# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_wmj18167
_database_code_depnum_ccdc_archive 'CCDC 1897635'
loop_
_audit_author_name
_audit_author_address
'Xiaobo Huang'
;Wenzhou University 
China
;
_audit_update_record             
;
2019-02-17 deposited with the CCDC.	2019-05-20 downloaded from the CCDC.
;
_audit_creation_date             2018-09-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C28 H26 N2 O2'
_chemical_formula_sum            'C28 H26 N2 O2'
_chemical_formula_weight         422.51
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0148 0.0070 '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 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0412 0.0250 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   20.0543(6)
_cell_length_b                   8.8607(3)
_cell_length_c                   25.1405(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4467.3(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    6105
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      45.048
_cell_measurement_theta_min      3.059
_shelx_estimated_absorpt_T_max   0.998
_shelx_estimated_absorpt_T_min   0.980
_exptl_absorpt_coefficient_mu    0.401
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.6264
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1226 before and 0.0822 after correction. The Ratio of minimum to maximum transmission is 0.8343. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.256
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1792
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.005
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1373
_diffrn_reflns_av_unetI/netI     0.0812
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            46033
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.994
_diffrn_reflns_theta_min         3.059
_diffrn_ambient_temperature      170.01
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2266
_reflns_number_total             4263
_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       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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         0.230
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     310
_refine_ls_number_reflns         4263
_refine_ls_number_restraints     48
_refine_ls_R_factor_all          0.1829
_refine_ls_R_factor_gt           0.0926
_refine_ls_restrained_S_all      1.066
_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)+(0.0508P)²+7.2994P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1703
_refine_ls_wR_factor_ref         0.2082
_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
C27 \\sim C28 \\sim C29 \\sim C30: within 2A with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(C27) \\sim Ueq, Uanis(C30) \\sim Ueq, Uanis(C29) \\sim Ueq: with sigma of
0.005 and sigma for terminal atoms of 0.01
3. Others
 Fixed Sof: C27(0.66667) H27A(0.66667) H27B(0.66667) C28(0.66667)
 H28A(0.66667) H28B(0.66667) H28C(0.66667) C29(0.33333) H29A(0.33333)
 H29B(0.33333) C30(0.33333) H30A(0.33333) H30B(0.33333) H30C(0.33333)
4.a Secondary CH2 refined with riding coordinates:
 C25(H25A,H25B), C27(H27A,H27B), C29(H29A,H29B)
4.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C7(H7), C8(H8), C10(H10), C12(H12),
 C14(H14), C15(H15), C17(H17), C18(H18), C19(H19), C20(H20), C21(H21)
4.c Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C), C28(H28A,H28B,H28C), C30(H30A,H30B,H30C)
;
_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
O1 O 0.37215(16) 0.4008(6) 0.36021(15) 0.130(2) Uani 1 1 d . . . . .
O2 O 0.26663(13) 0.3404(4) 0.37724(11) 0.0598(9) Uani 1 1 d . . . . .
N1 N 0.53456(15) 0.2419(4) 0.51345(12) 0.0478(9) Uani 1 1 d . . . . .
N2 N 0.2511(2) 0.1231(6) 0.48681(15) 0.0833(15) Uani 1 1 d . . . . .
C1 C 0.5065(2) -0.1367(5) 0.67439(16) 0.0487(11) Uani 1 1 d . . . . .
H1 H 0.540952 -0.138180 0.648436 0.058 Uiso 1 1 calc R . . . .
C2 C 0.5121(2) -0.2265(5) 0.71936(17) 0.0552(12) Uani 1 1 d . . . . .
H2 H 0.549667 -0.290508 0.723654 0.066 Uiso 1 1 calc R . . . .
C3 C 0.4632(2) -0.2231(6) 0.75779(18) 0.0621(13) Uani 1 1 d . . . . .
H3 H 0.466853 -0.284016 0.788734 0.074 Uiso 1 1 calc R . . . .
C4 C 0.4095(3) -0.1311(6) 0.75082(19) 0.0772(16) Uani 1 1 d . . . . .
H4 H 0.375971 -0.127345 0.777479 0.093 Uiso 1 1 calc R . . . .
C5 C 0.4028(2) -0.0431(5) 0.70571(17) 0.0614(13) Uani 1 1 d . . . . .
H5 H 0.364537 0.018882 0.701430 0.074 Uiso 1 1 calc R . . . .
C6 C 0.45147(19) -0.0449(5) 0.66687(15) 0.0420(10) Uani 1 1 d . . . . .
C7 C 0.4438(2) 0.0530(5) 0.61993(15) 0.0458(11) Uani 1 1 d . . . . .
H7 H 0.402164 0.102429 0.615549 0.055 Uiso 1 1 calc R . . . .
C8 C 0.49009(19) 0.0784(5) 0.58317(15) 0.0453(11) Uani 1 1 d . . . . .
H8 H 0.532620 0.033442 0.588253 0.054 Uiso 1 1 calc R . . . .
C9 C 0.48044(18) 0.1704(5) 0.53544(15) 0.0420(10) Uani 1 1 d . . . . .
C10 C 0.41931(19) 0.1804(5) 0.51137(15) 0.0482(11) Uani 1 1 d . . . . .
H10 H 0.382351 0.131367 0.527505 0.058 Uiso 1 1 calc R . . . .
C11 C 0.40896(19) 0.2612(5) 0.46315(16) 0.0485(11) Uani 1 1 d . . . . .
C12 C 0.46600(19) 0.3343(5) 0.44358(17) 0.0504(12) Uani 1 1 d . . . . .
H12 H 0.462017 0.392247 0.411943 0.061 Uiso 1 1 calc R . . . .
C13 C 0.52709(19) 0.3264(5) 0.46776(15) 0.0431(10) Uani 1 1 d . . . . .
C14 C 0.5844(2) 0.4100(5) 0.44663(16) 0.0474(11) Uani 1 1 d . . . . .
H14 H 0.615798 0.432249 0.467960 0.057 Uiso 1 1 calc R . . . .
C15 C 0.5903(2) 0.4529(5) 0.39662(16) 0.0506(11) Uani 1 1 d . . . . .
H15 H 0.556774 0.419390 0.372679 0.061 Uiso 1 1 calc R . . . .
C16 C 0.64343(19) 0.5470(5) 0.37434(16) 0.0432(10) Uani 1 1 d . . . . .
C17 C 0.6404(2) 0.5843(5) 0.32035(17) 0.0528(12) Uani 1 1 d . . . . .
H17 H 0.605165 0.545801 0.299041 0.063 Uiso 1 1 calc R . . . .
C18 C 0.6881(2) 0.6764(5) 0.29772(18) 0.0615(13) Uani 1 1 d . . . . .
H18 H 0.685148 0.701497 0.261057 0.074 Uiso 1 1 calc R . . . .
C19 C 0.7399(2) 0.7322(6) 0.32784(19) 0.0662(14) Uani 1 1 d . . . . .
H19 H 0.772743 0.795153 0.312089 0.079 Uiso 1 1 calc R . . . .
C20 C 0.7435(2) 0.6958(5) 0.38110(18) 0.0623(13) Uani 1 1 d . . . . .
H20 H 0.778963 0.734339 0.402154 0.075 Uiso 1 1 calc R . . . .
C21 C 0.6961(2) 0.6039(5) 0.40398(17) 0.0515(11) Uani 1 1 d . . . . .
H21 H 0.699556 0.578968 0.440633 0.062 Uiso 1 1 calc R . . . .
C22 C 0.34572(19) 0.2641(6) 0.43884(16) 0.0559(13) Uani 1 1 d . . . . .
C23 C 0.2920(2) 0.1884(6) 0.46432(18) 0.0641(15) Uani 1 1 d . . . . .
C24 C 0.3324(2) 0.3410(7) 0.38924(18) 0.0692(15) Uani 1 1 d . . . . .
C25 C 0.2485(2) 0.4270(7) 0.33039(17) 0.0795(17) Uani 1 1 d . . . . .
H25A H 0.263206 0.373798 0.297803 0.095 Uiso 1 1 calc R . . . .
H25B H 0.270179 0.527360 0.331344 0.095 Uiso 1 1 calc R . . . .
C26 C 0.1751(3) 0.4439(7) 0.3305(2) 0.094(2) Uani 1 1 d . . . . .
H26A H 0.161057 0.498208 0.298431 0.141 Uiso 1 1 calc GR . . . .
H26B H 0.161314 0.500769 0.362079 0.141 Uiso 1 1 calc GR . . . .
H26C H 0.154198 0.343894 0.331050 0.141 Uiso 1 1 calc GR . . . .
C27 C 0.6065(4) 0.2081(10) 0.5361(3) 0.046(2) Uani 0.6667 1 d . U P A 1
H27A H 0.609134 0.103299 0.549666 0.055 Uiso 0.6667 1 calc R . P A 1
H27B H 0.640591 0.221328 0.508023 0.055 Uiso 0.6667 1 calc R . P A 1
C28 C 0.6176(4) 0.3188(8) 0.5804(3) 0.065(2) Uani 0.6667 1 d . U P A 1
H28A H 0.611988 0.421691 0.566870 0.097 Uiso 0.6667 1 calc GR . P A 1
H28B H 0.662834 0.306673 0.594505 0.097 Uiso 0.6667 1 calc GR . P A 1
H28C H 0.585135 0.300256 0.608839 0.097 Uiso 0.6667 1 calc GR . P A 1
C29 C 0.5937(7) 0.2640(18) 0.5426(7) 0.033(3) Uani 0.3333 1 d . U P A 2
H29A H 0.586127 0.255642 0.575736 0.039 Uiso 0.3333 1 calc R . P A 2
H29B H 0.609459 0.351360 0.536610 0.039 Uiso 0.3333 1 calc R . P A 2
C30 C 0.6435(5) 0.1406(13) 0.5240(4) 0.032(3) Uani 0.3333 1 d . U P A 2
H30A H 0.653644 0.154951 0.486216 0.049 Uiso 0.3333 1 calc GR . P A 2
H30B H 0.623652 0.040648 0.529306 0.049 Uiso 0.3333 1 calc GR . P A 2
H30C H 0.684728 0.148259 0.544796 0.049 Uiso 0.3333 1 calc GR . P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C24 1.203(5) . ?
O2 C24 1.354(5) . ?
O2 C25 1.452(5) . ?
N1 C9 1.373(5) . ?
N1 C13 1.379(5) . ?
N1 C27 1.580(9) . ?
N1 C29 1.407(16) . ?
N2 C23 1.153(6) . ?
C1 H1 0.9500 . ?
C1 C2 1.387(6) . ?
C1 C6 1.385(5) . ?
C2 H2 0.9500 . ?
C2 C3 1.377(6) . ?
C3 H3 0.9500 . ?
C3 C4 1.361(6) . ?
C4 H4 0.9500 . ?
C4 C5 1.383(6) . ?
C5 H5 0.9500 . ?
C5 C6 1.380(5) . ?
C6 C7 1.473(5) . ?
C7 H7 0.9500 . ?
C7 C8 1.328(5) . ?
C8 H8 0.9500 . ?
C8 C9 1.464(5) . ?
C9 C10 1.370(5) . ?
C10 H10 0.9500 . ?
C10 C11 1.423(5) . ?
C11 C12 1.404(5) . ?
C11 C22 1.408(5) . ?
C12 H12 0.9500 . ?
C12 C13 1.370(5) . ?
C13 C14 1.467(5) . ?
C14 H14 0.8500 . ?
C14 C15 1.319(5) . ?
C15 H15 0.9500 . ?
C15 C16 1.464(5) . ?
C16 C17 1.398(5) . ?
C16 C21 1.387(5) . ?
C17 H17 0.9500 . ?
C17 C18 1.380(6) . ?
C18 H18 0.9500 . ?
C18 C19 1.377(6) . ?
C19 H19 0.9500 . ?
C19 C20 1.379(6) . ?
C20 H20 0.9500 . ?
C20 C21 1.378(6) . ?
C21 H21 0.9500 . ?
C22 C23 1.421(6) . ?
C22 C24 1.446(6) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C25 C26 1.481(7) . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C27 C28 1.501(10) . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C29 H29A 0.8500 . ?
C29 H29B 0.8500 . ?
C29 C30 1.553(16) . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?

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
C24 O2 C25 115.0(4) . . ?
C9 N1 C13 120.0(3) . . ?
C9 N1 C27 119.3(4) . . ?
C9 N1 C29 121.4(7) . . ?
C13 N1 C27 120.2(4) . . ?
C13 N1 C29 116.7(7) . . ?
C2 C1 H1 119.6 . . ?
C6 C1 H1 119.6 . . ?
C6 C1 C2 120.8(4) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 C1 120.2(4) . . ?
C3 C2 H2 119.9 . . ?
C2 C3 H3 120.5 . . ?
C4 C3 C2 119.1(4) . . ?
C4 C3 H3 120.5 . . ?
C3 C4 H4 119.3 . . ?
C3 C4 C5 121.3(5) . . ?
C5 C4 H4 119.3 . . ?
C4 C5 H5 119.8 . . ?
C6 C5 C4 120.3(4) . . ?
C6 C5 H5 119.8 . . ?
C1 C6 C7 122.6(4) . . ?
C5 C6 C1 118.3(4) . . ?
C5 C6 C7 119.1(4) . . ?
C6 C7 H7 117.1 . . ?
C8 C7 C6 125.8(4) . . ?
C8 C7 H7 117.1 . . ?
C7 C8 H8 117.5 . . ?
C7 C8 C9 124.9(4) . . ?
C9 C8 H8 117.5 . . ?
N1 C9 C8 118.9(3) . . ?
C10 C9 N1 120.0(4) . . ?
C10 C9 C8 121.1(4) . . ?
C9 C10 H10 118.7 . . ?
C9 C10 C11 122.6(4) . . ?
C11 C10 H10 118.7 . . ?
C12 C11 C10 114.3(4) . . ?
C12 C11 C22 125.0(4) . . ?
C22 C11 C10 120.7(4) . . ?
C11 C12 H12 118.3 . . ?
C13 C12 C11 123.4(4) . . ?
C13 C12 H12 118.3 . . ?
N1 C13 C14 119.4(4) . . ?
C12 C13 N1 119.6(4) . . ?
C12 C13 C14 121.0(4) . . ?
C13 C14 H14 117.9 . . ?
C15 C14 C13 124.1(4) . . ?
C15 C14 H14 117.9 . . ?
C14 C15 H15 116.8 . . ?
C14 C15 C16 126.4(4) . . ?
C16 C15 H15 116.8 . . ?
C17 C16 C15 118.3(4) . . ?
C21 C16 C15 123.7(4) . . ?
C21 C16 C17 118.0(4) . . ?
C16 C17 H17 119.7 . . ?
C18 C17 C16 120.6(4) . . ?
C18 C17 H17 119.7 . . ?
C17 C18 H18 119.7 . . ?
C19 C18 C17 120.6(4) . . ?
C19 C18 H18 119.7 . . ?
C18 C19 H19 120.3 . . ?
C18 C19 C20 119.3(4) . . ?
C20 C19 H19 120.3 . . ?
C19 C20 H20 119.8 . . ?
C21 C20 C19 120.5(5) . . ?
C21 C20 H20 119.8 . . ?
C16 C21 H21 119.5 . . ?
C20 C21 C16 121.0(4) . . ?
C20 C21 H21 119.5 . . ?
C11 C22 C23 118.6(4) . . ?
C11 C22 C24 123.3(4) . . ?
C23 C22 C24 118.1(4) . . ?
N2 C23 C22 176.1(5) . . ?
O1 C24 O2 120.8(4) . . ?
O1 C24 C22 127.5(4) . . ?
O2 C24 C22 111.7(4) . . ?
O2 C25 H25A 110.2 . . ?
O2 C25 H25B 110.2 . . ?
O2 C25 C26 107.5(4) . . ?
H25A C25 H25B 108.5 . . ?
C26 C25 H25A 110.2 . . ?
C26 C25 H25B 110.2 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
N1 C27 H27A 110.5 . . ?
N1 C27 H27B 110.5 . . ?
H27A C27 H27B 108.7 . . ?
C28 C27 N1 106.2(7) . . ?
C28 C27 H27A 110.5 . . ?
C28 C27 H27B 110.5 . . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
N1 C29 H29A 110.4 . . ?
N1 C29 H29B 110.4 . . ?
N1 C29 C30 106.7(11) . . ?
H29A C29 H29B 108.6 . . ?
C30 C29 H29A 110.4 . . ?
C30 C29 H29B 110.4 . . ?
C29 C30 H30A 109.5 . . ?
C29 C30 H30B 109.5 . . ?
C29 C30 H30C 109.5 . . ?
H30A C30 H30B 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?

_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_mjl18388
_database_code_depnum_ccdc_archive 'CCDC 1897637'
loop_
_audit_author_name
_audit_author_address
'Xiaobo Huang'
;Wenzhou University 
China
;
_audit_update_record             
;
2019-02-17 deposited with the CCDC.	2019-05-20 downloaded from the CCDC.
;
_audit_creation_date             2018-08-22
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C28 H24 F2 N2 O2'
_chemical_formula_sum            'C28 H24 F2 N2 O2'
_chemical_formula_weight         458.49
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0148 0.0070 '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'
F F 0.0583 0.0400 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0412 0.0250 '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                   16.7550(8)
_cell_length_b                   19.7470(10)
_cell_length_c                   7.6891(4)
_cell_angle_alpha                90
_cell_angle_beta                 98.211(3)
_cell_angle_gamma                90
_cell_volume                     2517.9(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9896
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      54.956
_cell_measurement_theta_min      3.029
_shelx_estimated_absorpt_T_max   0.986
_shelx_estimated_absorpt_T_min   0.964
_exptl_absorpt_coefficient_mu    0.457
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.5719
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1648 before and 0.0789 after correction. The Ratio of minimum to maximum transmission is 0.7617. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.209
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0647
_diffrn_reflns_av_unetI/netI     0.0460
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            26256
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         55.258
_diffrn_reflns_theta_min         3.027
_diffrn_ambient_temperature      170.02
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3444
_reflns_number_total             4795
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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         0.521
_refine_diff_density_min         -0.392
_refine_diff_density_rms         0.067
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     309
_refine_ls_number_reflns         4795
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0940
_refine_ls_R_factor_gt           0.0713
_refine_ls_restrained_S_all      1.056
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1230P)²+1.3870P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2004
_refine_ls_wR_factor_ref         0.2190
_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 Secondary CH2 refined with riding coordinates:
 C22(H22A,H22B), C27(H27A,H27B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5), C7(H7), C8(H8), C10(H10), C12(H12), C14(H14),
 C15(H15), C17(H17), C18(H18), C20(H20), C21(H21)
2.c Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C28(H28A,H28B,H28C)
;
_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
F1 F 0.88069(12) 0.13316(10) 0.7836(3) 0.0697(6) Uani 1 1 d . . . . .
F2 F -0.03200(11) 0.57311(13) 0.2467(3) 0.0817(7) Uani 1 1 d . . . . .
O1 O 0.72226(11) 0.52127(9) 0.2302(3) 0.0432(5) Uani 1 1 d . . . . .
O2 O 0.69623(12) 0.62818(9) 0.1379(3) 0.0483(5) Uani 1 1 d . . . . .
N1 N 0.46328(13) 0.39697(10) 0.3777(3) 0.0340(5) Uani 1 1 d . . . . .
N2 N 0.50083(15) 0.66521(12) 0.0723(4) 0.0512(7) Uani 1 1 d . . . . .
C1 C 0.69643(18) 0.21302(13) 0.5829(4) 0.0423(7) Uani 1 1 d . . . . .
H1 H 0.643999 0.200618 0.528330 0.051 Uiso 1 1 calc R . . . .
C2 C 0.75136(18) 0.16359(14) 0.6448(4) 0.0460(7) Uani 1 1 d . . . . .
H2 H 0.736744 0.117139 0.633988 0.055 Uiso 1 1 calc R . . . .
C3 C 0.82636(19) 0.18161(15) 0.7212(4) 0.0479(7) Uani 1 1 d . . . . .
C4 C 0.85022(19) 0.24840(17) 0.7444(4) 0.0534(8) Uani 1 1 d . . . . .
H4 H 0.902666 0.259936 0.800620 0.064 Uiso 1 1 calc R . . . .
C5 C 0.79483(18) 0.29776(14) 0.6827(4) 0.0451(7) Uani 1 1 d . . . . .
H5 H 0.809795 0.344052 0.696787 0.054 Uiso 1 1 calc R . . . .
C6 C 0.71787(17) 0.28157(13) 0.6005(4) 0.0390(6) Uani 1 1 d . . . . .
C7 C 0.66288(16) 0.33640(13) 0.5332(4) 0.0375(6) Uani 1 1 d . . . . .
H7 H 0.682491 0.381094 0.556663 0.045 Uiso 1 1 calc R . . . .
C8 C 0.58966(17) 0.33161(13) 0.4441(4) 0.0386(6) Uani 1 1 d . . . . .
H8 H 0.565412 0.288281 0.424460 0.046 Uiso 1 1 calc R . . . .
C9 C 0.54480(15) 0.39251(12) 0.3746(3) 0.0335(6) Uani 1 1 d . . . . .
C10 C 0.58550(16) 0.44487(12) 0.3084(3) 0.0351(6) Uani 1 1 d . . . . .
H10 H 0.641689 0.440303 0.304842 0.042 Uiso 1 1 calc R . . . .
C11 C 0.54627(15) 0.50525(12) 0.2456(3) 0.0322(6) Uani 1 1 d . . . . .
C12 C 0.46260(15) 0.50721(13) 0.2532(3) 0.0339(6) Uani 1 1 d . . . . .
H12 H 0.433154 0.546546 0.211916 0.041 Uiso 1 1 calc R . . . .
C13 C 0.42211(16) 0.45459(12) 0.3177(3) 0.0341(6) Uani 1 1 d . . . . .
C14 C 0.33647(16) 0.46142(13) 0.3310(4) 0.0362(6) Uani 1 1 d . . . . .
H14 H 0.316844 0.441935 0.429617 0.043 Uiso 1 1 calc R . . . .
C15 C 0.28420(16) 0.49369(13) 0.2114(4) 0.0363(6) Uani 1 1 d . . . . .
H15 H 0.303847 0.506965 0.106606 0.044 Uiso 1 1 calc R . . . .
C16 C 0.20044(16) 0.51085(12) 0.2235(4) 0.0374(6) Uani 1 1 d . . . . .
C17 C 0.15038(17) 0.53323(14) 0.0723(4) 0.0429(7) Uani 1 1 d . . . . .
H17 H 0.170475 0.534059 -0.037114 0.052 Uiso 1 1 calc R . . . .
C18 C 0.07247(18) 0.55401(16) 0.0805(5) 0.0518(8) Uani 1 1 d . . . . .
H18 H 0.038847 0.569220 -0.022036 0.062 Uiso 1 1 calc R . . . .
C19 C 0.04457(18) 0.55232(17) 0.2386(5) 0.0538(8) Uani 1 1 d . . . . .
C20 C 0.09125(18) 0.53055(17) 0.3905(4) 0.0517(8) Uani 1 1 d . . . . .
H20 H 0.069864 0.529566 0.498433 0.062 Uiso 1 1 calc R . . . .
C21 C 0.16912(17) 0.51030(14) 0.3834(4) 0.0428(7) Uani 1 1 d . . . . .
H21 H 0.202087 0.495793 0.487605 0.051 Uiso 1 1 calc R . . . .
C22 C 0.41856(17) 0.33798(13) 0.4359(4) 0.0386(6) Uani 1 1 d . . . . .
H22A H 0.376575 0.354287 0.504269 0.046 Uiso 1 1 calc R . . . .
H22B H 0.456266 0.308844 0.513765 0.046 Uiso 1 1 calc R . . . .
C23 C 0.3796(2) 0.29708(14) 0.2820(4) 0.0515(8) Uani 1 1 d . . . . .
H23A H 0.420835 0.282422 0.211598 0.077 Uiso 1 1 calc GR . . . .
H23B H 0.339346 0.324877 0.209523 0.077 Uiso 1 1 calc GR . . . .
H23C H 0.353346 0.257270 0.324606 0.077 Uiso 1 1 calc GR . . . .
C24 C 0.58726(16) 0.56172(12) 0.1833(3) 0.0343(6) Uani 1 1 d . . . . .
C25 C 0.54060(16) 0.61928(13) 0.1217(4) 0.0369(6) Uani 1 1 d . . . . .
C26 C 0.67278(16) 0.56554(13) 0.1868(3) 0.0352(6) Uani 1 1 d . . . . .
C27 C 0.78193(19) 0.63932(17) 0.1484(5) 0.0605(9) Uani 1 1 d . . . . .
H27A H 0.792534 0.670964 0.054486 0.073 Uiso 1 1 calc R . . . .
H27B H 0.809259 0.595924 0.130735 0.073 Uiso 1 1 calc R . . . .
C28 C 0.8147(3) 0.6681(3) 0.3234(9) 0.114(2) Uani 1 1 d . . . . .
H28A H 0.868823 0.686222 0.319389 0.171 Uiso 1 1 calc GR . . . .
H28B H 0.817383 0.632497 0.412800 0.171 Uiso 1 1 calc GR . . . .
H28C H 0.779264 0.704577 0.353060 0.171 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C3 1.360(3) . ?
F2 C19 1.357(3) . ?
O1 C26 1.218(3) . ?
O2 C26 1.367(3) . ?
O2 C27 1.444(4) . ?
N1 C9 1.372(3) . ?
N1 C13 1.376(3) . ?
N1 C22 1.488(3) . ?
N2 C25 1.157(3) . ?
C1 H1 0.9500 . ?
C1 C2 1.379(4) . ?
C1 C6 1.402(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.357(4) . ?
C3 C4 1.382(5) . ?
C4 H4 0.9500 . ?
C4 C5 1.382(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.390(4) . ?
C6 C7 1.467(4) . ?
C7 H7 0.9500 . ?
C7 C8 1.320(4) . ?
C8 H8 0.9500 . ?
C8 C9 1.477(4) . ?
C9 C10 1.376(4) . ?
C10 H10 0.9500 . ?
C10 C11 1.413(3) . ?
C11 C12 1.412(4) . ?
C11 C24 1.428(4) . ?
C12 H12 0.9500 . ?
C12 C13 1.372(4) . ?
C13 C14 1.459(4) . ?
C14 H14 0.9500 . ?
C14 C15 1.337(4) . ?
C15 H15 0.9500 . ?
C15 C16 1.460(4) . ?
C16 C17 1.404(4) . ?
C16 C21 1.404(4) . ?
C17 H17 0.9500 . ?
C17 C18 1.378(4) . ?
C18 H18 0.9500 . ?
C18 C19 1.363(5) . ?
C19 C20 1.379(5) . ?
C20 H20 0.9500 . ?
C20 C21 1.373(4) . ?
C21 H21 0.9500 . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C22 C23 1.502(4) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 C25 1.422(4) . ?
C24 C26 1.431(4) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C27 C28 1.491(7) . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?

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
C26 O2 C27 116.4(2) . . ?
C9 N1 C13 120.0(2) . . ?
C9 N1 C22 120.0(2) . . ?
C13 N1 C22 119.9(2) . . ?
C2 C1 H1 120.0 . . ?
C2 C1 C6 120.1(3) . . ?
C6 C1 H1 120.0 . . ?
C1 C2 H2 120.2 . . ?
C3 C2 C1 119.7(3) . . ?
C3 C2 H2 120.2 . . ?
F1 C3 C4 117.3(3) . . ?
C2 C3 F1 120.0(3) . . ?
C2 C3 C4 122.6(3) . . ?
C3 C4 H4 121.3 . . ?
C3 C4 C5 117.4(3) . . ?
C5 C4 H4 121.3 . . ?
C4 C5 H5 119.1 . . ?
C4 C5 C6 121.9(3) . . ?
C6 C5 H5 119.1 . . ?
C1 C6 C7 122.6(3) . . ?
C5 C6 C1 118.3(3) . . ?
C5 C6 C7 119.1(2) . . ?
C6 C7 H7 115.8 . . ?
C8 C7 C6 128.3(2) . . ?
C8 C7 H7 115.8 . . ?
C7 C8 H8 119.4 . . ?
C7 C8 C9 121.1(2) . . ?
C9 C8 H8 119.4 . . ?
N1 C9 C8 120.1(2) . . ?
N1 C9 C10 120.4(2) . . ?
C10 C9 C8 119.5(2) . . ?
C9 C10 H10 119.0 . . ?
C9 C10 C11 122.0(2) . . ?
C11 C10 H10 119.0 . . ?
C10 C11 C24 123.4(2) . . ?
C12 C11 C10 115.2(2) . . ?
C12 C11 C24 121.4(2) . . ?
C11 C12 H12 118.7 . . ?
C13 C12 C11 122.6(2) . . ?
C13 C12 H12 118.7 . . ?
N1 C13 C14 120.3(2) . . ?
C12 C13 N1 119.8(2) . . ?
C12 C13 C14 119.8(2) . . ?
C13 C14 H14 118.3 . . ?
C15 C14 C13 123.4(2) . . ?
C15 C14 H14 118.3 . . ?
C14 C15 H15 116.3 . . ?
C14 C15 C16 127.5(3) . . ?
C16 C15 H15 116.3 . . ?
C17 C16 C15 119.1(3) . . ?
C17 C16 C21 118.3(3) . . ?
C21 C16 C15 122.5(2) . . ?
C16 C17 H17 119.6 . . ?
C18 C17 C16 120.9(3) . . ?
C18 C17 H17 119.6 . . ?
C17 C18 H18 120.6 . . ?
C19 C18 C17 118.8(3) . . ?
C19 C18 H18 120.6 . . ?
F2 C19 C18 118.7(3) . . ?
F2 C19 C20 118.7(3) . . ?
C18 C19 C20 122.5(3) . . ?
C19 C20 H20 120.5 . . ?
C21 C20 C19 119.0(3) . . ?
C21 C20 H20 120.5 . . ?
C16 C21 H21 119.7 . . ?
C20 C21 C16 120.6(3) . . ?
C20 C21 H21 119.7 . . ?
N1 C22 H22A 109.4 . . ?
N1 C22 H22B 109.4 . . ?
N1 C22 C23 111.4(2) . . ?
H22A C22 H22B 108.0 . . ?
C23 C22 H22A 109.4 . . ?
C23 C22 H22B 109.4 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C11 C24 C26 124.3(2) . . ?
C25 C24 C11 117.9(2) . . ?
C25 C24 C26 117.7(2) . . ?
N2 C25 C24 178.2(3) . . ?
O1 C26 O2 120.9(2) . . ?
O1 C26 C24 127.4(2) . . ?
O2 C26 C24 111.6(2) . . ?
O2 C27 H27A 109.6 . . ?
O2 C27 H27B 109.6 . . ?
O2 C27 C28 110.1(3) . . ?
H27A C27 H27B 108.2 . . ?
C28 C27 H27A 109.6 . . ?
C28 C27 H27B 109.6 . . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.072 0.250 -0.311 173.8 8.7 ?
2 -0.072 0.750 -0.495 173.8 8.7 ?

_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_dd18140
_database_code_depnum_ccdc_archive 'CCDC 1897638'
loop_
_audit_author_name
_audit_author_address
'Xiaobo Huang'
;Wenzhou University 
China
;
_audit_update_record             
;
2019-02-17 deposited with the CCDC.	2019-05-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H24 Br2 N2 O2'
_chemical_formula_weight         580.31

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

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

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

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

_cell_length_a                   17.384(4)
_cell_length_b                   19.973(5)
_cell_length_c                   7.823(2)
_cell_angle_alpha                90
_cell_angle_beta                 98.170(10)
_cell_angle_gamma                90
_cell_volume                     2688.7(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    2198
_cell_measurement_theta_min      4.734
_cell_measurement_theta_max      53.340

_exptl_crystal_description       prismatic
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.434
_exptl_crystal_F_000             1168
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    3.041
_shelx_estimated_absorpt_T_min   0.642
_shelx_estimated_absorpt_T_max   0.793
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5896
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(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            10000
_diffrn_reflns_av_unetI/netI     0.0838
_diffrn_reflns_av_R_equivalents  0.0433
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.821
_diffrn_reflns_theta_max         25.499
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measured_fraction_theta_full 0.966
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_Laue_measured_fraction_full 0.966
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_point_group_measured_fraction_full 0.966
_reflns_number_total             4834
_reflns_number_gt                2802
_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)+(0.1209P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4834
_refine_ls_number_parameters     309
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.1311
_refine_ls_R_factor_gt           0.0719
_refine_ls_wR_factor_ref         0.2155
_refine_ls_wR_factor_gt          0.1798
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.026
_refine_ls_shift/su_max          0.008
_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 -0.03737(4) 0.42271(5) 0.24353(11) 0.0699(3) Uani 1 1 d . . . . .
Br2 Br 0.91025(6) 0.85769(5) 0.83942(12) 0.0872(4) Uani 1 1 d . . . . .
O1 O 0.7144(2) 0.4663(2) 0.2454(6) 0.0446(11) Uani 1 1 d . . . . .
O2 O 0.6828(2) 0.3653(2) 0.1311(6) 0.0463(11) Uani 1 1 d . . . . .
N1 N 0.4719(3) 0.6019(2) 0.3760(6) 0.0327(11) Uani 1 1 d . . . . .
N2 N 0.4919(3) 0.3380(3) 0.0665(8) 0.0542(15) Uani 1 1 d . . . . .
C1 C 0.4288(3) 0.5468(3) 0.3147(7) 0.0344(14) Uani 1 1 d . . . . .
C2 C 0.4656(3) 0.4929(3) 0.2497(7) 0.0332(14) Uani 1 1 d . . . . .
H2 H 0.4351 0.4556 0.2055 0.040 Uiso 1 1 calc R U . . .
C3 C 0.5459(3) 0.4912(3) 0.2467(7) 0.0348(14) Uani 1 1 d . . . . .
C4 C 0.5866(3) 0.5492(3) 0.3084(8) 0.0362(14) Uani 1 1 d . . . . .
H4 H 0.6410 0.5512 0.3055 0.043 Uiso 1 1 calc R U . . .
C5 C 0.5507(3) 0.6031(3) 0.3727(7) 0.0356(14) Uani 1 1 d . . . . .
C6 C 0.5961(4) 0.6615(3) 0.4416(8) 0.0411(15) Uani 1 1 d . . . . .
H6 H 0.5757 0.7052 0.4186 0.049 Uiso 1 1 calc R U . . .
C7 C 0.6654(3) 0.6538(3) 0.5359(8) 0.0385(15) Uani 1 1 d . . . . .
H7 H 0.6811 0.6088 0.5599 0.046 Uiso 1 1 calc R U . . .
C8 C 0.7204(4) 0.7048(3) 0.6074(8) 0.0416(15) Uani 1 1 d . . . . .
C9 C 0.7932(4) 0.6842(4) 0.6885(9) 0.0485(17) Uani 1 1 d . . . . .
H9 H 0.8044 0.6377 0.6983 0.058 Uiso 1 1 calc R U . . .
C10 C 0.8496(4) 0.7297(4) 0.7549(9) 0.058(2) Uani 1 1 d . . . . .
H10 H 0.8994 0.7149 0.8066 0.069 Uiso 1 1 calc R U . . .
C11 C 0.8318(4) 0.7962(4) 0.7443(9) 0.0542(19) Uani 1 1 d . . . . .
C12 C 0.7617(4) 0.8188(4) 0.6683(10) 0.0547(19) Uani 1 1 d . . . . .
H12 H 0.7514 0.8655 0.6631 0.066 Uiso 1 1 calc R U . . .
C13 C 0.7044(4) 0.7736(3) 0.5975(9) 0.0466(17) Uani 1 1 d . . . . .
H13 H 0.6553 0.7893 0.5435 0.056 Uiso 1 1 calc R U . . .
C14 C 0.3459(3) 0.5437(3) 0.3241(9) 0.0392(15) Uani 1 1 d . . . . .
H14 H 0.3269 0.5628 0.4213 0.047 Uiso 1 1 calc R U . . .
C15 C 0.2950(3) 0.5148(3) 0.2002(8) 0.0357(14) Uani 1 1 d . . . . .
H15 H 0.3140 0.5025 0.0967 0.043 Uiso 1 1 calc R U . . .
C16 C 0.2123(3) 0.5005(3) 0.2100(8) 0.0399(15) Uani 1 1 d . . . . .
C17 C 0.1793(4) 0.5088(3) 0.3608(9) 0.0463(17) Uani 1 1 d . . . . .
H17 H 0.2089 0.5285 0.4593 0.056 Uiso 1 1 calc R U . . .
C18 C 0.1040(4) 0.4886(4) 0.3685(10) 0.0544(19) Uani 1 1 d . . . . .
H18 H 0.0811 0.4958 0.4703 0.065 Uiso 1 1 calc R U . . .
C19 C 0.0626(3) 0.4581(4) 0.2279(9) 0.0493(18) Uani 1 1 d . . . . .
C20 C 0.0923(4) 0.4513(4) 0.0764(9) 0.0498(18) Uani 1 1 d . . . . .
H20 H 0.0617 0.4322 -0.0219 0.060 Uiso 1 1 calc R U . . .
C21 C 0.1675(4) 0.4725(3) 0.0674(9) 0.0453(16) Uani 1 1 d . . . . .
H21 H 0.1885 0.4677 -0.0376 0.054 Uiso 1 1 calc R U . . .
C22 C 0.5823(3) 0.4334(3) 0.1849(8) 0.0348(14) Uani 1 1 d . . . . .
C23 C 0.5323(3) 0.3801(3) 0.1184(8) 0.0374(15) Uani 1 1 d . . . . .
C24 C 0.6646(4) 0.4256(3) 0.1918(7) 0.0376(15) Uani 1 1 d . . . . .
C25 C 0.7648(4) 0.3512(4) 0.1368(13) 0.071(2) Uani 1 1 d . U . . .
H25A H 0.7933 0.3934 0.1244 0.086 Uiso 1 1 calc R U . . .
H25B H 0.7726 0.3215 0.0393 0.086 Uiso 1 1 calc R U . . .
C26 C 0.7959(5) 0.3188(5) 0.2998(15) 0.096(3) Uani 1 1 d . U . . .
H26A H 0.8528 0.3195 0.3138 0.145 Uiso 1 1 calc R U . . .
H26B H 0.7777 0.2724 0.2990 0.145 Uiso 1 1 calc R U . . .
H26C H 0.7780 0.3430 0.3959 0.145 Uiso 1 1 calc R U . . .
C27 C 0.4320(4) 0.6615(3) 0.4322(8) 0.0406(15) Uani 1 1 d . . . . .
H27A H 0.4693 0.6881 0.5125 0.049 Uiso 1 1 calc R U . . .
H27B H 0.3895 0.6470 0.4956 0.049 Uiso 1 1 calc R U . . .
C28 C 0.3990(4) 0.7049(3) 0.2828(9) 0.0508(17) Uani 1 1 d . . . . .
H28A H 0.3595 0.6797 0.2070 0.076 Uiso 1 1 calc R U . . .
H28B H 0.4407 0.7183 0.2178 0.076 Uiso 1 1 calc R U . . .
H28C H 0.3753 0.7448 0.3261 0.076 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
Br1 C19 1.896(6) . ?
Br2 C11 1.906(7) . ?
O1 C24 1.218(7) . ?
O2 C24 1.349(8) . ?
O2 C25 1.448(8) . ?
N1 C5 1.376(7) . ?
N1 C1 1.378(7) . ?
N1 C27 1.476(8) . ?
N2 C23 1.134(8) . ?
C1 C2 1.385(8) . ?
C1 C14 1.456(8) . ?
C2 C3 1.400(8) . ?
C2 H2 0.9500 . ?
C3 C4 1.407(8) . ?
C3 C22 1.433(9) . ?
C4 C5 1.374(9) . ?
C4 H4 0.9500 . ?
C5 C6 1.466(8) . ?
C6 C7 1.329(8) . ?
C6 H6 0.9500 . ?
C7 C8 1.453(8) . ?
C7 H7 0.9500 . ?
C8 C9 1.395(9) . ?
C8 C13 1.402(9) . ?
C9 C10 1.382(9) . ?
C9 H9 0.9500 . ?
C10 C11 1.364(11) . ?
C10 H10 0.9500 . ?
C11 C12 1.356(10) . ?
C12 C13 1.399(9) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 C15 1.346(8) . ?
C14 H14 0.9500 . ?
C15 C16 1.478(8) . ?
C15 H15 0.9500 . ?
C16 C21 1.385(9) . ?
C16 C17 1.393(9) . ?
C17 C18 1.379(9) . ?
C17 H17 0.9500 . ?
C18 C19 1.369(10) . ?
C18 H18 0.9500 . ?
C19 C20 1.365(10) . ?
C20 C21 1.385(9) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
C22 C23 1.425(9) . ?
C22 C24 1.433(8) . ?
C25 C26 1.462(13) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 C28 1.501(9) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?

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
C24 O2 C25 116.3(5) . . ?
C5 N1 C1 120.1(5) . . ?
C5 N1 C27 120.2(5) . . ?
C1 N1 C27 119.6(5) . . ?
N1 C1 C2 119.5(5) . . ?
N1 C1 C14 120.6(5) . . ?
C2 C1 C14 119.8(5) . . ?
C1 C2 C3 122.6(5) . . ?
C1 C2 H2 118.7 . . ?
C3 C2 H2 118.7 . . ?
C2 C3 C4 115.3(6) . . ?
C2 C3 C22 120.9(5) . . ?
C4 C3 C22 123.7(5) . . ?
C5 C4 C3 122.7(6) . . ?
C5 C4 H4 118.7 . . ?
C3 C4 H4 118.7 . . ?
C4 C5 N1 119.8(5) . . ?
C4 C5 C6 120.6(6) . . ?
N1 C5 C6 119.5(5) . . ?
C7 C6 C5 120.7(6) . . ?
C7 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
C6 C7 C8 128.9(6) . . ?
C6 C7 H7 115.6 . . ?
C8 C7 H7 115.6 . . ?
C9 C8 C13 118.3(6) . . ?
C9 C8 C7 118.3(6) . . ?
C13 C8 C7 123.4(6) . . ?
C10 C9 C8 121.8(7) . . ?
C10 C9 H9 119.1 . . ?
C8 C9 H9 119.1 . . ?
C11 C10 C9 118.4(7) . . ?
C11 C10 H10 120.8 . . ?
C9 C10 H10 120.8 . . ?
C12 C11 C10 122.2(6) . . ?
C12 C11 Br2 120.3(6) . . ?
C10 C11 Br2 117.5(6) . . ?
C11 C12 C13 120.2(7) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C12 C13 C8 119.1(6) . . ?
C12 C13 H13 120.4 . . ?
C8 C13 H13 120.4 . . ?
C15 C14 C1 122.4(6) . . ?
C15 C14 H14 118.8 . . ?
C1 C14 H14 118.8 . . ?
C14 C15 C16 126.2(6) . . ?
C14 C15 H15 116.9 . . ?
C16 C15 H15 116.9 . . ?
C21 C16 C17 118.6(6) . . ?
C21 C16 C15 118.4(6) . . ?
C17 C16 C15 122.8(6) . . ?
C18 C17 C16 120.7(6) . . ?
C18 C17 H17 119.7 . . ?
C16 C17 H17 119.7 . . ?
C19 C18 C17 119.2(7) . . ?
C19 C18 H18 120.4 . . ?
C17 C18 H18 120.4 . . ?
C20 C19 C18 121.5(6) . . ?
C20 C19 Br1 118.8(5) . . ?
C18 C19 Br1 119.7(6) . . ?
C19 C20 C21 119.3(6) . . ?
C19 C20 H20 120.3 . . ?
C21 C20 H20 120.3 . . ?
C16 C21 C20 120.6(6) . . ?
C16 C21 H21 119.7 . . ?
C20 C21 H21 119.7 . . ?
C23 C22 C3 116.7(5) . . ?
C23 C22 C24 119.1(6) . . ?
C3 C22 C24 124.1(5) . . ?
N2 C23 C22 179.2(7) . . ?
O1 C24 O2 121.8(6) . . ?
O1 C24 C22 126.7(6) . . ?
O2 C24 C22 111.5(5) . . ?
O2 C25 C26 110.7(8) . . ?
O2 C25 H25A 109.5 . . ?
C26 C25 H25A 109.5 . . ?
O2 C25 H25B 109.5 . . ?
C26 C25 H25B 109.5 . . ?
H25A C25 H25B 108.1 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
N1 C27 C28 112.1(5) . . ?
N1 C27 H27A 109.2 . . ?
C28 C27 H27A 109.2 . . ?
N1 C27 H27B 109.2 . . ?
C28 C27 H27B 109.2 . . ?
H27A C27 H27B 107.9 . . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C1 C2 -0.1(8) . . . . ?
C27 N1 C1 C2 175.1(5) . . . . ?
C5 N1 C1 C14 177.4(5) . . . . ?
C27 N1 C1 C14 -7.4(8) . . . . ?
N1 C1 C2 C3 1.4(8) . . . . ?
C14 C1 C2 C3 -176.2(5) . . . . ?
C1 C2 C3 C4 -2.3(8) . . . . ?
C1 C2 C3 C22 177.4(5) . . . . ?
C2 C3 C4 C5 2.1(8) . . . . ?
C22 C3 C4 C5 -177.6(6) . . . . ?
C3 C4 C5 N1 -0.9(9) . . . . ?
C3 C4 C5 C6 177.6(5) . . . . ?
C1 N1 C5 C4 -0.1(8) . . . . ?
C27 N1 C5 C4 -175.3(5) . . . . ?
C1 N1 C5 C6 -178.7(5) . . . . ?
C27 N1 C5 C6 6.1(8) . . . . ?
C4 C5 C6 C7 -39.8(9) . . . . ?
N1 C5 C6 C7 138.8(6) . . . . ?
C5 C6 C7 C8 176.5(6) . . . . ?
C6 C7 C8 C9 -173.8(7) . . . . ?
C6 C7 C8 C13 5.5(11) . . . . ?
C13 C8 C9 C10 -1.4(10) . . . . ?
C7 C8 C9 C10 178.0(7) . . . . ?
C8 C9 C10 C11 1.9(11) . . . . ?
C9 C10 C11 C12 -1.3(12) . . . . ?
C9 C10 C11 Br2 179.3(5) . . . . ?
C10 C11 C12 C13 0.1(12) . . . . ?
Br2 C11 C12 C13 179.6(5) . . . . ?
C11 C12 C13 C8 0.4(11) . . . . ?
C9 C8 C13 C12 0.2(10) . . . . ?
C7 C8 C13 C12 -179.1(6) . . . . ?
N1 C1 C14 C15 144.1(6) . . . . ?
C2 C1 C14 C15 -38.3(8) . . . . ?
C1 C14 C15 C16 170.4(6) . . . . ?
C14 C15 C16 C21 177.8(6) . . . . ?
C14 C15 C16 C17 -7.7(10) . . . . ?
C21 C16 C17 C18 0.9(10) . . . . ?
C15 C16 C17 C18 -173.6(6) . . . . ?
C16 C17 C18 C19 2.2(10) . . . . ?
C17 C18 C19 C20 -4.5(11) . . . . ?
C17 C18 C19 Br1 174.2(5) . . . . ?
C18 C19 C20 C21 3.5(11) . . . . ?
Br1 C19 C20 C21 -175.3(5) . . . . ?
C17 C16 C21 C20 -2.0(10) . . . . ?
C15 C16 C21 C20 172.8(6) . . . . ?
C19 C20 C21 C16 -0.2(10) . . . . ?
C2 C3 C22 C23 3.5(8) . . . . ?
C4 C3 C22 C23 -176.8(5) . . . . ?
C2 C3 C22 C24 -174.4(5) . . . . ?
C4 C3 C22 C24 5.4(9) . . . . ?
C25 O2 C24 O1 1.3(9) . . . . ?
C25 O2 C24 C22 -178.2(6) . . . . ?
C23 C22 C24 O1 -179.7(6) . . . . ?
C3 C22 C24 O1 -1.9(10) . . . . ?
C23 C22 C24 O2 -0.3(8) . . . . ?
C3 C22 C24 O2 177.5(5) . . . . ?
C24 O2 C25 C26 90.5(8) . . . . ?
C5 N1 C27 C28 94.1(6) . . . . ?
C1 N1 C27 C28 -81.1(7) . . . . ?

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 H28C O2 0.98 2.65 3.608(8) 165.9 2_655
C26 H26A Br1 0.98 2.91 3.641(10) 131.8 1_655
C25 H25A Br1 0.99 3.02 3.708(8) 127.9 1_655
C20 H20 Br2 0.95 2.99 3.746(8) 137.1 2_645
C18 H18 Br1 0.95 2.95 3.833(8) 154.4 3_566
C4 H4 O1 0.95 2.21 2.871(8) 125.4 .
C28 H28C O2 0.98 2.65 3.608(8) 165.9 2_655
C25 H25A Br1 0.99 3.02 3.708(8) 127.9 1_655
C20 H20 Br2 0.95 2.99 3.746(8) 137.1 2_645
C18 H18 Br1 0.95 2.95 3.833(8) 154.4 3_566
C4 H4 O1 0.95 2.21 2.871(8) 125.4 .
C4 H4 O1 0.95 2.21 2.871(8) 125.4 .
C18 H18 Br1 0.95 2.95 3.833(8) 154.4 3_566
C20 H20 Br2 0.95 2.99 3.746(8) 137.1 2_645
C25 H25A Br1 0.99 3.02 3.708(8) 127.9 1_655
C26 H26A Br1 0.98 2.91 3.641(10) 131.8 1_655
C28 H28C O2 0.98 2.65 3.608(8) 165.9 2_655

_refine_diff_density_max         1.494
_refine_diff_density_min         -0.866
_refine_diff_density_rms         0.114

_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_dd18141
_database_code_depnum_ccdc_archive 'CCDC 1897636'
loop_
_audit_author_name
_audit_author_address
'Xiaobo Huang'
;Wenzhou University 
China
;
_audit_update_record             
;
2019-02-17 deposited with the CCDC.	2019-05-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H24 Cl2 N2 O2'
_chemical_formula_weight         491.39

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   17.277(2)
_cell_length_b                   19.953(3)
_cell_length_c                   7.8040(11)
_cell_angle_alpha                90
_cell_angle_beta                 98.811(5)
_cell_angle_gamma                90
_cell_volume                     2658.5(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    2848
_cell_measurement_theta_min      5.190
_cell_measurement_theta_max      51.543

_exptl_crystal_description       prismatic
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.228
_exptl_crystal_F_000             1024
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.170
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    0.270
_shelx_estimated_absorpt_T_min   0.955
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5205
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(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            12237
_diffrn_reflns_av_unetI/netI     0.0850
_diffrn_reflns_av_R_equivalents  0.0601
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.386
_diffrn_reflns_theta_max         25.499
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.987
_reflns_number_total             4884
_reflns_number_gt                2581
_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)+(0.0671P)²+2.4561P] 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       0.0045(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4884
_refine_ls_number_parameters     310
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1443
_refine_ls_R_factor_gt           0.0692
_refine_ls_wR_factor_ref         0.1926
_refine_ls_wR_factor_gt          0.1488
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_restrained_S_all      1.016
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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
Cl1 Cl 0.09888(9) 0.86154(7) 0.17047(19) 0.0888(5) Uani 1 1 d . . . . .
Cl2 Cl 1.03606(7) 0.42574(7) 0.75598(19) 0.0774(5) Uani 1 1 d . . . . .
N1 N 0.5306(2) 0.60217(15) 0.6256(4) 0.0391(8) Uani 1 1 d . . . . .
N2 N 0.5068(2) 0.33648(18) 0.9321(5) 0.0587(11) Uani 1 1 d . . . . .
O1 O 0.28337(17) 0.46985(14) 0.7587(4) 0.0506(8) Uani 1 1 d . . . . .
O2 O 0.31415(16) 0.36693(13) 0.8679(4) 0.0543(8) Uani 1 1 d . . . . .
C1 C 0.5726(2) 0.54631(18) 0.6856(5) 0.0406(10) Uani 1 1 d . . . . .
C2 C 0.5353(2) 0.49327(18) 0.7492(5) 0.0401(10) Uani 1 1 d . . . . .
H2 H 0.5656 0.4554 0.7917 0.048 Uiso 1 1 calc R U . . .
C3 C 0.4542(2) 0.49222(18) 0.7546(5) 0.0392(10) Uani 1 1 d . . . . .
C4 C 0.4134(2) 0.55134(19) 0.6916(5) 0.0411(10) Uani 1 1 d . . . . .
H4 H 0.3588 0.5544 0.6944 0.049 Uiso 1 1 calc R U . . .
C5 C 0.4511(2) 0.60431(18) 0.6265(5) 0.0404(10) Uani 1 1 d . . . . .
C6 C 0.4055(2) 0.66354(19) 0.5576(5) 0.0446(11) Uani 1 1 d . . . . .
H14 H 0.4270 0.7071 0.5792 0.053 Uiso 1 1 calc R U . . .
C7 C 0.3345(3) 0.65636(19) 0.4652(5) 0.0457(11) Uani 1 1 d . . . . .
H7 H 0.3174 0.6115 0.4423 0.055 Uiso 1 1 calc R U . . .
C8 C 0.2796(2) 0.70857(19) 0.3946(5) 0.0437(10) Uani 1 1 d . . . . .
C9 C 0.2058(3) 0.6897(2) 0.3144(6) 0.0561(12) Uani 1 1 d . . . . .
H9 H 0.1933 0.6434 0.3060 0.067 Uiso 1 1 calc R U . . .
C10 C 0.1492(3) 0.7359(2) 0.2456(6) 0.0615(13) Uani 1 1 d . . . . .
H10 H 0.0987 0.7217 0.1920 0.074 Uiso 1 1 calc R U . . .
C11 C 0.1685(3) 0.8030(2) 0.2578(6) 0.0560(12) Uani 1 1 d . . . . .
C12 C 0.2415(3) 0.8236(2) 0.3348(6) 0.0580(13) Uani 1 1 d . . . . .
H12 H 0.2537 0.8701 0.3404 0.070 Uiso 1 1 calc R U . . .
C13 C 0.2974(3) 0.7774(2) 0.4045(6) 0.0517(12) Uani 1 1 d . . . . .
H13 H 0.3475 0.7921 0.4587 0.062 Uiso 1 1 calc R U . . .
C14 C 0.6562(2) 0.54243(19) 0.6752(5) 0.0431(10) Uani 1 1 d . . . . .
H14A H 0.6744 0.5620 0.5779 0.052 Uiso 1 1 calc R U . . .
C15 C 0.7084(2) 0.51269(19) 0.7958(5) 0.0433(10) Uani 1 1 d . . . . .
H15 H 0.6898 0.4997 0.8993 0.052 Uiso 1 1 calc R U . . .
C16 C 0.7905(2) 0.49786(19) 0.7874(5) 0.0427(10) Uani 1 1 d . . . . .
C17 C 0.8239(3) 0.5052(2) 0.6349(6) 0.0497(11) Uani 1 1 d . . . . .
H17 H 0.7937 0.5243 0.5349 0.060 Uiso 1 1 calc R U . . .
C18 C 0.8992(3) 0.4851(2) 0.6287(6) 0.0543(12) Uani 1 1 d . . . . .
H18 H 0.9211 0.4910 0.5253 0.065 Uiso 1 1 calc R U . . .
C19 C 0.9429(3) 0.4564(2) 0.7707(6) 0.0536(12) Uani 1 1 d . . . . .
C20 C 0.9136(3) 0.4495(2) 0.9242(6) 0.0538(12) Uani 1 1 d . . . . .
H20 H 0.9448 0.4309 1.0235 0.065 Uiso 1 1 calc R U . . .
C21 C 0.8377(3) 0.4704(2) 0.9308(6) 0.0501(11) Uani 1 1 d . . . . .
H21 H 0.8171 0.4658 1.0363 0.060 Uiso 1 1 calc R U . . .
C22 C 0.4172(2) 0.43510(18) 0.8166(5) 0.0382(10) Uani 1 1 d . . . . .
C23 C 0.4658(3) 0.3801(2) 0.8816(5) 0.0433(10) Uani 1 1 d . . . . .
C24 C 0.3341(3) 0.4285(2) 0.8099(5) 0.0439(10) Uani 1 1 d . . . . .
C25 C 0.2316(3) 0.3541(3) 0.8609(8) 0.0696(15) Uani 1 1 d . . . . .
H25A H 0.2036 0.3968 0.8724 0.083 Uiso 1 1 calc R U . . .
H25B H 0.2231 0.3245 0.9582 0.083 Uiso 1 1 calc R U . . .
C26 C 0.1999(4) 0.3214(4) 0.6926(12) 0.141(3) Uani 1 1 d . . . . .
H26A H 0.2053 0.3520 0.5969 0.211 Uiso 1 1 calc R U . . .
H26B H 0.1444 0.3107 0.6910 0.211 Uiso 1 1 calc R U . . .
H26C H 0.2291 0.2801 0.6795 0.211 Uiso 1 1 calc R U . . .
C27 C 0.5714(3) 0.66183(19) 0.5657(5) 0.0466(11) Uani 1 1 d . . . . .
H27A H 0.5337 0.6889 0.4859 0.056 Uiso 1 1 calc R U . . .
H27B H 0.6135 0.6468 0.5017 0.056 Uiso 1 1 calc R U . . .
C28 C 0.6061(3) 0.7042(2) 0.7187(6) 0.0591(13) Uani 1 1 d . . . . .
H28A H 0.6301 0.7443 0.6772 0.089 Uiso 1 1 calc R U . . .
H28B H 0.6460 0.6783 0.7935 0.089 Uiso 1 1 calc R U . . .
H28C H 0.5647 0.7175 0.7846 0.089 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
Cl1 C11 1.740(4) . ?
Cl2 C19 1.743(5) . ?
N1 C1 1.373(5) . ?
N1 C5 1.375(5) . ?
N1 C27 1.495(5) . ?
N2 C23 1.153(5) . ?
O1 C24 1.224(4) . ?
O2 C24 1.372(5) . ?
O2 C25 1.443(5) . ?
C1 C2 1.372(5) . ?
C1 C14 1.460(6) . ?
C2 C3 1.408(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.422(5) . ?
C3 C22 1.427(5) . ?
C4 C5 1.378(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.475(5) . ?
C6 C7 1.333(5) . ?
C6 H14 0.9500 . ?
C7 C8 1.458(5) . ?
C7 H7 0.9500 . ?
C8 C9 1.384(6) . ?
C8 C13 1.407(5) . ?
C9 C10 1.389(6) . ?
C9 H9 0.9500 . ?
C10 C11 1.380(6) . ?
C10 H10 0.9500 . ?
C11 C12 1.375(6) . ?
C12 C13 1.384(6) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 C15 1.338(5) . ?
C14 H14A 0.9500 . ?
C15 C16 1.461(5) . ?
C15 H15 0.9500 . ?
C16 C21 1.392(6) . ?
C16 C17 1.407(6) . ?
C17 C18 1.370(6) . ?
C17 H17 0.9500 . ?
C18 C19 1.366(6) . ?
C18 H18 0.9500 . ?
C19 C20 1.377(6) . ?
C20 C21 1.384(6) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
C22 C23 1.426(5) . ?
C22 C24 1.436(6) . ?
C25 C26 1.493(9) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 C28 1.509(6) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?

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
C1 N1 C5 120.0(3) . . ?
C1 N1 C27 120.2(3) . . ?
C5 N1 C27 119.8(3) . . ?
C24 O2 C25 116.3(3) . . ?
C2 C1 N1 119.7(4) . . ?
C2 C1 C14 120.2(4) . . ?
N1 C1 C14 120.0(4) . . ?
C1 C2 C3 123.2(4) . . ?
C1 C2 H2 118.4 . . ?
C3 C2 H2 118.4 . . ?
C2 C3 C4 114.8(4) . . ?
C2 C3 C22 121.4(3) . . ?
C4 C3 C22 123.8(4) . . ?
C5 C4 C3 121.8(4) . . ?
C5 C4 H4 119.1 . . ?
C3 C4 H4 119.1 . . ?
N1 C5 C4 120.4(3) . . ?
N1 C5 C6 120.0(4) . . ?
C4 C5 C6 119.6(4) . . ?
C7 C6 C5 120.5(4) . . ?
C7 C6 H14 119.8 . . ?
C5 C6 H14 119.8 . . ?
C6 C7 C8 128.2(4) . . ?
C6 C7 H7 115.9 . . ?
C8 C7 H7 115.9 . . ?
C9 C8 C13 117.9(4) . . ?
C9 C8 C7 118.5(4) . . ?
C13 C8 C7 123.6(4) . . ?
C8 C9 C10 122.7(4) . . ?
C8 C9 H9 118.7 . . ?
C10 C9 H9 118.7 . . ?
C11 C10 C9 117.9(5) . . ?
C11 C10 H10 121.1 . . ?
C9 C10 H10 121.1 . . ?
C12 C11 C10 121.2(4) . . ?
C12 C11 Cl1 120.2(4) . . ?
C10 C11 Cl1 118.6(4) . . ?
C11 C12 C13 120.6(4) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
C12 C13 C8 119.7(4) . . ?
C12 C13 H13 120.1 . . ?
C8 C13 H13 120.1 . . ?
C15 C14 C1 123.4(4) . . ?
C15 C14 H14A 118.3 . . ?
C1 C14 H14A 118.3 . . ?
C14 C15 C16 127.8(4) . . ?
C14 C15 H15 116.1 . . ?
C16 C15 H15 116.1 . . ?
C21 C16 C17 117.1(4) . . ?
C21 C16 C15 119.8(4) . . ?
C17 C16 C15 122.9(4) . . ?
C18 C17 C16 121.0(4) . . ?
C18 C17 H17 119.5 . . ?
C16 C17 H17 119.5 . . ?
C19 C18 C17 120.2(4) . . ?
C19 C18 H18 119.9 . . ?
C17 C18 H18 119.9 . . ?
C18 C19 C20 121.1(4) . . ?
C18 C19 Cl2 119.7(4) . . ?
C20 C19 Cl2 119.2(4) . . ?
C19 C20 C21 118.6(4) . . ?
C19 C20 H20 120.7 . . ?
C21 C20 H20 120.7 . . ?
C20 C21 C16 122.0(4) . . ?
C20 C21 H21 119.0 . . ?
C16 C21 H21 119.0 . . ?
C23 C22 C3 117.8(4) . . ?
C23 C22 C24 118.3(4) . . ?
C3 C22 C24 123.9(4) . . ?
N2 C23 C22 178.0(5) . . ?
O1 C24 O2 120.5(4) . . ?
O1 C24 C22 127.7(4) . . ?
O2 C24 C22 111.7(3) . . ?
O2 C25 C26 109.8(5) . . ?
O2 C25 H25A 109.7 . . ?
C26 C25 H25A 109.7 . . ?
O2 C25 H25B 109.7 . . ?
C26 C25 H25B 109.7 . . ?
H25A C25 H25B 108.2 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
N1 C27 C28 110.3(3) . . ?
N1 C27 H27A 109.6 . . ?
C28 C27 H27A 109.6 . . ?
N1 C27 H27B 109.6 . . ?
C28 C27 H27B 109.6 . . ?
H27A C27 H27B 108.1 . . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C1 C2 -1.2(5) . . . . ?
C27 N1 C1 C2 176.4(3) . . . . ?
C5 N1 C1 C14 176.4(3) . . . . ?
C27 N1 C1 C14 -6.0(5) . . . . ?
N1 C1 C2 C3 1.0(6) . . . . ?
C14 C1 C2 C3 -176.7(4) . . . . ?
C1 C2 C3 C4 -1.1(5) . . . . ?
C1 C2 C3 C22 177.9(4) . . . . ?
C2 C3 C4 C5 1.6(5) . . . . ?
C22 C3 C4 C5 -177.4(4) . . . . ?
C1 N1 C5 C4 1.7(5) . . . . ?
C27 N1 C5 C4 -175.9(3) . . . . ?
C1 N1 C5 C6 -178.3(3) . . . . ?
C27 N1 C5 C6 4.1(5) . . . . ?
C3 C4 C5 N1 -2.0(6) . . . . ?
C3 C4 C5 C6 178.0(3) . . . . ?
N1 C5 C6 C7 140.8(4) . . . . ?
C4 C5 C6 C7 -39.2(6) . . . . ?
C5 C6 C7 C8 176.6(4) . . . . ?
C6 C7 C8 C9 -174.6(4) . . . . ?
C6 C7 C8 C13 5.0(7) . . . . ?
C13 C8 C9 C10 -0.6(7) . . . . ?
C7 C8 C9 C10 179.0(4) . . . . ?
C8 C9 C10 C11 0.5(7) . . . . ?
C9 C10 C11 C12 0.2(7) . . . . ?
C9 C10 C11 Cl1 179.3(3) . . . . ?
C10 C11 C12 C13 -0.8(7) . . . . ?
Cl1 C11 C12 C13 -179.9(3) . . . . ?
C11 C12 C13 C8 0.7(7) . . . . ?
C9 C8 C13 C12 0.0(6) . . . . ?
C7 C8 C13 C12 -179.6(4) . . . . ?
C2 C1 C14 C15 -37.9(6) . . . . ?
N1 C1 C14 C15 144.5(4) . . . . ?
C1 C14 C15 C16 170.8(4) . . . . ?
C14 C15 C16 C21 175.8(4) . . . . ?
C14 C15 C16 C17 -9.3(6) . . . . ?
C21 C16 C17 C18 0.9(6) . . . . ?
C15 C16 C17 C18 -174.1(4) . . . . ?
C16 C17 C18 C19 1.1(6) . . . . ?
C17 C18 C19 C20 -2.5(7) . . . . ?
C17 C18 C19 Cl2 175.5(3) . . . . ?
C18 C19 C20 C21 1.9(7) . . . . ?
Cl2 C19 C20 C21 -176.0(3) . . . . ?
C19 C20 C21 C16 0.1(6) . . . . ?
C17 C16 C21 C20 -1.4(6) . . . . ?
C15 C16 C21 C20 173.7(4) . . . . ?
C2 C3 C22 C23 3.2(5) . . . . ?
C4 C3 C22 C23 -177.9(3) . . . . ?
C2 C3 C22 C24 -173.8(4) . . . . ?
C4 C3 C22 C24 5.1(6) . . . . ?
C25 O2 C24 O1 1.3(6) . . . . ?
C25 O2 C24 C22 -177.9(4) . . . . ?
C23 C22 C24 O1 180.0(4) . . . . ?
C3 C22 C24 O1 -3.1(7) . . . . ?
C23 C22 C24 O2 -0.9(5) . . . . ?
C3 C22 C24 O2 176.1(3) . . . . ?
C24 O2 C25 C26 91.9(5) . . . . ?
C1 N1 C27 C28 -81.9(4) . . . . ?
C5 N1 C27 C28 95.8(4) . . . . ?

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
C4 H4 O1 0.95 2.23 2.886(5) 124.9 .
C18 H18 Cl2 0.95 2.94 3.803(5) 152.3 3_766
C20 H20 Cl1 0.95 2.96 3.653(5) 131.2 2_646
C25 H25A Cl2 0.99 2.95 3.643(5) 127.5 1_455

_refine_diff_density_max         0.474
_refine_diff_density_min         -0.308
_refine_diff_density_rms         0.059

_shelxl_version_number           2013-4

