# 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_10521_sq
_database_code_depnum_ccdc_archive 'CCDC 1942273'
loop_
_audit_author_name
_audit_author_address
'Hongjin Shi'
;Qing Dao Agricultural University
China
;
_audit_update_record             
;
2019-07-21 deposited with the CCDC.	2020-02-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H21 Br N4 O5'
_chemical_formula_weight         597.42

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'
O O 0.0492 0.0322 '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'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

_cell_length_a                   36.052(2)
_cell_length_b                   9.1328(5)
_cell_length_c                   22.5526(10)
_cell_angle_alpha                90
_cell_angle_beta                 128.081(6)
_cell_angle_gamma                90
_cell_volume                     5845.0(7)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2040
_cell_measurement_theta_min      4.9770
_cell_measurement_theta_max      69.6290

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.358
_exptl_crystal_F_000             2432
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.130
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    2.289
_shelx_estimated_absorpt_T_min   0.755
_shelx_estimated_absorpt_T_max   0.787
_exptl_absorpt_correction_T_min  0.73360
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10171
_diffrn_reflns_av_unetI/netI     0.0811
_diffrn_reflns_av_R_equivalents  0.0502
_diffrn_reflns_limit_h_min       -42
_diffrn_reflns_limit_h_max       37
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         3.114
_diffrn_reflns_theta_max         67.238
_diffrn_reflns_theta_full        67.238
_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             5210
_reflns_number_gt                3437
_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.
 
 Structure factors included contributions from the .fab file.
 
 _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       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_structure_solution    'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.2000P)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_number_reflns         5210
_refine_ls_number_parameters     362
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1130
_refine_ls_R_factor_gt           0.0780
_refine_ls_wR_factor_ref         0.2975
_refine_ls_wR_factor_gt          0.2603
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_restrained_S_all      1.009
_refine_ls_shift/su_max          0.008
_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 0.14188(3) 0.80419(9) 0.45820(4) 0.0641(3) Uani 1 1 d . . . . .
N1 N 0.19710(19) 1.0024(5) 0.4049(3) 0.0426(11) Uani 1 1 d . . . . .
O6 O 0.06211(19) 0.9697(9) 0.0807(3) 0.0813(18) Uani 1 1 d . . . . .
O7 O 0.09321(19) 1.0220(8) 0.0192(3) 0.0791(18) Uani 1 1 d . . . . .
N4 N 0.4688(4) 0.9293(17) 0.4035(6) 0.115(4) Uani 1 1 d . . . . .
O1 O 0.22666(19) 1.1848(5) 0.3748(3) 0.0581(12) Uani 1 1 d . . . . .
O2 O 0.25246(16) 0.9879(6) 0.2417(2) 0.0552(12) Uani 1 1 d . . . . .
O3 O 0.28114(19) 1.1673(5) 0.3316(4) 0.0676(14) Uani 1 1 d . . . . .
H3 H 0.262870 1.178342 0.341387 0.101 Uiso 1 1 calc R U . . .
O4 O 0.4773(4) 0.8046(14) 0.3933(9) 0.165(5) Uani 1 1 d . . . . .
O5 O 0.4963(3) 1.0397(16) 0.4297(7) 0.154(5) Uani 1 1 d . . . . .
C1 C 0.1724(2) 0.7507(8) 0.4170(4) 0.0491(14) Uani 1 1 d . . . . .
C2 C 0.1726(3) 0.6025(7) 0.4023(4) 0.0573(17) Uani 1 1 d . . . . .
H2 H 0.160374 0.534861 0.416931 0.069 Uiso 1 1 calc R U . . .
C3 C 0.1906(3) 0.5537(8) 0.3665(5) 0.0638(19) Uani 1 1 d . . . . .
H3A H 0.191323 0.454075 0.358794 0.077 Uiso 1 1 calc R U . . .
C4 C 0.2075(3) 0.6538(7) 0.3423(4) 0.0530(15) Uani 1 1 d . . . . .
H4A H 0.218846 0.622398 0.316882 0.064 Uiso 1 1 calc R U . . .
C5 C 0.2074(2) 0.7998(7) 0.3563(3) 0.0441(13) Uani 1 1 d . . . . .
C6 C 0.1915(2) 0.8492(7) 0.3962(3) 0.0438(13) Uani 1 1 d . . . . .
C7 C 0.1938(2) 1.0972(8) 0.4542(4) 0.0509(15) Uani 1 1 d . . . . .
H7A H 0.218926 1.169050 0.477203 0.061 Uiso 1 1 calc R U . . .
H7B H 0.198900 1.037844 0.494288 0.061 Uiso 1 1 calc R U . . .
C8 C 0.1475(2) 1.1769(7) 0.4153(4) 0.0488(14) Uani 1 1 d . . . . .
C9 C 0.1157(3) 1.1922(12) 0.3391(5) 0.091(3) Uani 1 1 d . . . . .
H9 H 0.122077 1.149332 0.308861 0.110 Uiso 1 1 calc R U . . .
C10 C 0.0741(4) 1.2699(16) 0.3053(7) 0.114(4) Uani 1 1 d . . . . .
H10 H 0.053193 1.279634 0.253182 0.137 Uiso 1 1 calc R U . . .
C11 C 0.0639(4) 1.3326(14) 0.3492(8) 0.103(4) Uani 1 1 d . . . . .
H11 H 0.036093 1.384749 0.327446 0.124 Uiso 1 1 calc R U . . .
C12 C 0.0952(4) 1.3165(12) 0.4248(7) 0.094(3) Uani 1 1 d . . . . .
H12 H 0.088657 1.358194 0.455014 0.113 Uiso 1 1 calc R U . . .
C13 C 0.1371(3) 1.2390(11) 0.4584(5) 0.072(2) Uani 1 1 d . . . . .
H13 H 0.157997 1.229455 0.510576 0.086 Uiso 1 1 calc R U . . .
C14 C 0.2160(2) 1.0564(7) 0.3720(3) 0.0441(13) Uani 1 1 d . . . . .
C15 C 0.2218(2) 0.9313(6) 0.3332(3) 0.0414(12) Uani 1 1 d . . . . .
C16 C 0.1881(2) 0.9554(6) 0.2479(3) 0.0399(12) Uani 1 1 d . . . . .
C17 C 0.1388(2) 0.9494(8) 0.2075(4) 0.0521(15) Uani 1 1 d . . . . .
H17 H 0.125979 0.930651 0.232017 0.062 Uiso 1 1 calc R U . . .
C18 C 0.1106(2) 0.9715(9) 0.1321(4) 0.0571(16) Uani 1 1 d . . . . .
C19 C 0.1288(2) 1.0034(8) 0.0939(4) 0.0499(14) Uani 1 1 d . . . . .
C20 C 0.1762(2) 1.0076(8) 0.1315(4) 0.0537(16) Uani 1 1 d . . . . .
H20 H 0.188558 1.025981 0.106163 0.064 Uiso 1 1 calc R U . . .
C21 C 0.2058(2) 0.9836(7) 0.2090(4) 0.0447(13) Uani 1 1 d . . . . .
C22 C 0.0514(3) 1.0054(15) 0.0100(5) 0.091(3) Uani 1 1 d . . . . .
H22A H 0.032500 0.928127 -0.026127 0.109 Uiso 1 1 calc R U . . .
H22B H 0.033386 1.095583 -0.009223 0.109 Uiso 1 1 calc R U . . .
C23 C 0.2733(2) 0.9181(8) 0.3618(4) 0.0484(14) Uani 1 1 d . . . . .
H23A H 0.294400 0.940534 0.415179 0.058 Uiso 1 1 calc R U . . .
H23B H 0.279070 0.817603 0.355639 0.058 Uiso 1 1 calc R U . . .
C24 C 0.2846(2) 1.0182(7) 0.3214(4) 0.0458(13) Uani 1 1 d . . . . .
C25 C 0.3334(3) 0.9912(8) 0.3434(4) 0.0550(16) Uani 1 1 d . . . . .
C26 C 0.3675(3) 1.1034(13) 0.3818(5) 0.081(3) Uani 1 1 d . . . . .
H26 H 0.360456 1.190109 0.394579 0.098 Uiso 1 1 calc R U . . .
C27 C 0.4123(3) 1.0825(13) 0.4005(6) 0.090(3) Uani 1 1 d . . . . .
H27 H 0.435259 1.155203 0.425042 0.108 Uiso 1 1 calc R U . . .
C28 C 0.4210(3) 0.9536(13) 0.3817(6) 0.083(3) Uani 1 1 d . . . . .
C29 C 0.3879(4) 0.8465(11) 0.3406(7) 0.089(3) Uani 1 1 d . . . . .
H29 H 0.395344 0.760728 0.327734 0.107 Uiso 1 1 calc R U . . .
C30 C 0.3416(3) 0.8706(9) 0.3180(6) 0.077(2) Uani 1 1 d . . . . .
H30 H 0.317470 0.804502 0.286351 0.092 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 C1 1.891(6) . ?
N1 C14 1.371(8) . ?
N1 C6 1.410(8) . ?
N1 C7 1.471(7) . ?
O6 C18 1.380(9) . ?
O6 C22 1.427(11) . ?
O7 C19 1.359(8) . ?
O7 C22 1.397(10) . ?
N4 O4 1.238(16) . ?
N4 O5 1.274(17) . ?
N4 C28 1.487(13) . ?
O1 C14 1.224(8) . ?
O2 C21 1.358(8) . ?
O2 C24 1.442(8) . ?
O3 C24 1.400(8) . ?
C1 C6 1.380(9) . ?
C1 C2 1.394(10) . ?
C2 C3 1.384(10) . ?
C3 C4 1.385(10) . ?
C4 C5 1.371(9) . ?
C5 C6 1.405(8) . ?
C5 C15 1.522(8) . ?
C7 C8 1.508(9) . ?
C8 C9 1.363(12) . ?
C8 C13 1.365(10) . ?
C9 C10 1.387(14) . ?
C10 C11 1.376(16) . ?
C11 C12 1.351(17) . ?
C12 C13 1.394(13) . ?
C14 C15 1.531(8) . ?
C15 C16 1.530(8) . ?
C15 C23 1.548(8) . ?
C16 C21 1.392(8) . ?
C16 C17 1.411(9) . ?
C17 C18 1.354(10) . ?
C18 C19 1.398(10) . ?
C19 C20 1.362(10) . ?
C20 C21 1.394(9) . ?
C23 C24 1.515(8) . ?
C24 C25 1.522(9) . ?
C25 C30 1.356(11) . ?
C25 C26 1.414(12) . ?
C26 C27 1.409(12) . ?
C27 C28 1.352(15) . ?
C28 C29 1.369(15) . ?
C29 C30 1.431(12) . ?

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
C14 N1 C6 110.9(5) . . ?
C14 N1 C7 119.7(5) . . ?
C6 N1 C7 128.2(5) . . ?
C18 O6 C22 105.4(6) . . ?
C19 O7 C22 106.2(6) . . ?
O4 N4 O5 127.1(11) . . ?
O4 N4 C28 116.4(13) . . ?
O5 N4 C28 116.5(13) . . ?
C21 O2 C24 117.2(5) . . ?
C6 C1 C2 118.4(6) . . ?
C6 C1 Br1 124.3(5) . . ?
C2 C1 Br1 117.2(5) . . ?
C3 C2 C1 121.6(6) . . ?
C2 C3 C4 119.8(6) . . ?
C5 C4 C3 119.0(6) . . ?
C4 C5 C6 121.4(6) . . ?
C4 C5 C15 129.6(6) . . ?
C6 C5 C15 109.0(5) . . ?
C1 C6 C5 119.6(6) . . ?
C1 C6 N1 131.1(6) . . ?
C5 C6 N1 109.2(5) . . ?
N1 C7 C8 114.9(5) . . ?
C9 C8 C13 117.9(7) . . ?
C9 C8 C7 123.5(7) . . ?
C13 C8 C7 118.6(7) . . ?
C8 C9 C10 122.0(9) . . ?
C11 C10 C9 119.7(11) . . ?
C12 C11 C10 118.4(9) . . ?
C11 C12 C13 121.6(9) . . ?
C8 C13 C12 120.3(9) . . ?
O1 C14 N1 124.2(6) . . ?
O1 C14 C15 126.6(6) . . ?
N1 C14 C15 109.3(5) . . ?
C5 C15 C16 111.7(5) . . ?
C5 C15 C14 101.3(4) . . ?
C16 C15 C14 109.1(5) . . ?
C5 C15 C23 111.8(5) . . ?
C16 C15 C23 110.7(5) . . ?
C14 C15 C23 111.8(5) . . ?
C21 C16 C17 119.0(5) . . ?
C21 C16 C15 120.0(5) . . ?
C17 C16 C15 121.0(5) . . ?
C18 C17 C16 118.4(6) . . ?
C17 C18 O6 129.3(7) . . ?
C17 C18 C19 122.1(6) . . ?
O6 C18 C19 108.6(6) . . ?
O7 C19 C20 129.2(6) . . ?
O7 C19 C18 110.2(6) . . ?
C20 C19 C18 120.5(6) . . ?
C19 C20 C21 118.2(6) . . ?
O2 C21 C16 124.1(5) . . ?
O2 C21 C20 114.2(5) . . ?
C16 C21 C20 121.8(6) . . ?
O7 C22 O6 109.6(7) . . ?
C24 C23 C15 113.7(5) . . ?
O3 C24 O2 107.9(6) . . ?
O3 C24 C23 113.7(6) . . ?
O2 C24 C23 109.0(5) . . ?
O3 C24 C25 107.9(5) . . ?
O2 C24 C25 104.8(5) . . ?
C23 C24 C25 113.1(5) . . ?
C30 C25 C26 120.8(8) . . ?
C30 C25 C24 120.1(7) . . ?
C26 C25 C24 118.5(7) . . ?
C27 C26 C25 119.3(10) . . ?
C28 C27 C26 117.9(10) . . ?
C27 C28 C29 124.1(9) . . ?
C27 C28 N4 118.1(11) . . ?
C29 C28 N4 117.7(10) . . ?
C28 C29 C30 118.0(9) . . ?
C25 C30 C29 119.1(9) . . ?

_refine_diff_density_max         0.741
_refine_diff_density_min         -0.443
_refine_diff_density_rms         0.094




####################################################################### 
# 
# 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_exp_10890
_database_code_depnum_ccdc_archive 'CCDC 1973528'
loop_
_audit_author_name
_audit_author_address
'Hongjin Shi'
;QingDao Agriculture university
China
;
_audit_update_record             
;
2019-12-22 deposited with the CCDC.	2020-02-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H20 Cl N O5'
_chemical_formula_weight         509.92

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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           ?
_symmetry_space_group_name_H-M   ?

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.8076(8)
_cell_length_b                   10.9039(10)
_cell_length_c                   13.2998(11)
_cell_angle_alpha                74.813(8)
_cell_angle_beta                 84.488(7)
_cell_angle_gamma                78.227(8)
_cell_volume                     1205.51(19)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.405
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             528
_exptl_absorpt_coefficient_mu    1.766
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.8716
_exptl_absorpt_correction_T_max  0.8864
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7553
_diffrn_reflns_av_R_equivalents  0.0303
_diffrn_reflns_av_sigmaI/netI    0.0567
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.45
_diffrn_reflns_theta_max         67.23
_reflns_number_total             4296
_reflns_number_gt                2925
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0509P)²+0.6179P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4296
_refine_ls_number_parameters     334
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0874
_refine_ls_R_factor_gt           0.0599
_refine_ls_wR_factor_ref         0.1672
_refine_ls_wR_factor_gt          0.1538
_refine_ls_goodness_of_fit_ref   1.149
_refine_ls_restrained_S_all      1.149
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.20916(16) 1.44123(12) -0.00957(11) 0.0957(5) Uani 1 1 d . . .
N1 N 0.4050(3) 0.9509(2) 0.3223(2) 0.0374(6) Uani 1 1 d . . .
O1 O -0.1238(3) 0.9319(2) 0.2075(2) 0.0543(7) Uani 1 1 d . . .
O2 O -0.0833(3) 0.8305(2) 0.41254(19) 0.0496(6) Uani 1 1 d . . .
O3 O 0.0710(3) 0.4347(3) 0.6806(2) 0.0655(8) Uani 1 1 d . . .
O4 O 0.3296(3) 0.4302(3) 0.6286(2) 0.0681(8) Uani 1 1 d . . .
O5 O 0.2617(3) 0.9796(2) 0.47058(19) 0.0520(6) Uani 1 1 d . . .
C1 C 0.1340(5) 1.3102(4) 0.0671(3) 0.0626(11) Uani 1 1 d . . .
C2 C 0.0859(6) 1.2288(5) 0.0199(4) 0.0828(15) Uani 1 1 d . . .
H2 H 0.0934 1.2431 -0.0523 0.099 Uiso 1 1 calc R . .
C3 C 0.0263(6) 1.1253(4) 0.0805(3) 0.0729(13) Uani 1 1 d . . .
H3 H -0.0082 1.0705 0.0484 0.087 Uiso 1 1 calc R . .
C4 C 0.0163(4) 1.1005(3) 0.1877(3) 0.0424(8) Uani 1 1 d . . .
C5 C 0.0666(5) 1.1844(4) 0.2331(3) 0.0620(11) Uani 1 1 d . . .
H5 H 0.0616 1.1696 0.3054 0.074 Uiso 1 1 calc R . .
C6 C 0.1242(6) 1.2900(4) 0.1727(3) 0.0731(13) Uani 1 1 d . . .
H6 H 0.1561 1.3469 0.2039 0.088 Uiso 1 1 calc R . .
C7 C -0.0444(4) 0.9836(3) 0.2473(3) 0.0421(8) Uani 1 1 d . . .
C8 C 0.0067(4) 0.9257(3) 0.3582(3) 0.0399(7) Uani 1 1 d . . .
H8 H -0.0075 0.9947 0.3948 0.048 Uiso 1 1 calc R . .
C9 C 0.0166(4) 0.7315(3) 0.4730(3) 0.0405(8) Uani 1 1 d . . .
C10 C -0.0327(4) 0.6352(3) 0.5537(3) 0.0483(9) Uani 1 1 d . . .
H10 H -0.1367 0.6347 0.5736 0.058 Uiso 1 1 calc R . .
C11 C 0.0850(4) 0.5418(3) 0.6007(3) 0.0484(9) Uani 1 1 d . . .
C12 C 0.2260(5) 0.3686(4) 0.7039(4) 0.0751(13) Uani 1 1 d . . .
H12A H 0.2489 0.3714 0.7731 0.090 Uiso 1 1 calc R . .
H12B H 0.2375 0.2788 0.7023 0.090 Uiso 1 1 calc R . .
C13 C 0.2397(4) 0.5406(3) 0.5708(3) 0.0469(8) Uani 1 1 d . . .
C14 C 0.2885(4) 0.6365(3) 0.4937(3) 0.0447(8) Uani 1 1 d . . .
H14 H 0.3929 0.6363 0.4745 0.054 Uiso 1 1 calc R . .
C15 C 0.1701(4) 0.7350(3) 0.4457(2) 0.0377(7) Uani 1 1 d . . .
C16 C 0.1823(3) 0.8561(3) 0.3611(2) 0.0355(7) Uani 1 1 d . . .
C17 C 0.2634(4) 0.8345(3) 0.2599(2) 0.0364(7) Uani 1 1 d . . .
C18 C 0.2294(4) 0.7689(3) 0.1922(3) 0.0451(8) Uani 1 1 d . . .
H18 H 0.1442 0.7278 0.2055 0.054 Uiso 1 1 calc R . .
C19 C 0.3256(4) 0.7654(4) 0.1033(3) 0.0534(9) Uani 1 1 d . . .
H19 H 0.3038 0.7225 0.0561 0.064 Uiso 1 1 calc R . .
C20 C 0.4534(4) 0.8250(4) 0.0844(3) 0.0537(10) Uani 1 1 d . . .
H20 H 0.5157 0.8222 0.0242 0.064 Uiso 1 1 calc R . .
C21 C 0.4905(4) 0.8888(3) 0.1538(3) 0.0452(8) Uani 1 1 d . . .
H21 H 0.5777 0.9274 0.1418 0.054 Uiso 1 1 calc R . .
C22 C 0.3936(4) 0.8929(3) 0.2410(2) 0.0359(7) Uani 1 1 d . . .
C23 C 0.2843(4) 0.9374(3) 0.3940(3) 0.0382(7) Uani 1 1 d . . .
C24 C 0.5373(4) 1.0067(3) 0.3374(3) 0.0426(8) Uani 1 1 d . . .
H24A H 0.6296 0.9659 0.3041 0.051 Uiso 1 1 calc R . .
H24B H 0.5541 0.9861 0.4114 0.051 Uiso 1 1 calc R . .
C25 C 0.5175(4) 1.1512(3) 0.2946(3) 0.0404(8) Uani 1 1 d . . .
C26 C 0.4492(4) 1.2343(4) 0.3561(3) 0.0536(9) Uani 1 1 d . . .
H26 H 0.4106 1.2004 0.4230 0.064 Uiso 1 1 calc R . .
C27 C 0.4375(5) 1.3665(4) 0.3198(3) 0.0625(11) Uani 1 1 d . . .
H27 H 0.3918 1.4209 0.3621 0.075 Uiso 1 1 calc R . .
C28 C 0.4937(5) 1.4178(4) 0.2205(4) 0.0694(12) Uani 1 1 d . . .
H28 H 0.4859 1.5067 0.1955 0.083 Uiso 1 1 calc R . .
C29 C 0.5609(6) 1.3367(4) 0.1592(4) 0.0757(13) Uani 1 1 d . . .
H29 H 0.5985 1.3711 0.0921 0.091 Uiso 1 1 calc R . .
C30 C 0.5738(5) 1.2040(4) 0.1959(3) 0.0575(10) Uani 1 1 d . . .
H30 H 0.6209 1.1500 0.1535 0.069 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C1 1.736(4) . ?
N1 C23 1.363(4) . ?
N1 C22 1.409(4) . ?
N1 C24 1.471(4) . ?
O1 C7 1.215(4) . ?
O2 C9 1.371(4) . ?
O2 C8 1.436(4) . ?
O3 C11 1.375(4) . ?
O3 C12 1.429(5) . ?
O4 C13 1.382(4) . ?
O4 C12 1.418(5) . ?
O5 C23 1.207(4) . ?
C1 C6 1.361(6) . ?
C1 C2 1.364(6) . ?
C2 C3 1.372(6) . ?
C3 C4 1.378(5) . ?
C4 C5 1.380(5) . ?
C4 C7 1.485(5) . ?
C5 C6 1.380(5) . ?
C7 C8 1.517(5) . ?
C8 C16 1.577(4) . ?
C9 C15 1.371(4) . ?
C9 C10 1.396(4) . ?
C10 C11 1.364(5) . ?
C11 C13 1.380(5) . ?
C13 C14 1.366(4) . ?
C14 C15 1.401(5) . ?
C15 C16 1.509(4) . ?
C16 C17 1.513(4) . ?
C16 C23 1.545(4) . ?
C17 C18 1.375(4) . ?
C17 C22 1.394(4) . ?
C18 C19 1.391(5) . ?
C19 C20 1.382(5) . ?
C20 C21 1.390(5) . ?
C21 C22 1.377(4) . ?
C24 C25 1.509(4) . ?
C25 C30 1.377(5) . ?
C25 C26 1.386(5) . ?
C26 C27 1.381(5) . ?
C27 C28 1.378(6) . ?
C28 C29 1.367(6) . ?
C29 C30 1.386(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C23 N1 C22 111.6(2) . . ?
C23 N1 C24 122.4(3) . . ?
C22 N1 C24 125.7(3) . . ?
C9 O2 C8 106.8(2) . . ?
C11 O3 C12 105.8(3) . . ?
C13 O4 C12 105.6(3) . . ?
C6 C1 C2 121.1(4) . . ?
C6 C1 Cl1 119.9(4) . . ?
C2 C1 Cl1 119.0(4) . . ?
C1 C2 C3 119.0(4) . . ?
C2 C3 C4 121.7(4) . . ?
C3 C4 C5 117.9(4) . . ?
C3 C4 C7 118.0(3) . . ?
C5 C4 C7 124.1(3) . . ?
C4 C5 C6 120.9(4) . . ?
C1 C6 C5 119.5(4) . . ?
O1 C7 C4 121.8(3) . . ?
O1 C7 C8 121.2(3) . . ?
C4 C7 C8 116.9(3) . . ?
O2 C8 C7 110.7(3) . . ?
O2 C8 C16 107.1(2) . . ?
C7 C8 C16 111.7(3) . . ?
C15 C9 O2 113.5(3) . . ?
C15 C9 C10 123.1(3) . . ?
O2 C9 C10 123.4(3) . . ?
C11 C10 C9 114.2(3) . . ?
C10 C11 O3 127.0(3) . . ?
C10 C11 C13 123.4(3) . . ?
O3 C11 C13 109.6(3) . . ?
O4 C12 O3 108.5(3) . . ?
C14 C13 C11 122.5(3) . . ?
C14 C13 O4 127.7(3) . . ?
C11 C13 O4 109.8(3) . . ?
C13 C14 C15 115.2(3) . . ?
C9 C15 C14 121.5(3) . . ?
C9 C15 C16 109.3(3) . . ?
C14 C15 C16 129.2(3) . . ?
C15 C16 C17 115.4(3) . . ?
C15 C16 C23 111.0(3) . . ?
C17 C16 C23 102.3(2) . . ?
C15 C16 C8 99.9(2) . . ?
C17 C16 C8 117.8(3) . . ?
C23 C16 C8 110.8(2) . . ?
C18 C17 C22 120.5(3) . . ?
C18 C17 C16 130.9(3) . . ?
C22 C17 C16 108.5(3) . . ?
C17 C18 C19 118.3(3) . . ?
C20 C19 C18 120.8(3) . . ?
C19 C20 C21 121.2(3) . . ?
C22 C21 C20 117.6(3) . . ?
C21 C22 C17 121.6(3) . . ?
C21 C22 N1 128.7(3) . . ?
C17 C22 N1 109.7(3) . . ?
O5 C23 N1 126.3(3) . . ?
O5 C23 C16 125.8(3) . . ?
N1 C23 C16 107.9(3) . . ?
N1 C24 C25 114.5(3) . . ?
C30 C25 C26 118.3(3) . . ?
C30 C25 C24 121.1(3) . . ?
C26 C25 C24 120.6(3) . . ?
C27 C26 C25 121.1(3) . . ?
C28 C27 C26 119.9(4) . . ?
C29 C28 C27 119.5(4) . . ?
C28 C29 C30 120.7(4) . . ?
C25 C30 C29 120.5(4) . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        67.23
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.216
_refine_diff_density_min         -0.289
_refine_diff_density_rms         0.061
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
