# Electronic Supplementary Material (ESI) for ChemComm.
# 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_mo_dd19175_0m
_audit_block_doi                 10.5517/ccdc.csd.cc2419n5
_database_code_depnum_ccdc_archive 'CCDC 1967466'
loop_
_audit_author_name
_audit_author_address
LiMingrui
;School of Pharmaceutical Sciences, Nanjing Tech University, Nanjing
China
;
_audit_update_record             
;
2019-11-22 deposited with the CCDC.	2020-08-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H14 Br2 O4'
_chemical_formula_weight         454.11

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

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

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.5732(4)
_cell_length_b                   12.3258(6)
_cell_length_c                   22.4447(13)
_cell_angle_alpha                105.598(2)
_cell_angle_beta                 93.439(2)
_cell_angle_gamma                93.704(2)
_cell_volume                     1742.17(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9926
_cell_measurement_theta_min      4.361
_cell_measurement_theta_max      52.591

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.731
_exptl_crystal_F_000             896
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    4.671
_shelx_estimated_absorpt_T_min   0.455
_shelx_estimated_absorpt_T_max   0.582
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4243
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            34531
_diffrn_reflns_av_unetI/netI     0.0373
_diffrn_reflns_av_R_equivalents  0.0510
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         1.722
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             6816
_reflns_number_gt                4988
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0335P)²+1.3357P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6816
_refine_ls_number_parameters     435
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0594
_refine_ls_R_factor_gt           0.0376
_refine_ls_wR_factor_ref         0.0969
_refine_ls_wR_factor_gt          0.0865
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.020
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br -0.51018(6) 0.24656(3) 0.69800(2) 0.07025(14) Uani 1 1 d . . . . .
Br2 Br 0.02182(8) 0.96106(3) 0.37426(2) 0.07753(15) Uani 1 1 d . . . . .
Br3 Br 1.01222(7) 0.78090(4) 0.79985(2) 0.08635(16) Uani 1 1 d . . . . .
Br4 Br 0.48151(8) 0.04210(3) 1.11616(2) 0.07653(15) Uani 1 1 d . . . . .
C1 C 0.0153(5) 0.4424(3) 0.69068(15) 0.0517(8) Uani 1 1 d . . . . .
H1 H 0.1518 0.4482 0.7056 0.062 Uiso 1 1 calc R U . . .
C2 C -0.1204(5) 0.3632(3) 0.70313(16) 0.0564(9) Uani 1 1 d . . . . .
H2 H -0.0767 0.3160 0.7265 0.068 Uiso 1 1 calc R U . . .
C3 C -0.3208(5) 0.3548(2) 0.68057(14) 0.0474(7) Uani 1 1 d . . . . .
C4 C -0.3899(5) 0.4240(3) 0.64614(16) 0.0544(8) Uani 1 1 d . . . . .
H4 H -0.5265 0.4173 0.6312 0.065 Uiso 1 1 calc R U . . .
C5 C -0.2520(5) 0.5039(3) 0.63416(15) 0.0487(8) Uani 1 1 d . . . . .
H5 H -0.2966 0.5514 0.6111 0.058 Uiso 1 1 calc R U . . .
C6 C -0.0489(5) 0.5136(2) 0.65614(13) 0.0396(6) Uani 1 1 d . . . . .
C7 C 0.1058(5) 0.5973(2) 0.64379(13) 0.0400(7) Uani 1 1 d . . . . .
C8 C 0.0461(4) 0.6633(2) 0.59840(13) 0.0395(6) Uani 1 1 d . . . . .
H8A H -0.0249 0.7274 0.6196 0.047 Uiso 1 1 calc R U . . .
H8B H -0.0474 0.6154 0.5653 0.047 Uiso 1 1 calc R U . . .
C9 C 0.2307(4) 0.7055(2) 0.57055(13) 0.0368(6) Uani 1 1 d . . . . .
C10 C 0.3350(5) 0.6038(3) 0.53419(14) 0.0469(7) Uani 1 1 d . . . . .
H10 H 0.4573 0.6175 0.5176 0.056 Uiso 1 1 calc R U . . .
C11 C 0.3911(5) 0.7788(2) 0.61964(14) 0.0447(7) Uani 1 1 d . . . . .
C12 C 0.4469(7) 0.9299(3) 0.70943(18) 0.0859(14) Uani 1 1 d . . . . .
H12A H 0.5229 0.8871 0.7316 0.129 Uiso 1 1 calc R U . . .
H12B H 0.3725 0.9824 0.7378 0.129 Uiso 1 1 calc R U . . .
H12C H 0.5394 0.9704 0.6899 0.129 Uiso 1 1 calc R U . . .
C13 C 0.1747(4) 0.7707(2) 0.52311(13) 0.0380(6) Uani 1 1 d . . . . .
C14 C -0.0208(5) 0.7638(3) 0.49586(16) 0.0571(9) Uani 1 1 d . . . . .
H14 H -0.1244 0.7204 0.5074 0.069 Uiso 1 1 calc R U . . .
C15 C -0.0660(6) 0.8202(3) 0.45169(17) 0.0647(10) Uani 1 1 d . . . . .
H15 H -0.1993 0.8156 0.4342 0.078 Uiso 1 1 calc R U . . .
C16 C 0.0858(6) 0.8826(2) 0.43387(14) 0.0508(8) Uani 1 1 d . . . . .
C17 C 0.2816(6) 0.8896(3) 0.45895(17) 0.0635(10) Uani 1 1 d . . . . .
H17 H 0.3845 0.9316 0.4462 0.076 Uiso 1 1 calc R U . . .
C18 C 0.3272(5) 0.8337(3) 0.50357(16) 0.0578(9) Uani 1 1 d . . . . .
H18 H 0.4611 0.8385 0.5206 0.069 Uiso 1 1 calc R U . . .
C19 C 0.7617(5) 0.5278(3) 0.86746(16) 0.0561(8) Uani 1 1 d . . . . .
H19 H 0.8067 0.4838 0.8926 0.067 Uiso 1 1 calc R U . . .
C20 C 0.8958(6) 0.6072(3) 0.85474(18) 0.0653(10) Uani 1 1 d . . . . .
H20 H 1.0310 0.6176 0.8714 0.078 Uiso 1 1 calc R U . . .
C21 C 0.8278(5) 0.6712(3) 0.81706(15) 0.0528(8) Uani 1 1 d . . . . .
C22 C 0.6299(6) 0.6570(3) 0.79210(15) 0.0580(9) Uani 1 1 d . . . . .
H22 H 0.5863 0.7002 0.7664 0.070 Uiso 1 1 calc R U . . .
C23 C 0.4955(5) 0.5778(3) 0.80554(15) 0.0531(8) Uani 1 1 d . . . . .
H23 H 0.3602 0.5682 0.7891 0.064 Uiso 1 1 calc R U . . .
C24 C 0.5606(5) 0.5126(2) 0.84321(13) 0.0422(7) Uani 1 1 d . . . . .
C25 C 0.4089(5) 0.4277(3) 0.85626(14) 0.0446(7) Uani 1 1 d . . . . .
C26 C 0.4743(5) 0.3636(2) 0.90228(14) 0.0438(7) Uani 1 1 d . . . . .
H26A H 0.5449 0.4160 0.9390 0.053 Uiso 1 1 calc R U . . .
H26B H 0.5682 0.3090 0.8839 0.053 Uiso 1 1 calc R U . . .
C27 C 0.2890(4) 0.3028(2) 0.92057(13) 0.0416(7) Uani 1 1 d . . . . .
C28 C 0.1484(5) 0.3906(3) 0.95186(14) 0.0498(8) Uani 1 1 d . . . . .
H28 H 0.0155 0.3661 0.9570 0.060 Uiso 1 1 calc R U . . .
C29 C 0.1871(6) 0.2149(3) 0.86288(15) 0.0508(8) Uani 1 1 d . . . . .
C30 C -0.1199(7) 0.1247(4) 0.80749(18) 0.0876(14) Uani 1 1 d . . . . .
H30A H -0.0686 0.1357 0.7702 0.131 Uiso 1 1 calc R U . . .
H30B H -0.2644 0.1323 0.8065 0.131 Uiso 1 1 calc R U . . .
H30C H -0.0943 0.0505 0.8105 0.131 Uiso 1 1 calc R U . . .
C31 C 0.3406(5) 0.2399(2) 0.96990(13) 0.0423(7) Uani 1 1 d . . . . .
C32 C 0.1878(6) 0.1721(3) 0.98600(16) 0.0630(9) Uani 1 1 d . . . . .
H32 H 0.0563 0.1648 0.9668 0.076 Uiso 1 1 calc R U . . .
C33 C 0.2296(6) 0.1154(3) 1.03038(17) 0.0659(10) Uani 1 1 d . . . . .
H33 H 0.1261 0.0709 1.0411 0.079 Uiso 1 1 calc R U . . .
C34 C 0.4223(6) 0.1251(3) 1.05818(14) 0.0542(8) Uani 1 1 d . . . . .
C35 C 0.5738(6) 0.1932(3) 1.04422(16) 0.0627(9) Uani 1 1 d . . . . .
H35 H 0.7043 0.2008 1.0641 0.075 Uiso 1 1 calc R U . . .
C36 C 0.5323(5) 0.2507(3) 1.00041(15) 0.0555(8) Uani 1 1 d . . . . .
H36 H 0.6355 0.2976 0.9914 0.067 Uiso 1 1 calc R U . . .
O1 O 0.2782(3) 0.61106(19) 0.66874(10) 0.0557(6) Uani 1 1 d . . . . .
O2 O 0.2692(4) 0.50808(18) 0.52576(11) 0.0611(6) Uani 1 1 d . . . . .
O3 O 0.5725(4) 0.7726(2) 0.61747(12) 0.0678(7) Uani 1 1 d . . . . .
O4 O 0.3043(4) 0.85361(17) 0.66235(10) 0.0560(6) Uani 1 1 d . . . . .
O5 O 0.2364(3) 0.4112(2) 0.83138(11) 0.0594(6) Uani 1 1 d . . . . .
O6 O 0.2001(4) 0.48923(19) 0.97007(12) 0.0663(7) Uani 1 1 d . . . . .
O7 O 0.2825(4) 0.1557(2) 0.82531(11) 0.0712(7) Uani 1 1 d . . . . .
O8 O -0.0165(4) 0.2097(2) 0.86139(11) 0.0621(6) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C3 1.899(3) . ?
Br2 C16 1.892(3) . ?
Br3 C21 1.890(3) . ?
Br4 C34 1.897(3) . ?
C1 C2 1.375(4) . ?
C1 C6 1.387(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.370(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.376(4) . ?
C4 C5 1.385(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.382(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.492(4) . ?
C7 O1 1.214(3) . ?
C7 C8 1.514(4) . ?
C8 C9 1.522(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.528(4) . ?
C9 C11 1.531(4) . ?
C9 C13 1.539(4) . ?
C10 O2 1.191(4) . ?
C10 H10 0.9300 . ?
C11 O3 1.203(4) . ?
C11 O4 1.324(4) . ?
C12 O4 1.453(4) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C14 1.377(4) . ?
C13 C18 1.391(4) . ?
C14 C15 1.385(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.364(5) . ?
C15 H15 0.9300 . ?
C16 C17 1.362(5) . ?
C17 C18 1.389(5) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 C20 1.373(5) . ?
C19 C24 1.381(4) . ?
C19 H19 0.9300 . ?
C20 C21 1.377(5) . ?
C20 H20 0.9300 . ?
C21 C22 1.366(5) . ?
C22 C23 1.379(5) . ?
C22 H22 0.9300 . ?
C23 C24 1.382(4) . ?
C23 H23 0.9300 . ?
C24 C25 1.496(4) . ?
C25 O5 1.213(4) . ?
C25 C26 1.518(4) . ?
C26 C27 1.524(4) . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C27 C28 1.522(4) . ?
C27 C29 1.532(4) . ?
C27 C31 1.547(4) . ?
C28 O6 1.193(4) . ?
C28 H28 0.9300 . ?
C29 O7 1.195(4) . ?
C29 O8 1.334(4) . ?
C30 O8 1.467(4) . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?
C31 C36 1.378(4) . ?
C31 C32 1.390(4) . ?
C32 C33 1.386(5) . ?
C32 H32 0.9300 . ?
C33 C34 1.361(5) . ?
C33 H33 0.9300 . ?
C34 C35 1.366(5) . ?
C35 C36 1.383(4) . ?
C35 H35 0.9300 . ?
C36 H36 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 120.8(3) . . ?
C2 C1 H1 119.6 . . ?
C6 C1 H1 119.6 . . ?
C3 C2 C1 119.1(3) . . ?
C3 C2 H2 120.5 . . ?
C1 C2 H2 120.5 . . ?
C2 C3 C4 121.7(3) . . ?
C2 C3 Br1 119.5(2) . . ?
C4 C3 Br1 118.8(3) . . ?
C3 C4 C5 118.7(3) . . ?
C3 C4 H4 120.6 . . ?
C5 C4 H4 120.6 . . ?
C6 C5 C4 120.7(3) . . ?
C6 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
C5 C6 C1 119.0(3) . . ?
C5 C6 C7 122.7(3) . . ?
C1 C6 C7 118.4(3) . . ?
O1 C7 C6 120.8(3) . . ?
O1 C7 C8 120.3(3) . . ?
C6 C7 C8 119.0(3) . . ?
C7 C8 C9 112.2(2) . . ?
C7 C8 H8A 109.2 . . ?
C9 C8 H8A 109.2 . . ?
C7 C8 H8B 109.2 . . ?
C9 C8 H8B 109.2 . . ?
H8A C8 H8B 107.9 . . ?
C8 C9 C10 108.9(2) . . ?
C8 C9 C11 113.0(2) . . ?
C10 C9 C11 107.1(2) . . ?
C8 C9 C13 113.5(2) . . ?
C10 C9 C13 105.1(2) . . ?
C11 C9 C13 108.7(2) . . ?
O2 C10 C9 124.0(3) . . ?
O2 C10 H10 118.0 . . ?
C9 C10 H10 118.0 . . ?
O3 C11 O4 124.8(3) . . ?
O3 C11 C9 123.9(3) . . ?
O4 C11 C9 111.1(3) . . ?
O4 C12 H12A 109.5 . . ?
O4 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O4 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 C18 117.9(3) . . ?
C14 C13 C9 122.3(3) . . ?
C18 C13 C9 119.7(3) . . ?
C13 C14 C15 121.3(3) . . ?
C13 C14 H14 119.4 . . ?
C15 C14 H14 119.4 . . ?
C16 C15 C14 119.7(3) . . ?
C16 C15 H15 120.1 . . ?
C14 C15 H15 120.1 . . ?
C17 C16 C15 120.6(3) . . ?
C17 C16 Br2 120.0(3) . . ?
C15 C16 Br2 119.4(3) . . ?
C16 C17 C18 119.8(3) . . ?
C16 C17 H17 120.1 . . ?
C18 C17 H17 120.1 . . ?
C17 C18 C13 120.7(3) . . ?
C17 C18 H18 119.7 . . ?
C13 C18 H18 119.7 . . ?
C20 C19 C24 120.6(3) . . ?
C20 C19 H19 119.7 . . ?
C24 C19 H19 119.7 . . ?
C19 C20 C21 119.2(3) . . ?
C19 C20 H20 120.4 . . ?
C21 C20 H20 120.4 . . ?
C22 C21 C20 121.3(3) . . ?
C22 C21 Br3 119.5(3) . . ?
C20 C21 Br3 119.2(3) . . ?
C21 C22 C23 119.2(3) . . ?
C21 C22 H22 120.4 . . ?
C23 C22 H22 120.4 . . ?
C22 C23 C24 120.5(3) . . ?
C22 C23 H23 119.8 . . ?
C24 C23 H23 119.8 . . ?
C19 C24 C23 119.3(3) . . ?
C19 C24 C25 122.4(3) . . ?
C23 C24 C25 118.4(3) . . ?
O5 C25 C24 121.0(3) . . ?
O5 C25 C26 120.4(3) . . ?
C24 C25 C26 118.5(3) . . ?
C25 C26 C27 110.6(2) . . ?
C25 C26 H26A 109.5 . . ?
C27 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
C27 C26 H26B 109.5 . . ?
H26A C26 H26B 108.1 . . ?
C28 C27 C26 108.6(2) . . ?
C28 C27 C29 113.8(3) . . ?
C26 C27 C29 109.0(2) . . ?
C28 C27 C31 104.1(2) . . ?
C26 C27 C31 114.0(2) . . ?
C29 C27 C31 107.4(2) . . ?
O6 C28 C27 123.3(3) . . ?
O6 C28 H28 118.4 . . ?
C27 C28 H28 118.4 . . ?
O7 C29 O8 124.9(3) . . ?
O7 C29 C27 122.8(3) . . ?
O8 C29 C27 112.3(3) . . ?
O8 C30 H30A 109.5 . . ?
O8 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
O8 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C36 C31 C32 118.0(3) . . ?
C36 C31 C27 122.5(3) . . ?
C32 C31 C27 119.5(3) . . ?
C33 C32 C31 120.7(3) . . ?
C33 C32 H32 119.7 . . ?
C31 C32 H32 119.7 . . ?
C34 C33 C32 119.9(3) . . ?
C34 C33 H33 120.1 . . ?
C32 C33 H33 120.1 . . ?
C33 C34 C35 120.6(3) . . ?
C33 C34 Br4 119.7(3) . . ?
C35 C34 Br4 119.7(3) . . ?
C34 C35 C36 119.7(3) . . ?
C34 C35 H35 120.1 . . ?
C36 C35 H35 120.1 . . ?
C31 C36 C35 121.2(3) . . ?
C31 C36 H36 119.4 . . ?
C35 C36 H36 119.4 . . ?
C11 O4 C12 114.6(3) . . ?
C29 O8 C30 114.0(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
C6 C1 C2 C3 0.4(5) . . . . ?
C1 C2 C3 C4 -0.4(5) . . . . ?
C1 C2 C3 Br1 -179.5(3) . . . . ?
C2 C3 C4 C5 0.1(5) . . . . ?
Br1 C3 C4 C5 179.2(2) . . . . ?
C3 C4 C5 C6 0.2(5) . . . . ?
C4 C5 C6 C1 -0.2(5) . . . . ?
C4 C5 C6 C7 179.2(3) . . . . ?
C2 C1 C6 C5 -0.1(5) . . . . ?
C2 C1 C6 C7 -179.6(3) . . . . ?
C5 C6 C7 O1 172.8(3) . . . . ?
C1 C6 C7 O1 -7.7(4) . . . . ?
C5 C6 C7 C8 -8.6(4) . . . . ?
C1 C6 C7 C8 170.9(3) . . . . ?
O1 C7 C8 C9 22.5(4) . . . . ?
C6 C7 C8 C9 -156.1(2) . . . . ?
C7 C8 C9 C10 62.0(3) . . . . ?
C7 C8 C9 C11 -56.9(3) . . . . ?
C7 C8 C9 C13 178.8(2) . . . . ?
C8 C9 C10 O2 5.4(4) . . . . ?
C11 C9 C10 O2 128.0(3) . . . . ?
C13 C9 C10 O2 -116.5(3) . . . . ?
C8 C9 C11 O3 138.4(3) . . . . ?
C10 C9 C11 O3 18.5(4) . . . . ?
C13 C9 C11 O3 -94.6(3) . . . . ?
C8 C9 C11 O4 -45.2(3) . . . . ?
C10 C9 C11 O4 -165.2(2) . . . . ?
C13 C9 C11 O4 81.7(3) . . . . ?
C8 C9 C13 C14 -17.4(4) . . . . ?
C10 C9 C13 C14 101.6(3) . . . . ?
C11 C9 C13 C14 -144.0(3) . . . . ?
C8 C9 C13 C18 166.8(3) . . . . ?
C10 C9 C13 C18 -74.3(3) . . . . ?
C11 C9 C13 C18 40.1(4) . . . . ?
C18 C13 C14 C15 -1.8(5) . . . . ?
C9 C13 C14 C15 -177.7(3) . . . . ?
C13 C14 C15 C16 1.0(6) . . . . ?
C14 C15 C16 C17 0.3(6) . . . . ?
C14 C15 C16 Br2 -179.2(3) . . . . ?
C15 C16 C17 C18 -0.7(5) . . . . ?
Br2 C16 C17 C18 178.7(3) . . . . ?
C16 C17 C18 C13 -0.1(5) . . . . ?
C14 C13 C18 C17 1.3(5) . . . . ?
C9 C13 C18 C17 177.4(3) . . . . ?
C24 C19 C20 C21 -0.5(6) . . . . ?
C19 C20 C21 C22 -0.1(6) . . . . ?
C19 C20 C21 Br3 179.7(3) . . . . ?
C20 C21 C22 C23 0.7(5) . . . . ?
Br3 C21 C22 C23 -179.1(3) . . . . ?
C21 C22 C23 C24 -0.7(5) . . . . ?
C20 C19 C24 C23 0.4(5) . . . . ?
C20 C19 C24 C25 -179.5(3) . . . . ?
C22 C23 C24 C19 0.2(5) . . . . ?
C22 C23 C24 C25 -179.9(3) . . . . ?
C19 C24 C25 O5 -175.5(3) . . . . ?
C23 C24 C25 O5 4.6(4) . . . . ?
C19 C24 C25 C26 5.5(4) . . . . ?
C23 C24 C25 C26 -174.4(3) . . . . ?
O5 C25 C26 C27 -12.2(4) . . . . ?
C24 C25 C26 C27 166.9(2) . . . . ?
C25 C26 C27 C28 -61.6(3) . . . . ?
C25 C26 C27 C29 62.9(3) . . . . ?
C25 C26 C27 C31 -177.2(2) . . . . ?
C26 C27 C28 O6 -14.5(4) . . . . ?
C29 C27 C28 O6 -136.1(3) . . . . ?
C31 C27 C28 O6 107.3(3) . . . . ?
C28 C27 C29 O7 163.4(3) . . . . ?
C26 C27 C29 O7 42.1(4) . . . . ?
C31 C27 C29 O7 -81.9(4) . . . . ?
C28 C27 C29 O8 -19.3(4) . . . . ?
C26 C27 C29 O8 -140.7(3) . . . . ?
C31 C27 C29 O8 95.4(3) . . . . ?
C28 C27 C31 C36 -109.9(3) . . . . ?
C26 C27 C31 C36 8.3(4) . . . . ?
C29 C27 C31 C36 129.1(3) . . . . ?
C28 C27 C31 C32 68.1(3) . . . . ?
C26 C27 C31 C32 -173.8(3) . . . . ?
C29 C27 C31 C32 -52.9(4) . . . . ?
C36 C31 C32 C33 -1.5(5) . . . . ?
C27 C31 C32 C33 -179.5(3) . . . . ?
C31 C32 C33 C34 -0.6(6) . . . . ?
C32 C33 C34 C35 2.1(6) . . . . ?
C32 C33 C34 Br4 -177.2(3) . . . . ?
C33 C34 C35 C36 -1.5(6) . . . . ?
Br4 C34 C35 C36 177.8(3) . . . . ?
C32 C31 C36 C35 2.1(5) . . . . ?
C27 C31 C36 C35 -179.9(3) . . . . ?
C34 C35 C36 C31 -0.7(6) . . . . ?
O3 C11 O4 C12 -1.3(4) . . . . ?
C9 C11 O4 C12 -177.6(3) . . . . ?
O7 C29 O8 C30 -1.5(5) . . . . ?
C27 C29 O8 C30 -178.7(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C28 H28 O6 0.93 2.63 3.168(4) 117.7 2_567
C26 H26A O6 0.97 2.53 3.471(4) 163.9 2_667
C12 H12B O7 0.96 2.61 3.538(5) 162.5 1_565
C10 H10 O2 0.93 2.52 3.219(4) 132.6 2_666
C8 H8B O2 0.97 2.51 3.479(4) 175.8 2_566

_refine_diff_density_max         0.643
_refine_diff_density_min         -0.747
_refine_diff_density_rms         0.054

_shelxl_version_number           2013-4



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

data_mo_dd19075_0m
_database_code_depnum_ccdc_archive 'CCDC 1917689'
loop_
_audit_author_name
_audit_author_address
'Huang fei'
;Nanjing Tech University
China
;
_audit_update_record             
;
2019-05-22 deposited with the CCDC.	2020-08-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H21 N O2'
_chemical_formula_weight         367.43

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

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

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.8574(3)
_cell_length_b                   10.1476(3)
_cell_length_c                   13.2472(4)
_cell_angle_alpha                73.3980(10)
_cell_angle_beta                 88.8340(10)
_cell_angle_gamma                80.0530(10)
_cell_volume                     996.53(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    7108
_cell_measurement_theta_min      6.020
_cell_measurement_theta_max      54.946

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.225
_exptl_crystal_F_000             388
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.077
_shelx_estimated_absorpt_T_min   0.985
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6835
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14611
_diffrn_reflns_av_unetI/netI     0.0281
_diffrn_reflns_av_R_equivalents  0.0305
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.633
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             3897
_reflns_number_gt                3266
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0548P)²+0.2270P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       ?
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3897
_refine_ls_number_parameters     255
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0526
_refine_ls_R_factor_gt           0.0426
_refine_ls_wR_factor_ref         0.1151
_refine_ls_wR_factor_gt          0.1060
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_restrained_S_all      1.005
_refine_ls_shift/su_max          0.012
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.80832(14) 0.17620(10) 0.18795(8) 0.0524(3) Uani 1 1 d . . . . .
O2 O 0.65141(15) 0.38052(11) 0.09972(8) 0.0576(3) Uani 1 1 d . . . . .
N1 N 0.78279(14) 0.28255(11) 0.36977(8) 0.0358(3) Uani 1 1 d . . . . .
C1 C 0.79537(17) 0.36925(13) 0.43125(10) 0.0378(3) Uani 1 1 d . . . . .
C2 C 0.78707(18) 0.50206(14) 0.36587(11) 0.0421(3) Uani 1 1 d . . . . .
H2 H 0.7939 0.5807 0.3873 0.051 Uiso 1 1 calc R U . . .
C3 C 0.76643(17) 0.50021(13) 0.26097(11) 0.0382(3) Uani 1 1 d . . . . .
C4 C 0.76228(16) 0.36243(13) 0.26520(10) 0.0363(3) Uani 1 1 d . . . . .
C5 C 0.74516(17) 0.29506(14) 0.18269(11) 0.0384(3) Uani 1 1 d . . . . .
C6 C 0.6347(3) 0.3252(2) 0.01207(15) 0.0779(6) Uani 1 1 d . . . . .
H6A H 0.5870 0.3997 -0.0484 0.117 Uiso 1 1 calc R U . . .
H6B H 0.5596 0.2572 0.0302 0.117 Uiso 1 1 calc R U . . .
H6C H 0.7465 0.2818 -0.0039 0.117 Uiso 1 1 calc R U . . .
C7 C 0.73837(18) 0.14211(13) 0.40922(11) 0.0395(3) Uani 1 1 d . . . . .
H7A H 0.7489 0.1122 0.4856 0.047 Uiso 1 1 calc R U . . .
H7B H 0.8200 0.0772 0.3830 0.047 Uiso 1 1 calc R U . . .
C8 C 0.55775(18) 0.13718(14) 0.37616(10) 0.0386(3) Uani 1 1 d . . . . .
C9 C 0.5246(2) 0.02817(16) 0.34184(12) 0.0499(4) Uani 1 1 d . . . . .
H9 H 0.6147 -0.0435 0.3397 0.060 Uiso 1 1 calc R U . . .
C10 C 0.3601(2) 0.0232(2) 0.31052(14) 0.0637(5) Uani 1 1 d . . . . .
H10 H 0.3402 -0.0521 0.2885 0.076 Uiso 1 1 calc R U . . .
C11 C 0.2264(2) 0.1283(2) 0.31170(15) 0.0666(5) Uani 1 1 d . . . . .
H11 H 0.1161 0.1259 0.2891 0.080 Uiso 1 1 calc R U . . .
C12 C 0.2559(2) 0.2371(2) 0.34636(18) 0.0759(6) Uani 1 1 d . . . . .
H12 H 0.1652 0.3085 0.3482 0.091 Uiso 1 1 calc R U . . .
C13 C 0.4214(2) 0.24120(17) 0.37887(16) 0.0643(5) Uani 1 1 d . . . . .
H13 H 0.4404 0.3153 0.4028 0.077 Uiso 1 1 calc R U . . .
C14 C 0.82218(18) 0.31979(13) 0.54672(10) 0.0386(3) Uani 1 1 d . . . . .
C15 C 0.7198(2) 0.38728(16) 0.60962(12) 0.0532(4) Uani 1 1 d . . . . .
H15 H 0.6303 0.4599 0.5788 0.064 Uiso 1 1 calc R U . . .
C16 C 0.7488(2) 0.34816(18) 0.71731(13) 0.0618(5) Uani 1 1 d . . . . .
H16 H 0.6804 0.3956 0.7584 0.074 Uiso 1 1 calc R U . . .
C17 C 0.8787(2) 0.23900(17) 0.76407(12) 0.0551(4) Uani 1 1 d . . . . .
H17 H 0.8977 0.2123 0.8367 0.066 Uiso 1 1 calc R U . . .
C18 C 0.9802(2) 0.16957(16) 0.70300(12) 0.0487(4) Uani 1 1 d . . . . .
H18 H 1.0672 0.0951 0.7345 0.058 Uiso 1 1 calc R U . . .
C19 C 0.95332(18) 0.21017(14) 0.59519(11) 0.0429(3) Uani 1 1 d . . . . .
H19 H 1.0238 0.1637 0.5544 0.052 Uiso 1 1 calc R U . . .
C20 C 0.76174(18) 0.62406(14) 0.16861(11) 0.0411(3) Uani 1 1 d . . . . .
C21 C 0.8517(2) 0.61943(18) 0.07813(13) 0.0565(4) Uani 1 1 d . . . . .
H21 H 0.9132 0.5349 0.0729 0.068 Uiso 1 1 calc R U . . .
C22 C 0.8506(3) 0.7390(2) -0.00402(14) 0.0726(5) Uani 1 1 d . . . . .
H22 H 0.9102 0.7341 -0.0646 0.087 Uiso 1 1 calc R U . . .
C23 C 0.7626(3) 0.8649(2) 0.00269(16) 0.0773(6) Uani 1 1 d . . . . .
H23 H 0.7628 0.9452 -0.0530 0.093 Uiso 1 1 calc R U . . .
C24 C 0.6741(3) 0.87202(17) 0.09180(15) 0.0667(5) Uani 1 1 d . . . . .
H24 H 0.6151 0.9574 0.0970 0.080 Uiso 1 1 calc R U . . .
C25 C 0.6728(2) 0.75251(15) 0.17372(13) 0.0503(4) Uani 1 1 d . . . . .
H25 H 0.6112 0.7581 0.2335 0.060 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C5 1.2052(16) . ?
O2 C5 1.3305(17) . ?
O2 C6 1.4441(19) . ?
N1 C1 1.3747(16) . ?
N1 C4 1.3872(17) . ?
N1 C7 1.4713(16) . ?
C1 C2 1.3695(19) . ?
C1 C14 1.4745(19) . ?
C2 C3 1.4081(19) . ?
C2 H2 0.9300 . ?
C3 C4 1.3892(18) . ?
C3 C20 1.4782(19) . ?
C4 C5 1.4645(18) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 C8 1.5069(19) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.375(2) . ?
C8 C13 1.376(2) . ?
C9 C10 1.378(2) . ?
C9 H9 0.9300 . ?
C10 C11 1.365(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.366(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.389(3) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 C15 1.385(2) . ?
C14 C19 1.3907(19) . ?
C15 C16 1.379(2) . ?
C15 H15 0.9300 . ?
C16 C17 1.377(2) . ?
C16 H16 0.9300 . ?
C17 C18 1.376(2) . ?
C17 H17 0.9300 . ?
C18 C19 1.378(2) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 C25 1.388(2) . ?
C20 C21 1.387(2) . ?
C21 C22 1.378(2) . ?
C21 H21 0.9300 . ?
C22 C23 1.370(3) . ?
C22 H22 0.9300 . ?
C23 C24 1.371(3) . ?
C23 H23 0.9300 . ?
C24 C25 1.379(2) . ?
C24 H24 0.9300 . ?
C25 H25 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
C5 O2 C6 116.14(12) . . ?
C1 N1 C4 108.55(10) . . ?
C1 N1 C7 124.48(11) . . ?
C4 N1 C7 123.92(11) . . ?
C2 C1 N1 107.95(12) . . ?
C2 C1 C14 128.35(12) . . ?
N1 C1 C14 123.64(12) . . ?
C1 C2 C3 108.93(12) . . ?
C1 C2 H2 125.5 . . ?
C3 C2 H2 125.5 . . ?
C4 C3 C2 106.29(12) . . ?
C4 C3 C20 129.75(12) . . ?
C2 C3 C20 123.87(12) . . ?
N1 C4 C3 108.27(11) . . ?
N1 C4 C5 119.70(11) . . ?
C3 C4 C5 132.01(12) . . ?
O1 C5 O2 123.13(12) . . ?
O1 C5 C4 124.62(12) . . ?
O2 C5 C4 112.25(11) . . ?
O2 C6 H6A 109.5 . . ?
O2 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
O2 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N1 C7 C8 112.51(11) . . ?
N1 C7 H7A 109.1 . . ?
C8 C7 H7A 109.1 . . ?
N1 C7 H7B 109.1 . . ?
C8 C7 H7B 109.1 . . ?
H7A C7 H7B 107.8 . . ?
C9 C8 C13 117.95(14) . . ?
C9 C8 C7 120.72(12) . . ?
C13 C8 C7 121.33(13) . . ?
C8 C9 C10 121.21(15) . . ?
C8 C9 H9 119.4 . . ?
C10 C9 H9 119.4 . . ?
C11 C10 C9 120.34(16) . . ?
C11 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
C12 C11 C10 119.51(16) . . ?
C12 C11 H11 120.2 . . ?
C10 C11 H11 120.2 . . ?
C11 C12 C13 120.03(17) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
C8 C13 C12 120.94(16) . . ?
C8 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
C15 C14 C19 118.24(13) . . ?
C15 C14 C1 119.78(12) . . ?
C19 C14 C1 121.92(12) . . ?
C16 C15 C14 120.89(15) . . ?
C16 C15 H15 119.6 . . ?
C14 C15 H15 119.6 . . ?
C15 C16 C17 120.11(15) . . ?
C15 C16 H16 119.9 . . ?
C17 C16 H16 119.9 . . ?
C18 C17 C16 119.80(14) . . ?
C18 C17 H17 120.1 . . ?
C16 C17 H17 120.1 . . ?
C17 C18 C19 120.12(14) . . ?
C17 C18 H18 119.9 . . ?
C19 C18 H18 119.9 . . ?
C18 C19 C14 120.83(13) . . ?
C18 C19 H19 119.6 . . ?
C14 C19 H19 119.6 . . ?
C25 C20 C21 117.90(14) . . ?
C25 C20 C3 119.40(13) . . ?
C21 C20 C3 122.59(13) . . ?
C22 C21 C20 120.61(16) . . ?
C22 C21 H21 119.7 . . ?
C20 C21 H21 119.7 . . ?
C23 C22 C21 120.62(18) . . ?
C23 C22 H22 119.7 . . ?
C21 C22 H22 119.7 . . ?
C22 C23 C24 119.72(16) . . ?
C22 C23 H23 120.1 . . ?
C24 C23 H23 120.1 . . ?
C23 C24 C25 119.95(17) . . ?
C23 C24 H24 120.0 . . ?
C25 C24 H24 120.0 . . ?
C24 C25 C20 121.19(16) . . ?
C24 C25 H25 119.4 . . ?
C20 C25 H25 119.4 . . ?

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
C4 N1 C1 C2 -1.42(15) . . . . ?
C7 N1 C1 C2 -162.24(12) . . . . ?
C4 N1 C1 C14 -178.56(12) . . . . ?
C7 N1 C1 C14 20.63(19) . . . . ?
N1 C1 C2 C3 0.82(16) . . . . ?
C14 C1 C2 C3 177.78(13) . . . . ?
C1 C2 C3 C4 0.09(16) . . . . ?
C1 C2 C3 C20 -176.70(13) . . . . ?
C1 N1 C4 C3 1.49(15) . . . . ?
C7 N1 C4 C3 162.44(12) . . . . ?
C1 N1 C4 C5 -179.85(11) . . . . ?
C7 N1 C4 C5 -18.90(18) . . . . ?
C2 C3 C4 N1 -0.96(15) . . . . ?
C20 C3 C4 N1 175.57(13) . . . . ?
C2 C3 C4 C5 -179.40(14) . . . . ?
C20 C3 C4 C5 -2.9(2) . . . . ?
C6 O2 C5 O1 -2.8(2) . . . . ?
C6 O2 C5 C4 177.03(15) . . . . ?
N1 C4 C5 O1 -29.3(2) . . . . ?
C3 C4 C5 O1 149.03(15) . . . . ?
N1 C4 C5 O2 150.96(12) . . . . ?
C3 C4 C5 O2 -30.8(2) . . . . ?
C1 N1 C7 C8 106.75(14) . . . . ?
C4 N1 C7 C8 -51.20(16) . . . . ?
N1 C7 C8 C9 137.55(13) . . . . ?
N1 C7 C8 C13 -42.19(19) . . . . ?
C13 C8 C9 C10 0.3(2) . . . . ?
C7 C8 C9 C10 -179.42(14) . . . . ?
C8 C9 C10 C11 0.9(3) . . . . ?
C9 C10 C11 C12 -1.4(3) . . . . ?
C10 C11 C12 C13 0.8(3) . . . . ?
C9 C8 C13 C12 -1.0(3) . . . . ?
C7 C8 C13 C12 178.78(16) . . . . ?
C11 C12 C13 C8 0.4(3) . . . . ?
C2 C1 C14 C15 51.3(2) . . . . ?
N1 C1 C14 C15 -132.19(15) . . . . ?
C2 C1 C14 C19 -125.80(16) . . . . ?
N1 C1 C14 C19 50.72(19) . . . . ?
C19 C14 C15 C16 0.9(2) . . . . ?
C1 C14 C15 C16 -176.25(15) . . . . ?
C14 C15 C16 C17 -1.3(3) . . . . ?
C15 C16 C17 C18 0.4(3) . . . . ?
C16 C17 C18 C19 0.7(2) . . . . ?
C17 C18 C19 C14 -1.0(2) . . . . ?
C15 C14 C19 C18 0.2(2) . . . . ?
C1 C14 C19 C18 177.33(13) . . . . ?
C4 C3 C20 C25 143.37(15) . . . . ?
C2 C3 C20 C25 -40.6(2) . . . . ?
C4 C3 C20 C21 -40.6(2) . . . . ?
C2 C3 C20 C21 135.43(16) . . . . ?
C25 C20 C21 C22 -0.6(2) . . . . ?
C3 C20 C21 C22 -176.70(16) . . . . ?
C20 C21 C22 C23 0.8(3) . . . . ?
C21 C22 C23 C24 -0.2(3) . . . . ?
C22 C23 C24 C25 -0.6(3) . . . . ?
C23 C24 C25 C20 0.9(3) . . . . ?
C21 C20 C25 C24 -0.3(2) . . . . ?
C3 C20 C25 C24 175.98(15) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C6 H6A O2 0.96 2.59 3.385(2) 140.7 2_665

_refine_diff_density_max         0.211
_refine_diff_density_min         -0.151
_refine_diff_density_rms         0.029

_shelxl_version_number           2013-4



