# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2022

####################################################################### 
# 
# 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_c
_database_code_depnum_ccdc_archive 'CCDC 2152464'
loop_
_audit_author_name
_audit_author_address
'Jiangtao Sun'
;Changzhou University
China
;
_audit_update_record             
;
2022-02-16 deposited with the CCDC.	2022-05-02 downloaded from the CCDC.
;
_audit_creation_date             2020-10-18
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H20 Cl N O3'
_chemical_formula_sum            'C25 H20 Cl N O3'
_chemical_formula_weight         417.87
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_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                   19.1104(10)
_cell_length_b                   16.7231(10)
_cell_length_c                   13.9585(9)
_cell_angle_alpha                90
_cell_angle_beta                 110.918(2)
_cell_angle_gamma                90
_cell_volume                     4166.9(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9981
_cell_measurement_temperature    196.15
_cell_measurement_theta_max      27.460
_cell_measurement_theta_min      2.549
_shelx_estimated_absorpt_T_max   0.979
_shelx_estimated_absorpt_T_min   0.975
_exptl_absorpt_coefficient_mu    0.210
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6461
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1367 before and 0.0867 after correction.
The Ratio of minimum to maximum transmission is 0.8666.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1744
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0795
_diffrn_reflns_av_unetI/netI     0.0712
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            35429
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.496
_diffrn_reflns_theta_min         1.981
_diffrn_ambient_temperature      196.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           40.0
_diffrn_source_power             2.0
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                7205
_reflns_number_total             9535
_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 V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.368
_refine_diff_density_min         -0.345
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     543
_refine_ls_number_reflns         9535
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0895
_refine_ls_R_factor_gt           0.0640
_refine_ls_restrained_S_all      1.076
_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)+(0.0383P)²+2.9678P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1322
_refine_ls_wR_factor_ref         0.1442
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C16(H16), C33(H33)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C10(H10), C11(H11), C12(H12),
 C13(H13), C14(H14), C17(H17), C20(H20), C21(H21), C22(H22), C23(H23), C24(H24),
  C26(H26), C27(H27), C28(H28), C29(H29), C30(H30), C36(H36), C37(H37),
 C38(H38), C39(H39), C40(H40), C42(H42), C44(H44), C45(H45), C46(H46), C47(H47),
  C48(H48)
2.c Idealised Me refined as rotating group:
 C25(H25A,H25B,H25C), C50(H50A,H50B,H50C)
;
_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
Cl1 Cl 0.28426(4) 0.74465(5) 0.69367(6) 0.0474(2) Uani 1 1 d . . . . .
O1 O 0.44938(10) 0.54038(10) 0.89389(15) 0.0365(4) Uani 1 1 d . . . . .
O2 O 0.45305(9) 0.65710(10) 0.97394(13) 0.0285(4) Uani 1 1 d . . . . .
O3 O 0.54160(10) 0.83697(10) 0.89021(14) 0.0363(4) Uani 1 1 d . . . . .
N1 N 0.57793(10) 0.70808(11) 0.95874(15) 0.0229(4) Uani 1 1 d . . . . .
C1 C 0.64045(13) 0.78780(16) 1.1102(2) 0.0312(6) Uani 1 1 d . . . . .
H1 H 0.635324 0.833720 1.068143 0.037 Uiso 1 1 calc R U . . .
C2 C 0.67406(14) 0.79380(18) 1.2155(2) 0.0374(6) Uani 1 1 d . . . . .
H2 H 0.690802 0.844421 1.245980 0.045 Uiso 1 1 calc R U . . .
C3 C 0.68352(15) 0.7272(2) 1.2767(2) 0.0445(7) Uani 1 1 d . . . . .
H3 H 0.707671 0.731447 1.348916 0.053 Uiso 1 1 calc R U . . .
C4 C 0.65755(16) 0.65400(19) 1.2321(2) 0.0440(7) Uani 1 1 d . . . . .
H4 H 0.663768 0.608025 1.274293 0.053 Uiso 1 1 calc R U . . .
C5 C 0.62261(14) 0.64661(16) 1.1268(2) 0.0331(6) Uani 1 1 d . . . . .
H5 H 0.604764 0.596108 1.096894 0.040 Uiso 1 1 calc R U . . .
C6 C 0.61409(12) 0.71366(14) 1.06612(18) 0.0247(5) Uani 1 1 d . . . . .
C7 C 0.54163(12) 0.63925(13) 0.89375(17) 0.0206(5) Uani 1 1 d . . . . .
C8 C 0.47689(12) 0.60433(14) 0.92090(17) 0.0226(5) Uani 1 1 d . . . . .
C9 C 0.59252(12) 0.57711(13) 0.87456(17) 0.0221(5) Uani 1 1 d . . . . .
C10 C 0.66944(13) 0.57784(14) 0.92745(18) 0.0260(5) Uani 1 1 d . . . . .
H10 H 0.690891 0.616358 0.979768 0.031 Uiso 1 1 calc R U . . .
C11 C 0.71514(14) 0.52232(16) 0.9040(2) 0.0326(6) Uani 1 1 d . . . . .
H11 H 0.767654 0.522733 0.940721 0.039 Uiso 1 1 calc R U . . .
C12 C 0.68443(15) 0.46682(16) 0.8277(2) 0.0347(6) Uani 1 1 d . . . . .
H12 H 0.715799 0.429159 0.811603 0.042 Uiso 1 1 calc R U . . .
C13 C 0.60805(15) 0.46581(16) 0.7744(2) 0.0340(6) Uani 1 1 d . . . . .
H13 H 0.586975 0.427457 0.721778 0.041 Uiso 1 1 calc R U . . .
C14 C 0.56216(13) 0.52056(14) 0.79769(18) 0.0281(5) Uani 1 1 d . . . . .
H14 H 0.509660 0.519535 0.760983 0.034 Uiso 1 1 calc R U . . .
C15 C 0.54298(13) 0.76520(14) 0.88616(18) 0.0258(5) Uani 1 1 d . . . . .
C16 C 0.50980(12) 0.70254(13) 0.80350(17) 0.0226(5) Uani 1 1 d . . . . .
H16 H 0.540281 0.700091 0.758366 0.027 Uiso 1 1 calc R U . . .
C17 C 0.37943(13) 0.74486(15) 0.7620(2) 0.0302(5) Uani 1 1 d . . . . .
H17 H 0.398162 0.778985 0.820016 0.036 Uiso 1 1 calc R U . . .
C18 C 0.42779(12) 0.69980(14) 0.73769(17) 0.0239(5) Uani 1 1 d . . . . .
C19 C 0.40849(12) 0.64241(14) 0.65136(18) 0.0244(5) Uani 1 1 d . . . . .
C20 C 0.44536(14) 0.64529(15) 0.58186(19) 0.0303(5) Uani 1 1 d . . . . .
H20 H 0.479452 0.687646 0.586054 0.036 Uiso 1 1 calc R U . . .
C21 C 0.43338(15) 0.58767(17) 0.5067(2) 0.0384(6) Uani 1 1 d . . . . .
H21 H 0.458921 0.590738 0.459590 0.046 Uiso 1 1 calc R U . . .
C22 C 0.38408(16) 0.52550(17) 0.5002(2) 0.0404(7) Uani 1 1 d . . . . .
H22 H 0.376329 0.485274 0.449396 0.049 Uiso 1 1 calc R U . . .
C23 C 0.34644(15) 0.52218(16) 0.5675(2) 0.0394(6) Uani 1 1 d . . . . .
H23 H 0.312155 0.479830 0.562386 0.047 Uiso 1 1 calc R U . . .
C24 C 0.35789(13) 0.57977(16) 0.64254(19) 0.0315(6) Uani 1 1 d . . . . .
H24 H 0.331297 0.576871 0.688393 0.038 Uiso 1 1 calc R U . . .
C25 C 0.38692(15) 0.63341(17) 0.9952(2) 0.0405(7) Uani 1 1 d . . . . .
H25A H 0.343536 0.632088 0.930947 0.061 Uiso 1 1 calc R U . . .
H25B H 0.377798 0.671973 1.042253 0.061 Uiso 1 1 calc R U . . .
H25C H 0.394788 0.580170 1.026565 0.061 Uiso 1 1 calc R U . . .
Cl2 Cl 0.23184(3) 0.71862(4) 0.41900(6) 0.03892(17) Uani 1 1 d . . . . .
O4 O 0.06552(11) 0.95552(10) 0.45743(15) 0.0406(5) Uani 1 1 d . . . . .
O5 O 0.06510(9) 0.83997(10) 0.53762(13) 0.0279(4) Uani 1 1 d . . . . .
O6 O -0.02314(11) 0.65417(10) 0.37890(17) 0.0441(5) Uani 1 1 d . . . . .
N2 N -0.05873(10) 0.78539(11) 0.40181(15) 0.0232(4) Uani 1 1 d . . . . .
C26 C -0.04226(14) 0.96433(15) 0.2430(2) 0.0320(6) Uani 1 1 d . . . . .
H26 H 0.010381 0.966272 0.259010 0.038 Uiso 1 1 calc R U . . .
C27 C -0.08829(15) 1.01419(16) 0.1686(2) 0.0358(6) Uani 1 1 d . . . . .
H27 H -0.067257 1.049775 0.133166 0.043 Uiso 1 1 calc R U . . .
C28 C -0.16483(15) 1.01281(15) 0.1452(2) 0.0351(6) Uani 1 1 d . . . . .
H28 H -0.196507 1.046994 0.093508 0.042 Uiso 1 1 calc R U . . .
C29 C -0.19502(13) 0.96141(15) 0.19754(19) 0.0300(5) Uani 1 1 d . . . . .
H29 H -0.247555 0.961073 0.182754 0.036 Uiso 1 1 calc R U . . .
C30 C -0.14895(13) 0.91018(14) 0.27169(18) 0.0259(5) Uani 1 1 d . . . . .
H30 H -0.170230 0.874405 0.306614 0.031 Uiso 1 1 calc R U . . .
C31 C -0.07212(12) 0.91098(13) 0.29502(17) 0.0222(5) Uani 1 1 d . . . . .
C32 C -0.02159(12) 0.85193(13) 0.36881(18) 0.0217(5) Uani 1 1 d . . . . .
C33 C 0.01147(12) 0.78494(13) 0.31527(18) 0.0243(5) Uani 1 1 d . . . . .
H33 H -0.017669 0.784763 0.239844 0.029 Uiso 1 1 calc R U . . .
C34 C -0.02388(13) 0.72580(14) 0.3681(2) 0.0289(5) Uani 1 1 d . . . . .
C35 C -0.09610(12) 0.78428(14) 0.47286(18) 0.0251(5) Uani 1 1 d . . . . .
C36 C -0.10130(14) 0.85306(15) 0.5250(2) 0.0321(6) Uani 1 1 d . . . . .
H36 H -0.080111 0.901646 0.512767 0.039 Uiso 1 1 calc R U . . .
C37 C -0.13745(15) 0.85088(18) 0.5950(2) 0.0402(7) Uani 1 1 d . . . . .
H37 H -0.140189 0.897900 0.631697 0.048 Uiso 1 1 calc R U . . .
C38 C -0.16956(16) 0.7809(2) 0.6119(2) 0.0470(8) Uani 1 1 d . . . . .
H38 H -0.194882 0.779717 0.659389 0.056 Uiso 1 1 calc R U . . .
C39 C -0.16457(16) 0.7128(2) 0.5595(2) 0.0471(8) Uani 1 1 d . . . . .
H39 H -0.186691 0.664663 0.571182 0.057 Uiso 1 1 calc R U . . .
C40 C -0.12784(14) 0.71301(16) 0.4898(2) 0.0357(6) Uani 1 1 d . . . . .
H40 H -0.124378 0.665572 0.454293 0.043 Uiso 1 1 calc R U . . .
C41 C 0.09396(13) 0.78352(14) 0.33304(18) 0.0247(5) Uani 1 1 d . . . . .
C42 C 0.13731(13) 0.72997(15) 0.39656(19) 0.0286(5) Uani 1 1 d . . . . .
H42 H 0.115192 0.695655 0.432021 0.034 Uiso 1 1 calc R U . . .
C43 C 0.12014(13) 0.84441(14) 0.27581(19) 0.0268(5) Uani 1 1 d . . . . .
C44 C 0.17637(14) 0.89825(15) 0.3281(2) 0.0341(6) Uani 1 1 d . . . . .
H44 H 0.200377 0.893984 0.400409 0.041 Uiso 1 1 calc R U . . .
C45 C 0.19751(17) 0.95826(18) 0.2750(3) 0.0501(8) Uani 1 1 d . . . . .
H45 H 0.236010 0.994690 0.311248 0.060 Uiso 1 1 calc R U . . .
C46 C 0.1634(2) 0.9652(2) 0.1711(3) 0.0586(10) Uani 1 1 d . . . . .
H46 H 0.177886 1.006526 0.135367 0.070 Uiso 1 1 calc R U . . .
C47 C 0.1075(2) 0.9118(2) 0.1181(3) 0.0559(9) Uani 1 1 d . . . . .
H47 H 0.083775 0.916537 0.045805 0.067 Uiso 1 1 calc R U . . .
C48 C 0.08606(16) 0.85178(18) 0.1700(2) 0.0391(6) Uani 1 1 d . . . . .
H48 H 0.047816 0.815303 0.133129 0.047 Uiso 1 1 calc R U . . .
C49 C 0.04075(12) 0.89039(14) 0.45918(18) 0.0231(5) Uani 1 1 d . . . . .
C50 C 0.12305(15) 0.87087(18) 0.6278(2) 0.0440(7) Uani 1 1 d . . . . .
H50A H 0.168469 0.880804 0.612400 0.066 Uiso 1 1 calc R U . . .
H50B H 0.133962 0.831787 0.683558 0.066 Uiso 1 1 calc R U . . .
H50C H 0.106079 0.920992 0.648688 0.066 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 C17 1.726(2) . ?
O1 C8 1.192(3) . ?
O2 C8 1.332(3) . ?
O2 C25 1.452(3) . ?
O3 C15 1.202(3) . ?
N1 C6 1.412(3) . ?
N1 C7 1.476(3) . ?
N1 C15 1.379(3) . ?
C1 H1 0.9500 . ?
C1 C2 1.382(4) . ?
C1 C6 1.396(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.376(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.383(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.385(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.380(3) . ?
C7 C8 1.533(3) . ?
C7 C9 1.511(3) . ?
C7 C16 1.591(3) . ?
C9 C10 1.390(3) . ?
C9 C14 1.392(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.391(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.376(4) . ?
C12 H12 0.9500 . ?
C12 C13 1.382(4) . ?
C13 H13 0.9500 . ?
C13 C14 1.384(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.520(3) . ?
C16 H16 1.0000 . ?
C16 C18 1.508(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.327(3) . ?
C18 C19 1.481(3) . ?
C19 C20 1.389(3) . ?
C19 C24 1.401(3) . ?
C20 H20 0.9500 . ?
C20 C21 1.382(4) . ?
C21 H21 0.9500 . ?
C21 C22 1.384(4) . ?
C22 H22 0.9500 . ?
C22 C23 1.373(4) . ?
C23 H23 0.9500 . ?
C23 C24 1.382(4) . ?
C24 H24 0.9500 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
Cl2 C42 1.730(2) . ?
O4 C49 1.191(3) . ?
O5 C49 1.328(3) . ?
O5 C50 1.443(3) . ?
O6 C34 1.207(3) . ?
N2 C32 1.479(3) . ?
N2 C34 1.372(3) . ?
N2 C35 1.414(3) . ?
C26 H26 0.9500 . ?
C26 C27 1.376(3) . ?
C26 C31 1.395(3) . ?
C27 H27 0.9500 . ?
C27 C28 1.381(4) . ?
C28 H28 0.9500 . ?
C28 C29 1.380(4) . ?
C29 H29 0.9500 . ?
C29 C30 1.389(3) . ?
C30 H30 0.9500 . ?
C30 C31 1.386(3) . ?
C31 C32 1.503(3) . ?
C32 C33 1.597(3) . ?
C32 C49 1.533(3) . ?
C33 H33 1.0000 . ?
C33 C34 1.528(3) . ?
C33 C41 1.506(3) . ?
C35 C36 1.383(3) . ?
C35 C40 1.395(3) . ?
C36 H36 0.9500 . ?
C36 C37 1.384(4) . ?
C37 H37 0.9500 . ?
C37 C38 1.381(4) . ?
C38 H38 0.9500 . ?
C38 C39 1.375(5) . ?
C39 H39 0.9500 . ?
C39 C40 1.388(4) . ?
C40 H40 0.9500 . ?
C41 C42 1.323(3) . ?
C41 C43 1.487(3) . ?
C42 H42 0.9500 . ?
C43 C44 1.392(4) . ?
C43 C48 1.391(4) . ?
C44 H44 0.9500 . ?
C44 C45 1.391(4) . ?
C45 H45 0.9500 . ?
C45 C46 1.366(5) . ?
C46 H46 0.9500 . ?
C46 C47 1.386(5) . ?
C47 H47 0.9500 . ?
C47 C48 1.383(4) . ?
C48 H48 0.9500 . ?
C50 H50A 0.9800 . ?
C50 H50B 0.9800 . ?
C50 H50C 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
C8 O2 C25 115.32(19) . . ?
C6 N1 C7 130.42(19) . . ?
C15 N1 C6 131.3(2) . . ?
C15 N1 C7 95.19(17) . . ?
C2 C1 H1 120.3 . . ?
C2 C1 C6 119.4(3) . . ?
C6 C1 H1 120.3 . . ?
C1 C2 H2 119.7 . . ?
C3 C2 C1 120.6(3) . . ?
C3 C2 H2 119.7 . . ?
C2 C3 H3 120.3 . . ?
C2 C3 C4 119.4(3) . . ?
C4 C3 H3 120.3 . . ?
C3 C4 H4 119.5 . . ?
C3 C4 C5 121.1(3) . . ?
C5 C4 H4 119.5 . . ?
C4 C5 H5 120.5 . . ?
C6 C5 C4 119.0(3) . . ?
C6 C5 H5 120.5 . . ?
C1 C6 N1 119.3(2) . . ?
C5 C6 N1 120.3(2) . . ?
C5 C6 C1 120.4(2) . . ?
N1 C7 C8 112.87(18) . . ?
N1 C7 C9 117.01(18) . . ?
N1 C7 C16 86.03(16) . . ?
C8 C7 C16 109.58(17) . . ?
C9 C7 C8 114.15(18) . . ?
C9 C7 C16 113.93(18) . . ?
O1 C8 O2 124.8(2) . . ?
O1 C8 C7 124.6(2) . . ?
O2 C8 C7 110.57(19) . . ?
C10 C9 C7 121.7(2) . . ?
C10 C9 C14 119.1(2) . . ?
C14 C9 C7 119.1(2) . . ?
C9 C10 H10 119.9 . . ?
C9 C10 C11 120.2(2) . . ?
C11 C10 H10 119.9 . . ?
C10 C11 H11 119.9 . . ?
C12 C11 C10 120.1(2) . . ?
C12 C11 H11 119.9 . . ?
C11 C12 H12 120.0 . . ?
C11 C12 C13 120.1(2) . . ?
C13 C12 H12 120.0 . . ?
C12 C13 H13 119.9 . . ?
C12 C13 C14 120.1(2) . . ?
C14 C13 H13 119.9 . . ?
C9 C14 H14 119.8 . . ?
C13 C14 C9 120.4(2) . . ?
C13 C14 H14 119.8 . . ?
O3 C15 N1 132.1(2) . . ?
O3 C15 C16 135.5(2) . . ?
N1 C15 C16 92.39(18) . . ?
C7 C16 H16 109.1 . . ?
C15 C16 C7 85.38(17) . . ?
C15 C16 H16 109.1 . . ?
C18 C16 C7 118.86(18) . . ?
C18 C16 C15 123.00(19) . . ?
C18 C16 H16 109.1 . . ?
Cl1 C17 H17 118.3 . . ?
C18 C17 Cl1 123.4(2) . . ?
C18 C17 H17 118.3 . . ?
C17 C18 C16 119.6(2) . . ?
C17 C18 C19 125.6(2) . . ?
C19 C18 C16 114.72(19) . . ?
C20 C19 C18 120.3(2) . . ?
C20 C19 C24 118.1(2) . . ?
C24 C19 C18 121.3(2) . . ?
C19 C20 H20 119.4 . . ?
C21 C20 C19 121.2(2) . . ?
C21 C20 H20 119.4 . . ?
C20 C21 H21 120.1 . . ?
C20 C21 C22 119.9(2) . . ?
C22 C21 H21 120.1 . . ?
C21 C22 H22 120.1 . . ?
C23 C22 C21 119.8(3) . . ?
C23 C22 H22 120.1 . . ?
C22 C23 H23 119.6 . . ?
C22 C23 C24 120.7(2) . . ?
C24 C23 H23 119.6 . . ?
C19 C24 H24 119.8 . . ?
C23 C24 C19 120.4(2) . . ?
C23 C24 H24 119.8 . . ?
O2 C25 H25A 109.5 . . ?
O2 C25 H25B 109.5 . . ?
O2 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C49 O5 C50 115.2(2) . . ?
C34 N2 C32 95.39(17) . . ?
C34 N2 C35 131.3(2) . . ?
C35 N2 C32 130.32(19) . . ?
C27 C26 H26 119.7 . . ?
C27 C26 C31 120.7(2) . . ?
C31 C26 H26 119.7 . . ?
C26 C27 H27 119.8 . . ?
C26 C27 C28 120.4(2) . . ?
C28 C27 H27 119.8 . . ?
C27 C28 H28 120.2 . . ?
C29 C28 C27 119.5(2) . . ?
C29 C28 H28 120.2 . . ?
C28 C29 H29 119.8 . . ?
C28 C29 C30 120.3(2) . . ?
C30 C29 H29 119.8 . . ?
C29 C30 H30 119.8 . . ?
C31 C30 C29 120.4(2) . . ?
C31 C30 H30 119.8 . . ?
C26 C31 C32 119.7(2) . . ?
C30 C31 C26 118.7(2) . . ?
C30 C31 C32 121.5(2) . . ?
N2 C32 C31 116.46(18) . . ?
N2 C32 C33 86.10(16) . . ?
N2 C32 C49 112.19(18) . . ?
C31 C32 C33 113.89(19) . . ?
C31 C32 C49 114.11(18) . . ?
C49 C32 C33 110.99(17) . . ?
C32 C33 H33 109.3 . . ?
C34 C33 C32 84.91(17) . . ?
C34 C33 H33 109.3 . . ?
C41 C33 C32 119.99(18) . . ?
C41 C33 H33 109.3 . . ?
C41 C33 C34 121.8(2) . . ?
O6 C34 N2 131.6(2) . . ?
O6 C34 C33 135.7(2) . . ?
N2 C34 C33 92.74(18) . . ?
C36 C35 N2 120.5(2) . . ?
C36 C35 C40 120.3(2) . . ?
C40 C35 N2 119.3(2) . . ?
C35 C36 H36 120.1 . . ?
C35 C36 C37 119.8(2) . . ?
C37 C36 H36 120.1 . . ?
C36 C37 H37 119.8 . . ?
C38 C37 C36 120.5(3) . . ?
C38 C37 H37 119.8 . . ?
C37 C38 H38 120.3 . . ?
C39 C38 C37 119.4(3) . . ?
C39 C38 H38 120.3 . . ?
C38 C39 H39 119.4 . . ?
C38 C39 C40 121.3(3) . . ?
C40 C39 H39 119.4 . . ?
C35 C40 H40 120.7 . . ?
C39 C40 C35 118.7(3) . . ?
C39 C40 H40 120.7 . . ?
C42 C41 C33 119.3(2) . . ?
C42 C41 C43 125.0(2) . . ?
C43 C41 C33 115.7(2) . . ?
Cl2 C42 H42 118.0 . . ?
C41 C42 Cl2 124.0(2) . . ?
C41 C42 H42 118.0 . . ?
C44 C43 C41 120.4(2) . . ?
C48 C43 C41 120.8(2) . . ?
C48 C43 C44 118.8(2) . . ?
C43 C44 H44 119.9 . . ?
C45 C44 C43 120.2(3) . . ?
C45 C44 H44 119.9 . . ?
C44 C45 H45 119.7 . . ?
C46 C45 C44 120.5(3) . . ?
C46 C45 H45 119.7 . . ?
C45 C46 H46 120.1 . . ?
C45 C46 C47 119.8(3) . . ?
C47 C46 H46 120.1 . . ?
C46 C47 H47 119.9 . . ?
C48 C47 C46 120.2(3) . . ?
C48 C47 H47 119.9 . . ?
C43 C48 H48 119.8 . . ?
C47 C48 C43 120.5(3) . . ?
C47 C48 H48 119.8 . . ?
O4 C49 O5 124.9(2) . . ?
O4 C49 C32 124.4(2) . . ?
O5 C49 C32 110.65(19) . . ?
O5 C50 H50A 109.5 . . ?
O5 C50 H50B 109.5 . . ?
O5 C50 H50C 109.5 . . ?
H50A C50 H50B 109.5 . . ?
H50A C50 H50C 109.5 . . ?
H50B C50 H50C 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
Cl1 C17 C18 C16 -178.54(17) . . . . ?
Cl1 C17 C18 C19 -1.1(4) . . . . ?
O3 C15 C16 C7 -173.2(3) . . . . ?
O3 C15 C16 C18 -51.5(4) . . . . ?
N1 C7 C8 O1 -164.4(2) . . . . ?
N1 C7 C8 O2 19.0(3) . . . . ?
N1 C7 C9 C10 9.4(3) . . . . ?
N1 C7 C9 C14 -166.7(2) . . . . ?
N1 C7 C16 C15 -7.01(15) . . . . ?
N1 C7 C16 C18 -132.4(2) . . . . ?
N1 C15 C16 C7 7.50(16) . . . . ?
N1 C15 C16 C18 129.2(2) . . . . ?
C1 C2 C3 C4 -1.4(4) . . . . ?
C2 C1 C6 N1 178.3(2) . . . . ?
C2 C1 C6 C5 -1.1(3) . . . . ?
C2 C3 C4 C5 0.4(4) . . . . ?
C3 C4 C5 C6 0.3(4) . . . . ?
C4 C5 C6 N1 -179.3(2) . . . . ?
C4 C5 C6 C1 0.1(4) . . . . ?
C6 N1 C7 C8 59.4(3) . . . . ?
C6 N1 C7 C9 -76.1(3) . . . . ?
C6 N1 C7 C16 169.0(2) . . . . ?
C6 N1 C15 O3 11.5(4) . . . . ?
C6 N1 C15 C16 -169.1(2) . . . . ?
C6 C1 C2 C3 1.8(4) . . . . ?
C7 N1 C6 C1 -176.3(2) . . . . ?
C7 N1 C6 C5 3.1(3) . . . . ?
C7 N1 C15 O3 172.6(3) . . . . ?
C7 N1 C15 C16 -8.09(18) . . . . ?
C7 C9 C10 C11 -176.5(2) . . . . ?
C7 C9 C14 C13 176.3(2) . . . . ?
C7 C16 C18 C17 93.1(3) . . . . ?
C7 C16 C18 C19 -84.6(2) . . . . ?
C8 C7 C9 C10 -125.5(2) . . . . ?
C8 C7 C9 C14 58.4(3) . . . . ?
C8 C7 C16 C15 105.87(19) . . . . ?
C8 C7 C16 C18 -19.5(3) . . . . ?
C9 C7 C8 O1 -27.6(3) . . . . ?
C9 C7 C8 O2 155.86(18) . . . . ?
C9 C7 C16 C15 -124.87(19) . . . . ?
C9 C7 C16 C18 109.7(2) . . . . ?
C9 C10 C11 C12 0.5(4) . . . . ?
C10 C9 C14 C13 0.1(4) . . . . ?
C10 C11 C12 C13 -0.3(4) . . . . ?
C11 C12 C13 C14 0.0(4) . . . . ?
C12 C13 C14 C9 0.2(4) . . . . ?
C14 C9 C10 C11 -0.4(3) . . . . ?
C15 N1 C6 C1 -21.4(3) . . . . ?
C15 N1 C6 C5 157.9(2) . . . . ?
C15 N1 C7 C8 -101.9(2) . . . . ?
C15 N1 C7 C9 122.6(2) . . . . ?
C15 N1 C7 C16 7.74(17) . . . . ?
C15 C16 C18 C17 -11.3(3) . . . . ?
C15 C16 C18 C19 171.0(2) . . . . ?
C16 C7 C8 O1 101.6(3) . . . . ?
C16 C7 C8 O2 -75.0(2) . . . . ?
C16 C7 C9 C10 107.6(2) . . . . ?
C16 C7 C9 C14 -68.6(3) . . . . ?
C16 C18 C19 C20 -53.8(3) . . . . ?
C16 C18 C19 C24 120.5(2) . . . . ?
C17 C18 C19 C20 128.7(3) . . . . ?
C17 C18 C19 C24 -57.1(3) . . . . ?
C18 C19 C20 C21 173.7(2) . . . . ?
C18 C19 C24 C23 -173.4(2) . . . . ?
C19 C20 C21 C22 -0.3(4) . . . . ?
C20 C19 C24 C23 1.0(4) . . . . ?
C20 C21 C22 C23 1.1(4) . . . . ?
C21 C22 C23 C24 -0.8(4) . . . . ?
C22 C23 C24 C19 -0.3(4) . . . . ?
C24 C19 C20 C21 -0.7(4) . . . . ?
C25 O2 C8 O1 -2.4(3) . . . . ?
C25 O2 C8 C7 174.18(19) . . . . ?
N2 C32 C33 C34 -6.43(16) . . . . ?
N2 C32 C33 C41 -130.5(2) . . . . ?
N2 C32 C49 O4 -160.3(2) . . . . ?
N2 C32 C49 O5 22.2(2) . . . . ?
N2 C35 C36 C37 -179.4(2) . . . . ?
N2 C35 C40 C39 -179.8(2) . . . . ?
C26 C27 C28 C29 0.5(4) . . . . ?
C26 C31 C32 N2 -165.8(2) . . . . ?
C26 C31 C32 C33 -67.9(3) . . . . ?
C26 C31 C32 C49 61.0(3) . . . . ?
C27 C26 C31 C30 -1.2(4) . . . . ?
C27 C26 C31 C32 174.4(2) . . . . ?
C27 C28 C29 C30 -1.4(4) . . . . ?
C28 C29 C30 C31 1.0(4) . . . . ?
C29 C30 C31 C26 0.3(3) . . . . ?
C29 C30 C31 C32 -175.1(2) . . . . ?
C30 C31 C32 N2 9.6(3) . . . . ?
C30 C31 C32 C33 107.5(2) . . . . ?
C30 C31 C32 C49 -123.6(2) . . . . ?
C31 C26 C27 C28 0.8(4) . . . . ?
C31 C32 C33 C34 -123.71(19) . . . . ?
C31 C32 C33 C41 112.2(2) . . . . ?
C31 C32 C49 O4 -25.0(3) . . . . ?
C31 C32 C49 O5 157.46(18) . . . . ?
C32 N2 C34 O6 172.2(3) . . . . ?
C32 N2 C34 C33 -7.49(18) . . . . ?
C32 N2 C35 C36 -0.8(4) . . . . ?
C32 N2 C35 C40 179.1(2) . . . . ?
C32 C33 C34 O6 -172.7(3) . . . . ?
C32 C33 C34 N2 6.93(17) . . . . ?
C32 C33 C41 C42 103.4(3) . . . . ?
C32 C33 C41 C43 -76.6(3) . . . . ?
C33 C32 C49 O4 105.3(3) . . . . ?
C33 C32 C49 O5 -72.2(2) . . . . ?
C33 C41 C42 Cl2 176.70(17) . . . . ?
C33 C41 C43 C44 123.0(2) . . . . ?
C33 C41 C43 C48 -53.2(3) . . . . ?
C34 N2 C32 C31 122.0(2) . . . . ?
C34 N2 C32 C33 7.17(18) . . . . ?
C34 N2 C32 C49 -103.9(2) . . . . ?
C34 N2 C35 C36 154.5(2) . . . . ?
C34 N2 C35 C40 -25.6(4) . . . . ?
C34 C33 C41 C42 -0.4(3) . . . . ?
C34 C33 C41 C43 179.6(2) . . . . ?
C35 N2 C32 C31 -76.4(3) . . . . ?
C35 N2 C32 C33 168.8(2) . . . . ?
C35 N2 C32 C49 57.7(3) . . . . ?
C35 N2 C34 O6 10.8(4) . . . . ?
C35 N2 C34 C33 -168.9(2) . . . . ?
C35 C36 C37 C38 -1.2(4) . . . . ?
C36 C35 C40 C39 0.1(4) . . . . ?
C36 C37 C38 C39 0.8(4) . . . . ?
C37 C38 C39 C40 0.0(4) . . . . ?
C38 C39 C40 C35 -0.5(4) . . . . ?
C40 C35 C36 C37 0.7(4) . . . . ?
C41 C33 C34 O6 -50.3(4) . . . . ?
C41 C33 C34 N2 129.3(2) . . . . ?
C41 C43 C44 C45 -176.0(2) . . . . ?
C41 C43 C48 C47 175.8(2) . . . . ?
C42 C41 C43 C44 -57.0(3) . . . . ?
C42 C41 C43 C48 126.9(3) . . . . ?
C43 C41 C42 Cl2 -3.3(4) . . . . ?
C43 C44 C45 C46 0.1(4) . . . . ?
C44 C43 C48 C47 -0.4(4) . . . . ?
C44 C45 C46 C47 -0.3(5) . . . . ?
C45 C46 C47 C48 0.2(5) . . . . ?
C46 C47 C48 C43 0.2(4) . . . . ?
C48 C43 C44 C45 0.2(4) . . . . ?
C49 C32 C33 C34 105.85(19) . . . . ?
C49 C32 C33 C41 -18.2(3) . . . . ?
C50 O5 C49 O4 3.7(3) . . . . ?
C50 O5 C49 C32 -178.8(2) . . . . ?

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

data_a
_database_code_depnum_ccdc_archive 'CCDC 2152466'
loop_
_audit_author_name
_audit_author_address
'Jiangtao Sun'
;Changzhou University
China
;
_audit_update_record             
;
2022-02-16 deposited with the CCDC.	2022-05-02 downloaded from the CCDC.
;
_audit_creation_date             2020-09-09
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C27 H25 N O3'
_chemical_formula_sum            'C27 H25 N O3'
_chemical_formula_weight         411.48
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   9.8643(12)
_cell_length_b                   10.2577(12)
_cell_length_c                   12.3234(15)
_cell_angle_alpha                68.513(4)
_cell_angle_beta                 77.801(4)
_cell_angle_gamma                72.568(4)
_cell_volume                     1099.7(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1989
_cell_measurement_temperature    193
_cell_measurement_theta_max      27.454
_cell_measurement_theta_min      2.179
_shelx_estimated_absorpt_T_max   0.992
_shelx_estimated_absorpt_T_min   0.990
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6575
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1194 before and 0.0421 after correction.
The Ratio of minimum to maximum transmission is 0.8818.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.243
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             436
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0419
_diffrn_reflns_av_unetI/netI     0.0860
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9731
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.542
_diffrn_reflns_theta_min         2.178
_diffrn_ambient_temperature      193
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           40.0
_diffrn_source_power             2.0
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2918
_reflns_number_total             5033
_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 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.354
_refine_diff_density_min         -0.348
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     279
_refine_ls_number_reflns         5033
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1253
_refine_ls_R_factor_gt           0.0641
_refine_ls_restrained_S_all      1.015
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0460P)²+0.5363P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1247
_refine_ls_wR_factor_ref         0.1505
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C19(H19)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C15(H15), C14(H14), C13(H13), C9(H9), C23(H23), C7(H7), C27(H27),
 C6(H6), C24(H24), C8(H8), C25(H25), C26(H26)
2.c Fitted hexagon refined as free rotating group:
 C11(C10,C16,C15,C14,C13)
2.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C17(H17A,H17B,H17C), C28(H28A,H28B,H28C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O2 O 0.21940(19) 0.2527(2) 0.40391(16) 0.0381(5) Uani 1 1 d . . . . .
O3 O 0.57066(19) 0.54504(19) 0.10189(17) 0.0367(5) Uani 1 1 d . . . . .
O1 O 0.4234(2) 0.2321(2) 0.46691(17) 0.0452(5) Uani 1 1 d . . . . .
N1 N 0.5582(2) 0.3144(2) 0.23159(18) 0.0262(5) Uani 1 1 d . . . . .
C3 C 0.4154(2) 0.2776(2) 0.2608(2) 0.0240(5) Uani 1 1 d . . . . .
C4 C 0.4103(2) 0.1523(3) 0.2256(2) 0.0253(5) Uani 1 1 d . . . . .
C19 C 0.3556(2) 0.4384(2) 0.1813(2) 0.0243(5) Uani 1 1 d . . . . .
H19 H 0.324716 0.440817 0.108199 0.029 Uiso 1 1 calc R U . . .
C22 C 0.0965(3) 0.5829(3) 0.2081(2) 0.0265(6) Uani 1 1 d . . . . .
C2 C 0.3577(3) 0.2520(3) 0.3888(2) 0.0282(6) Uani 1 1 d . . . . .
C18 C 0.5096(3) 0.4511(3) 0.1607(2) 0.0270(6) Uani 1 1 d . . . . .
C20 C 0.2463(3) 0.5412(3) 0.2367(2) 0.0268(6) Uani 1 1 d . . . . .
C5 C 0.3503(3) 0.1689(3) 0.1281(2) 0.0291(6) Uani 1 1 d . . . . .
H5 H 0.307321 0.262818 0.079937 0.035 Uiso 1 1 calc R U . . .
C11 C 0.78006(16) 0.16895(19) 0.16194(13) 0.0315(6) Uani 1 1 d G . . . .
C10 C 0.70410(12) 0.23565(18) 0.24401(15) 0.0284(6) Uani 1 1 d G . . . .
C16 C 0.77114(17) 0.2298(2) 0.33479(14) 0.0373(7) Uani 1 1 d G . . . .
C15 C 0.91415(18) 0.1572(2) 0.34350(15) 0.0495(8) Uani 1 1 d G . . . .
H15 H 0.959977 0.153182 0.405549 0.059 Uiso 1 1 calc R U . . .
C14 C 0.99012(13) 0.0905(2) 0.26143(18) 0.0498(8) Uani 1 1 d G . . . .
H14 H 1.087860 0.040882 0.267390 0.060 Uiso 1 1 calc R U . . .
C13 C 0.92307(16) 0.09636(19) 0.17065(15) 0.0422(7) Uani 1 1 d G . . . .
H13 H 0.974992 0.050771 0.114560 0.051 Uiso 1 1 calc R U . . .
C9 C 0.4713(3) 0.0139(3) 0.2956(2) 0.0328(6) Uani 1 1 d . . . . .
H9 H 0.511520 0.001161 0.363482 0.039 Uiso 1 1 calc R U . . .
C23 C 0.0059(3) 0.7155(3) 0.2108(2) 0.0330(6) Uani 1 1 d . . . . .
H23 H 0.040700 0.780249 0.230096 0.040 Uiso 1 1 calc R U . . .
C7 C 0.4149(3) -0.0885(3) 0.1692(2) 0.0366(7) Uani 1 1 d . . . . .
H7 H 0.417236 -0.170387 0.149374 0.044 Uiso 1 1 calc R U . . .
C27 C 0.0422(3) 0.4919(3) 0.1777(2) 0.0346(6) Uani 1 1 d . . . . .
H27 H 0.101827 0.401014 0.174820 0.042 Uiso 1 1 calc R U . . .
C6 C 0.3527(3) 0.0486(3) 0.1004(2) 0.0358(7) Uani 1 1 d . . . . .
H6 H 0.311150 0.060875 0.033398 0.043 Uiso 1 1 calc R U . . .
C24 C -0.1339(3) 0.7544(3) 0.1859(3) 0.0388(7) Uani 1 1 d . . . . .
H24 H -0.194307 0.844878 0.189038 0.047 Uiso 1 1 calc R U . . .
C21 C 0.2845(3) 0.5913(3) 0.3075(3) 0.0380(7) Uani 1 1 d . . . . .
C8 C 0.4737(3) -0.1054(3) 0.2671(2) 0.0373(7) Uani 1 1 d . . . . .
H8 H 0.516087 -0.199559 0.315290 0.045 Uiso 1 1 calc R U . . .
C25 C -0.1858(3) 0.6624(3) 0.1566(3) 0.0380(7) Uani 1 1 d . . . . .
H25 H -0.281918 0.688848 0.139894 0.046 Uiso 1 1 calc R U . . .
C26 C -0.0971(3) 0.5318(3) 0.1516(3) 0.0387(7) Uani 1 1 d . . . . .
H26 H -0.131926 0.468778 0.130049 0.046 Uiso 1 1 calc R U . . .
C12 C 0.7148(3) 0.1792(3) 0.0572(3) 0.0393(7) Uani 1 1 d . . . . .
H12A H 0.659547 0.106177 0.081005 0.059 Uiso 1 1 calc R U . . .
H12B H 0.791088 0.162497 -0.005066 0.059 Uiso 1 1 calc R U . . .
H12C H 0.651559 0.275599 0.028157 0.059 Uiso 1 1 calc R U . . .
C17 C 0.7014(3) 0.3207(4) 0.4148(3) 0.0563(9) Uani 1 1 d . . . . .
H17A H 0.618788 0.395190 0.380761 0.084 Uiso 1 1 calc R U . . .
H17B H 0.770762 0.366884 0.423010 0.084 Uiso 1 1 calc R U . . .
H17C H 0.669787 0.258690 0.492209 0.084 Uiso 1 1 calc R U . . .
C28 C 0.1479(4) 0.2420(4) 0.5209(3) 0.0603(10) Uani 1 1 d . . . . .
H28A H 0.044872 0.258180 0.520682 0.090 Uiso 1 1 calc R U . . .
H28B H 0.165385 0.315056 0.546236 0.090 Uiso 1 1 calc R U . . .
H28C H 0.185004 0.145583 0.575011 0.090 Uiso 1 1 calc R U . . .
H21A H 0.217(3) 0.654(3) 0.344(2) 0.028(7) Uiso 1 1 d . . . . .
H21B H 0.386(3) 0.568(3) 0.319(2) 0.040(8) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 C2 1.336(3) . ?
O2 C28 1.445(3) . ?
O3 C18 1.212(3) . ?
O1 C2 1.195(3) . ?
N1 C3 1.504(3) . ?
N1 C18 1.355(3) . ?
N1 C10 1.433(2) . ?
C3 C4 1.517(3) . ?
C3 C19 1.583(3) . ?
C3 C2 1.512(4) . ?
C4 C5 1.383(3) . ?
C4 C9 1.390(3) . ?
C19 H19 1.0000 . ?
C19 C18 1.523(3) . ?
C19 C20 1.509(3) . ?
C22 C20 1.490(3) . ?
C22 C23 1.393(3) . ?
C22 C27 1.393(3) . ?
C20 C21 1.323(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.387(3) . ?
C11 C10 1.3900 . ?
C11 C13 1.3900 . ?
C11 C12 1.517(3) . ?
C10 C16 1.3900 . ?
C16 C15 1.3900 . ?
C16 C17 1.523(3) . ?
C15 H15 0.9500 . ?
C15 C14 1.3900 . ?
C14 H14 0.9500 . ?
C14 C13 1.3900 . ?
C13 H13 0.9500 . ?
C9 H9 0.9500 . ?
C9 C8 1.384(3) . ?
C23 H23 0.9500 . ?
C23 C24 1.383(3) . ?
C7 H7 0.9500 . ?
C7 C6 1.379(4) . ?
C7 C8 1.380(4) . ?
C27 H27 0.9500 . ?
C27 C26 1.384(3) . ?
C6 H6 0.9500 . ?
C24 H24 0.9500 . ?
C24 C25 1.379(4) . ?
C21 H21A 0.94(2) . ?
C21 H21B 0.99(3) . ?
C8 H8 0.9500 . ?
C25 H25 0.9500 . ?
C25 C26 1.378(4) . ?
C26 H26 0.9500 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
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
C2 O2 C28 115.3(2) . . ?
C18 N1 C3 94.95(17) . . ?
C18 N1 C10 127.5(2) . . ?
C10 N1 C3 136.10(19) . . ?
N1 C3 C4 114.97(19) . . ?
N1 C3 C19 85.80(17) . . ?
N1 C3 C2 112.73(19) . . ?
C4 C3 C19 119.93(18) . . ?
C2 C3 C4 109.4(2) . . ?
C2 C3 C19 112.36(19) . . ?
C5 C4 C3 123.7(2) . . ?
C5 C4 C9 119.1(2) . . ?
C9 C4 C3 117.2(2) . . ?
C3 C19 H19 111.2 . . ?
C18 C19 C3 85.56(17) . . ?
C18 C19 H19 111.2 . . ?
C20 C19 C3 119.0(2) . . ?
C20 C19 H19 111.2 . . ?
C20 C19 C18 116.47(19) . . ?
C23 C22 C20 120.7(2) . . ?
C27 C22 C20 121.6(2) . . ?
C27 C22 C23 117.8(2) . . ?
O2 C2 C3 109.8(2) . . ?
O1 C2 O2 123.6(2) . . ?
O1 C2 C3 126.6(2) . . ?
O3 C18 N1 131.6(2) . . ?
O3 C18 C19 134.7(2) . . ?
N1 C18 C19 93.7(2) . . ?
C22 C20 C19 117.5(2) . . ?
C21 C20 C19 120.2(2) . . ?
C21 C20 C22 122.3(2) . . ?
C4 C5 H5 119.9 . . ?
C4 C5 C6 120.1(2) . . ?
C6 C5 H5 119.9 . . ?
C10 C11 C13 120.0 . . ?
C10 C11 C12 122.20(14) . . ?
C13 C11 C12 117.71(14) . . ?
C11 C10 N1 119.41(13) . . ?
C11 C10 C16 120.0 . . ?
C16 C10 N1 120.56(13) . . ?
C10 C16 C17 122.11(15) . . ?
C15 C16 C10 120.0 . . ?
C15 C16 C17 117.13(15) . . ?
C16 C15 H15 120.0 . . ?
C14 C15 C16 120.0 . . ?
C14 C15 H15 120.0 . . ?
C15 C14 H14 120.0 . . ?
C15 C14 C13 120.0 . . ?
C13 C14 H14 120.0 . . ?
C11 C13 H13 120.0 . . ?
C14 C13 C11 120.0 . . ?
C14 C13 H13 120.0 . . ?
C4 C9 H9 119.8 . . ?
C8 C9 C4 120.4(2) . . ?
C8 C9 H9 119.8 . . ?
C22 C23 H23 119.4 . . ?
C24 C23 C22 121.1(2) . . ?
C24 C23 H23 119.4 . . ?
C6 C7 H7 120.4 . . ?
C6 C7 C8 119.3(2) . . ?
C8 C7 H7 120.4 . . ?
C22 C27 H27 119.5 . . ?
C26 C27 C22 121.0(2) . . ?
C26 C27 H27 119.5 . . ?
C5 C6 H6 119.7 . . ?
C7 C6 C5 120.7(2) . . ?
C7 C6 H6 119.7 . . ?
C23 C24 H24 119.9 . . ?
C25 C24 C23 120.2(2) . . ?
C25 C24 H24 119.9 . . ?
C20 C21 H21A 121.0(15) . . ?
C20 C21 H21B 120.4(15) . . ?
H21A C21 H21B 119(2) . . ?
C9 C8 H8 119.8 . . ?
C7 C8 C9 120.4(2) . . ?
C7 C8 H8 119.8 . . ?
C24 C25 H25 120.2 . . ?
C26 C25 C24 119.5(2) . . ?
C26 C25 H25 120.2 . . ?
C27 C26 H26 119.8 . . ?
C25 C26 C27 120.4(3) . . ?
C25 C26 H26 119.8 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O2 C28 H28A 109.5 . . ?
O2 C28 H28B 109.5 . . ?
O2 C28 H28C 109.5 . . ?
H28A C28 H28B 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
N1 C3 C4 C5 -102.7(3) . . . . ?
N1 C3 C4 C9 76.6(3) . . . . ?
N1 C3 C19 C18 1.35(17) . . . . ?
N1 C3 C19 C20 -116.6(2) . . . . ?
N1 C3 C2 O2 165.96(19) . . . . ?
N1 C3 C2 O1 -14.9(3) . . . . ?
N1 C10 C16 C15 -177.77(19) . . . . ?
N1 C10 C16 C17 -8.0(2) . . . . ?
C3 N1 C18 O3 -177.1(3) . . . . ?
C3 N1 C18 C19 1.57(19) . . . . ?
C3 N1 C10 C11 81.4(3) . . . . ?
C3 N1 C10 C16 -100.8(3) . . . . ?
C3 C4 C5 C6 178.6(2) . . . . ?
C3 C4 C9 C8 -178.4(2) . . . . ?
C3 C19 C18 O3 177.1(3) . . . . ?
C3 C19 C18 N1 -1.49(18) . . . . ?
C3 C19 C20 C22 -108.2(2) . . . . ?
C3 C19 C20 C21 72.0(3) . . . . ?
C4 C3 C19 C18 -115.1(2) . . . . ?
C4 C3 C19 C20 126.9(2) . . . . ?
C4 C3 C2 O2 -64.8(2) . . . . ?
C4 C3 C2 O1 114.3(3) . . . . ?
C4 C5 C6 C7 -0.1(4) . . . . ?
C4 C9 C8 C7 -0.4(4) . . . . ?
C19 C3 C4 C5 -2.7(4) . . . . ?
C19 C3 C4 C9 176.7(2) . . . . ?
C19 C3 C2 O2 71.0(2) . . . . ?
C19 C3 C2 O1 -109.9(3) . . . . ?
C22 C23 C24 C25 -0.7(4) . . . . ?
C22 C27 C26 C25 -0.8(5) . . . . ?
C2 C3 C4 C5 129.3(3) . . . . ?
C2 C3 C4 C9 -51.4(3) . . . . ?
C2 C3 C19 C18 114.2(2) . . . . ?
C2 C3 C19 C20 -3.7(3) . . . . ?
C18 N1 C3 C4 119.7(2) . . . . ?
C18 N1 C3 C19 -1.51(19) . . . . ?
C18 N1 C3 C2 -114.0(2) . . . . ?
C18 N1 C10 C11 -81.0(2) . . . . ?
C18 N1 C10 C16 96.8(2) . . . . ?
C18 C19 C20 C22 151.6(2) . . . . ?
C18 C19 C20 C21 -28.2(4) . . . . ?
C20 C19 C18 O3 -62.6(4) . . . . ?
C20 C19 C18 N1 118.8(2) . . . . ?
C20 C22 C23 C24 -179.2(3) . . . . ?
C20 C22 C27 C26 179.9(3) . . . . ?
C5 C4 C9 C8 0.9(4) . . . . ?
C11 C10 C16 C15 0.0 . . . . ?
C11 C10 C16 C17 169.7(2) . . . . ?
C10 N1 C3 C4 -46.4(3) . . . . ?
C10 N1 C3 C19 -167.6(2) . . . . ?
C10 N1 C3 C2 79.9(3) . . . . ?
C10 N1 C18 O3 -9.2(4) . . . . ?
C10 N1 C18 C19 169.42(19) . . . . ?
C10 C11 C13 C14 0.0 . . . . ?
C10 C16 C15 C14 0.0 . . . . ?
C16 C15 C14 C13 0.0 . . . . ?
C15 C14 C13 C11 0.0 . . . . ?
C13 C11 C10 N1 177.79(18) . . . . ?
C13 C11 C10 C16 0.0 . . . . ?
C9 C4 C5 C6 -0.7(4) . . . . ?
C23 C22 C20 C19 -152.3(2) . . . . ?
C23 C22 C20 C21 27.5(4) . . . . ?
C23 C22 C27 C26 -0.3(4) . . . . ?
C23 C24 C25 C26 -0.4(5) . . . . ?
C27 C22 C20 C19 27.5(4) . . . . ?
C27 C22 C20 C21 -152.7(3) . . . . ?
C27 C22 C23 C24 1.0(4) . . . . ?
C6 C7 C8 C9 -0.5(4) . . . . ?
C24 C25 C26 C27 1.1(5) . . . . ?
C8 C7 C6 C5 0.7(4) . . . . ?
C12 C11 C10 N1 1.4(2) . . . . ?
C12 C11 C10 C16 -176.4(2) . . . . ?
C12 C11 C13 C14 176.6(2) . . . . ?
C17 C16 C15 C14 -170.2(2) . . . . ?
C28 O2 C2 O1 6.1(4) . . . . ?
C28 O2 C2 C3 -174.8(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
