# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_hd_wql24
_database_code_depnum_ccdc_archive 'CCDC 1944631'
loop_
_audit_author_name
_audit_author_address
'Qilin Wang'
;Henan University
China
;
_audit_update_record             
;
2019-08-01 deposited with the CCDC.	2019-12-17 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C38 H42 Br N5 O3, 2(C H4 O)'
_chemical_formula_sum            'C40 H50 Br N5 O5'
_chemical_formula_iupac          ?
_chemical_formula_weight         760.76

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.9227(3)
_cell_length_b                   17.3502(4)
_cell_length_c                   17.7857(4)
_cell_angle_alpha                90
_cell_angle_beta                 90.6110(10)
_cell_angle_gamma                90
_cell_volume                     3678.96(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9922
_cell_measurement_theta_min      3.5589
_cell_measurement_theta_max      72.3720
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       prism
_exptl_crystal_colour            'translucent light yellow'
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_exptl_crystal_density_diffrn    1.374
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1600

_exptl_absorpt_coefficient_mu    1.937
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.32
_exptl_absorpt_correction_T_max  0.91

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'Ius Diamond'
_diffrn_source_type              Microfocus

_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  'Helixos MX multilayer Optic'

_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON II'
_diffrn_measurement_method       ?

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            36068
_diffrn_reflns_av_R_equivalents  0.0503
_diffrn_reflns_av_unetI/netI     0.0316
_diffrn_reflns_theta_min         3.56
_diffrn_reflns_theta_max         72.36
_diffrn_reflns_theta_full        72.36
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21

_refine_special_details          
;
;

_reflns_number_total             7252
_reflns_number_gt                6204
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0897
_refine_ls_R_factor_gt           0.0814
_refine_ls_wR_factor_gt          0.2343
_refine_ls_wR_factor_ref         0.2467
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_refine_ls_number_reflns         7252
_refine_ls_number_parameters     468
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1618P)²+4.8126P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         1.901
_refine_diff_density_min         -1.272
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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

_computing_data_collection       'Bruker Instrument Service vV6.2.9'
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 882)'
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br Br1 0.05262(4) 0.91737(3) 0.51741(3) 0.0642(2) Uani d . . . 1 . .
O O1 0.5143(2) 0.75815(15) 0.10367(15) 0.0411(6) Uani d . . . 1 . .
H H25 0.531535 0.804587 0.110485 0.062 Uiso calc U . R 1 . .
O O2 0.1960(2) 0.64175(18) 0.19320(15) 0.0471(6) Uani d . . . 1 . .
H H26 0.130501 0.648956 0.208597 0.071 Uiso calc U . R 1 . .
O O3 0.4582(2) 0.40598(16) 0.36178(16) 0.0449(6) Uani d . . . 1 . .
O O4 -0.1760(3) 0.7530(3) 0.1455(2) 0.0753(10) Uani d . . . 1 . .
H H44 -0.229159 0.723439 0.156344 0.113 Uiso calc U . R 1 . .
N N1 0.3216(2) 0.66081(18) 0.37545(15) 0.0359(6) Uani d . . . 1 . .
N N2 0.4910(2) 0.70979(17) 0.31365(16) 0.0344(6) Uani d . . . 1 . .
N N3 0.5984(3) 0.51914(19) 0.16670(17) 0.0415(7) Uani d . . . 1 . .
N N4 0.5909(3) 0.71019(18) 0.14400(16) 0.0379(6) Uani d . . . 1 . .
N N5 0.2534(3) 0.58881(18) 0.24266(17) 0.0380(6) Uani d . . . 1 . .
H H42 0.223264 0.548812 0.265186 0.046 Uiso calc U . R 1 . .
O O5 -0.0203(3) 0.6738(4) 0.2376(2) 0.1006(19) Uani d . . . 1 . .
H H45 -0.064529 0.698225 0.209296 0.151 Uiso calc U . R 1 . .
C C1 0.1292(3) 0.8332(2) 0.4750(2) 0.0442(8) Uani d . . . 1 . .
C C2 0.2168(3) 0.8013(2) 0.5156(2) 0.0436(8) Uani d . . . 1 . .
H H2 0.233095 0.818349 0.565311 0.052 Uiso calc U . R 1 . .
C C3 0.2804(3) 0.7443(2) 0.4830(2) 0.0419(8) Uani d . . . 1 . .
H H3 0.341758 0.722352 0.5099 0.05 Uiso calc U . R 1 . .
C C4 0.2547(3) 0.7186(2) 0.41046(19) 0.0368(7) Uani d . . . 1 . .
C C5 0.3770(3) 0.6828(2) 0.30317(18) 0.0344(7) Uani d . . . 1 . .
H H12 0.33248 0.72574 0.280059 0.041 Uiso calc U . R 1 . .
C C6 0.5700(3) 0.6499(2) 0.3404(2) 0.0376(7) Uani d . . . 1 . .
H H4 0.553341 0.637064 0.393328 0.045 Uiso calc U . R 1 . .
H H27 0.647487 0.670197 0.338519 0.045 Uiso calc U . R 1 . .
C C7 0.5620(3) 0.5767(2) 0.29268(19) 0.0358(7) Uani d . . . 1 . .
H H28 0.608 0.535575 0.317459 0.043 Uiso calc U . R 1 . .
C C8 0.6086(3) 0.5911(2) 0.2130(2) 0.0383(7) Uani d . . . 1 . .
H H15 0.689081 0.606952 0.216693 0.046 Uiso calc U . R 1 . .
C C9 0.7078(3) 0.4854(2) 0.1500(2) 0.0472(9) Uani d . . . 1 . .
H H17 0.759145 0.526655 0.133263 0.057 Uiso calc U . R 1 . .
H H16 0.699064 0.448175 0.10813 0.057 Uiso calc U . R 1 . .
C C10 0.7597(3) 0.4445(2) 0.2171(2) 0.0457(8) Uani d . . . 1 . .
C C11 0.8757(4) 0.4477(3) 0.2299(3) 0.0567(11) Uani d . . . 1 . .
H H21 0.920961 0.480596 0.200263 0.068 Uiso calc U . R 1 . .
C C12 0.9250(4) 0.4026(4) 0.2862(3) 0.0686(14) Uani d . . . 1 . .
H H20 1.003824 0.404713 0.294271 0.082 Uiso calc U . R 1 . .
C C13 0.8605(5) 0.3551(4) 0.3300(3) 0.0669(14) Uani d . . . 1 . .
H H1 0.895111 0.323715 0.367392 0.08 Uiso calc U . R 1 . .
C C14 0.3306(3) 0.5876(2) 0.40244(19) 0.0378(7) Uani d . . . 1 . .
C C15 0.3897(3) 0.5322(2) 0.36442(19) 0.0379(7) Uani d . . . 1 . .
C C16 0.4388(3) 0.5491(2) 0.28799(18) 0.0356(7) Uani d . . . 1 . .
H H29 0.434939 0.501349 0.256525 0.043 Uiso calc U . R 1 . .
C C17 0.4976(3) 0.7779(2) 0.3626(2) 0.0392(7) Uani d . . . 1 . .
H H11 0.484808 0.761656 0.415177 0.047 Uiso calc U . R 1 . .
H H5 0.437008 0.814128 0.348231 0.047 Uiso calc U . R 1 . .
C C18 0.6087(3) 0.8193(2) 0.3587(2) 0.0402(8) Uani d . . . 1 . .
C C19 0.6615(3) 0.8442(3) 0.4250(2) 0.0486(9) Uani d . . . 1 . .
H H6 0.629995 0.831952 0.472317 0.058 Uiso calc U . R 1 . .
C C20 0.7608(4) 0.8872(3) 0.4216(3) 0.0564(11) Uani d . . . 1 . .
H H10 0.794981 0.905639 0.466588 0.068 Uiso calc U . R 1 . .
C C21 0.8087(3) 0.9028(3) 0.3539(3) 0.0522(10) Uani d . . . 1 . .
H H7 0.876626 0.93133 0.351886 0.063 Uiso calc U . R 1 . .
C C22 0.7578(4) 0.8769(3) 0.2880(3) 0.0504(9) Uani d . . . 1 . .
H H9 0.791785 0.887077 0.240965 0.061 Uiso calc U . R 1 . .
C C23 0.6582(3) 0.8365(2) 0.2905(2) 0.0466(8) Uani d . . . 1 . .
H H8 0.623174 0.820171 0.244963 0.056 Uiso calc U . R 1 . .
C C24 0.3712(3) 0.6132(2) 0.24896(18) 0.0337(7) Uani d . . . 1 . .
C C25 0.4193(3) 0.6332(2) 0.17008(18) 0.0345(7) Uani d . . . 1 . .
H H24 0.376341 0.677192 0.147585 0.041 Uiso calc U . R 1 . .
C C26 0.4149(3) 0.5623(2) 0.1155(2) 0.0412(8) Uani d . . . 1 . .
H H14 0.369495 0.520998 0.138608 0.049 Uiso calc U . R 1 . .
H H13 0.377268 0.577833 0.068015 0.049 Uiso calc U . R 1 . .
C C27 0.5309(3) 0.5306(2) 0.0978(2) 0.0426(8) Uani d . . . 1 . .
H H23 0.52291 0.480884 0.07107 0.051 Uiso calc U . R 1 . .
H H22 0.570145 0.566983 0.064236 0.051 Uiso calc U . R 1 . .
C C28 0.5412(3) 0.6536(2) 0.17528(19) 0.0368(7) Uani d . . . 1 . .
C C29 0.7462(4) 0.3528(3) 0.3197(3) 0.0543(10) Uani d . . . 1 . .
H H18 0.701108 0.320845 0.3505 0.065 Uiso calc U . R 1 . .
C C30 0.6968(3) 0.3983(2) 0.2632(2) 0.0443(8) Uani d . . . 1 . .
H H19 0.617666 0.397205 0.25665 0.053 Uiso calc U . R 1 . .
C C31 0.4021(3) 0.4557(2) 0.3941(2) 0.0399(8) Uani d . . . 1 . .
C C32 0.3452(3) 0.4364(2) 0.4673(2) 0.0447(8) Uani d . . . 1 . .
H H31 0.398458 0.4459 0.509436 0.054 Uiso calc U . R 1 . .
H H30 0.326046 0.380896 0.467573 0.054 Uiso calc U . R 1 . .
C C33 0.2388(3) 0.4832(2) 0.4803(2) 0.0446(8) Uani d . . . 1 . .
C C34 0.1478(4) 0.4637(3) 0.4213(2) 0.0532(10) Uani d . . . 1 . .
H H32 0.175413 0.475948 0.370983 0.08 Uiso calc U . R 1 . .
H H34 0.080231 0.494067 0.431238 0.08 Uiso calc U . R 1 . .
H H33 0.129744 0.408681 0.42407 0.08 Uiso calc U . R 1 . .
C C35 0.1934(4) 0.4658(3) 0.5585(2) 0.0514(10) Uani d . . . 1 . .
H H35 0.172305 0.411345 0.561513 0.077 Uiso calc U . R 1 . .
H H37 0.127324 0.49799 0.567739 0.077 Uiso calc U . R 1 . .
H H36 0.251295 0.477072 0.596451 0.077 Uiso calc U . R 1 . .
C C36 0.2703(3) 0.5688(2) 0.4750(2) 0.0406(8) Uani d . . . 1 . .
H H39 0.201281 0.600354 0.478008 0.049 Uiso calc U . R 1 . .
H H38 0.319171 0.582567 0.518263 0.049 Uiso calc U . R 1 . .
C C37 0.1645(3) 0.7506(2) 0.37098(19) 0.0376(7) Uani d . . . 1 . .
H H41 0.146463 0.732815 0.321808 0.045 Uiso calc U . R 1 . .
C C38 0.1012(3) 0.8083(2) 0.4034(2) 0.0427(8) Uani d . . . 1 . .
H H40 0.039592 0.830449 0.376899 0.051 Uiso calc U . R 1 . .
C C40 -0.0758(4) 0.6523(4) 0.3026(3) 0.0710(14) Uani d . . . 1 . .
H H47 -0.020898 0.635663 0.340617 0.107 Uiso calc U . R 1 . .
H H46 -0.127365 0.609843 0.291187 0.107 Uiso calc U . R 1 . .
H H43 -0.118245 0.696385 0.321774 0.107 Uiso calc U . R 1 . .
C C41 -0.1423(5) 0.7385(4) 0.0748(4) 0.0752(15) Uani d . . . 1 . .
H H50 -0.189244 0.767426 0.039171 0.113 Uiso calc U . R 1 . .
H H49 -0.149209 0.683203 0.064469 0.113 Uiso calc U . R 1 . .
H H48 -0.063828 0.754236 0.069447 0.113 Uiso calc U . R 1 . .


_geom_special_details            
;

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Br1 C1 . 1.884(4) ?
O1 N4 . 1.424(4) ?
O1 H25 . 0.84 ?
O2 N5 . 1.440(4) ?
O2 H26 . 0.84 ?
O3 C31 . 1.237(5) ?
O4 C41 . 1.347(7) ?
O4 H44 . 0.84 ?
N1 C14 . 1.362(5) ?
N1 C4 . 1.428(5) ?
N1 C5 . 1.501(4) ?
N2 C5 . 1.448(4) ?
N2 C17 . 1.469(5) ?
N2 C6 . 1.478(4) ?
N3 C9 . 1.464(5) ?
N3 C27 . 1.472(5) ?
N3 C8 . 1.499(5) ?
N4 C28 . 1.277(5) ?
N5 C24 . 1.469(4) ?
N5 H42 . 0.88 ?
O5 C40 . 1.388(6) ?
O5 H45 . 0.84 ?
C1 C2 . 1.379(6) ?
C1 C38 . 1.383(6) ?
C2 C3 . 1.378(6) ?
C2 H2 . 0.95 ?
C3 C4 . 1.395(5) ?
C3 H3 . 0.95 ?
C4 C37 . 1.394(5) ?
C5 C24 . 1.546(5) ?
C5 H12 . 1.0 ?
C6 C7 . 1.528(5) ?
C6 H4 . 0.99 ?
C6 H27 . 0.99 ?
C7 C16 . 1.546(5) ?
C7 C8 . 1.547(5) ?
C7 H28 . 1.0 ?
C8 C28 . 1.504(5) ?
C8 H15 . 1.0 ?
C9 C10 . 1.515(6) ?
C9 H17 . 0.99 ?
C9 H16 . 0.99 ?
C10 C30 . 1.375(6) ?
C10 C11 . 1.400(6) ?
C11 C12 . 1.394(8) ?
C11 H21 . 0.95 ?
C12 C13 . 1.375(9) ?
C12 H20 . 0.95 ?
C13 C29 . 1.374(7) ?
C13 H1 . 0.95 ?
C14 C15 . 1.374(6) ?
C14 C36 . 1.519(5) ?
C15 C31 . 1.434(5) ?
C15 C16 . 1.515(5) ?
C16 C24 . 1.536(5) ?
C16 H29 . 1.0 ?
C17 C18 . 1.510(5) ?
C17 H11 . 0.99 ?
C17 H5 . 0.99 ?
C18 C23 . 1.386(6) ?
C18 C19 . 1.399(5) ?
C19 C20 . 1.402(6) ?
C19 H6 . 0.95 ?
C20 C21 . 1.364(7) ?
C20 H10 . 0.95 ?
C21 C22 . 1.388(7) ?
C21 H7 . 0.95 ?
C22 C23 . 1.381(6) ?
C22 H9 . 0.95 ?
C23 H8 . 0.95 ?
C24 C25 . 1.561(5) ?
C25 C28 . 1.497(5) ?
C25 C26 . 1.568(5) ?
C25 H24 . 1.0 ?
C26 C27 . 1.524(6) ?
C26 H14 . 0.99 ?
C26 H13 . 0.99 ?
C27 H23 . 0.99 ?
C27 H22 . 0.99 ?
C29 C30 . 1.402(6) ?
C29 H18 . 0.95 ?
C30 H19 . 0.95 ?
C31 C32 . 1.513(5) ?
C32 C33 . 1.526(6) ?
C32 H31 . 0.99 ?
C32 H30 . 0.99 ?
C33 C35 . 1.528(5) ?
C33 C36 . 1.534(6) ?
C33 C34 . 1.539(5) ?
C34 H32 . 0.98 ?
C34 H34 . 0.98 ?
C34 H33 . 0.98 ?
C35 H35 . 0.98 ?
C35 H37 . 0.98 ?
C35 H36 . 0.98 ?
C36 H39 . 0.99 ?
C36 H38 . 0.99 ?
C37 C38 . 1.383(5) ?
C37 H41 . 0.95 ?
C38 H40 . 0.95 ?
C40 H47 . 0.98 ?
C40 H46 . 0.98 ?
C40 H43 . 0.98 ?
C41 H50 . 0.98 ?
C41 H49 . 0.98 ?
C41 H48 . 0.98 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N4 O1 H25 . . 109.5 ?
N5 O2 H26 . . 109.5 ?
C41 O4 H44 . . 109.5 ?
C14 N1 C4 . . 122.9(3) ?
C14 N1 C5 . . 120.4(3) ?
C4 N1 C5 . . 116.6(3) ?
C5 N2 C17 . . 112.4(3) ?
C5 N2 C6 . . 114.1(3) ?
C17 N2 C6 . . 110.2(3) ?
C9 N3 C27 . . 111.5(3) ?
C9 N3 C8 . . 112.2(3) ?
C27 N3 C8 . . 112.6(3) ?
C28 N4 O1 . . 111.7(3) ?
O2 N5 C24 . . 108.1(3) ?
O2 N5 H42 . . 126.0 ?
C24 N5 H42 . . 126.0 ?
C40 O5 H45 . . 109.5 ?
C2 C1 C38 . . 122.1(4) ?
C2 C1 Br1 . . 118.0(3) ?
C38 C1 Br1 . . 119.8(3) ?
C3 C2 C1 . . 119.0(3) ?
C3 C2 H2 . . 120.5 ?
C1 C2 H2 . . 120.5 ?
C2 C3 C4 . . 120.2(3) ?
C2 C3 H3 . . 119.9 ?
C4 C3 H3 . . 119.9 ?
C37 C4 C3 . . 119.9(3) ?
C37 C4 N1 . . 119.4(3) ?
C3 C4 N1 . . 120.6(3) ?
N2 C5 N1 . . 113.1(3) ?
N2 C5 C24 . . 111.6(3) ?
N1 C5 C24 . . 108.6(3) ?
N2 C5 H12 . . 107.8 ?
N1 C5 H12 . . 107.8 ?
C24 C5 H12 . . 107.8 ?
N2 C6 C7 . . 111.7(3) ?
N2 C6 H4 . . 109.3 ?
C7 C6 H4 . . 109.3 ?
N2 C6 H27 . . 109.3 ?
C7 C6 H27 . . 109.3 ?
H4 C6 H27 . . 107.9 ?
C6 C7 C16 . . 109.9(3) ?
C6 C7 C8 . . 110.7(3) ?
C16 C7 C8 . . 110.5(3) ?
C6 C7 H28 . . 108.5 ?
C16 C7 H28 . . 108.5 ?
C8 C7 H28 . . 108.5 ?
N3 C8 C28 . . 108.4(3) ?
N3 C8 C7 . . 110.0(3) ?
C28 C8 C7 . . 109.2(3) ?
N3 C8 H15 . . 109.7 ?
C28 C8 H15 . . 109.7 ?
C7 C8 H15 . . 109.7 ?
N3 C9 C10 . . 112.6(3) ?
N3 C9 H17 . . 109.1 ?
C10 C9 H17 . . 109.1 ?
N3 C9 H16 . . 109.1 ?
C10 C9 H16 . . 109.1 ?
H17 C9 H16 . . 107.8 ?
C30 C10 C11 . . 118.0(4) ?
C30 C10 C9 . . 121.5(4) ?
C11 C10 C9 . . 120.3(4) ?
C12 C11 C10 . . 120.2(5) ?
C12 C11 H21 . . 119.9 ?
C10 C11 H21 . . 119.9 ?
C13 C12 C11 . . 120.6(5) ?
C13 C12 H20 . . 119.7 ?
C11 C12 H20 . . 119.7 ?
C29 C13 C12 . . 120.1(5) ?
C29 C13 H1 . . 120.0 ?
C12 C13 H1 . . 120.0 ?
N1 C14 C15 . . 121.2(3) ?
N1 C14 C36 . . 117.6(3) ?
C15 C14 C36 . . 121.2(3) ?
C14 C15 C31 . . 121.2(3) ?
C14 C15 C16 . . 120.8(3) ?
C31 C15 C16 . . 118.0(3) ?
C15 C16 C24 . . 109.8(3) ?
C15 C16 C7 . . 112.8(3) ?
C24 C16 C7 . . 107.0(3) ?
C15 C16 H29 . . 109.0 ?
C24 C16 H29 . . 109.0 ?
C7 C16 H29 . . 109.0 ?
N2 C17 C18 . . 113.4(3) ?
N2 C17 H11 . . 108.9 ?
C18 C17 H11 . . 108.9 ?
N2 C17 H5 . . 108.9 ?
C18 C17 H5 . . 108.9 ?
H11 C17 H5 . . 107.7 ?
C23 C18 C19 . . 118.7(4) ?
C23 C18 C17 . . 121.6(3) ?
C19 C18 C17 . . 119.7(4) ?
C18 C19 C20 . . 120.0(4) ?
C18 C19 H6 . . 120.0 ?
C20 C19 H6 . . 120.0 ?
C21 C20 C19 . . 120.4(4) ?
C21 C20 H10 . . 119.8 ?
C19 C20 H10 . . 119.8 ?
C20 C21 C22 . . 119.8(4) ?
C20 C21 H7 . . 120.1 ?
C22 C21 H7 . . 120.1 ?
C23 C22 C21 . . 120.4(4) ?
C23 C22 H9 . . 119.8 ?
C21 C22 H9 . . 119.8 ?
C22 C23 C18 . . 120.7(4) ?
C22 C23 H8 . . 119.6 ?
C18 C23 H8 . . 119.6 ?
N5 C24 C16 . . 108.8(3) ?
N5 C24 C5 . . 108.0(3) ?
C16 C24 C5 . . 105.3(3) ?
N5 C24 C25 . . 110.9(3) ?
C16 C24 C25 . . 111.8(3) ?
C5 C24 C25 . . 111.9(3) ?
C28 C25 C24 . . 111.3(3) ?
C28 C25 C26 . . 104.5(3) ?
C24 C25 C26 . . 111.8(3) ?
C28 C25 H24 . . 109.7 ?
C24 C25 H24 . . 109.7 ?
C26 C25 H24 . . 109.7 ?
C27 C26 C25 . . 112.7(3) ?
C27 C26 H14 . . 109.0 ?
C25 C26 H14 . . 109.0 ?
C27 C26 H13 . . 109.0 ?
C25 C26 H13 . . 109.0 ?
H14 C26 H13 . . 107.8 ?
N3 C27 C26 . . 111.5(3) ?
N3 C27 H23 . . 109.3 ?
C26 C27 H23 . . 109.3 ?
N3 C27 H22 . . 109.3 ?
C26 C27 H22 . . 109.3 ?
H23 C27 H22 . . 108.0 ?
N4 C28 C25 . . 127.5(3) ?
N4 C28 C8 . . 120.1(3) ?
C25 C28 C8 . . 111.7(3) ?
C13 C29 C30 . . 119.2(5) ?
C13 C29 H18 . . 120.4 ?
C30 C29 H18 . . 120.4 ?
C10 C30 C29 . . 121.9(4) ?
C10 C30 H19 . . 119.1 ?
C29 C30 H19 . . 119.1 ?
O3 C31 C15 . . 121.9(3) ?
O3 C31 C32 . . 119.7(3) ?
C15 C31 C32 . . 118.4(3) ?
C31 C32 C33 . . 113.2(3) ?
C31 C32 H31 . . 108.9 ?
C33 C32 H31 . . 108.9 ?
C31 C32 H30 . . 108.9 ?
C33 C32 H30 . . 108.9 ?
H31 C32 H30 . . 107.8 ?
C32 C33 C35 . . 109.6(3) ?
C32 C33 C36 . . 107.5(3) ?
C35 C33 C36 . . 109.6(3) ?
C32 C33 C34 . . 111.2(4) ?
C35 C33 C34 . . 108.8(3) ?
C36 C33 C34 . . 110.0(3) ?
C33 C34 H32 . . 109.5 ?
C33 C34 H34 . . 109.5 ?
H32 C34 H34 . . 109.5 ?
C33 C34 H33 . . 109.5 ?
H32 C34 H33 . . 109.5 ?
H34 C34 H33 . . 109.5 ?
C33 C35 H35 . . 109.5 ?
C33 C35 H37 . . 109.5 ?
H35 C35 H37 . . 109.5 ?
C33 C35 H36 . . 109.5 ?
H35 C35 H36 . . 109.5 ?
H37 C35 H36 . . 109.5 ?
C14 C36 C33 . . 112.2(3) ?
C14 C36 H39 . . 109.2 ?
C33 C36 H39 . . 109.2 ?
C14 C36 H38 . . 109.2 ?
C33 C36 H38 . . 109.2 ?
H39 C36 H38 . . 107.9 ?
C38 C37 C4 . . 120.0(3) ?
C38 C37 H41 . . 120.0 ?
C4 C37 H41 . . 120.0 ?
C37 C38 C1 . . 118.9(3) ?
C37 C38 H40 . . 120.6 ?
C1 C38 H40 . . 120.6 ?
O5 C40 H47 . . 109.5 ?
O5 C40 H46 . . 109.5 ?
H47 C40 H46 . . 109.5 ?
O5 C40 H43 . . 109.5 ?
H47 C40 H43 . . 109.5 ?
H46 C40 H43 . . 109.5 ?
O4 C41 H50 . . 109.5 ?
O4 C41 H49 . . 109.5 ?
H50 C41 H49 . . 109.5 ?
O4 C41 H48 . . 109.5 ?
H50 C41 H48 . . 109.5 ?
H49 C41 H48 . . 109.5 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C38 C1 C2 C3 . . . . 1.8(6) ?
Br1 C1 C2 C3 . . . . -174.3(3) ?
C1 C2 C3 C4 . . . . -1.1(6) ?
C2 C3 C4 C37 . . . . -0.1(6) ?
C2 C3 C4 N1 . . . . 178.5(3) ?
C14 N1 C4 C37 . . . . -117.7(4) ?
C5 N1 C4 C37 . . . . 58.3(4) ?
C14 N1 C4 C3 . . . . 63.7(5) ?
C5 N1 C4 C3 . . . . -120.3(4) ?
C17 N2 C5 N1 . . . . -59.5(4) ?
C6 N2 C5 N1 . . . . 66.8(4) ?
C17 N2 C5 C24 . . . . 177.7(3) ?
C6 N2 C5 C24 . . . . -56.0(4) ?
C14 N1 C5 N2 . . . . -89.1(4) ?
C4 N1 C5 N2 . . . . 94.8(3) ?
C14 N1 C5 C24 . . . . 35.4(4) ?
C4 N1 C5 C24 . . . . -140.7(3) ?
C5 N2 C6 C7 . . . . 50.2(4) ?
C17 N2 C6 C7 . . . . 177.6(3) ?
N2 C6 C7 C16 . . . . -52.9(4) ?
N2 C6 C7 C8 . . . . 69.5(4) ?
C9 N3 C8 C28 . . . . 128.9(3) ?
C27 N3 C8 C28 . . . . 2.2(4) ?
C9 N3 C8 C7 . . . . -111.7(3) ?
C27 N3 C8 C7 . . . . 121.5(3) ?
C6 C7 C8 N3 . . . . -179.1(3) ?
C16 C7 C8 N3 . . . . -57.0(4) ?
C6 C7 C8 C28 . . . . -60.3(4) ?
C16 C7 C8 C28 . . . . 61.8(4) ?
C27 N3 C9 C10 . . . . -157.5(3) ?
C8 N3 C9 C10 . . . . 75.2(4) ?
N3 C9 C10 C30 . . . . 42.4(5) ?
N3 C9 C10 C11 . . . . -143.2(4) ?
C30 C10 C11 C12 . . . . 2.4(6) ?
C9 C10 C11 C12 . . . . -172.2(4) ?
C10 C11 C12 C13 . . . . -0.5(7) ?
C11 C12 C13 C29 . . . . -1.4(8) ?
C4 N1 C14 C15 . . . . 175.6(3) ?
C5 N1 C14 C15 . . . . -0.2(5) ?
C4 N1 C14 C36 . . . . -2.8(5) ?
C5 N1 C14 C36 . . . . -178.7(3) ?
N1 C14 C15 C31 . . . . 178.0(3) ?
C36 C14 C15 C31 . . . . -3.7(5) ?
N1 C14 C15 C16 . . . . -5.1(5) ?
C36 C14 C15 C16 . . . . 173.3(3) ?
C14 C15 C16 C24 . . . . -25.8(4) ?
C31 C15 C16 C24 . . . . 151.3(3) ?
C14 C15 C16 C7 . . . . 93.6(4) ?
C31 C15 C16 C7 . . . . -89.4(4) ?
C6 C7 C16 C15 . . . . -58.9(4) ?
C8 C7 C16 C15 . . . . 178.6(3) ?
C6 C7 C16 C24 . . . . 62.0(3) ?
C8 C7 C16 C24 . . . . -60.5(4) ?
C5 N2 C17 C18 . . . . -165.0(3) ?
C6 N2 C17 C18 . . . . 66.5(4) ?
N2 C17 C18 C23 . . . . 46.9(5) ?
N2 C17 C18 C19 . . . . -135.8(4) ?
C23 C18 C19 C20 . . . . 1.6(6) ?
C17 C18 C19 C20 . . . . -175.7(4) ?
C18 C19 C20 C21 . . . . -2.3(7) ?
C19 C20 C21 C22 . . . . 1.0(7) ?
C20 C21 C22 C23 . . . . 1.0(7) ?
C21 C22 C23 C18 . . . . -1.6(7) ?
C19 C18 C23 C22 . . . . 0.3(6) ?
C17 C18 C23 C22 . . . . 177.6(4) ?
O2 N5 C24 C16 . . . . -168.6(3) ?
O2 N5 C24 C5 . . . . 77.5(3) ?
O2 N5 C24 C25 . . . . -45.3(4) ?
C15 C16 C24 N5 . . . . -57.8(4) ?
C7 C16 C24 N5 . . . . 179.4(3) ?
C15 C16 C24 C5 . . . . 57.8(3) ?
C7 C16 C24 C5 . . . . -65.0(3) ?
C15 C16 C24 C25 . . . . 179.5(3) ?
C7 C16 C24 C25 . . . . 56.7(3) ?
N2 C5 C24 N5 . . . . 179.0(3) ?
N1 C5 C24 N5 . . . . 53.6(3) ?
N2 C5 C24 C16 . . . . 62.8(3) ?
N1 C5 C24 C16 . . . . -62.5(3) ?
N2 C5 C24 C25 . . . . -58.8(3) ?
N1 C5 C24 C25 . . . . 175.9(3) ?
N5 C24 C25 C28 . . . . -176.6(3) ?
C16 C24 C25 C28 . . . . -55.0(4) ?
C5 C24 C25 C28 . . . . 62.8(4) ?
N5 C24 C25 C26 . . . . -60.2(4) ?
C16 C24 C25 C26 . . . . 61.4(4) ?
C5 C24 C25 C26 . . . . 179.2(3) ?
C28 C25 C26 C27 . . . . 9.6(4) ?
C24 C25 C26 C27 . . . . -110.9(3) ?
C9 N3 C27 C26 . . . . 177.3(3) ?
C8 N3 C27 C26 . . . . -55.5(4) ?
C25 C26 C27 N3 . . . . 48.9(4) ?
O1 N4 C28 C25 . . . . 3.1(5) ?
O1 N4 C28 C8 . . . . 172.8(3) ?
C24 C25 C28 N4 . . . . -134.5(4) ?
C26 C25 C28 N4 . . . . 104.7(4) ?
C24 C25 C28 C8 . . . . 55.0(4) ?
C26 C25 C28 C8 . . . . -65.8(3) ?
N3 C8 C28 N4 . . . . -109.7(4) ?
C7 C8 C28 N4 . . . . 130.4(3) ?
N3 C8 C28 C25 . . . . 61.5(4) ?
C7 C8 C28 C25 . . . . -58.3(4) ?
C12 C13 C29 C30 . . . . 1.2(7) ?
C11 C10 C30 C29 . . . . -2.6(6) ?
C9 C10 C30 C29 . . . . 171.9(4) ?
C13 C29 C30 C10 . . . . 0.8(6) ?
C14 C15 C31 O3 . . . . -177.5(3) ?
C16 C15 C31 O3 . . . . 5.4(5) ?
C14 C15 C31 C32 . . . . 2.0(5) ?
C16 C15 C31 C32 . . . . -175.1(3) ?
O3 C31 C32 C33 . . . . -151.4(4) ?
C15 C31 C32 C33 . . . . 29.1(5) ?
C31 C32 C33 C35 . . . . -174.5(3) ?
C31 C32 C33 C36 . . . . -55.4(4) ?
C31 C32 C33 C34 . . . . 65.1(4) ?
N1 C14 C36 C33 . . . . 153.0(3) ?
C15 C14 C36 C33 . . . . -25.4(5) ?
C32 C33 C36 C14 . . . . 53.1(4) ?
C35 C33 C36 C14 . . . . 172.2(3) ?
C34 C33 C36 C14 . . . . -68.1(4) ?
C3 C4 C37 C38 . . . . 0.7(6) ?
N1 C4 C37 C38 . . . . -178.0(3) ?
C4 C37 C38 C1 . . . . 0.0(6) ?
C2 C1 C38 C37 . . . . -1.3(6) ?
Br1 C1 C38 C37 . . . . 174.8(3) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O1 H25 O3 2_655 0.84 1.83 2.657(4) 167.5 ?
O2 H26 O5 . 0.84 1.93 2.763(5) 174.6 ?
O4 H44 N4 1_455 0.84 2.17 2.877(5) 142.2 ?
O5 H45 O4 . 0.84 1.98 2.821(6) 176.7 ?
C2 H2 O2 4_576 0.95 2.42 3.321(5) 157.6 ?
C3 H3 O1 4_576 0.95 2.66 3.502(4) 148.6 ?
C41 H49 Br1 4_575 0.98 3.09 3.715(6) 122.6 ?

####################################################################### 
# 
# 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_201809377
_database_code_depnum_ccdc_archive 'CCDC 1947690'
loop_
_audit_author_name
_audit_author_address
'Qilin Wang'
;Henan University
China
;
_audit_update_record             
;
2019-08-17 deposited with the CCDC.	2019-12-17 downloaded from the CCDC.
;
_audit_creation_date             2018-09-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C29 H27 Cl N2 O'
_chemical_formula_sum            'C29 H27 Cl N2 O'
_chemical_formula_weight         454.97
_chemical_melting_point          ?
_chemical_oxdiff_formula         C15H15O3N2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   10.8554(2)
_cell_length_b                   18.2505(2)
_cell_length_c                   12.2873(2)
_cell_angle_alpha                90
_cell_angle_beta                 105.0100(10)
_cell_angle_gamma                90
_cell_volume                     2351.26(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6504
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.8490
_cell_measurement_theta_min      4.4320
_shelx_estimated_absorpt_T_max   0.855
_shelx_estimated_absorpt_T_min   0.793
_exptl_absorpt_coefficient_mu    1.619
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92914
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.285
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0306
_diffrn_reflns_av_unetI/netI     0.0227
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            17116
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.066
_diffrn_reflns_theta_max         67.066
_diffrn_reflns_theta_min         4.217
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -68.00  -42.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  178.0000 -120.0000 52

#__ type_ start__ end____ width___ exp.time_
  2 omega -108.00  -75.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  178.0000 -120.0000 66

#__ type_ start__ end____ width___ exp.time_
  3 omega  -77.00  -51.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  178.0000   60.0000 52

#__ type_ start__ end____ width___ exp.time_
  4 omega -100.00  -66.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -77.0000  -60.0000 68

#__ type_ start__ end____ width___ exp.time_
  5 omega   50.00   77.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000   30.0000 54

#__ type_ start__ end____ width___ exp.time_
  6 omega   58.00   83.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000 -180.0000 50

#__ type_ start__ end____ width___ exp.time_
  7 omega  -33.00   57.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -37.0000 -150.0000 180

#__ type_ start__ end____ width___ exp.time_
  8 omega  -33.00    3.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -77.0000  150.0000 72

#__ type_ start__ end____ width___ exp.time_
  9 omega   19.00   55.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   77.0000 -120.0000 72

#__ type_ start__ end____ width___ exp.time_
 10 omega  -33.00   55.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -77.0000 -180.0000 176

#__ type_ start__ end____ width___ exp.time_
 11 omega    8.00   37.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   77.0000 -150.0000 58

#__ type_ start__ end____ width___ exp.time_
 12 omega   -3.00   25.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000   30.0000 56

#__ type_ start__ end____ width___ exp.time_
 13 omega  -31.00   26.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -77.0000   60.0000 114

#__ type_ start__ end____ width___ exp.time_
 14 omega   58.00  108.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000 -150.0000 100

#__ type_ start__ end____ width___ exp.time_
 15 omega   76.00  102.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   57.0000  -90.0000 52

#__ type_ start__ end____ width___ exp.time_
 16 omega   59.00  101.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   77.0000 -150.0000 84

#__ type_ start__ end____ width___ exp.time_
 17 omega   40.00   65.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -77.0000   60.0000 50

#__ type_ start__ end____ width___ exp.time_
 18 omega   23.00   68.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   57.0000   30.0000 90

#__ type_ start__ end____ width___ exp.time_
 19 omega   -1.00   52.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -57.0000 -180.0000 106

#__ type_ start__ end____ width___ exp.time_
 20 omega   38.00   85.00   0.5000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   90.0000 94

#__ type_ start__ end____ width___ exp.time_
 21 omega   40.00   67.00   0.5000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -180.0000 54

#__ type_ start__ end____ width___ exp.time_
 22 omega   65.00   99.00   0.5000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  120.0000 68

#__ type_ start__ end____ width___ exp.time_
 23 omega   70.00  109.00   0.5000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  150.0000 78

#__ type_ start__ end____ width___ exp.time_
 24 omega  107.00  144.00   0.5000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  178.0000  120.0000 74

#__ type_ start__ end____ width___ exp.time_
 25 omega   61.00   97.00   0.5000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  178.0000  120.0000 72

#__ type_ start__ end____ width___ exp.time_
 26 omega   45.00  153.00   0.5000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -15.0000    0.0000 216

#__ type_ start__ end____ width___ exp.time_
 27 omega   55.00  111.00   0.5000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000   90.0000 112

#__ type_ start__ end____ width___ exp.time_
 28 omega   49.00   95.00   0.5000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -150.0000 92

#__ type_ start__ end____ width___ exp.time_
 29 omega   49.00  115.00   0.5000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  -90.0000 132

#__ type_ start__ end____ width___ exp.time_
 30 omega   44.00  131.00   0.5000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000  -30.0000 174

#__ type_ start__ end____ width___ exp.time_
 31 omega   41.00  124.00   0.5000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -61.0000   60.0000 166

#__ type_ start__ end____ width___ exp.time_
 32 omega   96.00  137.00   0.5000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000    0.0000 82

#__ type_ start__ end____ width___ exp.time_
 33 omega   43.00   91.00   0.5000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -120.0000 96

#__ type_ start__ end____ width___ exp.time_
 34 omega   37.00   87.00   0.5000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -30.0000 100

#__ type_ start__ end____ width___ exp.time_
 35 omega   43.00  151.00   0.5000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -15.0000  120.0000 216

#__ type_ start__ end____ width___ exp.time_
 36 omega   79.00  137.00   0.5000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000 -120.0000 116
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0226261000
_diffrn_orient_matrix_UB_12      -0.0808169000
_diffrn_orient_matrix_UB_13      -0.0252511000
_diffrn_orient_matrix_UB_21      0.0588653000
_diffrn_orient_matrix_UB_22      -0.0138223000
_diffrn_orient_matrix_UB_23      0.1264910000
_diffrn_orient_matrix_UB_31      -0.1327522000
_diffrn_orient_matrix_UB_32      -0.0199418000
_diffrn_orient_matrix_UB_33      0.0146024000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3540
_reflns_number_total             4192
_reflns_odcompleteness_completeness 99.98
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.296
_refine_diff_density_min         -0.356
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     299
_refine_ls_number_reflns         4192
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0555
_refine_ls_R_factor_gt           0.0474
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0779P)²+0.3819P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1290
_refine_ls_wR_factor_ref         0.1396
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C20(H20), C22(H22)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C21(H21A,H21B), C23(H23A,H23B)
2.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C11(H11), C12(H12), C14(H14), C16(H16), C17(H17), C25(H25),
 C26(H26), C27(H27), C28(H28), C29(H29)
2.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.42105(17) 0.36319(9) 0.65974(15) 0.0495(4) Uani 1 1 d . . . . .
C2 C 0.29308(18) 0.40142(11) 0.63079(17) 0.0597(5) Uani 1 1 d . . . . .
H2A H 0.2450 0.3858 0.6831 0.072 Uiso 1 1 calc R . . . .
H2B H 0.3064 0.4539 0.6397 0.072 Uiso 1 1 calc R . . . .
C3 C 0.21633(17) 0.38546(12) 0.51183(18) 0.0635(5) Uani 1 1 d . . . . .
H3A H 0.1388 0.4144 0.4947 0.076 Uiso 1 1 calc R . . . .
H3B H 0.1925 0.3341 0.5052 0.076 Uiso 1 1 calc R . . . .
C4 C 0.29354(16) 0.40352(11) 0.42864(16) 0.0577(4) Uani 1 1 d . . . . .
H4A H 0.2464 0.3889 0.3535 0.069 Uiso 1 1 calc R . . . .
H4B H 0.3075 0.4560 0.4281 0.069 Uiso 1 1 calc R . . . .
C5 C 0.42025(15) 0.36459(9) 0.45978(14) 0.0451(4) Uani 1 1 d . . . . .
C6 C 0.47689(15) 0.34495(8) 0.56893(14) 0.0451(4) Uani 1 1 d . . . . .
C7 C 0.43059(14) 0.37969(9) 0.26479(14) 0.0462(4) Uani 1 1 d . . . . .
C8 C 0.43820(17) 0.45425(10) 0.24890(16) 0.0554(4) Uani 1 1 d . . . . .
H8 H 0.4708 0.4847 0.3103 0.066 Uiso 1 1 calc R . . . .
C9 C 0.3975(2) 0.48372(12) 0.14196(18) 0.0645(5) Uani 1 1 d . . . . .
H9 H 0.4024 0.5341 0.1324 0.077 Uiso 1 1 calc R . . . .
C10 C 0.34956(18) 0.43986(13) 0.04899(17) 0.0651(5) Uani 1 1 d . . . . .
C11 C 0.34273(19) 0.36506(13) 0.06613(17) 0.0665(5) Uani 1 1 d . . . . .
H11 H 0.3110 0.3345 0.0047 0.080 Uiso 1 1 calc R . . . .
C12 C 0.38214(17) 0.33494(11) 0.17281(16) 0.0565(4) Uani 1 1 d . . . . .
H12 H 0.3761 0.2847 0.1827 0.068 Uiso 1 1 calc R . . . .
C13 C 0.3059(3) 0.4724(2) -0.0678(2) 0.0989(9) Uani 1 1 d . . . . .
H13A H 0.3191 0.5245 -0.0637 0.148 Uiso 1 1 calc GR . . . .
H13B H 0.2170 0.4622 -0.0986 0.148 Uiso 1 1 calc GR . . . .
H13C H 0.3541 0.4513 -0.1153 0.148 Uiso 1 1 calc GR . . . .
C14 C 0.77009(17) 0.38566(11) 0.71735(15) 0.0554(4) Uani 1 1 d . . . . .
H14 H 0.7364 0.3739 0.7774 0.066 Uiso 1 1 calc R . . . .
C15 C 0.87433(18) 0.43174(12) 0.73463(18) 0.0636(5) Uani 1 1 d . . . . .
C16 C 0.92816(18) 0.44753(11) 0.6480(2) 0.0652(5) Uani 1 1 d . . . . .
H16 H 1.0005 0.4769 0.6607 0.078 Uiso 1 1 calc R . . . .
C17 C 0.87458(17) 0.41959(11) 0.54219(18) 0.0588(4) Uani 1 1 d . . . . .
H17 H 0.9118 0.4302 0.4838 0.071 Uiso 1 1 calc R . . . .
C18 C 0.76530(15) 0.37553(9) 0.52058(14) 0.0472(4) Uani 1 1 d . . . . .
C19 C 0.71521(15) 0.35683(9) 0.61195(14) 0.0464(4) Uani 1 1 d . . . . .
C20 C 0.60264(16) 0.30481(9) 0.59503(14) 0.0474(4) Uani 1 1 d . . . . .
H20 H 0.6114 0.2752 0.6631 0.057 Uiso 1 1 calc R . . . .
C21 C 0.60263(17) 0.25474(9) 0.49588(15) 0.0521(4) Uani 1 1 d . . . . .
H21A H 0.6803 0.2259 0.5113 0.063 Uiso 1 1 calc R . . . .
H21B H 0.5303 0.2216 0.4817 0.063 Uiso 1 1 calc R . . . .
C22 C 0.59410(15) 0.30409(9) 0.39571(14) 0.0479(4) Uani 1 1 d . . . . .
H22 H 0.5892 0.2732 0.3295 0.057 Uiso 1 1 calc R . . . .
C23 C 0.75242(18) 0.36991(11) 0.31662(16) 0.0578(4) Uani 1 1 d . . . . .
H23A H 0.7730 0.4217 0.3225 0.069 Uiso 1 1 calc R . . . .
H23B H 0.6831 0.3632 0.2494 0.069 Uiso 1 1 calc R . . . .
C24 C 0.86749(16) 0.32859(11) 0.30102(16) 0.0556(4) Uani 1 1 d . . . . .
C25 C 0.9206(3) 0.34975(17) 0.2156(2) 0.0854(7) Uani 1 1 d . . . . .
H25 H 0.8871 0.3897 0.1706 0.103 Uiso 1 1 calc R . . . .
C26 C 1.0229(3) 0.3121(3) 0.1962(3) 0.1198(12) Uani 1 1 d . . . . .
H26 H 1.0580 0.3269 0.1383 0.144 Uiso 1 1 calc R . . . .
C27 C 1.0730(3) 0.2535(2) 0.2611(4) 0.1167(13) Uani 1 1 d . . . . .
H27 H 1.1415 0.2280 0.2470 0.140 Uiso 1 1 calc R . . . .
C28 C 1.0226(2) 0.23220(15) 0.3469(3) 0.0959(9) Uani 1 1 d . . . . .
H28 H 1.0572 0.1924 0.3919 0.115 Uiso 1 1 calc R . . . .
C29 C 0.91991(19) 0.26976(12) 0.3672(2) 0.0712(6) Uani 1 1 d . . . . .
H29 H 0.8861 0.2552 0.4260 0.085 Uiso 1 1 calc R . . . .
Cl1 Cl 0.93898(6) 0.46743(5) 0.86881(6) 0.0994(3) Uani 1 1 d . . . . .
N1 N 0.47546(13) 0.34828(8) 0.37505(12) 0.0485(3) Uani 1 1 d . . . . .
N2 N 0.70744(14) 0.34915(9) 0.41348(13) 0.0538(4) Uani 1 1 d . . . . .
O1 O 0.47421(15) 0.34895(8) 0.75889(11) 0.0654(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 1.512(3) . ?
C1 C6 1.440(2) . ?
C1 O1 1.233(2) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.512(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.517(3) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C5 1.507(2) . ?
C5 C6 1.370(2) . ?
C5 N1 1.362(2) . ?
C6 C20 1.509(2) . ?
C7 C8 1.380(3) . ?
C7 C12 1.383(2) . ?
C7 N1 1.435(2) . ?
C8 H8 0.9300 . ?
C8 C9 1.382(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.381(3) . ?
C10 C11 1.386(3) . ?
C10 C13 1.512(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.383(3) . ?
C12 H12 0.9300 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14 0.9300 . ?
C14 C15 1.381(3) . ?
C14 C19 1.382(2) . ?
C15 C16 1.371(3) . ?
C15 Cl1 1.742(2) . ?
C16 H16 0.9300 . ?
C16 C17 1.378(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.400(3) . ?
C18 C19 1.410(2) . ?
C18 N2 1.389(2) . ?
C19 C20 1.519(2) . ?
C20 H20 0.9800 . ?
C20 C21 1.523(2) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C21 C22 1.509(2) . ?
C22 H22 0.9800 . ?
C22 N1 1.485(2) . ?
C22 N2 1.449(2) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C23 C24 1.513(2) . ?
C23 N2 1.449(2) . ?
C24 C25 1.377(3) . ?
C24 C29 1.378(3) . ?
C25 H25 0.9300 . ?
C25 C26 1.378(4) . ?
C26 H26 0.9300 . ?
C26 C27 1.361(6) . ?
C27 H27 0.9300 . ?
C27 C28 1.364(5) . ?
C28 H28 0.9300 . ?
C28 C29 1.385(3) . ?
C29 H29 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 118.02(16) . . ?
O1 C1 C2 119.73(16) . . ?
O1 C1 C6 122.25(17) . . ?
C1 C2 H2A 109.1 . . ?
C1 C2 H2B 109.1 . . ?
H2A C2 H2B 107.9 . . ?
C3 C2 C1 112.41(15) . . ?
C3 C2 H2A 109.1 . . ?
C3 C2 H2B 109.1 . . ?
C2 C3 H3A 109.6 . . ?
C2 C3 H3B 109.6 . . ?
C2 C3 C4 110.34(15) . . ?
H3A C3 H3B 108.1 . . ?
C4 C3 H3A 109.6 . . ?
C4 C3 H3B 109.6 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 108.1 . . ?
C5 C4 C3 110.72(16) . . ?
C5 C4 H4A 109.5 . . ?
C5 C4 H4B 109.5 . . ?
C6 C5 C4 121.37(15) . . ?
N1 C5 C4 117.54(15) . . ?
N1 C5 C6 121.07(14) . . ?
C1 C6 C20 119.14(15) . . ?
C5 C6 C1 121.71(15) . . ?
C5 C6 C20 119.14(14) . . ?
C8 C7 C12 119.37(17) . . ?
C8 C7 N1 120.61(15) . . ?
C12 C7 N1 120.00(16) . . ?
C7 C8 H8 119.9 . . ?
C7 C8 C9 120.13(18) . . ?
C9 C8 H8 119.9 . . ?
C8 C9 H9 119.3 . . ?
C10 C9 C8 121.33(19) . . ?
C10 C9 H9 119.3 . . ?
C9 C10 C11 117.93(19) . . ?
C9 C10 C13 121.0(2) . . ?
C11 C10 C13 121.0(2) . . ?
C10 C11 H11 119.3 . . ?
C12 C11 C10 121.32(19) . . ?
C12 C11 H11 119.3 . . ?
C7 C12 H12 120.0 . . ?
C11 C12 C7 119.91(18) . . ?
C11 C12 H12 120.0 . . ?
C10 C13 H13A 109.5 . . ?
C10 C13 H13B 109.5 . . ?
C10 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 C14 H14 119.6 . . ?
C15 C14 C19 120.87(18) . . ?
C19 C14 H14 119.6 . . ?
C14 C15 Cl1 119.09(17) . . ?
C16 C15 C14 120.37(18) . . ?
C16 C15 Cl1 120.52(16) . . ?
C15 C16 H16 120.2 . . ?
C15 C16 C17 119.63(18) . . ?
C17 C16 H16 120.2 . . ?
C16 C17 H17 119.3 . . ?
C16 C17 C18 121.42(18) . . ?
C18 C17 H17 119.3 . . ?
C17 C18 C19 118.06(16) . . ?
N2 C18 C17 122.11(16) . . ?
N2 C18 C19 119.82(15) . . ?
C14 C19 C18 119.50(16) . . ?
C14 C19 C20 120.18(15) . . ?
C18 C19 C20 120.32(15) . . ?
C6 C20 C19 112.17(13) . . ?
C6 C20 H20 109.4 . . ?
C6 C20 C21 107.98(14) . . ?
C19 C20 H20 109.4 . . ?
C19 C20 C21 108.54(14) . . ?
C21 C20 H20 109.4 . . ?
C20 C21 H21A 110.5 . . ?
C20 C21 H21B 110.5 . . ?
H21A C21 H21B 108.6 . . ?
C22 C21 C20 106.35(13) . . ?
C22 C21 H21A 110.5 . . ?
C22 C21 H21B 110.5 . . ?
C21 C22 H22 108.2 . . ?
N1 C22 C21 109.33(13) . . ?
N1 C22 H22 108.2 . . ?
N2 C22 C21 110.22(14) . . ?
N2 C22 H22 108.2 . . ?
N2 C22 N1 112.50(14) . . ?
H23A C23 H23B 107.4 . . ?
C24 C23 H23A 108.3 . . ?
C24 C23 H23B 108.3 . . ?
N2 C23 H23A 108.3 . . ?
N2 C23 H23B 108.3 . . ?
N2 C23 C24 116.01(16) . . ?
C25 C24 C23 118.6(2) . . ?
C25 C24 C29 118.6(2) . . ?
C29 C24 C23 122.81(18) . . ?
C24 C25 H25 119.8 . . ?
C24 C25 C26 120.5(3) . . ?
C26 C25 H25 119.8 . . ?
C25 C26 H26 119.7 . . ?
C27 C26 C25 120.5(3) . . ?
C27 C26 H26 119.7 . . ?
C26 C27 H27 120.1 . . ?
C26 C27 C28 119.8(2) . . ?
C28 C27 H27 120.1 . . ?
C27 C28 H28 120.0 . . ?
C27 C28 C29 120.1(3) . . ?
C29 C28 H28 120.0 . . ?
C24 C29 C28 120.5(3) . . ?
C24 C29 H29 119.7 . . ?
C28 C29 H29 119.7 . . ?
C5 N1 C7 121.69(13) . . ?
C5 N1 C22 121.47(14) . . ?
C7 N1 C22 116.47(13) . . ?
C18 N2 C22 119.84(14) . . ?
C18 N2 C23 121.44(15) . . ?
C22 N2 C23 118.58(15) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 -54.1(2) . . . . ?
C1 C6 C20 C19 -93.62(17) . . . . ?
C1 C6 C20 C21 146.83(15) . . . . ?
C2 C1 C6 C5 3.3(2) . . . . ?
C2 C1 C6 C20 -178.22(14) . . . . ?
C2 C3 C4 C5 54.0(2) . . . . ?
C3 C4 C5 C6 -26.5(2) . . . . ?
C3 C4 C5 N1 152.20(16) . . . . ?
C4 C5 C6 C1 -2.7(2) . . . . ?
C4 C5 C6 C20 178.87(15) . . . . ?
C4 C5 N1 C7 12.9(2) . . . . ?
C4 C5 N1 C22 -174.31(15) . . . . ?
C5 C6 C20 C19 84.89(18) . . . . ?
C5 C6 C20 C21 -34.67(19) . . . . ?
C6 C1 C2 C3 25.6(2) . . . . ?
C6 C5 N1 C7 -168.35(15) . . . . ?
C6 C5 N1 C22 4.4(2) . . . . ?
C6 C20 C21 C22 63.22(17) . . . . ?
C7 C8 C9 C10 -0.5(3) . . . . ?
C8 C7 C12 C11 0.4(3) . . . . ?
C8 C7 N1 C5 64.0(2) . . . . ?
C8 C7 N1 C22 -109.08(18) . . . . ?
C8 C9 C10 C11 0.4(3) . . . . ?
C8 C9 C10 C13 -179.62(19) . . . . ?
C9 C10 C11 C12 0.2(3) . . . . ?
C10 C11 C12 C7 -0.6(3) . . . . ?
C12 C7 C8 C9 0.1(3) . . . . ?
C12 C7 N1 C5 -117.61(18) . . . . ?
C12 C7 N1 C22 69.27(19) . . . . ?
C13 C10 C11 C12 -179.82(19) . . . . ?
C14 C15 C16 C17 2.7(3) . . . . ?
C14 C19 C20 C6 87.95(18) . . . . ?
C14 C19 C20 C21 -152.82(15) . . . . ?
C15 C14 C19 C18 -0.9(3) . . . . ?
C15 C14 C19 C20 178.54(16) . . . . ?
C15 C16 C17 C18 0.4(3) . . . . ?
C16 C17 C18 C19 -3.6(3) . . . . ?
C16 C17 C18 N2 177.61(17) . . . . ?
C17 C18 C19 C14 3.8(2) . . . . ?
C17 C18 C19 C20 -175.62(15) . . . . ?
C17 C18 N2 C22 -179.67(15) . . . . ?
C17 C18 N2 C23 -4.2(3) . . . . ?
C18 C19 C20 C6 -92.65(18) . . . . ?
C18 C19 C20 C21 26.58(19) . . . . ?
C19 C14 C15 C16 -2.4(3) . . . . ?
C19 C14 C15 Cl1 179.32(14) . . . . ?
C19 C18 N2 C22 1.6(2) . . . . ?
C19 C18 N2 C23 177.07(15) . . . . ?
C19 C20 C21 C22 -58.60(17) . . . . ?
C20 C21 C22 N1 -59.31(17) . . . . ?
C20 C21 C22 N2 64.85(17) . . . . ?
C21 C22 N1 C5 26.6(2) . . . . ?
C21 C22 N1 C7 -160.30(14) . . . . ?
C21 C22 N2 C18 -36.4(2) . . . . ?
C21 C22 N2 C23 147.95(15) . . . . ?
C23 C24 C25 C26 -177.9(3) . . . . ?
C23 C24 C29 C28 177.7(2) . . . . ?
C24 C23 N2 C18 80.9(2) . . . . ?
C24 C23 N2 C22 -103.56(19) . . . . ?
C24 C25 C26 C27 0.0(5) . . . . ?
C25 C24 C29 C28 -0.9(3) . . . . ?
C25 C26 C27 C28 -0.8(5) . . . . ?
C26 C27 C28 C29 0.6(5) . . . . ?
C27 C28 C29 C24 0.2(4) . . . . ?
C29 C24 C25 C26 0.8(4) . . . . ?
Cl1 C15 C16 C17 -179.12(15) . . . . ?
N1 C5 C6 C1 178.64(14) . . . . ?
N1 C5 C6 C20 0.2(2) . . . . ?
N1 C7 C8 C9 178.47(16) . . . . ?
N1 C7 C12 C11 -177.93(16) . . . . ?
N1 C22 N2 C18 85.89(18) . . . . ?
N1 C22 N2 C23 -89.74(18) . . . . ?
N2 C18 C19 C14 -177.39(15) . . . . ?
N2 C18 C19 C20 3.2(2) . . . . ?
N2 C22 N1 C5 -96.24(18) . . . . ?
N2 C22 N1 C7 76.89(18) . . . . ?
N2 C23 C24 C25 -175.0(2) . . . . ?
N2 C23 C24 C29 6.3(3) . . . . ?
O1 C1 C2 C3 -154.65(17) . . . . ?
O1 C1 C6 C5 -176.38(15) . . . . ?
O1 C1 C6 C20 2.1(2) . . . . ?

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

data_201810415
_database_code_depnum_ccdc_archive 'CCDC 1947693'
loop_
_audit_author_name
_audit_author_address
'Qilin Wang'
;Henan University
China
;
_audit_update_record             
;
2019-08-17 deposited with the CCDC.	2019-12-17 downloaded from the CCDC.
;
_audit_creation_date             2018-10-26
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C46 H42 Br N3 O'
_chemical_formula_sum            'C46 H42 Br N3 O'
_chemical_formula_weight         732.73
_chemical_melting_point          ?
_chemical_oxdiff_formula         C15H15O3N2Br1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   10.2078(3)
_cell_length_b                   19.1520(5)
_cell_length_c                   18.9514(4)
_cell_angle_alpha                90
_cell_angle_beta                 94.804(2)
_cell_angle_gamma                90
_cell_volume                     3691.96(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4592
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.8150
_cell_measurement_theta_min      4.6030
_shelx_estimated_absorpt_T_max   0.839
_shelx_estimated_absorpt_T_min   0.735
_exptl_absorpt_coefficient_mu    1.819
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.318
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1528
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0612
_diffrn_reflns_av_unetI/netI     0.0582
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            14208
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.077
_diffrn_reflns_theta_max         67.077
_diffrn_reflns_theta_min         4.618
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -43.00   20.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   37.0000  150.0000 63

#__ type_ start__ end____ width___ exp.time_
  2 omega -103.00  -30.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -77.0000 -150.0000 73

#__ type_ start__ end____ width___ exp.time_
  3 omega  -57.00  -32.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  178.0000 -180.0000 25

#__ type_ start__ end____ width___ exp.time_
  4 omega -108.00  -76.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  178.0000 -180.0000 32

#__ type_ start__ end____ width___ exp.time_
  5 omega   58.00  109.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000  -90.0000 51

#__ type_ start__ end____ width___ exp.time_
  6 omega   -1.00   81.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   19.0000   30.0000 82

#__ type_ start__ end____ width___ exp.time_
  7 omega    8.00   45.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   77.0000    0.0000 37

#__ type_ start__ end____ width___ exp.time_
  8 omega    1.00   39.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000  -60.0000 38

#__ type_ start__ end____ width___ exp.time_
  9 omega    2.00   49.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000 -120.0000 47

#__ type_ start__ end____ width___ exp.time_
 10 omega   76.00  101.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   77.0000    0.0000 25

#__ type_ start__ end____ width___ exp.time_
 11 omega   75.00  105.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000  150.0000 30

#__ type_ start__ end____ width___ exp.time_
 12 omega   46.00   77.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000  -60.0000 31

#__ type_ start__ end____ width___ exp.time_
 13 omega   40.00   84.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   90.0000 44

#__ type_ start__ end____ width___ exp.time_
 14 omega   57.00  105.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  -30.0000 48

#__ type_ start__ end____ width___ exp.time_
 15 omega   50.00   76.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  120.0000 26

#__ type_ start__ end____ width___ exp.time_
 16 omega  124.00  157.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000 -180.0000 33

#__ type_ start__ end____ width___ exp.time_
 17 omega   45.00   92.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000   60.0000 47

#__ type_ start__ end____ width___ exp.time_
 18 omega   58.00   91.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -180.0000 33

#__ type_ start__ end____ width___ exp.time_
 19 omega   44.00   89.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  150.0000 45

#__ type_ start__ end____ width___ exp.time_
 20 omega   44.00   98.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -120.0000 54

#__ type_ start__ end____ width___ exp.time_
 21 omega   38.00   98.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -60.0000 60

#__ type_ start__ end____ width___ exp.time_
 22 omega  111.00  169.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000  -90.0000 58
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.1391169000
_diffrn_orient_matrix_UB_12      -0.0170584000
_diffrn_orient_matrix_UB_13      -0.0208177000
_diffrn_orient_matrix_UB_21      0.0501147000
_diffrn_orient_matrix_UB_22      -0.0040021000
_diffrn_orient_matrix_UB_23      0.0788750000
_diffrn_orient_matrix_UB_31      -0.0326649000
_diffrn_orient_matrix_UB_32      -0.0785198000
_diffrn_orient_matrix_UB_33      0.0005240000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5036
_reflns_number_total             6586
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         1.014
_refine_diff_density_min         -0.541
_refine_diff_density_rms         0.077
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     473
_refine_ls_number_reflns         6586
_refine_ls_number_restraints     72
_refine_ls_R_factor_all          0.0870
_refine_ls_R_factor_gt           0.0701
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1123P)²+2.5906P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1909
_refine_ls_wR_factor_ref         0.2129
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C45A) \\sim Ueq, Uanis(C44A) \\sim Ueq, Uanis(C44) \\sim Ueq, Uanis(C45)
\\sim Ueq, Uanis(C46) \\sim Ueq, Uanis(C43) \\sim Ueq, Uanis(C43A) \\sim Ueq,
Uanis(C42A) \\sim Ueq, Uanis(C42) \\sim Ueq, Uanis(C41A) \\sim Ueq, Uanis(C41)
\\sim Ueq, Uanis(C46A) \\sim Ueq: with sigma of 0.01 and sigma for terminal
atoms of 0.02
Uanis(C40) = Uanis(C40A)
Uanis(C41) = Uanis(C41A)
Uanis(C46) = Uanis(C46A)
Uanis(C45) = Uanis(C45A)
Uanis(C44) = Uanis(C44A)
Uanis(C43) = Uanis(C43A)
Uanis(C42) = Uanis(C42A)
3. Others
 Sof(C40A)=Sof(H40C)=Sof(H40D)=1-FVAR(1)
 Sof(C40)=Sof(H40A)=Sof(H40B)=FVAR(1)
 Sof(C41A)=Sof(C42A)=Sof(H42A)=Sof(C43A)=Sof(H43A)=Sof(C44A)=Sof(H44A)=
 Sof(C45A)=Sof(H45A)=Sof(C46A)=Sof(H46A)=1-FVAR(2)
 Sof(C41)=Sof(C42)=Sof(H42)=Sof(C43)=Sof(H43)=Sof(C44)=Sof(H44)=Sof(C45)=
 Sof(H45)=Sof(C46)=Sof(H46)=FVAR(2)
4.a Ternary CH refined with riding coordinates:
 C15(H15), C22(H22), C23(H23), C31(H31)
4.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C12(H12A,H12B), C24(H24A,H24B), C40(H40A,H40B), C40A(H40C,H40D)
4.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5), C17(H17), C18(H18), C19(H19), C20(H20),
 C26(H26), C27(H27), C28(H28), C29(H29), C30(H30), C33(H33), C34(H34), C35(H35),
  C36(H36), C38(H38), C39(H39), C42A(H42A), C43A(H43A), C44A(H44A), C45A(H45A),
 C46A(H46A), C42(H42), C43(H43), C44(H44), C45(H45), C46(H46)
4.d Fitted hexagon refined as free rotating group:
 C41A(C42A,C43A,C44A,C45A,C46A)
4.e Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br -0.36009(6) 0.90671(4) 0.70401(3) 0.0917(3) Uani 1 1 d . . . . .
C1 C -0.2227(3) 0.81395(19) 0.5282(2) 0.0452(8) Uani 1 1 d . . . . .
H1 H -0.2328 0.7709 0.5057 0.054 Uiso 1 1 calc R . . . .
C2 C -0.2848(4) 0.8266(2) 0.5890(2) 0.0533(9) Uani 1 1 d . . . . .
H2 H -0.3349 0.7919 0.6081 0.064 Uiso 1 1 calc R . . . .
C3 C -0.2721(4) 0.8904(2) 0.62096(19) 0.0513(9) Uani 1 1 d . . . . .
C4 C -0.1988(4) 0.9419(2) 0.5952(2) 0.0558(10) Uani 1 1 d . . . . .
H4 H -0.1922 0.9853 0.6171 0.067 Uiso 1 1 calc R . . . .
C5 C -0.1336(4) 0.9283(2) 0.5353(2) 0.0482(8) Uani 1 1 d . . . . .
H5 H -0.0805 0.9627 0.5180 0.058 Uiso 1 1 calc R . . . .
C6 C -0.1458(3) 0.86489(17) 0.50060(16) 0.0355(7) Uani 1 1 d . . . . .
C7 C -0.0690(3) 0.89101(18) 0.38386(18) 0.0403(7) Uani 1 1 d . . . . .
C8 C 0.0219(3) 0.87891(18) 0.33594(19) 0.0412(7) Uani 1 1 d . . . . .
C9 C 0.0198(4) 0.9169(2) 0.2705(2) 0.0639(12) Uani 1 1 d . . . . .
C10 C -0.0760(5) 0.9780(2) 0.2602(2) 0.0648(11) Uani 1 1 d . . . . .
H10A H -0.0329 1.0199 0.2791 0.078 Uiso 1 1 calc R . . . .
H10B H -0.0974 0.9851 0.2099 0.078 Uiso 1 1 calc R . . . .
C11 C -0.2014(3) 0.96785(18) 0.29516(18) 0.0422(7) Uani 1 1 d . . . . .
C12 C -0.1704(4) 0.9491(2) 0.3736(2) 0.0536(9) Uani 1 1 d . . . . .
H12A H -0.1376 0.9903 0.3992 0.064 Uiso 1 1 calc R . . . .
H12B H -0.2506 0.9346 0.3934 0.064 Uiso 1 1 calc R . . . .
C13 C -0.2833(5) 0.9083(3) 0.2594(3) 0.0747(14) Uani 1 1 d . . . . .
H13A H -0.3627 0.9025 0.2826 0.112 Uiso 1 1 calc GR . . . .
H13B H -0.2334 0.8658 0.2629 0.112 Uiso 1 1 calc GR . . . .
H13C H -0.3051 0.9195 0.2105 0.112 Uiso 1 1 calc GR . . . .
C14 C -0.2870(5) 1.0325(3) 0.2904(3) 0.0763(15) Uani 1 1 d . . . . .
H14A H -0.3675 1.0232 0.3115 0.115 Uiso 1 1 calc GR . . . .
H14B H -0.3063 1.0450 0.2416 0.115 Uiso 1 1 calc GR . . . .
H14C H -0.2415 1.0702 0.3151 0.115 Uiso 1 1 calc GR . . . .
C15 C 0.1226(3) 0.82176(17) 0.35197(16) 0.0351(7) Uani 1 1 d . . . . .
H15 H 0.1559 0.8059 0.3077 0.042 Uiso 1 1 calc R . . . .
C16 C 0.2354(3) 0.84907(16) 0.40059(17) 0.0359(7) Uani 1 1 d . . . . .
C17 C 0.3363(4) 0.88669(19) 0.3727(2) 0.0475(8) Uani 1 1 d . . . . .
H17 H 0.3375 0.8911 0.3239 0.057 Uiso 1 1 calc R . . . .
C18 C 0.4345(4) 0.9175(2) 0.4168(3) 0.0569(10) Uani 1 1 d . . . . .
H18 H 0.5016 0.9419 0.3975 0.068 Uiso 1 1 calc R . . . .
C19 C 0.4332(4) 0.9122(2) 0.4892(3) 0.0579(11) Uani 1 1 d . . . . .
H19 H 0.4985 0.9335 0.5188 0.069 Uiso 1 1 calc R . . . .
C20 C 0.3335(4) 0.87467(18) 0.5176(2) 0.0479(8) Uani 1 1 d . . . . .
H20 H 0.3324 0.8716 0.5665 0.057 Uiso 1 1 calc R . . . .
C21 C 0.2354(3) 0.84162(16) 0.47442(17) 0.0371(7) Uani 1 1 d . . . . .
C22 C 0.1308(3) 0.79904(15) 0.50634(15) 0.0321(6) Uani 1 1 d . . . . .
H22 H 0.0986 0.8265 0.5450 0.038 Uiso 1 1 calc R . . . .
C23 C 0.0144(3) 0.78617(15) 0.45175(15) 0.0310(6) Uani 1 1 d . . . . .
H23 H -0.0385 0.7485 0.4698 0.037 Uiso 1 1 calc R . . . .
C24 C -0.0418(4) 0.72883(19) 0.33945(18) 0.0435(8) Uani 1 1 d . . . . .
H24A H -0.0115 0.7238 0.2926 0.052 Uiso 1 1 calc R . . . .
H24B H -0.1194 0.7583 0.3355 0.052 Uiso 1 1 calc R . . . .
C25 C -0.0773(3) 0.65819(18) 0.36675(17) 0.0400(7) Uani 1 1 d . . . . .
C26 C 0.0186(4) 0.60650(19) 0.37624(19) 0.0456(8) Uani 1 1 d . . . . .
H26 H 0.1041 0.6158 0.3654 0.055 Uiso 1 1 calc R . . . .
C27 C -0.0125(5) 0.5415(2) 0.4016(2) 0.0588(10) Uani 1 1 d . . . . .
H27 H 0.0521 0.5072 0.4075 0.071 Uiso 1 1 calc R . . . .
C28 C -0.1377(5) 0.5271(2) 0.4183(2) 0.0653(12) Uani 1 1 d . . . . .
H28 H -0.1581 0.4832 0.4353 0.078 Uiso 1 1 calc R . . . .
C29 C -0.2331(4) 0.5778(3) 0.4101(2) 0.0655(12) Uani 1 1 d . . . . .
H29 H -0.3179 0.5682 0.4219 0.079 Uiso 1 1 calc R . . . .
C30 C -0.2032(4) 0.6433(2) 0.3841(2) 0.0519(9) Uani 1 1 d . . . . .
H30 H -0.2683 0.6772 0.3783 0.062 Uiso 1 1 calc R . . . .
C31 C 0.1754(3) 0.72555(16) 0.53763(16) 0.0343(6) Uani 1 1 d . . . . .
H31 H 0.1763 0.6922 0.4985 0.041 Uiso 1 1 calc R . . . .
C32 C 0.0745(3) 0.70161(17) 0.58682(17) 0.0404(7) Uani 1 1 d . . . . .
C33 C -0.0290(4) 0.65703(18) 0.5660(2) 0.0477(8) Uani 1 1 d . . . . .
H33 H -0.0321 0.6354 0.5219 0.057 Uiso 1 1 calc R . . . .
C34 C -0.1281(5) 0.6444(2) 0.6104(3) 0.0667(12) Uani 1 1 d . . . . .
H34 H -0.1976 0.6150 0.5958 0.080 Uiso 1 1 calc R . . . .
C35 C -0.1231(5) 0.6753(3) 0.6754(3) 0.0771(15) Uani 1 1 d . . . . .
H35 H -0.1906 0.6678 0.7046 0.092 Uiso 1 1 calc R . . . .
C36 C -0.0178(6) 0.7181(3) 0.6985(2) 0.0741(14) Uani 1 1 d . . . . .
H36 H -0.0153 0.7386 0.7431 0.089 Uiso 1 1 calc R . . . .
C37 C 0.0843(4) 0.7305(2) 0.65525(19) 0.0528(9) Uani 1 1 d . . . . .
C38 C 0.2066(5) 0.7647(2) 0.6789(2) 0.0630(11) Uani 1 1 d . . . . .
H38 H 0.2118 0.7926 0.7191 0.076 Uiso 1 1 calc R . . . .
C39 C 0.3126(4) 0.7558(2) 0.6423(2) 0.0574(10) Uani 1 1 d . . . . .
H39 H 0.3941 0.7705 0.6624 0.069 Uiso 1 1 calc R . . . .
C40 C 0.4262(5) 0.7119(3) 0.5409(4) 0.0616(15) Uani 0.773(8) 1 d . . P A 1
H40A H 0.4945 0.6965 0.5761 0.074 Uiso 0.773(8) 1 calc R . P A 1
H40B H 0.4554 0.7552 0.5208 0.074 Uiso 0.773(8) 1 calc R . P A 1
C40A C 0.3876(17) 0.6662(10) 0.5679(12) 0.0616(15) Uani 0.227(8) 1 d . . P A 2
H40C H 0.3477 0.6255 0.5878 0.074 Uiso 0.227(8) 1 calc R . P A 2
H40D H 0.4719 0.6739 0.5944 0.074 Uiso 0.227(8) 1 calc R . P A 2
C41 C 0.4103(7) 0.6582(4) 0.4835(4) 0.0518(11) Uani 0.793(7) 1 d . U P A 1
C41A C 0.410(2) 0.6517(11) 0.4928(8) 0.0518(11) Uani 0.207(7) 1 d . U P A 2
C42A C 0.380(2) 0.5872(9) 0.4619(12) 0.0610(15) Uani 0.207(7) 1 d G U P A 2
H42A H 0.3524 0.5506 0.4893 0.073 Uiso 0.207(7) 1 calc R . P A 2
C43A C 0.391(2) 0.5774(9) 0.3900(12) 0.0703(17) Uani 0.207(7) 1 d G U P A 2
H43A H 0.3715 0.5343 0.3693 0.084 Uiso 0.207(7) 1 calc R . P A 2
C44A C 0.433(2) 0.6322(12) 0.3490(9) 0.0774(18) Uani 0.207(7) 1 d G U P A 2
H44A H 0.4403 0.6256 0.3009 0.093 Uiso 0.207(7) 1 calc R . P A 2
C45A C 0.4623(18) 0.6967(9) 0.3800(9) 0.082(2) Uani 0.207(7) 1 d G U P A 2
H45A H 0.4899 0.7333 0.3525 0.098 Uiso 0.207(7) 1 calc R . P A 2
C46A C 0.4509(19) 0.7064(8) 0.4519(10) 0.0700(17) Uani 0.207(7) 1 d G U P A 2
H46A H 0.4708 0.7496 0.4726 0.084 Uiso 0.207(7) 1 calc R . P A 2
C42 C 0.3903(6) 0.5886(3) 0.5000(4) 0.0610(15) Uani 0.793(7) 1 d . U P A 1
H42 H 0.3877 0.5749 0.5470 0.073 Uiso 0.793(7) 1 calc R . P A 1
C43 C 0.3741(6) 0.5399(3) 0.4459(4) 0.0703(17) Uani 0.793(7) 1 d . U P A 1
H43 H 0.3596 0.4934 0.4574 0.084 Uiso 0.793(7) 1 calc R . P A 1
C44 C 0.3788(7) 0.5575(4) 0.3767(4) 0.0774(18) Uani 0.793(7) 1 d . U P A 1
H44 H 0.3681 0.5238 0.3414 0.093 Uiso 0.793(7) 1 calc R . P A 1
C45 C 0.3995(7) 0.6255(5) 0.3604(4) 0.082(2) Uani 0.793(7) 1 d . U P A 1
H45 H 0.4034 0.6383 0.3133 0.098 Uiso 0.793(7) 1 calc R . P A 1
C46 C 0.4150(6) 0.6765(3) 0.4133(4) 0.0700(17) Uani 0.793(7) 1 d . U P A 1
H46 H 0.4285 0.7228 0.4011 0.084 Uiso 0.793(7) 1 calc R . P A 1
N1 N -0.0722(3) 0.84935(14) 0.44203(14) 0.0365(6) Uani 1 1 d . . . . .
N2 N 0.0611(2) 0.76250(13) 0.38629(13) 0.0329(5) Uani 1 1 d . . . . .
N3 N 0.3051(3) 0.72575(16) 0.57641(16) 0.0450(7) Uani 1 1 d . . . . .
O1 O 0.0948(4) 0.9028(2) 0.22473(19) 0.0924(14) 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 1.902(4) . ?
C1 H1 0.9300 . ?
C1 C2 1.383(5) . ?
C1 C6 1.382(5) . ?
C2 H2 0.9300 . ?
C2 C3 1.364(6) . ?
C3 C4 1.354(6) . ?
C4 H4 0.9300 . ?
C4 C5 1.388(5) . ?
C5 H5 0.9300 . ?
C5 C6 1.382(5) . ?
C6 N1 1.423(4) . ?
C7 C8 1.372(5) . ?
C7 C12 1.521(5) . ?
C7 N1 1.363(4) . ?
C8 C9 1.436(5) . ?
C8 C15 1.515(4) . ?
C9 C10 1.527(6) . ?
C9 O1 1.234(5) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.502(6) . ?
C11 C12 1.537(5) . ?
C11 C13 1.537(6) . ?
C11 C14 1.513(5) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15 0.9800 . ?
C15 C16 1.507(5) . ?
C15 N2 1.474(4) . ?
C16 C17 1.396(5) . ?
C16 C21 1.406(5) . ?
C17 H17 0.9300 . ?
C17 C18 1.382(6) . ?
C18 H18 0.9300 . ?
C18 C19 1.376(7) . ?
C19 H19 0.9300 . ?
C19 C20 1.391(6) . ?
C20 H20 0.9300 . ?
C20 C21 1.391(5) . ?
C21 C22 1.510(4) . ?
C22 H22 0.9800 . ?
C22 C23 1.529(4) . ?
C22 C31 1.580(4) . ?
C23 H23 0.9800 . ?
C23 N1 1.501(4) . ?
C23 N2 1.439(4) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C24 C25 1.504(5) . ?
C24 N2 1.467(4) . ?
C25 C26 1.394(5) . ?
C25 C30 1.383(5) . ?
C26 H26 0.9300 . ?
C26 C27 1.381(6) . ?
C27 H27 0.9300 . ?
C27 C28 1.371(7) . ?
C28 H28 0.9300 . ?
C28 C29 1.374(7) . ?
C29 H29 0.9300 . ?
C29 C30 1.391(6) . ?
C30 H30 0.9300 . ?
C31 H31 0.9800 . ?
C31 C32 1.517(5) . ?
C31 N3 1.459(4) . ?
C32 C33 1.390(5) . ?
C32 C37 1.406(5) . ?
C33 H33 0.9300 . ?
C33 C34 1.390(6) . ?
C34 H34 0.9300 . ?
C34 C35 1.364(8) . ?
C35 H35 0.9300 . ?
C35 C36 1.392(8) . ?
C36 H36 0.9300 . ?
C36 C37 1.399(6) . ?
C37 C38 1.446(7) . ?
C38 H38 0.9300 . ?
C38 C39 1.344(7) . ?
C39 H39 0.9300 . ?
C39 N3 1.371(5) . ?
C40 H40A 0.9700 . ?
C40 H40B 0.9700 . ?
C40 C41 1.496(9) . ?
C40 N3 1.481(6) . ?
C40A H40C 0.9700 . ?
C40A H40D 0.9700 . ?
C40A C41A 1.49(3) . ?
C40A N3 1.436(18) . ?
C41 C42 1.387(8) . ?
C41 C46 1.380(10) . ?
C41A C42A 1.3900 . ?
C41A C46A 1.3900 . ?
C42A H42A 0.9300 . ?
C42A C43A 1.3900 . ?
C43A H43A 0.9300 . ?
C43A C44A 1.3900 . ?
C44A H44A 0.9300 . ?
C44A C45A 1.3900 . ?
C45A H45A 0.9300 . ?
C45A C46A 1.3900 . ?
C46A H46A 0.9300 . ?
C42 H42 0.9300 . ?
C42 C43 1.387(9) . ?
C43 H43 0.9300 . ?
C43 C44 1.359(11) . ?
C44 H44 0.9300 . ?
C44 C45 1.359(11) . ?
C45 H45 0.9300 . ?
C45 C46 1.400(11) . ?
C46 H46 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 H1 119.8 . . ?
C6 C1 H1 119.8 . . ?
C6 C1 C2 120.4(4) . . ?
C1 C2 H2 120.2 . . ?
C3 C2 C1 119.6(4) . . ?
C3 C2 H2 120.2 . . ?
C2 C3 Br1 118.7(3) . . ?
C4 C3 Br1 119.5(3) . . ?
C4 C3 C2 121.8(3) . . ?
C3 C4 H4 120.8 . . ?
C3 C4 C5 118.4(4) . . ?
C5 C4 H4 120.8 . . ?
C4 C5 H5 119.2 . . ?
C6 C5 C4 121.6(3) . . ?
C6 C5 H5 119.2 . . ?
C1 C6 N1 120.1(3) . . ?
C5 C6 C1 118.2(3) . . ?
C5 C6 N1 121.5(3) . . ?
C8 C7 C12 122.0(3) . . ?
N1 C7 C8 120.0(3) . . ?
N1 C7 C12 118.0(3) . . ?
C7 C8 C9 121.6(3) . . ?
C7 C8 C15 118.4(3) . . ?
C9 C8 C15 120.0(3) . . ?
C8 C9 C10 117.4(3) . . ?
O1 C9 C8 122.1(4) . . ?
O1 C9 C10 120.5(4) . . ?
C9 C10 H10A 108.8 . . ?
C9 C10 H10B 108.8 . . ?
H10A C10 H10B 107.7 . . ?
C11 C10 C9 113.9(3) . . ?
C11 C10 H10A 108.8 . . ?
C11 C10 H10B 108.8 . . ?
C10 C11 C12 110.0(3) . . ?
C10 C11 C13 110.7(4) . . ?
C10 C11 C14 112.1(3) . . ?
C12 C11 C13 108.3(3) . . ?
C14 C11 C12 108.7(3) . . ?
C14 C11 C13 106.9(4) . . ?
C7 C12 C11 112.2(3) . . ?
C7 C12 H12A 109.2 . . ?
C7 C12 H12B 109.2 . . ?
C11 C12 H12A 109.2 . . ?
C11 C12 H12B 109.2 . . ?
H12A C12 H12B 107.9 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C8 C15 H15 109.3 . . ?
C16 C15 C8 110.0(3) . . ?
C16 C15 H15 109.3 . . ?
N2 C15 C8 109.7(3) . . ?
N2 C15 H15 109.3 . . ?
N2 C15 C16 109.2(2) . . ?
C17 C16 C15 119.9(3) . . ?
C17 C16 C21 119.4(3) . . ?
C21 C16 C15 120.6(3) . . ?
C16 C17 H17 119.6 . . ?
C18 C17 C16 120.8(4) . . ?
C18 C17 H17 119.6 . . ?
C17 C18 H18 119.9 . . ?
C19 C18 C17 120.3(4) . . ?
C19 C18 H18 119.9 . . ?
C18 C19 H19 120.3 . . ?
C18 C19 C20 119.5(4) . . ?
C20 C19 H19 120.3 . . ?
C19 C20 H20 119.3 . . ?
C19 C20 C21 121.4(4) . . ?
C21 C20 H20 119.3 . . ?
C16 C21 C22 120.8(3) . . ?
C20 C21 C16 118.6(3) . . ?
C20 C21 C22 120.6(3) . . ?
C21 C22 H22 107.6 . . ?
C21 C22 C23 110.6(2) . . ?
C21 C22 C31 116.1(3) . . ?
C23 C22 H22 107.6 . . ?
C23 C22 C31 107.1(2) . . ?
C31 C22 H22 107.6 . . ?
C22 C23 H23 107.5 . . ?
N1 C23 C22 111.7(2) . . ?
N1 C23 H23 107.5 . . ?
N2 C23 C22 109.8(2) . . ?
N2 C23 H23 107.5 . . ?
N2 C23 N1 112.5(2) . . ?
H24A C24 H24B 108.0 . . ?
C25 C24 H24A 109.3 . . ?
C25 C24 H24B 109.3 . . ?
N2 C24 H24A 109.3 . . ?
N2 C24 H24B 109.3 . . ?
N2 C24 C25 111.6(3) . . ?
C26 C25 C24 119.8(3) . . ?
C30 C25 C24 121.5(3) . . ?
C30 C25 C26 118.7(3) . . ?
C25 C26 H26 119.8 . . ?
C27 C26 C25 120.4(4) . . ?
C27 C26 H26 119.8 . . ?
C26 C27 H27 119.8 . . ?
C28 C27 C26 120.5(4) . . ?
C28 C27 H27 119.8 . . ?
C27 C28 H28 120.1 . . ?
C27 C28 C29 119.9(4) . . ?
C29 C28 H28 120.1 . . ?
C28 C29 H29 119.9 . . ?
C28 C29 C30 120.2(4) . . ?
C30 C29 H29 119.9 . . ?
C25 C30 C29 120.4(4) . . ?
C25 C30 H30 119.8 . . ?
C29 C30 H30 119.8 . . ?
C22 C31 H31 108.5 . . ?
C32 C31 C22 108.1(2) . . ?
C32 C31 H31 108.5 . . ?
N3 C31 C22 114.1(3) . . ?
N3 C31 H31 108.5 . . ?
N3 C31 C32 109.0(3) . . ?
C33 C32 C31 123.4(3) . . ?
C33 C32 C37 119.9(3) . . ?
C37 C32 C31 116.6(3) . . ?
C32 C33 H33 119.7 . . ?
C32 C33 C34 120.5(4) . . ?
C34 C33 H33 119.7 . . ?
C33 C34 H34 120.1 . . ?
C35 C34 C33 119.9(5) . . ?
C35 C34 H34 120.1 . . ?
C34 C35 H35 119.7 . . ?
C34 C35 C36 120.5(4) . . ?
C36 C35 H35 119.7 . . ?
C35 C36 H36 119.7 . . ?
C35 C36 C37 120.7(4) . . ?
C37 C36 H36 119.7 . . ?
C32 C37 C38 117.2(4) . . ?
C36 C37 C32 118.3(4) . . ?
C36 C37 C38 124.1(4) . . ?
C37 C38 H38 120.2 . . ?
C39 C38 C37 119.6(4) . . ?
C39 C38 H38 120.2 . . ?
C38 C39 H39 118.7 . . ?
C38 C39 N3 122.5(4) . . ?
N3 C39 H39 118.7 . . ?
H40A C40 H40B 107.6 . . ?
C41 C40 H40A 108.7 . . ?
C41 C40 H40B 108.7 . . ?
N3 C40 H40A 108.7 . . ?
N3 C40 H40B 108.7 . . ?
N3 C40 C41 114.2(5) . . ?
H40C C40A H40D 107.8 . . ?
C41A C40A H40C 108.9 . . ?
C41A C40A H40D 108.9 . . ?
N3 C40A H40C 108.9 . . ?
N3 C40A H40D 108.9 . . ?
N3 C40A C41A 113.2(17) . . ?
C42 C41 C40 120.3(7) . . ?
C46 C41 C40 121.0(6) . . ?
C46 C41 C42 118.6(7) . . ?
C42A C41A C40A 121.6(14) . . ?
C42A C41A C46A 120.0 . . ?
C46A C41A C40A 118.1(14) . . ?
C41A C42A H42A 120.0 . . ?
C43A C42A C41A 120.0 . . ?
C43A C42A H42A 120.0 . . ?
C42A C43A H43A 120.0 . . ?
C42A C43A C44A 120.0 . . ?
C44A C43A H43A 120.0 . . ?
C43A C44A H44A 120.0 . . ?
C45A C44A C43A 120.0 . . ?
C45A C44A H44A 120.0 . . ?
C44A C45A H45A 120.0 . . ?
C46A C45A C44A 120.0 . . ?
C46A C45A H45A 120.0 . . ?
C41A C46A H46A 120.0 . . ?
C45A C46A C41A 120.0 . . ?
C45A C46A H46A 120.0 . . ?
C41 C42 H42 120.3 . . ?
C43 C42 C41 119.3(7) . . ?
C43 C42 H42 120.3 . . ?
C42 C43 H43 118.8 . . ?
C44 C43 C42 122.3(6) . . ?
C44 C43 H43 118.8 . . ?
C43 C44 H44 120.8 . . ?
C43 C44 C45 118.5(7) . . ?
C45 C44 H44 120.8 . . ?
C44 C45 H45 119.5 . . ?
C44 C45 C46 121.0(7) . . ?
C46 C45 H45 119.5 . . ?
C41 C46 C45 120.2(6) . . ?
C41 C46 H46 119.9 . . ?
C45 C46 H46 119.9 . . ?
C6 N1 C23 114.6(2) . . ?
C7 N1 C6 123.9(3) . . ?
C7 N1 C23 121.2(3) . . ?
C23 N2 C15 108.8(2) . . ?
C23 N2 C24 112.8(3) . . ?
C24 N2 C15 112.4(2) . . ?
C31 N3 C40 121.8(3) . . ?
C39 N3 C31 116.0(3) . . ?
C39 N3 C40 120.3(4) . . ?
C39 N3 C40A 116.6(9) . . ?
C40A N3 C31 117.2(8) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Br1 C3 C4 C5 178.9(3) . . . . ?
C1 C2 C3 Br1 179.3(3) . . . . ?
C1 C2 C3 C4 -0.8(6) . . . . ?
C1 C6 N1 C7 133.2(4) . . . . ?
C1 C6 N1 C23 -52.6(4) . . . . ?
C2 C1 C6 C5 -0.3(5) . . . . ?
C2 C1 C6 N1 174.0(3) . . . . ?
C2 C3 C4 C5 -1.0(6) . . . . ?
C3 C4 C5 C6 2.2(6) . . . . ?
C4 C5 C6 C1 -1.6(6) . . . . ?
C4 C5 C6 N1 -175.7(3) . . . . ?
C5 C6 N1 C7 -52.7(5) . . . . ?
C5 C6 N1 C23 121.4(3) . . . . ?
C6 C1 C2 C3 1.4(6) . . . . ?
C7 C8 C9 C10 7.8(7) . . . . ?
C7 C8 C9 O1 -174.4(5) . . . . ?
C7 C8 C15 C16 -83.0(4) . . . . ?
C7 C8 C15 N2 37.3(4) . . . . ?
C8 C7 C12 C11 26.1(5) . . . . ?
C8 C7 N1 C6 168.3(3) . . . . ?
C8 C7 N1 C23 -5.5(5) . . . . ?
C8 C9 C10 C11 -32.9(6) . . . . ?
C8 C15 C16 C17 -82.3(4) . . . . ?
C8 C15 C16 C21 92.9(3) . . . . ?
C8 C15 N2 C23 -61.0(3) . . . . ?
C8 C15 N2 C24 64.7(3) . . . . ?
C9 C8 C15 C16 99.6(4) . . . . ?
C9 C8 C15 N2 -140.1(4) . . . . ?
C9 C10 C11 C12 52.8(5) . . . . ?
C9 C10 C11 C13 -66.8(5) . . . . ?
C9 C10 C11 C14 173.9(4) . . . . ?
C10 C11 C12 C7 -48.7(5) . . . . ?
C12 C7 C8 C9 -5.1(6) . . . . ?
C12 C7 C8 C15 177.6(3) . . . . ?
C12 C7 N1 C6 -13.1(5) . . . . ?
C12 C7 N1 C23 173.1(3) . . . . ?
C13 C11 C12 C7 72.4(4) . . . . ?
C14 C11 C12 C7 -171.8(4) . . . . ?
C15 C8 C9 C10 -174.8(4) . . . . ?
C15 C8 C9 O1 3.0(8) . . . . ?
C15 C16 C17 C18 174.2(3) . . . . ?
C15 C16 C21 C20 -172.6(3) . . . . ?
C15 C16 C21 C22 7.1(4) . . . . ?
C16 C15 N2 C23 59.7(3) . . . . ?
C16 C15 N2 C24 -174.6(3) . . . . ?
C16 C17 C18 C19 -0.8(6) . . . . ?
C16 C21 C22 C23 -16.1(4) . . . . ?
C16 C21 C22 C31 106.1(3) . . . . ?
C17 C16 C21 C20 2.7(5) . . . . ?
C17 C16 C21 C22 -177.7(3) . . . . ?
C17 C18 C19 C20 1.0(6) . . . . ?
C18 C19 C20 C21 0.7(6) . . . . ?
C19 C20 C21 C16 -2.5(5) . . . . ?
C19 C20 C21 C22 177.8(3) . . . . ?
C20 C21 C22 C23 163.5(3) . . . . ?
C20 C21 C22 C31 -74.2(4) . . . . ?
C21 C16 C17 C18 -1.1(5) . . . . ?
C21 C22 C23 N1 -77.7(3) . . . . ?
C21 C22 C23 N2 47.8(3) . . . . ?
C21 C22 C31 C32 162.1(3) . . . . ?
C21 C22 C31 N3 40.7(4) . . . . ?
C22 C23 N1 C6 -70.3(3) . . . . ?
C22 C23 N1 C7 104.0(3) . . . . ?
C22 C23 N2 C15 -72.3(3) . . . . ?
C22 C23 N2 C24 162.2(2) . . . . ?
C22 C31 C32 C33 95.9(4) . . . . ?
C22 C31 C32 C37 -80.0(3) . . . . ?
C22 C31 N3 C39 74.6(4) . . . . ?
C22 C31 N3 C40 -90.0(4) . . . . ?
C22 C31 N3 C40A -141.2(11) . . . . ?
C23 C22 C31 C32 -73.8(3) . . . . ?
C23 C22 C31 N3 164.8(3) . . . . ?
C24 C25 C26 C27 179.6(3) . . . . ?
C24 C25 C30 C29 -179.2(4) . . . . ?
C25 C24 N2 C15 164.4(3) . . . . ?
C25 C24 N2 C23 -72.2(4) . . . . ?
C25 C26 C27 C28 -0.5(6) . . . . ?
C26 C25 C30 C29 -0.3(5) . . . . ?
C26 C27 C28 C29 -0.2(7) . . . . ?
C27 C28 C29 C30 0.7(7) . . . . ?
C28 C29 C30 C25 -0.4(6) . . . . ?
C30 C25 C26 C27 0.8(5) . . . . ?
C31 C22 C23 N1 154.9(2) . . . . ?
C31 C22 C23 N2 -79.6(3) . . . . ?
C31 C32 C33 C34 -171.3(3) . . . . ?
C31 C32 C37 C36 170.5(3) . . . . ?
C31 C32 C37 C38 -16.1(5) . . . . ?
C32 C31 N3 C39 -46.3(4) . . . . ?
C32 C31 N3 C40 149.1(4) . . . . ?
C32 C31 N3 C40A 97.9(11) . . . . ?
C32 C33 C34 C35 -0.8(6) . . . . ?
C32 C37 C38 C39 -13.2(6) . . . . ?
C33 C32 C37 C36 -5.5(5) . . . . ?
C33 C32 C37 C38 167.8(3) . . . . ?
C33 C34 C35 C36 -1.6(7) . . . . ?
C34 C35 C36 C37 0.4(7) . . . . ?
C35 C36 C37 C32 3.2(7) . . . . ?
C35 C36 C37 C38 -169.7(4) . . . . ?
C36 C37 C38 C39 159.7(4) . . . . ?
C37 C32 C33 C34 4.4(5) . . . . ?
C37 C38 C39 N3 11.9(6) . . . . ?
C38 C39 N3 C31 20.2(5) . . . . ?
C38 C39 N3 C40 -175.0(4) . . . . ?
C38 C39 N3 C40A -124.2(10) . . . . ?
C40 C41 C42 C43 179.2(6) . . . . ?
C40 C41 C46 C45 -179.8(6) . . . . ?
C40A C41A C42A C43A 175(2) . . . . ?
C40A C41A C46A C45A -175(2) . . . . ?
C41 C40 N3 C31 -36.5(6) . . . . ?
C41 C40 N3 C39 159.6(5) . . . . ?
C41 C42 C43 C44 0.8(10) . . . . ?
C41A C40A N3 C31 55.8(17) . . . . ?
C41A C40A N3 C39 -160.2(12) . . . . ?
C41A C42A C43A C44A 0.0 . . . . ?
C42A C41A C46A C45A 0.0 . . . . ?
C42A C43A C44A C45A 0.0 . . . . ?
C43A C44A C45A C46A 0.0 . . . . ?
C44A C45A C46A C41A 0.0 . . . . ?
C46A C41A C42A C43A 0.0 . . . . ?
C42 C41 C46 C45 0.1(9) . . . . ?
C42 C43 C44 C45 -0.3(11) . . . . ?
C43 C44 C45 C46 -0.3(10) . . . . ?
C44 C45 C46 C41 0.4(10) . . . . ?
C46 C41 C42 C43 -0.7(9) . . . . ?
N1 C7 C8 C9 173.5(4) . . . . ?
N1 C7 C8 C15 -3.9(5) . . . . ?
N1 C7 C12 C11 -152.4(3) . . . . ?
N1 C23 N2 C15 52.7(3) . . . . ?
N1 C23 N2 C24 -72.7(3) . . . . ?
N2 C15 C16 C17 157.2(3) . . . . ?
N2 C15 C16 C21 -27.6(4) . . . . ?
N2 C23 N1 C6 165.7(3) . . . . ?
N2 C23 N1 C7 -20.1(4) . . . . ?
N2 C24 C25 C26 -59.6(4) . . . . ?
N2 C24 C25 C30 119.3(4) . . . . ?
N3 C31 C32 C33 -139.6(3) . . . . ?
N3 C31 C32 C37 44.4(4) . . . . ?
N3 C40 C41 C42 -69.0(8) . . . . ?
N3 C40 C41 C46 110.9(7) . . . . ?
N3 C40A C41A C42A -124.0(15) . . . . ?
N3 C40A C41A C46A 51(2) . . . . ?
O1 C9 C10 C11 149.3(5) . . . . ?

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

data_201810620
_database_code_depnum_ccdc_archive 'CCDC 1947688'
loop_
_audit_author_name
_audit_author_address
'Qilin Wang'
;Henan University
China
;
_audit_update_record             
;
2019-08-17 deposited with the CCDC.	2019-12-17 downloaded from the CCDC.
;
_audit_creation_date             2018-10-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C28 H29 N3 O'
_chemical_formula_sum            'C28 H29 N3 O'
_chemical_formula_weight         423.54
_chemical_melting_point          ?
_chemical_oxdiff_formula         C15H15O3N2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   9.0448(4)
_cell_length_b                   14.0503(6)
_cell_length_c                   18.8685(6)
_cell_angle_alpha                90
_cell_angle_beta                 102.053(4)
_cell_angle_gamma                90
_cell_volume                     2344.99(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2345
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.8790
_cell_measurement_theta_min      3.9340
_shelx_estimated_absorpt_T_max   0.929
_shelx_estimated_absorpt_T_min   0.879
_exptl_absorpt_coefficient_mu    0.573
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.200
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             904
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.13
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0370
_diffrn_reflns_av_unetI/netI     0.0425
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            9364
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.065
_diffrn_reflns_theta_max         67.065
_diffrn_reflns_theta_min         3.954
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -46.00    8.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   37.0000  -60.0000 54

#__ type_ start__ end____ width___ exp.time_
  2 omega  -41.00  -13.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   77.0000    0.0000 28

#__ type_ start__ end____ width___ exp.time_
  3 omega   10.00   36.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   77.0000    0.0000 26

#__ type_ start__ end____ width___ exp.time_
  4 omega   38.00   96.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   37.0000  -30.0000 58

#__ type_ start__ end____ width___ exp.time_
  5 omega    9.00   67.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000   60.0000 58

#__ type_ start__ end____ width___ exp.time_
  6 omega  -30.00    2.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -77.0000  -90.0000 32

#__ type_ start__ end____ width___ exp.time_
  7 omega   32.00   64.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   57.0000 -180.0000 32

#__ type_ start__ end____ width___ exp.time_
  8 omega   78.00  108.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000 -180.0000 30

#__ type_ start__ end____ width___ exp.time_
  9 omega   14.00   63.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -77.0000  -90.0000 49

#__ type_ start__ end____ width___ exp.time_
 10 omega   71.00  103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   57.0000 -180.0000 32

#__ type_ start__ end____ width___ exp.time_
 11 omega   57.00   82.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000  -30.0000 25

#__ type_ start__ end____ width___ exp.time_
 12 omega   58.00   87.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000 -120.0000 29

#__ type_ start__ end____ width___ exp.time_
 13 omega   42.00   83.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   90.0000 41

#__ type_ start__ end____ width___ exp.time_
 14 omega  103.00  173.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000   60.0000 70

#__ type_ start__ end____ width___ exp.time_
 15 omega   90.00  177.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000 -120.0000 87

#__ type_ start__ end____ width___ exp.time_
 16 omega   38.00   89.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  120.0000 51

#__ type_ start__ end____ width___ exp.time_
 17 omega  134.00  175.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000  120.0000 41

#__ type_ start__ end____ width___ exp.time_
 18 omega   91.00  130.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000  120.0000 39

#__ type_ start__ end____ width___ exp.time_
 19 omega   42.00   98.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000   30.0000 56

#__ type_ start__ end____ width___ exp.time_
 20 omega   74.00  109.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000   30.0000 35

#__ type_ start__ end____ width___ exp.time_
 21 omega   60.00   86.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  -30.0000 26

#__ type_ start__ end____ width___ exp.time_
 22 omega   45.00  132.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000   90.0000 87
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0012261000
_diffrn_orient_matrix_UB_12      0.0977823000
_diffrn_orient_matrix_UB_13      -0.0370444000
_diffrn_orient_matrix_UB_21      0.0409898000
_diffrn_orient_matrix_UB_22      0.0483960000
_diffrn_orient_matrix_UB_23      0.0748410000
_diffrn_orient_matrix_UB_31      0.1692540000
_diffrn_orient_matrix_UB_32      -0.0109986000
_diffrn_orient_matrix_UB_33      -0.0004882000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2936
_reflns_number_total             4187
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.200
_refine_diff_density_min         -0.134
_refine_diff_density_rms         0.033
_refine_ls_extinction_coef       0.0016(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     293
_refine_ls_number_reflns         4187
_refine_ls_number_restraints     13
_refine_ls_R_factor_all          0.0727
_refine_ls_R_factor_gt           0.0527
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0749P)²+0.1694P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1432
_refine_ls_wR_factor_ref         0.1669
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid bond restraints
 C27, C26
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
3. Uiso/Uaniso restraints and constraints
Uanis(C27) \\sim Ueq, Uanis(C26) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
4.a Ternary CH refined with riding coordinates:
 C17(H17), C21(H21)
4.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C6(H6A,H6B), C20(H20A,H20B), C22(H22A,H22B)
4.c Aromatic/amide H refined with riding coordinates:
 C10(H10), C11(H11), C13(H13), C14(H14), C19(H19), C24(H24), C25(H25),
 C26(H26), C27(H27), C28(H28)
4.d Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.0096(3) 0.44952(17) 0.14264(12) 0.0663(6) Uani 1 1 d . . . . .
C2 C 0.0095(2) 0.39449(15) 0.20890(11) 0.0572(5) Uani 1 1 d . . . . .
C3 C 0.1502(2) 0.36338(15) 0.24288(10) 0.0527(5) Uani 1 1 d . . . . .
C4 C 0.2850(2) 0.37319(17) 0.20841(11) 0.0610(5) Uani 1 1 d . . . . .
H4A H 0.3471 0.3166 0.2190 0.073 Uiso 1 1 calc R . . . .
H4B H 0.3451 0.4270 0.2301 0.073 Uiso 1 1 calc R . . . .
C5 C 0.2437(3) 0.38733(18) 0.12599(12) 0.0696(6) Uani 1 1 d . . . . .
C6 C 0.1277(3) 0.46740(19) 0.11073(12) 0.0763(7) Uani 1 1 d . . . . .
H6A H 0.1753 0.5263 0.1304 0.092 Uiso 1 1 calc R . . . .
H6B H 0.0956 0.4753 0.0587 0.092 Uiso 1 1 calc R . . . .
C7 C 0.1784(3) 0.2964(2) 0.08724(14) 0.0886(8) Uani 1 1 d . . . . .
H7A H 0.2513 0.2460 0.0983 0.133 Uiso 1 1 calc GR . . . .
H7B H 0.1548 0.3071 0.0359 0.133 Uiso 1 1 calc GR . . . .
H7C H 0.0881 0.2788 0.1032 0.133 Uiso 1 1 calc GR . . . .
C8 C 0.3879(4) 0.4152(3) 0.10028(16) 0.1029(10) Uani 1 1 d . . . . .
H8A H 0.4334 0.4694 0.1272 0.154 Uiso 1 1 calc GR . . . .
H8B H 0.3630 0.4306 0.0496 0.154 Uiso 1 1 calc GR . . . .
H8C H 0.4577 0.3628 0.1079 0.154 Uiso 1 1 calc GR . . . .
C9 C 0.3130(2) 0.28953(15) 0.35154(10) 0.0520(5) Uani 1 1 d . . . . .
C10 C 0.3315(3) 0.19723(16) 0.37695(11) 0.0615(5) Uani 1 1 d . . . . .
H10 H 0.2528 0.1537 0.3649 0.074 Uiso 1 1 calc R . . . .
C11 C 0.4678(3) 0.1698(2) 0.42045(12) 0.0766(7) Uani 1 1 d . . . . .
H11 H 0.4790 0.1077 0.4380 0.092 Uiso 1 1 calc R . . . .
C12 C 0.5880(3) 0.2327(2) 0.43845(12) 0.0808(8) Uani 1 1 d . . . . .
C13 C 0.5669(3) 0.3247(2) 0.41306(13) 0.0759(7) Uani 1 1 d . . . . .
H13 H 0.6461 0.3680 0.4244 0.091 Uiso 1 1 calc R . . . .
C14 C 0.4302(2) 0.35394(18) 0.37100(11) 0.0631(6) Uani 1 1 d . . . . .
H14 H 0.4171 0.4169 0.3558 0.076 Uiso 1 1 calc R . . . .
C15 C 0.7385(4) 0.2006(3) 0.48356(17) 0.1312(16) Uani 1 1 d . . . . .
H15A H 0.7967 0.1704 0.4528 0.197 Uiso 1 1 calc GR . . . .
H15B H 0.7215 0.1564 0.5198 0.197 Uiso 1 1 calc GR . . . .
H15C H 0.7928 0.2548 0.5067 0.197 Uiso 1 1 calc GR . . . .
C16 C 0.1136(3) 0.4325(2) 0.44500(13) 0.0794(7) Uani 1 1 d . . . . .
C17 C 0.0357(2) 0.31558(17) 0.34279(11) 0.0592(5) Uani 1 1 d . . . . .
H17 H 0.0527 0.2668 0.3808 0.071 Uiso 1 1 calc R . . . .
C18 C 0.0146(2) 0.41061(19) 0.37683(11) 0.0658(6) Uani 1 1 d . . . . .
C19 C -0.0904(3) 0.47289(19) 0.34621(13) 0.0709(6) Uani 1 1 d . . . . .
H19 H -0.1014 0.5295 0.3702 0.085 Uiso 1 1 calc R . . . .
C20 C -0.1908(3) 0.45382(19) 0.27427(13) 0.0712(6) Uani 1 1 d . . . . .
H20A H -0.1959 0.5100 0.2439 0.085 Uiso 1 1 calc R . . . .
H20B H -0.2922 0.4396 0.2806 0.085 Uiso 1 1 calc R . . . .
C21 C -0.1305(2) 0.37038(17) 0.23762(12) 0.0616(5) Uani 1 1 d . . . . .
H21 H -0.2097 0.3495 0.1969 0.074 Uiso 1 1 calc R . . . .
C22 C -0.0889(2) 0.19810(17) 0.25761(14) 0.0691(6) Uani 1 1 d . . . . .
H22A H -0.0487 0.1523 0.2952 0.083 Uiso 1 1 calc R . . . .
H22B H -0.0199 0.2015 0.2246 0.083 Uiso 1 1 calc R . . . .
C23 C -0.2416(2) 0.16519(16) 0.21696(12) 0.0600(5) Uani 1 1 d . . . . .
C24 C -0.3624(3) 0.16116(18) 0.25149(13) 0.0682(6) Uani 1 1 d . . . . .
H24 H -0.3488 0.1797 0.2997 0.082 Uiso 1 1 calc R . . . .
C25 C -0.5019(3) 0.13024(19) 0.21552(15) 0.0750(7) Uani 1 1 d . . . . .
H25 H -0.5814 0.1274 0.2397 0.090 Uiso 1 1 calc R . . . .
C26 C -0.5248(3) 0.10363(19) 0.14476(15) 0.0791(7) Uani 1 1 d . U . . .
H26 H -0.6196 0.0829 0.1206 0.095 Uiso 1 1 calc R . . . .
C27 C -0.4071(3) 0.1075(2) 0.10918(14) 0.0834(7) Uani 1 1 d . U . . .
H27 H -0.4226 0.0899 0.0607 0.100 Uiso 1 1 calc R . . . .
C28 C -0.2650(3) 0.13762(19) 0.14543(13) 0.0741(7) Uani 1 1 d . . . . .
H28 H -0.1853 0.1392 0.1213 0.089 Uiso 1 1 calc R . . . .
N1 N 0.17020(18) 0.31888(13) 0.30858(9) 0.0555(4) Uani 1 1 d . . . . .
N2 N 0.1918(3) 0.4500(2) 0.49875(12) 0.1054(9) Uani 1 1 d . . . . .
N3 N -0.09900(19) 0.29201(14) 0.29061(10) 0.0612(5) Uani 1 1 d . . . . .
O1 O -0.1332(2) 0.48328(14) 0.11377(9) 0.0904(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
C1 C2 1.449(3) . ?
C1 C6 1.510(3) . ?
C1 O1 1.232(3) . ?
C2 C3 1.372(3) . ?
C2 C21 1.516(3) . ?
C3 C4 1.503(3) . ?
C3 N1 1.366(2) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C5 1.535(3) . ?
C5 C6 1.524(3) . ?
C5 C7 1.529(4) . ?
C5 C8 1.535(4) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 C10 1.381(3) . ?
C9 C14 1.384(3) . ?
C9 N1 1.434(2) . ?
C10 H10 0.9300 . ?
C10 C11 1.386(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.388(4) . ?
C12 C13 1.377(4) . ?
C12 C15 1.516(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.385(3) . ?
C14 H14 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 C18 1.439(3) . ?
C16 N2 1.136(3) . ?
C17 H17 0.9800 . ?
C17 C18 1.511(3) . ?
C17 N1 1.492(2) . ?
C17 N3 1.436(3) . ?
C18 C19 1.331(3) . ?
C19 H19 0.9300 . ?
C19 C20 1.491(3) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 C21 1.519(3) . ?
C21 H21 0.9800 . ?
C21 N3 1.475(3) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C22 C23 1.506(3) . ?
C22 N3 1.470(3) . ?
C23 C24 1.385(3) . ?
C23 C28 1.377(3) . ?
C24 H24 0.9300 . ?
C24 C25 1.372(3) . ?
C25 H25 0.9300 . ?
C25 C26 1.360(4) . ?
C26 H26 0.9300 . ?
C26 C27 1.373(4) . ?
C27 H27 0.9300 . ?
C27 C28 1.390(4) . ?
C28 H28 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 118.23(19) . . ?
O1 C1 C2 121.3(2) . . ?
O1 C1 C6 120.4(2) . . ?
C1 C2 C21 118.03(19) . . ?
C3 C2 C1 120.3(2) . . ?
C3 C2 C21 121.63(18) . . ?
C2 C3 C4 121.73(18) . . ?
N1 C3 C2 120.25(19) . . ?
N1 C3 C4 117.97(17) . . ?
C3 C4 H4A 108.8 . . ?
C3 C4 H4B 108.8 . . ?
C3 C4 C5 113.72(18) . . ?
H4A C4 H4B 107.7 . . ?
C5 C4 H4A 108.8 . . ?
C5 C4 H4B 108.8 . . ?
C4 C5 C8 108.1(2) . . ?
C6 C5 C4 107.43(19) . . ?
C6 C5 C7 110.2(2) . . ?
C6 C5 C8 110.4(2) . . ?
C7 C5 C4 111.4(2) . . ?
C7 C5 C8 109.3(2) . . ?
C1 C6 C5 113.1(2) . . ?
C1 C6 H6A 109.0 . . ?
C1 C6 H6B 109.0 . . ?
C5 C6 H6A 109.0 . . ?
C5 C6 H6B 109.0 . . ?
H6A C6 H6B 107.8 . . ?
C5 C7 H7A 109.5 . . ?
C5 C7 H7B 109.5 . . ?
C5 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C5 C8 H8A 109.5 . . ?
C5 C8 H8B 109.5 . . ?
C5 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C10 C9 C14 119.4(2) . . ?
C10 C9 N1 119.73(19) . . ?
C14 C9 N1 120.75(19) . . ?
C9 C10 H10 120.1 . . ?
C9 C10 C11 119.7(2) . . ?
C11 C10 H10 120.1 . . ?
C10 C11 H11 119.3 . . ?
C10 C11 C12 121.5(3) . . ?
C12 C11 H11 119.3 . . ?
C11 C12 C15 120.9(3) . . ?
C13 C12 C11 117.9(2) . . ?
C13 C12 C15 121.1(3) . . ?
C12 C13 H13 119.3 . . ?
C12 C13 C14 121.3(2) . . ?
C14 C13 H13 119.3 . . ?
C9 C14 C13 120.1(2) . . ?
C9 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N2 C16 C18 179.8(4) . . ?
C18 C17 H17 108.7 . . ?
N1 C17 H17 108.7 . . ?
N1 C17 C18 110.08(18) . . ?
N3 C17 H17 108.7 . . ?
N3 C17 C18 109.31(18) . . ?
N3 C17 N1 111.23(16) . . ?
C16 C18 C17 117.3(2) . . ?
C19 C18 C16 120.1(2) . . ?
C19 C18 C17 122.6(2) . . ?
C18 C19 H19 119.3 . . ?
C18 C19 C20 121.4(2) . . ?
C20 C19 H19 119.3 . . ?
C19 C20 H20A 109.6 . . ?
C19 C20 H20B 109.6 . . ?
C19 C20 C21 110.16(19) . . ?
H20A C20 H20B 108.1 . . ?
C21 C20 H20A 109.6 . . ?
C21 C20 H20B 109.6 . . ?
C2 C21 C20 113.4(2) . . ?
C2 C21 H21 108.3 . . ?
C20 C21 H21 108.3 . . ?
N3 C21 C2 110.61(16) . . ?
N3 C21 C20 107.73(19) . . ?
N3 C21 H21 108.3 . . ?
H22A C22 H22B 108.0 . . ?
C23 C22 H22A 109.4 . . ?
C23 C22 H22B 109.4 . . ?
N3 C22 H22A 109.4 . . ?
N3 C22 H22B 109.4 . . ?
N3 C22 C23 111.07(18) . . ?
C24 C23 C22 120.2(2) . . ?
C28 C23 C22 121.5(2) . . ?
C28 C23 C24 118.3(2) . . ?
C23 C24 H24 119.5 . . ?
C25 C24 C23 120.9(2) . . ?
C25 C24 H24 119.5 . . ?
C24 C25 H25 119.7 . . ?
C26 C25 C24 120.6(2) . . ?
C26 C25 H25 119.7 . . ?
C25 C26 H26 120.2 . . ?
C25 C26 C27 119.6(2) . . ?
C27 C26 H26 120.2 . . ?
C26 C27 H27 119.9 . . ?
C26 C27 C28 120.2(2) . . ?
C28 C27 H27 119.9 . . ?
C23 C28 C27 120.3(2) . . ?
C23 C28 H28 119.8 . . ?
C27 C28 H28 119.8 . . ?
C3 N1 C9 125.25(16) . . ?
C3 N1 C17 116.19(16) . . ?
C9 N1 C17 117.76(15) . . ?
C17 N3 C21 107.98(17) . . ?
C17 N3 C22 112.23(18) . . ?
C22 N3 C21 113.78(18) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 -8.3(3) . . . . ?
C1 C2 C3 N1 174.19(19) . . . . ?
C1 C2 C21 C20 -76.1(2) . . . . ?
C1 C2 C21 N3 162.79(19) . . . . ?
C2 C1 C6 C5 30.8(3) . . . . ?
C2 C3 C4 C5 -19.8(3) . . . . ?
C2 C3 N1 C9 -175.26(19) . . . . ?
C2 C3 N1 C17 -5.8(3) . . . . ?
C2 C21 N3 C17 50.4(2) . . . . ?
C2 C21 N3 C22 -74.9(2) . . . . ?
C3 C2 C21 C20 105.7(2) . . . . ?
C3 C2 C21 N3 -15.4(3) . . . . ?
C3 C4 C5 C6 50.2(3) . . . . ?
C3 C4 C5 C7 -70.6(3) . . . . ?
C3 C4 C5 C8 169.3(2) . . . . ?
C4 C3 N1 C9 7.2(3) . . . . ?
C4 C3 N1 C17 176.63(18) . . . . ?
C4 C5 C6 C1 -55.5(3) . . . . ?
C6 C1 C2 C3 2.7(3) . . . . ?
C6 C1 C2 C21 -175.5(2) . . . . ?
C7 C5 C6 C1 66.0(3) . . . . ?
C8 C5 C6 C1 -173.2(2) . . . . ?
C9 C10 C11 C12 -1.0(3) . . . . ?
C10 C9 C14 C13 2.8(3) . . . . ?
C10 C9 N1 C3 -128.6(2) . . . . ?
C10 C9 N1 C17 62.1(3) . . . . ?
C10 C11 C12 C13 1.4(3) . . . . ?
C10 C11 C12 C15 -177.5(2) . . . . ?
C11 C12 C13 C14 0.2(3) . . . . ?
C12 C13 C14 C9 -2.3(3) . . . . ?
C14 C9 C10 C11 -1.2(3) . . . . ?
C14 C9 N1 C3 54.8(3) . . . . ?
C14 C9 N1 C17 -114.5(2) . . . . ?
C15 C12 C13 C14 179.1(2) . . . . ?
C16 C18 C19 C20 177.7(2) . . . . ?
C17 C18 C19 C20 -2.4(4) . . . . ?
C18 C17 N1 C3 -78.0(2) . . . . ?
C18 C17 N1 C9 92.3(2) . . . . ?
C18 C17 N3 C21 56.4(2) . . . . ?
C18 C17 N3 C22 -177.44(18) . . . . ?
C18 C19 C20 C21 -13.1(3) . . . . ?
C19 C20 C21 C2 -73.4(3) . . . . ?
C19 C20 C21 N3 49.3(3) . . . . ?
C20 C21 N3 C17 -74.0(2) . . . . ?
C20 C21 N3 C22 160.73(18) . . . . ?
C21 C2 C3 C4 169.81(19) . . . . ?
C21 C2 C3 N1 -7.7(3) . . . . ?
C22 C23 C24 C25 -179.2(2) . . . . ?
C22 C23 C28 C27 180.0(2) . . . . ?
C23 C22 N3 C17 166.70(18) . . . . ?
C23 C22 N3 C21 -70.3(2) . . . . ?
C23 C24 C25 C26 -0.6(4) . . . . ?
C24 C23 C28 C27 0.6(4) . . . . ?
C24 C25 C26 C27 0.2(4) . . . . ?
C25 C26 C27 C28 0.6(4) . . . . ?
C26 C27 C28 C23 -1.0(4) . . . . ?
C28 C23 C24 C25 0.2(4) . . . . ?
N1 C3 C4 C5 157.7(2) . . . . ?
N1 C9 C10 C11 -177.85(18) . . . . ?
N1 C9 C14 C13 179.41(19) . . . . ?
N1 C17 C18 C16 -76.9(2) . . . . ?
N1 C17 C18 C19 103.1(2) . . . . ?
N1 C17 N3 C21 -65.4(2) . . . . ?
N1 C17 N3 C22 60.8(2) . . . . ?
N3 C17 C18 C16 160.6(2) . . . . ?
N3 C17 C18 C19 -19.4(3) . . . . ?
N3 C17 N1 C3 43.3(3) . . . . ?
N3 C17 N1 C9 -146.42(19) . . . . ?
N3 C22 C23 C24 -54.5(3) . . . . ?
N3 C22 C23 C28 126.1(2) . . . . ?
O1 C1 C2 C3 -175.3(2) . . . . ?
O1 C1 C2 C21 6.5(3) . . . . ?
O1 C1 C6 C5 -151.1(2) . . . . ?

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

data_20190484
_database_code_depnum_ccdc_archive 'CCDC 1947691'
loop_
_audit_author_name
_audit_author_address
'Qilin Wang'
;Henan University
China
;
_audit_update_record             
;
2019-08-17 deposited with the CCDC.	2019-12-17 downloaded from the CCDC.
;
_audit_creation_date             2019-04-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C31 H31 Br N2 O'
_chemical_formula_sum            'C31 H31 Br N2 O'
_chemical_formula_weight         527.49
_chemical_melting_point          ?
_chemical_oxdiff_formula         C20H20N4O4Br1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   14.4850(5)
_cell_length_b                   10.8239(5)
_cell_length_c                   16.4134(7)
_cell_angle_alpha                90
_cell_angle_beta                 90.869(3)
_cell_angle_gamma                90
_cell_volume                     2573.07(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3325
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.7610
_cell_measurement_theta_min      4.0450
_shelx_estimated_absorpt_T_max   0.797
_shelx_estimated_absorpt_T_min   0.689
_exptl_absorpt_coefficient_mu    2.372
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90797
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.362
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1096
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0341
_diffrn_reflns_av_unetI/netI     0.0441
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            10451
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.055
_diffrn_reflns_theta_max         67.055
_diffrn_reflns_theta_min         4.040
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega -101.00  -17.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -57.0000    0.0000 84

#__ type_ start__ end____ width___ exp.time_
  2 omega -108.00  -75.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  178.0000   30.0000 33

#__ type_ start__ end____ width___ exp.time_
  3 omega   -3.00   22.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000 -180.0000 25

#__ type_ start__ end____ width___ exp.time_
  4 omega   58.00   85.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000 -180.0000 27

#__ type_ start__ end____ width___ exp.time_
  5 omega   18.00   58.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -37.0000   30.0000 40

#__ type_ start__ end____ width___ exp.time_
  6 omega   45.00   71.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000 -150.0000 26

#__ type_ start__ end____ width___ exp.time_
  7 omega  -31.00   21.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -57.0000  -60.0000 52

#__ type_ start__ end____ width___ exp.time_
  8 omega    0.00   26.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000 -150.0000 26

#__ type_ start__ end____ width___ exp.time_
  9 omega  -33.00   -7.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -37.0000 -150.0000 26

#__ type_ start__ end____ width___ exp.time_
 10 omega   13.00   59.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -37.0000 -150.0000 46

#__ type_ start__ end____ width___ exp.time_
 11 omega  -31.00   -5.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -37.0000   30.0000 26

#__ type_ start__ end____ width___ exp.time_
 12 omega    1.00   38.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000   90.0000 37

#__ type_ start__ end____ width___ exp.time_
 13 omega   52.00   77.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000   90.0000 25

#__ type_ start__ end____ width___ exp.time_
 14 omega   38.00   71.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000 -180.0000 33

#__ type_ start__ end____ width___ exp.time_
 15 omega   58.00   87.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -150.0000 29

#__ type_ start__ end____ width___ exp.time_
 16 omega   60.00   91.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  120.0000 31

#__ type_ start__ end____ width___ exp.time_
 17 omega   41.00  106.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000   30.0000 65

#__ type_ start__ end____ width___ exp.time_
 18 omega   42.00   97.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   90.0000 55

#__ type_ start__ end____ width___ exp.time_
 19 omega   67.00  113.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000 -180.0000 46

#__ type_ start__ end____ width___ exp.time_
 20 omega   38.00   72.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -30.0000 34

#__ type_ start__ end____ width___ exp.time_
 21 omega   47.00   78.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -150.0000 31

#__ type_ start__ end____ width___ exp.time_
 22 omega  134.00  175.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000 -150.0000 41

#__ type_ start__ end____ width___ exp.time_
 23 omega  103.00  129.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000 -150.0000 26

#__ type_ start__ end____ width___ exp.time_
 24 omega   57.00   99.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   30.0000 42

#__ type_ start__ end____ width___ exp.time_
 25 omega   67.00  109.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000   90.0000 42

#__ type_ start__ end____ width___ exp.time_
 26 omega   87.00  174.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000  -90.0000 87
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0560458000
_diffrn_orient_matrix_UB_12      -0.0882394000
_diffrn_orient_matrix_UB_13      -0.0553746000
_diffrn_orient_matrix_UB_21      -0.0365383000
_diffrn_orient_matrix_UB_22      0.1112162000
_diffrn_orient_matrix_UB_23      -0.0494024000
_diffrn_orient_matrix_UB_31      0.0826638000
_diffrn_orient_matrix_UB_32      -0.0106723000
_diffrn_orient_matrix_UB_33      -0.0574768000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3531
_reflns_number_total             4590
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.269
_refine_diff_density_min         -0.450
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     319
_refine_ls_number_reflns         4590
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0603
_refine_ls_R_factor_gt           0.0444
_refine_ls_restrained_S_all      1.015
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0616P)²+0.5371P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1123
_refine_ls_wR_factor_ref         0.1261
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7), C8(H8), C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C20(H20A,H20B), C22(H22A,H22B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C12(H12), C13(H13), C14(H14), C15(H15),
 C16(H16), C26(H26), C27(H27), C29(H29), C30(H30)
2.d Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C24(H24A,H24B,H24C), C31(H31A,H31B,H31C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br -0.04757(2) -0.01860(4) 0.37544(2) 0.06148(16) Uani 1 1 d . . . . .
C1 C 0.0167(2) 0.1485(3) 0.2134(2) 0.0582(9) Uani 1 1 d . . . . .
H1 H -0.0273 0.1965 0.2394 0.070 Uiso 1 1 calc R . . . .
C2 C 0.0205(3) 0.1495(4) 0.1293(2) 0.0659(10) Uani 1 1 d . . . . .
H2 H -0.0220 0.1952 0.0988 0.079 Uiso 1 1 calc R . . . .
C3 C 0.0885(2) 0.0815(3) 0.0911(2) 0.0572(9) Uani 1 1 d . . . . .
H3 H 0.0919 0.0820 0.0345 0.069 Uiso 1 1 calc R . . . .
C4 C 0.1509(2) 0.0133(3) 0.1365(2) 0.0468(7) Uani 1 1 d . . . . .
H4 H 0.1970 -0.0304 0.1103 0.056 Uiso 1 1 calc R . . . .
C5 C 0.14571(19) 0.0089(3) 0.22141(18) 0.0389(6) Uani 1 1 d . . . . .
C6 C 0.07751(19) 0.0770(3) 0.25988(19) 0.0433(7) Uani 1 1 d . . . . .
C7 C 0.06853(18) 0.0706(3) 0.35069(19) 0.0429(7) Uani 1 1 d . . . . .
H7 H 0.0648 0.1547 0.3724 0.051 Uiso 1 1 calc R . . . .
C8 C 0.14755(19) 0.0017(3) 0.39456(18) 0.0387(6) Uani 1 1 d . . . . .
H8 H 0.1255 -0.0259 0.4477 0.046 Uiso 1 1 calc R . . . .
C9 C 0.21534(18) -0.0645(3) 0.27126(17) 0.0379(6) Uani 1 1 d . . . . .
H9 H 0.2342 -0.1372 0.2400 0.046 Uiso 1 1 calc R . . . .
C10 C 0.2308(2) -0.1942(3) 0.39255(19) 0.0465(7) Uani 1 1 d . . . . .
H10A H 0.2878 -0.1537 0.4089 0.056 Uiso 1 1 calc R . . . .
H10B H 0.2463 -0.2621 0.3567 0.056 Uiso 1 1 calc R . . . .
C11 C 0.1842(2) -0.2452(3) 0.46757(18) 0.0431(7) Uani 1 1 d . . . . .
C12 C 0.2328(2) -0.2509(3) 0.5408(2) 0.0529(8) Uani 1 1 d . . . . .
H12 H 0.2932 -0.2218 0.5438 0.063 Uiso 1 1 calc R . . . .
C13 C 0.1926(3) -0.2993(4) 0.6094(2) 0.0658(10) Uani 1 1 d . . . . .
H13 H 0.2264 -0.3035 0.6579 0.079 Uiso 1 1 calc R . . . .
C14 C 0.1041(3) -0.3410(3) 0.6068(2) 0.0627(10) Uani 1 1 d . . . . .
H14 H 0.0773 -0.3722 0.6537 0.075 Uiso 1 1 calc R . . . .
C15 C 0.0541(2) -0.3370(3) 0.5350(2) 0.0593(9) Uani 1 1 d . . . . .
H15 H -0.0061 -0.3667 0.5328 0.071 Uiso 1 1 calc R . . . .
C16 C 0.0942(2) -0.2882(3) 0.4653(2) 0.0532(8) Uani 1 1 d . . . . .
H16 H 0.0602 -0.2845 0.4169 0.064 Uiso 1 1 calc R . . . .
C17 C 0.3757(2) 0.0158(3) 0.23299(18) 0.0443(7) Uani 1 1 d . . . . .
C18 C 0.29941(19) 0.0150(3) 0.28901(17) 0.0379(6) Uani 1 1 d . . . . .
C19 C 0.30071(18) 0.0868(3) 0.35691(17) 0.0371(6) Uani 1 1 d . . . . .
C20 C 0.38062(19) 0.1692(3) 0.37915(18) 0.0441(7) Uani 1 1 d . . . . .
H20A H 0.3909 0.1652 0.4376 0.053 Uiso 1 1 calc R . . . .
H20B H 0.3643 0.2537 0.3656 0.053 Uiso 1 1 calc R . . . .
C21 C 0.47084(19) 0.1367(3) 0.33685(18) 0.0451(7) Uani 1 1 d . . . . .
C22 C 0.4486(2) 0.1124(3) 0.24721(18) 0.0499(8) Uani 1 1 d . . . . .
H22A H 0.4284 0.1890 0.2221 0.060 Uiso 1 1 calc R . . . .
H22B H 0.5047 0.0866 0.2204 0.060 Uiso 1 1 calc R . . . .
C23 C 0.5155(3) 0.0230(4) 0.3754(3) 0.0699(11) Uani 1 1 d . . . . .
H23A H 0.4731 -0.0451 0.3727 0.105 Uiso 1 1 calc GR . . . .
H23B H 0.5310 0.0401 0.4314 0.105 Uiso 1 1 calc GR . . . .
H23C H 0.5705 0.0023 0.3466 0.105 Uiso 1 1 calc GR . . . .
C24 C 0.5361(2) 0.2485(4) 0.3442(2) 0.0673(11) Uani 1 1 d . . . . .
H24A H 0.5934 0.2297 0.3184 0.101 Uiso 1 1 calc GR . . . .
H24B H 0.5474 0.2668 0.4007 0.101 Uiso 1 1 calc GR . . . .
H24C H 0.5081 0.3188 0.3180 0.101 Uiso 1 1 calc GR . . . .
C25 C 0.22780(18) 0.1601(3) 0.48138(16) 0.0373(6) Uani 1 1 d . . . . .
C26 C 0.2034(2) 0.2837(3) 0.47661(17) 0.0433(7) Uani 1 1 d . . . . .
H26 H 0.1829 0.3173 0.4274 0.052 Uiso 1 1 calc R . . . .
C27 C 0.2097(2) 0.3566(3) 0.54552(19) 0.0486(7) Uani 1 1 d . . . . .
H27 H 0.1938 0.4397 0.5418 0.058 Uiso 1 1 calc R . . . .
C28 C 0.2391(2) 0.3099(3) 0.61995(18) 0.0452(7) Uani 1 1 d . . . . .
C29 C 0.2601(2) 0.1848(3) 0.62389(18) 0.0496(8) Uani 1 1 d . . . . .
H29 H 0.2781 0.1502 0.6735 0.060 Uiso 1 1 calc R . . . .
C30 C 0.2546(2) 0.1108(3) 0.55546(18) 0.0467(7) Uani 1 1 d . . . . .
H30 H 0.2691 0.0273 0.5594 0.056 Uiso 1 1 calc R . . . .
C31 C 0.2489(3) 0.3919(4) 0.6939(2) 0.0652(10) Uani 1 1 d . . . . .
H31A H 0.1897 0.4255 0.7072 0.098 Uiso 1 1 calc GR . . . .
H31B H 0.2909 0.4581 0.6824 0.098 Uiso 1 1 calc GR . . . .
H31C H 0.2723 0.3444 0.7390 0.098 Uiso 1 1 calc GR . . . .
N1 N 0.17235(16) -0.1058(2) 0.34771(14) 0.0388(5) Uani 1 1 d . . . . .
N2 N 0.22716(15) 0.0859(2) 0.40841(14) 0.0400(6) Uani 1 1 d . . . . .
O1 O 0.37940(16) -0.0556(3) 0.17501(14) 0.0657(7) 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 C7 1.986(3) . ?
C1 H1 0.9300 . ?
C1 C2 1.382(5) . ?
C1 C6 1.392(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.387(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.378(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.398(4) . ?
C5 C6 1.391(4) . ?
C5 C9 1.514(4) . ?
C6 C7 1.500(4) . ?
C7 H7 0.9800 . ?
C7 C8 1.536(4) . ?
C8 H8 0.9800 . ?
C8 N1 1.443(4) . ?
C8 N2 1.484(4) . ?
C9 H9 0.9800 . ?
C9 C18 1.516(4) . ?
C9 N1 1.478(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.517(4) . ?
C10 N1 1.468(4) . ?
C11 C12 1.386(4) . ?
C11 C16 1.384(4) . ?
C12 H12 0.9300 . ?
C12 C13 1.378(5) . ?
C13 H13 0.9300 . ?
C13 C14 1.360(6) . ?
C14 H14 0.9300 . ?
C14 C15 1.375(5) . ?
C15 H15 0.9300 . ?
C15 C16 1.394(5) . ?
C16 H16 0.9300 . ?
C17 C18 1.448(4) . ?
C17 C22 1.502(4) . ?
C17 O1 1.228(4) . ?
C18 C19 1.359(4) . ?
C19 C20 1.502(4) . ?
C19 N2 1.370(3) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 C21 1.530(4) . ?
C21 C22 1.524(4) . ?
C21 C23 1.524(5) . ?
C21 C24 1.539(5) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 C26 1.386(4) . ?
C25 C30 1.379(4) . ?
C25 N2 1.442(4) . ?
C26 H26 0.9300 . ?
C26 C27 1.381(4) . ?
C27 H27 0.9300 . ?
C27 C28 1.383(4) . ?
C28 C29 1.389(5) . ?
C28 C31 1.509(4) . ?
C29 H29 0.9300 . ?
C29 C30 1.381(4) . ?
C30 H30 0.9300 . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 H1 119.4 . . ?
C2 C1 C6 121.1(3) . . ?
C6 C1 H1 119.4 . . ?
C1 C2 H2 120.4 . . ?
C1 C2 C3 119.2(3) . . ?
C3 C2 H2 120.4 . . ?
C2 C3 H3 119.9 . . ?
C4 C3 C2 120.2(3) . . ?
C4 C3 H3 119.9 . . ?
C3 C4 H4 119.5 . . ?
C3 C4 C5 120.9(3) . . ?
C5 C4 H4 119.5 . . ?
C4 C5 C9 120.8(3) . . ?
C6 C5 C4 118.9(3) . . ?
C6 C5 C9 120.3(3) . . ?
C1 C6 C7 120.4(3) . . ?
C5 C6 C1 119.6(3) . . ?
C5 C6 C7 120.0(3) . . ?
Br1 C7 H7 109.0 . . ?
C6 C7 Br1 108.2(2) . . ?
C6 C7 H7 109.0 . . ?
C6 C7 C8 114.4(2) . . ?
C8 C7 Br1 107.2(2) . . ?
C8 C7 H7 109.0 . . ?
C7 C8 H8 108.3 . . ?
N1 C8 C7 109.3(2) . . ?
N1 C8 H8 108.3 . . ?
N1 C8 N2 112.2(2) . . ?
N2 C8 C7 110.2(2) . . ?
N2 C8 H8 108.3 . . ?
C5 C9 H9 109.1 . . ?
C5 C9 C18 109.4(2) . . ?
C18 C9 H9 109.1 . . ?
N1 C9 C5 109.3(2) . . ?
N1 C9 H9 109.1 . . ?
N1 C9 C18 110.8(2) . . ?
H10A C10 H10B 107.8 . . ?
C11 C10 H10A 109.1 . . ?
C11 C10 H10B 109.1 . . ?
N1 C10 H10A 109.1 . . ?
N1 C10 H10B 109.1 . . ?
N1 C10 C11 112.6(2) . . ?
C12 C11 C10 119.6(3) . . ?
C16 C11 C10 122.1(3) . . ?
C16 C11 C12 118.3(3) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 C11 120.6(3) . . ?
C13 C12 H12 119.7 . . ?
C12 C13 H13 119.6 . . ?
C14 C13 C12 120.8(4) . . ?
C14 C13 H13 119.6 . . ?
C13 C14 H14 120.0 . . ?
C13 C14 C15 120.0(3) . . ?
C15 C14 H14 120.0 . . ?
C14 C15 H15 120.2 . . ?
C14 C15 C16 119.7(3) . . ?
C16 C15 H15 120.2 . . ?
C11 C16 C15 120.6(3) . . ?
C11 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?
C18 C17 C22 116.6(3) . . ?
O1 C17 C18 122.1(3) . . ?
O1 C17 C22 121.3(3) . . ?
C17 C18 C9 120.0(2) . . ?
C19 C18 C9 118.9(2) . . ?
C19 C18 C17 121.1(3) . . ?
C18 C19 C20 122.7(2) . . ?
C18 C19 N2 120.1(3) . . ?
N2 C19 C20 117.3(2) . . ?
C19 C20 H20A 108.6 . . ?
C19 C20 H20B 108.6 . . ?
C19 C20 C21 114.4(2) . . ?
H20A C20 H20B 107.6 . . ?
C21 C20 H20A 108.6 . . ?
C21 C20 H20B 108.6 . . ?
C20 C21 C24 108.2(3) . . ?
C22 C21 C20 108.0(2) . . ?
C22 C21 C24 109.4(3) . . ?
C23 C21 C20 110.9(3) . . ?
C23 C21 C22 110.1(3) . . ?
C23 C21 C24 110.3(3) . . ?
C17 C22 C21 114.1(3) . . ?
C17 C22 H22A 108.7 . . ?
C17 C22 H22B 108.7 . . ?
C21 C22 H22A 108.7 . . ?
C21 C22 H22B 108.7 . . ?
H22A C22 H22B 107.6 . . ?
C21 C23 H23A 109.5 . . ?
C21 C23 H23B 109.5 . . ?
C21 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C21 C24 H24A 109.5 . . ?
C21 C24 H24B 109.5 . . ?
C21 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C26 C25 N2 119.5(3) . . ?
C30 C25 C26 119.5(3) . . ?
C30 C25 N2 121.0(3) . . ?
C25 C26 H26 120.3 . . ?
C27 C26 C25 119.5(3) . . ?
C27 C26 H26 120.3 . . ?
C26 C27 H27 119.0 . . ?
C26 C27 C28 122.0(3) . . ?
C28 C27 H27 119.0 . . ?
C27 C28 C29 117.5(3) . . ?
C27 C28 C31 121.2(3) . . ?
C29 C28 C31 121.2(3) . . ?
C28 C29 H29 119.4 . . ?
C30 C29 C28 121.2(3) . . ?
C30 C29 H29 119.4 . . ?
C25 C30 C29 120.3(3) . . ?
C25 C30 H30 119.8 . . ?
C29 C30 H30 119.8 . . ?
C28 C31 H31A 109.5 . . ?
C28 C31 H31B 109.5 . . ?
C28 C31 H31C 109.5 . . ?
H31A C31 H31B 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C8 N1 C9 108.7(2) . . ?
C8 N1 C10 113.9(2) . . ?
C10 N1 C9 112.0(2) . . ?
C19 N2 C8 121.3(2) . . ?
C19 N2 C25 120.9(2) . . ?
C25 N2 C8 117.7(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Br1 C7 C8 N1 79.6(2) . . . . ?
Br1 C7 C8 N2 -156.63(18) . . . . ?
C1 C2 C3 C4 0.4(6) . . . . ?
C1 C6 C7 Br1 68.0(3) . . . . ?
C1 C6 C7 C8 -172.6(3) . . . . ?
C2 C1 C6 C5 2.5(5) . . . . ?
C2 C1 C6 C7 -176.1(3) . . . . ?
C2 C3 C4 C5 1.5(5) . . . . ?
C3 C4 C5 C6 -1.4(5) . . . . ?
C3 C4 C5 C9 -179.0(3) . . . . ?
C4 C5 C6 C1 -0.6(4) . . . . ?
C4 C5 C6 C7 178.0(3) . . . . ?
C4 C5 C9 C18 86.3(3) . . . . ?
C4 C5 C9 N1 -152.2(3) . . . . ?
C5 C6 C7 Br1 -110.5(3) . . . . ?
C5 C6 C7 C8 8.9(4) . . . . ?
C5 C9 C18 C17 -89.7(3) . . . . ?
C5 C9 C18 C19 88.8(3) . . . . ?
C5 C9 N1 C8 -62.7(3) . . . . ?
C5 C9 N1 C10 170.6(2) . . . . ?
C6 C1 C2 C3 -2.4(6) . . . . ?
C6 C5 C9 C18 -91.3(3) . . . . ?
C6 C5 C9 N1 30.3(4) . . . . ?
C6 C7 C8 N1 -40.3(3) . . . . ?
C6 C7 C8 N2 83.4(3) . . . . ?
C7 C8 N1 C9 68.3(3) . . . . ?
C7 C8 N1 C10 -166.0(2) . . . . ?
C7 C8 N2 C19 -97.8(3) . . . . ?
C7 C8 N2 C25 86.8(3) . . . . ?
C9 C5 C6 C1 177.0(3) . . . . ?
C9 C5 C6 C7 -4.4(4) . . . . ?
C9 C18 C19 C20 -179.6(3) . . . . ?
C9 C18 C19 N2 0.5(4) . . . . ?
C10 C11 C12 C13 -178.6(3) . . . . ?
C10 C11 C16 C15 178.6(3) . . . . ?
C11 C10 N1 C8 60.8(3) . . . . ?
C11 C10 N1 C9 -175.3(2) . . . . ?
C11 C12 C13 C14 -0.8(6) . . . . ?
C12 C11 C16 C15 -0.6(5) . . . . ?
C12 C13 C14 C15 1.0(6) . . . . ?
C13 C14 C15 C16 -1.1(6) . . . . ?
C14 C15 C16 C11 0.9(6) . . . . ?
C16 C11 C12 C13 0.6(5) . . . . ?
C17 C18 C19 C20 -1.1(5) . . . . ?
C17 C18 C19 N2 179.0(3) . . . . ?
C18 C9 N1 C8 58.0(3) . . . . ?
C18 C9 N1 C10 -68.7(3) . . . . ?
C18 C17 C22 C21 38.1(4) . . . . ?
C18 C19 C20 C21 -18.7(4) . . . . ?
C18 C19 N2 C8 3.8(4) . . . . ?
C18 C19 N2 C25 179.1(3) . . . . ?
C19 C20 C21 C22 44.7(4) . . . . ?
C19 C20 C21 C23 -76.0(3) . . . . ?
C19 C20 C21 C24 162.9(3) . . . . ?
C20 C19 N2 C8 -176.1(3) . . . . ?
C20 C19 N2 C25 -0.8(4) . . . . ?
C20 C21 C22 C17 -54.9(4) . . . . ?
C22 C17 C18 C9 169.9(3) . . . . ?
C22 C17 C18 C19 -8.6(4) . . . . ?
C23 C21 C22 C17 66.3(4) . . . . ?
C24 C21 C22 C17 -172.4(3) . . . . ?
C25 C26 C27 C28 -0.6(5) . . . . ?
C26 C25 C30 C29 -2.1(4) . . . . ?
C26 C25 N2 C8 -101.9(3) . . . . ?
C26 C25 N2 C19 82.7(3) . . . . ?
C26 C27 C28 C29 -1.6(5) . . . . ?
C26 C27 C28 C31 177.7(3) . . . . ?
C27 C28 C29 C30 2.0(5) . . . . ?
C28 C29 C30 C25 -0.1(5) . . . . ?
C30 C25 C26 C27 2.5(4) . . . . ?
C30 C25 N2 C8 79.8(3) . . . . ?
C30 C25 N2 C19 -95.6(3) . . . . ?
C31 C28 C29 C30 -177.4(3) . . . . ?
N1 C8 N2 C19 24.3(4) . . . . ?
N1 C8 N2 C25 -151.1(2) . . . . ?
N1 C9 C18 C17 149.6(3) . . . . ?
N1 C9 C18 C19 -31.9(4) . . . . ?
N1 C10 C11 C12 -133.8(3) . . . . ?
N1 C10 C11 C16 47.0(4) . . . . ?
N2 C8 N1 C9 -54.2(3) . . . . ?
N2 C8 N1 C10 71.4(3) . . . . ?
N2 C19 C20 C21 161.2(3) . . . . ?
N2 C25 C26 C27 -175.9(3) . . . . ?
N2 C25 C30 C29 176.2(3) . . . . ?
O1 C17 C18 C9 -7.6(5) . . . . ?
O1 C17 C18 C19 173.9(3) . . . . ?
O1 C17 C22 C21 -144.3(3) . . . . ?

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

data_201803150_tw
_database_code_depnum_ccdc_archive 'CCDC 1944660'
loop_
_audit_author_name
_audit_author_address
'Qilin Wang'
;Henan University
China
;
_audit_update_record             
;
2019-08-01 deposited with the CCDC.	2019-12-17 downloaded from the CCDC.
;
_audit_creation_date             2018-03-05
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C39 H39 N5 O5'
_chemical_formula_sum            'C39 H39 N5 O5'
_chemical_formula_weight         657.75
_chemical_melting_point          ?
_chemical_oxdiff_formula         C40H30N3O5Br1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   11.80408(14)
_cell_length_b                   18.74504(18)
_cell_length_c                   31.2581(4)
_cell_angle_alpha                90
_cell_angle_beta                 79.1361(11)
_cell_angle_gamma                90
_cell_volume                     6792.46(13)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    13858
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.6640
_cell_measurement_theta_min      3.7250
_shelx_estimated_absorpt_T_max   0.934
_shelx_estimated_absorpt_T_min   0.879
_exptl_absorpt_coefficient_mu    0.697
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84160
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             2784
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.0253
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            11515
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.096
_diffrn_reflns_theta_max         67.096
_diffrn_reflns_theta_min         3.722
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -74.00  -16.80   0.4000   16.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -19.0000   60.0000 143

#__ type_ start__ end____ width___ exp.time_
  2 omega  -94.00  -62.80   0.4000   16.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  178.0000   90.0000 78

#__ type_ start__ end____ width___ exp.time_
  3 omega   24.00   50.00   0.4000   16.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   77.0000  -60.0000 65

#__ type_ start__ end____ width___ exp.time_
  4 omega    2.00   37.20   0.4000   16.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000   90.0000 88

#__ type_ start__ end____ width___ exp.time_
  5 omega   -6.00   68.00   0.4000   16.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -97.0000 -153.0000 185

#__ type_ start__ end____ width___ exp.time_
  6 omega    0.00   26.00   0.4000   16.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   19.0000   90.0000 65

#__ type_ start__ end____ width___ exp.time_
  7 omega   50.00  103.20   0.4000   16.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   57.0000  -90.0000 133

#__ type_ start__ end____ width___ exp.time_
  8 omega  -16.00   52.00   0.4000   16.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -57.0000   90.0000 170

#__ type_ start__ end____ width___ exp.time_
  9 omega   61.00   93.00   0.4000   16.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000 -150.0000 80

#__ type_ start__ end____ width___ exp.time_
 10 omega   45.00   74.20   0.4000   16.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000   90.0000 73

#__ type_ start__ end____ width___ exp.time_
 11 omega   46.00   72.00   0.4000   16.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   19.0000   90.0000 65

#__ type_ start__ end____ width___ exp.time_
 12 omega   60.00  103.20   0.4000   16.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   77.0000  -60.0000 108

#__ type_ start__ end____ width___ exp.time_
 13 omega   74.00  100.00   0.4000   52.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -97.0000 -153.0000 65

#__ type_ start__ end____ width___ exp.time_
 14 omega  100.80  178.00   0.4000   52.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000  -60.0000 193

#__ type_ start__ end____ width___ exp.time_
 15 omega   46.00   85.20   0.4000   52.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000   30.0000 98

#__ type_ start__ end____ width___ exp.time_
 16 omega   38.00  113.20   0.4000   52.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  -60.0000 188

#__ type_ start__ end____ width___ exp.time_
 17 omega   42.00  108.00   0.4000   52.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000   90.0000 165

#__ type_ start__ end____ width___ exp.time_
 18 omega   83.00  175.00   0.4000   52.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -120.0000 230

#__ type_ start__ end____ width___ exp.time_
 19 omega   40.00   90.00   0.4000   52.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  120.0000 125

#__ type_ start__ end____ width___ exp.time_
 20 omega   56.00   82.00   0.4000   52.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  150.0000 65

#__ type_ start__ end____ width___ exp.time_
 21 omega  111.00  169.00   0.4000   52.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000 -180.0000 145

#__ type_ start__ end____ width___ exp.time_
 22 omega   45.00   73.00   0.4000   52.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -180.0000 70

#__ type_ start__ end____ width___ exp.time_
 23 omega   68.00   94.00   0.4000   52.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000 -180.0000 65
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.1220333000
_diffrn_orient_matrix_UB_12      0.0177796000
_diffrn_orient_matrix_UB_13      -0.0076587000
_diffrn_orient_matrix_UB_21      0.0513503000
_diffrn_orient_matrix_UB_22      0.0252290000
_diffrn_orient_matrix_UB_23      -0.0465206000
_diffrn_orient_matrix_UB_31      -0.0115330000
_diffrn_orient_matrix_UB_32      -0.0761516000
_diffrn_orient_matrix_UB_33      -0.0172119000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                9893
_reflns_number_total             11515
_reflns_odcompleteness_completeness 94.43
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SIR2004 (Burla et al., 2007)'
_refine_diff_density_max         0.381
_refine_diff_density_min         -0.274
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     890
_refine_ls_number_reflns         11515
_refine_ls_number_restraints     44
_refine_ls_R_factor_all          0.0596
_refine_ls_R_factor_gt           0.0516
_refine_ls_restrained_S_all      1.056
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0903P)²+0.7126P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1400
_refine_ls_wR_factor_ref         0.1465
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.6569(10)
 0.3431(10)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3. Rigid bond restraints
 C36', C37'
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C24, C25
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
4. Uiso/Uaniso restraints and constraints
Uanis(C36') \\sim Ueq, Uanis(C37') \\sim Ueq, Uanis(C38') \\sim Ueq,
Uanis(C39') \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C24) \\sim Ueq, Uanis(C25) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(C33') \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
5.a Ternary CH refined with riding coordinates:
 C16(H16), C18(H18), C19(H19), C20(H20), C28(H28), C30(H30), C16'(H16'),
 C18'(H18'), C19'(H19'), C20'(H20'), C28'(H28'), C30'(H30')
5.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C4(H4A,H4B), C21(H21A,H21B), C33(H33A,H33B), C2'(H2'A,H2'B),
 C4'(H4'A,H4'B), C21'(H21C,H21D), C33'(H33C,H33D)
5.c Aromatic/amide H refined with riding coordinates:
 C10(H10), C11(H11), C13(H13), C14(H14), C23(H23), C24(H24), C25(H25),
 C26(H26), C27(H27), C31(H31), C32(H32), C35(H35), C36(H36), C37(H37), C38(H38),
  C39(H39), C10'(H10'), C11'(H11'), C13'(H13'), C14'(H14'), C23'(H23'),
 C24'(H24'), C25'(H25'), C26'(H26'), C27'(H27'), C31'(H31'), C32'(H32'),
 C35'(H35'), C36'(H36'), C37'(H37'), C38'(H38'), C39'(H39')
5.d Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C15(H15A,H15B,H15C), C7'(H7'A,H7'B,H7'C),
 C8'(H8'A,H8'B,H8'C), C15'(H15D,H15E,H15F)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3358(2) 0.83578(13) 0.45512(8) 0.0477(5) Uani 1 1 d . . . . .
C2 C 0.3112(3) 0.75714(14) 0.45657(8) 0.0580(7) Uani 1 1 d . . . . .
H2A H 0.2297 0.7500 0.4567 0.070 Uiso 1 1 calc R . . . .
H2B H 0.3275 0.7379 0.4836 0.070 Uiso 1 1 calc R . . . .
C3 C 0.3809(3) 0.71575(14) 0.41858(9) 0.0567(7) Uani 1 1 d . . . . .
C4 C 0.3596(3) 0.75061(13) 0.37664(8) 0.0542(6) Uani 1 1 d . . . . .
H4A H 0.4129 0.7303 0.3522 0.065 Uiso 1 1 calc R . . . .
H4B H 0.2821 0.7389 0.3729 0.065 Uiso 1 1 calc R . . . .
C5 C 0.3732(2) 0.83036(12) 0.37536(7) 0.0428(5) Uani 1 1 d . . . . .
C6 C 0.3679(2) 0.86930(12) 0.41277(7) 0.0415(5) Uani 1 1 d . . . . .
C7 C 0.5086(3) 0.71839(19) 0.42136(11) 0.0738(9) Uani 1 1 d . . . . .
H7A H 0.5522 0.6907 0.3981 0.111 Uiso 1 1 calc GR . . . .
H7B H 0.5190 0.6992 0.4488 0.111 Uiso 1 1 calc GR . . . .
H7C H 0.5348 0.7670 0.4189 0.111 Uiso 1 1 calc GR . . . .
C8 C 0.3377(4) 0.63923(15) 0.41979(11) 0.0842(11) Uani 1 1 d . . . . .
H8A H 0.2566 0.6391 0.4193 0.126 Uiso 1 1 calc GR . . . .
H8B H 0.3509 0.6165 0.4459 0.126 Uiso 1 1 calc GR . . . .
H8C H 0.3783 0.6139 0.3949 0.126 Uiso 1 1 calc GR . . . .
C9 C 0.3821(2) 0.82946(13) 0.29595(8) 0.0459(5) Uani 1 1 d . . . . .
C10 C 0.2775(3) 0.79860(15) 0.29218(10) 0.0577(6) Uani 1 1 d . . . . .
H10 H 0.2171 0.7981 0.3160 0.069 Uiso 1 1 calc R . . . .
C11 C 0.2629(3) 0.76909(15) 0.25380(10) 0.0664(8) Uani 1 1 d . . . . .
H11 H 0.1929 0.7476 0.2521 0.080 Uiso 1 1 calc R . . . .
C12 C 0.3495(4) 0.77032(16) 0.21753(11) 0.0759(10) Uani 1 1 d . . . . .
C13 C 0.4539(4) 0.80253(16) 0.22095(10) 0.0736(9) Uani 1 1 d . . . . .
H13 H 0.5131 0.8046 0.1967 0.088 Uiso 1 1 calc R . . . .
C14 C 0.4701(2) 0.83126(14) 0.25989(8) 0.0560(6) Uani 1 1 d . . . . .
H14 H 0.5406 0.8519 0.2619 0.067 Uiso 1 1 calc R . . . .
C15 C 0.3324(6) 0.7392(3) 0.17446(14) 0.125(2) Uani 1 1 d . . . . .
H15A H 0.3455 0.6886 0.1744 0.188 Uiso 1 1 calc GR . . . .
H15B H 0.3858 0.7608 0.1511 0.188 Uiso 1 1 calc GR . . . .
H15C H 0.2549 0.7483 0.1706 0.188 Uiso 1 1 calc GR . . . .
C16 C 0.40285(19) 0.94158(12) 0.33341(7) 0.0413(5) Uani 1 1 d . . . . .
H16 H 0.4465 0.9559 0.3049 0.050 Uiso 1 1 calc R . . . .
C17 C 0.46427(19) 0.97049(12) 0.36860(7) 0.0410(5) Uani 1 1 d . . . . .
C18 C 0.39490(19) 0.94762(12) 0.41232(7) 0.0409(5) Uani 1 1 d . . . . .
H18 H 0.4396 0.9578 0.4351 0.049 Uiso 1 1 calc R . . . .
C19 C 0.2860(2) 0.99488(12) 0.41981(7) 0.0430(5) Uani 1 1 d . . . . .
H19 H 0.2186 0.9746 0.4391 0.052 Uiso 1 1 calc R . . . .
C20 C 0.2640(2) 1.02219(12) 0.37527(7) 0.0436(5) Uani 1 1 d . . . . .
H20 H 0.1862 1.0421 0.3781 0.052 Uiso 1 1 calc R . . . .
C21 C 0.2581(2) 0.99893(15) 0.29805(8) 0.0533(6) Uani 1 1 d . . . . .
H21A H 0.2762 0.9620 0.2761 0.064 Uiso 1 1 calc R . . . .
H21B H 0.3055 1.0401 0.2881 0.064 Uiso 1 1 calc R . . . .
C22 C 0.1336(2) 1.01912(14) 0.30223(8) 0.0521(6) Uani 1 1 d . . . . .
C23 C 0.1029(3) 1.08333(18) 0.28504(11) 0.0734(9) Uani 1 1 d . . . . .
H23 H 0.1595 1.1150 0.2719 0.088 Uiso 1 1 calc R . . . .
C24 C -0.0133(4) 1.0996(2) 0.28770(14) 0.0930(10) Uani 1 1 d . U . . .
H24 H -0.0338 1.1421 0.2758 0.112 Uiso 1 1 calc R . . . .
C25 C -0.0972(4) 1.0547(3) 0.30735(13) 0.0940(11) Uani 1 1 d . U . . .
H25 H -0.1744 1.0669 0.3092 0.113 Uiso 1 1 calc R . . . .
C26 C -0.0689(3) 0.9920(2) 0.32435(14) 0.0874(11) Uani 1 1 d . . . . .
H26 H -0.1265 0.9613 0.3379 0.105 Uiso 1 1 calc R . . . .
C27 C 0.0466(3) 0.97405(17) 0.32145(11) 0.0692(8) Uani 1 1 d . . . . .
H27 H 0.0654 0.9307 0.3327 0.083 Uiso 1 1 calc R . . . .
C28 C 0.3155(2) 1.07382(12) 0.42990(8) 0.0481(5) Uani 1 1 d . . . . .
H28 H 0.2441 1.1007 0.4397 0.058 Uiso 1 1 calc R . . . .
C29 C 0.3532(2) 1.08160(12) 0.38060(8) 0.0466(5) Uani 1 1 d . . . . .
C30 C 0.4758(2) 1.05334(13) 0.36568(8) 0.0471(5) Uani 1 1 d . . . . .
H30 H 0.5048 1.0676 0.3354 0.057 Uiso 1 1 calc R . . . .
C31 C 0.5537(2) 1.08213(13) 0.39440(9) 0.0535(6) Uani 1 1 d . . . . .
H31 H 0.6310 1.0907 0.3828 0.064 Uiso 1 1 calc R . . . .
C32 C 0.5129(2) 1.09560(13) 0.43647(9) 0.0560(6) Uani 1 1 d . . . . .
H32 H 0.5658 1.1085 0.4537 0.067 Uiso 1 1 calc R . . . .
C33 C 0.3682(3) 1.07306(16) 0.50303(9) 0.0653(7) Uani 1 1 d . . . . .
H33A H 0.4237 1.0949 0.5182 0.078 Uiso 1 1 calc R . . . .
H33B H 0.3739 1.0218 0.5061 0.078 Uiso 1 1 calc R . . . .
C34 C 0.2497(3) 1.09646(16) 0.52399(9) 0.0620(7) Uani 1 1 d . . . . .
C35 C 0.1641(4) 1.0466(2) 0.53381(13) 0.0910(11) Uani 1 1 d . . . . .
H35 H 0.1805 0.9988 0.5273 0.109 Uiso 1 1 calc R . . . .
C36 C 0.0531(5) 1.0664(3) 0.55332(19) 0.1263(18) Uani 1 1 d . . . . .
H36 H -0.0042 1.0319 0.5596 0.152 Uiso 1 1 calc R . . . .
C37 C 0.0274(6) 1.1358(4) 0.56341(18) 0.136(2) Uani 1 1 d . . . . .
H37 H -0.0470 1.1490 0.5765 0.163 Uiso 1 1 calc R . . . .
C38 C 0.1124(6) 1.1856(3) 0.55410(18) 0.128(2) Uani 1 1 d . . . . .
H38 H 0.0959 1.2332 0.5609 0.154 Uiso 1 1 calc R . . . .
C39 C 0.2242(5) 1.1658(2) 0.53439(13) 0.0968(12) Uani 1 1 d . . . . .
H39 H 0.2816 1.2003 0.5283 0.116 Uiso 1 1 calc R . . . .
N1 N 0.39904(18) 0.86378(10) 0.33543(6) 0.0443(4) Uani 1 1 d . . . . .
N2 N 0.58617(17) 0.94048(11) 0.35991(7) 0.0494(5) Uani 1 1 d . . . . .
N3 N 0.28837(16) 0.97298(10) 0.33917(6) 0.0430(4) Uani 1 1 d . . . . .
N4 N 0.3385(2) 1.15339(12) 0.36133(8) 0.0596(6) Uani 1 1 d . . . . .
N5 N 0.3983(2) 1.09185(11) 0.45629(7) 0.0523(5) Uani 1 1 d . . . . .
O1 O 0.3265(2) 0.87118(10) 0.48858(5) 0.0620(5) Uani 1 1 d . . . . .
O2 O 0.62199(18) 0.91108(12) 0.38897(7) 0.0710(6) Uani 1 1 d . . . . .
O3 O 0.64289(18) 0.94943(14) 0.32353(7) 0.0757(6) Uani 1 1 d . . . . .
O4 O 0.2916(3) 1.19973(12) 0.38431(9) 0.1025(9) Uani 1 1 d . . . . .
O5 O 0.3707(3) 1.16153(13) 0.32282(9) 0.1080(11) Uani 1 1 d . . . . .
C1' C 0.9313(2) 0.33785(15) 0.45155(9) 0.0543(6) Uani 1 1 d . . . . .
C2' C 0.9609(3) 0.26051(15) 0.45474(8) 0.0588(7) Uani 1 1 d . . . . .
H2'A H 0.9151 0.2410 0.4812 0.071 Uiso 1 1 calc R . . . .
H2'B H 1.0414 0.2565 0.4571 0.071 Uiso 1 1 calc R . . . .
C3' C 0.9403(2) 0.21610(14) 0.41615(9) 0.0548(6) Uani 1 1 d . . . . .
C4' C 1.0094(3) 0.25073(14) 0.37467(8) 0.0556(6) Uani 1 1 d . . . . .
H4'A H 1.0908 0.2414 0.3734 0.067 Uiso 1 1 calc R . . . .
H4'B H 0.9874 0.2285 0.3494 0.067 Uiso 1 1 calc R . . . .
C5' C 0.9913(2) 0.33048(13) 0.37239(8) 0.0466(5) Uani 1 1 d . . . . .
C6' C 0.9511(2) 0.36994(13) 0.40829(8) 0.0471(5) Uani 1 1 d . . . . .
C7' C 0.8129(3) 0.21323(17) 0.41472(10) 0.0664(7) Uani 1 1 d . . . . .
H7'A H 0.7716 0.1931 0.4414 0.100 Uiso 1 1 calc GR . . . .
H7'B H 0.8013 0.1841 0.3906 0.100 Uiso 1 1 calc GR . . . .
H7'C H 0.7851 0.2606 0.4112 0.100 Uiso 1 1 calc GR . . . .
C8' C 0.9841(3) 0.13981(16) 0.42009(11) 0.0752(9) Uani 1 1 d . . . . .
H8'A H 1.0646 0.1411 0.4216 0.113 Uiso 1 1 calc GR . . . .
H8'B H 0.9736 0.1126 0.3951 0.113 Uiso 1 1 calc GR . . . .
H8'C H 0.9417 0.1181 0.4460 0.113 Uiso 1 1 calc GR . . . .
C9' C 1.0732(2) 0.32673(13) 0.29332(8) 0.0475(5) Uani 1 1 d . . . . .
C10' C 1.1807(2) 0.29679(15) 0.29265(10) 0.0579(7) Uani 1 1 d . . . . .
H10' H 1.2121 0.2950 0.3178 0.070 Uiso 1 1 calc R . . . .
C11' C 1.2411(3) 0.26929(15) 0.25325(11) 0.0722(9) Uani 1 1 d . . . . .
H11' H 1.3119 0.2472 0.2528 0.087 Uiso 1 1 calc R . . . .
C12' C 1.1993(3) 0.27380(16) 0.21539(11) 0.0732(9) Uani 1 1 d . . . . .
C13' C 1.0914(4) 0.30329(17) 0.21714(10) 0.0749(9) Uani 1 1 d . . . . .
H13' H 1.0609 0.3058 0.1918 0.090 Uiso 1 1 calc R . . . .
C14' C 1.0278(2) 0.32906(14) 0.25537(9) 0.0580(6) Uani 1 1 d . . . . .
H14' H 0.9547 0.3480 0.2559 0.070 Uiso 1 1 calc R . . . .
C15' C 1.2717(5) 0.2478(2) 0.17299(13) 0.1177(18) Uani 1 1 d . . . . .
H15D H 1.2832 0.1973 0.1746 0.177 Uiso 1 1 calc GR . . . .
H15E H 1.3450 0.2716 0.1681 0.177 Uiso 1 1 calc GR . . . .
H15F H 1.2326 0.2582 0.1494 0.177 Uiso 1 1 calc GR . . . .
C16' C 1.0069(2) 0.43910(13) 0.32823(8) 0.0452(5) Uani 1 1 d . . . . .
H16' H 0.9970 0.4516 0.2987 0.054 Uiso 1 1 calc R . . . .
C17' C 0.9048(2) 0.46824(13) 0.36057(8) 0.0458(5) Uani 1 1 d . . . . .
C18' C 0.9214(2) 0.44732(13) 0.40592(8) 0.0474(5) Uani 1 1 d . . . . .
H18' H 0.8500 0.4570 0.4268 0.057 Uiso 1 1 calc R . . . .
C19' C 1.0176(2) 0.49751(14) 0.41562(8) 0.0515(6) Uani 1 1 d . . . . .
H19' H 1.0611 0.4795 0.4372 0.062 Uiso 1 1 calc R . . . .
C20' C 1.0926(2) 0.52330(13) 0.37206(8) 0.0501(6) Uani 1 1 d . . . . .
H20' H 1.1652 0.5443 0.3769 0.060 Uiso 1 1 calc R . . . .
C21' C 1.1856(2) 0.49913(16) 0.29586(9) 0.0595(7) Uani 1 1 d . . . . .
H21C H 1.1484 0.5402 0.2856 0.071 Uiso 1 1 calc R . . . .
H21D H 1.1907 0.4622 0.2739 0.071 Uiso 1 1 calc R . . . .
C22' C 1.3055(2) 0.51989(15) 0.30071(9) 0.0577(7) Uani 1 1 d . . . . .
C23' C 1.3523(3) 0.58307(19) 0.28255(12) 0.0795(9) Uani 1 1 d . . . . .
H23' H 1.3072 0.6138 0.2694 0.095 Uiso 1 1 calc R . . . .
C24' C 1.4657(4) 0.6011(3) 0.28369(15) 0.1033(15) Uani 1 1 d . . . . .
H24' H 1.4962 0.6437 0.2713 0.124 Uiso 1 1 calc R . . . .
C25' C 1.5332(3) 0.5561(3) 0.30315(14) 0.0995(14) Uani 1 1 d . . . . .
H25' H 1.6098 0.5674 0.3035 0.119 Uiso 1 1 calc R . . . .
C26' C 1.4861(3) 0.4954(3) 0.32172(16) 0.0989(13) Uani 1 1 d . . . . .
H26' H 1.5308 0.4652 0.3354 0.119 Uiso 1 1 calc R . . . .
C27' C 1.3735(3) 0.47696(19) 0.32103(13) 0.0800(10) Uani 1 1 d . . . . .
H27' H 1.3432 0.4350 0.3344 0.096 Uiso 1 1 calc R . . . .
C28' C 0.9742(3) 0.57570(14) 0.42292(9) 0.0557(6) Uani 1 1 d . . . . .
H28' H 1.0304 0.6043 0.4348 0.067 Uiso 1 1 calc R . . . .
C29' C 0.9972(2) 0.58162(13) 0.37338(9) 0.0523(6) Uani 1 1 d . . . . .
C30' C 0.8960(2) 0.55103(13) 0.35516(8) 0.0504(6) Uani 1 1 d . . . . .
H30' H 0.9043 0.5632 0.3242 0.060 Uiso 1 1 calc R . . . .
C31' C 0.7839(3) 0.57992(15) 0.38006(9) 0.0586(7) Uani 1 1 d . . . . .
H31' H 0.7224 0.5874 0.3659 0.070 Uiso 1 1 calc R . . . .
C32' C 0.7722(3) 0.59495(17) 0.42234(10) 0.0681(8) Uani 1 1 d . . . . .
H32' H 0.6995 0.6086 0.4371 0.082 Uiso 1 1 calc R . . . .
C33' C 0.8398(4) 0.5800(3) 0.49234(13) 0.1177(16) Uani 1 1 d . U . . .
H33C H 0.8983 0.6059 0.5041 0.141 Uiso 1 1 calc R . . . .
H33D H 0.8504 0.5296 0.4976 0.141 Uiso 1 1 calc R . . . .
C34' C 0.7252(4) 0.6017(2) 0.51652(11) 0.0844(10) Uani 1 1 d . . . . .
C35' C 0.6977(5) 0.6706(3) 0.52943(15) 0.1081(14) Uani 1 1 d . . . . .
H35' H 0.7552 0.7050 0.5230 0.130 Uiso 1 1 calc R . . . .
C36' C 0.5918(6) 0.6919(3) 0.55101(19) 0.137(2) Uani 1 1 d . U . . .
H36' H 0.5774 0.7392 0.5591 0.164 Uiso 1 1 calc R . . . .
C37' C 0.5110(7) 0.6432(5) 0.5599(2) 0.167(3) Uani 1 1 d . U . . .
H37' H 0.4387 0.6573 0.5748 0.200 Uiso 1 1 calc R . . . .
C38' C 0.5263(7) 0.5743(4) 0.5489(3) 0.181(3) Uani 1 1 d . U . . .
H38' H 0.4660 0.5419 0.5557 0.217 Uiso 1 1 calc R . . . .
C39' C 0.6372(7) 0.5518(3) 0.5265(2) 0.149(2) Uani 1 1 d . U . . .
H39' H 0.6504 0.5043 0.5186 0.179 Uiso 1 1 calc R . . . .
N1' N 1.01108(18) 0.36099(10) 0.33169(6) 0.0456(4) Uani 1 1 d . . . . .
N2' N 0.79671(19) 0.43673(12) 0.34870(8) 0.0550(5) Uani 1 1 d . . . . .
N3' N 1.11258(17) 0.47298(11) 0.33659(7) 0.0474(5) Uani 1 1 d . . . . .
N4' N 1.0344(2) 0.65298(12) 0.35376(9) 0.0645(6) Uani 1 1 d . . . . .
N5' N 0.8592(2) 0.59173(13) 0.44557(8) 0.0609(6) Uani 1 1 d . . . . .
O1' O 0.8950(2) 0.37354(11) 0.48405(6) 0.0718(6) Uani 1 1 d . . . . .
O2' O 0.7287(2) 0.40624(14) 0.37631(8) 0.0832(7) Uani 1 1 d . . . . .
O3' O 0.7832(2) 0.44481(14) 0.31100(8) 0.0791(6) Uani 1 1 d . . . . .
O4' O 1.0620(3) 0.69826(14) 0.37696(10) 0.1136(11) Uani 1 1 d . . . . .
O5' O 1.0419(4) 0.66117(14) 0.31531(9) 0.1131(11) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.502(3) . ?
C1 C6 1.450(3) . ?
C1 O1 1.226(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.524(4) . ?
C3 C4 1.527(4) . ?
C3 C7 1.527(5) . ?
C3 C8 1.520(4) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C5 1.503(3) . ?
C5 C6 1.370(3) . ?
C5 N1 1.378(3) . ?
C6 C18 1.502(3) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 C10 1.388(4) . ?
C9 C14 1.382(4) . ?
C9 N1 1.439(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.361(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.376(5) . ?
C12 C13 1.394(6) . ?
C12 C15 1.516(4) . ?
C13 H13 0.9300 . ?
C13 C14 1.377(4) . ?
C14 H14 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16 0.9800 . ?
C16 C17 1.526(3) . ?
C16 N1 1.460(3) . ?
C16 N3 1.454(3) . ?
C17 C18 1.517(3) . ?
C17 C30 1.560(3) . ?
C17 N2 1.521(3) . ?
C18 H18 0.9800 . ?
C18 C19 1.542(3) . ?
C19 H19 0.9800 . ?
C19 C20 1.550(3) . ?
C19 C28 1.566(3) . ?
C20 H20 0.9800 . ?
C20 C29 1.563(3) . ?
C20 N3 1.444(3) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C21 C22 1.500(4) . ?
C21 N3 1.480(3) . ?
C22 C23 1.394(4) . ?
C22 C27 1.377(4) . ?
C23 H23 0.9300 . ?
C23 C24 1.393(5) . ?
C24 H24 0.9300 . ?
C24 C25 1.355(7) . ?
C25 H25 0.9300 . ?
C25 C26 1.356(6) . ?
C26 H26 0.9300 . ?
C26 C27 1.391(5) . ?
C27 H27 0.9300 . ?
C28 H28 0.9800 . ?
C28 C29 1.528(3) . ?
C28 N5 1.433(3) . ?
C29 C30 1.529(4) . ?
C29 N4 1.498(3) . ?
C30 H30 0.9800 . ?
C30 C31 1.501(3) . ?
C31 H31 0.9300 . ?
C31 C32 1.336(4) . ?
C32 H32 0.9300 . ?
C32 N5 1.380(4) . ?
C33 H33A 0.9700 . ?
C33 H33B 0.9700 . ?
C33 C34 1.495(4) . ?
C33 N5 1.479(4) . ?
C34 C35 1.368(5) . ?
C34 C39 1.359(5) . ?
C35 H35 0.9300 . ?
C35 C36 1.387(7) . ?
C36 H36 0.9300 . ?
C36 C37 1.359(8) . ?
C37 H37 0.9300 . ?
C37 C38 1.361(9) . ?
C38 H38 0.9300 . ?
C38 C39 1.397(7) . ?
C39 H39 0.9300 . ?
N2 O2 1.205(3) . ?
N2 O3 1.218(3) . ?
N4 O4 1.195(3) . ?
N4 O5 1.202(3) . ?
C1' C2' 1.499(4) . ?
C1' C6' 1.458(3) . ?
C1' O1' 1.224(3) . ?
C2' H2'A 0.9700 . ?
C2' H2'B 0.9700 . ?
C2' C3' 1.522(4) . ?
C3' C4' 1.540(3) . ?
C3' C7' 1.513(4) . ?
C3' C8' 1.534(4) . ?
C4' H4'A 0.9700 . ?
C4' H4'B 0.9700 . ?
C4' C5' 1.514(3) . ?
C5' C6' 1.353(3) . ?
C5' N1' 1.374(3) . ?
C6' C18' 1.497(3) . ?
C7' H7'A 0.9600 . ?
C7' H7'B 0.9600 . ?
C7' H7'C 0.9600 . ?
C8' H8'A 0.9600 . ?
C8' H8'B 0.9600 . ?
C8' H8'C 0.9600 . ?
C9' C10' 1.384(4) . ?
C9' C14' 1.391(4) . ?
C9' N1' 1.434(3) . ?
C10' H10' 0.9300 . ?
C10' C11' 1.400(4) . ?
C11' H11' 0.9300 . ?
C11' C12' 1.368(5) . ?
C12' C13' 1.381(6) . ?
C12' C15' 1.515(4) . ?
C13' H13' 0.9300 . ?
C13' C14' 1.373(4) . ?
C14' H14' 0.9300 . ?
C15' H15D 0.9600 . ?
C15' H15E 0.9600 . ?
C15' H15F 0.9600 . ?
C16' H16' 0.9800 . ?
C16' C17' 1.521(3) . ?
C16' N1' 1.470(3) . ?
C16' N3' 1.467(3) . ?
C17' C18' 1.519(3) . ?
C17' C30' 1.567(3) . ?
C17' N2' 1.514(3) . ?
C18' H18' 0.9800 . ?
C18' C19' 1.549(4) . ?
C19' H19' 0.9800 . ?
C19' C20' 1.555(3) . ?
C19' C28' 1.556(4) . ?
C20' H20' 0.9800 . ?
C20' C29' 1.565(4) . ?
C20' N3' 1.441(3) . ?
C21' H21C 0.9700 . ?
C21' H21D 0.9700 . ?
C21' C22' 1.504(4) . ?
C21' N3' 1.480(3) . ?
C22' C23' 1.383(4) . ?
C22' C27' 1.374(5) . ?
C23' H23' 0.9300 . ?
C23' C24' 1.387(6) . ?
C24' H24' 0.9300 . ?
C24' C25' 1.378(7) . ?
C25' H25' 0.9300 . ?
C25' C26' 1.349(6) . ?
C26' H26' 0.9300 . ?
C26' C27' 1.377(5) . ?
C27' H27' 0.9300 . ?
C28' H28' 0.9800 . ?
C28' C29' 1.525(4) . ?
C28' N5' 1.439(4) . ?
C29' C30' 1.528(4) . ?
C29' N4' 1.502(3) . ?
C30' H30' 0.9800 . ?
C30' C31' 1.504(4) . ?
C31' H31' 0.9300 . ?
C31' C32' 1.333(4) . ?
C32' H32' 0.9300 . ?
C32' N5' 1.366(4) . ?
C33' H33C 0.9700 . ?
C33' H33D 0.9700 . ?
C33' C34' 1.478(6) . ?
C33' N5' 1.453(5) . ?
C34' C35' 1.373(6) . ?
C34' C39' 1.388(7) . ?
C35' H35' 0.9300 . ?
C35' C36' 1.364(8) . ?
C36' H36' 0.9300 . ?
C36' C37' 1.312(9) . ?
C37' H37' 0.9300 . ?
C37' C38' 1.340(9) . ?
C38' H38' 0.9300 . ?
C38' C39' 1.427(10) . ?
C39' H39' 0.9300 . ?
N2' O2' 1.206(3) . ?
N2' O3' 1.228(3) . ?
N4' O4' 1.200(4) . ?
N4' O5' 1.198(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 118.0(2) . . ?
O1 C1 C2 121.3(2) . . ?
O1 C1 C6 120.7(2) . . ?
C1 C2 H2A 108.8 . . ?
C1 C2 H2B 108.8 . . ?
C1 C2 C3 113.8(2) . . ?
H2A C2 H2B 107.7 . . ?
C3 C2 H2A 108.8 . . ?
C3 C2 H2B 108.8 . . ?
C2 C3 C4 107.4(2) . . ?
C2 C3 C7 109.5(3) . . ?
C7 C3 C4 111.0(2) . . ?
C8 C3 C2 109.4(2) . . ?
C8 C3 C4 108.4(3) . . ?
C8 C3 C7 111.0(3) . . ?
C3 C4 H4A 108.6 . . ?
C3 C4 H4B 108.6 . . ?
H4A C4 H4B 107.6 . . ?
C5 C4 C3 114.5(2) . . ?
C5 C4 H4A 108.6 . . ?
C5 C4 H4B 108.6 . . ?
C6 C5 C4 121.3(2) . . ?
C6 C5 N1 119.8(2) . . ?
N1 C5 C4 118.7(2) . . ?
C1 C6 C18 116.8(2) . . ?
C5 C6 C1 120.7(2) . . ?
C5 C6 C18 122.5(2) . . ?
C3 C7 H7A 109.5 . . ?
C3 C7 H7B 109.5 . . ?
C3 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C3 C8 H8A 109.5 . . ?
C3 C8 H8B 109.5 . . ?
C3 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C10 C9 N1 121.9(2) . . ?
C14 C9 C10 119.0(2) . . ?
C14 C9 N1 118.9(2) . . ?
C9 C10 H10 119.8 . . ?
C11 C10 C9 120.4(3) . . ?
C11 C10 H10 119.8 . . ?
C10 C11 H11 119.3 . . ?
C10 C11 C12 121.4(3) . . ?
C12 C11 H11 119.3 . . ?
C11 C12 C13 118.3(3) . . ?
C11 C12 C15 121.5(4) . . ?
C13 C12 C15 120.2(4) . . ?
C12 C13 H13 119.7 . . ?
C14 C13 C12 120.6(3) . . ?
C14 C13 H13 119.7 . . ?
C9 C14 H14 119.9 . . ?
C13 C14 C9 120.2(3) . . ?
C13 C14 H14 119.9 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C16 H16 108.6 . . ?
N1 C16 H16 108.6 . . ?
N1 C16 C17 109.77(18) . . ?
N3 C16 H16 108.6 . . ?
N3 C16 C17 108.88(18) . . ?
N3 C16 N1 112.26(18) . . ?
C16 C17 C30 111.06(19) . . ?
C18 C17 C16 107.45(18) . . ?
C18 C17 C30 111.12(19) . . ?
C18 C17 N2 112.85(19) . . ?
N2 C17 C16 107.58(18) . . ?
N2 C17 C30 106.76(18) . . ?
C6 C18 C17 111.23(18) . . ?
C6 C18 H18 109.0 . . ?
C6 C18 C19 113.00(19) . . ?
C17 C18 H18 109.0 . . ?
C17 C18 C19 105.51(18) . . ?
C19 C18 H18 109.0 . . ?
C18 C19 H19 115.3 . . ?
C18 C19 C20 109.22(18) . . ?
C18 C19 C28 111.25(19) . . ?
C20 C19 H19 115.3 . . ?
C20 C19 C28 87.14(17) . . ?
C28 C19 H19 115.3 . . ?
C19 C20 H20 111.0 . . ?
C19 C20 C29 84.79(17) . . ?
C29 C20 H20 111.0 . . ?
N3 C20 C19 116.64(19) . . ?
N3 C20 H20 111.0 . . ?
N3 C20 C29 120.0(2) . . ?
H21A C21 H21B 107.7 . . ?
C22 C21 H21A 108.8 . . ?
C22 C21 H21B 108.8 . . ?
N3 C21 H21A 108.8 . . ?
N3 C21 H21B 108.8 . . ?
N3 C21 C22 113.6(2) . . ?
C23 C22 C21 120.4(3) . . ?
C27 C22 C21 121.4(3) . . ?
C27 C22 C23 118.1(3) . . ?
C22 C23 H23 120.3 . . ?
C24 C23 C22 119.4(4) . . ?
C24 C23 H23 120.3 . . ?
C23 C24 H24 119.4 . . ?
C25 C24 C23 121.2(4) . . ?
C25 C24 H24 119.4 . . ?
C24 C25 H25 119.9 . . ?
C24 C25 C26 120.2(4) . . ?
C26 C25 H25 119.9 . . ?
C25 C26 H26 120.2 . . ?
C25 C26 C27 119.7(4) . . ?
C27 C26 H26 120.2 . . ?
C22 C27 C26 121.4(3) . . ?
C22 C27 H27 119.3 . . ?
C26 C27 H27 119.3 . . ?
C19 C28 H28 109.7 . . ?
C29 C28 C19 85.46(17) . . ?
C29 C28 H28 109.7 . . ?
N5 C28 C19 122.7(2) . . ?
N5 C28 H28 109.7 . . ?
N5 C28 C29 117.2(2) . . ?
C28 C29 C20 88.01(18) . . ?
C28 C29 C30 110.7(2) . . ?
C30 C29 C20 109.79(19) . . ?
N4 C29 C20 117.7(2) . . ?
N4 C29 C28 117.2(2) . . ?
N4 C29 C30 111.3(2) . . ?
C17 C30 H30 109.7 . . ?
C29 C30 C17 105.06(19) . . ?
C29 C30 H30 109.7 . . ?
C31 C30 C17 112.3(2) . . ?
C31 C30 C29 110.1(2) . . ?
C31 C30 H30 109.7 . . ?
C30 C31 H31 119.7 . . ?
C32 C31 C30 120.6(2) . . ?
C32 C31 H31 119.7 . . ?
C31 C32 H32 117.5 . . ?
C31 C32 N5 125.0(2) . . ?
N5 C32 H32 117.5 . . ?
H33A C33 H33B 107.8 . . ?
C34 C33 H33A 108.9 . . ?
C34 C33 H33B 108.9 . . ?
N5 C33 H33A 108.9 . . ?
N5 C33 H33B 108.9 . . ?
N5 C33 C34 113.2(2) . . ?
C35 C34 C33 119.2(3) . . ?
C39 C34 C33 122.1(3) . . ?
C39 C34 C35 118.6(4) . . ?
C34 C35 H35 119.6 . . ?
C34 C35 C36 120.8(4) . . ?
C36 C35 H35 119.6 . . ?
C35 C36 H36 119.7 . . ?
C37 C36 C35 120.6(5) . . ?
C37 C36 H36 119.7 . . ?
C36 C37 H37 120.5 . . ?
C36 C37 C38 118.9(5) . . ?
C38 C37 H37 120.5 . . ?
C37 C38 H38 119.7 . . ?
C37 C38 C39 120.6(5) . . ?
C39 C38 H38 119.7 . . ?
C34 C39 C38 120.5(5) . . ?
C34 C39 H39 119.8 . . ?
C38 C39 H39 119.8 . . ?
C5 N1 C9 122.06(19) . . ?
C5 N1 C16 119.54(18) . . ?
C9 N1 C16 114.67(18) . . ?
O2 N2 C17 119.3(2) . . ?
O2 N2 O3 123.9(2) . . ?
O3 N2 C17 116.8(2) . . ?
C16 N3 C21 113.36(19) . . ?
C20 N3 C16 113.53(18) . . ?
C20 N3 C21 115.06(19) . . ?
O4 N4 C29 119.1(3) . . ?
O4 N4 O5 122.2(3) . . ?
O5 N4 C29 118.6(2) . . ?
C28 N5 C33 116.7(2) . . ?
C32 N5 C28 118.1(2) . . ?
C32 N5 C33 119.2(2) . . ?
C6' C1' C2' 117.5(2) . . ?
O1' C1' C2' 121.5(2) . . ?
O1' C1' C6' 120.9(3) . . ?
C1' C2' H2'A 108.8 . . ?
C1' C2' H2'B 108.8 . . ?
C1' C2' C3' 113.7(2) . . ?
H2'A C2' H2'B 107.7 . . ?
C3' C2' H2'A 108.8 . . ?
C3' C2' H2'B 108.8 . . ?
C2' C3' C4' 107.4(2) . . ?
C2' C3' C8' 109.8(2) . . ?
C7' C3' C2' 110.5(3) . . ?
C7' C3' C4' 111.2(2) . . ?
C7' C3' C8' 108.8(3) . . ?
C8' C3' C4' 109.1(2) . . ?
C3' C4' H4'A 108.9 . . ?
C3' C4' H4'B 108.9 . . ?
H4'A C4' H4'B 107.7 . . ?
C5' C4' C3' 113.5(2) . . ?
C5' C4' H4'A 108.9 . . ?
C5' C4' H4'B 108.9 . . ?
C6' C5' C4' 122.1(2) . . ?
C6' C5' N1' 120.8(2) . . ?
N1' C5' C4' 117.0(2) . . ?
C1' C6' C18' 116.6(2) . . ?
C5' C6' C1' 120.9(2) . . ?
C5' C6' C18' 122.5(2) . . ?
C3' C7' H7'A 109.5 . . ?
C3' C7' H7'B 109.5 . . ?
C3' C7' H7'C 109.5 . . ?
H7'A C7' H7'B 109.5 . . ?
H7'A C7' H7'C 109.5 . . ?
H7'B C7' H7'C 109.5 . . ?
C3' C8' H8'A 109.5 . . ?
C3' C8' H8'B 109.5 . . ?
C3' C8' H8'C 109.5 . . ?
H8'A C8' H8'B 109.5 . . ?
H8'A C8' H8'C 109.5 . . ?
H8'B C8' H8'C 109.5 . . ?
C10' C9' C14' 120.0(2) . . ?
C10' C9' N1' 121.1(2) . . ?
C14' C9' N1' 118.7(2) . . ?
C9' C10' H10' 120.8 . . ?
C9' C10' C11' 118.4(3) . . ?
C11' C10' H10' 120.8 . . ?
C10' C11' H11' 118.9 . . ?
C12' C11' C10' 122.1(3) . . ?
C12' C11' H11' 118.9 . . ?
C11' C12' C13' 118.1(3) . . ?
C11' C12' C15' 120.1(4) . . ?
C13' C12' C15' 121.8(4) . . ?
C12' C13' H13' 119.2 . . ?
C14' C13' C12' 121.6(3) . . ?
C14' C13' H13' 119.2 . . ?
C9' C14' H14' 120.1 . . ?
C13' C14' C9' 119.7(3) . . ?
C13' C14' H14' 120.1 . . ?
C12' C15' H15D 109.5 . . ?
C12' C15' H15E 109.5 . . ?
C12' C15' H15F 109.5 . . ?
H15D C15' H15E 109.5 . . ?
H15D C15' H15F 109.5 . . ?
H15E C15' H15F 109.5 . . ?
C17' C16' H16' 108.7 . . ?
N1' C16' H16' 108.7 . . ?
N1' C16' C17' 110.02(19) . . ?
N3' C16' H16' 108.7 . . ?
N3' C16' C17' 108.7(2) . . ?
N3' C16' N1' 112.12(19) . . ?
C16' C17' C30' 110.12(19) . . ?
C18' C17' C16' 107.6(2) . . ?
C18' C17' C30' 112.3(2) . . ?
N2' C17' C16' 107.2(2) . . ?
N2' C17' C18' 113.0(2) . . ?
N2' C17' C30' 106.5(2) . . ?
C6' C18' C17' 111.6(2) . . ?
C6' C18' H18' 109.1 . . ?
C6' C18' C19' 113.0(2) . . ?
C17' C18' H18' 109.1 . . ?
C17' C18' C19' 104.74(19) . . ?
C19' C18' H18' 109.1 . . ?
C18' C19' H19' 115.1 . . ?
C18' C19' C20' 109.6(2) . . ?
C18' C19' C28' 111.5(2) . . ?
C20' C19' H19' 115.1 . . ?
C20' C19' C28' 87.31(19) . . ?
C28' C19' H19' 115.1 . . ?
C19' C20' H20' 111.1 . . ?
C19' C20' C29' 84.60(19) . . ?
C29' C20' H20' 111.1 . . ?
N3' C20' C19' 117.0(2) . . ?
N3' C20' H20' 111.1 . . ?
N3' C20' C29' 119.3(2) . . ?
H21C C21' H21D 107.7 . . ?
C22' C21' H21C 108.8 . . ?
C22' C21' H21D 108.8 . . ?
N3' C21' H21C 108.8 . . ?
N3' C21' H21D 108.8 . . ?
N3' C21' C22' 113.9(2) . . ?
C23' C22' C21' 119.4(3) . . ?
C27' C22' C21' 122.6(3) . . ?
C27' C22' C23' 118.0(3) . . ?
C22' C23' H23' 119.7 . . ?
C22' C23' C24' 120.7(4) . . ?
C24' C23' H23' 119.7 . . ?
C23' C24' H24' 119.9 . . ?
C25' C24' C23' 120.2(4) . . ?
C25' C24' H24' 119.9 . . ?
C24' C25' H25' 120.6 . . ?
C26' C25' C24' 118.7(4) . . ?
C26' C25' H25' 120.6 . . ?
C25' C26' H26' 119.2 . . ?
C25' C26' C27' 121.7(4) . . ?
C27' C26' H26' 119.2 . . ?
C22' C27' C26' 120.7(4) . . ?
C22' C27' H27' 119.7 . . ?
C26' C27' H27' 119.7 . . ?
C19' C28' H28' 110.0 . . ?
C29' C28' C19' 85.92(19) . . ?
C29' C28' H28' 110.0 . . ?
N5' C28' C19' 121.6(2) . . ?
N5' C28' H28' 110.0 . . ?
N5' C28' C29' 117.1(2) . . ?
C28' C29' C20' 88.0(2) . . ?
C28' C29' C30' 110.4(2) . . ?
C30' C29' C20' 109.7(2) . . ?
N4' C29' C20' 117.2(2) . . ?
N4' C29' C28' 117.5(2) . . ?
N4' C29' C30' 111.8(2) . . ?
C17' C30' H30' 109.9 . . ?
C29' C30' C17' 105.0(2) . . ?
C29' C30' H30' 109.9 . . ?
C31' C30' C17' 111.7(2) . . ?
C31' C30' C29' 110.2(2) . . ?
C31' C30' H30' 109.9 . . ?
C30' C31' H31' 119.8 . . ?
C32' C31' C30' 120.4(3) . . ?
C32' C31' H31' 119.8 . . ?
C31' C32' H32' 117.6 . . ?
C31' C32' N5' 124.7(3) . . ?
N5' C32' H32' 117.6 . . ?
H33C C33' H33D 107.5 . . ?
C34' C33' H33C 108.4 . . ?
C34' C33' H33D 108.4 . . ?
N5' C33' H33C 108.4 . . ?
N5' C33' H33D 108.4 . . ?
N5' C33' C34' 115.3(4) . . ?
C35' C34' C33' 123.5(5) . . ?
C35' C34' C39' 116.3(5) . . ?
C39' C34' C33' 120.2(5) . . ?
C34' C35' H35' 117.8 . . ?
C36' C35' C34' 124.3(5) . . ?
C36' C35' H35' 117.8 . . ?
C35' C36' H36' 121.2 . . ?
C37' C36' C35' 117.6(6) . . ?
C37' C36' H36' 121.2 . . ?
C36' C37' H37' 118.1 . . ?
C36' C37' C38' 123.9(7) . . ?
C38' C37' H37' 118.1 . . ?
C37' C38' H38' 120.7 . . ?
C37' C38' C39' 118.6(6) . . ?
C39' C38' H38' 120.7 . . ?
C34' C39' C38' 119.3(6) . . ?
C34' C39' H39' 120.4 . . ?
C38' C39' H39' 120.4 . . ?
C5' N1' C9' 124.0(2) . . ?
C5' N1' C16' 118.73(19) . . ?
C9' N1' C16' 113.81(18) . . ?
O2' N2' C17' 119.2(2) . . ?
O2' N2' O3' 123.8(3) . . ?
O3' N2' C17' 117.0(2) . . ?
C16' N3' C21' 111.5(2) . . ?
C20' N3' C16' 113.54(19) . . ?
C20' N3' C21' 115.4(2) . . ?
O4' N4' C29' 118.3(3) . . ?
O5' N4' C29' 119.0(3) . . ?
O5' N4' O4' 122.6(3) . . ?
C28' N5' C33' 114.7(3) . . ?
C32' N5' C28' 118.8(2) . . ?
C32' N5' C33' 123.4(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 -54.7(3) . . . . ?
C1 C2 C3 C7 65.9(3) . . . . ?
C1 C2 C3 C8 -172.2(3) . . . . ?
C1 C6 C18 C17 160.8(2) . . . . ?
C1 C6 C18 C19 -80.7(3) . . . . ?
C2 C1 C6 C5 1.3(4) . . . . ?
C2 C1 C6 C18 -178.5(2) . . . . ?
C2 C3 C4 C5 49.0(3) . . . . ?
C3 C4 C5 C6 -19.8(4) . . . . ?
C3 C4 C5 N1 155.9(2) . . . . ?
C4 C5 C6 C1 -7.2(4) . . . . ?
C4 C5 C6 C18 172.6(2) . . . . ?
C4 C5 N1 C9 17.7(3) . . . . ?
C4 C5 N1 C16 174.8(2) . . . . ?
C5 C6 C18 C17 -18.9(3) . . . . ?
C5 C6 C18 C19 99.5(3) . . . . ?
C6 C1 C2 C3 31.4(4) . . . . ?
C6 C5 N1 C9 -166.6(2) . . . . ?
C6 C5 N1 C16 -9.5(3) . . . . ?
C6 C18 C19 C20 -98.7(2) . . . . ?
C6 C18 C19 C28 166.79(19) . . . . ?
C7 C3 C4 C5 -70.7(3) . . . . ?
C8 C3 C4 C5 167.0(3) . . . . ?
C9 C10 C11 C12 -1.5(5) . . . . ?
C10 C9 C14 C13 -0.2(4) . . . . ?
C10 C9 N1 C5 52.1(3) . . . . ?
C10 C9 N1 C16 -106.0(3) . . . . ?
C10 C11 C12 C13 0.2(5) . . . . ?
C10 C11 C12 C15 -178.4(3) . . . . ?
C11 C12 C13 C14 1.0(5) . . . . ?
C12 C13 C14 C9 -1.0(5) . . . . ?
C14 C9 C10 C11 1.5(4) . . . . ?
C14 C9 N1 C5 -132.0(3) . . . . ?
C14 C9 N1 C16 69.8(3) . . . . ?
C15 C12 C13 C14 179.7(3) . . . . ?
C16 C17 C18 C6 49.5(2) . . . . ?
C16 C17 C18 C19 -73.4(2) . . . . ?
C16 C17 C30 C29 70.5(2) . . . . ?
C16 C17 C30 C31 -169.8(2) . . . . ?
C16 C17 N2 O2 -128.3(2) . . . . ?
C16 C17 N2 O3 53.3(3) . . . . ?
C17 C16 N1 C5 42.5(3) . . . . ?
C17 C16 N1 C9 -158.82(19) . . . . ?
C17 C16 N3 C20 0.5(3) . . . . ?
C17 C16 N3 C21 134.2(2) . . . . ?
C17 C18 C19 C20 23.1(2) . . . . ?
C17 C18 C19 C28 -71.5(2) . . . . ?
C17 C30 C31 C32 -84.7(3) . . . . ?
C18 C17 C30 C29 -49.1(2) . . . . ?
C18 C17 C30 C31 70.6(3) . . . . ?
C18 C17 N2 O2 -9.9(3) . . . . ?
C18 C17 N2 O3 171.7(2) . . . . ?
C18 C19 C20 C29 -83.7(2) . . . . ?
C18 C19 C20 N3 37.4(3) . . . . ?
C18 C19 C28 C29 81.0(2) . . . . ?
C18 C19 C28 N5 -38.7(3) . . . . ?
C19 C20 C29 C28 -28.60(17) . . . . ?
C19 C20 C29 C30 82.7(2) . . . . ?
C19 C20 C29 N4 -148.5(2) . . . . ?
C19 C20 N3 C16 -51.5(3) . . . . ?
C19 C20 N3 C21 175.6(2) . . . . ?
C19 C28 C29 C20 28.26(17) . . . . ?
C19 C28 C29 C30 -82.2(2) . . . . ?
C19 C28 C29 N4 148.7(2) . . . . ?
C19 C28 N5 C32 85.4(3) . . . . ?
C19 C28 N5 C33 -67.3(3) . . . . ?
C20 C19 C28 C29 -28.54(17) . . . . ?
C20 C19 C28 N5 -148.2(2) . . . . ?
C20 C29 C30 C17 -21.7(2) . . . . ?
C20 C29 C30 C31 -142.9(2) . . . . ?
C20 C29 N4 O4 98.2(3) . . . . ?
C20 C29 N4 O5 -79.1(4) . . . . ?
C21 C22 C23 C24 177.3(3) . . . . ?
C21 C22 C27 C26 -178.4(3) . . . . ?
C22 C21 N3 C16 169.6(2) . . . . ?
C22 C21 N3 C20 -57.4(3) . . . . ?
C22 C23 C24 C25 1.1(6) . . . . ?
C23 C22 C27 C26 -0.9(5) . . . . ?
C23 C24 C25 C26 -1.0(6) . . . . ?
C24 C25 C26 C27 -0.1(6) . . . . ?
C25 C26 C27 C22 1.1(6) . . . . ?
C27 C22 C23 C24 -0.2(5) . . . . ?
C28 C19 C20 C29 27.87(17) . . . . ?
C28 C19 C20 N3 148.9(2) . . . . ?
C28 C29 C30 C17 73.8(2) . . . . ?
C28 C29 C30 C31 -47.3(3) . . . . ?
C28 C29 N4 O4 -4.9(4) . . . . ?
C28 C29 N4 O5 177.8(3) . . . . ?
C29 C20 N3 C16 48.4(3) . . . . ?
C29 C20 N3 C21 -84.5(3) . . . . ?
C29 C28 N5 C32 -17.6(3) . . . . ?
C29 C28 N5 C33 -170.2(2) . . . . ?
C29 C30 C31 C32 32.0(3) . . . . ?
C30 C17 C18 C6 171.17(19) . . . . ?
C30 C17 C18 C19 48.3(2) . . . . ?
C30 C17 N2 O2 112.5(2) . . . . ?
C30 C17 N2 O3 -65.9(3) . . . . ?
C30 C29 N4 O4 -133.8(3) . . . . ?
C30 C29 N4 O5 48.9(4) . . . . ?
C30 C31 C32 N5 -6.8(4) . . . . ?
C31 C32 N5 C28 -1.5(4) . . . . ?
C31 C32 N5 C33 150.4(3) . . . . ?
C33 C34 C35 C36 179.9(4) . . . . ?
C33 C34 C39 C38 -179.8(4) . . . . ?
C34 C33 N5 C28 -49.0(3) . . . . ?
C34 C33 N5 C32 158.7(2) . . . . ?
C34 C35 C36 C37 -0.6(8) . . . . ?
C35 C34 C39 C38 -0.9(6) . . . . ?
C35 C36 C37 C38 -0.1(10) . . . . ?
C36 C37 C38 C39 0.2(10) . . . . ?
C37 C38 C39 C34 0.3(8) . . . . ?
C39 C34 C35 C36 1.1(6) . . . . ?
N1 C5 C6 C1 177.2(2) . . . . ?
N1 C5 C6 C18 -3.0(4) . . . . ?
N1 C9 C10 C11 177.3(2) . . . . ?
N1 C9 C14 C13 -176.2(3) . . . . ?
N1 C16 C17 C18 -61.4(2) . . . . ?
N1 C16 C17 C30 176.87(18) . . . . ?
N1 C16 C17 N2 60.4(2) . . . . ?
N1 C16 N3 C20 122.3(2) . . . . ?
N1 C16 N3 C21 -104.0(2) . . . . ?
N2 C17 C18 C6 -69.0(2) . . . . ?
N2 C17 C18 C19 168.17(18) . . . . ?
N2 C17 C30 C29 -172.54(18) . . . . ?
N2 C17 C30 C31 -52.8(3) . . . . ?
N3 C16 C17 C18 61.9(2) . . . . ?
N3 C16 C17 C30 -59.9(2) . . . . ?
N3 C16 C17 N2 -176.37(18) . . . . ?
N3 C16 N1 C5 -78.8(3) . . . . ?
N3 C16 N1 C9 79.9(2) . . . . ?
N3 C20 C29 C28 -146.5(2) . . . . ?
N3 C20 C29 C30 -35.1(3) . . . . ?
N3 C20 C29 N4 93.6(3) . . . . ?
N3 C21 C22 C23 133.0(3) . . . . ?
N3 C21 C22 C27 -49.6(3) . . . . ?
N4 C29 C30 C17 -153.9(2) . . . . ?
N4 C29 C30 C31 85.0(2) . . . . ?
N5 C28 C29 C20 152.9(2) . . . . ?
N5 C28 C29 C30 42.5(3) . . . . ?
N5 C28 C29 N4 -86.7(3) . . . . ?
N5 C33 C34 C35 106.0(3) . . . . ?
N5 C33 C34 C39 -75.1(4) . . . . ?
O1 C1 C2 C3 -150.4(3) . . . . ?
O1 C1 C6 C5 -177.0(3) . . . . ?
O1 C1 C6 C18 3.2(4) . . . . ?
C1' C2' C3' C4' 55.8(3) . . . . ?
C1' C2' C3' C7' -65.6(3) . . . . ?
C1' C2' C3' C8' 174.3(3) . . . . ?
C1' C6' C18' C17' -160.0(2) . . . . ?
C1' C6' C18' C19' 82.2(3) . . . . ?
C2' C1' C6' C5' 1.9(4) . . . . ?
C2' C1' C6' C18' -179.8(2) . . . . ?
C2' C3' C4' C5' -48.8(3) . . . . ?
C3' C4' C5' C6' 20.5(4) . . . . ?
C3' C4' C5' N1' -155.7(2) . . . . ?
C4' C5' C6' C1' 4.6(4) . . . . ?
C4' C5' C6' C18' -173.6(2) . . . . ?
C4' C5' N1' C9' -15.9(4) . . . . ?
C4' C5' N1' C16' -173.4(2) . . . . ?
C5' C6' C18' C17' 18.3(3) . . . . ?
C5' C6' C18' C19' -99.5(3) . . . . ?
C6' C1' C2' C3' -33.9(4) . . . . ?
C6' C5' N1' C9' 167.8(2) . . . . ?
C6' C5' N1' C16' 10.3(4) . . . . ?
C6' C18' C19' C20' 97.5(2) . . . . ?
C6' C18' C19' C28' -167.5(2) . . . . ?
C7' C3' C4' C5' 72.2(3) . . . . ?
C8' C3' C4' C5' -167.8(3) . . . . ?
C9' C10' C11' C12' 2.7(4) . . . . ?
C10' C9' C14' C13' -1.7(4) . . . . ?
C10' C9' N1' C5' -50.8(3) . . . . ?
C10' C9' N1' C16' 107.7(3) . . . . ?
C10' C11' C12' C13' -3.4(5) . . . . ?
C10' C11' C12' C15' 175.8(3) . . . . ?
C11' C12' C13' C14' 1.5(5) . . . . ?
C12' C13' C14' C9' 1.1(5) . . . . ?
C14' C9' C10' C11' -0.1(4) . . . . ?
C14' C9' N1' C5' 134.4(3) . . . . ?
C14' C9' N1' C16' -67.1(3) . . . . ?
C15' C12' C13' C14' -177.7(3) . . . . ?
C16' C17' C18' C6' -48.2(3) . . . . ?
C16' C17' C18' C19' 74.4(2) . . . . ?
C16' C17' C30' C29' -71.8(2) . . . . ?
C16' C17' C30' C31' 168.8(2) . . . . ?
C16' C17' N2' O2' 126.7(3) . . . . ?
C16' C17' N2' O3' -54.2(3) . . . . ?
C17' C16' N1' C5' -42.7(3) . . . . ?
C17' C16' N1' C9' 157.6(2) . . . . ?
C17' C16' N3' C20' 0.0(3) . . . . ?
C17' C16' N3' C21' -132.5(2) . . . . ?
C17' C18' C19' C20' -24.3(3) . . . . ?
C17' C18' C19' C28' 70.7(2) . . . . ?
C17' C30' C31' C32' 83.7(3) . . . . ?
C18' C17' C30' C29' 48.1(3) . . . . ?
C18' C17' C30' C31' -71.4(3) . . . . ?
C18' C17' N2' O2' 8.3(3) . . . . ?
C18' C17' N2' O3' -172.5(2) . . . . ?
C18' C19' C20' C29' 84.5(2) . . . . ?
C18' C19' C20' N3' -35.8(3) . . . . ?
C18' C19' C28' C29' -81.9(2) . . . . ?
C18' C19' C28' N5' 37.6(3) . . . . ?
C19' C20' C29' C28' 28.01(19) . . . . ?
C19' C20' C29' C30' -83.0(2) . . . . ?
C19' C20' C29' N4' 148.1(2) . . . . ?
C19' C20' N3' C16' 50.2(3) . . . . ?
C19' C20' N3' C21' -179.2(2) . . . . ?
C19' C28' C29' C20' -27.94(19) . . . . ?
C19' C28' C29' C30' 82.4(2) . . . . ?
C19' C28' C29' N4' -147.8(2) . . . . ?
C19' C28' N5' C32' -87.9(3) . . . . ?
C19' C28' N5' C33' 72.8(4) . . . . ?
C20' C19' C28' C29' 28.15(19) . . . . ?
C20' C19' C28' N5' 147.6(3) . . . . ?
C20' C29' C30' C17' 22.7(3) . . . . ?
C20' C29' C30' C31' 143.2(2) . . . . ?
C20' C29' N4' O4' -91.2(4) . . . . ?
C20' C29' N4' O5' 84.5(4) . . . . ?
C21' C22' C23' C24' -175.2(3) . . . . ?
C21' C22' C27' C26' 174.8(4) . . . . ?
C22' C21' N3' C16' -167.5(2) . . . . ?
C22' C21' N3' C20' 61.0(3) . . . . ?
C22' C23' C24' C25' -0.2(7) . . . . ?
C23' C22' C27' C26' -2.4(5) . . . . ?
C23' C24' C25' C26' -1.4(7) . . . . ?
C24' C25' C26' C27' 1.1(7) . . . . ?
C25' C26' C27' C22' 0.8(7) . . . . ?
C27' C22' C23' C24' 2.1(5) . . . . ?
C28' C19' C20' C29' -27.43(19) . . . . ?
C28' C19' C20' N3' -147.7(2) . . . . ?
C28' C29' C30' C17' -72.7(2) . . . . ?
C28' C29' C30' C31' 47.8(3) . . . . ?
C28' C29' N4' O4' 11.7(4) . . . . ?
C28' C29' N4' O5' -172.6(3) . . . . ?
C29' C20' N3' C16' -49.3(3) . . . . ?
C29' C20' N3' C21' 81.3(3) . . . . ?
C29' C28' N5' C32' 14.9(4) . . . . ?
C29' C28' N5' C33' 175.5(3) . . . . ?
C29' C30' C31' C32' -32.7(4) . . . . ?
C30' C17' C18' C6' -169.6(2) . . . . ?
C30' C17' C18' C19' -46.9(3) . . . . ?
C30' C17' N2' O2' -115.4(3) . . . . ?
C30' C17' N2' O3' 63.7(3) . . . . ?
C30' C29' N4' O4' 140.9(3) . . . . ?
C30' C29' N4' O5' -43.4(4) . . . . ?
C30' C31' C32' N5' 5.7(5) . . . . ?
C31' C32' N5' C28' 4.4(5) . . . . ?
C31' C32' N5' C33' -154.5(4) . . . . ?
C33' C34' C35' C36' 178.7(5) . . . . ?
C33' C34' C39' C38' -178.4(6) . . . . ?
C34' C33' N5' C28' 175.2(4) . . . . ?
C34' C33' N5' C32' -25.2(6) . . . . ?
C34' C35' C36' C37' 0.0(11) . . . . ?
C35' C34' C39' C38' 0.0(9) . . . . ?
C35' C36' C37' C38' -0.5(13) . . . . ?
C36' C37' C38' C39' 0.7(15) . . . . ?
C37' C38' C39' C34' -0.5(12) . . . . ?
C39' C34' C35' C36' 0.2(8) . . . . ?
N1' C5' C6' C1' -179.3(2) . . . . ?
N1' C5' C6' C18' 2.5(4) . . . . ?
N1' C9' C10' C11' -174.9(2) . . . . ?
N1' C9' C14' C13' 173.2(2) . . . . ?
N1' C16' C17' C18' 60.5(3) . . . . ?
N1' C16' C17' C30' -176.86(19) . . . . ?
N1' C16' C17' N2' -61.4(2) . . . . ?
N1' C16' N3' C20' -121.8(2) . . . . ?
N1' C16' N3' C21' 105.7(2) . . . . ?
N2' C17' C18' C6' 69.9(3) . . . . ?
N2' C17' C18' C19' -167.43(19) . . . . ?
N2' C17' C30' C29' 172.32(19) . . . . ?
N2' C17' C30' C31' 52.8(3) . . . . ?
N3' C16' C17' C18' -62.6(2) . . . . ?
N3' C16' C17' C30' 60.0(3) . . . . ?
N3' C16' C17' N2' 175.53(18) . . . . ?
N3' C16' N1' C5' 78.3(3) . . . . ?
N3' C16' N1' C9' -81.4(3) . . . . ?
N3' C20' C29' C28' 146.0(2) . . . . ?
N3' C20' C29' C30' 35.0(3) . . . . ?
N3' C20' C29' N4' -93.8(3) . . . . ?
N3' C21' C22' C23' -134.7(3) . . . . ?
N3' C21' C22' C27' 48.1(4) . . . . ?
N4' C29' C30' C17' 154.5(2) . . . . ?
N4' C29' C30' C31' -85.0(3) . . . . ?
N5' C28' C29' C20' -151.5(2) . . . . ?
N5' C28' C29' C30' -41.2(3) . . . . ?
N5' C28' C29' N4' 88.6(3) . . . . ?
N5' C33' C34' C35' -82.4(6) . . . . ?
N5' C33' C34' C39' 96.0(6) . . . . ?
O1' C1' C2' C3' 148.1(3) . . . . ?
O1' C1' C6' C5' 179.9(3) . . . . ?
O1' C1' C6' C18' -1.8(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.6569(10)
2 0.3431(10)

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

data_201809362
_database_code_depnum_ccdc_archive 'CCDC 1947689'
loop_
_audit_author_name
_audit_author_address
'Qilin Wang'
;Henan University
China
;
_audit_update_record             
;
2019-08-17 deposited with the CCDC.	2019-12-17 downloaded from the CCDC.
;
_audit_creation_date             2018-09-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C45 H39 Cl2 N3 O'
_chemical_formula_sum            'C45 H39 Cl2 N3 O'
_chemical_formula_weight         708.69
_chemical_melting_point          ?
_chemical_oxdiff_formula         C15H15O3
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   13.58053(11)
_cell_length_b                   20.7753(2)
_cell_length_c                   29.2921(3)
_cell_angle_alpha                90
_cell_angle_beta                 102.8973(9)
_cell_angle_gamma                90
_cell_volume                     8055.96(13)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    11310
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.8680
_cell_measurement_theta_min      3.9470
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.725
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80582
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.169
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             2976
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0322
_diffrn_reflns_av_unetI/netI     0.0341
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            37627
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.075
_diffrn_reflns_theta_max         67.075
_diffrn_reflns_theta_min         3.352
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -86.00  -33.00   0.5000    4.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  178.0000 -180.0000 106

#__ type_ start__ end____ width___ exp.time_
  2 omega  -92.00  -66.00   0.5000    4.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  178.0000  -30.0000 52

#__ type_ start__ end____ width___ exp.time_
  3 omega  -24.00   35.00   0.5000    4.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   57.0000 -180.0000 118

#__ type_ start__ end____ width___ exp.time_
  4 omega  -87.00  -34.00   0.5000    4.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  178.0000  -60.0000 106

#__ type_ start__ end____ width___ exp.time_
  5 omega   -1.00  109.00   0.5000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   19.0000 -150.0000 220

#__ type_ start__ end____ width___ exp.time_
  6 omega  -14.00   34.00   0.5000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -57.0000   60.0000 96

#__ type_ start__ end____ width___ exp.time_
  7 omega   77.00  103.00   0.5000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000   90.0000 52

#__ type_ start__ end____ width___ exp.time_
  8 omega   59.00   93.00   0.5000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000    0.0000 68

#__ type_ start__ end____ width___ exp.time_
  9 omega   23.00   71.00   0.5000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   57.0000  -90.0000 96

#__ type_ start__ end____ width___ exp.time_
 10 omega   58.00  101.00   0.5000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000  150.0000 86

#__ type_ start__ end____ width___ exp.time_
 11 omega   82.00  109.00   0.5000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000  120.0000 54

#__ type_ start__ end____ width___ exp.time_
 12 omega   39.00   67.00   0.5000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000    0.0000 56

#__ type_ start__ end____ width___ exp.time_
 13 omega   74.00  110.00   0.5000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000  -30.0000 72

#__ type_ start__ end____ width___ exp.time_
 14 omega   77.00  104.00   0.5000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   57.0000  -90.0000 54

#__ type_ start__ end____ width___ exp.time_
 15 omega   97.00  156.00   0.5000   27.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000  150.0000 118

#__ type_ start__ end____ width___ exp.time_
 16 omega   39.00   98.00   0.5000   27.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -60.0000 118

#__ type_ start__ end____ width___ exp.time_
 17 omega   65.00  108.00   0.5000   27.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000   30.0000 86

#__ type_ start__ end____ width___ exp.time_
 18 omega  117.00  157.00   0.5000   27.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000   90.0000 80

#__ type_ start__ end____ width___ exp.time_
 19 omega   42.00   80.00   0.5000   27.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  120.0000 76

#__ type_ start__ end____ width___ exp.time_
 20 omega   53.00   79.00   0.5000   27.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -180.0000 52

#__ type_ start__ end____ width___ exp.time_
 21 omega   94.00  160.00   0.5000   27.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000   90.0000 132

#__ type_ start__ end____ width___ exp.time_
 22 omega   41.00   99.00   0.5000   27.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000    0.0000 116

#__ type_ start__ end____ width___ exp.time_
 23 omega   74.00  164.00   0.5000   27.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000   60.0000 180

#__ type_ start__ end____ width___ exp.time_
 24 omega   37.00  109.00   0.5000   27.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  -30.0000 144
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0564917000
_diffrn_orient_matrix_UB_12      -0.0647875000
_diffrn_orient_matrix_UB_13      0.0041741000
_diffrn_orient_matrix_UB_21      -0.0773419000
_diffrn_orient_matrix_UB_22      -0.0255756000
_diffrn_orient_matrix_UB_23      -0.0428702000
_diffrn_orient_matrix_UB_31      0.0661083000
_diffrn_orient_matrix_UB_32      0.0254026000
_diffrn_orient_matrix_UB_33      -0.0325096000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                10018
_reflns_number_total             14381
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         3.290
_refine_diff_density_min         -0.339
_refine_diff_density_rms         0.170
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.431
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     929
_refine_ls_number_reflns         14381
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1448
_refine_ls_R_factor_gt           0.1225
_refine_ls_restrained_S_all      1.431
_refine_ls_shift/su_max          0.546
_refine_ls_shift/su_mean         0.010
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3481
_refine_ls_wR_factor_ref         0.3780
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C36) = Uanis(C36A)
Uanis(C36') = Uanis(C1A)
3. Others
 Sof(H35C)=Sof(H35D)=Sof(C36A)=Sof(H36C)=Sof(H36D)=Sof(H37C)=Sof(H37D)=1-FVAR(1)
 Sof(H35A)=Sof(H35B)=Sof(C36)=Sof(H36A)=Sof(H36B)=Sof(H37A)=Sof(H37B)=FVAR(1)
 Sof(C1A)=Sof(H1AA)=Sof(H1AB)=Sof(H35G)=Sof(H35H)=Sof(H37G)=Sof(H37H)=1-FVAR(2)
 Sof(H35E)=Sof(H35F)=Sof(C36')=Sof(H36E)=Sof(H36F)=Sof(H37E)=Sof(H37F)=FVAR(2)
4.a Ternary CH refined with riding coordinates:
 C7(H7), C8(H8), C9(H9), C25(H25), C7'(H7'), C8'(H8'), C9'(H9'), C25'(H25')
4.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C26(H26A,H26B), C35(H35A,H35B), C35(H35C,H35D), C36(H36A,
 H36B), C36A(H36C,H36D), C37(H37A,H37B), C37(H37C,H37D), C1A(H1AA,H1AB),
 C10'(H10C,H10D), C26'(H26C,H26D), C35'(H35E,H35F), C35'(H35G,H35H), C36'(H36E,
 H36F), C37'(H37E,H37F), C37'(H37G,H37H)
4.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C12(H12), C13(H13), C14(H14), C15(H15), C16(H16),
 C18(H18), C19(H19), C21(H21), C23(H23), C24(H24), C28(H28), C29(H29), C30(H30),
  C31(H31), C32(H32), C40(H40), C41(H41), C43(H43), C44(H44), C2'(H2'),
 C3'(H3'), C5'(H5'), C12'(H12'), C13'(H13'), C14'(H14'), C15'(H15'), C16'(H16'),
  C18'(H18'), C19'(H19'), C21'(H21'), C23'(H23'), C24'(H24'), C28'(H28'),
 C29'(H29'), C30'(H30'), C31'(H31'), C32'(H32'), C40'(H40'), C41'(H41'),
 C43'(H43'), C44'(H44')
4.d Idealised Me refined as rotating group:
 C45(H45A,H45B,H45C), C45'(H45D,H45E,H45F)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1882(2) 0.7234(2) 0.42867(13) 0.0486(8) Uani 1 1 d . . . . .
C2 C 0.1256(3) 0.6859(2) 0.45040(14) 0.0581(10) Uani 1 1 d . . . . .
H2 H 0.0788 0.7061 0.4644 0.070 Uiso 1 1 calc R . . . .
C3 C 0.1324(3) 0.6212(3) 0.45124(16) 0.0650(12) Uani 1 1 d . . . . .
H3 H 0.0911 0.5971 0.4661 0.078 Uiso 1 1 calc R . . . .
C4 C 0.2011(3) 0.5905(2) 0.42992(16) 0.0629(11) Uani 1 1 d . . . . .
C5 C 0.2655(3) 0.6260(2) 0.40923(14) 0.0531(9) Uani 1 1 d . . . . .
H5 H 0.3127 0.6052 0.3957 0.064 Uiso 1 1 calc R . . . .
C6 C 0.2597(3) 0.6925(2) 0.40866(13) 0.0476(8) Uani 1 1 d . . . . .
C7 C 0.3289(2) 0.73337(18) 0.38660(13) 0.0456(8) Uani 1 1 d . . . . .
H7 H 0.3539 0.7079 0.3634 0.055 Uiso 1 1 calc R . . . .
C8 C 0.2700(3) 0.7912(2) 0.36276(14) 0.0510(9) Uani 1 1 d . . . . .
H8 H 0.3172 0.8183 0.3504 0.061 Uiso 1 1 calc R . . . .
C9 C 0.2380(3) 0.8289(2) 0.40182(14) 0.0528(9) Uani 1 1 d . . . . .
H9 H 0.1965 0.8654 0.3877 0.063 Uiso 1 1 calc R . . . .
C10 C 0.1253(3) 0.8247(3) 0.45684(16) 0.0623(11) Uani 1 1 d . . . . .
H10A H 0.1506 0.8684 0.4608 0.075 Uiso 1 1 calc R . . . .
H10B H 0.1407 0.8043 0.4874 0.075 Uiso 1 1 calc R . . . .
C11 C 0.0116(3) 0.8271(2) 0.43948(14) 0.0515(9) Uani 1 1 d . . . . .
C12 C -0.0386(3) 0.8024(3) 0.39712(16) 0.0683(12) Uani 1 1 d . . . . .
H12 H -0.0020 0.7831 0.3776 0.082 Uiso 1 1 calc R . . . .
C13 C -0.1426(3) 0.8060(3) 0.38309(17) 0.0787(15) Uani 1 1 d . . . . .
H13 H -0.1748 0.7890 0.3543 0.094 Uiso 1 1 calc R . . . .
C14 C -0.1984(3) 0.8339(3) 0.41079(18) 0.0741(14) Uani 1 1 d . . . . .
H14 H -0.2682 0.8368 0.4009 0.089 Uiso 1 1 calc R . . . .
C15 C -0.1501(4) 0.8576(3) 0.45338(19) 0.0737(13) Uani 1 1 d . . . . .
H15 H -0.1876 0.8759 0.4730 0.088 Uiso 1 1 calc R . . . .
C16 C -0.0448(3) 0.8548(2) 0.46777(16) 0.0620(10) Uani 1 1 d . . . . .
H16 H -0.0127 0.8717 0.4967 0.074 Uiso 1 1 calc R . . . .
C17 C 0.2678(3) 0.7747(2) 0.25646(14) 0.0572(10) Uani 1 1 d . . . . .
C18 C 0.3335(4) 0.7466(3) 0.23233(16) 0.0702(12) Uani 1 1 d . . . . .
H18 H 0.3426 0.7022 0.2337 0.084 Uiso 1 1 calc R . . . .
C19 C 0.3864(4) 0.7837(3) 0.20598(17) 0.0730(13) Uani 1 1 d . . . . .
H19 H 0.4313 0.7644 0.1904 0.088 Uiso 1 1 calc R . . . .
C20 C 0.3710(4) 0.8491(3) 0.20344(16) 0.0700(12) Uani 1 1 d . . . . .
C21 C 0.3022(4) 0.8778(2) 0.22416(15) 0.0647(11) Uani 1 1 d . . . . .
H21 H 0.2904 0.9218 0.2205 0.078 Uiso 1 1 calc R . . . .
C22 C 0.2492(3) 0.8417(2) 0.25086(15) 0.0591(10) Uani 1 1 d . . . . .
C23 C 0.1668(4) 0.8681(3) 0.26950(17) 0.0735(13) Uani 1 1 d . . . . .
H23 H 0.1405 0.9082 0.2593 0.088 Uiso 1 1 calc R . . . .
C24 C 0.1286(4) 0.8364(3) 0.30056(17) 0.0745(14) Uani 1 1 d . . . . .
H24 H 0.0709 0.8512 0.3093 0.089 Uiso 1 1 calc R . . . .
C25 C 0.1808(3) 0.7752(2) 0.32171(15) 0.0601(10) Uani 1 1 d . . . . .
H25 H 0.1322 0.7482 0.3331 0.072 Uiso 1 1 calc R . . . .
C26 C 0.2138(4) 0.6709(2) 0.28448(17) 0.0753(14) Uani 1 1 d . . . . .
H26A H 0.2050 0.6567 0.3148 0.090 Uiso 1 1 calc R . . . .
H26B H 0.2789 0.6552 0.2809 0.090 Uiso 1 1 calc R . . . .
C27 C 0.1329(3) 0.6401(2) 0.24730(15) 0.0589(10) Uani 1 1 d . . . . .
C28 C 0.0629(3) 0.6740(3) 0.21513(16) 0.0653(11) Uani 1 1 d . . . . .
H28 H 0.0664 0.7187 0.2145 0.078 Uiso 1 1 calc R . . . .
C29 C -0.0135(4) 0.6419(3) 0.18333(18) 0.0792(15) Uani 1 1 d . . . . .
H29 H -0.0606 0.6655 0.1619 0.095 Uiso 1 1 calc R . . . .
C30 C -0.0196(5) 0.5775(4) 0.1835(2) 0.0980(19) Uani 1 1 d . . . . .
H30 H -0.0697 0.5561 0.1620 0.118 Uiso 1 1 calc R . . . .
C31 C 0.0494(8) 0.5440(4) 0.2157(3) 0.153(4) Uani 1 1 d . . . . .
H31 H 0.0464 0.4993 0.2163 0.184 Uiso 1 1 calc R . . . .
C32 C 0.1235(6) 0.5757(3) 0.2476(3) 0.110(3) Uani 1 1 d . . . . .
H32 H 0.1683 0.5518 0.2699 0.132 Uiso 1 1 calc R . . . .
C33 C 0.4173(2) 0.75825(19) 0.42350(12) 0.0455(8) Uani 1 1 d . . . . .
C34 C 0.4106(3) 0.81615(19) 0.44367(14) 0.0480(8) Uani 1 1 d . . . . .
C35 C 0.4957(3) 0.8468(2) 0.47827(16) 0.0568(10) Uani 1 1 d . . . . .
H35A H 0.4691 0.8717 0.5008 0.068 Uiso 0.703(8) 1 calc R . P A 1
H35B H 0.5328 0.8756 0.4622 0.068 Uiso 0.703(8) 1 calc R . P A 1
H35C H 0.4968 0.8925 0.4717 0.068 Uiso 0.297(8) 1 calc R . P A 2
H35D H 0.4835 0.8418 0.5095 0.068 Uiso 0.297(8) 1 calc R . P A 2
C36 C 0.5666(4) 0.7939(3) 0.5036(2) 0.0603(14) Uani 0.703(8) 1 d . . P A 1
H36A H 0.6266 0.8138 0.5225 0.072 Uiso 0.703(8) 1 calc R . P A 1
H36B H 0.5329 0.7708 0.5245 0.072 Uiso 0.703(8) 1 calc R . P A 1
C36A C 0.5948(10) 0.8191(8) 0.4773(5) 0.0603(14) Uani 0.297(8) 1 d . . P A 2
H36C H 0.6418 0.8303 0.5064 0.072 Uiso 0.297(8) 1 calc R . P A 2
H36D H 0.6190 0.8391 0.4520 0.072 Uiso 0.297(8) 1 calc R . P A 2
C37 C 0.5968(3) 0.7481(2) 0.47138(17) 0.0648(11) Uani 1 1 d . . . . .
H37A H 0.6325 0.7128 0.4894 0.078 Uiso 0.703(8) 1 calc R . P A 1
H37B H 0.6437 0.7694 0.4557 0.078 Uiso 0.703(8) 1 calc R . P A 1
H37C H 0.5958 0.7280 0.5012 0.078 Uiso 0.297(8) 1 calc R . P A 2
H37D H 0.6599 0.7364 0.4633 0.078 Uiso 0.297(8) 1 calc R . P A 2
C38 C 0.5110(2) 0.72096(19) 0.43465(13) 0.0459(8) Uani 1 1 d . . . . .
C39 C 0.6033(3) 0.6312(2) 0.42094(15) 0.0543(9) Uani 1 1 d . . . . .
C40 C 0.6880(3) 0.6513(2) 0.40529(18) 0.0647(11) Uani 1 1 d . . . . .
H40 H 0.6875 0.6909 0.3904 0.078 Uiso 1 1 calc R . . . .
C41 C 0.7730(3) 0.6125(2) 0.41173(19) 0.0674(12) Uani 1 1 d . . . . .
H41 H 0.8285 0.6261 0.4006 0.081 Uiso 1 1 calc R . . . .
C42 C 0.7767(3) 0.5536(2) 0.43460(17) 0.0626(11) Uani 1 1 d . . . . .
C43 C 0.6932(4) 0.5342(2) 0.44894(18) 0.0652(11) Uani 1 1 d . . . . .
H43 H 0.6940 0.4944 0.4636 0.078 Uiso 1 1 calc R . . . .
C44 C 0.6061(3) 0.5717(2) 0.44250(17) 0.0628(10) Uani 1 1 d . . . . .
H44 H 0.5500 0.5568 0.4526 0.075 Uiso 1 1 calc R . . . .
C45 C 0.8714(4) 0.5131(3) 0.4430(2) 0.0850(16) Uani 1 1 d . . . . .
H45A H 0.8994 0.5141 0.4156 0.127 Uiso 1 1 calc GR . . . .
H45B H 0.8552 0.4695 0.4493 0.127 Uiso 1 1 calc GR . . . .
H45C H 0.9199 0.5299 0.4693 0.127 Uiso 1 1 calc GR . . . .
Cl1 Cl 0.20434(12) 0.50672(7) 0.42801(6) 0.0917(5) Uani 1 1 d . . . . .
Cl2 Cl 0.43871(13) 0.89581(10) 0.17151(6) 0.1064(6) Uani 1 1 d . . . . .
N1 N 0.1793(2) 0.79045(18) 0.42646(12) 0.0541(8) Uani 1 1 d . . . . .
N2 N 0.2166(3) 0.74060(19) 0.28452(13) 0.0652(9) Uani 1 1 d . . . . .
N3 N 0.5136(2) 0.66830(17) 0.41288(13) 0.0554(8) Uani 1 1 d . . . . .
O1 O 0.32815(19) 0.85427(13) 0.43418(11) 0.0553(7) Uani 1 1 d . . . . .
C1' C 0.7417(3) 0.2261(2) 0.41564(13) 0.0494(9) Uani 1 1 d . . . . .
C1A C 1.1279(5) 0.3045(4) 0.4818(3) 0.0604(15) Uani 0.532(8) 1 d . . P B 2
H1AA H 1.1886 0.3267 0.4979 0.072 Uiso 0.532(8) 1 calc R . P B 2
H1AB H 1.1015 0.2810 0.5051 0.072 Uiso 0.532(8) 1 calc R . P B 2
C2' C 0.6810(3) 0.1880(3) 0.43842(14) 0.0606(11) Uani 1 1 d . . . . .
H2' H 0.6320 0.2078 0.4512 0.073 Uiso 1 1 calc R . . . .
C3' C 0.6928(4) 0.1233(3) 0.44201(18) 0.0724(13) Uani 1 1 d . . . . .
H3' H 0.6529 0.0989 0.4575 0.087 Uiso 1 1 calc R . . . .
C4' C 0.7643(4) 0.0942(3) 0.4226(2) 0.0745(13) Uani 1 1 d . . . . .
C5' C 0.8246(3) 0.1290(2) 0.39930(16) 0.0591(10) Uani 1 1 d . . . . .
H5' H 0.8717 0.1082 0.3858 0.071 Uiso 1 1 calc R . . . .
C6' C 0.8140(3) 0.19493(19) 0.39634(12) 0.0466(8) Uani 1 1 d . . . . .
C7' C 0.8804(2) 0.23546(18) 0.37202(12) 0.0438(8) Uani 1 1 d . . . . .
H7' H 0.9042 0.2092 0.3488 0.053 Uiso 1 1 calc R . . . .
C8' C 0.8186(3) 0.29239(19) 0.34774(13) 0.0464(8) Uani 1 1 d . . . . .
H8' H 0.8644 0.3196 0.3345 0.056 Uiso 1 1 calc R . . . .
C9' C 0.7879(3) 0.33055(18) 0.38656(14) 0.0486(8) Uani 1 1 d . . . . .
H9' H 0.7453 0.3665 0.3722 0.058 Uiso 1 1 calc R . . . .
C10' C 0.6816(3) 0.3281(3) 0.44364(15) 0.0611(11) Uani 1 1 d . . . . .
H10C H 0.7141 0.3698 0.4497 0.073 Uiso 1 1 calc R . . . .
H10D H 0.6925 0.3053 0.4732 0.073 Uiso 1 1 calc R . . . .
C11' C 0.5682(3) 0.3388(2) 0.42596(14) 0.0520(9) Uani 1 1 d . . . . .
C12' C 0.5134(3) 0.3115(3) 0.38499(17) 0.0702(13) Uani 1 1 d . . . . .
H12' H 0.5454 0.2855 0.3669 0.084 Uiso 1 1 calc R . . . .
C13' C 0.4107(4) 0.3233(4) 0.37109(19) 0.0873(18) Uani 1 1 d . . . . .
H13' H 0.3738 0.3043 0.3438 0.105 Uiso 1 1 calc R . . . .
C14' C 0.3635(4) 0.3619(4) 0.3965(2) 0.100(2) Uani 1 1 d . . . . .
H14' H 0.2949 0.3703 0.3864 0.120 Uiso 1 1 calc R . . . .
C15' C 0.4171(4) 0.3886(4) 0.4373(2) 0.100(2) Uani 1 1 d . . . . .
H15' H 0.3847 0.4152 0.4549 0.120 Uiso 1 1 calc R . . . .
C16' C 0.5189(3) 0.3762(3) 0.45250(17) 0.0712(13) Uani 1 1 d . . . . .
H16' H 0.5544 0.3932 0.4808 0.085 Uiso 1 1 calc R . . . .
C17' C 0.8120(3) 0.2712(2) 0.24199(13) 0.0532(9) Uani 1 1 d . . . . .
C18' C 0.8756(3) 0.2415(2) 0.21716(15) 0.0619(11) Uani 1 1 d . . . . .
H18' H 0.8837 0.1971 0.2191 0.074 Uiso 1 1 calc R . . . .
C19' C 0.9274(3) 0.2764(3) 0.18958(16) 0.0671(12) Uani 1 1 d . . . . .
H19' H 0.9707 0.2557 0.1738 0.081 Uiso 1 1 calc R . . . .
C20' C 0.9138(3) 0.3423(3) 0.18587(16) 0.0658(11) Uani 1 1 d . . . . .
C21' C 0.8485(4) 0.3726(2) 0.20744(15) 0.0624(11) Uani 1 1 d . . . . .
H21' H 0.8391 0.4168 0.2038 0.075 Uiso 1 1 calc R . . . .
C22' C 0.7951(3) 0.3381(2) 0.23512(14) 0.0551(9) Uani 1 1 d . . . . .
C23' C 0.7141(3) 0.3662(2) 0.25418(16) 0.0632(11) Uani 1 1 d . . . . .
H23' H 0.6882 0.4062 0.2433 0.076 Uiso 1 1 calc R . . . .
C24' C 0.6769(3) 0.3367(2) 0.28613(15) 0.0627(11) Uani 1 1 d . . . . .
H24' H 0.6208 0.3529 0.2956 0.075 Uiso 1 1 calc R . . . .
C25' C 0.7282(3) 0.2749(2) 0.30739(14) 0.0531(9) Uani 1 1 d . . . . .
H25' H 0.6797 0.2491 0.3198 0.064 Uiso 1 1 calc R . . . .
C26' C 0.7615(4) 0.1687(2) 0.27271(15) 0.0640(11) Uani 1 1 d . . . . .
H26C H 0.7446 0.1557 0.3019 0.077 Uiso 1 1 calc R . . . .
H26D H 0.8295 0.1538 0.2735 0.077 Uiso 1 1 calc R . . . .
C27' C 0.6894(3) 0.1353(2) 0.23251(14) 0.0570(10) Uani 1 1 d . . . . .
C28' C 0.6096(3) 0.1659(3) 0.20398(15) 0.0637(11) Uani 1 1 d . . . . .
H28' H 0.6018 0.2101 0.2067 0.076 Uiso 1 1 calc R . . . .
C29' C 0.5398(4) 0.1314(3) 0.17080(18) 0.0760(14) Uani 1 1 d . . . . .
H29' H 0.4852 0.1527 0.1520 0.091 Uiso 1 1 calc R . . . .
C30' C 0.5505(5) 0.0669(3) 0.1656(2) 0.0901(17) Uani 1 1 d . . . . .
H30' H 0.5035 0.0441 0.1436 0.108 Uiso 1 1 calc R . . . .
C31' C 0.6319(6) 0.0360(3) 0.1933(3) 0.108(2) Uani 1 1 d . . . . .
H31' H 0.6404 -0.0080 0.1899 0.130 Uiso 1 1 calc R . . . .
C32' C 0.7013(5) 0.0702(3) 0.2265(2) 0.0854(16) Uani 1 1 d . . . . .
H32' H 0.7564 0.0489 0.2449 0.103 Uiso 1 1 calc R . . . .
C33' C 0.9702(2) 0.26284(18) 0.40722(13) 0.0445(8) Uani 1 1 d . . . . .
C34' C 0.9633(3) 0.32076(19) 0.42639(13) 0.0471(8) Uani 1 1 d . . . . .
C35' C 1.0489(3) 0.3550(2) 0.45845(16) 0.0574(10) Uani 1 1 d . . . . .
H35E H 1.0442 0.4007 0.4514 0.069 Uiso 0.468(8) 1 calc R . P B 1
H35F H 1.0425 0.3496 0.4905 0.069 Uiso 0.468(8) 1 calc R . P B 1
H35G H 1.0240 0.3785 0.4822 0.069 Uiso 0.532(8) 1 calc R . P B 2
H35H H 1.0796 0.3856 0.4408 0.069 Uiso 0.532(8) 1 calc R . P B 2
C36' C 1.1487(6) 0.3315(5) 0.4543(4) 0.0604(15) Uani 0.468(8) 1 d . . P B 1
H36E H 1.1986 0.3450 0.4817 0.072 Uiso 0.468(8) 1 calc R . P B 1
H36F H 1.1659 0.3513 0.4271 0.072 Uiso 0.468(8) 1 calc R . P B 1
C37' C 1.1543(3) 0.2595(2) 0.44972(19) 0.0678(12) Uani 1 1 d . . . . .
H37E H 1.1622 0.2408 0.4807 0.081 Uiso 0.468(8) 1 calc R . P B 1
H37F H 1.2147 0.2493 0.4387 0.081 Uiso 0.468(8) 1 calc R . P B 1
H37G H 1.1970 0.2265 0.4674 0.081 Uiso 0.532(8) 1 calc R . P B 2
H37H H 1.1937 0.2817 0.4307 0.081 Uiso 0.532(8) 1 calc R . P B 2
C38' C 1.0654(2) 0.22712(19) 0.41750(13) 0.0461(8) Uani 1 1 d . . . . .
C39' C 1.1577(3) 0.1347(2) 0.40687(15) 0.0556(9) Uani 1 1 d . . . . .
C40' C 1.2353(4) 0.1504(2) 0.38543(18) 0.0685(12) Uani 1 1 d . . . . .
H40' H 1.2310 0.1878 0.3676 0.082 Uiso 1 1 calc R . . . .
C41' C 1.3195(4) 0.1111(3) 0.3903(2) 0.0740(13) Uani 1 1 d . . . . .
H41' H 1.3707 0.1225 0.3754 0.089 Uiso 1 1 calc R . . . .
C42' C 1.3293(4) 0.0556(2) 0.41653(19) 0.0691(12) Uani 1 1 d . . . . .
C43' C 1.2517(4) 0.0406(2) 0.4377(2) 0.0750(13) Uani 1 1 d . . . . .
H43' H 1.2566 0.0036 0.4560 0.090 Uiso 1 1 calc R . . . .
C44' C 1.1662(4) 0.0790(2) 0.43273(17) 0.0660(11) Uani 1 1 d . . . . .
H44' H 1.1144 0.0669 0.4470 0.079 Uiso 1 1 calc R . . . .
C45' C 1.4205(5) 0.0131(3) 0.4213(3) 0.098(2) Uani 1 1 d . . . . .
H45D H 1.4002 -0.0282 0.4079 0.147 Uiso 1 1 calc GR . . . .
H45E H 1.4520 0.0081 0.4539 0.147 Uiso 1 1 calc GR . . . .
H45F H 1.4675 0.0324 0.4053 0.147 Uiso 1 1 calc GR . . . .
Cl1' Cl 0.77804(19) 0.01046(8) 0.42643(9) 0.1316(8) Uani 1 1 d . . . . .
Cl2' Cl 0.97913(12) 0.38586(9) 0.15117(5) 0.0950(5) Uani 1 1 d . . . . .
N1' N 0.7306(2) 0.29241(17) 0.41224(11) 0.0514(8) Uani 1 1 d . . . . .
N2' N 0.7606(3) 0.23861(17) 0.27039(12) 0.0574(8) Uani 1 1 d . . . . .
N3' N 1.0670(2) 0.17100(18) 0.39946(13) 0.0556(8) Uani 1 1 d . . . . .
O1' O 0.87776(19) 0.35725(13) 0.41761(11) 0.0557(7) 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 1.407(6) . ?
C1 C6 1.398(5) . ?
C1 N1 1.398(6) . ?
C2 C3 1.347(7) . ?
C3 C4 1.388(7) . ?
C4 C5 1.383(6) . ?
C4 Cl1 1.742(5) . ?
C5 C6 1.384(6) . ?
C6 C7 1.515(5) . ?
C7 C8 1.524(5) . ?
C7 C33 1.516(5) . ?
C8 C9 1.527(6) . ?
C8 C25 1.541(5) . ?
C9 N1 1.432(5) . ?
C9 O1 1.469(4) . ?
C10 C11 1.515(5) . ?
C10 N1 1.458(5) . ?
C11 C12 1.374(6) . ?
C11 C16 1.374(6) . ?
C12 C13 1.382(6) . ?
C13 C14 1.358(7) . ?
C14 C15 1.365(8) . ?
C15 C16 1.399(6) . ?
C17 C18 1.385(7) . ?
C17 C22 1.418(6) . ?
C17 N2 1.384(6) . ?
C18 C19 1.397(8) . ?
C19 C20 1.375(8) . ?
C20 C21 1.359(7) . ?
C20 Cl2 1.745(5) . ?
C21 C22 1.394(7) . ?
C22 C23 1.457(7) . ?
C23 C24 1.320(7) . ?
C24 C25 1.518(7) . ?
C25 N2 1.475(6) . ?
C26 C27 1.507(6) . ?
C26 N2 1.448(6) . ?
C27 C28 1.374(6) . ?
C27 C32 1.344(8) . ?
C28 C29 1.399(7) . ?
C29 C30 1.341(9) . ?
C30 C31 1.364(11) . ?
C31 C32 1.377(9) . ?
C33 C34 1.352(6) . ?
C33 C38 1.462(5) . ?
C34 C35 1.498(5) . ?
C34 O1 1.349(4) . ?
C35 C36 1.538(7) . ?
C35 C36A 1.470(14) . ?
C36 C37 1.462(8) . ?
C36A C37 1.486(17) . ?
C37 C38 1.508(5) . ?
C38 N3 1.271(5) . ?
C39 C40 1.394(6) . ?
C39 C44 1.386(6) . ?
C39 N3 1.416(5) . ?
C40 C41 1.386(6) . ?
C41 C42 1.391(7) . ?
C42 C43 1.356(7) . ?
C42 C45 1.510(6) . ?
C43 C44 1.393(6) . ?
C1' C2' 1.413(6) . ?
C1' C6' 1.397(5) . ?
C1' N1' 1.387(6) . ?
C1A C35' 1.548(9) . ?
C1A C37' 1.426(10) . ?
C2' C3' 1.357(8) . ?
C3' C4' 1.370(8) . ?
C4' C5' 1.382(7) . ?
C4' Cl1' 1.750(5) . ?
C5' C6' 1.378(6) . ?
C6' C7' 1.521(5) . ?
C7' C8' 1.530(5) . ?
C7' C33' 1.521(5) . ?
C8' C9' 1.519(5) . ?
C8' C25' 1.546(5) . ?
C9' N1' 1.435(5) . ?
C9' O1' 1.459(4) . ?
C10' C11' 1.527(5) . ?
C10' N1' 1.454(5) . ?
C11' C12' 1.384(6) . ?
C11' C16' 1.374(6) . ?
C12' C13' 1.385(6) . ?
C13' C14' 1.350(8) . ?
C14' C15' 1.371(9) . ?
C15' C16' 1.379(7) . ?
C17' C18' 1.392(6) . ?
C17' C22' 1.417(6) . ?
C17' N2' 1.377(6) . ?
C18' C19' 1.388(7) . ?
C19' C20' 1.382(7) . ?
C20' C21' 1.353(7) . ?
C20' Cl2' 1.745(5) . ?
C21' C22' 1.400(6) . ?
C22' C23' 1.462(6) . ?
C23' C24' 1.311(7) . ?
C24' C25' 1.524(6) . ?
C25' N2' 1.467(5) . ?
C26' C27' 1.520(6) . ?
C26' N2' 1.454(6) . ?
C27' C28' 1.369(6) . ?
C27' C32' 1.377(7) . ?
C28' C29' 1.395(7) . ?
C29' C30' 1.359(9) . ?
C30' C31' 1.376(9) . ?
C31' C32' 1.389(8) . ?
C33' C34' 1.340(5) . ?
C33' C38' 1.463(5) . ?
C34' C35' 1.501(5) . ?
C34' O1' 1.363(4) . ?
C35' C36' 1.471(10) . ?
C36' C37' 1.505(11) . ?
C37' C38' 1.514(5) . ?
C38' N3' 1.282(5) . ?
C39' C40' 1.380(6) . ?
C39' C44' 1.374(7) . ?
C39' N3' 1.420(5) . ?
C40' C41' 1.388(6) . ?
C41' C42' 1.375(7) . ?
C42' C43' 1.373(7) . ?
C42' C45' 1.501(6) . ?
C43' C44' 1.389(7) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 118.7(4) . . ?
C6 C1 N1 120.1(3) . . ?
N1 C1 C2 121.2(4) . . ?
C3 C2 C1 121.0(4) . . ?
C2 C3 C4 120.1(4) . . ?
C3 C4 Cl1 119.9(4) . . ?
C5 C4 C3 120.4(4) . . ?
C5 C4 Cl1 119.7(4) . . ?
C4 C5 C6 119.8(4) . . ?
C1 C6 C7 118.4(4) . . ?
C5 C6 C1 119.9(4) . . ?
C5 C6 C7 121.7(4) . . ?
C6 C7 C8 109.0(3) . . ?
C6 C7 C33 110.8(3) . . ?
C33 C7 C8 108.0(3) . . ?
C7 C8 C9 105.6(3) . . ?
C7 C8 C25 115.3(4) . . ?
C9 C8 C25 113.0(3) . . ?
N1 C9 C8 112.1(3) . . ?
N1 C9 O1 110.7(3) . . ?
O1 C9 C8 109.4(3) . . ?
N1 C10 C11 115.1(3) . . ?
C12 C11 C10 123.6(4) . . ?
C12 C11 C16 118.0(4) . . ?
C16 C11 C10 118.3(4) . . ?
C11 C12 C13 121.1(4) . . ?
C14 C13 C12 121.0(5) . . ?
C13 C14 C15 118.8(4) . . ?
C14 C15 C16 120.7(4) . . ?
C11 C16 C15 120.4(4) . . ?
C18 C17 C22 118.2(4) . . ?
N2 C17 C18 123.6(4) . . ?
N2 C17 C22 118.1(4) . . ?
C17 C18 C19 121.2(5) . . ?
C20 C19 C18 119.0(5) . . ?
C19 C20 Cl2 119.1(4) . . ?
C21 C20 C19 121.4(5) . . ?
C21 C20 Cl2 119.5(4) . . ?
C20 C21 C22 120.4(5) . . ?
C17 C22 C23 117.3(4) . . ?
C21 C22 C17 119.5(4) . . ?
C21 C22 C23 122.9(4) . . ?
C24 C23 C22 121.5(4) . . ?
C23 C24 C25 118.7(4) . . ?
C24 C25 C8 110.6(4) . . ?
N2 C25 C8 110.5(3) . . ?
N2 C25 C24 107.9(4) . . ?
N2 C26 C27 116.2(4) . . ?
C28 C27 C26 123.9(4) . . ?
C32 C27 C26 118.3(4) . . ?
C32 C27 C28 117.6(5) . . ?
C27 C28 C29 120.6(5) . . ?
C30 C29 C28 120.7(5) . . ?
C29 C30 C31 118.5(6) . . ?
C30 C31 C32 120.7(7) . . ?
C27 C32 C31 121.9(6) . . ?
C34 C33 C7 119.7(3) . . ?
C34 C33 C38 120.9(3) . . ?
C38 C33 C7 119.3(3) . . ?
C33 C34 C35 123.8(3) . . ?
O1 C34 C33 124.5(3) . . ?
O1 C34 C35 111.7(3) . . ?
C34 C35 C36 109.2(4) . . ?
C36A C35 C34 113.1(7) . . ?
C37 C36 C35 112.8(5) . . ?
C35 C36A C37 115.5(11) . . ?
C36 C37 C38 114.9(4) . . ?
C36A C37 C38 115.1(6) . . ?
C33 C38 C37 117.1(3) . . ?
N3 C38 C33 117.6(3) . . ?
N3 C38 C37 125.2(3) . . ?
C40 C39 N3 121.7(4) . . ?
C44 C39 C40 118.4(4) . . ?
C44 C39 N3 119.8(4) . . ?
C41 C40 C39 120.3(4) . . ?
C40 C41 C42 121.1(4) . . ?
C41 C42 C45 120.4(5) . . ?
C43 C42 C41 117.9(4) . . ?
C43 C42 C45 121.7(5) . . ?
C42 C43 C44 122.4(4) . . ?
C39 C44 C43 119.8(4) . . ?
C1 N1 C9 121.7(3) . . ?
C1 N1 C10 120.5(4) . . ?
C9 N1 C10 116.6(4) . . ?
C17 N2 C25 118.8(4) . . ?
C17 N2 C26 121.8(4) . . ?
C26 N2 C25 118.3(4) . . ?
C38 N3 C39 120.2(3) . . ?
C34 O1 C9 117.1(3) . . ?
C6' C1' C2' 117.9(4) . . ?
N1' C1' C2' 121.6(4) . . ?
N1' C1' C6' 120.4(4) . . ?
C37' C1A C35' 113.9(6) . . ?
C3' C2' C1' 121.4(4) . . ?
C2' C3' C4' 119.2(4) . . ?
C3' C4' C5' 121.8(5) . . ?
C3' C4' Cl1' 119.1(4) . . ?
C5' C4' Cl1' 119.1(4) . . ?
C6' C5' C4' 119.1(4) . . ?
C1' C6' C7' 118.4(3) . . ?
C5' C6' C1' 120.5(4) . . ?
C5' C6' C7' 121.0(3) . . ?
C6' C7' C8' 109.0(3) . . ?
C33' C7' C6' 111.0(3) . . ?
C33' C7' C8' 107.4(3) . . ?
C7' C8' C25' 115.7(3) . . ?
C9' C8' C7' 105.6(3) . . ?
C9' C8' C25' 113.0(3) . . ?
N1' C9' C8' 112.1(3) . . ?
N1' C9' O1' 111.0(3) . . ?
O1' C9' C8' 109.5(3) . . ?
N1' C10' C11' 115.4(3) . . ?
C12' C11' C10' 122.8(4) . . ?
C16' C11' C10' 118.1(4) . . ?
C16' C11' C12' 119.1(4) . . ?
C11' C12' C13' 119.6(5) . . ?
C14' C13' C12' 120.9(5) . . ?
C13' C14' C15' 119.8(4) . . ?
C14' C15' C16' 120.3(5) . . ?
C11' C16' C15' 120.3(5) . . ?
C18' C17' C22' 117.4(4) . . ?
N2' C17' C18' 123.7(4) . . ?
N2' C17' C22' 118.7(4) . . ?
C19' C18' C17' 121.8(5) . . ?
C20' C19' C18' 119.1(4) . . ?
C19' C20' Cl2' 118.9(4) . . ?
C21' C20' C19' 121.0(5) . . ?
C21' C20' Cl2' 120.1(4) . . ?
C20' C21' C22' 120.6(5) . . ?
C17' C22' C23' 116.7(4) . . ?
C21' C22' C17' 119.8(4) . . ?
C21' C22' C23' 123.3(4) . . ?
C24' C23' C22' 121.8(4) . . ?
C23' C24' C25' 118.2(4) . . ?
C24' C25' C8' 109.1(3) . . ?
N2' C25' C8' 111.6(3) . . ?
N2' C25' C24' 108.4(3) . . ?
N2' C26' C27' 115.0(4) . . ?
C28' C27' C26' 123.1(4) . . ?
C28' C27' C32' 118.5(4) . . ?
C32' C27' C26' 118.2(4) . . ?
C27' C28' C29' 120.6(5) . . ?
C30' C29' C28' 120.8(5) . . ?
C29' C30' C31' 119.1(5) . . ?
C30' C31' C32' 120.3(6) . . ?
C27' C32' C31' 120.7(5) . . ?
C34' C33' C7' 120.0(3) . . ?
C34' C33' C38' 120.7(3) . . ?
C38' C33' C7' 119.2(3) . . ?
C33' C34' C35' 124.9(3) . . ?
C33' C34' O1' 123.8(3) . . ?
O1' C34' C35' 111.3(3) . . ?
C34' C35' C1A 108.5(4) . . ?
C36' C35' C34' 112.9(5) . . ?
C35' C36' C37' 113.8(7) . . ?
C1A C37' C38' 114.8(4) . . ?
C36' C37' C38' 116.6(4) . . ?
C33' C38' C37' 116.6(3) . . ?
N3' C38' C33' 118.1(3) . . ?
N3' C38' C37' 125.3(3) . . ?
C40' C39' N3' 121.9(4) . . ?
C44' C39' C40' 118.2(4) . . ?
C44' C39' N3' 119.7(4) . . ?
C39' C40' C41' 120.6(4) . . ?
C42' C41' C40' 121.7(4) . . ?
C41' C42' C45' 121.3(5) . . ?
C43' C42' C41' 117.1(4) . . ?
C43' C42' C45' 121.6(5) . . ?
C42' C43' C44' 122.0(5) . . ?
C39' C44' C43' 120.4(4) . . ?
C1' N1' C9' 121.5(3) . . ?
C1' N1' C10' 121.3(4) . . ?
C9' N1' C10' 115.4(3) . . ?
C17' N2' C25' 118.0(3) . . ?
C17' N2' C26' 121.3(4) . . ?
C26' N2' C25' 118.7(4) . . ?
C38' N3' C39' 120.9(3) . . ?
C34' O1' C9' 117.7(3) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
