# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_Compound_1_isbd_10
_database_code_depnum_ccdc_archive 'CCDC 1505866'
_audit_update_record             
;
2016-09-22 deposited with the CCDC.
2017-01-29 downloaded from the CCDC.
;
_audit_creation_date             2014-08-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C15 H12 N2 O'
_chemical_formula_sum            'C15 H12 N2 O'
_chemical_formula_weight         236.27
_chemical_melting_point          ?

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.4554(3)
_cell_length_b                   11.8767(3)
_cell_length_c                   10.4401(2)
_cell_angle_alpha                90
_cell_angle_beta                 91.738(2)
_cell_angle_gamma                90
_cell_volume                     1171.88(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3285
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      75.8460
_cell_measurement_theta_min      3.7700
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.685
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79556
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.21
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0196
_diffrn_reflns_av_unetI/netI     0.0194
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5796
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.493
_diffrn_reflns_theta_min         4.679
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.3829
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -37.00  -11.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787  -57.0000    0.0000 26

#__ type_ start__ end____ width___ exp.time_
  2 omega -113.00  -76.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787  -57.0000    0.0000 37

#__ type_ start__ end____ width___ exp.time_
  3 omega  -50.00   32.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787   38.0000  150.0000 82

#__ type_ start__ end____ width___ exp.time_
  4 omega  -82.00  -56.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787 -152.0000  141.0000 26

#__ type_ start__ end____ width___ exp.time_
  5 omega   96.00  122.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.3787  178.0000 -180.0000 26

#__ type_ start__ end____ width___ exp.time_
  6 omega   60.00  128.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.3787  178.0000  -30.0000 68

#__ type_ start__ end____ width___ exp.time_
  7 omega   36.00   80.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000 -180.0000 44

#__ type_ start__ end____ width___ exp.time_
  8 omega   63.00  102.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  178.0000  150.0000 39

#__ type_ start__ end____ width___ exp.time_
  9 omega   53.00   82.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000   90.0000 29

#__ type_ start__ end____ width___ exp.time_
 10 omega   80.00  109.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000 -150.0000 29

#__ type_ start__ end____ width___ exp.time_
 11 omega   34.00  101.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000    0.0000 67

#__ type_ start__ end____ width___ exp.time_
 12 omega   47.00   73.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000  -30.0000 26

#__ type_ start__ end____ width___ exp.time_
 13 omega   89.00  115.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000  -30.0000 26

#__ type_ start__ end____ width___ exp.time_
 14 omega   83.00  109.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000  -30.0000 26

#__ type_ start__ end____ width___ exp.time_
 15 omega  111.00  169.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  112.0000 -120.0000 58

#__ type_ start__ end____ width___ exp.time_
 16 omega   50.00   76.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000 -150.0000 26

#__ type_ start__ end____ width___ exp.time_
 17 omega   73.00   98.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000  -30.0000 25

#__ type_ start__ end____ width___ exp.time_
 18 omega   36.00   90.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000   90.0000 54

#__ type_ start__ end____ width___ exp.time_
 19 omega   44.00   70.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000  -30.0000 26

#__ type_ start__ end____ width___ exp.time_
 20 omega   83.00  113.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000   30.0000 30

#__ type_ start__ end____ width___ exp.time_
 21 omega   45.00   93.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000 -180.0000 48

#__ type_ start__ end____ width___ exp.time_
 22 omega   98.00  133.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  152.0000 -176.0000 35

#__ type_ start__ end____ width___ exp.time_
 23 omega  140.00  177.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000  -30.0000 37

#__ type_ start__ end____ width___ exp.time_
 24 omega   99.00  124.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   30.0000 -150.0000 25
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0215878000
_diffrn_orient_matrix_UB_12      0.1231704000
_diffrn_orient_matrix_UB_13      -0.0415809000
_diffrn_orient_matrix_UB_21      0.1101341000
_diffrn_orient_matrix_UB_22      -0.0386397000
_diffrn_orient_matrix_UB_23      -0.0965480000
_diffrn_orient_matrix_UB_31      -0.1182071000
_diffrn_orient_matrix_UB_32      -0.0132374000
_diffrn_orient_matrix_UB_33      -0.1035703000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2018
_reflns_number_total             2277
_reflns_odcompleteness_completeness 92.04
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     80.95
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.251
_refine_diff_density_min         -0.162
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2277
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0421
_refine_ls_R_factor_gt           0.0370
_refine_ls_restrained_S_all      1.051
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0466P)²+0.4312P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0929
_refine_ls_wR_factor_ref         0.0970
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C9(H9), C14(H14), C15(H15), C16(H16), C17(H17),
 C18(H18)
2.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C2 C 0.34824(14) 0.69298(11) 0.01959(11) 0.0233(3) Uani 1 1 d . . . . .
C3 C 0.30926(13) 0.59633(11) 0.10889(11) 0.0218(3) Uani 1 1 d . . . . .
C4 C 0.44433(13) 0.55382(11) 0.16385(11) 0.0218(3) Uani 1 1 d . . . . .
C5 C 0.55115(13) 0.62101(11) 0.11251(11) 0.0213(3) Uani 1 1 d . . . . .
C6 C 0.69257(14) 0.60623(12) 0.14556(12) 0.0262(3) Uani 1 1 d . . . . .
H6 H 0.7619 0.6522 0.1120 0.031 Uiso 1 1 calc R . . . .
C7 C 0.72725(14) 0.51972(12) 0.23122(13) 0.0280(3) Uani 1 1 d . . . . .
H7 H 0.8216 0.5080 0.2555 0.034 Uiso 1 1 calc R . . . .
C8 C 0.62427(15) 0.45098(12) 0.28089(13) 0.0294(3) Uani 1 1 d . . . . .
H8 H 0.6503 0.3933 0.3371 0.035 Uiso 1 1 calc R . . . .
C9 C 0.48177(14) 0.46726(11) 0.24762(12) 0.0251(3) Uani 1 1 d . . . . .
H9 H 0.4128 0.4208 0.2811 0.030 Uiso 1 1 calc R . . . .
C10 C 0.57507(15) 0.77980(12) -0.04650(13) 0.0301(3) Uani 1 1 d . . . . .
H10A H 0.6228 0.8321 0.0099 0.045 Uiso 1 1 calc GR . . . .
H10B H 0.5132 0.8201 -0.1049 0.045 Uiso 1 1 calc GR . . . .
H10C H 0.6435 0.7387 -0.0939 0.045 Uiso 1 1 calc GR . . . .
C13 C 0.13456(13) 0.48387(11) 0.20145(12) 0.0223(3) Uani 1 1 d . . . . .
C14 C 0.05858(13) 0.39382(11) 0.14913(12) 0.0245(3) Uani 1 1 d . . . . .
H14 H 0.0439 0.3889 0.0608 0.029 Uiso 1 1 calc R . . . .
C15 C 0.00472(14) 0.31144(12) 0.22802(14) 0.0282(3) Uani 1 1 d . . . . .
H15 H -0.0431 0.2500 0.1924 0.034 Uiso 1 1 calc R . . . .
C16 C 0.02214(14) 0.32043(12) 0.36062(13) 0.0283(3) Uani 1 1 d . . . . .
H16 H -0.0154 0.2659 0.4138 0.034 Uiso 1 1 calc R . . . .
C17 C 0.09587(14) 0.41131(12) 0.41255(13) 0.0273(3) Uani 1 1 d . . . . .
H17 H 0.1075 0.4173 0.5011 0.033 Uiso 1 1 calc R . . . .
C18 C 0.15250(13) 0.49340(12) 0.33482(12) 0.0248(3) Uani 1 1 d . . . . .
H18 H 0.2018 0.5540 0.3707 0.030 Uiso 1 1 calc R . . . .
N1 N 0.49288(12) 0.70186(9) 0.02811(10) 0.0241(3) Uani 1 1 d . . . . .
N12 N 0.17909(11) 0.57028(9) 0.11784(10) 0.0236(2) Uani 1 1 d . . . . .
O11 O 0.26908(10) 0.75199(8) -0.04420(9) 0.0301(2) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C2 C3 1.5309(17) . ?
C2 N1 1.3719(17) . ?
C2 O11 1.2102(16) . ?
C3 C4 1.4734(17) . ?
C3 N12 1.2753(17) . ?
C4 C5 1.4061(17) . ?
C4 C9 1.3886(18) . ?
C5 C6 1.3821(18) . ?
C5 N1 1.4044(16) . ?
C6 H6 0.9300 . ?
C6 C7 1.3948(19) . ?
C7 H7 0.9300 . ?
C7 C8 1.384(2) . ?
C8 H8 0.9300 . ?
C8 C9 1.3946(19) . ?
C9 H9 0.9300 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C10 N1 1.4506(17) . ?
C13 C14 1.3909(18) . ?
C13 C18 1.4021(18) . ?
C13 N12 1.4194(17) . ?
C14 H14 0.9300 . ?
C14 C15 1.3858(19) . ?
C15 H15 0.9300 . ?
C15 C16 1.393(2) . ?
C16 H16 0.9300 . ?
C16 C17 1.386(2) . ?
C17 H17 0.9300 . ?
C17 C18 1.3864(19) . ?
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
N1 C2 C3 106.03(10) . . ?
O11 C2 C3 127.81(12) . . ?
O11 C2 N1 126.15(12) . . ?
C4 C3 C2 105.79(10) . . ?
N12 C3 C2 118.51(11) . . ?
N12 C3 C4 135.68(12) . . ?
C5 C4 C3 106.34(11) . . ?
C9 C4 C3 134.46(12) . . ?
C9 C4 C5 119.20(12) . . ?
C6 C5 C4 122.24(12) . . ?
C6 C5 N1 126.99(12) . . ?
N1 C5 C4 110.77(11) . . ?
C5 C6 H6 121.3 . . ?
C5 C6 C7 117.42(12) . . ?
C7 C6 H6 121.3 . . ?
C6 C7 H7 119.3 . . ?
C8 C7 C6 121.37(13) . . ?
C8 C7 H7 119.3 . . ?
C7 C8 H8 119.7 . . ?
C7 C8 C9 120.70(13) . . ?
C9 C8 H8 119.7 . . ?
C4 C9 C8 119.04(12) . . ?
C4 C9 H9 120.5 . . ?
C8 C9 H9 120.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N1 C10 H10A 109.5 . . ?
N1 C10 H10B 109.5 . . ?
N1 C10 H10C 109.5 . . ?
C14 C13 C18 119.84(12) . . ?
C14 C13 N12 118.27(11) . . ?
C18 C13 N12 121.55(12) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 C13 120.28(12) . . ?
C15 C14 H14 119.9 . . ?
C14 C15 H15 119.9 . . ?
C14 C15 C16 120.13(13) . . ?
C16 C15 H15 119.9 . . ?
C15 C16 H16 120.3 . . ?
C17 C16 C15 119.42(13) . . ?
C17 C16 H16 120.3 . . ?
C16 C17 H17 119.4 . . ?
C16 C17 C18 121.14(12) . . ?
C18 C17 H17 119.4 . . ?
C13 C18 H18 120.4 . . ?
C17 C18 C13 119.16(12) . . ?
C17 C18 H18 120.4 . . ?
C2 N1 C5 111.07(10) . . ?
C2 N1 C10 124.29(11) . . ?
C5 N1 C10 124.53(11) . . ?
C3 N12 C13 121.70(11) . . ?

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
C2 C3 C4 C5 0.85(13) . . . . ?
C2 C3 C4 C9 -178.32(13) . . . . ?
C2 C3 N12 C13 -178.12(10) . . . . ?
C3 C2 N1 C5 0.36(13) . . . . ?
C3 C2 N1 C10 176.74(11) . . . . ?
C3 C4 C5 C6 178.64(11) . . . . ?
C3 C4 C5 N1 -0.67(13) . . . . ?
C3 C4 C9 C8 -179.44(13) . . . . ?
C4 C3 N12 C13 3.4(2) . . . . ?
C4 C5 C6 C7 1.15(19) . . . . ?
C4 C5 N1 C2 0.19(14) . . . . ?
C4 C5 N1 C10 -176.18(11) . . . . ?
C5 C4 C9 C8 1.47(18) . . . . ?
C5 C6 C7 C8 0.26(19) . . . . ?
C6 C5 N1 C2 -179.08(12) . . . . ?
C6 C5 N1 C10 4.6(2) . . . . ?
C6 C7 C8 C9 -0.8(2) . . . . ?
C7 C8 C9 C4 -0.1(2) . . . . ?
C9 C4 C5 C6 -2.04(18) . . . . ?
C9 C4 C5 N1 178.65(11) . . . . ?
C13 C14 C15 C16 2.25(19) . . . . ?
C14 C13 C18 C17 1.11(19) . . . . ?
C14 C13 N12 C3 -122.00(13) . . . . ?
C14 C15 C16 C17 -1.1(2) . . . . ?
C15 C16 C17 C18 0.0(2) . . . . ?
C16 C17 C18 C13 -0.01(19) . . . . ?
C18 C13 C14 C15 -2.23(19) . . . . ?
C18 C13 N12 C3 64.73(17) . . . . ?
N1 C2 C3 C4 -0.75(13) . . . . ?
N1 C2 C3 N12 -179.62(11) . . . . ?
N1 C5 C6 C7 -179.66(12) . . . . ?
N12 C3 C4 C5 179.43(14) . . . . ?
N12 C3 C4 C9 0.3(3) . . . . ?
N12 C13 C14 C15 -175.62(11) . . . . ?
N12 C13 C18 C17 174.28(11) . . . . ?
O11 C2 C3 C4 -179.36(12) . . . . ?
O11 C2 C3 N12 1.8(2) . . . . ?
O11 C2 N1 C5 179.01(12) . . . . ?
O11 C2 N1 C10 -4.6(2) . . . . ?


####################################################################### 
# 
# 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_Compound_2_as32
_database_code_depnum_ccdc_archive 'CCDC 1505868'
_audit_update_record             
;
2016-09-22 deposited with the CCDC.
2017-01-29 downloaded from the CCDC.
;
_audit_creation_date             2016-08-29
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.08.23 svn.r3337 for OlexSys, GUI svn.r5217)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C17 H16 N2 O'
_chemical_formula_sum            'C17 H16 N2 O'
_chemical_formula_weight         264.32
_chemical_melting_point          ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.2483(3)
_cell_length_b                   8.1749(2)
_cell_length_c                   16.2529(6)
_cell_angle_alpha                90
_cell_angle_beta                 102.182(3)
_cell_angle_gamma                90
_cell_volume                     1330.99(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4499
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      32.1060
_cell_measurement_theta_min      3.2150
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96561
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.06
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0266
_diffrn_reflns_av_unetI/netI     0.0248
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            11162
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.500
_diffrn_reflns_theta_min         2.802
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 16.2096
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -96.00  -54.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -25.4031  -38.0000  -30.0000 42

#__ type_ start__ end____ width___ exp.time_
  2 omega  -91.00  -35.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -25.4031 -178.0000   90.0000 56

#__ type_ start__ end____ width___ exp.time_
  3 omega  -63.00  -37.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -25.4031 -178.0000  120.0000 26

#__ type_ start__ end____ width___ exp.time_
  4 omega   -4.00   93.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       26.4968   77.0000   30.0000 97

#__ type_ start__ end____ width___ exp.time_
  5 omega   58.00   99.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       26.4968  178.0000 -150.0000 41

#__ type_ start__ end____ width___ exp.time_
  6 omega  -92.00  -27.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -25.4031  -57.0000  150.0000 65

#__ type_ start__ end____ width___ exp.time_
  7 omega  -43.00   43.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -25.4031   57.0000   30.0000 86

#__ type_ start__ end____ width___ exp.time_
  8 omega   27.00   57.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       26.4968  -77.0000   30.0000 30
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0135527000
_diffrn_orient_matrix_UB_12      -0.0634800000
_diffrn_orient_matrix_UB_13      0.0303766000
_diffrn_orient_matrix_UB_21      -0.0411905000
_diffrn_orient_matrix_UB_22      0.0391882000
_diffrn_orient_matrix_UB_23      0.0240093000
_diffrn_orient_matrix_UB_31      -0.0559987000
_diffrn_orient_matrix_UB_32      -0.0442834000
_diffrn_orient_matrix_UB_33      -0.0222132000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2689
_reflns_number_total             3053
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.01
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.305
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         3053
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0434
_refine_ls_R_factor_gt           0.0377
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0442P)²+0.4988P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0924
_refine_ls_wR_factor_ref         0.0965
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C14(H14), C15(H15), C16(H16), C17(H17), C18(H18)
2.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C19(H19A,H19B,H19C), C20(H20A,H20B,H20C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.47606(9) 0.81979(11) 0.09172(6) 0.0159(2) Uani 1 1 d . . . . .
C2 C 0.34999(11) 0.76792(14) 0.09519(7) 0.0167(2) Uani 1 1 d . . . . .
C3 C 0.28118(11) 0.91437(13) 0.12654(7) 0.0151(2) Uani 1 1 d . . . . .
C4 C 0.38034(11) 1.04594(13) 0.14040(6) 0.0146(2) Uani 1 1 d . . . . .
C5 C 0.49722(11) 0.98540(13) 0.11805(6) 0.0148(2) Uani 1 1 d . . . . .
C6 C 0.61114(11) 1.08168(14) 0.12354(7) 0.0163(2) Uani 1 1 d . . . . .
C7 C 0.60069(11) 1.24142(14) 0.15386(7) 0.0182(2) Uani 1 1 d . . . . .
H7 H 0.6742 1.3102 0.1590 0.022 Uiso 1 1 calc R . . . .
C8 C 0.48649(11) 1.30195(14) 0.17654(7) 0.0183(2) Uani 1 1 d . . . . .
H8 H 0.4860 1.4087 0.1962 0.022 Uiso 1 1 calc R . . . .
C9 C 0.37257(11) 1.20541(14) 0.17034(7) 0.0159(2) Uani 1 1 d . . . . .
C10 C 0.57096(11) 0.70814(14) 0.06630(7) 0.0194(2) Uani 1 1 d . . . . .
H10A H 0.5337 0.6000 0.0600 0.029 Uiso 1 1 calc GR . . . .
H10B H 0.6522 0.7071 0.1085 0.029 Uiso 1 1 calc GR . . . .
H10C H 0.5896 0.7437 0.0137 0.029 Uiso 1 1 calc GR . . . .
O11 O 0.30436(8) 0.63225(10) 0.07693(6) 0.0228(2) Uani 1 1 d . . . . .
N12 N 0.16226(9) 0.92275(12) 0.13837(6) 0.0186(2) Uani 1 1 d . . . . .
C13 C 0.07382(11) 0.78623(14) 0.12216(7) 0.0170(2) Uani 1 1 d . . . . .
C14 C -0.00803(12) 0.76418(15) 0.04295(7) 0.0202(2) Uani 1 1 d . . . . .
H14 H -0.0017 0.8346 -0.0010 0.024 Uiso 1 1 calc R . . . .
C15 C -0.09930(12) 0.63609(15) 0.03003(8) 0.0218(3) Uani 1 1 d . . . . .
H15 H -0.1531 0.6199 -0.0230 0.026 Uiso 1 1 calc R . . . .
C16 C -0.11074(11) 0.53232(15) 0.09560(8) 0.0213(3) Uani 1 1 d . . . . .
H16 H -0.1714 0.4463 0.0864 0.026 Uiso 1 1 calc R . . . .
C17 C -0.03162(12) 0.55710(15) 0.17482(8) 0.0237(3) Uani 1 1 d . . . . .
H17 H -0.0399 0.4883 0.2190 0.028 Uiso 1 1 calc R . . . .
C18 C 0.06013(12) 0.68458(15) 0.18841(8) 0.0217(3) Uani 1 1 d . . . . .
H18 H 0.1124 0.7019 0.2419 0.026 Uiso 1 1 calc R . . . .
C19 C 0.24955(12) 1.27040(14) 0.19572(7) 0.0199(2) Uani 1 1 d . . . . .
H19A H 0.1732 1.2517 0.1511 0.030 Uiso 1 1 calc GR . . . .
H19B H 0.2596 1.3857 0.2066 0.030 Uiso 1 1 calc GR . . . .
H19C H 0.2373 1.2153 0.2457 0.030 Uiso 1 1 calc GR . . . .
C20 C 0.73961(11) 1.02838(15) 0.09973(7) 0.0199(2) Uani 1 1 d . . . . .
H20A H 0.7860 0.9534 0.1412 0.030 Uiso 1 1 calc GR . . . .
H20B H 0.7947 1.1224 0.0971 0.030 Uiso 1 1 calc GR . . . .
H20C H 0.7196 0.9755 0.0458 0.030 Uiso 1 1 calc GR . . . .


_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
N1 C2 1.3723(14) . ?
N1 C5 1.4226(14) . ?
N1 C10 1.4558(14) . ?
C2 C3 1.5303(15) . ?
C2 O11 1.2158(14) . ?
C3 C4 1.4642(15) . ?
C3 N12 1.2751(14) . ?
C4 C5 1.4126(15) . ?
C4 C9 1.3997(15) . ?
C5 C6 1.3952(15) . ?
C6 C7 1.4078(16) . ?
C6 C20 1.5126(15) . ?
C7 H7 0.9300 . ?
C7 C8 1.3902(16) . ?
C8 H8 0.9300 . ?
C8 C9 1.3951(16) . ?
C9 C19 1.5037(16) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
N12 C13 1.4267(14) . ?
C13 C14 1.3920(16) . ?
C13 C18 1.3906(16) . ?
C14 H14 0.9300 . ?
C14 C15 1.3901(16) . ?
C15 H15 0.9300 . ?
C15 C16 1.3863(17) . ?
C16 H16 0.9300 . ?
C16 C17 1.3840(18) . ?
C17 H17 0.9300 . ?
C17 C18 1.3897(17) . ?
C18 H18 0.9300 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?

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
C2 N1 C5 111.52(9) . . ?
C2 N1 C10 120.61(9) . . ?
C5 N1 C10 127.84(9) . . ?
N1 C2 C3 106.02(9) . . ?
O11 C2 N1 126.07(11) . . ?
O11 C2 C3 127.91(10) . . ?
C4 C3 C2 105.80(9) . . ?
N12 C3 C2 127.91(10) . . ?
N12 C3 C4 126.28(10) . . ?
C5 C4 C3 107.56(9) . . ?
C9 C4 C3 130.48(10) . . ?
C9 C4 C5 121.96(10) . . ?
C4 C5 N1 109.09(9) . . ?
C6 C5 N1 128.94(10) . . ?
C6 C5 C4 121.97(10) . . ?
C5 C6 C7 114.91(10) . . ?
C5 C6 C20 125.66(10) . . ?
C7 C6 C20 119.43(10) . . ?
C6 C7 H7 118.2 . . ?
C8 C7 C6 123.61(10) . . ?
C8 C7 H7 118.2 . . ?
C7 C8 H8 119.4 . . ?
C7 C8 C9 121.20(11) . . ?
C9 C8 H8 119.4 . . ?
C4 C9 C19 122.48(10) . . ?
C8 C9 C4 116.35(10) . . ?
C8 C9 C19 121.17(10) . . ?
N1 C10 H10A 109.5 . . ?
N1 C10 H10B 109.5 . . ?
N1 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C3 N12 C13 121.35(10) . . ?
C14 C13 N12 120.50(10) . . ?
C18 C13 N12 119.24(10) . . ?
C18 C13 C14 119.94(10) . . ?
C13 C14 H14 120.3 . . ?
C15 C14 C13 119.48(11) . . ?
C15 C14 H14 120.3 . . ?
C14 C15 H15 119.7 . . ?
C16 C15 C14 120.54(11) . . ?
C16 C15 H15 119.7 . . ?
C15 C16 H16 120.1 . . ?
C17 C16 C15 119.84(11) . . ?
C17 C16 H16 120.1 . . ?
C16 C17 H17 119.9 . . ?
C16 C17 C18 120.11(11) . . ?
C18 C17 H17 119.9 . . ?
C13 C18 H18 120.0 . . ?
C17 C18 C13 120.03(11) . . ?
C17 C18 H18 120.0 . . ?
C9 C19 H19A 109.5 . . ?
C9 C19 H19B 109.5 . . ?
C9 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C6 C20 H20A 109.5 . . ?
C6 C20 H20B 109.5 . . ?
C6 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C2 C3 C4 -0.76(11) . . . . ?
N1 C2 C3 N12 179.09(11) . . . . ?
N1 C5 C6 C7 -178.73(10) . . . . ?
N1 C5 C6 C20 1.54(18) . . . . ?
C2 N1 C5 C4 0.32(12) . . . . ?
C2 N1 C5 C6 179.88(11) . . . . ?
C2 C3 C4 C5 0.95(11) . . . . ?
C2 C3 C4 C9 -178.61(11) . . . . ?
C2 C3 N12 C13 -0.21(17) . . . . ?
C3 C4 C5 N1 -0.81(12) . . . . ?
C3 C4 C5 C6 179.59(9) . . . . ?
C3 C4 C9 C8 179.83(11) . . . . ?
C3 C4 C9 C19 0.57(18) . . . . ?
C3 N12 C13 C14 -89.86(14) . . . . ?
C3 N12 C13 C18 96.66(13) . . . . ?
C4 C3 N12 C13 179.61(10) . . . . ?
C4 C5 C6 C7 0.78(15) . . . . ?
C4 C5 C6 C20 -178.95(10) . . . . ?
C5 N1 C2 C3 0.29(12) . . . . ?
C5 N1 C2 O11 -179.55(11) . . . . ?
C5 C4 C9 C8 0.32(15) . . . . ?
C5 C4 C9 C19 -178.95(10) . . . . ?
C5 C6 C7 C8 -0.37(16) . . . . ?
C6 C7 C8 C9 -0.06(17) . . . . ?
C7 C8 C9 C4 0.10(16) . . . . ?
C7 C8 C9 C19 179.37(10) . . . . ?
C9 C4 C5 N1 178.80(9) . . . . ?
C9 C4 C5 C6 -0.80(16) . . . . ?
C10 N1 C2 C3 178.28(9) . . . . ?
C10 N1 C2 O11 -1.57(17) . . . . ?
C10 N1 C5 C4 -177.49(10) . . . . ?
C10 N1 C5 C6 2.07(18) . . . . ?
O11 C2 C3 C4 179.08(11) . . . . ?
O11 C2 C3 N12 -1.07(19) . . . . ?
N12 C3 C4 C5 -178.90(10) . . . . ?
N12 C3 C4 C9 1.53(19) . . . . ?
N12 C13 C14 C15 -176.03(10) . . . . ?
N12 C13 C18 C17 176.01(10) . . . . ?
C13 C14 C15 C16 1.06(18) . . . . ?
C14 C13 C18 C17 2.49(18) . . . . ?
C14 C15 C16 C17 0.60(18) . . . . ?
C15 C16 C17 C18 -0.71(18) . . . . ?
C16 C17 C18 C13 -0.83(18) . . . . ?
C18 C13 C14 C15 -2.60(17) . . . . ?
C20 C6 C7 C8 179.38(10) . . . . ?


####################################################################### 
# 
# 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_Compound_3_AS_22
_database_code_depnum_ccdc_archive 'CCDC 1505867'
_audit_update_record             
;
2016-09-22 deposited with the CCDC.
2017-01-29 downloaded from the CCDC.
;
_audit_creation_date             2016-08-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C23 H28 N2 O'
_chemical_formula_sum            'C23 H28 N2 O'
_chemical_formula_weight         348.47
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C23 H28 N2 O'
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.5182(6)
_cell_length_b                   29.4795(14)
_cell_length_c                   8.4782(5)
_cell_angle_alpha                90
_cell_angle_beta                 115.150(8)
_cell_angle_gamma                90
_cell_volume                     1927.1(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3972
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.4820
_cell_measurement_theta_min      3.3500
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74687
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.201
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.04
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0284
_diffrn_reflns_av_unetI/netI     0.0307
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       38
_diffrn_reflns_limit_k_min       -37
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            15518
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_min         2.642
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 16.2096
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -38.00  -12.00   1.0000   75.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.4241   57.0000  150.0000 26

#__ type_ start__ end____ width___ exp.time_
  2 omega  -61.00   43.00   1.0000   75.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.4241   19.0000  -30.0000 104

#__ type_ start__ end____ width___ exp.time_
  3 omega  -91.00  -61.00   1.0000   75.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.4241 -178.0000  -60.0000 30

#__ type_ start__ end____ width___ exp.time_
  4 omega  -58.00  -32.00   1.0000   75.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.4241   99.0000   92.0000 26

#__ type_ start__ end____ width___ exp.time_
  5 omega  -19.00   51.00   1.0000   75.0000
omega____ theta____ kappa____ phi______ frames
    -       23.5178   19.0000    0.0000 70

#__ type_ start__ end____ width___ exp.time_
  6 omega  -73.00  -47.00   1.0000   75.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.4241 -178.0000  120.0000 26

#__ type_ start__ end____ width___ exp.time_
  7 omega   48.00   75.00   1.0000   75.0000
omega____ theta____ kappa____ phi______ frames
    -       23.5178  178.0000  150.0000 27

#__ type_ start__ end____ width___ exp.time_
  8 omega   -7.00   91.00   1.0000   75.0000
omega____ theta____ kappa____ phi______ frames
    -       23.5178   77.0000  150.0000 98
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0442588000
_diffrn_orient_matrix_UB_12      -0.0176992000
_diffrn_orient_matrix_UB_13      0.0588802000
_diffrn_orient_matrix_UB_21      -0.0118463000
_diffrn_orient_matrix_UB_22      -0.0144003000
_diffrn_orient_matrix_UB_23      -0.0711661000
_diffrn_orient_matrix_UB_31      0.0798159000
_diffrn_orient_matrix_UB_32      0.0076400000
_diffrn_orient_matrix_UB_33      0.0020813000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3571
_reflns_number_total             4310
_reflns_odcompleteness_completeness 96.85
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.51
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.299
_refine_diff_density_min         -0.204
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     242
_refine_ls_number_reflns         4310
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0598
_refine_ls_R_factor_gt           0.0470
_refine_ls_restrained_S_all      1.070
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0332P)²+1.0215P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0994
_refine_ls_wR_factor_ref         0.1053
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C21(H21), C24(H24)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C17(H17), C18(H18), C19(H19)
2.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C22(H22A,H22B,
 H22C), C23(H23A,H23B,H23C), C25(H25A,H25B,H25C), C26(H26A,H26B,H26C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.38630(16) 0.47291(4) 0.16372(14) 0.0170(3) Uani 1 1 d . . . . .
C2 C 0.29563(19) 0.43297(5) 0.13547(17) 0.0174(3) Uani 1 1 d . . . . .
C3 C 0.40725(18) 0.40078(4) 0.28208(17) 0.0141(3) Uani 1 1 d . . . . .
C4 C 0.55716(18) 0.42775(4) 0.39609(17) 0.0143(3) Uani 1 1 d . . . . .
C5 C 0.54329(18) 0.47093(5) 0.31943(16) 0.0148(3) Uani 1 1 d . . . . .
C6 C 0.67104(19) 0.50391(5) 0.39068(18) 0.0175(3) Uani 1 1 d . . . . .
C7 C 0.81075(19) 0.49153(5) 0.54675(18) 0.0200(3) Uani 1 1 d . . . . .
H7 H 0.8989 0.5126 0.6003 0.024 Uiso 1 1 calc R . . . .
C8 C 0.82482(19) 0.44954(5) 0.62597(18) 0.0201(3) Uani 1 1 d . . . . .
H8 H 0.9206 0.4435 0.7301 0.024 Uiso 1 1 calc R . . . .
C9 C 0.69758(18) 0.41623(5) 0.55191(17) 0.0165(3) Uani 1 1 d . . . . .
C10 C 0.3064(2) 0.51292(5) 0.05901(18) 0.0209(3) Uani 1 1 d . . . . .
H10A H 0.3697 0.5214 -0.0069 0.031 Uiso 1 1 calc GR . . . .
H10B H 0.3085 0.5375 0.1342 0.031 Uiso 1 1 calc GR . . . .
H10C H 0.1885 0.5062 -0.0192 0.031 Uiso 1 1 calc GR . . . .
O11 O 0.15456(14) 0.42529(4) 0.01686(13) 0.0254(3) Uani 1 1 d . . . . .
N12 N 0.38122(15) 0.35885(4) 0.29972(14) 0.0157(2) Uani 1 1 d . . . . .
C13 C 0.7119(2) 0.37095(5) 0.63878(19) 0.0226(3) Uani 1 1 d . . . . .
H13A H 0.6130 0.3664 0.6635 0.034 Uiso 1 1 calc GR . . . .
H13B H 0.8158 0.3702 0.7455 0.034 Uiso 1 1 calc GR . . . .
H13C H 0.7162 0.3473 0.5627 0.034 Uiso 1 1 calc GR . . . .
C14 C 0.6710(2) 0.55019(5) 0.31297(19) 0.0229(3) Uani 1 1 d . . . . .
H14A H 0.6396 0.5471 0.1905 0.034 Uiso 1 1 calc GR . . . .
H14B H 0.7847 0.5633 0.3691 0.034 Uiso 1 1 calc GR . . . .
H14C H 0.5888 0.5695 0.3300 0.034 Uiso 1 1 calc GR . . . .
C15 C 0.23288(18) 0.33480(5) 0.17963(17) 0.0165(3) Uani 1 1 d . . . . .
C16 C 0.25852(19) 0.30408(5) 0.06522(18) 0.0181(3) Uani 1 1 d . . . . .
C17 C 0.1180(2) 0.27790(5) -0.04387(19) 0.0222(3) Uani 1 1 d . . . . .
H17 H 0.1308 0.2584 -0.1238 0.027 Uiso 1 1 calc R . . . .
C18 C -0.0406(2) 0.28056(5) -0.0349(2) 0.0235(3) Uani 1 1 d . . . . .
H18 H -0.1332 0.2628 -0.1082 0.028 Uiso 1 1 calc R . . . .
C19 C -0.0609(2) 0.30973(5) 0.08322(19) 0.0216(3) Uani 1 1 d . . . . .
H19 H -0.1667 0.3106 0.0907 0.026 Uiso 1 1 calc R . . . .
C20 C 0.07330(19) 0.33774(5) 0.19097(18) 0.0179(3) Uani 1 1 d . . . . .
C21 C 0.04419(19) 0.36977(5) 0.31665(19) 0.0205(3) Uani 1 1 d . . . . .
H21 H 0.1461 0.3895 0.3681 0.025 Uiso 1 1 calc R . . . .
C22 C -0.1133(2) 0.39998(6) 0.2245(2) 0.0338(4) Uani 1 1 d . . . . .
H22A H -0.1030 0.4154 0.1296 0.051 Uiso 1 1 calc GR . . . .
H22B H -0.1199 0.4219 0.3053 0.051 Uiso 1 1 calc GR . . . .
H22C H -0.2164 0.3817 0.1804 0.051 Uiso 1 1 calc GR . . . .
C23 C 0.0286(3) 0.34377(6) 0.4647(2) 0.0354(4) Uani 1 1 d . . . . .
H23A H -0.0741 0.3253 0.4187 0.053 Uiso 1 1 calc GR . . . .
H23B H 0.0214 0.3648 0.5477 0.053 Uiso 1 1 calc GR . . . .
H23C H 0.1285 0.3247 0.5209 0.053 Uiso 1 1 calc GR . . . .
C24 C 0.4331(2) 0.30169(5) 0.05659(19) 0.0198(3) Uani 1 1 d . . . . .
H24 H 0.5220 0.3113 0.1701 0.024 Uiso 1 1 calc R . . . .
C25 C 0.4802(2) 0.25373(6) 0.0213(2) 0.0311(4) Uani 1 1 d . . . . .
H25A H 0.4730 0.2331 0.1056 0.047 Uiso 1 1 calc GR . . . .
H25B H 0.5962 0.2537 0.0297 0.047 Uiso 1 1 calc GR . . . .
H25C H 0.4009 0.2444 -0.0936 0.047 Uiso 1 1 calc GR . . . .
C26 C 0.4363(2) 0.33520(6) -0.0801(2) 0.0316(4) Uani 1 1 d . . . . .
H26A H 0.3490 0.3269 -0.1928 0.047 Uiso 1 1 calc GR . . . .
H26B H 0.5482 0.3345 -0.0817 0.047 Uiso 1 1 calc GR . . . .
H26C H 0.4135 0.3652 -0.0514 0.047 Uiso 1 1 calc GR . . . .


_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
N1 C2 1.3722(18) . ?
N1 C5 1.4262(18) . ?
N1 C10 1.4590(17) . ?
C2 C3 1.5313(19) . ?
C2 O11 1.2163(17) . ?
C3 C4 1.4654(19) . ?
C3 N12 1.2758(17) . ?
C4 C5 1.4112(18) . ?
C4 C9 1.3958(19) . ?
C5 C6 1.3914(19) . ?
C6 C7 1.401(2) . ?
C6 C14 1.5149(19) . ?
C7 H7 0.9300 . ?
C7 C8 1.389(2) . ?
C8 H8 0.9300 . ?
C8 C9 1.398(2) . ?
C9 C13 1.5042(19) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
N12 C15 1.4292(18) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 C16 1.4102(19) . ?
C15 C20 1.406(2) . ?
C16 C17 1.394(2) . ?
C16 C24 1.522(2) . ?
C17 H17 0.9300 . ?
C17 C18 1.388(2) . ?
C18 H18 0.9300 . ?
C18 C19 1.386(2) . ?
C19 H19 0.9300 . ?
C19 C20 1.391(2) . ?
C20 C21 1.5209(19) . ?
C21 H21 0.9800 . ?
C21 C22 1.521(2) . ?
C21 C23 1.524(2) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 H24 0.9800 . ?
C24 C25 1.533(2) . ?
C24 C26 1.531(2) . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?

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
C2 N1 C5 111.30(11) . . ?
C2 N1 C10 120.34(12) . . ?
C5 N1 C10 127.42(12) . . ?
N1 C2 C3 106.30(12) . . ?
O11 C2 N1 126.08(13) . . ?
O11 C2 C3 127.61(13) . . ?
C4 C3 C2 105.41(11) . . ?
N12 C3 C2 128.07(13) . . ?
N12 C3 C4 126.47(13) . . ?
C5 C4 C3 107.85(12) . . ?
C9 C4 C3 130.42(12) . . ?
C9 C4 C5 121.71(13) . . ?
C4 C5 N1 108.98(12) . . ?
C6 C5 N1 128.75(12) . . ?
C6 C5 C4 122.25(13) . . ?
C5 C6 C7 114.94(13) . . ?
C5 C6 C14 125.81(13) . . ?
C7 C6 C14 119.24(13) . . ?
C6 C7 H7 118.2 . . ?
C8 C7 C6 123.58(13) . . ?
C8 C7 H7 118.2 . . ?
C7 C8 H8 119.4 . . ?
C7 C8 C9 121.17(13) . . ?
C9 C8 H8 119.4 . . ?
C4 C9 C8 116.31(13) . . ?
C4 C9 C13 122.54(13) . . ?
C8 C9 C13 121.14(13) . . ?
N1 C10 H10A 109.5 . . ?
N1 C10 H10B 109.5 . . ?
N1 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C3 N12 C15 122.84(12) . . ?
C9 C13 H13A 109.5 . . ?
C9 C13 H13B 109.5 . . ?
C9 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C6 C14 H14A 109.5 . . ?
C6 C14 H14B 109.5 . . ?
C6 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C16 C15 N12 117.39(12) . . ?
C20 C15 N12 120.57(12) . . ?
C20 C15 C16 121.58(13) . . ?
C15 C16 C24 120.21(13) . . ?
C17 C16 C15 118.15(13) . . ?
C17 C16 C24 121.57(13) . . ?
C16 C17 H17 119.5 . . ?
C18 C17 C16 120.93(13) . . ?
C18 C17 H17 119.5 . . ?
C17 C18 H18 120.1 . . ?
C19 C18 C17 119.88(14) . . ?
C19 C18 H18 120.1 . . ?
C18 C19 H19 119.2 . . ?
C18 C19 C20 121.52(14) . . ?
C20 C19 H19 119.2 . . ?
C15 C20 C21 122.45(13) . . ?
C19 C20 C15 117.85(13) . . ?
C19 C20 C21 119.70(13) . . ?
C20 C21 H21 107.6 . . ?
C20 C21 C23 111.22(12) . . ?
C22 C21 C20 111.99(13) . . ?
C22 C21 H21 107.6 . . ?
C22 C21 C23 110.56(13) . . ?
C23 C21 H21 107.6 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C21 C23 H23A 109.5 . . ?
C21 C23 H23B 109.5 . . ?
C21 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C16 C24 H24 107.6 . . ?
C16 C24 C25 113.21(12) . . ?
C16 C24 C26 109.76(12) . . ?
C25 C24 H24 107.6 . . ?
C26 C24 H24 107.6 . . ?
C26 C24 C25 110.92(13) . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C24 C26 H26A 109.5 . . ?
C24 C26 H26B 109.5 . . ?
C24 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C2 C3 C4 3.88(14) . . . . ?
N1 C2 C3 N12 -173.50(13) . . . . ?
N1 C5 C6 C7 179.85(12) . . . . ?
N1 C5 C6 C14 -1.1(2) . . . . ?
C2 N1 C5 C4 0.48(15) . . . . ?
C2 N1 C5 C6 178.74(13) . . . . ?
C2 C3 C4 C5 -3.62(14) . . . . ?
C2 C3 C4 C9 177.90(13) . . . . ?
C2 C3 N12 C15 -1.6(2) . . . . ?
C3 C4 C5 N1 2.12(14) . . . . ?
C3 C4 C5 C6 -176.28(12) . . . . ?
C3 C4 C9 C8 177.25(13) . . . . ?
C3 C4 C9 C13 -3.7(2) . . . . ?
C3 N12 C15 C16 106.08(15) . . . . ?
C3 N12 C15 C20 -81.55(17) . . . . ?
C4 C3 N12 C15 -178.42(12) . . . . ?
C4 C5 C6 C7 -2.10(18) . . . . ?
C4 C5 C6 C14 176.93(12) . . . . ?
C5 N1 C2 C3 -2.73(14) . . . . ?
C5 N1 C2 O11 177.17(13) . . . . ?
C5 C4 C9 C8 -1.05(18) . . . . ?
C5 C4 C9 C13 177.96(12) . . . . ?
C5 C6 C7 C8 0.74(19) . . . . ?
C6 C7 C8 C9 0.5(2) . . . . ?
C7 C8 C9 C4 -0.30(19) . . . . ?
C7 C8 C9 C13 -179.33(13) . . . . ?
C9 C4 C5 N1 -179.24(11) . . . . ?
C9 C4 C5 C6 2.37(19) . . . . ?
C10 N1 C2 C3 -172.42(11) . . . . ?
C10 N1 C2 O11 7.5(2) . . . . ?
C10 N1 C5 C4 169.27(12) . . . . ?
C10 N1 C5 C6 -12.5(2) . . . . ?
O11 C2 C3 C4 -176.02(14) . . . . ?
O11 C2 C3 N12 6.6(2) . . . . ?
N12 C3 C4 C5 173.81(13) . . . . ?
N12 C3 C4 C9 -4.7(2) . . . . ?
N12 C15 C16 C17 175.37(12) . . . . ?
N12 C15 C16 C24 -7.54(19) . . . . ?
N12 C15 C20 C19 -173.02(12) . . . . ?
N12 C15 C20 C21 6.4(2) . . . . ?
C14 C6 C7 C8 -178.36(13) . . . . ?
C15 C16 C17 C18 -2.7(2) . . . . ?
C15 C16 C24 C25 145.92(14) . . . . ?
C15 C16 C24 C26 -89.55(16) . . . . ?
C15 C20 C21 C22 126.69(15) . . . . ?
C15 C20 C21 C23 -109.04(16) . . . . ?
C16 C15 C20 C19 -1.0(2) . . . . ?
C16 C15 C20 C21 178.43(13) . . . . ?
C16 C17 C18 C19 0.3(2) . . . . ?
C17 C16 C24 C25 -37.09(19) . . . . ?
C17 C16 C24 C26 87.44(17) . . . . ?
C17 C18 C19 C20 1.9(2) . . . . ?
C18 C19 C20 C15 -1.6(2) . . . . ?
C18 C19 C20 C21 179.00(13) . . . . ?
C19 C20 C21 C22 -53.91(18) . . . . ?
C19 C20 C21 C23 70.36(18) . . . . ?
C20 C15 C16 C17 3.1(2) . . . . ?
C20 C15 C16 C24 -179.82(12) . . . . ?
C24 C16 C17 C18 -179.77(13) . . . . ?


####################################################################### 
# 
# 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_Compound_4_lcb_007
_database_code_depnum_ccdc_archive 'CCDC 1505870'
_audit_update_record             
;
2016-09-22 deposited with the CCDC.
2017-01-29 downloaded from the CCDC.
;
_audit_creation_date             2015-02-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C15 H12 N2 O, C9 H7 N O2'
_chemical_formula_sum            'C24 H19 N3 O3'
_chemical_formula_weight         397.42
_chemical_melting_point          ?

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

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

_cell_length_a                   7.8377(2)
_cell_length_b                   8.33995(19)
_cell_length_c                   31.7116(6)
_cell_angle_alpha                85.8492(17)
_cell_angle_beta                 85.7112(18)
_cell_angle_gamma                69.989(2)
_cell_volume                     1939.83(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    21591
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      75.9670
_cell_measurement_theta_min      5.5530
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.743
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78316
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.09
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0546
_diffrn_reflns_av_unetI/netI     0.0281
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            46094
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.493
_diffrn_reflns_theta_min         2.798
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.3829
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -51.00  -13.00   1.0000    1.8800
omega____ theta____ kappa____ phi______ frames
    -      -40.3787  -57.0000   90.0000 38

#__ type_ start__ end____ width___ exp.time_
  2 omega -111.00  -11.00   1.0000    1.8800
omega____ theta____ kappa____ phi______ frames
    -      -40.3787  -57.0000  -30.0000 100

#__ type_ start__ end____ width___ exp.time_
  3 omega -114.00  -26.00   1.0000    1.8800
omega____ theta____ kappa____ phi______ frames
    -      -40.3787  -57.0000 -120.0000 88

#__ type_ start__ end____ width___ exp.time_
  4 omega  -69.00   33.00   1.0000    1.8800
omega____ theta____ kappa____ phi______ frames
    -      -40.3787   57.0000   30.0000 102

#__ type_ start__ end____ width___ exp.time_
  5 omega -114.00  -69.00   1.0000    1.8800
omega____ theta____ kappa____ phi______ frames
    -      -40.3787  -57.0000   90.0000 45

#__ type_ start__ end____ width___ exp.time_
  6 omega -106.00  -53.00   1.0000    1.8800
omega____ theta____ kappa____ phi______ frames
    -      -40.3787 -163.0000   74.0834 53

#__ type_ start__ end____ width___ exp.time_
  7 omega   55.00  126.00   1.0000    1.8800
omega____ theta____ kappa____ phi______ frames
    -       40.3787 -178.0000    0.0000 71

#__ type_ start__ end____ width___ exp.time_
  8 omega   55.00  129.00   1.0000    1.8800
omega____ theta____ kappa____ phi______ frames
    -       40.3787 -178.0000 -150.0000 74

#__ type_ start__ end____ width___ exp.time_
  9 omega   14.00   45.00   1.0000    1.8800
omega____ theta____ kappa____ phi______ frames
    -       40.3787   38.0000 -180.0000 31

#__ type_ start__ end____ width___ exp.time_
 10 omega    8.00   35.00   1.0000    1.8800
omega____ theta____ kappa____ phi______ frames
    -       44.0000   85.0000 -105.0699 27

#__ type_ start__ end____ width___ exp.time_
 11 omega    7.00   32.00   1.0000    1.8800
omega____ theta____ kappa____ phi______ frames
    -       44.0000   88.0000  -91.4038 25

#__ type_ start__ end____ width___ exp.time_
 12 omega   12.00   37.00   1.0000    1.8800
omega____ theta____ kappa____ phi______ frames
    -       48.0000   84.0000   38.3692 25

#__ type_ start__ end____ width___ exp.time_
 13 omega   22.00   48.00   1.0000    1.8800
omega____ theta____ kappa____ phi______ frames
    -       56.0000   78.0000  162.5277 26

#__ type_ start__ end____ width___ exp.time_
 14 omega   22.00   47.00   1.0000    1.8800
omega____ theta____ kappa____ phi______ frames
    -       56.0000   78.0000  -37.9348 25

#__ type_ start__ end____ width___ exp.time_
 15 omega   22.00   47.00   1.0000    1.8800
omega____ theta____ kappa____ phi______ frames
    -       56.0000   78.0000  105.6922 25

#__ type_ start__ end____ width___ exp.time_
 16 omega   31.00   57.00   1.0000    1.8800
omega____ theta____ kappa____ phi______ frames
    -       64.0000   76.0000   16.7745 26

#__ type_ start__ end____ width___ exp.time_
 17 omega  121.00  146.00   1.0000    1.8800
omega____ theta____ kappa____ phi______ frames
    -       68.0000   76.0000  -28.9162 25

#__ type_ start__ end____ width___ exp.time_
 18 omega   35.00   66.00   1.0000    1.8800
omega____ theta____ kappa____ phi______ frames
    -       68.0000   75.0000  -78.8325 31

#__ type_ start__ end____ width___ exp.time_
 19 omega   35.00   63.00   1.0000    1.8800
omega____ theta____ kappa____ phi______ frames
    -       68.0000   76.0000  -28.9162 28

#__ type_ start__ end____ width___ exp.time_
 20 omega   35.00   64.00   1.0000    1.8800
omega____ theta____ kappa____ phi______ frames
    -       68.0000   76.0000   45.9825 29

#__ type_ start__ end____ width___ exp.time_
 21 omega   35.00   62.00   1.0000    1.8800
omega____ theta____ kappa____ phi______ frames
    -       68.0000   76.0000  119.6347 27

#__ type_ start__ end____ width___ exp.time_
 22 omega   35.00   63.00   1.0000    1.8800
omega____ theta____ kappa____ phi______ frames
    -       68.0000   76.0000 -159.3435 28

#__ type_ start__ end____ width___ exp.time_
 23 omega   38.00   64.00   1.0000    1.8800
omega____ theta____ kappa____ phi______ frames
    -       68.0000   75.0000 -123.0666 26

#__ type_ start__ end____ width___ exp.time_
 24 omega  110.00  136.00   1.0000    1.8800
omega____ theta____ kappa____ phi______ frames
    -       68.0000   75.0000  -78.8325 26

#__ type_ start__ end____ width___ exp.time_
 25 omega   38.00   64.00   1.0000    1.8800
omega____ theta____ kappa____ phi______ frames
    -       72.0000   77.0000   87.6638 26

#__ type_ start__ end____ width___ exp.time_
 26 omega   39.00   66.00   1.0000    1.8800
omega____ theta____ kappa____ phi______ frames
    -       72.0000   76.0000  146.7777 27

#__ type_ start__ end____ width___ exp.time_
 27 omega  123.00  153.00   1.0000    1.8800
omega____ theta____ kappa____ phi______ frames
    -       76.0000   73.0000 -144.8218 30

#__ type_ start__ end____ width___ exp.time_
 28 omega   44.00   70.00   1.0000    1.8800
omega____ theta____ kappa____ phi______ frames
    -       76.0000   73.0000 -144.8218 26

#__ type_ start__ end____ width___ exp.time_
 29 omega   47.00   73.00   1.0000    7.5200
omega____ theta____ kappa____ phi______ frames
    -       80.0000   73.0000  -20.9677 26

#__ type_ start__ end____ width___ exp.time_
 30 omega   47.00   72.00   1.0000    7.5200
omega____ theta____ kappa____ phi______ frames
    -       80.0000   76.0000  157.8323 25

#__ type_ start__ end____ width___ exp.time_
 31 omega   58.00   84.00   1.0000    7.5200
omega____ theta____ kappa____ phi______ frames
    -       88.0000   58.0000   45.1220 26

#__ type_ start__ end____ width___ exp.time_
 32 omega   56.00   82.00   1.0000    7.5200
omega____ theta____ kappa____ phi______ frames
    -       88.0000   70.0000   -6.1171 26

#__ type_ start__ end____ width___ exp.time_
 33 omega   58.00   84.00   1.0000    7.5200
omega____ theta____ kappa____ phi______ frames
    -       88.0000   62.0000  108.2330 26

#__ type_ start__ end____ width___ exp.time_
 34 omega   58.00   84.00   1.0000    7.5200
omega____ theta____ kappa____ phi______ frames
    -       88.0000   64.0000 -142.2332 26

#__ type_ start__ end____ width___ exp.time_
 35 omega  138.00  164.00   1.0000    7.5200
omega____ theta____ kappa____ phi______ frames
    -       92.0000   72.0000   40.1196 26

#__ type_ start__ end____ width___ exp.time_
 36 omega   59.00  129.00   1.0000    7.5200
omega____ theta____ kappa____ phi______ frames
    -       92.0000   72.0000   40.1196 70

#__ type_ start__ end____ width___ exp.time_
 37 omega   62.00   87.00   1.0000    7.5200
omega____ theta____ kappa____ phi______ frames
    -       92.0000   57.0000   92.3394 25

#__ type_ start__ end____ width___ exp.time_
 38 omega   65.00  103.00   1.0000    7.5200
omega____ theta____ kappa____ phi______ frames
    -       96.0000   66.0000  126.2527 38

#__ type_ start__ end____ width___ exp.time_
 39 omega   68.00  115.00   1.0000    7.5200
omega____ theta____ kappa____ phi______ frames
    -       96.0000   64.0000  -61.1896 47

#__ type_ start__ end____ width___ exp.time_
 40 omega   69.00   97.00   1.0000    7.5200
omega____ theta____ kappa____ phi______ frames
    -      100.0000   66.0000  166.9621 28

#__ type_ start__ end____ width___ exp.time_
 41 omega   76.00  123.00   1.0000    7.5200
omega____ theta____ kappa____ phi______ frames
    -      108.0000   69.0000 -114.5732 47

#__ type_ start__ end____ width___ exp.time_
 42 omega   41.00   66.00   1.0000    7.5200
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000  -90.0000 25

#__ type_ start__ end____ width___ exp.time_
 43 omega   84.00  149.00   1.0000    7.5200
omega____ theta____ kappa____ phi______ frames
    -      113.0000  178.0000   60.0000 65

#__ type_ start__ end____ width___ exp.time_
 44 omega  117.00  177.00   1.0000    7.5200
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000   60.0000 60

#__ type_ start__ end____ width___ exp.time_
 45 omega   36.00  115.00   1.0000    7.5200
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000   60.0000 79

#__ type_ start__ end____ width___ exp.time_
 46 omega   79.00  105.00   1.0000    7.5200
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000   30.0000 26

#__ type_ start__ end____ width___ exp.time_
 47 omega   39.00  115.00   1.0000    7.5200
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000 -180.0000 76

#__ type_ start__ end____ width___ exp.time_
 48 omega   82.00  168.00   1.0000    7.5200
omega____ theta____ kappa____ phi______ frames
    -      113.0000   73.0000 -134.6326 86

#__ type_ start__ end____ width___ exp.time_
 49 omega   83.00  148.00   1.0000    7.5200
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000   60.0000 65

#__ type_ start__ end____ width___ exp.time_
 50 omega   53.00   97.00   1.0000    7.5200
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000  120.0000 44

#__ type_ start__ end____ width___ exp.time_
 51 omega   79.00  127.00   1.0000    7.5200
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000    0.0000 48

#__ type_ start__ end____ width___ exp.time_
 52 omega  141.00  171.00   1.0000    7.5200
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000  150.0000 30

#__ type_ start__ end____ width___ exp.time_
 53 omega   79.00  124.00   1.0000    7.5200
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000  150.0000 45

#__ type_ start__ end____ width___ exp.time_
 54 omega  121.00  147.00   1.0000    7.5200
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000   90.0000 26

#__ type_ start__ end____ width___ exp.time_
 55 omega   79.00  105.00   1.0000    7.5200
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000   90.0000 26

#__ type_ start__ end____ width___ exp.time_
 56 omega   85.00  111.00   1.0000    7.5200
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000 -150.0000 26

#__ type_ start__ end____ width___ exp.time_
 57 omega  130.00  156.00   1.0000    7.5200
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000   30.0000 26

#__ type_ start__ end____ width___ exp.time_
 58 omega   79.00  106.00   1.0000    7.5200
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000   60.0000 27

#__ type_ start__ end____ width___ exp.time_
 59 omega   39.00   92.00   1.0000    7.5200
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000    0.0000 53

#__ type_ start__ end____ width___ exp.time_
 60 omega   37.00   72.00   1.0000    7.5200
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000 -120.0000 35

#__ type_ start__ end____ width___ exp.time_
 61 omega  152.00  177.00   1.0000    7.5200
omega____ theta____ kappa____ phi______ frames
    -      113.0000  112.0000  -60.0000 25

#__ type_ start__ end____ width___ exp.time_
 62 omega   70.00  114.00   1.0000    7.5200
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000  -90.0000 44

#__ type_ start__ end____ width___ exp.time_
 63 omega  104.00  137.00   1.0000    7.5200
omega____ theta____ kappa____ phi______ frames
    -      113.0000  112.0000  -60.0000 33

#__ type_ start__ end____ width___ exp.time_
 64 omega   49.00  111.00   1.0000    7.5200
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000  120.0000 62

#__ type_ start__ end____ width___ exp.time_
 65 omega   79.00  177.00   1.0000    7.5200
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000  -60.0000 98

#__ type_ start__ end____ width___ exp.time_
 66 omega   76.00  113.00   1.0000    7.5200
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000    0.0000 37

#__ type_ start__ end____ width___ exp.time_
 67 omega   38.00   83.00   1.0000    7.5200
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000  150.0000 45

#__ type_ start__ end____ width___ exp.time_
 68 omega   85.00  177.00   1.0000    7.5200
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000  -90.0000 92

#__ type_ start__ end____ width___ exp.time_
 69 omega   86.00  172.00   1.0000    7.5200
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000   90.0000 86

#__ type_ start__ end____ width___ exp.time_
 70 omega   99.00  129.00   1.0000    7.5200
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000  120.0000 30

#__ type_ start__ end____ width___ exp.time_
 71 omega   34.00   73.00   1.0000    7.5200
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000  120.0000 39

#__ type_ start__ end____ width___ exp.time_
 72 omega  102.00  165.00   1.0000    7.5200
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000 -120.0000 63

#__ type_ start__ end____ width___ exp.time_
 73 omega  109.00  135.00   1.0000    7.5200
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000 -180.0000 26

#__ type_ start__ end____ width___ exp.time_
 74 omega   54.00   89.00   1.0000    7.5200
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000    0.0000 35

#__ type_ start__ end____ width___ exp.time_
 75 omega   88.00  178.00   1.0000    7.5200
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000 -180.0000 90

#__ type_ start__ end____ width___ exp.time_
 76 omega   79.00  106.00   1.0000    7.5200
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000 -180.0000 27

#__ type_ start__ end____ width___ exp.time_
 77 omega   83.00  152.00   1.0000    7.5200
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000  150.0000 69

#__ type_ start__ end____ width___ exp.time_
 78 omega   48.00   97.00   1.0000    7.5200
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000 -180.0000 49

#__ type_ start__ end____ width___ exp.time_
 79 omega   79.00  125.00   1.0000    7.5200
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000 -150.0000 46

#__ type_ start__ end____ width___ exp.time_
 80 omega   85.00  143.00   1.0000    7.5200
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000  120.0000 58

#__ type_ start__ end____ width___ exp.time_
 81 omega   80.00  176.00   1.0000    7.5200
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000  120.0000 96

#__ type_ start__ end____ width___ exp.time_
 82 omega   88.00  115.00   1.0000    7.5200
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000    0.0000 27

#__ type_ start__ end____ width___ exp.time_
 83 omega   46.00   72.00   1.0000    7.5200
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000    0.0000 26

#__ type_ start__ end____ width___ exp.time_
 84 omega   83.00  177.00   1.0000    7.5200
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000   30.0000 94

#__ type_ start__ end____ width___ exp.time_
 85 omega  142.00  170.00   1.0000    7.5200
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000    0.0000 28

#__ type_ start__ end____ width___ exp.time_
 86 omega   84.00  134.00   1.0000    7.5200
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000    0.0000 50

#__ type_ start__ end____ width___ exp.time_
 87 omega  140.00  165.00   1.0000    7.5200
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000  -30.0000 25

#__ type_ start__ end____ width___ exp.time_
 88 omega  110.00  157.00   1.0000    7.5200
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000  -60.0000 47

#__ type_ start__ end____ width___ exp.time_
 89 omega  121.00  170.00   1.0000    7.5200
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000 -150.0000 49

#__ type_ start__ end____ width___ exp.time_
 90 omega   79.00  106.00   1.0000    7.5200
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000  -30.0000 27
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0981946000
_diffrn_orient_matrix_UB_12      0.1947404000
_diffrn_orient_matrix_UB_13      -0.0003700000
_diffrn_orient_matrix_UB_21      0.1386327000
_diffrn_orient_matrix_UB_22      0.0252383000
_diffrn_orient_matrix_UB_23      -0.0345959000
_diffrn_orient_matrix_UB_31      -0.1225709000
_diffrn_orient_matrix_UB_32      -0.0135458000
_diffrn_orient_matrix_UB_33      -0.0343838000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                7226
_reflns_number_total             7703
_reflns_odcompleteness_completeness 94.68
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     80.95
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.292
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.203
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     545
_refine_ls_number_reflns         7703
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0637
_refine_ls_R_factor_gt           0.0608
_refine_ls_restrained_S_all      1.203
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0178P)²+3.6448P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1443
_refine_ls_wR_factor_ref         0.1456
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C9(H9), C14(H14), C15(H15), C16(H16), C17(H17),
 C18(H18), C24(H24), C25(H25), C26(H26), C27(H27), C6A(H6A), C7A(H7A), C8A(H8A),
  C9A(H9A), C14A(H14A), C15A(H15A), C16A(H16A), C17A(H17A), C18A(H18A),
 C24A(H24A), C25A(H25A), C26A(H26A), C27A(H27A)
2.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C28(H28A,H28B,H28C), C10A(H10D,H10E,H10F), C28A(H28D,
 H28E,H28F)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O11 O 0.2867(2) 1.0501(2) 0.19482(6) 0.0240(4) Uani 1 1 d . . . . .
O29 O 0.3161(3) 0.5244(3) 0.48188(6) 0.0355(5) Uani 1 1 d . . . . .
O30 O 0.1827(3) 0.6060(2) 0.56946(6) 0.0271(4) Uani 1 1 d . . . . .
N1 N 0.4976(3) 0.7946(3) 0.21649(6) 0.0200(4) Uani 1 1 d . . . . .
N12 N 0.3244(3) 1.1529(3) 0.27776(7) 0.0210(4) Uani 1 1 d . . . . .
N19 N 0.3072(3) 0.8049(3) 0.47788(7) 0.0255(5) Uani 1 1 d . . . . .
C2 C 0.3864(3) 0.9581(3) 0.22114(8) 0.0189(5) Uani 1 1 d . . . . .
C3 C 0.4147(3) 1.0040(3) 0.26551(7) 0.0176(5) Uani 1 1 d . . . . .
C4 C 0.5475(3) 0.8495(3) 0.28411(8) 0.0186(5) Uani 1 1 d . . . . .
C5 C 0.5910(3) 0.7256(3) 0.25355(8) 0.0190(5) Uani 1 1 d . . . . .
C6 C 0.7055(4) 0.5610(3) 0.26112(8) 0.0244(5) Uani 1 1 d . . . . .
H6 H 0.7325 0.4804 0.2406 0.029 Uiso 1 1 calc R . . . .
C7 C 0.7795(4) 0.5193(3) 0.30067(9) 0.0273(6) Uani 1 1 d . . . . .
H7 H 0.8584 0.4092 0.3066 0.033 Uiso 1 1 calc R . . . .
C8 C 0.7380(4) 0.6391(3) 0.33157(8) 0.0254(6) Uani 1 1 d . . . . .
H8 H 0.7882 0.6076 0.3579 0.030 Uiso 1 1 calc R . . . .
C9 C 0.6217(4) 0.8060(3) 0.32348(8) 0.0215(5) Uani 1 1 d . . . . .
H9 H 0.5945 0.8864 0.3440 0.026 Uiso 1 1 calc R . . . .
C10 C 0.5114(4) 0.7018(3) 0.17860(8) 0.0249(5) Uani 1 1 d . . . . .
H10A H 0.4476 0.6219 0.1838 0.037 Uiso 1 1 calc GR . . . .
H10B H 0.6370 0.6413 0.1712 0.037 Uiso 1 1 calc GR . . . .
H10C H 0.4587 0.7809 0.1557 0.037 Uiso 1 1 calc GR . . . .
C13 C 0.3558(3) 1.2036(3) 0.31770(8) 0.0190(5) Uani 1 1 d . . . . .
C14 C 0.5161(3) 1.2356(3) 0.32314(8) 0.0218(5) Uani 1 1 d . . . . .
H14 H 0.6064 1.2165 0.3015 0.026 Uiso 1 1 calc R . . . .
C15 C 0.5397(4) 1.2960(3) 0.36107(8) 0.0232(5) Uani 1 1 d . . . . .
H15 H 0.6479 1.3142 0.3651 0.028 Uiso 1 1 calc R . . . .
C16 C 0.4037(4) 1.3297(3) 0.39313(8) 0.0240(5) Uani 1 1 d . . . . .
H16 H 0.4199 1.3713 0.4184 0.029 Uiso 1 1 calc R . . . .
C17 C 0.2429(4) 1.3009(3) 0.38719(8) 0.0253(6) Uani 1 1 d . . . . .
H17 H 0.1513 1.3237 0.4086 0.030 Uiso 1 1 calc R . . . .
C18 C 0.2180(4) 1.2383(3) 0.34953(8) 0.0221(5) Uani 1 1 d . . . . .
H18 H 0.1099 1.2197 0.3456 0.027 Uiso 1 1 calc R . . . .
C20 C 0.2863(4) 0.6614(3) 0.49698(8) 0.0251(5) Uani 1 1 d . . . . .
C21 C 0.2107(3) 0.7073(3) 0.54300(8) 0.0213(5) Uani 1 1 d . . . . .
C22 C 0.1882(3) 0.8883(3) 0.54517(8) 0.0211(5) Uani 1 1 d . . . . .
C23 C 0.2485(3) 0.9411(3) 0.50561(8) 0.0222(5) Uani 1 1 d . . . . .
C24 C 0.2446(4) 1.1066(4) 0.49753(9) 0.0280(6) Uani 1 1 d . . . . .
H24 H 0.2865 1.1414 0.4715 0.034 Uiso 1 1 calc R . . . .
C25 C 0.1756(4) 1.2205(4) 0.52981(10) 0.0325(6) Uani 1 1 d . . . . .
H25 H 0.1699 1.3335 0.5249 0.039 Uiso 1 1 calc R . . . .
C26 C 0.1152(4) 1.1694(4) 0.56898(9) 0.0315(6) Uani 1 1 d . . . . .
H26 H 0.0695 1.2482 0.5899 0.038 Uiso 1 1 calc R . . . .
C27 C 0.1225(4) 1.0012(4) 0.57732(8) 0.0260(6) Uani 1 1 d . . . . .
H27 H 0.0844 0.9655 0.6037 0.031 Uiso 1 1 calc R . . . .
C28 C 0.3760(4) 0.8180(4) 0.43440(9) 0.0354(7) Uani 1 1 d . . . . .
H28A H 0.2845 0.9028 0.4186 0.053 Uiso 1 1 calc GR . . . .
H28B H 0.4064 0.7096 0.4219 0.053 Uiso 1 1 calc GR . . . .
H28C H 0.4826 0.8502 0.4340 0.053 Uiso 1 1 calc GR . . . .
O11A O 0.9545(2) 0.0612(2) 0.31358(5) 0.0212(4) Uani 1 1 d . . . . .
N1A N 1.0940(3) -0.2022(3) 0.28535(6) 0.0195(4) Uani 1 1 d . . . . .
N12A N 0.8209(3) 0.1623(3) 0.22962(6) 0.0194(4) Uani 1 1 d . . . . .
C2A C 0.9873(3) -0.0333(3) 0.28438(7) 0.0179(5) Uani 1 1 d . . . . .
C3A C 0.9181(3) 0.0096(3) 0.23961(7) 0.0171(5) Uani 1 1 d . . . . .
C4A C 0.9852(3) -0.1522(3) 0.21815(8) 0.0185(5) Uani 1 1 d . . . . .
C5A C 1.0865(3) -0.2764(3) 0.24742(7) 0.0181(5) Uani 1 1 d . . . . .
C6A C 1.1582(4) -0.4475(3) 0.23907(8) 0.0231(5) Uani 1 1 d . . . . .
H6A H 1.2253 -0.5281 0.2588 0.028 Uiso 1 1 calc R . . . .
C7A C 1.1260(4) -0.4942(3) 0.19994(9) 0.0255(6) Uani 1 1 d . . . . .
H7A H 1.1701 -0.6089 0.1936 0.031 Uiso 1 1 calc R . . . .
C8A C 1.0294(4) -0.3734(3) 0.17019(8) 0.0251(5) Uani 1 1 d . . . . .
H8A H 1.0125 -0.4080 0.1440 0.030 Uiso 1 1 calc R . . . .
C9A C 0.9573(3) -0.2009(3) 0.17890(8) 0.0215(5) Uani 1 1 d . . . . .
H9A H 0.8921 -0.1203 0.1590 0.026 Uiso 1 1 calc R . . . .
C10A C 1.1835(4) -0.2969(3) 0.32247(8) 0.0236(5) Uani 1 1 d . . . . .
H10D H 1.1270 -0.3789 0.3326 0.035 Uiso 1 1 calc GR . . . .
H10E H 1.1728 -0.2192 0.3442 0.035 Uiso 1 1 calc GR . . . .
H10F H 1.3097 -0.3550 0.3151 0.035 Uiso 1 1 calc GR . . . .
C13A C 0.7633(3) 0.2092(3) 0.18754(8) 0.0198(5) Uani 1 1 d . . . . .
C14A C 0.8843(4) 0.2365(3) 0.15561(8) 0.0250(5) Uani 1 1 d . . . . .
H14A H 1.0060 0.2125 0.1608 0.030 Uiso 1 1 calc R . . . .
C15A C 0.8205(4) 0.3002(4) 0.11592(8) 0.0271(6) Uani 1 1 d . . . . .
H15A H 0.8996 0.3220 0.0947 0.033 Uiso 1 1 calc R . . . .
C16A C 0.6406(4) 0.3315(3) 0.10749(8) 0.0237(5) Uani 1 1 d . . . . .
H16A H 0.5993 0.3729 0.0808 0.028 Uiso 1 1 calc R . . . .
C17A C 0.5229(4) 0.3007(4) 0.13927(8) 0.0262(6) Uani 1 1 d . . . . .
H17A H 0.4030 0.3181 0.1336 0.031 Uiso 1 1 calc R . . . .
C18A C 0.5826(4) 0.2440(3) 0.17952(8) 0.0223(5) Uani 1 1 d . . . . .
H18A H 0.5013 0.2294 0.2011 0.027 Uiso 1 1 calc R . . . .
O29A O 1.1969(3) 0.4924(3) -0.02329(6) 0.0338(5) Uani 1 1 d . . . . .
O30A O 1.2125(3) 0.4025(2) 0.06808(6) 0.0305(4) Uani 1 1 d . . . . .
N19A N 1.2258(3) 0.2079(3) -0.02604(7) 0.0258(5) Uani 1 1 d . . . . .
C20A C 1.2133(4) 0.3526(3) -0.00683(8) 0.0240(5) Uani 1 1 d . . . . .
C21A C 1.2234(4) 0.3022(3) 0.04140(8) 0.0233(5) Uani 1 1 d . . . . .
C22A C 1.2442(4) 0.1207(3) 0.04491(8) 0.0225(5) Uani 1 1 d . . . . .
C23A C 1.2429(3) 0.0699(3) 0.00378(8) 0.0224(5) Uani 1 1 d . . . . .
C24A C 1.2548(4) -0.0938(4) -0.00369(9) 0.0305(6) Uani 1 1 d . . . . .
H24A H 1.2530 -0.1270 -0.0310 0.037 Uiso 1 1 calc R . . . .
C25A C 1.2696(4) -0.2080(4) 0.03129(10) 0.0344(7) Uani 1 1 d . . . . .
H25A H 1.2778 -0.3196 0.0271 0.041 Uiso 1 1 calc R . . . .
C26A C 1.2726(4) -0.1609(4) 0.07217(10) 0.0330(6) Uani 1 1 d . . . . .
H26A H 1.2837 -0.2408 0.0947 0.040 Uiso 1 1 calc R . . . .
C27A C 1.2591(4) 0.0060(4) 0.07961(8) 0.0272(6) Uani 1 1 d . . . . .
H27A H 1.2601 0.0394 0.1069 0.033 Uiso 1 1 calc R . . . .
C28A C 1.2191(4) 0.1975(4) -0.07137(8) 0.0352(7) Uani 1 1 d . . . . .
H28D H 1.1118 0.1737 -0.0771 0.053 Uiso 1 1 calc GR . . . .
H28E H 1.3249 0.1078 -0.0815 0.053 Uiso 1 1 calc GR . . . .
H28F H 1.2160 0.3043 -0.0854 0.053 Uiso 1 1 calc GR . . . .


_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
O11 C2 1.221(3) . ?
O29 C20 1.212(3) . ?
O30 C21 1.209(3) . ?
N1 C2 1.356(3) . ?
N1 C5 1.411(3) . ?
N1 C10 1.454(3) . ?
N12 C3 1.273(3) . ?
N12 C13 1.428(3) . ?
N19 C20 1.357(4) . ?
N19 C23 1.415(3) . ?
N19 C28 1.453(3) . ?
C2 C3 1.536(3) . ?
C3 C4 1.468(3) . ?
C4 C5 1.406(3) . ?
C4 C9 1.388(3) . ?
C5 C6 1.374(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.392(4) . ?
C7 H7 0.9300 . ?
C7 C8 1.391(4) . ?
C8 H8 0.9300 . ?
C8 C9 1.396(4) . ?
C9 H9 0.9300 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C13 C14 1.396(4) . ?
C13 C18 1.391(4) . ?
C14 H14 0.9300 . ?
C14 C15 1.386(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.387(4) . ?
C16 H16 0.9300 . ?
C16 C17 1.389(4) . ?
C17 H17 0.9300 . ?
C17 C18 1.390(4) . ?
C18 H18 0.9300 . ?
C20 C21 1.557(3) . ?
C21 C22 1.465(4) . ?
C22 C23 1.402(3) . ?
C22 C27 1.385(4) . ?
C23 C24 1.376(4) . ?
C24 H24 0.9300 . ?
C24 C25 1.396(4) . ?
C25 H25 0.9300 . ?
C25 C26 1.386(4) . ?
C26 H26 0.9300 . ?
C26 C27 1.391(4) . ?
C27 H27 0.9300 . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
O11A C2A 1.215(3) . ?
N1A C2A 1.369(3) . ?
N1A C5A 1.406(3) . ?
N1A C10A 1.453(3) . ?
N12A C3A 1.271(3) . ?
N12A C13A 1.425(3) . ?
C2A C3A 1.532(3) . ?
C3A C4A 1.468(3) . ?
C4A C5A 1.405(3) . ?
C4A C9A 1.392(3) . ?
C5A C6A 1.380(3) . ?
C6A H6A 0.9300 . ?
C6A C7A 1.393(4) . ?
C7A H7A 0.9300 . ?
C7A C8A 1.388(4) . ?
C8A H8A 0.9300 . ?
C8A C9A 1.394(3) . ?
C9A H9A 0.9300 . ?
C10A H10D 0.9600 . ?
C10A H10E 0.9600 . ?
C10A H10F 0.9600 . ?
C13A C14A 1.396(4) . ?
C13A C18A 1.385(4) . ?
C14A H14A 0.9300 . ?
C14A C15A 1.390(4) . ?
C15A H15A 0.9300 . ?
C15A C16A 1.387(4) . ?
C16A H16A 0.9300 . ?
C16A C17A 1.385(4) . ?
C17A H17A 0.9300 . ?
C17A C18A 1.386(4) . ?
C18A H18A 0.9300 . ?
O29A C20A 1.212(3) . ?
O30A C21A 1.211(3) . ?
N19A C20A 1.361(3) . ?
N19A C23A 1.412(3) . ?
N19A C28A 1.452(3) . ?
C20A C21A 1.557(3) . ?
C21A C22A 1.463(4) . ?
C22A C23A 1.402(3) . ?
C22A C27A 1.389(4) . ?
C23A C24A 1.372(4) . ?
C24A H24A 0.9300 . ?
C24A C25A 1.394(4) . ?
C25A H25A 0.9300 . ?
C25A C26A 1.386(4) . ?
C26A H26A 0.9300 . ?
C26A C27A 1.395(4) . ?
C27A H27A 0.9300 . ?
C28A H28D 0.9600 . ?
C28A H28E 0.9600 . ?
C28A H28F 0.9600 . ?

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
C2 N1 C5 111.3(2) . . ?
C2 N1 C10 123.7(2) . . ?
C5 N1 C10 125.0(2) . . ?
C3 N12 C13 120.1(2) . . ?
C20 N19 C23 110.9(2) . . ?
C20 N19 C28 124.5(2) . . ?
C23 N19 C28 124.6(2) . . ?
O11 C2 N1 126.4(2) . . ?
O11 C2 C3 127.4(2) . . ?
N1 C2 C3 106.2(2) . . ?
N12 C3 C2 118.6(2) . . ?
N12 C3 C4 135.7(2) . . ?
C4 C3 C2 105.71(19) . . ?
C5 C4 C3 106.4(2) . . ?
C9 C4 C3 133.9(2) . . ?
C9 C4 C5 119.6(2) . . ?
C4 C5 N1 110.4(2) . . ?
C6 C5 N1 127.2(2) . . ?
C6 C5 C4 122.3(2) . . ?
C5 C6 H6 121.3 . . ?
C5 C6 C7 117.5(2) . . ?
C7 C6 H6 121.3 . . ?
C6 C7 H7 119.3 . . ?
C8 C7 C6 121.4(2) . . ?
C8 C7 H7 119.3 . . ?
C7 C8 H8 119.7 . . ?
C7 C8 C9 120.6(2) . . ?
C9 C8 H8 119.7 . . ?
C4 C9 C8 118.6(2) . . ?
C4 C9 H9 120.7 . . ?
C8 C9 H9 120.7 . . ?
N1 C10 H10A 109.5 . . ?
N1 C10 H10B 109.5 . . ?
N1 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C14 C13 N12 120.0(2) . . ?
C18 C13 N12 119.5(2) . . ?
C18 C13 C14 120.2(2) . . ?
C13 C14 H14 120.2 . . ?
C15 C14 C13 119.5(2) . . ?
C15 C14 H14 120.2 . . ?
C14 C15 H15 119.7 . . ?
C14 C15 C16 120.7(3) . . ?
C16 C15 H15 119.7 . . ?
C15 C16 H16 120.2 . . ?
C15 C16 C17 119.5(2) . . ?
C17 C16 H16 120.2 . . ?
C16 C17 H17 119.7 . . ?
C16 C17 C18 120.5(2) . . ?
C18 C17 H17 119.7 . . ?
C13 C18 H18 120.2 . . ?
C17 C18 C13 119.5(2) . . ?
C17 C18 H18 120.2 . . ?
O29 C20 N19 128.1(2) . . ?
O29 C20 C21 125.6(3) . . ?
N19 C20 C21 106.2(2) . . ?
O30 C21 C20 123.8(2) . . ?
O30 C21 C22 131.2(2) . . ?
C22 C21 C20 105.1(2) . . ?
C23 C22 C21 106.9(2) . . ?
C27 C22 C21 132.0(2) . . ?
C27 C22 C23 121.1(2) . . ?
C22 C23 N19 110.9(2) . . ?
C24 C23 N19 128.1(2) . . ?
C24 C23 C22 121.0(2) . . ?
C23 C24 H24 121.2 . . ?
C23 C24 C25 117.7(3) . . ?
C25 C24 H24 121.2 . . ?
C24 C25 H25 119.2 . . ?
C26 C25 C24 121.6(3) . . ?
C26 C25 H25 119.2 . . ?
C25 C26 H26 119.7 . . ?
C25 C26 C27 120.5(3) . . ?
C27 C26 H26 119.7 . . ?
C22 C27 C26 118.0(3) . . ?
C22 C27 H27 121.0 . . ?
C26 C27 H27 121.0 . . ?
N19 C28 H28A 109.5 . . ?
N19 C28 H28B 109.5 . . ?
N19 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C2A N1A C5A 110.8(2) . . ?
C2A N1A C10A 124.4(2) . . ?
C5A N1A C10A 124.4(2) . . ?
C3A N12A C13A 120.5(2) . . ?
O11A C2A N1A 126.2(2) . . ?
O11A C2A C3A 127.7(2) . . ?
N1A C2A C3A 106.10(19) . . ?
N12A C3A C2A 119.0(2) . . ?
N12A C3A C4A 135.4(2) . . ?
C4A C3A C2A 105.63(19) . . ?
C5A C4A C3A 106.6(2) . . ?
C9A C4A C3A 133.7(2) . . ?
C9A C4A C5A 119.5(2) . . ?
C4A C5A N1A 110.6(2) . . ?
C6A C5A N1A 126.9(2) . . ?
C6A C5A C4A 122.4(2) . . ?
C5A C6A H6A 121.4 . . ?
C5A C6A C7A 117.2(2) . . ?
C7A C6A H6A 121.4 . . ?
C6A C7A H7A 119.3 . . ?
C8A C7A C6A 121.4(2) . . ?
C8A C7A H7A 119.3 . . ?
C7A C8A H8A 119.5 . . ?
C7A C8A C9A 121.0(2) . . ?
C9A C8A H8A 119.5 . . ?
C4A C9A C8A 118.4(2) . . ?
C4A C9A H9A 120.8 . . ?
C8A C9A H9A 120.8 . . ?
N1A C10A H10D 109.5 . . ?
N1A C10A H10E 109.5 . . ?
N1A C10A H10F 109.5 . . ?
H10D C10A H10E 109.5 . . ?
H10D C10A H10F 109.5 . . ?
H10E C10A H10F 109.5 . . ?
C14A C13A N12A 119.9(2) . . ?
C18A C13A N12A 119.5(2) . . ?
C18A C13A C14A 120.2(2) . . ?
C13A C14A H14A 120.4 . . ?
C15A C14A C13A 119.1(2) . . ?
C15A C14A H14A 120.4 . . ?
C14A C15A H15A 119.6 . . ?
C16A C15A C14A 120.8(3) . . ?
C16A C15A H15A 119.6 . . ?
C15A C16A H16A 120.3 . . ?
C17A C16A C15A 119.4(2) . . ?
C17A C16A H16A 120.3 . . ?
C16A C17A H17A 119.8 . . ?
C16A C17A C18A 120.5(3) . . ?
C18A C17A H17A 119.8 . . ?
C13A C18A C17A 119.9(2) . . ?
C13A C18A H18A 120.0 . . ?
C17A C18A H18A 120.0 . . ?
C20A N19A C23A 111.4(2) . . ?
C20A N19A C28A 124.3(2) . . ?
C23A N19A C28A 124.3(2) . . ?
O29A C20A N19A 127.9(2) . . ?
O29A C20A C21A 126.5(2) . . ?
N19A C20A C21A 105.6(2) . . ?
O30A C21A C20A 123.2(2) . . ?
O30A C21A C22A 131.4(2) . . ?
C22A C21A C20A 105.4(2) . . ?
C23A C22A C21A 107.0(2) . . ?
C27A C22A C21A 132.1(2) . . ?
C27A C22A C23A 120.9(2) . . ?
C22A C23A N19A 110.6(2) . . ?
C24A C23A N19A 127.9(2) . . ?
C24A C23A C22A 121.5(3) . . ?
C23A C24A H24A 121.4 . . ?
C23A C24A C25A 117.3(3) . . ?
C25A C24A H24A 121.4 . . ?
C24A C25A H25A 118.9 . . ?
C26A C25A C24A 122.2(3) . . ?
C26A C25A H25A 118.9 . . ?
C25A C26A H26A 119.9 . . ?
C25A C26A C27A 120.3(3) . . ?
C27A C26A H26A 119.9 . . ?
C22A C27A C26A 117.8(3) . . ?
C22A C27A H27A 121.1 . . ?
C26A C27A H27A 121.1 . . ?
N19A C28A H28D 109.5 . . ?
N19A C28A H28E 109.5 . . ?
N19A C28A H28F 109.5 . . ?
H28D C28A H28E 109.5 . . ?
H28D C28A H28F 109.5 . . ?
H28E C28A H28F 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O11 C2 C3 N12 1.2(4) . . . . ?
O11 C2 C3 C4 -180.0(2) . . . . ?
O29 C20 C21 O30 4.2(4) . . . . ?
O29 C20 C21 C22 -176.6(3) . . . . ?
O30 C21 C22 C23 177.5(3) . . . . ?
O30 C21 C22 C27 -2.6(5) . . . . ?
N1 C2 C3 N12 -179.9(2) . . . . ?
N1 C2 C3 C4 -1.1(3) . . . . ?
N1 C5 C6 C7 -178.2(2) . . . . ?
N12 C3 C4 C5 178.2(3) . . . . ?
N12 C3 C4 C9 2.3(5) . . . . ?
N12 C13 C14 C15 175.6(2) . . . . ?
N12 C13 C18 C17 -174.8(2) . . . . ?
N19 C20 C21 O30 -177.0(2) . . . . ?
N19 C20 C21 C22 2.2(3) . . . . ?
N19 C23 C24 C25 178.2(3) . . . . ?
C2 N1 C5 C4 -2.5(3) . . . . ?
C2 N1 C5 C6 175.6(3) . . . . ?
C2 C3 C4 C5 -0.4(3) . . . . ?
C2 C3 C4 C9 -176.2(3) . . . . ?
C3 N12 C13 C14 71.7(3) . . . . ?
C3 N12 C13 C18 -115.0(3) . . . . ?
C3 C4 C5 N1 1.7(3) . . . . ?
C3 C4 C5 C6 -176.6(2) . . . . ?
C3 C4 C9 C8 175.4(3) . . . . ?
C4 C5 C6 C7 -0.3(4) . . . . ?
C5 N1 C2 O11 -178.9(2) . . . . ?
C5 N1 C2 C3 2.2(3) . . . . ?
C5 C4 C9 C8 -0.1(4) . . . . ?
C5 C6 C7 C8 0.6(4) . . . . ?
C6 C7 C8 C9 -0.7(4) . . . . ?
C7 C8 C9 C4 0.4(4) . . . . ?
C9 C4 C5 N1 178.3(2) . . . . ?
C9 C4 C5 C6 0.0(4) . . . . ?
C10 N1 C2 O11 -1.3(4) . . . . ?
C10 N1 C2 C3 179.8(2) . . . . ?
C10 N1 C5 C4 179.8(2) . . . . ?
C10 N1 C5 C6 -2.0(4) . . . . ?
C13 N12 C3 C2 -176.0(2) . . . . ?
C13 N12 C3 C4 5.6(4) . . . . ?
C13 C14 C15 C16 -1.9(4) . . . . ?
C14 C13 C18 C17 -1.6(4) . . . . ?
C14 C15 C16 C17 0.6(4) . . . . ?
C15 C16 C17 C18 0.2(4) . . . . ?
C16 C17 C18 C13 0.3(4) . . . . ?
C18 C13 C14 C15 2.4(4) . . . . ?
C20 N19 C23 C22 1.0(3) . . . . ?
C20 N19 C23 C24 -178.5(3) . . . . ?
C20 C21 C22 C23 -1.6(3) . . . . ?
C20 C21 C22 C27 178.3(3) . . . . ?
C21 C22 C23 N19 0.5(3) . . . . ?
C21 C22 C23 C24 180.0(2) . . . . ?
C21 C22 C27 C26 -178.8(3) . . . . ?
C22 C23 C24 C25 -1.1(4) . . . . ?
C23 N19 C20 O29 176.8(3) . . . . ?
C23 N19 C20 C21 -1.9(3) . . . . ?
C23 C22 C27 C26 1.1(4) . . . . ?
C23 C24 C25 C26 1.0(4) . . . . ?
C24 C25 C26 C27 0.2(5) . . . . ?
C25 C26 C27 C22 -1.2(4) . . . . ?
C27 C22 C23 N19 -179.3(2) . . . . ?
C27 C22 C23 C24 0.1(4) . . . . ?
C28 N19 C20 O29 -1.6(5) . . . . ?
C28 N19 C20 C21 179.7(2) . . . . ?
C28 N19 C23 C22 179.4(3) . . . . ?
C28 N19 C23 C24 0.0(4) . . . . ?
O11A C2A C3A N12A 3.5(4) . . . . ?
O11A C2A C3A C4A -175.4(2) . . . . ?
N1A C2A C3A N12A -177.1(2) . . . . ?
N1A C2A C3A C4A 4.1(3) . . . . ?
N1A C5A C6A C7A 176.5(2) . . . . ?
N12A C3A C4A C5A -179.6(3) . . . . ?
N12A C3A C4A C9A -4.6(5) . . . . ?
N12A C13A C14A C15A -173.0(2) . . . . ?
N12A C13A C18A C17A 175.7(2) . . . . ?
C2A N1A C5A C4A 5.4(3) . . . . ?
C2A N1A C5A C6A -171.6(2) . . . . ?
C2A C3A C4A C5A -1.0(3) . . . . ?
C2A C3A C4A C9A 173.9(3) . . . . ?
C3A N12A C13A C14A -78.2(3) . . . . ?
C3A N12A C13A C18A 108.3(3) . . . . ?
C3A C4A C5A N1A -2.4(3) . . . . ?
C3A C4A C5A C6A 174.7(2) . . . . ?
C3A C4A C9A C8A -173.4(3) . . . . ?
C4A C5A C6A C7A -0.2(4) . . . . ?
C5A N1A C2A O11A 173.8(2) . . . . ?
C5A N1A C2A C3A -5.7(3) . . . . ?
C5A C4A C9A C8A 1.0(4) . . . . ?
C5A C6A C7A C8A 1.5(4) . . . . ?
C6A C7A C8A C9A -1.6(4) . . . . ?
C7A C8A C9A C4A 0.3(4) . . . . ?
C9A C4A C5A N1A -178.2(2) . . . . ?
C9A C4A C5A C6A -1.1(4) . . . . ?
C10A N1A C2A O11A 1.2(4) . . . . ?
C10A N1A C2A C3A -178.3(2) . . . . ?
C10A N1A C5A C4A 177.9(2) . . . . ?
C10A N1A C5A C6A 1.0(4) . . . . ?
C13A N12A C3A C2A 176.2(2) . . . . ?
C13A N12A C3A C4A -5.4(4) . . . . ?
C13A C14A C15A C16A -1.9(4) . . . . ?
C14A C13A C18A C17A 2.2(4) . . . . ?
C14A C15A C16A C17A 0.7(4) . . . . ?
C15A C16A C17A C18A 2.0(4) . . . . ?
C16A C17A C18A C13A -3.5(4) . . . . ?
C18A C13A C14A C15A 0.5(4) . . . . ?
O29A C20A C21A O30A 1.2(4) . . . . ?
O29A C20A C21A C22A -179.6(3) . . . . ?
O30A C21A C22A C23A 178.0(3) . . . . ?
O30A C21A C22A C27A -0.4(5) . . . . ?
N19A C20A C21A O30A -178.5(3) . . . . ?
N19A C20A C21A C22A 0.7(3) . . . . ?
N19A C23A C24A C25A -179.6(3) . . . . ?
C20A N19A C23A C22A -0.7(3) . . . . ?
C20A N19A C23A C24A 178.5(3) . . . . ?
C20A C21A C22A C23A -1.1(3) . . . . ?
C20A C21A C22A C27A -179.5(3) . . . . ?
C21A C22A C23A N19A 1.1(3) . . . . ?
C21A C22A C23A C24A -178.1(2) . . . . ?
C21A C22A C27A C26A 178.2(3) . . . . ?
C22A C23A C24A C25A -0.5(4) . . . . ?
C23A N19A C20A O29A -179.7(3) . . . . ?
C23A N19A C20A C21A 0.0(3) . . . . ?
C23A C22A C27A C26A 0.0(4) . . . . ?
C23A C24A C25A C26A 0.0(5) . . . . ?
C24A C25A C26A C27A 0.5(5) . . . . ?
C25A C26A C27A C22A -0.5(4) . . . . ?
C27A C22A C23A N19A 179.7(2) . . . . ?
C27A C22A C23A C24A 0.5(4) . . . . ?
C28A N19A C20A O29A -0.8(5) . . . . ?
C28A N19A C20A C21A 178.9(2) . . . . ?
C28A N19A C23A C22A -179.6(3) . . . . ?
C28A N19A C23A C24A -0.4(4) . . . . ?


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

data_Compound_5_lcb_003
_database_code_depnum_ccdc_archive 'CCDC 1505869'
_audit_update_record             
;
2016-09-22 deposited with the CCDC.
2017-01-29 downloaded from the CCDC.
;
_audit_creation_date             2015-01-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.06 svn.r3119 for OlexSys, GUI svn.r4979)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C30 H24 Br4 Hg2 N4 O2'
_chemical_formula_sum            'C30 H24 Br4 Hg2 N4 O2'
_chemical_formula_weight         1193.35
_chemical_melting_point          ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Hg Hg -2.3894 9.2266 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   23.6723(11)
_cell_length_b                   19.9737(5)
_cell_length_c                   14.0418(4)
_cell_angle_alpha                90
_cell_angle_beta                 101.024(3)
_cell_angle_gamma                90
_cell_volume                     6516.8(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    5047
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.6800
_cell_measurement_theta_min      2.8150
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    14.351
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.46856
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    2.433
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             4384
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.06
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0713
_diffrn_reflns_av_unetI/netI     0.1113
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            35683
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.998
_diffrn_reflns_theta_min         2.572
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 16.2096
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -25.00   15.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.8777  -99.0000 -180.0000 40

#__ type_ start__ end____ width___ exp.time_
  2 omega  -37.00    8.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.8777   57.0000   90.0000 45

#__ type_ start__ end____ width___ exp.time_
  3 omega  -83.00  -11.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.8777  -57.0000 -120.0000 72

#__ type_ start__ end____ width___ exp.time_
  4 omega   40.00   67.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       18.8152  178.0000  120.0000 27

#__ type_ start__ end____ width___ exp.time_
  5 omega   -1.00   72.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       18.8152   38.0000 -180.0000 73

#__ type_ start__ end____ width___ exp.time_
  6 omega  -56.00  -31.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.8777  -38.0000  120.0000 25
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0170314000
_diffrn_orient_matrix_UB_12      0.0292570000
_diffrn_orient_matrix_UB_13      0.0004475000
_diffrn_orient_matrix_UB_21      0.0242986000
_diffrn_orient_matrix_UB_22      -0.0200656000
_diffrn_orient_matrix_UB_23      -0.0030603000
_diffrn_orient_matrix_UB_31      -0.0071363000
_diffrn_orient_matrix_UB_32      0.0014668000
_diffrn_orient_matrix_UB_33      -0.0513891000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                9725
_reflns_number_total             13989
_reflns_odcompleteness_completeness 99.85
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         2.940
_refine_diff_density_min         -1.708
_refine_diff_density_rms         0.325
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.127
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     665
_refine_ls_number_reflns         13989
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1071
_refine_ls_R_factor_gt           0.0676
_refine_ls_restrained_S_all      1.127
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0237P)²+73.9840P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1179
_refine_ls_wR_factor_ref         0.1325
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C14C) = Uanis(C15C) = Uanis(C16C)
Uanis(C3B) = Uanis(C2B)
Uanis(C13B) = Uanis(C18B) = Uanis(C14B)
Uanis(C7A) = Uanis(C8A)
Uanis(C13A) = Uanis(C14A) = Uanis(C15A)
Uanis(C9B) = Uanis(C8B) = Uanis(C7B)
Uanis(C3) = Uanis(C2) = Uanis(O11) = Uanis(N12)
Uanis(C3A) = Uanis(C4A)
Uanis(C10A) = Uanis(N1A) = Uanis(C5A)
3.a Aromatic/amide H refined with riding coordinates:
 C6A(H6A), C6C(H6C), C7A(H7A), C7C(H7C), C8A(H8A), C8C(H8C), C9A(H9A),
 C9C(H9C), C14A(H14A), C14C(H14C), C15A(H15A), C15C(H15C), C16A(H16A),
 C16C(H16C), C17A(H17A), C17C(H17C), C18A(H18A), C18C(H18C), C6B(H6B), C7B(H7B),
  C8B(H8B), C9B(H9B), C14B(H14B), C15B(H15B), C16B(H16B), C17B(H17B),
 C18B(H18B), C6(H6), C7(H7), C8(H8), C9(H9), C14(H14), C15(H15), C16(H16),
 C17(H17), C18(H18)
3.b Idealised Me refined as rotating group:
 C10A(H10D,H10E,H10F), C10C(H10A,H10B,H10C), C10B(H10G,H10H,H10I), C10(H10J,
 H10K,H10L)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Hg3A Hg 0.51438(3) 0.84319(3) 0.39140(4) 0.02104(14) Uani 1 1 d . . . . .
Hg3C Hg 0.62990(3) 0.96605(3) 0.28929(4) 0.02178(14) Uani 1 1 d . . . . .
Br4A Br 0.52540(7) 0.86106(7) 0.22363(10) 0.0238(3) Uani 1 1 d . . . . .
Br4C Br 0.64948(7) 0.96603(7) 0.12380(10) 0.0262(3) Uani 1 1 d . . . . .
Br5A Br 0.52744(7) 0.83392(8) 0.56708(10) 0.0324(4) Uani 1 1 d . . . . .
Br5C Br 0.59444(7) 0.99313(7) 0.43784(10) 0.0257(3) Uani 1 1 d . . . . .
O11A O 0.4042(4) 0.8786(5) 0.3431(6) 0.023(2) Uani 1 1 d . . . . .
O11C O 0.7414(4) 0.9976(5) 0.3520(7) 0.028(2) Uani 1 1 d . . . . .
N1A N 0.3153(5) 0.8315(5) 0.3072(7) 0.0179(17) Uani 1 1 d . . . . .
N1C N 0.8288(5) 0.9423(5) 0.3889(8) 0.017(3) Uani 1 1 d . . . . .
N12A N 0.4438(5) 0.7439(6) 0.3591(8) 0.021(3) Uani 1 1 d . . . . .
N12C N 0.6939(5) 0.8668(5) 0.3571(8) 0.018(3) Uani 1 1 d . . . . .
C2A C 0.3718(6) 0.8295(7) 0.3293(9) 0.018(3) Uani 1 1 d . . . . .
C2C C 0.7705(6) 0.9466(7) 0.3681(9) 0.019(3) Uani 1 1 d . . . . .
C3A C 0.3894(6) 0.7562(7) 0.3352(9) 0.017(2) Uani 1 1 d . . . . .
C3C C 0.7480(6) 0.8759(6) 0.3731(8) 0.013(3) Uani 1 1 d . . . . .
C4A C 0.3362(6) 0.7179(7) 0.3183(9) 0.017(2) Uani 1 1 d . . . . .
C4C C 0.7981(6) 0.8331(7) 0.4022(9) 0.018(3) Uani 1 1 d . . . . .
C5A C 0.2916(6) 0.7653(7) 0.3023(9) 0.0179(17) Uani 1 1 d . . . . .
C5C C 0.8474(6) 0.8752(7) 0.4104(9) 0.020(3) Uani 1 1 d . . . . .
C6A C 0.2359(6) 0.7475(7) 0.2840(8) 0.021(3) Uani 1 1 d . . . . .
H6A H 0.2070 0.7796 0.2706 0.025 Uiso 1 1 calc R . . . .
C6C C 0.9020(7) 0.8519(7) 0.4350(9) 0.023(3) Uani 1 1 d . . . . .
H6C H 0.9334 0.8806 0.4387 0.027 Uiso 1 1 calc R . . . .
C7A C 0.2221(7) 0.6780(7) 0.2855(9) 0.024(2) Uani 1 1 d . . . . .
H7A H 0.1838 0.6645 0.2751 0.029 Uiso 1 1 calc R . . . .
C7C C 0.9100(6) 0.7833(7) 0.4545(9) 0.022(3) Uani 1 1 d . . . . .
H7C H 0.9469 0.7658 0.4723 0.026 Uiso 1 1 calc R . . . .
C8A C 0.2655(7) 0.6309(7) 0.3024(9) 0.024(2) Uani 1 1 d . . . . .
H8A H 0.2562 0.5857 0.3047 0.029 Uiso 1 1 calc R . . . .
C8C C 0.8627(6) 0.7421(7) 0.4471(9) 0.020(3) Uani 1 1 d . . . . .
H8C H 0.8688 0.6968 0.4605 0.025 Uiso 1 1 calc R . . . .
C9A C 0.3234(6) 0.6503(6) 0.3160(9) 0.019(3) Uani 1 1 d . . . . .
H9A H 0.3526 0.6185 0.3234 0.023 Uiso 1 1 calc R . . . .
C9C C 0.8068(7) 0.7647(7) 0.4207(9) 0.022(3) Uani 1 1 d . . . . .
H9C H 0.7758 0.7354 0.4154 0.027 Uiso 1 1 calc R . . . .
C10A C 0.2794(6) 0.8922(6) 0.3059(9) 0.0179(17) Uani 1 1 d . . . . .
H10D H 0.3037 0.9304 0.3234 0.027 Uiso 1 1 calc GR . . . .
H10E H 0.2542 0.8870 0.3515 0.027 Uiso 1 1 calc GR . . . .
H10F H 0.2569 0.8985 0.2420 0.027 Uiso 1 1 calc GR . . . .
C10C C 0.8667(6) 1.0000(7) 0.3942(10) 0.026(4) Uani 1 1 d . . . . .
H10A H 0.8843 1.0081 0.4607 0.040 Uiso 1 1 calc GR . . . .
H10B H 0.8448 1.0385 0.3684 0.040 Uiso 1 1 calc GR . . . .
H10C H 0.8961 0.9914 0.3571 0.040 Uiso 1 1 calc GR . . . .
C13A C 0.4649(6) 0.6758(7) 0.3644(9) 0.0197(18) Uani 1 1 d . . . . .
C13C C 0.6703(6) 0.8005(6) 0.3673(10) 0.020(3) Uani 1 1 d . . . . .
C14A C 0.4668(6) 0.6386(7) 0.2796(10) 0.0197(18) Uani 1 1 d . . . . .
H14A H 0.4513 0.6559 0.2187 0.024 Uiso 1 1 calc R . . . .
C14C C 0.6576(6) 0.7607(7) 0.2858(10) 0.0210(19) Uani 1 1 d . . . . .
H14C H 0.6645 0.7751 0.2261 0.025 Uiso 1 1 calc R . . . .
C15A C 0.4922(6) 0.5759(7) 0.2889(10) 0.0197(18) Uani 1 1 d . . . . .
H15A H 0.4953 0.5519 0.2334 0.024 Uiso 1 1 calc R . . . .
C15C C 0.6345(6) 0.6986(7) 0.2970(10) 0.0210(19) Uani 1 1 d . . . . .
H15C H 0.6278 0.6701 0.2437 0.025 Uiso 1 1 calc R . . . .
C16A C 0.5129(6) 0.5486(7) 0.3783(10) 0.023(3) Uani 1 1 d . . . . .
H16A H 0.5285 0.5057 0.3829 0.028 Uiso 1 1 calc R . . . .
C16C C 0.6207(6) 0.6768(7) 0.3806(10) 0.0210(19) Uani 1 1 d . . . . .
H16C H 0.6038 0.6351 0.3843 0.025 Uiso 1 1 calc R . . . .
C17A C 0.5106(6) 0.5850(6) 0.4624(10) 0.019(3) Uani 1 1 d . . . . .
H17A H 0.5245 0.5663 0.5230 0.023 Uiso 1 1 calc R . . . .
C17C C 0.6330(7) 0.7191(8) 0.4619(11) 0.034(4) Uani 1 1 d . . . . .
H17C H 0.6251 0.7047 0.5210 0.040 Uiso 1 1 calc R . . . .
C18A C 0.4875(6) 0.6493(7) 0.4552(9) 0.021(3) Uani 1 1 d . . . . .
H18A H 0.4872 0.6743 0.5109 0.025 Uiso 1 1 calc R . . . .
C18C C 0.6564(6) 0.7815(7) 0.4551(10) 0.025(4) Uani 1 1 d . . . . .
H18C H 0.6627 0.8104 0.5081 0.030 Uiso 1 1 calc R . . . .
Hg3B Hg 0.87885(2) 0.42839(3) 0.47398(4) 0.01889(13) Uani 1 1 d . . . . .
Br4B Br 0.87945(6) 0.43231(7) 0.29962(9) 0.0216(3) Uani 1 1 d . . . . .
Br5B Br 0.89370(7) 0.44079(7) 0.64973(9) 0.0219(3) Uani 1 1 d . . . . .
O11B O 0.7647(4) 0.4302(4) 0.4549(6) 0.021(2) Uani 1 1 d . . . . .
N1B N 0.6878(5) 0.3567(6) 0.4383(7) 0.019(3) Uani 1 1 d . . . . .
N12B N 0.8324(5) 0.3112(5) 0.4647(7) 0.018(3) Uani 1 1 d . . . . .
C2B C 0.7441(6) 0.3737(7) 0.4515(9) 0.016(2) Uani 1 1 d . . . . .
C3B C 0.7784(6) 0.3085(7) 0.4608(9) 0.016(2) Uani 1 1 d . . . . .
C4B C 0.7360(6) 0.2541(6) 0.4505(9) 0.017(3) Uani 1 1 d . . . . .
C5B C 0.6822(6) 0.2859(7) 0.4415(9) 0.019(3) Uani 1 1 d . . . . .
C6B C 0.6313(6) 0.2501(7) 0.4331(8) 0.015(3) Uani 1 1 d . . . . .
H6B H 0.5958 0.2715 0.4251 0.018 Uiso 1 1 calc R . . . .
C7B C 0.6359(6) 0.1805(7) 0.4373(8) 0.0182(18) Uani 1 1 d . . . . .
H7B H 0.6030 0.1547 0.4359 0.022 Uiso 1 1 calc R . . . .
C8B C 0.6897(6) 0.1485(7) 0.4437(8) 0.0182(18) Uani 1 1 d . . . . .
H8B H 0.6919 0.1020 0.4431 0.022 Uiso 1 1 calc R . . . .
C9B C 0.7376(6) 0.1856(7) 0.4505(8) 0.0182(18) Uani 1 1 d . . . . .
H9B H 0.7729 0.1641 0.4555 0.022 Uiso 1 1 calc R . . . .
C10B C 0.6411(6) 0.4031(7) 0.4256(9) 0.021(3) Uani 1 1 d . . . . .
H10G H 0.6142 0.3923 0.3674 0.032 Uiso 1 1 calc GR . . . .
H10H H 0.6555 0.4476 0.4207 0.032 Uiso 1 1 calc GR . . . .
H10I H 0.6222 0.4005 0.4803 0.032 Uiso 1 1 calc GR . . . .
C13B C 0.8689(6) 0.2524(6) 0.4746(9) 0.0143(17) Uani 1 1 d . . . . .
C14B C 0.8998(5) 0.2405(6) 0.4010(9) 0.0143(17) Uani 1 1 d . . . . .
H14B H 0.8970 0.2699 0.3490 0.017 Uiso 1 1 calc R . . . .
C15B C 0.9349(6) 0.1841(6) 0.4063(10) 0.022(3) Uani 1 1 d . . . . .
H15B H 0.9562 0.1756 0.3585 0.027 Uiso 1 1 calc R . . . .
C16B C 0.9374(6) 0.1409(7) 0.4840(10) 0.021(3) Uani 1 1 d . . . . .
H16B H 0.9602 0.1027 0.4871 0.025 Uiso 1 1 calc R . . . .
C17B C 0.9066(6) 0.1529(7) 0.5579(10) 0.024(3) Uani 1 1 d . . . . .
H17B H 0.9088 0.1236 0.6099 0.029 Uiso 1 1 calc R . . . .
C18B C 0.8731(6) 0.2095(6) 0.5512(9) 0.0143(17) Uani 1 1 d . . . . .
H18B H 0.8527 0.2188 0.6001 0.017 Uiso 1 1 calc R . . . .
Hg13 Hg 0.03808(2) 0.06501(3) 0.19923(4) 0.01727(13) Uani 1 1 d . . . . .
Br14 Br 0.02551(6) 0.01914(7) 0.35685(9) 0.0210(3) Uani 1 1 d . . . . .
Br15 Br 0.03744(7) 0.08579(7) 0.02593(9) 0.0254(4) Uani 1 1 d . . . . .
O11 O 0.0154(4) 0.1895(4) 0.2336(6) 0.0194(14) Uani 1 1 d . . . . .
N1 N 0.0607(5) 0.2886(5) 0.2858(7) 0.018(3) Uani 1 1 d . . . . .
N12 N 0.1299(5) 0.1374(5) 0.2588(7) 0.0194(14) Uani 1 1 d . . . . .
C2 C 0.0585(7) 0.2222(7) 0.2631(9) 0.0194(14) Uani 1 1 d . . . . .
C3 C 0.1208(6) 0.1972(7) 0.2789(9) 0.0194(14) Uani 1 1 d . . . . .
C4 C 0.1566(7) 0.2568(7) 0.3123(9) 0.022(3) Uani 1 1 d . . . . .
C5 C 0.1173(6) 0.3102(7) 0.3124(9) 0.019(3) Uani 1 1 d . . . . .
C6 C 0.1366(6) 0.3740(6) 0.3410(9) 0.016(3) Uani 1 1 d . . . . .
H6 H 0.1106 0.4086 0.3434 0.020 Uiso 1 1 calc R . . . .
C7 C 0.1963(7) 0.3853(7) 0.3664(10) 0.024(4) Uani 1 1 d . . . . .
H7 H 0.2101 0.4279 0.3842 0.029 Uiso 1 1 calc R . . . .
C8 C 0.2346(6) 0.3329(7) 0.3649(10) 0.022(3) Uani 1 1 d . . . . .
H8 H 0.2739 0.3406 0.3827 0.027 Uiso 1 1 calc R . . . .
C9 C 0.2150(6) 0.2691(7) 0.3373(9) 0.022(3) Uani 1 1 d . . . . .
H9 H 0.2411 0.2346 0.3356 0.026 Uiso 1 1 calc R . . . .
C10 C 0.0112(6) 0.3315(7) 0.2764(11) 0.027(4) Uani 1 1 d . . . . .
H10J H 0.0115 0.3628 0.2247 0.040 Uiso 1 1 calc GR . . . .
H10K H 0.0121 0.3553 0.3360 0.040 Uiso 1 1 calc GR . . . .
H10L H -0.0232 0.3049 0.2621 0.040 Uiso 1 1 calc GR . . . .
C13 C 0.1886(6) 0.1111(7) 0.2701(10) 0.020(3) Uani 1 1 d . . . . .
C14 C 0.2203(8) 0.1000(8) 0.3601(11) 0.040(5) Uani 1 1 d . . . . .
H14 H 0.2048 0.1098 0.4146 0.048 Uiso 1 1 calc R . . . .
C15 C 0.2750(8) 0.0743(8) 0.3712(13) 0.041(5) Uani 1 1 d . . . . .
H15 H 0.2963 0.0671 0.4332 0.049 Uiso 1 1 calc R . . . .
C16 C 0.2984(7) 0.0595(7) 0.2925(13) 0.038(4) Uani 1 1 d . . . . .
H16 H 0.3359 0.0437 0.2996 0.046 Uiso 1 1 calc R . . . .
C17 C 0.2642(8) 0.0688(7) 0.2006(13) 0.042(5) Uani 1 1 d . . . . .
H17 H 0.2792 0.0576 0.1462 0.051 Uiso 1 1 calc R . . . .
C18 C 0.2096(7) 0.0937(6) 0.1877(10) 0.027(4) Uani 1 1 d . . . . .
H18 H 0.1873 0.0989 0.1260 0.032 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Hg3A Br4A 2.4455(14) . ?
Hg3A Br5A 2.4339(15) . ?
Hg3A O11A 2.662(10) . ?
Hg3A N12A 2.577(12) . ?
Hg3C Br4A 3.2396(15) . ?
Hg3C Br4C 2.4549(15) . ?
Hg3C Br5C 2.4532(16) . ?
Hg3C O11C 2.693(10) . ?
Hg3C N12C 2.565(11) . ?
O11A C2A 1.237(15) . ?
O11C C2C 1.226(16) . ?
N1A C2A 1.315(17) . ?
N1A C5A 1.433(17) . ?
N1A C10A 1.478(16) . ?
N1C C2C 1.358(17) . ?
N1C C5C 1.424(17) . ?
N1C C10C 1.453(16) . ?
N12A C3A 1.292(17) . ?
N12A C13A 1.445(17) . ?
N12C C3C 1.272(16) . ?
N12C C13C 1.455(16) . ?
C2A C3A 1.520(18) . ?
C2C C3C 1.515(17) . ?
C3A C4A 1.452(18) . ?
C3C C4C 1.454(18) . ?
C4A C5A 1.405(19) . ?
C4A C9A 1.383(17) . ?
C4C C5C 1.427(19) . ?
C4C C9C 1.398(18) . ?
C5A C6A 1.342(19) . ?
C5C C6C 1.35(2) . ?
C6A H6A 0.9300 . ?
C6A C7A 1.426(19) . ?
C6C H6C 0.9300 . ?
C6C C7C 1.403(19) . ?
C7A H7A 0.9300 . ?
C7A C8A 1.38(2) . ?
C7C H7C 0.9300 . ?
C7C C8C 1.38(2) . ?
C8A H8A 0.9300 . ?
C8A C9A 1.403(19) . ?
C8C H8C 0.9300 . ?
C8C C9C 1.381(19) . ?
C9A H9A 0.9300 . ?
C9C H9C 0.9300 . ?
C10A H10D 0.9600 . ?
C10A H10E 0.9600 . ?
C10A H10F 0.9600 . ?
C10C H10A 0.9600 . ?
C10C H10B 0.9600 . ?
C10C H10C 0.9600 . ?
C13A C14A 1.412(18) . ?
C13A C18A 1.390(17) . ?
C13C C14C 1.378(18) . ?
C13C C18C 1.388(19) . ?
C14A H14A 0.9300 . ?
C14A C15A 1.386(18) . ?
C14C H14C 0.9300 . ?
C14C C15C 1.376(18) . ?
C15A H15A 0.9300 . ?
C15A C16A 1.370(18) . ?
C15C H15C 0.9300 . ?
C15C C16C 1.349(18) . ?
C16A H16A 0.9300 . ?
C16A C17A 1.397(18) . ?
C16C H16C 0.9300 . ?
C16C C17C 1.406(19) . ?
C17A H17A 0.9300 . ?
C17A C18A 1.391(18) . ?
C17C H17C 0.9300 . ?
C17C C18C 1.376(19) . ?
C18A H18A 0.9300 . ?
C18C H18C 0.9300 . ?
Hg3B Br4B 2.4524(14) . ?
Hg3B Br5B 2.4379(14) . ?
Hg3B O11B 2.665(10) . ?
Hg3B N12B 2.578(11) . ?
O11B C2B 1.225(15) . ?
N1B C2B 1.352(17) . ?
N1B C5B 1.422(17) . ?
N1B C10B 1.428(17) . ?
N12B C3B 1.270(17) . ?
N12B C13B 1.450(16) . ?
C2B C3B 1.527(18) . ?
C3B C4B 1.468(18) . ?
C4B C5B 1.406(19) . ?
C4B C9B 1.369(18) . ?
C5B C6B 1.388(18) . ?
C6B H6B 0.9300 . ?
C6B C7B 1.395(18) . ?
C7B H7B 0.9300 . ?
C7B C8B 1.413(19) . ?
C8B H8B 0.9300 . ?
C8B C9B 1.342(18) . ?
C9B H9B 0.9300 . ?
C10B H10G 0.9600 . ?
C10B H10H 0.9600 . ?
C10B H10I 0.9600 . ?
C13B C14B 1.395(17) . ?
C13B C18B 1.364(17) . ?
C14B H14B 0.9300 . ?
C14B C15B 1.394(18) . ?
C15B H15B 0.9300 . ?
C15B C16B 1.382(18) . ?
C16B H16B 0.9300 . ?
C16B C17B 1.399(19) . ?
C17B H17B 0.9300 . ?
C17B C18B 1.374(18) . ?
C18B H18B 0.9300 . ?
Hg13 Br14 2.4654(14) . ?
Hg13 Br15 2.4658(14) . ?
Hg13 O11 2.609(9) . ?
Hg13 N12 2.612(12) . ?
O11 C2 1.214(16) . ?
N1 C2 1.362(16) . ?
N1 C5 1.390(17) . ?
N1 C10 1.438(17) . ?
N12 C3 1.257(16) . ?
N12 C13 1.464(18) . ?
C2 C3 1.53(2) . ?
C3 C4 1.483(19) . ?
C4 C5 1.416(19) . ?
C4 C9 1.380(19) . ?
C5 C6 1.386(18) . ?
C6 H6 0.9300 . ?
C6 C7 1.408(19) . ?
C7 H7 0.9300 . ?
C7 C8 1.387(19) . ?
C8 H8 0.9300 . ?
C8 C9 1.386(18) . ?
C9 H9 0.9300 . ?
C10 H10J 0.9600 . ?
C10 H10K 0.9600 . ?
C10 H10L 0.9600 . ?
C13 C14 1.359(19) . ?
C13 C18 1.388(19) . ?
C14 H14 0.9300 . ?
C14 C15 1.37(2) . ?
C15 H15 0.9300 . ?
C15 C16 1.36(2) . ?
C16 H16 0.9300 . ?
C16 C17 1.40(2) . ?
C17 H17 0.9300 . ?
C17 C18 1.36(2) . ?
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
Br4A Hg3A O11A 89.8(2) . . ?
Br4A Hg3A N12A 97.3(2) . . ?
Br5A Hg3A Br4A 166.22(6) . . ?
Br5A Hg3A O11A 101.9(2) . . ?
Br5A Hg3A N12A 94.1(2) . . ?
N12A Hg3A O11A 65.7(3) . . ?
Br4C Hg3C Br4A 90.15(5) . . ?
Br4C Hg3C O11C 87.7(2) . . ?
Br4C Hg3C N12C 98.4(3) . . ?
Br5C Hg3C Br4A 91.03(5) . . ?
Br5C Hg3C Br4C 164.19(5) . . ?
Br5C Hg3C O11C 98.3(2) . . ?
Br5C Hg3C N12C 97.4(3) . . ?
O11C Hg3C Br4A 153.1(2) . . ?
N12C Hg3C Br4A 88.3(2) . . ?
N12C Hg3C O11C 65.6(3) . . ?
Hg3A Br4A Hg3C 92.10(4) . . ?
C2A O11A Hg3A 112.2(9) . . ?
C2C O11C Hg3C 110.3(8) . . ?
C2A N1A C5A 110.8(11) . . ?
C2A N1A C10A 125.8(11) . . ?
C5A N1A C10A 122.4(11) . . ?
C2C N1C C5C 111.5(11) . . ?
C2C N1C C10C 123.5(11) . . ?
C5C N1C C10C 124.9(12) . . ?
C3A N12A Hg3A 118.7(9) . . ?
C3A N12A C13A 120.6(12) . . ?
C13A N12A Hg3A 120.7(9) . . ?
C3C N12C Hg3C 117.3(8) . . ?
C3C N12C C13C 120.4(12) . . ?
C13C N12C Hg3C 122.0(8) . . ?
O11A C2A N1A 125.8(13) . . ?
O11A C2A C3A 126.8(13) . . ?
N1A C2A C3A 107.4(11) . . ?
O11C C2C N1C 127.2(13) . . ?
O11C C2C C3C 126.3(13) . . ?
N1C C2C C3C 106.4(12) . . ?
N12A C3A C2A 116.5(12) . . ?
N12A C3A C4A 137.1(13) . . ?
C4A C3A C2A 106.2(12) . . ?
N12C C3C C2C 118.5(12) . . ?
N12C C3C C4C 134.8(12) . . ?
C4C C3C C2C 106.6(12) . . ?
C5A C4A C3A 105.9(12) . . ?
C9A C4A C3A 134.2(14) . . ?
C9A C4A C5A 119.9(13) . . ?
C5C C4C C3C 106.7(12) . . ?
C9C C4C C3C 135.2(14) . . ?
C9C C4C C5C 118.1(13) . . ?
C4A C5A N1A 109.8(12) . . ?
C6A C5A N1A 128.0(13) . . ?
C6A C5A C4A 122.2(13) . . ?
N1C C5C C4C 108.8(12) . . ?
C6C C5C N1C 128.2(13) . . ?
C6C C5C C4C 123.0(14) . . ?
C5A C6A H6A 120.8 . . ?
C5A C6A C7A 118.4(14) . . ?
C7A C6A H6A 120.8 . . ?
C5C C6C H6C 120.9 . . ?
C5C C6C C7C 118.1(14) . . ?
C7C C6C H6C 120.9 . . ?
C6A C7A H7A 119.9 . . ?
C8A C7A C6A 120.1(14) . . ?
C8A C7A H7A 119.9 . . ?
C6C C7C H7C 120.2 . . ?
C8C C7C C6C 119.5(13) . . ?
C8C C7C H7C 120.2 . . ?
C7A C8A H8A 119.7 . . ?
C7A C8A C9A 120.6(14) . . ?
C9A C8A H8A 119.7 . . ?
C7C C8C H8C 118.4 . . ?
C7C C8C C9C 123.2(14) . . ?
C9C C8C H8C 118.4 . . ?
C4A C9A C8A 118.6(14) . . ?
C4A C9A H9A 120.7 . . ?
C8A C9A H9A 120.7 . . ?
C4C C9C H9C 121.0 . . ?
C8C C9C C4C 118.0(14) . . ?
C8C C9C H9C 121.0 . . ?
N1A C10A H10D 109.5 . . ?
N1A C10A H10E 109.5 . . ?
N1A C10A H10F 109.5 . . ?
H10D C10A H10E 109.5 . . ?
H10D C10A H10F 109.5 . . ?
H10E C10A H10F 109.5 . . ?
N1C C10C H10A 109.5 . . ?
N1C C10C H10B 109.5 . . ?
N1C C10C H10C 109.5 . . ?
H10A C10C H10B 109.5 . . ?
H10A C10C H10C 109.5 . . ?
H10B C10C H10C 109.5 . . ?
C14A C13A N12A 121.2(12) . . ?
C18A C13A N12A 118.4(12) . . ?
C18A C13A C14A 120.3(13) . . ?
C14C C13C N12C 118.0(12) . . ?
C14C C13C C18C 122.0(13) . . ?
C18C C13C N12C 119.8(12) . . ?
C13A C14A H14A 120.7 . . ?
C15A C14A C13A 118.7(13) . . ?
C15A C14A H14A 120.7 . . ?
C13C C14C H14C 121.5 . . ?
C15C C14C C13C 116.9(13) . . ?
C15C C14C H14C 121.5 . . ?
C14A C15A H15A 119.4 . . ?
C16A C15A C14A 121.2(13) . . ?
C16A C15A H15A 119.4 . . ?
C14C C15C H15C 118.1 . . ?
C16C C15C C14C 123.9(14) . . ?
C16C C15C H15C 118.1 . . ?
C15A C16A H16A 119.9 . . ?
C15A C16A C17A 120.2(13) . . ?
C17A C16A H16A 119.9 . . ?
C15C C16C H16C 121.1 . . ?
C15C C16C C17C 117.8(14) . . ?
C17C C16C H16C 121.1 . . ?
C16A C17A H17A 120.1 . . ?
C18A C17A C16A 119.8(13) . . ?
C18A C17A H17A 120.1 . . ?
C16C C17C H17C 119.6 . . ?
C18C C17C C16C 120.8(14) . . ?
C18C C17C H17C 119.6 . . ?
C13A C18A C17A 119.7(13) . . ?
C13A C18A H18A 120.1 . . ?
C17A C18A H18A 120.1 . . ?
C13C C18C H18C 120.8 . . ?
C17C C18C C13C 118.4(13) . . ?
C17C C18C H18C 120.8 . . ?
Br4B Hg3B O11B 95.65(19) . . ?
Br4B Hg3B N12B 93.6(2) . . ?
Br5B Hg3B Br4B 168.56(5) . . ?
Br5B Hg3B O11B 92.73(19) . . ?
Br5B Hg3B N12B 97.0(2) . . ?
N12B Hg3B O11B 65.9(3) . . ?
C2B O11B Hg3B 112.3(9) . . ?
C2B N1B C5B 110.0(12) . . ?
C2B N1B C10B 125.0(12) . . ?
C5B N1B C10B 125.1(12) . . ?
C3B N12B Hg3B 117.2(9) . . ?
C3B N12B C13B 123.1(11) . . ?
C13B N12B Hg3B 119.4(8) . . ?
O11B C2B N1B 127.6(13) . . ?
O11B C2B C3B 125.5(13) . . ?
N1B C2B C3B 106.9(12) . . ?
N12B C3B C2B 118.8(12) . . ?
N12B C3B C4B 134.4(13) . . ?
C4B C3B C2B 106.3(12) . . ?
C5B C4B C3B 105.4(11) . . ?
C9B C4B C3B 136.1(14) . . ?
C9B C4B C5B 118.5(14) . . ?
C4B C5B N1B 111.3(12) . . ?
C6B C5B N1B 126.5(13) . . ?
C6B C5B C4B 122.1(13) . . ?
C5B C6B H6B 121.6 . . ?
C5B C6B C7B 116.7(13) . . ?
C7B C6B H6B 121.6 . . ?
C6B C7B H7B 119.5 . . ?
C6B C7B C8B 121.1(13) . . ?
C8B C7B H7B 119.5 . . ?
C7B C8B H8B 120.2 . . ?
C9B C8B C7B 119.6(14) . . ?
C9B C8B H8B 120.2 . . ?
C4B C9B H9B 119.1 . . ?
C8B C9B C4B 121.9(14) . . ?
C8B C9B H9B 119.1 . . ?
N1B C10B H10G 109.5 . . ?
N1B C10B H10H 109.5 . . ?
N1B C10B H10I 109.5 . . ?
H10G C10B H10H 109.5 . . ?
H10G C10B H10I 109.5 . . ?
H10H C10B H10I 109.5 . . ?
C14B C13B N12B 116.9(11) . . ?
C18B C13B N12B 122.4(12) . . ?
C18B C13B C14B 120.6(12) . . ?
C13B C14B H14B 120.4 . . ?
C15B C14B C13B 119.2(12) . . ?
C15B C14B H14B 120.4 . . ?
C14B C15B H15B 120.6 . . ?
C16B C15B C14B 118.8(13) . . ?
C16B C15B H15B 120.6 . . ?
C15B C16B H16B 119.1 . . ?
C15B C16B C17B 121.9(13) . . ?
C17B C16B H16B 119.1 . . ?
C16B C17B H17B 121.1 . . ?
C18B C17B C16B 117.8(13) . . ?
C18B C17B H17B 121.1 . . ?
C13B C18B C17B 121.6(13) . . ?
C13B C18B H18B 119.2 . . ?
C17B C18B H18B 119.2 . . ?
Br14 Hg13 Br15 165.80(5) . . ?
Br14 Hg13 O11 97.12(19) . . ?
Br14 Hg13 N12 98.9(2) . . ?
Br15 Hg13 O11 93.41(19) . . ?
Br15 Hg13 N12 94.1(2) . . ?
O11 Hg13 N12 66.5(3) . . ?
C2 O11 Hg13 112.8(9) . . ?
C2 N1 C5 111.0(12) . . ?
C2 N1 C10 124.3(13) . . ?
C5 N1 C10 124.6(12) . . ?
C3 N12 Hg13 115.5(10) . . ?
C3 N12 C13 121.1(13) . . ?
C13 N12 Hg13 123.4(8) . . ?
O11 C2 N1 126.6(14) . . ?
O11 C2 C3 126.6(13) . . ?
N1 C2 C3 106.8(12) . . ?
N12 C3 C2 118.6(13) . . ?
N12 C3 C4 136.1(14) . . ?
C4 C3 C2 105.2(11) . . ?
C5 C4 C3 105.6(13) . . ?
C9 C4 C3 135.0(13) . . ?
C9 C4 C5 119.4(13) . . ?
N1 C5 C4 111.5(12) . . ?
C6 C5 N1 127.6(13) . . ?
C6 C5 C4 120.9(13) . . ?
C5 C6 H6 120.7 . . ?
C5 C6 C7 118.6(13) . . ?
C7 C6 H6 120.7 . . ?
C6 C7 H7 119.9 . . ?
C8 C7 C6 120.1(13) . . ?
C8 C7 H7 119.9 . . ?
C7 C8 H8 119.5 . . ?
C9 C8 C7 120.9(14) . . ?
C9 C8 H8 119.5 . . ?
C4 C9 C8 120.0(14) . . ?
C4 C9 H9 120.0 . . ?
C8 C9 H9 120.0 . . ?
N1 C10 H10J 109.5 . . ?
N1 C10 H10K 109.5 . . ?
N1 C10 H10L 109.5 . . ?
H10J C10 H10K 109.5 . . ?
H10J C10 H10L 109.5 . . ?
H10K C10 H10L 109.5 . . ?
C14 C13 N12 120.2(14) . . ?
C14 C13 C18 120.8(15) . . ?
C18 C13 N12 118.9(12) . . ?
C13 C14 H14 119.8 . . ?
C13 C14 C15 120.5(17) . . ?
C15 C14 H14 119.8 . . ?
C14 C15 H15 119.6 . . ?
C16 C15 C14 120.8(17) . . ?
C16 C15 H15 119.6 . . ?
C15 C16 H16 121.1 . . ?
C15 C16 C17 117.7(16) . . ?
C17 C16 H16 121.1 . . ?
C16 C17 H17 118.7 . . ?
C18 C17 C16 122.6(17) . . ?
C18 C17 H17 118.7 . . ?
C13 C18 H18 121.2 . . ?
C17 C18 C13 117.5(15) . . ?
C17 C18 H18 121.2 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Hg3A O11A C2A N1A 178.2(11) . . . . ?
Hg3A O11A C2A C3A -1.5(16) . . . . ?
Hg3A N12A C3A C2A -0.7(15) . . . . ?
Hg3A N12A C3A C4A -174.3(13) . . . . ?
Hg3A N12A C13A C14A -102.9(13) . . . . ?
Hg3A N12A C13A C18A 72.1(15) . . . . ?
Hg3C O11C C2C N1C 171.1(11) . . . . ?
Hg3C O11C C2C C3C -11.8(16) . . . . ?
Hg3C N12C C3C C2C 10.5(15) . . . . ?
Hg3C N12C C3C C4C -173.7(12) . . . . ?
Hg3C N12C C13C C14C 80.0(15) . . . . ?
Hg3C N12C C13C C18C -94.2(14) . . . . ?
O11A C2A C3A N12A 2(2) . . . . ?
O11A C2A C3A C4A 177.1(13) . . . . ?
O11C C2C C3C N12C 2(2) . . . . ?
O11C C2C C3C C4C -175.1(13) . . . . ?
N1A C2A C3A N12A -178.1(11) . . . . ?
N1A C2A C3A C4A -2.6(14) . . . . ?
N1A C5A C6A C7A -178.2(12) . . . . ?
N1C C2C C3C N12C 179.4(11) . . . . ?
N1C C2C C3C C4C 2.5(14) . . . . ?
N1C C5C C6C C7C 179.1(12) . . . . ?
N12A C3A C4A C5A 175.0(15) . . . . ?
N12A C3A C4A C9A -5(3) . . . . ?
N12A C13A C14A C15A 174.1(13) . . . . ?
N12A C13A C18A C17A -176.9(13) . . . . ?
N12C C3C C4C C5C -178.2(14) . . . . ?
N12C C3C C4C C9C 3(3) . . . . ?
N12C C13C C14C C15C -178.9(12) . . . . ?
N12C C13C C18C C17C 178.6(13) . . . . ?
C2A N1A C5A C4A -2.8(15) . . . . ?
C2A N1A C5A C6A 178.3(13) . . . . ?
C2A C3A C4A C5A 1.0(14) . . . . ?
C2A C3A C4A C9A -178.7(14) . . . . ?
C2C N1C C5C C4C 0.6(15) . . . . ?
C2C N1C C5C C6C -179.5(13) . . . . ?
C2C C3C C4C C5C -2.1(14) . . . . ?
C2C C3C C4C C9C 179.1(14) . . . . ?
C3A N12A C13A C14A 74.9(18) . . . . ?
C3A N12A C13A C18A -110.1(15) . . . . ?
C3A C4A C5A N1A 0.9(14) . . . . ?
C3A C4A C5A C6A 179.9(12) . . . . ?
C3A C4A C9A C8A 176.4(13) . . . . ?
C3C N12C C13C C14C -93.2(16) . . . . ?
C3C N12C C13C C18C 92.5(17) . . . . ?
C3C C4C C5C N1C 1.0(14) . . . . ?
C3C C4C C5C C6C -178.9(12) . . . . ?
C3C C4C C9C C8C 179.6(14) . . . . ?
C4A C5A C6A C7A 3.0(19) . . . . ?
C4C C5C C6C C7C -1(2) . . . . ?
C5A N1A C2A O11A -176.5(12) . . . . ?
C5A N1A C2A C3A 3.3(14) . . . . ?
C5A C4A C9A C8A -3.1(19) . . . . ?
C5A C6A C7A C8A -2.1(19) . . . . ?
C5C N1C C2C O11C 175.6(13) . . . . ?
C5C N1C C2C C3C -1.9(14) . . . . ?
C5C C4C C9C C8C 0.8(18) . . . . ?
C5C C6C C7C C8C 0.8(19) . . . . ?
C6A C7A C8A C9A -1.4(19) . . . . ?
C6C C7C C8C C9C 0(2) . . . . ?
C7A C8A C9A C4A 4.0(19) . . . . ?
C7C C8C C9C C4C -1.1(19) . . . . ?
C9A C4A C5A N1A -179.4(11) . . . . ?
C9A C4A C5A C6A 0(2) . . . . ?
C9C C4C C5C N1C -179.9(11) . . . . ?
C9C C4C C5C C6C 0(2) . . . . ?
C10A N1A C2A O11A -8(2) . . . . ?
C10A N1A C2A C3A 172.0(11) . . . . ?
C10A N1A C5A C4A -171.9(11) . . . . ?
C10A N1A C5A C6A 9(2) . . . . ?
C10C N1C C2C O11C -1(2) . . . . ?
C10C N1C C2C C3C -178.2(11) . . . . ?
C10C N1C C5C C4C 176.8(12) . . . . ?
C10C N1C C5C C6C -3(2) . . . . ?
C13A N12A C3A C2A -178.6(11) . . . . ?
C13A N12A C3A C4A 8(2) . . . . ?
C13A C14A C15A C16A 3(2) . . . . ?
C13C N12C C3C C2C -175.9(11) . . . . ?
C13C N12C C3C C4C 0(2) . . . . ?
C13C C14C C15C C16C 4(2) . . . . ?
C14A C13A C18A C17A -2(2) . . . . ?
C14A C15A C16A C17A -2(2) . . . . ?
C14C C13C C18C C17C 5(2) . . . . ?
C14C C15C C16C C17C -2(2) . . . . ?
C15A C16A C17A C18A 0(2) . . . . ?
C15C C16C C17C C18C 2(2) . . . . ?
C16A C17A C18A C13A 2(2) . . . . ?
C16C C17C C18C C13C -3(2) . . . . ?
C18A C13A C14A C15A -1(2) . . . . ?
C18C C13C C14C C15C -5(2) . . . . ?
Hg3B O11B C2B N1B -177.1(10) . . . . ?
Hg3B O11B C2B C3B 2.3(15) . . . . ?
Hg3B N12B C3B C2B 6.2(15) . . . . ?
Hg3B N12B C3B C4B 176.5(11) . . . . ?
Hg3B N12B C13B C14B -66.6(13) . . . . ?
Hg3B N12B C13B C18B 114.2(12) . . . . ?
O11B C2B C3B N12B -6(2) . . . . ?
O11B C2B C3B C4B -178.9(12) . . . . ?
N1B C2B C3B N12B 173.4(11) . . . . ?
N1B C2B C3B C4B 0.6(13) . . . . ?
N1B C5B C6B C7B 179.3(11) . . . . ?
N12B C3B C4B C5B -174.1(14) . . . . ?
N12B C3B C4B C9B 8(3) . . . . ?
N12B C13B C14B C15B -179.1(12) . . . . ?
N12B C13B C18B C17B 178.1(12) . . . . ?
C2B N1B C5B C4B -4.2(15) . . . . ?
C2B N1B C5B C6B 178.4(12) . . . . ?
C2B C3B C4B C5B -3.0(13) . . . . ?
C2B C3B C4B C9B 179.2(14) . . . . ?
C3B N12B C13B C14B 120.5(14) . . . . ?
C3B N12B C13B C18B -58.7(18) . . . . ?
C3B C4B C5B N1B 4.4(14) . . . . ?
C3B C4B C5B C6B -178.0(12) . . . . ?
C3B C4B C9B C8B 176.7(13) . . . . ?
C4B C5B C6B C7B 2.1(19) . . . . ?
C5B N1B C2B O11B -178.5(12) . . . . ?
C5B N1B C2B C3B 2.1(13) . . . . ?
C5B C4B C9B C8B -0.9(19) . . . . ?
C5B C6B C7B C8B -3.8(18) . . . . ?
C6B C7B C8B C9B 3.3(19) . . . . ?
C7B C8B C9B C4B -0.8(19) . . . . ?
C9B C4B C5B N1B -177.3(11) . . . . ?
C9B C4B C5B C6B 0(2) . . . . ?
C10B N1B C2B O11B 0(2) . . . . ?
C10B N1B C2B C3B -179.6(11) . . . . ?
C10B N1B C5B C4B 177.4(11) . . . . ?
C10B N1B C5B C6B 0(2) . . . . ?
C13B N12B C3B C2B 179.3(10) . . . . ?
C13B N12B C3B C4B -10(2) . . . . ?
C13B C14B C15B C16B 0.9(19) . . . . ?
C14B C13B C18B C17B -1(2) . . . . ?
C14B C15B C16B C17B -1(2) . . . . ?
C15B C16B C17B C18B 0(2) . . . . ?
C16B C17B C18B C13B 1(2) . . . . ?
C18B C13B C14B C15B 0.2(19) . . . . ?
Hg13 O11 C2 N1 178.8(10) . . . . ?
Hg13 O11 C2 C3 1.0(16) . . . . ?
Hg13 N12 C3 C2 -2.3(15) . . . . ?
Hg13 N12 C3 C4 -178.5(13) . . . . ?
Hg13 N12 C13 C14 -106.8(14) . . . . ?
Hg13 N12 C13 C18 69.0(15) . . . . ?
O11 C2 C3 N12 1(2) . . . . ?
O11 C2 C3 C4 178.2(13) . . . . ?
N1 C2 C3 N12 -177.2(11) . . . . ?
N1 C2 C3 C4 0.0(14) . . . . ?
N1 C5 C6 C7 179.2(12) . . . . ?
N12 C3 C4 C5 175.2(15) . . . . ?
N12 C3 C4 C9 -2(3) . . . . ?
N12 C13 C14 C15 179.0(14) . . . . ?
N12 C13 C18 C17 -179.4(13) . . . . ?
C2 N1 C5 C4 -2.4(15) . . . . ?
C2 N1 C5 C6 -179.3(13) . . . . ?
C2 C3 C4 C5 -1.4(14) . . . . ?
C2 C3 C4 C9 -178.8(15) . . . . ?
C3 N12 C13 C14 72.3(18) . . . . ?
C3 N12 C13 C18 -111.8(15) . . . . ?
C3 C4 C5 N1 2.3(15) . . . . ?
C3 C4 C5 C6 179.5(12) . . . . ?
C3 C4 C9 C8 179.0(14) . . . . ?
C4 C5 C6 C7 2.5(19) . . . . ?
C5 N1 C2 O11 -176.8(13) . . . . ?
C5 N1 C2 C3 1.4(14) . . . . ?
C5 C4 C9 C8 2(2) . . . . ?
C5 C6 C7 C8 -1.7(19) . . . . ?
C6 C7 C8 C9 1(2) . . . . ?
C7 C8 C9 C4 -1(2) . . . . ?
C9 C4 C5 N1 -179.8(12) . . . . ?
C9 C4 C5 C6 -3(2) . . . . ?
C10 N1 C2 O11 -1(2) . . . . ?
C10 N1 C2 C3 177.1(12) . . . . ?
C10 N1 C5 C4 -178.1(12) . . . . ?
C10 N1 C5 C6 5(2) . . . . ?
C13 N12 C3 C2 178.5(11) . . . . ?
C13 N12 C3 C4 2(2) . . . . ?
C13 C14 C15 C16 0(3) . . . . ?
C14 C13 C18 C17 -4(2) . . . . ?
C14 C15 C16 C17 -2(3) . . . . ?
C15 C16 C17 C18 2(3) . . . . ?
C16 C17 C18 C13 1(2) . . . . ?
C18 C13 C14 C15 3(2) . . . . ?

# start Validation Reply Form
_vrf_PLAT213_Compound_5_lcb_003  
;
PROBLEM: Atom C6B             has ADP max/min Ratio .....        4.4 prolat
RESPONSE: Problem is due to the low diffraction ability
and low quality of the crystals.
;
_vrf_PLAT342_Compound_5_lcb_003  
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.02012 Ang.  
RESPONSE: Problem is due to the low diffraction ability
and low quality of the crystals.
;
_vrf_PLAT971_Compound_5_lcb_003  
;
PROBLEM: Check Calcd Residual Density  1.89A From    C10C       2.99 eA-3  
RESPONSE: Problem is due to the low diffraction ability
and low quality of the crystals.
;
_vrf_PLAT973_Compound_5_lcb_003  
;
PROBLEM: Check Calcd Positive Residual Density on    Hg3C       1.98 eA-3  
RESPONSE: Problem is due to the low diffraction ability
and low quality of the crystals.
;
# end Validation Reply Form
####################################################################### 
# 
# 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_Compound_6_as_v
_database_code_depnum_ccdc_archive 'CCDC 1506944'
_audit_update_record             
;
2016-09-27 deposited with the CCDC.
2017-01-29 downloaded from the CCDC.
;
_audit_creation_date             2016-09-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         '0.5(C30 H24 Br4 Cd2 N4 O2)'
_chemical_formula_sum            'C15 H12 Br2 Cd N2 O'
_chemical_formula_weight         508.49
_chemical_melting_point          ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cd Cd -0.8075 1.2024 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   7.2618(3)
_cell_length_b                   11.2036(10)
_cell_length_c                   20.2141(11)
_cell_angle_alpha                93.876(6)
_cell_angle_beta                 98.487(4)
_cell_angle_gamma                107.037(6)
_cell_volume                     1544.46(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3350
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.6420
_cell_measurement_theta_min      3.8750
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    6.587
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85401
_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.
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    2.187
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             968
_exptl_crystal_size_max          0.3548
_exptl_crystal_size_mid          0.2105
_exptl_crystal_size_min          0.0495
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.0507
_diffrn_reflns_Laue_measured_fraction_full 0.973
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            11894
_diffrn_reflns_point_group_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         2.980
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3829
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -28.00   70.00   1.0000   77.5000
omega____ theta____ kappa____ phi______ frames
    -      -10.4139   19.0000  150.0000 98

#__ type_ start__ end____ width___ exp.time_
  2 omega  -14.00   27.00   1.0000   77.5000
omega____ theta____ kappa____ phi______ frames
    -      -10.4139  -99.0000  -90.0000 41

#__ type_ start__ end____ width___ exp.time_
  3 omega  -85.00   12.00   1.0000   77.5000
omega____ theta____ kappa____ phi______ frames
    -      -10.4139  -38.0000  -30.0000 97

#__ type_ start__ end____ width___ exp.time_
  4 omega  -77.00  -48.00   1.0000   77.5000
omega____ theta____ kappa____ phi______ frames
    -      -10.4139  -38.0000  -90.0000 29

#__ type_ start__ end____ width___ exp.time_
  5 omega  -46.00   39.00   1.0000   77.5000
omega____ theta____ kappa____ phi______ frames
    -       12.1327  -57.0000 -150.0000 85
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Mo at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0400221000
_diffrn_orient_matrix_UB_12      0.0616993000
_diffrn_orient_matrix_UB_13      0.0171909000
_diffrn_orient_matrix_UB_21      0.0772307000
_diffrn_orient_matrix_UB_22      -0.0176898000
_diffrn_orient_matrix_UB_23      0.0181854000
_diffrn_orient_matrix_UB_31      0.0565793000
_diffrn_orient_matrix_UB_32      0.0180429000
_diffrn_orient_matrix_UB_33      -0.0254923000
loop_
_diffrn_oxdiff_twin_id
_diffrn_oxdiff_twin_ratio
_diffrn_oxdiff_twin_reflns_isolated
_diffrn_oxdiff_twin_reflns_overlapped
1 0.4641 7961 6911
2 0.5359 7940 6911

_diffrn_oxdiff_twin_integration_method simultaneous
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                9405
_reflns_number_total             11894
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         3.394
_refine_diff_density_min         -1.914
_refine_diff_density_rms         0.335
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     304
_refine_ls_number_reflns         11894
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0824
_refine_ls_R_factor_gt           0.0685
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1433P)²+4.0359P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1938
_refine_ls_wR_factor_ref         0.2022
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.4621(16) 0.5379(16)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3. Uiso/Uaniso restraints and constraints
C8' \\sim C9': within 2A with sigma of 0.001 and sigma for terminal atoms of
0.01
Uanis(N12') = Uanis(O11')
Uanis(C3') = Uanis(C2')
Uanis(N12) = Uanis(O11) = Uanis(Cd13)
Uanis(C13) = Uanis(C3) = Uanis(C2)
Uanis(N1) = Uanis(C4)
Uanis(C6) = Uanis(C9)
Uanis(C7') = Uanis(C8') = Uanis(C6') = Uanis(C9')
Uanis(C18) = Uanis(C17) = Uanis(C16)
4.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C9(H9), C14(H14), C15(H15), C16(H16), C17(H17),
 C18(H18), C6'(H6'), C7'(H7'), C8'(H8'), C9'(H9'), C14'(H14'), C15'(H15'),
 C16'(H16'), C17'(H17'), C18'(H18')
4.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C10'(H10D,H10E,H10F)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.4616(16) 0.0796(11) 0.0937(5) 0.014(2) Uani 1 1 d . . . . .
C2 C 0.5496(19) 0.1970(13) 0.0804(7) 0.0130(17) Uani 1 1 d . . . . .
C3 C 0.6800(18) 0.2733(13) 0.1438(6) 0.0130(17) Uani 1 1 d . . . . .
C4 C 0.6504(19) 0.1822(13) 0.1947(6) 0.014(2) Uani 1 1 d . . . . .
C5 C 0.5198(19) 0.0690(13) 0.1629(6) 0.015(3) Uani 1 1 d . . . . .
C6 C 0.4652(19) -0.0345(14) 0.1955(7) 0.016(2) Uani 1 1 d . . . . .
H6 H 0.3763 -0.1111 0.1725 0.020 Uiso 1 1 calc R . . . .
C7 C 0.542(2) -0.0254(14) 0.2630(7) 0.020(3) Uani 1 1 d . . . . .
H7 H 0.5033 -0.0962 0.2869 0.024 Uiso 1 1 calc R . . . .
C8 C 0.674(2) 0.0839(14) 0.2959(7) 0.019(3) Uani 1 1 d . . . . .
H8 H 0.7268 0.0865 0.3420 0.023 Uiso 1 1 calc R . . . .
C9 C 0.7337(19) 0.1939(14) 0.2631(7) 0.016(2) Uani 1 1 d . . . . .
H9 H 0.8241 0.2702 0.2860 0.020 Uiso 1 1 calc R . . . .
C10 C 0.323(2) -0.0206(13) 0.0477(7) 0.019(3) Uani 1 1 d . . . . .
H10A H 0.3777 -0.0898 0.0412 0.029 Uiso 1 1 calc GR . . . .
H10B H 0.2935 0.0102 0.0044 0.029 Uiso 1 1 calc GR . . . .
H10C H 0.2021 -0.0506 0.0662 0.029 Uiso 1 1 calc GR . . . .
O11 O 0.5251(12) 0.2376(8) 0.0256(4) 0.0117(3) Uani 1 1 d . . . . .
N12 N 0.7847(15) 0.3824(10) 0.1377(5) 0.0117(3) Uani 1 1 d . . . . .
Cd13 Cd 0.73121(13) 0.44946(9) 0.02577(4) 0.0117(3) Uani 1 1 d . . . . .
C13 C 0.9107(18) 0.4683(13) 0.1928(6) 0.0130(17) Uani 1 1 d . . . . .
Br14 Br 0.50292(19) 0.55889(13) 0.09139(6) 0.0155(3) Uani 1 1 d . . . . .
C14 C 0.841(2) 0.4901(13) 0.2515(7) 0.018(3) Uani 1 1 d . . . . .
H14 H 0.7100 0.4468 0.2557 0.021 Uiso 1 1 calc R . . . .
Br15 Br 1.01877(19) 0.66432(13) 0.02747(7) 0.0156(3) Uani 1 1 d . . . . .
C15 C 0.965(2) 0.5765(15) 0.3038(7) 0.029(4) Uani 1 1 d . . . . .
H15 H 0.9209 0.5902 0.3448 0.034 Uiso 1 1 calc R . . . .
C16 C 1.154(2) 0.6431(14) 0.2962(7) 0.0223(19) Uani 1 1 d . . . . .
H16 H 1.2378 0.7051 0.3308 0.027 Uiso 1 1 calc R . . . .
C17 C 1.218(2) 0.6173(14) 0.2375(7) 0.0223(19) Uani 1 1 d . . . . .
H17 H 1.3492 0.6584 0.2328 0.027 Uiso 1 1 calc R . . . .
C18 C 1.093(2) 0.5322(14) 0.1853(8) 0.0223(19) Uani 1 1 d . . . . .
H18 H 1.1370 0.5188 0.1441 0.027 Uiso 1 1 calc R . . . .
N1' N -0.0215(15) -0.0707(10) 0.2436(5) 0.011(2) Uani 1 1 d . . . . .
C2' C 0.0617(18) -0.0399(12) 0.3089(6) 0.010(2) Uani 1 1 d . . . . .
Cd13' Cd 0.23468(13) 0.00737(9) 0.46187(4) 0.0136(3) Uani 1 1 d . . . . .
C3' C 0.1901(18) 0.0977(12) 0.3168(6) 0.010(2) Uani 1 1 d . . . . .
Br14' Br 0.51195(19) 0.12492(13) 0.56689(6) 0.0173(3) Uani 1 1 d . . . . .
C4' C 0.1632(19) 0.1389(13) 0.2488(6) 0.014(3) Uani 1 1 d . . . . .
Br15' Br 0.00145(19) 0.16357(13) 0.47929(7) 0.0182(4) Uani 1 1 d . . . . .
C5' C 0.0317(19) 0.0313(13) 0.2064(7) 0.014(3) Uani 1 1 d . . . . .
C6' C -0.023(2) 0.0360(14) 0.1391(6) 0.0165(8) Uani 1 1 d . . . . .
H6' H -0.1124 -0.0356 0.1116 0.020 Uiso 1 1 calc R . . . .
C7' C 0.0518(19) 0.1451(13) 0.1118(7) 0.0165(8) Uani 1 1 d . . . . .
H7' H 0.0155 0.1486 0.0650 0.020 Uiso 1 1 calc R . . . .
C8' C 0.1839(19) 0.2532(14) 0.1533(6) 0.0165(8) Uani 1 1 d . U . . .
H8' H 0.2362 0.3283 0.1341 0.020 Uiso 1 1 calc R . . . .
C9' C 0.2368(19) 0.2482(14) 0.2229(6) 0.0165(8) Uani 1 1 d . U . . .
H9' H 0.3224 0.3201 0.2512 0.020 Uiso 1 1 calc R . . . .
C10' C -0.153(2) -0.1934(14) 0.2154(7) 0.021(3) Uani 1 1 d . . . . .
H10D H -0.1763 -0.2473 0.2514 0.032 Uiso 1 1 calc GR . . . .
H10E H -0.0941 -0.2311 0.1823 0.032 Uiso 1 1 calc GR . . . .
H10F H -0.2773 -0.1849 0.1934 0.032 Uiso 1 1 calc GR . . . .
O11' O 0.0416(13) -0.1022(8) 0.3562(4) 0.0134(16) Uani 1 1 d . . . . .
N12' N 0.2925(16) 0.1433(10) 0.3738(5) 0.0134(16) Uani 1 1 d . . . . .
C13' C 0.4111(19) 0.2731(13) 0.3902(6) 0.014(3) Uani 1 1 d . . . . .
C14' C 0.330(2) 0.3686(14) 0.3799(7) 0.020(3) Uani 1 1 d . . . . .
H14' H 0.1974 0.3501 0.3592 0.024 Uiso 1 1 calc R . . . .
C15' C 0.447(2) 0.4943(14) 0.4005(7) 0.024(4) Uani 1 1 d . . . . .
H15' H 0.3923 0.5608 0.3942 0.029 Uiso 1 1 calc R . . . .
C16' C 0.634(3) 0.5197(16) 0.4288(8) 0.031(4) Uani 1 1 d . . . . .
H16' H 0.7114 0.6046 0.4422 0.037 Uiso 1 1 calc R . . . .
C17' C 0.717(2) 0.4219(16) 0.4392(7) 0.026(4) Uani 1 1 d . . . . .
H17' H 0.8517 0.4402 0.4582 0.031 Uiso 1 1 calc R . . . .
C18' C 0.599(2) 0.2984(13) 0.4207(6) 0.016(3) Uani 1 1 d . . . . .
H18' H 0.6501 0.2312 0.4298 0.019 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C2 1.348(17) . ?
N1 C5 1.423(16) . ?
N1 C10 1.435(18) . ?
C2 C3 1.514(19) . ?
C2 O11 1.234(15) . ?
C3 C4 1.492(17) . ?
C3 N12 1.260(17) . ?
C4 C5 1.39(2) . ?
C4 C9 1.407(18) . ?
C5 C6 1.359(19) . ?
C6 H6 0.9500 . ?
C6 C7 1.381(19) . ?
C7 H7 0.9500 . ?
C7 C8 1.37(2) . ?
C8 H8 0.9500 . ?
C8 C9 1.424(18) . ?
C9 H9 0.9500 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
O11 Cd13 2.407(9) . ?
N12 Cd13 2.445(10) . ?
N12 C13 1.428(18) . ?
Cd13 Br14 2.7624(16) . ?
Cd13 Br14 2.6828(15) 2_665 ?
Cd13 Br15 2.6792(16) . ?
Cd13 Br15 2.7977(16) 2_765 ?
C13 C14 1.393(19) . ?
C13 C18 1.346(19) . ?
Br14 Cd13 2.6828(15) 2_665 ?
C14 H14 0.9500 . ?
C14 C15 1.39(2) . ?
Br15 Cd13 2.7977(16) 2_765 ?
C15 H15 0.9500 . ?
C15 C16 1.40(2) . ?
C16 H16 0.9500 . ?
C16 C17 1.38(2) . ?
C17 H17 0.9500 . ?
C17 C18 1.39(2) . ?
C18 H18 0.9500 . ?
N1' C2' 1.344(16) . ?
N1' C5' 1.401(16) . ?
N1' C10' 1.446(18) . ?
C2' C3' 1.533(18) . ?
C2' O11' 1.222(14) . ?
Cd13' Br14' 2.7780(16) 2_656 ?
Cd13' Br14' 2.6649(17) . ?
Cd13' Br15' 2.6472(16) 2_556 ?
Cd13' Br15' 2.8080(17) . ?
Cd13' O11' 2.406(9) . ?
Cd13' N12' 2.424(10) . ?
C3' C4' 1.484(17) . ?
C3' N12' 1.260(17) . ?
Br14' Cd13' 2.7780(16) 2_656 ?
C4' C5' 1.43(2) . ?
C4' C9' 1.358(19) . ?
Br15' Cd13' 2.6473(16) 2_556 ?
C5' C6' 1.369(18) . ?
C6' H6' 0.9500 . ?
C6' C7' 1.374(19) . ?
C7' H7' 0.9500 . ?
C7' C8' 1.43(2) . ?
C8' H8' 0.9500 . ?
C8' C9' 1.413(17) . ?
C9' H9' 0.9500 . ?
C10' H10D 0.9800 . ?
C10' H10E 0.9800 . ?
C10' H10F 0.9800 . ?
N12' C13' 1.443(18) . ?
C13' C14' 1.376(19) . ?
C13' C18' 1.348(19) . ?
C14' H14' 0.9500 . ?
C14' C15' 1.41(2) . ?
C15' H15' 0.9500 . ?
C15' C16' 1.33(2) . ?
C16' H16' 0.9500 . ?
C16' C17' 1.41(2) . ?
C17' H17' 0.9500 . ?
C17' C18' 1.39(2) . ?
C18' H18' 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
C2 N1 C5 109.7(12) . . ?
C2 N1 C10 126.9(11) . . ?
C5 N1 C10 123.3(11) . . ?
N1 C2 C3 109.4(11) . . ?
O11 C2 N1 125.7(13) . . ?
O11 C2 C3 124.9(12) . . ?
C4 C3 C2 102.9(11) . . ?
N12 C3 C2 116.6(11) . . ?
N12 C3 C4 140.2(13) . . ?
C5 C4 C3 108.0(11) . . ?
C5 C4 C9 120.6(12) . . ?
C9 C4 C3 131.3(13) . . ?
C4 C5 N1 110.0(11) . . ?
C6 C5 N1 127.5(13) . . ?
C6 C5 C4 122.5(12) . . ?
C5 C6 H6 120.9 . . ?
C5 C6 C7 118.3(14) . . ?
C7 C6 H6 120.9 . . ?
C6 C7 H7 119.5 . . ?
C8 C7 C6 121.0(13) . . ?
C8 C7 H7 119.5 . . ?
C7 C8 H8 119.0 . . ?
C7 C8 C9 122.1(13) . . ?
C9 C8 H8 119.0 . . ?
C4 C9 C8 115.6(13) . . ?
C4 C9 H9 122.2 . . ?
C8 C9 H9 122.2 . . ?
N1 C10 H10A 109.5 . . ?
N1 C10 H10B 109.5 . . ?
N1 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C2 O11 Cd13 112.9(8) . . ?
C3 N12 Cd13 115.2(9) . . ?
C3 N12 C13 123.8(11) . . ?
C13 N12 Cd13 120.7(8) . . ?
O11 Cd13 N12 70.2(3) . . ?
O11 Cd13 Br14 84.2(2) . 2_665 ?
O11 Cd13 Br14 94.7(2) . . ?
O11 Cd13 Br15 84.8(2) . 2_765 ?
O11 Cd13 Br15 168.5(2) . . ?
N12 Cd13 Br14 150.6(2) . 2_665 ?
N12 Cd13 Br14 79.0(3) . . ?
N12 Cd13 Br15 95.3(3) . 2_765 ?
N12 Cd13 Br15 106.0(3) . . ?
Br14 Cd13 Br14 89.34(5) 2_665 . ?
Br14 Cd13 Br15 96.50(5) 2_665 2_765 ?
Br14 Cd13 Br15 174.06(5) . 2_765 ?
Br15 Cd13 Br14 101.85(5) . 2_665 ?
Br15 Cd13 Br14 95.16(5) . . ?
Br15 Cd13 Br15 84.75(5) . 2_765 ?
C14 C13 N12 120.0(11) . . ?
C18 C13 N12 118.9(12) . . ?
C18 C13 C14 121.0(14) . . ?
Cd13 Br14 Cd13 90.66(5) 2_665 . ?
C13 C14 H14 120.5 . . ?
C15 C14 C13 118.9(13) . . ?
C15 C14 H14 120.5 . . ?
Cd13 Br15 Cd13 95.25(5) . 2_765 ?
C14 C15 H15 119.9 . . ?
C14 C15 C16 120.2(14) . . ?
C16 C15 H15 119.9 . . ?
C15 C16 H16 120.6 . . ?
C17 C16 C15 118.8(14) . . ?
C17 C16 H16 120.6 . . ?
C16 C17 H17 119.6 . . ?
C16 C17 C18 120.8(14) . . ?
C18 C17 H17 119.6 . . ?
C13 C18 C17 120.2(15) . . ?
C13 C18 H18 119.9 . . ?
C17 C18 H18 119.9 . . ?
C2' N1' C5' 111.8(11) . . ?
C2' N1' C10' 124.2(11) . . ?
C5' N1' C10' 124.1(11) . . ?
N1' C2' C3' 107.0(10) . . ?
O11' C2' N1' 129.9(12) . . ?
O11' C2' C3' 123.1(12) . . ?
Br14' Cd13' Br14' 85.79(5) . 2_656 ?
Br14' Cd13' Br15' 94.55(5) . . ?
Br14' Cd13' Br15' 172.31(5) 2_656 . ?
Br15' Cd13' Br14' 98.97(5) 2_556 2_656 ?
Br15' Cd13' Br14' 100.67(5) 2_556 . ?
Br15' Cd13' Br15' 88.52(5) 2_556 . ?
O11' Cd13' Br14' 83.7(2) . 2_656 ?
O11' Cd13' Br14' 167.9(2) . . ?
O11' Cd13' Br15' 87.0(2) . 2_556 ?
O11' Cd13' Br15' 95.1(2) . . ?
O11' Cd13' N12' 70.4(3) . . ?
N12' Cd13' Br14' 104.8(3) . . ?
N12' Cd13' Br14' 95.9(3) . 2_656 ?
N12' Cd13' Br15' 151.3(3) . 2_556 ?
N12' Cd13' Br15' 76.6(3) . . ?
C4' C3' C2' 105.4(11) . . ?
N12' C3' C2' 117.4(11) . . ?
N12' C3' C4' 137.1(12) . . ?
Cd13' Br14' Cd13' 94.21(5) . 2_656 ?
C5' C4' C3' 105.4(11) . . ?
C9' C4' C3' 134.0(13) . . ?
C9' C4' C5' 120.6(12) . . ?
Cd13' Br15' Cd13' 91.48(5) 2_556 . ?
N1' C5' C4' 110.4(11) . . ?
C6' C5' N1' 128.6(13) . . ?
C6' C5' C4' 120.9(12) . . ?
C5' C6' H6' 120.3 . . ?
C5' C6' C7' 119.5(14) . . ?
C7' C6' H6' 120.3 . . ?
C6' C7' H7' 119.9 . . ?
C6' C7' C8' 120.3(12) . . ?
C8' C7' H7' 119.9 . . ?
C7' C8' H8' 120.1 . . ?
C9' C8' C7' 119.8(13) . . ?
C9' C8' H8' 120.1 . . ?
C4' C9' C8' 118.9(14) . . ?
C4' C9' H9' 120.5 . . ?
C8' C9' H9' 120.5 . . ?
N1' C10' H10D 109.5 . . ?
N1' C10' H10E 109.5 . . ?
N1' C10' H10F 109.5 . . ?
H10D C10' H10E 109.5 . . ?
H10D C10' H10F 109.5 . . ?
H10E C10' H10F 109.5 . . ?
C2' O11' Cd13' 113.8(8) . . ?
C3' N12' Cd13' 115.0(9) . . ?
C3' N12' C13' 123.8(11) . . ?
C13' N12' Cd13' 120.4(8) . . ?
C14' C13' N12' 120.7(12) . . ?
C18' C13' N12' 118.4(12) . . ?
C18' C13' C14' 120.7(14) . . ?
C13' C14' H14' 120.4 . . ?
C13' C14' C15' 119.3(14) . . ?
C15' C14' H14' 120.4 . . ?
C14' C15' H15' 119.9 . . ?
C16' C15' C14' 120.2(15) . . ?
C16' C15' H15' 119.9 . . ?
C15' C16' H16' 119.6 . . ?
C15' C16' C17' 120.7(15) . . ?
C17' C16' H16' 119.6 . . ?
C16' C17' H17' 120.8 . . ?
C18' C17' C16' 118.4(14) . . ?
C18' C17' H17' 120.8 . . ?
C13' C18' C17' 120.6(14) . . ?
C13' C18' H18' 119.7 . . ?
C17' C18' H18' 119.7 . . ?

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-1 -12 -11 0.0115 -1.2426 -12.2607 -11.0808 -0.9967 -0.0806 -0.0091
-2 -7 26 0.1269 -1.6464 -6.7584 26.1910 -0.0326 0.4687 -0.8828
-8 10 -10 0.0853 -8.3663 9.5062 -9.9693 0.0803 -0.9956 -0.0477
10 -7 -4 0.1032 10.1459 -6.6041 -3.6422 -0.0640 0.8342 0.5477
10 -8 3 0.0969 9.6679 -8.2213 2.6909 -0.0741 0.9410 0.3301
1 12 12 0.0279 0.8818 12.0898 12.4631 0.9955 0.0809 -0.0497
-1 8 -25 0.1257 -0.5033 8.2723 -25.2041 0.0570 -0.6436 0.7633

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.4621(16)
2 0.5379(16)

