# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_b180129b_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1820660'
loop_
_audit_author_name
_audit_author_address
'Sun bingbing' 'Ren Ai Road NO. 199'
_audit_update_record             
;
2018-01-30 deposited with the CCDC.	2019-04-02 downloaded from the CCDC.
;
_audit_creation_date             2018-01-29
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C33 H23 Cl N4 O, C2 H3 N'
_chemical_formula_sum            'C35 H26 Cl N5 O'
_chemical_formula_weight         568.06
_chemical_absolute_configuration ad
_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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_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'

_cell_length_a                   11.351(2)
_cell_length_b                   11.9996(17)
_cell_length_c                   21.215(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2889.7(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4144
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.55
_cell_measurement_theta_min      2.47
_shelx_estimated_absorpt_T_max   0.951
_shelx_estimated_absorpt_T_min   0.905
_exptl_absorpt_coefficient_mu    0.170
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5492
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.1153 before and 0.0545 after correction. The Ratio of minimum to maximum transmission is 0.7365. 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    1.306
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1184
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.6
_exptl_crystal_size_min          0.3
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0382
_diffrn_reflns_av_unetI/netI     0.0685
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            11645
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.339
_diffrn_reflns_theta_min         2.470
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.781
_reflns_Friedel_fraction_full    0.986
_reflns_Friedel_fraction_max     0.987
_reflns_number_gt                5563
_reflns_number_total             7159
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SIR2004 (Burla et al., 2007)'
_refine_diff_density_max         0.317
_refine_diff_density_min         -0.279
_refine_diff_density_rms         0.068
_refine_ls_abs_structure_details 
;
 Flack x determined using 1911 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     386
_refine_ls_number_reflns         7159
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0864
_refine_ls_R_factor_gt           0.0640
_refine_ls_restrained_S_all      1.078
_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)+(0.0882P)²+1.7407P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1786
_refine_ls_wR_factor_ref         0.1920
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N4-H4A = N4-H4B
 0.8 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C24(H24)
3.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C11(H11), C12(H12), C13(H13),
 C14(H14), C15(H15), C18(H18), C19(H19), C20(H20), C21(H21), C22(H22), C23(H23),
  C27(H27), C28(H28), C29(H29), C30(H30)
3.c Idealised Me refined as rotating group:
 C34(H34A,H34B,H34C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2009(4) 0.9357(4) 0.8310(2) 0.0317(9) Uani 1 1 d . . . . .
C2 C 0.2164(6) 1.0480(4) 0.8238(3) 0.0502(14) Uani 1 1 d . . . . .
H2 H 0.2340 1.0781 0.7846 0.060 Uiso 1 1 calc R . . . .
C3 C 0.2054(8) 1.1163(5) 0.8766(4) 0.073(2) Uani 1 1 d . . . . .
H3 H 0.2152 1.1929 0.8723 0.087 Uiso 1 1 calc R . . . .
C4 C 0.1805(6) 1.0723(6) 0.9344(3) 0.0609(17) Uani 1 1 d . . . . .
H4 H 0.1725 1.1191 0.9691 0.073 Uiso 1 1 calc R . . . .
C5 C 0.1672(6) 0.9604(5) 0.9413(3) 0.0530(15) Uani 1 1 d . . . . .
H5 H 0.1534 0.9303 0.9810 0.064 Uiso 1 1 calc R . . . .
C6 C 0.1744(5) 0.8919(4) 0.8895(3) 0.0448(12) Uani 1 1 d . . . . .
H6 H 0.1614 0.8158 0.8939 0.054 Uiso 1 1 calc R . . . .
C7 C 0.2538(4) 0.7598(3) 0.7763(2) 0.0265(8) Uani 1 1 d . . . . .
C8 C 0.2288(4) 0.7150(3) 0.7093(2) 0.0250(8) Uani 1 1 d . . . . .
C9 C 0.1580(4) 0.8135(3) 0.6833(2) 0.0267(8) Uani 1 1 d . . . . .
C10 C 0.0983(4) 0.8172(4) 0.6223(2) 0.0344(10) Uani 1 1 d . . . . .
C11 C -0.0081(5) 0.8761(4) 0.6166(3) 0.0483(13) Uani 1 1 d . . . . .
H11 H -0.0396 0.9131 0.6513 0.058 Uiso 1 1 calc R . . . .
C12 C -0.0662(6) 0.8788(5) 0.5587(4) 0.066(2) Uani 1 1 d . . . . .
H12 H -0.1362 0.9184 0.5546 0.079 Uiso 1 1 calc R . . . .
C13 C -0.0212(7) 0.8238(6) 0.5081(3) 0.067(2) Uani 1 1 d . . . . .
H13 H -0.0610 0.8262 0.4697 0.080 Uiso 1 1 calc R . . . .
C14 C 0.0808(7) 0.7656(7) 0.5126(3) 0.0635(18) Uani 1 1 d . . . . .
H14 H 0.1108 0.7287 0.4776 0.076 Uiso 1 1 calc R . . . .
C15 C 0.1407(5) 0.7611(5) 0.5698(2) 0.0469(12) Uani 1 1 d . . . . .
H15 H 0.2100 0.7200 0.5729 0.056 Uiso 1 1 calc R . . . .
C16 C 0.3473(4) 0.6932(3) 0.6776(2) 0.0262(8) Uani 1 1 d . . . . .
C17 C 0.4372(4) 0.7837(4) 0.6787(2) 0.0308(9) Uani 1 1 d . . . . .
C18 C 0.5467(5) 0.7604(4) 0.7047(3) 0.0404(11) Uani 1 1 d . . . . .
H18 H 0.5600 0.6908 0.7226 0.048 Uiso 1 1 calc R . . . .
C19 C 0.6366(5) 0.8389(5) 0.7046(3) 0.0522(14) Uani 1 1 d . . . . .
H19 H 0.7099 0.8213 0.7214 0.063 Uiso 1 1 calc R . . . .
C20 C 0.6166(6) 0.9424(5) 0.6795(3) 0.0534(15) Uani 1 1 d . . . . .
H20 H 0.6767 0.9950 0.6788 0.064 Uiso 1 1 calc R . . . .
C21 C 0.5098(6) 0.9680(4) 0.6559(3) 0.0495(14) Uani 1 1 d . . . . .
H21 H 0.4967 1.0393 0.6402 0.059 Uiso 1 1 calc R . . . .
C22 C 0.4176(5) 0.8900(4) 0.6543(3) 0.0422(12) Uani 1 1 d . . . . .
H22 H 0.3447 0.9089 0.6373 0.051 Uiso 1 1 calc R . . . .
C23 C 0.3762(4) 0.5941(4) 0.6552(2) 0.0283(9) Uani 1 1 d . . . . .
H23 H 0.4508 0.5872 0.6374 0.034 Uiso 1 1 calc R . . . .
C24 C 0.3011(4) 0.4926(3) 0.65565(19) 0.0248(8) Uani 1 1 d . . . . .
H24 H 0.3446 0.4342 0.6780 0.030 Uiso 1 1 calc R . . . .
C25 C 0.2775(4) 0.4505(4) 0.5890(2) 0.0293(9) Uani 1 1 d . . . . .
C26 C 0.3590(4) 0.3831(4) 0.5579(2) 0.0363(10) Uani 1 1 d . . . . .
C27 C 0.3377(5) 0.3428(5) 0.4981(3) 0.0477(13) Uani 1 1 d . . . . .
H27 H 0.3930 0.2973 0.4785 0.057 Uiso 1 1 calc R . . . .
C28 C 0.2345(6) 0.3700(5) 0.4674(3) 0.0567(16) Uani 1 1 d . . . . .
H28 H 0.2196 0.3427 0.4272 0.068 Uiso 1 1 calc R . . . .
C29 C 0.1547(6) 0.4373(5) 0.4965(3) 0.0516(14) Uani 1 1 d . . . . .
H29 H 0.0862 0.4579 0.4755 0.062 Uiso 1 1 calc R . . . .
C30 C 0.1749(5) 0.4755(4) 0.5573(2) 0.0396(11) Uani 1 1 d . . . . .
H30 H 0.1180 0.5190 0.5770 0.048 Uiso 1 1 calc R . . . .
C31 C 0.1880(3) 0.5128(3) 0.6913(2) 0.0244(8) Uani 1 1 d . . . . .
C32 C 0.1164(4) 0.4160(4) 0.7011(2) 0.0302(9) Uani 1 1 d . . . . .
C33 C 0.1536(3) 0.6113(3) 0.71476(19) 0.0243(8) Uani 1 1 d . . . . .
Cl1 Cl 0.49071(12) 0.34642(15) 0.59422(8) 0.0589(4) Uani 1 1 d . . . . .
N1 N 0.2062(3) 0.8639(3) 0.77809(18) 0.0284(8) Uani 1 1 d . . . . .
N2 N 0.1485(3) 0.8940(3) 0.72238(18) 0.0287(8) Uani 1 1 d . . . . .
N3 N 0.0651(4) 0.3364(3) 0.7076(2) 0.0441(11) Uani 1 1 d . . . . .
N4 N 0.0516(4) 0.6250(3) 0.7485(2) 0.0365(9) Uani 1 1 d D . . . .
O1 O 0.3065(3) 0.7126(3) 0.81778(15) 0.0357(7) Uani 1 1 d . . . . .
C34 C 0.1180(8) 0.1536(8) 0.5834(5) 0.090(3) Uani 1 1 d . . . . .
H34A H 0.1410 0.1115 0.5470 0.135 Uiso 1 1 calc GR . . . .
H34B H 0.1041 0.2297 0.5715 0.135 Uiso 1 1 calc GR . . . .
H34C H 0.0472 0.1226 0.6008 0.135 Uiso 1 1 calc GR . . . .
C35 C 0.2099(7) 0.1494(6) 0.6296(4) 0.0660(18) Uani 1 1 d . . . . .
N5 N 0.2807(8) 0.1483(7) 0.6675(4) 0.100(2) Uani 1 1 d . . . . .
H4A H 0.014(9) 0.569(5) 0.748(5) 0.120 Uiso 1 1 d DR . . . .
H4B H 0.029(9) 0.688(4) 0.753(5) 0.120 Uiso 1 1 d DR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.367(7) . ?
C1 C6 1.381(7) . ?
C1 N1 1.417(6) . ?
C2 H2 0.9300 . ?
C2 C3 1.392(9) . ?
C3 H3 0.9300 . ?
C3 C4 1.364(10) . ?
C4 H4 0.9300 . ?
C4 C5 1.359(9) . ?
C5 H5 0.9300 . ?
C5 C6 1.375(8) . ?
C6 H6 0.9300 . ?
C7 C8 1.545(6) . ?
C7 N1 1.362(5) . ?
C7 O1 1.205(5) . ?
C8 C9 1.532(6) . ?
C8 C16 1.526(6) . ?
C8 C33 1.514(5) . ?
C9 C10 1.462(7) . ?
C9 N2 1.278(6) . ?
C10 C11 1.404(7) . ?
C10 C15 1.387(8) . ?
C11 H11 0.9300 . ?
C11 C12 1.396(8) . ?
C12 H12 0.9300 . ?
C12 C13 1.359(11) . ?
C13 H13 0.9300 . ?
C13 C14 1.357(11) . ?
C14 H14 0.9300 . ?
C14 C15 1.392(8) . ?
C15 H15 0.9300 . ?
C16 C17 1.490(6) . ?
C16 C23 1.323(6) . ?
C17 C18 1.389(7) . ?
C17 C22 1.394(7) . ?
C18 H18 0.9300 . ?
C18 C19 1.389(7) . ?
C19 H19 0.9300 . ?
C19 C20 1.371(9) . ?
C20 H20 0.9300 . ?
C20 C21 1.347(10) . ?
C21 H21 0.9300 . ?
C21 C22 1.405(7) . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?
C23 C24 1.486(6) . ?
C24 H24 0.9800 . ?
C24 C25 1.526(6) . ?
C24 C31 1.510(5) . ?
C25 C26 1.394(6) . ?
C25 C30 1.378(7) . ?
C26 C27 1.378(7) . ?
C26 Cl1 1.739(5) . ?
C27 H27 0.9300 . ?
C27 C28 1.380(9) . ?
C28 H28 0.9300 . ?
C28 C29 1.361(9) . ?
C29 H29 0.9300 . ?
C29 C30 1.388(7) . ?
C30 H30 0.9300 . ?
C31 C32 1.433(6) . ?
C31 C33 1.340(6) . ?
C32 N3 1.127(6) . ?
C33 N4 1.371(6) . ?
N1 N2 1.399(5) . ?
N4 H4A 0.80(3) . ?
N4 H4B 0.81(3) . ?
C34 H34A 0.9600 . ?
C34 H34B 0.9600 . ?
C34 H34C 0.9600 . ?
C34 C35 1.432(12) . ?
C35 N5 1.138(10) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 120.2(5) . . ?
C2 C1 N1 120.4(5) . . ?
C6 C1 N1 119.3(4) . . ?
C1 C2 H2 120.7 . . ?
C1 C2 C3 118.7(6) . . ?
C3 C2 H2 120.7 . . ?
C2 C3 H3 119.6 . . ?
C4 C3 C2 120.9(6) . . ?
C4 C3 H3 119.6 . . ?
C3 C4 H4 119.9 . . ?
C5 C4 C3 120.1(6) . . ?
C5 C4 H4 119.9 . . ?
C4 C5 H5 120.1 . . ?
C4 C5 C6 119.8(6) . . ?
C6 C5 H5 120.1 . . ?
C1 C6 H6 119.9 . . ?
C5 C6 C1 120.3(5) . . ?
C5 C6 H6 119.9 . . ?
N1 C7 C8 105.8(3) . . ?
O1 C7 C8 126.9(4) . . ?
O1 C7 N1 127.4(4) . . ?
C9 C8 C7 99.2(3) . . ?
C16 C8 C7 107.6(3) . . ?
C16 C8 C9 115.9(3) . . ?
C33 C8 C7 108.6(3) . . ?
C33 C8 C9 111.4(3) . . ?
C33 C8 C16 112.9(3) . . ?
C10 C9 C8 125.9(4) . . ?
N2 C9 C8 113.2(4) . . ?
N2 C9 C10 120.8(4) . . ?
C11 C10 C9 119.3(5) . . ?
C15 C10 C9 122.3(4) . . ?
C15 C10 C11 118.4(5) . . ?
C10 C11 H11 120.2 . . ?
C12 C11 C10 119.5(6) . . ?
C12 C11 H11 120.2 . . ?
C11 C12 H12 119.7 . . ?
C13 C12 C11 120.5(6) . . ?
C13 C12 H12 119.7 . . ?
C12 C13 H13 119.5 . . ?
C14 C13 C12 120.9(6) . . ?
C14 C13 H13 119.5 . . ?
C13 C14 H14 120.0 . . ?
C13 C14 C15 120.0(7) . . ?
C15 C14 H14 120.0 . . ?
C10 C15 C14 120.7(6) . . ?
C10 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
C17 C16 C8 118.1(4) . . ?
C23 C16 C8 122.1(4) . . ?
C23 C16 C17 119.4(4) . . ?
C18 C17 C16 118.1(4) . . ?
C18 C17 C22 118.4(4) . . ?
C22 C17 C16 123.5(4) . . ?
C17 C18 H18 119.3 . . ?
C17 C18 C19 121.3(5) . . ?
C19 C18 H18 119.3 . . ?
C18 C19 H19 120.2 . . ?
C20 C19 C18 119.6(5) . . ?
C20 C19 H19 120.2 . . ?
C19 C20 H20 120.0 . . ?
C21 C20 C19 120.0(5) . . ?
C21 C20 H20 120.0 . . ?
C20 C21 H21 119.1 . . ?
C20 C21 C22 121.8(5) . . ?
C22 C21 H21 119.1 . . ?
C17 C22 C21 118.8(5) . . ?
C17 C22 H22 120.6 . . ?
C21 C22 H22 120.6 . . ?
C16 C23 H23 116.9 . . ?
C16 C23 C24 126.3(4) . . ?
C24 C23 H23 116.9 . . ?
C23 C24 H24 107.5 . . ?
C23 C24 C25 111.4(3) . . ?
C23 C24 C31 111.1(3) . . ?
C25 C24 H24 107.5 . . ?
C31 C24 H24 107.5 . . ?
C31 C24 C25 111.7(3) . . ?
C26 C25 C24 121.0(4) . . ?
C30 C25 C24 121.9(4) . . ?
C30 C25 C26 117.1(4) . . ?
C25 C26 Cl1 120.5(4) . . ?
C27 C26 C25 121.5(5) . . ?
C27 C26 Cl1 118.0(4) . . ?
C26 C27 H27 120.0 . . ?
C26 C27 C28 120.0(5) . . ?
C28 C27 H27 120.0 . . ?
C27 C28 H28 120.3 . . ?
C29 C28 C27 119.4(5) . . ?
C29 C28 H28 120.3 . . ?
C28 C29 H29 119.8 . . ?
C28 C29 C30 120.5(6) . . ?
C30 C29 H29 119.8 . . ?
C25 C30 C29 121.4(5) . . ?
C25 C30 H30 119.3 . . ?
C29 C30 H30 119.3 . . ?
C32 C31 C24 115.1(4) . . ?
C33 C31 C24 125.1(4) . . ?
C33 C31 C32 119.8(4) . . ?
N3 C32 C31 176.2(5) . . ?
C31 C33 C8 122.2(4) . . ?
C31 C33 N4 123.0(4) . . ?
N4 C33 C8 114.7(4) . . ?
C7 N1 C1 126.7(4) . . ?
C7 N1 N2 113.5(3) . . ?
N2 N1 C1 119.5(3) . . ?
C9 N2 N1 108.3(3) . . ?
C33 N4 H4A 110(9) . . ?
C33 N4 H4B 116(8) . . ?
H4A N4 H4B 129(10) . . ?
H34A C34 H34B 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C35 C34 H34A 109.5 . . ?
C35 C34 H34B 109.5 . . ?
C35 C34 H34C 109.5 . . ?
N5 C35 C34 177.6(10) . . ?


_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_1204-2
_database_code_depnum_ccdc_archive 'CCDC 1821024'
loop_
_audit_author_name
_audit_author_address
sun-bingbing 'soochow university'
_audit_update_record             
;
2018-01-31 deposited with the CCDC.	2019-04-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C33 H23 Cl N4 O'
_chemical_formula_weight         527
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   9.3289(4)
_cell_length_b                   10.9229(5)
_cell_length_c                   12.8668(6)
_cell_angle_alpha                87.2370(10)
_cell_angle_beta                 78.6140(10)
_cell_angle_gamma                85.6810(10)
_cell_volume                     1280.91(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    9468
_cell_measurement_theta_min      2.23
_cell_measurement_theta_max      27.43

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.366
_exptl_crystal_F_000             548
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_min          0.15
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_max          0.20
_exptl_absorpt_coefficient_mu    0.185
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            42789
_diffrn_reflns_av_unetI/netI     0.0209
_diffrn_reflns_av_R_equivalents  0.0327
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.615
_diffrn_reflns_theta_max         27.533
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5906
_reflns_number_gt                5029
_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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_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)+(0.0629P)²+0.5001P]
 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         5876
_refine_ls_number_parameters     352
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0479
_refine_ls_R_factor_gt           0.0369
_refine_ls_wR_factor_ref         0.1242
_refine_ls_wR_factor_gt          0.1022
_refine_ls_goodness_of_fit_ref   1.148
_refine_ls_restrained_S_all      1.148
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 1.27865(4) 0.34765(4) 0.95327(3) 0.03102(12) Uani 1 1 d . . . . .
N1 N 0.52519(13) 0.40603(11) 0.70061(10) 0.0173(2) Uani 1 1 d . . . . .
N2 N 0.53987(13) 0.27767(11) 0.70280(10) 0.0166(2) Uani 1 1 d . . . . .
N3 N 0.89317(16) 0.36192(14) 1.10708(11) 0.0302(3) Uani 1 1 d . . . . .
N4 N 0.62479(14) 0.36065(14) 0.95514(10) 0.0267(3) Uani 1 1 d . . . . .
H4A H 0.6267 0.3660 1.0229 0.032 Uiso 1 1 calc R U . . .
H4B H 0.5404 0.3632 0.9341 0.032 Uiso 1 1 calc R U . . .
O1 O 0.68775(12) 0.12387(10) 0.76815(10) 0.0253(2) Uani 1 1 d . . . . .
C1 C 0.65332(15) 0.23043(13) 0.75000(11) 0.0172(3) Uani 1 1 d . . . . .
C2 C 0.73492(15) 0.34328(12) 0.76898(11) 0.0151(3) Uani 1 1 d . . . . .
C3 C 0.62926(15) 0.44592(13) 0.73934(11) 0.0158(3) Uani 1 1 d . . . . .
C4 C 0.45672(15) 0.21524(13) 0.64305(11) 0.0165(3) Uani 1 1 d . . . . .
C5 C 0.40821(16) 0.27783(14) 0.55805(12) 0.0207(3) Uani 1 1 d . . . . .
H5 H 0.4289 0.3611 0.5413 0.025 Uiso 1 1 calc R U . . .
C6 C 0.32946(17) 0.21678(15) 0.49832(12) 0.0237(3) Uani 1 1 d . . . . .
H6 H 0.2946 0.2591 0.4410 0.028 Uiso 1 1 calc R U . . .
C7 C 0.30103(17) 0.09489(15) 0.52135(12) 0.0241(3) Uani 1 1 d . . . . .
H7 H 0.2479 0.0535 0.4795 0.029 Uiso 1 1 calc R U . . .
C8 C 0.35029(18) 0.03375(14) 0.60546(13) 0.0251(3) Uani 1 1 d . . . . .
H8 H 0.3315 -0.0501 0.6209 0.030 Uiso 1 1 calc R U . . .
C9 C 0.42695(17) 0.09365(14) 0.66768(12) 0.0216(3) Uani 1 1 d . . . . .
H9 H 0.4586 0.0518 0.7264 0.026 Uiso 1 1 calc R U . . .
C10 C 0.63438(16) 0.57709(13) 0.75548(11) 0.0171(3) Uani 1 1 d . . . . .
C11 C 0.50582(17) 0.65361(14) 0.76117(11) 0.0204(3) Uani 1 1 d . . . . .
H11 H 0.4169 0.6200 0.7551 0.024 Uiso 1 1 calc R U . . .
C12 C 0.50829(18) 0.77788(14) 0.77568(12) 0.0241(3) Uani 1 1 d . . . . .
H12 H 0.4210 0.8296 0.7792 0.029 Uiso 1 1 calc R U . . .
C13 C 0.63805(19) 0.82774(14) 0.78516(12) 0.0258(3) Uani 1 1 d . . . . .
H13 H 0.6394 0.9133 0.7949 0.031 Uiso 1 1 calc R U . . .
C14 C 0.76490(19) 0.75232(14) 0.78039(13) 0.0251(3) Uani 1 1 d . . . . .
H14 H 0.8532 0.7863 0.7873 0.030 Uiso 1 1 calc R U . . .
C15 C 0.76409(17) 0.62714(14) 0.76557(12) 0.0209(3) Uani 1 1 d . . . . .
H15 H 0.8516 0.5758 0.7623 0.025 Uiso 1 1 calc R U . . .
C16 C 0.75264(15) 0.34838(12) 0.88280(11) 0.0159(3) Uani 1 1 d . . . . .
C17 C 0.88619(15) 0.34383(13) 0.90931(11) 0.0166(3) Uani 1 1 d . . . . .
C18 C 0.89195(15) 0.35349(14) 1.01866(12) 0.0196(3) Uani 1 1 d . . . . .
C19 C 1.02967(15) 0.32319(13) 0.83274(11) 0.0164(3) Uani 1 1 d . . . . .
H19 H 1.0908 0.3934 0.8371 0.020 Uiso 1 1 calc R U . . .
C20 C 1.00829(16) 0.31847(13) 0.72089(11) 0.0175(3) Uani 1 1 d . . . . .
H20 H 1.0936 0.3049 0.6675 0.021 Uiso 1 1 calc R U . . .
C21 C 0.88048(15) 0.33155(12) 0.68980(11) 0.0158(3) Uani 1 1 d . . . . .
C22 C 0.87174(15) 0.31836(14) 0.57623(11) 0.0179(3) Uani 1 1 d . . . . .
C23 C 0.82475(17) 0.41542(14) 0.51412(12) 0.0234(3) Uani 1 1 d . . . . .
H23 H 0.7978 0.4939 0.5435 0.028 Uiso 1 1 calc R U . . .
C24 C 0.81723(19) 0.39740(16) 0.40914(13) 0.0281(4) Uani 1 1 d . . . . .
H24 H 0.7844 0.4636 0.3672 0.034 Uiso 1 1 calc R U . . .
C25 C 0.85715(19) 0.28389(17) 0.36551(12) 0.0283(4) Uani 1 1 d . . . . .
H25 H 0.8511 0.2720 0.2939 0.034 Uiso 1 1 calc R U . . .
C26 C 0.90602(19) 0.18737(16) 0.42603(13) 0.0280(3) Uani 1 1 d . . . . .
H26 H 0.9351 0.1097 0.3956 0.034 Uiso 1 1 calc R U . . .
C27 C 0.91254(17) 0.20409(14) 0.53109(12) 0.0227(3) Uani 1 1 d . . . . .
H27 H 0.9450 0.1374 0.5727 0.027 Uiso 1 1 calc R U . . .
C28 C 1.11006(16) 0.20543(14) 0.86638(11) 0.0194(3) Uani 1 1 d . . . . .
C29 C 1.06511(18) 0.09099(15) 0.84746(13) 0.0248(3) Uani 1 1 d . . . . .
H29 H 0.9884 0.0870 0.8092 0.030 Uiso 1 1 calc R U . . .
C30 C 1.1299(2) -0.01693(16) 0.88339(14) 0.0326(4) Uani 1 1 d . . . . .
H30 H 1.0978 -0.0940 0.8697 0.039 Uiso 1 1 calc R U . . .
C31 C 1.2419(2) -0.01206(18) 0.93928(14) 0.0376(5) Uani 1 1 d . . . . .
H31 H 1.2860 -0.0860 0.9643 0.045 Uiso 1 1 calc R U . . .
C32 C 1.2894(2) 0.09956(19) 0.95872(13) 0.0345(4) Uani 1 1 d . . . . .
H32 H 1.3669 0.1030 0.9964 0.041 Uiso 1 1 calc R U . . .
C33 C 1.22281(17) 0.20678(16) 0.92256(12) 0.0246(3) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C33 1.7481(18) . ?
N1 C3 1.2871(18) . ?
N1 N2 1.3979(16) . ?
N2 C1 1.3770(18) . ?
N2 C4 1.4226(18) . ?
N3 C18 1.148(2) . ?
N4 C16 1.3625(19) . ?
O1 C1 1.2082(18) . ?
C1 C2 1.5499(19) . ?
C2 C16 1.5101(19) . ?
C2 C3 1.5214(18) . ?
C2 C21 1.5292(19) . ?
C3 C10 1.4632(19) . ?
C4 C9 1.386(2) . ?
C4 C5 1.395(2) . ?
C5 C6 1.386(2) . ?
C6 C7 1.384(2) . ?
C7 C8 1.382(2) . ?
C8 C9 1.388(2) . ?
C10 C15 1.396(2) . ?
C10 C11 1.401(2) . ?
C11 C12 1.382(2) . ?
C12 C13 1.393(2) . ?
C13 C14 1.383(2) . ?
C14 C15 1.390(2) . ?
C16 C17 1.352(2) . ?
C17 C18 1.428(2) . ?
C17 C19 1.5062(19) . ?
C19 C20 1.4951(19) . ?
C19 C28 1.528(2) . ?
C20 C21 1.326(2) . ?
C21 C22 1.4939(19) . ?
C22 C23 1.393(2) . ?
C22 C27 1.397(2) . ?
C23 C24 1.390(2) . ?
C24 C25 1.381(3) . ?
C25 C26 1.384(2) . ?
C26 C27 1.387(2) . ?
C28 C33 1.390(2) . ?
C28 C29 1.395(2) . ?
C29 C30 1.385(2) . ?
C30 C31 1.385(3) . ?
C31 C32 1.379(3) . ?
C32 C33 1.388(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 N1 N2 108.67(11) . . ?
C1 N2 N1 112.90(11) . . ?
C1 N2 C4 128.32(12) . . ?
N1 N2 C4 117.84(11) . . ?
O1 C1 N2 128.01(13) . . ?
O1 C1 C2 126.71(12) . . ?
N2 C1 C2 105.18(11) . . ?
C16 C2 C3 112.21(11) . . ?
C16 C2 C21 113.56(11) . . ?
C3 C2 C21 113.46(11) . . ?
C16 C2 C1 112.26(11) . . ?
C3 C2 C1 99.69(10) . . ?
C21 C2 C1 104.57(11) . . ?
N1 C3 C10 120.78(13) . . ?
N1 C3 C2 112.84(12) . . ?
C10 C3 C2 126.32(12) . . ?
C9 C4 C5 120.66(13) . . ?
C9 C4 N2 120.53(13) . . ?
C5 C4 N2 118.80(13) . . ?
C6 C5 C4 119.07(14) . . ?
C7 C6 C5 120.69(14) . . ?
C8 C7 C6 119.67(14) . . ?
C7 C8 C9 120.68(15) . . ?
C4 C9 C8 119.22(14) . . ?
C15 C10 C11 119.54(13) . . ?
C15 C10 C3 121.45(13) . . ?
C11 C10 C3 119.01(13) . . ?
C12 C11 C10 120.00(14) . . ?
C11 C12 C13 120.36(15) . . ?
C14 C13 C12 119.79(14) . . ?
C13 C14 C15 120.47(15) . . ?
C14 C15 C10 119.84(14) . . ?
C17 C16 N4 123.23(13) . . ?
C17 C16 C2 121.81(13) . . ?
N4 C16 C2 114.94(12) . . ?
C16 C17 C18 117.77(13) . . ?
C16 C17 C19 124.83(13) . . ?
C18 C17 C19 117.33(12) . . ?
N3 C18 C17 178.42(16) . . ?
C20 C19 C17 111.83(11) . . ?
C20 C19 C28 111.36(12) . . ?
C17 C19 C28 109.02(11) . . ?
C21 C20 C19 125.60(13) . . ?
C20 C21 C22 120.86(13) . . ?
C20 C21 C2 122.03(12) . . ?
C22 C21 C2 116.61(12) . . ?
C23 C22 C27 119.07(14) . . ?
C23 C22 C21 122.53(13) . . ?
C27 C22 C21 118.39(13) . . ?
C24 C23 C22 120.01(15) . . ?
C25 C24 C23 120.42(15) . . ?
C24 C25 C26 120.04(15) . . ?
C25 C26 C27 119.98(15) . . ?
C26 C27 C22 120.47(14) . . ?
C33 C28 C29 117.29(14) . . ?
C33 C28 C19 122.27(14) . . ?
C29 C28 C19 120.30(13) . . ?
C30 C29 C28 121.38(16) . . ?
C31 C30 C29 119.76(17) . . ?
C32 C31 C30 120.29(16) . . ?
C31 C32 C33 119.19(17) . . ?
C32 C33 C28 122.10(16) . . ?
C32 C33 Cl1 118.56(13) . . ?
C28 C33 Cl1 119.30(12) . . ?

_refine_diff_density_max         0.571
_refine_diff_density_min         -0.515
_refine_diff_density_rms         0.112

_shelxl_version_number           2013-2



