# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2020

####################################################################### 
# 
# 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_190309b
_database_code_depnum_ccdc_archive 'CCDC 2034320'
loop_
_audit_author_name
_audit_author_address
'Tao Xu'
;Ocean University of China
China
;
_audit_update_record             
;
2020-09-27 deposited with the CCDC.	2020-12-09 downloaded from the CCDC.
;
_audit_creation_date             2020-09-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
;
_chemical_name_common            ?
_chemical_name_systematic        wd-2n
_chemical_formula_moiety         'C46 H46 N2 O5 S'
_chemical_formula_sum            'C46 H46 N2 O5 S'
_chemical_formula_weight         738.91
_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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, -y, z+1/2'
3 '-x, y+1/2, -z+1/2'
4 'x+1/2, -y+1/2, -z'
5 '-x, -y, -z'
6 'x-1/2, y, -z-1/2'
7 'x, -y-1/2, z-1/2'
8 '-x-1/2, y-1/2, z'

_cell_length_a                   21.3754(10)
_cell_length_b                   15.8343(7)
_cell_length_c                   24.1944(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     8188.9(6)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2499
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      49.7200
_cell_measurement_theta_min      4.1990
_exptl_absorpt_coefficient_mu    1.075
_exptl_absorpt_correction_T_max  0.8909
_exptl_absorpt_correction_T_min  0.7048
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.199
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       sheet
_exptl_crystal_F_000             3136
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.11
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0520
_diffrn_reflns_av_unetI/netI     0.0720
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            18721
_diffrn_reflns_theta_full        66.05
_diffrn_reflns_theta_max         66.05
_diffrn_reflns_theta_min         3.65
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.1281
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                3624
_reflns_number_total             7135
_reflns_threshold_expression     >2sigma(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  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2008)'
_refine_diff_density_max         0.241
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       0.00045(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     495
_refine_ls_number_reflns         7135
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1283
_refine_ls_R_factor_gt           0.0608
_refine_ls_restrained_S_all      1.056
_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)+(0.0469P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1258
_refine_ls_wR_factor_ref         0.1551
_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. Others
 Fixed Uiso: H1(0.13) H1A(0.069) H5(0.092) H6(0.109) H7(0.1) H8(0.075)
 H9(0.056) H11(0.063) H15(0.061) H17A(0.137) H17B(0.137) H17C(0.137)
 H18A(0.167) H18B(0.167) H18C(0.167) H19A(0.129) H19B(0.129) H19C(0.129)
 H21A(0.12) H21B(0.12) H21C(0.12) H22A(0.157) H22B(0.157) H22C(0.157)
 H23A(0.16) H23B(0.16) H23C(0.16) H25(0.063) H26(0.067) H27(0.073) H29(0.094)
 H30(0.103) H32(0.09) H33(0.091) H35(0.073) H36(0.088) H37(0.096) H38(0.094)
 H39(0.075) H41(0.092) H42(0.094) H44(0.124) H45(0.117) H46A(0.175) H46B(0.175)
 H46C(0.175)
 Fixed X: H1(0.2897) H1A(0.5429) H5(0.7688) H6(0.8076) H7(0.7423) H8(0.635)
 H9(0.5174) H11(0.46) H15(0.4362) H17A(0.2932) H17B(0.2911) H17C(0.2727)
 H18A(0.4531) H18B(0.4) H18C(0.4019) H19A(0.3579) H19B(0.3633) H19C(0.4233)
 H21A(0.3387) H21B(0.4055) H21C(0.36) H22A(0.3554) H22B(0.3757) H22C(0.3049)
 H23A(0.2419) H23B(0.2552) H23C(0.2607) H25(0.5677) H26(0.5209) H27(0.6027)
 H29(0.6418) H30(0.6354) H32(0.5032) H33(0.5094) H35(0.5175) H36(0.4567)
 H37(0.3757) H38(0.3518) H39(0.4117) H41(0.7616) H42(0.773) H44(0.5937)
 H45(0.5824) H46A(0.6642) H46B(0.7339) H46C(0.6802)
 Fixed Y: H1(0.2699) H1A(0.3229) H5(0.3703) H6(0.5003) H7(0.6058) H8(0.5869)
 H9(0.5357) H11(0.4692) H15(0.3914) H17A(0.4694) H17B(0.4144) H17C(0.3744)
 H18A(0.4345) H18B(0.442) H18C(0.5048) H19A(0.2584) H19B(0.2959) H19C(0.2861)
 H21A(0.2701) H21B(0.2851) H21C(0.3616) H22A(0.1887) H22B(0.1713) H22C(0.1665)
 H23A(0.2714) H23B(0.3229) H23C(0.3669) H25(0.4389) H26(0.5659) H27(0.4396)
 H29(0.4414) H30(0.4862) H32(0.6514) H33(0.6082) H35(0.6726) H36(0.7911)
 H37(0.7898) H38(0.6674) H39(0.5478) H41(0.3292) H42(0.3906) H44(0.3451)
 H45(0.2824) H46A(0.4674) H46B(0.437) H46C(0.3808)
 Fixed Z: H1(0.8778) H1A(0.8789) H5(0.8746) H6(0.8479) H7(0.818) H8(0.8163)
 H9(0.863) H11(0.9346) H15(0.7799) H17A(0.9838) H17B(1.0377) H17C(0.9807)
 H18A(1.017) H18B(1.0614) H18C(1.0114) H19A(0.9897) H19B(1.0495) H19C(1.0127)
 H21A(0.704) H21B(0.7291) H21C(0.7202) H22A(0.8397) H22B(0.7784) H22C(0.795)
 H23A(0.8011) H23B(0.7471) H23C(0.8049) H25(0.7451) H26(0.6744) H27(0.6469)
 H29(0.5519) H30(0.4608) H32(0.5028) H33(0.5936) H35(0.8263) H36(0.8135)
 H37(0.751) H38(0.7048) H39(0.717) H41(0.9761) H42(1.0615) H44(1.0938)
 H45(1.0093) H46A(1.1431) H46B(1.1467) H46C(1.171)
;
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.64005(13) 0.33236(16) 0.87723(11) 0.0656(8) Uani 1 1 d . . .
N2 N 0.56374(19) 0.6021(3) 0.41689(15) 0.0951(12) Uani 1 1 d . . .
O1 O 0.30459(11) 0.29469(15) 0.90446(9) 0.0869(8) Uani 1 1 d . . .
H1 H 0.2897 0.2699 0.8778 0.130 Uiso 1 1 calc RD . .
O2 O 0.52796(18) 0.6601(2) 0.40662(12) 0.1190(12) Uani 1 1 d . . .
O3 O 0.59229(16) 0.5618(3) 0.38204(13) 0.1595(17) Uani 1 1 d . . .
O4 O 0.60986(15) 0.19700(14) 0.91960(12) 0.1121(11) Uani 1 1 d . . .
O5 O 0.72193(14) 0.22758(17) 0.89919(11) 0.1087(10) Uani 1 1 d . . .
S1 S 0.66175(6) 0.25389(6) 0.91853(4) 0.0853(4) Uani 1 1 d . . .
C1 C 0.57718(15) 0.35669(19) 0.87056(12) 0.0579(9) Uani 1 1 d . . .
H1A H 0.5429 0.3229 0.8789 0.069 Uiso 1 1 calc R . .
C2 C 0.57375(14) 0.43574(18) 0.85035(12) 0.0473(7) Uani 1 1 d . . .
C3 C 0.63733(14) 0.46620(19) 0.84502(12) 0.0499(8) Uani 1 1 d . . .
C4 C 0.67773(16) 0.4024(2) 0.86249(13) 0.0604(9) Uani 1 1 d . . .
C5 C 0.74212(17) 0.4134(3) 0.86341(14) 0.0769(11) Uani 1 1 d . . .
H5 H 0.7688 0.3703 0.8746 0.092 Uiso 1 1 calc R . .
C6 C 0.76468(18) 0.4906(3) 0.84707(16) 0.0910(13) Uani 1 1 d . . .
H6 H 0.8076 0.5003 0.8479 0.109 Uiso 1 1 calc R . .
C7 C 0.72524(17) 0.5546(3) 0.82932(15) 0.0833(12) Uani 1 1 d . . .
H7 H 0.7423 0.6058 0.8180 0.100 Uiso 1 1 calc R . .
C8 C 0.66132(15) 0.5437(2) 0.82807(13) 0.0622(9) Uani 1 1 d . . .
H8 H 0.6350 0.5869 0.8163 0.075 Uiso 1 1 calc R . .
C9 C 0.51566(13) 0.48647(18) 0.83852(12) 0.0469(7) Uani 1 1 d . . .
H9 H 0.5174 0.5357 0.8630 0.056 Uiso 1 1 calc R . .
C10 C 0.45640(13) 0.43786(18) 0.85469(12) 0.0474(7) Uani 1 1 d . . .
C11 C 0.43771(14) 0.43706(18) 0.90909(12) 0.0525(8) Uani 1 1 d . . .
H11 H 0.4600 0.4692 0.9346 0.063 Uiso 1 1 calc R . .
C12 C 0.38665(14) 0.38999(19) 0.92752(12) 0.0526(8) Uani 1 1 d . . .
C13 C 0.35505(15) 0.34279(19) 0.88748(13) 0.0572(9) Uani 1 1 d . . .
C14 C 0.37162(14) 0.34257(19) 0.83131(13) 0.0514(8) Uani 1 1 d . . .
C15 C 0.42341(14) 0.39087(18) 0.81662(12) 0.0507(8) Uani 1 1 d . . .
H15 H 0.4362 0.3914 0.7799 0.061 Uiso 1 1 calc R . .
C16 C 0.36908(17) 0.3874(2) 0.98930(13) 0.0628(9) Uani 1 1 d . . .
C17 C 0.29993(18) 0.4139(2) 0.99876(15) 0.0910(13) Uani 1 1 d . . .
H17A H 0.2932 0.4694 0.9838 0.137 Uiso 1 1 calc R . .
H17B H 0.2911 0.4144 1.0377 0.137 Uiso 1 1 calc R . .
H17C H 0.2727 0.3744 0.9807 0.137 Uiso 1 1 calc R . .
C18 C 0.4098(2) 0.4478(3) 1.02291(14) 0.1116(17) Uani 1 1 d . . .
H18A H 0.4531 0.4345 1.0170 0.167 Uiso 1 1 calc R . .
H18B H 0.4000 0.4420 1.0614 0.167 Uiso 1 1 calc R . .
H18C H 0.4019 0.5048 1.0114 0.167 Uiso 1 1 calc R . .
C19 C 0.37934(18) 0.2987(2) 1.01243(15) 0.0862(12) Uani 1 1 d . . .
H19A H 0.3579 0.2584 0.9897 0.129 Uiso 1 1 calc R . .
H19B H 0.3633 0.2959 1.0495 0.129 Uiso 1 1 calc R . .
H19C H 0.4233 0.2861 1.0127 0.129 Uiso 1 1 calc R . .
C20 C 0.33618(16) 0.2900(2) 0.78808(14) 0.0646(9) Uani 1 1 d . . .
C21 C 0.36254(17) 0.3029(2) 0.72994(14) 0.0799(11) Uani 1 1 d . . .
H21A H 0.3387 0.2701 0.7040 0.120 Uiso 1 1 calc R . .
H21B H 0.4055 0.2851 0.7291 0.120 Uiso 1 1 calc R . .
H21C H 0.3600 0.3616 0.7202 0.120 Uiso 1 1 calc R . .
C22 C 0.3438(2) 0.1951(2) 0.80156(16) 0.1045(15) Uani 1 1 d . . .
H22A H 0.3554 0.1887 0.8397 0.157 Uiso 1 1 calc RD . .
H22B H 0.3757 0.1713 0.7784 0.157 Uiso 1 1 calc R . .
H22C H 0.3049 0.1665 0.7950 0.157 Uiso 1 1 calc R . .
C23 C 0.26705(16) 0.3152(3) 0.78500(16) 0.1064(15) Uani 1 1 d . . .
H23A H 0.2419 0.2714 0.8011 0.160 Uiso 1 1 calc RD . .
H23B H 0.2552 0.3229 0.7471 0.160 Uiso 1 1 calc R . .
H23C H 0.2607 0.3669 0.8049 0.160 Uiso 1 1 calc R . .
C24 C 0.51265(13) 0.52121(17) 0.78016(12) 0.0449(7) Uani 1 1 d . . .
C25 C 0.54427(15) 0.48709(18) 0.73773(12) 0.0529(8) Uani 1 1 d . . .
H25 H 0.5677 0.4389 0.7451 0.063 Uiso 1 1 calc R . .
C26 C 0.54513(15) 0.51845(19) 0.68182(12) 0.0561(8) Uani 1 1 d . . .
H26 H 0.5209 0.5659 0.6744 0.067 Uiso 1 1 calc R . .
C27 C 0.57729(16) 0.4860(2) 0.63986(13) 0.0607(9) Uani 1 1 d . . .
H27 H 0.6027 0.4396 0.6469 0.073 Uiso 1 1 calc R . .
C28 C 0.57548(16) 0.5186(2) 0.58316(13) 0.0585(9) Uani 1 1 d . . .
C29 C 0.61356(17) 0.4836(3) 0.54238(15) 0.0784(11) Uani 1 1 d . . .
H29 H 0.6418 0.4414 0.5519 0.094 Uiso 1 1 calc R . .
C30 C 0.61024(18) 0.5105(3) 0.48785(15) 0.0857(12) Uani 1 1 d . . .
H30 H 0.6354 0.4862 0.4608 0.103 Uiso 1 1 calc R . .
C31 C 0.56942(19) 0.5731(3) 0.47484(14) 0.0703(10) Uani 1 1 d . . .
C32 C 0.53125(18) 0.6093(2) 0.51309(15) 0.0750(10) Uani 1 1 d . . .
H32 H 0.5032 0.6514 0.5028 0.090 Uiso 1 1 calc R . .
C33 C 0.53477(19) 0.5828(2) 0.56715(14) 0.0758(11) Uani 1 1 d . . .
H33 H 0.5094 0.6082 0.5936 0.091 Uiso 1 1 calc R . .
C34 C 0.47189(14) 0.59674(18) 0.77309(12) 0.0509(8) Uani 1 1 d . . .
C35 C 0.48428(15) 0.67080(18) 0.80154(13) 0.0612(9) Uani 1 1 d . . .
H35 H 0.5175 0.6726 0.8263 0.073 Uiso 1 1 calc R . .
C36 C 0.44797(17) 0.7421(2) 0.79369(16) 0.0730(10) Uani 1 1 d . . .
H36 H 0.4567 0.7911 0.8135 0.088 Uiso 1 1 calc R . .
C37 C 0.39929(18) 0.7412(2) 0.75696(17) 0.0799(11) Uani 1 1 d . . .
H37 H 0.3757 0.7898 0.7510 0.096 Uiso 1 1 calc R . .
C38 C 0.38554(17) 0.6686(2) 0.72905(16) 0.0786(11) Uani 1 1 d . . .
H38 H 0.3518 0.6674 0.7048 0.094 Uiso 1 1 calc R . .
C39 C 0.42139(15) 0.5967(2) 0.73656(13) 0.0624(9) Uani 1 1 d . . .
H39 H 0.4117 0.5478 0.7170 0.075 Uiso 1 1 calc R . .
C40 C 0.6705(2) 0.2993(2) 0.98386(15) 0.0685(10) Uani 1 1 d . . .
C41 C 0.72759(19) 0.3322(2) 0.99990(16) 0.0767(11) Uani 1 1 d . . .
H41 H 0.7616 0.3292 0.9761 0.092 Uiso 1 1 calc R . .
C42 C 0.73427(19) 0.3693(2) 1.05099(16) 0.0784(11) Uani 1 1 d . . .
H42 H 0.7730 0.3906 1.0615 0.094 Uiso 1 1 calc R . .
C43 C 0.6844(2) 0.3754(3) 1.08689(16) 0.0812(12) Uani 1 1 d . . .
C44 C 0.6279(2) 0.3420(3) 1.0702(2) 0.1037(15) Uani 1 1 d . . .
H44 H 0.5937 0.3451 1.0938 0.124 Uiso 1 1 calc R . .
C45 C 0.6210(2) 0.3045(3) 1.0195(2) 0.0976(14) Uani 1 1 d . . .
H45 H 0.5824 0.2824 1.0093 0.117 Uiso 1 1 calc R . .
C46 C 0.6913(2) 0.4191(3) 1.14191(16) 0.1164(17) Uani 1 1 d . . .
H46A H 0.6642 0.4674 1.1431 0.175 Uiso 1 1 calc R . .
H46B H 0.7339 0.4370 1.1467 0.175 Uiso 1 1 calc R . .
H46C H 0.6802 0.3808 1.1710 0.175 Uiso 1 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
N1 S1 1.661(3) . ?
N1 C1 1.407(4) . ?
N1 C4 1.416(4) . ?
N2 O2 1.220(4) . ?
N2 O3 1.221(4) . ?
N2 C31 1.480(4) . ?
O1 H1 0.8200 . ?
O1 C13 1.383(3) . ?
O4 S1 1.429(3) . ?
O5 S1 1.431(3) . ?
S1 C40 1.747(4) . ?
C1 H1A 0.9300 . ?
C1 C2 1.346(4) . ?
C2 C3 1.448(4) . ?
C2 C9 1.506(4) . ?
C3 C4 1.395(4) . ?
C3 C8 1.392(4) . ?
C4 C5 1.387(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.372(5) . ?
C6 H6 0.9300 . ?
C6 C7 1.386(5) . ?
C7 H7 0.9300 . ?
C7 C8 1.377(4) . ?
C8 H8 0.9300 . ?
C9 H9 0.9800 . ?
C9 C10 1.533(4) . ?
C9 C24 1.517(4) . ?
C10 C11 1.376(4) . ?
C10 C15 1.378(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.395(4) . ?
C12 C13 1.398(4) . ?
C12 C16 1.542(4) . ?
C13 C14 1.404(4) . ?
C14 C15 1.392(4) . ?
C14 C20 1.536(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.553(4) . ?
C16 C18 1.527(4) . ?
C16 C19 1.528(4) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 C21 1.529(4) . ?
C20 C22 1.546(5) . ?
C20 C23 1.532(4) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 C25 1.343(4) . ?
C24 C34 1.490(4) . ?
C25 H25 0.9300 . ?
C25 C26 1.441(4) . ?
C26 H26 0.9300 . ?
C26 C27 1.329(4) . ?
C27 H27 0.9300 . ?
C27 C28 1.466(4) . ?
C28 C29 1.394(4) . ?
C28 C33 1.393(4) . ?
C29 H29 0.9300 . ?
C29 C30 1.388(5) . ?
C30 H30 0.9300 . ?
C30 C31 1.358(5) . ?
C31 C32 1.360(4) . ?
C32 H32 0.9300 . ?
C32 C33 1.376(4) . ?
C33 H33 0.9300 . ?
C34 C35 1.385(4) . ?
C34 C39 1.395(4) . ?
C35 H35 0.9300 . ?
C35 C36 1.384(4) . ?
C36 H36 0.9300 . ?
C36 C37 1.368(5) . ?
C37 H37 0.9300 . ?
C37 C38 1.366(5) . ?
C38 H38 0.9300 . ?
C38 C39 1.384(4) . ?
C39 H39 0.9300 . ?
C40 C41 1.382(5) . ?
C40 C45 1.367(5) . ?
C41 H41 0.9300 . ?
C41 C42 1.376(5) . ?
C42 H42 0.9300 . ?
C42 C43 1.378(5) . ?
C43 C44 1.379(5) . ?
C43 C46 1.508(5) . ?
C44 H44 0.9300 . ?
C44 C45 1.370(5) . ?
C45 H45 0.9300 . ?
C46 H46A 0.9600 . ?
C46 H46B 0.9600 . ?
C46 H46C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 S1 122.7(2) . . ?
C1 N1 C4 107.4(3) . . ?
C4 N1 S1 125.4(2) . . ?
O2 N2 O3 124.5(4) . . ?
O2 N2 C31 118.5(4) . . ?
O3 N2 C31 116.8(4) . . ?
C13 O1 H1 109.5 . . ?
N1 S1 C40 105.44(15) . . ?
O4 S1 N1 105.42(16) . . ?
O4 S1 O5 121.34(18) . . ?
O4 S1 C40 109.0(2) . . ?
O5 S1 N1 105.79(17) . . ?
O5 S1 C40 108.65(19) . . ?
N1 C1 H1A 124.8 . . ?
C2 C1 N1 110.4(3) . . ?
C2 C1 H1A 124.8 . . ?
C1 C2 C3 106.9(3) . . ?
C1 C2 C9 127.6(3) . . ?
C3 C2 C9 125.4(3) . . ?
C4 C3 C2 108.2(3) . . ?
C8 C3 C2 131.7(3) . . ?
C8 C3 C4 120.0(3) . . ?
C3 C4 N1 106.9(3) . . ?
C5 C4 N1 131.2(3) . . ?
C5 C4 C3 121.9(3) . . ?
C4 C5 H5 121.4 . . ?
C6 C5 C4 117.1(4) . . ?
C6 C5 H5 121.4 . . ?
C5 C6 H6 119.1 . . ?
C5 C6 C7 121.8(4) . . ?
C7 C6 H6 119.1 . . ?
C6 C7 H7 119.4 . . ?
C8 C7 C6 121.3(4) . . ?
C8 C7 H7 119.4 . . ?
C3 C8 H8 121.0 . . ?
C7 C8 C3 118.0(3) . . ?
C7 C8 H8 121.0 . . ?
C2 C9 H9 106.1 . . ?
C2 C9 C10 111.4(2) . . ?
C2 C9 C24 113.9(2) . . ?
C10 C9 H9 106.1 . . ?
C24 C9 H9 106.1 . . ?
C24 C9 C10 112.6(2) . . ?
C11 C10 C9 119.3(3) . . ?
C11 C10 C15 119.1(3) . . ?
C15 C10 C9 121.6(3) . . ?
C10 C11 H11 118.7 . . ?
C10 C11 C12 122.5(3) . . ?
C12 C11 H11 118.7 . . ?
C11 C12 C13 116.3(3) . . ?
C11 C12 C16 121.0(3) . . ?
C13 C12 C16 122.7(3) . . ?
O1 C13 C12 117.7(3) . . ?
O1 C13 C14 118.9(3) . . ?
C12 C13 C14 123.4(3) . . ?
C13 C14 C20 122.4(3) . . ?
C15 C14 C13 116.5(3) . . ?
C15 C14 C20 121.1(3) . . ?
C10 C15 C14 122.2(3) . . ?
C10 C15 H15 118.9 . . ?
C14 C15 H15 118.9 . . ?
C12 C16 C17 111.6(3) . . ?
C18 C16 C12 111.2(3) . . ?
C18 C16 C17 107.1(3) . . ?
C18 C16 C19 107.4(3) . . ?
C19 C16 C12 110.1(3) . . ?
C19 C16 C17 109.3(3) . . ?
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 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C14 C20 C22 109.3(3) . . ?
C21 C20 C14 111.9(3) . . ?
C21 C20 C22 106.6(3) . . ?
C21 C20 C23 106.0(3) . . ?
C23 C20 C14 111.6(3) . . ?
C23 C20 C22 111.4(3) . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C20 C22 H22A 109.5 . . ?
C20 C22 H22B 109.5 . . ?
C20 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C20 C23 H23A 109.5 . . ?
C20 C23 H23B 109.5 . . ?
C20 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C25 C24 C9 123.0(3) . . ?
C25 C24 C34 122.0(3) . . ?
C34 C24 C9 115.0(2) . . ?
C24 C25 H25 117.1 . . ?
C24 C25 C26 125.8(3) . . ?
C26 C25 H25 117.1 . . ?
C25 C26 H26 116.9 . . ?
C27 C26 C25 126.2(3) . . ?
C27 C26 H26 116.9 . . ?
C26 C27 H27 117.8 . . ?
C26 C27 C28 124.4(3) . . ?
C28 C27 H27 117.8 . . ?
C29 C28 C27 120.5(3) . . ?
C33 C28 C27 122.2(3) . . ?
C33 C28 C29 117.3(3) . . ?
C28 C29 H29 119.3 . . ?
C30 C29 C28 121.4(4) . . ?
C30 C29 H29 119.3 . . ?
C29 C30 H30 120.8 . . ?
C31 C30 C29 118.5(4) . . ?
C31 C30 H30 120.8 . . ?
C30 C31 N2 119.9(4) . . ?
C30 C31 C32 122.4(3) . . ?
C32 C31 N2 117.7(4) . . ?
C31 C32 H32 120.5 . . ?
C31 C32 C33 119.0(4) . . ?
C33 C32 H32 120.5 . . ?
C28 C33 H33 119.3 . . ?
C32 C33 C28 121.4(3) . . ?
C32 C33 H33 119.3 . . ?
C35 C34 C24 120.7(3) . . ?
C35 C34 C39 117.6(3) . . ?
C39 C34 C24 121.6(3) . . ?
C34 C35 H35 119.5 . . ?
C36 C35 C34 121.0(3) . . ?
C36 C35 H35 119.5 . . ?
C35 C36 H36 119.8 . . ?
C37 C36 C35 120.5(3) . . ?
C37 C36 H36 119.8 . . ?
C36 C37 H37 120.2 . . ?
C38 C37 C36 119.6(3) . . ?
C38 C37 H37 120.2 . . ?
C37 C38 H38 119.7 . . ?
C37 C38 C39 120.6(4) . . ?
C39 C38 H38 119.7 . . ?
C34 C39 H39 119.6 . . ?
C38 C39 C34 120.7(3) . . ?
C38 C39 H39 119.6 . . ?
C41 C40 S1 120.2(3) . . ?
C45 C40 S1 120.9(4) . . ?
C45 C40 C41 118.9(4) . . ?
C40 C41 H41 119.8 . . ?
C42 C41 C40 120.3(4) . . ?
C42 C41 H41 119.8 . . ?
C41 C42 H42 119.5 . . ?
C41 C42 C43 121.0(4) . . ?
C43 C42 H42 119.5 . . ?
C42 C43 C44 117.8(4) . . ?
C42 C43 C46 120.9(5) . . ?
C44 C43 C46 121.3(4) . . ?
C43 C44 H44 119.3 . . ?
C45 C44 C43 121.5(4) . . ?
C45 C44 H44 119.3 . . ?
C40 C45 C44 120.5(4) . . ?
C40 C45 H45 119.7 . . ?
C44 C45 H45 119.7 . . ?
C43 C46 H46A 109.5 . . ?
C43 C46 H46B 109.5 . . ?
C43 C46 H46C 109.5 . . ?
H46A C46 H46B 109.5 . . ?
H46A C46 H46C 109.5 . . ?
H46B C46 H46C 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 S1 C40 C41 -90.0(3) . . . . ?
N1 S1 C40 C45 88.8(3) . . . . ?
N1 C1 C2 C3 -1.8(3) . . . . ?
N1 C1 C2 C9 -178.3(3) . . . . ?
N1 C4 C5 C6 -179.0(3) . . . . ?
N2 C31 C32 C33 179.0(3) . . . . ?
O1 C13 C14 C15 -178.9(3) . . . . ?
O1 C13 C14 C20 -0.7(5) . . . . ?
O2 N2 C31 C30 -178.0(4) . . . . ?
O2 N2 C31 C32 4.2(6) . . . . ?
O3 N2 C31 C30 7.0(6) . . . . ?
O3 N2 C31 C32 -170.8(4) . . . . ?
O4 S1 C40 C41 157.2(3) . . . . ?
O4 S1 C40 C45 -24.0(4) . . . . ?
O5 S1 C40 C41 23.0(3) . . . . ?
O5 S1 C40 C45 -158.2(3) . . . . ?
S1 N1 C1 C2 160.1(2) . . . . ?
S1 N1 C4 C3 -159.1(2) . . . . ?
S1 N1 C4 C5 20.8(5) . . . . ?
S1 C40 C41 C42 178.9(3) . . . . ?
S1 C40 C45 C44 -178.5(3) . . . . ?
C1 N1 S1 O4 28.9(3) . . . . ?
C1 N1 S1 O5 158.6(3) . . . . ?
C1 N1 S1 C40 -86.4(3) . . . . ?
C1 N1 C4 C3 -2.5(3) . . . . ?
C1 N1 C4 C5 177.4(3) . . . . ?
C1 C2 C3 C4 0.3(4) . . . . ?
C1 C2 C3 C8 -177.7(3) . . . . ?
C1 C2 C9 C10 2.3(4) . . . . ?
C1 C2 C9 C24 -126.5(3) . . . . ?
C2 C3 C4 N1 1.4(3) . . . . ?
C2 C3 C4 C5 -178.5(3) . . . . ?
C2 C3 C8 C7 177.7(3) . . . . ?
C2 C9 C10 C11 81.1(3) . . . . ?
C2 C9 C10 C15 -95.0(3) . . . . ?
C2 C9 C24 C25 23.2(4) . . . . ?
C2 C9 C24 C34 -156.7(2) . . . . ?
C3 C2 C9 C10 -173.6(3) . . . . ?
C3 C2 C9 C24 57.7(4) . . . . ?
C3 C4 C5 C6 0.9(5) . . . . ?
C4 N1 S1 O4 -177.9(3) . . . . ?
C4 N1 S1 O5 -48.2(3) . . . . ?
C4 N1 S1 C40 66.8(3) . . . . ?
C4 N1 C1 C2 2.7(4) . . . . ?
C4 C3 C8 C7 -0.1(5) . . . . ?
C4 C5 C6 C7 -1.2(6) . . . . ?
C5 C6 C7 C8 0.9(6) . . . . ?
C6 C7 C8 C3 -0.3(5) . . . . ?
C8 C3 C4 N1 179.6(3) . . . . ?
C8 C3 C4 C5 -0.3(5) . . . . ?
C9 C2 C3 C4 176.8(3) . . . . ?
C9 C2 C3 C8 -1.1(5) . . . . ?
C9 C10 C11 C12 -175.9(3) . . . . ?
C9 C10 C15 C14 176.3(3) . . . . ?
C9 C24 C25 C26 -177.8(3) . . . . ?
C9 C24 C34 C35 60.8(4) . . . . ?
C9 C24 C34 C39 -121.3(3) . . . . ?
C10 C9 C24 C25 -104.9(3) . . . . ?
C10 C9 C24 C34 75.2(3) . . . . ?
C10 C11 C12 C13 0.2(5) . . . . ?
C10 C11 C12 C16 177.1(3) . . . . ?
C11 C10 C15 C14 0.1(5) . . . . ?
C11 C12 C13 O1 179.3(3) . . . . ?
C11 C12 C13 C14 -1.3(5) . . . . ?
C11 C12 C16 C17 125.1(3) . . . . ?
C11 C12 C16 C18 5.5(5) . . . . ?
C11 C12 C16 C19 -113.3(3) . . . . ?
C12 C13 C14 C15 1.7(5) . . . . ?
C12 C13 C14 C20 179.9(3) . . . . ?
C13 C12 C16 C17 -58.3(4) . . . . ?
C13 C12 C16 C18 -177.8(3) . . . . ?
C13 C12 C16 C19 63.4(4) . . . . ?
C13 C14 C15 C10 -1.1(5) . . . . ?
C13 C14 C20 C21 178.5(3) . . . . ?
C13 C14 C20 C22 -63.7(4) . . . . ?
C13 C14 C20 C23 59.9(4) . . . . ?
C15 C10 C11 C12 0.4(5) . . . . ?
C15 C14 C20 C21 -3.4(4) . . . . ?
C15 C14 C20 C22 114.4(3) . . . . ?
C15 C14 C20 C23 -122.0(3) . . . . ?
C16 C12 C13 O1 2.5(5) . . . . ?
C16 C12 C13 C14 -178.1(3) . . . . ?
C20 C14 C15 C10 -179.3(3) . . . . ?
C24 C9 C10 C11 -149.5(3) . . . . ?
C24 C9 C10 C15 34.4(4) . . . . ?
C24 C25 C26 C27 178.5(3) . . . . ?
C24 C34 C35 C36 177.6(3) . . . . ?
C24 C34 C39 C38 -177.5(3) . . . . ?
C25 C24 C34 C35 -119.0(3) . . . . ?
C25 C24 C34 C39 58.9(4) . . . . ?
C25 C26 C27 C28 178.2(3) . . . . ?
C26 C27 C28 C29 176.3(3) . . . . ?
C26 C27 C28 C33 -6.1(5) . . . . ?
C27 C28 C29 C30 176.6(3) . . . . ?
C27 C28 C33 C32 -176.3(3) . . . . ?
C28 C29 C30 C31 1.0(6) . . . . ?
C29 C28 C33 C32 1.4(5) . . . . ?
C29 C30 C31 N2 -178.7(3) . . . . ?
C29 C30 C31 C32 -1.0(6) . . . . ?
C30 C31 C32 C33 1.2(6) . . . . ?
C31 C32 C33 C28 -1.4(6) . . . . ?
C33 C28 C29 C30 -1.2(6) . . . . ?
C34 C24 C25 C26 2.0(5) . . . . ?
C34 C35 C36 C37 -0.8(5) . . . . ?
C35 C34 C39 C38 0.4(5) . . . . ?
C35 C36 C37 C38 1.8(6) . . . . ?
C36 C37 C38 C39 -1.7(6) . . . . ?
C37 C38 C39 C34 0.6(6) . . . . ?
C39 C34 C35 C36 -0.3(5) . . . . ?
C40 C41 C42 C43 -0.7(5) . . . . ?
C41 C40 C45 C44 0.3(6) . . . . ?
C41 C42 C43 C44 0.8(6) . . . . ?
C41 C42 C43 C46 -177.6(3) . . . . ?
C42 C43 C44 C45 -0.4(6) . . . . ?
C43 C44 C45 C40 -0.2(7) . . . . ?
C45 C40 C41 C42 0.1(5) . . . . ?
C46 C43 C44 C45 178.0(4) . . . . ?

_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_200731d
_database_code_depnum_ccdc_archive 'CCDC 2034321'
loop_
_audit_author_name
_audit_author_address
'Tao Xu'
;Ocean University of China
China
;
_audit_update_record             
;
2020-09-27 deposited with the CCDC.	2020-12-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        wd-5d
_chemical_name_common            wd-5d
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H12 Cl N O2'
_chemical_formula_weight         285.72

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'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Fdd2

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'-x+1/4, y+1/4, z+1/4'
'x+1/4, -y+1/4, z+1/4'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'-x+1/4, y+3/4, z+3/4'
'x+1/4, -y+3/4, z+3/4'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'-x+3/4, y+1/4, z+3/4'
'x+3/4, -y+1/4, z+3/4'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'-x+3/4, y+3/4, z+1/4'
'x+3/4, -y+3/4, z+1/4'

_cell_length_a                   24.528(2)
_cell_length_b                   32.202(3)
_cell_length_c                   7.0287(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     5551.6(9)
_cell_formula_units_Z            16
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1493
_cell_measurement_theta_min      3.027
_cell_measurement_theta_max      21.095

_exptl_crystal_description       sheet
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ??
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2368
_exptl_absorpt_coefficient_mu    0.275
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9344
_exptl_absorpt_correction_T_max  0.9704
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6890
_diffrn_reflns_av_R_equivalents  0.0565
_diffrn_reflns_av_sigmaI/netI    0.1017
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       -36
_diffrn_reflns_limit_k_max       38
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         2.53
_diffrn_reflns_theta_max         25.02
_reflns_number_total             2437
_reflns_number_gt                1408
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0771P)²+8.6000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.6(2)
_refine_ls_number_reflns         2437
_refine_ls_number_parameters     181
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1253
_refine_ls_R_factor_gt           0.0644
_refine_ls_wR_factor_ref         0.1973
_refine_ls_wR_factor_gt          0.1674
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.83472(5) 0.28197(5) 0.1862(6) 0.1150(10) Uani 1 1 d . . .
N1 N 0.79299(19) 0.12882(14) 0.1995(9) 0.0624(12) Uani 1 1 d . . .
O1 O 0.80788(16) 0.09305(12) 0.1824(9) 0.0834(13) Uani 1 1 d . . .
O2 O 0.74540(16) 0.13875(13) 0.2061(10) 0.0826(13) Uani 1 1 d . . .
C1 C 0.85679(18) 0.23108(14) 0.1989(11) 0.0560(14) Uani 1 1 d . . .
C2 C 0.81865(18) 0.20095(15) 0.1994(11) 0.0552(14) Uani 1 1 d . . .
H2 H 0.7818 0.2078 0.1961 0.066 Uiso 1 1 calc R . .
C3 C 0.83437(19) 0.16067(14) 0.2048(9) 0.0490(12) Uani 1 1 d . . .
C4 C 0.8876(2) 0.15041(15) 0.2180(9) 0.0522(14) Uani 1 1 d . . .
H4 H 0.8980 0.1227 0.2284 0.063 Uiso 1 1 calc R . .
C5 C 0.92535(17) 0.18074(14) 0.2158(9) 0.0470(12) Uani 1 1 d . . .
H5 H 0.9619 0.1732 0.2191 0.056 Uiso 1 1 calc R . .
C6 C 0.91234(16) 0.22277(15) 0.2088(10) 0.0426(12) Uani 1 1 d . . .
C7 C 0.95287(17) 0.25454(15) 0.1985(10) 0.0498(12) Uani 1 1 d . . .
H7 H 0.9405 0.2815 0.1795 0.060 Uiso 1 1 calc R . .
C8 C 1.00586(19) 0.24962(17) 0.2132(11) 0.0496(12) Uani 1 1 d . . .
H8 H 1.0188 0.2228 0.2326 0.060 Uiso 1 1 calc R . .
C9 C 1.04497(17) 0.28212(16) 0.2017(10) 0.0502(12) Uani 1 1 d . . .
H9 H 1.0323 0.3090 0.1824 0.060 Uiso 1 1 calc R . .
C10 C 1.0984(2) 0.27647(18) 0.2167(11) 0.0578(15) Uani 1 1 d . . .
H10 H 1.1102 0.2494 0.2367 0.069 Uiso 1 1 calc R . .
C11 C 1.14089(19) 0.30844(17) 0.2050(10) 0.0575(14) Uani 1 1 d . . .
C12 C 1.1943(2) 0.2958(2) 0.2065(15) 0.087(2) Uani 1 1 d . . .
H12 H 1.2030 0.2677 0.2124 0.104 Uiso 1 1 calc R . .
C13 C 1.2350(3) 0.3256(4) 0.1991(17) 0.115(3) Uani 1 1 d . . .
H13 H 1.2713 0.3171 0.1985 0.138 Uiso 1 1 calc R . .
C14 C 1.2240(3) 0.3650(3) 0.1929(16) 0.103(3) Uani 1 1 d . . .
H14 H 1.2522 0.3842 0.1885 0.124 Uiso 1 1 calc R . .
C15 C 1.1711(3) 0.3785(2) 0.1929(12) 0.091(2) Uani 1 1 d . . .
H15 H 1.1633 0.4068 0.1864 0.109 Uiso 1 1 calc R . .
C16 C 1.1293(3) 0.3498(2) 0.2024(11) 0.0706(17) Uani 1 1 d . . .
H16 H 1.0933 0.3587 0.2071 0.085 Uiso 1 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 C1 1.728(5) . ?
N1 O2 1.211(5) . ?
N1 O1 1.214(6) . ?
N1 C3 1.444(6) . ?
C1 C2 1.348(6) . ?
C1 C6 1.390(6) . ?
C2 C3 1.354(7) . ?
C2 H2 0.9300 . ?
C3 C4 1.349(7) . ?
C4 C5 1.346(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.391(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.428(6) . ?
C7 C8 1.313(7) . ?
C7 H7 0.9300 . ?
C8 C9 1.422(7) . ?
C8 H8 0.9300 . ?
C9 C10 1.328(6) . ?
C9 H9 0.9300 . ?
C10 C11 1.467(7) . ?
C10 H10 0.9300 . ?
C11 C16 1.361(8) . ?
C11 C12 1.372(7) . ?
C12 C13 1.386(10) . ?
C12 H12 0.9300 . ?
C13 C14 1.299(13) . ?
C13 H13 0.9300 . ?
C14 C15 1.368(11) . ?
C14 H14 0.9300 . ?
C15 C16 1.383(8) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?

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
O2 N1 O1 123.0(4) . . ?
O2 N1 C3 119.3(4) . . ?
O1 N1 C3 117.7(4) . . ?
C2 C1 C6 122.8(4) . . ?
C2 C1 Cl1 117.7(4) . . ?
C6 C1 Cl1 119.5(3) . . ?
C1 C2 C3 119.5(5) . . ?
C1 C2 H2 120.3 . . ?
C3 C2 H2 120.3 . . ?
C4 C3 C2 120.8(4) . . ?
C4 C3 N1 120.5(4) . . ?
C2 C3 N1 118.7(5) . . ?
C5 C4 C3 119.1(5) . . ?
C5 C4 H4 120.4 . . ?
C3 C4 H4 120.4 . . ?
C4 C5 C6 123.3(4) . . ?
C4 C5 H5 118.4 . . ?
C6 C5 H5 118.4 . . ?
C1 C6 C5 114.4(4) . . ?
C1 C6 C7 122.8(4) . . ?
C5 C6 C7 122.6(4) . . ?
C8 C7 C6 126.8(5) . . ?
C8 C7 H7 116.6 . . ?
C6 C7 H7 116.6 . . ?
C7 C8 C9 125.1(5) . . ?
C7 C8 H8 117.5 . . ?
C9 C8 H8 117.5 . . ?
C10 C9 C8 124.1(5) . . ?
C10 C9 H9 118.0 . . ?
C8 C9 H9 118.0 . . ?
C9 C10 C11 126.9(5) . . ?
C9 C10 H10 116.5 . . ?
C11 C10 H10 116.5 . . ?
C16 C11 C12 119.4(5) . . ?
C16 C11 C10 122.6(5) . . ?
C12 C11 C10 118.0(6) . . ?
C11 C12 C13 118.8(7) . . ?
C11 C12 H12 120.6 . . ?
C13 C12 H12 120.6 . . ?
C14 C13 C12 121.9(8) . . ?
C14 C13 H13 119.1 . . ?
C12 C13 H13 119.1 . . ?
C13 C14 C15 120.6(7) . . ?
C13 C14 H14 119.7 . . ?
C15 C14 H14 119.7 . . ?
C14 C15 C16 119.3(8) . . ?
C14 C15 H15 120.4 . . ?
C16 C15 H15 120.4 . . ?
C11 C16 C15 120.1(7) . . ?
C11 C16 H16 120.0 . . ?
C15 C16 H16 120.0 . . ?

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
C6 C1 C2 C3 -1.7(13) . . . . ?
Cl1 C1 C2 C3 178.5(6) . . . . ?
C1 C2 C3 C4 2.9(12) . . . . ?
C1 C2 C3 N1 -178.2(7) . . . . ?
O2 N1 C3 C4 173.0(7) . . . . ?
O1 N1 C3 C4 -9.4(11) . . . . ?
O2 N1 C3 C2 -5.9(11) . . . . ?
O1 N1 C3 C2 171.7(7) . . . . ?
C2 C3 C4 C5 -3.4(12) . . . . ?
N1 C3 C4 C5 177.7(6) . . . . ?
C3 C4 C5 C6 2.9(11) . . . . ?
C2 C1 C6 C5 1.1(12) . . . . ?
Cl1 C1 C6 C5 -179.1(5) . . . . ?
C2 C1 C6 C7 176.7(7) . . . . ?
Cl1 C1 C6 C7 -3.5(11) . . . . ?
C4 C5 C6 C1 -1.7(11) . . . . ?
C4 C5 C6 C7 -177.3(7) . . . . ?
C1 C6 C7 C8 177.5(8) . . . . ?
C5 C6 C7 C8 -7.3(13) . . . . ?
C6 C7 C8 C9 179.8(7) . . . . ?
C7 C8 C9 C10 -179.9(8) . . . . ?
C8 C9 C10 C11 179.6(7) . . . . ?
C9 C10 C11 C16 9.3(13) . . . . ?
C9 C10 C11 C12 -174.1(8) . . . . ?
C16 C11 C12 C13 -2.1(15) . . . . ?
C10 C11 C12 C13 -178.8(8) . . . . ?
C11 C12 C13 C14 0.8(19) . . . . ?
C12 C13 C14 C15 0(2) . . . . ?
C13 C14 C15 C16 1.0(17) . . . . ?
C12 C11 C16 C15 2.8(13) . . . . ?
C10 C11 C16 C15 179.5(7) . . . . ?
C14 C15 C16 C11 -2.3(14) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.231
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.051
