# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# 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_wyt0504_2_0m
_database_code_depnum_ccdc_archive 'CCDC 1967881'
loop_
_audit_author_name
_audit_author_address
'yating wen'
;JiLin University
China
;
_audit_update_record             
;
2019-11-25 deposited with the CCDC.	2021-11-10 downloaded from the CCDC.
;
_audit_creation_date             2018-05-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.04.18 svn.r3501 for OlexSys, GUI svn.r5488)
;
_chemical_name_common            ?
_chemical_name_systematic        wyt-1
_chemical_formula_moiety         '4(C21 H14 Cl N O)'
_chemical_formula_sum            'C84 H56 Cl4 N4 O4'
_chemical_formula_weight         1327.13
_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'

_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_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   9.7641(3)
_cell_length_b                   17.2051(6)
_cell_length_c                   9.8141(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.6015(14)
_cell_angle_gamma                90.00
_cell_volume                     1615.01(10)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    9954
_cell_measurement_temperature    293
_cell_measurement_theta_max      27.454
_cell_measurement_theta_min      2.934
_exptl_absorpt_coefficient_mu    0.243
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.365
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             688
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          1
_exptl_crystal_size_mid          1
_exptl_crystal_size_min          1
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0175
_diffrn_reflns_av_unetI/netI     0.0240
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            16013
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.93
_diffrn_ambient_temperature      293
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.961
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measurement_device_type  'CCD Area Detector'
_diffrn_measurement_method       ?
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71076
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                5641
_reflns_number_total             7126
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.209
_refine_diff_density_min         -0.417
_refine_diff_density_rms         0.064
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     433
_refine_ls_number_reflns         7126
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0575
_refine_ls_R_factor_gt           0.0440
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0559P)²+0.4285P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1078
_refine_ls_wR_factor_ref         0.1168
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C18(H18), C19(H19), C21(H21), C25(H25), C26(H26), C31(H31), C32(H32),
 C33(H33), C36(H36), C37(H37), C40(H40), C41(H41), C43(H43), C45(H45), C22(H22),
  C23(H23), C24(H24), C27(H27), C28(H28), C29(H29), C30(H30), C34(H34),
 C35(H35), C38(H38), C39(H39), C42(H42), C44(H44), C46(H46)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
Cl1 Cl 0.32981(6) 0.40973(4) 0.49572(5) 0.06883(17) Uani 1 d . . .
O3 O 0.27778(14) 0.45531(6) 1.15863(12) 0.0480(3) Uani 1 d . . .
N4 N 0.23807(14) 0.58093(7) 1.09154(13) 0.0357(3) Uani 1 d . . .
C6 C 0.18545(16) 0.63514(8) 0.98259(15) 0.0336(3) Uani 1 d . . .
C7 C 0.33239(18) 0.66639(9) 1.28502(16) 0.0403(4) Uani 1 d . . .
C8 C 0.28356(16) 0.48395(8) 0.92355(16) 0.0341(3) Uani 1 d . . .
C9 C 0.25848(16) 0.70421(9) 0.97343(15) 0.0352(3) Uani 1 d . . .
C12 C 0.26618(16) 0.50457(9) 1.06758(16) 0.0347(3) Uani 1 d . . .
C14 C 0.23818(17) 0.60826(9) 1.23068(15) 0.0376(3) Uani 1 d . . .
C16 C 0.31527(18) 0.43725(10) 0.66267(16) 0.0427(4) Uani 1 d . . .
C18 C 0.42300(18) 0.70508(10) 1.20428(18) 0.0437(4) Uani 1 d . . .
H18 H 0.5121 0.7188 1.2515 0.052 Uiso 1 calc . . R
C19 C 0.37040(17) 0.52505(10) 0.85364(17) 0.0402(3) Uani 1 d . . .
H19 H 0.4172 0.5689 0.8946 0.048 Uiso 1 calc . . R
C21 C 0.21649(19) 0.41783(9) 0.86269(18) 0.0428(4) Uani 1 d . . .
H21 H 0.1616 0.3886 0.9108 0.051 Uiso 1 calc . . R
C25 C 0.06299(17) 0.61849(10) 0.88761(17) 0.0412(4) Uani 1 d . . .
H25 H 0.0148 0.5726 0.8957 0.049 Uiso 1 calc . . R
C26 C 0.38994(17) 0.72252(9) 1.06927(17) 0.0408(4) Uani 1 d . . .
H26 H 0.4571 0.7490 1.0322 0.049 Uiso 1 calc . . R
C31 C 0.01273(18) 0.67002(12) 0.78117(18) 0.0505(4) Uani 1 d . . .
H31 H -0.0672 0.6580 0.7156 0.061 Uiso 1 calc . . R
C32 C 0.0817(2) 0.73944(12) 0.77261(17) 0.0505(4) Uani 1 d . . .
H32 H 0.0464 0.7749 0.7029 0.061 Uiso 1 calc . . R
C33 C 0.38796(18) 0.50131(10) 0.72324(18) 0.0446(4) Uani 1 d . . .
H33 H 0.4479 0.5282 0.6773 0.054 Uiso 1 calc . . R
C36 C 0.2306(2) 0.39490(10) 0.73069(18) 0.0488(4) Uani 1 d . . .
H36 H 0.1833 0.3514 0.6889 0.059 Uiso 1 calc . . R
C37 C 0.20280(19) 0.75628(10) 0.86707(17) 0.0439(4) Uani 1 d . . .
H37 H 0.2484 0.8031 0.8600 0.053 Uiso 1 calc . . R
C40 C 0.3352(2) 0.69025(11) 1.42245(18) 0.0543(5) Uani 1 d . . .
H40 H 0.3990 0.7280 1.4623 0.065 Uiso 1 calc . . R
C41 C 0.1476(2) 0.57689(11) 1.30779(19) 0.0504(4) Uani 1 d . . .
H41 H 0.0843 0.5386 1.2695 0.061 Uiso 1 calc . . R
C43 C 0.2458(3) 0.65901(12) 1.49910(19) 0.0635(6) Uani 1 d . . .
H43 H 0.2489 0.6760 1.5897 0.076 Uiso 1 calc . . R
C45 C 0.1516(2) 0.60273(13) 1.4424(2) 0.0627(6) Uani 1 d . . .
H45 H 0.0905 0.5820 1.4942 0.075 Uiso 1 calc . . R
Cl2 Cl 0.82982(6) 1.09021(4) 0.49566(5) 0.06849(17) Uani 1 d . . .
O2 O 0.77770(14) 1.04470(6) 1.15855(12) 0.0478(3) Uani 1 d . . .
N1 N 0.73812(14) 0.91904(7) 1.09147(13) 0.0356(3) Uani 1 d . . .
C5 C 0.78365(16) 1.01620(8) 0.92352(16) 0.0338(3) Uani 1 d . . .
C10 C 0.76604(16) 0.99552(8) 1.06759(16) 0.0346(3) Uani 1 d . . .
C11 C 0.68545(16) 0.86481(8) 0.98238(15) 0.0334(3) Uani 1 d . . .
C13 C 0.83263(18) 0.83356(9) 1.28514(16) 0.0401(4) Uani 1 d . . .
C15 C 0.81543(18) 1.06273(10) 0.66261(17) 0.0428(4) Uani 1 d . . .
C17 C 0.75864(16) 0.79577(9) 0.97346(15) 0.0351(3) Uani 1 d . . .
C20 C 0.73820(17) 0.89171(9) 1.23043(15) 0.0380(3) Uani 1 d . . .
C22 C 0.71665(19) 1.08213(9) 0.86265(18) 0.0427(4) Uani 1 d . . .
H22 H 0.6618 1.1114 0.9107 0.051 Uiso 1 calc . . R
C23 C 0.56306(17) 0.88151(10) 0.88760(17) 0.0411(4) Uani 1 d . . .
H23 H 0.5150 0.9274 0.8957 0.049 Uiso 1 calc . . R
C24 C 0.87055(17) 0.97492(9) 0.85355(17) 0.0399(3) Uani 1 d . . .
H24 H 0.9172 0.9310 0.8944 0.048 Uiso 1 calc . . R
C27 C 0.92304(18) 0.79489(10) 1.20422(18) 0.0440(4) Uani 1 d . . .
H27 H 1.0121 0.7811 1.2513 0.053 Uiso 1 calc . . R
C28 C 0.70279(19) 0.74377(10) 0.86721(17) 0.0438(4) Uani 1 d . . .
H28 H 0.7483 0.6969 0.8602 0.053 Uiso 1 calc . . R
C29 C 0.5819(2) 0.76046(12) 0.77271(18) 0.0509(4) Uani 1 d . . .
H29 H 0.5467 0.7250 0.7030 0.061 Uiso 1 calc . . R
C30 C 0.88985(17) 0.77753(9) 1.06934(17) 0.0408(4) Uani 1 d . . .
H30 H 0.9570 0.7511 1.0323 0.049 Uiso 1 calc . . R
C34 C 0.88806(18) 0.99873(10) 0.72331(18) 0.0449(4) Uani 1 d . . .
H34 H 0.9480 0.9719 0.6774 0.054 Uiso 1 calc . . R
C35 C 0.51257(19) 0.82999(12) 0.78117(17) 0.0502(4) Uani 1 d . . .
H35 H 0.4325 0.8420 0.7156 0.060 Uiso 1 calc . . R
C38 C 0.7306(2) 1.10504(10) 0.73066(18) 0.0486(4) Uani 1 d . . .
H38 H 0.6831 1.1485 0.6888 0.058 Uiso 1 calc . . R
C39 C 0.6473(2) 0.92324(11) 1.30765(19) 0.0503(4) Uani 1 d . . .
H39 H 0.5839 0.9616 1.2694 0.060 Uiso 1 calc . . R
C42 C 0.8352(2) 0.80975(11) 1.42257(18) 0.0539(5) Uani 1 d . . .
H42 H 0.8989 0.7719 1.4624 0.065 Uiso 1 calc . . R
C44 C 0.7459(3) 0.84101(13) 1.49917(19) 0.0636(6) Uani 1 d . . .
H44 H 0.7491 0.8242 1.5898 0.076 Uiso 1 calc . . R
C46 C 0.6516(2) 0.89718(13) 1.4422(2) 0.0630(5) Uani 1 d . . .
H46 H 0.5905 0.9178 1.4941 0.076 Uiso 1 calc . . R


_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 C16 1.7385(16) . ?
O3 C12 1.2201(19) . ?
N4 C6 1.4340(19) . ?
N4 C12 1.3721(19) . ?
N4 C14 1.4440(18) . ?
C6 C9 1.398(2) . ?
C6 C25 1.390(2) . ?
C7 C14 1.390(2) . ?
C7 C18 1.461(3) . ?
C7 C40 1.405(2) . ?
C8 C12 1.500(2) . ?
C8 C19 1.387(2) . ?
C8 C21 1.387(2) . ?
C9 C26 1.465(2) . ?
C9 C37 1.400(2) . ?
C14 C41 1.384(2) . ?
C16 C33 1.379(3) . ?
C16 C36 1.372(3) . ?
C18 C26 1.333(2) . ?
C19 C33 1.386(2) . ?
C21 C36 1.387(2) . ?
C25 C31 1.383(3) . ?
C31 C32 1.382(3) . ?
C32 C37 1.378(3) . ?
C40 C43 1.372(3) . ?
C41 C45 1.386(3) . ?
C43 C45 1.374(3) . ?
Cl2 C15 1.7379(16) . ?
O2 C10 1.2186(18) . ?
N1 C10 1.3734(19) . ?
N1 C11 1.4351(19) . ?
N1 C20 1.4424(19) . ?
C5 C10 1.501(2) . ?
C5 C22 1.384(2) . ?
C5 C24 1.389(2) . ?
C11 C17 1.398(2) . ?
C11 C23 1.389(2) . ?
C13 C20 1.393(2) . ?
C13 C27 1.461(2) . ?
C13 C42 1.405(2) . ?
C15 C34 1.379(3) . ?
C15 C38 1.373(3) . ?
C17 C28 1.399(2) . ?
C17 C30 1.463(2) . ?
C20 C39 1.388(2) . ?
C22 C38 1.387(2) . ?
C23 C35 1.383(3) . ?
C24 C34 1.385(2) . ?
C27 C30 1.332(2) . ?
C28 C29 1.377(3) . ?
C29 C35 1.385(3) . ?
C39 C46 1.387(3) . ?
C42 C44 1.371(3) . ?
C44 C46 1.373(3) . ?

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
C6 N4 C14 115.17(11) . . ?
C12 N4 C6 123.30(12) . . ?
C12 N4 C14 120.78(12) . . ?
C9 C6 N4 119.33(13) . . ?
C25 C6 N4 119.79(14) . . ?
C25 C6 C9 120.88(15) . . ?
C14 C7 C18 123.07(14) . . ?
C14 C7 C40 117.52(17) . . ?
C40 C7 C18 119.36(16) . . ?
C19 C8 C12 122.81(14) . . ?
C21 C8 C12 117.84(14) . . ?
C21 C8 C19 119.21(14) . . ?
C6 C9 C26 122.27(14) . . ?
C6 C9 C37 117.73(15) . . ?
C37 C9 C26 120.00(15) . . ?
O3 C12 N4 122.13(14) . . ?
O3 C12 C8 120.96(13) . . ?
N4 C12 C8 116.91(13) . . ?
C7 C14 N4 118.13(14) . . ?
C41 C14 N4 120.74(15) . . ?
C41 C14 C7 121.12(15) . . ?
C33 C16 Cl1 119.43(13) . . ?
C36 C16 Cl1 119.04(14) . . ?
C36 C16 C33 121.53(15) . . ?
C26 C18 C7 126.11(16) . . ?
C33 C19 C8 120.51(15) . . ?
C8 C21 C36 120.58(16) . . ?
C31 C25 C6 120.07(17) . . ?
C18 C26 C9 126.54(16) . . ?
C32 C31 C25 119.79(16) . . ?
C37 C32 C31 120.22(17) . . ?
C16 C33 C19 119.00(16) . . ?
C16 C36 C21 119.08(16) . . ?
C32 C37 C9 121.26(17) . . ?
C43 C40 C7 121.35(19) . . ?
C14 C41 C45 119.82(19) . . ?
C40 C43 C45 120.13(17) . . ?
C43 C45 C41 120.02(19) . . ?
C10 N1 C11 123.31(12) . . ?
C10 N1 C20 120.74(12) . . ?
C11 N1 C20 115.18(12) . . ?
C22 C5 C10 117.86(13) . . ?
C22 C5 C24 119.24(14) . . ?
C24 C5 C10 122.78(14) . . ?
O2 C10 N1 122.19(14) . . ?
O2 C10 C5 120.93(14) . . ?
N1 C10 C5 116.88(13) . . ?
C17 C11 N1 119.22(13) . . ?
C23 C11 N1 119.75(14) . . ?
C23 C11 C17 121.04(14) . . ?
C20 C13 C27 122.89(14) . . ?
C20 C13 C42 117.52(16) . . ?
C42 C13 C27 119.54(16) . . ?
C34 C15 Cl2 119.51(13) . . ?
C38 C15 Cl2 119.04(14) . . ?
C38 C15 C34 121.44(15) . . ?
C11 C17 C28 117.56(14) . . ?
C11 C17 C30 122.31(14) . . ?
C28 C17 C30 120.13(14) . . ?
C13 C20 N1 118.23(14) . . ?
C39 C20 N1 120.66(15) . . ?
C39 C20 C13 121.10(15) . . ?
C5 C22 C38 120.64(15) . . ?
C35 C23 C11 120.09(16) . . ?
C34 C24 C5 120.39(15) . . ?
C30 C27 C13 126.12(15) . . ?
C29 C28 C17 121.44(16) . . ?
C28 C29 C35 120.19(16) . . ?
C27 C30 C17 126.71(15) . . ?
C15 C34 C24 119.13(15) . . ?
C23 C35 C29 119.64(16) . . ?
C15 C38 C22 119.07(16) . . ?
C46 C39 C20 119.54(19) . . ?
C44 C42 C13 121.44(18) . . ?
C42 C44 C46 120.08(17) . . ?
C44 C46 C39 120.29(19) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: DCM'
####################################################################### 
# 
# 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_wyt0612_2_0m
_database_code_depnum_ccdc_archive 'CCDC 1967882'
loop_
_audit_author_name
_audit_author_address
'yating wen'
;JiLin University
China
;
_audit_update_record             
;
2021-01-19 deposited with the CCDC.	2021-11-10 downloaded from the CCDC.
;
_audit_creation_date             2018-06-30
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.04.18 svn.r3501 for OlexSys, GUI svn.r5488)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         '4(C21 H14 Cl N O)'
_chemical_formula_sum            'C84 H56 Cl4 N4 O4'
_chemical_formula_weight         1327.13
_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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P 21 c a'
_space_group_name_Hall           'P -2ac 2a'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 'x+1/2, -y, -z'
3 'x+1/2, y, -z+1/2'
4 'x, -y, z+1/2'

_cell_length_a                   7.3045(17)
_cell_length_b                   10.194(3)
_cell_length_c                   22.727(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1692.2(7)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    9505
_cell_measurement_temperature    293
_cell_measurement_theta_max      27.433
_cell_measurement_theta_min      3.350
_exptl_absorpt_coefficient_mu    0.232
_exptl_absorpt_correction_T_max  0.9886
_exptl_absorpt_correction_T_min  0.9886
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0489
_diffrn_reflns_av_unetI/netI     0.0451
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            18791
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         3.32
_diffrn_ambient_temperature      293
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'CCD Area Detector'
_diffrn_measurement_method       ?
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71076
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2761
_reflns_number_total             3774
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.187
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.67(9)
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3774
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0853
_refine_ls_R_factor_gt           0.0549
_refine_ls_restrained_S_all      1.092
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0177P)²+0.7528P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0896
_refine_ls_wR_factor_ref         0.0994
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C8(H8), C10(H10), C12(H12), C13(H13), C14(H14), C15(H15), C16(H16),
 C17(H17), C18(H18), C20(H20), C21(H21), C22(H22), C23(H23)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
Cl1 Cl 0.24044(16) 0.84061(8) 0.26287(3) 0.0764(3) Uani 1 d . . .
N1 N 0.2000(3) 0.33581(19) 0.06847(8) 0.0390(6) Uani 1 d . . .
O2 O -0.0049(4) 0.4797(2) 0.03194(9) 0.0675(7) Uani 1 d . . .
C3 C 0.1572(4) 0.2377(3) 0.02519(10) 0.0426(7) Uani 1 d . . .
C4 C 0.3279(4) 0.2056(3) 0.14811(11) 0.0402(7) Uani 1 d . . .
C5 C 0.2071(5) 0.7262(3) 0.20693(12) 0.0516(8) Uani 1 d . . .
C6 C 0.1483(5) 0.1662(4) -0.07426(13) 0.0686(10) Uani 1 d . . .
H6 H 0.1728 0.1810 -0.1148 0.082 Uiso 1 calc . . R
C7 C 0.3513(4) 0.3050(2) 0.10654(10) 0.0373(6) Uani 1 d . . .
C8 C 0.2309(5) 0.7634(3) 0.14968(12) 0.0599(9) Uani 1 d . . .
H8 H 0.2685 0.8502 0.1403 0.072 Uiso 1 calc . . R
C9 C 0.1084(4) 0.4525(3) 0.06901(11) 0.0430(7) Uani 1 d . . .
C10 C 0.1279(4) 0.5100(3) 0.17688(12) 0.0482(7) Uani 1 d . . .
H10 H 0.0941 0.4226 0.1864 0.058 Uiso 1 calc . . R
C11 C 0.1506(4) 0.5456(2) 0.11845(10) 0.0418(7) Uani 1 d . . .
C12 C 0.1540(5) 0.6005(3) 0.22134(11) 0.0531(8) Uani 1 d . . .
H12 H 0.1356 0.5764 0.2613 0.064 Uiso 1 calc . . R
C13 C 0.0544(5) 0.0906(3) 0.10660(14) 0.0576(9) Uani 1 d . . .
H13 H -0.0503 0.0399 0.1164 0.069 Uiso 1 calc . . R
C14 C 0.4731(5) 0.1828(3) 0.18677(12) 0.0570(9) Uani 1 d . . .
H14 H 0.4607 0.1174 0.2163 0.068 Uiso 1 calc . . R
C15 C 0.1624(5) 0.1272(3) 0.15127(12) 0.0543(8) Uani 1 d . . .
H15 H 0.1266 0.0985 0.1893 0.065 Uiso 1 calc . . R
C16 C 0.1939(4) 0.2617(3) -0.03349(10) 0.0524(8) Uani 1 d . . .
H16 H 0.2490 0.3417 -0.0455 0.063 Uiso 1 calc . . R
C17 C 0.1993(5) 0.6728(3) 0.10549(12) 0.0589(10) Uani 1 d . . .
H17 H 0.2114 0.6988 0.0655 0.071 Uiso 1 calc . . R
C18 C 0.5135(5) 0.3732(3) 0.10162(12) 0.0510(8) Uani 1 d . . .
H18 H 0.5281 0.4379 0.0719 0.061 Uiso 1 calc . . R
C19 C 0.0808(4) 0.1207(3) 0.04441(12) 0.0464(7) Uani 1 d . . .
C20 C 0.6321(6) 0.2521(4) 0.18311(13) 0.0732(11) Uani 1 d . . .
H20 H 0.7284 0.2351 0.2102 0.088 Uiso 1 calc . . R
C21 C 0.0348(5) 0.0279(3) 0.00151(16) 0.0645(9) Uani 1 d . . .
H21 H -0.0209 -0.0524 0.0130 0.077 Uiso 1 calc . . R
C22 C 0.6544(5) 0.3468(4) 0.14030(14) 0.0722(10) Uani 1 d . . .
H22 H 0.7664 0.3937 0.1375 0.087 Uiso 1 calc . . R
C23 C 0.0692(5) 0.0516(4) -0.05721(16) 0.0758(11) Uani 1 d . . .
H23 H 0.0374 -0.0123 -0.0858 0.091 Uiso 1 calc . . R


_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 C5 1.743(3) . ?
N1 C3 1.437(3) . ?
N1 C7 1.439(3) . ?
N1 C9 1.365(3) . ?
O2 C9 1.213(3) . ?
C3 C16 1.382(3) . ?
C3 C19 1.387(4) . ?
C4 C7 1.396(3) . ?
C4 C14 1.397(4) . ?
C4 C15 1.451(4) . ?
C5 C8 1.366(4) . ?
C5 C12 1.378(4) . ?
C6 C16 1.384(4) . ?
C6 C23 1.360(5) . ?
C7 C18 1.378(4) . ?
C8 C17 1.384(4) . ?
C9 C11 1.503(4) . ?
C10 C11 1.387(3) . ?
C10 C12 1.381(4) . ?
C11 C17 1.376(4) . ?
C13 C15 1.338(4) . ?
C13 C19 1.459(4) . ?
C14 C20 1.362(5) . ?
C18 C22 1.380(4) . ?
C19 C21 1.399(4) . ?
C20 C22 1.380(5) . ?
C21 C23 1.379(5) . ?

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 C7 115.2(2) . . ?
C9 N1 C3 120.4(2) . . ?
C9 N1 C7 124.2(2) . . ?
C16 C3 N1 119.7(3) . . ?
C16 C3 C19 122.3(2) . . ?
C19 C3 N1 118.1(2) . . ?
C7 C4 C14 117.0(3) . . ?
C7 C4 C15 122.4(3) . . ?
C14 C4 C15 120.6(3) . . ?
C8 C5 Cl1 119.4(2) . . ?
C8 C5 C12 121.3(3) . . ?
C12 C5 Cl1 119.2(2) . . ?
C23 C6 C16 121.0(3) . . ?
C4 C7 N1 118.1(2) . . ?
C18 C7 N1 120.1(2) . . ?
C18 C7 C4 121.8(2) . . ?
C5 C8 C17 119.0(3) . . ?
N1 C9 C11 117.2(2) . . ?
O2 C9 N1 121.8(2) . . ?
O2 C9 C11 121.0(2) . . ?
C12 C10 C11 120.6(3) . . ?
C10 C11 C9 121.7(2) . . ?
C17 C11 C9 119.2(2) . . ?
C17 C11 C10 118.9(2) . . ?
C5 C12 C10 119.1(2) . . ?
C15 C13 C19 126.7(3) . . ?
C20 C14 C4 121.5(3) . . ?
C13 C15 C4 127.4(3) . . ?
C3 C16 C6 118.4(3) . . ?
C11 C17 C8 121.1(2) . . ?
C7 C18 C22 119.4(3) . . ?
C3 C19 C13 122.6(2) . . ?
C3 C19 C21 117.3(3) . . ?
C21 C19 C13 120.1(3) . . ?
C14 C20 C22 120.4(3) . . ?
C23 C21 C19 120.8(3) . . ?
C18 C22 C20 119.9(4) . . ?
C6 C23 C21 120.3(3) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
