# 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_M2579a
_database_code_depnum_ccdc_archive 'CCDC 1970736'
loop_
_audit_author_name
_audit_author_address
xiaxf
;Jiangnan University
China
;
_audit_update_record             
;
2019-12-09 deposited with the CCDC.	2020-11-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H12 N2 O2'
_chemical_formula_weight         252.27

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'

_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'

_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+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-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                   12.7787(5)
_cell_length_b                   13.1791(6)
_cell_length_c                   14.9158(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2512.00(19)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3475
_cell_measurement_theta_min      2.61
_cell_measurement_theta_max      28.02

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_F_000             1056
_exptl_transmission_factor_min   0.983
_exptl_transmission_factor_max   0.989
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_exptl_absorpt_coefficient_mu    0.091
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12410
_diffrn_reflns_av_unetI/netI     0.0337
_diffrn_reflns_av_R_equivalents  0.0542
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.606
_diffrn_reflns_theta_max         25.092
_diffrn_reflns_theta_full        25.092
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2235
_reflns_number_gt                1734
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.1400P)²+0.0362P] 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         2235
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0719
_refine_ls_R_factor_gt           0.0531
_refine_ls_wR_factor_ref         0.2053
_refine_ls_wR_factor_gt          0.1775
_refine_ls_goodness_of_fit_ref   1.120
_refine_ls_restrained_S_all      1.120
_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_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 0.18158(18) 0.25441(19) 0.66497(17) 0.0250(6) Uani 1 1 d . . . . .
C2 C 0.21721(18) 0.15781(18) 0.66683(17) 0.0218(6) Uani 1 1 d . . . . .
C3 C 0.39953(19) 0.08890(19) 0.61081(18) 0.0271(6) Uani 1 1 d . . . . .
H3A H 0.3895 0.0194 0.6254 0.032 Uiso 1 1 calc R U . . .
C4 C 0.49149(19) 0.1216(2) 0.57169(18) 0.0310(7) Uani 1 1 d . . . . .
H4A H 0.5454 0.0739 0.5595 0.037 Uiso 1 1 calc R U . . .
C5 C 0.50649(19) 0.2234(2) 0.54976(18) 0.0327(7) Uani 1 1 d . . . . .
H5A H 0.5706 0.2435 0.5229 0.039 Uiso 1 1 calc R U . . .
C6 C 0.4308(2) 0.2956(2) 0.56605(17) 0.0304(7) Uani 1 1 d . . . . .
H6A H 0.4406 0.3650 0.5511 0.036 Uiso 1 1 calc R U . . .
C7 C 0.33978(19) 0.2610(2) 0.60540(16) 0.0246(6) Uani 1 1 d . . . . .
C8 C 0.32184(17) 0.16047(18) 0.62838(17) 0.0225(6) Uani 1 1 d . . . . .
C9 C 0.0826(2) 0.3007(2) 0.69656(19) 0.0321(7) Uani 1 1 d . . . . .
H9A H 0.0835 0.3737 0.6841 0.048 Uiso 1 1 calc R U . . .
H9B H 0.0234 0.2693 0.6652 0.048 Uiso 1 1 calc R U . . .
H9C H 0.0753 0.2896 0.7612 0.048 Uiso 1 1 calc R U . . .
C10 C 0.29355(18) 0.05527(19) 0.82652(17) 0.0247(6) Uani 1 1 d . . . . .
H10A H 0.3222 0.1173 0.8052 0.030 Uiso 1 1 calc R U . . .
C11 C 0.20829(16) 0.01532(18) 0.78142(16) 0.0211(6) Uani 1 1 d . . . . .
C12 C 0.16867(18) -0.07743(19) 0.81246(18) 0.0262(6) Uani 1 1 d . . . . .
H12A H 0.1121 -0.1094 0.7823 0.031 Uiso 1 1 calc R U . . .
C13 C 0.21264(19) -0.1216(2) 0.88705(19) 0.0301(6) Uani 1 1 d . . . . .
H13A H 0.1855 -0.1835 0.9099 0.036 Uiso 1 1 calc R U . . .
C14 C 0.29725(18) -0.0747(2) 0.92859(18) 0.0276(7) Uani 1 1 d . . . . .
H14A H 0.3268 -0.1054 0.9803 0.033 Uiso 1 1 calc R U . . .
C15 C 0.16196(17) 0.06956(18) 0.70443(16) 0.0216(6) Uani 1 1 d . . . . .
N1 N 0.33843(15) 0.01196(18) 0.89847(14) 0.0269(6) Uani 1 1 d . . . . .
N2 N 0.07273(15) 0.03597(15) 0.67697(13) 0.0242(5) Uani 1 1 d . . . . .
O1 O 0.25366(13) 0.32014(12) 0.62711(12) 0.0280(5) Uani 1 1 d . . . . .
O2 O 0.03475(13) 0.08965(14) 0.60330(12) 0.0284(5) Uani 1 1 d . . . . .
H2A H -0.0234 0.0656 0.5878 0.043 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.352(3) . ?
C1 O1 1.385(3) . ?
C1 C9 1.481(4) . ?
C2 C8 1.455(3) . ?
C2 C15 1.472(3) . ?
C3 C4 1.381(3) . ?
C3 C8 1.394(3) . ?
C3 H3A 0.9500 . ?
C4 C5 1.394(4) . ?
C4 H4A 0.9500 . ?
C5 C6 1.379(4) . ?
C5 H5A 0.9500 . ?
C6 C7 1.380(4) . ?
C6 H6A 0.9500 . ?
C7 C8 1.387(3) . ?
C7 O1 1.387(3) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 N1 1.344(3) . ?
C10 C11 1.384(3) . ?
C10 H10A 0.9500 . ?
C11 C12 1.402(3) . ?
C11 C15 1.476(3) . ?
C12 C13 1.376(4) . ?
C12 H12A 0.9500 . ?
C13 C14 1.391(4) . ?
C13 H13A 0.9500 . ?
C14 N1 1.335(3) . ?
C14 H14A 0.9500 . ?
C15 N2 1.290(3) . ?
N2 O2 1.394(3) . ?
O2 H2A 0.8400 . ?

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 O1 111.9(2) . . ?
C2 C1 C9 132.0(2) . . ?
O1 C1 C9 116.1(2) . . ?
C1 C2 C8 106.2(2) . . ?
C1 C2 C15 126.2(2) . . ?
C8 C2 C15 127.6(2) . . ?
C4 C3 C8 118.3(2) . . ?
C4 C3 H3A 120.8 . . ?
C8 C3 H3A 120.8 . . ?
C3 C4 C5 121.1(3) . . ?
C3 C4 H4A 119.5 . . ?
C5 C4 H4A 119.5 . . ?
C6 C5 C4 121.8(2) . . ?
C6 C5 H5A 119.1 . . ?
C4 C5 H5A 119.1 . . ?
C5 C6 C7 115.9(2) . . ?
C5 C6 H6A 122.0 . . ?
C7 C6 H6A 122.0 . . ?
C6 C7 C8 124.1(2) . . ?
C6 C7 O1 125.6(2) . . ?
C8 C7 O1 110.4(2) . . ?
C7 C8 C3 118.8(2) . . ?
C7 C8 C2 105.8(2) . . ?
C3 C8 C2 135.4(2) . . ?
C1 C9 H9A 109.5 . . ?
C1 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C1 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N1 C10 C11 124.2(2) . . ?
N1 C10 H10A 117.9 . . ?
C11 C10 H10A 117.9 . . ?
C10 C11 C12 117.1(2) . . ?
C10 C11 C15 120.6(2) . . ?
C12 C11 C15 122.3(2) . . ?
C13 C12 C11 119.3(2) . . ?
C13 C12 H12A 120.4 . . ?
C11 C12 H12A 120.4 . . ?
C12 C13 C14 119.3(2) . . ?
C12 C13 H13A 120.3 . . ?
C14 C13 H13A 120.3 . . ?
N1 C14 C13 122.5(2) . . ?
N1 C14 H14A 118.8 . . ?
C13 C14 H14A 118.8 . . ?
N2 C15 C2 125.0(2) . . ?
N2 C15 C11 115.8(2) . . ?
C2 C15 C11 119.1(2) . . ?
C14 N1 C10 117.6(2) . . ?
C15 N2 O2 112.57(19) . . ?
C1 O1 C7 105.74(19) . . ?
N2 O2 H2A 109.5 . . ?

_refine_diff_density_max         0.553
_refine_diff_density_min         -0.503
_refine_diff_density_rms         0.060



####################################################################### 
# 
# 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_jiaorq_1128
_database_code_depnum_ccdc_archive 'CCDC 1970737'
loop_
_audit_author_name
_audit_author_address
xiaxfjiaorq
;Jiangnan University
China
;
_audit_update_record             
;
2019-12-09 deposited with the CCDC.	2020-11-30 downloaded from the CCDC.
;
_audit_creation_date             2019-12-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '3(C17 H15 N O2)'
_chemical_formula_sum            'C51 H45 N3 O6'
_chemical_formula_weight         795.90
_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'

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

_cell_length_a                   11.9534(6)
_cell_length_b                   14.3176(7)
_cell_length_c                   14.6657(11)
_cell_angle_alpha                61.766(6)
_cell_angle_beta                 75.556(5)
_cell_angle_gamma                87.984(4)
_cell_volume                     2131.3(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3465
_cell_measurement_temperature    293.32(10)
_cell_measurement_theta_max      69.7310
_cell_measurement_theta_min      10.1930
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.653
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.24048
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.240
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0343
_diffrn_reflns_av_unetI/netI     0.0494
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            13457
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        66.597
_diffrn_reflns_theta_max         66.597
_diffrn_reflns_theta_min         4.813
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      293.32(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     77.00 103.00   1.00    6.00    --  108.00-111.00  30.00   26
  2  ω    108.00 134.00   1.00    6.00    --  108.00 -38.00 -60.00   26
  3  ω     85.00 140.00   1.00    6.00    --  108.00 -25.00-150.00   55
  4  ω     92.00 169.00   1.00    6.00    --  108.00  38.00 -60.00   77
  5  ω    130.00 158.00   1.00    6.00    --  108.00  38.00  30.00   28
  6  ω    106.00 131.00   1.00    6.00    --  108.00 111.00 -90.00   25
  7  ω     99.00 176.00   1.00    6.00    --  108.00  63.00-120.00   77
  8  ω     96.00 178.00   1.00    6.00    --  108.00  50.00-180.00   82
  9  ω     71.00 124.00   1.00    4.00    --   54.00  77.00 -30.00   53
 10  ω     70.00 114.00   1.00    4.00    --   54.00  57.00 120.00   44
 11  ω     37.00  67.00   1.00    2.00    --    0.00  57.00 120.00   30
 12  ω     26.00  86.00   1.00    4.00    --   54.00  77.00  30.00   60
 13  ω     39.00 123.00   1.00    4.00    --   54.00  57.00-120.00   84
 14  ω     46.00  87.00   1.00    6.00    --  108.00 -38.00 -60.00   41
 15  ω     60.00 138.00   1.00    6.00    --  108.00 -77.00 -90.00   78
 16  ω     59.00 115.00   1.00    6.00    --  108.00-111.00 -90.00   56
 17  ω     40.00 127.00   1.00    6.00    --  108.00 -50.00-180.00   87
 18  ω     40.00  65.00   1.00    6.00    --  108.00-111.00   0.00   25
 19  ω     43.00 134.00   1.00    6.00    --  108.00 -91.00  90.00   91
 20  ω     37.00 115.00   1.00    6.00    --  108.00-111.00  90.00   78
 21  ω     38.00 126.00   1.00    6.00    --  108.00 -50.00  90.00   88
 22  ω     10.00  53.00   1.00    4.00    --   54.00 -62.00  58.00   43
 23  ω      0.00  69.00   1.00    4.00    --   54.00 -57.00 -90.00   69
 24  ω     17.00  43.00   1.00    4.00    --   54.00 -57.00-150.00   26
 25  ω     24.00  74.00   1.00    4.00    --   54.00-125.00-150.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0151362000
_diffrn_orient_matrix_UB_12      -0.0520444000
_diffrn_orient_matrix_UB_13      -0.0727649000
_diffrn_orient_matrix_UB_21      0.1156552000
_diffrn_orient_matrix_UB_22      0.0695727000
_diffrn_orient_matrix_UB_23      -0.0690968000
_diffrn_orient_matrix_UB_31      0.0653871000
_diffrn_orient_matrix_UB_32      -0.0866516000
_diffrn_orient_matrix_UB_33      0.0722169000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5273
_reflns_number_total             7412
_reflns_odcompleteness_completeness 98.28
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.231
_refine_diff_density_min         -0.170
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     550
_refine_ls_number_reflns         7412
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0763
_refine_ls_R_factor_gt           0.0516
_refine_ls_restrained_S_all      1.015
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0708P)²+0.2442P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1319
_refine_ls_wR_factor_ref         0.1516
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C21(H21), C27(H27), C28(H28), C30(H30), C31(H31), C34(H34), C35(H35),
 C36(H36), C38(H38), C39(H39), C42(H42), C43(H43), C46(H46), C48(H48), C49(H49),
  C50(H50), C51(H51), C52(H52), C53(H53), C54(H54), C55(H55), C56(H56),
 C57(H57), C58(H58)
2.b Idealised Me refined as rotating group:
 C37(H37A,H37B,H37C), C40(H40A,H40B,H40C), C44(H44A,H44B,H44C), C47(H47A,H47B,
 H47C), C59(H59A,H59B,H59C), C60(H60A,H60B,H60C)
2.c Idealised tetrahedral OH refined as rotating group:
 O1(H1), O5(H5), O8(H8)
;
_atom_sites_solution_hydrogens   geom
_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
O1 O 0.49112(12) 0.89259(12) 0.24084(14) 0.0501(4) Uani 1 1 d . . . . .
H1 H 0.491966 0.952262 0.235431 0.075 Uiso 1 1 calc GR . . . .
O2 O 0.29539(13) 1.30124(13) 0.22413(13) 0.0538(4) Uani 1 1 d . . . . .
N3 N 0.60209(14) 0.87759(13) 0.19178(14) 0.0432(4) Uani 1 1 d . . . . .
N4 N 0.57994(14) 1.10179(14) 0.16450(15) 0.0458(4) Uani 1 1 d . . . . .
O5 O 0.69594(12) 1.08371(13) 0.13123(16) 0.0581(4) Uani 1 1 d . . . . .
H5 H 0.697582 1.025721 0.132696 0.087 Uiso 1 1 calc GR . . . .
O6 O 0.85979(14) 0.69318(13) 0.07182(13) 0.0580(4) Uani 1 1 d . . . . .
O7 O -0.23198(15) 0.70534(13) 0.42300(13) 0.0566(4) Uani 1 1 d . . . . .
O8 O 0.07504(14) 0.90087(12) 0.55351(15) 0.0581(4) Uani 1 1 d . . . . .
H8 H 0.078919 0.961206 0.546170 0.087 Uiso 1 1 calc GR . . . .
N9 N -0.01399(15) 0.88892(14) 0.51171(15) 0.0483(4) Uani 1 1 d . . . . .
C10 C 0.71999(17) 0.76146(16) 0.15050(16) 0.0403(4) Uani 1 1 d . . . . .
C11 C 0.34655(17) 1.17387(16) 0.17564(16) 0.0409(4) Uani 1 1 d . . . . .
C12 C 0.60542(16) 0.78624(15) 0.19464(16) 0.0379(4) Uani 1 1 d . . . . .
C13 C 0.45008(17) 1.22309(16) 0.17661(16) 0.0401(4) Uani 1 1 d . . . . .
C14 C 0.56952(17) 1.19618(16) 0.15180(16) 0.0397(4) Uani 1 1 d . . . . .
C15 C 0.74232(19) 0.69408(17) 0.10857(18) 0.0477(5) Uani 1 1 d . . . . .
C16 C 0.41439(19) 1.29856(17) 0.20588(18) 0.0468(5) Uani 1 1 d . . . . .
C17 C -0.12040(18) 0.77528(16) 0.48412(17) 0.0429(5) Uani 1 1 d . . . . .
C18 C -0.23327(18) 0.81577(16) 0.49438(16) 0.0428(5) Uani 1 1 d . . . . .
C19 C 0.50275(18) 0.70596(16) 0.24355(17) 0.0430(5) Uani 1 1 d . . . . .
C20 C -0.02298(17) 0.79700(16) 0.51849(16) 0.0414(4) Uani 1 1 d . . . . .
C21 C 0.32266(19) 1.09748(19) 0.1486(2) 0.0531(5) Uani 1 1 d . . . . .
H21 H 0.381558 1.061672 0.128004 0.064 Uiso 1 1 calc R . . . .
C22 C 0.25523(18) 1.22517(18) 0.20513(17) 0.0478(5) Uani 1 1 d . . . . .
C23 C 0.05131(18) 0.71024(17) 0.56590(18) 0.0453(5) Uani 1 1 d . . . . .
C24 C 0.66908(17) 1.27905(17) 0.10594(18) 0.0460(5) Uani 1 1 d . . . . .
C25 C 0.83153(17) 0.80728(16) 0.13998(17) 0.0436(5) Uani 1 1 d . . . . .
C26 C -0.2975(2) 0.77025(18) 0.45628(18) 0.0494(5) Uani 1 1 d . . . . .
C27 C 0.5083(2) 0.60774(18) 0.33302(19) 0.0580(6) Uani 1 1 d . . . . .
H27 H 0.574098 0.595487 0.358559 0.070 Uiso 1 1 calc R . . . .
C28 C 0.6760(2) 1.36647(19) 0.0042(2) 0.0603(6) Uani 1 1 d . . . . .
H28 H 0.619859 1.369993 -0.030988 0.072 Uiso 1 1 calc R . . . .
C29 C 0.91376(19) 0.76271(19) 0.09042(19) 0.0532(5) Uani 1 1 d . . . . .
C30 C -0.28710(19) 0.88169(18) 0.53448(18) 0.0500(5) Uani 1 1 d . . . . .
H30 H -0.246690 0.914451 0.559969 0.060 Uiso 1 1 calc R . . . .
C31 C -0.0021(2) 0.61916(19) 0.66044(19) 0.0596(6) Uani 1 1 d . . . . .
H31 H -0.081323 0.614345 0.690768 0.072 Uiso 1 1 calc R . . . .
C32 C 0.40630(19) 0.7238(2) 0.20357(19) 0.0524(5) Uani 1 1 d . . . . .
C33 C -0.1243(2) 0.71027(18) 0.44117(19) 0.0515(5) Uani 1 1 d . . . . .
C34 C 0.8700(2) 0.87712(19) 0.1693(2) 0.0585(6) Uani 1 1 d . . . . .
H34 H 0.817934 0.907014 0.204353 0.070 Uiso 1 1 calc R . . . .
C35 C -0.4625(2) 0.8505(2) 0.4949(2) 0.0683(7) Uani 1 1 d . . . . .
H35 H -0.539172 0.863954 0.494918 0.082 Uiso 1 1 calc R . . . .
C36 C -0.4117(2) 0.7855(2) 0.4552(2) 0.0625(6) Uani 1 1 d . . . . .
H36 H -0.451906 0.753468 0.428967 0.075 Uiso 1 1 calc R . . . .
C37 C 0.4721(2) 1.3739(2) 0.2261(3) 0.0704(7) Uani 1 1 d . . . . .
H37A H 0.466194 1.445596 0.174080 0.106 Uiso 1 1 calc GR . . . .
H37B H 0.552447 1.361730 0.220472 0.106 Uiso 1 1 calc GR . . . .
H37C H 0.435192 1.363293 0.296832 0.106 Uiso 1 1 calc GR . . . .
C38 C -0.4019(2) 0.8971(2) 0.5354(2) 0.0630(7) Uani 1 1 d . . . . .
H38 H -0.439647 0.939339 0.563538 0.076 Uiso 1 1 calc R . . . .
C39 C 0.1409(2) 1.2034(2) 0.2122(2) 0.0622(7) Uani 1 1 d . . . . .
H39 H 0.081738 1.238447 0.233659 0.075 Uiso 1 1 calc R . . . .
C40 C 0.6697(2) 0.6244(2) 0.0927(2) 0.0653(7) Uani 1 1 d . . . . .
H40A H 0.697034 0.636007 0.020425 0.098 Uiso 1 1 calc GR . . . .
H40B H 0.590531 0.640790 0.105257 0.098 Uiso 1 1 calc GR . . . .
H40C H 0.674200 0.551297 0.141957 0.098 Uiso 1 1 calc GR . . . .
C41 C 0.7515(2) 1.2732(2) 0.1598(2) 0.0623(7) Uani 1 1 d . . . . .
C42 C 0.4163(3) 0.5302(2) 0.3824(2) 0.0782(9) Uani 1 1 d . . . . .
H42 H 0.419222 0.466086 0.442317 0.094 Uiso 1 1 calc R . . . .
C43 C 1.0320(2) 0.7859(2) 0.0646(2) 0.0717(8) Uani 1 1 d . . . . .
H43 H 1.084466 0.755347 0.030574 0.086 Uiso 1 1 calc R . . . .
C44 C -0.0406(3) 0.6471(2) 0.4075(2) 0.0720(7) Uani 1 1 d . . . . .
H44A H -0.072943 0.574296 0.443075 0.108 Uiso 1 1 calc GR . . . .
H44B H 0.029967 0.650685 0.426216 0.108 Uiso 1 1 calc GR . . . .
H44C H -0.024351 0.675240 0.331227 0.108 Uiso 1 1 calc GR . . . .
C45 C 0.1688(2) 0.7179(2) 0.5189(2) 0.0634(7) Uani 1 1 d . . . . .
C46 C 0.2089(2) 1.0759(2) 0.1531(3) 0.0710(8) Uani 1 1 d . . . . .
H46 H 0.191634 1.025947 0.133862 0.085 Uiso 1 1 calc R . . . .
C47 C 0.3981(2) 0.8244(3) 0.1077(2) 0.0734(8) Uani 1 1 d . . . . .
H47A H 0.366466 0.875485 0.129585 0.110 Uiso 1 1 calc GR . . . .
H47B H 0.348384 0.810728 0.072204 0.110 Uiso 1 1 calc GR . . . .
H47C H 0.473978 0.852136 0.059427 0.110 Uiso 1 1 calc GR . . . .
C48 C 0.9883(2) 0.9005(3) 0.1445(3) 0.0817(9) Uani 1 1 d . . . . .
H48 H 1.016035 0.946872 0.163494 0.098 Uiso 1 1 calc R . . . .
C49 C 0.1196(2) 1.1276(3) 0.1859(3) 0.0755(8) Uani 1 1 d . . . . .
H49 H 0.043807 1.109874 0.189868 0.091 Uiso 1 1 calc R . . . .
C50 C 0.3146(2) 0.6419(3) 0.2558(3) 0.0751(8) Uani 1 1 d . . . . .
H50 H 0.248666 0.651817 0.230650 0.090 Uiso 1 1 calc R . . . .
C51 C 1.0671(2) 0.8565(3) 0.0920(3) 0.0860(10) Uani 1 1 d . . . . .
H51 H 1.146026 0.875799 0.075131 0.103 Uiso 1 1 calc R . . . .
C52 C 0.0608(3) 0.5360(2) 0.7097(3) 0.0818(9) Uani 1 1 d . . . . .
H52 H 0.024675 0.475695 0.773311 0.098 Uiso 1 1 calc R . . . .
C53 C 0.3215(3) 0.5474(3) 0.3436(3) 0.0826(9) Uani 1 1 d . . . . .
H53 H 0.260000 0.494312 0.376901 0.099 Uiso 1 1 calc R . . . .
C54 C 0.8446(3) 1.4419(3) 0.0094(3) 0.0898(10) Uani 1 1 d . . . . .
H54 H 0.904247 1.496534 -0.022768 0.108 Uiso 1 1 calc R . . . .
C55 C 0.2305(3) 0.6305(3) 0.5716(3) 0.0900(10) Uani 1 1 d . . . . .
H55 H 0.309600 0.632860 0.542430 0.108 Uiso 1 1 calc R . . . .
C56 C 0.7646(3) 1.4467(2) -0.0438(3) 0.0818(9) Uani 1 1 d . . . . .
H56 H 0.769781 1.503484 -0.111746 0.098 Uiso 1 1 calc R . . . .
C57 C 0.8396(2) 1.3590(3) 0.1088(3) 0.0848(10) Uani 1 1 d . . . . .
H57 H 0.894880 1.358834 0.143599 0.102 Uiso 1 1 calc R . . . .
C58 C 0.1752(4) 0.5432(3) 0.6646(3) 0.0936(11) Uani 1 1 d . . . . .
H58 H 0.217604 0.487085 0.697902 0.112 Uiso 1 1 calc R . . . .
C59 C 0.2278(3) 0.8121(3) 0.4149(3) 0.1006(12) Uani 1 1 d . . . . .
H59A H 0.178901 0.832915 0.366882 0.151 Uiso 1 1 calc GR . . . .
H59B H 0.299992 0.794017 0.383708 0.151 Uiso 1 1 calc GR . . . .
H59C H 0.242410 0.870104 0.427359 0.151 Uiso 1 1 calc GR . . . .
C60 C 0.7459(3) 1.1838(3) 0.2674(3) 0.0951(11) Uani 1 1 d . . . . .
H60A H 0.666261 1.158711 0.306465 0.143 Uiso 1 1 calc GR . . . .
H60B H 0.782319 1.207500 0.305286 0.143 Uiso 1 1 calc GR . . . .
H60C H 0.785592 1.127081 0.260517 0.143 Uiso 1 1 calc GR . . . .


_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
O1 H1 0.8200 . ?
O1 N3 1.405(2) . ?
O2 C16 1.383(3) . ?
O2 C22 1.373(3) . ?
N3 C12 1.288(3) . ?
N4 O5 1.409(2) . ?
N4 C14 1.280(3) . ?
O5 H5 0.8200 . ?
O6 C15 1.375(3) . ?
O6 C29 1.368(3) . ?
O7 C26 1.379(3) . ?
O7 C33 1.389(3) . ?
O8 H8 0.8200 . ?
O8 N9 1.405(2) . ?
N9 C20 1.278(3) . ?
C10 C12 1.470(3) . ?
C10 C15 1.357(3) . ?
C10 C25 1.447(3) . ?
C11 C13 1.452(3) . ?
C11 C21 1.387(3) . ?
C11 C22 1.388(3) . ?
C12 C19 1.491(3) . ?
C13 C14 1.468(3) . ?
C13 C16 1.360(3) . ?
C14 C24 1.490(3) . ?
C15 C40 1.478(3) . ?
C16 C37 1.478(3) . ?
C17 C18 1.451(3) . ?
C17 C20 1.474(3) . ?
C17 C33 1.356(3) . ?
C18 C26 1.386(3) . ?
C18 C30 1.394(3) . ?
C19 C27 1.412(3) . ?
C19 C32 1.383(3) . ?
C20 C23 1.493(3) . ?
C21 H21 0.9300 . ?
C21 C46 1.384(3) . ?
C22 C39 1.380(3) . ?
C23 C31 1.392(3) . ?
C23 C45 1.384(3) . ?
C24 C28 1.407(3) . ?
C24 C41 1.386(3) . ?
C25 C29 1.393(3) . ?
C25 C34 1.391(3) . ?
C26 C36 1.377(3) . ?
C27 H27 0.9300 . ?
C27 C42 1.376(4) . ?
C28 H28 0.9300 . ?
C28 C56 1.373(4) . ?
C29 C43 1.377(3) . ?
C30 H30 0.9300 . ?
C30 C38 1.380(3) . ?
C31 H31 0.9300 . ?
C31 C52 1.378(4) . ?
C32 C47 1.485(4) . ?
C32 C50 1.409(3) . ?
C33 C44 1.475(3) . ?
C34 H34 0.9300 . ?
C34 C48 1.380(3) . ?
C35 H35 0.9300 . ?
C35 C36 1.368(4) . ?
C35 C38 1.394(4) . ?
C36 H36 0.9300 . ?
C37 H37A 0.9600 . ?
C37 H37B 0.9600 . ?
C37 H37C 0.9600 . ?
C38 H38 0.9300 . ?
C39 H39 0.9300 . ?
C39 C49 1.363(4) . ?
C40 H40A 0.9600 . ?
C40 H40B 0.9600 . ?
C40 H40C 0.9600 . ?
C41 C57 1.416(4) . ?
C41 C60 1.475(4) . ?
C42 H42 0.9300 . ?
C42 C53 1.357(5) . ?
C43 H43 0.9300 . ?
C43 C51 1.364(5) . ?
C44 H44A 0.9600 . ?
C44 H44B 0.9600 . ?
C44 H44C 0.9600 . ?
C45 C55 1.419(4) . ?
C45 C59 1.492(4) . ?
C46 H46 0.9300 . ?
C46 C49 1.393(4) . ?
C47 H47A 0.9600 . ?
C47 H47B 0.9600 . ?
C47 H47C 0.9600 . ?
C48 H48 0.9300 . ?
C48 C51 1.389(5) . ?
C49 H49 0.9300 . ?
C50 H50 0.9300 . ?
C50 C53 1.375(5) . ?
C51 H51 0.9300 . ?
C52 H52 0.9300 . ?
C52 C58 1.346(5) . ?
C53 H53 0.9300 . ?
C54 H54 0.9300 . ?
C54 C56 1.357(5) . ?
C54 C57 1.365(5) . ?
C55 H55 0.9300 . ?
C55 C58 1.362(5) . ?
C56 H56 0.9300 . ?
C57 H57 0.9300 . ?
C58 H58 0.9300 . ?
C59 H59A 0.9600 . ?
C59 H59B 0.9600 . ?
C59 H59C 0.9600 . ?
C60 H60A 0.9600 . ?
C60 H60B 0.9600 . ?
C60 H60C 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
N3 O1 H1 109.5 . . ?
C22 O2 C16 106.65(16) . . ?
C12 N3 O1 112.41(16) . . ?
C14 N4 O5 112.94(16) . . ?
N4 O5 H5 109.5 . . ?
C29 O6 C15 106.95(17) . . ?
C26 O7 C33 106.21(17) . . ?
N9 O8 H8 109.5 . . ?
C20 N9 O8 112.66(17) . . ?
C15 C10 C12 127.04(19) . . ?
C15 C10 C25 106.45(19) . . ?
C25 C10 C12 126.48(19) . . ?
C21 C11 C13 136.0(2) . . ?
C21 C11 C22 118.30(19) . . ?
C22 C11 C13 105.65(19) . . ?
N3 C12 C10 115.97(17) . . ?
N3 C12 C19 123.77(18) . . ?
C10 C12 C19 120.20(18) . . ?
C11 C13 C14 126.85(19) . . ?
C16 C13 C11 106.40(18) . . ?
C16 C13 C14 126.75(19) . . ?
N4 C14 C13 115.70(17) . . ?
N4 C14 C24 123.87(18) . . ?
C13 C14 C24 120.22(18) . . ?
O6 C15 C40 114.4(2) . . ?
C10 C15 O6 111.03(19) . . ?
C10 C15 C40 134.6(2) . . ?
O2 C16 C37 114.0(2) . . ?
C13 C16 O2 110.95(19) . . ?
C13 C16 C37 135.0(2) . . ?
C18 C17 C20 126.47(19) . . ?
C33 C17 C18 106.45(19) . . ?
C33 C17 C20 127.0(2) . . ?
C26 C18 C17 105.84(19) . . ?
C26 C18 C30 118.2(2) . . ?
C30 C18 C17 135.9(2) . . ?
C27 C19 C12 116.94(19) . . ?
C32 C19 C12 122.74(19) . . ?
C32 C19 C27 120.3(2) . . ?
N9 C20 C17 115.90(19) . . ?
N9 C20 C23 124.62(19) . . ?
C17 C20 C23 119.29(18) . . ?
C11 C21 H21 120.9 . . ?
C46 C21 C11 118.3(2) . . ?
C46 C21 H21 120.9 . . ?
O2 C22 C11 110.35(18) . . ?
O2 C22 C39 125.3(2) . . ?
C39 C22 C11 124.3(2) . . ?
C31 C23 C20 117.4(2) . . ?
C45 C23 C20 122.3(2) . . ?
C45 C23 C31 120.2(2) . . ?
C28 C24 C14 116.96(19) . . ?
C41 C24 C14 122.8(2) . . ?
C41 C24 C28 120.2(2) . . ?
C29 C25 C10 105.5(2) . . ?
C34 C25 C10 135.9(2) . . ?
C34 C25 C29 118.5(2) . . ?
O7 C26 C18 110.34(19) . . ?
O7 C26 C36 125.2(2) . . ?
C36 C26 C18 124.5(2) . . ?
C19 C27 H27 120.0 . . ?
C42 C27 C19 120.0(3) . . ?
C42 C27 H27 120.0 . . ?
C24 C28 H28 119.6 . . ?
C56 C28 C24 120.8(3) . . ?
C56 C28 H28 119.6 . . ?
O6 C29 C25 110.08(19) . . ?
O6 C29 C43 125.5(2) . . ?
C43 C29 C25 124.4(3) . . ?
C18 C30 H30 120.9 . . ?
C38 C30 C18 118.3(2) . . ?
C38 C30 H30 120.9 . . ?
C23 C31 H31 119.5 . . ?
C52 C31 C23 120.9(3) . . ?
C52 C31 H31 119.5 . . ?
C19 C32 C47 122.2(2) . . ?
C19 C32 C50 117.9(2) . . ?
C50 C32 C47 119.9(2) . . ?
O7 C33 C44 113.9(2) . . ?
C17 C33 O7 111.2(2) . . ?
C17 C33 C44 134.9(2) . . ?
C25 C34 H34 121.2 . . ?
C48 C34 C25 117.6(3) . . ?
C48 C34 H34 121.2 . . ?
C36 C35 H35 119.3 . . ?
C36 C35 C38 121.5(2) . . ?
C38 C35 H35 119.3 . . ?
C26 C36 H36 121.9 . . ?
C35 C36 C26 116.2(2) . . ?
C35 C36 H36 121.9 . . ?
C16 C37 H37A 109.5 . . ?
C16 C37 H37B 109.5 . . ?
C16 C37 H37C 109.5 . . ?
H37A C37 H37B 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
C30 C38 C35 121.3(2) . . ?
C30 C38 H38 119.3 . . ?
C35 C38 H38 119.3 . . ?
C22 C39 H39 121.9 . . ?
C49 C39 C22 116.2(2) . . ?
C49 C39 H39 121.9 . . ?
C15 C40 H40A 109.5 . . ?
C15 C40 H40B 109.5 . . ?
C15 C40 H40C 109.5 . . ?
H40A C40 H40B 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?
C24 C41 C57 117.2(3) . . ?
C24 C41 C60 121.8(2) . . ?
C57 C41 C60 121.0(3) . . ?
C27 C42 H42 120.1 . . ?
C53 C42 C27 119.9(3) . . ?
C53 C42 H42 120.1 . . ?
C29 C43 H43 122.1 . . ?
C51 C43 C29 115.7(3) . . ?
C51 C43 H43 122.1 . . ?
C33 C44 H44A 109.5 . . ?
C33 C44 H44B 109.5 . . ?
C33 C44 H44C 109.5 . . ?
H44A C44 H44B 109.5 . . ?
H44A C44 H44C 109.5 . . ?
H44B C44 H44C 109.5 . . ?
C23 C45 C55 117.2(3) . . ?
C23 C45 C59 121.7(3) . . ?
C55 C45 C59 121.1(3) . . ?
C21 C46 H46 119.3 . . ?
C21 C46 C49 121.4(3) . . ?
C49 C46 H46 119.3 . . ?
C32 C47 H47A 109.5 . . ?
C32 C47 H47B 109.5 . . ?
C32 C47 H47C 109.5 . . ?
H47A C47 H47B 109.5 . . ?
H47A C47 H47C 109.5 . . ?
H47B C47 H47C 109.5 . . ?
C34 C48 H48 119.1 . . ?
C34 C48 C51 121.8(3) . . ?
C51 C48 H48 119.1 . . ?
C39 C49 C46 121.5(2) . . ?
C39 C49 H49 119.2 . . ?
C46 C49 H49 119.2 . . ?
C32 C50 H50 119.6 . . ?
C53 C50 C32 120.7(3) . . ?
C53 C50 H50 119.6 . . ?
C43 C51 C48 121.9(2) . . ?
C43 C51 H51 119.1 . . ?
C48 C51 H51 119.1 . . ?
C31 C52 H52 120.4 . . ?
C58 C52 C31 119.1(3) . . ?
C58 C52 H52 120.4 . . ?
C42 C53 C50 121.2(3) . . ?
C42 C53 H53 119.4 . . ?
C50 C53 H53 119.4 . . ?
C56 C54 H54 119.2 . . ?
C56 C54 C57 121.6(3) . . ?
C57 C54 H54 119.2 . . ?
C45 C55 H55 119.6 . . ?
C58 C55 C45 120.7(3) . . ?
C58 C55 H55 119.6 . . ?
C28 C56 H56 120.4 . . ?
C54 C56 C28 119.1(3) . . ?
C54 C56 H56 120.4 . . ?
C41 C57 H57 119.5 . . ?
C54 C57 C41 121.1(3) . . ?
C54 C57 H57 119.5 . . ?
C52 C58 C55 121.8(3) . . ?
C52 C58 H58 119.1 . . ?
C55 C58 H58 119.1 . . ?
C45 C59 H59A 109.5 . . ?
C45 C59 H59B 109.5 . . ?
C45 C59 H59C 109.5 . . ?
H59A C59 H59B 109.5 . . ?
H59A C59 H59C 109.5 . . ?
H59B C59 H59C 109.5 . . ?
C41 C60 H60A 109.5 . . ?
C41 C60 H60B 109.5 . . ?
C41 C60 H60C 109.5 . . ?
H60A C60 H60B 109.5 . . ?
H60A C60 H60C 109.5 . . ?
H60B C60 H60C 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
O1 N3 C12 C10 -176.62(16) . . . . ?
O1 N3 C12 C19 0.6(3) . . . . ?
O2 C22 C39 C49 177.4(2) . . . . ?
N3 C12 C19 C27 -116.8(2) . . . . ?
N3 C12 C19 C32 64.5(3) . . . . ?
N4 C14 C24 C28 111.2(2) . . . . ?
N4 C14 C24 C41 -69.7(3) . . . . ?
O5 N4 C14 C13 175.17(17) . . . . ?
O5 N4 C14 C24 0.4(3) . . . . ?
O6 C29 C43 C51 -179.0(3) . . . . ?
O7 C26 C36 C35 177.9(2) . . . . ?
O8 N9 C20 C17 175.37(18) . . . . ?
O8 N9 C20 C23 0.4(3) . . . . ?
N9 C20 C23 C31 113.3(3) . . . . ?
N9 C20 C23 C45 -67.1(3) . . . . ?
C10 C12 C19 C27 60.3(3) . . . . ?
C10 C12 C19 C32 -118.4(2) . . . . ?
C10 C25 C29 O6 -0.7(2) . . . . ?
C10 C25 C29 C43 179.4(2) . . . . ?
C10 C25 C34 C48 179.2(3) . . . . ?
C11 C13 C14 N4 -24.0(3) . . . . ?
C11 C13 C14 C24 150.9(2) . . . . ?
C11 C13 C16 O2 0.2(2) . . . . ?
C11 C13 C16 C37 177.4(3) . . . . ?
C11 C21 C46 C49 -1.3(4) . . . . ?
C11 C22 C39 C49 -1.3(4) . . . . ?
C12 C10 C15 O6 178.05(18) . . . . ?
C12 C10 C15 C40 -0.8(4) . . . . ?
C12 C10 C25 C29 -177.68(19) . . . . ?
C12 C10 C25 C34 4.7(4) . . . . ?
C12 C19 C27 C42 179.7(2) . . . . ?
C12 C19 C32 C47 0.6(4) . . . . ?
C12 C19 C32 C50 179.5(2) . . . . ?
C13 C11 C21 C46 -176.2(2) . . . . ?
C13 C11 C22 O2 -0.2(2) . . . . ?
C13 C11 C22 C39 178.7(2) . . . . ?
C13 C14 C24 C28 -63.4(3) . . . . ?
C13 C14 C24 C41 115.8(2) . . . . ?
C14 C13 C16 O2 -179.35(18) . . . . ?
C14 C13 C16 C37 -2.1(4) . . . . ?
C14 C24 C28 C56 179.7(2) . . . . ?
C14 C24 C41 C57 -177.9(2) . . . . ?
C14 C24 C41 C60 -0.2(4) . . . . ?
C15 O6 C29 C25 0.7(2) . . . . ?
C15 O6 C29 C43 -179.5(2) . . . . ?
C15 C10 C12 N3 -154.3(2) . . . . ?
C15 C10 C12 C19 28.4(3) . . . . ?
C15 C10 C25 C29 0.4(2) . . . . ?
C15 C10 C25 C34 -177.2(3) . . . . ?
C16 O2 C22 C11 0.3(2) . . . . ?
C16 O2 C22 C39 -178.6(2) . . . . ?
C16 C13 C14 N4 155.4(2) . . . . ?
C16 C13 C14 C24 -29.6(3) . . . . ?
C17 C18 C26 O7 -0.3(2) . . . . ?
C17 C18 C26 C36 177.9(2) . . . . ?
C17 C18 C30 C38 -176.3(2) . . . . ?
C17 C20 C23 C31 -61.5(3) . . . . ?
C17 C20 C23 C45 118.1(2) . . . . ?
C18 C17 C20 N9 -32.8(3) . . . . ?
C18 C17 C20 C23 142.5(2) . . . . ?
C18 C17 C33 O7 -0.2(3) . . . . ?
C18 C17 C33 C44 177.9(3) . . . . ?
C18 C26 C36 C35 0.0(4) . . . . ?
C18 C30 C38 C35 -1.6(4) . . . . ?
C19 C27 C42 C53 1.4(4) . . . . ?
C19 C32 C50 C53 -0.1(4) . . . . ?
C20 C17 C18 C26 -177.1(2) . . . . ?
C20 C17 C18 C30 0.2(4) . . . . ?
C20 C17 C33 O7 177.24(19) . . . . ?
C20 C17 C33 C44 -4.7(4) . . . . ?
C20 C23 C31 C52 -179.3(2) . . . . ?
C20 C23 C45 C55 179.7(2) . . . . ?
C20 C23 C45 C59 -2.5(4) . . . . ?
C21 C11 C13 C14 -4.3(4) . . . . ?
C21 C11 C13 C16 176.2(2) . . . . ?
C21 C11 C22 O2 -177.16(19) . . . . ?
C21 C11 C22 C39 1.8(3) . . . . ?
C21 C46 C49 C39 1.7(5) . . . . ?
C22 O2 C16 C13 -0.3(2) . . . . ?
C22 O2 C16 C37 -178.2(2) . . . . ?
C22 C11 C13 C14 179.5(2) . . . . ?
C22 C11 C13 C16 0.0(2) . . . . ?
C22 C11 C21 C46 -0.4(3) . . . . ?
C22 C39 C49 C46 -0.4(4) . . . . ?
C23 C31 C52 C58 -0.7(5) . . . . ?
C23 C45 C55 C58 0.0(5) . . . . ?
C24 C28 C56 C54 -1.5(5) . . . . ?
C24 C41 C57 C54 -2.0(5) . . . . ?
C25 C10 C12 N3 23.5(3) . . . . ?
C25 C10 C12 C19 -153.84(19) . . . . ?
C25 C10 C15 O6 0.0(2) . . . . ?
C25 C10 C15 C40 -178.9(3) . . . . ?
C25 C29 C43 C51 0.9(4) . . . . ?
C25 C34 C48 C51 0.1(5) . . . . ?
C26 O7 C33 C17 0.0(3) . . . . ?
C26 O7 C33 C44 -178.5(2) . . . . ?
C26 C18 C30 C38 0.8(3) . . . . ?
C27 C19 C32 C47 -178.1(2) . . . . ?
C27 C19 C32 C50 0.8(3) . . . . ?
C27 C42 C53 C50 -0.7(5) . . . . ?
C28 C24 C41 C57 1.1(4) . . . . ?
C28 C24 C41 C60 178.8(3) . . . . ?
C29 O6 C15 C10 -0.4(2) . . . . ?
C29 O6 C15 C40 178.7(2) . . . . ?
C29 C25 C34 C48 1.8(4) . . . . ?
C29 C43 C51 C48 1.2(5) . . . . ?
C30 C18 C26 O7 -178.17(19) . . . . ?
C30 C18 C26 C36 0.0(3) . . . . ?
C31 C23 C45 C55 -0.7(4) . . . . ?
C31 C23 C45 C59 177.1(3) . . . . ?
C31 C52 C58 C55 0.0(5) . . . . ?
C32 C19 C27 C42 -1.5(4) . . . . ?
C32 C50 C53 C42 0.0(5) . . . . ?
C33 O7 C26 C18 0.2(2) . . . . ?
C33 O7 C26 C36 -177.9(2) . . . . ?
C33 C17 C18 C26 0.3(2) . . . . ?
C33 C17 C18 C30 177.6(2) . . . . ?
C33 C17 C20 N9 150.3(2) . . . . ?
C33 C17 C20 C23 -34.4(3) . . . . ?
C34 C25 C29 O6 177.5(2) . . . . ?
C34 C25 C29 C43 -2.4(4) . . . . ?
C34 C48 C51 C43 -1.7(5) . . . . ?
C36 C35 C38 C30 1.7(4) . . . . ?
C38 C35 C36 C26 -0.9(4) . . . . ?
C41 C24 C28 C56 0.6(4) . . . . ?
C45 C23 C31 C52 1.0(4) . . . . ?
C45 C55 C58 C52 0.3(5) . . . . ?
C47 C32 C50 C53 178.9(3) . . . . ?
C56 C54 C57 C41 1.2(5) . . . . ?
C57 C54 C56 C28 0.6(5) . . . . ?
C59 C45 C55 C58 -177.8(3) . . . . ?
C60 C41 C57 C54 -179.8(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.062
_oxdiff_exptl_absorpt_empirical_full_min 0.577
####################################################################### 
# 
# 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_cu_hh2_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1974019'
loop_
_audit_author_name
_audit_author_address
xiaxfHH
;Jiangnan University
China
;
_audit_update_record             
;
2019-12-25 deposited with the CCDC.	2020-11-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H12 Cl0 F N O S'
_chemical_formula_weight         285.33

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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 '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           56
_space_group_name_H-M_alt        'P c c n'
_space_group_name_Hall           '-P 2ab 2ac'

_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+1/2, -y+1/2, z'
'x+1/2, -y, -z+1/2'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'-x-1/2, y, z-1/2'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.6155(3)
_cell_length_b                   28.9732(8)
_cell_length_c                   8.2494(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2776.24(12)
_cell_formula_units_Z            8
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    9978
_cell_measurement_theta_min      3.0505
_cell_measurement_theta_max      66.6015

_exptl_crystal_description       block
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.365
_exptl_crystal_F_000             1184
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    2.130
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6185
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  D8VENTURE
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            105558
_diffrn_reflns_av_unetI/netI     0.0169
_diffrn_reflns_av_R_equivalents  0.0835
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         3.050
_diffrn_reflns_theta_max         67.021
_diffrn_reflns_theta_full        67.021
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             2460
_reflns_number_gt                2103
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0559P)²+0.7313P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2460
_refine_ls_number_parameters     185
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0457
_refine_ls_R_factor_gt           0.0386
_refine_ls_wR_factor_ref         0.1057
_refine_ls_wR_factor_gt          0.1010
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_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_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
S1 S -0.23195(5) 0.18001(2) 0.02386(7) 0.06243(19) Uani 1 1 d . . . . .
H1 H -0.0518(18) 0.0174(8) -0.094(3) 0.075 Uiso 1 1 d . U . . .
F1 F 0.19091(17) 0.01113(5) 0.6227(2) 0.1228(6) Uani 1 1 d . . . . .
O1 O -0.05885(17) 0.04733(5) -0.05424(18) 0.0857(6) Uani 1 1 d . . . . .
N1 N -0.00498(16) 0.04470(5) 0.09648(19) 0.0624(5) Uani 1 1 d . . . . .
C00A C -0.07341(15) 0.12359(5) 0.1117(2) 0.0449(4) Uani 1 1 d . . . . .
C00B C 0.04099(14) 0.08400(6) 0.3386(2) 0.0464(4) Uani 1 1 d . . . . .
C00C C -0.01249(15) 0.08231(5) 0.1763(2) 0.0466(4) Uani 1 1 d . . . . .
C00G C -0.01426(16) 0.16076(5) 0.0311(2) 0.0468(4) Uani 1 1 d . . . . .
C00I C -0.18884(16) 0.12873(6) 0.1156(2) 0.0513(4) Uani 1 1 d . . . . .
C00K C -0.09173(17) 0.19419(6) -0.0268(2) 0.0530(4) Uani 1 1 d . . . . .
C00L C 0.10302(18) 0.16662(7) 0.0043(2) 0.0590(5) Uani 1 1 d . . . . .
H00L H 0.155576 0.145295 0.044526 0.071 Uiso 1 1 calc R U . . .
C00N C 0.09480(19) 0.04557(6) 0.4056(2) 0.0621(5) Uani 1 1 d . . . . .
H00N H 0.099249 0.018051 0.347853 0.075 Uiso 1 1 calc R U . . .
C00O C 0.03768(18) 0.12424(6) 0.4282(2) 0.0606(5) Uani 1 1 d . . . . .
H00O H 0.002586 0.150312 0.384843 0.073 Uiso 1 1 calc R U . . .
C00S C -0.0531(2) 0.23187(6) -0.1168(3) 0.0682(6) Uani 1 1 d . . . . .
H00S H -0.104720 0.253508 -0.157463 0.082 Uiso 1 1 calc R U . . .
C00T C -0.27683(18) 0.09627(7) 0.1807(3) 0.0707(6) Uani 1 1 d . . . . .
H00A H -0.240537 0.074662 0.252562 0.106 Uiso 1 1 calc R U . . .
H00B H -0.312243 0.079898 0.092620 0.106 Uiso 1 1 calc R U . . .
H00C H -0.334443 0.113325 0.238746 0.106 Uiso 1 1 calc R U . . .
C00W C 0.1411(2) 0.04889(8) 0.5579(3) 0.0717(6) Uani 1 1 d . . . . .
C00X C 0.1380(2) 0.08823(9) 0.6479(3) 0.0763(6) Uani 1 1 d . . . . .
H00X H 0.170268 0.089255 0.751034 0.092 Uiso 1 1 calc R U . . .
C00Y C 0.1404(2) 0.20420(7) -0.0823(3) 0.0755(6) Uani 1 1 d . . . . .
H00Y H 0.218839 0.208314 -0.100131 0.091 Uiso 1 1 calc R U . . .
C012 C 0.0859(2) 0.12636(8) 0.5817(3) 0.0758(6) Uani 1 1 d . . . . .
H012 H 0.082814 0.153763 0.640259 0.091 Uiso 1 1 calc R U . . .
C013 C 0.0625(2) 0.23623(7) -0.1438(3) 0.0777(6) Uani 1 1 d . . . . .
H013 H 0.089610 0.261039 -0.204332 0.093 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C00K 1.731(2) . ?
S1 C00I 1.7407(17) . ?
F1 C00W 1.348(2) . ?
O1 N1 1.394(2) . ?
O1 H1 0.93(2) . ?
N1 C00C 1.276(2) . ?
C00A C00I 1.349(3) . ?
C00A C00G 1.440(2) . ?
C00A C00C 1.488(2) . ?
C00B C00O 1.381(2) . ?
C00B C00N 1.391(2) . ?
C00B C00C 1.477(2) . ?
C00G C00L 1.391(3) . ?
C00G C00K 1.406(2) . ?
C00I C00T 1.489(3) . ?
C00K C00S 1.395(3) . ?
C00L C00Y 1.373(3) . ?
C00L H00L 0.9300 . ?
C00N C00W 1.370(3) . ?
C00N H00N 0.9300 . ?
C00O C012 1.386(3) . ?
C00O H00O 0.9300 . ?
C00S C013 1.367(3) . ?
C00S H00S 0.9300 . ?
C00T H00A 0.9600 . ?
C00T H00B 0.9600 . ?
C00T H00C 0.9600 . ?
C00W C00X 1.361(3) . ?
C00X C012 1.373(3) . ?
C00X H00X 0.9300 . ?
C00Y C013 1.392(3) . ?
C00Y H00Y 0.9300 . ?
C012 H012 0.9300 . ?
C013 H013 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
C00K S1 C00I 92.10(9) . . ?
N1 O1 H1 102.7(14) . . ?
C00C N1 O1 112.49(13) . . ?
C00I C00A C00G 113.73(15) . . ?
C00I C00A C00C 123.55(15) . . ?
C00G C00A C00C 122.64(15) . . ?
C00O C00B C00N 118.41(17) . . ?
C00O C00B C00C 120.10(15) . . ?
C00N C00B C00C 121.49(16) . . ?
N1 C00C C00B 117.85(15) . . ?
N1 C00C C00A 122.28(15) . . ?
C00B C00C C00A 119.87(14) . . ?
C00L C00G C00K 119.27(17) . . ?
C00L C00G C00A 129.22(16) . . ?
C00K C00G C00A 111.51(16) . . ?
C00A C00I C00T 128.37(16) . . ?
C00A C00I S1 111.70(13) . . ?
C00T C00I S1 119.89(14) . . ?
C00S C00K C00G 120.96(19) . . ?
C00S C00K S1 128.10(16) . . ?
C00G C00K S1 110.91(13) . . ?
C00Y C00L C00G 119.34(19) . . ?
C00Y C00L H00L 120.3 . . ?
C00G C00L H00L 120.3 . . ?
C00W C00N C00B 118.96(19) . . ?
C00W C00N H00N 120.5 . . ?
C00B C00N H00N 120.5 . . ?
C00B C00O C012 121.02(18) . . ?
C00B C00O H00O 119.5 . . ?
C012 C00O H00O 119.5 . . ?
C013 C00S C00K 118.36(19) . . ?
C013 C00S H00S 120.8 . . ?
C00K C00S H00S 120.8 . . ?
C00I C00T H00A 109.5 . . ?
C00I C00T H00B 109.5 . . ?
H00A C00T H00B 109.5 . . ?
C00I C00T H00C 109.5 . . ?
H00A C00T H00C 109.5 . . ?
H00B C00T H00C 109.5 . . ?
F1 C00W C00X 118.3(2) . . ?
F1 C00W C00N 118.4(2) . . ?
C00X C00W C00N 123.30(19) . . ?
C00W C00X C012 117.9(2) . . ?
C00W C00X H00X 121.0 . . ?
C012 C00X H00X 121.0 . . ?
C00L C00Y C013 120.8(2) . . ?
C00L C00Y H00Y 119.6 . . ?
C013 C00Y H00Y 119.6 . . ?
C00X C012 C00O 120.4(2) . . ?
C00X C012 H012 119.8 . . ?
C00O C012 H012 119.8 . . ?
C00S C013 C00Y 121.2(2) . . ?
C00S C013 H013 119.4 . . ?
C00Y C013 H013 119.4 . . ?

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
O1 N1 C00C C00B 179.84(16) . . . . ?
O1 N1 C00C C00A 0.3(3) . . . . ?
C00O C00B C00C N1 178.44(19) . . . . ?
C00N C00B C00C N1 -2.0(3) . . . . ?
C00O C00B C00C C00A -2.1(3) . . . . ?
C00N C00B C00C C00A 177.50(17) . . . . ?
C00I C00A C00C N1 80.1(2) . . . . ?
C00G C00A C00C N1 -96.5(2) . . . . ?
C00I C00A C00C C00B -99.3(2) . . . . ?
C00G C00A C00C C00B 84.0(2) . . . . ?
C00I C00A C00G C00L -179.60(18) . . . . ?
C00C C00A C00G C00L -2.7(3) . . . . ?
C00I C00A C00G C00K -0.4(2) . . . . ?
C00C C00A C00G C00K 176.48(15) . . . . ?
C00G C00A C00I C00T 176.60(18) . . . . ?
C00C C00A C00I C00T -0.3(3) . . . . ?
C00G C00A C00I S1 -1.07(19) . . . . ?
C00C C00A C00I S1 -177.95(13) . . . . ?
C00K S1 C00I C00A 1.76(14) . . . . ?
C00K S1 C00I C00T -176.14(16) . . . . ?
C00L C00G C00K C00S 3.0(3) . . . . ?
C00A C00G C00K C00S -176.30(16) . . . . ?
C00L C00G C00K S1 -179.01(14) . . . . ?
C00A C00G C00K S1 1.73(19) . . . . ?
C00I S1 C00K C00S 175.88(18) . . . . ?
C00I S1 C00K C00G -1.99(14) . . . . ?
C00K C00G C00L C00Y -1.9(3) . . . . ?
C00A C00G C00L C00Y 177.21(19) . . . . ?
C00O C00B C00N C00W 0.7(3) . . . . ?
C00C C00B C00N C00W -178.84(19) . . . . ?
C00N C00B C00O C012 -0.5(3) . . . . ?
C00C C00B C00O C012 179.05(19) . . . . ?
C00G C00K C00S C013 -1.7(3) . . . . ?
S1 C00K C00S C013 -179.41(17) . . . . ?
C00B C00N C00W F1 178.6(2) . . . . ?
C00B C00N C00W C00X -0.4(3) . . . . ?
F1 C00W C00X C012 -179.2(2) . . . . ?
C00N C00W C00X C012 -0.1(4) . . . . ?
C00G C00L C00Y C013 -0.3(3) . . . . ?
C00W C00X C012 C00O 0.3(4) . . . . ?
C00B C00O C012 C00X 0.0(4) . . . . ?
C00K C00S C013 C00Y -0.5(3) . . . . ?
C00L C00Y C013 C00S 1.5(4) . . . . ?

_refine_diff_density_max         0.162
_refine_diff_density_min         -0.278
_refine_diff_density_rms         0.048



####################################################################### 
# 
# 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_C200605a_a
_database_code_depnum_ccdc_archive 'CCDC 2008347'
loop_
_audit_author_name
_audit_author_address
'Xiaofeng Xia'
;Jiangnan University
China
;
_audit_update_record             
;
2020-06-06 deposited with the CCDC.	2020-11-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C40 H40 Br2 Cl2 N4 O6 S2'
_chemical_formula_weight         967.60

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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 '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 c a 21'
_space_group_name_Hall           'P 2c -2ac'

_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+1/2'
'x+1/2, -y, z'
'-x+1/2, y, z+1/2'

_cell_length_a                   7.9608(3)
_cell_length_b                   23.8872(9)
_cell_length_c                   21.8984(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4164.2(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    9084
_cell_measurement_theta_min      4.04
_cell_measurement_theta_max      66.33

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.543
_exptl_crystal_F_000             1968
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_exptl_absorpt_coefficient_mu    5.010
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.422
_exptl_absorpt_correction_T_max  0.449
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            25004
_diffrn_reflns_av_unetI/netI     0.0394
_diffrn_reflns_av_R_equivalents  0.0460
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         3.701
_diffrn_reflns_theta_max         66.710
_diffrn_reflns_theta_full        66.710
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             7334
_reflns_number_gt                6818
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.933
_reflns_Friedel_fraction_max     0.989
_reflns_Friedel_fraction_full    0.989

_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0910P)²] 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_abs_structure_details 
; 
 Flack x determined using 2886 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.071(5)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         7334
_refine_ls_number_parameters     511
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0406
_refine_ls_R_factor_gt           0.0358
_refine_ls_wR_factor_ref         0.1114
_refine_ls_wR_factor_gt          0.1058
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_restrained_S_all      1.001
_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_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 0.4004(5) 0.75001(17) 0.52454(19) 0.0387(9) Uani 1 1 d . . . . .
C2 C 0.5303(7) 0.7347(3) 0.5617(3) 0.0693(16) Uani 1 1 d . . . . .
H2 H 0.5322 0.7458 0.6023 0.083 Uiso 1 1 calc R U . . .
C3 C 0.6569(8) 0.7029(3) 0.5385(3) 0.0794(19) Uani 1 1 d . . . . .
H3 H 0.7473 0.6937 0.5635 0.095 Uiso 1 1 calc R U . . .
C4 C 0.6550(7) 0.6839(2) 0.4788(3) 0.0634(15) Uani 1 1 d . . . . .
C5 C 0.5266(8) 0.7008(3) 0.4424(3) 0.0661(14) Uani 1 1 d . . . . .
H5 H 0.5249 0.6897 0.4017 0.079 Uiso 1 1 calc R U . . .
C6 C 0.3987(7) 0.7339(3) 0.4647(2) 0.0626(14) Uani 1 1 d . . . . .
H6 H 0.3119 0.7453 0.4391 0.075 Uiso 1 1 calc R U . . .
C7 C 0.7905(9) 0.6452(3) 0.4558(4) 0.106(3) Uani 1 1 d . . . . .
H7A H 0.7547 0.6282 0.4183 0.159 Uiso 1 1 calc R U . . .
H7B H 0.8113 0.6165 0.4857 0.159 Uiso 1 1 calc R U . . .
H7C H 0.8916 0.6661 0.4489 0.159 Uiso 1 1 calc R U . . .
C8 C 0.1849(5) 0.91480(16) 0.4051(2) 0.0373(9) Uani 1 1 d . . . . .
C9 C 0.0846(5) 0.91393(16) 0.46348(19) 0.0371(8) Uani 1 1 d . . . . .
C10 C 0.2130(6) 0.88567(17) 0.5051(2) 0.0425(10) Uani 1 1 d . . . . .
H10 H 0.2155 0.9027 0.5458 0.051 Uiso 1 1 calc R U . . .
C11 C 0.0094(6) 0.81889(19) 0.4680(2) 0.0461(10) Uani 1 1 d . . . . .
H11A H -0.0649 0.7909 0.4854 0.055 Uiso 1 1 calc R U . . .
H11B H 0.0435 0.8070 0.4275 0.055 Uiso 1 1 calc R U . . .
C12 C -0.0751(5) 0.87605(19) 0.4660(2) 0.0432(9) Uani 1 1 d . . . . .
C13 C 0.1296(5) 0.92978(18) 0.3422(2) 0.0396(9) Uani 1 1 d . . . . .
C14 C 0.1844(6) 0.89696(19) 0.2941(2) 0.0469(10) Uani 1 1 d . . . . .
H14 H 0.2490 0.8654 0.3021 0.056 Uiso 1 1 calc R U . . .
C15 C 0.1444(7) 0.9104(2) 0.2339(2) 0.0565(12) Uani 1 1 d . . . . .
H15 H 0.1827 0.8886 0.2016 0.068 Uiso 1 1 calc R U . . .
C16 C 0.0472(7) 0.9567(3) 0.2238(2) 0.0584(12) Uani 1 1 d . . . . .
C17 C -0.0081(9) 0.9901(3) 0.2700(3) 0.0655(16) Uani 1 1 d . . . . .
H17 H -0.0744 1.0212 0.2616 0.079 Uiso 1 1 calc R U . . .
C18 C 0.0356(8) 0.9773(3) 0.3296(3) 0.0598(14) Uani 1 1 d . . . . .
H18 H 0.0017 1.0006 0.3613 0.072 Uiso 1 1 calc R U . . .
C19 C -0.1963(6) 0.8825(2) 0.4124(3) 0.0568(12) Uani 1 1 d . . . . .
H19A H -0.1399 0.8728 0.3751 0.085 Uiso 1 1 calc R U . . .
H19B H -0.2344 0.9206 0.4102 0.085 Uiso 1 1 calc R U . . .
H19C H -0.2909 0.8581 0.4182 0.085 Uiso 1 1 calc R U . . .
C20 C -0.1706(7) 0.8849(3) 0.5265(3) 0.0624(13) Uani 1 1 d . . . . .
H20A H -0.2258 0.9206 0.5258 0.094 Uiso 1 1 calc R U . . .
H20B H -0.0927 0.8838 0.5599 0.094 Uiso 1 1 calc R U . . .
H20C H -0.2526 0.8558 0.5314 0.094 Uiso 1 1 calc R U . . .
C21 C 0.5142(5) 0.74717(16) 0.77949(19) 0.0345(8) Uani 1 1 d . . . . .
C22 C 0.5007(6) 0.7761(2) 0.7252(2) 0.0541(12) Uani 1 1 d . . . . .
H22 H 0.4020 0.7747 0.7025 0.065 Uiso 1 1 calc R U . . .
C23 C 0.6358(7) 0.8070(3) 0.7050(3) 0.0586(12) Uani 1 1 d . . . . .
H23 H 0.6269 0.8267 0.6685 0.070 Uiso 1 1 calc R U . . .
C24 C 0.7851(6) 0.8095(2) 0.7379(3) 0.0522(11) Uani 1 1 d . . . . .
C25 C 0.7934(5) 0.7801(2) 0.7920(2) 0.0532(12) Uani 1 1 d . . . . .
H25 H 0.8917 0.7815 0.8149 0.064 Uiso 1 1 calc R U . . .
C26 C 0.6599(5) 0.74857(19) 0.8132(2) 0.0463(10) Uani 1 1 d . . . . .
H26 H 0.6685 0.7287 0.8496 0.056 Uiso 1 1 calc R U . . .
C27 C 0.9292(8) 0.8442(4) 0.7148(4) 0.091(2) Uani 1 1 d . . . . .
H27A H 0.9738 0.8662 0.7477 0.136 Uiso 1 1 calc R U . . .
H27B H 0.8905 0.8685 0.6829 0.136 Uiso 1 1 calc R U . . .
H27C H 1.0153 0.8199 0.6992 0.136 Uiso 1 1 calc R U . . .
C28 C 0.2907(5) 0.58335(15) 0.6487(2) 0.0364(9) Uani 1 1 d . . . . .
C29 C 0.1971(5) 0.58555(15) 0.70945(18) 0.0347(8) Uani 1 1 d . . . . .
C30 C 0.3312(5) 0.61392(17) 0.7486(2) 0.0395(9) Uani 1 1 d . . . . .
H30 H 0.3440 0.5956 0.7884 0.047 Uiso 1 1 calc R U . . .
C31 C 0.1247(5) 0.68074(16) 0.71492(19) 0.0359(8) Uani 1 1 d . . . . .
H31A H 0.1597 0.6922 0.6744 0.043 Uiso 1 1 calc R U . . .
H31B H 0.0510 0.7091 0.7320 0.043 Uiso 1 1 calc R U . . .
C32 C 0.0388(5) 0.62334(17) 0.71346(19) 0.0354(8) Uani 1 1 d . . . . .
C33 C 0.2265(5) 0.56600(17) 0.58822(19) 0.0389(8) Uani 1 1 d . . . . .
C34 C 0.1472(7) 0.5149(2) 0.5794(2) 0.0511(12) Uani 1 1 d . . . . .
H34 H 0.1282 0.4912 0.6124 0.061 Uiso 1 1 calc R U . . .
C35 C 0.0961(7) 0.4993(2) 0.5210(3) 0.0584(13) Uani 1 1 d . . . . .
H35 H 0.0436 0.4650 0.5147 0.070 Uiso 1 1 calc R U . . .
C36 C 0.1236(6) 0.5349(2) 0.4723(2) 0.0454(10) Uani 1 1 d . . . . .
C37 C 0.2041(6) 0.5854(2) 0.4798(2) 0.0481(10) Uani 1 1 d . . . . .
H37 H 0.2236 0.6090 0.4467 0.058 Uiso 1 1 calc R U . . .
C38 C 0.2552(6) 0.60031(17) 0.5382(2) 0.0438(9) Uani 1 1 d . . . . .
H38 H 0.3103 0.6342 0.5440 0.053 Uiso 1 1 calc R U . . .
C39 C -0.0534(6) 0.6136(2) 0.7735(2) 0.0484(10) Uani 1 1 d . . . . .
H39A H -0.1373 0.6421 0.7789 0.073 Uiso 1 1 calc R U . . .
H39B H 0.0252 0.6152 0.8067 0.073 Uiso 1 1 calc R U . . .
H39C H -0.1063 0.5775 0.7727 0.073 Uiso 1 1 calc R U . . .
C40 C -0.0831(6) 0.6181(2) 0.6605(2) 0.0497(11) Uani 1 1 d . . . . .
H40A H -0.1191 0.5799 0.6569 0.075 Uiso 1 1 calc R U . . .
H40B H -0.0285 0.6295 0.6235 0.075 Uiso 1 1 calc R U . . .
H40C H -0.1788 0.6417 0.6678 0.075 Uiso 1 1 calc R U . . .
Cl1 Cl 0.04274(17) 0.98496(4) 0.48553(6) 0.0520(3) Uani 1 1 d . . . . .
Cl2 Cl 0.15836(16) 0.51463(4) 0.73381(5) 0.0494(3) Uani 1 1 d . . . . .
N1 N 0.1544(5) 0.82842(15) 0.50704(18) 0.0433(8) Uani 1 1 d . . . . .
N2 N 0.3387(5) 0.90204(17) 0.4125(2) 0.0484(9) Uani 1 1 d . . . . .
N3 N 0.2699(4) 0.67074(13) 0.75461(17) 0.0382(7) Uani 1 1 d . . . . .
N4 N 0.4441(5) 0.59860(17) 0.6532(2) 0.0487(9) Uani 1 1 d . . . . .
O1 O 0.2833(6) 0.81542(17) 0.60863(16) 0.0718(12) Uani 1 1 d . . . . .
O2 O 0.0972(6) 0.74333(16) 0.5664(2) 0.0739(12) Uani 1 1 d . . . . .
O3 O 0.3701(4) 0.89042(15) 0.47477(17) 0.0548(9) Uani 1 1 d . . . . .
O4 O 0.3876(5) 0.67922(14) 0.85870(15) 0.0522(8) Uani 1 1 d . . . . .
O5 O 0.2062(4) 0.75376(12) 0.81671(17) 0.0490(7) Uani 1 1 d . . . . .
O6 O 0.4836(4) 0.61238(15) 0.71377(17) 0.0527(8) Uani 1 1 d . . . . .
S1 S 0.22500(16) 0.78429(4) 0.55743(5) 0.0472(3) Uani 1 1 d . . . . .
S2 S 0.33538(12) 0.71242(4) 0.80812(5) 0.0363(2) Uani 1 1 d . . . . .
Br1 Br -0.00945(12) 0.97505(4) 0.14179(3) 0.0963(3) Uani 1 1 d . . . . .
Br2 Br 0.05008(9) 0.51358(3) 0.39322(3) 0.0698(2) 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
C1 C6 1.365(7) . ?
C1 C2 1.366(7) . ?
C1 S1 1.772(4) . ?
C2 C3 1.360(9) . ?
C2 H2 0.9300 . ?
C3 C4 1.383(10) . ?
C3 H3 0.9300 . ?
C4 C5 1.357(9) . ?
C4 C7 1.508(8) . ?
C5 C6 1.379(8) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 N2 1.272(6) . ?
C8 C13 1.490(6) . ?
C8 C9 1.507(6) . ?
C9 C10 1.526(6) . ?
C9 C12 1.561(6) . ?
C9 Cl1 1.795(4) . ?
C10 O3 1.421(6) . ?
C10 N1 1.446(6) . ?
C10 H10 0.9800 . ?
C11 N1 1.455(6) . ?
C11 C12 1.523(6) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C19 1.526(6) . ?
C12 C20 1.542(7) . ?
C13 C14 1.384(6) . ?
C13 C18 1.387(7) . ?
C14 C15 1.394(7) . ?
C14 H14 0.9300 . ?
C15 C16 1.368(8) . ?
C15 H15 0.9300 . ?
C16 C17 1.362(9) . ?
C16 Br1 1.902(5) . ?
C17 C18 1.385(8) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 C26 1.376(6) . ?
C21 C22 1.380(7) . ?
C21 S2 1.763(4) . ?
C22 C23 1.377(7) . ?
C22 H22 0.9300 . ?
C23 C24 1.391(8) . ?
C23 H23 0.9300 . ?
C24 C25 1.379(7) . ?
C24 C27 1.502(7) . ?
C25 C26 1.382(7) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
C28 N4 1.278(6) . ?
C28 C33 1.478(6) . ?
C28 C29 1.527(6) . ?
C29 C30 1.528(6) . ?
C29 C32 1.552(5) . ?
C29 Cl2 1.803(4) . ?
C30 O6 1.434(6) . ?
C30 N3 1.448(5) . ?
C30 H30 0.9800 . ?
C31 N3 1.466(5) . ?
C31 C32 1.532(6) . ?
C31 H31A 0.9700 . ?
C31 H31B 0.9700 . ?
C32 C40 1.517(6) . ?
C32 C39 1.523(6) . ?
C33 C38 1.386(6) . ?
C33 C34 1.388(6) . ?
C34 C35 1.394(8) . ?
C34 H34 0.9300 . ?
C35 C36 1.381(8) . ?
C35 H35 0.9300 . ?
C36 C37 1.375(7) . ?
C36 Br2 1.898(5) . ?
C37 C38 1.389(7) . ?
C37 H37 0.9300 . ?
C38 H38 0.9300 . ?
C39 H39A 0.9600 . ?
C39 H39B 0.9600 . ?
C39 H39C 0.9600 . ?
C40 H40A 0.9600 . ?
C40 H40B 0.9600 . ?
C40 H40C 0.9600 . ?
N1 S1 1.626(4) . ?
N2 O3 1.415(6) . ?
N3 S2 1.624(3) . ?
N4 O6 1.401(6) . ?
O1 S1 1.423(4) . ?
O2 S1 1.425(4) . ?
O4 S2 1.424(3) . ?
O5 S2 1.438(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 C1 C2 120.2(5) . . ?
C6 C1 S1 120.8(4) . . ?
C2 C1 S1 118.6(4) . . ?
C3 C2 C1 119.3(5) . . ?
C3 C2 H2 120.4 . . ?
C1 C2 H2 120.4 . . ?
C2 C3 C4 121.8(5) . . ?
C2 C3 H3 119.1 . . ?
C4 C3 H3 119.1 . . ?
C5 C4 C3 117.8(5) . . ?
C5 C4 C7 121.6(7) . . ?
C3 C4 C7 120.6(6) . . ?
C4 C5 C6 121.2(5) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 H5 119.4 . . ?
C1 C6 C5 119.6(5) . . ?
C1 C6 H6 120.2 . . ?
C5 C6 H6 120.2 . . ?
C4 C7 H7A 109.5 . . ?
C4 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C4 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N2 C8 C13 117.3(4) . . ?
N2 C8 C9 113.6(4) . . ?
C13 C8 C9 129.1(3) . . ?
C8 C9 C10 99.0(3) . . ?
C8 C9 C12 118.0(4) . . ?
C10 C9 C12 105.5(3) . . ?
C8 C9 Cl1 108.3(3) . . ?
C10 C9 Cl1 112.4(3) . . ?
C12 C9 Cl1 112.8(3) . . ?
O3 C10 N1 111.9(4) . . ?
O3 C10 C9 106.0(3) . . ?
N1 C10 C9 102.7(3) . . ?
O3 C10 H10 111.9 . . ?
N1 C10 H10 111.9 . . ?
C9 C10 H10 111.9 . . ?
N1 C11 C12 103.1(4) . . ?
N1 C11 H11A 111.1 . . ?
C12 C11 H11A 111.1 . . ?
N1 C11 H11B 111.1 . . ?
C12 C11 H11B 111.1 . . ?
H11A C11 H11B 109.1 . . ?
C11 C12 C19 113.1(4) . . ?
C11 C12 C20 108.4(4) . . ?
C19 C12 C20 109.6(4) . . ?
C11 C12 C9 99.3(3) . . ?
C19 C12 C9 115.4(4) . . ?
C20 C12 C9 110.6(4) . . ?
C14 C13 C18 118.8(4) . . ?
C14 C13 C8 118.4(4) . . ?
C18 C13 C8 122.7(4) . . ?
C13 C14 C15 121.2(4) . . ?
C13 C14 H14 119.4 . . ?
C15 C14 H14 119.4 . . ?
C16 C15 C14 117.9(5) . . ?
C16 C15 H15 121.0 . . ?
C14 C15 H15 121.0 . . ?
C17 C16 C15 122.4(5) . . ?
C17 C16 Br1 119.3(4) . . ?
C15 C16 Br1 118.2(4) . . ?
C16 C17 C18 119.3(5) . . ?
C16 C17 H17 120.3 . . ?
C18 C17 H17 120.3 . . ?
C17 C18 C13 120.3(5) . . ?
C17 C18 H18 119.9 . . ?
C13 C18 H18 119.9 . . ?
C12 C19 H19A 109.5 . . ?
C12 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C12 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C12 C20 H20A 109.5 . . ?
C12 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C12 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C26 C21 C22 121.0(4) . . ?
C26 C21 S2 120.1(3) . . ?
C22 C21 S2 118.7(3) . . ?
C23 C22 C21 119.0(4) . . ?
C23 C22 H22 120.5 . . ?
C21 C22 H22 120.5 . . ?
C22 C23 C24 121.6(5) . . ?
C22 C23 H23 119.2 . . ?
C24 C23 H23 119.2 . . ?
C25 C24 C23 117.6(4) . . ?
C25 C24 C27 122.2(5) . . ?
C23 C24 C27 120.1(5) . . ?
C24 C25 C26 122.0(4) . . ?
C24 C25 H25 119.0 . . ?
C26 C25 H25 119.0 . . ?
C21 C26 C25 118.8(4) . . ?
C21 C26 H26 120.6 . . ?
C25 C26 H26 120.6 . . ?
C24 C27 H27A 109.5 . . ?
C24 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C24 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
N4 C28 C33 118.7(4) . . ?
N4 C28 C29 112.9(4) . . ?
C33 C28 C29 128.4(3) . . ?
C28 C29 C30 99.4(3) . . ?
C28 C29 C32 117.8(3) . . ?
C30 C29 C32 106.1(3) . . ?
C28 C29 Cl2 108.0(3) . . ?
C30 C29 Cl2 111.7(3) . . ?
C32 C29 Cl2 113.0(3) . . ?
O6 C30 N3 110.9(4) . . ?
O6 C30 C29 106.3(3) . . ?
N3 C30 C29 103.4(3) . . ?
O6 C30 H30 111.9 . . ?
N3 C30 H30 111.9 . . ?
C29 C30 H30 111.9 . . ?
N3 C31 C32 102.6(3) . . ?
N3 C31 H31A 111.2 . . ?
C32 C31 H31A 111.2 . . ?
N3 C31 H31B 111.2 . . ?
C32 C31 H31B 111.2 . . ?
H31A C31 H31B 109.2 . . ?
C40 C32 C39 109.8(4) . . ?
C40 C32 C31 112.0(4) . . ?
C39 C32 C31 109.5(3) . . ?
C40 C32 C29 115.4(4) . . ?
C39 C32 C29 110.6(4) . . ?
C31 C32 C29 99.2(3) . . ?
C38 C33 C34 119.0(4) . . ?
C38 C33 C28 119.0(4) . . ?
C34 C33 C28 121.9(4) . . ?
C33 C34 C35 119.7(5) . . ?
C33 C34 H34 120.2 . . ?
C35 C34 H34 120.2 . . ?
C36 C35 C34 119.9(4) . . ?
C36 C35 H35 120.1 . . ?
C34 C35 H35 120.1 . . ?
C37 C36 C35 121.4(4) . . ?
C37 C36 Br2 119.3(4) . . ?
C35 C36 Br2 119.3(4) . . ?
C36 C37 C38 118.1(4) . . ?
C36 C37 H37 120.9 . . ?
C38 C37 H37 120.9 . . ?
C33 C38 C37 121.9(4) . . ?
C33 C38 H38 119.1 . . ?
C37 C38 H38 119.1 . . ?
C32 C39 H39A 109.5 . . ?
C32 C39 H39B 109.5 . . ?
H39A C39 H39B 109.5 . . ?
C32 C39 H39C 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 109.5 . . ?
C32 C40 H40A 109.5 . . ?
C32 C40 H40B 109.5 . . ?
H40A C40 H40B 109.5 . . ?
C32 C40 H40C 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?
C10 N1 C11 112.7(3) . . ?
C10 N1 S1 121.4(3) . . ?
C11 N1 S1 124.9(3) . . ?
C8 N2 O3 109.8(4) . . ?
C30 N3 C31 111.4(3) . . ?
C30 N3 S2 122.1(3) . . ?
C31 N3 S2 125.5(3) . . ?
C28 N4 O6 110.8(4) . . ?
N2 O3 C10 108.1(3) . . ?
N4 O6 C30 108.6(3) . . ?
O1 S1 O2 118.9(3) . . ?
O1 S1 N1 108.0(2) . . ?
O2 S1 N1 107.0(2) . . ?
O1 S1 C1 107.8(2) . . ?
O2 S1 C1 107.5(2) . . ?
N1 S1 C1 107.2(2) . . ?
O4 S2 O5 119.3(2) . . ?
O4 S2 N3 108.27(19) . . ?
O5 S2 N3 106.60(19) . . ?
O4 S2 C21 107.7(2) . . ?
O5 S2 C21 107.48(18) . . ?
N3 S2 C21 106.94(19) . . ?

_refine_diff_density_max         0.453
_refine_diff_density_min         -0.622
_refine_diff_density_rms         0.055



####################################################################### 
# 
# 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_s
_database_code_depnum_ccdc_archive 'CCDC 1973197'
loop_
_audit_author_name
_audit_author_address
xiaxfgg
;Jiangnan University
China
;
_audit_update_record             
;
2019-12-20 deposited with the CCDC.	2020-11-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H12 Br N O2'
_chemical_formula_weight         330.18

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'
Br Br -0.6763 1.2805 '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'

_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                   6.8906(3)
_cell_length_b                   10.6824(5)
_cell_length_c                   10.8082(5)
_cell_angle_alpha                67.251(2)
_cell_angle_beta                 75.267(2)
_cell_angle_gamma                84.165(2)
_cell_volume                     709.56(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    9872
_cell_measurement_theta_min      4.4883
_cell_measurement_theta_max      66.5371

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            WHITE
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.545
_exptl_crystal_F_000             332
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    3.954
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4362
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  D8VENTURE
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23482
_diffrn_reflns_av_unetI/netI     0.0271
_diffrn_reflns_av_R_equivalents  0.0569
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         4.488
_diffrn_reflns_theta_max         66.563
_diffrn_reflns_theta_full        66.563
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             2480
_reflns_number_gt                2237
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0559P)²+0.4160P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.0048(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2480
_refine_ls_number_parameters     186
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0391
_refine_ls_R_factor_gt           0.0355
_refine_ls_wR_factor_ref         0.1063
_refine_ls_wR_factor_gt          0.1036
_refine_ls_goodness_of_fit_ref   1.137
_refine_ls_restrained_S_all      1.138
_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_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
Br1 Br 0.90943(6) 0.41365(4) -0.31719(3) 0.0636(2) Uani 1 1 d . . . . .
O1 O 0.6541(3) 0.48902(18) 0.2188(2) 0.0437(5) Uani 1 1 d . . . . .
O2 O 0.9709(4) 0.1603(2) 0.4219(2) 0.0559(6) Uani 1 1 d D . . . .
H2 H 1.036(6) 0.106(3) 0.484(3) 0.084 Uiso 1 1 d D U . . .
N1 N 0.8776(4) 0.0673(2) 0.3911(2) 0.0428(5) Uani 1 1 d . . . . .
C1 C 0.7864(4) 0.5712(3) -0.1524(3) 0.0457(7) Uani 1 1 d . . . . .
H1 H 0.797451 0.642606 -0.237290 0.055 Uiso 1 1 calc R U . . .
C2 C 0.8308(4) 0.4392(3) -0.1470(3) 0.0425(6) Uani 1 1 d . . . . .
C3 C 0.8208(4) 0.3283(3) -0.0248(3) 0.0375(6) Uani 1 1 d . . . . .
H3 H 0.852644 0.241268 -0.023729 0.045 Uiso 1 1 calc R U . . .
C4 C 0.7264(4) 0.5960(3) -0.0326(3) 0.0432(6) Uani 1 1 d . . . . .
H4 H 0.695708 0.683244 -0.033712 0.052 Uiso 1 1 calc R U . . .
C5 C 0.7139(4) 0.4853(3) 0.0895(3) 0.0369(6) Uani 1 1 d . . . . .
C6 C 0.7607(4) 0.3536(2) 0.0965(3) 0.0341(5) Uani 1 1 d . . . . .
C7 C 0.6669(4) 0.3575(3) 0.3099(3) 0.0415(6) Uani 1 1 d . . . . .
C8 C 0.5986(6) 0.3366(4) 0.4578(3) 0.0612(9) Uani 1 1 d . . . . .
H8AB H 0.467832 0.376101 0.474343 0.092 Uiso 1 1 calc R U . . .
H8AC H 0.691180 0.378979 0.482465 0.092 Uiso 1 1 calc R U . . .
H8A H 0.592602 0.241089 0.512542 0.092 Uiso 1 1 calc R U . . .
C9 C 0.7330(4) 0.2718(3) 0.2429(3) 0.0369(6) Uani 1 1 d . . . . .
C10 C 0.7678(4) 0.1249(3) 0.3040(3) 0.0375(6) Uani 1 1 d . . . . .
C11 C 0.6737(4) 0.0340(3) 0.2608(3) 0.0384(6) Uani 1 1 d . . . . .
C12 C 0.4820(5) 0.0618(3) 0.2394(3) 0.0501(7) Uani 1 1 d . . . . .
H12 H 0.412736 0.136520 0.253093 0.060 Uiso 1 1 calc R U . . .
C13 C 0.3921(6) -0.0204(4) 0.1979(4) 0.0624(9) Uani 1 1 d . . . . .
H13 H 0.262407 -0.001510 0.184865 0.075 Uiso 1 1 calc R U . . .
C14 C 0.4945(6) -0.1298(4) 0.1759(4) 0.0652(10) Uani 1 1 d . . . . .
H14 H 0.435245 -0.183718 0.145764 0.078 Uiso 1 1 calc R U . . .
C15 C 0.6830(6) -0.1598(4) 0.1981(4) 0.0628(9) Uani 1 1 d . . . . .
H15 H 0.750842 -0.235079 0.184778 0.075 Uiso 1 1 calc R U . . .
C16 C 0.7741(5) -0.0779(3) 0.2405(3) 0.0524(7) Uani 1 1 d . . . . .
H16 H 0.902724 -0.098538 0.255334 0.063 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C2 1.898(3) . ?
O1 C5 1.369(3) . ?
O1 C7 1.378(3) . ?
O2 N1 1.416(3) . ?
O2 H2 0.893(10) . ?
N1 C10 1.287(3) . ?
C1 C4 1.375(4) . ?
C1 C2 1.393(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.383(4) . ?
C3 C6 1.392(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.379(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.388(4) . ?
C6 C9 1.454(3) . ?
C7 C9 1.353(4) . ?
C7 C8 1.480(4) . ?
C8 H8AB 0.9600 . ?
C8 H8AC 0.9600 . ?
C8 H8A 0.9600 . ?
C9 C10 1.469(4) . ?
C10 C11 1.488(4) . ?
C11 C12 1.381(4) . ?
C11 C16 1.383(4) . ?
C12 C13 1.383(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.372(6) . ?
C13 H13 0.9300 . ?
C14 C15 1.364(6) . ?
C14 H14 0.9300 . ?
C15 C16 1.392(4) . ?
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
C5 O1 C7 106.2(2) . . ?
N1 O2 H2 103(3) . . ?
C10 N1 O2 113.4(2) . . ?
C4 C1 C2 120.2(2) . . ?
C4 C1 H1 119.9 . . ?
C2 C1 H1 119.9 . . ?
C3 C2 C1 123.1(3) . . ?
C3 C2 Br1 119.4(2) . . ?
C1 C2 Br1 117.4(2) . . ?
C2 C3 C6 116.7(2) . . ?
C2 C3 H3 121.7 . . ?
C6 C3 H3 121.7 . . ?
C1 C4 C5 116.7(3) . . ?
C1 C4 H4 121.6 . . ?
C5 C4 H4 121.6 . . ?
O1 C5 C4 125.4(2) . . ?
O1 C5 C6 110.8(2) . . ?
C4 C5 C6 123.8(3) . . ?
C5 C6 C3 119.5(2) . . ?
C5 C6 C9 105.1(2) . . ?
C3 C6 C9 135.4(2) . . ?
C9 C7 O1 111.5(2) . . ?
C9 C7 C8 133.0(3) . . ?
O1 C7 C8 115.4(3) . . ?
C7 C8 H8AB 109.5 . . ?
C7 C8 H8AC 109.5 . . ?
H8AB C8 H8AC 109.5 . . ?
C7 C8 H8A 109.5 . . ?
H8AB C8 H8A 109.5 . . ?
H8AC C8 H8A 109.5 . . ?
C7 C9 C6 106.3(2) . . ?
C7 C9 C10 127.5(2) . . ?
C6 C9 C10 126.2(2) . . ?
N1 C10 C9 125.2(2) . . ?
N1 C10 C11 116.5(2) . . ?
C9 C10 C11 118.3(2) . . ?
C12 C11 C16 118.9(3) . . ?
C12 C11 C10 119.6(3) . . ?
C16 C11 C10 121.5(3) . . ?
C11 C12 C13 120.7(3) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
C14 C13 C12 119.9(3) . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C15 C14 C13 120.2(3) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C14 C15 C16 120.2(3) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
C11 C16 C15 120.1(3) . . ?
C11 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?

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
C4 C1 C2 C3 -1.0(4) . . . . ?
C4 C1 C2 Br1 179.3(2) . . . . ?
C1 C2 C3 C6 0.8(4) . . . . ?
Br1 C2 C3 C6 -179.51(18) . . . . ?
C2 C1 C4 C5 0.2(4) . . . . ?
C7 O1 C5 C4 -179.0(3) . . . . ?
C7 O1 C5 C6 1.1(3) . . . . ?
C1 C4 C5 O1 -178.9(2) . . . . ?
C1 C4 C5 C6 0.9(4) . . . . ?
O1 C5 C6 C3 178.7(2) . . . . ?
C4 C5 C6 C3 -1.2(4) . . . . ?
O1 C5 C6 C9 -2.0(3) . . . . ?
C4 C5 C6 C9 178.2(3) . . . . ?
C2 C3 C6 C5 0.3(4) . . . . ?
C2 C3 C6 C9 -178.8(3) . . . . ?
C5 O1 C7 C9 0.3(3) . . . . ?
C5 O1 C7 C8 -177.0(3) . . . . ?
O1 C7 C9 C6 -1.5(3) . . . . ?
C8 C7 C9 C6 175.2(3) . . . . ?
O1 C7 C9 C10 179.3(2) . . . . ?
C8 C7 C9 C10 -4.0(5) . . . . ?
C5 C6 C9 C7 2.1(3) . . . . ?
C3 C6 C9 C7 -178.7(3) . . . . ?
C5 C6 C9 C10 -178.7(2) . . . . ?
C3 C6 C9 C10 0.5(5) . . . . ?
O2 N1 C10 C9 -1.7(4) . . . . ?
O2 N1 C10 C11 176.8(2) . . . . ?
C7 C9 C10 N1 -53.3(4) . . . . ?
C6 C9 C10 N1 127.7(3) . . . . ?
C7 C9 C10 C11 128.2(3) . . . . ?
C6 C9 C10 C11 -50.9(4) . . . . ?
N1 C10 C11 C12 142.6(3) . . . . ?
C9 C10 C11 C12 -38.7(4) . . . . ?
N1 C10 C11 C16 -37.7(4) . . . . ?
C9 C10 C11 C16 140.9(3) . . . . ?
C16 C11 C12 C13 -0.3(4) . . . . ?
C10 C11 C12 C13 179.4(3) . . . . ?
C11 C12 C13 C14 -0.8(5) . . . . ?
C12 C13 C14 C15 1.6(6) . . . . ?
C13 C14 C15 C16 -1.3(6) . . . . ?
C12 C11 C16 C15 0.6(5) . . . . ?
C10 C11 C16 C15 -179.0(3) . . . . ?
C14 C15 C16 C11 0.2(5) . . . . ?

_refine_diff_density_max         0.564
_refine_diff_density_min         -0.592
_refine_diff_density_rms         0.062



####################################################################### 
# 
# 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_20200910_x1_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2031399'
loop_
_audit_author_name
_audit_author_address
xiaxfbr
;Jiangnan University
China
;
_audit_update_record             
;
2020-09-11 deposited with the CCDC.	2020-11-30 downloaded from the CCDC.
;
_audit_creation_date             2020-09-10
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H24 Cl N O5'
_chemical_formula_sum            'C20 H24 Cl N O5'
_chemical_formula_weight         393.85
_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.207(7)
_cell_length_b                   11.693(11)
_cell_length_c                   12.233(9)
_cell_angle_alpha                78.96(3)
_cell_angle_beta                 84.63(3)
_cell_angle_gamma                87.16(3)
_cell_volume                     1006.9(15)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9982
_cell_measurement_temperature    169(2)
_cell_measurement_theta_max      27.45
_cell_measurement_theta_min      3.19
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.220
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_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    1.299
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             416
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   0.4876
_exptl_transmission_factor_min   0.1278
_diffrn_reflns_av_R_equivalents  0.0740
_diffrn_reflns_av_unetI/netI     0.0349
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            29675
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_min         2.840
_diffrn_ambient_temperature      169.36
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3633
_reflns_number_total             4618
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_refine_diff_density_max         0.658
_refine_diff_density_min         -0.419
_refine_diff_density_rms         0.102
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     249
_refine_ls_number_reflns         4618
_refine_ls_number_restraints     204
_refine_ls_R_factor_all          0.0684
_refine_ls_R_factor_gt           0.0535
_refine_ls_restrained_S_all      1.040
_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)+(0.0817P)²+0.4369P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1479
_refine_ls_wR_factor_ref         0.1627
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C19(H19A,H19B), C16(H16A,H16B)
3.b Aromatic/amide H refined with riding coordinates:
 C14(H14), C4(H4), C3(H3), C2(H2), C6(H6)
3.c Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C11(H11A,H11B,H11C), C10(H10A,H10B,H10C), C17(H17A,H17B,
 H17C)
3.d Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.71026(8) 0.16366(5) 0.57253(4) 0.05463(19) Uani 1 1 d . . . . .
O2 O 0.7744(2) 0.78185(12) 0.41008(12) 0.0446(3) Uani 1 1 d . . . . .
O1 O 0.6058(2) 0.62134(13) 0.00033(12) 0.0528(4) Uani 1 1 d . . . . .
H1 H 0.550910 0.601624 -0.050441 0.079 Uiso 1 1 calc R U . . .
N1 N 0.6103(2) 0.52783(13) 0.09131(13) 0.0387(4) Uani 1 1 d . . . . .
O4 O 0.5159(3) 0.98524(15) 0.17926(16) 0.0685(5) Uani 1 1 d . . . . .
C8 C 0.7642(3) 0.66733(14) 0.17782(14) 0.0317(4) Uani 1 1 d . . . . .
O3 O 0.8013(4) 0.97274(14) 0.35508(16) 0.0856(7) Uani 1 1 d . . . . .
C7 C 0.6900(2) 0.55153(14) 0.17333(14) 0.0307(4) Uani 1 1 d . . . . .
C14 C 0.6603(3) 0.75383(15) 0.20896(15) 0.0362(4) Uani 1 1 d . . . . .
H14 H 0.529025 0.751191 0.225971 0.043 Uiso 1 1 calc R U . . .
C5 C 0.7021(2) 0.45511(14) 0.27153(14) 0.0299(3) Uani 1 1 d . . . . .
C4 C 0.6936(3) 0.47930(15) 0.37928(15) 0.0339(4) Uani 1 1 d . . . . .
H4 H 0.686236 0.558022 0.389327 0.041 Uiso 1 1 calc R U . . .
C9 C 0.9709(3) 0.69331(16) 0.15523(16) 0.0366(4) Uani 1 1 d . . . . .
O5 O 0.7819(4) 1.04169(18) 0.0839(2) 0.0964(8) Uani 1 1 d . . . . .
C3 C 0.6958(3) 0.38989(17) 0.47202(15) 0.0370(4) Uani 1 1 d . . . . .
H3 H 0.688086 0.406980 0.545203 0.044 Uiso 1 1 calc R U . . .
C2 C 0.7238(3) 0.24912(16) 0.35048(17) 0.0408(4) Uani 1 1 d . . . . .
H2 H 0.736168 0.170294 0.340894 0.049 Uiso 1 1 calc R U . . .
C6 C 0.7198(3) 0.33878(16) 0.25853(16) 0.0373(4) Uani 1 1 d . . . . .
H6 H 0.729207 0.320993 0.185585 0.045 Uiso 1 1 calc R U . . .
C1 C 0.7095(3) 0.27562(16) 0.45639(16) 0.0362(4) Uani 1 1 d . . . . .
C13 C 0.7743(3) 0.85754(16) 0.21442(16) 0.0401(4) Uani 1 1 d . . . . .
C12 C 0.9699(3) 0.82407(18) 0.1637(2) 0.0487(5) Uani 1 1 d . . . . .
H12A H 1.066559 0.837329 0.211937 0.058 Uiso 1 1 calc R U . . .
H12B H 0.996902 0.872476 0.088639 0.058 Uiso 1 1 calc R U . . .
C18 C 0.7830(3) 0.87874(17) 0.33326(17) 0.0437(5) Uani 1 1 d . . . . .
C19 C 0.7842(3) 0.7963(2) 0.52489(17) 0.0483(5) Uani 1 1 d . . . . .
H19A H 0.673524 0.841518 0.549403 0.058 Uiso 1 1 calc R U . . .
H19B H 0.897313 0.838622 0.531033 0.058 Uiso 1 1 calc R U . . .
C15 C 0.6950(4) 0.97194(18) 0.14986(18) 0.0525(5) Uani 1 1 d . . . . .
C20 C 0.7907(3) 0.6767(2) 0.5962(2) 0.0563(6) Uani 1 1 d . . . . .
H20A H 0.896647 0.631321 0.568441 0.084 Uiso 1 1 calc R U . . .
H20B H 0.674721 0.637535 0.593104 0.084 Uiso 1 1 calc R U . . .
H20C H 0.804960 0.683164 0.673666 0.084 Uiso 1 1 calc R U . . .
C11 C 1.0853(3) 0.6193(2) 0.2445(2) 0.0610(6) Uani 1 1 d . . . . .
H11A H 1.033098 0.630209 0.318820 0.092 Uiso 1 1 calc R U . . .
H11B H 1.214972 0.643578 0.232256 0.092 Uiso 1 1 calc R U . . .
H11C H 1.080811 0.536885 0.239334 0.092 Uiso 1 1 calc R U . . .
C10 C 1.0500(4) 0.6744(2) 0.0393(2) 0.0593(6) Uani 1 1 d . . . . .
H10A H 1.048662 0.591339 0.036255 0.089 Uiso 1 1 calc R U . . .
H10B H 1.178361 0.700932 0.024871 0.089 Uiso 1 1 calc R U . . .
H10C H 0.973538 0.718925 -0.017383 0.089 Uiso 1 1 calc R U . . .
C16 C 0.4261(5) 1.0966(3) 0.1338(3) 0.0933(11) Uani 1 1 d . . . . .
H16A H 0.504893 1.161319 0.140963 0.112 Uiso 1 1 calc R U . . .
H16B H 0.411047 1.100889 0.053527 0.112 Uiso 1 1 calc R U . . .
C17 C 0.2507(6) 1.1075(3) 0.1922(4) 0.1181(15) Uani 1 1 d . . . . .
H17A H 0.198715 1.186548 0.169309 0.177 Uiso 1 1 calc R U . . .
H17B H 0.264295 1.092474 0.272704 0.177 Uiso 1 1 calc R U . . .
H17C H 0.166827 1.050931 0.175308 0.177 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C1 1.738(2) . ?
O2 C18 1.326(3) . ?
O2 C19 1.455(3) . ?
O1 H1 0.8400 . ?
O1 N1 1.405(2) . ?
N1 C7 1.282(2) . ?
O4 C15 1.317(3) . ?
O4 C16 1.459(3) . ?
C8 C7 1.492(3) . ?
C8 C14 1.322(3) . ?
C8 C9 1.524(3) . ?
O3 C18 1.196(3) . ?
C7 C5 1.488(2) . ?
C14 H14 0.9500 . ?
C14 C13 1.513(3) . ?
C5 C4 1.395(3) . ?
C5 C6 1.398(3) . ?
C4 H4 0.9500 . ?
C4 C3 1.388(3) . ?
C9 C12 1.552(3) . ?
C9 C11 1.535(3) . ?
C9 C10 1.530(3) . ?
O5 C15 1.189(3) . ?
C3 H3 0.9500 . ?
C3 C1 1.383(3) . ?
C2 H2 0.9500 . ?
C2 C6 1.385(3) . ?
C2 C1 1.382(3) . ?
C6 H6 0.9500 . ?
C13 C12 1.549(3) . ?
C13 C18 1.528(3) . ?
C13 C15 1.531(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C19 C20 1.501(3) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.405(6) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C18 O2 C19 115.91(16) . . ?
N1 O1 H1 109.5 . . ?
C7 N1 O1 113.35(15) . . ?
C15 O4 C16 116.9(2) . . ?
C7 C8 C9 122.58(16) . . ?
C14 C8 C7 123.59(18) . . ?
C14 C8 C9 113.67(16) . . ?
N1 C7 C8 125.06(16) . . ?
N1 C7 C5 115.86(15) . . ?
C5 C7 C8 119.05(15) . . ?
C8 C14 H14 123.9 . . ?
C8 C14 C13 112.28(18) . . ?
C13 C14 H14 123.9 . . ?
C4 C5 C7 120.33(16) . . ?
C4 C5 C6 118.53(16) . . ?
C6 C5 C7 121.14(16) . . ?
C5 C4 H4 119.5 . . ?
C3 C4 C5 120.91(17) . . ?
C3 C4 H4 119.5 . . ?
C8 C9 C12 101.66(15) . . ?
C8 C9 C11 111.37(17) . . ?
C8 C9 C10 112.25(17) . . ?
C11 C9 C12 110.73(18) . . ?
C10 C9 C12 111.20(18) . . ?
C10 C9 C11 109.5(2) . . ?
C4 C3 H3 120.5 . . ?
C1 C3 C4 119.09(17) . . ?
C1 C3 H3 120.5 . . ?
C6 C2 H2 120.4 . . ?
C1 C2 H2 120.4 . . ?
C1 C2 C6 119.24(18) . . ?
C5 C6 H6 119.5 . . ?
C2 C6 C5 120.92(17) . . ?
C2 C6 H6 119.5 . . ?
C3 C1 Cl1 119.09(15) . . ?
C2 C1 Cl1 119.63(16) . . ?
C2 C1 C3 121.27(17) . . ?
C14 C13 C12 102.90(16) . . ?
C14 C13 C18 113.33(16) . . ?
C14 C13 C15 112.56(19) . . ?
C18 C13 C12 110.90(18) . . ?
C18 C13 C15 104.93(17) . . ?
C15 C13 C12 112.45(18) . . ?
C9 C12 H12A 110.1 . . ?
C9 C12 H12B 110.1 . . ?
C13 C12 C9 107.96(16) . . ?
C13 C12 H12A 110.1 . . ?
C13 C12 H12B 110.1 . . ?
H12A C12 H12B 108.4 . . ?
O2 C18 C13 113.36(16) . . ?
O3 C18 O2 123.0(2) . . ?
O3 C18 C13 123.63(19) . . ?
O2 C19 H19A 110.2 . . ?
O2 C19 H19B 110.2 . . ?
O2 C19 C20 107.36(19) . . ?
H19A C19 H19B 108.5 . . ?
C20 C19 H19A 110.2 . . ?
C20 C19 H19B 110.2 . . ?
O4 C15 C13 110.82(18) . . ?
O5 C15 O4 123.7(2) . . ?
O5 C15 C13 125.5(3) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O4 C16 H16A 109.7 . . ?
O4 C16 H16B 109.7 . . ?
H16A C16 H16B 108.2 . . ?
C17 C16 O4 109.6(3) . . ?
C17 C16 H16A 109.7 . . ?
C17 C16 H16B 109.7 . . ?
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 . . ?

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
O1 N1 C7 C8 2.9(3) . . . . ?
O1 N1 C7 C5 -178.96(15) . . . . ?
N1 C7 C5 C4 -147.23(18) . . . . ?
N1 C7 C5 C6 32.0(3) . . . . ?
C8 C7 C5 C4 31.0(2) . . . . ?
C8 C7 C5 C6 -149.80(18) . . . . ?
C8 C14 C13 C12 7.6(2) . . . . ?
C8 C14 C13 C18 -112.2(2) . . . . ?
C8 C14 C13 C15 128.93(19) . . . . ?
C8 C9 C12 C13 11.8(2) . . . . ?
C7 C8 C14 C13 175.48(16) . . . . ?
C7 C8 C9 C12 176.91(16) . . . . ?
C7 C8 C9 C11 -65.1(2) . . . . ?
C7 C8 C9 C10 58.0(2) . . . . ?
C7 C5 C4 C3 176.93(16) . . . . ?
C7 C5 C6 C2 -177.50(17) . . . . ?
C14 C8 C7 N1 83.9(3) . . . . ?
C14 C8 C7 C5 -94.2(2) . . . . ?
C14 C8 C9 C12 -7.5(2) . . . . ?
C14 C8 C9 C11 110.5(2) . . . . ?
C14 C8 C9 C10 -126.4(2) . . . . ?
C14 C13 C12 C9 -12.0(2) . . . . ?
C14 C13 C18 O2 30.9(3) . . . . ?
C14 C13 C18 O3 -151.1(2) . . . . ?
C14 C13 C15 O4 50.8(3) . . . . ?
C14 C13 C15 O5 -130.9(3) . . . . ?
C5 C4 C3 C1 1.0(3) . . . . ?
C4 C5 C6 C2 1.7(3) . . . . ?
C4 C3 C1 Cl1 -179.45(14) . . . . ?
C4 C3 C1 C2 1.0(3) . . . . ?
C9 C8 C7 N1 -100.9(2) . . . . ?
C9 C8 C7 C5 81.0(2) . . . . ?
C9 C8 C14 C13 -0.1(2) . . . . ?
C6 C5 C4 C3 -2.3(3) . . . . ?
C6 C2 C1 Cl1 178.88(15) . . . . ?
C6 C2 C1 C3 -1.6(3) . . . . ?
C1 C2 C6 C5 0.2(3) . . . . ?
C12 C13 C18 O2 -84.2(2) . . . . ?
C12 C13 C18 O3 93.7(3) . . . . ?
C12 C13 C15 O4 166.51(19) . . . . ?
C12 C13 C15 O5 -15.2(3) . . . . ?
C18 O2 C19 C20 -174.70(18) . . . . ?
C18 C13 C12 C9 109.50(19) . . . . ?
C18 C13 C15 O4 -72.8(2) . . . . ?
C18 C13 C15 O5 105.4(3) . . . . ?
C19 O2 C18 O3 1.4(3) . . . . ?
C19 O2 C18 C13 179.34(17) . . . . ?
C15 O4 C16 C17 -166.4(3) . . . . ?
C15 C13 C12 C9 -133.36(19) . . . . ?
C15 C13 C18 O2 154.13(19) . . . . ?
C15 C13 C18 O3 -27.9(3) . . . . ?
C11 C9 C12 C13 -106.6(2) . . . . ?
C10 C9 C12 C13 131.5(2) . . . . ?
C16 O4 C15 O5 -5.0(4) . . . . ?
C16 O4 C15 C13 173.3(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
