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

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

data_1a
_audit_block_doi                 10.5517/cc1kq6q6
_database_code_depnum_ccdc_archive 'CCDC 1451318'
_audit_update_record             
;
2016-02-02 deposited with the CCDC.
2016-04-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H20 N4 O2'
_chemical_formula_sum            'C23 H20 N4 O2'
_chemical_formula_weight         384.43

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

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

_cell_length_a                   12.735(4)
_cell_length_b                   11.493(4)
_cell_length_c                   15.844(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 123.376(17)
_cell_angle_gamma                90.00
_cell_volume                     1936.5(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4805
_cell_measurement_theta_min      2.36
_cell_measurement_theta_max      25.04

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             808
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.979
_exptl_absorpt_correction_T_max  0.983
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18511
_diffrn_reflns_av_R_equivalents  0.0586
_diffrn_reflns_av_sigmaI/netI    0.0657
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.35
_diffrn_reflns_theta_max         27.41
_reflns_number_total             4385
_reflns_number_gt                2595
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0663P)²+0.3361P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4385
_refine_ls_number_parameters     264
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1180
_refine_ls_R_factor_gt           0.0565
_refine_ls_wR_factor_ref         0.1403
_refine_ls_wR_factor_gt          0.1179
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_restrained_S_all      1.014
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.5814(2) 0.42301(18) 0.41374(15) 0.0416(5) Uani 1 1 d . . .
H1 H 0.5868 0.4673 0.3672 0.050 Uiso 1 1 calc R . .
C2 C 0.4653(2) 0.4015(2) 0.39737(17) 0.0487(6) Uani 1 1 d . . .
H2 H 0.3933 0.4311 0.3400 0.058 Uiso 1 1 calc R . .
C3 C 0.4551(2) 0.3365(2) 0.46552(18) 0.0524(6) Uani 1 1 d . . .
H3 H 0.3767 0.3209 0.4541 0.063 Uiso 1 1 calc R . .
C4 C 0.5630(2) 0.2947(2) 0.55099(18) 0.0590(7) Uani 1 1 d . . .
H4 H 0.5571 0.2521 0.5982 0.071 Uiso 1 1 calc R . .
C5 C 0.6797(2) 0.31540(19) 0.56726(16) 0.0484(6) Uani 1 1 d . . .
H5 H 0.7514 0.2858 0.6248 0.058 Uiso 1 1 calc R . .
C6 C 0.69098(18) 0.37967(15) 0.49878(14) 0.0339(5) Uani 1 1 d . . .
C7 C 0.81754(18) 0.39317(15) 0.51247(15) 0.0365(5) Uani 1 1 d . . .
H7A H 0.8822 0.3682 0.5803 0.044 Uiso 1 1 calc R . .
H7B H 0.8206 0.3414 0.4655 0.044 Uiso 1 1 calc R . .
C8 C 0.7392(3) 0.5131(2) 0.14137(17) 0.0655(7) Uani 1 1 d . . .
H8A H 0.7980 0.4578 0.1448 0.098 Uiso 1 1 calc R . .
H8B H 0.7364 0.5804 0.1043 0.098 Uiso 1 1 calc R . .
H8C H 0.6572 0.4783 0.1078 0.098 Uiso 1 1 calc R . .
C9 C 0.78145(18) 0.47376(18) 0.31313(15) 0.0383(5) Uani 1 1 d . . .
C10 C 0.83066(17) 0.54762(16) 0.40720(14) 0.0309(4) Uani 1 1 d . . .
C11 C 0.85292(17) 0.65511(16) 0.38810(13) 0.0310(4) Uani 1 1 d . . .
C12 C 0.82063(18) 0.65851(18) 0.28388(15) 0.0373(5) Uani 1 1 d . . .
C13 C 0.68826(18) 0.84576(17) 0.40552(15) 0.0393(5) Uani 1 1 d . . .
H13 H 0.6664 0.7753 0.4207 0.047 Uiso 1 1 calc R . .
C14 C 0.60363(19) 0.93754(18) 0.36952(15) 0.0430(5) Uani 1 1 d . . .
H14 H 0.5260 0.9277 0.3613 0.052 Uiso 1 1 calc R . .
C15 C 0.63254(19) 1.04352(17) 0.34554(14) 0.0400(5) Uani 1 1 d . . .
C16 C 0.5398(2) 1.1432(2) 0.30594(19) 0.0619(7) Uani 1 1 d . . .
H16A H 0.4675 1.1233 0.2407 0.093 Uiso 1 1 calc R . .
H16B H 0.5787 1.2116 0.3002 0.093 Uiso 1 1 calc R . .
H16C H 0.5143 1.1582 0.3518 0.093 Uiso 1 1 calc R . .
C17 C 0.7488(2) 1.05441(17) 0.35834(17) 0.0485(6) Uani 1 1 d . . .
H17 H 0.7703 1.1246 0.3425 0.058 Uiso 1 1 calc R . .
C18 C 0.83401(19) 0.96272(17) 0.39432(16) 0.0426(5) Uani 1 1 d . . .
H18 H 0.9112 0.9723 0.4017 0.051 Uiso 1 1 calc R . .
C19 C 0.80520(17) 0.85750(15) 0.41917(13) 0.0301(4) Uani 1 1 d . . .
C20 C 0.89866(17) 0.75616(16) 0.45985(13) 0.0318(5) Uani 1 1 d . . .
H20 H 0.9782 0.7837 0.4709 0.038 Uiso 1 1 calc R . .
C21 C 0.92467(17) 0.70721(16) 0.55902(13) 0.0324(5) Uani 1 1 d . . .
C22 C 0.98435(19) 0.78424(17) 0.64254(15) 0.0377(5) Uani 1 1 d . . .
C23 C 0.89381(17) 0.59771(16) 0.57298(13) 0.0317(5) Uani 1 1 d . . .
N1 N 0.84805(14) 0.51233(12) 0.49708(11) 0.0330(4) Uani 1 1 d . . .
N2 N 0.77874(16) 0.54737(15) 0.24330(12) 0.0433(5) Uani 1 1 d . . .
N3 N 1.03482(18) 0.84924(16) 0.70845(14) 0.0545(5) Uani 1 1 d . . .
N4 N 0.90811(17) 0.56524(15) 0.66089(12) 0.0488(5) Uani 1 1 d . . .
H4A H 0.9373 0.6138 0.7101 0.059 Uiso 1 1 d R . .
H4B H 0.8880 0.4960 0.6675 0.059 Uiso 1 1 d R . .
O1 O 0.74903(15) 0.37253(13) 0.29834(11) 0.0548(4) Uani 1 1 d . . .
O2 O 0.82697(15) 0.74000(13) 0.23835(12) 0.0543(4) 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
C1 C2 1.376(3) . ?
C1 C6 1.394(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.376(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.380(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.382(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.384(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.511(3) . ?
C7 N1 1.480(2) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 N2 1.457(3) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 O1 1.213(2) . ?
C9 N2 1.378(3) . ?
C9 C10 1.519(3) . ?
C10 C11 1.339(3) . ?
C10 N1 1.376(2) . ?
C11 C12 1.466(3) . ?
C11 C20 1.501(3) . ?
C12 O2 1.212(2) . ?
C12 N2 1.397(3) . ?
C13 C14 1.387(3) . ?
C13 C19 1.389(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.385(3) . ?
C14 H14 0.9300 . ?
C15 C17 1.385(3) . ?
C15 C16 1.512(3) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 C18 1.390(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.382(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.531(3) . ?
C20 C21 1.524(3) . ?
C20 H20 0.9800 . ?
C21 C23 1.372(3) . ?
C21 C22 1.416(3) . ?
C22 N3 1.150(2) . ?
C23 N4 1.354(2) . ?
C23 N1 1.406(2) . ?
N4 H4A 0.8600 . ?
N4 H4B 0.8600 . ?

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 C1 C6 121.3(2) . . ?
C2 C1 H1 119.4 . . ?
C6 C1 H1 119.4 . . ?
C1 C2 C3 120.3(2) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 H2 119.9 . . ?
C2 C3 C4 119.1(2) . . ?
C2 C3 H3 120.4 . . ?
C4 C3 H3 120.4 . . ?
C3 C4 C5 120.7(2) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C4 C5 C6 120.7(2) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C5 C6 C1 117.9(2) . . ?
C5 C6 C7 120.31(18) . . ?
C1 C6 C7 121.59(18) . . ?
N1 C7 C6 115.30(15) . . ?
N1 C7 H7A 108.4 . . ?
C6 C7 H7A 108.4 . . ?
N1 C7 H7B 108.4 . . ?
C6 C7 H7B 108.4 . . ?
H7A C7 H7B 107.5 . . ?
N2 C8 H8A 109.5 . . ?
N2 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
N2 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O1 C9 N2 125.31(19) . . ?
O1 C9 C10 129.66(19) . . ?
N2 C9 C10 105.03(16) . . ?
C11 C10 N1 124.90(17) . . ?
C11 C10 C9 108.56(17) . . ?
N1 C10 C9 126.53(17) . . ?
C10 C11 C12 108.43(16) . . ?
C10 C11 C20 125.81(17) . . ?
C12 C11 C20 125.73(16) . . ?
O2 C12 N2 124.49(19) . . ?
O2 C12 C11 128.45(19) . . ?
N2 C12 C11 107.06(17) . . ?
C14 C13 C19 120.96(19) . . ?
C14 C13 H13 119.5 . . ?
C19 C13 H13 119.5 . . ?
C15 C14 C13 121.2(2) . . ?
C15 C14 H14 119.4 . . ?
C13 C14 H14 119.4 . . ?
C14 C15 C17 117.61(18) . . ?
C14 C15 C16 121.0(2) . . ?
C17 C15 C16 121.3(2) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 C17 C18 121.47(19) . . ?
C15 C17 H17 119.3 . . ?
C18 C17 H17 119.3 . . ?
C19 C18 C17 120.7(2) . . ?
C19 C18 H18 119.7 . . ?
C17 C18 H18 119.7 . . ?
C18 C19 C13 118.07(18) . . ?
C18 C19 C20 121.24(17) . . ?
C13 C19 C20 120.69(17) . . ?
C11 C20 C21 105.60(15) . . ?
C11 C20 C19 112.45(15) . . ?
C21 C20 C19 113.11(15) . . ?
C11 C20 H20 108.5 . . ?
C21 C20 H20 108.5 . . ?
C19 C20 H20 108.5 . . ?
C23 C21 C22 118.47(17) . . ?
C23 C21 C20 125.86(16) . . ?
C22 C21 C20 115.67(16) . . ?
N3 C22 C21 177.2(2) . . ?
N4 C23 C21 122.03(17) . . ?
N4 C23 N1 116.45(16) . . ?
C21 C23 N1 121.52(17) . . ?
C10 N1 C23 115.74(15) . . ?
C10 N1 C7 122.40(15) . . ?
C23 N1 C7 121.84(15) . . ?
C9 N2 C12 110.93(16) . . ?
C9 N2 C8 124.38(18) . . ?
C12 N2 C8 124.69(19) . . ?
C23 N4 H4A 120.0 . . ?
C23 N4 H4B 120.0 . . ?
H4A N4 H4B 120.0 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N4 H4A O2 0.86 2.39 2.997(2) 128.5 4_576
N4 H4B N3 0.86 2.36 3.053(3) 138.5 2_746

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        27.41
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.237
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.048
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1p
_audit_block_doi                 10.5517/cc1kq6r7
_database_code_depnum_ccdc_archive 'CCDC 1451319'
_audit_update_record             
;
2016-02-02 deposited with the CCDC.
2016-04-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H19 Cl N4 O3'
_chemical_formula_sum            'C22 H19 Cl N4 O3'
_chemical_formula_weight         422.86

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

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

_cell_length_a                   26.111(16)
_cell_length_b                   9.630(5)
_cell_length_c                   19.502(11)
_cell_angle_alpha                90
_cell_angle_beta                 110.954(18)
_cell_angle_gamma                90
_cell_volume                     4580(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    7957
_cell_measurement_theta_min      2.24
_cell_measurement_theta_max      27.47

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.227
_exptl_crystal_F_000             1760
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.280
_exptl_absorpt_coefficient_mu    0.195
_shelx_estimated_absorpt_T_min   0.933
_shelx_estimated_absorpt_T_max   0.947
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.932
_exptl_absorpt_correction_T_max  0.947
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21651
_diffrn_reflns_av_unetI/netI     0.0276
_diffrn_reflns_av_R_equivalents  0.0353
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.263
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4042
_reflns_number_gt                3120
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0746P)²+2.8290P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0020(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4042
_refine_ls_number_parameters     274
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0662
_refine_ls_R_factor_gt           0.0514
_refine_ls_wR_factor_ref         0.1453
_refine_ls_wR_factor_gt          0.1379
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_restrained_S_all      1.086
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.82260(9) 0.6197(2) -0.03937(13) 0.0490(6) Uani 1 1 d . . . . .
H1 H 0.7870 0.6545 -0.0575 0.059 Uiso 1 1 calc R U . . .
C2 C 0.84233(11) 0.5429(3) -0.08394(13) 0.0557(6) Uani 1 1 d . . . . .
H2 H 0.8199 0.5279 -0.1325 0.067 Uiso 1 1 calc R U . . .
C3 C 0.89441(11) 0.4874(3) -0.05868(15) 0.0585(7) Uani 1 1 d . . . . .
C4 C 0.91480(15) 0.3980(4) -0.1075(2) 0.0989(12) Uani 1 1 d . . . . .
H4A H 0.9449 0.3418 -0.0776 0.148 Uiso 1 1 calc R U . . .
H4B H 0.9268 0.4564 -0.1387 0.148 Uiso 1 1 calc R U . . .
H4C H 0.8856 0.3391 -0.1372 0.148 Uiso 1 1 calc R U . . .
C5 C 0.92706(10) 0.5123(3) 0.01406(16) 0.0638(7) Uani 1 1 d . . . . .
H5 H 0.9621 0.4742 0.0327 0.077 Uiso 1 1 calc R U . . .
C6 C 0.90867(9) 0.5924(2) 0.05928(13) 0.0524(6) Uani 1 1 d . . . . .
H6 H 0.9315 0.6110 0.1073 0.063 Uiso 1 1 calc R U . . .
C7 C 0.85582(8) 0.6449(2) 0.03228(11) 0.0382(5) Uani 1 1 d . . . . .
C8 C 0.82627(12) 1.2149(3) -0.01228(14) 0.0621(7) Uani 1 1 d . . . . .
H8A H 0.8576 1.2710 0.0139 0.093 Uiso 1 1 calc R U . . .
H8B H 0.7934 1.2678 -0.0212 0.093 Uiso 1 1 calc R U . . .
H8C H 0.8285 1.1864 -0.0583 0.093 Uiso 1 1 calc R U . . .
C9 C 0.83401(9) 0.9585(2) 0.01225(12) 0.0411(5) Uani 1 1 d . . . . .
C10 C 0.83222(8) 0.8697(2) 0.07505(11) 0.0357(5) Uani 1 1 d . . . . .
C11 C 0.82232(8) 0.95075(19) 0.12441(10) 0.0323(4) Uani 1 1 d . . . . .
C12 C 0.81731(8) 1.0948(2) 0.09807(11) 0.0361(5) Uani 1 1 d . . . . .
C13 C 0.92061(9) 0.8660(3) 0.26529(13) 0.0503(6) Uani 1 1 d . . . . .
H13 H 0.9207 0.7971 0.2319 0.060 Uiso 1 1 calc R U . . .
C14 C 0.96953(10) 0.9019(3) 0.32080(16) 0.0666(8) Uani 1 1 d . . . . .
H14 H 1.0021 0.8577 0.3244 0.080 Uiso 1 1 calc R U . . .
C15 C 0.96929(11) 1.0032(4) 0.37008(15) 0.0734(9) Uani 1 1 d . . . . .
C16 C 0.92110(11) 1.0672(4) 0.36651(15) 0.0791(9) Uani 1 1 d . . . . .
H16 H 0.9212 1.1341 0.4009 0.095 Uiso 1 1 calc R U . . .
C17 C 0.87229(10) 1.0304(3) 0.31073(13) 0.0569(7) Uani 1 1 d . . . . .
H17 H 0.8397 1.0730 0.3083 0.068 Uiso 1 1 calc R U . . .
C18 C 0.87149(8) 0.9316(2) 0.25890(11) 0.0357(5) Uani 1 1 d . . . . .
C19 C 0.81851(8) 0.89794(18) 0.19451(10) 0.0315(4) Uani 1 1 d . . . . .
H19 H 0.7879 0.9449 0.2027 0.038 Uiso 1 1 calc R U . . .
C20 C 0.80556(8) 0.74251(19) 0.18425(11) 0.0336(4) Uani 1 1 d . . . . .
C21 C 0.78038(8) 0.6741(2) 0.23105(11) 0.0356(5) Uani 1 1 d . . . . .
C22 C 0.81824(8) 0.6641(2) 0.13318(11) 0.0369(5) Uani 1 1 d . . . . .
Cl1 Cl 1.03140(4) 1.05171(17) 0.43741(5) 0.1415(6) Uani 1 1 d . . . . .
N1 N 0.83588(7) 0.72722(16) 0.07996(9) 0.0412(4) Uani 1 1 d . . . . .
N2 N 0.82530(8) 1.09291(17) 0.03113(10) 0.0437(4) Uani 1 1 d . . . . .
N3 N 0.76332(8) 0.75477(18) 0.27511(10) 0.0500(5) Uani 1 1 d . . . . .
H3A H 0.7488 0.7176 0.3039 0.060 Uiso 1 1 calc R U . . .
H3B H 0.7670 0.8435 0.2745 0.060 Uiso 1 1 calc R U . . .
N4 N 0.81408(9) 0.52431(18) 0.12821(12) 0.0581(6) Uani 1 1 d . . . . .
H4D H 0.8029 0.4785 0.1581 0.070 Uiso 1 1 calc R U . . .
H4E H 0.8226 0.4811 0.0952 0.070 Uiso 1 1 calc R U . . .
O1 O 0.84048(8) 0.92496(17) -0.04337(9) 0.0610(5) Uani 1 1 d . . . . .
O2 O 0.80770(7) 1.19958(14) 0.12628(9) 0.0510(4) Uani 1 1 d . . . . .
O3 O 0.77446(6) 0.54490(14) 0.23332(8) 0.0469(4) 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
C1 C2 1.374(3) . ?
C1 C7 1.377(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.378(4) . ?
C2 H2 0.9300 . ?
C3 C5 1.390(4) . ?
C3 C4 1.515(4) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C5 C6 1.381(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.384(3) . ?
C6 H6 0.9300 . ?
C7 N1 1.453(2) . ?
C8 N2 1.454(3) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 O1 1.200(3) . ?
C9 N2 1.387(3) . ?
C9 C10 1.508(3) . ?
C10 C11 1.334(3) . ?
C10 N1 1.377(3) . ?
C11 C12 1.469(3) . ?
C11 C19 1.495(3) . ?
C12 O2 1.218(2) . ?
C12 N2 1.394(3) . ?
C13 C14 1.391(4) . ?
C13 C18 1.395(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.371(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.380(4) . ?
C15 Cl1 1.746(3) . ?
C16 C17 1.393(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.383(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.534(3) . ?
C19 C20 1.532(3) . ?
C19 H19 0.9800 . ?
C20 C22 1.381(3) . ?
C20 C21 1.459(3) . ?
C21 O3 1.256(2) . ?
C21 N3 1.347(3) . ?
C22 N4 1.352(3) . ?
C22 N1 1.414(2) . ?
N3 H3A 0.8600 . ?
N3 H3B 0.8600 . ?
N4 H4D 0.8600 . ?
N4 H4E 0.8600 . ?

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 C1 C7 119.6(2) . . ?
C2 C1 H1 120.2 . . ?
C7 C1 H1 120.2 . . ?
C1 C2 C3 121.9(2) . . ?
C1 C2 H2 119.1 . . ?
C3 C2 H2 119.1 . . ?
C2 C3 C5 117.7(2) . . ?
C2 C3 C4 121.3(3) . . ?
C5 C3 C4 121.0(3) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C6 C5 C3 121.5(2) . . ?
C6 C5 H5 119.3 . . ?
C3 C5 H5 119.3 . . ?
C5 C6 C7 119.2(2) . . ?
C5 C6 H6 120.4 . . ?
C7 C6 H6 120.4 . . ?
C1 C7 C6 120.13(19) . . ?
C1 C7 N1 120.37(19) . . ?
C6 C7 N1 119.49(19) . . ?
N2 C8 H8A 109.5 . . ?
N2 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
N2 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O1 C9 N2 125.49(19) . . ?
O1 C9 C10 129.5(2) . . ?
N2 C9 C10 104.95(17) . . ?
C11 C10 N1 124.02(17) . . ?
C11 C10 C9 108.94(18) . . ?
N1 C10 C9 126.88(17) . . ?
C10 C11 C12 108.43(17) . . ?
C10 C11 C19 123.65(17) . . ?
C12 C11 C19 127.91(17) . . ?
O2 C12 N2 123.91(18) . . ?
O2 C12 C11 129.18(18) . . ?
N2 C12 C11 106.91(16) . . ?
C14 C13 C18 121.1(2) . . ?
C14 C13 H13 119.5 . . ?
C18 C13 H13 119.5 . . ?
C15 C14 C13 119.3(2) . . ?
C15 C14 H14 120.3 . . ?
C13 C14 H14 120.3 . . ?
C14 C15 C16 121.0(2) . . ?
C14 C15 Cl1 118.8(2) . . ?
C16 C15 Cl1 120.2(3) . . ?
C15 C16 C17 119.3(3) . . ?
C15 C16 H16 120.4 . . ?
C17 C16 H16 120.4 . . ?
C18 C17 C16 121.1(2) . . ?
C18 C17 H17 119.5 . . ?
C16 C17 H17 119.5 . . ?
C17 C18 C13 118.2(2) . . ?
C17 C18 C19 121.14(18) . . ?
C13 C18 C19 120.59(19) . . ?
C11 C19 C20 107.27(15) . . ?
C11 C19 C18 109.96(15) . . ?
C20 C19 C18 113.91(15) . . ?
C11 C19 H19 108.5 . . ?
C20 C19 H19 108.5 . . ?
C18 C19 H19 108.5 . . ?
C22 C20 C21 118.82(17) . . ?
C22 C20 C19 121.98(16) . . ?
C21 C20 C19 119.17(16) . . ?
O3 C21 N3 118.42(17) . . ?
O3 C21 C20 123.91(17) . . ?
N3 C21 C20 117.66(17) . . ?
N4 C22 C20 124.23(18) . . ?
N4 C22 N1 114.48(17) . . ?
C20 C22 N1 121.29(17) . . ?
C10 N1 C22 116.53(15) . . ?
C10 N1 C7 122.10(16) . . ?
C22 N1 C7 121.36(16) . . ?
C9 N2 C12 110.76(16) . . ?
C9 N2 C8 124.13(19) . . ?
C12 N2 C8 125.08(18) . . ?
C21 N3 H3A 120.0 . . ?
C21 N3 H3B 120.0 . . ?
H3A N3 H3B 120.0 . . ?
C22 N4 H4D 120.0 . . ?
C22 N4 H4E 120.0 . . ?
H4D N4 H4E 120.0 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N3 H3A O2 0.86 2.34 3.158(3) 157.8 4_645
N3 H3B O3 0.86 2.20 2.948(3) 145.3 4_655
N4 H4D O3 0.86 1.97 2.613(3) 130.3 .

_refine_diff_density_max         0.370
_refine_diff_density_min         -0.490
_refine_diff_density_rms         0.049

loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.500 -0.149 0.250 169 36 ' '
2 0.500 0.149 0.750 169 36 ' '
3 0.000 0.351 0.250 169 36 ' '
4 0.000 0.649 0.750 169 36 ' '
_platon_squeeze_details          
; 
;


####################################################################### 
# 
# 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_2b
_audit_block_doi                 10.5517/cc1kq6s8
_database_code_depnum_ccdc_archive 'CCDC 1451320'
_audit_update_record             
;
2016-02-02 deposited with the CCDC.
2016-04-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C27 H27 Cl N2 O4'
_chemical_formula_sum            'C27 H27 Cl N2 O4'
_chemical_formula_weight         478.96

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.2100(10)
_cell_length_b                   10.2429(11)
_cell_length_c                   15.4674(18)
_cell_angle_alpha                103.787(3)
_cell_angle_beta                 97.732(3)
_cell_angle_gamma                100.546(3)
_cell_volume                     1368.7(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    8487
_cell_measurement_theta_min      2.29
_cell_measurement_theta_max      27.42

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.162
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             504
_exptl_absorpt_coefficient_mu    0.172
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.953
_exptl_absorpt_correction_T_max  0.966
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20646
_diffrn_reflns_av_R_equivalents  0.0490
_diffrn_reflns_av_sigmaI/netI    0.0502
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.38
_diffrn_reflns_theta_max         27.56
_reflns_number_total             6244
_reflns_number_gt                4394
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0864P)²+0.1551P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6244
_refine_ls_number_parameters     312
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0815
_refine_ls_R_factor_gt           0.0553
_refine_ls_wR_factor_ref         0.1664
_refine_ls_wR_factor_gt          0.1551
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_restrained_S_all      1.086
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.9141(2) 0.7460(2) -0.08793(12) 0.0503(5) Uani 1 1 d . . .
H1A H 0.9707 0.8156 -0.1066 0.060 Uiso 1 1 calc R . .
C2 C 0.9338(3) 0.6115(2) -0.11430(14) 0.0607(6) Uani 1 1 d . . .
H2 H 1.0044 0.5929 -0.1505 0.073 Uiso 1 1 calc R . .
C3 C 0.8522(3) 0.5052(2) -0.08857(13) 0.0560(5) Uani 1 1 d . . .
C4 C 0.8758(3) 0.3596(2) -0.11825(17) 0.0805(8) Uani 1 1 d . . .
H4A H 0.9130 0.3471 -0.1740 0.121 Uiso 1 1 calc R . .
H4B H 0.7820 0.2948 -0.1270 0.121 Uiso 1 1 calc R . .
H4C H 0.9474 0.3448 -0.0724 0.121 Uiso 1 1 calc R . .
C5 C 0.7492(3) 0.5365(2) -0.03416(13) 0.0547(5) Uani 1 1 d . . .
H5 H 0.6930 0.4668 -0.0155 0.066 Uiso 1 1 calc R . .
C6 C 0.7277(2) 0.67025(19) -0.00663(12) 0.0456(4) Uani 1 1 d . . .
H6 H 0.6579 0.6889 0.0302 0.055 Uiso 1 1 calc R . .
C7 C 0.8102(2) 0.77568(17) -0.03402(10) 0.0385(4) Uani 1 1 d . . .
C8 C 0.6692(2) 1.09722(18) 0.05538(11) 0.0401(4) Uani 1 1 d . . .
C9 C 0.74358(18) 0.97943(17) 0.06259(10) 0.0347(4) Uani 1 1 d . . .
C10 C 0.75632(18) 0.96980(16) 0.14943(10) 0.0345(4) Uani 1 1 d . . .
C11 C 0.68899(19) 1.07696(18) 0.19834(11) 0.0403(4) Uani 1 1 d . . .
C12 C 0.5761(3) 1.2706(2) 0.16594(15) 0.0641(6) Uani 1 1 d . . .
H12A H 0.6125 1.3386 0.1360 0.096 Uiso 1 1 calc R . .
H12B H 0.6028 1.3097 0.2304 0.096 Uiso 1 1 calc R . .
H12C H 0.4687 1.2415 0.1485 0.096 Uiso 1 1 calc R . .
C13 C 0.8113(2) 0.7223(2) 0.29540(13) 0.0501(5) Uani 1 1 d . . .
H13 H 0.9157 0.7397 0.3087 0.060 Uiso 1 1 calc R . .
C14 C 0.7278(3) 0.6310(2) 0.33334(15) 0.0584(5) Uani 1 1 d . . .
H14 H 0.7755 0.5891 0.3725 0.070 Uiso 1 1 calc R . .
C15 C 0.5753(3) 0.60401(19) 0.31234(14) 0.0535(5) Uani 1 1 d . . .
C16 C 0.5038(2) 0.6642(2) 0.25490(15) 0.0603(6) Uani 1 1 d . . .
H16 H 0.3994 0.6433 0.2403 0.072 Uiso 1 1 calc R . .
C17 C 0.5881(2) 0.7572(2) 0.21813(13) 0.0499(5) Uani 1 1 d . . .
H17 H 0.5391 0.7990 0.1794 0.060 Uiso 1 1 calc R . .
C18 C 0.74322(19) 0.78826(17) 0.23836(11) 0.0374(4) Uani 1 1 d . . .
C19 C 0.84026(18) 0.88698(16) 0.19783(10) 0.0332(3) Uani 1 1 d . . .
H19 H 0.8787 0.8277 0.1508 0.040 Uiso 1 1 calc R . .
C20 C 0.97962(18) 0.97820(16) 0.26443(10) 0.0329(3) Uani 1 1 d . . .
C21 C 1.11572(18) 1.00455(16) 0.22673(10) 0.0346(4) Uani 1 1 d . . .
C22 C 1.2586(2) 1.0879(2) 0.28923(12) 0.0510(5) Uani 1 1 d . . .
H22A H 1.2658 1.1844 0.2915 0.061 Uiso 1 1 calc R . .
H22B H 1.3430 1.0604 0.2643 0.061 Uiso 1 1 calc R . .
C23 C 1.2715(2) 1.0728(2) 0.38579(12) 0.0456(4) Uani 1 1 d . . .
C24 C 1.4103(3) 1.1741(3) 0.44710(15) 0.0729(7) Uani 1 1 d . . .
H24A H 1.4023 1.2667 0.4486 0.109 Uiso 1 1 calc R . .
H24B H 1.4986 1.1565 0.4240 0.109 Uiso 1 1 calc R . .
H24C H 1.4174 1.1628 0.5073 0.109 Uiso 1 1 calc R . .
C25 C 1.2817(3) 0.9252(2) 0.38625(15) 0.0619(6) Uani 1 1 d . . .
H25A H 1.3742 0.9080 0.3689 0.093 Uiso 1 1 calc R . .
H25B H 1.1984 0.8611 0.3441 0.093 Uiso 1 1 calc R . .
H25C H 1.2789 0.9142 0.4460 0.093 Uiso 1 1 calc R . .
C26 C 1.1315(2) 1.10606(19) 0.41982(11) 0.0433(4) Uani 1 1 d . . .
H26A H 1.1265 1.0788 0.4754 0.052 Uiso 1 1 calc R . .
H26B H 1.1409 1.2051 0.4342 0.052 Uiso 1 1 calc R . .
C27 C 0.98773(19) 1.03729(17) 0.35423(10) 0.0354(4) Uani 1 1 d . . .
Cl1 Cl 0.47087(9) 0.49011(6) 0.36053(5) 0.0908(3) Uani 1 1 d . . .
N1 N 0.78203(17) 0.91017(14) -0.01328(9) 0.0405(3) Uani 1 1 d . . .
H1B H 0.7906 0.9530 -0.0545 0.049 Uiso 1 1 calc R . .
N2 N 0.64300(18) 1.15291(16) 0.14018(10) 0.0465(4) Uani 1 1 d . . .
O1 O 0.63724(16) 1.13462(14) -0.01178(9) 0.0551(4) Uani 1 1 d . . .
O2 O 0.67178(15) 1.10161(15) 0.27745(8) 0.0523(4) Uani 1 1 d . . .
O3 O 1.11232(14) 0.96294(13) 0.14517(8) 0.0460(3) Uani 1 1 d . . .
O4 O 0.86812(14) 1.03879(14) 0.39478(8) 0.0470(3) Uani 1 1 d . . .
H4D H 0.7932 1.0312 0.3571 0.070 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
C1 C7 1.379(3) . ?
C1 C2 1.393(3) . ?
C1 H1A 0.9300 . ?
C2 C3 1.377(3) . ?
C2 H2 0.9300 . ?
C3 C5 1.382(3) . ?
C3 C4 1.517(3) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C5 C6 1.393(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.389(3) . ?
C6 H6 0.9300 . ?
C7 N1 1.418(2) . ?
C8 O1 1.209(2) . ?
C8 N2 1.372(2) . ?
C8 C9 1.511(2) . ?
C9 N1 1.346(2) . ?
C9 C10 1.361(2) . ?
C10 C11 1.463(2) . ?
C10 C19 1.505(2) . ?
C11 O2 1.2271(19) . ?
C11 N2 1.395(2) . ?
C12 N2 1.450(3) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C18 1.385(3) . ?
C13 C14 1.389(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.359(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.362(3) . ?
C15 Cl1 1.7429(19) . ?
C16 C17 1.393(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.381(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.529(2) . ?
C19 C20 1.526(2) . ?
C19 H19 0.9800 . ?
C20 C27 1.362(2) . ?
C20 C21 1.460(2) . ?
C21 O3 1.2257(18) . ?
C21 C22 1.499(3) . ?
C22 C23 1.529(2) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 C26 1.521(3) . ?
C23 C24 1.526(3) . ?
C23 C25 1.533(3) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C26 C27 1.495(2) . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C27 O4 1.340(2) . ?
N1 H1B 0.8600 . ?
O4 H4D 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
C7 C1 C2 119.72(19) . . ?
C7 C1 H1A 120.1 . . ?
C2 C1 H1A 120.1 . . ?
C3 C2 C1 122.21(19) . . ?
C3 C2 H2 118.9 . . ?
C1 C2 H2 118.9 . . ?
C2 C3 C5 117.46(18) . . ?
C2 C3 C4 121.2(2) . . ?
C5 C3 C4 121.4(2) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C3 C5 C6 121.5(2) . . ?
C3 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
C7 C6 C5 120.12(18) . . ?
C7 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
C1 C7 C6 119.03(17) . . ?
C1 C7 N1 119.50(16) . . ?
C6 C7 N1 121.30(16) . . ?
O1 C8 N2 126.47(17) . . ?
O1 C8 C9 127.08(16) . . ?
N2 C8 C9 106.45(13) . . ?
N1 C9 C10 134.70(16) . . ?
N1 C9 C8 116.85(14) . . ?
C10 C9 C8 108.44(14) . . ?
C9 C10 C11 106.54(14) . . ?
C9 C10 C19 131.21(14) . . ?
C11 C10 C19 121.63(13) . . ?
O2 C11 N2 122.40(15) . . ?
O2 C11 C10 128.36(16) . . ?
N2 C11 C10 109.23(14) . . ?
N2 C12 H12A 109.5 . . ?
N2 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
N2 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C18 C13 C14 121.75(19) . . ?
C18 C13 H13 119.1 . . ?
C14 C13 H13 119.1 . . ?
C15 C14 C13 118.90(19) . . ?
C15 C14 H14 120.6 . . ?
C13 C14 H14 120.6 . . ?
C14 C15 C16 121.24(18) . . ?
C14 C15 Cl1 118.77(17) . . ?
C16 C15 Cl1 119.99(17) . . ?
C15 C16 C17 119.62(19) . . ?
C15 C16 H16 120.2 . . ?
C17 C16 H16 120.2 . . ?
C18 C17 C16 120.91(18) . . ?
C18 C17 H17 119.5 . . ?
C16 C17 H17 119.5 . . ?
C17 C18 C13 117.56(16) . . ?
C17 C18 C19 122.73(15) . . ?
C13 C18 C19 119.67(15) . . ?
C10 C19 C20 111.54(13) . . ?
C10 C19 C18 115.01(13) . . ?
C20 C19 C18 113.54(12) . . ?
C10 C19 H19 105.2 . . ?
C20 C19 H19 105.2 . . ?
C18 C19 H19 105.2 . . ?
C27 C20 C21 117.84(14) . . ?
C27 C20 C19 126.26(14) . . ?
C21 C20 C19 115.90(13) . . ?
O3 C21 C20 120.67(15) . . ?
O3 C21 C22 120.57(15) . . ?
C20 C21 C22 118.72(14) . . ?
C21 C22 C23 114.18(14) . . ?
C21 C22 H22A 108.7 . . ?
C23 C22 H22A 108.7 . . ?
C21 C22 H22B 108.7 . . ?
C23 C22 H22B 108.7 . . ?
H22A C22 H22B 107.6 . . ?
C26 C23 C24 109.21(17) . . ?
C26 C23 C22 107.15(15) . . ?
C24 C23 C22 110.45(16) . . ?
C26 C23 C25 110.36(16) . . ?
C24 C23 C25 109.44(17) . . ?
C22 C23 C25 110.21(16) . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C23 C25 H25A 109.5 . . ?
C23 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C23 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C27 C26 C23 114.37(14) . . ?
C27 C26 H26A 108.7 . . ?
C23 C26 H26A 108.7 . . ?
C27 C26 H26B 108.7 . . ?
C23 C26 H26B 108.7 . . ?
H26A C26 H26B 107.6 . . ?
O4 C27 C20 124.13(15) . . ?
O4 C27 C26 111.80(13) . . ?
C20 C27 C26 124.07(15) . . ?
C9 N1 C7 128.38(14) . . ?
C9 N1 H1B 115.8 . . ?
C7 N1 H1B 115.8 . . ?
C8 N2 C11 109.24(14) . . ?
C8 N2 C12 125.93(15) . . ?
C11 N2 C12 124.82(15) . . ?
C27 O4 H4D 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O4 H4D O2 0.82 1.91 2.6602(18) 152.3 .
N1 H1B O3 0.86 2.03 2.8518(17) 158.4 2_775

_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full        27.56
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         0.202
_refine_diff_density_min         -0.406
_refine_diff_density_rms         0.044



loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.000 0.500 0.500 202 66 ' '
_platon_squeeze_details          
; 
;
####################################################################### 
# 
# 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_3b
_audit_block_doi                 10.5517/cc1kq6t9
_database_code_depnum_ccdc_archive 'CCDC 1451321'
_audit_update_record             
;
2016-02-02 deposited with the CCDC.
2016-04-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H22 N2 O3'
_chemical_formula_sum            'C25 H22 N2 O3'
_chemical_formula_weight         398.45

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'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   'P b c a '
_symmetry_space_group_name_Hall  '-P 2ac 2ab '

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

_cell_length_a                   18.3822(14)
_cell_length_b                   10.3349(9)
_cell_length_c                   21.4316(18)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     4071.5(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9946
_cell_measurement_theta_min      2.45
_cell_measurement_theta_max      27.33

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.300
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1680
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.976
_exptl_absorpt_correction_T_max  0.981
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            33724
_diffrn_reflns_av_R_equivalents  0.0557
_diffrn_reflns_av_sigmaI/netI    0.0416
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.20
_diffrn_reflns_theta_max         27.51
_reflns_number_total             4661
_reflns_number_gt                3139
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0681P)²+1.0753P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4661
_refine_ls_number_parameters     273
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0902
_refine_ls_R_factor_gt           0.0540
_refine_ls_wR_factor_ref         0.1438
_refine_ls_wR_factor_gt          0.1267
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.022
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.26564(10) 0.62777(18) 0.09583(9) 0.0506(5) Uani 1 1 d . . .
H1 H 0.2834 0.6898 0.0683 0.061 Uiso 1 1 calc R . .
C2 C 0.30496(11) 0.5936(2) 0.14889(10) 0.0594(6) Uani 1 1 d . . .
H2 H 0.3489 0.6348 0.1570 0.071 Uiso 1 1 calc R . .
C3 C 0.28045(11) 0.5006(2) 0.18959(9) 0.0551(5) Uani 1 1 d . . .
C4 C 0.32427(16) 0.4618(3) 0.24683(12) 0.0960(9) Uani 1 1 d . . .
H4A H 0.2976 0.4839 0.2838 0.144 Uiso 1 1 calc R . .
H4B H 0.3700 0.5068 0.2467 0.144 Uiso 1 1 calc R . .
H4C H 0.3329 0.3702 0.2461 0.144 Uiso 1 1 calc R . .
C5 C 0.21590(12) 0.4395(2) 0.17632(9) 0.0585(5) Uani 1 1 d . . .
H5 H 0.1990 0.3747 0.2027 0.070 Uiso 1 1 calc R . .
C6 C 0.17570(10) 0.47294(19) 0.12427(8) 0.0498(5) Uani 1 1 d . . .
H6 H 0.1320 0.4309 0.1159 0.060 Uiso 1 1 calc R . .
C7 C 0.20033(9) 0.56839(16) 0.08493(7) 0.0358(4) Uani 1 1 d . . .
C8 C 0.20271(13) 0.2392(2) -0.11520(12) 0.0760(7) Uani 1 1 d . . .
H8A H 0.2504 0.2544 -0.1320 0.114 Uiso 1 1 calc R . .
H8B H 0.1707 0.2120 -0.1481 0.114 Uiso 1 1 calc R . .
H8C H 0.2052 0.1730 -0.0839 0.114 Uiso 1 1 calc R . .
C9 C 0.20341(10) 0.41425(17) -0.03427(8) 0.0422(4) Uani 1 1 d . . .
C10 C 0.15114(8) 0.52202(15) -0.01861(7) 0.0340(4) Uani 1 1 d . . .
C11 C 0.09907(9) 0.52680(15) -0.06200(7) 0.0350(4) Uani 1 1 d . . .
C12 C 0.11053(10) 0.41822(17) -0.10524(8) 0.0414(4) Uani 1 1 d . . .
C13 C 0.09790(12) 0.81180(19) -0.12264(9) 0.0564(5) Uani 1 1 d . . .
H13 H 0.1272 0.8269 -0.0880 0.068 Uiso 1 1 calc R . .
C14 C 0.10477(17) 0.8891(2) -0.17540(12) 0.0866(9) Uani 1 1 d . . .
H14 H 0.1389 0.9555 -0.1758 0.104 Uiso 1 1 calc R . .
C15 C 0.0622(2) 0.8688(3) -0.22653(12) 0.0920(10) Uani 1 1 d . . .
H15 H 0.0669 0.9213 -0.2615 0.110 Uiso 1 1 calc R . .
C16 C 0.01250(15) 0.7708(3) -0.22584(10) 0.0891(9) Uani 1 1 d . . .
H16 H -0.0169 0.7567 -0.2605 0.107 Uiso 1 1 calc R . .
C17 C 0.00567(11) 0.6926(3) -0.17400(9) 0.0657(6) Uani 1 1 d . . .
H17 H -0.0278 0.6251 -0.1743 0.079 Uiso 1 1 calc R . .
C18 C 0.04781(9) 0.71307(16) -0.12166(7) 0.0384(4) Uani 1 1 d . . .
C19 C 0.04035(9) 0.62593(15) -0.06428(7) 0.0353(4) Uani 1 1 d . . .
H19 H -0.0067 0.5815 -0.0663 0.042 Uiso 1 1 calc R . .
C20 C -0.01900(9) 0.78438(16) 0.00936(8) 0.0419(4) Uani 1 1 d . . .
C21 C 0.04391(8) 0.70220(15) -0.00372(7) 0.0340(4) Uani 1 1 d . . .
C22 C 0.09906(8) 0.69374(15) 0.03840(7) 0.0350(4) Uani 1 1 d . . .
C23 C 0.10248(11) 0.77905(18) 0.09528(8) 0.0481(5) Uani 1 1 d . . .
H23A H 0.1529 0.7994 0.1045 0.058 Uiso 1 1 calc R . .
H23B H 0.0825 0.7330 0.1308 0.058 Uiso 1 1 calc R . .
C24 C 0.06036(12) 0.90350(19) 0.08549(10) 0.0569(5) Uani 1 1 d . . .
H24A H 0.0586 0.9516 0.1243 0.068 Uiso 1 1 calc R . .
H24B H 0.0851 0.9564 0.0547 0.068 Uiso 1 1 calc R . .
C25 C -0.01585(11) 0.87604(19) 0.06370(10) 0.0544(5) Uani 1 1 d . . .
H25A H -0.0434 0.8397 0.0981 0.065 Uiso 1 1 calc R . .
H25B H -0.0388 0.9569 0.0519 0.065 Uiso 1 1 calc R . .
N1 N 0.15599(7) 0.60402(13) 0.03149(6) 0.0368(3) Uani 1 1 d . . .
N2 N 0.17523(9) 0.35766(14) -0.08755(7) 0.0482(4) Uani 1 1 d . . .
O1 O 0.25847(7) 0.38265(14) -0.00849(7) 0.0610(4) Uani 1 1 d . . .
O2 O 0.07189(8) 0.38268(13) -0.14773(6) 0.0580(4) Uani 1 1 d . . .
O3 O -0.07423(7) 0.77507(13) -0.02233(6) 0.0582(4) 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
C1 C7 1.368(2) . ?
C1 C2 1.393(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.374(3) . ?
C2 H2 0.9300 . ?
C3 C5 1.374(3) . ?
C3 C4 1.521(3) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C5 C6 1.382(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.374(2) . ?
C6 H6 0.9300 . ?
C7 N1 1.453(2) . ?
C8 N2 1.451(2) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 O1 1.198(2) . ?
C9 N2 1.384(2) . ?
C9 C10 1.509(2) . ?
C10 C11 1.335(2) . ?
C10 N1 1.371(2) . ?
C11 C12 1.470(2) . ?
C11 C19 1.489(2) . ?
C12 O2 1.212(2) . ?
C12 N2 1.396(2) . ?
C13 C18 1.375(3) . ?
C13 C14 1.390(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.363(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.364(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.380(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.380(2) . ?
C17 H17 0.9300 . ?
C18 C19 1.530(2) . ?
C19 C21 1.520(2) . ?
C19 H19 0.9800 . ?
C20 O3 1.225(2) . ?
C20 C21 1.462(2) . ?
C20 C25 1.502(3) . ?
C21 C22 1.360(2) . ?
C22 N1 1.406(2) . ?
C22 C23 1.506(2) . ?
C23 C24 1.516(3) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C24 C25 1.504(3) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?

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
C7 C1 C2 118.73(18) . . ?
C7 C1 H1 120.6 . . ?
C2 C1 H1 120.6 . . ?
C3 C2 C1 121.71(18) . . ?
C3 C2 H2 119.1 . . ?
C1 C2 H2 119.1 . . ?
C2 C3 C5 118.25(17) . . ?
C2 C3 C4 121.5(2) . . ?
C5 C3 C4 120.2(2) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C3 C5 C6 120.92(19) . . ?
C3 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C7 C6 C5 119.90(17) . . ?
C7 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
C1 C7 C6 120.42(15) . . ?
C1 C7 N1 120.86(15) . . ?
C6 C7 N1 118.72(14) . . ?
N2 C8 H8A 109.5 . . ?
N2 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
N2 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O1 C9 N2 125.56(17) . . ?
O1 C9 C10 129.53(17) . . ?
N2 C9 C10 104.90(14) . . ?
C11 C10 N1 124.70(15) . . ?
C11 C10 C9 109.20(14) . . ?
N1 C10 C9 126.10(14) . . ?
C10 C11 C12 107.93(15) . . ?
C10 C11 C19 124.60(15) . . ?
C12 C11 C19 127.47(14) . . ?
O2 C12 N2 124.57(17) . . ?
O2 C12 C11 128.37(17) . . ?
N2 C12 C11 107.04(14) . . ?
C18 C13 C14 120.0(2) . . ?
C18 C13 H13 120.0 . . ?
C14 C13 H13 120.0 . . ?
C15 C14 C13 120.9(2) . . ?
C15 C14 H14 119.6 . . ?
C13 C14 H14 119.6 . . ?
C14 C15 C16 119.3(2) . . ?
C14 C15 H15 120.3 . . ?
C16 C15 H15 120.3 . . ?
C15 C16 C17 120.3(2) . . ?
C15 C16 H16 119.8 . . ?
C17 C16 H16 119.8 . . ?
C18 C17 C16 120.9(2) . . ?
C18 C17 H17 119.5 . . ?
C16 C17 H17 119.5 . . ?
C13 C18 C17 118.53(17) . . ?
C13 C18 C19 120.61(15) . . ?
C17 C18 C19 120.84(17) . . ?
C11 C19 C21 107.32(12) . . ?
C11 C19 C18 111.48(13) . . ?
C21 C19 C18 112.15(13) . . ?
C11 C19 H19 108.6 . . ?
C21 C19 H19 108.6 . . ?
C18 C19 H19 108.6 . . ?
O3 C20 C21 120.24(17) . . ?
O3 C20 C25 120.74(16) . . ?
C21 C20 C25 118.97(16) . . ?
C22 C21 C20 119.99(15) . . ?
C22 C21 C19 124.43(14) . . ?
C20 C21 C19 115.53(14) . . ?
C21 C22 N1 121.83(14) . . ?
C21 C22 C23 122.04(15) . . ?
N1 C22 C23 116.12(14) . . ?
C22 C23 C24 111.32(15) . . ?
C22 C23 H23A 109.4 . . ?
C24 C23 H23A 109.4 . . ?
C22 C23 H23B 109.4 . . ?
C24 C23 H23B 109.4 . . ?
H23A C23 H23B 108.0 . . ?
C25 C24 C23 111.02(17) . . ?
C25 C24 H24A 109.4 . . ?
C23 C24 H24A 109.4 . . ?
C25 C24 H24B 109.4 . . ?
C23 C24 H24B 109.4 . . ?
H24A C24 H24B 108.0 . . ?
C20 C25 C24 113.31(16) . . ?
C20 C25 H25A 108.9 . . ?
C24 C25 H25A 108.9 . . ?
C20 C25 H25B 108.9 . . ?
C24 C25 H25B 108.9 . . ?
H25A C25 H25B 107.7 . . ?
C10 N1 C22 116.21(13) . . ?
C10 N1 C7 119.81(13) . . ?
C22 N1 C7 120.11(13) . . ?
C9 N2 C12 110.70(14) . . ?
C9 N2 C8 124.29(17) . . ?
C12 N2 C8 124.32(16) . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        27.51
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.168
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.048
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_3i
_audit_block_doi                 10.5517/cc1kq6vb
_database_code_depnum_ccdc_archive 'CCDC 1451322'
_audit_update_record             
;
2016-02-02 deposited with the CCDC.
2016-04-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C27 H25 N3 O6'
_chemical_formula_sum            'C27 H25 N3 O6'
_chemical_formula_weight         487.50

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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.8773(12)
_cell_length_b                   10.7530(13)
_cell_length_c                   12.1284(14)
_cell_angle_alpha                72.632(4)
_cell_angle_beta                 84.794(4)
_cell_angle_gamma                80.203(4)
_cell_volume                     1210.4(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    7386
_cell_measurement_theta_min      2.26
_cell_measurement_theta_max      27.40

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             512
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.974
_exptl_absorpt_correction_T_max  0.981
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17546
_diffrn_reflns_av_R_equivalents  0.0475
_diffrn_reflns_av_sigmaI/netI    0.0513
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.76
_diffrn_reflns_theta_max         27.58
_reflns_number_total             5508
_reflns_number_gt                3796
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0919P)²+0.1900P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5508
_refine_ls_number_parameters     329
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0874
_refine_ls_R_factor_gt           0.0548
_refine_ls_wR_factor_ref         0.1720
_refine_ls_wR_factor_gt          0.1501
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.36909(19) 0.64484(19) 0.77359(17) 0.0477(5) Uani 1 1 d . . .
H1 H 0.3179 0.7286 0.7591 0.057 Uiso 1 1 calc R . .
C2 C 0.3391(2) 0.5459(2) 0.87061(17) 0.0558(5) Uani 1 1 d . . .
H2 H 0.2668 0.5628 0.9213 0.067 Uiso 1 1 calc R . .
C3 C 0.4164(2) 0.42121(19) 0.89292(15) 0.0496(5) Uani 1 1 d . . .
C4 C 0.4482(4) 0.1986(2) 1.0089(2) 0.0947(10) Uani 1 1 d . . .
H4A H 0.4477 0.1711 0.9405 0.142 Uiso 1 1 calc R . .
H4B H 0.4034 0.1406 1.0722 0.142 Uiso 1 1 calc R . .
H4C H 0.5415 0.1958 1.0271 0.142 Uiso 1 1 calc R . .
C5 C 0.5237(2) 0.39579(19) 0.81758(16) 0.0505(5) Uani 1 1 d . . .
H5 H 0.5763 0.3126 0.8324 0.061 Uiso 1 1 calc R . .
C6 C 0.55221(19) 0.49546(18) 0.71982(16) 0.0455(4) Uani 1 1 d . . .
H6 H 0.6238 0.4787 0.6684 0.055 Uiso 1 1 calc R . .
C7 C 0.47596(17) 0.61843(17) 0.69806(14) 0.0371(4) Uani 1 1 d . . .
C8 C 0.1494(2) 0.7581(2) 0.3226(2) 0.0615(6) Uani 1 1 d . . .
H8A H 0.1288 0.6701 0.3552 0.092 Uiso 1 1 calc R . .
H8B H 0.1646 0.7758 0.2404 0.092 Uiso 1 1 calc R . .
H8C H 0.0736 0.8198 0.3389 0.092 Uiso 1 1 calc R . .
C9 C 0.31216(17) 0.70107(18) 0.48285(16) 0.0416(4) Uani 1 1 d . . .
C10 C 0.44007(16) 0.75377(16) 0.49753(14) 0.0356(4) Uani 1 1 d . . .
C11 C 0.47273(16) 0.84078(16) 0.39746(14) 0.0359(4) Uani 1 1 d . . .
C12 C 0.36691(18) 0.85560(17) 0.31603(16) 0.0410(4) Uani 1 1 d . . .
C13 C 0.7611(2) 0.94226(18) 0.19824(16) 0.0477(5) Uani 1 1 d . . .
H13 H 0.7343 1.0325 0.1854 0.057 Uiso 1 1 calc R . .
C14 C 0.8601(2) 0.8966(2) 0.12498(17) 0.0537(5) Uani 1 1 d . . .
H14 H 0.9002 0.9553 0.0633 0.064 Uiso 1 1 calc R . .
C15 C 0.89766(18) 0.7630(2) 0.14527(15) 0.0445(4) Uani 1 1 d . . .
C16 C 0.83811(19) 0.67307(19) 0.23350(17) 0.0473(5) Uani 1 1 d . . .
H16 H 0.8629 0.5830 0.2440 0.057 Uiso 1 1 calc R . .
C17 C 0.74031(18) 0.71998(17) 0.30631(16) 0.0430(4) Uani 1 1 d . . .
H17 H 0.6995 0.6605 0.3669 0.052 Uiso 1 1 calc R . .
C18 C 0.70187(16) 0.85447(16) 0.29053(14) 0.0358(4) Uani 1 1 d . . .
C19 C 0.59976(16) 0.90432(16) 0.37594(14) 0.0349(4) Uani 1 1 d . . .
H19 H 0.5740 0.9999 0.3451 0.042 Uiso 1 1 calc R . .
C20 C 0.66348(15) 0.87393(15) 0.49199(14) 0.0340(4) Uani 1 1 d . . .
C21 C 0.77651(17) 0.94566(17) 0.49388(16) 0.0406(4) Uani 1 1 d . . .
C22 C 0.86583(19) 0.9007(2) 0.59623(18) 0.0531(5) Uani 1 1 d . . .
H22A H 0.8475 0.9663 0.6380 0.064 Uiso 1 1 calc R . .
H22B H 0.9611 0.8974 0.5681 0.064 Uiso 1 1 calc R . .
C23 C 0.84830(18) 0.7673(2) 0.68085(16) 0.0471(5) Uani 1 1 d . . .
C24 C 0.9163(2) 0.6542(2) 0.6330(2) 0.0723(7) Uani 1 1 d . . .
H24A H 0.8779 0.6637 0.5605 0.108 Uiso 1 1 calc R . .
H24B H 0.9003 0.5717 0.6868 0.108 Uiso 1 1 calc R . .
H24C H 1.0135 0.6563 0.6216 0.108 Uiso 1 1 calc R . .
C25 C 0.9111(2) 0.7537(3) 0.7951(2) 0.0741(7) Uani 1 1 d . . .
H25A H 1.0080 0.7567 0.7825 0.111 Uiso 1 1 calc R . .
H25B H 0.8964 0.6712 0.8496 0.111 Uiso 1 1 calc R . .
H25C H 0.8684 0.8248 0.8251 0.111 Uiso 1 1 calc R . .
C26 C 0.69404(18) 0.76183(19) 0.70147(15) 0.0426(4) Uani 1 1 d . . .
H26A H 0.6803 0.6759 0.7524 0.051 Uiso 1 1 calc R . .
H26B H 0.6528 0.8274 0.7396 0.051 Uiso 1 1 calc R . .
C27 C 0.62376(16) 0.78629(16) 0.59125(14) 0.0340(4) Uani 1 1 d . . .
N1 N 0.51145(14) 0.72027(14) 0.59572(12) 0.0377(3) Uani 1 1 d . . .
N2 N 0.27240(15) 0.77142(15) 0.37291(13) 0.0460(4) Uani 1 1 d . . .
N3 N 1.00961(19) 0.7148(2) 0.07226(15) 0.0610(5) Uani 1 1 d . . .
O1 O 0.37774(19) 0.32880(15) 0.98928(12) 0.0754(5) Uani 1 1 d . . .
O2 O 0.25773(14) 0.61422(14) 0.54807(12) 0.0590(4) Uani 1 1 d . . .
O3 O 0.35748(14) 0.92578(14) 0.21740(11) 0.0567(4) Uani 1 1 d . . .
O4 O 1.0326(2) 0.5979(2) 0.08265(18) 0.1098(8) Uani 1 1 d . . .
O5 O 1.0744(2) 0.7940(2) 0.00557(17) 0.0897(6) Uani 1 1 d . . .
O6 O 0.79741(14) 1.04162(13) 0.41250(13) 0.0573(4) 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
C1 C2 1.379(3) . ?
C1 C7 1.383(2) . ?
C1 H1 0.9300 . ?
C2 C3 1.388(3) . ?
C2 H2 0.9300 . ?
C3 O1 1.362(2) . ?
C3 C5 1.382(3) . ?
C4 O1 1.415(3) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C5 C6 1.385(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.369(3) . ?
C6 H6 0.9300 . ?
C7 N1 1.450(2) . ?
C8 N2 1.454(2) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 O2 1.200(2) . ?
C9 N2 1.377(2) . ?
C9 C10 1.515(2) . ?
C10 C11 1.344(2) . ?
C10 N1 1.362(2) . ?
C11 C12 1.459(2) . ?
C11 C19 1.495(2) . ?
C12 O3 1.211(2) . ?
C12 N2 1.402(2) . ?
C13 C18 1.387(2) . ?
C13 C14 1.388(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.373(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.374(3) . ?
C15 N3 1.475(3) . ?
C16 C17 1.383(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.390(2) . ?
C17 H17 0.9300 . ?
C18 C19 1.528(2) . ?
C19 C20 1.517(2) . ?
C19 H19 0.9800 . ?
C20 C27 1.362(2) . ?
C20 C21 1.466(2) . ?
C21 O6 1.228(2) . ?
C21 C22 1.499(3) . ?
C22 C23 1.521(3) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 C25 1.527(3) . ?
C23 C24 1.530(3) . ?
C23 C26 1.530(2) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C26 C27 1.495(2) . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C27 N1 1.404(2) . ?
N3 O4 1.209(3) . ?
N3 O5 1.212(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C7 119.42(17) . . ?
C2 C1 H1 120.3 . . ?
C7 C1 H1 120.3 . . ?
C1 C2 C3 120.32(17) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
O1 C3 C5 123.66(18) . . ?
O1 C3 C2 116.36(17) . . ?
C5 C3 C2 119.96(16) . . ?
O1 C4 H4A 109.5 . . ?
O1 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
O1 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C3 C5 C6 119.29(18) . . ?
C3 C5 H5 120.4 . . ?
C6 C5 H5 120.4 . . ?
C7 C6 C5 120.65(16) . . ?
C7 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
C6 C7 C1 120.36(15) . . ?
C6 C7 N1 118.60(15) . . ?
C1 C7 N1 121.03(16) . . ?
N2 C8 H8A 109.5 . . ?
N2 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
N2 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O2 C9 N2 125.94(16) . . ?
O2 C9 C10 129.43(17) . . ?
N2 C9 C10 104.57(14) . . ?
C11 C10 N1 124.71(14) . . ?
C11 C10 C9 109.05(15) . . ?
N1 C10 C9 126.24(14) . . ?
C10 C11 C12 107.99(14) . . ?
C10 C11 C19 124.28(15) . . ?
C12 C11 C19 127.69(15) . . ?
O3 C12 N2 124.15(17) . . ?
O3 C12 C11 128.69(17) . . ?
N2 C12 C11 107.17(14) . . ?
C18 C13 C14 120.54(17) . . ?
C18 C13 H13 119.7 . . ?
C14 C13 H13 119.7 . . ?
C15 C14 C13 118.75(17) . . ?
C15 C14 H14 120.6 . . ?
C13 C14 H14 120.6 . . ?
C14 C15 C16 122.35(17) . . ?
C14 C15 N3 118.61(17) . . ?
C16 C15 N3 119.00(18) . . ?
C15 C16 C17 118.24(17) . . ?
C15 C16 H16 120.9 . . ?
C17 C16 H16 120.9 . . ?
C16 C17 C18 121.19(16) . . ?
C16 C17 H17 119.4 . . ?
C18 C17 H17 119.4 . . ?
C13 C18 C17 118.87(16) . . ?
C13 C18 C19 120.69(15) . . ?
C17 C18 C19 120.41(14) . . ?
C11 C19 C20 106.93(12) . . ?
C11 C19 C18 112.13(14) . . ?
C20 C19 C18 110.62(13) . . ?
C11 C19 H19 109.0 . . ?
C20 C19 H19 109.0 . . ?
C18 C19 H19 109.0 . . ?
C27 C20 C21 119.26(15) . . ?
C27 C20 C19 124.90(14) . . ?
C21 C20 C19 115.84(13) . . ?
O6 C21 C20 120.24(16) . . ?
O6 C21 C22 120.52(15) . . ?
C20 C21 C22 119.25(15) . . ?
C21 C22 C23 115.93(15) . . ?
C21 C22 H22A 108.3 . . ?
C23 C22 H22A 108.3 . . ?
C21 C22 H22B 108.3 . . ?
C23 C22 H22B 108.3 . . ?
H22A C22 H22B 107.4 . . ?
C22 C23 C25 109.51(17) . . ?
C22 C23 C24 111.46(18) . . ?
C25 C23 C24 109.54(18) . . ?
C22 C23 C26 107.71(15) . . ?
C25 C23 C26 109.28(16) . . ?
C24 C23 C26 109.30(17) . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C23 C25 H25A 109.5 . . ?
C23 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C23 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C27 C26 C23 112.06(14) . . ?
C27 C26 H26A 109.2 . . ?
C23 C26 H26A 109.2 . . ?
C27 C26 H26B 109.2 . . ?
C23 C26 H26B 109.2 . . ?
H26A C26 H26B 107.9 . . ?
C20 C27 N1 121.59(15) . . ?
C20 C27 C26 121.01(14) . . ?
N1 C27 C26 117.33(14) . . ?
C10 N1 C27 116.51(13) . . ?
C10 N1 C7 121.58(13) . . ?
C27 N1 C7 121.88(14) . . ?
C9 N2 C12 111.05(14) . . ?
C9 N2 C8 124.15(16) . . ?
C12 N2 C8 124.80(16) . . ?
O4 N3 O5 123.3(2) . . ?
O4 N3 C15 118.2(2) . . ?
O5 N3 C15 118.5(2) . . ?
C3 O1 C4 117.28(17) . . ?

_diffrn_measured_fraction_theta_max 0.985
_diffrn_reflns_theta_full        27.58
_diffrn_measured_fraction_theta_full 0.985
_refine_diff_density_max         0.276
_refine_diff_density_min         -0.277
_refine_diff_density_rms         0.077
####################################################################### 
# 
# 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_3l
_audit_block_doi                 10.5517/cc1kq6wc
_database_code_depnum_ccdc_archive 'CCDC 1451323'
_audit_update_record             
;
2016-02-02 deposited with the CCDC.
2016-04-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H21 Br N2 O3'
_chemical_formula_sum            'C25 H21 Br N2 O3'
_chemical_formula_weight         477.35

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

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   10.4623(14)
_cell_length_b                   18.222(2)
_cell_length_c                   24.717(3)
_cell_angle_alpha                90
_cell_angle_beta                 108.973(5)
_cell_angle_gamma                90
_cell_volume                     4456.1(10)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9927
_cell_measurement_theta_min      2.25
_cell_measurement_theta_max      25.00

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.423
_exptl_crystal_F_000             1952
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.220
_exptl_absorpt_coefficient_mu    1.874
_shelx_estimated_absorpt_T_min   0.642
_shelx_estimated_absorpt_T_max   0.683
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.620
_exptl_absorpt_correction_T_max  0.662
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            46712
_diffrn_reflns_av_unetI/netI     0.0509
_diffrn_reflns_av_R_equivalents  0.0422
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         1.417
_diffrn_reflns_theta_max         27.604
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             10301
_reflns_number_gt                6232
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0885P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         10301
_refine_ls_number_parameters     563
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0950
_refine_ls_R_factor_gt           0.0514
_refine_ls_wR_factor_ref         0.1569
_refine_ls_wR_factor_gt          0.1438
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.82985(4) 1.04075(2) 0.97060(2) 0.07285(16) Uani 1 1 d . . . . .
Br2 Br 0.54072(5) 0.34167(2) 0.50981(2) 0.07484(17) Uani 1 1 d . . . . .
C1 C 0.7937(3) 0.86552(17) 0.86159(12) 0.0470(7) Uani 1 1 d . . . . .
H1 H 0.7481 0.8209 0.8548 0.056 Uiso 1 1 calc R U . . .
C2 C 0.7843(3) 0.91065(19) 0.90495(12) 0.0512(8) Uani 1 1 d . . . . .
H2 H 0.7335 0.8968 0.9279 0.061 Uiso 1 1 calc R U . . .
C3 C 0.8519(3) 0.97663(18) 0.91333(12) 0.0482(8) Uani 1 1 d . . . . .
C4 C 0.9284(3) 0.99802(18) 0.88113(14) 0.0514(8) Uani 1 1 d . . . . .
H4 H 0.9742 1.0426 0.8881 0.062 Uiso 1 1 calc R U . . .
C5 C 0.9373(3) 0.95233(16) 0.83765(13) 0.0465(7) Uani 1 1 d . . . . .
H5 H 0.9883 0.9662 0.8148 0.056 Uiso 1 1 calc R U . . .
C6 C 0.8701(3) 0.88640(16) 0.82855(11) 0.0393(6) Uani 1 1 d . . . . .
C7 C 0.6449(3) 0.88339(17) 0.71721(12) 0.0417(7) Uani 1 1 d . . . . .
C8 C 0.7642(3) 0.83188(15) 0.73412(11) 0.0381(7) Uani 1 1 d . . . . .
C9 C 0.7466(3) 0.77972(16) 0.69457(11) 0.0388(6) Uani 1 1 d . . . . .
C10 C 0.6130(3) 0.78889(18) 0.65216(12) 0.0454(7) Uani 1 1 d . . . . .
C11 C 0.4252(3) 0.8818(2) 0.63863(15) 0.0640(9) Uani 1 1 d . . . . .
H11A H 0.3793 0.8889 0.6661 0.096 Uiso 1 1 calc R U . . .
H11B H 0.3754 0.8475 0.6100 0.096 Uiso 1 1 calc R U . . .
H11C H 0.4319 0.9278 0.6209 0.096 Uiso 1 1 calc R U . . .
C12 C 0.8632(4) 0.6872(2) 0.59780(15) 0.0638(10) Uani 1 1 d . . . . .
H12 H 0.7966 0.6521 0.5945 0.077 Uiso 1 1 calc R U . . .
C13 C 0.9174(5) 0.6944(2) 0.55471(16) 0.0750(11) Uani 1 1 d . . . . .
H13 H 0.8884 0.6630 0.5234 0.090 Uiso 1 1 calc R U . . .
C14 C 1.0121(4) 0.7458(2) 0.55596(14) 0.0561(9) Uani 1 1 d . . . . .
C15 C 1.0739(5) 0.7535(3) 0.50840(17) 0.0910(14) Uani 1 1 d . . . . .
H15A H 1.1692 0.7439 0.5234 0.136 Uiso 1 1 calc R U . . .
H15B H 1.0592 0.8024 0.4932 0.136 Uiso 1 1 calc R U . . .
H15C H 1.0322 0.7189 0.4785 0.136 Uiso 1 1 calc R U . . .
C16 C 1.0521(3) 0.7908(2) 0.60284(14) 0.0563(8) Uani 1 1 d . . . . .
H16 H 1.1153 0.8274 0.6047 0.068 Uiso 1 1 calc R U . . .
C17 C 1.0006(3) 0.78323(18) 0.64776(13) 0.0490(7) Uani 1 1 d . . . . .
H17 H 1.0314 0.8140 0.6794 0.059 Uiso 1 1 calc R U . . .
C18 C 0.9047(3) 0.73077(15) 0.64616(12) 0.0400(7) Uani 1 1 d . . . . .
C19 C 0.8485(3) 0.72195(16) 0.69568(12) 0.0414(7) Uani 1 1 d . . . . .
H19 H 0.8055 0.6737 0.6928 0.050 Uiso 1 1 calc R U . . .
C20 C 0.9596(3) 0.72747(15) 0.75279(12) 0.0402(7) Uani 1 1 d . . . . .
C21 C 0.9722(3) 0.78253(16) 0.79078(12) 0.0416(7) Uani 1 1 d . . . . .
C22 C 1.0908(3) 0.7878(2) 0.84514(14) 0.0571(9) Uani 1 1 d . . . . .
H22A H 1.1228 0.8381 0.8506 0.069 Uiso 1 1 calc R U . . .
H22B H 1.0619 0.7745 0.8774 0.069 Uiso 1 1 calc R U . . .
C23 C 1.2026(5) 0.7392(3) 0.8438(3) 0.160(3) Uani 1 1 d . . . . .
H23A H 1.2599 0.7678 0.8278 0.192 Uiso 1 1 calc R U . . .
H23B H 1.2554 0.7292 0.8833 0.192 Uiso 1 1 calc R U . . .
C24 C 1.1814(4) 0.6737(3) 0.81617(17) 0.0814(13) Uani 1 1 d . . . . .
H24A H 1.1798 0.6359 0.8436 0.098 Uiso 1 1 calc R U . . .
H24B H 1.2583 0.6638 0.8035 0.098 Uiso 1 1 calc R U . . .
C25 C 1.0573(4) 0.6664(2) 0.76622(15) 0.0565(9) Uani 1 1 d . . . . .
C26 C 0.6447(4) 0.51218(18) 0.62546(15) 0.0646(10) Uani 1 1 d . . . . .
H26 H 0.6783 0.5596 0.6263 0.077 Uiso 1 1 calc R U . . .
C27 C 0.6225(5) 0.46969(19) 0.57704(15) 0.0684(11) Uani 1 1 d . . . . .
H27 H 0.6389 0.4886 0.5449 0.082 Uiso 1 1 calc R U . . .
C28 C 0.5764(3) 0.39971(17) 0.57688(12) 0.0468(7) Uani 1 1 d . . . . .
C29 C 0.5497(3) 0.37111(16) 0.62362(12) 0.0427(7) Uani 1 1 d . . . . .
H29 H 0.5179 0.3233 0.6229 0.051 Uiso 1 1 calc R U . . .
C30 C 0.5712(3) 0.41484(15) 0.67214(12) 0.0401(7) Uani 1 1 d . . . . .
H30 H 0.5541 0.3965 0.7042 0.048 Uiso 1 1 calc R U . . .
C31 C 0.6178(3) 0.48526(15) 0.67197(12) 0.0378(6) Uani 1 1 d . . . . .
C32 C 0.8679(3) 0.48049(17) 0.77736(13) 0.0448(7) Uani 1 1 d . . . . .
C33 C 0.7519(3) 0.53338(15) 0.76629(12) 0.0362(6) Uani 1 1 d . . . . .
C34 C 0.7817(3) 0.58315(15) 0.80819(12) 0.0388(6) Uani 1 1 d . . . . .
C35 C 0.9179(3) 0.56811(18) 0.84689(14) 0.0482(7) Uani 1 1 d . . . . .
C36 C 1.0991(4) 0.4756(2) 0.8482(2) 0.0769(12) Uani 1 1 d . . . . .
H36A H 1.0966 0.4245 0.8572 0.115 Uiso 1 1 calc R U . . .
H36B H 1.1490 0.5021 0.8821 0.115 Uiso 1 1 calc R U . . .
H36C H 1.1421 0.4815 0.8196 0.115 Uiso 1 1 calc R U . . .
C37 C 0.7013(4) 0.67304(19) 0.91483(14) 0.0664(10) Uani 1 1 d . . . . .
H37 H 0.7724 0.7051 0.9177 0.080 Uiso 1 1 calc R U . . .
C38 C 0.6551(6) 0.6642(2) 0.96073(15) 0.0906(15) Uani 1 1 d . . . . .
H38 H 0.6959 0.6905 0.9941 0.109 Uiso 1 1 calc R U . . .
C39 C 0.5506(5) 0.6176(2) 0.95838(17) 0.0807(13) Uani 1 1 d . . . . .
C40 C 0.4988(8) 0.6106(3) 1.0093(2) 0.151(3) Uani 1 1 d . . . . .
H40A H 0.4183 0.6394 1.0024 0.226 Uiso 1 1 calc R U . . .
H40B H 0.5668 0.6278 1.0433 0.226 Uiso 1 1 calc R U . . .
H40C H 0.4789 0.5601 1.0141 0.226 Uiso 1 1 calc R U . . .
C41 C 0.4928(4) 0.5801(2) 0.90935(16) 0.0669(10) Uani 1 1 d . . . . .
H41 H 0.4209 0.5487 0.9067 0.080 Uiso 1 1 calc R U . . .
C42 C 0.5389(3) 0.58757(17) 0.86286(13) 0.0497(8) Uani 1 1 d . . . . .
H42 H 0.4988 0.5602 0.8299 0.060 Uiso 1 1 calc R U . . .
C43 C 0.6431(3) 0.63485(15) 0.86477(11) 0.0402(7) Uani 1 1 d . . . . .
C44 C 0.6901(3) 0.64445(14) 0.81272(11) 0.0357(6) Uani 1 1 d . . . . .
H44 H 0.7389 0.6910 0.8163 0.043 Uiso 1 1 calc R U . . .
C45 C 0.5721(3) 0.64493(14) 0.75768(11) 0.0336(6) Uani 1 1 d . . . . .
C46 C 0.5448(3) 0.59122(14) 0.71763(11) 0.0354(6) Uani 1 1 d . . . . .
C47 C 0.4174(3) 0.58970(17) 0.66775(13) 0.0482(7) Uani 1 1 d . . . . .
H47A H 0.3890 0.5392 0.6587 0.058 Uiso 1 1 calc R U . . .
H47B H 0.4339 0.6110 0.6347 0.058 Uiso 1 1 calc R U . . .
C48 C 0.3048(3) 0.63251(19) 0.68075(15) 0.0571(8) Uani 1 1 d . . . . .
H48A H 0.2263 0.6354 0.6465 0.069 Uiso 1 1 calc R U . . .
H48B H 0.2787 0.6071 0.7100 0.069 Uiso 1 1 calc R U . . .
C49 C 0.3528(3) 0.70861(18) 0.70099(14) 0.0554(8) Uani 1 1 d . . . . .
H49A H 0.3636 0.7363 0.6693 0.066 Uiso 1 1 calc R U . . .
H49B H 0.2844 0.7330 0.7132 0.066 Uiso 1 1 calc R U . . .
C50 C 0.4836(3) 0.70897(16) 0.74927(12) 0.0419(7) Uani 1 1 d . . . . .
N1 N 0.8752(2) 0.83866(12) 0.78225(10) 0.0408(6) Uani 1 1 d . . . . .
N2 N 0.5585(2) 0.85335(15) 0.66698(10) 0.0485(6) Uani 1 1 d . . . . .
N3 N 0.6339(2) 0.53277(12) 0.72098(10) 0.0379(5) Uani 1 1 d . . . . .
N4 N 0.9620(2) 0.50406(14) 0.82665(11) 0.0489(6) Uani 1 1 d . . . . .
O1 O 0.6251(2) 0.93785(13) 0.73973(10) 0.0586(6) Uani 1 1 d . . . . .
O2 O 0.5555(2) 0.74934(14) 0.61247(9) 0.0621(6) Uani 1 1 d . . . . .
O3 O 1.0337(3) 0.61037(14) 0.73701(12) 0.0744(7) Uani 1 1 d . . . . .
O4 O 0.8782(2) 0.42774(12) 0.74945(10) 0.0592(6) Uani 1 1 d . . . . .
O5 O 0.9848(2) 0.60318(13) 0.88776(10) 0.0614(6) Uani 1 1 d . . . . .
O6 O 0.5183(2) 0.76286(11) 0.78029(9) 0.0549(6) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C3 1.906(3) . ?
Br2 C28 1.898(3) . ?
C1 C6 1.370(4) . ?
C1 C2 1.380(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.376(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.357(5) . ?
C4 C5 1.386(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.373(4) . ?
C5 H5 0.9300 . ?
C6 N1 1.452(3) . ?
C7 O1 1.189(3) . ?
C7 N2 1.388(4) . ?
C7 C8 1.508(4) . ?
C8 C9 1.333(4) . ?
C8 N1 1.371(4) . ?
C9 C10 1.459(4) . ?
C9 C19 1.492(4) . ?
C10 O2 1.208(4) . ?
C10 N2 1.406(4) . ?
C11 N2 1.438(4) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C13 1.366(5) . ?
C12 C18 1.382(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.355(5) . ?
C13 H13 0.9300 . ?
C14 C16 1.370(5) . ?
C14 C15 1.521(4) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 C17 1.390(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.377(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.529(4) . ?
C19 C20 1.512(4) . ?
C19 H19 0.9800 . ?
C20 C21 1.351(4) . ?
C20 C25 1.473(4) . ?
C21 N1 1.408(4) . ?
C21 C22 1.507(4) . ?
C22 C23 1.475(6) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 C24 1.358(6) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C24 C25 1.479(6) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C25 O3 1.229(4) . ?
C26 C31 1.361(4) . ?
C26 C27 1.380(5) . ?
C26 H26 0.9300 . ?
C27 C28 1.363(4) . ?
C27 H27 0.9300 . ?
C28 C29 1.376(4) . ?
C29 C30 1.396(4) . ?
C29 H29 0.9300 . ?
C30 C31 1.373(4) . ?
C30 H30 0.9300 . ?
C31 N3 1.454(3) . ?
C32 O4 1.208(4) . ?
C32 N4 1.363(4) . ?
C32 C33 1.503(4) . ?
C33 C34 1.335(4) . ?
C33 N3 1.371(4) . ?
C34 C35 1.461(4) . ?
C34 C44 1.499(4) . ?
C35 O5 1.208(4) . ?
C35 N4 1.406(4) . ?
C36 N4 1.453(4) . ?
C36 H36A 0.9600 . ?
C36 H36B 0.9600 . ?
C36 H36C 0.9600 . ?
C37 C43 1.377(4) . ?
C37 C38 1.380(5) . ?
C37 H37 0.9300 . ?
C38 C39 1.370(6) . ?
C38 H38 0.9300 . ?
C39 C41 1.351(6) . ?
C39 C40 1.528(5) . ?
C40 H40A 0.9600 . ?
C40 H40B 0.9600 . ?
C40 H40C 0.9600 . ?
C41 C42 1.390(4) . ?
C41 H41 0.9300 . ?
C42 C43 1.378(4) . ?
C42 H42 0.9300 . ?
C43 C44 1.529(4) . ?
C44 C45 1.511(4) . ?
C44 H44 0.9800 . ?
C45 C46 1.355(4) . ?
C45 C50 1.462(4) . ?
C46 N3 1.400(3) . ?
C46 C47 1.493(4) . ?
C47 C48 1.531(4) . ?
C47 H47A 0.9700 . ?
C47 H47B 0.9700 . ?
C48 C49 1.504(5) . ?
C48 H48A 0.9700 . ?
C48 H48B 0.9700 . ?
C49 C50 1.495(4) . ?
C49 H49A 0.9700 . ?
C49 H49B 0.9700 . ?
C50 O6 1.226(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
C6 C1 C2 120.0(3) . . ?
C6 C1 H1 120.0 . . ?
C2 C1 H1 120.0 . . ?
C3 C2 C1 118.3(3) . . ?
C3 C2 H2 120.8 . . ?
C1 C2 H2 120.8 . . ?
C4 C3 C2 122.4(3) . . ?
C4 C3 Br1 119.8(2) . . ?
C2 C3 Br1 117.8(2) . . ?
C3 C4 C5 118.9(3) . . ?
C3 C4 H4 120.6 . . ?
C5 C4 H4 120.6 . . ?
C6 C5 C4 119.5(3) . . ?
C6 C5 H5 120.2 . . ?
C4 C5 H5 120.2 . . ?
C1 C6 C5 120.8(3) . . ?
C1 C6 N1 118.8(3) . . ?
C5 C6 N1 120.4(2) . . ?
O1 C7 N2 125.9(3) . . ?
O1 C7 C8 130.1(3) . . ?
N2 C7 C8 104.0(2) . . ?
C9 C8 N1 125.2(3) . . ?
C9 C8 C7 109.7(3) . . ?
N1 C8 C7 125.1(2) . . ?
C8 C9 C10 108.5(3) . . ?
C8 C9 C19 124.2(3) . . ?
C10 C9 C19 127.3(2) . . ?
O2 C10 N2 125.0(3) . . ?
O2 C10 C9 128.5(3) . . ?
N2 C10 C9 106.5(2) . . ?
N2 C11 H11A 109.5 . . ?
N2 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
N2 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 C18 121.7(3) . . ?
C13 C12 H12 119.1 . . ?
C18 C12 H12 119.1 . . ?
C14 C13 C12 122.3(3) . . ?
C14 C13 H13 118.8 . . ?
C12 C13 H13 118.8 . . ?
C13 C14 C16 116.9(3) . . ?
C13 C14 C15 122.5(3) . . ?
C16 C14 C15 120.6(4) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C16 C17 121.6(3) . . ?
C14 C16 H16 119.2 . . ?
C17 C16 H16 119.2 . . ?
C18 C17 C16 121.0(3) . . ?
C18 C17 H17 119.5 . . ?
C16 C17 H17 119.5 . . ?
C17 C18 C12 116.4(3) . . ?
C17 C18 C19 121.1(3) . . ?
C12 C18 C19 122.5(3) . . ?
C9 C19 C20 107.3(2) . . ?
C9 C19 C18 111.7(2) . . ?
C20 C19 C18 111.2(2) . . ?
C9 C19 H19 108.9 . . ?
C20 C19 H19 108.9 . . ?
C18 C19 H19 108.9 . . ?
C21 C20 C25 120.0(3) . . ?
C21 C20 C19 124.8(3) . . ?
C25 C20 C19 115.2(3) . . ?
C20 C21 N1 122.2(3) . . ?
C20 C21 C22 122.2(3) . . ?
N1 C21 C22 115.6(3) . . ?
C23 C22 C21 111.8(3) . . ?
C23 C22 H22A 109.3 . . ?
C21 C22 H22A 109.3 . . ?
C23 C22 H22B 109.3 . . ?
C21 C22 H22B 109.3 . . ?
H22A C22 H22B 107.9 . . ?
C24 C23 C22 122.5(4) . . ?
C24 C23 H23A 106.7 . . ?
C22 C23 H23A 106.7 . . ?
C24 C23 H23B 106.7 . . ?
C22 C23 H23B 106.7 . . ?
H23A C23 H23B 106.6 . . ?
C23 C24 C25 117.0(4) . . ?
C23 C24 H24A 108.0 . . ?
C25 C24 H24A 108.0 . . ?
C23 C24 H24B 108.0 . . ?
C25 C24 H24B 108.0 . . ?
H24A C24 H24B 107.3 . . ?
O3 C25 C20 120.2(3) . . ?
O3 C25 C24 121.3(3) . . ?
C20 C25 C24 118.5(3) . . ?
C31 C26 C27 120.5(3) . . ?
C31 C26 H26 119.7 . . ?
C27 C26 H26 119.7 . . ?
C28 C27 C26 119.1(3) . . ?
C28 C27 H27 120.4 . . ?
C26 C27 H27 120.4 . . ?
C27 C28 C29 121.3(3) . . ?
C27 C28 Br2 119.5(2) . . ?
C29 C28 Br2 119.1(2) . . ?
C28 C29 C30 119.0(3) . . ?
C28 C29 H29 120.5 . . ?
C30 C29 H29 120.5 . . ?
C31 C30 C29 119.3(3) . . ?
C31 C30 H30 120.4 . . ?
C29 C30 H30 120.4 . . ?
C26 C31 C30 120.7(3) . . ?
C26 C31 N3 119.3(3) . . ?
C30 C31 N3 119.9(2) . . ?
O4 C32 N4 126.1(3) . . ?
O4 C32 C33 128.5(3) . . ?
N4 C32 C33 105.5(3) . . ?
C34 C33 N3 124.1(3) . . ?
C34 C33 C32 108.9(3) . . ?
N3 C33 C32 127.1(2) . . ?
C33 C34 C35 108.2(3) . . ?
C33 C34 C44 124.8(3) . . ?
C35 C34 C44 127.0(3) . . ?
O5 C35 N4 124.7(3) . . ?
O5 C35 C34 128.7(3) . . ?
N4 C35 C34 106.6(3) . . ?
N4 C36 H36A 109.5 . . ?
N4 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
N4 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
C43 C37 C38 120.6(4) . . ?
C43 C37 H37 119.7 . . ?
C38 C37 H37 119.7 . . ?
C39 C38 C37 121.7(4) . . ?
C39 C38 H38 119.2 . . ?
C37 C38 H38 119.2 . . ?
C41 C39 C38 118.0(3) . . ?
C41 C39 C40 121.4(5) . . ?
C38 C39 C40 120.6(4) . . ?
C39 C40 H40A 109.5 . . ?
C39 C40 H40B 109.5 . . ?
H40A C40 H40B 109.5 . . ?
C39 C40 H40C 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?
C39 C41 C42 121.1(4) . . ?
C39 C41 H41 119.4 . . ?
C42 C41 H41 119.4 . . ?
C43 C42 C41 121.1(3) . . ?
C43 C42 H42 119.5 . . ?
C41 C42 H42 119.5 . . ?
C37 C43 C42 117.4(3) . . ?
C37 C43 C44 122.0(3) . . ?
C42 C43 C44 120.6(2) . . ?
C34 C44 C45 107.0(2) . . ?
C34 C44 C43 111.4(2) . . ?
C45 C44 C43 111.5(2) . . ?
C34 C44 H44 109.0 . . ?
C45 C44 H44 109.0 . . ?
C43 C44 H44 109.0 . . ?
C46 C45 C50 120.0(3) . . ?
C46 C45 C44 124.7(2) . . ?
C50 C45 C44 115.3(2) . . ?
C45 C46 N3 121.9(3) . . ?
C45 C46 C47 122.4(2) . . ?
N3 C46 C47 115.7(2) . . ?
C46 C47 C48 111.0(2) . . ?
C46 C47 H47A 109.4 . . ?
C48 C47 H47A 109.4 . . ?
C46 C47 H47B 109.4 . . ?
C48 C47 H47B 109.4 . . ?
H47A C47 H47B 108.0 . . ?
C49 C48 C47 110.1(3) . . ?
C49 C48 H48A 109.6 . . ?
C47 C48 H48A 109.6 . . ?
C49 C48 H48B 109.6 . . ?
C47 C48 H48B 109.6 . . ?
H48A C48 H48B 108.2 . . ?
C50 C49 C48 112.9(3) . . ?
C50 C49 H49A 109.0 . . ?
C48 C49 H49A 109.0 . . ?
C50 C49 H49B 109.0 . . ?
C48 C49 H49B 109.0 . . ?
H49A C49 H49B 107.8 . . ?
O6 C50 C45 120.4(3) . . ?
O6 C50 C49 120.7(3) . . ?
C45 C50 C49 118.9(3) . . ?
C8 N1 C21 115.5(2) . . ?
C8 N1 C6 120.0(2) . . ?
C21 N1 C6 121.8(2) . . ?
C7 N2 C10 111.2(2) . . ?
C7 N2 C11 122.7(3) . . ?
C10 N2 C11 125.8(3) . . ?
C33 N3 C46 116.6(2) . . ?
C33 N3 C31 121.0(2) . . ?
C46 N3 C31 120.6(2) . . ?
C32 N4 C35 110.7(2) . . ?
C32 N4 C36 123.7(3) . . ?
C35 N4 C36 124.4(3) . . ?

_refine_diff_density_max         0.759
_refine_diff_density_min         -0.797
_refine_diff_density_rms         0.082

loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.000 0.000 0.500 142 48 ' '
2 0.000 0.500 1.000 142 48 ' '
_platon_squeeze_details          
;
;


