# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2018

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

data_isbd_11
_database_code_depnum_ccdc_archive 'CCDC 1412864'
_audit_update_record             
;
2017-03-12 deposited with the CCDC.
2018-10-29 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 O2'
_chemical_formula_sum            'C15 H12 N2 O2'
_chemical_formula_weight         252.27
_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                   10.1494(6)
_cell_length_b                   7.7078(5)
_cell_length_c                   15.2882(7)
_cell_angle_alpha                90
_cell_angle_beta                 101.259(6)
_cell_angle_gamma                90
_cell_volume                     1172.96(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2050
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      75.4100
_cell_measurement_theta_min      5.7910
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.788
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73396
_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    1.429
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.19
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0265
_diffrn_reflns_av_unetI/netI     0.0302
_diffrn_reflns_Laue_measured_fraction_full 0.963
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            5151
_diffrn_reflns_point_group_measured_fraction_full 0.963
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.494
_diffrn_reflns_theta_min         4.442
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.3829
_diffrn_measured_fraction_theta_full 0.963
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega -121.00  -44.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787  178.0000 -120.0000 77

#__ type_ start__ end____ width___ exp.time_
  2 omega -113.00  -13.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787  -57.0000 -180.0000 100

#__ type_ start__ end____ width___ exp.time_
  3 omega  -49.00  -21.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787   38.0000  -30.0000 28

#__ type_ start__ end____ width___ exp.time_
  4 omega  -16.00   35.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787   38.0000   60.0000 51

#__ type_ start__ end____ width___ exp.time_
  5 omega   35.00   89.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000  -30.0000 54

#__ type_ start__ end____ width___ exp.time_
  6 omega   62.00  115.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000 -120.0000 53

#__ type_ start__ end____ width___ exp.time_
  7 omega   30.00  109.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000  -30.0000 79

#__ type_ start__ end____ width___ exp.time_
  8 omega   43.00  106.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000   60.0000 63

#__ type_ start__ end____ width___ exp.time_
  9 omega   56.00   90.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000   60.0000 34

#__ type_ start__ end____ width___ exp.time_
 10 omega   45.00   88.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000  -90.0000 43

#__ type_ start__ end____ width___ exp.time_
 11 omega   91.00  132.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000    0.0000 41

#__ type_ start__ end____ width___ exp.time_
 12 omega  145.00  171.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000    0.0000 26

#__ type_ start__ end____ width___ exp.time_
 13 omega   36.00   61.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000  -30.0000 25

#__ type_ start__ end____ width___ exp.time_
 14 omega   85.00  113.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000  -30.0000 28

#__ type_ start__ end____ width___ exp.time_
 15 omega  140.00  173.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   30.0000  -90.0000 33

#__ type_ start__ end____ width___ exp.time_
 16 omega   66.00  105.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000   60.0000 39

#__ type_ start__ end____ width___ exp.time_
 17 omega  106.00  131.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   30.0000  -90.0000 25
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0886546000
_diffrn_orient_matrix_UB_12      -0.1639741000
_diffrn_orient_matrix_UB_13      -0.0104200000
_diffrn_orient_matrix_UB_21      -0.1177456000
_diffrn_orient_matrix_UB_22      0.1073663000
_diffrn_orient_matrix_UB_23      0.0215829000
_diffrn_orient_matrix_UB_31      -0.0471437000
_diffrn_orient_matrix_UB_32      0.0400518000
_diffrn_orient_matrix_UB_33      -0.0998148000
_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                1767
_reflns_number_total             2236
_reflns_odcompleteness_completeness 89.92
_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         0.248
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         2236
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0516
_refine_ls_R_factor_gt           0.0370
_refine_ls_restrained_S_all      1.024
_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)+(0.0538P)²+0.2833P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0920
_refine_ls_wR_factor_ref         0.1027
_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, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C9(H9), C15(H15), C16(H16), C17(H17), C18(H18)
2.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C)
2.c Idealised tetrahedral OH refined as rotating group:
 O19(H19)
;
_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 1.02136(15) 0.7958(2) 0.47924(10) 0.0182(3) Uani 1 1 d . . . . .
C3 C 0.89249(15) 0.7299(2) 0.41902(9) 0.0178(3) Uani 1 1 d . . . . .
C4 C 0.82088(15) 0.6328(2) 0.47787(9) 0.0179(3) Uani 1 1 d . . . . .
C5 C 0.90424(15) 0.6340(2) 0.56306(9) 0.0171(3) Uani 1 1 d . . . . .
C6 C 0.87278(15) 0.5459(2) 0.63458(9) 0.0198(3) Uani 1 1 d . . . . .
H6 H 0.9291 0.5487 0.6904 0.024 Uiso 1 1 calc R . . . .
C7 C 0.75272(16) 0.4523(2) 0.61968(10) 0.0212(3) Uani 1 1 d . . . . .
H7 H 0.7286 0.3915 0.6667 0.025 Uiso 1 1 calc R . . . .
C8 C 0.66856(16) 0.4479(2) 0.53642(10) 0.0211(3) Uani 1 1 d . . . . .
H8 H 0.5894 0.3840 0.5284 0.025 Uiso 1 1 calc R . . . .
C9 C 0.70171(15) 0.5383(2) 0.46480(10) 0.0202(3) Uani 1 1 d . . . . .
H9 H 0.6451 0.5355 0.4091 0.024 Uiso 1 1 calc R . . . .
C10 C 1.12567(15) 0.7672(2) 0.63960(9) 0.0206(3) Uani 1 1 d . . . . .
H10A H 1.0864 0.8156 0.6864 0.031 Uiso 1 1 calc GR . . . .
H10B H 1.1893 0.8478 0.6239 0.031 Uiso 1 1 calc GR . . . .
H10C H 1.1705 0.6607 0.6597 0.031 Uiso 1 1 calc GR . . . .
C13 C 0.75333(15) 0.7113(2) 0.27704(9) 0.0195(3) Uani 1 1 d . . . . .
C14 C 0.75957(15) 0.6052(2) 0.20277(9) 0.0191(3) Uani 1 1 d . . . . .
C15 C 0.64413(16) 0.5798(2) 0.13764(10) 0.0221(4) Uani 1 1 d . . . . .
H15 H 0.6473 0.5090 0.0888 0.027 Uiso 1 1 calc R . . . .
C16 C 0.52420(16) 0.6604(2) 0.14558(10) 0.0247(4) Uani 1 1 d . . . . .
H16 H 0.4480 0.6452 0.1013 0.030 Uiso 1 1 calc R . . . .
C17 C 0.51772(17) 0.7631(2) 0.21894(11) 0.0258(4) Uani 1 1 d . . . . .
H17 H 0.4371 0.8153 0.2244 0.031 Uiso 1 1 calc R . . . .
C18 C 0.63185(16) 0.7877(2) 0.28424(10) 0.0235(4) Uani 1 1 d . . . . .
H18 H 0.6270 0.8563 0.3336 0.028 Uiso 1 1 calc R . . . .
N1 N 1.02066(13) 0.73321(17) 0.56193(8) 0.0174(3) Uani 1 1 d . . . . .
N12 N 0.87522(13) 0.75802(18) 0.33524(8) 0.0199(3) Uani 1 1 d . . . . .
O11 O 1.10908(11) 0.88817(15) 0.45869(7) 0.0210(3) Uani 1 1 d . . . . .
O19 O 0.87976(11) 0.53264(16) 0.19964(7) 0.0218(3) Uani 1 1 d . . . . .
H19 H 0.8760 0.4852 0.1512 0.033 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
C2 C3 1.532(2) . ?
C2 N1 1.3544(19) . ?
C2 O11 1.2277(19) . ?
C3 C4 1.467(2) . ?
C3 N12 1.2770(19) . ?
C4 C5 1.4077(19) . ?
C4 C9 1.393(2) . ?
C5 C6 1.377(2) . ?
C5 N1 1.410(2) . ?
C6 H6 0.9300 . ?
C6 C7 1.396(2) . ?
C7 H7 0.9300 . ?
C7 C8 1.388(2) . ?
C8 H8 0.9300 . ?
C8 C9 1.393(2) . ?
C9 H9 0.9300 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C10 N1 1.4562(17) . ?
C13 C14 1.411(2) . ?
C13 C18 1.390(2) . ?
C13 N12 1.4220(19) . ?
C14 C15 1.3953(19) . ?
C14 O19 1.3513(19) . ?
C15 H15 0.9300 . ?
C15 C16 1.393(2) . ?
C16 H16 0.9300 . ?
C16 C17 1.385(2) . ?
C17 H17 0.9300 . ?
C17 C18 1.387(2) . ?
C18 H18 0.9300 . ?
O19 H19 0.8200 . ?

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 106.46(13) . . ?
O11 C2 C3 127.98(13) . . ?
O11 C2 N1 125.56(14) . . ?
C4 C3 C2 105.52(12) . . ?
N12 C3 C2 118.71(15) . . ?
N12 C3 C4 135.59(15) . . ?
C5 C4 C3 106.49(13) . . ?
C9 C4 C3 134.36(13) . . ?
C9 C4 C5 118.97(14) . . ?
C4 C5 N1 110.23(13) . . ?
C6 C5 C4 122.75(14) . . ?
C6 C5 N1 127.01(13) . . ?
C5 C6 H6 121.4 . . ?
C5 C6 C7 117.11(13) . . ?
C7 C6 H6 121.4 . . ?
C6 C7 H7 119.2 . . ?
C8 C7 C6 121.59(15) . . ?
C8 C7 H7 119.2 . . ?
C7 C8 H8 119.7 . . ?
C7 C8 C9 120.56(15) . . ?
C9 C8 H8 119.7 . . ?
C4 C9 C8 119.02(13) . . ?
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 N12 118.70(14) . . ?
C18 C13 C14 119.29(14) . . ?
C18 C13 N12 121.33(14) . . ?
C15 C14 C13 119.49(14) . . ?
O19 C14 C13 116.81(12) . . ?
O19 C14 C15 123.70(14) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 C14 120.11(15) . . ?
C16 C15 H15 119.9 . . ?
C15 C16 H16 119.8 . . ?
C17 C16 C15 120.40(14) . . ?
C17 C16 H16 119.8 . . ?
C16 C17 H17 120.1 . . ?
C16 C17 C18 119.75(16) . . ?
C18 C17 H17 120.1 . . ?
C13 C18 H18 119.5 . . ?
C17 C18 C13 120.95(15) . . ?
C17 C18 H18 119.5 . . ?
C2 N1 C5 111.21(12) . . ?
C2 N1 C10 124.10(13) . . ?
C5 N1 C10 124.68(12) . . ?
C3 N12 C13 121.12(14) . . ?
C14 O19 H19 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
C2 C3 C4 C5 -3.07(16) . . . . ?
C2 C3 C4 C9 -177.90(17) . . . . ?
C2 C3 N12 C13 -175.27(14) . . . . ?
C3 C2 N1 C5 -0.56(17) . . . . ?
C3 C2 N1 C10 -179.49(13) . . . . ?
C3 C4 C5 C6 -176.05(14) . . . . ?
C3 C4 C5 N1 2.87(17) . . . . ?
C3 C4 C9 C8 174.38(16) . . . . ?
C4 C3 N12 C13 10.4(3) . . . . ?
C4 C5 C6 C7 0.2(2) . . . . ?
C4 C5 N1 C2 -1.46(18) . . . . ?
C4 C5 N1 C10 177.46(14) . . . . ?
C5 C4 C9 C8 0.0(2) . . . . ?
C5 C6 C7 C8 0.1(2) . . . . ?
C6 C5 N1 C2 177.40(15) . . . . ?
C6 C5 N1 C10 -3.7(2) . . . . ?
C6 C7 C8 C9 -0.3(3) . . . . ?
C7 C8 C9 C4 0.2(2) . . . . ?
C9 C4 C5 C6 -0.3(2) . . . . ?
C9 C4 C5 N1 178.65(14) . . . . ?
C13 C14 C15 C16 0.7(2) . . . . ?
C14 C13 C18 C17 -1.0(2) . . . . ?
C14 C13 N12 C3 -126.03(17) . . . . ?
C14 C15 C16 C17 -1.4(2) . . . . ?
C15 C16 C17 C18 0.9(3) . . . . ?
C16 C17 C18 C13 0.3(3) . . . . ?
C18 C13 C14 C15 0.5(2) . . . . ?
C18 C13 C14 O19 -179.27(14) . . . . ?
C18 C13 N12 C3 63.5(2) . . . . ?
N1 C2 C3 C4 2.26(16) . . . . ?
N1 C2 C3 N12 -173.61(14) . . . . ?
N1 C5 C6 C7 -178.51(15) . . . . ?
N12 C3 C4 C5 171.75(18) . . . . ?
N12 C3 C4 C9 -3.1(3) . . . . ?
N12 C13 C14 C15 -170.19(14) . . . . ?
N12 C13 C14 O19 10.1(2) . . . . ?
N12 C13 C18 C17 169.42(15) . . . . ?
O11 C2 C3 C4 -177.26(15) . . . . ?
O11 C2 C3 N12 6.9(2) . . . . ?
O11 C2 N1 C5 178.97(15) . . . . ?
O11 C2 N1 C10 0.0(2) . . . . ?
O19 C14 C15 C16 -179.57(15) . . . . ?


####################################################################### 
# 
# 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_as115
_database_code_depnum_ccdc_archive 'CCDC 1538866'
_audit_update_record             
;
2017-03-19 deposited with the CCDC.
2018-10-29 downloaded from the CCDC.
;
_audit_creation_date             2016-09-21
_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         'C38 H39 Cu N5 O2, B F4, 0.3(H2O)'
_chemical_formula_sum            'C38 H39 B Cu F4 N5 O2.30'
_chemical_formula_weight         752.89
_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'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   12.8485(3)
_cell_length_b                   14.2133(3)
_cell_length_c                   21.2613(5)
_cell_angle_alpha                90
_cell_angle_beta                 106.297(2)
_cell_angle_gamma                90
_cell_volume                     3726.72(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    10018
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.9470
_cell_measurement_theta_min      3.4670
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.647
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95661
_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.
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1562
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.03
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0310
_diffrn_reflns_av_unetI/netI     0.0365
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            25734
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.000
_diffrn_reflns_theta_min         3.035
_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 0.990
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -35.00   -8.00   1.0000   37.5000
omega____ theta____ kappa____ phi______ frames
    -      -10.9969  -19.0000   30.0000 27

#__ type_ start__ end____ width___ exp.time_
  2 omega  -48.00   16.00   1.0000   37.5000
omega____ theta____ kappa____ phi______ frames
    -      -10.9969  -57.0000  120.0000 64

#__ type_ start__ end____ width___ exp.time_
  3 omega    4.00   44.00   1.0000   37.5000
omega____ theta____ kappa____ phi______ frames
    -       12.8719  -99.0000  120.0000 40

#__ type_ start__ end____ width___ exp.time_
  4 omega  -57.00   17.00   1.0000   37.5000
omega____ theta____ kappa____ phi______ frames
    -       12.8719  -38.0000 -120.0000 74

#__ type_ start__ end____ width___ exp.time_
  5 omega  -30.00    2.00   1.0000   37.5000
omega____ theta____ kappa____ phi______ frames
    -      -10.9969   38.0000 -150.0000 32

#__ type_ start__ end____ width___ exp.time_
  6 omega    7.00   32.00   1.0000   37.5000
omega____ theta____ kappa____ phi______ frames
    -      -10.9969   38.0000 -150.0000 25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0156390000
_diffrn_orient_matrix_UB_12      -0.0467443000
_diffrn_orient_matrix_UB_13      -0.0100312000
_diffrn_orient_matrix_UB_21      -0.0119315000
_diffrn_orient_matrix_UB_22      0.0140255000
_diffrn_orient_matrix_UB_23      -0.0332886000
_diffrn_orient_matrix_UB_31      0.0540361000
_diffrn_orient_matrix_UB_32      -0.0104079000
_diffrn_orient_matrix_UB_33      0.0001330000
_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                7026
_reflns_number_total             8807
_reflns_odcompleteness_completeness 99.02
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.04
_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 1.171.37.35 (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    'ShelXS (Sheldrick, 2015)'
_refine_diff_density_max         1.148
_refine_diff_density_min         -0.929
_refine_diff_density_rms         0.073
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     479
_refine_ls_number_reflns         8807
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0647
_refine_ls_R_factor_gt           0.0484
_refine_ls_restrained_S_all      1.019
_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)+(0.0547P)²+5.3371P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1181
_refine_ls_wR_factor_ref         0.1302
_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. Restrained distances
 O31A-O31B
 1.2 with sigma of 0.05
3. Uiso/Uaniso restraints and constraints
Uanis(F28A) = Uanis(F28B) = Uanis(F29A) = Uanis(F29B) = Uanis(F30A) =
Uanis(F30B)
Uanis(O31A) = Uanis(O31B)
4. Others
 Sof(F28B)=Sof(F29B)=Sof(F30B)=1-FVAR(1)
 Sof(F28A)=Sof(F29A)=Sof(F30A)=FVAR(1)
 Fixed Sof: O31A(0.21) O31B(0.09)
5.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C6'(H6'), C7(H7), C7'(H7'), C8(H8), C8'(H8'), C9(H9), C9'(H9'),
 C15(H15), C15'(H15'), C17(H17), C17'(H17')
5.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C10'(H10D,H10E,H10F), C19(H19A,H19B,H19C), C19'(H19D,
 H19E,H19F), C20(H20A,H20B,H20C), C20'(H20D,H20E,H20F), C21(H21A,H21B,H21C),
 C21'(H21D,H21E,H21F), C25(H25A,H25B,H25C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.10291(16) 0.34137(13) 0.55333(10) 0.0206(4) Uani 1 1 d . . . . .
N1' N 0.49328(15) 0.43395(14) 0.31103(10) 0.0196(4) Uani 1 1 d . . . . .
C2 C 0.13395(18) 0.36483(16) 0.49921(12) 0.0204(5) Uani 1 1 d . . . . .
C2' C 0.39774(19) 0.41843(16) 0.32549(11) 0.0189(5) Uani 1 1 d . . . . .
C3 C 0.17682(17) 0.27586(16) 0.47626(11) 0.0181(4) Uani 1 1 d . . . . .
C3' C 0.36917(17) 0.50987(15) 0.35294(11) 0.0166(4) Uani 1 1 d . . . . .
C4 C 0.16602(18) 0.20163(16) 0.52133(11) 0.0190(4) Uani 1 1 d . . . . .
C4' C 0.45174(18) 0.57808(16) 0.34863(11) 0.0177(4) Uani 1 1 d . . . . .
C5 C 0.12050(17) 0.24435(16) 0.56694(12) 0.0186(4) Uani 1 1 d . . . . .
C5' C 0.52640(18) 0.52840(16) 0.32393(11) 0.0178(4) Uani 1 1 d . . . . .
C6 C 0.09847(19) 0.19479(17) 0.61731(12) 0.0221(5) Uani 1 1 d . . . . .
H6 H 0.0687 0.2239 0.6474 0.027 Uiso 1 1 calc R . . . .
C6' C 0.61744(19) 0.57037(19) 0.31469(12) 0.0236(5) Uani 1 1 d . . . . .
H6' H 0.6661 0.5368 0.2982 0.028 Uiso 1 1 calc R . . . .
C7 C 0.1228(2) 0.09882(17) 0.62116(13) 0.0262(5) Uani 1 1 d . . . . .
H7 H 0.1077 0.0631 0.6542 0.031 Uiso 1 1 calc R . . . .
C7' C 0.6337(2) 0.66507(19) 0.33099(13) 0.0280(5) Uani 1 1 d . . . . .
H7' H 0.6945 0.6954 0.3251 0.034 Uiso 1 1 calc R . . . .
C8 C 0.1688(2) 0.05540(17) 0.57706(12) 0.0272(5) Uani 1 1 d . . . . .
H8 H 0.1847 -0.0085 0.5812 0.033 Uiso 1 1 calc R . . . .
C8' C 0.5614(2) 0.71526(18) 0.35578(14) 0.0282(5) Uani 1 1 d . . . . .
H8' H 0.5748 0.7784 0.3666 0.034 Uiso 1 1 calc R . . . .
C9 C 0.1914(2) 0.10644(17) 0.52660(12) 0.0247(5) Uani 1 1 d . . . . .
H9 H 0.2227 0.0775 0.4971 0.030 Uiso 1 1 calc R . . . .
C9' C 0.4694(2) 0.67266(17) 0.36472(13) 0.0240(5) Uani 1 1 d . . . . .
H9' H 0.4208 0.7066 0.3811 0.029 Uiso 1 1 calc R . . . .
C10 C 0.0547(2) 0.40531(18) 0.59037(14) 0.0280(6) Uani 1 1 d . . . . .
H10A H 0.0591 0.4685 0.5755 0.042 Uiso 1 1 calc GR . . . .
H10B H 0.0930 0.4010 0.6361 0.042 Uiso 1 1 calc GR . . . .
H10C H -0.0200 0.3887 0.5841 0.042 Uiso 1 1 calc GR . . . .
C10' C 0.5546(2) 0.36172(19) 0.28886(14) 0.0311(6) Uani 1 1 d . . . . .
H10D H 0.5251 0.3010 0.2938 0.047 Uiso 1 1 calc GR . . . .
H10E H 0.6291 0.3643 0.3146 0.047 Uiso 1 1 calc GR . . . .
H10F H 0.5503 0.3721 0.2436 0.047 Uiso 1 1 calc GR . . . .
O11 O 0.12902(14) 0.44193(12) 0.47337(9) 0.0273(4) Uani 1 1 d . . . . .
O11' O 0.34510(14) 0.34628(11) 0.31829(9) 0.0247(4) Uani 1 1 d . . . . .
N12 N 0.21250(15) 0.27967(13) 0.42561(10) 0.0182(4) Uani 1 1 d . . . . .
N12' N 0.28717(15) 0.51042(13) 0.37628(9) 0.0168(4) Uani 1 1 d . . . . .
C13 C 0.25036(18) 0.19360(16) 0.40383(11) 0.0182(4) Uani 1 1 d . . . . .
C13' C 0.25880(17) 0.59883(15) 0.40062(11) 0.0166(4) Uani 1 1 d . . . . .
C14 C 0.1749(2) 0.13033(18) 0.36564(12) 0.0222(5) Uani 1 1 d . . . . .
C14' C 0.19894(18) 0.66433(16) 0.35568(12) 0.0191(5) Uani 1 1 d . . . . .
C15 C 0.2143(2) 0.04732(18) 0.34634(12) 0.0264(5) Uani 1 1 d . . . . .
H15 H 0.1653 0.0046 0.3210 0.032 Uiso 1 1 calc R . . . .
C15' C 0.17436(19) 0.74935(17) 0.38080(12) 0.0219(5) Uani 1 1 d . . . . .
H15' H 0.1359 0.7945 0.3518 0.026 Uiso 1 1 calc R . . . .
C16 C 0.3238(2) 0.02601(18) 0.36340(13) 0.0292(6) Uani 1 1 d . . . . .
C16' C 0.20509(19) 0.76932(17) 0.44743(13) 0.0241(5) Uani 1 1 d . . . . .
C17 C 0.3962(2) 0.09136(18) 0.40051(14) 0.0288(6) Uani 1 1 d . . . . .
H17 H 0.4700 0.0783 0.4118 0.035 Uiso 1 1 calc R . . . .
C17' C 0.2630(2) 0.70133(18) 0.49015(12) 0.0245(5) Uani 1 1 d . . . . .
H17' H 0.2836 0.7136 0.5349 0.029 Uiso 1 1 calc R . . . .
C18 C 0.36166(19) 0.17558(17) 0.42125(12) 0.0230(5) Uani 1 1 d . . . . .
C18' C 0.29104(18) 0.61544(17) 0.46807(12) 0.0209(5) Uani 1 1 d . . . . .
C19 C 0.4411(2) 0.2436(2) 0.46286(15) 0.0351(6) Uani 1 1 d . . . . .
H19A H 0.4251 0.3061 0.4457 0.053 Uiso 1 1 calc GR . . . .
H19B H 0.5133 0.2267 0.4626 0.053 Uiso 1 1 calc GR . . . .
H19C H 0.4358 0.2416 0.5070 0.053 Uiso 1 1 calc GR . . . .
C19' C 0.3584(2) 0.54556(19) 0.51553(13) 0.0285(6) Uani 1 1 d . . . . .
H19D H 0.3367 0.4829 0.5007 0.043 Uiso 1 1 calc GR . . . .
H19E H 0.3479 0.5549 0.5580 0.043 Uiso 1 1 calc GR . . . .
H19F H 0.4336 0.5543 0.5181 0.043 Uiso 1 1 calc GR . . . .
C20 C 0.3639(3) -0.0659(2) 0.34307(17) 0.0435(8) Uani 1 1 d . . . . .
H20A H 0.3644 -0.1131 0.3754 0.065 Uiso 1 1 calc GR . . . .
H20B H 0.4361 -0.0577 0.3393 0.065 Uiso 1 1 calc GR . . . .
H20C H 0.3168 -0.0854 0.3016 0.065 Uiso 1 1 calc GR . . . .
C20' C 0.1784(2) 0.86248(19) 0.47312(15) 0.0361(6) Uani 1 1 d . . . . .
H20D H 0.1528 0.9055 0.4373 0.054 Uiso 1 1 calc GR . . . .
H20E H 0.2423 0.8877 0.5035 0.054 Uiso 1 1 calc GR . . . .
H20F H 0.1232 0.8535 0.4950 0.054 Uiso 1 1 calc GR . . . .
C21 C 0.0553(2) 0.1498(2) 0.34772(14) 0.0327(6) Uani 1 1 d . . . . .
H21A H 0.0313 0.1491 0.3866 0.049 Uiso 1 1 calc GR . . . .
H21B H 0.0173 0.1023 0.3180 0.049 Uiso 1 1 calc GR . . . .
H21C H 0.0409 0.2104 0.3272 0.049 Uiso 1 1 calc GR . . . .
C21' C 0.1633(2) 0.64530(18) 0.28334(12) 0.0276(5) Uani 1 1 d . . . . .
H21D H 0.2228 0.6559 0.2653 0.041 Uiso 1 1 calc GR . . . .
H21E H 0.1045 0.6866 0.2627 0.041 Uiso 1 1 calc GR . . . .
H21F H 0.1396 0.5812 0.2758 0.041 Uiso 1 1 calc GR . . . .
Cu22 Cu 0.19817(2) 0.39757(2) 0.37429(2) 0.02064(9) Uani 1 1 d . . . . .
N23 N 0.05546(18) 0.40599(16) 0.31111(12) 0.0304(5) Uani 1 1 d . . . . .
C24 C -0.0318(2) 0.4118(2) 0.28060(15) 0.0327(6) Uani 1 1 d . . . . .
C25 C -0.1439(3) 0.4195(3) 0.2408(2) 0.0586(10) Uani 1 1 d . . . . .
H25A H -0.1469 0.4141 0.1953 0.088 Uiso 1 1 calc GR . . . .
H25B H -0.1727 0.4794 0.2484 0.088 Uiso 1 1 calc GR . . . .
H25C H -0.1860 0.3701 0.2523 0.088 Uiso 1 1 calc GR . . . .
B26 B 0.7254(3) 0.1695(2) 0.30969(16) 0.0313(7) Uani 1 1 d . . . . .
F27 F 0.79731(13) 0.09658(11) 0.30973(9) 0.0362(4) Uani 1 1 d . . . . .
F28A F 0.6583(5) 0.1426(4) 0.3492(3) 0.0532(5) Uani 0.474(4) 1 d . . P A 1
F28B F 0.6906(4) 0.1730(3) 0.3622(2) 0.0532(5) Uani 0.526(4) 1 d . . P A 2
F29A F 0.7841(4) 0.2510(3) 0.3406(3) 0.0532(5) Uani 0.474(4) 1 d . . P A 1
F29B F 0.7778(3) 0.2553(3) 0.3011(2) 0.0532(5) Uani 0.526(4) 1 d . . P A 2
F30A F 0.6701(5) 0.1941(4) 0.2498(3) 0.0532(5) Uani 0.474(4) 1 d . . P A 1
F30B F 0.6392(4) 0.1621(3) 0.2516(2) 0.0532(5) Uani 0.526(4) 1 d . . P A 2
O31A O 0.9088(10) 0.3386(11) 0.4235(7) 0.064(4) Uani 0.21 1 d D . P B 1
O31B O 0.838(2) 0.393(2) 0.3978(15) 0.064(4) Uani 0.09 1 d D . P C 2


_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 1.361(3) . ?
N1 C5 1.414(3) . ?
N1 C10 1.450(3) . ?
N1' C2' 1.364(3) . ?
N1' C5' 1.412(3) . ?
N1' C10' 1.451(3) . ?
C2 C3 1.514(3) . ?
C2 O11 1.219(3) . ?
C2' C3' 1.512(3) . ?
C2' O11' 1.214(3) . ?
C3 C4 1.458(3) . ?
C3 N12 1.285(3) . ?
C3' C4' 1.459(3) . ?
C3' N12' 1.284(3) . ?
C4 C5 1.403(3) . ?
C4 C9 1.389(3) . ?
C4' C5' 1.406(3) . ?
C4' C9' 1.390(3) . ?
C5 C6 1.376(3) . ?
C5' C6' 1.375(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.397(3) . ?
C6' H6' 0.9300 . ?
C6' C7' 1.391(4) . ?
C7 H7 0.9300 . ?
C7 C8 1.386(4) . ?
C7' H7' 0.9300 . ?
C7' C8' 1.387(4) . ?
C8 H8 0.9300 . ?
C8 C9 1.392(3) . ?
C8' H8' 0.9300 . ?
C8' C9' 1.388(3) . ?
C9 H9 0.9300 . ?
C9' H9' 0.9300 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C10' H10D 0.9600 . ?
C10' H10E 0.9600 . ?
C10' H10F 0.9600 . ?
N12 C13 1.440(3) . ?
N12 Cu22 1.9799(19) . ?
N12' C13' 1.444(3) . ?
N12' Cu22 1.9633(19) . ?
C13 C14 1.402(3) . ?
C13 C18 1.397(3) . ?
C13' C14' 1.400(3) . ?
C13' C18' 1.397(3) . ?
C14 C15 1.391(4) . ?
C14 C21 1.501(4) . ?
C14' C15' 1.393(3) . ?
C14' C21' 1.501(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.384(4) . ?
C15' H15' 0.9300 . ?
C15' C16' 1.389(4) . ?
C16 C17 1.392(4) . ?
C16 C20 1.512(4) . ?
C16' C17' 1.390(4) . ?
C16' C20' 1.508(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.391(4) . ?
C17' H17' 0.9300 . ?
C17' C18' 1.391(3) . ?
C18 C19 1.501(4) . ?
C18' C19' 1.504(3) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C19' H19D 0.9600 . ?
C19' H19E 0.9600 . ?
C19' H19F 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C20' H20D 0.9600 . ?
C20' H20E 0.9600 . ?
C20' H20F 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C21' H21D 0.9600 . ?
C21' H21E 0.9600 . ?
C21' H21F 0.9600 . ?
Cu22 N23 1.949(2) . ?
N23 C24 1.129(4) . ?
C24 C25 1.456(4) . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
B26 F27 1.389(3) . ?
B26 F28A 1.414(6) . ?
B26 F28B 1.314(6) . ?
B26 F29A 1.437(6) . ?
B26 F29B 1.430(5) . ?
B26 F30A 1.320(6) . ?
B26 F30B 1.412(6) . ?

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 110.12(19) . . ?
C2 N1 C10 125.2(2) . . ?
C5 N1 C10 124.6(2) . . ?
C2' N1' C5' 110.55(18) . . ?
C2' N1' C10' 124.3(2) . . ?
C5' N1' C10' 125.0(2) . . ?
N1 C2 C3 106.70(19) . . ?
O11 C2 N1 127.6(2) . . ?
O11 C2 C3 125.7(2) . . ?
N1' C2' C3' 106.22(19) . . ?
O11' C2' N1' 127.8(2) . . ?
O11' C2' C3' 126.0(2) . . ?
C4 C3 C2 106.40(19) . . ?
N12 C3 C2 118.9(2) . . ?
N12 C3 C4 134.7(2) . . ?
C4' C3' C2' 106.70(18) . . ?
N12' C3' C2' 118.0(2) . . ?
N12' C3' C4' 135.2(2) . . ?
C5 C4 C3 106.0(2) . . ?
C9 C4 C3 134.0(2) . . ?
C9 C4 C5 120.0(2) . . ?
C5' C4' C3' 105.91(19) . . ?
C9' C4' C3' 134.3(2) . . ?
C9' C4' C5' 119.7(2) . . ?
C4 C5 N1 110.7(2) . . ?
C6 C5 N1 127.1(2) . . ?
C6 C5 C4 122.2(2) . . ?
C4' C5' N1' 110.49(19) . . ?
C6' C5' N1' 127.4(2) . . ?
C6' C5' C4' 122.2(2) . . ?
C5 C6 H6 121.5 . . ?
C5 C6 C7 117.0(2) . . ?
C7 C6 H6 121.5 . . ?
C5' C6' H6' 121.3 . . ?
C5' C6' C7' 117.3(2) . . ?
C7' C6' H6' 121.3 . . ?
C6 C7 H7 119.1 . . ?
C8 C7 C6 121.7(2) . . ?
C8 C7 H7 119.1 . . ?
C6' C7' H7' 119.3 . . ?
C8' C7' C6' 121.5(2) . . ?
C8' C7' H7' 119.3 . . ?
C7 C8 H8 119.7 . . ?
C7 C8 C9 120.7(2) . . ?
C9 C8 H8 119.7 . . ?
C7' C8' H8' 119.5 . . ?
C7' C8' C9' 121.0(2) . . ?
C9' C8' H8' 119.5 . . ?
C4 C9 C8 118.4(2) . . ?
C4 C9 H9 120.8 . . ?
C8 C9 H9 120.8 . . ?
C4' C9' H9' 120.8 . . ?
C8' C9' C4' 118.4(2) . . ?
C8' C9' H9' 120.8 . . ?
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 . . ?
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 . . ?
C3 N12 C13 117.78(19) . . ?
C3 N12 Cu22 119.85(16) . . ?
C13 N12 Cu22 121.97(14) . . ?
C3' N12' C13' 117.42(19) . . ?
C3' N12' Cu22 121.51(16) . . ?
C13' N12' Cu22 120.97(13) . . ?
C14 C13 N12 119.3(2) . . ?
C18 C13 N12 118.9(2) . . ?
C18 C13 C14 121.7(2) . . ?
C14' C13' N12' 118.7(2) . . ?
C18' C13' N12' 118.9(2) . . ?
C18' C13' C14' 122.4(2) . . ?
C13 C14 C21 121.4(2) . . ?
C15 C14 C13 117.7(2) . . ?
C15 C14 C21 120.9(2) . . ?
C13' C14' C21' 122.1(2) . . ?
C15' C14' C13' 117.1(2) . . ?
C15' C14' C21' 120.8(2) . . ?
C14 C15 H15 118.8 . . ?
C16 C15 C14 122.4(2) . . ?
C16 C15 H15 118.8 . . ?
C14' C15' H15' 118.7 . . ?
C16' C15' C14' 122.6(2) . . ?
C16' C15' H15' 118.7 . . ?
C15 C16 C17 118.1(2) . . ?
C15 C16 C20 121.1(3) . . ?
C17 C16 C20 120.8(3) . . ?
C15' C16' C17' 118.1(2) . . ?
C15' C16' C20' 121.4(2) . . ?
C17' C16' C20' 120.5(2) . . ?
C16 C17 H17 118.9 . . ?
C18 C17 C16 122.2(2) . . ?
C18 C17 H17 118.9 . . ?
C16' C17' H17' 119.0 . . ?
C16' C17' C18' 122.1(2) . . ?
C18' C17' H17' 119.0 . . ?
C13 C18 C19 121.0(2) . . ?
C17 C18 C13 117.9(2) . . ?
C17 C18 C19 121.1(2) . . ?
C13' C18' C19' 121.7(2) . . ?
C17' C18' C13' 117.7(2) . . ?
C17' C18' C19' 120.5(2) . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C18' C19' H19D 109.5 . . ?
C18' C19' H19E 109.5 . . ?
C18' C19' H19F 109.5 . . ?
H19D C19' H19E 109.5 . . ?
H19D C19' H19F 109.5 . . ?
H19E C19' H19F 109.5 . . ?
C16 C20 H20A 109.5 . . ?
C16 C20 H20B 109.5 . . ?
C16 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C16' C20' H20D 109.5 . . ?
C16' C20' H20E 109.5 . . ?
C16' C20' H20F 109.5 . . ?
H20D C20' H20E 109.5 . . ?
H20D C20' H20F 109.5 . . ?
H20E C20' H20F 109.5 . . ?
C14 C21 H21A 109.5 . . ?
C14 C21 H21B 109.5 . . ?
C14 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C14' C21' H21D 109.5 . . ?
C14' C21' H21E 109.5 . . ?
C14' C21' H21F 109.5 . . ?
H21D C21' H21E 109.5 . . ?
H21D C21' H21F 109.5 . . ?
H21E C21' H21F 109.5 . . ?
N12' Cu22 N12 135.73(8) . . ?
N23 Cu22 N12 110.84(9) . . ?
N23 Cu22 N12' 113.22(9) . . ?
C24 N23 Cu22 172.0(2) . . ?
N23 C24 C25 179.5(4) . . ?
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 . . ?
F27 B26 F28A 108.3(3) . . ?
F27 B26 F29A 109.7(3) . . ?
F27 B26 F29B 107.4(3) . . ?
F27 B26 F30B 107.7(3) . . ?
F28A B26 F29A 106.0(3) . . ?
F28B B26 F27 114.3(3) . . ?
F28B B26 F29B 111.2(3) . . ?
F28B B26 F30B 112.0(3) . . ?
F30A B26 F27 112.1(3) . . ?
F30A B26 F28A 113.1(4) . . ?
F30A B26 F29A 107.4(4) . . ?
F30B B26 F29B 103.5(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C2 C3 C4 0.6(2) . . . . ?
N1 C2 C3 N12 -179.4(2) . . . . ?
N1 C5 C6 C7 -180.0(2) . . . . ?
N1' C2' C3' C4' 3.6(2) . . . . ?
N1' C2' C3' N12' -173.4(2) . . . . ?
N1' C5' C6' C7' -180.0(2) . . . . ?
C2 N1 C5 C4 0.9(3) . . . . ?
C2 N1 C5 C6 -179.5(2) . . . . ?
C2 C3 C4 C5 -0.1(2) . . . . ?
C2 C3 C4 C9 -179.3(3) . . . . ?
C2 C3 N12 C13 -178.51(19) . . . . ?
C2 C3 N12 Cu22 -5.7(3) . . . . ?
C2' N1' C5' C4' 0.7(3) . . . . ?
C2' N1' C5' C6' -179.1(2) . . . . ?
C2' C3' C4' C5' -3.1(2) . . . . ?
C2' C3' C4' C9' 179.0(3) . . . . ?
C2' C3' N12' C13' -178.24(19) . . . . ?
C2' C3' N12' Cu22 -1.8(3) . . . . ?
C3 C4 C5 N1 -0.5(3) . . . . ?
C3 C4 C5 C6 179.9(2) . . . . ?
C3 C4 C9 C8 -179.7(3) . . . . ?
C3 N12 C13 C14 81.0(3) . . . . ?
C3 N12 C13 C18 -99.2(3) . . . . ?
C3' C4' C5' N1' 1.6(3) . . . . ?
C3' C4' C5' C6' -178.5(2) . . . . ?
C3' C4' C9' C8' 177.6(3) . . . . ?
C3' N12' C13' C14' 80.6(3) . . . . ?
C3' N12' C13' C18' -100.1(2) . . . . ?
C4 C3 N12 C13 1.5(4) . . . . ?
C4 C3 N12 Cu22 174.4(2) . . . . ?
C4 C5 C6 C7 -0.4(4) . . . . ?
C4' C3' N12' C13' 6.0(4) . . . . ?
C4' C3' N12' Cu22 -177.6(2) . . . . ?
C4' C5' C6' C7' 0.2(4) . . . . ?
C5 N1 C2 C3 -0.9(3) . . . . ?
C5 N1 C2 O11 179.2(2) . . . . ?
C5 C4 C9 C8 1.1(4) . . . . ?
C5 C6 C7 C8 1.1(4) . . . . ?
C5' N1' C2' C3' -2.6(2) . . . . ?
C5' N1' C2' O11' 177.5(2) . . . . ?
C5' C4' C9' C8' -0.1(4) . . . . ?
C5' C6' C7' C8' 0.2(4) . . . . ?
C6 C7 C8 C9 -0.7(4) . . . . ?
C6' C7' C8' C9' -0.5(4) . . . . ?
C7 C8 C9 C4 -0.4(4) . . . . ?
C7' C8' C9' C4' 0.4(4) . . . . ?
C9 C4 C5 N1 178.9(2) . . . . ?
C9 C4 C5 C6 -0.7(4) . . . . ?
C9' C4' C5' N1' 179.9(2) . . . . ?
C9' C4' C5' C6' -0.2(4) . . . . ?
C10 N1 C2 C3 -178.6(2) . . . . ?
C10 N1 C2 O11 1.5(4) . . . . ?
C10 N1 C5 C4 178.6(2) . . . . ?
C10 N1 C5 C6 -1.8(4) . . . . ?
C10' N1' C2' C3' 174.3(2) . . . . ?
C10' N1' C2' O11' -5.6(4) . . . . ?
C10' N1' C5' C4' -176.2(2) . . . . ?
C10' N1' C5' C6' 3.9(4) . . . . ?
O11 C2 C3 C4 -179.5(2) . . . . ?
O11 C2 C3 N12 0.6(4) . . . . ?
O11' C2' C3' C4' -176.6(2) . . . . ?
O11' C2' C3' N12' 6.5(4) . . . . ?
N12 C3 C4 C5 179.9(3) . . . . ?
N12 C3 C4 C9 0.6(5) . . . . ?
N12 C13 C14 C15 -179.1(2) . . . . ?
N12 C13 C14 C21 -0.9(3) . . . . ?
N12 C13 C18 C17 179.0(2) . . . . ?
N12 C13 C18 C19 0.9(3) . . . . ?
N12' C3' C4' C5' 173.1(3) . . . . ?
N12' C3' C4' C9' -4.9(5) . . . . ?
N12' C13' C14' C15' -179.11(19) . . . . ?
N12' C13' C14' C21' 0.2(3) . . . . ?
N12' C13' C18' C17' 179.8(2) . . . . ?
N12' C13' C18' C19' 2.7(3) . . . . ?
C13 C14 C15 C16 -0.1(4) . . . . ?
C13' C14' C15' C16' -1.2(3) . . . . ?
C14 C13 C18 C17 -1.2(4) . . . . ?
C14 C13 C18 C19 -179.3(2) . . . . ?
C14 C15 C16 C17 -0.9(4) . . . . ?
C14 C15 C16 C20 178.5(2) . . . . ?
C14' C13' C18' C17' -0.9(3) . . . . ?
C14' C13' C18' C19' -178.0(2) . . . . ?
C14' C15' C16' C17' 0.3(4) . . . . ?
C14' C15' C16' C20' 179.3(2) . . . . ?
C15 C16 C17 C18 0.8(4) . . . . ?
C15' C16' C17' C18' 0.5(4) . . . . ?
C16 C17 C18 C13 0.2(4) . . . . ?
C16 C17 C18 C19 178.2(3) . . . . ?
C16' C17' C18' C13' -0.1(4) . . . . ?
C16' C17' C18' C19' 177.0(2) . . . . ?
C18 C13 C14 C15 1.1(3) . . . . ?
C18 C13 C14 C21 179.3(2) . . . . ?
C18' C13' C14' C15' 1.6(3) . . . . ?
C18' C13' C14' C21' -179.1(2) . . . . ?
C20 C16 C17 C18 -178.5(3) . . . . ?
C20' C16' C17' C18' -178.6(2) . . . . ?
C21 C14 C15 C16 -178.3(2) . . . . ?
C21' C14' C15' C16' 179.4(2) . . . . ?
Cu22 N12 C13 C14 -91.7(2) . . . . ?
Cu22 N12 C13 C18 88.1(2) . . . . ?
Cu22 N12' C13' C14' -95.8(2) . . . . ?
Cu22 N12' C13' C18' 83.5(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_isbd21
_database_code_depnum_ccdc_archive 'CCDC 1538862'
_audit_update_record             
;
2017-03-19 deposited with the CCDC.
2018-10-29 downloaded from the CCDC.
;
_audit_creation_date             2016-08-25
_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         'C18 H18 N2 O'
_chemical_formula_sum            'C18 H18 N2 O'
_chemical_formula_weight         278.34
_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                   6.9194(4)
_cell_length_b                   8.6089(5)
_cell_length_c                   24.9101(16)
_cell_angle_alpha                90
_cell_angle_beta                 96.141(6)
_cell_angle_gamma                90
_cell_volume                     1475.34(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5105
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.6340
_cell_measurement_theta_min      3.2840
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.97170
_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    1.253
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.10
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0256
_diffrn_reflns_av_unetI/netI     0.0209
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            15790
_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         27.499
_diffrn_reflns_theta_min         2.882
_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  -86.00   38.00   1.0000   12.0300
omega____ theta____ kappa____ phi______ frames
    -      -22.5803    0.0000 -150.0000 124

#__ type_ start__ end____ width___ exp.time_
  2 omega  -97.00  -65.00   1.0000   12.0300
omega____ theta____ kappa____ phi______ frames
    -      -22.5803 -178.0000  -30.0000 32

#__ type_ start__ end____ width___ exp.time_
  3 omega  -98.00  -57.00   1.0000   12.0300
omega____ theta____ kappa____ phi______ frames
    -      -22.5803  178.0000 -180.0000 41

#__ type_ start__ end____ width___ exp.time_
  4 omega    6.00   65.00   1.0000   12.0300
omega____ theta____ kappa____ phi______ frames
    -       23.5178  -99.0000 -180.0000 59

#__ type_ start__ end____ width___ exp.time_
  5 omega   -8.00   50.00   1.0000   12.0300
omega____ theta____ kappa____ phi______ frames
    -      -22.5803   38.0000   60.0000 58

#__ type_ start__ end____ width___ exp.time_
  6 omega  -77.00  -51.00   1.0000   12.0300
omega____ theta____ kappa____ phi______ frames
    -      -22.5803  121.0000 -157.0000 26

#__ type_ start__ end____ width___ exp.time_
  7 omega  -36.00   -2.00   1.0000   12.0300
omega____ theta____ kappa____ phi______ frames
    -      -22.5803  121.0000 -157.0000 34

#__ type_ start__ end____ width___ exp.time_
  8 omega  -69.00  -43.00   1.0000   12.0300
omega____ theta____ kappa____ phi______ frames
    -      -22.5803 -178.0000   90.0000 26

#__ type_ start__ end____ width___ exp.time_
  9 omega  -46.00   30.00   1.0000   12.0300
omega____ theta____ kappa____ phi______ frames
    -      -22.5803   77.0000    0.0000 76

#__ type_ start__ end____ width___ exp.time_
 10 omega  -97.00  -69.00   1.0000   12.0300
omega____ theta____ kappa____ phi______ frames
    -      -22.5803  153.0000    0.0000 28

#__ type_ start__ end____ width___ exp.time_
 11 omega  -11.00   15.00   1.0000   12.0300
omega____ theta____ kappa____ phi______ frames
    -      -22.5803   57.0000 -150.0000 26

#__ type_ start__ end____ width___ exp.time_
 12 omega  -66.00  -41.00   1.0000   12.0300
omega____ theta____ kappa____ phi______ frames
    -      -22.5803  -19.0000  -30.0000 25
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0242821000
_diffrn_orient_matrix_UB_12      -0.0772515000
_diffrn_orient_matrix_UB_13      0.0065177000
_diffrn_orient_matrix_UB_21      -0.0866985000
_diffrn_orient_matrix_UB_22      0.0268812000
_diffrn_orient_matrix_UB_23      0.0097858000
_diffrn_orient_matrix_UB_31      -0.0505308000
_diffrn_orient_matrix_UB_32      -0.0091984000
_diffrn_orient_matrix_UB_33      -0.0260959000
_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                2913
_reflns_number_total             3379
_reflns_odcompleteness_completeness 99.88
_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         0.276
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         3379
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0516
_refine_ls_R_factor_gt           0.0444
_refine_ls_restrained_S_all      1.030
_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)+(0.0506P)²+0.9122P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1101
_refine_ls_wR_factor_ref         0.1158
_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), C15(H15), C17(H17)
2.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C19(H19A,H19B,H19C), C20(H20A,H20B,H20C), C21(H21A,H21B,
 H21C)
;
_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 0.26308(16) 0.27825(13) 0.00630(4) 0.0164(2) Uani 1 1 d . . . . .
C2 C 0.33008(19) 0.41358(15) 0.02992(5) 0.0156(3) Uani 1 1 d . . . . .
C3 C 0.46036(18) 0.36795(15) 0.08111(5) 0.0151(3) Uani 1 1 d . . . . .
C4 C 0.44957(19) 0.19769(15) 0.08361(5) 0.0157(3) Uani 1 1 d . . . . .
C5 C 0.32857(18) 0.14900(15) 0.03768(5) 0.0161(3) Uani 1 1 d . . . . .
C6 C 0.2874(2) -0.00594(16) 0.02767(6) 0.0196(3) Uani 1 1 d . . . . .
H6 H 0.2067 -0.0368 -0.0027 0.024 Uiso 1 1 calc R . . . .
C7 C 0.3709(2) -0.11474(16) 0.06474(6) 0.0219(3) Uani 1 1 d . . . . .
H7 H 0.3468 -0.2199 0.0587 0.026 Uiso 1 1 calc R . . . .
C8 C 0.4893(2) -0.06870(16) 0.11046(6) 0.0221(3) Uani 1 1 d . . . . .
H8 H 0.5422 -0.1432 0.1348 0.027 Uiso 1 1 calc R . . . .
C9 C 0.5296(2) 0.08799(16) 0.12030(5) 0.0191(3) Uani 1 1 d . . . . .
H9 H 0.6089 0.1185 0.1510 0.023 Uiso 1 1 calc R . . . .
C10 C 0.1359(2) 0.27394(17) -0.04409(5) 0.0206(3) Uani 1 1 d . . . . .
H10A H 0.0114 0.3164 -0.0384 0.031 Uiso 1 1 calc GR . . . .
H10B H 0.1202 0.1684 -0.0562 0.031 Uiso 1 1 calc GR . . . .
H10C H 0.1922 0.3342 -0.0709 0.031 Uiso 1 1 calc GR . . . .
O11 O 0.29003(14) 0.54389(11) 0.01341(4) 0.0193(2) Uani 1 1 d . . . . .
N12 N 0.54421(16) 0.47405(13) 0.11061(4) 0.0165(2) Uani 1 1 d . . . . .
C13 C 0.66689(19) 0.43613(15) 0.15843(5) 0.0162(3) Uani 1 1 d . . . . .
C14 C 0.8462(2) 0.36017(16) 0.15737(5) 0.0183(3) Uani 1 1 d . . . . .
C15 C 0.9584(2) 0.33320(17) 0.20653(6) 0.0221(3) Uani 1 1 d . . . . .
H15 H 1.0762 0.2812 0.2064 0.027 Uiso 1 1 calc R . . . .
C16 C 0.9008(2) 0.38113(17) 0.25550(6) 0.0239(3) Uani 1 1 d . . . . .
C17 C 0.7261(2) 0.46087(16) 0.25491(5) 0.0224(3) Uani 1 1 d . . . . .
H17 H 0.6874 0.4960 0.2874 0.027 Uiso 1 1 calc R . . . .
C18 C 0.6073(2) 0.49003(15) 0.20739(5) 0.0186(3) Uani 1 1 d . . . . .
C19 C 0.9233(2) 0.30796(18) 0.10599(6) 0.0241(3) Uani 1 1 d . . . . .
H19A H 0.9046 0.1980 0.1017 0.036 Uiso 1 1 calc GR . . . .
H19B H 1.0594 0.3315 0.1077 0.036 Uiso 1 1 calc GR . . . .
H19C H 0.8550 0.3611 0.0758 0.036 Uiso 1 1 calc GR . . . .
C20 C 1.0252(3) 0.3484(2) 0.30782(6) 0.0365(4) Uani 1 1 d . . . . .
H20A H 1.0917 0.2514 0.3050 0.055 Uiso 1 1 calc GR . . . .
H20B H 0.9443 0.3428 0.3368 0.055 Uiso 1 1 calc GR . . . .
H20C H 1.1187 0.4302 0.3149 0.055 Uiso 1 1 calc GR . . . .
C21 C 0.4163(2) 0.57349(18) 0.20814(6) 0.0249(3) Uani 1 1 d . . . . .
H21A H 0.4011 0.6475 0.1792 0.037 Uiso 1 1 calc GR . . . .
H21B H 0.4142 0.6265 0.2420 0.037 Uiso 1 1 calc GR . . . .
H21C H 0.3119 0.4996 0.2037 0.037 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 1.3639(16) . ?
N1 C5 1.4066(17) . ?
N1 C10 1.4544(16) . ?
C2 C3 1.5320(17) . ?
C2 O11 1.2166(16) . ?
C3 C4 1.4693(18) . ?
C3 N12 1.2727(17) . ?
C4 C5 1.4075(18) . ?
C4 C9 1.3876(18) . ?
C5 C6 1.3810(19) . ?
C6 H6 0.9300 . ?
C6 C7 1.396(2) . ?
C7 H7 0.9300 . ?
C7 C8 1.387(2) . ?
C8 H8 0.9300 . ?
C8 C9 1.3939(19) . ?
C9 H9 0.9300 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
N12 C13 1.4248(16) . ?
C13 C14 1.4050(19) . ?
C13 C18 1.4072(18) . ?
C14 C15 1.3976(19) . ?
C14 C19 1.5069(19) . ?
C15 H15 0.9300 . ?
C15 C16 1.386(2) . ?
C16 C17 1.388(2) . ?
C16 C20 1.510(2) . ?
C17 H17 0.9300 . ?
C17 C18 1.3900(19) . ?
C18 C21 1.506(2) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 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 111.20(11) . . ?
C2 N1 C10 122.72(11) . . ?
C5 N1 C10 126.06(11) . . ?
N1 C2 C3 106.42(11) . . ?
O11 C2 N1 125.96(12) . . ?
O11 C2 C3 127.61(12) . . ?
C4 C3 C2 105.25(10) . . ?
N12 C3 C2 119.20(12) . . ?
N12 C3 C4 135.53(12) . . ?
C5 C4 C3 106.92(11) . . ?
C9 C4 C3 133.51(12) . . ?
C9 C4 C5 119.57(12) . . ?
N1 C5 C4 110.15(11) . . ?
C6 C5 N1 128.01(12) . . ?
C6 C5 C4 121.85(12) . . ?
C5 C6 H6 121.1 . . ?
C5 C6 C7 117.76(13) . . ?
C7 C6 H6 121.1 . . ?
C6 C7 H7 119.4 . . ?
C8 C7 C6 121.15(13) . . ?
C8 C7 H7 119.4 . . ?
C7 C8 H8 119.7 . . ?
C7 C8 C9 120.68(13) . . ?
C9 C8 H8 119.7 . . ?
C4 C9 C8 118.99(13) . . ?
C4 C9 H9 120.5 . . ?
C8 C9 H9 120.5 . . ?
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 120.82(11) . . ?
C14 C13 N12 122.63(12) . . ?
C14 C13 C18 120.72(12) . . ?
C18 C13 N12 116.45(12) . . ?
C13 C14 C19 123.25(12) . . ?
C15 C14 C13 118.03(12) . . ?
C15 C14 C19 118.72(13) . . ?
C14 C15 H15 118.8 . . ?
C16 C15 C14 122.43(14) . . ?
C16 C15 H15 118.8 . . ?
C15 C16 C17 118.03(13) . . ?
C15 C16 C20 120.87(15) . . ?
C17 C16 C20 121.10(14) . . ?
C16 C17 H17 118.9 . . ?
C16 C17 C18 122.22(13) . . ?
C18 C17 H17 118.9 . . ?
C13 C18 C21 120.45(12) . . ?
C17 C18 C13 118.49(13) . . ?
C17 C18 C21 121.04(13) . . ?
C14 C19 H19A 109.5 . . ?
C14 C19 H19B 109.5 . . ?
C14 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C16 C20 H20A 109.5 . . ?
C16 C20 H20B 109.5 . . ?
C16 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C18 C21 H21A 109.5 . . ?
C18 C21 H21B 109.5 . . ?
C18 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 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 -2.33(13) . . . . ?
N1 C2 C3 N12 179.10(11) . . . . ?
N1 C5 C6 C7 179.55(13) . . . . ?
C2 N1 C5 C4 -1.84(15) . . . . ?
C2 N1 C5 C6 178.29(13) . . . . ?
C2 C3 C4 C5 1.26(13) . . . . ?
C2 C3 C4 C9 -178.16(14) . . . . ?
C2 C3 N12 C13 -179.82(11) . . . . ?
C3 C4 C5 N1 0.21(14) . . . . ?
C3 C4 C5 C6 -179.91(12) . . . . ?
C3 C4 C9 C8 179.93(14) . . . . ?
C3 N12 C13 C14 67.88(17) . . . . ?
C3 N12 C13 C18 -117.17(14) . . . . ?
C4 C3 N12 C13 2.2(2) . . . . ?
C4 C5 C6 C7 -0.3(2) . . . . ?
C5 N1 C2 C3 2.55(14) . . . . ?
C5 N1 C2 O11 -176.38(13) . . . . ?
C5 C4 C9 C8 0.6(2) . . . . ?
C5 C6 C7 C8 0.8(2) . . . . ?
C6 C7 C8 C9 -0.7(2) . . . . ?
C7 C8 C9 C4 0.0(2) . . . . ?
C9 C4 C5 N1 179.73(12) . . . . ?
C9 C4 C5 C6 -0.4(2) . . . . ?
C10 N1 C2 C3 -179.10(11) . . . . ?
C10 N1 C2 O11 2.0(2) . . . . ?
C10 N1 C5 C4 179.89(12) . . . . ?
C10 N1 C5 C6 0.0(2) . . . . ?
O11 C2 C3 C4 176.58(13) . . . . ?
O11 C2 C3 N12 -2.0(2) . . . . ?
N12 C3 C4 C5 179.48(14) . . . . ?
N12 C3 C4 C9 0.1(3) . . . . ?
N12 C13 C14 C15 177.82(12) . . . . ?
N12 C13 C14 C19 -1.7(2) . . . . ?
N12 C13 C18 C17 -177.62(12) . . . . ?
N12 C13 C18 C21 4.03(19) . . . . ?
C13 C14 C15 C16 -1.3(2) . . . . ?
C14 C13 C18 C17 -2.6(2) . . . . ?
C14 C13 C18 C21 179.08(12) . . . . ?
C14 C15 C16 C17 -1.0(2) . . . . ?
C14 C15 C16 C20 179.39(14) . . . . ?
C15 C16 C17 C18 1.6(2) . . . . ?
C16 C17 C18 C13 0.2(2) . . . . ?
C16 C17 C18 C21 178.51(13) . . . . ?
C18 C13 C14 C15 3.08(19) . . . . ?
C18 C13 C14 C19 -176.39(13) . . . . ?
C19 C14 C15 C16 178.23(14) . . . . ?
C20 C16 C17 C18 -178.83(14) . . . . ?


####################################################################### 
# 
# 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_isbd_16_2
_database_code_depnum_ccdc_archive 'CCDC 1538858'
_audit_update_record             
;
2017-03-19 deposited with the CCDC.
2018-10-29 downloaded from the CCDC.
;
_audit_creation_date             2016-11-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.11.07 svn.r3352 for OlexSys, GUI svn.r5261)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C15 H11 Br N2 O'
_chemical_formula_sum            'C15 H11 Br N2 O'
_chemical_formula_weight         315.17
_chemical_melting_point          ?

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   8.1114(2)
_cell_length_b                   16.2246(4)
_cell_length_c                   19.1312(4)
_cell_angle_alpha                90
_cell_angle_beta                 95.696(2)
_cell_angle_gamma                90
_cell_volume                     2505.32(10)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2907
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      76.0180
_cell_measurement_theta_min      4.6480
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    4.408
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.53921
_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.
;
_exptl_crystal_colour            'translucent colorless'
_exptl_crystal_density_diffrn    1.671
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1264
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0411
_diffrn_reflns_av_unetI/netI     0.0401
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            6338
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.439
_diffrn_reflns_theta_min         4.646
_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 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   31.00   87.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -       40.3787  -19.0000  -60.0000 56

#__ type_ start__ end____ width___ exp.time_
  2 omega   40.00   90.00   1.0000   10.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000   30.0000 50

#__ type_ start__ end____ width___ exp.time_
  3 omega   54.00   80.00   1.0000   10.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000   60.0000 26

#__ type_ start__ end____ width___ exp.time_
  4 omega   31.00  109.00   1.0000   10.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000   60.0000 78

#__ type_ start__ end____ width___ exp.time_
  5 omega   37.00  102.00   1.0000   10.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000    0.0000 65

#__ type_ start__ end____ width___ exp.time_
  6 omega   58.00   99.00   1.0000   10.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000  -90.0000 41

#__ type_ start__ end____ width___ exp.time_
  7 omega   76.00  106.00   1.0000   10.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000 -150.0000 30

#__ type_ start__ end____ width___ exp.time_
  8 omega   52.00   86.00   1.0000   10.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000 -120.0000 34

#__ type_ start__ end____ width___ exp.time_
  9 omega   86.00  154.00   1.0000   10.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000 -120.0000 68

#__ type_ start__ end____ width___ exp.time_
 10 omega   88.00  178.00   1.0000   10.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000  -60.0000 90

#__ type_ start__ end____ width___ exp.time_
 11 omega   95.00  148.00   1.0000   10.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  178.0000  -90.0000 53

#__ type_ start__ end____ width___ exp.time_
 12 omega  -27.00   22.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787   38.0000 -150.0000 49

#__ type_ start__ end____ width___ exp.time_
 13 omega   30.00   55.00   1.0000   10.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000 -150.0000 25

#__ type_ start__ end____ width___ exp.time_
 14 omega    9.00   79.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -       40.3787  -99.0000 -120.0000 70

#__ type_ start__ end____ width___ exp.time_
 15 omega -110.00  -23.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787  -38.0000  -90.0000 87

#__ type_ start__ end____ width___ exp.time_
 16 omega -106.00  -15.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787  -38.0000    0.0000 91

#__ type_ start__ end____ width___ exp.time_
 17 omega   -6.00   21.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787   38.0000  -60.0000 27
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.1042633000
_diffrn_orient_matrix_UB_12      -0.0332456000
_diffrn_orient_matrix_UB_13      -0.0568921000
_diffrn_orient_matrix_UB_21      0.0139276000
_diffrn_orient_matrix_UB_22      -0.0840638000
_diffrn_orient_matrix_UB_23      0.0375547000
_diffrn_orient_matrix_UB_31      -0.1592873000
_diffrn_orient_matrix_UB_32      -0.0290660000
_diffrn_orient_matrix_UB_33      -0.0435914000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2213
_reflns_number_total             2482
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     72.42
_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 1.171.37.35 (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    'ShelXS (Sheldrick, 2015)'
_refine_diff_density_max         0.886
_refine_diff_density_min         -0.616
_refine_diff_density_rms         0.098
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2482
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0399
_refine_ls_R_factor_gt           0.0346
_refine_ls_restrained_S_all      1.050
_refine_ls_shift/su_max          0.00
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0589P)²+0.5702P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0907
_refine_ls_wR_factor_ref         0.0955
_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), 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     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.1926(3) 0.66525(12) 0.81201(11) 0.0159(4) Uani 1 1 d . . . . .
C2 C 0.1964(3) 0.58142(15) 0.80322(12) 0.0153(5) Uani 1 1 d . . . . .
C3 C 0.2570(3) 0.56652(15) 0.73078(12) 0.0137(5) Uani 1 1 d . . . . .
C4 C 0.2846(3) 0.64935(14) 0.70206(13) 0.0139(4) Uani 1 1 d . . . . .
C5 C 0.2465(3) 0.70614(15) 0.75400(13) 0.0145(5) Uani 1 1 d . . . . .
C6 C 0.2662(3) 0.79018(15) 0.74541(14) 0.0164(5) Uani 1 1 d . . . . .
H6 H 0.2404 0.8270 0.7799 0.020 Uiso 1 1 calc R . . . .
C7 C 0.3256(3) 0.81826(15) 0.68392(14) 0.0163(5) Uani 1 1 d . . . . .
H7 H 0.3404 0.8744 0.6769 0.020 Uiso 1 1 calc R . . . .
C8 C 0.3628(3) 0.76190(15) 0.63293(13) 0.0151(5) Uani 1 1 d . . . . .
C9 C 0.3432(3) 0.67705(15) 0.64047(13) 0.0144(5) Uani 1 1 d . . . . .
H9 H 0.3684 0.6405 0.6056 0.017 Uiso 1 1 calc R . . . .
C10 C 0.1327(3) 0.70607(16) 0.87198(14) 0.0178(5) Uani 1 1 d . . . . .
H10A H 0.0339 0.7364 0.8570 0.027 Uiso 1 1 calc GR . . . .
H10B H 0.2160 0.7432 0.8925 0.027 Uiso 1 1 calc GR . . . .
H10C H 0.1085 0.6656 0.9061 0.027 Uiso 1 1 calc GR . . . .
O11 O 0.1550(2) 0.52986(11) 0.84384(9) 0.0190(4) Uani 1 1 d . . . . .
N12 N 0.2763(3) 0.49271(12) 0.71108(11) 0.0146(4) Uani 1 1 d . . . . .
C13 C 0.3139(3) 0.47501(14) 0.64187(12) 0.0141(5) Uani 1 1 d . . . . .
C14 C 0.2037(3) 0.49666(14) 0.58376(13) 0.0163(5) Uani 1 1 d . . . . .
H14 H 0.1101 0.5279 0.5898 0.020 Uiso 1 1 calc R . . . .
C15 C 0.2350(3) 0.47117(16) 0.51704(13) 0.0182(5) Uani 1 1 d . . . . .
H15 H 0.1627 0.4860 0.4783 0.022 Uiso 1 1 calc R . . . .
C16 C 0.3735(3) 0.42368(15) 0.50779(13) 0.0179(5) Uani 1 1 d . . . . .
H16 H 0.3927 0.4061 0.4631 0.022 Uiso 1 1 calc R . . . .
C17 C 0.4832(3) 0.40244(15) 0.56532(14) 0.0195(5) Uani 1 1 d . . . . .
H17 H 0.5770 0.3714 0.5589 0.023 Uiso 1 1 calc R . . . .
C18 C 0.4534(3) 0.42739(14) 0.63250(13) 0.0171(5) Uani 1 1 d . . . . .
H18 H 0.5262 0.4124 0.6710 0.021 Uiso 1 1 calc R . . . .
Br19 Br 0.44569(3) 0.80251(2) 0.54980(2) 0.02081(13) 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
N1 C2 1.371(3) . ?
N1 C5 1.400(3) . ?
N1 C10 1.450(3) . ?
C2 C3 1.535(3) . ?
C2 O11 1.212(3) . ?
C3 C4 1.477(3) . ?
C3 N12 1.270(3) . ?
C4 C5 1.412(3) . ?
C4 C9 1.388(3) . ?
C5 C6 1.384(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.391(4) . ?
C7 H7 0.9300 . ?
C7 C8 1.392(4) . ?
C8 C9 1.395(3) . ?
C8 Br19 1.905(2) . ?
C9 H9 0.9300 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
N12 C13 1.417(3) . ?
C13 C14 1.400(4) . ?
C13 C18 1.397(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.389(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.388(4) . ?
C16 H16 0.9300 . ?
C16 C17 1.389(4) . ?
C17 H17 0.9300 . ?
C17 C18 1.391(4) . ?
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
C2 N1 C5 111.1(2) . . ?
C2 N1 C10 124.3(2) . . ?
C5 N1 C10 124.5(2) . . ?
N1 C2 C3 106.3(2) . . ?
O11 C2 N1 126.5(2) . . ?
O11 C2 C3 127.2(2) . . ?
C4 C3 C2 105.45(19) . . ?
N12 C3 C2 118.5(2) . . ?
N12 C3 C4 136.0(2) . . ?
C5 C4 C3 106.3(2) . . ?
C9 C4 C3 133.4(2) . . ?
C9 C4 C5 120.2(2) . . ?
N1 C5 C4 110.9(2) . . ?
C6 C5 N1 127.6(2) . . ?
C6 C5 C4 121.6(2) . . ?
C5 C6 H6 120.8 . . ?
C5 C6 C7 118.5(2) . . ?
C7 C6 H6 120.8 . . ?
C6 C7 H7 120.2 . . ?
C6 C7 C8 119.7(2) . . ?
C8 C7 H7 120.2 . . ?
C7 C8 C9 122.8(2) . . ?
C7 C8 Br19 118.49(18) . . ?
C9 C8 Br19 118.75(19) . . ?
C4 C9 C8 117.3(2) . . ?
C4 C9 H9 121.3 . . ?
C8 C9 H9 121.3 . . ?
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 120.8(2) . . ?
C14 C13 N12 120.7(2) . . ?
C18 C13 N12 119.0(2) . . ?
C18 C13 C14 119.9(2) . . ?
C13 C14 H14 120.2 . . ?
C15 C14 C13 119.6(2) . . ?
C15 C14 H14 120.2 . . ?
C14 C15 H15 119.8 . . ?
C16 C15 C14 120.4(2) . . ?
C16 C15 H15 119.8 . . ?
C15 C16 H16 120.0 . . ?
C15 C16 C17 120.0(2) . . ?
C17 C16 H16 120.0 . . ?
C16 C17 H17 119.9 . . ?
C16 C17 C18 120.2(2) . . ?
C18 C17 H17 119.9 . . ?
C13 C18 H18 120.1 . . ?
C17 C18 C13 119.8(2) . . ?
C17 C18 H18 120.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C2 C3 C4 -0.1(3) . . . . ?
N1 C2 C3 N12 177.8(2) . . . . ?
N1 C5 C6 C7 178.4(2) . . . . ?
C2 N1 C5 C4 1.8(3) . . . . ?
C2 N1 C5 C6 -177.0(3) . . . . ?
C2 C3 C4 C5 1.1(3) . . . . ?
C2 C3 C4 C9 177.7(3) . . . . ?
C2 C3 N12 C13 172.9(2) . . . . ?
C3 C4 C5 N1 -1.8(3) . . . . ?
C3 C4 C5 C6 177.1(2) . . . . ?
C3 C4 C9 C8 -175.9(3) . . . . ?
C3 N12 C13 C14 -61.6(3) . . . . ?
C3 N12 C13 C18 125.5(3) . . . . ?
C4 C3 N12 C13 -10.1(5) . . . . ?
C4 C5 C6 C7 -0.2(4) . . . . ?
C5 N1 C2 C3 -1.0(3) . . . . ?
C5 N1 C2 O11 -178.9(3) . . . . ?
C5 C4 C9 C8 0.3(4) . . . . ?
C5 C6 C7 C8 0.3(4) . . . . ?
C6 C7 C8 C9 0.0(4) . . . . ?
C6 C7 C8 Br19 -179.4(2) . . . . ?
C7 C8 C9 C4 -0.3(4) . . . . ?
C9 C4 C5 N1 -178.9(2) . . . . ?
C9 C4 C5 C6 -0.1(4) . . . . ?
C10 N1 C2 C3 176.1(2) . . . . ?
C10 N1 C2 O11 -1.8(4) . . . . ?
C10 N1 C5 C4 -175.3(2) . . . . ?
C10 N1 C5 C6 5.9(4) . . . . ?
O11 C2 C3 C4 177.8(3) . . . . ?
O11 C2 C3 N12 -4.3(4) . . . . ?
N12 C3 C4 C5 -176.2(3) . . . . ?
N12 C3 C4 C9 0.4(5) . . . . ?
N12 C13 C14 C15 -173.3(2) . . . . ?
N12 C13 C18 C17 173.6(2) . . . . ?
C13 C14 C15 C16 0.8(4) . . . . ?
C14 C13 C18 C17 0.7(4) . . . . ?
C14 C15 C16 C17 -1.0(4) . . . . ?
C15 C16 C17 C18 1.1(4) . . . . ?
C16 C17 C18 C13 -1.0(4) . . . . ?
C18 C13 C14 C15 -0.6(4) . . . . ?
Br19 C8 C9 C4 179.18(18) . . . . ?

####################################################################### 
# 
# 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_isbd_13
_database_code_depnum_ccdc_archive 'CCDC 1538860'
_audit_update_record             
;
2017-03-19 deposited with the CCDC.
2018-10-29 downloaded from the CCDC.
;
_audit_creation_date             2016-10-15
_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         'C21 H24 N2 O'
_chemical_formula_sum            'C21 H24 N2 O'
_chemical_formula_weight         320.42
_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      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                   8.47970(10)
_cell_length_b                   15.0831(2)
_cell_length_c                   28.0078(4)
_cell_angle_alpha                90
_cell_angle_beta                 93.3600(10)
_cell_angle_gamma                90
_cell_volume                     3576.04(8)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    15958
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      75.9810
_cell_measurement_theta_min      3.2650
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.571
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81707
_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.
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.190
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1376
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.04
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0487
_diffrn_reflns_av_unetI/netI     0.0256
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            41223
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.463
_diffrn_reflns_theta_min         3.329
_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 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega -116.00  -18.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787  -38.0000 -120.0000 98

#__ type_ start__ end____ width___ exp.time_
  2 omega -106.00  -80.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787 -141.0000 -163.0000 26

#__ type_ start__ end____ width___ exp.time_
  3 omega -128.00  -89.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787 -178.0000  150.0000 39

#__ type_ start__ end____ width___ exp.time_
  4 omega  -43.00  -13.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787   38.0000 -150.0000 30

#__ type_ start__ end____ width___ exp.time_
  5 omega  -49.00   36.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787   38.0000  150.0000 85

#__ type_ start__ end____ width___ exp.time_
  6 omega   68.00  127.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -       40.3787  178.0000 -180.0000 59

#__ type_ start__ end____ width___ exp.time_
  7 omega   36.00   75.00   1.0000   37.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000    0.0000 39

#__ type_ start__ end____ width___ exp.time_
  8 omega   75.00  101.00   1.0000   37.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000 -180.0000 26

#__ type_ start__ end____ width___ exp.time_
  9 omega   90.00  163.00   1.0000   37.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000  120.0000 73

#__ type_ start__ end____ width___ exp.time_
 10 omega   89.00  115.00   1.0000   37.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000   60.0000 26

#__ type_ start__ end____ width___ exp.time_
 11 omega  100.00  126.00   1.0000   37.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000   30.0000 26

#__ type_ start__ end____ width___ exp.time_
 12 omega  153.00  178.00   1.0000   37.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000   30.0000 25

#__ type_ start__ end____ width___ exp.time_
 13 omega   77.00  140.00   1.0000   37.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -61.0000   30.0000 63

#__ type_ start__ end____ width___ exp.time_
 14 omega   61.00  101.00   1.0000   37.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  178.0000  -60.0000 40

#__ type_ start__ end____ width___ exp.time_
 15 omega   57.00   99.00   1.0000   37.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  178.0000    0.0000 42

#__ type_ start__ end____ width___ exp.time_
 16 omega  107.00  133.00   1.0000   37.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  178.0000 -150.0000 26

#__ type_ start__ end____ width___ exp.time_
 17 omega   62.00   88.00   1.0000   37.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000   30.0000 26

#__ type_ start__ end____ width___ exp.time_
 18 omega   30.00   84.00   1.0000   37.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000 -120.0000 54

#__ type_ start__ end____ width___ exp.time_
 19 omega  150.00  178.00   1.0000   37.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   30.0000 -180.0000 28

#__ type_ start__ end____ width___ exp.time_
 20 omega   84.00  113.00   1.0000   37.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000  150.0000 29

#__ type_ start__ end____ width___ exp.time_
 21 omega  124.00  168.00   1.0000   37.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  112.0000  -30.0000 44

#__ type_ start__ end____ width___ exp.time_
 22 omega   39.00   65.00   1.0000   37.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000 -180.0000 26

#__ type_ start__ end____ width___ exp.time_
 23 omega  108.00  142.00   1.0000   37.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  112.0000   60.0000 34

#__ type_ start__ end____ width___ exp.time_
 24 omega   86.00  112.00   1.0000   37.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000    0.0000 26

#__ type_ start__ end____ width___ exp.time_
 25 omega   58.00   84.00   1.0000   37.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  178.0000 -150.0000 26

#__ type_ start__ end____ width___ exp.time_
 26 omega   38.00   63.00   1.0000   37.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000    0.0000 25

#__ type_ start__ end____ width___ exp.time_
 27 omega   70.00   96.00   1.0000   37.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000    0.0000 26

#__ type_ start__ end____ width___ exp.time_
 28 omega   44.00  109.00   1.0000   37.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000   30.0000 65

#__ type_ start__ end____ width___ exp.time_
 29 omega   73.00  114.00   1.0000   37.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000  -30.0000 41

#__ type_ start__ end____ width___ exp.time_
 30 omega  100.00  126.00   1.0000   37.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -61.0000  -30.0000 26

#__ type_ start__ end____ width___ exp.time_
 31 omega   84.00  126.00   1.0000   37.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000   60.0000 42

#__ type_ start__ end____ width___ exp.time_
 32 omega  145.00  170.00   1.0000   37.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000   60.0000 25

#__ type_ start__ end____ width___ exp.time_
 33 omega   58.00   83.00   1.0000   37.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000   60.0000 25

#__ type_ start__ end____ width___ exp.time_
 34 omega   49.00   91.00   1.0000   37.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000   30.0000 42

#__ type_ start__ end____ width___ exp.time_
 35 omega   47.00   72.00   1.0000   37.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -61.0000  -30.0000 25

#__ type_ start__ end____ width___ exp.time_
 36 omega  -69.00  -39.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787  178.0000 -180.0000 30

#__ type_ start__ end____ width___ exp.time_
 37 omega  -50.00   23.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787   38.0000 -120.0000 73

#__ type_ start__ end____ width___ exp.time_
 38 omega -129.00  -82.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787  178.0000 -180.0000 47

#__ type_ start__ end____ width___ exp.time_
 39 omega  -12.00   23.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787   38.0000  -90.0000 35

#__ type_ start__ end____ width___ exp.time_
 40 omega   53.00   84.00   1.0000   37.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000    0.0000 31

#__ type_ start__ end____ width___ exp.time_
 41 omega   80.00  105.00   1.0000   37.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000  150.0000 25

#__ type_ start__ end____ width___ exp.time_
 42 omega   61.00  105.00   1.0000   37.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -54.0000 -122.4374 44

#__ type_ start__ end____ width___ exp.time_
 43 omega  144.00  178.00   1.0000   37.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000 -150.0000 34

#__ type_ start__ end____ width___ exp.time_
 44 omega   93.00  134.00   1.0000   37.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000 -150.0000 41

#__ type_ start__ end____ width___ exp.time_
 45 omega   83.00  121.00   1.0000   37.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   30.0000 -150.0000 38

#__ type_ start__ end____ width___ exp.time_
 46 omega   58.00  147.00   1.0000   37.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  178.0000   30.0000 89

#__ type_ start__ end____ width___ exp.time_
 47 omega   71.00  110.00   1.0000   37.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000  -90.0000 39

#__ type_ start__ end____ width___ exp.time_
 48 omega  109.00  138.00   1.0000   37.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  112.0000   30.0000 29

#__ type_ start__ end____ width___ exp.time_
 49 omega   34.00   60.00   1.0000   37.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000   60.0000 26

#__ type_ start__ end____ width___ exp.time_
 50 omega   81.00  107.00   1.0000   37.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000 -150.0000 26

#__ type_ start__ end____ width___ exp.time_
 51 omega   35.00   81.00   1.0000   37.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000  -90.0000 46

#__ type_ start__ end____ width___ exp.time_
 52 omega  108.00  137.00   1.0000   37.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -61.0000  -60.0000 29

#__ type_ start__ end____ width___ exp.time_
 53 omega   73.00   98.00   1.0000   37.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000  120.0000 25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0603773000
_diffrn_orient_matrix_UB_12      0.0717242000
_diffrn_orient_matrix_UB_13      0.0335668000
_diffrn_orient_matrix_UB_21      0.0500025000
_diffrn_orient_matrix_UB_22      0.0725463000
_diffrn_orient_matrix_UB_23      -0.0347434000
_diffrn_orient_matrix_UB_31      -0.1643147000
_diffrn_orient_matrix_UB_32      -0.0042484000
_diffrn_orient_matrix_UB_33      -0.0264921000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6137
_reflns_number_total             7097
_reflns_odcompleteness_completeness 95.60
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     80.07
_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 1.171.37.35 (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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.306
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     443
_refine_ls_number_reflns         7097
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0445
_refine_ls_R_factor_gt           0.0378
_refine_ls_restrained_S_all      1.027
_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)+(0.0519P)²+1.0230P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0972
_refine_ls_wR_factor_ref         0.1024
_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:
 C19(H19), C22(H22), C19A(H19A), C22A(H22A)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C9(H9), C15(H15), C16(H16), C17(H17), C6A(H6A),
 C7A(H7A), C8A(H8A), C9A(H9A), C15A(H15A), C16A(H16A), C17A(H17A)
2.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C20(H20A,H20B,H20C), C21(H21A,H21B,H21C), C23(H23A,H23B,
 H23C), C24(H24A,H24B,H24C), C10A(H10D,H10E,H10F), C20A(H20D,H20E,H20F),
 C21A(H21D,H21E,H21F), C23A(H23D,H23E,H23F), C24A(H24D,H24E,H24F)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.33681(11) 0.67396(6) 0.32763(3) 0.01669(19) Uani 1 1 d . . . . .
C2 C 0.19113(13) 0.71231(7) 0.32890(4) 0.0153(2) Uani 1 1 d . . . . .
C3 C 0.21803(13) 0.81224(7) 0.32441(4) 0.0141(2) Uani 1 1 d . . . . .
C4 C 0.38923(13) 0.82380(8) 0.32168(4) 0.0156(2) Uani 1 1 d . . . . .
C5 C 0.45527(13) 0.73828(8) 0.32333(4) 0.0162(2) Uani 1 1 d . . . . .
C6 C 0.61575(14) 0.72451(8) 0.32120(4) 0.0205(2) Uani 1 1 d . . . . .
H6 H 0.6583 0.6677 0.3221 0.025 Uiso 1 1 calc R . . . .
C7 C 0.71137(14) 0.79910(9) 0.31758(4) 0.0239(3) Uani 1 1 d . . . . .
H7 H 0.8199 0.7918 0.3161 0.029 Uiso 1 1 calc R . . . .
C8 C 0.64834(14) 0.88421(9) 0.31608(5) 0.0239(3) Uani 1 1 d . . . . .
H8 H 0.7151 0.9328 0.3138 0.029 Uiso 1 1 calc R . . . .
C9 C 0.48560(14) 0.89761(8) 0.31804(4) 0.0197(2) Uani 1 1 d . . . . .
H9 H 0.4431 0.9545 0.3169 0.024 Uiso 1 1 calc R . . . .
C10 C 0.36478(15) 0.57905(8) 0.33085(4) 0.0237(3) Uani 1 1 d . . . . .
H10A H 0.3982 0.5576 0.3008 0.036 Uiso 1 1 calc GR . . . .
H10B H 0.2691 0.5495 0.3384 0.036 Uiso 1 1 calc GR . . . .
H10C H 0.4456 0.5673 0.3555 0.036 Uiso 1 1 calc GR . . . .
O11 O 0.06596(10) 0.67446(6) 0.33307(3) 0.02060(18) Uani 1 1 d . . . . .
N12 N 0.09950(11) 0.86376(6) 0.32329(3) 0.01510(19) Uani 1 1 d . . . . .
C13 C 0.11633(12) 0.95730(7) 0.31931(4) 0.0157(2) Uani 1 1 d . . . . .
C14 C 0.11955(13) 0.99591(8) 0.27359(4) 0.0176(2) Uani 1 1 d . . . . .
C15 C 0.11918(14) 1.08815(8) 0.27048(4) 0.0229(2) Uani 1 1 d . . . . .
H15 H 0.1194 1.1151 0.2406 0.027 Uiso 1 1 calc R . . . .
C16 C 0.11854(16) 1.14024(8) 0.31130(5) 0.0281(3) Uani 1 1 d . . . . .
H16 H 0.1182 1.2017 0.3087 0.034 Uiso 1 1 calc R . . . .
C17 C 0.11846(16) 1.10052(9) 0.35611(5) 0.0263(3) Uani 1 1 d . . . . .
H17 H 0.1197 1.1361 0.3832 0.032 Uiso 1 1 calc R . . . .
C18 C 0.11652(13) 1.00893(8) 0.36135(4) 0.0196(2) Uani 1 1 d . . . . .
C19 C 0.12244(14) 0.93782(8) 0.22916(4) 0.0199(2) Uani 1 1 d . . . . .
H19 H 0.1910 0.8871 0.2372 0.024 Uiso 1 1 calc R . . . .
C20 C 0.19122(18) 0.98574(9) 0.18701(5) 0.0300(3) Uani 1 1 d . . . . .
H20A H 0.1228 1.0337 0.1769 0.045 Uiso 1 1 calc GR . . . .
H20B H 0.2003 0.9449 0.1610 0.045 Uiso 1 1 calc GR . . . .
H20C H 0.2938 1.0087 0.1967 0.045 Uiso 1 1 calc GR . . . .
C21 C -0.04175(18) 0.90142(10) 0.21493(5) 0.0327(3) Uani 1 1 d . . . . .
H21A H -0.0780 0.8658 0.2405 0.049 Uiso 1 1 calc GR . . . .
H21B H -0.0368 0.8658 0.1866 0.049 Uiso 1 1 calc GR . . . .
H21C H -0.1136 0.9498 0.2087 0.049 Uiso 1 1 calc GR . . . .
C22 C 0.11883(14) 0.96447(9) 0.41036(4) 0.0223(2) Uani 1 1 d . . . . .
H22 H 0.2049 0.9210 0.4117 0.027 Uiso 1 1 calc R . . . .
C23 C 0.15141(17) 1.02964(10) 0.45173(5) 0.0313(3) Uani 1 1 d . . . . .
H23A H 0.2470 1.0617 0.4469 0.047 Uiso 1 1 calc GR . . . .
H23B H 0.1626 0.9975 0.4813 0.047 Uiso 1 1 calc GR . . . .
H23C H 0.0650 1.0706 0.4529 0.047 Uiso 1 1 calc GR . . . .
C24 C -0.03459(16) 0.91397(10) 0.41800(5) 0.0292(3) Uani 1 1 d . . . . .
H24A H -0.1215 0.9549 0.4171 0.044 Uiso 1 1 calc GR . . . .
H24B H -0.0263 0.8848 0.4485 0.044 Uiso 1 1 calc GR . . . .
H24C H -0.0521 0.8706 0.3931 0.044 Uiso 1 1 calc GR . . . .
N1A N 0.84162(11) 0.52790(6) 0.43607(3) 0.01625(19) Uani 1 1 d . . . . .
C2A C 0.69284(13) 0.49256(7) 0.43391(4) 0.0149(2) Uani 1 1 d . . . . .
C3A C 0.71453(13) 0.39155(7) 0.43239(4) 0.0142(2) Uani 1 1 d . . . . .
C4A C 0.88631(13) 0.37681(7) 0.43385(4) 0.0154(2) Uani 1 1 d . . . . .
C5A C 0.95689(13) 0.46120(7) 0.43612(4) 0.0158(2) Uani 1 1 d . . . . .
C6A C 1.11902(14) 0.47218(8) 0.43746(4) 0.0202(2) Uani 1 1 d . . . . .
H6A H 1.1644 0.5283 0.4389 0.024 Uiso 1 1 calc R . . . .
C7A C 1.21192(14) 0.39595(9) 0.43659(4) 0.0233(3) Uani 1 1 d . . . . .
H7A H 1.3213 0.4014 0.4374 0.028 Uiso 1 1 calc R . . . .
C8A C 1.14413(14) 0.31173(8) 0.43453(4) 0.0231(3) Uani 1 1 d . . . . .
H8A H 1.2087 0.2619 0.4342 0.028 Uiso 1 1 calc R . . . .
C9A C 0.98006(14) 0.30129(8) 0.43297(4) 0.0192(2) Uani 1 1 d . . . . .
H9A H 0.9347 0.2451 0.4314 0.023 Uiso 1 1 calc R . . . .
C10A C 0.87610(15) 0.62220(8) 0.43700(4) 0.0216(2) Uani 1 1 d . . . . .
H10D H 0.9385 0.6364 0.4657 0.032 Uiso 1 1 calc GR . . . .
H10E H 0.7790 0.6550 0.4363 0.032 Uiso 1 1 calc GR . . . .
H10F H 0.9336 0.6376 0.4097 0.032 Uiso 1 1 calc GR . . . .
O11A O 0.56909(10) 0.53331(6) 0.43292(3) 0.02119(18) Uani 1 1 d . . . . .
N12A N 0.59267(11) 0.34241(6) 0.43059(3) 0.01470(19) Uani 1 1 d . . . . .
C13A C 0.60230(12) 0.24831(7) 0.42944(4) 0.0149(2) Uani 1 1 d . . . . .
C14A C 0.57498(12) 0.20260(8) 0.47202(4) 0.0164(2) Uani 1 1 d . . . . .
C15A C 0.57602(14) 0.11029(8) 0.47099(4) 0.0211(2) Uani 1 1 d . . . . .
H15A H 0.5613 0.0788 0.4989 0.025 Uiso 1 1 calc R . . . .
C16A C 0.59865(15) 0.06463(8) 0.42899(5) 0.0251(3) Uani 1 1 d . . . . .
H16A H 0.5997 0.0030 0.4289 0.030 Uiso 1 1 calc R . . . .
C17A C 0.61969(14) 0.11103(8) 0.38702(4) 0.0228(2) Uani 1 1 d . . . . .
H17A H 0.6331 0.0797 0.3589 0.027 Uiso 1 1 calc R . . . .
C18A C 0.62122(13) 0.20327(8) 0.38598(4) 0.0176(2) Uani 1 1 d . . . . .
C19A C 0.54596(14) 0.25407(8) 0.51742(4) 0.0183(2) Uani 1 1 d . . . . .
H19A H 0.4886 0.3083 0.5079 0.022 Uiso 1 1 calc R . . . .
C20A C 0.44427(15) 0.20300(9) 0.55143(4) 0.0240(3) Uani 1 1 d . . . . .
H20D H 0.3490 0.1835 0.5344 0.036 Uiso 1 1 calc GR . . . .
H20E H 0.4182 0.2410 0.5773 0.036 Uiso 1 1 calc GR . . . .
H20F H 0.5019 0.1525 0.5639 0.036 Uiso 1 1 calc GR . . . .
C21A C 0.70191(15) 0.28210(8) 0.54354(4) 0.0238(3) Uani 1 1 d . . . . .
H21D H 0.7590 0.2303 0.5545 0.036 Uiso 1 1 calc GR . . . .
H21E H 0.6802 0.3187 0.5704 0.036 Uiso 1 1 calc GR . . . .
H21F H 0.7642 0.3148 0.5220 0.036 Uiso 1 1 calc GR . . . .
C22A C 0.63952(14) 0.25457(8) 0.33973(4) 0.0214(2) Uani 1 1 d . . . . .
H22A H 0.7211 0.2997 0.3463 0.026 Uiso 1 1 calc R . . . .
C23A C 0.69292(18) 0.19672(10) 0.29886(5) 0.0314(3) Uani 1 1 d . . . . .
H23D H 0.7869 0.1650 0.3093 0.047 Uiso 1 1 calc GR . . . .
H23E H 0.7145 0.2336 0.2721 0.047 Uiso 1 1 calc GR . . . .
H23F H 0.6109 0.1552 0.2896 0.047 Uiso 1 1 calc GR . . . .
C24A C 0.48622(17) 0.30302(10) 0.32381(5) 0.0309(3) Uani 1 1 d . . . . .
H24D H 0.4045 0.2604 0.3162 0.046 Uiso 1 1 calc GR . . . .
H24E H 0.5033 0.3383 0.2960 0.046 Uiso 1 1 calc GR . . . .
H24F H 0.4549 0.3407 0.3492 0.046 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 1.3664(15) . ?
N1 C5 1.4067(15) . ?
N1 C10 1.4530(15) . ?
C2 C3 1.5307(15) . ?
C2 O11 1.2168(14) . ?
C3 C4 1.4686(15) . ?
C3 N12 1.2694(15) . ?
C4 C5 1.4059(16) . ?
C4 C9 1.3883(16) . ?
C5 C6 1.3813(16) . ?
C6 H6 0.9300 . ?
C6 C7 1.3940(18) . ?
C7 H7 0.9300 . ?
C7 C8 1.3902(18) . ?
C8 H8 0.9300 . ?
C8 C9 1.3990(16) . ?
C9 H9 0.9300 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
N12 C13 1.4230(14) . ?
C13 C14 1.4084(16) . ?
C13 C18 1.4117(16) . ?
C14 C15 1.3939(17) . ?
C14 C19 1.5233(15) . ?
C15 H15 0.9300 . ?
C15 C16 1.3875(18) . ?
C16 H16 0.9300 . ?
C16 C17 1.3906(19) . ?
C17 H17 0.9300 . ?
C17 C18 1.3894(18) . ?
C18 C22 1.5267(16) . ?
C19 H19 0.9800 . ?
C19 C20 1.5288(16) . ?
C19 C21 1.5276(18) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 H22 0.9800 . ?
C22 C23 1.5324(17) . ?
C22 C24 1.5333(18) . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
N1A C2A 1.3676(14) . ?
N1A C5A 1.4027(14) . ?
N1A C10A 1.4520(14) . ?
C2A C3A 1.5354(15) . ?
C2A O11A 1.2151(14) . ?
C3A C4A 1.4718(15) . ?
C3A N12A 1.2703(15) . ?
C4A C5A 1.4064(16) . ?
C4A C9A 1.3901(16) . ?
C5A C6A 1.3831(16) . ?
C6A H6A 0.9300 . ?
C6A C7A 1.3948(18) . ?
C7A H7A 0.9300 . ?
C7A C8A 1.3942(18) . ?
C8A H8A 0.9300 . ?
C8A C9A 1.3983(16) . ?
C9A H9A 0.9300 . ?
C10A H10D 0.9600 . ?
C10A H10E 0.9600 . ?
C10A H10F 0.9600 . ?
N12A C13A 1.4221(14) . ?
C13A C14A 1.4084(15) . ?
C13A C18A 1.4111(15) . ?
C14A C15A 1.3926(16) . ?
C14A C19A 1.5221(15) . ?
C15A H15A 0.9300 . ?
C15A C16A 1.3863(18) . ?
C16A H16A 0.9300 . ?
C16A C17A 1.3884(18) . ?
C17A H17A 0.9300 . ?
C17A C18A 1.3917(17) . ?
C18A C22A 1.5247(16) . ?
C19A H19A 0.9800 . ?
C19A C20A 1.5298(16) . ?
C19A C21A 1.5327(16) . ?
C20A H20D 0.9600 . ?
C20A H20E 0.9600 . ?
C20A H20F 0.9600 . ?
C21A H21D 0.9600 . ?
C21A H21E 0.9600 . ?
C21A H21F 0.9600 . ?
C22A H22A 0.9800 . ?
C22A C23A 1.5288(17) . ?
C22A C24A 1.5345(18) . ?
C23A H23D 0.9600 . ?
C23A H23E 0.9600 . ?
C23A H23F 0.9600 . ?
C24A H24D 0.9600 . ?
C24A H24E 0.9600 . ?
C24A H24F 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 111.19(9) . . ?
C2 N1 C10 124.05(10) . . ?
C5 N1 C10 124.75(10) . . ?
N1 C2 C3 105.99(9) . . ?
O11 C2 N1 126.79(11) . . ?
O11 C2 C3 127.22(10) . . ?
C4 C3 C2 105.88(9) . . ?
N12 C3 C2 118.90(10) . . ?
N12 C3 C4 135.21(10) . . ?
C5 C4 C3 106.41(10) . . ?
C9 C4 C3 133.39(11) . . ?
C9 C4 C5 120.20(10) . . ?
C4 C5 N1 110.52(10) . . ?
C6 C5 N1 127.60(11) . . ?
C6 C5 C4 121.88(11) . . ?
C5 C6 H6 121.3 . . ?
C5 C6 C7 117.42(11) . . ?
C7 C6 H6 121.3 . . ?
C6 C7 H7 119.2 . . ?
C8 C7 C6 121.55(11) . . ?
C8 C7 H7 119.2 . . ?
C7 C8 H8 119.6 . . ?
C7 C8 C9 120.70(11) . . ?
C9 C8 H8 119.6 . . ?
C4 C9 C8 118.25(11) . . ?
C4 C9 H9 120.9 . . ?
C8 C9 H9 120.9 . . ?
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 121.73(9) . . ?
C14 C13 N12 119.25(10) . . ?
C14 C13 C18 122.08(11) . . ?
C18 C13 N12 118.47(10) . . ?
C13 C14 C19 120.46(10) . . ?
C15 C14 C13 118.00(11) . . ?
C15 C14 C19 121.54(10) . . ?
C14 C15 H15 119.5 . . ?
C16 C15 C14 120.92(12) . . ?
C16 C15 H15 119.5 . . ?
C15 C16 H16 120.0 . . ?
C15 C16 C17 119.99(12) . . ?
C17 C16 H16 120.0 . . ?
C16 C17 H17 119.2 . . ?
C18 C17 C16 121.63(11) . . ?
C18 C17 H17 119.2 . . ?
C13 C18 C22 120.46(11) . . ?
C17 C18 C13 117.37(11) . . ?
C17 C18 C22 122.15(11) . . ?
C14 C19 H19 107.4 . . ?
C14 C19 C20 112.59(10) . . ?
C14 C19 C21 111.21(10) . . ?
C20 C19 H19 107.4 . . ?
C21 C19 H19 107.4 . . ?
C21 C19 C20 110.58(11) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C18 C22 H22 107.4 . . ?
C18 C22 C23 112.97(11) . . ?
C18 C22 C24 112.17(10) . . ?
C23 C22 H22 107.4 . . ?
C23 C22 C24 109.26(10) . . ?
C24 C22 H22 107.4 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C22 C24 H24A 109.5 . . ?
C22 C24 H24B 109.5 . . ?
C22 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C2A N1A C5A 111.19(9) . . ?
C2A N1A C10A 124.53(10) . . ?
C5A N1A C10A 124.26(10) . . ?
N1A C2A C3A 106.04(9) . . ?
O11A C2A N1A 126.66(10) . . ?
O11A C2A C3A 127.30(10) . . ?
C4A C3A C2A 105.61(9) . . ?
N12A C3A C2A 118.79(10) . . ?
N12A C3A C4A 135.59(10) . . ?
C5A C4A C3A 106.40(9) . . ?
C9A C4A C3A 133.59(11) . . ?
C9A C4A C5A 120.01(10) . . ?
N1A C5A C4A 110.76(10) . . ?
C6A C5A N1A 127.28(11) . . ?
C6A C5A C4A 121.96(11) . . ?
C5A C6A H6A 121.2 . . ?
C5A C6A C7A 117.53(11) . . ?
C7A C6A H6A 121.2 . . ?
C6A C7A H7A 119.3 . . ?
C8A C7A C6A 121.33(11) . . ?
C8A C7A H7A 119.3 . . ?
C7A C8A H8A 119.6 . . ?
C7A C8A C9A 120.73(11) . . ?
C9A C8A H8A 119.6 . . ?
C4A C9A C8A 118.43(11) . . ?
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 . . ?
C3A N12A C13A 122.39(9) . . ?
C14A C13A N12A 117.18(10) . . ?
C14A C13A C18A 121.83(10) . . ?
C18A C13A N12A 120.63(10) . . ?
C13A C14A C19A 120.03(10) . . ?
C15A C14A C13A 118.06(10) . . ?
C15A C14A C19A 121.91(10) . . ?
C14A C15A H15A 119.5 . . ?
C16A C15A C14A 121.03(11) . . ?
C16A C15A H15A 119.5 . . ?
C15A C16A H16A 120.0 . . ?
C15A C16A C17A 119.94(11) . . ?
C17A C16A H16A 120.0 . . ?
C16A C17A H17A 119.2 . . ?
C16A C17A C18A 121.57(11) . . ?
C18A C17A H17A 119.2 . . ?
C13A C18A C22A 120.73(10) . . ?
C17A C18A C13A 117.48(11) . . ?
C17A C18A C22A 121.78(10) . . ?
C14A C19A H19A 107.5 . . ?
C14A C19A C20A 112.83(10) . . ?
C14A C19A C21A 111.23(10) . . ?
C20A C19A H19A 107.5 . . ?
C20A C19A C21A 110.10(10) . . ?
C21A C19A H19A 107.5 . . ?
C19A C20A H20D 109.5 . . ?
C19A C20A H20E 109.5 . . ?
C19A C20A H20F 109.5 . . ?
H20D C20A H20E 109.5 . . ?
H20D C20A H20F 109.5 . . ?
H20E C20A H20F 109.5 . . ?
C19A C21A H21D 109.5 . . ?
C19A C21A H21E 109.5 . . ?
C19A C21A H21F 109.5 . . ?
H21D C21A H21E 109.5 . . ?
H21D C21A H21F 109.5 . . ?
H21E C21A H21F 109.5 . . ?
C18A C22A H22A 107.4 . . ?
C18A C22A C23A 113.32(10) . . ?
C18A C22A C24A 111.22(10) . . ?
C23A C22A H22A 107.4 . . ?
C23A C22A C24A 109.72(10) . . ?
C24A C22A H22A 107.4 . . ?
C22A C23A H23D 109.5 . . ?
C22A C23A H23E 109.5 . . ?
C22A C23A H23F 109.5 . . ?
H23D C23A H23E 109.5 . . ?
H23D C23A H23F 109.5 . . ?
H23E C23A H23F 109.5 . . ?
C22A C24A H24D 109.5 . . ?
C22A C24A H24E 109.5 . . ?
C22A C24A H24F 109.5 . . ?
H24D C24A H24E 109.5 . . ?
H24D C24A H24F 109.5 . . ?
H24E C24A H24F 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 -1.14(11) . . . . ?
N1 C2 C3 N12 178.08(9) . . . . ?
N1 C5 C6 C7 -179.12(10) . . . . ?
C2 N1 C5 C4 0.13(12) . . . . ?
C2 N1 C5 C6 179.65(10) . . . . ?
C2 C3 C4 C5 1.21(11) . . . . ?
C2 C3 C4 C9 -178.92(12) . . . . ?
C2 C3 N12 C13 179.81(9) . . . . ?
C3 C4 C5 N1 -0.87(12) . . . . ?
C3 C4 C5 C6 179.57(10) . . . . ?
C3 C4 C9 C8 -179.84(11) . . . . ?
C3 N12 C13 C14 86.99(13) . . . . ?
C3 N12 C13 C18 -98.01(12) . . . . ?
C4 C3 N12 C13 -1.25(18) . . . . ?
C4 C5 C6 C7 0.36(16) . . . . ?
C5 N1 C2 C3 0.65(11) . . . . ?
C5 N1 C2 O11 -178.94(10) . . . . ?
C5 C4 C9 C8 0.02(16) . . . . ?
C5 C6 C7 C8 -0.10(18) . . . . ?
C6 C7 C8 C9 -0.19(19) . . . . ?
C7 C8 C9 C4 0.23(18) . . . . ?
C9 C4 C5 N1 179.24(10) . . . . ?
C9 C4 C5 C6 -0.32(16) . . . . ?
C10 N1 C2 C3 -179.97(9) . . . . ?
C10 N1 C2 O11 0.44(17) . . . . ?
C10 N1 C5 C4 -179.26(10) . . . . ?
C10 N1 C5 C6 0.27(17) . . . . ?
O11 C2 C3 C4 178.44(10) . . . . ?
O11 C2 C3 N12 -2.33(16) . . . . ?
N12 C3 C4 C5 -177.83(12) . . . . ?
N12 C3 C4 C9 2.0(2) . . . . ?
N12 C13 C14 C15 173.30(10) . . . . ?
N12 C13 C14 C19 -6.38(16) . . . . ?
N12 C13 C18 C17 -174.23(10) . . . . ?
N12 C13 C18 C22 7.31(15) . . . . ?
C13 C14 C15 C16 1.14(18) . . . . ?
C13 C14 C19 C20 -156.80(11) . . . . ?
C13 C14 C19 C21 78.46(13) . . . . ?
C13 C18 C22 C23 168.69(11) . . . . ?
C13 C18 C22 C24 -67.27(14) . . . . ?
C14 C13 C18 C17 0.62(17) . . . . ?
C14 C13 C18 C22 -177.84(10) . . . . ?
C14 C15 C16 C17 0.1(2) . . . . ?
C15 C14 C19 C20 23.53(16) . . . . ?
C15 C14 C19 C21 -101.21(13) . . . . ?
C15 C16 C17 C18 -1.0(2) . . . . ?
C16 C17 C18 C13 0.66(19) . . . . ?
C16 C17 C18 C22 179.10(12) . . . . ?
C17 C18 C22 C23 -9.70(16) . . . . ?
C17 C18 C22 C24 114.34(13) . . . . ?
C18 C13 C14 C15 -1.51(16) . . . . ?
C18 C13 C14 C19 178.81(10) . . . . ?
C19 C14 C15 C16 -179.19(11) . . . . ?
N1A C2A C3A C4A -0.09(11) . . . . ?
N1A C2A C3A N12A 179.54(9) . . . . ?
N1A C5A C6A C7A -179.19(11) . . . . ?
C2A N1A C5A C4A 0.09(12) . . . . ?
C2A N1A C5A C6A 179.22(11) . . . . ?
C2A C3A C4A C5A 0.13(11) . . . . ?
C2A C3A C4A C9A -179.19(12) . . . . ?
C2A C3A N12A C13A -179.53(9) . . . . ?
C3A C4A C5A N1A -0.14(12) . . . . ?
C3A C4A C5A C6A -179.33(10) . . . . ?
C3A C4A C9A C8A 179.43(11) . . . . ?
C3A N12A C13A C14A 103.95(12) . . . . ?
C3A N12A C13A C18A -82.79(13) . . . . ?
C4A C3A N12A C13A -0.05(19) . . . . ?
C4A C5A C6A C7A -0.14(17) . . . . ?
C5A N1A C2A C3A 0.00(11) . . . . ?
C5A N1A C2A O11A -179.33(10) . . . . ?
C5A C4A C9A C8A 0.18(17) . . . . ?
C5A C6A C7A C8A -0.11(18) . . . . ?
C6A C7A C8A C9A 0.40(19) . . . . ?
C7A C8A C9A C4A -0.43(18) . . . . ?
C9A C4A C5A N1A 179.29(10) . . . . ?
C9A C4A C5A C6A 0.11(16) . . . . ?
C10A N1A C2A C3A 178.57(10) . . . . ?
C10A N1A C2A O11A -0.76(17) . . . . ?
C10A N1A C5A C4A -178.48(10) . . . . ?
C10A N1A C5A C6A 0.65(18) . . . . ?
O11A C2A C3A C4A 179.24(10) . . . . ?
O11A C2A C3A N12A -1.14(16) . . . . ?
N12A C3A C4A C5A -179.40(12) . . . . ?
N12A C3A C4A C9A 1.3(2) . . . . ?
N12A C13A C14A C15A 176.83(10) . . . . ?
N12A C13A C14A C19A -3.35(15) . . . . ?
N12A C13A C18A C17A -176.02(10) . . . . ?
N12A C13A C18A C22A 2.89(16) . . . . ?
C13A C14A C15A C16A -1.85(17) . . . . ?
C13A C14A C19A C20A 152.25(10) . . . . ?
C13A C14A C19A C21A -83.44(12) . . . . ?
C13A C18A C22A C23A 167.89(11) . . . . ?
C13A C18A C22A C24A -67.95(14) . . . . ?
C14A C13A C18A C17A -3.08(16) . . . . ?
C14A C13A C18A C22A 175.82(10) . . . . ?
C14A C15A C16A C17A -0.43(19) . . . . ?
C15A C14A C19A C20A -27.93(15) . . . . ?
C15A C14A C19A C21A 96.38(13) . . . . ?
C15A C16A C17A C18A 1.03(19) . . . . ?
C16A C17A C18A C13A 0.69(18) . . . . ?
C16A C17A C18A C22A -178.20(11) . . . . ?
C17A C18A C22A C23A -13.25(16) . . . . ?
C17A C18A C22A C24A 110.91(13) . . . . ?
C18A C13A C14A C15A 3.66(16) . . . . ?
C18A C13A C14A C19A -176.52(10) . . . . ?
C19A C14A C15A C16A 178.33(11) . . . . ?


####################################################################### 
# 
# 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_as_53
_database_code_depnum_ccdc_archive 'CCDC 1538863'
_audit_update_record             
;
2017-03-19 deposited with the CCDC.
2018-10-29 downloaded from the CCDC.
;
_audit_creation_date             2016-11-15
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.11.07 svn.r3352 for OlexSys, GUI svn.r5261)
;
_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_absolute_configuration ?
_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      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y+1/2, z+1/2'
'x+1/2, -y+1/2, z'

_cell_length_a                   9.6713(4)
_cell_length_b                   9.0619(4)
_cell_length_c                   15.8838(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1392.07(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5110
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.7640
_cell_measurement_theta_min      3.3260
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.97284
_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            'translucent colorless'
_exptl_crystal_density_diffrn    1.261
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.05
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0174
_diffrn_reflns_av_unetI/netI     0.0155
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            11892
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.491
_diffrn_reflns_theta_min         3.081
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 16.2096
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -91.00   -1.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.4241  -57.0000   60.0000 90

#__ type_ start__ end____ width___ exp.time_
  2 omega  -90.00  -13.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.4241  -77.0000  -60.0000 77

#__ type_ start__ end____ width___ exp.time_
  3 omega  -49.00   42.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.4241   77.0000   60.0000 91

#__ type_ start__ end____ width___ exp.time_
  4 omega  -66.00  -39.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.4241 -178.0000  120.0000 27

#__ type_ start__ end____ width___ exp.time_
  5 omega  -24.00   31.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.4241   57.0000  150.0000 55

#__ type_ start__ end____ width___ exp.time_
  6 omega   -7.00   22.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.4241   57.0000  -90.0000 29

#__ type_ start__ end____ width___ exp.time_
  7 omega  -37.00   52.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -       23.5178  -77.0000  -30.0000 89
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0462180000
_diffrn_orient_matrix_UB_12      -0.0516507000
_diffrn_orient_matrix_UB_13      -0.0183367000
_diffrn_orient_matrix_UB_21      0.0016835000
_diffrn_orient_matrix_UB_22      0.0426075000
_diffrn_orient_matrix_UB_23      -0.0374183000
_diffrn_orient_matrix_UB_31      0.0568370000
_diffrn_orient_matrix_UB_32      0.0406426000
_diffrn_orient_matrix_UB_33      0.0160792000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.931
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                3104
_reflns_number_total             3197
_reflns_odcompleteness_completeness 99.71
_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, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.189
_refine_diff_density_min         -0.172
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details 
;
 Refined as a perfect inversion twin.
;
_refine_ls_abs_structure_Flack   ?
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         3197
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0311
_refine_ls_R_factor_gt           0.0299
_refine_ls_restrained_S_all      1.071
_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)+(0.0361P)²+0.2567P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0741
_refine_ls_wR_factor_ref         0.0751
_refine_special_details          
;
 Refined as a 2-component perfect inversion twin.
;
_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:
 C10(H10)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C9(H9), C16(H16), C17(H17), C18(H18), C19(H19),
 C20(H20)
2.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C)
;
_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 0.13474(15) -0.50749(17) -0.69532(9) 0.0213(3) Uani 1 1 d . . . . .
C2 C 0.11472(19) -0.4908(2) -0.78047(11) 0.0219(4) Uani 1 1 d . . . . .
C3 C -0.03872(18) -0.52231(19) -0.79718(11) 0.0195(3) Uani 1 1 d . . . . .
C4 C -0.09887(18) -0.55898(18) -0.71508(10) 0.0195(3) Uani 1 1 d . . . . .
C5 C 0.00790(18) -0.54340(18) -0.65563(11) 0.0208(3) Uani 1 1 d . . . . .
C6 C -0.01662(19) -0.5603(2) -0.57037(11) 0.0252(4) Uani 1 1 d . . . . .
H6 H 0.0538 -0.5482 -0.5311 0.030 Uiso 1 1 calc R . . . .
C7 C -0.1507(2) -0.5963(2) -0.54542(12) 0.0275(4) Uani 1 1 d . . . . .
H7 H -0.1697 -0.6074 -0.4884 0.033 Uiso 1 1 calc R . . . .
C8 C -0.25633(19) -0.6159(2) -0.60334(12) 0.0265(4) Uani 1 1 d . . . . .
H8 H -0.3442 -0.6420 -0.5849 0.032 Uiso 1 1 calc R . . . .
C9 C -0.23152(18) -0.5967(2) -0.68927(11) 0.0229(3) Uani 1 1 d . . . . .
H9 H -0.3022 -0.6088 -0.7283 0.027 Uiso 1 1 calc R . . . .
C10 C 0.25713(19) -0.4541(2) -0.64856(12) 0.0249(4) Uani 1 1 d . . . . .
H10 H 0.2510 -0.4933 -0.5912 0.030 Uiso 1 1 calc R . . . .
C11 C 0.2506(2) -0.2860(2) -0.64246(17) 0.0391(5) Uani 1 1 d . . . . .
H11A H 0.2525 -0.2443 -0.6980 0.059 Uiso 1 1 calc GR . . . .
H11B H 0.3285 -0.2507 -0.6109 0.059 Uiso 1 1 calc GR . . . .
H11C H 0.1666 -0.2575 -0.6146 0.059 Uiso 1 1 calc GR . . . .
C12 C 0.3923(2) -0.5084(3) -0.68620(15) 0.0338(5) Uani 1 1 d . . . . .
H12A H 0.3900 -0.6140 -0.6909 0.051 Uiso 1 1 calc GR . . . .
H12B H 0.4677 -0.4797 -0.6504 0.051 Uiso 1 1 calc GR . . . .
H12C H 0.4046 -0.4657 -0.7410 0.051 Uiso 1 1 calc GR . . . .
O13 O 0.19984(14) -0.45332(15) -0.83268(8) 0.0273(3) Uani 1 1 d . . . . .
N14 N -0.08580(16) -0.50263(18) -0.87084(10) 0.0237(3) Uani 1 1 d . . . . .
C15 C -0.22908(18) -0.5208(2) -0.88831(11) 0.0220(4) Uani 1 1 d . . . . .
C16 C -0.3115(2) -0.3955(2) -0.89321(12) 0.0284(4) Uani 1 1 d . . . . .
H16 H -0.2745 -0.3032 -0.8811 0.034 Uiso 1 1 calc R . . . .
C17 C -0.4493(2) -0.4092(2) -0.91628(14) 0.0348(5) Uani 1 1 d . . . . .
H17 H -0.5054 -0.3259 -0.9184 0.042 Uiso 1 1 calc R . . . .
C18 C -0.5039(2) -0.5463(2) -0.93616(13) 0.0323(4) Uani 1 1 d . . . . .
H18 H -0.5959 -0.5546 -0.9524 0.039 Uiso 1 1 calc R . . . .
C19 C -0.4213(2) -0.6704(2) -0.93177(12) 0.0300(4) Uani 1 1 d . . . . .
H19 H -0.4579 -0.7624 -0.9452 0.036 Uiso 1 1 calc R . . . .
C20 C -0.28374(19) -0.6586(2) -0.90735(12) 0.0281(4) Uani 1 1 d . . . . .
H20 H -0.2286 -0.7425 -0.9038 0.034 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 1.375(2) . ?
N1 C5 1.417(2) . ?
N1 C10 1.479(2) . ?
C2 C3 1.534(2) . ?
C2 O13 1.217(2) . ?
C3 C4 1.466(2) . ?
C3 N14 1.268(2) . ?
C4 C5 1.406(2) . ?
C4 C9 1.389(2) . ?
C5 C6 1.383(2) . ?
C6 H6 0.9300 . ?
C6 C7 1.394(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.386(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.397(2) . ?
C9 H9 0.9300 . ?
C10 H10 0.9800 . ?
C10 C11 1.527(3) . ?
C10 C12 1.519(3) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
N14 C15 1.423(2) . ?
C15 C16 1.389(3) . ?
C15 C20 1.390(3) . ?
C16 H16 0.9300 . ?
C16 C17 1.388(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.386(3) . ?
C18 H18 0.9300 . ?
C18 C19 1.382(3) . ?
C19 H19 0.9300 . ?
C19 C20 1.390(3) . ?
C20 H20 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
C2 N1 C5 109.94(14) . . ?
C2 N1 C10 124.81(15) . . ?
C5 N1 C10 123.00(15) . . ?
N1 C2 C3 106.62(14) . . ?
O13 C2 N1 127.30(17) . . ?
O13 C2 C3 126.03(16) . . ?
C4 C3 C2 105.78(14) . . ?
N14 C3 C2 118.74(15) . . ?
N14 C3 C4 135.24(17) . . ?
C5 C4 C3 106.45(15) . . ?
C9 C4 C3 133.19(16) . . ?
C9 C4 C5 120.30(16) . . ?
C4 C5 N1 111.10(15) . . ?
C6 C5 N1 127.54(16) . . ?
C6 C5 C4 121.35(16) . . ?
C5 C6 H6 121.2 . . ?
C5 C6 C7 117.62(17) . . ?
C7 C6 H6 121.2 . . ?
C6 C7 H7 119.1 . . ?
C8 C7 C6 121.78(17) . . ?
C8 C7 H7 119.1 . . ?
C7 C8 H8 119.8 . . ?
C7 C8 C9 120.38(17) . . ?
C9 C8 H8 119.8 . . ?
C4 C9 C8 118.53(16) . . ?
C4 C9 H9 120.7 . . ?
C8 C9 H9 120.7 . . ?
N1 C10 H10 107.5 . . ?
N1 C10 C11 108.97(15) . . ?
N1 C10 C12 112.65(16) . . ?
C11 C10 H10 107.5 . . ?
C12 C10 H10 107.5 . . ?
C12 C10 C11 112.56(18) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C3 N14 C15 120.90(15) . . ?
C16 C15 N14 118.37(16) . . ?
C16 C15 C20 120.27(17) . . ?
C20 C15 N14 121.12(16) . . ?
C15 C16 H16 120.2 . . ?
C17 C16 C15 119.52(18) . . ?
C17 C16 H16 120.2 . . ?
C16 C17 H17 119.8 . . ?
C18 C17 C16 120.39(19) . . ?
C18 C17 H17 119.8 . . ?
C17 C18 H18 120.1 . . ?
C19 C18 C17 119.88(19) . . ?
C19 C18 H18 120.1 . . ?
C18 C19 H19 119.8 . . ?
C18 C19 C20 120.32(18) . . ?
C20 C19 H19 119.8 . . ?
C15 C20 H20 120.2 . . ?
C19 C20 C15 119.60(17) . . ?
C19 C20 H20 120.2 . . ?

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
N1 C2 C3 C4 -0.76(17) . . . . ?
N1 C2 C3 N14 174.48(16) . . . . ?
N1 C5 C6 C7 -179.92(17) . . . . ?
C2 N1 C5 C4 3.10(19) . . . . ?
C2 N1 C5 C6 -175.87(17) . . . . ?
C2 N1 C10 C11 72.1(2) . . . . ?
C2 N1 C10 C12 -53.5(2) . . . . ?
C2 C3 C4 C5 2.52(17) . . . . ?
C2 C3 C4 C9 179.71(18) . . . . ?
C2 C3 N14 C15 -175.79(15) . . . . ?
C3 C4 C5 N1 -3.47(18) . . . . ?
C3 C4 C5 C6 175.57(16) . . . . ?
C3 C4 C9 C8 -175.76(18) . . . . ?
C3 N14 C15 C16 99.8(2) . . . . ?
C3 N14 C15 C20 -85.7(2) . . . . ?
C4 C3 N14 C15 -2.3(3) . . . . ?
C4 C5 C6 C7 1.2(3) . . . . ?
C5 N1 C2 C3 -1.33(18) . . . . ?
C5 N1 C2 O13 176.26(18) . . . . ?
C5 N1 C10 C11 -89.1(2) . . . . ?
C5 N1 C10 C12 145.23(18) . . . . ?
C5 C4 C9 C8 1.1(3) . . . . ?
C5 C6 C7 C8 0.5(3) . . . . ?
C6 C7 C8 C9 -1.4(3) . . . . ?
C7 C8 C9 C4 0.6(3) . . . . ?
C9 C4 C5 N1 178.90(16) . . . . ?
C9 C4 C5 C6 -2.1(2) . . . . ?
C10 N1 C2 C3 -164.64(16) . . . . ?
C10 N1 C2 O13 12.9(3) . . . . ?
C10 N1 C5 C4 166.77(15) . . . . ?
C10 N1 C5 C6 -12.2(3) . . . . ?
O13 C2 C3 C4 -178.38(18) . . . . ?
O13 C2 C3 N14 -3.1(3) . . . . ?
N14 C3 C4 C5 -171.5(2) . . . . ?
N14 C3 C4 C9 5.6(3) . . . . ?
N14 C15 C16 C17 175.27(18) . . . . ?
N14 C15 C20 C19 -174.00(17) . . . . ?
C15 C16 C17 C18 -1.4(3) . . . . ?
C16 C15 C20 C19 0.3(3) . . . . ?
C16 C17 C18 C19 1.0(3) . . . . ?
C17 C18 C19 C20 0.1(3) . . . . ?
C18 C19 C20 C15 -0.8(3) . . . . ?
C20 C15 C16 C17 0.8(3) . . . . ?

####################################################################### 
# 
# 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_xrd_23
_database_code_depnum_ccdc_archive 'CCDC 1538859'
_audit_update_record             
;
2017-03-19 deposited with the CCDC.
2018-10-29 downloaded from the CCDC.
;
_audit_creation_date             2016-03-18
_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         '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 0.0181 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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   13.6078(3)
_cell_length_b                   19.5284(6)
_cell_length_c                   11.3494(3)
_cell_angle_alpha                90
_cell_angle_beta                 108.884(3)
_cell_angle_gamma                90
_cell_volume                     2853.65(14)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3846
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      75.5020
_cell_measurement_theta_min      4.0870
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.614
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88028
_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.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.230
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1120
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.11
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0288
_diffrn_reflns_av_unetI/netI     0.0271
_diffrn_reflns_Laue_measured_fraction_full 0.971
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8586
_diffrn_reflns_point_group_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.307
_diffrn_reflns_theta_min         4.113
_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 0.971
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -14.00   32.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.4354   38.0000   60.0000 46

#__ type_ start__ end____ width___ exp.time_
  2 omega   -2.00   29.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.4354   38.0000  -90.0000 31

#__ type_ start__ end____ width___ exp.time_
  3 omega  -50.00  -24.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.4354   38.0000  -90.0000 26

#__ type_ start__ end____ width___ exp.time_
  4 omega -115.00  -13.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.4354  -57.0000  120.0000 102

#__ type_ start__ end____ width___ exp.time_
  5 omega   46.00   71.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000   90.0000 25

#__ type_ start__ end____ width___ exp.time_
  6 omega   37.00   63.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -77.0000   90.0000 26

#__ type_ start__ end____ width___ exp.time_
  7 omega   61.00  109.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -95.0000  120.0000 48

#__ type_ start__ end____ width___ exp.time_
  8 omega  109.00  135.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -77.0000   90.0000 26

#__ type_ start__ end____ width___ exp.time_
  9 omega  106.00  140.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -77.0000   60.0000 34

#__ type_ start__ end____ width___ exp.time_
 10 omega   99.00  141.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -61.0000   30.0000 42

#__ type_ start__ end____ width___ exp.time_
 11 omega   87.00  113.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -125.0000  120.0000 26

#__ type_ start__ end____ width___ exp.time_
 12 omega   86.00  116.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -111.0000   63.0000 30

#__ type_ start__ end____ width___ exp.time_
 13 omega   80.00  105.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -95.0000   30.0000 25

#__ type_ start__ end____ width___ exp.time_
 14 omega   70.00  106.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -95.0000   90.0000 36

#__ type_ start__ end____ width___ exp.time_
 15 omega   71.00   97.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000    0.0000 26

#__ type_ start__ end____ width___ exp.time_
 16 omega   51.00   90.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000  -90.0000 39

#__ type_ start__ end____ width___ exp.time_
 17 omega   65.00   91.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000 -120.0000 26

#__ type_ start__ end____ width___ exp.time_
 18 omega  113.00  175.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   30.0000 -180.0000 62

#__ type_ start__ end____ width___ exp.time_
 19 omega  118.00  177.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  125.0000 -180.0000 59

#__ type_ start__ end____ width___ exp.time_
 20 omega   81.00  160.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000 -180.0000 79

#__ type_ start__ end____ width___ exp.time_
 21 omega   62.00   94.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   15.0000   30.0000 32

#__ type_ start__ end____ width___ exp.time_
 22 omega  108.00  134.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   15.0000   30.0000 26

#__ type_ start__ end____ width___ exp.time_
 23 omega   83.00  115.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   61.0000  120.0000 32

#__ type_ start__ end____ width___ exp.time_
 24 omega  101.00  136.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   30.0000  150.0000 35

#__ type_ start__ end____ width___ exp.time_
 25 omega  149.00  174.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   30.0000  150.0000 25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0711756000
_diffrn_orient_matrix_UB_12      0.0267413000
_diffrn_orient_matrix_UB_13      -0.1264662000
_diffrn_orient_matrix_UB_21      -0.0455028000
_diffrn_orient_matrix_UB_22      -0.0724045000
_diffrn_orient_matrix_UB_23      -0.0334970000
_diffrn_orient_matrix_UB_31      -0.0846643000
_diffrn_orient_matrix_UB_32      0.0163943000
_diffrn_orient_matrix_UB_33      0.0588540000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2474
_reflns_number_total             2881
_reflns_odcompleteness_completeness 91.47
_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 1.171.37.35 (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         0.213
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         2881
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0455
_refine_ls_R_factor_gt           0.0384
_refine_ls_restrained_S_all      1.035
_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)+(0.0543P)²+1.2773P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0975
_refine_ls_wR_factor_ref         0.1035
_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), C15(H15), C16(H16), C17(H17)
2.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C21(H21A,H21B,H21C), C22(H22A,H22B,H22C)
;
_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 0.99171(7) 0.22519(6) 0.05962(9) 0.0219(2) Uani 1 1 d . . . . .
C2 C 1.08353(9) 0.22930(6) 0.15575(10) 0.0211(2) Uani 1 1 d . . . . .
C3 C 1.12473(8) 0.30165(6) 0.15109(10) 0.0191(2) Uani 1 1 d . . . . .
C4 C 1.05005(9) 0.33492(6) 0.04284(10) 0.0203(2) Uani 1 1 d . . . . .
C5 C 0.97125(9) 0.28656(7) -0.00856(10) 0.0215(3) Uani 1 1 d . . . . .
C6 C 0.88677(9) 0.30077(7) -0.11230(11) 0.0269(3) Uani 1 1 d . . . . .
H6 H 0.8349 0.2685 -0.1456 0.032 Uiso 1 1 calc R . . . .
C7 C 0.88286(10) 0.36547(8) -0.16460(11) 0.0303(3) Uani 1 1 d . . . . .
H7 H 0.8272 0.3764 -0.2349 0.036 Uiso 1 1 calc R . . . .
C8 C 0.95951(10) 0.41437(7) -0.11525(12) 0.0290(3) Uani 1 1 d . . . . .
H8 H 0.9541 0.4573 -0.1523 0.035 Uiso 1 1 calc R . . . .
C9 C 1.04462(9) 0.39930(7) -0.01016(11) 0.0241(3) Uani 1 1 d . . . . .
H9 H 1.0963 0.4317 0.0233 0.029 Uiso 1 1 calc R . . . .
C10 C 0.92813(10) 0.16393(7) 0.02632(12) 0.0283(3) Uani 1 1 d . . . . .
H10A H 0.8597 0.1735 0.0289 0.042 Uiso 1 1 calc GR . . . .
H10B H 0.9588 0.1280 0.0842 0.042 Uiso 1 1 calc GR . . . .
H10C H 0.9239 0.1498 -0.0562 0.042 Uiso 1 1 calc GR . . . .
O11 O 1.12479(7) 0.18371(5) 0.22766(8) 0.0276(2) Uani 1 1 d . . . . .
N12 N 1.20885(8) 0.32022(5) 0.23345(9) 0.0214(2) Uani 1 1 d . . . . .
C13 C 1.25124(8) 0.38634(6) 0.22862(10) 0.0199(2) Uani 1 1 d . . . . .
C14 C 1.23698(9) 0.43783(7) 0.30729(11) 0.0227(3) Uani 1 1 d . . . . .
C15 C 1.28778(10) 0.49982(7) 0.31066(11) 0.0269(3) Uani 1 1 d . . . . .
H15 H 1.2792 0.5345 0.3627 0.032 Uiso 1 1 calc R . . . .
C16 C 1.35092(10) 0.51118(7) 0.23825(12) 0.0295(3) Uani 1 1 d . . . . .
H16 H 1.3840 0.5531 0.2413 0.035 Uiso 1 1 calc R . . . .
C17 C 1.36440(10) 0.45948(8) 0.16132(12) 0.0287(3) Uani 1 1 d . . . . .
H17 H 1.4068 0.4671 0.1128 0.034 Uiso 1 1 calc R . . . .
C18 C 1.31572(9) 0.39630(7) 0.15529(11) 0.0240(3) Uani 1 1 d . . . . .
C21 C 1.33143(12) 0.33987(8) 0.07284(14) 0.0358(3) Uani 1 1 d . . . . .
H21A H 1.3593 0.3003 0.1225 0.054 Uiso 1 1 calc GR . . . .
H21B H 1.3790 0.3549 0.0315 0.054 Uiso 1 1 calc GR . . . .
H21C H 1.2660 0.3284 0.0119 0.054 Uiso 1 1 calc GR . . . .
C22 C 1.16760(11) 0.42610(8) 0.38498(13) 0.0333(3) Uani 1 1 d . . . . .
H22A H 1.0963 0.4278 0.3327 0.050 Uiso 1 1 calc GR . . . .
H22B H 1.1800 0.4610 0.4477 0.050 Uiso 1 1 calc GR . . . .
H22C H 1.1822 0.3820 0.4241 0.050 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 1.3694(15) . ?
N1 C5 1.4046(16) . ?
N1 C10 1.4529(16) . ?
C2 C3 1.5273(17) . ?
C2 O11 1.2154(15) . ?
C3 C4 1.4683(15) . ?
C3 N12 1.2740(15) . ?
C4 C5 1.4062(17) . ?
C4 C9 1.3854(18) . ?
C5 C6 1.3815(16) . ?
C6 H6 0.9300 . ?
C6 C7 1.390(2) . ?
C7 H7 0.9300 . ?
C7 C8 1.3912(19) . ?
C8 H8 0.9300 . ?
C8 C9 1.3987(17) . ?
C9 H9 0.9300 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
N12 C13 1.4225(16) . ?
C13 C14 1.3994(17) . ?
C13 C18 1.4047(16) . ?
C14 C15 1.3883(19) . ?
C14 C22 1.5034(17) . ?
C15 H15 0.9300 . ?
C15 C16 1.3856(19) . ?
C16 H16 0.9300 . ?
C16 C17 1.385(2) . ?
C17 H17 0.9300 . ?
C17 C18 1.3915(19) . ?
C18 C21 1.5050(18) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 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 110.86(10) . . ?
C2 N1 C10 124.64(11) . . ?
C5 N1 C10 124.33(10) . . ?
N1 C2 C3 106.08(10) . . ?
O11 C2 N1 126.59(12) . . ?
O11 C2 C3 127.30(11) . . ?
C4 C3 C2 106.02(9) . . ?
N12 C3 C2 119.38(11) . . ?
N12 C3 C4 134.60(12) . . ?
C5 C4 C3 106.15(10) . . ?
C9 C4 C3 133.64(11) . . ?
C9 C4 C5 120.20(11) . . ?
N1 C5 C4 110.85(10) . . ?
C6 C5 N1 127.08(12) . . ?
C6 C5 C4 122.07(12) . . ?
C5 C6 H6 121.5 . . ?
C5 C6 C7 116.94(12) . . ?
C7 C6 H6 121.5 . . ?
C6 C7 H7 118.9 . . ?
C6 C7 C8 122.15(11) . . ?
C8 C7 H7 118.9 . . ?
C7 C8 H8 119.8 . . ?
C7 C8 C9 120.32(13) . . ?
C9 C8 H8 119.8 . . ?
C4 C9 C8 118.31(12) . . ?
C4 C9 H9 120.8 . . ?
C8 C9 H9 120.8 . . ?
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 120.61(10) . . ?
C14 C13 N12 119.08(11) . . ?
C14 C13 C18 121.38(12) . . ?
C18 C13 N12 119.17(11) . . ?
C13 C14 C22 120.52(12) . . ?
C15 C14 C13 118.26(11) . . ?
C15 C14 C22 121.22(12) . . ?
C14 C15 H15 119.3 . . ?
C16 C15 C14 121.48(12) . . ?
C16 C15 H15 119.3 . . ?
C15 C16 H16 120.3 . . ?
C17 C16 C15 119.41(12) . . ?
C17 C16 H16 120.3 . . ?
C16 C17 H17 119.4 . . ?
C16 C17 C18 121.28(12) . . ?
C18 C17 H17 119.4 . . ?
C13 C18 C21 120.57(12) . . ?
C17 C18 C13 118.19(11) . . ?
C17 C18 C21 121.24(11) . . ?
C18 C21 H21A 109.5 . . ?
C18 C21 H21B 109.5 . . ?
C18 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C14 C22 H22A 109.5 . . ?
C14 C22 H22B 109.5 . . ?
C14 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 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 -1.97(12) . . . . ?
N1 C2 C3 N12 177.95(10) . . . . ?
N1 C5 C6 C7 179.96(11) . . . . ?
C2 N1 C5 C4 -1.02(13) . . . . ?
C2 N1 C5 C6 179.15(11) . . . . ?
C2 C3 C4 C5 1.37(12) . . . . ?
C2 C3 C4 C9 -179.40(12) . . . . ?
C2 C3 N12 C13 177.50(10) . . . . ?
C3 C4 C5 N1 -0.31(12) . . . . ?
C3 C4 C5 C6 179.52(11) . . . . ?
C3 C4 C9 C8 -179.31(12) . . . . ?
C3 N12 C13 C14 101.34(13) . . . . ?
C3 N12 C13 C18 -85.56(14) . . . . ?
C4 C3 N12 C13 -2.6(2) . . . . ?
C4 C5 C6 C7 0.15(18) . . . . ?
C5 N1 C2 C3 1.83(12) . . . . ?
C5 N1 C2 O11 -176.32(11) . . . . ?
C5 C4 C9 C8 -0.17(17) . . . . ?
C5 C6 C7 C8 -0.47(19) . . . . ?
C6 C7 C8 C9 0.5(2) . . . . ?
C7 C8 C9 C4 -0.14(19) . . . . ?
C9 C4 C5 N1 -179.67(10) . . . . ?
C9 C4 C5 C6 0.17(17) . . . . ?
C10 N1 C2 C3 177.21(10) . . . . ?
C10 N1 C2 O11 -0.94(19) . . . . ?
C10 N1 C5 C4 -176.42(10) . . . . ?
C10 N1 C5 C6 3.75(19) . . . . ?
O11 C2 C3 C4 176.17(11) . . . . ?
O11 C2 C3 N12 -3.91(18) . . . . ?
N12 C3 C4 C5 -178.53(13) . . . . ?
N12 C3 C4 C9 0.7(2) . . . . ?
N12 C13 C14 C15 173.45(10) . . . . ?
N12 C13 C14 C22 -7.06(16) . . . . ?
N12 C13 C18 C17 -173.86(11) . . . . ?
N12 C13 C18 C21 6.05(17) . . . . ?
C13 C14 C15 C16 0.20(17) . . . . ?
C14 C13 C18 C17 -0.92(17) . . . . ?
C14 C13 C18 C21 178.99(11) . . . . ?
C14 C15 C16 C17 -0.46(19) . . . . ?
C15 C16 C17 C18 0.01(19) . . . . ?
C16 C17 C18 C13 0.66(18) . . . . ?
C16 C17 C18 C21 -179.26(12) . . . . ?
C18 C13 C14 C15 0.50(16) . . . . ?
C18 C13 C14 C22 180.00(11) . . . . ?
C22 C14 C15 C16 -179.29(12) . . . . ?


####################################################################### 
# 
# 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_as_56
_database_code_depnum_ccdc_archive 'CCDC 1538865'
_audit_update_record             
;
2017-03-19 deposited with the CCDC.
2018-10-29 downloaded from the CCDC.
;
_audit_creation_date             2016-11-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.11.07 svn.r3352 for OlexSys, GUI svn.r5261)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C20 H14 N2 O'
_chemical_formula_sum            'C20 H14 N2 O'
_chemical_formula_weight         298.33
_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                   9.9809(7)
_cell_length_b                   10.7407(4)
_cell_length_c                   14.9870(10)
_cell_angle_alpha                73.451(5)
_cell_angle_beta                 78.454(6)
_cell_angle_gamma                86.790(4)
_cell_volume                     1508.92(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4107
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      75.5690
_cell_measurement_theta_min      3.1120
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.651
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86225
_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.
;
_exptl_crystal_colour            'translucent colorless'
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.09
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0220
_diffrn_reflns_av_unetI/netI     0.0330
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            10430
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.473
_diffrn_reflns_theta_min         3.135
_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 0.999
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -37.00   12.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787   38.0000  120.0000 49

#__ type_ start__ end____ width___ exp.time_
  2 omega  -65.00   29.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787   57.0000    0.0000 94

#__ type_ start__ end____ width___ exp.time_
  3 omega   69.00  130.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.3787  178.0000  150.0000 61

#__ type_ start__ end____ width___ exp.time_
  4 omega  102.00  169.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  112.0000  -30.0000 67

#__ type_ start__ end____ width___ exp.time_
  5 omega  109.00  177.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   30.0000  -60.0000 68

#__ type_ start__ end____ width___ exp.time_
  6 omega  104.00  174.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   30.0000   60.0000 70

#__ type_ start__ end____ width___ exp.time_
  7 omega  111.00  138.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000  -60.0000 27

#__ type_ start__ end____ width___ exp.time_
  8 omega   89.00  114.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000  -60.0000 25

#__ type_ start__ end____ width___ exp.time_
  9 omega   60.00  133.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000 -150.0000 73

#__ type_ start__ end____ width___ exp.time_
 10 omega   61.00  114.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000 -180.0000 53

#__ type_ start__ end____ width___ exp.time_
 11 omega   36.00   88.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000  -60.0000 52

#__ type_ start__ end____ width___ exp.time_
 12 omega   50.00  109.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000    0.0000 59

#__ type_ start__ end____ width___ exp.time_
 13 omega   73.00  100.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000  120.0000 27

#__ type_ start__ end____ width___ exp.time_
 14 omega   48.00   89.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000   90.0000 41

#__ type_ start__ end____ width___ exp.time_
 15 omega   52.00   91.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000  150.0000 39

#__ type_ start__ end____ width___ exp.time_
 16 omega   43.00   68.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000  120.0000 25

#__ type_ start__ end____ width___ exp.time_
 17 omega   42.00   85.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000   60.0000 43

#__ type_ start__ end____ width___ exp.time_
 18 omega   38.00   78.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000   30.0000 40

#__ type_ start__ end____ width___ exp.time_
 19 omega   34.00   60.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000  -60.0000 26

#__ type_ start__ end____ width___ exp.time_
 20 omega   39.00   67.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000  -60.0000 28

#__ type_ start__ end____ width___ exp.time_
 21 omega   40.00   70.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000  -90.0000 30

#__ type_ start__ end____ width___ exp.time_
 22 omega -117.00  -15.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787  -77.0000 -120.0000 102

#__ type_ start__ end____ width___ exp.time_
 23 omega -116.00  -12.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787  -77.0000  150.0000 104
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.1178415000
_diffrn_orient_matrix_UB_12      0.0029032000
_diffrn_orient_matrix_UB_13      0.0518946000
_diffrn_orient_matrix_UB_21      -0.1024938000
_diffrn_orient_matrix_UB_22      -0.0265899000
_diffrn_orient_matrix_UB_23      0.0950044000
_diffrn_orient_matrix_UB_31      0.0206633000
_diffrn_orient_matrix_UB_32      -0.1472202000
_diffrn_orient_matrix_UB_33      0.0149311000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4799
_reflns_number_total             5945
_reflns_odcompleteness_completeness 99.81
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     69.95
_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 1.171.37.35 (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    'ShelXS (Sheldrick, 2015)'
_refine_diff_density_max         0.332
_refine_diff_density_min         -0.168
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     415
_refine_ls_number_reflns         5945
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0559
_refine_ls_R_factor_gt           0.0435
_refine_ls_restrained_S_all      1.023
_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)+(0.0572P)²+0.4076P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1102
_refine_ls_wR_factor_ref         0.1209
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C9(H9), C11(H11), C12(H12), C13(H13), C14(H14),
 C15(H15), C19(H19), C20(H20), C21(H21), C22(H22), C23(H23), C6A(H6A), C7A(H7A),
  C8A(H8A), C9A(H9A), C11A(H11A), C12A(H12A), C13A(H13A), C14A(H14A),
 C15A(H15A), C19A(H19A), C20A(H20A), C21A(H21A), C22A(H22A), C23A(H23A)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.74886(15) 0.39972(14) 0.41669(10) 0.0359(3) Uani 1 1 d . . . . .
C2 C 0.62528(17) 0.33749(16) 0.45043(11) 0.0336(3) Uani 1 1 d . . . . .
C3 C 0.65222(17) 0.20799(16) 0.52091(12) 0.0331(3) Uani 1 1 d . . . . .
C4 C 0.80082(16) 0.20601(16) 0.52060(11) 0.0315(3) Uani 1 1 d . . . . .
C5 C 0.85321(17) 0.32389(16) 0.45748(12) 0.0325(3) Uani 1 1 d . . . . .
C6 C 0.98956(18) 0.35665(17) 0.44095(12) 0.0368(4) Uani 1 1 d . . . . .
H6 H 1.0228 0.4357 0.3996 0.044 Uiso 1 1 calc R . . . .
C7 C 1.07537(18) 0.26648(18) 0.48881(14) 0.0407(4) Uani 1 1 d . . . . .
H7 H 1.1678 0.2858 0.4790 0.049 Uiso 1 1 calc R . . . .
C8 C 1.02580(19) 0.14816(18) 0.55087(14) 0.0412(4) Uani 1 1 d . . . . .
H8 H 1.0853 0.0895 0.5818 0.049 Uiso 1 1 calc R . . . .
C9 C 0.88829(18) 0.11702(17) 0.56701(12) 0.0371(4) Uani 1 1 d . . . . .
H9 H 0.8552 0.0378 0.6082 0.044 Uiso 1 1 calc R . . . .
C10 C 0.77101(17) 0.52475(16) 0.34789(12) 0.0338(3) Uani 1 1 d . . . . .
C11 C 0.71228(17) 0.63436(17) 0.37078(12) 0.0362(4) Uani 1 1 d . . . . .
H11 H 0.6557 0.6275 0.4294 0.043 Uiso 1 1 calc R . . . .
C12 C 0.73947(18) 0.75505(17) 0.30438(14) 0.0398(4) Uani 1 1 d . . . . .
H12 H 0.7012 0.8297 0.3187 0.048 Uiso 1 1 calc R . . . .
C13 C 0.82318(17) 0.76421(17) 0.21733(13) 0.0398(4) Uani 1 1 d . . . . .
H13 H 0.8423 0.8451 0.1737 0.048 Uiso 1 1 calc R . . . .
C14 C 0.87833(18) 0.65402(19) 0.19499(13) 0.0421(4) Uani 1 1 d . . . . .
H14 H 0.9336 0.6608 0.1360 0.051 Uiso 1 1 calc R . . . .
C15 C 0.85192(19) 0.53314(18) 0.25995(13) 0.0393(4) Uani 1 1 d . . . . .
H15 H 0.8882 0.4585 0.2446 0.047 Uiso 1 1 calc R . . . .
O16 O 0.51658(12) 0.37730(12) 0.42866(9) 0.0388(3) Uani 1 1 d . . . . .
N17 N 0.55401(15) 0.13076(14) 0.56470(10) 0.0350(3) Uani 1 1 d . . . . .
C18 C 0.57918(16) 0.01478(16) 0.63496(12) 0.0328(3) Uani 1 1 d . . . . .
C19 C 0.59675(18) -0.10400(18) 0.61446(13) 0.0398(4) Uani 1 1 d . . . . .
H19 H 0.5967 -0.1089 0.5535 0.048 Uiso 1 1 calc R . . . .
C20 C 0.61438(18) -0.21549(17) 0.68582(14) 0.0408(4) Uani 1 1 d . . . . .
H20 H 0.6274 -0.2951 0.6724 0.049 Uiso 1 1 calc R . . . .
C21 C 0.61262(17) -0.20854(17) 0.77677(13) 0.0387(4) Uani 1 1 d . . . . .
H21 H 0.6252 -0.2833 0.8242 0.046 Uiso 1 1 calc R . . . .
C22 C 0.59219(17) -0.09056(17) 0.79701(13) 0.0368(4) Uani 1 1 d . . . . .
H22 H 0.5896 -0.0864 0.8585 0.044 Uiso 1 1 calc R . . . .
C23 C 0.57550(17) 0.02175(17) 0.72660(12) 0.0339(3) Uani 1 1 d . . . . .
H23 H 0.5620 0.1011 0.7405 0.041 Uiso 1 1 calc R . . . .
N1A N 0.57044(14) 0.73120(13) 0.08816(10) 0.0314(3) Uani 1 1 d . . . . .
C2A C 0.64464(16) 0.84490(15) 0.05135(11) 0.0304(3) Uani 1 1 d . . . . .
C3A C 0.77330(16) 0.81438(16) -0.01376(11) 0.0312(3) Uani 1 1 d . . . . .
C4A C 0.76242(17) 0.67590(16) -0.00887(12) 0.0343(4) Uani 1 1 d . . . . .
C5A C 0.64026(16) 0.63059(16) 0.05466(12) 0.0323(3) Uani 1 1 d . . . . .
C6A C 0.59882(18) 0.50283(17) 0.07779(14) 0.0393(4) Uani 1 1 d . . . . .
H6A H 0.5178 0.4738 0.1203 0.047 Uiso 1 1 calc R . . . .
C7A C 0.6820(2) 0.41910(18) 0.03554(16) 0.0472(5) Uani 1 1 d . . . . .
H7A H 0.6557 0.3329 0.0494 0.057 Uiso 1 1 calc R . . . .
C8A C 0.8035(2) 0.46164(19) -0.02693(17) 0.0508(5) Uani 1 1 d . . . . .
H8A H 0.8576 0.4037 -0.0542 0.061 Uiso 1 1 calc R . . . .
C9A C 0.84535(18) 0.58985(18) -0.04920(14) 0.0423(4) Uani 1 1 d . . . . .
H9A H 0.9276 0.6178 -0.0905 0.051 Uiso 1 1 calc R . . . .
C10A C 0.44285(16) 0.71661(15) 0.15389(12) 0.0299(3) Uani 1 1 d . . . . .
C11A C 0.33232(16) 0.79436(15) 0.12885(12) 0.0303(3) Uani 1 1 d . . . . .
H11A H 0.3409 0.8556 0.0699 0.036 Uiso 1 1 calc R . . . .
C12A C 0.20953(17) 0.77910(16) 0.19307(13) 0.0339(3) Uani 1 1 d . . . . .
H12A H 0.1353 0.8310 0.1773 0.041 Uiso 1 1 calc R . . . .
C13A C 0.19601(18) 0.68683(16) 0.28101(13) 0.0364(4) Uani 1 1 d . . . . .
H13A H 0.1128 0.6764 0.3234 0.044 Uiso 1 1 calc R . . . .
C14A C 0.30722(18) 0.61049(16) 0.30518(12) 0.0362(4) Uani 1 1 d . . . . .
H14A H 0.2983 0.5489 0.3640 0.043 Uiso 1 1 calc R . . . .
C15A C 0.43167(17) 0.62542(15) 0.24223(12) 0.0334(3) Uani 1 1 d . . . . .
H15A H 0.5066 0.5752 0.2588 0.040 Uiso 1 1 calc R . . . .
O16A O 0.61357(12) 0.94845(11) 0.06707(8) 0.0335(3) Uani 1 1 d . . . . .
N17A N 0.86179(14) 0.90304(13) -0.05446(10) 0.0331(3) Uani 1 1 d . . . . .
C18A C 0.97900(17) 0.88224(16) -0.12118(13) 0.0354(4) Uani 1 1 d . . . . .
C19A C 1.10842(18) 0.89547(17) -0.10335(15) 0.0424(4) Uani 1 1 d . . . . .
H19A H 1.1178 0.9118 -0.0472 0.051 Uiso 1 1 calc R . . . .
C20A C 1.22242(19) 0.88404(19) -0.16975(17) 0.0493(5) Uani 1 1 d . . . . .
H20A H 1.3089 0.8930 -0.1580 0.059 Uiso 1 1 calc R . . . .
C21A C 1.21037(19) 0.85924(18) -0.25444(16) 0.0494(5) Uani 1 1 d . . . . .
H21A H 1.2879 0.8501 -0.2983 0.059 Uiso 1 1 calc R . . . .
C22A C 1.08192(19) 0.84846(17) -0.27197(14) 0.0438(4) Uani 1 1 d . . . . .
H22A H 1.0727 0.8332 -0.3285 0.053 Uiso 1 1 calc R . . . .
C23A C 0.96588(18) 0.86015(18) -0.20596(14) 0.0403(4) Uani 1 1 d . . . . .
H23A H 0.8795 0.8532 -0.2185 0.048 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 1.369(2) . ?
N1 C5 1.414(2) . ?
N1 C10 1.438(2) . ?
C2 C3 1.535(2) . ?
C2 O16 1.215(2) . ?
C3 C4 1.481(2) . ?
C3 N17 1.266(2) . ?
C4 C5 1.402(2) . ?
C4 C9 1.389(2) . ?
C5 C6 1.381(2) . ?
C6 H6 0.9300 . ?
C6 C7 1.394(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.392(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.388(2) . ?
C9 H9 0.9300 . ?
C10 C11 1.386(3) . ?
C10 C15 1.383(2) . ?
C11 H11 0.9300 . ?
C11 C12 1.393(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.382(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.376(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.385(3) . ?
C15 H15 0.9300 . ?
N17 C18 1.431(2) . ?
C18 C19 1.389(3) . ?
C18 C23 1.390(2) . ?
C19 H19 0.9300 . ?
C19 C20 1.390(3) . ?
C20 H20 0.9300 . ?
C20 C21 1.383(3) . ?
C21 H21 0.9300 . ?
C21 C22 1.380(3) . ?
C22 H22 0.9300 . ?
C22 C23 1.385(2) . ?
C23 H23 0.9300 . ?
N1A C2A 1.378(2) . ?
N1A C5A 1.411(2) . ?
N1A C10A 1.431(2) . ?
C2A C3A 1.530(2) . ?
C2A O16A 1.212(2) . ?
C3A C4A 1.477(2) . ?
C3A N17A 1.268(2) . ?
C4A C5A 1.403(2) . ?
C4A C9A 1.392(3) . ?
C5A C6A 1.382(2) . ?
C6A H6A 0.9300 . ?
C6A C7A 1.389(3) . ?
C7A H7A 0.9300 . ?
C7A C8A 1.386(3) . ?
C8A H8A 0.9300 . ?
C8A C9A 1.389(3) . ?
C9A H9A 0.9300 . ?
C10A C11A 1.393(2) . ?
C10A C15A 1.392(2) . ?
C11A H11A 0.9300 . ?
C11A C12A 1.384(2) . ?
C12A H12A 0.9300 . ?
C12A C13A 1.392(2) . ?
C13A H13A 0.9300 . ?
C13A C14A 1.388(3) . ?
C14A H14A 0.9300 . ?
C14A C15A 1.388(2) . ?
C15A H15A 0.9300 . ?
N17A C18A 1.431(2) . ?
C18A C19A 1.393(2) . ?
C18A C23A 1.389(3) . ?
C19A H19A 0.9300 . ?
C19A C20A 1.379(3) . ?
C20A H20A 0.9300 . ?
C20A C21A 1.398(3) . ?
C21A H21A 0.9300 . ?
C21A C22A 1.377(3) . ?
C22A H22A 0.9300 . ?
C22A C23A 1.390(3) . ?
C23A H23A 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
C2 N1 C5 110.99(14) . . ?
C2 N1 C10 124.89(14) . . ?
C5 N1 C10 124.12(14) . . ?
N1 C2 C3 106.11(14) . . ?
O16 C2 N1 126.65(16) . . ?
O16 C2 C3 127.24(15) . . ?
C4 C3 C2 105.72(13) . . ?
N17 C3 C2 119.79(15) . . ?
N17 C3 C4 134.49(16) . . ?
C5 C4 C3 106.23(14) . . ?
C9 C4 C3 134.18(15) . . ?
C9 C4 C5 119.59(15) . . ?
C4 C5 N1 110.94(14) . . ?
C6 C5 N1 126.89(15) . . ?
C6 C5 C4 122.16(15) . . ?
C5 C6 H6 121.3 . . ?
C5 C6 C7 117.32(15) . . ?
C7 C6 H6 121.3 . . ?
C6 C7 H7 119.3 . . ?
C8 C7 C6 121.45(16) . . ?
C8 C7 H7 119.3 . . ?
C7 C8 H8 119.8 . . ?
C9 C8 C7 120.48(16) . . ?
C9 C8 H8 119.8 . . ?
C4 C9 H9 120.5 . . ?
C8 C9 C4 118.98(16) . . ?
C8 C9 H9 120.5 . . ?
C11 C10 N1 119.78(16) . . ?
C15 C10 N1 119.02(16) . . ?
C15 C10 C11 121.20(16) . . ?
C10 C11 H11 120.6 . . ?
C10 C11 C12 118.78(17) . . ?
C12 C11 H11 120.6 . . ?
C11 C12 H12 119.9 . . ?
C13 C12 C11 120.18(17) . . ?
C13 C12 H12 119.9 . . ?
C12 C13 H13 119.9 . . ?
C14 C13 C12 120.27(16) . . ?
C14 C13 H13 119.9 . . ?
C13 C14 H14 119.8 . . ?
C13 C14 C15 120.35(17) . . ?
C15 C14 H14 119.8 . . ?
C10 C15 C14 119.18(18) . . ?
C10 C15 H15 120.4 . . ?
C14 C15 H15 120.4 . . ?
C3 N17 C18 119.05(15) . . ?
C19 C18 N17 121.13(15) . . ?
C19 C18 C23 120.36(16) . . ?
C23 C18 N17 118.34(15) . . ?
C18 C19 H19 120.3 . . ?
C18 C19 C20 119.43(17) . . ?
C20 C19 H19 120.3 . . ?
C19 C20 H20 119.9 . . ?
C21 C20 C19 120.30(17) . . ?
C21 C20 H20 119.9 . . ?
C20 C21 H21 120.1 . . ?
C22 C21 C20 119.90(17) . . ?
C22 C21 H21 120.1 . . ?
C21 C22 H22 119.7 . . ?
C21 C22 C23 120.60(17) . . ?
C23 C22 H22 119.7 . . ?
C18 C23 H23 120.3 . . ?
C22 C23 C18 119.39(16) . . ?
C22 C23 H23 120.3 . . ?
C2A N1A C5A 110.48(13) . . ?
C2A N1A C10A 124.52(14) . . ?
C5A N1A C10A 124.97(13) . . ?
N1A C2A C3A 106.21(14) . . ?
O16A C2A N1A 126.77(16) . . ?
O16A C2A C3A 127.02(14) . . ?
C4A C3A C2A 105.87(13) . . ?
N17A C3A C2A 118.73(15) . . ?
N17A C3A C4A 135.34(16) . . ?
C5A C4A C3A 106.21(15) . . ?
C9A C4A C3A 134.43(16) . . ?
C9A C4A C5A 119.32(16) . . ?
C4A C5A N1A 111.18(14) . . ?
C6A C5A N1A 126.94(16) . . ?
C6A C5A C4A 121.88(16) . . ?
C5A C6A H6A 121.1 . . ?
C5A C6A C7A 117.86(17) . . ?
C7A C6A H6A 121.1 . . ?
C6A C7A H7A 119.4 . . ?
C8A C7A C6A 121.21(17) . . ?
C8A C7A H7A 119.4 . . ?
C7A C8A H8A 119.7 . . ?
C7A C8A C9A 120.69(18) . . ?
C9A C8A H8A 119.7 . . ?
C4A C9A H9A 120.5 . . ?
C8A C9A C4A 119.04(17) . . ?
C8A C9A H9A 120.5 . . ?
C11A C10A N1A 119.57(14) . . ?
C15A C10A N1A 119.36(15) . . ?
C15A C10A C11A 121.07(15) . . ?
C10A C11A H11A 120.5 . . ?
C12A C11A C10A 118.94(15) . . ?
C12A C11A H11A 120.5 . . ?
C11A C12A H12A 119.7 . . ?
C11A C12A C13A 120.69(16) . . ?
C13A C12A H12A 119.7 . . ?
C12A C13A H13A 120.1 . . ?
C14A C13A C12A 119.73(16) . . ?
C14A C13A H13A 120.1 . . ?
C13A C14A H14A 119.8 . . ?
C13A C14A C15A 120.45(16) . . ?
C15A C14A H14A 119.8 . . ?
C10A C15A H15A 120.4 . . ?
C14A C15A C10A 119.11(16) . . ?
C14A C15A H15A 120.4 . . ?
C3A N17A C18A 120.84(15) . . ?
C19A C18A N17A 118.53(17) . . ?
C23A C18A N17A 121.32(15) . . ?
C23A C18A C19A 119.93(17) . . ?
C18A C19A H19A 120.3 . . ?
C20A C19A C18A 119.3(2) . . ?
C20A C19A H19A 120.3 . . ?
C19A C20A H20A 119.4 . . ?
C19A C20A C21A 121.17(18) . . ?
C21A C20A H20A 119.4 . . ?
C20A C21A H21A 120.5 . . ?
C22A C21A C20A 118.98(18) . . ?
C22A C21A H21A 120.5 . . ?
C21A C22A H22A 119.7 . . ?
C21A C22A C23A 120.6(2) . . ?
C23A C22A H22A 119.7 . . ?
C18A C23A C22A 119.96(17) . . ?
C18A C23A H23A 120.0 . . ?
C22A C23A H23A 120.0 . . ?

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 -0.81(18) . . . . ?
N1 C2 C3 N17 178.72(15) . . . . ?
N1 C5 C6 C7 -179.74(17) . . . . ?
N1 C10 C11 C12 177.53(15) . . . . ?
N1 C10 C15 C14 -177.23(16) . . . . ?
C2 N1 C5 C4 0.3(2) . . . . ?
C2 N1 C5 C6 -179.08(17) . . . . ?
C2 N1 C10 C11 66.0(2) . . . . ?
C2 N1 C10 C15 -114.5(2) . . . . ?
C2 C3 C4 C5 0.99(18) . . . . ?
C2 C3 C4 C9 -178.95(18) . . . . ?
C2 C3 N17 C18 -175.66(15) . . . . ?
C3 C4 C5 N1 -0.84(19) . . . . ?
C3 C4 C5 C6 178.60(16) . . . . ?
C3 C4 C9 C8 -178.96(18) . . . . ?
C3 N17 C18 C19 -99.7(2) . . . . ?
C3 N17 C18 C23 85.0(2) . . . . ?
C4 C3 N17 C18 3.7(3) . . . . ?
C4 C5 C6 C7 0.9(3) . . . . ?
C5 N1 C2 C3 0.32(18) . . . . ?
C5 N1 C2 O16 -179.67(17) . . . . ?
C5 N1 C10 C11 -114.94(19) . . . . ?
C5 N1 C10 C15 64.6(2) . . . . ?
C5 C4 C9 C8 1.1(3) . . . . ?
C5 C6 C7 C8 -0.1(3) . . . . ?
C6 C7 C8 C9 -0.2(3) . . . . ?
C7 C8 C9 C4 -0.3(3) . . . . ?
C9 C4 C5 N1 179.11(15) . . . . ?
C9 C4 C5 C6 -1.4(3) . . . . ?
C10 N1 C2 C3 179.49(15) . . . . ?
C10 N1 C2 O16 -0.5(3) . . . . ?
C10 N1 C5 C4 -178.85(15) . . . . ?
C10 N1 C5 C6 1.7(3) . . . . ?
C10 C11 C12 C13 0.3(3) . . . . ?
C11 C10 C15 C14 2.3(3) . . . . ?
C11 C12 C13 C14 1.1(3) . . . . ?
C12 C13 C14 C15 -0.8(3) . . . . ?
C13 C14 C15 C10 -0.8(3) . . . . ?
C15 C10 C11 C12 -2.0(3) . . . . ?
O16 C2 C3 C4 179.18(17) . . . . ?
O16 C2 C3 N17 -1.3(3) . . . . ?
N17 C3 C4 C5 -178.43(19) . . . . ?
N17 C3 C4 C9 1.6(3) . . . . ?
N17 C18 C19 C20 -176.89(15) . . . . ?
N17 C18 C23 C22 176.52(14) . . . . ?
C18 C19 C20 C21 0.9(3) . . . . ?
C19 C18 C23 C22 1.2(2) . . . . ?
C19 C20 C21 C22 0.5(3) . . . . ?
C20 C21 C22 C23 -1.0(3) . . . . ?
C21 C22 C23 C18 0.2(2) . . . . ?
C23 C18 C19 C20 -1.7(3) . . . . ?
N1A C2A C3A C4A -0.09(16) . . . . ?
N1A C2A C3A N17A -177.75(14) . . . . ?
N1A C5A C6A C7A 179.00(17) . . . . ?
N1A C10A C11A C12A 179.93(14) . . . . ?
N1A C10A C15A C14A -179.15(15) . . . . ?
C2A N1A C5A C4A -2.06(19) . . . . ?
C2A N1A C5A C6A 178.53(17) . . . . ?
C2A N1A C10A C11A 58.9(2) . . . . ?
C2A N1A C10A C15A -120.61(17) . . . . ?
C2A C3A C4A C5A -1.08(17) . . . . ?
C2A C3A C4A C9A -178.60(19) . . . . ?
C2A C3A N17A C18A -175.53(14) . . . . ?
C3A C4A C5A N1A 1.91(18) . . . . ?
C3A C4A C5A C6A -178.65(15) . . . . ?
C3A C4A C9A C8A 178.56(19) . . . . ?
C3A N17A C18A C19A -121.41(18) . . . . ?
C3A N17A C18A C23A 64.0(2) . . . . ?
C4A C3A N17A C18A 7.7(3) . . . . ?
C4A C5A C6A C7A -0.4(3) . . . . ?
C5A N1A C2A C3A 1.26(17) . . . . ?
C5A N1A C2A O16A -179.15(15) . . . . ?
C5A N1A C10A C11A -123.51(17) . . . . ?
C5A N1A C10A C15A 57.0(2) . . . . ?
C5A C4A C9A C8A 1.3(3) . . . . ?
C5A C6A C7A C8A 0.8(3) . . . . ?
C6A C7A C8A C9A -0.1(3) . . . . ?
C7A C8A C9A C4A -0.9(3) . . . . ?
C9A C4A C5A N1A 179.88(15) . . . . ?
C9A C4A C5A C6A -0.7(3) . . . . ?
C10A N1A C2A C3A 179.14(14) . . . . ?
C10A N1A C2A O16A -1.3(3) . . . . ?
C10A N1A C5A C4A -179.93(14) . . . . ?
C10A N1A C5A C6A 0.7(3) . . . . ?
C10A C11A C12A C13A -0.6(2) . . . . ?
C11A C10A C15A C14A 1.3(2) . . . . ?
C11A C12A C13A C14A 0.9(3) . . . . ?
C12A C13A C14A C15A -0.1(3) . . . . ?
C13A C14A C15A C10A -1.0(3) . . . . ?
C15A C10A C11A C12A -0.5(2) . . . . ?
O16A C2A C3A C4A -179.68(15) . . . . ?
O16A C2A C3A N17A 2.7(2) . . . . ?
N17A C3A C4A C5A 176.00(18) . . . . ?
N17A C3A C4A C9A -1.5(3) . . . . ?
N17A C18A C19A C20A -175.86(16) . . . . ?
N17A C18A C23A C22A 175.93(16) . . . . ?
C18A C19A C20A C21A -0.1(3) . . . . ?
C19A C18A C23A C22A 1.4(3) . . . . ?
C19A C20A C21A C22A 1.2(3) . . . . ?
C20A C21A C22A C23A -0.9(3) . . . . ?
C21A C22A C23A C18A -0.3(3) . . . . ?
C23A C18A C19A C20A -1.2(3) . . . . ?


####################################################################### 
# 
# 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_lcb_009
_database_code_depnum_ccdc_archive 'CCDC 1538868'
_audit_update_record             
;
2017-03-19 deposited with the CCDC.
2018-10-29 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         'C30 H24 Cl2 Cu N4 O2'
_chemical_formula_sum            'C30 H24 Cl2 Cu N4 O2'
_chemical_formula_weight         606.97
_chemical_melting_point          ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -1.9646 0.5888 '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                   8.0870(8)
_cell_length_b                   9.2417(10)
_cell_length_c                   9.6103(10)
_cell_angle_alpha                75.944(9)
_cell_angle_beta                 75.005(9)
_cell_angle_gamma                79.112(9)
_cell_volume                     666.90(13)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    5129
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      75.0780
_cell_measurement_theta_min      4.8750
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.293
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78764
_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    1.511
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             311
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.08
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0394
_diffrn_reflns_av_unetI/netI     0.0274
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            11073
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.490
_diffrn_reflns_theta_min         4.867
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.3829
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega    5.00   35.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.2537   38.0000   90.0000 30

#__ type_ start__ end____ width___ exp.time_
  2 omega  -35.00   36.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.2537   38.0000   60.0000 71

#__ type_ start__ end____ width___ exp.time_
  3 omega  -34.00   31.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.2537   38.0000  -30.0000 65

#__ type_ start__ end____ width___ exp.time_
  4 omega   56.00  121.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       40.2537 -178.0000  -30.0000 65

#__ type_ start__ end____ width___ exp.time_
  5 omega   71.00  104.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       40.2537  178.0000   60.0000 33

#__ type_ start__ end____ width___ exp.time_
  6 omega   23.00  115.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       40.2537   38.0000 -180.0000 92

#__ type_ start__ end____ width___ exp.time_
  7 omega   24.00   79.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       40.2537  -99.0000   90.0000 55

#__ type_ start__ end____ width___ exp.time_
  8 omega   79.00  112.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000 -120.0000 33

#__ type_ start__ end____ width___ exp.time_
  9 omega  135.00  174.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000  -90.0000 39

#__ type_ start__ end____ width___ exp.time_
 10 omega   75.00  176.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   15.0000   30.0000 101

#__ type_ start__ end____ width___ exp.time_
 11 omega   36.00   84.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000   90.0000 48

#__ type_ start__ end____ width___ exp.time_
 12 omega   71.00  115.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000 -180.0000 44

#__ type_ start__ end____ width___ exp.time_
 13 omega   79.00  166.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000 -120.0000 87

#__ type_ start__ end____ width___ exp.time_
 14 omega   78.00  104.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000  120.0000 26

#__ type_ start__ end____ width___ exp.time_
 15 omega   35.00   82.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000  -30.0000 47

#__ type_ start__ end____ width___ exp.time_
 16 omega   49.00   90.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000  150.0000 41

#__ type_ start__ end____ width___ exp.time_
 17 omega  100.00  126.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000   60.0000 26

#__ type_ start__ end____ width___ exp.time_
 18 omega   68.00  106.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   15.0000 -120.0000 38

#__ type_ start__ end____ width___ exp.time_
 19 omega  125.00  152.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   15.0000 -120.0000 27

#__ type_ start__ end____ width___ exp.time_
 20 omega   78.00  104.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000   60.0000 26

#__ type_ start__ end____ width___ exp.time_
 21 omega   69.00   95.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000    0.0000 26

#__ type_ start__ end____ width___ exp.time_
 22 omega  110.00  140.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000    0.0000 30

#__ type_ start__ end____ width___ exp.time_
 23 omega   71.00  108.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   15.0000  120.0000 37

#__ type_ start__ end____ width___ exp.time_
 24 omega  143.00  169.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   15.0000  120.0000 26

#__ type_ start__ end____ width___ exp.time_
 25 omega   65.00   92.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000   60.0000 27

#__ type_ start__ end____ width___ exp.time_
 26 omega   70.00  115.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000   60.0000 45

#__ type_ start__ end____ width___ exp.time_
 27 omega   69.00  110.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000    0.0000 41

#__ type_ start__ end____ width___ exp.time_
 28 omega   40.00   67.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000  120.0000 27

#__ type_ start__ end____ width___ exp.time_
 29 omega   74.00  100.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000  -90.0000 26

#__ type_ start__ end____ width___ exp.time_
 30 omega   30.00   55.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000  -90.0000 25

#__ type_ start__ end____ width___ exp.time_
 31 omega  102.00  173.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  112.0000   60.0000 71

#__ type_ start__ end____ width___ exp.time_
 32 omega   43.00   98.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000  -60.0000 55

#__ type_ start__ end____ width___ exp.time_
 33 omega   82.00  111.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000    0.0000 29

#__ type_ start__ end____ width___ exp.time_
 34 omega   29.00   59.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000   60.0000 30

#__ type_ start__ end____ width___ exp.time_
 35 omega   43.00   71.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000   60.0000 28

#__ type_ start__ end____ width___ exp.time_
 36 omega   41.00   89.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000 -180.0000 48

#__ type_ start__ end____ width___ exp.time_
 37 omega   64.00  111.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000  -60.0000 47

#__ type_ start__ end____ width___ exp.time_
 38 omega   -6.00   19.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0000   98.0000 -138.2201 25

#__ type_ start__ end____ width___ exp.time_
 39 omega  -37.00  -11.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.2537  -57.0000   90.0000 26

#__ type_ start__ end____ width___ exp.time_
 40 omega  -94.00  -67.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.2537  -57.0000   90.0000 27

#__ type_ start__ end____ width___ exp.time_
 41 omega  -42.00  -11.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.2537  -57.0000    0.0000 31

#__ type_ start__ end____ width___ exp.time_
 42 omega  -22.00   37.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.2537   77.0000  120.0000 59

#__ type_ start__ end____ width___ exp.time_
 43 omega -113.00  -49.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.2537  -57.0000    0.0000 64

#__ type_ start__ end____ width___ exp.time_
 44 omega    6.00   31.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       44.0000   90.0000   57.2094 25

#__ type_ start__ end____ width___ exp.time_
 45 omega   17.00   42.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       52.0000   81.0000 -121.3571 25

#__ type_ start__ end____ width___ exp.time_
 46 omega   18.00   44.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       52.0000   80.0000    2.7117 26

#__ type_ start__ end____ width___ exp.time_
 47 omega   17.00   42.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       52.0000   82.0000  131.2681 25

#__ type_ start__ end____ width___ exp.time_
 48 omega   25.00   57.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   77.0000  -65.7735 32

#__ type_ start__ end____ width___ exp.time_
 49 omega   90.00  117.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       60.0000   75.0000   50.8530 27

#__ type_ start__ end____ width___ exp.time_
 50 omega   28.00   54.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       60.0000   75.0000   50.8530 26

#__ type_ start__ end____ width___ exp.time_
 51 omega   30.00   56.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       60.0000   75.0000  144.4554 26

#__ type_ start__ end____ width___ exp.time_
 52 omega   34.00   60.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       68.0000   77.0000   71.8239 26

#__ type_ start__ end____ width___ exp.time_
 53 omega   38.00   65.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       68.0000   77.0000 -147.7439 27

#__ type_ start__ end____ width___ exp.time_
 54 omega   34.00   71.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       68.0000   77.0000  -24.8904 37

#__ type_ start__ end____ width___ exp.time_
 55 omega  115.00  146.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       68.0000   77.0000  -24.8904 31

#__ type_ start__ end____ width___ exp.time_
 56 omega   46.00   73.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       72.0000   54.0000   45.3578 27

#__ type_ start__ end____ width___ exp.time_
 57 omega   38.00   64.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       72.0000   77.0000  172.6703 26

#__ type_ start__ end____ width___ exp.time_
 58 omega   41.00   68.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       72.0000   76.0000 -103.6673 27

#__ type_ start__ end____ width___ exp.time_
 59 omega   45.00   71.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       76.0000   67.0000 -111.9973 26

#__ type_ start__ end____ width___ exp.time_
 60 omega   44.00   77.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       76.0000   72.0000  117.6696 33

#__ type_ start__ end____ width___ exp.time_
 61 omega   51.00  108.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       84.0000   75.0000   70.5382 57

#__ type_ start__ end____ width___ exp.time_
 62 omega   51.00   86.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       84.0000   76.0000  -84.0500 35

#__ type_ start__ end____ width___ exp.time_
 63 omega   52.00   92.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       84.0000   68.0000  163.9626 40

#__ type_ start__ end____ width___ exp.time_
 64 omega   87.00  158.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000  150.0000 71

#__ type_ start__ end____ width___ exp.time_
 65 omega  133.00  159.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000  -30.0000 26

#__ type_ start__ end____ width___ exp.time_
 66 omega   84.00  111.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000  -30.0000 27

#__ type_ start__ end____ width___ exp.time_
 67 omega   79.00  106.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000  -30.0000 27

#__ type_ start__ end____ width___ exp.time_
 68 omega  121.00  152.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000   60.0000 31

#__ type_ start__ end____ width___ exp.time_
 69 omega   80.00  121.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000  120.0000 41

#__ type_ start__ end____ width___ exp.time_
 70 omega   82.00  108.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000   60.0000 26

#__ type_ start__ end____ width___ exp.time_
 71 omega   82.00  107.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000  -90.0000 25

#__ type_ start__ end____ width___ exp.time_
 72 omega   85.00  111.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000   30.0000 26

#__ type_ start__ end____ width___ exp.time_
 73 omega   85.00  116.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000  120.0000 31

#__ type_ start__ end____ width___ exp.time_
 74 omega   84.00  123.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000   30.0000 39

#__ type_ start__ end____ width___ exp.time_
 75 omega   79.00  134.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000  150.0000 55

#__ type_ start__ end____ width___ exp.time_
 76 omega   80.00  105.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   72.0000  -72.0595 25
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.1179318000
_diffrn_orient_matrix_UB_12      -0.0185546000
_diffrn_orient_matrix_UB_13      -0.1503957000
_diffrn_orient_matrix_UB_21      -0.1441349000
_diffrn_orient_matrix_UB_22      -0.0614309000
_diffrn_orient_matrix_UB_23      -0.0372217000
_diffrn_orient_matrix_UB_31      -0.0701961000
_diffrn_orient_matrix_UB_32      0.1611093000
_diffrn_orient_matrix_UB_33      -0.0688371000
_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                2338
_reflns_number_total             2632
_reflns_odcompleteness_completeness 94.05
_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         0.329
_refine_diff_density_min         -0.494
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     179
_refine_ls_number_reflns         2632
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0330
_refine_ls_R_factor_gt           0.0281
_refine_ls_restrained_S_all      1.035
_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)+(0.0376P)²+0.3129P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0704
_refine_ls_wR_factor_ref         0.0735
_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
Cu19 Cu 0.5000 0.5000 1.0000 0.01205(10) Uani 1 2 d S T P . .
Cl20 Cl 0.76405(5) 0.55750(4) 0.86844(4) 0.01677(11) Uani 1 1 d . . . . .
O11 O 0.44953(15) 0.72849(13) 1.12486(13) 0.0175(2) Uani 1 1 d . . . . .
N1 N 0.29531(18) 0.96418(16) 1.05959(16) 0.0171(3) Uani 1 1 d . . . . .
N12 N 0.38890(16) 0.67330(15) 0.86486(15) 0.0132(3) Uani 1 1 d . . . . .
C2 C 0.3701(2) 0.82215(19) 1.04395(18) 0.0148(3) Uani 1 1 d . . . . .
C3 C 0.3391(2) 0.80161(18) 0.90120(18) 0.0141(3) Uani 1 1 d . . . . .
C4 C 0.2495(2) 0.94495(18) 0.83643(19) 0.0158(3) Uani 1 1 d . . . . .
C5 C 0.2223(2) 1.03839(19) 0.93805(19) 0.0166(3) Uani 1 1 d . . . . .
C6 C 0.1351(2) 1.18337(19) 0.9153(2) 0.0213(4) Uani 1 1 d . . . . .
H6 H 0.1174 1.2445 0.9831 0.026 Uiso 1 1 calc R . . . .
C7 C 0.0752(2) 1.23331(19) 0.7857(2) 0.0234(4) Uani 1 1 d . . . . .
H7 H 0.0142 1.3294 0.7680 0.028 Uiso 1 1 calc R . . . .
C8 C 0.1039(2) 1.1436(2) 0.6819(2) 0.0222(4) Uani 1 1 d . . . . .
H8 H 0.0646 1.1814 0.5956 0.027 Uiso 1 1 calc R . . . .
C9 C 0.1915(2) 0.99740(19) 0.7067(2) 0.0185(3) Uani 1 1 d . . . . .
H9 H 0.2105 0.9368 0.6381 0.022 Uiso 1 1 calc R . . . .
C10 C 0.2883(2) 1.0276(2) 1.1859(2) 0.0211(4) Uani 1 1 d . . . . .
H10A H 0.1755 1.0248 1.2498 0.032 Uiso 1 1 calc GR . . . .
H10B H 0.3116 1.1299 1.1528 0.032 Uiso 1 1 calc GR . . . .
H10C H 0.3733 0.9698 1.2384 0.032 Uiso 1 1 calc GR . . . .
C13 C 0.3585(2) 0.65773(17) 0.72846(18) 0.0141(3) Uani 1 1 d . . . . .
C14 C 0.2044(2) 0.61232(19) 0.72940(19) 0.0172(3) Uani 1 1 d . . . . .
H14 H 0.1253 0.5854 0.8174 0.021 Uiso 1 1 calc R . . . .
C15 C 0.1704(2) 0.6078(2) 0.5957(2) 0.0193(3) Uani 1 1 d . . . . .
H15 H 0.0665 0.5795 0.5942 0.023 Uiso 1 1 calc R . . . .
C16 C 0.2903(2) 0.64526(19) 0.46441(19) 0.0196(4) Uani 1 1 d . . . . .
H16 H 0.2666 0.6420 0.3756 0.024 Uiso 1 1 calc R . . . .
C17 C 0.4453(2) 0.6875(2) 0.46628(19) 0.0196(3) Uani 1 1 d . . . . .
H17 H 0.5258 0.7119 0.3785 0.024 Uiso 1 1 calc R . . . .
C18 C 0.4809(2) 0.69361(19) 0.59865(19) 0.0171(3) Uani 1 1 d . . . . .
H18 H 0.5850 0.7213 0.6002 0.021 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
Cu19 Cl20 2.2684(4) 2_667 ?
Cu19 Cl20 2.2684(4) . ?
Cu19 N12 2.0270(14) . ?
Cu19 N12 2.0270(14) 2_667 ?
O11 C2 1.220(2) . ?
N1 C2 1.364(2) . ?
N1 C5 1.414(2) . ?
N1 C10 1.455(2) . ?
N12 C3 1.280(2) . ?
N12 C13 1.439(2) . ?
C2 C3 1.518(2) . ?
C3 C4 1.462(2) . ?
C4 C5 1.405(2) . ?
C4 C9 1.390(2) . ?
C5 C6 1.386(2) . ?
C6 H6 0.9300 . ?
C6 C7 1.395(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.394(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.398(2) . ?
C9 H9 0.9300 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C13 C14 1.385(2) . ?
C13 C18 1.389(2) . ?
C14 H14 0.9300 . ?
C14 C15 1.394(2) . ?
C15 H15 0.9300 . ?
C15 C16 1.390(3) . ?
C16 H16 0.9300 . ?
C16 C17 1.387(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.391(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
Cl20 Cu19 Cl20 180.0 2_667 . ?
N12 Cu19 Cl20 90.59(4) 2_667 . ?
N12 Cu19 Cl20 90.59(4) . 2_667 ?
N12 Cu19 Cl20 89.41(4) . . ?
N12 Cu19 Cl20 89.41(4) 2_667 2_667 ?
N12 Cu19 N12 180.00(7) . 2_667 ?
C2 N1 C5 110.32(14) . . ?
C2 N1 C10 124.39(15) . . ?
C5 N1 C10 125.27(14) . . ?
C3 N12 Cu19 120.07(12) . . ?
C3 N12 C13 117.45(14) . . ?
C13 N12 Cu19 122.46(10) . . ?
O11 C2 N1 128.25(16) . . ?
O11 C2 C3 125.36(15) . . ?
N1 C2 C3 106.38(14) . . ?
N12 C3 C2 118.81(15) . . ?
N12 C3 C4 134.61(16) . . ?
C4 C3 C2 106.56(13) . . ?
C5 C4 C3 105.76(15) . . ?
C9 C4 C3 133.89(16) . . ?
C9 C4 C5 120.34(15) . . ?
C4 C5 N1 110.89(14) . . ?
C6 C5 N1 127.04(16) . . ?
C6 C5 C4 122.07(17) . . ?
C5 C6 H6 121.6 . . ?
C5 C6 C7 116.85(17) . . ?
C7 C6 H6 121.6 . . ?
C6 C7 H7 119.0 . . ?
C8 C7 C6 122.03(16) . . ?
C8 C7 H7 119.0 . . ?
C7 C8 H8 119.8 . . ?
C7 C8 C9 120.47(17) . . ?
C9 C8 H8 119.8 . . ?
C4 C9 C8 118.21(17) . . ?
C4 C9 H9 120.9 . . ?
C8 C9 H9 120.9 . . ?
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 118.89(15) . . ?
C14 C13 C18 121.57(16) . . ?
C18 C13 N12 119.49(15) . . ?
C13 C14 H14 120.7 . . ?
C13 C14 C15 118.64(16) . . ?
C15 C14 H14 120.7 . . ?
C14 C15 H15 119.7 . . ?
C16 C15 C14 120.60(16) . . ?
C16 C15 H15 119.7 . . ?
C15 C16 H16 120.1 . . ?
C17 C16 C15 119.81(17) . . ?
C17 C16 H16 120.1 . . ?
C16 C17 H17 119.8 . . ?
C16 C17 C18 120.37(16) . . ?
C18 C17 H17 119.8 . . ?
C13 C18 C17 118.99(16) . . ?
C13 C18 H18 120.5 . . ?
C17 C18 H18 120.5 . . ?

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
Cu19 N12 C3 C2 1.91(19) . . . . ?
Cu19 N12 C3 C4 -176.54(14) . . . . ?
Cu19 N12 C13 C14 88.74(16) . . . . ?
Cu19 N12 C13 C18 -93.58(16) . . . . ?
O11 C2 C3 N12 5.0(2) . . . . ?
O11 C2 C3 C4 -176.16(15) . . . . ?
N1 C2 C3 N12 -176.17(14) . . . . ?
N1 C2 C3 C4 2.68(17) . . . . ?
N1 C5 C6 C7 179.50(16) . . . . ?
N12 C3 C4 C5 175.62(18) . . . . ?
N12 C3 C4 C9 -3.5(3) . . . . ?
N12 C13 C14 C15 175.47(14) . . . . ?
N12 C13 C18 C17 -175.87(15) . . . . ?
C2 N1 C5 C4 -0.57(19) . . . . ?
C2 N1 C5 C6 179.75(16) . . . . ?
C2 C3 C4 C5 -2.96(17) . . . . ?
C2 C3 C4 C9 177.89(18) . . . . ?
C3 N12 C13 C14 -89.65(19) . . . . ?
C3 N12 C13 C18 88.02(18) . . . . ?
C3 C4 C5 N1 2.27(18) . . . . ?
C3 C4 C5 C6 -178.04(15) . . . . ?
C3 C4 C9 C8 178.09(17) . . . . ?
C4 C5 C6 C7 -0.1(3) . . . . ?
C5 N1 C2 O11 177.46(16) . . . . ?
C5 N1 C2 C3 -1.33(17) . . . . ?
C5 C4 C9 C8 -1.0(2) . . . . ?
C5 C6 C7 C8 -1.2(3) . . . . ?
C6 C7 C8 C9 1.5(3) . . . . ?
C7 C8 C9 C4 -0.4(3) . . . . ?
C9 C4 C5 N1 -178.44(15) . . . . ?
C9 C4 C5 C6 1.3(3) . . . . ?
C10 N1 C2 O11 -4.1(3) . . . . ?
C10 N1 C2 C3 177.09(14) . . . . ?
C10 N1 C5 C4 -178.97(15) . . . . ?
C10 N1 C5 C6 1.4(3) . . . . ?
C13 N12 C3 C2 -179.66(13) . . . . ?
C13 N12 C3 C4 1.9(3) . . . . ?
C13 C14 C15 C16 1.3(3) . . . . ?
C14 C13 C18 C17 1.7(2) . . . . ?
C14 C15 C16 C17 0.0(3) . . . . ?
C15 C16 C17 C18 -0.4(3) . . . . ?
C16 C17 C18 C13 -0.4(3) . . . . ?
C18 C13 C14 C15 -2.2(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_pd_157
_database_code_depnum_ccdc_archive 'CCDC 1538870'
_audit_update_record             
;
2017-03-19 deposited with the CCDC.
2018-10-29 downloaded from the CCDC.
;
_audit_creation_date             2016-12-01
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.11.24 svn.r3356 for OlexSys, GUI svn.r5267)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C30 H24 Br Cu N4 O4'
_chemical_formula_sum            'C30 H24 Br Cu N4 O4'
_chemical_formula_weight         647.98
_chemical_melting_point          ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -1.9646 0.5888 '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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   17.9161(9)
_cell_length_b                   6.9866(5)
_cell_length_c                   21.0116(9)
_cell_angle_alpha                90
_cell_angle_beta                 91.316(5)
_cell_angle_gamma                90
_cell_volume                     2629.4(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1484
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      75.2970
_cell_measurement_theta_min      4.1960
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.330
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.26707
_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.
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.637
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1312
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0701
_diffrn_reflns_av_unetI/netI     0.0831
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            4917
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.490
_diffrn_reflns_theta_min         4.209
_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 0.9864
_diffrn_measured_fraction_theta_max 0.9585
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega -103.00  -66.00   1.0000   23.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787 -150.0000  168.0000 37

#__ type_ start__ end____ width___ exp.time_
  2 omega  -46.00  -17.00   1.0000   23.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787  -32.0000   33.0000 29

#__ type_ start__ end____ width___ exp.time_
  3 omega -114.00  -16.00   1.0000   23.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787  -57.0000  150.0000 98

#__ type_ start__ end____ width___ exp.time_
  4 omega   59.00  128.00   1.0000   23.0000
omega____ theta____ kappa____ phi______ frames
    -       40.3787  178.0000   90.0000 69

#__ type_ start__ end____ width___ exp.time_
  5 omega   95.00  121.00   1.0000   23.0000
omega____ theta____ kappa____ phi______ frames
    -       40.3787  178.0000 -180.0000 26

#__ type_ start__ end____ width___ exp.time_
  6 omega   50.00  107.00   1.0000   65.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000  -90.0000 57

#__ type_ start__ end____ width___ exp.time_
  7 omega   35.00   71.00   1.0000   65.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000  120.0000 36

#__ type_ start__ end____ width___ exp.time_
  8 omega   39.00   78.00   1.0000   65.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000 -150.0000 39

#__ type_ start__ end____ width___ exp.time_
  9 omega   82.00  115.00   1.0000   65.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   30.0000 -120.0000 33

#__ type_ start__ end____ width___ exp.time_
 10 omega   35.00   85.00   1.0000   65.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000   60.0000 50

#__ type_ start__ end____ width___ exp.time_
 11 omega  142.00  177.00   1.0000   65.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   30.0000 -120.0000 35

#__ type_ start__ end____ width___ exp.time_
 12 omega   72.00  113.00   1.0000   65.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000   60.0000 41

#__ type_ start__ end____ width___ exp.time_
 13 omega  136.00  178.00   1.0000   65.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  112.0000 -150.0000 42

#__ type_ start__ end____ width___ exp.time_
 14 omega   42.00   97.00   1.0000   65.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000  -30.0000 55

#__ type_ start__ end____ width___ exp.time_
 15 omega   58.00  125.00   1.0000   65.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  178.0000  -30.0000 67
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0093166000
_diffrn_orient_matrix_UB_12      -0.2163150000
_diffrn_orient_matrix_UB_13      0.0112700000
_diffrn_orient_matrix_UB_21      0.0772515000
_diffrn_orient_matrix_UB_22      -0.0361800000
_diffrn_orient_matrix_UB_23      -0.0285499000
_diffrn_orient_matrix_UB_31      0.0369190000
_diffrn_orient_matrix_UB_32      0.0212337000
_diffrn_orient_matrix_UB_33      0.0665571000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2011
_reflns_number_total             2547
_reflns_odcompleteness_completeness 98.64
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     69.95
_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 1.171.37.35 (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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.435
_refine_diff_density_min         -1.498
_refine_diff_density_rms         0.158
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2547
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0892
_refine_ls_R_factor_gt           0.0757
_refine_ls_restrained_S_all      1.022
_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)+(0.1347P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1958
_refine_ls_wR_factor_ref         0.2125
_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, All O(H) groups
2. Restrained distances
 O19A-H19A = O19B-H19B
 0.9 with sigma of 0.02
 Br21_$1-H19B
 2.5 with sigma of 0.02
 O19B-C14
 1.3 with sigma of 0.02
3. Others
 Sof(H18)=Sof(O19B)=Sof(H19B)=1-FVAR(1)
 Sof(H14)=Sof(O19A)=Sof(H19A)=FVAR(1)
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)
4.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.5900(3) 0.7090(8) 0.4394(2) 0.0343(10) Uani 1 1 d . . . . .
C2 C 0.5682(3) 0.6643(8) 0.3788(3) 0.0301(11) Uani 1 1 d . . . . .
C3 C 0.4834(3) 0.6698(7) 0.3768(2) 0.0233(9) Uani 1 1 d . . . . .
C4 C 0.4606(3) 0.7203(8) 0.4411(2) 0.0271(10) Uani 1 1 d . . . . .
C5 C 0.5271(3) 0.7381(8) 0.4777(2) 0.0314(11) Uani 1 1 d . . . . .
C6 C 0.5263(4) 0.7791(9) 0.5419(3) 0.0410(14) Uani 1 1 d . . . . .
H6 H 0.5702 0.7933 0.5658 0.049 Uiso 1 1 calc R . . . .
C7 C 0.4570(4) 0.7982(10) 0.5692(2) 0.0441(15) Uani 1 1 d . . . . .
H7 H 0.4551 0.8249 0.6125 0.053 Uiso 1 1 calc R . . . .
C8 C 0.3904(4) 0.7793(10) 0.5347(2) 0.0420(14) Uani 1 1 d . . . . .
H8 H 0.3450 0.7927 0.5549 0.050 Uiso 1 1 calc R . . . .
C9 C 0.3918(3) 0.7401(9) 0.4697(2) 0.0339(11) Uani 1 1 d . . . . .
H9 H 0.3476 0.7275 0.4459 0.041 Uiso 1 1 calc R . . . .
C10 C 0.6671(4) 0.7137(11) 0.4627(3) 0.0470(15) Uani 1 1 d . . . . .
H10A H 0.6992 0.6647 0.4306 0.071 Uiso 1 1 calc GR . . . .
H10B H 0.6721 0.6363 0.5004 0.071 Uiso 1 1 calc GR . . . .
H10C H 0.6810 0.8432 0.4727 0.071 Uiso 1 1 calc GR . . . .
O11 O 0.6080(2) 0.6252(7) 0.33459(19) 0.0385(9) Uani 1 1 d . . . . .
N12 N 0.4490(2) 0.6309(6) 0.32449(19) 0.0251(8) Uani 1 1 d . . . . .
C13 C 0.3688(3) 0.6448(8) 0.3237(2) 0.0278(11) Uani 1 1 d . . . . .
C14 C 0.3357(4) 0.8247(11) 0.3220(3) 0.0441(16) Uani 1 1 d D . . . .
H14 H 0.3654 0.9338 0.3208 0.053 Uiso 0.651(14) 1 calc R . . A 1
C15 C 0.2586(5) 0.8420(16) 0.3220(3) 0.064(3) Uani 1 1 d . . . . .
H15 H 0.2367 0.9626 0.3215 0.077 Uiso 1 1 calc R . . . .
C16 C 0.2154(4) 0.6831(19) 0.3229(3) 0.070(3) Uani 1 1 d . . . . .
H16 H 0.1637 0.6954 0.3224 0.084 Uiso 1 1 calc R . . . .
C17 C 0.2470(4) 0.5034(18) 0.3245(3) 0.067(3) Uani 1 1 d . . . . .
H17 H 0.2168 0.3953 0.3252 0.081 Uiso 1 1 calc R . . . .
C18 C 0.3251(4) 0.4834(11) 0.3249(2) 0.0402(14) Uani 1 1 d . . . . .
H18 H 0.3468 0.3626 0.3259 0.048 Uiso 0.349(14) 1 calc R . . A 2
O19A O 0.3501(4) 0.3152(11) 0.3318(4) 0.047(2) Uani 0.651(14) 1 d D . . A 1
H19A H 0.388(6) 0.31(2) 0.305(6) 0.070 Uiso 0.651(14) 1 d DR . . A 1
O19B O 0.3661(8) 0.9814(19) 0.3314(7) 0.049(4) Uani 0.349(14) 1 d D . . A 2
H19B H 0.394(11) 1.00(3) 0.297(5) 0.073 Uiso 0.349(14) 1 d DR . . A 2
Cu20 Cu 0.5000 0.53353(18) 0.2500 0.0289(3) Uani 1 2 d S T P . .
Br21 Br 0.5000 0.18497(13) 0.2500 0.0351(3) Uani 1 2 d DS T P . .


_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 1.360(7) . ?
N1 C5 1.415(8) . ?
N1 C10 1.457(7) . ?
C2 C3 1.518(7) . ?
C2 O11 1.216(7) . ?
C3 C4 1.463(6) . ?
C3 N12 1.279(7) . ?
C4 C5 1.410(7) . ?
C4 C9 1.389(7) . ?
C5 C6 1.378(7) . ?
C6 H6 0.9300 . ?
C6 C7 1.385(11) . ?
C7 H7 0.9300 . ?
C7 C8 1.388(11) . ?
C8 H8 0.9300 . ?
C8 C9 1.396(7) . ?
C9 H9 0.9300 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
N12 C13 1.440(6) . ?
N12 Cu20 1.953(4) . ?
C13 C14 1.389(8) . ?
C13 C18 1.373(9) . ?
C14 H14 0.9300 . ?
C14 C15 1.386(10) . ?
C14 O19B 1.237(14) . ?
C15 H15 0.9300 . ?
C15 C16 1.355(15) . ?
C16 H16 0.9300 . ?
C16 C17 1.378(15) . ?
C17 H17 0.9300 . ?
C17 C18 1.405(10) . ?
C18 H18 0.9300 . ?
C18 O19A 1.265(11) . ?
O19A H19A 0.90(2) . ?
O19B H19B 0.90(2) . ?
Cu20 N12 1.953(4) 2_655 ?
Cu20 Br21 2.4353(16) . ?

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 110.5(4) . . ?
C2 N1 C10 124.8(5) . . ?
C5 N1 C10 124.6(5) . . ?
N1 C2 C3 106.6(4) . . ?
O11 C2 N1 127.3(5) . . ?
O11 C2 C3 126.1(5) . . ?
C4 C3 C2 106.4(4) . . ?
N12 C3 C2 118.8(4) . . ?
N12 C3 C4 134.8(5) . . ?
C5 C4 C3 105.9(5) . . ?
C9 C4 C3 133.8(5) . . ?
C9 C4 C5 120.1(5) . . ?
C4 C5 N1 110.5(4) . . ?
C6 C5 N1 127.8(5) . . ?
C6 C5 C4 121.6(6) . . ?
C5 C6 H6 121.5 . . ?
C5 C6 C7 117.0(6) . . ?
C7 C6 H6 121.5 . . ?
C6 C7 H7 118.6 . . ?
C6 C7 C8 122.9(5) . . ?
C8 C7 H7 118.6 . . ?
C7 C8 H8 120.2 . . ?
C7 C8 C9 119.6(6) . . ?
C9 C8 H8 120.2 . . ?
C4 C9 C8 118.6(5) . . ?
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 . . ?
C3 N12 C13 117.2(4) . . ?
C3 N12 Cu20 122.5(4) . . ?
C13 N12 Cu20 120.0(3) . . ?
C14 C13 N12 119.1(5) . . ?
C18 C13 N12 120.9(5) . . ?
C18 C13 C14 120.0(6) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 C13 120.2(8) . . ?
C15 C14 H14 119.9 . . ?
O19B C14 C13 127.6(9) . . ?
O19B C14 C15 110.9(9) . . ?
C14 C15 H15 120.0 . . ?
C16 C15 C14 119.9(8) . . ?
C16 C15 H15 120.0 . . ?
C15 C16 H16 119.6 . . ?
C15 C16 C17 120.8(7) . . ?
C17 C16 H16 119.6 . . ?
C16 C17 H17 120.0 . . ?
C16 C17 C18 120.0(8) . . ?
C18 C17 H17 120.0 . . ?
C13 C18 C17 119.1(8) . . ?
C13 C18 H18 120.5 . . ?
C17 C18 H18 120.5 . . ?
O19A C18 C13 124.3(6) . . ?
O19A C18 C17 116.3(8) . . ?
C18 O19A H19A 103(10) . . ?
C14 O19B H19B 106(7) . . ?
N12 Cu20 N12 139.2(3) . 2_655 ?
N12 Cu20 Br21 110.38(13) . . ?
N12 Cu20 Br21 110.38(13) 2_655 . ?

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 -0.2(6) . . . . ?
N1 C2 C3 N12 -179.4(5) . . . . ?
N1 C5 C6 C7 -178.9(6) . . . . ?
C2 N1 C5 C4 -2.5(7) . . . . ?
C2 N1 C5 C6 177.6(6) . . . . ?
C2 C3 C4 C5 -1.3(6) . . . . ?
C2 C3 C4 C9 -177.1(6) . . . . ?
C2 C3 N12 C13 -177.7(5) . . . . ?
C2 C3 N12 Cu20 7.9(7) . . . . ?
C3 C4 C5 N1 2.3(6) . . . . ?
C3 C4 C5 C6 -177.9(5) . . . . ?
C3 C4 C9 C8 175.9(6) . . . . ?
C3 N12 C13 C14 75.5(6) . . . . ?
C3 N12 C13 C18 -104.4(6) . . . . ?
C4 C3 N12 C13 3.4(9) . . . . ?
C4 C3 N12 Cu20 -171.1(5) . . . . ?
C4 C5 C6 C7 1.3(9) . . . . ?
C5 N1 C2 C3 1.6(6) . . . . ?
C5 N1 C2 O11 -177.7(6) . . . . ?
C5 C4 C9 C8 0.6(9) . . . . ?
C5 C6 C7 C8 -0.5(10) . . . . ?
C6 C7 C8 C9 -0.3(11) . . . . ?
C7 C8 C9 C4 0.2(10) . . . . ?
C9 C4 C5 N1 178.8(5) . . . . ?
C9 C4 C5 C6 -1.4(9) . . . . ?
C10 N1 C2 C3 177.8(5) . . . . ?
C10 N1 C2 O11 -1.5(10) . . . . ?
C10 N1 C5 C4 -178.8(6) . . . . ?
C10 N1 C5 C6 1.4(10) . . . . ?
O11 C2 C3 C4 179.1(6) . . . . ?
O11 C2 C3 N12 -0.1(8) . . . . ?
N12 C3 C4 C5 177.8(6) . . . . ?
N12 C3 C4 C9 2.0(11) . . . . ?
N12 C13 C14 C15 -179.2(5) . . . . ?
N12 C13 C14 O19B -13.0(13) . . . . ?
N12 C13 C18 C17 179.7(5) . . . . ?
N12 C13 C18 O19A 6.0(9) . . . . ?
C13 C14 C15 C16 -0.9(10) . . . . ?
C14 C13 C18 C17 -0.2(8) . . . . ?
C14 C13 C18 O19A -173.9(6) . . . . ?
C14 C15 C16 C17 0.7(11) . . . . ?
C15 C16 C17 C18 -0.3(10) . . . . ?
C16 C17 C18 C13 0.0(8) . . . . ?
C16 C17 C18 O19A 174.2(7) . . . . ?
C18 C13 C14 C15 0.7(9) . . . . ?
C18 C13 C14 O19B 166.8(10) . . . . ?
O19B C14 C15 C16 -169.2(9) . . . . ?
Cu20 N12 C13 C14 -109.9(5) . . . . ?
Cu20 N12 C13 C18 70.2(5) . . . . ?

####################################################################### 
# 
# 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_pd_163
_database_code_depnum_ccdc_archive 'CCDC 1538871'
_audit_update_record             
;
2017-03-19 deposited with the CCDC.
2018-10-29 downloaded from the CCDC.
;
_audit_creation_date             2017-01-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5292)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C32 H28 Cl2 Cu N4 O2'
_chemical_formula_sum            'C32 H28 Cl2 Cu N4 O2'
_chemical_formula_weight         635.02
_chemical_melting_point          ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -1.9646 0.5888 '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                   8.9050(7)
_cell_length_b                   9.2277(4)
_cell_length_c                   9.8071(7)
_cell_angle_alpha                74.790(5)
_cell_angle_beta                 65.400(7)
_cell_angle_gamma                76.151(5)
_cell_volume                     699.24(9)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    2054
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      75.7930
_cell_measurement_theta_min      5.0230
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.167
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79119
_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.
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.508
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             327
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.05
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0352
_diffrn_reflns_av_unetI/netI     0.0535
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4591
_diffrn_reflns_point_group_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.498
_diffrn_reflns_theta_min         5.022
_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 0.974
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega -111.00  -14.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787  -57.0000  -30.0000 97

#__ type_ start__ end____ width___ exp.time_
  2 omega   -5.00   36.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787   38.0000 -120.0000 41

#__ type_ start__ end____ width___ exp.time_
  3 omega  -37.00   36.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787   38.0000  120.0000 73

#__ type_ start__ end____ width___ exp.time_
  4 omega  -66.00   11.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787   57.0000 -150.0000 77

#__ type_ start__ end____ width___ exp.time_
  5 omega   84.00  121.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -       40.3787  178.0000 -180.0000 37

#__ type_ start__ end____ width___ exp.time_
  6 omega   62.00  130.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -       40.3787  178.0000   30.0000 68

#__ type_ start__ end____ width___ exp.time_
  7 omega   87.00  177.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   30.0000  -90.0000 90

#__ type_ start__ end____ width___ exp.time_
  8 omega   35.00   91.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000  -60.0000 56

#__ type_ start__ end____ width___ exp.time_
  9 omega  108.00  147.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000 -150.0000 39

#__ type_ start__ end____ width___ exp.time_
 10 omega   35.00   76.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000 -120.0000 41

#__ type_ start__ end____ width___ exp.time_
 11 omega  129.00  176.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   30.0000 -150.0000 47

#__ type_ start__ end____ width___ exp.time_
 12 omega   76.00  143.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -61.0000   90.0000 67

#__ type_ start__ end____ width___ exp.time_
 13 omega   89.00  114.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000 -180.0000 25

#__ type_ start__ end____ width___ exp.time_
 14 omega   67.00  113.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000  -60.0000 46

#__ type_ start__ end____ width___ exp.time_
 15 omega  122.00  148.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  112.0000 -150.0000 26

#__ type_ start__ end____ width___ exp.time_
 16 omega   96.00  125.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   15.0000    0.0000 29

#__ type_ start__ end____ width___ exp.time_
 17 omega   54.00  111.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000   60.0000 57

#__ type_ start__ end____ width___ exp.time_
 18 omega   43.00  122.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -61.0000   30.0000 79

#__ type_ start__ end____ width___ exp.time_
 19 omega  130.00  175.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   15.0000    0.0000 45

#__ type_ start__ end____ width___ exp.time_
 20 omega   57.00   93.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000  -30.0000 36

#__ type_ start__ end____ width___ exp.time_
 21 omega   35.00   87.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000   90.0000 52

#__ type_ start__ end____ width___ exp.time_
 22 omega   62.00   87.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000 -180.0000 25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.1252817000
_diffrn_orient_matrix_UB_12      0.0114141000
_diffrn_orient_matrix_UB_13      -0.1665857000
_diffrn_orient_matrix_UB_21      -0.1242934000
_diffrn_orient_matrix_UB_22      -0.0512202000
_diffrn_orient_matrix_UB_23      -0.0431730000
_diffrn_orient_matrix_UB_31      -0.0766333000
_diffrn_orient_matrix_UB_32      0.1668907000
_diffrn_orient_matrix_UB_33      -0.0358193000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2294
_reflns_number_total             2689
_reflns_odcompleteness_completeness 96.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     72.42
_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 1.171.37.35 (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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.618
_refine_diff_density_min         -0.429
_refine_diff_density_rms         0.075
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     189
_refine_ls_number_reflns         2689
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0468
_refine_ls_R_factor_gt           0.0389
_refine_ls_restrained_S_all      1.041
_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)+(0.0524P)²+0.0465P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0959
_refine_ls_wR_factor_ref         0.1030
_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), C9(H9), 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)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.2997(2) 0.4647(2) 0.5861(2) 0.0179(4) Uani 1 1 d . . . . .
C2 C 0.3713(3) 0.3222(2) 0.5601(2) 0.0158(4) Uani 1 1 d . . . . .
C3 C 0.3437(3) 0.3051(3) 0.4224(2) 0.0161(4) Uani 1 1 d . . . . .
C4 C 0.2574(3) 0.4517(2) 0.3714(2) 0.0162(4) Uani 1 1 d . . . . .
C5 C 0.2313(3) 0.5438(3) 0.4755(2) 0.0173(4) Uani 1 1 d . . . . .
C6 C 0.1470(3) 0.6896(3) 0.4655(3) 0.0207(5) Uani 1 1 d . . . . .
H6 H 0.1297 0.7496 0.5350 0.025 Uiso 1 1 calc R . . . .
C7 C 0.0886(3) 0.7437(3) 0.3472(3) 0.0216(5) Uani 1 1 d . . . . .
H7 H 0.0307 0.8418 0.3389 0.026 Uiso 1 1 calc R . . . .
C8 C 0.1135(3) 0.6565(3) 0.2403(3) 0.0194(5) Uani 1 1 d . . . . .
C9 C 0.1989(3) 0.5083(3) 0.2532(2) 0.0188(4) Uani 1 1 d . . . . .
H9 H 0.2163 0.4481 0.1838 0.023 Uiso 1 1 calc R . . . .
C10 C 0.2865(3) 0.5262(3) 0.7132(3) 0.0222(5) Uani 1 1 d . . . . .
H10A H 0.1739 0.5302 0.7868 0.033 Uiso 1 1 calc GR . . . .
H10B H 0.3161 0.6267 0.6769 0.033 Uiso 1 1 calc GR . . . .
H10C H 0.3609 0.4624 0.7601 0.033 Uiso 1 1 calc GR . . . .
O11 O 0.4461(2) 0.22451(18) 0.62964(17) 0.0196(3) Uani 1 1 d . . . . .
N12 N 0.3920(2) 0.1766(2) 0.38028(19) 0.0151(4) Uani 1 1 d . . . . .
C13 C 0.3705(3) 0.1628(2) 0.2474(2) 0.0162(4) Uani 1 1 d . . . . .
C14 C 0.4871(3) 0.2121(3) 0.1039(3) 0.0202(5) Uani 1 1 d . . . . .
H14 H 0.5796 0.2496 0.0945 0.024 Uiso 1 1 calc R . . . .
C15 C 0.4632(3) 0.2043(3) -0.0254(2) 0.0220(5) Uani 1 1 d . . . . .
H15 H 0.5404 0.2360 -0.1220 0.026 Uiso 1 1 calc R . . . .
C16 C 0.3239(3) 0.1491(3) -0.0099(2) 0.0216(5) Uani 1 1 d . . . . .
H16 H 0.3080 0.1442 -0.0964 0.026 Uiso 1 1 calc R . . . .
C17 C 0.2086(3) 0.1013(3) 0.1333(3) 0.0218(5) Uani 1 1 d . . . . .
H17 H 0.1145 0.0664 0.1425 0.026 Uiso 1 1 calc R . . . .
C18 C 0.2326(3) 0.1051(3) 0.2640(2) 0.0200(5) Uani 1 1 d . . . . .
H18 H 0.1575 0.0697 0.3604 0.024 Uiso 1 1 calc R . . . .
C19 C 0.0499(3) 0.7241(3) 0.1132(3) 0.0251(5) Uani 1 1 d . . . . .
H19A H -0.0624 0.7751 0.1541 0.038 Uiso 1 1 calc GR . . . .
H19B H 0.0515 0.6447 0.0658 0.038 Uiso 1 1 calc GR . . . .
H19C H 0.1201 0.7955 0.0389 0.038 Uiso 1 1 calc GR . . . .
Cu20 Cu 0.5000 0.0000 0.5000 0.01419(14) Uani 1 2 d S T P . .
Cl21 Cl 0.75527(6) 0.05975(6) 0.33252(6) 0.01959(15) 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
N1 C2 1.356(3) . ?
N1 C5 1.416(3) . ?
N1 C10 1.452(3) . ?
C2 C3 1.522(3) . ?
C2 O11 1.221(3) . ?
C3 C4 1.462(3) . ?
C3 N12 1.275(3) . ?
C4 C5 1.407(3) . ?
C4 C9 1.394(3) . ?
C5 C6 1.375(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.393(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.400(4) . ?
C8 C9 1.399(3) . ?
C8 C19 1.508(3) . ?
C9 H9 0.9300 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
N12 C13 1.435(3) . ?
N12 Cu20 2.0361(17) . ?
C13 C14 1.392(3) . ?
C13 C18 1.385(4) . ?
C14 H14 0.9300 . ?
C14 C15 1.392(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.387(4) . ?
C16 H16 0.9300 . ?
C16 C17 1.383(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.395(3) . ?
C18 H18 0.9300 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
Cu20 N12 2.0361(17) 2_656 ?
Cu20 Cl21 2.2772(6) . ?
Cu20 Cl21 2.2772(6) 2_656 ?

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 110.30(19) . . ?
C2 N1 C10 125.40(19) . . ?
C5 N1 C10 124.23(19) . . ?
N1 C2 C3 106.69(18) . . ?
O11 C2 N1 128.2(2) . . ?
O11 C2 C3 125.1(2) . . ?
C4 C3 C2 106.28(18) . . ?
N12 C3 C2 118.63(18) . . ?
N12 C3 C4 135.1(2) . . ?
C5 C4 C3 105.81(19) . . ?
C9 C4 C3 134.1(2) . . ?
C9 C4 C5 120.0(2) . . ?
C4 C5 N1 110.87(19) . . ?
C6 C5 N1 127.3(2) . . ?
C6 C5 C4 121.8(2) . . ?
C5 C6 H6 121.3 . . ?
C5 C6 C7 117.3(2) . . ?
C7 C6 H6 121.3 . . ?
C6 C7 H7 118.6 . . ?
C6 C7 C8 122.7(2) . . ?
C8 C7 H7 118.6 . . ?
C7 C8 C19 119.7(2) . . ?
C9 C8 C7 118.9(2) . . ?
C9 C8 C19 121.4(2) . . ?
C4 C9 C8 119.2(2) . . ?
C4 C9 H9 120.4 . . ?
C8 C9 H9 120.4 . . ?
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 118.28(17) . . ?
C3 N12 Cu20 119.47(14) . . ?
C13 N12 Cu20 122.24(14) . . ?
C14 C13 N12 118.9(2) . . ?
C18 C13 N12 119.62(19) . . ?
C18 C13 C14 121.5(2) . . ?
C13 C14 H14 120.5 . . ?
C15 C14 C13 119.1(2) . . ?
C15 C14 H14 120.5 . . ?
C14 C15 H15 120.1 . . ?
C16 C15 C14 119.9(2) . . ?
C16 C15 H15 120.1 . . ?
C15 C16 H16 119.8 . . ?
C17 C16 C15 120.5(2) . . ?
C17 C16 H16 119.8 . . ?
C16 C17 H17 119.8 . . ?
C16 C17 C18 120.3(2) . . ?
C18 C17 H17 119.8 . . ?
C13 C18 C17 118.7(2) . . ?
C13 C18 H18 120.6 . . ?
C17 C18 H18 120.6 . . ?
C8 C19 H19A 109.5 . . ?
C8 C19 H19B 109.5 . . ?
C8 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N12 Cu20 N12 180.0 . 2_656 ?
N12 Cu20 Cl21 90.93(5) . 2_656 ?
N12 Cu20 Cl21 90.93(5) 2_656 . ?
N12 Cu20 Cl21 89.07(5) 2_656 2_656 ?
N12 Cu20 Cl21 89.07(5) . . ?
Cl21 Cu20 Cl21 180.0 . 2_656 ?

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 2.3(2) . . . . ?
N1 C2 C3 N12 -176.1(2) . . . . ?
N1 C5 C6 C7 -179.2(2) . . . . ?
C2 N1 C5 C4 0.0(3) . . . . ?
C2 N1 C5 C6 179.1(2) . . . . ?
C2 C3 C4 C5 -2.2(2) . . . . ?
C2 C3 C4 C9 179.8(2) . . . . ?
C2 C3 N12 C13 -177.99(19) . . . . ?
C2 C3 N12 Cu20 0.9(3) . . . . ?
C3 C4 C5 N1 1.4(3) . . . . ?
C3 C4 C5 C6 -177.6(2) . . . . ?
C3 C4 C9 C8 177.4(2) . . . . ?
C3 N12 C13 C14 81.3(3) . . . . ?
C3 N12 C13 C18 -96.9(3) . . . . ?
C4 C3 N12 C13 4.2(4) . . . . ?
C4 C3 N12 Cu20 -176.9(2) . . . . ?
C4 C5 C6 C7 -0.3(3) . . . . ?
C5 N1 C2 C3 -1.5(2) . . . . ?
C5 N1 C2 O11 177.7(2) . . . . ?
C5 C4 C9 C8 -0.4(3) . . . . ?
C5 C6 C7 C8 -0.4(4) . . . . ?
C6 C7 C8 C9 0.7(4) . . . . ?
C6 C7 C8 C19 -178.6(2) . . . . ?
C7 C8 C9 C4 -0.3(3) . . . . ?
C9 C4 C5 N1 179.8(2) . . . . ?
C9 C4 C5 C6 0.7(3) . . . . ?
C10 N1 C2 C3 175.6(2) . . . . ?
C10 N1 C2 O11 -5.3(4) . . . . ?
C10 N1 C5 C4 -177.0(2) . . . . ?
C10 N1 C5 C6 2.0(4) . . . . ?
O11 C2 C3 C4 -176.9(2) . . . . ?
O11 C2 C3 N12 4.7(3) . . . . ?
N12 C3 C4 C5 175.8(3) . . . . ?
N12 C3 C4 C9 -2.2(5) . . . . ?
N12 C13 C14 C15 -177.5(2) . . . . ?
N12 C13 C18 C17 176.1(2) . . . . ?
C13 C14 C15 C16 0.5(3) . . . . ?
C14 C13 C18 C17 -2.0(3) . . . . ?
C14 C15 C16 C17 -0.2(4) . . . . ?
C15 C16 C17 C18 -1.3(4) . . . . ?
C16 C17 C18 C13 2.3(3) . . . . ?
C18 C13 C14 C15 0.6(3) . . . . ?
C19 C8 C9 C4 179.0(2) . . . . ?
Cu20 N12 C13 C14 -97.6(2) . . . . ?
Cu20 N12 C13 C18 84.2(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_xrd_15
_database_code_depnum_ccdc_archive 'CCDC 1538872'
_audit_update_record             
;
2017-03-19 deposited with the CCDC.
2018-10-29 downloaded from the CCDC.
;
_audit_creation_date             2015-10-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.21 svn.r3230 for OlexSys, GUI svn.r5103)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C30 H24 Cu I N4 O2'
_chemical_formula_sum            'C30 H24 Cu I N4 O2'
_chemical_formula_weight         662.97
_chemical_melting_point          ?
_chemical_oxdiff_formula         'Cu2 C10 O10'
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'
Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.3257 6.8362 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   17.9067(5)
_cell_length_b                   6.9140(2)
_cell_length_c                   21.1065(7)
_cell_angle_alpha                90
_cell_angle_beta                 90.872(3)
_cell_angle_gamma                90
_cell_volume                     2612.82(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5465
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      75.7770
_cell_measurement_theta_min      4.1710
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    10.744
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.35240
_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            brown
_exptl_crystal_density_diffrn    1.685
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1320
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.07
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0435
_diffrn_reflns_av_unetI/netI     0.0342
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            9321
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.964
_diffrn_reflns_theta_min         4.190
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.3829
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -86.00  -10.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787   19.0000  150.0000 76

#__ type_ start__ end____ width___ exp.time_
  2 omega -100.00  -56.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787 -164.0000  103.0000 44

#__ type_ start__ end____ width___ exp.time_
  3 omega  -92.00  -65.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787  132.0000   60.0000 27

#__ type_ start__ end____ width___ exp.time_
  4 omega  -50.00   32.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787   38.0000  -30.0000 82

#__ type_ start__ end____ width___ exp.time_
  5 omega   93.00  127.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       40.3787  178.0000   30.0000 34

#__ type_ start__ end____ width___ exp.time_
  6 omega   81.00  118.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       40.3787  164.0000  127.0000 37

#__ type_ start__ end____ width___ exp.time_
  7 omega   42.00   97.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000  -60.0000 55

#__ type_ start__ end____ width___ exp.time_
  8 omega   65.00  110.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -61.0000  -60.0000 45

#__ type_ start__ end____ width___ exp.time_
  9 omega   96.00  124.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000 -150.0000 28

#__ type_ start__ end____ width___ exp.time_
 10 omega  137.00  164.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  112.0000   90.0000 27

#__ type_ start__ end____ width___ exp.time_
 11 omega  102.00  132.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  112.0000   90.0000 30

#__ type_ start__ end____ width___ exp.time_
 12 omega   65.00   90.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000 -180.0000 25

#__ type_ start__ end____ width___ exp.time_
 13 omega   36.00   68.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000  150.0000 32

#__ type_ start__ end____ width___ exp.time_
 14 omega   30.00   98.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000  -30.0000 68

#__ type_ start__ end____ width___ exp.time_
 15 omega   48.00   74.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000  150.0000 26

#__ type_ start__ end____ width___ exp.time_
 16 omega   53.00   92.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   15.0000  -30.0000 39

#__ type_ start__ end____ width___ exp.time_
 17 omega   53.00   78.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000  -60.0000 25

#__ type_ start__ end____ width___ exp.time_
 18 omega   62.00  116.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -117.0000 -107.0000 54

#__ type_ start__ end____ width___ exp.time_
 19 omega  106.00  132.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   15.0000  -30.0000 26

#__ type_ start__ end____ width___ exp.time_
 20 omega   62.00  104.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  178.0000  120.0000 42

#__ type_ start__ end____ width___ exp.time_
 21 omega  115.00  140.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  178.0000  120.0000 25

#__ type_ start__ end____ width___ exp.time_
 22 omega  102.00  172.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  112.0000    0.0000 70

#__ type_ start__ end____ width___ exp.time_
 23 omega   70.00  114.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000 -150.0000 44

#__ type_ start__ end____ width___ exp.time_
 24 omega   55.00   89.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000 -150.0000 34

#__ type_ start__ end____ width___ exp.time_
 25 omega   65.00   92.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000  -60.0000 27

#__ type_ start__ end____ width___ exp.time_
 26 omega   66.00  109.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000  -90.0000 43

#__ type_ start__ end____ width___ exp.time_
 27 omega   65.00   99.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -49.0000 -149.1123 34

#__ type_ start__ end____ width___ exp.time_
 28 omega   75.00  109.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000    0.0000 34

#__ type_ start__ end____ width___ exp.time_
 29 omega  142.00  178.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   10.0000   83.6873 36

#__ type_ start__ end____ width___ exp.time_
 30 omega  152.00  178.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000  120.0000 26

#__ type_ start__ end____ width___ exp.time_
 31 omega   88.00  134.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000   60.0000 46

#__ type_ start__ end____ width___ exp.time_
 32 omega   44.00   77.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   10.0000   83.6873 33

#__ type_ start__ end____ width___ exp.time_
 33 omega -111.00  -29.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787  -57.0000   60.0000 82

#__ type_ start__ end____ width___ exp.time_
 34 omega  -48.00    2.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787   38.0000 -180.0000 50
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0060632000
_diffrn_orient_matrix_UB_12      -0.0956974000
_diffrn_orient_matrix_UB_13      0.0656575000
_diffrn_orient_matrix_UB_21      0.0112017000
_diffrn_orient_matrix_UB_22      0.1985340000
_diffrn_orient_matrix_UB_23      0.0319305000
_diffrn_orient_matrix_UB_31      -0.0850505000
_diffrn_orient_matrix_UB_32      0.0329603000
_diffrn_orient_matrix_UB_33      -0.0015789000
_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                2404
_reflns_number_total             2477
_reflns_odcompleteness_completeness 94.40
_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, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.869
_refine_diff_density_min         -0.872
_refine_diff_density_rms         0.114
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         2477
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0325
_refine_ls_R_factor_gt           0.0312
_refine_ls_restrained_S_all      1.049
_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)+(0.0501P)²+4.3124P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0781
_refine_ls_wR_factor_ref         0.0796
_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(C14A) = Uanis(C14B) = Uanis(C15B) = Uanis(C16B) = Uanis(C17B) =
Uanis(C18B) = Uanis(C13) = Uanis(C15A) = Uanis(C16A) = Uanis(C17A) =
Uanis(C18A) = Uanis(I20)
Uanis(C10) = Uanis(N1)
3. Others
 Sof(C14B)=Sof(H14B)=Sof(C15B)=Sof(H15B)=Sof(C16B)=Sof(H16B)=Sof(C17B)=
 Sof(H17B)=Sof(C18B)=Sof(H18B)=1-FVAR(1)
 Sof(C14A)=Sof(H14A)=Sof(C15A)=Sof(H15A)=Sof(C16A)=Sof(H16A)=Sof(C17A)=
 Sof(H17A)=Sof(C18A)=Sof(H18A)=FVAR(1)
4.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C9(H9), C14A(H14A), C14B(H14B), C15B(H15B),
 C16B(H16B), C17B(H17B), C18B(H18B), C15A(H15A), C16A(H16A), C17A(H17A),
 C18A(H18A)
4.b Fitted hexagon refined as free rotating group:
 C14B(C15B,C16B,C17B,C18B,C13)
4.c 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
I20 I 0.5000 -0.36765(4) 0.7500 0.01394(11) Uani 1 2 d S T P . .
Cu19 Cu 0.5000 0.00338(9) 0.7500 0.01125(15) Uani 1 2 d S T P . .
O11 O 0.39036(11) 0.1110(3) 0.66603(12) 0.0173(5) Uani 1 1 d . . . . .
N1 N 0.41074(14) 0.2084(4) 0.56239(14) 0.0195(4) Uani 1 1 d . . . . .
N12 N 0.55002(13) 0.1087(3) 0.67599(12) 0.0104(5) Uani 1 1 d . . . . .
C2 C 0.43118(16) 0.1551(4) 0.62250(16) 0.0126(6) Uani 1 1 d . . . . .
C3 C 0.51564(15) 0.1576(4) 0.62434(15) 0.0102(5) Uani 1 1 d . . . . .
C4 C 0.53968(16) 0.2114(4) 0.56084(14) 0.0129(6) Uani 1 1 d . . . . .
C5 C 0.47367(16) 0.2377(4) 0.52464(15) 0.0151(6) Uani 1 1 d . . . . .
C6 C 0.47513(19) 0.2817(5) 0.46068(16) 0.0210(6) Uani 1 1 d . . . . .
H6 H 0.4313 0.3000 0.4373 0.025 Uiso 1 1 calc R . . . .
C7 C 0.5448(2) 0.2978(5) 0.43266(16) 0.0225(7) Uani 1 1 d . . . . .
H7 H 0.5474 0.3264 0.3897 0.027 Uiso 1 1 calc R . . . .
C8 C 0.61073(18) 0.2717(5) 0.46763(15) 0.0202(6) Uani 1 1 d . . . . .
H8 H 0.6565 0.2829 0.4477 0.024 Uiso 1 1 calc R . . . .
C9 C 0.60879(16) 0.2292(4) 0.53199(15) 0.0159(6) Uani 1 1 d . . . . .
H9 H 0.6528 0.2129 0.5553 0.019 Uiso 1 1 calc R . . . .
C10 C 0.33429(16) 0.2161(5) 0.53896(16) 0.0195(4) Uani 1 1 d . . . . .
H10A H 0.3014 0.1683 0.5709 0.029 Uiso 1 1 calc GR . . . .
H10B H 0.3294 0.1377 0.5016 0.029 Uiso 1 1 calc GR . . . .
H10C H 0.3214 0.3474 0.5289 0.029 Uiso 1 1 calc GR . . . .
C14A C 0.6705(4) 0.2889(9) 0.6819(3) 0.01394(11) Uani 0.491(12) 1 d . . . A 1
H14A H 0.6467 0.4075 0.6868 0.017 Uiso 0.491(12) 1 calc R . . A 1
C14B C 0.6593(3) 0.3069(4) 0.6756(2) 0.01394(11) Uani 0.509(12) 1 d . . . A 2
H14B H 0.6277 0.4135 0.6745 0.017 Uiso 0.509(12) 1 calc R . . A 2
C15B C 0.7363(3) 0.3333(9) 0.6765(2) 0.01394(11) Uani 0.509(12) 1 d G . . A 2
H15B H 0.7561 0.4577 0.6759 0.017 Uiso 0.509(12) 1 calc R . . A 2
C16B C 0.78362(13) 0.1740(13) 0.6781(2) 0.01394(11) Uani 0.509(12) 1 d G . . A
2
H16B H 0.8351 0.1918 0.6787 0.017 Uiso 0.509(12) 1 calc R . . A 2
C17B C 0.7540(2) -0.0118(10) 0.6789(2) 0.01394(11) Uani 0.509(12) 1 d G . . A 2
H17B H 0.7857 -0.1184 0.6800 0.017 Uiso 0.509(12) 1 calc R . . A 2
C18B C 0.6770(2) -0.0382(5) 0.6780(2) 0.01394(11) Uani 0.509(12) 1 d G . . A 2
H18B H 0.6572 -0.1626 0.6786 0.017 Uiso 0.509(12) 1 calc R . . A 2
C13 C 0.62970(11) 0.1211(4) 0.67638(14) 0.01394(11) Uani 1 1 d G . . . .
C15A C 0.7481(4) 0.2781(14) 0.6801(3) 0.01394(11) Uani 0.491(12) 1 d . . . A 1
H15A H 0.7758 0.3917 0.6817 0.017 Uiso 0.491(12) 1 calc R . . A 1
C16A C 0.7850(3) 0.1031(15) 0.6760(3) 0.01394(11) Uani 0.491(12) 1 d . . . A 1
H16A H 0.8369 0.0996 0.6759 0.017 Uiso 0.491(12) 1 calc R . . A 1
C17A C 0.7437(3) -0.0697(13) 0.6721(3) 0.01394(11) Uani 0.491(12) 1 d . . . A 1
H17A H 0.7687 -0.1871 0.6687 0.017 Uiso 0.491(12) 1 calc R . . A 1
C18A C 0.6662(3) -0.0674(10) 0.6734(3) 0.01394(11) Uani 0.491(12) 1 d . . . A 1
H18A H 0.6387 -0.1814 0.6723 0.017 Uiso 0.491(12) 1 calc R . . A 1


_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
I20 Cu19 2.5653(6) . ?
Cu19 N12 1.953(2) 2_656 ?
Cu19 N12 1.953(2) . ?
O11 C2 1.221(4) . ?
N1 C2 1.366(4) . ?
N1 C5 1.404(4) . ?
N1 C10 1.449(4) . ?
N12 C3 1.289(4) . ?
N12 C13 1.429(3) . ?
C2 C3 1.513(4) . ?
C3 C4 1.462(4) . ?
C4 C5 1.409(4) . ?
C4 C9 1.393(4) . ?
C5 C6 1.385(5) . ?
C6 H6 0.9300 . ?
C6 C7 1.393(5) . ?
C7 H7 0.9300 . ?
C7 C8 1.395(5) . ?
C8 H8 0.9300 . ?
C8 C9 1.391(4) . ?
C9 H9 0.9300 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C14A H14A 0.9300 . ?
C14A C13 1.376(7) . ?
C14A C15A 1.392(8) . ?
C14B H14B 0.9300 . ?
C14B C15B 1.3900 . ?
C14B C13 1.3900 . ?
C15B H15B 0.9300 . ?
C15B C16B 1.3900 . ?
C16B H16B 0.9300 . ?
C16B C17B 1.3900 . ?
C17B H17B 0.9300 . ?
C17B C18B 1.3900 . ?
C18B H18B 0.9300 . ?
C18B C13 1.3900 . ?
C13 C18A 1.460(7) . ?
C15A H15A 0.9300 . ?
C15A C16A 1.382(8) . ?
C16A H16A 0.9300 . ?
C16A C17A 1.407(8) . ?
C17A H17A 0.9300 . ?
C17A C18A 1.388(8) . ?
C18A H18A 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
N12 Cu19 I20 111.89(7) 2_656 . ?
N12 Cu19 I20 111.89(7) . . ?
N12 Cu19 N12 136.22(14) . 2_656 ?
C2 N1 C5 111.1(2) . . ?
C2 N1 C10 124.4(3) . . ?
C5 N1 C10 124.3(3) . . ?
C3 N12 Cu19 123.72(19) . . ?
C3 N12 C13 117.0(2) . . ?
C13 N12 Cu19 119.2(2) . . ?
O11 C2 N1 127.7(3) . . ?
O11 C2 C3 126.4(3) . . ?
N1 C2 C3 105.9(3) . . ?
N12 C3 C2 118.9(3) . . ?
N12 C3 C4 134.3(3) . . ?
C4 C3 C2 106.7(2) . . ?
C5 C4 C3 105.9(2) . . ?
C9 C4 C3 134.4(3) . . ?
C9 C4 C5 119.7(3) . . ?
N1 C5 C4 110.3(3) . . ?
C6 C5 N1 127.7(3) . . ?
C6 C5 C4 121.9(3) . . ?
C5 C6 H6 121.2 . . ?
C5 C6 C7 117.5(3) . . ?
C7 C6 H6 121.2 . . ?
C6 C7 H7 119.3 . . ?
C6 C7 C8 121.4(3) . . ?
C8 C7 H7 119.3 . . ?
C7 C8 H8 119.6 . . ?
C9 C8 C7 120.7(3) . . ?
C9 C8 H8 119.6 . . ?
C4 C9 H9 120.6 . . ?
C8 C9 C4 118.8(3) . . ?
C8 C9 H9 120.6 . . ?
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 . . ?
C13 C14A H14A 120.6 . . ?
C13 C14A C15A 118.8(5) . . ?
C15A C14A H14A 120.6 . . ?
C15B C14B H14B 120.0 . . ?
C15B C14B C13 120.0 . . ?
C13 C14B H14B 120.0 . . ?
C14B C15B H15B 120.0 . . ?
C16B C15B C14B 120.0 . . ?
C16B C15B H15B 120.0 . . ?
C15B C16B H16B 120.0 . . ?
C15B C16B C17B 120.0 . . ?
C17B C16B H16B 120.0 . . ?
C16B C17B H17B 120.0 . . ?
C16B C17B C18B 120.0 . . ?
C18B C17B H17B 120.0 . . ?
C17B C18B H18B 120.0 . . ?
C13 C18B C17B 120.0 . . ?
C13 C18B H18B 120.0 . . ?
N12 C13 C18A 113.2(3) . . ?
C14A C13 N12 125.5(3) . . ?
C14A C13 C18A 121.3(4) . . ?
C14B C13 N12 115.9(3) . . ?
C18B C13 N12 124.1(3) . . ?
C18B C13 C14B 120.0 . . ?
C14A C15A H15A 119.1 . . ?
C16A C15A C14A 121.8(6) . . ?
C16A C15A H15A 119.1 . . ?
C15A C16A H16A 120.1 . . ?
C15A C16A C17A 119.8(5) . . ?
C17A C16A H16A 120.1 . . ?
C16A C17A H17A 119.6 . . ?
C18A C17A C16A 120.9(6) . . ?
C18A C17A H17A 119.6 . . ?
C13 C18A H18A 121.3 . . ?
C17A C18A C13 117.4(5) . . ?
C17A C18A H18A 121.3 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cu19 N12 C3 C2 7.0(4) . . . . ?
Cu19 N12 C3 C4 -169.5(2) . . . . ?
Cu19 N12 C13 C14A -107.5(5) . . . . ?
Cu19 N12 C13 C14B -114.1(2) . . . . ?
Cu19 N12 C13 C18B 65.3(3) . . . . ?
Cu19 N12 C13 C18A 69.6(4) . . . . ?
O11 C2 C3 N12 0.2(4) . . . . ?
O11 C2 C3 C4 177.6(3) . . . . ?
N1 C2 C3 N12 -178.7(3) . . . . ?
N1 C2 C3 C4 -1.3(3) . . . . ?
N1 C5 C6 C7 -177.8(3) . . . . ?
N12 C3 C4 C5 176.6(3) . . . . ?
N12 C3 C4 C9 0.4(6) . . . . ?
N12 C13 C18A C17A 178.6(5) . . . . ?
C2 N1 C5 C4 -2.5(4) . . . . ?
C2 N1 C5 C6 176.1(3) . . . . ?
C2 C3 C4 C5 -0.2(3) . . . . ?
C2 C3 C4 C9 -176.4(3) . . . . ?
C3 N12 C13 C14A 76.8(5) . . . . ?
C3 N12 C13 C14B 70.1(3) . . . . ?
C3 N12 C13 C18B -110.5(3) . . . . ?
C3 N12 C13 C18A -106.1(4) . . . . ?
C3 C4 C5 N1 1.6(3) . . . . ?
C3 C4 C5 C6 -177.1(3) . . . . ?
C3 C4 C9 C8 175.5(3) . . . . ?
C4 C5 C6 C7 0.6(5) . . . . ?
C5 N1 C2 O11 -176.6(3) . . . . ?
C5 N1 C2 C3 2.3(3) . . . . ?
C5 C4 C9 C8 -0.3(4) . . . . ?
C5 C6 C7 C8 -0.4(5) . . . . ?
C6 C7 C8 C9 -0.2(5) . . . . ?
C7 C8 C9 C4 0.5(5) . . . . ?
C9 C4 C5 N1 178.4(3) . . . . ?
C9 C4 C5 C6 -0.2(5) . . . . ?
C10 N1 C2 O11 -2.0(5) . . . . ?
C10 N1 C2 C3 176.9(3) . . . . ?
C10 N1 C5 C4 -177.2(3) . . . . ?
C10 N1 C5 C6 1.4(5) . . . . ?
C14A C13 C18A C17A -4.1(9) . . . . ?
C14A C15A C16A C17A 1.5(10) . . . . ?
C14B C15B C16B C17B 0.0 . . . . ?
C14B C13 C18A C17A 3.1(9) . . . . ?
C15B C14B C13 N12 179.4(3) . . . . ?
C15B C14B C13 C14A 29(2) . . . . ?
C15B C14B C13 C18B 0.0 . . . . ?
C15B C14B C13 C18A -5.1(5) . . . . ?
C15B C16B C17B C18B 0.0 . . . . ?
C16B C17B C18B C13 0.0 . . . . ?
C17B C18B C13 N12 -179.4(3) . . . . ?
C17B C18B C13 C14A -5.7(4) . . . . ?
C17B C18B C13 C14B 0.0 . . . . ?
C17B C18B C13 C18A 160(2) . . . . ?
C18B C13 C18A C17A -19.7(16) . . . . ?
C13 N12 C3 C2 -177.4(2) . . . . ?
C13 N12 C3 C4 6.1(5) . . . . ?
C13 C14A C15A C16A -3.2(9) . . . . ?
C13 C14B C15B C16B 0.0 . . . . ?
C15A C14A C13 N12 -178.6(4) . . . . ?
C15A C14A C13 C14B -146(2) . . . . ?
C15A C14A C13 C18B 7.8(7) . . . . ?
C15A C14A C13 C18A 4.5(9) . . . . ?
C15A C16A C17A C18A -1.1(10) . . . . ?
C16A C17A C18A C13 2.3(9) . . . . ?



####################################################################### 
# 
# 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_pd_145
_database_code_depnum_ccdc_archive 'CCDC 1538877'
_audit_update_record             
;
2017-03-19 deposited with the CCDC.
2018-10-29 downloaded from the CCDC.
;
_audit_creation_date             2016-11-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.11.07 svn.r3352 for OlexSys, GUI svn.r5261)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C36 H36 Cl2 Cu2 N4 O2'
_chemical_formula_sum            'C36 H36 Cl2 Cu2 N4 O2'
_chemical_formula_weight         754.67
_chemical_melting_point          ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -1.9646 0.5888 '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                   15.435(8)
_cell_length_b                   8.1831(15)
_cell_length_c                   14.316(6)
_cell_angle_alpha                90
_cell_angle_beta                 114.64(5)
_cell_angle_gamma                90
_cell_volume                     1643.5(13)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1059
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      74.3920
_cell_measurement_theta_min      5.4360
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.405
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.24588
_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.
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.525
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.04
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1286
_diffrn_reflns_av_unetI/netI     0.1499
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5753
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.983
_diffrn_reflns_theta_min         3.150
_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 0.985
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega -119.00   -9.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      -39.8787  -77.0000 -180.0000 110

#__ type_ start__ end____ width___ exp.time_
  2 omega -109.00  -34.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      -39.8787  178.0000 -180.0000 75

#__ type_ start__ end____ width___ exp.time_
  3 omega  -71.00  -44.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      -39.8787  178.0000    0.0000 27

#__ type_ start__ end____ width___ exp.time_
  4 omega    2.00   57.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       39.8787  -99.0000   30.0000 55

#__ type_ start__ end____ width___ exp.time_
  5 omega   47.00   87.00   1.0000   45.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000  150.0000 40

#__ type_ start__ end____ width___ exp.time_
  6 omega   38.00   75.00   1.0000   45.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000 -120.0000 37

#__ type_ start__ end____ width___ exp.time_
  7 omega   43.00   91.00   1.0000   45.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000  -60.0000 48

#__ type_ start__ end____ width___ exp.time_
  8 omega   74.00  104.00   1.0000   45.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000 -120.0000 30

#__ type_ start__ end____ width___ exp.time_
  9 omega   34.00  107.00   1.0000   45.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000 -180.0000 73

#__ type_ start__ end____ width___ exp.time_
 10 omega   61.00   96.00   1.0000   45.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000  -30.0000 35

#__ type_ start__ end____ width___ exp.time_
 11 omega   37.00   78.00   1.0000   45.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000   60.0000 41

#__ type_ start__ end____ width___ exp.time_
 12 omega   88.00  170.00   1.0000   45.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000   90.0000 82

#__ type_ start__ end____ width___ exp.time_
 13 omega   56.00   95.00   1.0000   45.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000 -180.0000 39

#__ type_ start__ end____ width___ exp.time_
 14 omega   69.00   96.00   1.0000   45.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000  120.0000 27

#__ type_ start__ end____ width___ exp.time_
 15 omega  132.00  157.00   1.0000   45.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  112.0000 -150.0000 25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0687795000
_diffrn_orient_matrix_UB_12      0.1435315000
_diffrn_orient_matrix_UB_13      0.0128049000
_diffrn_orient_matrix_UB_21      -0.0842501000
_diffrn_orient_matrix_UB_22      0.1055988000
_diffrn_orient_matrix_UB_23      -0.0715362000
_diffrn_orient_matrix_UB_31      -0.0156544000
_diffrn_orient_matrix_UB_32      0.0608946000
_diffrn_orient_matrix_UB_33      0.0935985000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1493
_reflns_number_total             3059
_reflns_odcompleteness_completeness 98.24
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     69.95
_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 1.171.37.35 (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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         2.901
_refine_diff_density_min         -2.029
_refine_diff_density_rms         0.234
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.372
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         3059
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2246
_refine_ls_R_factor_gt           0.1451
_refine_ls_restrained_S_all      1.372
_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)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3741
_refine_ls_wR_factor_ref         0.4590
_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), C15(H15), C17(H17)
2.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C19(H19A,H19B,H19C), C20(H20A,H20B,H20C), C21(H21A,H21B,
 H21C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.6574(7) 0.4904(10) 0.7665(7) 0.040(2) Uani 1 1 d . . . . .
C2 C 0.6249(8) 0.3713(13) 0.6933(10) 0.043(3) Uani 1 1 d . . . . .
C3 C 0.6910(9) 0.3648(13) 0.6395(9) 0.046(3) Uani 1 1 d . . . . .
C4 C 0.7661(9) 0.4847(13) 0.6954(9) 0.045(3) Uani 1 1 d . . . . .
C5 C 0.7416(9) 0.5581(12) 0.7694(10) 0.043(3) Uani 1 1 d . . . . .
C6 C 0.7965(8) 0.6776(12) 0.8359(10) 0.045(3) Uani 1 1 d . . . . .
H6 H 0.7792 0.7258 0.8845 0.054 Uiso 1 1 calc R . . . .
C7 C 0.8796(8) 0.7218(13) 0.8260(10) 0.047(3) Uani 1 1 d . . . . .
H7 H 0.9185 0.8013 0.8699 0.057 Uiso 1 1 calc R . . . .
C8 C 0.9073(9) 0.6520(13) 0.7530(11) 0.052(3) Uani 1 1 d . . . . .
H8 H 0.9633 0.6850 0.7489 0.062 Uiso 1 1 calc R . . . .
C9 C 0.8496(9) 0.5326(13) 0.6868(10) 0.046(3) Uani 1 1 d . . . . .
H9 H 0.8663 0.4853 0.6376 0.055 Uiso 1 1 calc R . . . .
C10 C 0.6069(9) 0.5436(12) 0.8291(10) 0.045(3) Uani 1 1 d . . . . .
H10A H 0.6476 0.5287 0.9006 0.068 Uiso 1 1 calc GR . . . .
H10B H 0.5500 0.4797 0.8113 0.068 Uiso 1 1 calc GR . . . .
H10C H 0.5902 0.6570 0.8160 0.068 Uiso 1 1 calc GR . . . .
O11 O 0.5525(6) 0.2868(9) 0.6705(7) 0.049(2) Uani 1 1 d . . . . .
N12 N 0.6742(6) 0.2623(10) 0.5683(7) 0.041(2) Uani 1 1 d . . . . .
C13 C 0.7379(8) 0.2626(12) 0.5178(10) 0.047(3) Uani 1 1 d . . . . .
C14 C 0.7235(8) 0.3781(11) 0.4396(10) 0.044(3) Uani 1 1 d . . . . .
C15 C 0.7921(8) 0.3791(12) 0.3980(9) 0.041(3) Uani 1 1 d . . . . .
H15 H 0.7842 0.4529 0.3457 0.049 Uiso 1 1 calc R . . . .
C16 C 0.8707(9) 0.2758(13) 0.4311(10) 0.047(3) Uani 1 1 d . . . . .
C17 C 0.8778(9) 0.1596(12) 0.5058(10) 0.048(3) Uani 1 1 d . . . . .
H17 H 0.9284 0.0861 0.5275 0.058 Uiso 1 1 calc R . . . .
C18 C 0.8137(8) 0.1502(14) 0.5478(10) 0.045(3) Uani 1 1 d . . . . .
C19 C 0.8224(10) 0.0151(13) 0.6272(10) 0.057(4) Uani 1 1 d . . . . .
H19A H 0.7735 -0.0652 0.5958 0.085 Uiso 1 1 calc GR . . . .
H19B H 0.8153 0.0630 0.6849 0.085 Uiso 1 1 calc GR . . . .
H19C H 0.8838 -0.0359 0.6502 0.085 Uiso 1 1 calc GR . . . .
C20 C 0.9452(9) 0.2844(15) 0.3892(11) 0.054(3) Uani 1 1 d . . . . .
H20A H 1.0026 0.2326 0.4363 0.081 Uiso 1 1 calc GR . . . .
H20B H 0.9582 0.3967 0.3803 0.081 Uiso 1 1 calc GR . . . .
H20C H 0.9224 0.2294 0.3241 0.081 Uiso 1 1 calc GR . . . .
C21 C 0.6382(10) 0.4883(13) 0.4027(10) 0.052(3) Uani 1 1 d . . . . .
H21A H 0.5825 0.4260 0.3935 0.078 Uiso 1 1 calc GR . . . .
H21B H 0.6298 0.5367 0.3384 0.078 Uiso 1 1 calc GR . . . .
H21C H 0.6476 0.5728 0.4525 0.078 Uiso 1 1 calc GR . . . .
Cu22 Cu 0.56483(14) 0.1183(2) 0.53363(15) 0.0518(8) Uani 1 1 d . . . . .
Cl23 Cl 0.4181(2) 0.1471(3) 0.4043(3) 0.0544(10) 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
N1 C2 1.365(15) . ?
N1 C5 1.398(15) . ?
N1 C10 1.477(15) . ?
C2 C3 1.514(18) . ?
C2 O11 1.236(13) . ?
C3 C4 1.475(16) . ?
C3 N12 1.260(15) . ?
C4 C5 1.400(18) . ?
C4 C9 1.400(18) . ?
C5 C6 1.382(16) . ?
C6 H6 0.9300 . ?
C6 C7 1.394(16) . ?
C7 H7 0.9300 . ?
C7 C8 1.406(18) . ?
C8 H8 0.9300 . ?
C8 C9 1.394(17) . ?
C9 H9 0.9300 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
N12 C13 1.444(16) . ?
N12 Cu22 1.946(9) . ?
C13 C14 1.410(17) . ?
C13 C18 1.407(15) . ?
C14 C15 1.414(17) . ?
C14 C21 1.499(15) . ?
C15 H15 0.9300 . ?
C15 C16 1.390(16) . ?
C16 C17 1.401(17) . ?
C16 C20 1.504(17) . ?
C17 H17 0.9300 . ?
C17 C18 1.358(18) . ?
C18 C19 1.550(17) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
Cu22 Cu22 2.659(4) 3_656 ?
Cu22 Cl23 2.262(4) . ?
Cu22 Cl23 2.319(3) 3_656 ?
Cl23 Cu22 2.319(3) 3_656 ?

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 110.2(10) . . ?
C2 N1 C10 124.0(10) . . ?
C5 N1 C10 125.8(9) . . ?
N1 C2 C3 107.8(9) . . ?
O11 C2 N1 127.2(12) . . ?
O11 C2 C3 125.0(12) . . ?
C4 C3 C2 104.2(10) . . ?
N12 C3 C2 118.6(12) . . ?
N12 C3 C4 137.0(14) . . ?
C5 C4 C3 107.2(12) . . ?
C5 C4 C9 119.7(11) . . ?
C9 C4 C3 133.1(13) . . ?
N1 C5 C4 110.4(10) . . ?
C6 C5 N1 126.6(12) . . ?
C6 C5 C4 122.9(12) . . ?
C5 C6 H6 122.0 . . ?
C5 C6 C7 116.0(12) . . ?
C7 C6 H6 122.0 . . ?
C6 C7 H7 118.4 . . ?
C6 C7 C8 123.3(11) . . ?
C8 C7 H7 118.4 . . ?
C7 C8 H8 120.5 . . ?
C9 C8 C7 118.9(12) . . ?
C9 C8 H8 120.5 . . ?
C4 C9 H9 120.4 . . ?
C8 C9 C4 119.1(13) . . ?
C8 C9 H9 120.4 . . ?
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 116.8(11) . . ?
C3 N12 Cu22 118.3(10) . . ?
C13 N12 Cu22 125.0(7) . . ?
C14 C13 N12 118.9(10) . . ?
C18 C13 N12 119.9(11) . . ?
C18 C13 C14 121.2(12) . . ?
C13 C14 C15 116.0(10) . . ?
C13 C14 C21 120.5(12) . . ?
C15 C14 C21 123.4(11) . . ?
C14 C15 H15 118.2 . . ?
C16 C15 C14 123.6(11) . . ?
C16 C15 H15 118.2 . . ?
C15 C16 C17 116.9(12) . . ?
C15 C16 C20 122.7(11) . . ?
C17 C16 C20 120.4(11) . . ?
C16 C17 H17 118.8 . . ?
C18 C17 C16 122.5(11) . . ?
C18 C17 H17 118.8 . . ?
C13 C18 C19 119.8(12) . . ?
C17 C18 C13 119.6(12) . . ?
C17 C18 C19 120.6(11) . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C16 C20 H20A 109.5 . . ?
C16 C20 H20B 109.5 . . ?
C16 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C14 C21 H21A 109.5 . . ?
C14 C21 H21B 109.5 . . ?
C14 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
N12 Cu22 Cu22 167.2(3) . 3_656 ?
N12 Cu22 Cl23 127.7(3) . . ?
N12 Cu22 Cl23 121.4(3) . 3_656 ?
Cl23 Cu22 Cu22 53.52(11) 3_656 3_656 ?
Cl23 Cu22 Cu22 55.53(10) . 3_656 ?
Cl23 Cu22 Cl23 109.05(11) . 3_656 ?
Cu22 Cl23 Cu22 70.95(11) . 3_656 ?

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 3.6(12) . . . . ?
N1 C2 C3 N12 -180.0(9) . . . . ?
N1 C5 C6 C7 177.9(11) . . . . ?
C2 N1 C5 C4 0.8(13) . . . . ?
C2 N1 C5 C6 -177.7(11) . . . . ?
C2 C3 C4 C5 -3.1(11) . . . . ?
C2 C3 C4 C9 177.2(12) . . . . ?
C2 C3 N12 C13 178.8(9) . . . . ?
C2 C3 N12 Cu22 -0.6(13) . . . . ?
C3 C4 C5 N1 1.6(12) . . . . ?
C3 C4 C5 C6 -179.9(10) . . . . ?
C3 C4 C9 C8 -179.8(11) . . . . ?
C3 N12 C13 C14 -81.9(13) . . . . ?
C3 N12 C13 C18 97.3(12) . . . . ?
C4 C3 N12 C13 -6.2(18) . . . . ?
C4 C3 N12 Cu22 174.4(10) . . . . ?
C4 C5 C6 C7 -0.4(17) . . . . ?
C5 N1 C2 C3 -2.8(12) . . . . ?
C5 N1 C2 O11 180.0(12) . . . . ?
C5 C4 C9 C8 0.5(17) . . . . ?
C5 C6 C7 C8 0.4(18) . . . . ?
C6 C7 C8 C9 -0.1(18) . . . . ?
C7 C8 C9 C4 -0.4(18) . . . . ?
C9 C4 C5 N1 -178.6(10) . . . . ?
C9 C4 C5 C6 -0.1(17) . . . . ?
C10 N1 C2 C3 174.4(9) . . . . ?
C10 N1 C2 O11 -2.9(19) . . . . ?
C10 N1 C5 C4 -176.3(10) . . . . ?
C10 N1 C5 C6 5.3(18) . . . . ?
O11 C2 C3 C4 -179.1(11) . . . . ?
O11 C2 C3 N12 -2.6(17) . . . . ?
N12 C3 C4 C5 -178.5(12) . . . . ?
N12 C3 C4 C9 2(2) . . . . ?
N12 C13 C14 C15 175.9(10) . . . . ?
N12 C13 C14 C21 -5.6(16) . . . . ?
N12 C13 C18 C17 -174.7(10) . . . . ?
N12 C13 C18 C19 6.2(16) . . . . ?
C13 C14 C15 C16 -0.8(17) . . . . ?
C14 C13 C18 C17 4.4(17) . . . . ?
C14 C13 C18 C19 -174.6(10) . . . . ?
C14 C15 C16 C17 3.6(17) . . . . ?
C14 C15 C16 C20 -177.1(11) . . . . ?
C15 C16 C17 C18 -2.4(17) . . . . ?
C16 C17 C18 C13 -1.4(18) . . . . ?
C16 C17 C18 C19 177.6(11) . . . . ?
C18 C13 C14 C15 -3.3(16) . . . . ?
C18 C13 C14 C21 175.2(11) . . . . ?
C20 C16 C17 C18 178.2(12) . . . . ?
C21 C14 C15 C16 -179.2(11) . . . . ?
Cu22 N12 C13 C14 97.5(10) . . . . ?
Cu22 N12 C13 C18 -83.3(12) . . . . ?

# start Validation Reply Form
_vrf_PLAT084_pd_145              
;
PROBLEM: High wR2 Value (i.e. > 0.25) ...................       0.46 Report
RESPONSE: Due to the small size and low diffraction ability of the crystals.
;
_vrf_PLAT973_pd_145              
;
PROBLEM: Check Calcd Positive Residual Density on    Cu22       2.01 eA-3  
RESPONSE: Due to the small size and low diffraction ability of the crystals.
;
_vrf_PLAT341_pd_145              
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.01841 Ang.  
RESPONSE: Due to the small size and low diffraction ability of the crystals.
;
_vrf_PLAT971_pd_145              
;
PROBLEM: Check Calcd Residual Density  0.89A From    Cu22       2.64 eA-3  
RESPONSE: Due to the small size and low diffraction ability 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_as110
_database_code_depnum_ccdc_archive 'CCDC 1538873'
_audit_update_record             
;
2017-03-19 deposited with the CCDC.
2018-10-29 downloaded from the CCDC.
;
_audit_creation_date             2016-09-21
_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         'C36 H36 Br2 Cu2 N4 O2'
_chemical_formula_sum            'C36 H36 Br2 Cu2 N4 O2'
_chemical_formula_weight         843.59
_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'
Cu Cu 0.3201 1.2651 '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                   15.4205(6)
_cell_length_b                   7.92427(19)
_cell_length_c                   14.7380(5)
_cell_angle_alpha                90
_cell_angle_beta                 112.819(4)
_cell_angle_gamma                90
_cell_volume                     1659.98(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5251
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.9500
_cell_measurement_theta_min      4.1200
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.728
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.58566
_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.
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.688
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.05
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0350
_diffrn_reflns_av_unetI/netI     0.0402
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            11026
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.500
_diffrn_reflns_theta_min         3.040
_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 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   67.00  100.00   1.0000   32.5000
omega____ theta____ kappa____ phi______ frames
    -       12.8719  178.0000  -60.0000 33

#__ type_ start__ end____ width___ exp.time_
  2 omega  -48.00   13.00   1.0000   32.5000
omega____ theta____ kappa____ phi______ frames
    -       12.8719  -77.0000 -180.0000 61

#__ type_ start__ end____ width___ exp.time_
  3 omega  -64.00   46.00   1.0000   32.5000
omega____ theta____ kappa____ phi______ frames
    -       12.8719  -19.0000 -150.0000 110

#__ type_ start__ end____ width___ exp.time_
  4 omega   -6.00   51.00   1.0000   32.5000
omega____ theta____ kappa____ phi______ frames
    -       12.8719   19.0000  -90.0000 57
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0272577000
_diffrn_orient_matrix_UB_12      -0.0700214000
_diffrn_orient_matrix_UB_13      -0.0254952000
_diffrn_orient_matrix_UB_21      0.0414753000
_diffrn_orient_matrix_UB_22      -0.0411158000
_diffrn_orient_matrix_UB_23      0.0016692000
_diffrn_orient_matrix_UB_31      0.0054143000
_diffrn_orient_matrix_UB_32      -0.0376619000
_diffrn_orient_matrix_UB_33      0.0455101000
_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                3196
_reflns_number_total             3798
_reflns_odcompleteness_completeness 99.72
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.04
_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 1.171.37.35 (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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.902
_refine_diff_density_min         -0.517
_refine_diff_density_rms         0.098
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         3798
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0452
_refine_ls_R_factor_gt           0.0332
_refine_ls_restrained_S_all      1.046
_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)+(0.0378P)²+1.1509P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0753
_refine_ls_wR_factor_ref         0.0816
_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), C15(H15), C17(H17)
2.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C19(H19A,H19B,H19C), C20(H20A,H20B,H20C), C21(H21A,H21B,
 H21C)
;
_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 0.15776(15) 0.0188(3) 0.26742(14) 0.0148(5) Uani 1 1 d . . . . .
C2 C 0.12351(19) 0.1330(3) 0.19314(18) 0.0148(5) Uani 1 1 d . . . . .
C3 C 0.19257(19) 0.1347(3) 0.14266(19) 0.0149(5) Uani 1 1 d . . . . .
C4 C 0.26754(19) 0.0166(3) 0.19577(17) 0.0149(5) Uani 1 1 d . . . . .
C5 C 0.24231(19) -0.0509(3) 0.27076(17) 0.0147(5) Uani 1 1 d . . . . .
C6 C 0.2979(2) -0.1681(3) 0.33648(19) 0.0182(6) Uani 1 1 d . . . . .
H6 H 0.2806 -0.2132 0.3853 0.022 Uiso 1 1 calc R . . . .
C7 C 0.3807(2) -0.2167(4) 0.32737(19) 0.0190(6) Uani 1 1 d . . . . .
H7 H 0.4196 -0.2953 0.3712 0.023 Uiso 1 1 calc R . . . .
C8 C 0.4069(2) -0.1508(3) 0.2544(2) 0.0193(6) Uani 1 1 d . . . . .
H8 H 0.4630 -0.1851 0.2505 0.023 Uiso 1 1 calc R . . . .
C9 C 0.35006(19) -0.0339(3) 0.18694(18) 0.0171(6) Uani 1 1 d . . . . .
H9 H 0.3669 0.0090 0.1374 0.021 Uiso 1 1 calc R . . . .
C10 C 0.1087(2) -0.0314(4) 0.32995(19) 0.0203(6) Uani 1 1 d . . . . .
H10A H 0.0568 0.0436 0.3194 0.030 Uiso 1 1 calc GR . . . .
H10B H 0.1513 -0.0262 0.3977 0.030 Uiso 1 1 calc GR . . . .
H10C H 0.0857 -0.1446 0.3140 0.030 Uiso 1 1 calc GR . . . .
O11 O 0.05287(14) 0.2177(2) 0.16964(13) 0.0198(4) Uani 1 1 d . . . . .
N12 N 0.17449(16) 0.2340(3) 0.06832(15) 0.0153(5) Uani 1 1 d . . . . .
C13 C 0.24016(19) 0.2342(3) 0.02044(18) 0.0151(5) Uani 1 1 d . . . . .
C14 C 0.2249(2) 0.1254(3) -0.05876(19) 0.0160(5) Uani 1 1 d . . . . .
C15 C 0.2929(2) 0.1222(3) -0.09946(19) 0.0182(6) Uani 1 1 d . . . . .
H15 H 0.2844 0.0499 -0.1519 0.022 Uiso 1 1 calc R . . . .
C16 C 0.3728(2) 0.2229(4) -0.06446(18) 0.0178(6) Uani 1 1 d . . . . .
C17 C 0.3821(2) 0.3369(3) 0.01103(19) 0.0178(6) Uani 1 1 d . . . . .
H17 H 0.4336 0.4092 0.0330 0.021 Uiso 1 1 calc R . . . .
C18 C 0.31653(19) 0.3451(3) 0.05421(19) 0.0164(6) Uani 1 1 d . . . . .
C19 C 0.3272(2) 0.4719(4) 0.1336(2) 0.0255(7) Uani 1 1 d . . . . .
H19A H 0.2759 0.5506 0.1106 0.038 Uiso 1 1 calc GR . . . .
H19B H 0.3855 0.5315 0.1499 0.038 Uiso 1 1 calc GR . . . .
H19C H 0.3271 0.4148 0.1910 0.038 Uiso 1 1 calc GR . . . .
C20 C 0.4475(2) 0.2162(4) -0.1072(2) 0.0238(6) Uani 1 1 d . . . . .
H20A H 0.4469 0.1071 -0.1357 0.036 Uiso 1 1 calc GR . . . .
H20B H 0.5081 0.2360 -0.0559 0.036 Uiso 1 1 calc GR . . . .
H20C H 0.4349 0.3013 -0.1570 0.036 Uiso 1 1 calc GR . . . .
C21 C 0.1389(2) 0.0150(4) -0.0974(2) 0.0234(6) Uani 1 1 d . . . . .
H21A H 0.1445 -0.0737 -0.0511 0.035 Uiso 1 1 calc GR . . . .
H21B H 0.1332 -0.0331 -0.1593 0.035 Uiso 1 1 calc GR . . . .
H21C H 0.0841 0.0815 -0.1066 0.035 Uiso 1 1 calc GR . . . .
Cu22 Cu 0.06264(2) 0.38121(4) 0.03396(2) 0.01831(10) Uani 1 1 d . . . . .
Br23 Br 0.08685(2) 0.66946(3) 0.09684(2) 0.02054(9) 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
N1 C2 1.359(3) . ?
N1 C5 1.399(3) . ?
N1 C10 1.456(3) . ?
C2 C3 1.517(4) . ?
C2 O11 1.210(3) . ?
C3 C4 1.457(4) . ?
C3 N12 1.289(3) . ?
C4 C5 1.412(4) . ?
C4 C9 1.388(4) . ?
C5 C6 1.375(4) . ?
C6 H6 0.9300 . ?
C6 C7 1.390(4) . ?
C7 H7 0.9300 . ?
C7 C8 1.389(4) . ?
C8 H8 0.9300 . ?
C8 C9 1.392(4) . ?
C9 H9 0.9300 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
O11 Cu22 2.4359(19) . ?
N12 C13 1.441(3) . ?
N12 Cu22 1.978(2) . ?
C13 C14 1.396(4) . ?
C13 C18 1.397(4) . ?
C14 C15 1.395(4) . ?
C14 C21 1.504(4) . ?
C15 H15 0.9300 . ?
C15 C16 1.389(4) . ?
C16 C17 1.396(4) . ?
C16 C20 1.513(4) . ?
C17 H17 0.9300 . ?
C17 C18 1.389(4) . ?
C18 C19 1.502(4) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
Cu22 Cu22 2.6036(7) 3_565 ?
Cu22 Br23 2.3968(5) 3_565 ?
Cu22 Br23 2.4387(4) . ?
Br23 Cu22 2.3967(5) 3_565 ?

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 110.9(2) . . ?
C2 N1 C10 123.8(2) . . ?
C5 N1 C10 125.1(2) . . ?
N1 C2 C3 105.9(2) . . ?
O11 C2 N1 128.7(2) . . ?
O11 C2 C3 125.4(2) . . ?
C4 C3 C2 107.0(2) . . ?
N12 C3 C2 117.5(2) . . ?
N12 C3 C4 135.6(2) . . ?
C5 C4 C3 105.2(2) . . ?
C9 C4 C3 134.5(2) . . ?
C9 C4 C5 120.4(2) . . ?
N1 C5 C4 111.0(2) . . ?
C6 C5 N1 127.5(2) . . ?
C6 C5 C4 121.5(3) . . ?
C5 C6 H6 121.2 . . ?
C5 C6 C7 117.7(2) . . ?
C7 C6 H6 121.2 . . ?
C6 C7 H7 119.2 . . ?
C8 C7 C6 121.6(3) . . ?
C8 C7 H7 119.2 . . ?
C7 C8 H8 119.6 . . ?
C7 C8 C9 120.8(3) . . ?
C9 C8 H8 119.6 . . ?
C4 C9 C8 118.1(2) . . ?
C4 C9 H9 121.0 . . ?
C8 C9 H9 121.0 . . ?
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 Cu22 101.23(16) . . ?
C3 N12 C13 117.1(2) . . ?
C3 N12 Cu22 117.21(18) . . ?
C13 N12 Cu22 125.63(17) . . ?
C14 C13 N12 119.1(2) . . ?
C14 C13 C18 122.1(2) . . ?
C18 C13 N12 118.8(2) . . ?
C13 C14 C21 120.9(2) . . ?
C15 C14 C13 117.4(2) . . ?
C15 C14 C21 121.7(2) . . ?
C14 C15 H15 118.8 . . ?
C16 C15 C14 122.4(2) . . ?
C16 C15 H15 118.8 . . ?
C15 C16 C17 118.0(3) . . ?
C15 C16 C20 122.3(2) . . ?
C17 C16 C20 119.6(3) . . ?
C16 C17 H17 119.1 . . ?
C18 C17 C16 121.8(3) . . ?
C18 C17 H17 119.1 . . ?
C13 C18 C19 121.4(2) . . ?
C17 C18 C13 118.0(2) . . ?
C17 C18 C19 120.6(3) . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C16 C20 H20A 109.5 . . ?
C16 C20 H20B 109.5 . . ?
C16 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C14 C21 H21A 109.5 . . ?
C14 C21 H21B 109.5 . . ?
C14 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
O11 Cu22 Cu22 115.30(5) . 3_565 ?
O11 Cu22 Br23 103.61(5) . . ?
N12 Cu22 O11 78.56(8) . . ?
N12 Cu22 Cu22 165.44(7) . 3_565 ?
N12 Cu22 Br23 125.32(6) . 3_565 ?
N12 Cu22 Br23 117.72(6) . . ?
Br23 Cu22 O11 102.99(5) 3_565 . ?
Br23 Cu22 Cu22 56.646(14) . 3_565 ?
Br23 Cu22 Cu22 58.206(14) 3_565 3_565 ?
Br23 Cu22 Br23 114.853(15) 3_565 . ?
Cu22 Br23 Cu22 65.147(15) 3_565 . ?

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 -1.2(3) . . . . ?
N1 C2 C3 N12 179.5(2) . . . . ?
N1 C2 O11 Cu22 178.1(2) . . . . ?
N1 C5 C6 C7 -178.4(2) . . . . ?
C2 N1 C5 C4 -0.3(3) . . . . ?
C2 N1 C5 C6 179.0(3) . . . . ?
C2 C3 C4 C5 1.0(3) . . . . ?
C2 C3 C4 C9 -178.4(3) . . . . ?
C2 C3 N12 C13 -179.6(2) . . . . ?
C2 C3 N12 Cu22 3.3(3) . . . . ?
C3 C2 O11 Cu22 -2.1(3) . . . . ?
C3 C4 C5 N1 -0.5(3) . . . . ?
C3 C4 C5 C6 -179.8(2) . . . . ?
C3 C4 C9 C8 178.7(3) . . . . ?
C3 N12 C13 C14 91.7(3) . . . . ?
C3 N12 C13 C18 -89.1(3) . . . . ?
C4 C3 N12 C13 1.3(4) . . . . ?
C4 C3 N12 Cu22 -175.7(2) . . . . ?
C4 C5 C6 C7 0.8(4) . . . . ?
C5 N1 C2 C3 0.9(3) . . . . ?
C5 N1 C2 O11 -179.3(3) . . . . ?
C5 C4 C9 C8 -0.6(4) . . . . ?
C5 C6 C7 C8 -0.4(4) . . . . ?
C6 C7 C8 C9 -0.6(4) . . . . ?
C7 C8 C9 C4 1.0(4) . . . . ?
C9 C4 C5 N1 179.0(2) . . . . ?
C9 C4 C5 C6 -0.3(4) . . . . ?
C10 N1 C2 C3 -175.1(2) . . . . ?
C10 N1 C2 O11 4.7(4) . . . . ?
C10 N1 C5 C4 175.6(2) . . . . ?
C10 N1 C5 C6 -5.1(4) . . . . ?
O11 C2 C3 C4 179.0(3) . . . . ?
O11 C2 C3 N12 -0.3(4) . . . . ?
N12 C3 C4 C5 -179.9(3) . . . . ?
N12 C3 C4 C9 0.7(5) . . . . ?
N12 C13 C14 C15 -176.4(2) . . . . ?
N12 C13 C14 C21 3.0(4) . . . . ?
N12 C13 C18 C17 176.4(2) . . . . ?
N12 C13 C18 C19 -4.7(4) . . . . ?
C13 C14 C15 C16 -0.5(4) . . . . ?
C14 C13 C18 C17 -4.4(4) . . . . ?
C14 C13 C18 C19 174.5(3) . . . . ?
C14 C15 C16 C17 -3.2(4) . . . . ?
C14 C15 C16 C20 178.5(3) . . . . ?
C15 C16 C17 C18 3.2(4) . . . . ?
C16 C17 C18 C13 0.5(4) . . . . ?
C16 C17 C18 C19 -178.5(3) . . . . ?
C18 C13 C14 C15 4.5(4) . . . . ?
C18 C13 C14 C21 -176.2(2) . . . . ?
C20 C16 C17 C18 -178.5(2) . . . . ?
C21 C14 C15 C16 -179.8(3) . . . . ?
Cu22 N12 C13 C14 -91.6(3) . . . . ?
Cu22 N12 C13 C18 87.6(3) . . . . ?

####################################################################### 
# 
# 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_xrd_14_0m
_database_code_depnum_ccdc_archive 'CCDC 1538874'
_audit_update_record             
;
2017-03-19 deposited with the CCDC.
2018-10-29 downloaded from the CCDC.
;
_audit_creation_date             2015-07-01
_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         'C30 H24 Br Cu N4 O2'
_chemical_formula_sum            'C30 H24 Br Cu N4 O2'
_chemical_formula_weight         615.98
_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'
Cu Cu 0.3201 1.2651 '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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   17.9841(19)
_cell_length_b                   6.9520(8)
_cell_length_c                   21.036(2)
_cell_angle_alpha                90
_cell_angle_beta                 91.011(2)
_cell_angle_gamma                90
_cell_volume                     2629.6(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2093
_cell_measurement_temperature    210(2)
_cell_measurement_theta_max      24.00
_cell_measurement_theta_min      2.95
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.386
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.2383
_exptl_absorpt_correction_T_max  0.2651
_exptl_absorpt_process_details   'SADABS; Bruker, 2007'
_exptl_crystal_colour            'dark red'
_exptl_crystal_density_diffrn    1.556
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1248
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.05
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0445
_diffrn_reflns_av_unetI/netI     0.0470
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            13152
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.725
_diffrn_reflns_theta_min         1.937
_diffrn_ambient_temperature      210(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1797
_reflns_number_total             2796
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.077
_refine_diff_density_min         -0.339
_refine_diff_density_rms         0.070
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.893
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         2796
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0687
_refine_ls_R_factor_gt           0.0386
_refine_ls_restrained_S_all      0.893
_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)+(0.0500P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0874
_refine_ls_wR_factor_ref         0.0946
_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(C14A) = Uanis(C14B) = Uanis(C15A) = Uanis(C15B) = Uanis(C16A) =
Uanis(C16B) = Uanis(C17A) = Uanis(C17B) = Uanis(C18A) = Uanis(C18B)
3. Others
 Sof(C14B)=Sof(H14B)=Sof(C15B)=Sof(H15B)=Sof(C16B)=Sof(H16B)=Sof(C17B)=
 Sof(H17B)=Sof(C18B)=Sof(H18B)=1-FVAR(1)
 Sof(C14A)=Sof(H14A)=Sof(C15A)=Sof(H15A)=Sof(C16A)=Sof(H16A)=Sof(C17A)=
 Sof(H17A)=Sof(C18A)=Sof(H18A)=FVAR(1)
4.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C9(H9), C14A(H14A), C14B(H14B), C15A(H15A),
 C15B(H15B), C16A(H16A), C16B(H16B), C17A(H17A), C17B(H17B), C18A(H18A),
 C18B(H18B)
4.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C)
;
_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
C0AA C 0.56976(18) 0.6727(4) 0.37975(17) 0.0445(8) Uani 1 1 d . . . . .
N1 N 0.58974(15) 0.7143(4) 0.44144(14) 0.0515(7) Uani 1 1 d . . . . .
C1AA C 0.48532(16) 0.6783(4) 0.37740(14) 0.0369(7) Uani 1 1 d . . . . .
C2AA C 0.46139(18) 0.7232(4) 0.44193(14) 0.0396(7) Uani 1 1 d . . . . .
C5 C 0.52680(19) 0.7405(4) 0.47903(16) 0.0469(8) Uani 1 1 d . . . . .
C6 C 0.5245(2) 0.7755(5) 0.54384(17) 0.0607(10) Uani 1 1 d . . . . .
H6 H 0.5679 0.7873 0.5683 0.073 Uiso 1 1 calc R . . . .
C7 C 0.4550(3) 0.7925(5) 0.57086(18) 0.0677(12) Uani 1 1 d . . . . .
H7 H 0.4520 0.8165 0.6142 0.081 Uiso 1 1 calc R . . . .
C8 C 0.3909(2) 0.7748(5) 0.53544(17) 0.0608(10) Uani 1 1 d . . . . .
H8 H 0.3453 0.7860 0.5552 0.073 Uiso 1 1 calc R . . . .
C9 C 0.3927(2) 0.7403(5) 0.47048(15) 0.0487(8) Uani 1 1 d . . . . .
H9 H 0.3488 0.7289 0.4466 0.058 Uiso 1 1 calc R . . . .
C10 C 0.6663(2) 0.7191(6) 0.4646(2) 0.0727(12) Uani 1 1 d . . . . .
H10A H 0.6988 0.6814 0.4311 0.109 Uiso 1 1 calc GR . . . .
H10B H 0.6721 0.6320 0.4997 0.109 Uiso 1 1 calc GR . . . .
H10C H 0.6786 0.8472 0.4783 0.109 Uiso 1 1 calc GR . . . .
O11 O 0.61024(12) 0.6381(4) 0.33609(12) 0.0592(6) Uani 1 1 d . . . . .
N12 N 0.45150(12) 0.6404(4) 0.32495(11) 0.0386(6) Uani 1 1 d . . . . .
C13 C 0.37179(16) 0.6577(5) 0.32379(13) 0.0432(8) Uani 1 1 d . . . . .
C14A C 0.3452(5) 0.853(2) 0.3225(5) 0.0493(10) Uani 0.569(9) 1 d . . . A 1
H14A H 0.3781 0.9560 0.3223 0.059 Uiso 0.569(9) 1 calc R . . A 1
C14B C 0.3325(7) 0.812(2) 0.3194(7) 0.0493(10) Uani 0.431(9) 1 d . . . A 2
H14B H 0.3565 0.9301 0.3159 0.059 Uiso 0.431(9) 1 calc R . . A 2
C15A C 0.2698(4) 0.8826(15) 0.3215(3) 0.0493(10) Uani 0.569(9) 1 d . . . A 1
H15A H 0.2511 1.0073 0.3203 0.059 Uiso 0.569(9) 1 calc R . . A 1
C15B C 0.2527(6) 0.8072(17) 0.3198(4) 0.0493(10) Uani 0.431(9) 1 d . . . A 2
H15B H 0.2251 0.9204 0.3181 0.059 Uiso 0.431(9) 1 calc R . . A 2
C16A C 0.2205(5) 0.7246(15) 0.3222(3) 0.0493(10) Uani 0.569(9) 1 d . . . A 1
H16A H 0.1694 0.7453 0.3217 0.059 Uiso 0.569(9) 1 calc R . . A 1
C16B C 0.2189(6) 0.636(2) 0.3225(4) 0.0493(10) Uani 0.431(9) 1 d . . . A 2
H16B H 0.1672 0.6318 0.3220 0.059 Uiso 0.431(9) 1 calc R . . A 2
C17A C 0.2474(4) 0.5440(14) 0.3237(3) 0.0493(10) Uani 0.569(9) 1 d . . . A 1
H17A H 0.2148 0.4402 0.3250 0.059 Uiso 0.569(9) 1 calc R . . A 1
C17B C 0.2584(5) 0.4653(18) 0.3261(5) 0.0493(10) Uani 0.431(9) 1 d . . . A 2
H17B H 0.2333 0.3484 0.3276 0.059 Uiso 0.431(9) 1 calc R . . A 2
C18A C 0.3248(6) 0.512(2) 0.3232(5) 0.0493(10) Uani 0.569(9) 1 d . . . A 1
H18A H 0.3429 0.3865 0.3224 0.059 Uiso 0.569(9) 1 calc R . . A 1
C18B C 0.3350(8) 0.469(2) 0.3275(7) 0.0493(10) Uani 0.431(9) 1 d . . . A 2
H18B H 0.3625 0.3565 0.3308 0.059 Uiso 0.431(9) 1 calc R . . A 2
Cu19 Cu 0.5000 0.53621(9) 0.2500 0.0489(2) Uani 1 2 d S T P . .
Br20 Br 0.5000 0.19282(8) 0.2500 0.0640(2) Uani 1 2 d S T P . .


_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
C0AA N1 1.371(4) . ?
C0AA C1AA 1.519(4) . ?
C0AA O11 1.206(4) . ?
N1 C5 1.404(4) . ?
N1 C10 1.453(4) . ?
C1AA C2AA 1.465(4) . ?
C1AA N12 1.278(4) . ?
C2AA C5 1.405(4) . ?
C2AA C9 1.389(4) . ?
C5 C6 1.386(5) . ?
C6 H6 0.9300 . ?
C6 C7 1.386(6) . ?
C7 H7 0.9300 . ?
C7 C8 1.368(6) . ?
C8 H8 0.9300 . ?
C8 C9 1.388(5) . ?
C9 H9 0.9300 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
N12 C13 1.438(4) . ?
N12 Cu19 1.954(2) . ?
C13 C14A 1.439(15) . ?
C13 C14B 1.288(19) . ?
C13 C18A 1.320(15) . ?
C13 C18B 1.470(19) . ?
C14A H14A 0.9300 . ?
C14A C15A 1.371(11) . ?
C14B H14B 0.9300 . ?
C14B C15B 1.436(14) . ?
C15A H15A 0.9300 . ?
C15A C16A 1.412(9) . ?
C15B H15B 0.9300 . ?
C15B C16B 1.337(12) . ?
C16A H16A 0.9300 . ?
C16A C17A 1.346(9) . ?
C16B H16B 0.9300 . ?
C16B C17B 1.386(12) . ?
C17A H17A 0.9300 . ?
C17A C18A 1.411(11) . ?
C17B H17B 0.9300 . ?
C17B C18B 1.377(15) . ?
C18A H18A 0.9300 . ?
C18B H18B 0.9300 . ?
Cu19 N12 1.954(2) 2_655 ?
Cu19 Br20 2.3872(9) . ?

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 C0AA C1AA 105.7(3) . . ?
O11 C0AA N1 127.7(3) . . ?
O11 C0AA C1AA 126.6(3) . . ?
C0AA N1 C5 111.1(3) . . ?
C0AA N1 C10 123.6(3) . . ?
C5 N1 C10 125.2(3) . . ?
C2AA C1AA C0AA 106.6(3) . . ?
N12 C1AA C0AA 118.9(3) . . ?
N12 C1AA C2AA 134.5(3) . . ?
C5 C2AA C1AA 106.0(3) . . ?
C9 C2AA C1AA 134.2(3) . . ?
C9 C2AA C5 119.7(3) . . ?
N1 C5 C2AA 110.6(3) . . ?
C6 C5 N1 128.0(3) . . ?
C6 C5 C2AA 121.4(3) . . ?
C5 C6 H6 121.3 . . ?
C7 C6 C5 117.5(4) . . ?
C7 C6 H6 121.3 . . ?
C6 C7 H7 119.1 . . ?
C8 C7 C6 121.8(4) . . ?
C8 C7 H7 119.1 . . ?
C7 C8 H8 119.4 . . ?
C7 C8 C9 121.2(4) . . ?
C9 C8 H8 119.4 . . ?
C2AA C9 H9 120.8 . . ?
C8 C9 C2AA 118.5(3) . . ?
C8 C9 H9 120.8 . . ?
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 . . ?
C1AA N12 C13 117.2(2) . . ?
C1AA N12 Cu19 124.1(2) . . ?
C13 N12 Cu19 118.43(18) . . ?
N12 C13 C14A 114.2(4) . . ?
N12 C13 C18B 112.0(5) . . ?
C14B C13 N12 128.0(5) . . ?
C14B C13 C18B 120.0(6) . . ?
C18A C13 N12 125.0(4) . . ?
C18A C13 C14A 120.8(5) . . ?
C13 C14A H14A 121.0 . . ?
C15A C14A C13 118.1(6) . . ?
C15A C14A H14A 121.0 . . ?
C13 C14B H14B 119.1 . . ?
C13 C14B C15B 121.8(10) . . ?
C15B C14B H14B 119.1 . . ?
C14A C15A H15A 119.9 . . ?
C14A C15A C16A 120.2(7) . . ?
C16A C15A H15A 119.9 . . ?
C14B C15B H15B 120.8 . . ?
C16B C15B C14B 118.5(9) . . ?
C16B C15B H15B 120.8 . . ?
C15A C16A H16A 120.0 . . ?
C17A C16A C15A 120.0(7) . . ?
C17A C16A H16A 120.0 . . ?
C15B C16B H16B 119.0 . . ?
C15B C16B C17B 122.1(9) . . ?
C17B C16B H16B 119.0 . . ?
C16A C17A H17A 119.9 . . ?
C16A C17A C18A 120.2(8) . . ?
C18A C17A H17A 119.9 . . ?
C16B C17B H17B 120.2 . . ?
C18B C17B C16B 119.7(9) . . ?
C18B C17B H17B 120.2 . . ?
C13 C18A C17A 120.6(8) . . ?
C13 C18A H18A 119.7 . . ?
C17A C18A H18A 119.7 . . ?
C13 C18B H18B 121.0 . . ?
C17B C18B C13 117.9(9) . . ?
C17B C18B H18B 121.0 . . ?
N12 Cu19 N12 136.50(15) . 2_655 ?
N12 Cu19 Br20 111.75(8) 2_655 . ?
N12 Cu19 Br20 111.75(8) . . ?

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
C0AA N1 C5 C2AA -2.1(4) . . . . ?
C0AA N1 C5 C6 176.8(3) . . . . ?
C0AA C1AA C2AA C5 -0.5(3) . . . . ?
C0AA C1AA C2AA C9 -177.0(3) . . . . ?
C0AA C1AA N12 C13 -176.6(3) . . . . ?
C0AA C1AA N12 Cu19 9.9(4) . . . . ?
N1 C0AA C1AA C2AA -0.7(3) . . . . ?
N1 C0AA C1AA N12 -178.6(3) . . . . ?
N1 C5 C6 C7 -178.7(3) . . . . ?
C1AA C0AA N1 C5 1.7(3) . . . . ?
C1AA C0AA N1 C10 178.4(3) . . . . ?
C1AA C2AA C5 N1 1.6(3) . . . . ?
C1AA C2AA C5 C6 -177.5(3) . . . . ?
C1AA C2AA C9 C8 176.2(3) . . . . ?
C1AA N12 C13 C14A 74.9(5) . . . . ?
C1AA N12 C13 C14B 78.5(9) . . . . ?
C1AA N12 C13 C18A -106.0(7) . . . . ?
C1AA N12 C13 C18B -102.2(7) . . . . ?
C2AA C1AA N12 C13 6.2(5) . . . . ?
C2AA C1AA N12 Cu19 -167.3(3) . . . . ?
C2AA C5 C6 C7 0.2(5) . . . . ?
C5 C2AA C9 C8 0.2(5) . . . . ?
C5 C6 C7 C8 0.3(5) . . . . ?
C6 C7 C8 C9 -0.5(6) . . . . ?
C7 C8 C9 C2AA 0.3(5) . . . . ?
C9 C2AA C5 N1 178.6(3) . . . . ?
C9 C2AA C5 C6 -0.4(5) . . . . ?
C10 N1 C5 C2AA -178.8(3) . . . . ?
C10 N1 C5 C6 0.1(5) . . . . ?
O11 C0AA N1 C5 -178.1(3) . . . . ?
O11 C0AA N1 C10 -1.4(6) . . . . ?
O11 C0AA C1AA C2AA 179.1(3) . . . . ?
O11 C0AA C1AA N12 1.2(5) . . . . ?
N12 C1AA C2AA C5 176.9(3) . . . . ?
N12 C1AA C2AA C9 0.5(6) . . . . ?
N12 C13 C14A C15A -179.8(6) . . . . ?
N12 C13 C14B C15B -179.1(7) . . . . ?
N12 C13 C18A C17A 178.4(6) . . . . ?
N12 C13 C18B C17B -179.2(8) . . . . ?
C13 C14A C15A C16A 0.4(11) . . . . ?
C13 C14B C15B C16B -2.4(17) . . . . ?
C14A C13 C14B C15B -165(5) . . . . ?
C14A C13 C18A C17A -2.5(12) . . . . ?
C14A C13 C18B C17B 4.5(16) . . . . ?
C14A C15A C16A C17A -0.2(10) . . . . ?
C14B C13 C14A C15A 12(4) . . . . ?
C14B C13 C18A C17A -5.3(12) . . . . ?
C14B C13 C18B C17B 0.1(15) . . . . ?
C14B C15B C16B C17B 1.1(13) . . . . ?
C15A C16A C17A C18A -1.3(10) . . . . ?
C15B C16B C17B C18B 0.6(13) . . . . ?
C16A C17A C18A C13 2.7(12) . . . . ?
C16B C17B C18B C13 -1.3(15) . . . . ?
C18A C13 C14A C15A 0.9(12) . . . . ?
C18A C13 C14B C15B 4.8(14) . . . . ?
C18A C13 C18B C17B -13(3) . . . . ?
C18B C13 C14A C15A -3.6(13) . . . . ?
C18B C13 C14B C15B 1.7(16) . . . . ?
C18B C13 C18A C17A 163(5) . . . . ?
Cu19 N12 C13 C14A -111.3(5) . . . . ?
Cu19 N12 C13 C14B -107.6(9) . . . . ?
Cu19 N12 C13 C18A 67.9(6) . . . . ?
Cu19 N12 C13 C18B 71.6(7) . . . . ?
####################################################################### 
# 
# 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_isbd_19
_database_code_depnum_ccdc_archive 'CCDC 1538861'
_audit_update_record             
;
2017-03-19 deposited with the CCDC.
2018-10-29 downloaded from the CCDC.
;
_audit_creation_date             2016-11-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.11.07 svn.r3352 for OlexSys, GUI svn.r5261)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C16 H14 N2 O'
_chemical_formula_sum            'C16 H14 N2 O'
_chemical_formula_weight         250.29
_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           11
_space_group_name_H-M_alt        'P 1 21/m 1'
_space_group_name_Hall           '-P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, z'

_cell_length_a                   9.0075(8)
_cell_length_b                   6.8883(8)
_cell_length_c                   10.3867(11)
_cell_angle_alpha                90
_cell_angle_beta                 98.932(8)
_cell_angle_gamma                90
_cell_volume                     636.64(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1858
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      75.2540
_cell_measurement_theta_min      4.2790
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.659
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.46636
_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.
;
_exptl_crystal_colour            'translucent colorless'
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             264
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0705
_diffrn_reflns_av_unetI/netI     0.0465
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5071
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.427
_diffrn_reflns_theta_min         4.309
_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 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega -116.00  -13.00   1.0000    8.5000
omega____ theta____ kappa____ phi______ frames
    -      -40.2537  -77.0000  120.0000 103

#__ type_ start__ end____ width___ exp.time_
  2 omega -109.00  -69.00   1.0000    8.5000
omega____ theta____ kappa____ phi______ frames
    -      -40.2537 -151.0000 -132.0000 40

#__ type_ start__ end____ width___ exp.time_
  3 omega    6.00   36.00   1.0000    8.5000
omega____ theta____ kappa____ phi______ frames
    -      -40.2537   38.0000 -120.0000 30

#__ type_ start__ end____ width___ exp.time_
  4 omega   59.00  118.00   1.0000    8.5000
omega____ theta____ kappa____ phi______ frames
    -       40.2537  178.0000  150.0000 59

#__ type_ start__ end____ width___ exp.time_
  5 omega   47.00   95.00   1.0000   16.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000  -60.0000 48

#__ type_ start__ end____ width___ exp.time_
  6 omega   61.00   95.00   1.0000   16.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000 -150.0000 34

#__ type_ start__ end____ width___ exp.time_
  7 omega   30.00   70.00   1.0000   16.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000 -150.0000 40

#__ type_ start__ end____ width___ exp.time_
  8 omega   36.00   86.00   1.0000   16.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000   90.0000 50

#__ type_ start__ end____ width___ exp.time_
  9 omega   56.00  106.00   1.0000   16.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000  150.0000 50

#__ type_ start__ end____ width___ exp.time_
 10 omega   29.00   99.00   1.0000   16.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000 -120.0000 70

#__ type_ start__ end____ width___ exp.time_
 11 omega   48.00   87.00   1.0000   16.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000 -180.0000 39

#__ type_ start__ end____ width___ exp.time_
 12 omega   41.00   66.00   1.0000   16.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000 -150.0000 25

#__ type_ start__ end____ width___ exp.time_
 13 omega  127.00  170.00   1.0000   16.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   15.0000   30.0000 43

#__ type_ start__ end____ width___ exp.time_
 14 omega   55.00   95.00   1.0000   16.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   15.0000   30.0000 40

#__ type_ start__ end____ width___ exp.time_
 15 omega -114.00  -20.00   1.0000    8.5000
omega____ theta____ kappa____ phi______ frames
    -      -40.2537  -38.0000  150.0000 94

#__ type_ start__ end____ width___ exp.time_
 16 omega   89.00  117.00   1.0000    8.5000
omega____ theta____ kappa____ phi______ frames
    -       40.2537 -178.0000   30.0000 28

#__ type_ start__ end____ width___ exp.time_
 17 omega   95.00  128.00   1.0000    8.5000
omega____ theta____ kappa____ phi______ frames
    -       40.2537  178.0000 -150.0000 33

#__ type_ start__ end____ width___ exp.time_
 18 omega   60.00   86.00   1.0000    8.5000
omega____ theta____ kappa____ phi______ frames
    -       40.2537 -178.0000   30.0000 26

#__ type_ start__ end____ width___ exp.time_
 19 omega   86.00  113.00   1.0000   16.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000 -180.0000 27

#__ type_ start__ end____ width___ exp.time_
 20 omega  135.00  161.00   1.0000   16.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000  150.0000 26

#__ type_ start__ end____ width___ exp.time_
 21 omega   83.00  110.00   1.0000   16.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000  150.0000 27

#__ type_ start__ end____ width___ exp.time_
 22 omega  142.00  172.00   1.0000   16.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000   90.0000 30

#__ type_ start__ end____ width___ exp.time_
 23 omega  144.00  172.00   1.0000   16.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000  120.0000 28

#__ type_ start__ end____ width___ exp.time_
 24 omega   84.00  109.00   1.0000   16.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000   60.0000 25

#__ type_ start__ end____ width___ exp.time_
 25 omega   89.00  129.00   1.0000   16.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   30.0000 -150.0000 40

#__ type_ start__ end____ width___ exp.time_
 26 omega  121.00  148.00   1.0000   16.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000 -180.0000 27

#__ type_ start__ end____ width___ exp.time_
 27 omega   79.00  106.00   1.0000   16.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000   90.0000 27

#__ type_ start__ end____ width___ exp.time_
 28 omega   79.00  109.00   1.0000   16.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000  120.0000 30

#__ type_ start__ end____ width___ exp.time_
 29 omega   87.00  114.00   1.0000   16.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000 -180.0000 27

#__ type_ start__ end____ width___ exp.time_
 30 omega   83.00  139.00   1.0000   16.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000  120.0000 56

#__ type_ start__ end____ width___ exp.time_
 31 omega   85.00  112.00   1.0000   16.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000 -150.0000 27

#__ type_ start__ end____ width___ exp.time_
 32 omega   88.00  133.00   1.0000   16.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000   90.0000 45

#__ type_ start__ end____ width___ exp.time_
 33 omega   80.00  107.00   1.0000   16.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000  150.0000 27

#__ type_ start__ end____ width___ exp.time_
 34 omega   86.00  126.00   1.0000   16.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000  120.0000 40

#__ type_ start__ end____ width___ exp.time_
 35 omega   79.00  145.00   1.0000   16.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000   60.0000 66

#__ type_ start__ end____ width___ exp.time_
 36 omega   89.00  116.00   1.0000   16.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   30.0000 -180.0000 27

#__ type_ start__ end____ width___ exp.time_
 37 omega   83.00  109.00   1.0000   16.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000   90.0000 26

#__ type_ start__ end____ width___ exp.time_
 38 omega   84.00  111.00   1.0000   16.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000 -180.0000 27
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.1385971000
_diffrn_orient_matrix_UB_12      -0.0769648000
_diffrn_orient_matrix_UB_13      0.0541557000
_diffrn_orient_matrix_UB_21      0.0748243000
_diffrn_orient_matrix_UB_22      0.0531434000
_diffrn_orient_matrix_UB_23      0.1391484000
_diffrn_orient_matrix_UB_31      -0.0718788000
_diffrn_orient_matrix_UB_32      0.2031528000
_diffrn_orient_matrix_UB_33      -0.0157217000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1107
_reflns_number_total             1373
_reflns_odcompleteness_completeness 99.71
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     72.42
_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 1.171.37.35 (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    'ShelXS (Sheldrick, 2015)'
_refine_diff_density_max         0.538
_refine_diff_density_min         -0.311
_refine_diff_density_rms         0.096
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     123
_refine_ls_number_reflns         1373
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0828
_refine_ls_R_factor_gt           0.0694
_refine_ls_restrained_S_all      1.062
_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)+(0.1441P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1766
_refine_ls_wR_factor_ref         0.1970
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C9(H9), C14(H14), C15(H15), C16(H16)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.4131(2) 0.2500 0.3286(2) 0.0279(6) Uani 1 2 d S T P . .
C2 C 0.2606(3) 0.2500 0.3311(3) 0.0261(6) Uani 1 2 d S T P . .
C3 C 0.2434(2) 0.2500 0.4749(2) 0.0210(6) Uani 1 2 d S T P . .
C4 C 0.3971(2) 0.2500 0.5484(2) 0.0214(6) Uani 1 2 d S T P . .
C5 C 0.4936(3) 0.2500 0.4555(3) 0.0251(6) Uani 1 2 d S T P . .
C6 C 0.6489(3) 0.2500 0.4931(3) 0.0331(7) Uani 1 2 d S T P . .
H6 H 0.7134 0.2500 0.4313 0.040 Uiso 1 2 calc RS T P . .
C7 C 0.7042(3) 0.2500 0.6248(3) 0.0365(8) Uani 1 2 d S T P . .
H7 H 0.8078 0.2500 0.6509 0.044 Uiso 1 2 calc RS T P . .
C8 C 0.6113(3) 0.2500 0.7196(3) 0.0304(7) Uani 1 2 d S T P . .
C9 C 0.4549(2) 0.2500 0.6812(3) 0.0239(6) Uani 1 2 d S T P . .
H9 H 0.3908 0.2500 0.7432 0.029 Uiso 1 2 calc RS T P . .
C10 C 0.4801(4) 0.2500 0.2103(3) 0.0371(7) Uani 1 2 d S T P . .
H10A H 0.544(3) 0.140(4) 0.211(2) 0.034(6) Uiso 1 1 d . . . . .
H10B H 0.403(5) 0.2500 0.132(5) 0.062(13) Uiso 1 2 d S T P . .
O11 O 0.1616(2) 0.2500 0.23804(19) 0.0341(5) Uani 1 2 d S T P . .
N12 N 0.1130(2) 0.2500 0.5088(2) 0.0227(5) Uani 1 2 d S T P . .
C13 C 0.1067(2) 0.2500 0.6443(2) 0.0214(6) Uani 1 2 d S T P . .
C14 C 0.10190(17) 0.4257(3) 0.71086(17) 0.0250(5) Uani 1 1 d . . . . .
H14 H 0.0986 0.5428 0.6660 0.030 Uiso 1 1 calc R . . . .
C15 C 0.10208(19) 0.4239(3) 0.84361(19) 0.0306(5) Uani 1 1 d . . . . .
H15 H 0.0996 0.5408 0.8880 0.037 Uiso 1 1 calc R . . . .
C16 C 0.1059(3) 0.2500 0.9124(3) 0.0325(6) Uani 1 2 d S T P . .
H16 H 0.1109 0.2500 1.0025 0.039 Uiso 1 2 calc RS T P . .
C19 C 0.6777(3) 0.2500 0.8621(4) 0.0424(8) Uani 1 2 d S T P . .
H19A H 0.603(5) 0.2500 0.915(5) 0.056(12) Uiso 1 2 d S T P . .
H19B H 0.746(4) 0.137(5) 0.884(3) 0.067(10) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C2 1.377(3) . ?
N1 C5 1.403(4) . ?
N1 C10 1.450(4) . ?
C2 C3 1.526(3) . ?
C2 O11 1.209(3) . ?
C3 C4 1.473(3) . ?
C3 N12 1.277(3) . ?
C4 C5 1.396(3) . ?
C4 C9 1.396(3) . ?
C5 C6 1.393(4) . ?
C6 H6 0.9300 . ?
C6 C7 1.381(5) . ?
C7 H7 0.9300 . ?
C7 C8 1.388(4) . ?
C8 C9 1.403(3) . ?
C8 C19 1.508(4) . ?
C9 H9 0.9300 . ?
C10 H10A 0.95(2) . ?
C10 H10B 0.99(5) . ?
N12 C13 1.417(3) . ?
C13 C14 1.398(2) 4_565 ?
C13 C14 1.398(2) . ?
C14 H14 0.9300 . ?
C14 C15 1.379(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.392(2) . ?
C16 C15 1.392(2) 4_565 ?
C16 H16 0.9300 . ?
C19 H19A 0.94(5) . ?
C19 H19B 1.00(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C5 110.7(2) . . ?
C2 N1 C10 124.3(3) . . ?
C5 N1 C10 125.0(2) . . ?
N1 C2 C3 105.8(2) . . ?
O11 C2 N1 126.8(2) . . ?
O11 C2 C3 127.4(2) . . ?
C4 C3 C2 106.1(2) . . ?
N12 C3 C2 120.5(2) . . ?
N12 C3 C4 133.4(2) . . ?
C5 C4 C3 106.1(2) . . ?
C5 C4 C9 120.4(2) . . ?
C9 C4 C3 133.5(2) . . ?
C4 C5 N1 111.3(2) . . ?
C6 C5 N1 127.9(3) . . ?
C6 C5 C4 120.8(3) . . ?
C5 C6 H6 121.0 . . ?
C7 C6 C5 118.0(3) . . ?
C7 C6 H6 121.0 . . ?
C6 C7 H7 118.7 . . ?
C6 C7 C8 122.5(2) . . ?
C8 C7 H7 118.7 . . ?
C7 C8 C9 119.2(3) . . ?
C7 C8 C19 120.4(2) . . ?
C9 C8 C19 120.4(3) . . ?
C4 C9 C8 119.0(2) . . ?
C4 C9 H9 120.5 . . ?
C8 C9 H9 120.5 . . ?
N1 C10 H10A 108.6(15) . . ?
N1 C10 H10B 112(3) . . ?
H10A C10 H10B 111(2) . . ?
C3 N12 C13 117.00(19) . . ?
C14 C13 N12 120.02(11) . . ?
C14 C13 N12 120.02(11) 4_565 . ?
C14 C13 C14 120.0(2) . 4_565 ?
C13 C14 H14 120.3 . . ?
C15 C14 C13 119.45(17) . . ?
C15 C14 H14 120.3 . . ?
C14 C15 H15 119.4 . . ?
C14 C15 C16 121.11(18) . . ?
C16 C15 H15 119.4 . . ?
C15 C16 C15 118.7(3) 4_565 . ?
C15 C16 H16 120.6 4_565 . ?
C15 C16 H16 120.6 . . ?
C8 C19 H19A 111(3) . . ?
C8 C19 H19B 111(2) . . ?
H19A C19 H19B 110(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
N1 C2 C3 C4 0.000(0) . . . . ?
N1 C2 C3 N12 180.000(0) . . . . ?
N1 C5 C6 C7 180.000(1) . . . . ?
C2 N1 C5 C4 0.000(0) . . . . ?
C2 N1 C5 C6 180.000(1) . . . . ?
C2 C3 C4 C5 0.000(0) . . . . ?
C2 C3 C4 C9 180.000(1) . . . . ?
C2 C3 N12 C13 180.000(0) . . . . ?
C3 C4 C5 N1 0.000(0) . . . . ?
C3 C4 C5 C6 180.000(1) . . . . ?
C3 C4 C9 C8 180.000(1) . . . . ?
C3 N12 C13 C14 90.72(17) . . . . ?
C3 N12 C13 C14 -90.73(17) . . . 4_565 ?
C4 C3 N12 C13 0.000(1) . . . . ?
C4 C5 C6 C7 0.000(1) . . . . ?
C5 N1 C2 C3 0.000(0) . . . . ?
C5 N1 C2 O11 180.000(0) . . . . ?
C5 C4 C9 C8 0.000(1) . . . . ?
C5 C6 C7 C8 0.000(1) . . . . ?
C6 C7 C8 C9 0.000(1) . . . . ?
C6 C7 C8 C19 180.000(1) . . . . ?
C7 C8 C9 C4 0.000(1) . . . . ?
C9 C4 C5 N1 180.000(1) . . . . ?
C9 C4 C5 C6 0.000(1) . . . . ?
C10 N1 C2 C3 180.000(0) . . . . ?
C10 N1 C2 O11 0.000(1) . . . . ?
C10 N1 C5 C4 180.000(0) . . . . ?
C10 N1 C5 C6 0.000(1) . . . . ?
O11 C2 C3 C4 180.000(0) . . . . ?
O11 C2 C3 N12 0.000(1) . . . . ?
N12 C3 C4 C5 180.000(1) . . . . ?
N12 C3 C4 C9 0.000(1) . . . . ?
N12 C13 C14 C15 -177.32(16) . . . . ?
C13 C14 C15 C16 -0.5(3) . . . . ?
C14 C13 C14 C15 4.1(3) 4_565 . . . ?
C14 C15 C16 C15 -3.1(3) . . . 4_565 ?
C19 C8 C9 C4 180.000(1) . . . . ?


####################################################################### 
# 
# 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_pd_123
_database_code_depnum_ccdc_archive 'CCDC 1538876'
_audit_update_record             
;
2017-03-19 deposited with the CCDC.
2018-10-29 downloaded from the CCDC.
;
_audit_creation_date             2016-10-14
_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         'C32 H28 Br2 Cu2 N4 O2'
_chemical_formula_sum            'C32 H28 Br2 Cu2 N4 O2'
_chemical_formula_weight         787.48
_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'
Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   8.6213(4)
_cell_length_b                   9.3911(5)
_cell_length_c                   10.1721(4)
_cell_angle_alpha                90.122(4)
_cell_angle_beta                 97.663(3)
_cell_angle_gamma                115.574(5)
_cell_volume                     734.60(7)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    4926
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      76.1600
_cell_measurement_theta_min      4.3700
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    5.273
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66073
_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.
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.780
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.09
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0534
_diffrn_reflns_av_unetI/netI     0.0389
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            10404
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.498
_diffrn_reflns_theta_min         4.396
_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 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega -113.00  -14.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787  -57.0000   60.0000 99

#__ type_ start__ end____ width___ exp.time_
  2 omega  -50.00   36.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787   38.0000 -150.0000 86

#__ type_ start__ end____ width___ exp.time_
  3 omega  -40.00   33.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787   38.0000  -30.0000 73

#__ type_ start__ end____ width___ exp.time_
  4 omega   -1.00   24.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787   77.0000   60.0000 25

#__ type_ start__ end____ width___ exp.time_
  5 omega   57.00   88.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       40.3787  178.0000  -30.0000 31

#__ type_ start__ end____ width___ exp.time_
  6 omega   89.00  127.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       40.3787  178.0000  -30.0000 38

#__ type_ start__ end____ width___ exp.time_
  7 omega   61.00  130.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       40.3787  178.0000  120.0000 69

#__ type_ start__ end____ width___ exp.time_
  8 omega   55.00  115.00   1.0000   13.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000  -30.0000 60

#__ type_ start__ end____ width___ exp.time_
  9 omega   29.00  109.00   1.0000   13.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000 -150.0000 80

#__ type_ start__ end____ width___ exp.time_
 10 omega   53.00   84.00   1.0000   13.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000 -180.0000 31

#__ type_ start__ end____ width___ exp.time_
 11 omega   47.00   76.00   1.0000   13.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000   90.0000 29

#__ type_ start__ end____ width___ exp.time_
 12 omega  130.00  177.00   1.0000   13.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000   60.0000 47

#__ type_ start__ end____ width___ exp.time_
 13 omega   36.00   78.00   1.0000   13.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000   60.0000 42

#__ type_ start__ end____ width___ exp.time_
 14 omega   82.00  115.00   1.0000   13.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000   60.0000 33

#__ type_ start__ end____ width___ exp.time_
 15 omega   66.00  113.00   1.0000   13.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000  150.0000 47

#__ type_ start__ end____ width___ exp.time_
 16 omega   86.00  123.00   1.0000   13.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000   30.0000 37

#__ type_ start__ end____ width___ exp.time_
 17 omega   44.00   76.00   1.0000   13.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000    0.0000 32

#__ type_ start__ end____ width___ exp.time_
 18 omega  153.00  178.00   1.0000   13.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000    0.0000 -150.0000 25

#__ type_ start__ end____ width___ exp.time_
 19 omega   90.00  115.00   1.0000   13.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000 -150.0000 25

#__ type_ start__ end____ width___ exp.time_
 20 omega  133.00  174.00   1.0000   13.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000   30.0000 41

#__ type_ start__ end____ width___ exp.time_
 21 omega   79.00  128.00   1.0000   13.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000    0.0000 -150.0000 49

#__ type_ start__ end____ width___ exp.time_
 22 omega   77.00  111.00   1.0000   13.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000  -90.0000 34

#__ type_ start__ end____ width___ exp.time_
 23 omega  142.00  177.00   1.0000   13.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000  120.0000 35

#__ type_ start__ end____ width___ exp.time_
 24 omega   40.00   65.00   1.0000   13.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000   60.0000 25

#__ type_ start__ end____ width___ exp.time_
 25 omega   90.00  135.00   1.0000   13.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000   60.0000 45

#__ type_ start__ end____ width___ exp.time_
 26 omega   51.00   97.00   1.0000   13.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000  -90.0000 46

#__ type_ start__ end____ width___ exp.time_
 27 omega   89.00  166.00   1.0000   13.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000  -60.0000 77

#__ type_ start__ end____ width___ exp.time_
 28 omega   36.00   62.00   1.0000   13.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000  120.0000 26

#__ type_ start__ end____ width___ exp.time_
 29 omega   89.00  114.00   1.0000   13.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000  120.0000 25

#__ type_ start__ end____ width___ exp.time_
 30 omega   89.00  116.00   1.0000   13.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -61.0000 -120.0000 27

#__ type_ start__ end____ width___ exp.time_
 31 omega   47.00   90.00   1.0000   13.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000 -120.0000 43

#__ type_ start__ end____ width___ exp.time_
 32 omega   86.00  113.00   1.0000   13.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000  120.0000 27

#__ type_ start__ end____ width___ exp.time_
 33 omega   50.00   77.00   1.0000   13.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000  150.0000 27

#__ type_ start__ end____ width___ exp.time_
 34 omega   59.00   91.00   1.0000   13.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000   90.0000 32

#__ type_ start__ end____ width___ exp.time_
 35 omega   61.00   88.00   1.0000   13.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -61.0000 -180.0000 27

#__ type_ start__ end____ width___ exp.time_
 36 omega   37.00   87.00   1.0000   13.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000   60.0000 50

#__ type_ start__ end____ width___ exp.time_
 37 omega  105.00  171.00   1.0000   13.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000    0.0000 66

#__ type_ start__ end____ width___ exp.time_
 38 omega   73.00  100.00   1.0000   13.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000    0.0000 27

#__ type_ start__ end____ width___ exp.time_
 39 omega   53.00   78.00   1.0000   13.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000 -120.0000 25

#__ type_ start__ end____ width___ exp.time_
 40 omega   79.00  142.00   1.0000   13.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -64.0000  -14.9017 63

#__ type_ start__ end____ width___ exp.time_
 41 omega  -45.00  -17.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787  -38.0000 -180.0000 28

#__ type_ start__ end____ width___ exp.time_
 42 omega -112.00  -55.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787  -38.0000 -180.0000 57

#__ type_ start__ end____ width___ exp.time_
 43 omega  -50.00   16.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787   38.0000  150.0000 66

#__ type_ start__ end____ width___ exp.time_
 44 omega    6.00   32.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       44.0000   90.0000   85.5754 26

#__ type_ start__ end____ width___ exp.time_
 45 omega   10.00   35.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       44.0000   79.0000 -140.3096 25

#__ type_ start__ end____ width___ exp.time_
 46 omega   13.00   38.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       48.0000   83.0000 -172.1227 25

#__ type_ start__ end____ width___ exp.time_
 47 omega   17.00   43.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       52.0000   81.0000  -82.6170 26

#__ type_ start__ end____ width___ exp.time_
 48 omega   18.00   43.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       52.0000   80.0000    7.0187 25

#__ type_ start__ end____ width___ exp.time_
 49 omega   22.00   47.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   78.0000  -41.6887 25

#__ type_ start__ end____ width___ exp.time_
 50 omega   30.00   70.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       60.0000   65.0000  -11.8221 40

#__ type_ start__ end____ width___ exp.time_
 51 omega   61.00   88.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       60.0000   76.0000  149.6596 27

#__ type_ start__ end____ width___ exp.time_
 52 omega   28.00   53.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       60.0000   76.0000  149.6596 25

#__ type_ start__ end____ width___ exp.time_
 53 omega   36.00   63.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       64.0000   77.0000  154.6798 27

#__ type_ start__ end____ width___ exp.time_
 54 omega   32.00   64.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       64.0000   77.0000   66.7984 32

#__ type_ start__ end____ width___ exp.time_
 55 omega   35.00   62.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       68.0000   75.0000 -156.6453 27

#__ type_ start__ end____ width___ exp.time_
 56 omega   37.00   87.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       68.0000   77.0000  -90.9120 50

#__ type_ start__ end____ width___ exp.time_
 57 omega  107.00  134.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       68.0000   77.0000   -7.0817 27

#__ type_ start__ end____ width___ exp.time_
 58 omega   35.00   62.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       68.0000   77.0000   -7.0817 27

#__ type_ start__ end____ width___ exp.time_
 59 omega   36.00   63.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       68.0000   75.0000 -123.3939 27

#__ type_ start__ end____ width___ exp.time_
 60 omega   38.00   69.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       68.0000   77.0000   35.5733 31

#__ type_ start__ end____ width___ exp.time_
 61 omega  107.00  134.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       68.0000   75.0000 -156.6453 27

#__ type_ start__ end____ width___ exp.time_
 62 omega   46.00   72.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       76.0000   60.0000  124.3769 26

#__ type_ start__ end____ width___ exp.time_
 63 omega   44.00   71.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       76.0000   70.0000  168.2889 27

#__ type_ start__ end____ width___ exp.time_
 64 omega   57.00   84.00   1.0000   13.5000
omega____ theta____ kappa____ phi______ frames
    -       80.0000   52.0000   91.4992 27

#__ type_ start__ end____ width___ exp.time_
 65 omega   52.00   77.00   1.0000   13.5000
omega____ theta____ kappa____ phi______ frames
    -       84.0000   72.0000    6.4562 25

#__ type_ start__ end____ width___ exp.time_
 66 omega   62.00   87.00   1.0000   13.5000
omega____ theta____ kappa____ phi______ frames
    -       88.0000   63.0000 -171.7239 25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0804156000
_diffrn_orient_matrix_UB_12      0.0734272000
_diffrn_orient_matrix_UB_13      0.1425390000
_diffrn_orient_matrix_UB_21      0.0165649000
_diffrn_orient_matrix_UB_22      -0.1520818000
_diffrn_orient_matrix_UB_23      0.0379975000
_diffrn_orient_matrix_UB_31      0.1827354000
_diffrn_orient_matrix_UB_32      0.0685652000
_diffrn_orient_matrix_UB_33      -0.0411783000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2532
_reflns_number_total             2914
_reflns_odcompleteness_completeness 97.82
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     77.49
_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 1.171.37.35 (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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.925
_refine_diff_density_min         -0.695
_refine_diff_density_rms         0.111
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         2914
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0414
_refine_ls_R_factor_gt           0.0347
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0518P)²+0.5666P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0868
_refine_ls_wR_factor_ref         0.0919
_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), C9(H9), C15(H15), C16(H16), C17(H17), C18(H18), C19(H19)
2.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C13(H13A,H13B,H13C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.8375(3) 0.5729(3) 0.4815(2) 0.0134(5) Uani 1 1 d . . . . .
C2 C 0.8639(4) 0.5374(3) 0.6092(3) 0.0129(6) Uani 1 1 d . . . . .
C3 C 0.7011(4) 0.3909(3) 0.6305(3) 0.0117(5) Uani 1 1 d . . . . .
C4 C 0.5848(4) 0.3494(3) 0.5043(3) 0.0128(5) Uani 1 1 d . . . . .
C5 C 0.6719(4) 0.4643(3) 0.4175(3) 0.0128(6) Uani 1 1 d . . . . .
C6 C 0.5960(4) 0.4653(4) 0.2892(3) 0.0144(6) Uani 1 1 d . . . . .
H6 H 0.6549 0.5408 0.2323 0.017 Uiso 1 1 calc R . . . .
C7 C 0.4270(4) 0.3482(4) 0.2485(3) 0.0153(6) Uani 1 1 d . . . . .
H7 H 0.3732 0.3467 0.1626 0.018 Uiso 1 1 calc R . . . .
C8 C 0.3364(4) 0.2337(3) 0.3321(3) 0.0147(6) Uani 1 1 d . . . . .
C9 C 0.4160(4) 0.2347(3) 0.4603(3) 0.0133(6) Uani 1 1 d . . . . .
H9 H 0.3568 0.1589 0.5170 0.016 Uiso 1 1 calc R . . . .
C10 C 0.9540(4) 0.7119(3) 0.4227(3) 0.0159(6) Uani 1 1 d . . . . .
H10A H 0.8981 0.7796 0.4014 0.024 Uiso 1 1 calc GR . . . .
H10B H 0.9829 0.6802 0.3432 0.024 Uiso 1 1 calc GR . . . .
H10C H 1.0583 0.7679 0.4848 0.024 Uiso 1 1 calc GR . . . .
O11 O 0.9923(3) 0.6066(2) 0.6926(2) 0.0160(4) Uani 1 1 d . . . . .
N12 N 0.6986(3) 0.3439(3) 0.7494(2) 0.0117(5) Uani 1 1 d . . . . .
C13 C 0.1563(4) 0.1064(4) 0.2809(3) 0.0179(6) Uani 1 1 d . . . . .
H13A H 0.1648 0.0142 0.2487 0.027 Uiso 1 1 calc GR . . . .
H13B H 0.1025 0.1446 0.2098 0.027 Uiso 1 1 calc GR . . . .
H13C H 0.0872 0.0795 0.3516 0.027 Uiso 1 1 calc GR . . . .
C14 C 0.5560(4) 0.2042(3) 0.7812(3) 0.0122(5) Uani 1 1 d . . . . .
C15 C 0.5075(4) 0.0595(4) 0.7129(3) 0.0152(6) Uani 1 1 d . . . . .
H15 H 0.5641 0.0528 0.6432 0.018 Uiso 1 1 calc R . . . .
C16 C 0.3731(4) -0.0753(4) 0.7499(3) 0.0169(6) Uani 1 1 d . . . . .
H16 H 0.3391 -0.1725 0.7045 0.020 Uiso 1 1 calc R . . . .
C17 C 0.2899(4) -0.0645(4) 0.8547(3) 0.0193(6) Uani 1 1 d . . . . .
H17 H 0.1996 -0.1544 0.8789 0.023 Uiso 1 1 calc R . . . .
C18 C 0.3413(4) 0.0803(4) 0.9231(3) 0.0214(7) Uani 1 1 d . . . . .
H18 H 0.2841 0.0871 0.9925 0.026 Uiso 1 1 calc R . . . .
C19 C 0.4772(4) 0.2149(4) 0.8889(3) 0.0178(6) Uani 1 1 d . . . . .
H19 H 0.5151 0.3110 0.9375 0.021 Uiso 1 1 calc R . . . .
Cu20 Cu 0.89880(6) 0.46396(5) 0.88857(4) 0.01610(13) Uani 1 1 d . . . . .
Br21 Br 0.91192(4) 0.66257(4) 1.04419(3) 0.01618(11) 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
N1 C2 1.356(4) . ?
N1 C5 1.412(4) . ?
N1 C10 1.449(4) . ?
C2 C3 1.525(4) . ?
C2 O11 1.222(4) . ?
C3 C4 1.457(4) . ?
C3 N12 1.288(4) . ?
C4 C5 1.410(4) . ?
C4 C9 1.396(4) . ?
C5 C6 1.382(4) . ?
C6 H6 0.9300 . ?
C6 C7 1.399(4) . ?
C7 H7 0.9300 . ?
C7 C8 1.395(4) . ?
C8 C9 1.389(4) . ?
C8 C13 1.514(4) . ?
C9 H9 0.9300 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
O11 Cu20 2.435(2) . ?
N12 C14 1.432(4) . ?
N12 Cu20 1.979(2) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C15 1.390(4) . ?
C14 C19 1.389(4) . ?
C15 H15 0.9300 . ?
C15 C16 1.392(4) . ?
C16 H16 0.9300 . ?
C16 C17 1.388(5) . ?
C17 H17 0.9300 . ?
C17 C18 1.387(5) . ?
C18 H18 0.9300 . ?
C18 C19 1.387(4) . ?
C19 H19 0.9300 . ?
Cu20 Cu20 2.5614(8) 2_767 ?
Cu20 Br21 2.3990(5) . ?
Cu20 Br21 2.4336(6) 2_767 ?
Br21 Cu20 2.4336(6) 2_767 ?

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 110.3(2) . . ?
C2 N1 C10 125.0(2) . . ?
C5 N1 C10 124.4(2) . . ?
N1 C2 C3 106.7(2) . . ?
O11 C2 N1 127.7(3) . . ?
O11 C2 C3 125.6(3) . . ?
C4 C3 C2 106.2(2) . . ?
N12 C3 C2 115.7(3) . . ?
N12 C3 C4 138.1(3) . . ?
C5 C4 C3 106.0(2) . . ?
C9 C4 C3 134.7(3) . . ?
C9 C4 C5 119.2(3) . . ?
C4 C5 N1 110.8(2) . . ?
C6 C5 N1 127.3(3) . . ?
C6 C5 C4 121.9(3) . . ?
C5 C6 H6 121.4 . . ?
C5 C6 C7 117.3(3) . . ?
C7 C6 H6 121.4 . . ?
C6 C7 H7 118.8 . . ?
C8 C7 C6 122.3(3) . . ?
C8 C7 H7 118.8 . . ?
C7 C8 C13 120.0(3) . . ?
C9 C8 C7 119.2(3) . . ?
C9 C8 C13 120.8(3) . . ?
C4 C9 H9 120.0 . . ?
C8 C9 C4 120.0(3) . . ?
C8 C9 H9 120.0 . . ?
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 Cu20 101.46(18) . . ?
C3 N12 C14 121.1(2) . . ?
C3 N12 Cu20 119.12(19) . . ?
C14 N12 Cu20 119.76(18) . . ?
C8 C13 H13A 109.5 . . ?
C8 C13 H13B 109.5 . . ?
C8 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 C14 N12 120.8(3) . . ?
C19 C14 N12 118.1(3) . . ?
C19 C14 C15 120.9(3) . . ?
C14 C15 H15 120.3 . . ?
C14 C15 C16 119.4(3) . . ?
C16 C15 H15 120.3 . . ?
C15 C16 H16 120.0 . . ?
C17 C16 C15 120.0(3) . . ?
C17 C16 H16 120.0 . . ?
C16 C17 H17 120.0 . . ?
C18 C17 C16 120.1(3) . . ?
C18 C17 H17 120.0 . . ?
C17 C18 H18 119.7 . . ?
C17 C18 C19 120.5(3) . . ?
C19 C18 H18 119.7 . . ?
C14 C19 H19 120.5 . . ?
C18 C19 C14 119.1(3) . . ?
C18 C19 H19 120.5 . . ?
O11 Cu20 Cu20 121.25(6) . 2_767 ?
N12 Cu20 O11 77.98(9) . . ?
N12 Cu20 Cu20 160.29(8) . 2_767 ?
N12 Cu20 Br21 124.65(7) . . ?
N12 Cu20 Br21 115.49(7) . 2_767 ?
Br21 Cu20 O11 104.04(5) . . ?
Br21 Cu20 O11 107.87(6) 2_767 . ?
Br21 Cu20 Cu20 57.338(19) 2_767 2_767 ?
Br21 Cu20 Cu20 58.652(19) . 2_767 ?
Br21 Cu20 Br21 115.990(19) . 2_767 ?
Cu20 Br21 Cu20 64.009(19) . 2_767 ?

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 0.2(3) . . . . ?
N1 C2 C3 N12 -176.6(2) . . . . ?
N1 C2 O11 Cu20 175.6(3) . . . . ?
N1 C5 C6 C7 -177.8(3) . . . . ?
C2 N1 C5 C4 -1.3(3) . . . . ?
C2 N1 C5 C6 177.4(3) . . . . ?
C2 C3 C4 C5 -0.9(3) . . . . ?
C2 C3 C4 C9 -176.5(3) . . . . ?
C2 C3 N12 C14 -177.6(2) . . . . ?
C2 C3 N12 Cu20 0.6(3) . . . . ?
C3 C2 O11 Cu20 -5.1(3) . . . . ?
C3 C4 C5 N1 1.4(3) . . . . ?
C3 C4 C5 C6 -177.4(3) . . . . ?
C3 C4 C9 C8 175.7(3) . . . . ?
C3 N12 C14 C15 56.4(4) . . . . ?
C3 N12 C14 C19 -128.7(3) . . . . ?
C4 C3 N12 C14 7.1(5) . . . . ?
C4 C3 N12 Cu20 -174.8(3) . . . . ?
C4 C5 C6 C7 0.8(4) . . . . ?
C5 N1 C2 C3 0.7(3) . . . . ?
C5 N1 C2 O11 -179.9(3) . . . . ?
C5 C4 C9 C8 0.6(4) . . . . ?
C5 C6 C7 C8 -0.2(4) . . . . ?
C6 C7 C8 C9 -0.2(5) . . . . ?
C6 C7 C8 C13 -177.8(3) . . . . ?
C7 C8 C9 C4 0.0(4) . . . . ?
C9 C4 C5 N1 177.7(3) . . . . ?
C9 C4 C5 C6 -1.0(4) . . . . ?
C10 N1 C2 C3 174.4(3) . . . . ?
C10 N1 C2 O11 -6.1(5) . . . . ?
C10 N1 C5 C4 -175.2(3) . . . . ?
C10 N1 C5 C6 3.6(5) . . . . ?
O11 C2 C3 C4 -179.3(3) . . . . ?
O11 C2 C3 N12 4.0(4) . . . . ?
N12 C3 C4 C5 174.7(3) . . . . ?
N12 C3 C4 C9 -0.8(6) . . . . ?
N12 C14 C15 C16 177.3(3) . . . . ?
N12 C14 C19 C18 -178.7(3) . . . . ?
C13 C8 C9 C4 177.5(3) . . . . ?
C14 C15 C16 C17 -0.4(5) . . . . ?
C15 C14 C19 C18 -3.9(5) . . . . ?
C15 C16 C17 C18 -0.5(5) . . . . ?
C16 C17 C18 C19 -0.8(5) . . . . ?
C17 C18 C19 C14 2.9(5) . . . . ?
C19 C14 C15 C16 2.6(5) . . . . ?
Cu20 N12 C14 C15 -121.7(3) . . . . ?
Cu20 N12 C14 C19 53.1(3) . . . . ?


####################################################################### 
# 
# 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_pd_112
_database_code_depnum_ccdc_archive 'CCDC 1538875'
_audit_update_record             
;
2017-03-19 deposited with the CCDC.
2018-10-29 downloaded from the CCDC.
;
_audit_creation_date             2016-10-18
_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         'C36 H36 Cu2 I2 N4 O2'
_chemical_formula_sum            'C36 H36 Cu2 I2 N4 O2'
_chemical_formula_weight         937.57
_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'
Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.3257 6.8362 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      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                   15.5090(16)
_cell_length_b                   7.8740(9)
_cell_length_c                   15.023(2)
_cell_angle_alpha                90
_cell_angle_beta                 111.451(14)
_cell_angle_gamma                90
_cell_volume                     1707.5(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1387
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      75.2960
_cell_measurement_theta_min      5.9340
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    16.036
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64498
_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.
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.824
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             920
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.02
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1407
_diffrn_reflns_av_unetI/netI     0.1389
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            9644
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.475
_diffrn_reflns_theta_min         3.061
_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 0.997
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -48.00   29.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787   38.0000  150.0000 77

#__ type_ start__ end____ width___ exp.time_
  2 omega -120.00  -36.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787  178.0000 -180.0000 84

#__ type_ start__ end____ width___ exp.time_
  3 omega  -37.00   52.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       40.3787  -77.0000  150.0000 89

#__ type_ start__ end____ width___ exp.time_
  4 omega  101.00  128.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       40.3787  178.0000 -150.0000 27

#__ type_ start__ end____ width___ exp.time_
  5 omega   75.00  107.00   1.0000   27.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000   90.0000 32

#__ type_ start__ end____ width___ exp.time_
  6 omega   29.00   99.00   1.0000   27.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000  -90.0000 70

#__ type_ start__ end____ width___ exp.time_
  7 omega   69.00   97.00   1.0000   27.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000  150.0000 28

#__ type_ start__ end____ width___ exp.time_
  8 omega   88.00  114.00   1.0000   27.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000  120.0000 26

#__ type_ start__ end____ width___ exp.time_
  9 omega  103.00  168.00   1.0000   27.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  112.0000 -150.0000 65

#__ type_ start__ end____ width___ exp.time_
 10 omega   76.00  107.00   1.0000   27.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000  -30.0000 31

#__ type_ start__ end____ width___ exp.time_
 11 omega  151.00  177.00   1.0000   27.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   30.0000   30.0000 26

#__ type_ start__ end____ width___ exp.time_
 12 omega   89.00  114.00   1.0000   27.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000 -150.0000 25

#__ type_ start__ end____ width___ exp.time_
 13 omega   53.00   79.00   1.0000   27.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   15.0000  -60.0000 26

#__ type_ start__ end____ width___ exp.time_
 14 omega  153.00  178.00   1.0000   27.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   15.0000  -60.0000 25

#__ type_ start__ end____ width___ exp.time_
 15 omega   83.00  155.00   1.0000   27.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   30.0000   60.0000 72

#__ type_ start__ end____ width___ exp.time_
 16 omega   67.00  107.00   1.0000   27.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000 -180.0000 40

#__ type_ start__ end____ width___ exp.time_
 17 omega   90.00  115.00   1.0000   27.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000  -90.0000 25

#__ type_ start__ end____ width___ exp.time_
 18 omega   45.00   71.00   1.0000   27.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000 -150.0000 26

#__ type_ start__ end____ width___ exp.time_
 19 omega   94.00  146.00   1.0000   27.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000 -150.0000 52

#__ type_ start__ end____ width___ exp.time_
 20 omega   65.00   99.00   1.0000   27.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000  -30.0000 34

#__ type_ start__ end____ width___ exp.time_
 21 omega   41.00   66.00   1.0000   27.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000  -90.0000 25

#__ type_ start__ end____ width___ exp.time_
 22 omega  115.00  140.00   1.0000   27.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   30.0000   30.0000 25

#__ type_ start__ end____ width___ exp.time_
 23 omega   36.00   61.00   1.0000   27.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000   60.0000 25

#__ type_ start__ end____ width___ exp.time_
 24 omega   39.00   89.00   1.0000   27.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000  -60.0000 50

#__ type_ start__ end____ width___ exp.time_
 25 omega   84.00  134.00   1.0000   27.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   30.0000 -150.0000 50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0029787000
_diffrn_orient_matrix_UB_12      -0.1922028000
_diffrn_orient_matrix_UB_13      -0.0173597000
_diffrn_orient_matrix_UB_21      0.0314709000
_diffrn_orient_matrix_UB_22      0.0357526000
_diffrn_orient_matrix_UB_23      -0.0844013000
_diffrn_orient_matrix_UB_31      0.1019428000
_diffrn_orient_matrix_UB_32      -0.0049931000
_diffrn_orient_matrix_UB_33      0.0687019000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2268
_reflns_number_total             3370
_reflns_odcompleteness_completeness 94.62
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     80.07
_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 1.171.37.35 (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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         2.200
_refine_diff_density_min         -1.239
_refine_diff_density_rms         0.250
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         3370
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1073
_refine_ls_R_factor_gt           0.0710
_refine_ls_restrained_S_all      1.014
_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)+(0.0924P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1714
_refine_ls_wR_factor_ref         0.2048
_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), C15(H15), C17(H17)
2.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C19(H19A,H19B,H19C), C20(H20A,H20B,H20C), C21(H21A,H21B,
 H21C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.6594(6) 0.5340(13) 0.7680(7) 0.030(2) Uani 1 1 d . . . . .
C2 C 0.6253(7) 0.6394(15) 0.6950(8) 0.027(2) Uani 1 1 d . . . . .
C3 C 0.6929(6) 0.6445(14) 0.6425(8) 0.025(2) Uani 1 1 d . . . . .
C4 C 0.7691(6) 0.5256(15) 0.6976(7) 0.025(2) Uani 1 1 d . . . . .
C5 C 0.7434(6) 0.4645(14) 0.7728(8) 0.025(2) Uani 1 1 d . . . . .
C6 C 0.7972(7) 0.3461(16) 0.8383(9) 0.032(2) Uani 1 1 d . . . . .
H6 H 0.7795 0.3052 0.8872 0.038 Uiso 1 1 calc R . . . .
C7 C 0.8793(7) 0.2905(15) 0.8281(8) 0.026(2) Uani 1 1 d . . . . .
H7 H 0.9172 0.2128 0.8715 0.032 Uiso 1 1 calc R . . . .
C8 C 0.9049(6) 0.3506(14) 0.7533(8) 0.025(2) Uani 1 1 d . . . . .
H8 H 0.9584 0.3097 0.7464 0.030 Uiso 1 1 calc R . . . .
C9 C 0.8505(7) 0.4714(16) 0.6891(8) 0.030(2) Uani 1 1 d . . . . .
H9 H 0.8688 0.5148 0.6412 0.036 Uiso 1 1 calc R . . . .
C10 C 0.6089(7) 0.4805(14) 0.8296(8) 0.025(2) Uani 1 1 d . . . . .
H10A H 0.5999 0.3597 0.8249 0.037 Uiso 1 1 calc GR . . . .
H10B H 0.5498 0.5362 0.8092 0.037 Uiso 1 1 calc GR . . . .
H10C H 0.6441 0.5107 0.8947 0.037 Uiso 1 1 calc GR . . . .
O11 O 0.5542(5) 0.7246(11) 0.6688(6) 0.0316(18) Uani 1 1 d . . . . .
N12 N 0.6766(6) 0.7366(12) 0.5676(7) 0.0258(18) Uani 1 1 d . . . . .
C13 C 0.7429(6) 0.7332(15) 0.5213(8) 0.025(2) Uani 1 1 d . . . . .
C14 C 0.7282(7) 0.6286(18) 0.4434(9) 0.034(3) Uani 1 1 d . . . . .
C15 C 0.7979(7) 0.6239(14) 0.4031(9) 0.027(2) Uani 1 1 d . . . . .
H15 H 0.7903 0.5514 0.3519 0.033 Uiso 1 1 calc R . . . .
C16 C 0.8762(7) 0.7224(16) 0.4370(8) 0.029(2) Uani 1 1 d . . . . .
C17 C 0.8872(6) 0.8305(15) 0.5151(8) 0.027(2) Uani 1 1 d . . . . .
H17 H 0.9404 0.8965 0.5394 0.033 Uiso 1 1 calc R . . . .
C18 C 0.8201(7) 0.8417(15) 0.5578(8) 0.029(2) Uani 1 1 d . . . . .
C19 C 0.6422(7) 0.5214(15) 0.4024(9) 0.032(2) Uani 1 1 d . . . . .
H19A H 0.5884 0.5926 0.3863 0.048 Uiso 1 1 calc GR . . . .
H19B H 0.6410 0.4387 0.4489 0.048 Uiso 1 1 calc GR . . . .
H19C H 0.6425 0.4646 0.3460 0.048 Uiso 1 1 calc GR . . . .
C20 C 0.9519(7) 0.7158(17) 0.3959(9) 0.033(3) Uani 1 1 d . . . . .
H20A H 0.9432 0.8064 0.3507 0.049 Uiso 1 1 calc GR . . . .
H20B H 0.9494 0.6088 0.3644 0.049 Uiso 1 1 calc GR . . . .
H20C H 1.0112 0.7280 0.4466 0.049 Uiso 1 1 calc GR . . . .
C21 C 0.8348(7) 0.9614(18) 0.6384(10) 0.040(3) Uani 1 1 d . . . . .
H21A H 0.7821 1.0349 0.6239 0.060 Uiso 1 1 calc GR . . . .
H21B H 0.8892 1.0282 0.6478 0.060 Uiso 1 1 calc GR . . . .
H21C H 0.8427 0.8984 0.6956 0.060 Uiso 1 1 calc GR . . . .
Cu22 Cu 0.56213(9) 0.8815(2) 0.53474(12) 0.0276(4) Uani 1 1 d . . . . .
I23 I 0.40775(4) 0.81072(9) 0.40212(5) 0.0281(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
N1 C2 1.322(15) . ?
N1 C5 1.390(13) . ?
N1 C10 1.476(12) . ?
C2 C3 1.525(13) . ?
C2 O11 1.226(14) . ?
C3 C4 1.498(15) . ?
C3 N12 1.283(15) . ?
C4 C5 1.413(15) . ?
C4 C9 1.382(15) . ?
C5 C6 1.390(16) . ?
C6 H6 0.9300 . ?
C6 C7 1.408(15) . ?
C7 H7 0.9300 . ?
C7 C8 1.404(15) . ?
C8 H8 0.9300 . ?
C8 C9 1.397(16) . ?
C9 H9 0.9300 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
O11 Cu22 2.403(9) . ?
N12 C13 1.437(11) . ?
N12 Cu22 2.015(9) . ?
C13 C14 1.381(18) . ?
C13 C18 1.408(15) . ?
C14 C15 1.419(14) . ?
C14 C19 1.506(16) . ?
C15 H15 0.9300 . ?
C15 C16 1.372(16) . ?
C16 C17 1.409(17) . ?
C16 C20 1.514(12) . ?
C17 H17 0.9300 . ?
C17 C18 1.411(14) . ?
C18 C21 1.484(17) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
Cu22 Cu22 2.610(3) 3_676 ?
Cu22 I23 2.5541(17) . ?
Cu22 I23 2.582(2) 3_676 ?
I23 Cu22 2.582(2) 3_676 ?

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 111.9(9) . . ?
C2 N1 C10 123.8(9) . . ?
C5 N1 C10 123.9(10) . . ?
N1 C2 C3 107.7(9) . . ?
O11 C2 N1 130.5(10) . . ?
O11 C2 C3 121.8(11) . . ?
C4 C3 C2 104.5(9) . . ?
N12 C3 C2 121.1(9) . . ?
N12 C3 C4 134.4(9) . . ?
C5 C4 C3 105.0(9) . . ?
C9 C4 C3 134.8(10) . . ?
C9 C4 C5 120.2(10) . . ?
N1 C5 C4 111.0(10) . . ?
C6 C5 N1 127.5(10) . . ?
C6 C5 C4 121.5(9) . . ?
C5 C6 H6 121.2 . . ?
C5 C6 C7 117.6(11) . . ?
C7 C6 H6 121.2 . . ?
C6 C7 H7 119.5 . . ?
C8 C7 C6 121.0(11) . . ?
C8 C7 H7 119.5 . . ?
C7 C8 H8 119.8 . . ?
C9 C8 C7 120.4(9) . . ?
C9 C8 H8 119.8 . . ?
C4 C9 C8 119.2(10) . . ?
C4 C9 H9 120.4 . . ?
C8 C9 H9 120.4 . . ?
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 Cu22 103.6(7) . . ?
C3 N12 C13 117.9(9) . . ?
C3 N12 Cu22 114.1(7) . . ?
C13 N12 Cu22 127.9(7) . . ?
C14 C13 N12 119.7(9) . . ?
C14 C13 C18 123.1(9) . . ?
C18 C13 N12 117.2(10) . . ?
C13 C14 C15 117.5(10) . . ?
C13 C14 C19 121.8(10) . . ?
C15 C14 C19 120.7(11) . . ?
C14 C15 H15 118.8 . . ?
C16 C15 C14 122.4(11) . . ?
C16 C15 H15 118.8 . . ?
C15 C16 C17 118.1(9) . . ?
C15 C16 C20 122.8(11) . . ?
C17 C16 C20 119.0(10) . . ?
C16 C17 H17 118.9 . . ?
C16 C17 C18 122.2(10) . . ?
C18 C17 H17 118.9 . . ?
C13 C18 C17 116.6(10) . . ?
C13 C18 C21 124.0(10) . . ?
C17 C18 C21 119.4(10) . . ?
C14 C19 H19A 109.5 . . ?
C14 C19 H19B 109.5 . . ?
C14 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C16 C20 H20A 109.5 . . ?
C16 C20 H20B 109.5 . . ?
C16 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C18 C21 H21A 109.5 . . ?
C18 C21 H21B 109.5 . . ?
C18 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
O11 Cu22 Cu22 116.49(19) . 3_676 ?
O11 Cu22 I23 103.4(2) . 3_676 ?
O11 Cu22 I23 102.76(19) . . ?
N12 Cu22 O11 79.3(3) . . ?
N12 Cu22 Cu22 163.5(3) . 3_676 ?
N12 Cu22 I23 123.9(3) . . ?
N12 Cu22 I23 114.6(3) . 3_676 ?
I23 Cu22 Cu22 59.98(6) . 3_676 ?
I23 Cu22 Cu22 58.93(7) 3_676 3_676 ?
I23 Cu22 I23 118.91(6) . 3_676 ?
Cu22 I23 Cu22 61.09(6) . 3_676 ?

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 0.1(12) . . . . ?
N1 C2 C3 N12 179.5(10) . . . . ?
N1 C2 O11 Cu22 177.0(11) . . . . ?
N1 C5 C6 C7 178.6(11) . . . . ?
C2 N1 C5 C4 -0.2(13) . . . . ?
C2 N1 C5 C6 -178.1(11) . . . . ?
C2 C3 C4 C5 -0.2(11) . . . . ?
C2 C3 C4 C9 179.8(12) . . . . ?
C2 C3 N12 C13 -179.3(10) . . . . ?
C2 C3 N12 Cu22 4.4(13) . . . . ?
C3 C2 O11 Cu22 -2.1(12) . . . . ?
C3 C4 C5 N1 0.3(12) . . . . ?
C3 C4 C5 C6 178.3(10) . . . . ?
C3 C4 C9 C8 -177.4(11) . . . . ?
C3 N12 C13 C14 96.9(14) . . . . ?
C3 N12 C13 C18 -84.3(14) . . . . ?
C4 C3 N12 C13 0.0(19) . . . . ?
C4 C3 N12 Cu22 -176.4(10) . . . . ?
C4 C5 C6 C7 0.9(16) . . . . ?
C5 N1 C2 C3 0.0(13) . . . . ?
C5 N1 C2 O11 -179.2(12) . . . . ?
C5 C4 C9 C8 2.6(17) . . . . ?
C5 C6 C7 C8 -1.1(17) . . . . ?
C6 C7 C8 C9 2.1(17) . . . . ?
C7 C8 C9 C4 -2.8(17) . . . . ?
C9 C4 C5 N1 -179.7(10) . . . . ?
C9 C4 C5 C6 -1.7(16) . . . . ?
C10 N1 C2 C3 -172.8(10) . . . . ?
C10 N1 C2 O11 8(2) . . . . ?
C10 N1 C5 C4 172.7(10) . . . . ?
C10 N1 C5 C6 -5.3(18) . . . . ?
O11 C2 C3 C4 179.4(10) . . . . ?
O11 C2 C3 N12 -1.2(17) . . . . ?
N12 C3 C4 C5 -179.5(12) . . . . ?
N12 C3 C4 C9 0(2) . . . . ?
N12 C13 C14 C15 -177.0(10) . . . . ?
N12 C13 C14 C19 2.3(18) . . . . ?
N12 C13 C18 C17 176.6(10) . . . . ?
N12 C13 C18 C21 -1.9(18) . . . . ?
C13 C14 C15 C16 -2.1(19) . . . . ?
C14 C13 C18 C17 -4.6(18) . . . . ?
C14 C13 C18 C21 176.8(12) . . . . ?
C14 C15 C16 C17 0.5(18) . . . . ?
C14 C15 C16 C20 178.7(11) . . . . ?
C15 C16 C17 C18 -1.0(17) . . . . ?
C16 C17 C18 C13 2.9(17) . . . . ?
C16 C17 C18 C21 -178.5(11) . . . . ?
C18 C13 C14 C15 4.3(19) . . . . ?
C18 C13 C14 C19 -176.4(11) . . . . ?
C19 C14 C15 C16 178.5(11) . . . . ?
C20 C16 C17 C18 -179.2(11) . . . . ?
Cu22 N12 C13 C14 -87.3(14) . . . . ?
Cu22 N12 C13 C18 91.5(12) . . . . ?


####################################################################### 
# 
# 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_xrd_321
_database_code_depnum_ccdc_archive 'CCDC 1538882'
_audit_update_record             
;
2018-05-13 deposited with the CCDC.
2018-10-29 downloaded from the CCDC.
;
_audit_creation_date             2016-12-29
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.11.30 svn.r3356 for OlexSys, GUI svn.r5269)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C20 H14 Cu I N2 O'
_chemical_formula_sum            'C20 H14 Cu I N2 O'
_chemical_formula_weight         488.77
_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'
Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.3257 6.8362 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      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                   12.7900(8)
_cell_length_b                   17.0969(8)
_cell_length_c                   7.9810(5)
_cell_angle_alpha                90
_cell_angle_beta                 102.964(7)
_cell_angle_gamma                90
_cell_volume                     1700.72(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2042
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      75.8310
_cell_measurement_theta_min      3.6020
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    16.141
_exptl_absorpt_correction_T_max  0.933
_exptl_absorpt_correction_T_min  0.632
_exptl_absorpt_correction_type   gaussian
_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)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'dark red'
_exptl_crystal_density_diffrn    1.909
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             952
_exptl_crystal_size_max          0.2195
_exptl_crystal_size_mid          0.0681
_exptl_crystal_size_min          0.0167
_exptl_special_details           
;
 ?
;

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
-2 11 0 0.0323 -2.0120 10.9883 -0.0021 0.8449 0.2094 0.5323
8 1 0 0.0084 8.0206 0.9920 0.0073 0.1408 -0.9767 -0.1347
-8 -1 0 0.0084 -8.0206 -0.9920 -0.0073 -0.1408 0.9767 0.1347
3 -6 -4 0.0970 3.0080 -5.9903 -4.0071 -0.0770 -0.0253 -0.9589
2 4 -5 0.0955 1.9984 3.9996 -5.0107 0.7897 0.1458 -0.6498
-3 3 5 0.0955 -3.0053 2.9928 5.0096 -0.2499 -0.0458 0.9824
2 -11 0 0.0323 2.0120 -10.9883 0.0021 -0.8449 -0.2094 -0.5323


_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0636
_diffrn_reflns_av_unetI/netI     0.0821
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            6610
_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         69.963
_diffrn_reflns_theta_min         3.546
_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 0.9994
_diffrn_measured_fraction_theta_max 0.9760
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega -114.00  -13.00   1.0000   37.5000
omega____ theta____ kappa____ phi______ frames
    -      -40.2537  -57.0000 -180.0000 101

#__ type_ start__ end____ width___ exp.time_
  2 omega  -49.00   30.00   1.0000   37.5000
omega____ theta____ kappa____ phi______ frames
    -      -40.2537   38.0000  -30.0000 79

#__ type_ start__ end____ width___ exp.time_
  3 omega   65.00   91.00   1.0000   37.5000
omega____ theta____ kappa____ phi______ frames
    -       40.2537  178.0000  120.0000 26

#__ type_ start__ end____ width___ exp.time_
  4 omega   29.00   62.00   1.0000   37.5000
omega____ theta____ kappa____ phi______ frames
    -       40.2537   57.0000  150.0000 33

#__ type_ start__ end____ width___ exp.time_
  5 omega   44.00  104.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000  150.0000 60

#__ type_ start__ end____ width___ exp.time_
  6 omega   52.00   91.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000 -180.0000 39

#__ type_ start__ end____ width___ exp.time_
  7 omega  103.00  177.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  112.0000 -150.0000 74

#__ type_ start__ end____ width___ exp.time_
  8 omega   37.00   91.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000  -90.0000 54

#__ type_ start__ end____ width___ exp.time_
  9 omega   43.00   80.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000    0.0000 37

#__ type_ start__ end____ width___ exp.time_
 10 omega   42.00   82.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000  -60.0000 40

#__ type_ start__ end____ width___ exp.time_
 11 omega   64.00   91.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -61.0000  -30.0000 27

#__ type_ start__ end____ width___ exp.time_
 12 omega  118.00  143.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -61.0000  -30.0000 25

#__ type_ start__ end____ width___ exp.time_
 13 omega   43.00   93.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000  150.0000 50

#__ type_ start__ end____ width___ exp.time_
 14 omega   85.00  172.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000 -180.0000 87
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0079523000
_diffrn_orient_matrix_UB_12      0.0783312000
_diffrn_orient_matrix_UB_13      -0.0919101000
_diffrn_orient_matrix_UB_21      -0.1213122000
_diffrn_orient_matrix_UB_22      -0.0031755000
_diffrn_orient_matrix_UB_23      -0.0800173000
_diffrn_orient_matrix_UB_31      -0.0224188000
_diffrn_orient_matrix_UB_32      0.0443682000
_diffrn_orient_matrix_UB_33      0.1561468000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2521
_reflns_number_total             3217
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.37.35 (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    'ShelXS (Sheldrick, 2015)'
_refine_diff_density_max         2.208
_refine_diff_density_min         -0.902
_refine_diff_density_rms         0.181
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.991
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0686
_refine_ls_R_factor_gt           0.0509
_refine_ls_restrained_S_all      0.991
_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)+(0.0698P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1225
_refine_ls_wR_factor_ref         0.1340
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C9(H9), C12(H12), C13(H13), C14(H14), C15(H15),
 C16(H16), C19(H19), C20(H20), C21(H21), C22(H22), C23(H23)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.5466(5) 0.5800(3) 0.8473(7) 0.0178(12) Uani 1 1 d . . . . .
C2 C 0.4503(5) 0.6180(4) 0.7928(9) 0.0177(13) Uani 1 1 d . . . . .
C3 C 0.3740(5) 0.5610(4) 0.6836(8) 0.0172(13) Uani 1 1 d . . . . .
C4 C 0.4349(5) 0.4907(4) 0.6719(9) 0.0178(13) Uani 1 1 d . . . . .
C5 C 0.5395(5) 0.5031(4) 0.7756(9) 0.0174(13) Uani 1 1 d . . . . .
C6 C 0.6169(5) 0.4459(4) 0.8015(9) 0.0199(14) Uani 1 1 d . . . . .
H6 H 0.6826 0.4528 0.8783 0.024 Uiso 1 1 calc R . . . .
C7 C 0.5922(6) 0.3761(4) 0.7064(10) 0.0237(15) Uani 1 1 d . . . . .
H7 H 0.6436 0.3368 0.7194 0.028 Uiso 1 1 calc R . . . .
C8 C 0.4934(6) 0.3643(4) 0.5939(9) 0.0206(14) Uani 1 1 d . . . . .
H8 H 0.4808 0.3187 0.5287 0.025 Uiso 1 1 calc R . . . .
C9 C 0.4136(5) 0.4206(4) 0.5791(9) 0.0195(14) Uani 1 1 d . . . . .
H9 H 0.3463 0.4119 0.5081 0.023 Uiso 1 1 calc R . . . .
C10 C 0.6424(5) 0.6176(4) 0.9407(9) 0.0198(14) Uani 1 1 d . . . . .
O11 O 0.4283(4) 0.6855(3) 0.8224(6) 0.0197(10) Uani 1 1 d . . . . .
C12 C 0.7410(6) 0.6064(4) 0.9000(10) 0.0248(15) Uani 1 1 d . . . . .
H12 H 0.7472 0.5721 0.8124 0.030 Uiso 1 1 calc R . . . .
C13 C 0.8301(6) 0.6462(4) 0.9892(10) 0.0241(15) Uani 1 1 d . . . . .
H13 H 0.8962 0.6380 0.9617 0.029 Uiso 1 1 calc R . . . .
C14 C 0.8225(6) 0.6983(4) 1.1193(10) 0.0263(16) Uani 1 1 d . . . . .
H14 H 0.8824 0.7262 1.1766 0.032 Uiso 1 1 calc R . . . .
C15 C 0.7230(6) 0.7082(4) 1.1629(10) 0.0248(15) Uani 1 1 d . . . . .
H15 H 0.7173 0.7418 1.2520 0.030 Uiso 1 1 calc R . . . .
C16 C 0.6334(6) 0.6684(4) 1.0749(9) 0.0231(15) Uani 1 1 d . . . . .
H16 H 0.5676 0.6753 1.1042 0.028 Uiso 1 1 calc R . . . .
N17 N 0.2781(4) 0.5853(3) 0.6248(7) 0.0179(11) Uani 1 1 d . . . . .
C18 C 0.1985(5) 0.5357(4) 0.5202(9) 0.0197(14) Uani 1 1 d . . . . .
C19 C 0.1714(5) 0.4647(4) 0.5826(10) 0.0246(15) Uani 1 1 d . . . . .
H19 H 0.2060 0.4475 0.6915 0.030 Uiso 1 1 calc R . . . .
C20 C 0.0911(6) 0.4190(4) 0.4793(12) 0.0314(18) Uani 1 1 d . . . . .
H20 H 0.0717 0.3714 0.5198 0.038 Uiso 1 1 calc R . . . .
C21 C 0.0408(6) 0.4449(4) 0.3169(11) 0.0308(17) Uani 1 1 d . . . . .
H21 H -0.0122 0.4144 0.2482 0.037 Uiso 1 1 calc R . . . .
C22 C 0.0692(6) 0.5164(5) 0.2558(11) 0.0315(18) Uani 1 1 d . . . . .
H22 H 0.0357 0.5330 0.1459 0.038 Uiso 1 1 calc R . . . .
C23 C 0.1474(5) 0.5632(4) 0.3580(9) 0.0201(14) Uani 1 1 d . . . . .
H23 H 0.1650 0.6116 0.3190 0.024 Uiso 1 1 calc R . . . .
Cu24 Cu 0.23187(8) 0.69125(5) 0.68788(14) 0.0211(3) Uani 1 1 d . . . . .
I25 I 0.15770(3) 0.79333(2) 0.45984(5) 0.02194(16) 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
N1 C2 1.374(9) . ?
N1 C5 1.429(8) . ?
N1 C10 1.436(8) . ?
C2 C3 1.510(9) . ?
C2 O11 1.223(8) . ?
C3 C4 1.446(9) . ?
C3 N17 1.281(9) . ?
C4 C5 1.422(9) . ?
C4 C9 1.402(9) . ?
C5 C6 1.374(9) . ?
C6 H6 0.9300 . ?
C6 C7 1.411(9) . ?
C7 H7 0.9300 . ?
C7 C8 1.391(10) . ?
C8 H8 0.9300 . ?
C8 C9 1.390(9) . ?
C9 H9 0.9300 . ?
C10 C12 1.384(11) . ?
C10 C16 1.404(10) . ?
C12 H12 0.9300 . ?
C12 C13 1.380(10) . ?
C13 H13 0.9300 . ?
C13 C14 1.388(11) . ?
C14 H14 0.9300 . ?
C14 C15 1.403(12) . ?
C15 H15 0.9300 . ?
C15 C16 1.381(10) . ?
C16 H16 0.9300 . ?
N17 C18 1.438(8) . ?
N17 Cu24 2.005(5) . ?
C18 C19 1.386(10) . ?
C18 C23 1.394(10) . ?
C19 H19 0.9300 . ?
C19 C20 1.401(10) . ?
C20 H20 0.9300 . ?
C20 C21 1.384(12) . ?
C21 H21 0.9300 . ?
C21 C22 1.394(12) . ?
C22 H22 0.9300 . ?
C22 C23 1.393(10) . ?
C23 H23 0.9300 . ?
Cu24 I25 2.5699(12) 4_576 ?
Cu24 I25 2.5464(10) . ?
I25 Cu24 2.5699(12) 4_575 ?

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(5) . . ?
C2 N1 C10 123.6(5) . . ?
C5 N1 C10 126.1(6) . . ?
N1 C2 C3 107.1(5) . . ?
O11 C2 N1 127.9(6) . . ?
O11 C2 C3 125.0(6) . . ?
C4 C3 C2 106.7(5) . . ?
N17 C3 C2 116.3(6) . . ?
N17 C3 C4 137.0(6) . . ?
C5 C4 C3 106.8(6) . . ?
C9 C4 C3 134.4(6) . . ?
C9 C4 C5 118.7(6) . . ?
C4 C5 N1 109.7(6) . . ?
C6 C5 N1 128.0(6) . . ?
C6 C5 C4 122.2(6) . . ?
C5 C6 H6 121.5 . . ?
C5 C6 C7 117.0(6) . . ?
C7 C6 H6 121.5 . . ?
C6 C7 H7 118.9 . . ?
C8 C7 C6 122.1(6) . . ?
C8 C7 H7 118.9 . . ?
C7 C8 H8 120.1 . . ?
C9 C8 C7 119.8(6) . . ?
C9 C8 H8 120.1 . . ?
C4 C9 H9 120.2 . . ?
C8 C9 C4 119.7(6) . . ?
C8 C9 H9 120.2 . . ?
C12 C10 N1 122.2(6) . . ?
C12 C10 C16 120.0(6) . . ?
C16 C10 N1 117.8(6) . . ?
C10 C12 H12 120.0 . . ?
C13 C12 C10 120.1(7) . . ?
C13 C12 H12 120.0 . . ?
C12 C13 H13 119.5 . . ?
C12 C13 C14 120.9(7) . . ?
C14 C13 H13 119.5 . . ?
C13 C14 H14 120.6 . . ?
C13 C14 C15 118.9(6) . . ?
C15 C14 H14 120.6 . . ?
C14 C15 H15 119.7 . . ?
C16 C15 C14 120.7(7) . . ?
C16 C15 H15 119.7 . . ?
C10 C16 H16 120.3 . . ?
C15 C16 C10 119.4(7) . . ?
C15 C16 H16 120.3 . . ?
C3 N17 C18 121.1(5) . . ?
C3 N17 Cu24 120.9(4) . . ?
C18 N17 Cu24 117.9(4) . . ?
C19 C18 N17 120.6(6) . . ?
C19 C18 C23 121.7(6) . . ?
C23 C18 N17 117.7(6) . . ?
C18 C19 H19 120.4 . . ?
C18 C19 C20 119.1(7) . . ?
C20 C19 H19 120.4 . . ?
C19 C20 H20 120.1 . . ?
C21 C20 C19 119.9(7) . . ?
C21 C20 H20 120.1 . . ?
C20 C21 H21 119.8 . . ?
C20 C21 C22 120.3(7) . . ?
C22 C21 H21 119.8 . . ?
C21 C22 H22 119.7 . . ?
C23 C22 C21 120.5(7) . . ?
C23 C22 H22 119.7 . . ?
C18 C23 H23 120.8 . . ?
C22 C23 C18 118.4(7) . . ?
C22 C23 H23 120.8 . . ?
N17 Cu24 I25 119.37(17) . 4_576 ?
N17 Cu24 I25 121.56(17) . . ?
I25 Cu24 I25 112.61(4) . 4_576 ?
Cu24 I25 Cu24 121.67(4) . 4_575 ?

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 -3.3(8) . . . . ?
N1 C2 C3 N17 177.9(6) . . . . ?
N1 C5 C6 C7 -176.0(7) . . . . ?
N1 C10 C12 C13 177.5(6) . . . . ?
N1 C10 C16 C15 -177.3(6) . . . . ?
C2 N1 C5 C4 -0.3(8) . . . . ?
C2 N1 C5 C6 -178.2(7) . . . . ?
C2 N1 C10 C12 -134.6(7) . . . . ?
C2 N1 C10 C16 44.0(9) . . . . ?
C2 C3 C4 C5 3.1(8) . . . . ?
C2 C3 C4 C9 -173.4(8) . . . . ?
C2 C3 N17 C18 -179.6(6) . . . . ?
C2 C3 N17 Cu24 -3.4(8) . . . . ?
C3 C4 C5 N1 -1.8(8) . . . . ?
C3 C4 C5 C6 176.2(6) . . . . ?
C3 C4 C9 C8 177.9(7) . . . . ?
C3 N17 C18 C19 58.7(10) . . . . ?
C3 N17 C18 C23 -123.7(7) . . . . ?
C4 C3 N17 C18 2.1(13) . . . . ?
C4 C3 N17 Cu24 178.3(7) . . . . ?
C4 C5 C6 C7 6.3(11) . . . . ?
C5 N1 C2 C3 2.2(8) . . . . ?
C5 N1 C2 O11 -176.7(7) . . . . ?
C5 N1 C10 C12 35.5(10) . . . . ?
C5 N1 C10 C16 -145.9(6) . . . . ?
C5 C4 C9 C8 1.7(10) . . . . ?
C5 C6 C7 C8 -1.4(11) . . . . ?
C6 C7 C8 C9 -3.2(11) . . . . ?
C7 C8 C9 C4 3.0(11) . . . . ?
C9 C4 C5 N1 175.3(6) . . . . ?
C9 C4 C5 C6 -6.6(11) . . . . ?
C10 N1 C2 C3 173.8(6) . . . . ?
C10 N1 C2 O11 -5.1(12) . . . . ?
C10 N1 C5 C4 -171.6(6) . . . . ?
C10 N1 C5 C6 10.5(12) . . . . ?
C10 C12 C13 C14 -0.6(11) . . . . ?
O11 C2 C3 C4 175.7(7) . . . . ?
O11 C2 C3 N17 -3.1(11) . . . . ?
C12 C10 C16 C15 1.3(10) . . . . ?
C12 C13 C14 C15 2.0(11) . . . . ?
C13 C14 C15 C16 -1.7(11) . . . . ?
C14 C15 C16 C10 0.1(10) . . . . ?
C16 C10 C12 C13 -1.1(10) . . . . ?
N17 C3 C4 C5 -178.5(8) . . . . ?
N17 C3 C4 C9 5.0(15) . . . . ?
N17 C18 C19 C20 178.0(7) . . . . ?
N17 C18 C23 C22 -179.2(6) . . . . ?
C18 C19 C20 C21 0.5(12) . . . . ?
C19 C18 C23 C22 -1.7(11) . . . . ?
C19 C20 C21 C22 -0.3(12) . . . . ?
C20 C21 C22 C23 -0.9(12) . . . . ?
C21 C22 C23 C18 1.9(11) . . . . ?
C23 C18 C19 C20 0.5(11) . . . . ?
Cu24 N17 C18 C19 -117.6(6) . . . . ?
Cu24 N17 C18 C23 60.0(8) . . . . ?


####################################################################### 
# 
# 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_xrd_21
_database_code_depnum_ccdc_archive 'CCDC 1538880'
_audit_update_record             
;
2017-03-19 deposited with the CCDC.
2018-10-29 downloaded from the CCDC.
;
_audit_creation_date             2016-03-18
_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         'C34 H32 Cu2 I2 N4 O2'
_chemical_formula_sum            'C34 H32 Cu2 I2 N4 O2'
_chemical_formula_weight         909.51
_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'
Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.3257 6.8362 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   27.2980(4)
_cell_length_b                   8.22746(15)
_cell_length_c                   14.3942(3)
_cell_angle_alpha                90
_cell_angle_beta                 93.2951(13)
_cell_angle_gamma                90
_cell_volume                     3227.49(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    10696
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      75.2940
_cell_measurement_theta_min      5.5730
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    16.944
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.22793
_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.
;
_exptl_crystal_colour            'dark red'
_exptl_crystal_density_diffrn    1.872
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       lamina
_exptl_crystal_F_000             1776
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.02
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0676
_diffrn_reflns_av_unetI/netI     0.0318
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            23592
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.493
_diffrn_reflns_theta_min         3.243
_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 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -35.00   15.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.3104   38.0000  -60.0000 50

#__ type_ start__ end____ width___ exp.time_
  2 omega  -42.00   28.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.3104   38.0000 -120.0000 70

#__ type_ start__ end____ width___ exp.time_
  3 omega  -46.00   33.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.3104   38.0000    0.0000 79

#__ type_ start__ end____ width___ exp.time_
  4 omega  -60.00  -16.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.3104   77.0000   90.0000 44

#__ type_ start__ end____ width___ exp.time_
  5 omega   94.00  119.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       41.3104  178.0000 -120.0000 25

#__ type_ start__ end____ width___ exp.time_
  6 omega  105.00  173.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   61.0000  -60.0000 68

#__ type_ start__ end____ width___ exp.time_
  7 omega  137.00  177.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   30.0000  -90.0000 40

#__ type_ start__ end____ width___ exp.time_
  8 omega  105.00  135.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   30.0000  -60.0000 30

#__ type_ start__ end____ width___ exp.time_
  9 omega   97.00  130.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   30.0000  -90.0000 33

#__ type_ start__ end____ width___ exp.time_
 10 omega   88.00  113.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   45.0000  -60.0000 25

#__ type_ start__ end____ width___ exp.time_
 11 omega   98.00  178.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   61.0000 -180.0000 80

#__ type_ start__ end____ width___ exp.time_
 12 omega  109.00  136.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -61.0000 -180.0000 27

#__ type_ start__ end____ width___ exp.time_
 13 omega   64.00   98.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -61.0000 -180.0000 34

#__ type_ start__ end____ width___ exp.time_
 14 omega   61.00   87.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000  -90.0000 26

#__ type_ start__ end____ width___ exp.time_
 15 omega   51.00   80.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -95.0000  -60.0000 29

#__ type_ start__ end____ width___ exp.time_
 16 omega   56.00  103.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -77.0000    0.0000 47

#__ type_ start__ end____ width___ exp.time_
 17 omega  105.00  131.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -77.0000   60.0000 26

#__ type_ start__ end____ width___ exp.time_
 18 omega   69.00   95.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000    0.0000 26

#__ type_ start__ end____ width___ exp.time_
 19 omega   60.00   92.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -77.0000   60.0000 32

#__ type_ start__ end____ width___ exp.time_
 20 omega   57.00   93.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -61.0000   60.0000 36

#__ type_ start__ end____ width___ exp.time_
 21 omega   50.00   81.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000    0.0000 31

#__ type_ start__ end____ width___ exp.time_
 22 omega   63.00   88.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   15.0000   60.0000 25

#__ type_ start__ end____ width___ exp.time_
 23 omega   86.00  111.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   61.0000  120.0000 25

#__ type_ start__ end____ width___ exp.time_
 24 omega  128.00  154.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   45.0000  150.0000 26

#__ type_ start__ end____ width___ exp.time_
 25 omega  129.00  159.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  125.0000  150.0000 30

#__ type_ start__ end____ width___ exp.time_
 26 omega  102.00  167.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  125.0000  120.0000 65

#__ type_ start__ end____ width___ exp.time_
 27 omega   44.00   84.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000   30.0000 40

#__ type_ start__ end____ width___ exp.time_
 28 omega   50.00   75.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000   90.0000 25

#__ type_ start__ end____ width___ exp.time_
 29 omega   40.00   85.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -26.0000  139.0000 45

#__ type_ start__ end____ width___ exp.time_
 30 omega   39.00   64.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000   90.0000 25

#__ type_ start__ end____ width___ exp.time_
 31 omega   33.00  106.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -95.0000   60.0000 73

#__ type_ start__ end____ width___ exp.time_
 32 omega   42.00   67.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000 -120.0000 25

#__ type_ start__ end____ width___ exp.time_
 33 omega   48.00   95.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000 -180.0000 47

#__ type_ start__ end____ width___ exp.time_
 34 omega  -70.00  -10.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.3104  -77.0000  -90.0000 60

#__ type_ start__ end____ width___ exp.time_
 35 omega -114.00  -88.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.3104  -77.0000  -90.0000 26

#__ type_ start__ end____ width___ exp.time_
 36 omega  -46.00  -13.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.3104  -57.0000   60.0000 33

#__ type_ start__ end____ width___ exp.time_
 37 omega  -69.00  -13.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.3104  -57.0000  -60.0000 56

#__ type_ start__ end____ width___ exp.time_
 38 omega  -53.00  -13.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.3104  -57.0000    0.0000 40

#__ type_ start__ end____ width___ exp.time_
 39 omega  -42.00  -11.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.3104  -77.0000  -30.0000 31

#__ type_ start__ end____ width___ exp.time_
 40 omega   82.00  109.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   72.0000   77.2249 27

#__ type_ start__ end____ width___ exp.time_
 41 omega   84.00  113.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   56.0000  107.7438 29

#__ type_ start__ end____ width___ exp.time_
 42 omega   85.00  133.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   50.0000   57.6670 48

#__ type_ start__ end____ width___ exp.time_
 43 omega   80.00  105.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000   90.0000 25

#__ type_ start__ end____ width___ exp.time_
 44 omega   79.00  105.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000    0.0000 26

#__ type_ start__ end____ width___ exp.time_
 45 omega  129.00  160.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000    0.0000 31

#__ type_ start__ end____ width___ exp.time_
 46 omega  143.00  169.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   30.0000  120.0000 26

#__ type_ start__ end____ width___ exp.time_
 47 omega   83.00  134.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   61.0000   30.0000 51

#__ type_ start__ end____ width___ exp.time_
 48 omega  125.00  155.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -15.0000   60.0000 30

#__ type_ start__ end____ width___ exp.time_
 49 omega   84.00  111.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   55.0000  106.8643 27

#__ type_ start__ end____ width___ exp.time_
 50 omega   79.00  110.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000   60.0000 31

#__ type_ start__ end____ width___ exp.time_
 51 omega   79.00  105.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000  -30.0000 26

#__ type_ start__ end____ width___ exp.time_
 52 omega   79.00  127.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000   30.0000 48

#__ type_ start__ end____ width___ exp.time_
 53 omega   87.00  131.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   45.0000  -30.0000 44

#__ type_ start__ end____ width___ exp.time_
 54 omega   88.00  136.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   30.0000   90.0000 48

#__ type_ start__ end____ width___ exp.time_
 55 omega   44.00   70.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000  120.0000 26

#__ type_ start__ end____ width___ exp.time_
 56 omega   34.00   84.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -15.0000   60.0000 50

#__ type_ start__ end____ width___ exp.time_
 57 omega   86.00  112.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   45.0000    0.0000 26

#__ type_ start__ end____ width___ exp.time_
 58 omega   86.00  177.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   45.0000   30.0000 91

#__ type_ start__ end____ width___ exp.time_
 59 omega   86.00  116.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   30.0000  120.0000 30

#__ type_ start__ end____ width___ exp.time_
 60 omega  117.00  143.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   61.0000    0.0000 26

#__ type_ start__ end____ width___ exp.time_
 61 omega   84.00  110.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   61.0000  -30.0000 26

#__ type_ start__ end____ width___ exp.time_
 62 omega   84.00  109.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   61.0000   60.0000 25

#__ type_ start__ end____ width___ exp.time_
 63 omega  118.00  154.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  125.0000   30.0000 36

#__ type_ start__ end____ width___ exp.time_
 64 omega   87.00  113.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   45.0000   90.0000 26

#__ type_ start__ end____ width___ exp.time_
 65 omega   83.00  112.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   61.0000    0.0000 29

#__ type_ start__ end____ width___ exp.time_
 66 omega   62.00   88.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -32.0000   34.4067 26

#__ type_ start__ end____ width___ exp.time_
 67 omega   87.00  112.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   45.0000   60.0000 25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0048364000
_diffrn_orient_matrix_UB_12      -0.0481543000
_diffrn_orient_matrix_UB_13      -0.1035764000
_diffrn_orient_matrix_UB_21      0.0549984000
_diffrn_orient_matrix_UB_22      -0.0430502000
_diffrn_orient_matrix_UB_23      0.0033437000
_diffrn_orient_matrix_UB_31      -0.0121520000
_diffrn_orient_matrix_UB_32      -0.1757050000
_diffrn_orient_matrix_UB_33      0.0275469000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3041
_reflns_number_total             3212
_reflns_odcompleteness_completeness 94.26
_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 1.171.37.35 (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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         1.616
_refine_diff_density_min         -1.544
_refine_diff_density_rms         0.174
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         3212
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0373
_refine_ls_R_factor_gt           0.0354
_refine_ls_restrained_S_all      1.065
_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)+(0.0769P)²+0.3698P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0978
_refine_ls_wR_factor_ref         0.1004
_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), C15(H15), C16(H16), C17(H17)
2.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C21(H21A,H21B,H21C), C22(H22B,H22A,H22C)
;
_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 0.16649(9) -0.2243(4) 0.28411(19) 0.0183(5) Uani 1 1 d . . . . .
C2 C 0.18250(12) -0.1106(4) 0.3459(2) 0.0178(6) Uani 1 1 d . . . . .
C3 C 0.14801(11) -0.1142(4) 0.4247(2) 0.0162(6) Uani 1 1 d . . . . .
C4 C 0.11038(11) -0.2344(4) 0.3989(2) 0.0172(6) Uani 1 1 d . . . . .
C5 C 0.12374(11) -0.3003(4) 0.3136(2) 0.0180(6) Uani 1 1 d . . . . .
C6 C 0.09783(14) -0.4249(4) 0.2691(3) 0.0217(7) Uani 1 1 d . . . . .
H6 H 0.1071 -0.4672 0.2128 0.026 Uiso 1 1 calc R . . . .
C7 C 0.05723(12) -0.4837(5) 0.3127(3) 0.0239(7) Uani 1 1 d . . . . .
H7 H 0.0391 -0.5684 0.2850 0.029 Uiso 1 1 calc R . . . .
C8 C 0.04288(14) -0.4196(4) 0.3965(3) 0.0248(8) Uani 1 1 d . . . . .
H8 H 0.0153 -0.4609 0.4232 0.030 Uiso 1 1 calc R . . . .
C9 C 0.06939(11) -0.2947(4) 0.4406(3) 0.0214(7) Uani 1 1 d . . . . .
H9 H 0.0600 -0.2524 0.4968 0.026 Uiso 1 1 calc R . . . .
C10 C 0.19149(12) -0.2718(4) 0.2016(2) 0.0228(7) Uani 1 1 d . . . . .
H10A H 0.2036 -0.3808 0.2091 0.034 Uiso 1 1 calc GR . . . .
H10B H 0.2184 -0.1992 0.1932 0.034 Uiso 1 1 calc GR . . . .
H10C H 0.1689 -0.2666 0.1480 0.034 Uiso 1 1 calc GR . . . .
O11 O 0.21824(8) -0.0212(3) 0.34346(17) 0.0185(4) Uani 1 1 d . . . . .
N12 N 0.15779(9) -0.0220(3) 0.4952(2) 0.0165(5) Uani 1 1 d . . . . .
C13 C 0.12655(11) -0.0308(4) 0.5723(2) 0.0169(6) Uani 1 1 d . . . . .
C14 C 0.14113(11) -0.1300(4) 0.6481(2) 0.0180(6) Uani 1 1 d . . . . .
C15 C 0.11052(12) -0.1389(4) 0.7223(2) 0.0190(6) Uani 1 1 d . . . . .
H15 H 0.1193 -0.2039 0.7734 0.023 Uiso 1 1 calc R . . . .
C16 C 0.06674(12) -0.0509(5) 0.7203(3) 0.0216(7) Uani 1 1 d . . . . .
H16 H 0.0461 -0.0601 0.7692 0.026 Uiso 1 1 calc R . . . .
C17 C 0.05404(12) 0.0496(4) 0.6462(3) 0.0205(7) Uani 1 1 d . . . . .
H17 H 0.0254 0.1106 0.6470 0.025 Uiso 1 1 calc R . . . .
C18 C 0.08338(12) 0.0620(4) 0.5697(3) 0.0184(7) Uani 1 1 d . . . . .
Cu19 Cu 0.21682(2) 0.12786(6) 0.48472(3) 0.01818(14) Uani 1 1 d . . . . .
I20 I 0.30240(2) 0.07618(2) 0.56172(2) 0.01823(12) Uani 1 1 d . . . . .
C21 C 0.06900(12) 0.1695(5) 0.4887(3) 0.0252(7) Uani 1 1 d . . . . .
H21A H 0.0970 0.2304 0.4714 0.038 Uiso 1 1 calc GR . . . .
H21B H 0.0437 0.2429 0.5056 0.038 Uiso 1 1 calc GR . . . .
H21C H 0.0571 0.1039 0.4370 0.038 Uiso 1 1 calc GR . . . .
C22 C 0.18810(12) -0.2265(4) 0.6493(2) 0.0218(7) Uani 1 1 d . . . . .
H22B H 0.1942 -0.2749 0.7096 0.033 Uiso 1 1 calc GR . . . .
H22A H 0.2148 -0.1558 0.6363 0.033 Uiso 1 1 calc GR . . . .
H22C H 0.1852 -0.3104 0.6030 0.033 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 1.347(5) . ?
N1 C5 1.411(4) . ?
N1 C10 1.457(4) . ?
C2 C3 1.515(4) . ?
C2 O11 1.224(4) . ?
C3 C4 1.459(4) . ?
C3 N12 1.282(5) . ?
C4 C5 1.408(5) . ?
C4 C9 1.392(4) . ?
C5 C6 1.382(5) . ?
C6 H6 0.9300 . ?
C6 C7 1.392(5) . ?
C7 H7 0.9300 . ?
C7 C8 1.394(6) . ?
C8 H8 0.9300 . ?
C8 C9 1.389(5) . ?
C9 H9 0.9300 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
O11 Cu19 2.377(2) . ?
N12 C13 1.440(4) . ?
N12 Cu19 2.041(3) . ?
C13 C14 1.401(5) . ?
C13 C18 1.403(4) . ?
C14 C15 1.396(5) . ?
C14 C22 1.508(4) . ?
C15 H15 0.9300 . ?
C15 C16 1.396(5) . ?
C16 H16 0.9300 . ?
C16 C17 1.378(5) . ?
C17 H17 0.9300 . ?
C17 C18 1.402(5) . ?
C18 C21 1.498(5) . ?
Cu19 Cu19 2.7246(10) 7_556 ?
Cu19 I20 2.5631(5) . ?
Cu19 I20 2.5711(5) 7_556 ?
I20 Cu19 2.5711(5) 7_556 ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22C 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 110.6(3) . . ?
C2 N1 C10 125.1(3) . . ?
C5 N1 C10 124.1(3) . . ?
N1 C2 C3 106.8(3) . . ?
O11 C2 N1 128.8(3) . . ?
O11 C2 C3 124.3(3) . . ?
C4 C3 C2 106.3(3) . . ?
N12 C3 C2 118.1(3) . . ?
N12 C3 C4 135.6(3) . . ?
C5 C4 C3 105.6(3) . . ?
C9 C4 C3 134.7(3) . . ?
C9 C4 C5 119.6(3) . . ?
C4 C5 N1 110.6(3) . . ?
C6 C5 N1 126.8(3) . . ?
C6 C5 C4 122.6(3) . . ?
C5 C6 H6 121.7 . . ?
C5 C6 C7 116.6(3) . . ?
C7 C6 H6 121.7 . . ?
C6 C7 H7 119.0 . . ?
C6 C7 C8 122.0(3) . . ?
C8 C7 H7 119.0 . . ?
C7 C8 H8 119.6 . . ?
C9 C8 C7 120.7(3) . . ?
C9 C8 H8 119.6 . . ?
C4 C9 H9 120.8 . . ?
C8 C9 C4 118.5(3) . . ?
C8 C9 H9 120.8 . . ?
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 Cu19 103.5(2) . . ?
C3 N12 C13 118.3(3) . . ?
C3 N12 Cu19 115.3(2) . . ?
C13 N12 Cu19 126.3(2) . . ?
C14 C13 N12 118.4(3) . . ?
C14 C13 C18 122.6(3) . . ?
C18 C13 N12 119.1(3) . . ?
C13 C14 C22 121.3(3) . . ?
C15 C14 C13 118.1(3) . . ?
C15 C14 C22 120.6(3) . . ?
C14 C15 H15 119.8 . . ?
C14 C15 C16 120.4(3) . . ?
C16 C15 H15 119.8 . . ?
C15 C16 H16 119.9 . . ?
C17 C16 C15 120.3(3) . . ?
C17 C16 H16 119.9 . . ?
C16 C17 H17 119.3 . . ?
C16 C17 C18 121.5(3) . . ?
C18 C17 H17 119.3 . . ?
C13 C18 C21 121.6(3) . . ?
C17 C18 C13 117.1(3) . . ?
C17 C18 C21 121.2(3) . . ?
O11 Cu19 Cu19 118.38(6) . 7_556 ?
O11 Cu19 I20 106.23(6) . 7_556 ?
O11 Cu19 I20 103.00(6) . . ?
N12 Cu19 O11 78.66(10) . . ?
N12 Cu19 Cu19 162.55(8) . 7_556 ?
N12 Cu19 I20 116.18(8) . 7_556 ?
N12 Cu19 I20 124.86(8) . . ?
I20 Cu19 Cu19 58.092(16) . 7_556 ?
I20 Cu19 Cu19 57.806(19) 7_556 7_556 ?
I20 Cu19 I20 115.898(19) . 7_556 ?
Cu19 I20 Cu19 64.101(19) . 7_556 ?
C18 C21 H21A 109.5 . . ?
C18 C21 H21B 109.5 . . ?
C18 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C14 C22 H22B 109.5 . . ?
C14 C22 H22A 109.5 . . ?
C14 C22 H22C 109.5 . . ?
H22B C22 H22A 109.5 . . ?
H22B C22 H22C 109.5 . . ?
H22A C22 H22C 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 -2.5(3) . . . . ?
N1 C2 C3 N12 175.9(3) . . . . ?
N1 C2 O11 Cu19 -178.2(3) . . . . ?
N1 C5 C6 C7 178.4(3) . . . . ?
C2 N1 C5 C4 0.2(4) . . . . ?
C2 N1 C5 C6 -178.4(3) . . . . ?
C2 C3 C4 C5 2.6(3) . . . . ?
C2 C3 C4 C9 179.3(3) . . . . ?
C2 C3 N12 C13 -176.9(3) . . . . ?
C2 C3 N12 Cu19 4.1(4) . . . . ?
C3 C2 O11 Cu19 0.0(4) . . . . ?
C3 C4 C5 N1 -1.8(4) . . . . ?
C3 C4 C5 C6 176.9(3) . . . . ?
C3 C4 C9 C8 -176.1(4) . . . . ?
C3 N12 C13 C14 96.1(4) . . . . ?
C3 N12 C13 C18 -85.1(4) . . . . ?
C4 C3 N12 C13 0.8(6) . . . . ?
C4 C3 N12 Cu19 -178.2(3) . . . . ?
C4 C5 C6 C7 0.0(5) . . . . ?
C5 N1 C2 C3 1.4(3) . . . . ?
C5 N1 C2 O11 179.9(3) . . . . ?
C5 C4 C9 C8 0.2(5) . . . . ?
C5 C6 C7 C8 0.7(5) . . . . ?
C6 C7 C8 C9 -1.0(6) . . . . ?
C7 C8 C9 C4 0.4(5) . . . . ?
C9 C4 C5 N1 -179.1(3) . . . . ?
C9 C4 C5 C6 -0.4(5) . . . . ?
C10 N1 C2 C3 -174.3(3) . . . . ?
C10 N1 C2 O11 4.2(6) . . . . ?
C10 N1 C5 C4 176.0(3) . . . . ?
C10 N1 C5 C6 -2.6(5) . . . . ?
O11 C2 C3 C4 178.9(3) . . . . ?
O11 C2 C3 N12 -2.7(5) . . . . ?
N12 C3 C4 C5 -175.4(4) . . . . ?
N12 C3 C4 C9 1.3(7) . . . . ?
N12 C13 C14 C15 -179.6(3) . . . . ?
N12 C13 C14 C22 -0.4(5) . . . . ?
N12 C13 C18 C17 180.0(3) . . . . ?
N12 C13 C18 C21 0.2(5) . . . . ?
C13 C14 C15 C16 0.0(5) . . . . ?
C14 C13 C18 C17 -1.3(5) . . . . ?
C14 C13 C18 C21 178.9(3) . . . . ?
C14 C15 C16 C17 -2.0(5) . . . . ?
C15 C16 C17 C18 2.4(6) . . . . ?
C16 C17 C18 C13 -0.8(5) . . . . ?
C16 C17 C18 C21 179.0(3) . . . . ?
C18 C13 C14 C15 1.7(5) . . . . ?
C18 C13 C14 C22 -179.2(3) . . . . ?
Cu19 N12 C13 C14 -85.0(4) . . . . ?
Cu19 N12 C13 C18 93.8(3) . . . . ?
C22 C14 C15 C16 -179.2(3) . . . . ?


####################################################################### 
# 
# 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_xrd_38_2
_database_code_depnum_ccdc_archive 'CCDC 1538881'
_audit_update_record             
;
2017-03-19 deposited with the CCDC.
2018-10-29 downloaded from the CCDC.
;
_audit_creation_date             2016-09-01
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.08.25 svn.r3337 for OlexSys, GUI svn.r5221)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C34 H32 Br2 Cu2 N4 O2'
_chemical_formula_sum            'C34 H32 Br2 Cu2 N4 O2'
_chemical_formula_weight         815.53
_chemical_melting_point          ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -1.9646 0.5888 '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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   26.9791(11)
_cell_length_b                   8.2871(3)
_cell_length_c                   14.1074(5)
_cell_angle_alpha                90
_cell_angle_beta                 94.972(3)
_cell_angle_gamma                90
_cell_volume                     3142.2(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4403
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      75.9900
_cell_measurement_theta_min      5.5750
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    4.954
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.51218
_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.
;
_exptl_crystal_colour            'dark red'
_exptl_crystal_density_diffrn    1.724
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1632
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.07
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0502
_diffrn_reflns_av_unetI/netI     0.0383
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            11659
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.468
_diffrn_reflns_theta_min         3.289
_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 0.995
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -29.00   26.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      -41.3104   38.0000   90.0000 55

#__ type_ start__ end____ width___ exp.time_
  2 omega  -16.00   11.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      -41.3104   38.0000  -30.0000 27

#__ type_ start__ end____ width___ exp.time_
  3 omega  -50.00   31.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      -41.3104   38.0000  -60.0000 81

#__ type_ start__ end____ width___ exp.time_
  4 omega   36.00   75.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       41.3104  -99.0000  -60.0000 39

#__ type_ start__ end____ width___ exp.time_
  5 omega   30.00   57.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -95.0000  -60.0000 27

#__ type_ start__ end____ width___ exp.time_
  6 omega   80.00  108.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -95.0000  -60.0000 28

#__ type_ start__ end____ width___ exp.time_
  7 omega   75.00  109.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -125.0000 -120.0000 34

#__ type_ start__ end____ width___ exp.time_
  8 omega   78.00  109.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -95.0000 -120.0000 31

#__ type_ start__ end____ width___ exp.time_
  9 omega   91.00  121.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -125.0000 -180.0000 30

#__ type_ start__ end____ width___ exp.time_
 10 omega   63.00  133.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -61.0000 -150.0000 70

#__ type_ start__ end____ width___ exp.time_
 11 omega   86.00  172.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   30.0000  -90.0000 86

#__ type_ start__ end____ width___ exp.time_
 12 omega  108.00  178.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   30.0000 -150.0000 70

#__ type_ start__ end____ width___ exp.time_
 13 omega   66.00  130.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       41.3104  178.0000 -180.0000 64

#__ type_ start__ end____ width___ exp.time_
 14 omega  129.00  176.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   30.0000  120.0000 47

#__ type_ start__ end____ width___ exp.time_
 15 omega  101.00  177.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   61.0000  150.0000 76

#__ type_ start__ end____ width___ exp.time_
 16 omega   84.00  111.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   30.0000  120.0000 27

#__ type_ start__ end____ width___ exp.time_
 17 omega   46.00   97.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000   60.0000 51

#__ type_ start__ end____ width___ exp.time_
 18 omega   62.00   96.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -95.0000    0.0000 34

#__ type_ start__ end____ width___ exp.time_
 19 omega   73.00  121.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -125.0000   90.0000 48

#__ type_ start__ end____ width___ exp.time_
 20 omega   50.00   90.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000  120.0000 40

#__ type_ start__ end____ width___ exp.time_
 21 omega   36.00  129.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -77.0000   60.0000 93

#__ type_ start__ end____ width___ exp.time_
 22 omega   44.00   72.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -125.0000   90.0000 28

#__ type_ start__ end____ width___ exp.time_
 23 omega   39.00   98.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000  -60.0000 59

#__ type_ start__ end____ width___ exp.time_
 24 omega   48.00   85.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000 -120.0000 37

#__ type_ start__ end____ width___ exp.time_
 25 omega   31.00   73.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -95.0000 -120.0000 42

#__ type_ start__ end____ width___ exp.time_
 26 omega -113.00  -38.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      -41.3104  -57.0000  150.0000 75
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0532018500
_diffrn_orient_matrix_UB_12      -0.0314884500
_diffrn_orient_matrix_UB_13      -0.0274709000
_diffrn_orient_matrix_UB_21      0.0201937500
_diffrn_orient_matrix_UB_22      0.1282117500
_diffrn_orient_matrix_UB_23      0.0724450000
_diffrn_orient_matrix_UB_31      0.0070290500
_diffrn_orient_matrix_UB_32      -0.1307670500
_diffrn_orient_matrix_UB_33      0.0775591000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2698
_reflns_number_total             3120
_reflns_odcompleteness_completeness 99.32
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     72.42
_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 1.171.37.35 (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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         1.268
_refine_diff_density_min         -0.440
_refine_diff_density_rms         0.119
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         3120
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0472
_refine_ls_R_factor_gt           0.0386
_refine_ls_restrained_S_all      1.033
_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)+(0.0716P)²+0.0829P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0966
_refine_ls_wR_factor_ref         0.1049
_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), C15(H15), C16(H16), C17(H17)
2.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C21(H21A,H21B,H21C), C22(H22A,H22B,H22C)
;
_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 0.33254(10) 0.2633(3) 0.71631(16) 0.0191(5) Uani 1 1 d . . . . .
C2 C 0.31692(11) 0.3839(4) 0.6556(2) 0.0179(6) Uani 1 1 d . . . . .
C3 C 0.35179(11) 0.3821(4) 0.5766(2) 0.0179(6) Uani 1 1 d . . . . .
C4 C 0.38859(11) 0.2576(4) 0.60072(19) 0.0185(6) Uani 1 1 d . . . . .
C5 C 0.37460(11) 0.1876(4) 0.6862(2) 0.0187(6) Uani 1 1 d . . . . .
C6 C 0.40079(12) 0.0607(4) 0.7294(2) 0.0227(6) Uani 1 1 d . . . . .
H6 H 0.3913 0.0145 0.7852 0.027 Uiso 1 1 calc R . . . .
C7 C 0.44189(13) 0.0044(4) 0.6866(2) 0.0247(6) Uani 1 1 d . . . . .
H7 H 0.4598 -0.0824 0.7138 0.030 Uiso 1 1 calc R . . . .
C8 C 0.45712(13) 0.0743(4) 0.6041(2) 0.0242(6) Uani 1 1 d . . . . .
H8 H 0.4854 0.0357 0.5784 0.029 Uiso 1 1 calc R . . . .
C9 C 0.43037(12) 0.2014(4) 0.5596(2) 0.0219(6) Uani 1 1 d . . . . .
H9 H 0.4402 0.2474 0.5041 0.026 Uiso 1 1 calc R . . . .
C10 C 0.30792(13) 0.2157(4) 0.8000(2) 0.0239(6) Uani 1 1 d . . . . .
H10A H 0.2831 0.2944 0.8121 0.036 Uiso 1 1 calc GR . . . .
H10B H 0.3321 0.2088 0.8540 0.036 Uiso 1 1 calc GR . . . .
H10C H 0.2924 0.1124 0.7890 0.036 Uiso 1 1 calc GR . . . .
O11 O 0.28182(8) 0.4754(3) 0.65974(15) 0.0215(4) Uani 1 1 d . . . . .
N12 N 0.34214(9) 0.4812(3) 0.50658(17) 0.0175(5) Uani 1 1 d . . . . .
C13 C 0.37325(11) 0.4725(3) 0.42832(19) 0.0171(6) Uani 1 1 d . . . . .
C14 C 0.41545(12) 0.5696(4) 0.4295(2) 0.0193(6) Uani 1 1 d . . . . .
C15 C 0.44456(12) 0.5585(4) 0.3526(2) 0.0213(6) Uani 1 1 d . . . . .
H15 H 0.4731 0.6211 0.3518 0.026 Uiso 1 1 calc R . . . .
C16 C 0.43137(12) 0.4548(4) 0.2769(2) 0.0226(6) Uani 1 1 d . . . . .
H16 H 0.4513 0.4475 0.2264 0.027 Uiso 1 1 calc R . . . .
C17 C 0.38856(12) 0.3625(4) 0.2770(2) 0.0211(6) Uani 1 1 d . . . . .
H17 H 0.3798 0.2945 0.2258 0.025 Uiso 1 1 calc R . . . .
C18 C 0.35823(12) 0.3692(3) 0.3520(2) 0.0190(6) Uani 1 1 d . . . . .
Cu19 Cu 0.28483(2) 0.63041(6) 0.51518(3) 0.02071(14) Uani 1 1 d . . . . .
Br20 Br 0.20230(2) 0.59023(4) 0.43752(2) 0.02174(13) Uani 1 1 d . . . . .
C21 C 0.31193(13) 0.2686(4) 0.3527(2) 0.0238(6) Uani 1 1 d . . . . .
H21A H 0.3044 0.2210 0.2911 0.036 Uiso 1 1 calc GR . . . .
H21B H 0.2847 0.3357 0.3678 0.036 Uiso 1 1 calc GR . . . .
H21C H 0.3171 0.1850 0.3995 0.036 Uiso 1 1 calc GR . . . .
C22 C 0.42898(13) 0.6845(4) 0.5108(2) 0.0278(7) Uani 1 1 d . . . . .
H22A H 0.4400 0.6241 0.5668 0.042 Uiso 1 1 calc GR . . . .
H22B H 0.4003 0.7474 0.5230 0.042 Uiso 1 1 calc GR . . . .
H22C H 0.4552 0.7548 0.4943 0.042 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 1.359(4) . ?
N1 C5 1.395(4) . ?
N1 C10 1.458(4) . ?
C2 C3 1.520(4) . ?
C2 O11 1.219(4) . ?
C3 C4 1.452(4) . ?
C3 N12 1.293(4) . ?
C4 C5 1.419(4) . ?
C4 C9 1.392(4) . ?
C5 C6 1.379(5) . ?
C6 H6 0.9300 . ?
C6 C7 1.388(5) . ?
C7 H7 0.9300 . ?
C7 C8 1.394(5) . ?
C8 H8 0.9300 . ?
C8 C9 1.395(5) . ?
C9 H9 0.9300 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
O11 Cu19 2.417(2) . ?
N12 C13 1.445(4) . ?
N12 Cu19 1.992(3) . ?
C13 C14 1.393(4) . ?
C13 C18 1.407(4) . ?
C14 C15 1.397(4) . ?
C14 C22 1.511(4) . ?
C15 H15 0.9300 . ?
C15 C16 1.392(4) . ?
C16 H16 0.9300 . ?
C16 C17 1.385(5) . ?
C17 H17 0.9300 . ?
C17 C18 1.394(4) . ?
C18 C21 1.502(4) . ?
Cu19 Cu19 2.7395(9) 7_566 ?
Cu19 Br20 2.4179(6) . ?
Cu19 Br20 2.4259(5) 7_566 ?
Br20 Cu19 2.4259(5) 7_566 ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 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 110.8(2) . . ?
C2 N1 C10 124.8(3) . . ?
C5 N1 C10 124.3(3) . . ?
N1 C2 C3 106.1(3) . . ?
O11 C2 N1 128.8(3) . . ?
O11 C2 C3 125.0(3) . . ?
C4 C3 C2 106.8(2) . . ?
N12 C3 C2 117.2(3) . . ?
N12 C3 C4 136.0(3) . . ?
C5 C4 C3 105.3(3) . . ?
C9 C4 C3 134.6(3) . . ?
C9 C4 C5 120.1(3) . . ?
N1 C5 C4 111.0(3) . . ?
C6 C5 N1 127.4(3) . . ?
C6 C5 C4 121.6(3) . . ?
C5 C6 H6 121.2 . . ?
C5 C6 C7 117.5(3) . . ?
C7 C6 H6 121.2 . . ?
C6 C7 H7 119.1 . . ?
C6 C7 C8 121.9(3) . . ?
C8 C7 H7 119.1 . . ?
C7 C8 H8 119.6 . . ?
C7 C8 C9 120.7(3) . . ?
C9 C8 H8 119.6 . . ?
C4 C9 C8 118.1(3) . . ?
C4 C9 H9 120.9 . . ?
C8 C9 H9 120.9 . . ?
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 Cu19 101.96(18) . . ?
C3 N12 C13 117.4(2) . . ?
C3 N12 Cu19 117.0(2) . . ?
C13 N12 Cu19 125.64(19) . . ?
C14 C13 N12 119.3(2) . . ?
C14 C13 C18 122.8(3) . . ?
C18 C13 N12 117.8(3) . . ?
C13 C14 C15 117.8(3) . . ?
C13 C14 C22 121.1(3) . . ?
C15 C14 C22 121.1(3) . . ?
C14 C15 H15 119.6 . . ?
C16 C15 C14 120.9(3) . . ?
C16 C15 H15 119.6 . . ?
C15 C16 H16 120.1 . . ?
C17 C16 C15 119.9(3) . . ?
C17 C16 H16 120.1 . . ?
C16 C17 H17 119.2 . . ?
C16 C17 C18 121.5(3) . . ?
C18 C17 H17 119.2 . . ?
C13 C18 C21 121.2(3) . . ?
C17 C18 C13 117.1(3) . . ?
C17 C18 C21 121.7(3) . . ?
O11 Cu19 Cu19 116.33(6) . 7_566 ?
O11 Cu19 Br20 106.83(5) . 7_566 ?
O11 Cu19 Br20 102.25(6) . . ?
N12 Cu19 O11 78.73(9) . . ?
N12 Cu19 Cu19 164.87(7) . 7_566 ?
N12 Cu19 Br20 121.07(7) . 7_566 ?
N12 Cu19 Br20 125.17(7) . . ?
Br20 Cu19 Cu19 55.697(17) . 7_566 ?
Br20 Cu19 Cu19 55.419(18) 7_566 7_566 ?
Br20 Cu19 Br20 111.12(2) . 7_566 ?
Cu19 Br20 Cu19 68.88(2) . 7_566 ?
C18 C21 H21A 109.5 . . ?
C18 C21 H21B 109.5 . . ?
C18 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C14 C22 H22A 109.5 . . ?
C14 C22 H22B 109.5 . . ?
C14 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 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 -2.5(3) . . . . ?
N1 C2 C3 N12 175.8(3) . . . . ?
N1 C2 O11 Cu19 -177.2(3) . . . . ?
N1 C5 C6 C7 -179.9(3) . . . . ?
C2 N1 C5 C4 -0.5(3) . . . . ?
C2 N1 C5 C6 -180.0(3) . . . . ?
C2 C3 C4 C5 2.2(3) . . . . ?
C2 C3 C4 C9 -177.7(3) . . . . ?
C2 C3 N12 C13 -176.0(2) . . . . ?
C2 C3 N12 Cu19 3.0(3) . . . . ?
C3 C2 O11 Cu19 1.2(3) . . . . ?
C3 C4 C5 N1 -1.2(3) . . . . ?
C3 C4 C5 C6 178.4(3) . . . . ?
C3 C4 C9 C8 -179.2(3) . . . . ?
C3 N12 C13 C14 -91.6(3) . . . . ?
C3 N12 C13 C18 90.6(3) . . . . ?
C4 C3 N12 C13 1.6(5) . . . . ?
C4 C3 N12 Cu19 -179.4(3) . . . . ?
C4 C5 C6 C7 0.6(4) . . . . ?
C5 N1 C2 C3 1.8(3) . . . . ?
C5 N1 C2 O11 -179.6(3) . . . . ?
C5 C4 C9 C8 0.9(4) . . . . ?
C5 C6 C7 C8 1.2(5) . . . . ?
C6 C7 C8 C9 -2.0(5) . . . . ?
C7 C8 C9 C4 0.8(5) . . . . ?
C9 C4 C5 N1 178.7(3) . . . . ?
C9 C4 C5 C6 -1.7(4) . . . . ?
C10 N1 C2 C3 -176.4(3) . . . . ?
C10 N1 C2 O11 2.2(5) . . . . ?
C10 N1 C5 C4 177.8(3) . . . . ?
C10 N1 C5 C6 -1.8(5) . . . . ?
O11 C2 C3 C4 178.8(3) . . . . ?
O11 C2 C3 N12 -2.9(4) . . . . ?
N12 C3 C4 C5 -175.6(3) . . . . ?
N12 C3 C4 C9 4.5(6) . . . . ?
N12 C13 C14 C15 -179.8(3) . . . . ?
N12 C13 C14 C22 -0.4(4) . . . . ?
N12 C13 C18 C17 179.8(3) . . . . ?
N12 C13 C18 C21 -1.2(4) . . . . ?
C13 C14 C15 C16 0.7(4) . . . . ?
C14 C13 C18 C17 2.2(4) . . . . ?
C14 C13 C18 C21 -178.8(3) . . . . ?
C14 C15 C16 C17 0.8(5) . . . . ?
C15 C16 C17 C18 -0.8(5) . . . . ?
C16 C17 C18 C13 -0.7(4) . . . . ?
C16 C17 C18 C21 -179.7(3) . . . . ?
C18 C13 C14 C15 -2.2(4) . . . . ?
C18 C13 C14 C22 177.2(3) . . . . ?
Cu19 N12 C13 C14 89.4(3) . . . . ?
Cu19 N12 C13 C18 -88.3(3) . . . . ?
C22 C14 C15 C16 -178.7(3) . . . . ?

####################################################################### 
# 
# 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_xrd_16
_database_code_depnum_ccdc_archive 'CCDC 1538879'
_audit_update_record             
;
2017-03-19 deposited with the CCDC.
2018-10-29 downloaded from the CCDC.
;
_audit_creation_date             2015-11-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C15 H12 Cu I N2 O'
_chemical_formula_sum            'C15 H12 Cu I N2 O'
_chemical_formula_weight         426.71
_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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   8.5695(9)
_cell_length_b                   9.3493(7)
_cell_length_c                   10.6986(11)
_cell_angle_alpha                74.782(9)
_cell_angle_beta                 75.057(9)
_cell_angle_gamma                63.915(10)
_cell_volume                     732.76(14)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2003
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.2970
_cell_measurement_theta_min      3.4030
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.592
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87133
_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    1.934
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       lamina
_exptl_crystal_F_000             412
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.01
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0315
_diffrn_reflns_av_unetI/netI     0.0583
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6003
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.494
_diffrn_reflns_theta_min         2.827
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 16.2096
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   19.00   46.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.4081   57.0000  -90.0000 27

#__ type_ start__ end____ width___ exp.time_
  2 omega  -42.00   48.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.4081   57.0000 -120.0000 90

#__ type_ start__ end____ width___ exp.time_
  3 omega   -8.00   20.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.4081  -99.0000 -150.0000 28

#__ type_ start__ end____ width___ exp.time_
  4 omega  -50.00   50.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.4081   77.0000  -30.0000 100

#__ type_ start__ end____ width___ exp.time_
  5 omega  -25.00    0.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.4081  -99.0000 -180.0000 25

#__ type_ start__ end____ width___ exp.time_
  6 omega    4.00   46.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -       21.3456   57.0000   90.0000 42

#__ type_ start__ end____ width___ exp.time_
  7 omega  -48.00   51.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -       21.3456  -77.0000  120.0000 99
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0803583000
_diffrn_orient_matrix_UB_12      -0.0383005000
_diffrn_orient_matrix_UB_13      0.0251704000
_diffrn_orient_matrix_UB_21      0.0090565000
_diffrn_orient_matrix_UB_22      -0.0757531000
_diffrn_orient_matrix_UB_23      -0.0094585000
_diffrn_orient_matrix_UB_31      0.0467899000
_diffrn_orient_matrix_UB_32      0.0121198000
_diffrn_orient_matrix_UB_33      -0.0642554000
_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                2866
_reflns_number_total             3355
_reflns_odcompleteness_completeness 99.85
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.50
_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, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.875
_refine_diff_density_min         -0.792
_refine_diff_density_rms         0.127
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         3355
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0425
_refine_ls_R_factor_gt           0.0329
_refine_ls_restrained_S_all      1.015
_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)+(0.0149P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0561
_refine_ls_wR_factor_ref         0.0602
_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
N1 N 0.2359(4) 0.4641(4) 0.5255(3) 0.0186(7) Uani 1 1 d . . . . .
C2 C 0.3058(4) 0.4583(4) 0.3957(3) 0.0161(8) Uani 1 1 d . . . . .
C3 C 0.2961(4) 0.3119(4) 0.3661(3) 0.0139(7) Uani 1 1 d . . . . .
C4 C 0.2159(4) 0.2381(5) 0.4893(3) 0.0176(8) Uani 1 1 d . . . . .
C5 C 0.1784(4) 0.3375(4) 0.5814(3) 0.0172(8) Uani 1 1 d . . . . .
C6 C 0.0946(5) 0.3070(5) 0.7087(3) 0.0228(9) Uani 1 1 d . . . . .
H6 H 0.0708 0.3722 0.7693 0.027 Uiso 1 1 calc R . . . .
C7 C 0.0472(5) 0.1759(5) 0.7424(3) 0.0274(10) Uani 1 1 d . . . . .
H7 H -0.0106 0.1543 0.8269 0.033 Uiso 1 1 calc R . . . .
C8 C 0.0838(5) 0.0755(5) 0.6531(3) 0.0262(9) Uani 1 1 d . . . . .
H8 H 0.0520 -0.0124 0.6791 0.031 Uiso 1 1 calc R . . . .
C9 C 0.1680(5) 0.1064(5) 0.5252(3) 0.0211(8) Uani 1 1 d . . . . .
H9 H 0.1917 0.0406 0.4650 0.025 Uiso 1 1 calc R . . . .
C10 C 0.2216(5) 0.5872(5) 0.5928(4) 0.0253(9) Uani 1 1 d . . . . .
H10A H 0.2981 0.5380 0.6575 0.038 Uiso 1 1 calc GR . . . .
H10B H 0.1022 0.6372 0.6350 0.038 Uiso 1 1 calc GR . . . .
H10C H 0.2550 0.6676 0.5302 0.038 Uiso 1 1 calc GR . . . .
O11 O 0.3665(3) 0.5489(3) 0.3169(2) 0.0211(6) Uani 1 1 d . . . . .
N12 N 0.3496(3) 0.2870(3) 0.2465(3) 0.0142(6) Uani 1 1 d . . . . .
C13 C 0.3518(4) 0.1480(4) 0.2115(3) 0.0157(8) Uani 1 1 d . . . . .
C14 C 0.4608(5) -0.0063(5) 0.2632(3) 0.0215(8) Uani 1 1 d . . . . .
H14 H 0.5299 -0.0211 0.3235 0.026 Uiso 1 1 calc R . . . .
C15 C 0.4656(5) -0.1387(5) 0.2235(4) 0.0232(9) Uani 1 1 d . . . . .
H15 H 0.5375 -0.2425 0.2584 0.028 Uiso 1 1 calc R . . . .
C16 C 0.3648(5) -0.1179(5) 0.1329(3) 0.0219(8) Uani 1 1 d . . . . .
H16 H 0.3676 -0.2072 0.1081 0.026 Uiso 1 1 calc R . . . .
C17 C 0.2597(5) 0.0368(5) 0.0793(3) 0.0218(8) Uani 1 1 d . . . . .
H17 H 0.1922 0.0515 0.0178 0.026 Uiso 1 1 calc R . . . .
C18 C 0.2549(4) 0.1708(5) 0.1174(3) 0.0193(8) Uani 1 1 d . . . . .
H18 H 0.1868 0.2748 0.0797 0.023 Uiso 1 1 calc R . . . .
Cu19 Cu 0.43545(5) 0.43902(5) 0.10954(4) 0.01798(11) Uani 1 1 d . . . . .
I20 I 0.76892(3) 0.36925(3) 0.05686(2) 0.02043(8) 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
N1 C2 1.368(4) . ?
N1 C5 1.410(5) . ?
N1 C10 1.458(4) . ?
C2 C3 1.523(5) . ?
C2 O11 1.219(4) . ?
C3 C4 1.469(4) . ?
C3 N12 1.290(4) . ?
C4 C5 1.411(5) . ?
C4 C9 1.396(5) . ?
C5 C6 1.387(5) . ?
C6 H6 0.9300 . ?
C6 C7 1.389(5) . ?
C7 H7 0.9300 . ?
C7 C8 1.396(5) . ?
C8 H8 0.9300 . ?
C8 C9 1.395(5) . ?
C9 H9 0.9300 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
N12 C13 1.435(4) . ?
N12 Cu19 1.995(3) . ?
C13 C14 1.386(5) . ?
C13 C18 1.383(5) . ?
C14 H14 0.9300 . ?
C14 C15 1.392(5) . ?
C15 H15 0.9300 . ?
C15 C16 1.380(5) . ?
C16 H16 0.9300 . ?
C16 C17 1.384(5) . ?
C17 H17 0.9300 . ?
C17 C18 1.397(5) . ?
C18 H18 0.9300 . ?
Cu19 Cu19 2.5273(8) 2_665 ?
Cu19 I20 2.5732(6) 2_665 ?
Cu19 I20 2.5754(6) . ?
I20 Cu19 2.5732(6) 2_665 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C5 110.3(3) . . ?
C2 N1 C10 123.6(3) . . ?
C5 N1 C10 126.1(3) . . ?
N1 C2 C3 106.4(3) . . ?
O11 C2 N1 128.3(3) . . ?
O11 C2 C3 125.2(3) . . ?
C4 C3 C2 106.5(3) . . ?
N12 C3 C2 116.9(3) . . ?
N12 C3 C4 136.6(3) . . ?
C5 C4 C3 105.5(3) . . ?
C9 C4 C3 134.3(3) . . ?
C9 C4 C5 120.1(3) . . ?
N1 C5 C4 111.2(3) . . ?
C6 C5 N1 127.4(3) . . ?
C6 C5 C4 121.3(4) . . ?
C5 C6 H6 121.1 . . ?
C5 C6 C7 117.7(4) . . ?
C7 C6 H6 121.1 . . ?
C6 C7 H7 119.0 . . ?
C6 C7 C8 121.9(3) . . ?
C8 C7 H7 119.0 . . ?
C7 C8 H8 119.9 . . ?
C9 C8 C7 120.2(4) . . ?
C9 C8 H8 119.9 . . ?
C4 C9 H9 120.7 . . ?
C8 C9 C4 118.6(3) . . ?
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 . . ?
C3 N12 C13 120.4(3) . . ?
C3 N12 Cu19 120.1(2) . . ?
C13 N12 Cu19 119.6(2) . . ?
C14 C13 N12 120.3(3) . . ?
C18 C13 N12 118.9(3) . . ?
C18 C13 C14 120.6(3) . . ?
C13 C14 H14 120.4 . . ?
C13 C14 C15 119.1(4) . . ?
C15 C14 H14 120.4 . . ?
C14 C15 H15 119.6 . . ?
C16 C15 C14 120.9(4) . . ?
C16 C15 H15 119.6 . . ?
C15 C16 H16 120.2 . . ?
C15 C16 C17 119.6(3) . . ?
C17 C16 H16 120.2 . . ?
C16 C17 H17 119.9 . . ?
C16 C17 C18 120.1(3) . . ?
C18 C17 H17 119.9 . . ?
C13 C18 C17 119.6(3) . . ?
C13 C18 H18 120.2 . . ?
C17 C18 H18 120.2 . . ?
N12 Cu19 Cu19 160.56(8) . 2_665 ?
N12 Cu19 I20 116.92(8) . 2_665 ?
N12 Cu19 I20 118.23(8) . . ?
Cu19 Cu19 I20 60.65(2) 2_665 2_665 ?
Cu19 Cu19 I20 60.56(2) 2_665 . ?
I20 Cu19 I20 121.205(19) 2_665 . ?
Cu19 I20 Cu19 58.796(19) 2_665 . ?

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 -0.1(4) . . . . ?
N1 C2 C3 N12 177.4(3) . . . . ?
N1 C5 C6 C7 179.2(3) . . . . ?
C2 N1 C5 C4 2.4(4) . . . . ?
C2 N1 C5 C6 -177.3(3) . . . . ?
C2 C3 C4 C5 1.4(4) . . . . ?
C2 C3 C4 C9 178.0(4) . . . . ?
C2 C3 N12 C13 177.4(3) . . . . ?
C2 C3 N12 Cu19 -1.2(4) . . . . ?
C3 C4 C5 N1 -2.3(4) . . . . ?
C3 C4 C5 C6 177.4(3) . . . . ?
C3 C4 C9 C8 -176.5(4) . . . . ?
C3 N12 C13 C14 -64.3(4) . . . . ?
C3 N12 C13 C18 121.1(4) . . . . ?
C4 C3 N12 C13 -6.1(6) . . . . ?
C4 C3 N12 Cu19 175.3(3) . . . . ?
C4 C5 C6 C7 -0.5(5) . . . . ?
C5 N1 C2 C3 -1.3(4) . . . . ?
C5 N1 C2 O11 179.3(3) . . . . ?
C5 C4 C9 C8 -0.3(5) . . . . ?
C5 C6 C7 C8 0.9(6) . . . . ?
C6 C7 C8 C9 -1.0(6) . . . . ?
C7 C8 C9 C4 0.6(6) . . . . ?
C9 C4 C5 N1 -179.5(3) . . . . ?
C9 C4 C5 C6 0.2(5) . . . . ?
C10 N1 C2 C3 179.8(3) . . . . ?
C10 N1 C2 O11 0.4(6) . . . . ?
C10 N1 C5 C4 -178.8(3) . . . . ?
C10 N1 C5 C6 1.5(6) . . . . ?
O11 C2 C3 C4 179.4(3) . . . . ?
O11 C2 C3 N12 -3.1(5) . . . . ?
N12 C3 C4 C5 -175.4(4) . . . . ?
N12 C3 C4 C9 1.3(8) . . . . ?
N12 C13 C14 C15 -177.4(3) . . . . ?
N12 C13 C18 C17 178.1(3) . . . . ?
C13 C14 C15 C16 0.7(5) . . . . ?
C14 C13 C18 C17 3.5(5) . . . . ?
C14 C15 C16 C17 1.0(5) . . . . ?
C15 C16 C17 C18 -0.4(5) . . . . ?
C16 C17 C18 C13 -1.8(5) . . . . ?
C18 C13 C14 C15 -2.9(5) . . . . ?
Cu19 N12 C13 C14 114.3(3) . . . . ?
Cu19 N12 C13 C18 -60.3(3) . . . . ?



####################################################################### 
# 
# 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_pd_127
_database_code_depnum_ccdc_archive 'CCDC 1538878'
_audit_update_record             
;
2017-03-19 deposited with the CCDC.
2018-10-29 downloaded from the CCDC.
;
_audit_creation_date             2016-10-15
_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         'C21 H24 Br Cu N2 O, C21 H24 Br0.7 Cu0.7 N2 O'
_chemical_formula_sum            'C42 H48 Br1.70 Cu1.70 N4 O2'
_chemical_formula_weight         884.71
_chemical_melting_point          ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -1.9646 0.5888 '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                   11.0842(4)
_cell_length_b                   11.7852(5)
_cell_length_c                   17.1333(5)
_cell_angle_alpha                99.747(3)
_cell_angle_beta                 108.723(3)
_cell_angle_gamma                102.672(3)
_cell_volume                     1997.24(13)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    10674
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      75.4800
_cell_measurement_theta_min      3.9740
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.451
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70706
_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.
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.471
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             906
_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  0.0634
_diffrn_reflns_av_unetI/netI     0.0505
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            27863
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.486
_diffrn_reflns_theta_min         3.981
_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 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -24.00   36.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      -40.2537   38.0000   60.0000 60

#__ type_ start__ end____ width___ exp.time_
  2 omega  -60.00   32.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      -40.2537   57.0000  150.0000 92

#__ type_ start__ end____ width___ exp.time_
  3 omega    3.00   76.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -       40.2537  -99.0000 -150.0000 73

#__ type_ start__ end____ width___ exp.time_
  4 omega   68.00  111.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000  -60.0000 43

#__ type_ start__ end____ width___ exp.time_
  5 omega   77.00  115.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000    0.0000 38

#__ type_ start__ end____ width___ exp.time_
  6 omega   80.00  115.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000   60.0000 35

#__ type_ start__ end____ width___ exp.time_
  7 omega   90.00  147.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000  120.0000 57

#__ type_ start__ end____ width___ exp.time_
  8 omega  108.00  133.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   15.0000    0.0000 25

#__ type_ start__ end____ width___ exp.time_
  9 omega  120.00  171.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   30.0000   60.0000 51

#__ type_ start__ end____ width___ exp.time_
 10 omega  123.00  175.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000  120.0000 52

#__ type_ start__ end____ width___ exp.time_
 11 omega  102.00  155.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  112.0000   60.0000 53

#__ type_ start__ end____ width___ exp.time_
 12 omega  112.00  156.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000  -60.0000 44

#__ type_ start__ end____ width___ exp.time_
 13 omega  126.00  154.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   15.0000 -120.0000 28

#__ type_ start__ end____ width___ exp.time_
 14 omega  152.00  177.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000 -120.0000 25

#__ type_ start__ end____ width___ exp.time_
 15 omega   99.00  139.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000 -120.0000 40

#__ type_ start__ end____ width___ exp.time_
 16 omega   82.00  170.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   30.0000    0.0000 88

#__ type_ start__ end____ width___ exp.time_
 17 omega  113.00  138.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000 -150.0000 25

#__ type_ start__ end____ width___ exp.time_
 18 omega   92.00  147.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000 -180.0000 55

#__ type_ start__ end____ width___ exp.time_
 19 omega   79.00  115.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000 -180.0000 36

#__ type_ start__ end____ width___ exp.time_
 20 omega   68.00  111.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000 -120.0000 43

#__ type_ start__ end____ width___ exp.time_
 21 omega   72.00   97.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -61.0000 -180.0000 25

#__ type_ start__ end____ width___ exp.time_
 22 omega   60.00   85.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000 -150.0000 25

#__ type_ start__ end____ width___ exp.time_
 23 omega   51.00   78.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000 -180.0000 27

#__ type_ start__ end____ width___ exp.time_
 24 omega   45.00   74.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000 -150.0000 29

#__ type_ start__ end____ width___ exp.time_
 25 omega   67.00   94.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   15.0000 -180.0000 27

#__ type_ start__ end____ width___ exp.time_
 26 omega   74.00  107.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   15.0000 -120.0000 33

#__ type_ start__ end____ width___ exp.time_
 27 omega   41.00   97.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000 -150.0000 56

#__ type_ start__ end____ width___ exp.time_
 28 omega   40.00   66.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000 -150.0000 26

#__ type_ start__ end____ width___ exp.time_
 29 omega   29.00  101.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000 -180.0000 72

#__ type_ start__ end____ width___ exp.time_
 30 omega   39.00  100.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -54.0000  -30.9678 61

#__ type_ start__ end____ width___ exp.time_
 31 omega   82.00  126.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -87.0000   25.4318 44

#__ type_ start__ end____ width___ exp.time_
 32 omega   82.00  115.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000   90.0000 33

#__ type_ start__ end____ width___ exp.time_
 33 omega   81.00  109.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000   90.0000 28

#__ type_ start__ end____ width___ exp.time_
 34 omega   72.00  115.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000   30.0000 43

#__ type_ start__ end____ width___ exp.time_
 35 omega   64.00   89.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000  150.0000 25

#__ type_ start__ end____ width___ exp.time_
 36 omega   52.00   85.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000  120.0000 33

#__ type_ start__ end____ width___ exp.time_
 37 omega   52.00   96.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -61.0000   30.0000 44

#__ type_ start__ end____ width___ exp.time_
 38 omega   49.00   76.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000    0.0000 27

#__ type_ start__ end____ width___ exp.time_
 39 omega   55.00   80.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000    0.0000 25

#__ type_ start__ end____ width___ exp.time_
 40 omega   40.00   98.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -56.0000   64.0000 58

#__ type_ start__ end____ width___ exp.time_
 41 omega   44.00   69.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000   90.0000 25

#__ type_ start__ end____ width___ exp.time_
 42 omega   38.00   65.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000   30.0000 27

#__ type_ start__ end____ width___ exp.time_
 43 omega   30.00   82.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000   60.0000 52

#__ type_ start__ end____ width___ exp.time_
 44 omega   84.00  113.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   30.0000   60.0000 29

#__ type_ start__ end____ width___ exp.time_
 45 omega   93.00  122.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000  120.0000 29

#__ type_ start__ end____ width___ exp.time_
 46 omega  102.00  132.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000  150.0000 30

#__ type_ start__ end____ width___ exp.time_
 47 omega   63.00  100.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  178.0000  -60.0000 37

#__ type_ start__ end____ width___ exp.time_
 48 omega   68.00   93.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  178.0000 -150.0000 25

#__ type_ start__ end____ width___ exp.time_
 49 omega  120.00  147.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  178.0000 -150.0000 27

#__ type_ start__ end____ width___ exp.time_
 50 omega -109.00  -49.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      -40.2537  -57.0000    0.0000 60

#__ type_ start__ end____ width___ exp.time_
 51 omega -114.00  -16.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      -40.2537  -57.0000  -90.0000 98

#__ type_ start__ end____ width___ exp.time_
 52 omega -127.00  -72.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      -40.2537  178.0000  -60.0000 55

#__ type_ start__ end____ width___ exp.time_
 53 omega   85.00  121.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   56.0000 -153.0000 36

#__ type_ start__ end____ width___ exp.time_
 54 omega -112.00  -11.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      -40.2537  -56.0000   64.0000 101

#__ type_ start__ end____ width___ exp.time_
 55 omega -114.00  -14.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      -40.2537  -38.0000  120.0000 100

#__ type_ start__ end____ width___ exp.time_
 56 omega    6.00   31.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -       44.0000   89.0000  -66.8482 25

#__ type_ start__ end____ width___ exp.time_
 57 omega   13.00   38.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -       48.0000   81.0000  175.9105 25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0846063000
_diffrn_orient_matrix_UB_12      0.0723537000
_diffrn_orient_matrix_UB_13      -0.0478833000
_diffrn_orient_matrix_UB_21      0.1166165000
_diffrn_orient_matrix_UB_22      0.1162286000
_diffrn_orient_matrix_UB_23      0.0462998000
_diffrn_orient_matrix_UB_31      0.0529738000
_diffrn_orient_matrix_UB_32      -0.0224226000
_diffrn_orient_matrix_UB_33      -0.0723017000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6860
_reflns_number_total             7935
_reflns_odcompleteness_completeness 94.89
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     80.07
_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 1.171.37.35 (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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         1.246
_refine_diff_density_min         -0.885
_refine_diff_density_rms         0.105
_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     491
_refine_ls_number_reflns         7935
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0575
_refine_ls_R_factor_gt           0.0492
_refine_ls_restrained_S_all      1.040
_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)+(0.0708P)²+2.2897P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1232
_refine_ls_wR_factor_ref         0.1305
_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(C24B) = Uanis(C24A)
Uanis(C23B) = Uanis(C23A)
Uanis(C22A) = Uanis(C22B)
3. Others
 Sof(C22B)=Sof(H22B)=Sof(C23B)=Sof(H23D)=Sof(H23E)=Sof(H23F)=Sof(C24B)=
 Sof(H24D)=Sof(H24E)=Sof(H24F)=1-FVAR(1)
 Sof(C22A)=Sof(H22A)=Sof(C23A)=Sof(H23A)=Sof(H23B)=Sof(H23C)=Sof(C24A)=
 Sof(H24A)=Sof(H24B)=Sof(H24C)=Sof(Br25A)=Sof(Cu25A)=FVAR(1)
4.a Ternary CH refined with riding coordinates:
 C19(H19), C22(H22), C19A(H19A), C22A(H22A), C22B(H22B)
4.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C9(H9), C15(H15), C16(H16), C17(H17), C6A(H6A),
 C7A(H7A), C8A(H8A), C9A(H9A), C15A(H15A), C16A(H16A), C17A(H17A)
4.c Idealised Me refined as rotating group:
 C10(H10D,H10E,H10F), C20(H20D,H20E,H20F), C21(H21D,H21E,H21F), C23(H23G,H23H,
 H23I), C24(H24G,H24H,H24I), C10A(H10A,H10B,H10C), C20A(H20A,H20B,H20C),
 C21A(H21A,H21B,H21C), C23A(H23A,H23B,H23C), C23B(H23D,H23E,H23F), C24A(H24A,
 H24B,H24C), C24B(H24D,H24E,H24F)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.0576(3) -0.0404(2) 0.10225(16) 0.0199(5) Uani 1 1 d . . . . .
C2 C 0.1718(3) -0.0321(3) 0.08705(19) 0.0184(6) Uani 1 1 d . . . . .
C3 C 0.2766(3) 0.0761(3) 0.15477(18) 0.0169(5) Uani 1 1 d . . . . .
C4 C 0.2125(3) 0.1230(3) 0.20983(19) 0.0190(6) Uani 1 1 d . . . . .
C5 C 0.0783(3) 0.0503(3) 0.17433(19) 0.0194(6) Uani 1 1 d . . . . .
C6 C -0.0134(3) 0.0723(3) 0.2090(2) 0.0240(6) Uani 1 1 d . . . . .
H6 H -0.1018 0.0249 0.1850 0.029 Uiso 1 1 calc R . . . .
C7 C 0.0312(3) 0.1680(3) 0.2813(2) 0.0274(7) Uani 1 1 d . . . . .
H7 H -0.0287 0.1844 0.3058 0.033 Uiso 1 1 calc R . . . .
C8 C 0.1637(3) 0.2400(3) 0.3178(2) 0.0252(6) Uani 1 1 d . . . . .
H8 H 0.1907 0.3028 0.3664 0.030 Uiso 1 1 calc R . . . .
C9 C 0.2550(3) 0.2186(3) 0.2823(2) 0.0231(6) Uani 1 1 d . . . . .
H9 H 0.3430 0.2669 0.3063 0.028 Uiso 1 1 calc R . . . .
C10 C -0.0683(3) -0.1332(3) 0.0510(2) 0.0245(6) Uani 1 1 d . . . . .
H10D H -0.0814 -0.1948 0.0802 0.037 Uiso 1 1 calc GR . . . .
H10E H -0.0660 -0.1679 -0.0032 0.037 Uiso 1 1 calc GR . . . .
H10F H -0.1402 -0.0979 0.0422 0.037 Uiso 1 1 calc GR . . . .
O11 O 0.1886(2) -0.0957(2) 0.02953(14) 0.0229(4) Uani 1 1 d . . . . .
N12 N 0.3922(3) 0.1086(2) 0.15078(15) 0.0173(5) Uani 1 1 d . . . . .
C13 C 0.4889(3) 0.2168(3) 0.21273(18) 0.0182(6) Uani 1 1 d . . . . .
C14 C 0.5775(3) 0.2057(3) 0.28875(19) 0.0212(6) Uani 1 1 d . . . . .
C15 C 0.6692(3) 0.3120(3) 0.3459(2) 0.0261(7) Uani 1 1 d . . . . .
H15 H 0.7288 0.3081 0.3972 0.031 Uiso 1 1 calc R . . . .
C16 C 0.6741(4) 0.4225(3) 0.3284(2) 0.0293(7) Uani 1 1 d . . . . .
H16 H 0.7370 0.4917 0.3674 0.035 Uiso 1 1 calc R . . . .
C17 C 0.5850(3) 0.4305(3) 0.2527(2) 0.0262(7) Uani 1 1 d . . . . .
H17 H 0.5882 0.5055 0.2416 0.031 Uiso 1 1 calc R . . . .
C18 C 0.4904(3) 0.3271(3) 0.19291(19) 0.0211(6) Uani 1 1 d . . . . .
C19 C 0.5743(3) 0.0850(3) 0.3096(2) 0.0266(7) Uani 1 1 d . . . . .
H19 H 0.5049 0.0222 0.2612 0.032 Uiso 1 1 calc R . . . .
C20 C 0.5389(5) 0.0808(5) 0.3885(3) 0.0480(11) Uani 1 1 d . . . . .
H20D H 0.6098 0.1363 0.4379 0.072 Uiso 1 1 calc GR . . . .
H20E H 0.5264 0.0008 0.3962 0.072 Uiso 1 1 calc GR . . . .
H20F H 0.4581 0.1026 0.3810 0.072 Uiso 1 1 calc GR . . . .
C21 C 0.7079(4) 0.0582(3) 0.3221(2) 0.0310(7) Uani 1 1 d . . . . .
H21D H 0.7284 0.0613 0.2720 0.047 Uiso 1 1 calc GR . . . .
H21E H 0.7016 -0.0205 0.3314 0.047 Uiso 1 1 calc GR . . . .
H21F H 0.7770 0.1171 0.3705 0.047 Uiso 1 1 calc GR . . . .
C22 C 0.3924(3) 0.3385(3) 0.1107(2) 0.0244(6) Uani 1 1 d . . . . .
H22 H 0.3445 0.2572 0.0733 0.029 Uiso 1 1 calc R . . . .
C23 C 0.2898(4) 0.3968(3) 0.1283(2) 0.0310(7) Uani 1 1 d . . . . .
H23G H 0.2424 0.3495 0.1555 0.046 Uiso 1 1 calc GR . . . .
H23H H 0.2281 0.4008 0.0754 0.046 Uiso 1 1 calc GR . . . .
H23I H 0.3347 0.4766 0.1650 0.046 Uiso 1 1 calc GR . . . .
C24 C 0.4626(4) 0.4103(4) 0.0637(2) 0.0332(8) Uani 1 1 d . . . . .
H24G H 0.5101 0.4905 0.0991 0.050 Uiso 1 1 calc GR . . . .
H24H H 0.3979 0.4137 0.0118 0.050 Uiso 1 1 calc GR . . . .
H24I H 0.5242 0.3719 0.0504 0.050 Uiso 1 1 calc GR . . . .
Cu25 Cu 0.44149(5) 0.02825(4) 0.06175(3) 0.02087(13) Uani 1 1 d . . . . .
Br26 Br 0.59419(3) -0.08874(3) 0.07082(2) 0.02468(11) Uani 1 1 d . . . . .
N1A N 0.5583(3) 0.3597(3) 0.60215(18) 0.0287(6) Uani 1 1 d . . . . .
C2A C 0.6724(4) 0.4017(3) 0.5894(2) 0.0272(7) Uani 1 1 d . . . . .
C3A C 0.7833(3) 0.3841(3) 0.6624(2) 0.0238(6) Uani 1 1 d . . . . .
C4A C 0.7208(4) 0.3336(3) 0.7168(2) 0.0255(7) Uani 1 1 d . . . . .
C5A C 0.5834(4) 0.3202(3) 0.6776(2) 0.0279(7) Uani 1 1 d . . . . .
C6A C 0.4927(4) 0.2752(3) 0.7121(2) 0.0315(7) Uani 1 1 d . . . . .
H6A H 0.4024 0.2664 0.6855 0.038 Uiso 1 1 calc R . . . .
C7A C 0.5414(4) 0.2433(3) 0.7884(3) 0.0346(8) Uani 1 1 d . . . . .
H7A H 0.4824 0.2134 0.8134 0.042 Uiso 1 1 calc R . . . .
C8A C 0.6759(4) 0.2549(3) 0.8281(2) 0.0349(8) Uani 1 1 d . . . . .
H8A H 0.7054 0.2322 0.8787 0.042 Uiso 1 1 calc R . . . .
C9A C 0.7671(4) 0.3003(3) 0.7926(2) 0.0288(7) Uani 1 1 d . . . . .
H9A H 0.8571 0.3082 0.8191 0.035 Uiso 1 1 calc R . . . .
C10A C 0.4256(4) 0.3478(4) 0.5421(2) 0.0376(9) Uani 1 1 d . . . . .
H10A H 0.3712 0.2658 0.5265 0.056 Uiso 1 1 calc GR . . . .
H10B H 0.4324 0.3702 0.4920 0.056 Uiso 1 1 calc GR . . . .
H10C H 0.3859 0.3996 0.5684 0.056 Uiso 1 1 calc GR . . . .
O11A O 0.6862(3) 0.4423(3) 0.53114(16) 0.0362(6) Uani 1 1 d . . . . .
N12A N 0.9020(3) 0.4095(3) 0.66072(17) 0.0255(6) Uani 1 1 d . . . . .
C13A C 1.0047(4) 0.3771(3) 0.7218(2) 0.0256(7) Uani 1 1 d . . . . .
C14A C 1.0877(3) 0.4589(3) 0.8003(2) 0.0269(7) Uani 1 1 d . . . . .
C15A C 1.1895(3) 0.4246(4) 0.8536(2) 0.0295(7) Uani 1 1 d . . . . .
H15A H 1.2447 0.4767 0.9066 0.035 Uiso 1 1 calc R . . . .
C16A C 1.2105(4) 0.3146(3) 0.8297(2) 0.0297(7) Uani 1 1 d . . . . .
H16A H 1.2806 0.2941 0.8655 0.036 Uiso 1 1 calc R . . . .
C17A C 1.1272(4) 0.2363(4) 0.7528(3) 0.0386(9) Uani 1 1 d . . . . .
H17A H 1.1420 0.1627 0.7370 0.046 Uiso 1 1 calc R . . . .
C18A C 1.0211(5) 0.2634(4) 0.6977(2) 0.0386(9) Uani 1 1 d . . . . .
C19A C 1.0698(4) 0.5817(4) 0.8291(3) 0.0409(10) Uani 1 1 d . . . . .
H19A H 0.9891 0.5875 0.7865 0.049 Uiso 1 1 calc R . . . .
C20A C 1.1880(5) 0.6842(4) 0.8365(3) 0.0466(10) Uani 1 1 d . . . . .
H20A H 1.2680 0.6796 0.8778 0.070 Uiso 1 1 calc GR . . . .
H20B H 1.1733 0.7600 0.8541 0.070 Uiso 1 1 calc GR . . . .
H20C H 1.1969 0.6772 0.7821 0.070 Uiso 1 1 calc GR . . . .
C21A C 1.0529(5) 0.5966(5) 0.9154(4) 0.0553(13) Uani 1 1 d . . . . .
H21A H 0.9764 0.5346 0.9105 0.083 Uiso 1 1 calc GR . . . .
H21B H 1.0407 0.6740 0.9320 0.083 Uiso 1 1 calc GR . . . .
H21C H 1.1309 0.5906 0.9578 0.083 Uiso 1 1 calc GR . . . .
C22A C 0.9184(6) 0.1680(5) 0.6164(3) 0.0302(11) Uani 0.7025(18) 1 d . . P A 1
H22A H 0.8773 0.2117 0.5765 0.036 Uiso 0.7025(18) 1 calc R . P A 1
C22B C 0.9683(15) 0.1978(13) 0.5989(8) 0.0302(11) Uani 0.2975(18) 1 d . . P A 2
H22B H 0.9104 0.2416 0.5693 0.036 Uiso 0.2975(18) 1 calc R . P A 2
C23A C 0.9888(8) 0.0952(6) 0.5735(4) 0.0474(14) Uani 0.7025(18) 1 d . . P A 1
H23A H 1.0730 0.1469 0.5793 0.071 Uiso 0.7025(18) 1 calc GR . P A 1
H23B H 0.9345 0.0616 0.5140 0.071 Uiso 0.7025(18) 1 calc GR . P A 1
H23C H 1.0032 0.0314 0.6001 0.071 Uiso 0.7025(18) 1 calc GR . P A 1
C23B C 1.0691(18) 0.1871(15) 0.5505(9) 0.0474(14) Uani 0.2975(18) 1 d . . P A 2
H23D H 1.1194 0.2662 0.5534 0.071 Uiso 0.2975(18) 1 calc GR . P A 2
H23E H 1.0195 0.1436 0.4918 0.071 Uiso 0.2975(18) 1 calc GR . P A 2
H23F H 1.1289 0.1449 0.5772 0.071 Uiso 0.2975(18) 1 calc GR . P A 2
C24A C 0.8060(6) 0.0835(5) 0.6302(4) 0.0383(11) Uani 0.7025(18) 1 d . . P A 1
H24A H 0.8429 0.0426 0.6717 0.057 Uiso 0.7025(18) 1 calc GR . P A 1
H24B H 0.7490 0.0255 0.5773 0.057 Uiso 0.7025(18) 1 calc GR . P A 1
H24C H 0.7552 0.1293 0.6503 0.057 Uiso 0.7025(18) 1 calc GR . P A 1
C24B C 0.8795(14) 0.0799(12) 0.5911(9) 0.0383(11) Uani 0.2975(18) 1 d . . P A 2
H24D H 0.9318 0.0270 0.6081 0.057 Uiso 0.2975(18) 1 calc GR . P A 2
H24E H 0.8190 0.0460 0.5329 0.057 Uiso 0.2975(18) 1 calc GR . P A 2
H24F H 0.8299 0.0901 0.6272 0.057 Uiso 0.2975(18) 1 calc GR . P A 2
Br25A Br 0.97414(4) 0.64950(4) 0.52243(3) 0.02293(15) Uani 0.7025(18) 1 d . . P
A 1
Cu25A Cu 0.94080(7) 0.47058(7) 0.56973(4) 0.02309(19) Uani 0.7025(18) 1 d . . P
A 1


_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 1.359(4) . ?
N1 C5 1.408(4) . ?
N1 C10 1.461(4) . ?
C2 C3 1.518(4) . ?
C2 O11 1.223(4) . ?
C3 C4 1.459(4) . ?
C3 N12 1.282(4) . ?
C4 C5 1.415(4) . ?
C4 C9 1.397(4) . ?
C5 C6 1.380(4) . ?
C6 H6 0.9300 . ?
C6 C7 1.392(5) . ?
C7 H7 0.9300 . ?
C7 C8 1.397(5) . ?
C8 H8 0.9300 . ?
C8 C9 1.382(4) . ?
C9 H9 0.9300 . ?
C10 H10D 0.9600 . ?
C10 H10E 0.9600 . ?
C10 H10F 0.9600 . ?
N12 C13 1.454(4) . ?
N12 Cu25 1.948(2) . ?
C13 C14 1.404(4) . ?
C13 C18 1.396(5) . ?
C14 C15 1.396(5) . ?
C14 C19 1.520(5) . ?
C15 H15 0.9300 . ?
C15 C16 1.379(5) . ?
C16 H16 0.9300 . ?
C16 C17 1.387(5) . ?
C17 H17 0.9300 . ?
C17 C18 1.401(4) . ?
C18 C22 1.526(4) . ?
C19 H19 0.9800 . ?
C19 C20 1.530(5) . ?
C19 C21 1.537(5) . ?
C20 H20D 0.9600 . ?
C20 H20E 0.9600 . ?
C20 H20F 0.9600 . ?
C21 H21D 0.9600 . ?
C21 H21E 0.9600 . ?
C21 H21F 0.9600 . ?
C22 H22 0.9800 . ?
C22 C23 1.533(5) . ?
C22 C24 1.522(5) . ?
C23 H23G 0.9600 . ?
C23 H23H 0.9600 . ?
C23 H23I 0.9600 . ?
C24 H24G 0.9600 . ?
C24 H24H 0.9600 . ?
C24 H24I 0.9600 . ?
Cu25 Cu25 2.8752(8) 2_655 ?
Cu25 Br26 2.3911(6) . ?
Cu25 Br26 2.4327(6) 2_655 ?
Br26 Cu25 2.4328(6) 2_655 ?
N1A C2A 1.353(5) . ?
N1A C5A 1.412(5) . ?
N1A C10A 1.460(4) . ?
C2A C3A 1.526(4) . ?
C2A O11A 1.216(5) . ?
C3A C4A 1.458(5) . ?
C3A N12A 1.294(5) . ?
C4A C5A 1.412(5) . ?
C4A C9A 1.392(5) . ?
C5A C6A 1.377(5) . ?
C6A H6A 0.9300 . ?
C6A C7A 1.396(6) . ?
C7A H7A 0.9300 . ?
C7A C8A 1.390(6) . ?
C8A H8A 0.9300 . ?
C8A C9A 1.394(5) . ?
C9A H9A 0.9300 . ?
C10A H10A 0.9600 . ?
C10A H10B 0.9600 . ?
C10A H10C 0.9600 . ?
N12A C13A 1.449(4) . ?
N12A Cu25A 1.952(3) . ?
C13A C14A 1.400(5) . ?
C13A C18A 1.403(5) . ?
C14A C15A 1.391(5) . ?
C14A C19A 1.525(5) . ?
C15A H15A 0.9300 . ?
C15A C16A 1.384(5) . ?
C16A H16A 0.9300 . ?
C16A C17A 1.368(6) . ?
C17A H17A 0.9300 . ?
C17A C18A 1.390(6) . ?
C18A C22A 1.546(6) . ?
C18A C22B 1.590(12) . ?
C19A H19A 0.9800 . ?
C19A C20A 1.529(7) . ?
C19A C21A 1.537(7) . ?
C20A H20A 0.9600 . ?
C20A H20B 0.9600 . ?
C20A H20C 0.9600 . ?
C21A H21A 0.9600 . ?
C21A H21B 0.9600 . ?
C21A H21C 0.9600 . ?
C22A H22A 0.9800 . ?
C22A C23A 1.528(7) . ?
C22A C24A 1.525(9) . ?
C22B H22B 0.9800 . ?
C22B C23B 1.60(2) . ?
C22B C24B 1.47(2) . ?
C23A H23A 0.9600 . ?
C23A H23B 0.9600 . ?
C23A H23C 0.9600 . ?
C23B H23D 0.9600 . ?
C23B H23E 0.9600 . ?
C23B H23F 0.9600 . ?
C24A H24A 0.9600 . ?
C24A H24B 0.9600 . ?
C24A H24C 0.9600 . ?
C24B H24D 0.9600 . ?
C24B H24E 0.9600 . ?
C24B H24F 0.9600 . ?
Br25A Cu25A 2.4839(7) 2_766 ?
Br25A Cu25A 2.3808(9) . ?
Cu25A Br25A 2.4839(7) 2_766 ?

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 111.0(3) . . ?
C2 N1 C10 123.8(3) . . ?
C5 N1 C10 125.2(3) . . ?
N1 C2 C3 106.2(2) . . ?
O11 C2 N1 128.0(3) . . ?
O11 C2 C3 125.8(3) . . ?
C4 C3 C2 106.6(2) . . ?
N12 C3 C2 118.5(3) . . ?
N12 C3 C4 134.8(3) . . ?
C5 C4 C3 105.8(3) . . ?
C9 C4 C3 134.3(3) . . ?
C9 C4 C5 119.9(3) . . ?
N1 C5 C4 110.4(3) . . ?
C6 C5 N1 128.2(3) . . ?
C6 C5 C4 121.5(3) . . ?
C5 C6 H6 121.2 . . ?
C5 C6 C7 117.6(3) . . ?
C7 C6 H6 121.2 . . ?
C6 C7 H7 119.2 . . ?
C6 C7 C8 121.7(3) . . ?
C8 C7 H7 119.2 . . ?
C7 C8 H8 119.7 . . ?
C9 C8 C7 120.6(3) . . ?
C9 C8 H8 119.7 . . ?
C4 C9 H9 120.6 . . ?
C8 C9 C4 118.7(3) . . ?
C8 C9 H9 120.6 . . ?
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 . . ?
C3 N12 C13 118.0(2) . . ?
C3 N12 Cu25 123.8(2) . . ?
C13 N12 Cu25 118.07(19) . . ?
C14 C13 N12 118.8(3) . . ?
C18 C13 N12 118.1(3) . . ?
C18 C13 C14 123.1(3) . . ?
C13 C14 C19 122.5(3) . . ?
C15 C14 C13 116.7(3) . . ?
C15 C14 C19 120.8(3) . . ?
C14 C15 H15 119.0 . . ?
C16 C15 C14 121.9(3) . . ?
C16 C15 H15 119.0 . . ?
C15 C16 H16 120.0 . . ?
C15 C16 C17 120.0(3) . . ?
C17 C16 H16 120.0 . . ?
C16 C17 H17 119.6 . . ?
C16 C17 C18 120.8(3) . . ?
C18 C17 H17 119.6 . . ?
C13 C18 C17 117.5(3) . . ?
C13 C18 C22 122.7(3) . . ?
C17 C18 C22 119.8(3) . . ?
C14 C19 H19 108.0 . . ?
C14 C19 C20 111.0(3) . . ?
C14 C19 C21 111.0(3) . . ?
C20 C19 H19 108.0 . . ?
C20 C19 C21 110.7(3) . . ?
C21 C19 H19 108.0 . . ?
C19 C20 H20D 109.5 . . ?
C19 C20 H20E 109.5 . . ?
C19 C20 H20F 109.5 . . ?
H20D C20 H20E 109.5 . . ?
H20D C20 H20F 109.5 . . ?
H20E C20 H20F 109.5 . . ?
C19 C21 H21D 109.5 . . ?
C19 C21 H21E 109.5 . . ?
C19 C21 H21F 109.5 . . ?
H21D C21 H21E 109.5 . . ?
H21D C21 H21F 109.5 . . ?
H21E C21 H21F 109.5 . . ?
C18 C22 H22 108.0 . . ?
C18 C22 C23 111.2(3) . . ?
C23 C22 H22 108.0 . . ?
C24 C22 C18 112.1(3) . . ?
C24 C22 H22 108.0 . . ?
C24 C22 C23 109.3(3) . . ?
C22 C23 H23G 109.5 . . ?
C22 C23 H23H 109.5 . . ?
C22 C23 H23I 109.5 . . ?
H23G C23 H23H 109.5 . . ?
H23G C23 H23I 109.5 . . ?
H23H C23 H23I 109.5 . . ?
C22 C24 H24G 109.5 . . ?
C22 C24 H24H 109.5 . . ?
C22 C24 H24I 109.5 . . ?
H24G C24 H24H 109.5 . . ?
H24G C24 H24I 109.5 . . ?
H24H C24 H24I 109.5 . . ?
N12 Cu25 Cu25 165.04(8) . 2_655 ?
N12 Cu25 Br26 129.79(8) . . ?
N12 Cu25 Br26 120.85(8) . 2_655 ?
Br26 Cu25 Cu25 54.085(17) . 2_655 ?
Br26 Cu25 Cu25 52.751(16) 2_655 2_655 ?
Br26 Cu25 Br26 106.835(19) . 2_655 ?
Cu25 Br26 Cu25 73.166(19) . 2_655 ?
C2A N1A C5A 111.2(3) . . ?
C2A N1A C10A 124.3(3) . . ?
C5A N1A C10A 124.4(3) . . ?
N1A C2A C3A 106.1(3) . . ?
O11A C2A N1A 128.1(3) . . ?
O11A C2A C3A 125.8(3) . . ?
C4A C3A C2A 106.5(3) . . ?
N12A C3A C2A 117.7(3) . . ?
N12A C3A C4A 135.7(3) . . ?
C5A C4A C3A 105.9(3) . . ?
C9A C4A C3A 134.6(3) . . ?
C9A C4A C5A 119.5(3) . . ?
N1A C5A C4A 110.3(3) . . ?
C6A C5A N1A 127.6(3) . . ?
C6A C5A C4A 122.1(3) . . ?
C5A C6A H6A 121.3 . . ?
C5A C6A C7A 117.4(4) . . ?
C7A C6A H6A 121.3 . . ?
C6A C7A H7A 119.2 . . ?
C8A C7A C6A 121.7(4) . . ?
C8A C7A H7A 119.2 . . ?
C7A C8A H8A 119.7 . . ?
C7A C8A C9A 120.5(3) . . ?
C9A C8A H8A 119.7 . . ?
C4A C9A C8A 118.8(4) . . ?
C4A C9A H9A 120.6 . . ?
C8A C9A H9A 120.6 . . ?
N1A C10A H10A 109.5 . . ?
N1A C10A H10B 109.5 . . ?
N1A C10A H10C 109.5 . . ?
H10A C10A H10B 109.5 . . ?
H10A C10A H10C 109.5 . . ?
H10B C10A H10C 109.5 . . ?
C3A N12A C13A 118.8(3) . . ?
C3A N12A Cu25A 121.9(2) . . ?
C13A N12A Cu25A 118.8(2) . . ?
C14A C13A N12A 120.8(3) . . ?
C14A C13A C18A 121.7(3) . . ?
C18A C13A N12A 117.4(3) . . ?
C13A C14A C19A 122.8(3) . . ?
C15A C14A C13A 117.7(3) . . ?
C15A C14A C19A 119.5(3) . . ?
C14A C15A H15A 119.3 . . ?
C16A C15A C14A 121.5(3) . . ?
C16A C15A H15A 119.3 . . ?
C15A C16A H16A 120.3 . . ?
C17A C16A C15A 119.4(3) . . ?
C17A C16A H16A 120.3 . . ?
C16A C17A H17A 119.0 . . ?
C16A C17A C18A 122.0(4) . . ?
C18A C17A H17A 119.0 . . ?
C13A C18A C22A 121.1(4) . . ?
C13A C18A C22B 118.7(6) . . ?
C17A C18A C13A 117.6(4) . . ?
C17A C18A C22A 121.1(4) . . ?
C17A C18A C22B 117.9(6) . . ?
C14A C19A H19A 108.4 . . ?
C14A C19A C20A 111.5(3) . . ?
C14A C19A C21A 110.9(4) . . ?
C20A C19A H19A 108.4 . . ?
C20A C19A C21A 109.1(4) . . ?
C21A C19A H19A 108.4 . . ?
C19A C20A H20A 109.5 . . ?
C19A C20A H20B 109.5 . . ?
C19A C20A H20C 109.5 . . ?
H20A C20A H20B 109.5 . . ?
H20A C20A H20C 109.5 . . ?
H20B C20A H20C 109.5 . . ?
C19A C21A H21A 109.5 . . ?
C19A C21A H21B 109.5 . . ?
C19A C21A H21C 109.5 . . ?
H21A C21A H21B 109.5 . . ?
H21A C21A H21C 109.5 . . ?
H21B C21A H21C 109.5 . . ?
C18A C22A H22A 107.1 . . ?
C23A C22A C18A 110.2(5) . . ?
C23A C22A H22A 107.1 . . ?
C24A C22A C18A 114.9(4) . . ?
C24A C22A H22A 107.1 . . ?
C24A C22A C23A 110.1(5) . . ?
C18A C22B H22B 106.0 . . ?
C18A C22B C23B 121.3(11) . . ?
C23B C22B H22B 106.0 . . ?
C24B C22B C18A 103.7(10) . . ?
C24B C22B H22B 106.0 . . ?
C24B C22B C23B 112.7(12) . . ?
C22A C23A H23A 109.5 . . ?
C22A C23A H23B 109.5 . . ?
C22A C23A H23C 109.5 . . ?
H23A C23A H23B 109.5 . . ?
H23A C23A H23C 109.5 . . ?
H23B C23A H23C 109.5 . . ?
C22B C23B H23D 109.5 . . ?
C22B C23B H23E 109.5 . . ?
C22B C23B H23F 109.5 . . ?
H23D C23B H23E 109.5 . . ?
H23D C23B H23F 109.5 . . ?
H23E C23B H23F 109.5 . . ?
C22A C24A H24A 109.5 . . ?
C22A C24A H24B 109.5 . . ?
C22A C24A H24C 109.5 . . ?
H24A C24A H24B 109.5 . . ?
H24A C24A H24C 109.5 . . ?
H24B C24A H24C 109.5 . . ?
C22B C24B H24D 109.5 . . ?
C22B C24B H24E 109.5 . . ?
C22B C24B H24F 109.5 . . ?
H24D C24B H24E 109.5 . . ?
H24D C24B H24F 109.5 . . ?
H24E C24B H24F 109.5 . . ?
Cu25A Br25A Cu25A 81.49(3) . 2_766 ?
N12A Cu25A Br25A 141.47(9) . . ?
N12A Cu25A Br25A 118.90(9) . 2_766 ?
Br25A Cu25A Br25A 98.51(3) . 2_766 ?

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 2.2(3) . . . . ?
N1 C2 C3 N12 -175.2(3) . . . . ?
N1 C5 C6 C7 179.9(3) . . . . ?
C2 N1 C5 C4 -0.2(4) . . . . ?
C2 N1 C5 C6 179.0(3) . . . . ?
C2 C3 C4 C5 -2.3(3) . . . . ?
C2 C3 C4 C9 179.4(3) . . . . ?
C2 C3 N12 C13 176.1(3) . . . . ?
C2 C3 N12 Cu25 0.7(4) . . . . ?
C3 C4 C5 N1 1.6(3) . . . . ?
C3 C4 C5 C6 -177.7(3) . . . . ?
C3 C4 C9 C8 178.0(3) . . . . ?
C3 N12 C13 C14 92.7(3) . . . . ?
C3 N12 C13 C18 -88.3(3) . . . . ?
C4 C3 N12 C13 -0.3(5) . . . . ?
C4 C3 N12 Cu25 -175.7(3) . . . . ?
C4 C5 C6 C7 -0.9(5) . . . . ?
C5 N1 C2 C3 -1.2(3) . . . . ?
C5 N1 C2 O11 -179.4(3) . . . . ?
C5 C4 C9 C8 -0.1(5) . . . . ?
C5 C6 C7 C8 0.2(5) . . . . ?
C6 C7 C8 C9 0.6(6) . . . . ?
C7 C8 C9 C4 -0.6(5) . . . . ?
C9 C4 C5 N1 -179.7(3) . . . . ?
C9 C4 C5 C6 0.9(5) . . . . ?
C10 N1 C2 C3 179.9(3) . . . . ?
C10 N1 C2 O11 1.7(5) . . . . ?
C10 N1 C5 C4 178.6(3) . . . . ?
C10 N1 C5 C6 -2.1(5) . . . . ?
O11 C2 C3 C4 -179.6(3) . . . . ?
O11 C2 C3 N12 3.1(5) . . . . ?
N12 C3 C4 C5 174.4(3) . . . . ?
N12 C3 C4 C9 -3.9(6) . . . . ?
N12 C13 C14 C15 179.5(3) . . . . ?
N12 C13 C14 C19 -1.3(4) . . . . ?
N12 C13 C18 C17 -179.3(3) . . . . ?
N12 C13 C18 C22 1.9(4) . . . . ?
C13 C14 C15 C16 -0.7(5) . . . . ?
C13 C14 C19 C20 -116.2(4) . . . . ?
C13 C14 C19 C21 120.3(3) . . . . ?
C13 C18 C22 C23 108.1(3) . . . . ?
C13 C18 C22 C24 -129.1(3) . . . . ?
C14 C13 C18 C17 -0.4(5) . . . . ?
C14 C13 C18 C22 -179.1(3) . . . . ?
C14 C15 C16 C17 0.8(5) . . . . ?
C15 C14 C19 C20 63.0(4) . . . . ?
C15 C14 C19 C21 -60.5(4) . . . . ?
C15 C16 C17 C18 -0.7(5) . . . . ?
C16 C17 C18 C13 0.4(5) . . . . ?
C16 C17 C18 C22 179.2(3) . . . . ?
C17 C18 C22 C23 -70.6(4) . . . . ?
C17 C18 C22 C24 52.2(4) . . . . ?
C18 C13 C14 C15 0.5(4) . . . . ?
C18 C13 C14 C19 179.8(3) . . . . ?
C19 C14 C15 C16 -180.0(3) . . . . ?
Cu25 N12 C13 C14 -91.6(3) . . . . ?
Cu25 N12 C13 C18 87.4(3) . . . . ?
N1A C2A C3A C4A -2.0(4) . . . . ?
N1A C2A C3A N12A 174.9(3) . . . . ?
N1A C5A C6A C7A -179.1(3) . . . . ?
C2A N1A C5A C4A -1.4(4) . . . . ?
C2A N1A C5A C6A 178.1(3) . . . . ?
C2A C3A C4A C5A 1.2(4) . . . . ?
C2A C3A C4A C9A -178.5(4) . . . . ?
C2A C3A N12A C13A -171.0(3) . . . . ?
C2A C3A N12A Cu25A 0.9(4) . . . . ?
C3A C4A C5A N1A 0.0(4) . . . . ?
C3A C4A C5A C6A -179.6(3) . . . . ?
C3A C4A C9A C8A 179.3(4) . . . . ?
C3A N12A C13A C14A -92.2(4) . . . . ?
C3A N12A C13A C18A 90.5(4) . . . . ?
C4A C3A N12A C13A 4.8(6) . . . . ?
C4A C3A N12A Cu25A 176.7(3) . . . . ?
C4A C5A C6A C7A 0.3(5) . . . . ?
C5A N1A C2A C3A 2.1(4) . . . . ?
C5A N1A C2A O11A -179.9(4) . . . . ?
C5A C4A C9A C8A -0.3(5) . . . . ?
C5A C6A C7A C8A -0.7(6) . . . . ?
C6A C7A C8A C9A 0.6(6) . . . . ?
C7A C8A C9A C4A -0.1(6) . . . . ?
C9A C4A C5A N1A 179.7(3) . . . . ?
C9A C4A C5A C6A 0.2(5) . . . . ?
C10A N1A C2A C3A -173.4(3) . . . . ?
C10A N1A C2A O11A 4.7(6) . . . . ?
C10A N1A C5A C4A 174.1(3) . . . . ?
C10A N1A C5A C6A -6.5(6) . . . . ?
O11A C2A C3A C4A 179.8(3) . . . . ?
O11A C2A C3A N12A -3.2(5) . . . . ?
N12A C3A C4A C5A -174.9(4) . . . . ?
N12A C3A C4A C9A 5.4(7) . . . . ?
N12A C13A C14A C15A -176.1(3) . . . . ?
N12A C13A C14A C19A 4.5(6) . . . . ?
N12A C13A C18A C17A 174.3(4) . . . . ?
N12A C13A C18A C22A -10.6(6) . . . . ?
N12A C13A C18A C22B 21.6(9) . . . . ?
C13A C14A C15A C16A 1.4(6) . . . . ?
C13A C14A C19A C20A -114.6(4) . . . . ?
C13A C14A C19A C21A 123.7(4) . . . . ?
C13A C18A C22A C23A 144.2(5) . . . . ?
C13A C18A C22A C24A -90.8(6) . . . . ?
C13A C18A C22B C23B 106.8(12) . . . . ?
C13A C18A C22B C24B -125.3(9) . . . . ?
C14A C13A C18A C17A -2.9(6) . . . . ?
C14A C13A C18A C22A 172.2(4) . . . . ?
C14A C13A C18A C22B -155.6(7) . . . . ?
C14A C15A C16A C17A -1.9(6) . . . . ?
C15A C14A C19A C20A 66.1(5) . . . . ?
C15A C14A C19A C21A -55.7(5) . . . . ?
C15A C16A C17A C18A -0.2(7) . . . . ?
C16A C17A C18A C13A 2.5(7) . . . . ?
C16A C17A C18A C22A -172.6(4) . . . . ?
C16A C17A C18A C22B 155.4(7) . . . . ?
C17A C18A C22A C23A -40.9(7) . . . . ?
C17A C18A C22A C24A 84.2(6) . . . . ?
C17A C18A C22B C23B -45.8(14) . . . . ?
C17A C18A C22B C24B 82.1(11) . . . . ?
C18A C13A C14A C15A 1.0(6) . . . . ?
C18A C13A C14A C19A -178.4(4) . . . . ?
C19A C14A C15A C16A -179.2(4) . . . . ?
C22A C18A C22B C23B -150(2) . . . . ?
C22A C18A C22B C24B -22.3(8) . . . . ?
C22B C18A C22A C23A 50.8(11) . . . . ?
C22B C18A C22A C24A 175.8(13) . . . . ?
Cu25A N12A C13A C14A 95.6(3) . . . . ?
Cu25A N12A C13A C18A -81.6(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_xrd_31
_database_code_depnum_ccdc_archive 'CCDC 1538883'
_audit_update_record             
;
2017-03-19 deposited with the CCDC.
2018-10-29 downloaded from the CCDC.
;
_audit_creation_date             2016-07-04
_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         'C30 H22 Br4 Cu2 N4 O2'
_chemical_formula_sum            'C30 H22 Br4 Cu2 N4 O2'
_chemical_formula_weight         917.23
_chemical_melting_point          ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -1.9646 0.5888 '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                   8.5542(4)
_cell_length_b                   9.5043(6)
_cell_length_c                   10.1464(4)
_cell_angle_alpha                90.501(4)
_cell_angle_beta                 96.474(4)
_cell_angle_gamma                115.484(6)
_cell_volume                     738.40(7)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    3227
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      75.8110
_cell_measurement_theta_min      4.3820
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    8.417
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.44076
_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.
;
_exptl_crystal_colour            'dark red'
_exptl_crystal_density_diffrn    2.063
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             444
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.05
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0382
_diffrn_reflns_av_unetI/netI     0.0466
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6459
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.443
_diffrn_reflns_theta_min         4.395
_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 0.997
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -25.00   26.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.4354  -77.0000  -90.0000 51

#__ type_ start__ end____ width___ exp.time_
  2 omega   28.00   56.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.4354  -77.0000  -90.0000 28

#__ type_ start__ end____ width___ exp.time_
  3 omega   39.00   73.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.4354  -99.0000 -180.0000 34

#__ type_ start__ end____ width___ exp.time_
  4 omega   40.00   73.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -125.0000 -150.0000 33

#__ type_ start__ end____ width___ exp.time_
  5 omega   91.00  121.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -125.0000 -150.0000 30

#__ type_ start__ end____ width___ exp.time_
  6 omega   55.00  106.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -125.0000  -30.0000 51

#__ type_ start__ end____ width___ exp.time_
  7 omega   94.00  121.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -125.0000   30.0000 27

#__ type_ start__ end____ width___ exp.time_
  8 omega   59.00   90.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000  -30.0000 31

#__ type_ start__ end____ width___ exp.time_
  9 omega   56.00   83.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000   60.0000 27

#__ type_ start__ end____ width___ exp.time_
 10 omega   42.00  143.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -77.0000  -60.0000 101

#__ type_ start__ end____ width___ exp.time_
 11 omega   83.00  172.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   61.0000   90.0000 89

#__ type_ start__ end____ width___ exp.time_
 12 omega  142.00  176.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  125.0000    0.0000 34

#__ type_ start__ end____ width___ exp.time_
 13 omega  143.00  170.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  125.0000  -90.0000 27

#__ type_ start__ end____ width___ exp.time_
 14 omega   97.00  130.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  125.0000  -90.0000 33

#__ type_ start__ end____ width___ exp.time_
 15 omega   94.00  128.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  125.0000    0.0000 34

#__ type_ start__ end____ width___ exp.time_
 16 omega   99.00  152.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  125.0000   30.0000 53

#__ type_ start__ end____ width___ exp.time_
 17 omega   79.00  157.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000  -30.0000 78

#__ type_ start__ end____ width___ exp.time_
 18 omega   83.00  174.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000    0.0000 91

#__ type_ start__ end____ width___ exp.time_
 19 omega   61.00  123.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.4354  178.0000   60.0000 62

#__ type_ start__ end____ width___ exp.time_
 20 omega    0.00   26.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.4354   38.0000 -150.0000 26

#__ type_ start__ end____ width___ exp.time_
 21 omega  -50.00   33.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.4354   38.0000 -180.0000 83

#__ type_ start__ end____ width___ exp.time_
 22 omega -105.00  -15.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.4354  -57.0000   30.0000 90

#__ type_ start__ end____ width___ exp.time_
 23 omega   40.00   77.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -95.0000 -150.0000 37

#__ type_ start__ end____ width___ exp.time_
 24 omega   49.00  116.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -125.0000  150.0000 67

#__ type_ start__ end____ width___ exp.time_
 25 omega  -82.00   -5.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.4354   19.0000  150.0000 77

#__ type_ start__ end____ width___ exp.time_
 26 omega  -79.00  -25.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.4354  -38.0000  120.0000 54

#__ type_ start__ end____ width___ exp.time_
 27 omega -115.00  -84.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.4354  -38.0000  120.0000 31

#__ type_ start__ end____ width___ exp.time_
 28 omega   75.00  118.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.4354  178.0000  150.0000 43

#__ type_ start__ end____ width___ exp.time_
 29 omega    7.00   32.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.4354   84.0000 -125.2968 25

#__ type_ start__ end____ width___ exp.time_
 30 omega   11.00   36.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       46.0000   84.0000   86.3254 25

#__ type_ start__ end____ width___ exp.time_
 31 omega   16.00   41.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       50.0000   81.0000  148.7820 25

#__ type_ start__ end____ width___ exp.time_
 32 omega   20.00   45.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   81.0000  -82.8940 25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0968473000
_diffrn_orient_matrix_UB_12      0.1722514000
_diffrn_orient_matrix_UB_13      0.0530665000
_diffrn_orient_matrix_UB_21      0.1163237000
_diffrn_orient_matrix_UB_22      -0.0424900000
_diffrn_orient_matrix_UB_23      0.1034853000
_diffrn_orient_matrix_UB_31      0.1325384000
_diffrn_orient_matrix_UB_32      0.0299712000
_diffrn_orient_matrix_UB_33      -0.0996019000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2537
_reflns_number_total             2921
_reflns_odcompleteness_completeness 99.59
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_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 1.171.37.35 (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, 2008)'
_computing_structure_solution    'ShelXs (Sheldrick, 2008)'
_refine_diff_density_max         0.794
_refine_diff_density_min         -0.701
_refine_diff_density_rms         0.128
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2921
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0418
_refine_ls_R_factor_gt           0.0336
_refine_ls_restrained_S_all      1.042
_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)+(0.0446P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0784
_refine_ls_wR_factor_ref         0.0835
_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), 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
N1 N -0.3373(4) -0.0710(4) 0.5139(3) 0.0113(6) Uani 1 1 d . . . . .
C2 C -0.3662(5) -0.0321(4) 0.3866(3) 0.0103(7) Uani 1 1 d . . . . .
C3 C -0.2049(5) 0.1142(4) 0.3649(3) 0.0099(7) Uani 1 1 d . . . . .
C4 C -0.0865(5) 0.1536(4) 0.4898(3) 0.0105(7) Uani 1 1 d . . . . .
C5 C -0.1726(5) 0.0364(4) 0.5755(3) 0.0121(7) Uani 1 1 d . . . . .
C6 C -0.0953(5) 0.0323(4) 0.7021(3) 0.0116(7) Uani 1 1 d . . . . .
H6 H -0.1527 -0.0462 0.7573 0.014 Uiso 1 1 calc R . . . .
C7 C 0.0705(5) 0.1491(4) 0.7440(3) 0.0134(7) Uani 1 1 d . . . . .
H7 H 0.1251 0.1502 0.8289 0.016 Uiso 1 1 calc R . . . .
C8 C 0.1556(5) 0.2645(4) 0.6596(3) 0.0112(7) Uani 1 1 d . . . . .
C9 C 0.0799(5) 0.2695(4) 0.5326(3) 0.0117(7) Uani 1 1 d . . . . .
H9 H 0.1386 0.3479 0.4778 0.014 Uiso 1 1 calc R . . . .
C10 C -0.4523(5) -0.2118(4) 0.5698(3) 0.0151(7) Uani 1 1 d . . . . .
H10A H -0.5587 -0.2633 0.5101 0.023 Uiso 1 1 calc GR . . . .
H10B H -0.4783 -0.1856 0.6536 0.023 Uiso 1 1 calc GR . . . .
H10C H -0.3964 -0.2801 0.5828 0.023 Uiso 1 1 calc GR . . . .
O11 O -0.4944(3) -0.0986(3) 0.3051(2) 0.0136(5) Uani 1 1 d . . . . .
N12 N -0.1999(4) 0.1630(4) 0.2468(3) 0.0110(6) Uani 1 1 d . . . . .
C13 C -0.0563(4) 0.3007(4) 0.2147(3) 0.0106(7) Uani 1 1 d . . . . .
C14 C 0.0272(5) 0.2899(5) 0.1077(4) 0.0164(8) Uani 1 1 d . . . . .
H14 H -0.0083 0.1948 0.0601 0.020 Uiso 1 1 calc R . . . .
C15 C 0.1647(5) 0.4234(5) 0.0730(4) 0.0186(8) Uani 1 1 d . . . . .
H15 H 0.2232 0.4168 0.0030 0.022 Uiso 1 1 calc R . . . .
C16 C 0.2158(5) 0.5662(5) 0.1414(4) 0.0176(8) Uani 1 1 d . . . . .
H16 H 0.3083 0.6549 0.1179 0.021 Uiso 1 1 calc R . . . .
C17 C 0.1270(5) 0.5756(5) 0.2457(4) 0.0169(8) Uani 1 1 d . . . . .
H17 H 0.1588 0.6716 0.2905 0.020 Uiso 1 1 calc R . . . .
C18 C -0.0077(5) 0.4437(4) 0.2833(3) 0.0132(7) Uani 1 1 d . . . . .
H18 H -0.0654 0.4504 0.3537 0.016 Uiso 1 1 calc R . . . .
Cu19 Cu -0.39932(7) 0.04451(7) 0.10977(5) 0.01470(14) Uani 1 1 d . . . . .
Br20 Br -0.39410(5) -0.14939(5) -0.04164(3) 0.01482(11) Uani 1 1 d . . . . .
Br21 Br 0.37961(5) 0.42456(5) 0.72423(4) 0.01684(11) 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
N1 C2 1.371(4) . ?
N1 C5 1.404(5) . ?
N1 C10 1.445(4) . ?
C2 C3 1.520(5) . ?
C2 O11 1.215(4) . ?
C3 C4 1.465(5) . ?
C3 N12 1.287(4) . ?
C4 C5 1.412(5) . ?
C4 C9 1.390(5) . ?
C5 C6 1.386(5) . ?
C6 H6 0.9300 . ?
C6 C7 1.388(5) . ?
C7 H7 0.9300 . ?
C7 C8 1.391(5) . ?
C8 C9 1.387(5) . ?
C8 Br21 1.899(4) . ?
C9 H9 0.9300 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
O11 Cu19 2.428(2) . ?
N12 C13 1.429(5) . ?
N12 Cu19 1.974(3) . ?
C13 C14 1.391(5) . ?
C13 C18 1.391(5) . ?
C14 H14 0.9300 . ?
C14 C15 1.391(5) . ?
C15 H15 0.9300 . ?
C15 C16 1.385(6) . ?
C16 H16 0.9300 . ?
C16 C17 1.393(5) . ?
C17 H17 0.9300 . ?
C17 C18 1.382(5) . ?
C18 H18 0.9300 . ?
Cu19 Cu19 2.5481(11) 2_455 ?
Cu19 Br20 2.4180(6) 2_455 ?
Cu19 Br20 2.4073(6) . ?
Br20 Cu19 2.4180(6) 2_455 ?

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 110.1(3) . . ?
C2 N1 C10 124.2(3) . . ?
C5 N1 C10 125.3(3) . . ?
N1 C2 C3 106.6(3) . . ?
O11 C2 N1 128.0(3) . . ?
O11 C2 C3 125.3(3) . . ?
C4 C3 C2 106.3(3) . . ?
N12 C3 C2 116.4(3) . . ?
N12 C3 C4 137.1(3) . . ?
C5 C4 C3 105.7(3) . . ?
C9 C4 C3 134.5(3) . . ?
C9 C4 C5 119.8(3) . . ?
N1 C5 C4 111.3(3) . . ?
C6 C5 N1 126.8(3) . . ?
C6 C5 C4 121.9(4) . . ?
C5 C6 H6 121.1 . . ?
C5 C6 C7 117.9(3) . . ?
C7 C6 H6 121.1 . . ?
C6 C7 H7 119.8 . . ?
C6 C7 C8 120.4(3) . . ?
C8 C7 H7 119.8 . . ?
C7 C8 Br21 118.4(3) . . ?
C9 C8 C7 122.3(3) . . ?
C9 C8 Br21 119.2(3) . . ?
C4 C9 H9 121.1 . . ?
C8 C9 C4 117.8(3) . . ?
C8 C9 H9 121.1 . . ?
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 Cu19 101.4(2) . . ?
C3 N12 C13 121.5(3) . . ?
C3 N12 Cu19 118.2(3) . . ?
C13 N12 Cu19 120.2(2) . . ?
C14 C13 N12 118.1(3) . . ?
C14 C13 C18 120.7(3) . . ?
C18 C13 N12 121.0(3) . . ?
C13 C14 H14 120.5 . . ?
C15 C14 C13 119.0(4) . . ?
C15 C14 H14 120.5 . . ?
C14 C15 H15 119.6 . . ?
C16 C15 C14 120.9(3) . . ?
C16 C15 H15 119.6 . . ?
C15 C16 H16 120.4 . . ?
C15 C16 C17 119.3(4) . . ?
C17 C16 H16 120.4 . . ?
C16 C17 H17 119.6 . . ?
C18 C17 C16 120.7(4) . . ?
C18 C17 H17 119.6 . . ?
C13 C18 H18 120.3 . . ?
C17 C18 C13 119.4(3) . . ?
C17 C18 H18 120.3 . . ?
O11 Cu19 Cu19 118.98(7) . 2_455 ?
N12 Cu19 O11 78.31(11) . . ?
N12 Cu19 Cu19 162.69(9) . 2_455 ?
N12 Cu19 Br20 121.42(8) . . ?
N12 Cu19 Br20 119.15(8) . 2_455 ?
Br20 Cu19 O11 103.16(6) . . ?
Br20 Cu19 O11 106.49(6) 2_455 . ?
Br20 Cu19 Cu19 57.92(2) 2_455 2_455 ?
Br20 Cu19 Cu19 58.33(2) . 2_455 ?
Br20 Cu19 Br20 116.25(2) . 2_455 ?
Cu19 Br20 Cu19 63.75(2) . 2_455 ?

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 -0.6(3) . . . . ?
N1 C2 C3 N12 174.5(3) . . . . ?
N1 C2 O11 Cu19 -173.8(3) . . . . ?
N1 C5 C6 C7 179.1(3) . . . . ?
C2 N1 C5 C4 0.9(4) . . . . ?
C2 N1 C5 C6 -177.5(3) . . . . ?
C2 C3 C4 C5 1.1(3) . . . . ?
C2 C3 C4 C9 178.4(3) . . . . ?
C2 C3 N12 C13 179.0(3) . . . . ?
C2 C3 N12 Cu19 0.2(4) . . . . ?
C3 C2 O11 Cu19 6.7(3) . . . . ?
C3 C4 C5 N1 -1.2(4) . . . . ?
C3 C4 C5 C6 177.3(3) . . . . ?
C3 C4 C9 C8 -176.8(3) . . . . ?
C3 N12 C13 C14 126.8(3) . . . . ?
C3 N12 C13 C18 -57.0(5) . . . . ?
C4 C3 N12 C13 -7.9(6) . . . . ?
C4 C3 N12 Cu19 173.3(3) . . . . ?
C4 C5 C6 C7 0.8(5) . . . . ?
C5 N1 C2 C3 -0.2(3) . . . . ?
C5 N1 C2 O11 -179.7(3) . . . . ?
C5 C4 C9 C8 0.2(5) . . . . ?
C5 C6 C7 C8 -0.8(5) . . . . ?
C6 C7 C8 C9 0.6(5) . . . . ?
C6 C7 C8 Br21 178.3(2) . . . . ?
C7 C8 C9 C4 -0.3(5) . . . . ?
C9 C4 C5 N1 -179.0(3) . . . . ?
C9 C4 C5 C6 -0.5(5) . . . . ?
C10 N1 C2 C3 -173.8(3) . . . . ?
C10 N1 C2 O11 6.6(5) . . . . ?
C10 N1 C5 C4 174.5(3) . . . . ?
C10 N1 C5 C6 -3.9(5) . . . . ?
O11 C2 C3 C4 179.0(3) . . . . ?
O11 C2 C3 N12 -5.9(5) . . . . ?
N12 C3 C4 C5 -172.5(4) . . . . ?
N12 C3 C4 C9 4.8(7) . . . . ?
N12 C13 C14 C15 178.5(3) . . . . ?
N12 C13 C18 C17 -177.2(3) . . . . ?
C13 C14 C15 C16 -1.6(6) . . . . ?
C14 C13 C18 C17 -1.1(5) . . . . ?
C14 C15 C16 C17 -0.4(6) . . . . ?
C15 C16 C17 C18 1.6(6) . . . . ?
C16 C17 C18 C13 -0.9(6) . . . . ?
C18 C13 C14 C15 2.3(5) . . . . ?
Cu19 N12 C13 C14 -54.4(4) . . . . ?
Cu19 N12 C13 C18 121.8(3) . . . . ?
Br21 C8 C9 C4 -177.9(2) . . . . ?



