041 Uiso 1 1 calc R U . . .
H17B H 0.1223 1.0305 0.7204 0.041 Uiso 1 1 calc R U . . .
C18 C 0.26824(11) 1.05740(6) 0.78870(5) 0.0300(2) Uani 1 1 d . . . . .
C19 C 0.21266(12) 1.06739(7) 0.85304(6) 0.0373(3) Uani 1 1 d . . . . .
H19 H 0.1361 1.0409 0.8651 0.045 Uiso 1 1 calc R U . . .
C20 C 0.26767(15) 1.11542(7) 0.89948(6) 0.0457(3) Uani 1 1 d . . . . .
H20 H 0.2282 1.1220 0.9430 0.055 Uiso 1 1 calc R U . . .
C21 C 0.37940(16) 1.15368(7) 0.88293(7) 0.0508(4) Uani 1 1 d . . . . .
H21 H 0.4173 1.1865 0.9149 0.061 Uiso 1 1 calc R U . . .
C22 C 0.43619(14) 1.14392(7) 0.81934(8) 0.0473(3) Uani 1 1 d . . . . .
H22 H 0.5136 1.1700 0.8079 0.057 Uiso 1 1 calc R U . . .
C23 C 0.38052(12) 1.09623(6) 0.77220(6) 0.0365(3) Uani 1 1 d . . . . .
H23 H 0.4196 1.0902 0.7285 0.044 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
O1 C1 1.2423(13) . ?
N1 C1 1.3360(14) . ?
N1 C11 1.4117(13) . ?
N2 C12 1.3890(14) . ?
N2 C17 1.4547(13) . ?
N2 C2 1.4659(13) . ?
N3 C3 1.3664(16) . ?
N3 C10 1.3759(16) . ?
C1 C2 1.5201(14) . ?
C2 C4 1.5119(14) . ?
C3 C4 1.3665(15) . ?
C4 C5 1.4436(15) . ?
C5 C6 1.4017(16) . ?
C5 C10 1.4201(15) . ?
C6 C7 1.3827(18) . ?
C7 C8 1.404(2) . ?
C8 C9 1.372(2) . ?
C9 C10 1.3961(17) . ?
C11 C16 1.3842(15) . ?
C11 C12 1.4044(15) . ?
C12 C13 1.3987(15) . ?
C13 C14 1.3880(18) . ?
C14 C15 1.3834(19) . ?
C15 C16 1.3906(16) . ?
C17 C18 1.5173(15) . ?
C18 C23 1.3868(16) . ?
C18 C19 1.3940(15) . ?
C19 C20 1.3834(18) . ?
C20 C21 1.377(2) . ?
C21 C22 1.385(2) . ?
C22 C23 1.3914(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
C1 N1 C11 123.97(9) . . ?
C12 N2 C17 119.98(9) . . ?
C12 N2 C2 118.35(8) . . ?
C17 N2 C2 116.01(8) . . ?
C3 N3 C10 108.74(9) . . ?
O1 C1 N1 122.35(9) . . ?
O1 C1 C2 120.78(9) . . ?
N1 C1 C2 116.87(9) . . ?
N2 C2 C4 116.93(8) . . ?
N2 C2 C1 109.16(8) . . ?
C4 C2 C1 112.04(8) . . ?
N3 C3 C4 110.65(10) . . ?
C3 C4 C5 106.49(9) . . ?
C3 C4 C2 121.48(10) . . ?
C5 C4 C2 132.03(9) . . ?
C6 C5 C10 117.97(10) . . ?
C6 C5 C4 135.78(10) . . ?
C10 C5 C4 106.23(10) . . ?
C7 C6 C5 119.47(11) . . ?
C6 C7 C8 121.17(13) . . ?
C9 C8 C7 121.10(12) . . ?
C8 C9 C10 117.82(12) . . ?
N3 C10 C9 129.59(11) . . ?
N3 C10 C5 107.90(10) . . ?
C9 C10 C5 122.48(11) . . ?
C16 C11 C12 121.76(10) . . ?
C16 C11 N1 120.07(9) . . ?
C12 C11 N1 118.14(9) . . ?
N2 C12 C13 124.68(10) . . ?
N2 C12 C11 117.60(9) . . ?
C13 C12 C11 117.67(10) . . ?
C14 C13 C12 120.44(11) . . ?
C15 C14 C13 121.05(11) . . ?
C14 C15 C16 119.46(11) . . ?
C11 C16 C15 119.60(11) . . ?
N2 C17 C18 113.62(9) . . ?
C23 C18 C19 118.71(11) . . ?
C23 C18 C17 122.36(10) . . ?
C19 C18 C17 118.90(10) . . ?
C20 C19 C18 120.80(12) . . ?
C21 C20 C19 120.27(12) . . ?
C20 C21 C22 119.55(12) . . ?
C21 C22 C23 120.41(13) . . ?
C18 C23 C22 120.25(12) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O1 0.870(17) 1.951(17) 2.8154(12) 172.6(14) 5_676
N3 H3 O1 0.880(19) 2.153(19) 3.0095(12) 164.4(16) 5_576

_refine_diff_density_max         0.256
_refine_diff_density_min         -0.160
_refine_diff_density_rms         0.033

####################################################################### 
# 
# 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_ic18196
_database_code_depnum_ccdc_archive 'CCDC 1816892'
_audit_update_record             
;
2018-01-15 deposited with the CCDC.
2018-05-15 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            'C23 H18 Br N3 O'
_chemical_formula_weight         432.31

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

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

_cell_length_a                   19.2070(5)
_cell_length_b                   10.1247(3)
_cell_length_c                   19.7884(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3848.15(18)
_cell_formula_units_Z            8
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    9671
_cell_measurement_theta_min      4.37
_cell_measurement_theta_max      70.05

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.492
_exptl_crystal_F_000             1760
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.271
_exptl_crystal_size_mid          0.244
_exptl_crystal_size_min          0.113
_exptl_absorpt_coefficient_mu    3.057
_shelx_estimated_absorpt_T_min   0.491
_shelx_estimated_absorpt_T_max   0.724
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5463
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22356
_diffrn_reflns_av_unetI/netI     0.0108
_diffrn_reflns_av_R_equivalents  0.0169
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         4.604
_diffrn_reflns_theta_max         69.962
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             3624
_reflns_number_gt                3536
_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       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0457P)²+3.9941P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3624
_refine_ls_number_parameters     261
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0371
_refine_ls_R_factor_gt           0.0365
_refine_ls_wR_factor_ref         0.0945
_refine_ls_wR_factor_gt          0.0939
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_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 0.39027(2) 0.25454(3) 0.17685(2) 0.05330(13) Uani 1 1 d . . . . .
O1 O 0.49011(6) 0.16967(11) 0.52776(6) 0.0251(3) Uani 1 1 d . . . . .
N1 N 0.44258(9) 0.59210(16) 0.41943(9) 0.0311(4) Uani 1 1 d . . . . .
H1 H 0.4614(14) 0.667(3) 0.4271(13) 0.049(8) Uiso 1 1 d . . . . .
N2 N 0.42864(8) 0.05846(14) 0.44908(8) 0.0218(3) Uani 1 1 d . . . . .
H2 H 0.4558(12) -0.007(2) 0.4518(11) 0.029(6) Uiso 1 1 d . . . . .
N3 N 0.31646(7) 0.21524(14) 0.47288(8) 0.0243(3) Uani 1 1 d . . . . .
C1 C 0.43889(9) 0.16202(16) 0.48975(8) 0.0196(3) Uani 1 1 d . . . . .
C2 C 0.38484(9) 0.27159(16) 0.48737(9) 0.0197(3) Uani 1 1 d . . . . .
H2A H 0.3819 0.3074 0.5344 0.024 Uiso 1 1 calc R U . . .
C3 C 0.42443(9) 0.50645(17) 0.46969(9) 0.0254(4) Uani 1 1 d . . . . .
H3 H 0.4237 0.5278 0.5164 0.030 Uiso 1 1 calc R U . . .
C4 C 0.40741(8) 0.38566(16) 0.44349(9) 0.0190(3) Uani 1 1 d . . . . .
C5 C 0.41525(8) 0.39695(16) 0.37109(9) 0.0197(3) Uani 1 1 d . . . . .
C6 C 0.40318(9) 0.31343(18) 0.31603(9) 0.0233(4) Uani 1 1 d . . . . .
H6 H 0.3889 0.2245 0.3226 0.028 Uiso 1 1 calc R U . . .
C7 C 0.41256(10) 0.3638(2) 0.25204(9) 0.0304(4) Uani 1 1 d . . . . .
C8 C 0.43414(12) 0.4934(2) 0.23969(11) 0.0391(5) Uani 1 1 d . . . . .
H8 H 0.4399 0.5236 0.1946 0.047 Uiso 1 1 calc R U . . .
C9 C 0.44695(11) 0.5768(2) 0.29301(11) 0.0375(5) Uani 1 1 d . . . . .
H9 H 0.4621 0.6649 0.2856 0.045 Uiso 1 1 calc R U . . .
C10 C 0.43710(9) 0.52868(17) 0.35852(10) 0.0262(4) Uani 1 1 d . . . . .
C11 C 0.36892(9) 0.04177(16) 0.40865(9) 0.0212(3) Uani 1 1 d . . . . .
C12 C 0.36851(10) -0.05290(18) 0.35790(9) 0.0279(4) Uani 1 1 d . . . . .
H12 H 0.4087 -0.1051 0.3497 0.033 Uiso 1 1 calc R U . . .
C13 C 0.30900(11) -0.0708(2) 0.31917(10) 0.0355(5) Uani 1 1 d . . . . .
H13 H 0.3081 -0.1351 0.2842 0.043 Uiso 1 1 calc R U . . .
C14 C 0.25102(11) 0.0061(2) 0.33210(11) 0.0368(5) Uani 1 1 d . . . . .
H14 H 0.2103 -0.0058 0.3056 0.044 Uiso 1 1 calc R U . . .
C15 C 0.25110(10) 0.1003(2) 0.38289(10) 0.0312(4) Uani 1 1 d . . . . .
H15 H 0.2102 0.1505 0.3915 0.037 Uiso 1 1 calc R U . . .
C16 C 0.31083(9) 0.12200(17) 0.42157(9) 0.0224(4) Uani 1 1 d . . . . .
C17 C 0.25706(10) 0.29667(18) 0.49166(10) 0.0288(4) Uani 1 1 d . . . . .
H17A H 0.2294 0.3158 0.4506 0.035 Uiso 1 1 calc R U . . .
H17B H 0.2743 0.3819 0.5096 0.035 Uiso 1 1 calc R U . . .
C18 C 0.20993(9) 0.23371(17) 0.54401(9) 0.0230(4) Uani 1 1 d . . . . .
C19 C 0.14478(10) 0.2896(2) 0.55640(10) 0.0295(4) Uani 1 1 d . . . . .
H19 H 0.1301 0.3641 0.5309 0.035 Uiso 1 1 calc R U . . .
C20 C 0.10122(11) 0.2376(2) 0.60540(12) 0.0368(5) Uani 1 1 d . . . . .
H20 H 0.0570 0.2767 0.6134 0.044 Uiso 1 1 calc R U . . .
C21 C 0.12179(12) 0.1288(3) 0.64270(11) 0.0418(5) Uani 1 1 d . . . . .
H21 H 0.0918 0.0927 0.6761 0.050 Uiso 1 1 calc R U . . .
C22 C 0.18620(12) 0.0732(2) 0.63107(11) 0.0411(5) Uani 1 1 d . . . . .
H22 H 0.2007 -0.0010 0.6569 0.049 Uiso 1 1 calc R U . . .
C23 C 0.23016(10) 0.12483(19) 0.58181(10) 0.0305(4) Uani 1 1 d . . . . .
H23 H 0.2743 0.0853 0.5740 0.037 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 C7 1.903(2) . ?
O1 C1 1.241(2) . ?
N1 C3 1.365(2) . ?
N1 C10 1.370(3) . ?
N1 H1 0.85(3) . ?
N2 C1 1.336(2) . ?
N2 C11 1.409(2) . ?
N2 H2 0.84(2) . ?
N3 C16 1.391(2) . ?
N3 C17 1.456(2) . ?
N3 C2 1.460(2) . ?
C1 C2 1.520(2) . ?
C2 C4 1.509(2) . ?
C2 H2A 1.0000 . ?
C3 C4 1.368(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.445(2) . ?
C5 C6 1.399(2) . ?
C5 C10 1.420(2) . ?
C6 C7 1.377(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.398(3) . ?
C8 C9 1.374(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.398(3) . ?
C9 H9 0.9500 . ?
C11 C12 1.388(3) . ?
C11 C16 1.404(2) . ?
C12 C13 1.388(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.383(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.385(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.396(3) . ?
C15 H15 0.9500 . ?
C17 C18 1.516(2) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C23 1.388(3) . ?
C18 C19 1.395(3) . ?
C19 C20 1.385(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.383(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.379(3) . ?
C21 H21 0.9500 . ?
C22 C23 1.392(3) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 N1 C10 108.90(15) . . ?
C3 N1 H1 122.9(18) . . ?
C10 N1 H1 127.3(18) . . ?
C1 N2 C11 123.79(15) . . ?
C1 N2 H2 118.9(15) . . ?
C11 N2 H2 116.5(15) . . ?
C16 N3 C17 120.66(15) . . ?
C16 N3 C2 118.59(14) . . ?
C17 N3 C2 115.69(14) . . ?
O1 C1 N2 122.07(15) . . ?
O1 C1 C2 120.98(15) . . ?
N2 C1 C2 116.95(15) . . ?
N3 C2 C4 116.39(14) . . ?
N3 C2 C1 109.58(13) . . ?
C4 C2 C1 112.36(14) . . ?
N3 C2 H2A 105.9 . . ?
C4 C2 H2A 105.9 . . ?
C1 C2 H2A 105.9 . . ?
N1 C3 C4 110.65(16) . . ?
N1 C3 H3 124.7 . . ?
C4 C3 H3 124.7 . . ?
C3 C4 C5 106.27(15) . . ?
C3 C4 C2 122.33(16) . . ?
C5 C4 C2 131.39(15) . . ?
C6 C5 C10 118.70(16) . . ?
C6 C5 C4 135.01(16) . . ?
C10 C5 C4 106.19(15) . . ?
C7 C6 C5 118.09(17) . . ?
C7 C6 H6 121.0 . . ?
C5 C6 H6 121.0 . . ?
C6 C7 C8 123.19(18) . . ?
C6 C7 Br1 118.33(15) . . ?
C8 C7 Br1 118.40(15) . . ?
C9 C8 C7 119.73(18) . . ?
C9 C8 H8 120.1 . . ?
C7 C8 H8 120.1 . . ?
C8 C9 C10 118.28(18) . . ?
C8 C9 H9 120.9 . . ?
C10 C9 H9 120.9 . . ?
N1 C10 C9 129.97(17) . . ?
N1 C10 C5 107.98(16) . . ?
C9 C10 C5 122.00(18) . . ?
C12 C11 C16 121.79(16) . . ?
C12 C11 N2 119.88(16) . . ?
C16 C11 N2 118.32(15) . . ?
C13 C12 C11 119.62(18) . . ?
C13 C12 H12 120.2 . . ?
C11 C12 H12 120.2 . . ?
C14 C13 C12 119.16(19) . . ?
C14 C13 H13 120.4 . . ?
C12 C13 H13 120.4 . . ?
C13 C14 C15 121.41(18) . . ?
C13 C14 H14 119.3 . . ?
C15 C14 H14 119.3 . . ?
C14 C15 C16 120.45(18) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 H15 119.8 . . ?
N3 C16 C15 124.81(17) . . ?
N3 C16 C11 117.65(15) . . ?
C15 C16 C11 117.52(17) . . ?
N3 C17 C18 113.84(15) . . ?
N3 C17 H17A 108.8 . . ?
C18 C17 H17A 108.8 . . ?
N3 C17 H17B 108.8 . . ?
C18 C17 H17B 108.8 . . ?
H17A C17 H17B 107.7 . . ?
C23 C18 C19 118.61(18) . . ?
C23 C18 C17 122.34(17) . . ?
C19 C18 C17 119.01(16) . . ?
C20 C19 C18 120.70(19) . . ?
C20 C19 H19 119.6 . . ?
C18 C19 H19 119.6 . . ?
C21 C20 C19 120.3(2) . . ?
C21 C20 H20 119.9 . . ?
C19 C20 H20 119.9 . . ?
C22 C21 C20 119.51(19) . . ?
C22 C21 H21 120.2 . . ?
C20 C21 H21 120.2 . . ?
C21 C22 C23 120.5(2) . . ?
C21 C22 H22 119.7 . . ?
C23 C22 H22 119.7 . . ?
C18 C23 C22 120.41(19) . . ?
C18 C23 H23 119.8 . . ?
C22 C23 H23 119.8 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O1 0.85(3) 2.10(3) 2.930(2) 165(2) 5_666
N2 H2 O1 0.84(2) 1.99(2) 2.8249(19) 170(2) 5_656
C2 H2A Br1 1.00 2.89 3.7604(18) 145.6 7_566
C9 H9 Br1 0.95 3.07 3.656(2) 121.6 3_655

_refine_diff_density_max         1.095
_refine_diff_density_min         -1.036
_refine_diff_density_rms         0.053

####################################################################### 
# 
# 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_ic18595
_database_code_depnum_ccdc_archive 'CCDC 1816894'
_audit_update_record             
;
2018-01-15 deposited with the CCDC.
2018-05-15 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            'C15 H14 N2 O2'
_chemical_formula_weight         254.28

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   28.8295(7)
_cell_length_b                   4.67620(10)
_cell_length_c                   20.3019(5)
_cell_angle_alpha                90
_cell_angle_beta                 117.3759(6)
_cell_angle_gamma                90
_cell_volume                     2430.43(10)
_cell_formula_units_Z            8
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    9997
_cell_measurement_theta_min      3.19
_cell_measurement_theta_max      70.04

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.390
_exptl_crystal_F_000             1072
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.362
_exptl_crystal_size_mid          0.109
_exptl_crystal_size_min          0.064
_exptl_absorpt_coefficient_mu    0.761
_shelx_estimated_absorpt_T_min   0.770
_shelx_estimated_absorpt_T_max   0.953
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6290
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7758
_diffrn_reflns_av_unetI/netI     0.0164
_diffrn_reflns_av_R_equivalents  0.0196
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         4.518
_diffrn_reflns_theta_max         69.965
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             2301
_reflns_number_gt                2215
_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       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0419P)²+2.0032P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2301
_refine_ls_number_parameters     178
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0374
_refine_ls_R_factor_gt           0.0365
_refine_ls_wR_factor_ref         0.0935
_refine_ls_wR_factor_gt          0.0927
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.061
_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 0.23715(3) 0.81424(19) 0.40223(5) 0.0298(2) Uani 1 1 d . . . . .
O2 O 0.23483(3) 0.2808(2) 0.31495(5) 0.0331(2) Uani 1 1 d . . . . .
H2 H 0.2362(7) 0.128(4) 0.3472(10) 0.050 Uiso 1 1 d . U . . .
N1 N 0.29002(4) 0.4869(2) 0.48403(6) 0.0259(2) Uani 1 1 d . . . . .
H1 H 0.2826(6) 0.553(4) 0.5188(9) 0.039 Uiso 1 1 d . U . . .
N2 N 0.32783(4) 0.3343(2) 0.38661(5) 0.0281(2) Uani 1 1 d . . . . .
C1 C 0.26763(4) 0.6082(3) 0.41723(7) 0.0249(3) Uani 1 1 d . . . . .
C2 C 0.27743(5) 0.4692(3) 0.35686(7) 0.0270(3) Uani 1 1 d . . . . .
H2A H 0.2769 0.6245 0.3227 0.032 Uiso 1 1 calc R U . . .
C3 C 0.32858(4) 0.2745(3) 0.50509(7) 0.0247(3) Uani 1 1 d . . . . .
C4 C 0.34817(5) 0.1515(3) 0.57479(7) 0.0303(3) Uani 1 1 d . . . . .
H4 H 0.3342 0.2039 0.6073 0.036 Uiso 1 1 calc R U . . .
C5 C 0.38815(5) -0.0478(3) 0.59723(8) 0.0357(3) Uani 1 1 d . . . . .
H5 H 0.4017 -0.1327 0.6450 0.043 Uiso 1 1 calc R U . . .
C6 C 0.40818(5) -0.1217(3) 0.54931(8) 0.0367(3) Uani 1 1 d . . . . .
H6 H 0.4358 -0.2569 0.5646 0.044 Uiso 1 1 calc R U . . .
C7 C 0.38839(5) -0.0006(3) 0.47933(8) 0.0329(3) Uani 1 1 d . . . . .
H7 H 0.4027 -0.0538 0.4472 0.040 Uiso 1 1 calc R U . . .
C8 C 0.34784(4) 0.1983(3) 0.45527(7) 0.0257(3) Uani 1 1 d . . . . .
C9 C 0.34297(5) 0.2377(3) 0.33013(7) 0.0323(3) Uani 1 1 d . . . . .
H9A H 0.3127 0.2616 0.2805 0.039 Uiso 1 1 calc R U . . .
H9B H 0.3513 0.0310 0.3375 0.039 Uiso 1 1 calc R U . . .
C10 C 0.38919(5) 0.3938(3) 0.33131(7) 0.0270(3) Uani 1 1 d . . . . .
C11 C 0.43003(5) 0.4988(3) 0.39591(7) 0.0312(3) Uani 1 1 d . . . . .
H11 H 0.4297 0.4700 0.4420 0.037 Uiso 1 1 calc R U . . .
C12 C 0.47121(5) 0.6451(3) 0.39402(8) 0.0369(3) Uani 1 1 d . . . . .
H12 H 0.4986 0.7188 0.4386 0.044 Uiso 1 1 calc R U . . .
C13 C 0.47251(6) 0.6837(4) 0.32757(9) 0.0459(4) Uani 1 1 d . . . . .
H13 H 0.5007 0.7840 0.3261 0.055 Uiso 1 1 calc R U . . .
C14 C 0.43255(6) 0.5757(4) 0.26304(9) 0.0517(4) Uani 1 1 d . . . . .
H14 H 0.4336 0.5988 0.2173 0.062 Uiso 1 1 calc R U . . .
C15 C 0.39101(6) 0.4341(4) 0.26483(8) 0.0402(3) Uani 1 1 d . . . . .
H15 H 0.3634 0.3637 0.2200 0.048 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
O1 C1 1.2439(15) . ?
O2 C2 1.4311(15) . ?
N1 C1 1.3313(16) . ?
N1 C3 1.4030(15) . ?
N2 C8 1.3933(16) . ?
N2 C2 1.4375(16) . ?
N2 C9 1.4731(15) . ?
C1 C2 1.5241(17) . ?
C3 C4 1.3844(17) . ?
C3 C8 1.4053(17) . ?
C4 C5 1.3862(18) . ?
C5 C6 1.384(2) . ?
C6 C7 1.385(2) . ?
C7 C8 1.3944(18) . ?
C9 C10 1.5101(18) . ?
C10 C15 1.3875(18) . ?
C10 C11 1.3881(18) . ?
C11 C12 1.3861(19) . ?
C12 C13 1.379(2) . ?
C13 C14 1.382(2) . ?
C14 C15 1.383(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C3 123.86(10) . . ?
C8 N2 C2 119.63(10) . . ?
C8 N2 C9 120.27(11) . . ?
C2 N2 C9 114.31(10) . . ?
O1 C1 N1 122.44(11) . . ?
O1 C1 C2 120.32(10) . . ?
N1 C1 C2 117.08(11) . . ?
O2 C2 N2 113.87(10) . . ?
O2 C2 C1 108.35(9) . . ?
N2 C2 C1 112.00(10) . . ?
C4 C3 N1 119.95(11) . . ?
C4 C3 C8 121.32(11) . . ?
N1 C3 C8 118.69(11) . . ?
C3 C4 C5 120.13(12) . . ?
C6 C5 C4 119.30(12) . . ?
C5 C6 C7 120.68(12) . . ?
C6 C7 C8 121.04(12) . . ?
N2 C8 C7 123.36(11) . . ?
N2 C8 C3 119.04(11) . . ?
C7 C8 C3 117.51(11) . . ?
N2 C9 C10 114.49(10) . . ?
C15 C10 C11 118.43(12) . . ?
C15 C10 C9 118.55(11) . . ?
C11 C10 C9 123.01(11) . . ?
C12 C11 C10 120.90(12) . . ?
C13 C12 C11 120.05(13) . . ?
C12 C13 C14 119.59(14) . . ?
C13 C14 C15 120.28(14) . . ?
C14 C15 C10 120.72(13) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2 O1 0.96(2) 1.84(2) 2.7920(13) 175.2(16) 1_545
N1 H1 O1 0.881(18) 2.030(18) 2.9109(14) 176.9(16) 7_566

_refine_diff_density_max         0.349
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.035

####################################################################### 
# 
# 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_ic18614
_database_code_depnum_ccdc_archive 'CCDC 1816895'
_audit_update_record             
;
2018-01-15 deposited with the CCDC.
2018-05-15 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            'C15 H12 N2 O2'
_chemical_formula_weight         252.27

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   6.6642(2)
_cell_length_b                   7.5948(2)
_cell_length_c                   12.0893(3)
_cell_angle_alpha                86.2570(7)
_cell_angle_beta                 87.5435(7)
_cell_angle_gamma                79.1977(7)
_cell_volume                     599.46(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    9982
_cell_measurement_theta_min      7.17
_cell_measurement_theta_max      70.09

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.398
_exptl_crystal_F_000             264
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.241
_exptl_crystal_size_mid          0.164
_exptl_crystal_size_min          0.061
_exptl_absorpt_coefficient_mu    0.771
_shelx_estimated_absorpt_T_min   0.836
_shelx_estimated_absorpt_T_max   0.954
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6296
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4360
_diffrn_reflns_av_unetI/netI     0.0172
_diffrn_reflns_av_R_equivalents  0.0128
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         7.169
_diffrn_reflns_theta_max         69.988
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             2256
_reflns_number_gt                2151
_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       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0446P)²+0.1643P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2256
_refine_ls_number_parameters     176
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0366
_refine_ls_R_factor_gt           0.0355
_refine_ls_wR_factor_ref         0.0936
_refine_ls_wR_factor_gt          0.0925
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.055
_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 1.53504(11) 0.28331(10) 0.07563(6) 0.0292(2) Uani 1 1 d . . . . .
O2 O 1.32042(14) 0.07490(12) 0.20671(9) 0.0473(3) Uani 1 1 d . . . . .
N1 N 1.26566(13) 0.51409(12) 0.08135(7) 0.0247(2) Uani 1 1 d . . . . .
H1 H 1.336(2) 0.582(2) 0.0349(13) 0.041(4) Uiso 1 1 d . . . . .
N2 N 1.03992(13) 0.29839(11) 0.20600(7) 0.0235(2) Uani 1 1 d . . . . .
C1 C 1.35912(16) 0.34483(14) 0.10701(8) 0.0241(2) Uani 1 1 d . . . . .
C2 C 1.23845(17) 0.22687(14) 0.17842(9) 0.0283(3) Uani 1 1 d . . . . .
C3 C 1.06467(16) 0.58534(14) 0.11305(8) 0.0229(2) Uani 1 1 d . . . . .
C4 C 0.98066(17) 0.76274(14) 0.08051(9) 0.0269(2) Uani 1 1 d . . . . .
H4 H 1.0606 0.8348 0.0374 0.032 Uiso 1 1 calc R U . . .
C5 C 0.78120(17) 0.83336(14) 0.11102(9) 0.0285(3) Uani 1 1 d . . . . .
H5 H 0.7229 0.9535 0.0884 0.034 Uiso 1 1 calc R U . . .
C6 C 0.66649(17) 0.72746(15) 0.17506(9) 0.0279(3) Uani 1 1 d . . . . .
H6 H 0.5297 0.7764 0.1967 0.033 Uiso 1 1 calc R U . . .
C7 C 0.74882(16) 0.55145(14) 0.20787(9) 0.0254(2) Uani 1 1 d . . . . .
H7 H 0.6686 0.4808 0.2519 0.030 Uiso 1 1 calc R U . . .
C8 C 0.94956(16) 0.47770(13) 0.17640(8) 0.0221(2) Uani 1 1 d . . . . .
C9 C 0.91523(17) 0.17804(14) 0.26472(9) 0.0263(2) Uani 1 1 d . . . . .
H9A H 0.9879 0.0524 0.2597 0.032 Uiso 1 1 calc R U . . .
H9B H 0.7844 0.1902 0.2265 0.032 Uiso 1 1 calc R U . . .
C10 C 0.86931(17) 0.21437(14) 0.38559(9) 0.0270(2) Uani 1 1 d . . . . .
C11 C 0.6783(2) 0.2028(2) 0.43133(11) 0.0456(3) Uani 1 1 d . . . . .
H11 H 0.5759 0.1765 0.3860 0.055 Uiso 1 1 calc R U . . .
C12 C 0.6350(2) 0.2291(3) 0.54311(12) 0.0586(4) Uani 1 1 d . . . . .
H12 H 0.5036 0.2200 0.5740 0.070 Uiso 1 1 calc R U . . .
C13 C 0.7817(2) 0.2684(2) 0.60919(11) 0.0483(4) Uani 1 1 d . . . . .
H13 H 0.7514 0.2883 0.6854 0.058 Uiso 1 1 calc R U . . .
C14 C 0.9719(2) 0.2786(2) 0.56447(11) 0.0453(3) Uani 1 1 d . . . . .
H14 H 1.0740 0.3047 0.6100 0.054 Uiso 1 1 calc R U . . .
C15 C 1.01618(19) 0.25114(18) 0.45300(10) 0.0375(3) Uani 1 1 d . . . . .
H15 H 1.1488 0.2577 0.4229 0.045 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
O1 C1 1.2314(13) . ?
O2 C2 1.2148(13) . ?
N1 C1 1.3420(13) . ?
N1 C3 1.3947(13) . ?
N2 C2 1.3687(14) . ?
N2 C8 1.4116(13) . ?
N2 C9 1.4762(13) . ?
C1 C2 1.5179(15) . ?
C3 C8 1.3951(15) . ?
C3 C4 1.3966(14) . ?
C4 C5 1.3810(16) . ?
C5 C6 1.3889(16) . ?
C6 C7 1.3856(15) . ?
C7 C8 1.3969(15) . ?
C9 C10 1.5126(15) . ?
C10 C15 1.3786(17) . ?
C10 C11 1.3817(17) . ?
C11 C12 1.389(2) . ?
C12 C13 1.375(2) . ?
C13 C14 1.370(2) . ?
C14 C15 1.3879(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
C1 N1 C3 124.27(9) . . ?
C2 N2 C8 122.81(9) . . ?
C2 N2 C9 117.56(9) . . ?
C8 N2 C9 119.57(9) . . ?
O1 C1 N1 123.16(10) . . ?
O1 C1 C2 119.69(9) . . ?
N1 C1 C2 117.15(9) . . ?
O2 C2 N2 123.53(10) . . ?
O2 C2 C1 119.06(10) . . ?
N2 C2 C1 117.40(9) . . ?
N1 C3 C8 119.43(9) . . ?
N1 C3 C4 119.75(10) . . ?
C8 C3 C4 120.82(10) . . ?
C5 C4 C3 119.92(10) . . ?
C4 C5 C6 119.53(10) . . ?
C7 C6 C5 120.91(10) . . ?
C6 C7 C8 120.13(10) . . ?
C3 C8 C7 118.69(9) . . ?
C3 C8 N2 118.83(9) . . ?
C7 C8 N2 122.48(10) . . ?
N2 C9 C10 114.14(9) . . ?
C15 C10 C11 118.83(11) . . ?
C15 C10 C9 121.67(10) . . ?
C11 C10 C9 119.43(11) . . ?
C10 C11 C12 120.46(13) . . ?
C13 C12 C11 120.20(13) . . ?
C14 C13 C12 119.59(12) . . ?
C13 C14 C15 120.36(13) . . ?
C10 C15 C14 120.55(12) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O1 0.912(16) 1.903(16) 2.8110(12) 173.3(14) 2_865
C9 H9B O1 0.99 2.50 3.4326(13) 157.2 1_455

_refine_diff_density_max         0.193
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.032

####################################################################### 
# 
# 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_ic18529_sq
_database_code_depnum_ccdc_archive 'CCDC 1816893'
_audit_update_record             
;
2018-01-15 deposited with the CCDC.
2018-05-15 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            'C49 H42 Cl2 N6 O3'
_chemical_formula_weight         833.78

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   10.3326(2)
_cell_length_b                   20.1095(4)
_cell_length_c                   22.0811(4)
_cell_angle_alpha                90
_cell_angle_beta                 95.5803(8)
_cell_angle_gamma                90
_cell_volume                     4566.34(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    9995
_cell_measurement_theta_min      2.98
_cell_measurement_theta_max      70.28

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.213
_exptl_crystal_F_000             1744
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.223
_exptl_crystal_size_mid          0.196
_exptl_crystal_size_min          0.038
_exptl_absorpt_coefficient_mu    1.652
_shelx_estimated_absorpt_T_min   0.710
_shelx_estimated_absorpt_T_max   0.940
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6652
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            30022
_diffrn_reflns_av_unetI/netI     0.0184
_diffrn_reflns_av_R_equivalents  0.0218
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.979
_diffrn_reflns_theta_max         69.977
_diffrn_reflns_theta_full        67.679
_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             8662
_reflns_number_gt                7380
_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. 
  
 Structure factors included contributions from the .fab file. 
  
 _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       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0622P)²+2.2727P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8662
_refine_ls_number_parameters     559
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0539
_refine_ls_R_factor_gt           0.0453
_refine_ls_wR_factor_ref         0.1311
_refine_ls_wR_factor_gt          0.1194
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.001
_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
Cl1 Cl 0.44190(6) 0.39499(4) 0.43504(3) 0.0765(2) Uani 1 1 d . . . . .
O1 O 0.07187(10) 0.60188(6) 0.20567(6) 0.0391(3) Uani 1 1 d . . . . .
N1 N 0.19064(13) 0.53077(7) 0.26730(7) 0.0360(3) Uani 1 1 d . . . . .
H1 H 0.256(2) 0.5600(11) 0.2714(10) 0.048(6) Uiso 1 1 d . . . . .
N2 N 0.02522(13) 0.42938(7) 0.23435(8) 0.0403(3) Uani 1 1 d . . . . .
N3 N -0.33955(14) 0.54239(7) 0.28002(8) 0.0422(4) Uani 1 1 d . . . . .
H3 H -0.417(2) 0.5588(12) 0.2729(11) 0.059(7) Uiso 1 1 d . . . . .
C1 C 0.08373(14) 0.54742(8) 0.23204(8) 0.0320(3) Uani 1 1 d . . . . .
C2 C -0.02656(14) 0.49707(8) 0.22506(8) 0.0324(3) Uani 1 1 d . . . . .
H2A H -0.0631 0.4994 0.1815 0.039 Uiso 1 1 calc R U . . .
C3 C 0.12066(16) 0.41793(8) 0.28194(9) 0.0371(4) Uani 1 1 d . . . . .
C4 C 0.14137(19) 0.35749(9) 0.31209(10) 0.0474(5) Uani 1 1 d . . . . .
H4A H 0.0866 0.3207 0.3006 0.057 Uiso 1 1 calc R U . . .
C5 C 0.2399(2) 0.35001(10) 0.35835(10) 0.0534(5) Uani 1 1 d . . . . .
H5 H 0.2521 0.3085 0.3787 0.064 Uiso 1 1 calc R U . . .
C6 C 0.32050(19) 0.40269(11) 0.37512(10) 0.0503(5) Uani 1 1 d . . . . .
C7 C 0.30653(16) 0.46330(9) 0.34503(9) 0.0419(4) Uani 1 1 d . . . . .
H7 H 0.3640 0.4992 0.3559 0.050 Uiso 1 1 calc R U . . .
C8 C 0.20695(15) 0.47012(8) 0.29898(8) 0.0358(4) Uani 1 1 d . . . . .
C9 C -0.13605(14) 0.51609(7) 0.26197(8) 0.0304(3) Uani 1 1 d . . . . .
C10 C -0.26099(15) 0.52516(8) 0.23657(9) 0.0373(4) Uani 1 1 d . . . . .
H10 H -0.2889 0.5201 0.1945 0.045 Uiso 1 1 calc R U . . .
C11 C -0.26614(16) 0.54687(8) 0.33506(9) 0.0385(4) Uani 1 1 d . . . . .
C12 C -0.3039(2) 0.56312(10) 0.39220(11) 0.0536(5) Uani 1 1 d . . . . .
H12 H -0.3914 0.5746 0.3974 0.064 Uiso 1 1 calc R U . . .
C13 C -0.2101(2) 0.56194(11) 0.44066(11) 0.0585(6) Uani 1 1 d . . . . .
H13 H -0.2330 0.5726 0.4802 0.070 Uiso 1 1 calc R U . . .
C14 C -0.0815(2) 0.54536(10) 0.43293(9) 0.0507(5) Uani 1 1 d . . . . .
H14 H -0.0186 0.5453 0.4673 0.061 Uiso 1 1 calc R U . . .
C15 C -0.04338(17) 0.52906(8) 0.37662(8) 0.0382(4) Uani 1 1 d . . . . .
H15 H 0.0444 0.5175 0.3723 0.046 Uiso 1 1 calc R U . . .
C16 C -0.13629(15) 0.52982(7) 0.32587(8) 0.0317(3) Uani 1 1 d . . . . .
C17 C -0.06551(18) 0.37627(9) 0.21522(11) 0.0487(5) Uani 1 1 d . . . . .
H17A H -0.1421 0.3957 0.1911 0.058 Uiso 1 1 calc R U . . .
H17B H -0.0962 0.3553 0.2518 0.058 Uiso 1 1 calc R U . . .
C18 C -0.00718(19) 0.32344(9) 0.17768(9) 0.0438(4) Uani 1 1 d . . . . .
C19 C -0.0611(2) 0.26023(10) 0.17522(12) 0.0594(6) Uani 1 1 d . . . . .
H19 H -0.1313 0.2506 0.1986 0.071 Uiso 1 1 calc R U . . .
C20 C -0.0155(3) 0.21151(13) 0.13987(15) 0.0845(10) Uani 1 1 d . . . . .
H20 H -0.0534 0.1684 0.1393 0.101 Uiso 1 1 calc R U . . .
C21 C 0.0842(4) 0.22441(16) 0.10542(14) 0.0936(12) Uani 1 1 d . . . . .
H21 H 0.1146 0.1906 0.0803 0.112 Uiso 1 1 calc R U . . .
C22 C 0.1411(3) 0.28680(18) 0.10714(12) 0.0897(10) Uani 1 1 d . . . . .
H22 H 0.2110 0.2958 0.0834 0.108 Uiso 1 1 calc R U . . .
C23 C 0.0954(3) 0.33657(12) 0.14405(11) 0.0634(6) Uani 1 1 d . . . . .
H23 H 0.1351 0.3792 0.1459 0.076 Uiso 1 1 calc R U . . .
Cl2 Cl 0.02955(5) 0.83686(3) 0.05851(2) 0.05767(15) Uani 1 1 d . . . . .
O2 O 0.41372(10) 0.61023(6) 0.26264(6) 0.0402(3) Uani 1 1 d . . . . .
N4 N 0.28886(13) 0.68888(7) 0.21395(7) 0.0344(3) Uani 1 1 d . . . . .
H4 H 0.225(2) 0.6601(11) 0.2087(10) 0.047(6) Uiso 1 1 d . . . . .
N5 N 0.46180(13) 0.78663(7) 0.24934(7) 0.0377(3) Uani 1 1 d . . . . .
N6 N 0.82107(15) 0.67453(8) 0.19627(10) 0.0520(5) Uani 1 1 d . . . . .
H6 H 0.895(3) 0.6601(12) 0.2034(11) 0.059(7) Uiso 1 1 d . . . . .
C24 C 0.39985(14) 0.66802(8) 0.24426(8) 0.0324(3) Uani 1 1 d . . . . .
C25 C 0.51040(15) 0.71799(8) 0.25498(8) 0.0333(3) Uani 1 1 d . . . . .
H25 H 0.5464 0.7124 0.2984 0.040 Uiso 1 1 calc R U . . .
C26 C 0.36267(15) 0.80200(8) 0.20444(8) 0.0331(3) Uani 1 1 d . . . . .
C27 C 0.34159(18) 0.86439(8) 0.17799(9) 0.0400(4) Uani 1 1 d . . . . .
H27 H 0.3982 0.9000 0.1906 0.048 Uiso 1 1 calc R U . . .
C28 C 0.23976(19) 0.87551(9) 0.13367(9) 0.0425(4) Uani 1 1 d . . . . .
H28 H 0.2282 0.9182 0.1155 0.051 Uiso 1 1 calc R U . . .
C29 C 0.15507(17) 0.82461(9) 0.11588(8) 0.0405(4) Uani 1 1 d . . . . .
C30 C 0.16961(16) 0.76219(8) 0.14260(8) 0.0357(4) Uani 1 1 d . . . . .
H30 H 0.1101 0.7274 0.1310 0.043 Uiso 1 1 calc R U . . .
C31 C 0.27238(14) 0.75165(8) 0.18647(8) 0.0318(3) Uani 1 1 d . . . . .
C32 C 0.61927(14) 0.70035(8) 0.21697(8) 0.0337(3) Uani 1 1 d . . . . .
C33 C 0.74575(16) 0.69273(9) 0.24070(10) 0.0424(4) Uani 1 1 d . . . . .
H33 H 0.7765 0.6992 0.2822 0.051 Uiso 1 1 calc R U . . .
C34 C 0.74362(19) 0.66720(9) 0.14269(11) 0.0487(5) Uani 1 1 d . . . . .
C35 C 0.7760(3) 0.64646(12) 0.08581(14) 0.0708(7) Uani 1 1 d . . . . .
H35 H 0.8629 0.6351 0.0795 0.085 Uiso 1 1 calc R U . . .
C36 C 0.6778(3) 0.64298(15) 0.03928(14) 0.0831(9) Uani 1 1 d . . . . .
H36 H 0.6969 0.6286 0.0001 0.100 Uiso 1 1 calc R U . . .
C37 C 0.5496(3) 0.66024(14) 0.04860(11) 0.0720(7) Uani 1 1 d . . . . .
H37 H 0.4834 0.6573 0.0157 0.086 Uiso 1 1 calc R U . . .
C38 C 0.5179(2) 0.68135(11) 0.10463(9) 0.0514(5) Uani 1 1 d . . . . .
H38 H 0.4311 0.6938 0.1101 0.062 Uiso 1 1 calc R U . . .
C39 C 0.61515(16) 0.68429(8) 0.15343(9) 0.0381(4) Uani 1 1 d . . . . .
C40 C 0.55633(17) 0.83761(9) 0.27017(10) 0.0440(4) Uani 1 1 d . . . . .
H40A H 0.5776 0.8641 0.2346 0.053 Uiso 1 1 calc R U . . .
H40B H 0.6372 0.8155 0.2875 0.053 Uiso 1 1 calc R U . . .
C41 C 0.51047(17) 0.88422(9) 0.31728(8) 0.0382(4) Uani 1 1 d . . . . .
C42 C 0.4137(2) 0.86699(11) 0.35314(9) 0.0497(5) Uani 1 1 d . . . . .
H42 H 0.3701 0.8256 0.3469 0.060 Uiso 1 1 calc R U . . .
C43 C 0.3796(3) 0.90975(15) 0.39819(10) 0.0698(7) Uani 1 1 d . . . . .
H43 H 0.3126 0.8975 0.4226 0.084 Uiso 1 1 calc R U . . .
C44 C 0.4422(3) 0.97003(15) 0.40787(11) 0.0761(8) Uani 1 1 d . . . . .
H44 H 0.4195 0.9989 0.4392 0.091 Uiso 1 1 calc R U . . .
C45 C 0.5374(3) 0.98797(12) 0.37178(12) 0.0695(7) Uani 1 1 d . . . . .
H45 H 0.5802 1.0296 0.3778 0.083 Uiso 1 1 calc R U . . .
C46 C 0.5709(2) 0.94550(10) 0.32679(11) 0.0535(5) Uani 1 1 d . . . . .
H46 H 0.6366 0.9584 0.3019 0.064 Uiso 1 1 calc R U . . .
O3 O 0.3589(7) 0.6528(4) 0.3839(2) 0.293(4) Uani 1 1 d . . . . .
C47 C 0.3283(4) 0.6531(3) 0.43141(17) 0.1153(13) Uani 1 1 d . U . . .
C48 C 0.3236(5) 0.7144(2) 0.4663(2) 0.1369(18) Uani 1 1 d . . . . .
H48A H 0.3905 0.7451 0.4546 0.205 Uiso 1 1 calc R U . . .
H48B H 0.3392 0.7043 0.5098 0.205 Uiso 1 1 calc R U . . .
H48C H 0.2377 0.7349 0.4578 0.205 Uiso 1 1 calc R U . . .
C49 C 0.2818(4) 0.5945(3) 0.4617(2) 0.1270(16) Uani 1 1 d . . . . .
H49A H 0.3548 0.5643 0.4727 0.190 Uiso 1 1 calc R U . . .
H49D H 0.2160 0.5717 0.4342 0.190 Uiso 1 1 calc R U . . .
H49B H 0.2433 0.6081 0.4986 0.190 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
Cl1 C6 1.739(2) . ?
O1 C1 1.241(2) . ?
N1 C1 1.331(2) . ?
N1 C8 1.408(2) . ?
N2 C3 1.389(2) . ?
N2 C17 1.456(2) . ?
N2 C2 1.470(2) . ?
N3 C10 1.360(2) . ?
N3 C11 1.372(3) . ?
C1 C2 1.521(2) . ?
C2 C9 1.507(2) . ?
C3 C4 1.392(3) . ?
C3 C8 1.404(2) . ?
C4 C5 1.378(3) . ?
C5 C6 1.376(3) . ?
C6 C7 1.389(3) . ?
C7 C8 1.381(3) . ?
C9 C10 1.369(2) . ?
C9 C16 1.438(2) . ?
C11 C12 1.395(3) . ?
C11 C16 1.418(2) . ?
C12 C13 1.373(3) . ?
C13 C14 1.397(3) . ?
C14 C15 1.380(3) . ?
C15 C16 1.403(2) . ?
C17 C18 1.509(3) . ?
C18 C23 1.378(3) . ?
C18 C19 1.387(3) . ?
C19 C20 1.365(4) . ?
C20 C21 1.364(5) . ?
C21 C22 1.385(5) . ?
C22 C23 1.401(4) . ?
Cl2 C29 1.7401(19) . ?
O2 C24 1.235(2) . ?
N4 C24 1.338(2) . ?
N4 C31 1.404(2) . ?
N5 C26 1.389(2) . ?
N5 C40 1.459(2) . ?
N5 C25 1.470(2) . ?
N6 C33 1.360(3) . ?
N6 C34 1.370(3) . ?
C24 C25 1.522(2) . ?
C25 C32 1.510(2) . ?
C26 C27 1.392(2) . ?
C26 C31 1.407(2) . ?
C27 C28 1.384(3) . ?
C28 C29 1.379(3) . ?
C29 C30 1.389(2) . ?
C30 C31 1.382(2) . ?
C32 C33 1.368(2) . ?
C32 C39 1.436(3) . ?
C34 C35 1.394(3) . ?
C34 C39 1.413(2) . ?
C35 C36 1.374(4) . ?
C36 C37 1.404(4) . ?
C37 C38 1.377(3) . ?
C38 C39 1.401(3) . ?
C40 C41 1.510(3) . ?
C41 C42 1.379(3) . ?
C41 C46 1.388(3) . ?
C42 C43 1.386(3) . ?
C43 C44 1.381(4) . ?
C44 C45 1.373(4) . ?
C45 C46 1.379(3) . ?
O3 C47 1.125(5) . ?
C47 C48 1.456(6) . ?
C47 C49 1.461(7) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C8 124.12(14) . . ?
C3 N2 C17 119.19(16) . . ?
C3 N2 C2 118.77(13) . . ?
C17 N2 C2 115.05(14) . . ?
C10 N3 C11 108.98(14) . . ?
O1 C1 N1 122.34(14) . . ?
O1 C1 C2 120.08(14) . . ?
N1 C1 C2 117.57(14) . . ?
N2 C2 C9 116.23(14) . . ?
N2 C2 C1 110.09(12) . . ?
C9 C2 C1 111.77(13) . . ?
N2 C3 C4 124.84(17) . . ?
N2 C3 C8 117.68(15) . . ?
C4 C3 C8 117.40(17) . . ?
C5 C4 C3 121.17(19) . . ?
C6 C5 C4 119.97(18) . . ?
C5 C6 C7 120.99(19) . . ?
C5 C6 Cl1 120.61(16) . . ?
C7 C6 Cl1 118.40(18) . . ?
C8 C7 C6 118.32(18) . . ?
C7 C8 C3 122.08(16) . . ?
C7 C8 N1 119.75(15) . . ?
C3 C8 N1 118.16(15) . . ?
C10 C9 C16 106.55(14) . . ?
C10 C9 C2 122.69(16) . . ?
C16 C9 C2 130.74(14) . . ?
N3 C10 C9 110.40(16) . . ?
N3 C11 C12 129.59(17) . . ?
N3 C11 C16 107.85(16) . . ?
C12 C11 C16 122.54(18) . . ?
C13 C12 C11 117.51(18) . . ?
C12 C13 C14 121.16(19) . . ?
C15 C14 C13 121.7(2) . . ?
C14 C15 C16 118.97(17) . . ?
C15 C16 C11 118.14(16) . . ?
C15 C16 C9 135.67(15) . . ?
C11 C16 C9 106.19(14) . . ?
N2 C17 C18 113.30(15) . . ?
C23 C18 C19 118.8(2) . . ?
C23 C18 C17 122.06(18) . . ?
C19 C18 C17 119.10(19) . . ?
C20 C19 C18 121.4(3) . . ?
C21 C20 C19 120.3(3) . . ?
C20 C21 C22 119.9(2) . . ?
C21 C22 C23 119.8(3) . . ?
C18 C23 C22 119.8(3) . . ?
C24 N4 C31 124.07(14) . . ?
C26 N5 C40 119.55(15) . . ?
C26 N5 C25 119.43(13) . . ?
C40 N5 C25 114.86(13) . . ?
C33 N6 C34 108.94(15) . . ?
O2 C24 N4 121.73(14) . . ?
O2 C24 C25 120.59(14) . . ?
N4 C24 C25 117.68(14) . . ?
N5 C25 C32 116.13(14) . . ?
N5 C25 C24 111.20(12) . . ?
C32 C25 C24 110.29(14) . . ?
N5 C26 C27 125.05(15) . . ?
N5 C26 C31 117.62(14) . . ?
C27 C26 C31 117.24(16) . . ?
C28 C27 C26 121.30(16) . . ?
C29 C28 C27 119.97(16) . . ?
C28 C29 C30 120.69(17) . . ?
C28 C29 Cl2 120.65(14) . . ?
C30 C29 Cl2 118.65(15) . . ?
C31 C30 C29 118.70(16) . . ?
C30 C31 N4 119.56(14) . . ?
C30 C31 C26 122.03(15) . . ?
N4 C31 C26 118.42(14) . . ?
C33 C32 C39 106.58(16) . . ?
C33 C32 C25 123.29(17) . . ?
C39 C32 C25 130.01(14) . . ?
N6 C33 C32 110.24(18) . . ?
N6 C34 C35 129.7(2) . . ?
N6 C34 C39 107.94(18) . . ?
C35 C34 C39 122.3(2) . . ?
C36 C35 C34 117.7(2) . . ?
C35 C36 C37 121.1(2) . . ?
C38 C37 C36 121.2(3) . . ?
C37 C38 C39 119.3(2) . . ?
C38 C39 C34 118.39(19) . . ?
C38 C39 C32 135.38(16) . . ?
C34 C39 C32 106.23(17) . . ?
N5 C40 C41 114.08(14) . . ?
C42 C41 C46 118.49(19) . . ?
C42 C41 C40 122.23(17) . . ?
C46 C41 C40 119.23(17) . . ?
C41 C42 C43 120.4(2) . . ?
C44 C43 C42 120.5(2) . . ?
C45 C44 C43 119.5(2) . . ?
C44 C45 C46 120.0(2) . . ?
C45 C46 C41 121.2(2) . . ?
O3 C47 C48 121.7(7) . . ?
O3 C47 C49 123.9(6) . . ?
C48 C47 C49 114.3(3) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O2 0.90(2) 1.94(2) 2.8148(18) 165(2) .
N3 H3 O2 0.86(3) 2.03(3) 2.8841(18) 171(2) 1_455
N4 H4 O1 0.88(2) 1.97(2) 2.8357(17) 172(2) .
N6 H6 O1 0.82(3) 2.16(3) 2.9645(19) 165(2) 1_655

_refine_diff_density_max         0.517
_refine_diff_density_min         -0.369
_refine_diff_density_rms         0.041



