# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2021

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

data_mo_1225_6_0m
_database_code_depnum_ccdc_archive 'CCDC 2088970'
loop_
_audit_author_name
_audit_author_address
shan
;Nanjing University of Science and Technology
China
;
_audit_update_record             
;
2021-06-09 deposited with the CCDC.	2021-08-12 downloaded from the CCDC.
;
_audit_creation_date             2021-06-09
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_chemical_formula_moiety         '2(C H2 Cl2), C44 H32 O4'
_chemical_formula_sum            'C46 H36 Cl4 O4'
_chemical_formula_weight         794.61
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Cl 0.14873 0.16029 11.46040 7.19640 6.25560 1.64550 0.01040 1.16620 18.51940
47.77840 -9.55739974976
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2ybc (x-z,y,z)'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x+1/2,y+1/2,-z+1/2
3 -x,-y,-z
4 x-1/2,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   8.3317(3)
_cell_length_b                   14.2855(5)
_cell_length_c                   15.6527(6)
_cell_angle_alpha                90
_cell_angle_beta                 100.3454(12)
_cell_angle_gamma                90
_cell_volume                     1832.74(12)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4955
_cell_measurement_theta_max      26.047
_cell_measurement_theta_min      2.597
_exptl_absorpt_coefficient_mu    0.370
_exptl_absorpt_correction_T_max  0.0276
_exptl_absorpt_correction_T_min  0.0115
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0652 before and 0.0574 after correction. The Ratio of minimum to maximum transmission is 0.4167. The λ/2 correction factor is Not present.'
_exptl_crystal_density_diffrn    1.4398
_exptl_crystal_F_000             825.5249
_diffrn_reflns_av_R_equivalents  0.0500
_diffrn_reflns_av_unetI/netI     0.0286
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            23189
_diffrn_reflns_theta_full        26.3854
_diffrn_reflns_theta_max         26.39
_diffrn_reflns_theta_min         2.60
_diffrn_ambient_temperature      150.0
_diffrn_measured_fraction_theta_full 0.9984
_diffrn_measured_fraction_theta_max 0.9984
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              8
_reflns_limit_h_min              -10
_reflns_limit_k_max              17
_reflns_limit_k_min              0
_reflns_limit_l_max              19
_reflns_limit_l_min              -7
_reflns_number_gt                2897
_reflns_number_total             3754
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_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  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         2.0672
_refine_diff_density_min         -0.8061
_refine_diff_density_rms         0.1178
_refine_ls_d_res_high            0.7996
_refine_ls_d_res_low             7.8429
_refine_ls_goodness_of_fit_ref   1.0648
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    33
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3754
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0965
_refine_ls_R_factor_gt           0.0786
_refine_ls_restrained_S_all      1.0648
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1526P)²+3.6522P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2382
_refine_ls_wR_factor_ref         0.2642
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C19(H19a,H19b), C21(H21a,H21b), C27(H27a,H27b)
2.b Aromatic/amide H refined with riding coordinates:
 C22(H22), C15(H15), C6(H6), C7(H7), C23(H23), C9(H9), C20(H20), C8(H8),
 C12(H12), C16(H16), C25(H25), C26(H26)
;
_atom_sites_solution_primary     iterative
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_refinement_flags_posn
Cl1 Cl 0.41362(16) 0.29127(10) 0.73275(9) 0.0577(4) Uani 1.000000 .
Cl2 Cl 0.74904(17) 0.22539(9) 0.76690(9) 0.0580(4) Uani 1.000000 .
O3 O 0.4630(4) 0.6256(2) 1.0045(2) 0.0495(8) Uani 1.000000 .
O4 O 0.5501(4) 0.9730(2) 0.6170(2) 0.0483(8) Uani 1.000000 .
C5 C 0.1301(4) 0.4174(3) 0.5853(2) 0.0308(8) Uani 1.000000 .
C6 C 0.4722(5) 0.5346(3) 0.7109(3) 0.0324(8) Uani 1.000000 .
C7 C 0.5453(5) 0.5570(3) 0.7947(3) 0.0351(9) Uani 1.000000 .
C8 C 0.2846(5) 0.7153(3) 0.5890(2) 0.0316(8) Uani 1.000000 .
C9 C 0.5417(5) 0.7524(3) 0.5044(3) 0.0363(9) Uani 1.000000 .
C10 C 0.3011(5) 0.5289(3) 0.6888(2) 0.0305(8) Uani 1.000000 .
C11 C 0.2266(4) 0.4996(3) 0.5988(2) 0.0285(7) Uani 1.000000 .
C12 C 0.1040(4) 0.3785(3) 0.5024(3) 0.0321(8) Uani 1.000000 .
C13 C 0.4529(5) 0.5761(3) 0.8579(2) 0.0347(8) Uani 1.000000 .
C14 C 0.3373(4) 0.6450(3) 0.5381(2) 0.0302(8) Uani 1.000000 .
C15 C 0.2089(5) 0.5472(3) 0.7530(2) 0.0340(8) Uani 1.000000 .
C16 C 0.1344(4) 0.4289(3) 0.4319(2) 0.0324(8) Uani 1.000000 .
C17 C 0.1908(4) 0.5206(3) 0.4412(2) 0.0308(8) Uani 1.000000 .
C18 C 0.2556(4) 0.5525(3) 0.5260(2) 0.0291(8) Uani 1.000000 .
C19 C 0.1478(5) 0.5839(3) 0.3631(2) 0.0347(8) Uani 1.000000 .
C20 C 0.3584(5) 0.8023(3) 0.5985(2) 0.0325(8) Uani 1.000000 .
C21 C 0.0332(5) 0.3752(3) 0.6491(3) 0.0346(8) Uani 1.000000 .
C22 C 0.2830(5) 0.5713(3) 0.8366(3) 0.0357(9) Uani 1.000000 .
C23 C 0.4678(5) 0.6656(3) 0.4957(3) 0.0335(8) Uani 1.000000 .
C24 C 0.4893(5) 0.8212(3) 0.5562(3) 0.0333(8) Uani 1.000000 .
C25 C 0.5763(5) 0.9119(3) 0.5685(3) 0.0402(9) Uani 1.000000 .
C26 C 0.5330(6) 0.6026(3) 0.9463(3) 0.0413(10) Uani 1.000000 .
C27 C 0.6066(7) 0.3053(4) 0.7967(4) 0.0562(13) Uani 1.000000 .
H22 H 0.2184(5) 0.5845(3) 0.8794(3) 0.0428(10) Uiso 1.000000 R
H15 H 0.0933(5) 0.5431(3) 0.7392(2) 0.0408(10) Uiso 1.000000 R
H6 H 0.5374(5) 0.5231(3) 0.6681(3) 0.0389(10) Uiso 1.000000 R
H7 H 0.6609(5) 0.5594(3) 0.8093(3) 0.0421(10) Uiso 1.000000 R
H23 H 0.5058(5) 0.6193(3) 0.4606(3) 0.0401(10) Uiso 1.000000 R
H9 H 0.6292(5) 0.7654(3) 0.4748(3) 0.0435(10) Uiso 1.000000 R
H20 H 0.3207(5) 0.8488(3) 0.6335(2) 0.0390(10) Uiso 1.000000 R
H8 H 0.1957(5) 0.7029(3) 0.6178(2) 0.0379(10) Uiso 1.000000 R
H12 H 0.0645(4) 0.3161(3) 0.4943(3) 0.0385(10) Uiso 1.000000 R
H16 H 0.1166(4) 0.4005(3) 0.3761(2) 0.0389(10) Uiso 1.000000 R
H19a H 0.2260(5) 0.6368(3) 0.3690(2) 0.0416(10) Uiso 1.000000 R
H19b H 0.1600(5) 0.5485(3) 0.3103(2) 0.0416(10) Uiso 1.000000 R
H21a H 0.0279(5) 0.3064(3) 0.6410(3) 0.0415(10) Uiso 1.000000 R
H21b H 0.0903(5) 0.3880(3) 0.7090(3) 0.0415(10) Uiso 1.000000 R
H25 H 0.6595(5) 0.9227(3) 0.5354(3) 0.0482(11) Uiso 1.000000 R
H26 H 0.6488(6) 0.6015(3) 0.9587(3) 0.0495(11) Uiso 1.000000 R
H27a H 0.6452(7) 0.3701(4) 0.7902(4) 0.0675(15) Uiso 1.000000 R
H27b H 0.5992(7) 0.2957(4) 0.8585(4) 0.0675(15) Uiso 1.000000 R


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 C27 1.746(6) . ?
Cl2 C27 1.769(6) . ?
O3 C26 1.211(6) . ?
O4 C25 1.201(5) . ?
C5 C11 1.417(5) . ?
C5 C12 1.392(5) . ?
C5 C21 1.517(5) . ?
C6 C7 1.382(6) . ?
C6 C10 1.407(5) . ?
C7 C13 1.385(6) . ?
C8 C14 1.401(5) . ?
C8 C20 1.382(6) . ?
C9 C23 1.381(6) . ?
C9 C24 1.393(6) . ?
C10 C11 1.494(5) . ?
C10 C15 1.395(5) . ?
C11 C18 1.423(5) . ?
C12 C16 1.379(5) . ?
C13 C22 1.396(6) . ?
C13 C26 1.474(5) . ?
C14 C18 1.483(5) . ?
C14 C23 1.402(5) . ?
C15 C22 1.386(5) . ?
C16 C17 1.390(6) . ?
C17 C18 1.416(5) . ?
C17 C19 1.511(5) . ?
C19 C21 1.596(6) 3_566 ?
C20 C24 1.400(5) . ?
C24 C25 1.480(6) . ?

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
C12 C5 C11 117.3(3) . . ?
C21 C5 C11 125.9(3) . . ?
C21 C5 C12 116.2(3) . . ?
C10 C6 C7 120.1(4) . . ?
C13 C7 C6 121.1(4) . . ?
C20 C8 C14 121.8(3) . . ?
C24 C9 C23 120.7(4) . . ?
C11 C10 C6 118.6(3) . . ?
C15 C10 C6 118.5(3) . . ?
C15 C10 C11 122.9(3) . . ?
C10 C11 C5 120.1(3) . . ?
C18 C11 C5 119.6(3) . . ?
C18 C11 C10 120.3(3) . . ?
C16 C12 C5 121.1(4) . . ?
C22 C13 C7 119.3(4) . . ?
C26 C13 C7 120.3(4) . . ?
C26 C13 C22 120.4(4) . . ?
C18 C14 C8 121.8(3) . . ?
C23 C14 C8 117.9(4) . . ?
C23 C14 C18 120.3(3) . . ?
C22 C15 C10 121.1(4) . . ?
C17 C16 C12 121.1(4) . . ?
C18 C17 C16 117.8(3) . . ?
C19 C17 C16 117.0(3) . . ?
C19 C17 C18 124.1(3) . . ?
C14 C18 C11 120.8(3) . . ?
C17 C18 C11 119.2(3) . . ?
C17 C18 C14 119.7(3) . . ?
C21 C19 C17 113.4(3) 3_566 . ?
C24 C20 C8 119.5(4) . . ?
C19 C21 C5 112.3(3) 3_566 . ?
C15 C22 C13 119.9(4) . . ?
C14 C23 C9 120.8(4) . . ?
C20 C24 C9 119.4(4) . . ?
C25 C24 C9 119.7(4) . . ?
C25 C24 C20 120.8(4) . . ?
C24 C25 O4 125.3(4) . . ?
C13 C26 O3 125.3(4) . . ?
Cl2 C27 Cl1 111.5(3) . . ?


_olex2_submission_special_instructions 'No special instructions were received'
