# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_bacba
_database_code_depnum_ccdc_archive 'CCDC 1411558'
_audit_update_record             
;
2015-07-08 deposited with the CCDC.
2015-09-20 downloaded from the CCDC.
;


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          371
_chemical_formula_moiety         ?
_chemical_formula_sum            'C41 H42 Cl2 N2 O10'
_chemical_formula_weight         793.67

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/c

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

_cell_length_a                   14.910(3)
_cell_length_b                   35.478(7)
_cell_length_c                   7.4293(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.21(3)
_cell_angle_gamma                90.00
_cell_volume                     3879.3(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    6254
_cell_measurement_theta_min      1.80
_cell_measurement_theta_max      26.38

_exptl_crystal_description       rod
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.359
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1664
_exptl_absorpt_coefficient_mu    0.229
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9346
_exptl_absorpt_correction_T_max  0.9887
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_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            7879
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0243
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -44
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         1.80
_diffrn_reflns_theta_max         26.38
_reflns_number_total             7879
_reflns_number_gt                6254
_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)+(0.0394P)²+2.5655P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    noref
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       ?
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         7879
_refine_ls_number_parameters     533
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0610
_refine_ls_R_factor_gt           0.0430
_refine_ls_wR_factor_ref         0.1068
_refine_ls_wR_factor_gt          0.0966
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_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
O1B O 0.09743(8) -0.01089(3) 1.15259(16) 0.0294(3) Uani 1 1 d . . .
O2B O 0.12472(9) -0.03132(3) 0.88249(17) 0.0312(3) Uani 1 1 d . . .
N2 N 0.16299(11) 0.03547(5) 0.4362(2) 0.0265(3) Uani 1 1 d . . .
O4E O -0.07640(9) 0.09969(4) 0.06758(19) 0.0382(3) Uani 1 1 d . . .
O3E O 0.04735(9) 0.09105(4) 0.27610(19) 0.0416(3) Uani 1 1 d . . .
C1B C 0.19609(11) 0.08447(5) 0.7588(2) 0.0236(3) Uani 1 1 d . . .
C10B C 0.11541(12) 0.02902(5) 0.5952(2) 0.0272(4) Uani 1 1 d . . .
H10C H 0.1028 0.0018 0.6055 0.033 Uiso 1 1 calc R . .
H10D H 0.0565 0.0425 0.5754 0.033 Uiso 1 1 calc R . .
C3B C 0.30588(12) 0.13293(5) 0.7204(3) 0.0334(4) Uani 1 1 d . . .
H3B H 0.3659 0.1400 0.7066 0.040 Uiso 1 1 calc R . .
C9B C 0.11556(11) -0.00556(5) 0.9928(2) 0.0238(3) Uani 1 1 d . . .
C7E C 0.00037(12) 0.11099(5) 0.1666(2) 0.0295(4) Uani 1 1 d . . .
C8B C 0.12567(12) 0.03544(5) 0.9391(2) 0.0258(4) Uani 1 1 d . . .
H8C H 0.1603 0.0488 1.0450 0.031 Uiso 1 1 calc R . .
H8D H 0.0643 0.0469 0.9150 0.031 Uiso 1 1 calc R . .
C4B C 0.23956(13) 0.15999(5) 0.7207(2) 0.0313(4) Uani 1 1 d . . .
C2B C 0.28388(12) 0.09523(5) 0.7403(2) 0.0292(4) Uani 1 1 d . . .
H2B H 0.3295 0.0765 0.7414 0.035 Uiso 1 1 calc R . .
C1E C 0.02343(12) 0.15106(5) 0.1325(2) 0.0287(4) Uani 1 1 d . . .
C6E C -0.03127(13) 0.17320(5) 0.0043(3) 0.0344(4) Uani 1 1 d . . .
H6E H -0.0846 0.1628 -0.0650 0.041 Uiso 1 1 calc R . .
C7B C 0.17255(11) 0.04280(4) 0.7727(2) 0.0230(3) Uani 1 1 d . . .
H7B H 0.2308 0.0283 0.7907 0.028 Uiso 1 1 calc R . .
C6B C 0.13076(12) 0.11254(5) 0.7597(2) 0.0303(4) Uani 1 1 d . . .
H6B H 0.0706 0.1057 0.7730 0.036 Uiso 1 1 calc R . .
C2E C 0.10126(13) 0.16670(6) 0.2340(3) 0.0360(4) Uani 1 1 d . . .
H2E H 0.1393 0.1517 0.3207 0.043 Uiso 1 1 calc R . .
C3E C 0.12331(14) 0.20399(6) 0.2090(3) 0.0437(5) Uani 1 1 d . . .
H3E H 0.1758 0.2147 0.2800 0.052 Uiso 1 1 calc R . .
C5B C 0.15206(13) 0.15036(5) 0.7414(3) 0.0339(4) Uani 1 1 d . . .
H5B H 0.1071 0.1693 0.7431 0.041 Uiso 1 1 calc R . .
C4E C 0.06889(15) 0.22585(6) 0.0807(3) 0.0447(5) Uani 1 1 d . . .
H4E H 0.0843 0.2514 0.0633 0.054 Uiso 1 1 calc R . .
C5E C -0.00771(14) 0.21041(6) -0.0220(3) 0.0421(5) Uani 1 1 d . . .
H5E H -0.0445 0.2253 -0.1111 0.051 Uiso 1 1 calc R . .
O1A O 0.64545(8) -0.00785(3) 1.49809(16) 0.0309(3) Uani 1 1 d . . .
O2A O 0.56616(8) -0.01725(3) 1.22172(17) 0.0318(3) Uani 1 1 d . . .
N1 N 0.60430(11) 0.04256(5) 0.7579(2) 0.0273(3) Uani 1 1 d . . .
C10A C 0.64523(12) 0.03131(5) 0.9461(2) 0.0269(4) Uani 1 1 d . . .
H10A H 0.7117 0.0356 0.9636 0.032 Uiso 1 1 calc R . .
H10B H 0.6348 0.0041 0.9632 0.032 Uiso 1 1 calc R . .
C1A C 0.61481(12) 0.09592(5) 1.0606(2) 0.0270(4) Uani 1 1 d . . .
C9A C 0.61564(11) 0.00256(5) 1.3338(2) 0.0249(4) Uani 1 1 d . . .
C7A C 0.60386(11) 0.05387(5) 1.0879(2) 0.0255(4) Uani 1 1 d . . .
H7A H 0.5374 0.0482 1.0709 0.031 Uiso 1 1 calc R . .
C8A C 0.64604(12) 0.04121(5) 1.2801(2) 0.0291(4) Uani 1 1 d . . .
H8A H 0.7130 0.0411 1.2885 0.035 Uiso 1 1 calc R . .
H8B H 0.6305 0.0599 1.3689 0.035 Uiso 1 1 calc R . .
C6A C 0.54100(13) 0.11768(5) 0.9856(3) 0.0368(4) Uani 1 1 d . . .
H6A H 0.4833 0.1060 0.9530 0.044 Uiso 1 1 calc R . .
C2A C 0.69841(13) 0.11368(6) 1.1074(3) 0.0414(5) Uani 1 1 d . . .
H2A H 0.7500 0.0993 1.1581 0.050 Uiso 1 1 calc R . .
C4A C 0.63261(15) 0.17280(5) 1.0053(3) 0.0429(5) Uani 1 1 d . . .
C5A C 0.54948(14) 0.15612(6) 0.9571(3) 0.0439(5) Uani 1 1 d . . .
H5A H 0.4983 0.1706 0.9049 0.053 Uiso 1 1 calc R . .
C3A C 0.70755(15) 0.15205(6) 1.0812(3) 0.0497(6) Uani 1 1 d . . .
H3A H 0.7648 0.1640 1.1152 0.060 Uiso 1 1 calc R . .
O4C O 0.90222(9) 0.07395(4) 0.66970(19) 0.0358(3) Uani 1 1 d . . .
O3C O 0.75612(9) 0.07862(4) 0.6972(2) 0.0453(4) Uani 1 1 d . . .
C2C C 0.90188(12) 0.14652(5) 0.5211(2) 0.0322(4) Uani 1 1 d . . .
H2C H 0.9516 0.1306 0.5072 0.039 Uiso 1 1 calc R . .
C7C C 0.82478(12) 0.09246(5) 0.6571(2) 0.0311(4) Uani 1 1 d . . .
C3C C 0.90283(14) 0.18405(6) 0.4702(3) 0.0419(5) Uani 1 1 d . . .
H3C H 0.9521 0.1937 0.4172 0.050 Uiso 1 1 calc R . .
C6C C 0.75717(15) 0.15577(7) 0.6181(4) 0.0565(6) Uani 1 1 d . . .
H6C H 0.7066 0.1460 0.6663 0.068 Uiso 1 1 calc R . .
C1C C 0.82820(12) 0.13205(5) 0.5927(3) 0.0332(4) Uani 1 1 d . . .
C4C C 0.83214(17) 0.20749(7) 0.4964(4) 0.0620(7) Uani 1 1 d . . .
H4C H 0.8329 0.2332 0.4618 0.074 Uiso 1 1 calc R . .
C5C C 0.75989(17) 0.19353(7) 0.5734(5) 0.0729(9) Uani 1 1 d . . .
H5C H 0.7124 0.2099 0.5953 0.088 Uiso 1 1 calc R . .
O4D O 0.43207(10) 0.07166(4) 0.4344(2) 0.0465(4) Uani 1 1 d . . .
O3D O 0.29737(11) 0.08134(5) 0.2610(2) 0.0592(5) Uani 1 1 d . . .
C1D C 0.40050(14) 0.13305(6) 0.3171(3) 0.0397(5) Uani 1 1 d . . .
C6D C 0.34413(14) 0.15695(6) 0.2030(3) 0.0436(5) Uani 1 1 d . . .
H6D H 0.2899 0.1474 0.1332 0.052 Uiso 1 1 calc R . .
C5D C 0.36623(17) 0.19459(7) 0.1898(3) 0.0539(6) Uani 1 1 d . . .
H5D H 0.3276 0.2108 0.1100 0.065 Uiso 1 1 calc R . .
C7D C 0.37106(14) 0.09286(6) 0.3321(3) 0.0416(5) Uani 1 1 d . . .
C4D C 0.44448(19) 0.20863(7) 0.2926(4) 0.0674(7) Uani 1 1 d . . .
H4D H 0.4594 0.2346 0.2856 0.081 Uiso 1 1 calc R . .
C2D C 0.47965(16) 0.14715(7) 0.4176(4) 0.0586(6) Uani 1 1 d . . .
H2D H 0.5193 0.1309 0.4947 0.070 Uiso 1 1 calc R . .
C3D C 0.50084(19) 0.18472(8) 0.4058(5) 0.0767(9) Uani 1 1 d . . .
H3D H 0.5548 0.1943 0.4763 0.092 Uiso 1 1 calc R . .
Cl2 Cl 0.26771(4) 0.207322(13) 0.69528(8) 0.04969(16) Uani 1 1 d . . .
Cl1 Cl 0.64340(5) 0.221047(16) 0.97070(12) 0.0752(2) Uani 1 1 d . . .
H11D H 0.1606(14) 0.0597(7) 0.407(3) 0.041(6) Uiso 1 1 d . . .
H11B H 0.6197(14) 0.0659(6) 0.736(3) 0.038(6) Uiso 1 1 d . . .
H11F H 0.1360(15) 0.0217(6) 0.332(3) 0.047(6) Uiso 1 1 d . . .
H11C H 0.6248(15) 0.0257(7) 0.665(3) 0.051(6) Uiso 1 1 d . . .
H7C H 0.9002(18) 0.0523(8) 0.726(4) 0.068(8) Uiso 1 1 d . . .
H7E H -0.0891(18) 0.0756(8) 0.086(4) 0.070(8) Uiso 1 1 d . . .
H7D H 0.397(2) 0.0466(9) 0.452(4) 0.095(10) Uiso 1 1 d . . .
H11A H 0.5413(16) 0.0404(6) 0.744(3) 0.044(6) Uiso 1 1 d . . .
H11E H 0.2212(16) 0.0273(6) 0.463(3) 0.043(6) Uiso 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
O1B C9B 1.273(2) . ?
O2B C9B 1.250(2) . ?
N2 C10B 1.490(2) . ?
O4E C7E 1.320(2) . ?
O3E C7E 1.213(2) . ?
C1B C2B 1.391(2) . ?
C1B C6B 1.394(2) . ?
C1B C7B 1.527(2) . ?
C10B C7B 1.531(2) . ?
C3B C4B 1.379(3) . ?
C3B C2B 1.391(2) . ?
C9B C8B 1.522(2) . ?
C7E C1E 1.494(2) . ?
C8B C7B 1.537(2) . ?
C4B C5B 1.381(3) . ?
C4B Cl2 1.7485(18) . ?
C1E C6E 1.393(3) . ?
C1E C2E 1.394(3) . ?
C6E C5E 1.388(3) . ?
C6B C5B 1.391(3) . ?
C2E C3E 1.383(3) . ?
C3E C4E 1.386(3) . ?
C4E C5E 1.381(3) . ?
O1A C9A 1.285(2) . ?
O2A C9A 1.239(2) . ?
N1 C10A 1.488(2) . ?
C10A C7A 1.530(2) . ?
C1A C6A 1.386(3) . ?
C1A C2A 1.390(3) . ?
C1A C7A 1.518(2) . ?
C9A C8A 1.517(2) . ?
C7A C8A 1.533(2) . ?
C6A C5A 1.389(3) . ?
C2A C3A 1.385(3) . ?
C4A C5A 1.369(3) . ?
C4A C3A 1.381(3) . ?
C4A Cl1 1.742(2) . ?
O4C C7C 1.318(2) . ?
O3C C7C 1.215(2) . ?
C2C C3C 1.385(3) . ?
C2C C1C 1.393(3) . ?
C7C C1C 1.487(3) . ?
C3C C4C 1.381(3) . ?
C6C C5C 1.382(3) . ?
C6C C1C 1.389(3) . ?
C4C C5C 1.389(3) . ?
O4D C7D 1.323(2) . ?
O3D C7D 1.212(2) . ?
C1D C6D 1.384(3) . ?
C1D C2D 1.385(3) . ?
C1D C7D 1.501(3) . ?
C6D C5D 1.383(3) . ?
C5D C4D 1.381(4) . ?
C4D C3D 1.381(4) . ?
C2D C3D 1.376(4) . ?

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
C2B C1B C6B 118.29(15) . . ?
C2B C1B C7B 120.16(15) . . ?
C6B C1B C7B 121.53(15) . . ?
N2 C10B C7B 111.34(14) . . ?
C4B C3B C2B 119.21(17) . . ?
O2B C9B O1B 124.38(15) . . ?
O2B C9B C8B 120.08(15) . . ?
O1B C9B C8B 115.54(14) . . ?
O3E C7E O4E 123.57(17) . . ?
O3E C7E C1E 123.02(17) . . ?
O4E C7E C1E 113.41(15) . . ?
C9B C8B C7B 116.74(14) . . ?
C3B C4B C5B 121.26(16) . . ?
C3B C4B Cl2 118.94(14) . . ?
C5B C4B Cl2 119.80(14) . . ?
C3B C2B C1B 121.07(16) . . ?
C6E C1E C2E 119.40(17) . . ?
C6E C1E C7E 121.81(16) . . ?
C2E C1E C7E 118.78(16) . . ?
C5E C6E C1E 119.94(18) . . ?
C1B C7B C10B 110.67(13) . . ?
C1B C7B C8B 110.98(13) . . ?
C10B C7B C8B 112.12(13) . . ?
C5B C6B C1B 121.21(16) . . ?
C3E C2E C1E 120.23(18) . . ?
C2E C3E C4E 120.13(19) . . ?
C4B C5B C6B 118.96(16) . . ?
C5E C4E C3E 119.97(19) . . ?
C4E C5E C6E 120.32(19) . . ?
N1 C10A C7A 110.89(14) . . ?
C6A C1A C2A 118.08(17) . . ?
C6A C1A C7A 120.36(16) . . ?
C2A C1A C7A 121.56(16) . . ?
O2A C9A O1A 123.60(16) . . ?
O2A C9A C8A 120.46(15) . . ?
O1A C9A C8A 115.94(14) . . ?
C1A C7A C10A 111.01(14) . . ?
C1A C7A C8A 112.06(14) . . ?
C10A C7A C8A 109.74(14) . . ?
C9A C8A C7A 114.49(14) . . ?
C1A C6A C5A 121.48(18) . . ?
C3A C2A C1A 120.99(19) . . ?
C5A C4A C3A 121.05(18) . . ?
C5A C4A Cl1 119.18(16) . . ?
C3A C4A Cl1 119.76(16) . . ?
C4A C5A C6A 119.05(19) . . ?
C4A C3A C2A 119.35(19) . . ?
C3C C2C C1C 120.13(18) . . ?
O3C C7C O4C 122.97(18) . . ?
O3C C7C C1C 122.29(17) . . ?
O4C C7C C1C 114.73(15) . . ?
C4C C3C C2C 119.93(19) . . ?
C5C C6C C1C 120.1(2) . . ?
C6C C1C C2C 119.58(18) . . ?
C6C C1C C7C 117.53(17) . . ?
C2C C1C C7C 122.73(17) . . ?
C3C C4C C5C 120.2(2) . . ?
C6C C5C C4C 119.9(2) . . ?
C6D C1D C2D 119.3(2) . . ?
C6D C1D C7D 118.11(19) . . ?
C2D C1D C7D 122.50(19) . . ?
C5D C6D C1D 120.5(2) . . ?
C4D C5D C6D 119.9(2) . . ?
O3D C7D O4D 123.4(2) . . ?
O3D C7D C1D 122.9(2) . . ?
O4D C7D C1D 113.60(17) . . ?
C3D C4D C5D 119.5(2) . . ?
C3D C2D C1D 120.0(2) . . ?
C2D C3D C4D 120.7(2) . . ?

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
O2B C9B C8B C7B -16.6(2) . . . . ?
O1B C9B C8B C7B 163.64(14) . . . . ?
C2B C3B C4B C5B 0.3(3) . . . . ?
C2B C3B C4B Cl2 -179.94(14) . . . . ?
C4B C3B C2B C1B 0.6(3) . . . . ?
C6B C1B C2B C3B -1.0(3) . . . . ?
C7B C1B C2B C3B 177.50(16) . . . . ?
O3E C7E C1E C6E 179.24(18) . . . . ?
O4E C7E C1E C6E -1.5(2) . . . . ?
O3E C7E C1E C2E -1.6(3) . . . . ?
O4E C7E C1E C2E 177.63(16) . . . . ?
C2E C1E C6E C5E 0.4(3) . . . . ?
C7E C1E C6E C5E 179.49(18) . . . . ?
C2B C1B C7B C10B -106.38(17) . . . . ?
C6B C1B C7B C10B 72.1(2) . . . . ?
C2B C1B C7B C8B 128.46(16) . . . . ?
C6B C1B C7B C8B -53.1(2) . . . . ?
N2 C10B C7B C1B 56.98(18) . . . . ?
N2 C10B C7B C8B -178.51(14) . . . . ?
C9B C8B C7B C1B -167.95(14) . . . . ?
C9B C8B C7B C10B 67.71(19) . . . . ?
C2B C1B C6B C5B 0.5(3) . . . . ?
C7B C1B C6B C5B -178.04(16) . . . . ?
C6E C1E C2E C3E 0.8(3) . . . . ?
C7E C1E C2E C3E -178.39(18) . . . . ?
C1E C2E C3E C4E -1.1(3) . . . . ?
C3B C4B C5B C6B -0.9(3) . . . . ?
Cl2 C4B C5B C6B 179.39(14) . . . . ?
C1B C6B C5B C4B 0.5(3) . . . . ?
C2E C3E C4E C5E 0.3(3) . . . . ?
C3E C4E C5E C6E 0.9(3) . . . . ?
C1E C6E C5E C4E -1.2(3) . . . . ?
C6A C1A C7A C10A 105.51(19) . . . . ?
C2A C1A C7A C10A -73.8(2) . . . . ?
C6A C1A C7A C8A -131.39(18) . . . . ?
C2A C1A C7A C8A 49.3(2) . . . . ?
N1 C10A C7A C1A -56.57(18) . . . . ?
N1 C10A C7A C8A 179.01(14) . . . . ?
O2A C9A C8A C7A 5.2(2) . . . . ?
O1A C9A C8A C7A -175.86(14) . . . . ?
C1A C7A C8A C9A 163.96(14) . . . . ?
C10A C7A C8A C9A -72.23(18) . . . . ?
C2A C1A C6A C5A 0.1(3) . . . . ?
C7A C1A C6A C5A -179.18(18) . . . . ?
C6A C1A C2A C3A 0.5(3) . . . . ?
C7A C1A C2A C3A 179.79(19) . . . . ?
C3A C4A C5A C6A 0.0(3) . . . . ?
Cl1 C4A C5A C6A -179.70(17) . . . . ?
C1A C6A C5A C4A -0.4(3) . . . . ?
C5A C4A C3A C2A 0.6(4) . . . . ?
Cl1 C4A C3A C2A -179.69(18) . . . . ?
C1A C2A C3A C4A -0.9(4) . . . . ?
C1C C2C C3C C4C 2.3(3) . . . . ?
C5C C6C C1C C2C -0.3(4) . . . . ?
C5C C6C C1C C7C 175.2(2) . . . . ?
C3C C2C C1C C6C -2.1(3) . . . . ?
C3C C2C C1C C7C -177.38(18) . . . . ?
O3C C7C C1C C6C 14.4(3) . . . . ?
O4C C7C C1C C6C -164.65(19) . . . . ?
O3C C7C C1C C2C -170.28(19) . . . . ?
O4C C7C C1C C2C 10.7(3) . . . . ?
C2C C3C C4C C5C -0.2(4) . . . . ?
C1C C6C C5C C4C 2.4(5) . . . . ?
C3C C4C C5C C6C -2.2(5) . . . . ?
C2D C1D C6D C5D -0.3(3) . . . . ?
C7D C1D C6D C5D 177.4(2) . . . . ?
C1D C6D C5D C4D -0.8(3) . . . . ?
C6D C1D C7D O3D -6.2(3) . . . . ?
C2D C1D C7D O3D 171.4(2) . . . . ?
C6D C1D C7D O4D 175.65(18) . . . . ?
C2D C1D C7D O4D -6.7(3) . . . . ?
C6D C5D C4D C3D 1.1(4) . . . . ?
C6D C1D C2D C3D 1.1(4) . . . . ?
C7D C1D C2D C3D -176.5(3) . . . . ?
C1D C2D C3D C4D -0.8(5) . . . . ?
C5D C4D C3D C2D -0.3(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        26.38
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.550
_refine_diff_density_min         -0.383
_refine_diff_density_rms         0.041
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methanol:water=1:1'
####################################################################### 
# 
# 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_bacnaphtacid
_database_code_depnum_ccdc_archive 'CCDC 1411559'
_audit_update_record             
;
2015-07-08 deposited with the CCDC.
2015-09-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          468-473
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H20 Cl N O5'
_chemical_formula_weight         401.83

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/c

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

_cell_length_a                   6.6251(13)
_cell_length_b                   34.490(7)
_cell_length_c                   8.4698(17)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.75(3)
_cell_angle_gamma                90.00
_cell_volume                     1925.6(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    3098
_cell_measurement_theta_min      2.36
_cell_measurement_theta_max      27.12

_exptl_crystal_description       chunk
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.386
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             840
_exptl_absorpt_coefficient_mu    0.231
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9030
_exptl_absorpt_correction_T_max  0.9750
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_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            25873
_diffrn_reflns_av_R_equivalents  0.0452
_diffrn_reflns_av_sigmaI/netI    0.0343
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -44
_diffrn_reflns_limit_k_max       44
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.36
_diffrn_reflns_theta_max         27.12
_reflns_number_total             4260
_reflns_number_gt                3098
_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)+(0.0434P)²+0.6337P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    noref
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       ?
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4260
_refine_ls_number_parameters     274
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0655
_refine_ls_R_factor_gt           0.0424
_refine_ls_wR_factor_ref         0.1065
_refine_ls_wR_factor_gt          0.0955
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.022
_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 0.40614(11) 0.217164(17) 0.65237(8) 0.0738(2) Uani 1 1 d . . .
O5 O 1.33887(16) 0.05220(3) 0.45929(14) 0.0305(3) Uani 1 1 d . . .
O4 O 1.06860(17) 0.04579(3) 0.59262(14) 0.0325(3) Uani 1 1 d . . .
C19 C 1.0813(2) 0.10029(5) 0.42138(18) 0.0245(3) Uani 1 1 d . . .
O2 O 0.73764(18) 0.01647(4) 1.30324(15) 0.0362(3) Uani 1 1 d . . .
C18 C 1.1833(2) 0.12024(5) 0.3112(2) 0.0282(4) Uani 1 1 d . . .
O1 O 1.00495(18) 0.02542(4) 1.16781(15) 0.0399(3) Uani 1 1 d . . .
C10 C 0.6479(2) 0.02934(5) 0.84966(18) 0.0256(4) Uani 1 1 d . . .
H10A H 0.7110 0.0066 0.9061 0.031 Uiso 1 1 calc R . .
H10B H 0.5011 0.0289 0.8627 0.031 Uiso 1 1 calc R . .
C16 C 0.9155(3) 0.16947(5) 0.2831(2) 0.0323(4) Uani 1 1 d . . .
N1 N 0.6754(2) 0.02601(4) 0.67684(16) 0.0248(3) Uani 1 1 d . . .
C7 C 0.7403(2) 0.06609(5) 0.92579(19) 0.0257(3) Uani 1 1 d . . .
H7 H 0.8892 0.0659 0.9149 0.031 Uiso 1 1 calc R . .
C22 C 1.1663(2) 0.06405(5) 0.49545(19) 0.0264(4) Uani 1 1 d . . .
C21 C 0.8135(3) 0.14874(5) 0.3961(2) 0.0338(4) Uani 1 1 d . . .
H21 H 0.6883 0.1582 0.4262 0.041 Uiso 1 1 calc R . .
C4 C 0.6521(2) 0.10348(5) 0.85414(18) 0.0269(4) Uani 1 1 d . . .
C20 C 0.8934(2) 0.11546(5) 0.4617(2) 0.0291(4) Uani 1 1 d . . .
H20 H 0.8219 0.1020 0.5364 0.035 Uiso 1 1 calc R . .
C1 C 0.5013(3) 0.17350(5) 0.7319(2) 0.0415(5) Uani 1 1 d . . .
C17 C 1.1022(3) 0.15502(5) 0.2390(2) 0.0305(4) Uani 1 1 d . . .
C9 C 0.8340(2) 0.03376(5) 1.19244(19) 0.0289(4) Uani 1 1 d . . .
C8 C 0.7109(3) 0.06494(5) 1.1036(2) 0.0314(4) Uani 1 1 d . . .
H8A H 0.7494 0.0904 1.1514 0.038 Uiso 1 1 calc R . .
H8B H 0.5655 0.0606 1.1157 0.038 Uiso 1 1 calc R . .
C13 C 1.1200(3) 0.20828(6) 0.0556(2) 0.0494(5) Uani 1 1 d . . .
H13 H 1.1871 0.2214 -0.0228 0.059 Uiso 1 1 calc R . .
C5 C 0.7770(3) 0.13565(5) 0.8467(2) 0.0350(4) Uani 1 1 d . . .
H5 H 0.9166 0.1336 0.8843 0.042 Uiso 1 1 calc R . .
C3 C 0.4475(3) 0.10760(5) 0.8008(2) 0.0336(4) Uani 1 1 d . . .
H3 H 0.3584 0.0862 0.8069 0.040 Uiso 1 1 calc R . .
C6 C 0.7032(3) 0.17058(6) 0.7860(2) 0.0428(5) Uani 1 1 d . . .
H6 H 0.7908 0.1923 0.7817 0.051 Uiso 1 1 calc R . .
C12 C 1.2026(3) 0.17508(6) 0.1232(2) 0.0396(5) Uani 1 1 d . . .
H12 H 1.3273 0.1655 0.0927 0.048 Uiso 1 1 calc R . .
C15 C 0.8364(3) 0.20418(6) 0.2116(2) 0.0438(5) Uani 1 1 d . . .
H15 H 0.7123 0.2144 0.2408 0.053 Uiso 1 1 calc R . .
C14 C 0.9371(4) 0.22304(6) 0.1010(3) 0.0507(5) Uani 1 1 d . . .
H14 H 0.8827 0.2463 0.0545 0.061 Uiso 1 1 calc R . .
C2 C 0.3719(3) 0.14251(6) 0.7391(2) 0.0405(5) Uani 1 1 d . . .
H2 H 0.2324 0.1450 0.7021 0.049 Uiso 1 1 calc R . .
O3 O 1.36208(18) 0.10805(4) 0.26633(16) 0.0399(3) Uani 1 1 d . . .
H11C H 0.576(3) 0.0395(6) 0.615(2) 0.038(5) Uiso 1 1 d . . .
H11A H 0.668(3) -0.0001(6) 0.642(2) 0.036(5) Uiso 1 1 d . . .
H11B H 0.799(3) 0.0356(5) 0.654(2) 0.037(5) Uiso 1 1 d . . .
H18 H 1.386(3) 0.0872(7) 0.327(3) 0.064(8) Uiso 1 1 d . . .
H9 H 0.813(4) -0.0044(7) 1.345(3) 0.070(8) Uiso 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
Cl1 C1 1.7418(19) . ?
O5 C22 1.2799(19) . ?
O4 C22 1.2647(19) . ?
C19 C18 1.388(2) . ?
C19 C20 1.423(2) . ?
C19 C22 1.484(2) . ?
O2 C9 1.328(2) . ?
C18 O3 1.3473(19) . ?
C18 C17 1.427(2) . ?
O1 C9 1.2068(19) . ?
C10 N1 1.497(2) . ?
C10 C7 1.522(2) . ?
C16 C17 1.417(2) . ?
C16 C15 1.418(3) . ?
C16 C21 1.419(3) . ?
C7 C4 1.517(2) . ?
C7 C8 1.539(2) . ?
C21 C20 1.359(2) . ?
C4 C5 1.389(2) . ?
C4 C3 1.393(2) . ?
C1 C6 1.374(3) . ?
C1 C2 1.375(3) . ?
C17 C12 1.419(2) . ?
C9 C8 1.505(2) . ?
C13 C12 1.370(3) . ?
C13 C14 1.403(3) . ?
C5 C6 1.380(3) . ?
C3 C2 1.386(2) . ?
C15 C14 1.368(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
C18 C19 C20 118.38(15) . . ?
C18 C19 C22 120.81(14) . . ?
C20 C19 C22 120.81(14) . . ?
O3 C18 C19 122.41(16) . . ?
O3 C18 C17 116.43(15) . . ?
C19 C18 C17 121.16(14) . . ?
N1 C10 C7 113.27(13) . . ?
C17 C16 C15 118.64(17) . . ?
C17 C16 C21 119.18(16) . . ?
C15 C16 C21 122.18(17) . . ?
C4 C7 C10 114.59(13) . . ?
C4 C7 C8 109.40(13) . . ?
C10 C7 C8 107.97(13) . . ?
O4 C22 O5 121.63(15) . . ?
O4 C22 C19 119.83(14) . . ?
O5 C22 C19 118.54(14) . . ?
C20 C21 C16 120.59(16) . . ?
C5 C4 C3 117.93(16) . . ?
C5 C4 C7 119.35(14) . . ?
C3 C4 C7 122.67(15) . . ?
C21 C20 C19 121.78(15) . . ?
C6 C1 C2 121.24(18) . . ?
C6 C1 Cl1 119.68(16) . . ?
C2 C1 Cl1 119.08(16) . . ?
C16 C17 C12 119.50(17) . . ?
C16 C17 C18 118.90(15) . . ?
C12 C17 C18 121.59(16) . . ?
O1 C9 O2 122.74(16) . . ?
O1 C9 C8 123.72(16) . . ?
O2 C9 C8 113.53(14) . . ?
C9 C8 C7 113.10(13) . . ?
C12 C13 C14 120.55(19) . . ?
C6 C5 C4 121.59(17) . . ?
C2 C3 C4 120.95(17) . . ?
C1 C6 C5 119.02(18) . . ?
C13 C12 C17 120.10(19) . . ?
C14 C15 C16 120.58(19) . . ?
C15 C14 C13 120.62(19) . . ?
C1 C2 C3 119.26(18) . . ?

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
C20 C19 C18 O3 179.86(15) . . . . ?
C22 C19 C18 O3 -0.1(2) . . . . ?
C20 C19 C18 C17 -0.3(2) . . . . ?
C22 C19 C18 C17 179.72(15) . . . . ?
N1 C10 C7 C4 60.55(17) . . . . ?
N1 C10 C7 C8 -177.28(13) . . . . ?
C18 C19 C22 O4 -178.26(15) . . . . ?
C20 C19 C22 O4 1.8(2) . . . . ?
C18 C19 C22 O5 2.2(2) . . . . ?
C20 C19 C22 O5 -177.79(15) . . . . ?
C17 C16 C21 C20 0.1(3) . . . . ?
C15 C16 C21 C20 179.68(17) . . . . ?
C10 C7 C4 C5 -146.07(15) . . . . ?
C8 C7 C4 C5 92.55(18) . . . . ?
C10 C7 C4 C3 36.7(2) . . . . ?
C8 C7 C4 C3 -84.68(19) . . . . ?
C16 C21 C20 C19 0.5(3) . . . . ?
C18 C19 C20 C21 -0.4(2) . . . . ?
C22 C19 C20 C21 179.55(16) . . . . ?
C15 C16 C17 C12 -1.1(3) . . . . ?
C21 C16 C17 C12 178.49(16) . . . . ?
C15 C16 C17 C18 179.60(16) . . . . ?
C21 C16 C17 C18 -0.8(2) . . . . ?
O3 C18 C17 C16 -179.26(15) . . . . ?
C19 C18 C17 C16 0.9(2) . . . . ?
O3 C18 C17 C12 1.4(2) . . . . ?
C19 C18 C17 C12 -178.36(16) . . . . ?
O1 C9 C8 C7 39.1(2) . . . . ?
O2 C9 C8 C7 -141.89(15) . . . . ?
C4 C7 C8 C9 -166.82(14) . . . . ?
C10 C7 C8 C9 67.88(18) . . . . ?
C3 C4 C5 C6 -1.1(3) . . . . ?
C7 C4 C5 C6 -178.49(16) . . . . ?
C5 C4 C3 C2 1.4(3) . . . . ?
C7 C4 C3 C2 178.64(16) . . . . ?
C2 C1 C6 C5 0.8(3) . . . . ?
Cl1 C1 C6 C5 -179.11(14) . . . . ?
C4 C5 C6 C1 0.1(3) . . . . ?
C14 C13 C12 C17 0.8(3) . . . . ?
C16 C17 C12 C13 0.4(3) . . . . ?
C18 C17 C12 C13 179.65(17) . . . . ?
C17 C16 C15 C14 0.7(3) . . . . ?
C21 C16 C15 C14 -178.84(19) . . . . ?
C16 C15 C14 C13 0.4(3) . . . . ?
C12 C13 C14 C15 -1.1(3) . . . . ?
C6 C1 C2 C3 -0.6(3) . . . . ?
Cl1 C1 C2 C3 179.35(14) . . . . ?
C4 C3 C2 C1 -0.6(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        27.12
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.296
_refine_diff_density_min         -0.450
_refine_diff_density_rms         0.041
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethanol:water=1:1'
####################################################################### 
# 
# 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_bacmaleic
_database_code_depnum_ccdc_archive 'CCDC 1411560'
_audit_update_record             
;
2015-07-08 deposited with the CCDC.
2015-09-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H16 Cl N O6'
_chemical_melting_point          453-459

_exptl_crystal_description       chunk
_exptl_crystal_colour            colorless

_diffrn_ambient_temperature      173(2)
_chemical_formula_weight         329.73

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21'
_symmetry_int_tables_number      4
_chemical_absolute_configuration ad

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

_cell_length_a                   5.7206(11)
_cell_length_b                   13.677(3)
_cell_length_c                   9.6377(19)
_cell_angle_alpha                90.00
_cell_angle_beta                 106.78(3)
_cell_angle_gamma                90.00
_cell_volume                     722.0(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    3605
_cell_measurement_theta_min      2.21
_cell_measurement_theta_max      28.37
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.517
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             344
_exptl_absorpt_coefficient_mu    0.295
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9220
_exptl_absorpt_correction_T_max  0.9544
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;
_diffrn_radiation_probe          ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_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            6260
_diffrn_reflns_av_R_equivalents  0.0210
_diffrn_reflns_av_sigmaI/netI    0.0360
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.21
_diffrn_reflns_theta_max         28.37
_reflns_number_total             3605
_reflns_number_gt                3345
_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)+(0.0444P)²+0.0130P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    noref
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.006(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.03(5)
_refine_ls_number_reflns         3605
_refine_ls_number_parameters     220
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0369
_refine_ls_R_factor_gt           0.0330
_refine_ls_wR_factor_ref         0.0807
_refine_ls_wR_factor_gt          0.0783
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_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 0.47749(9) 0.65979(4) -0.12156(4) 0.03260(13) Uani 1 1 d . . .
C3 C 0.5091(3) 0.65615(15) 0.29842(17) 0.0218(3) Uani 1 1 d . . .
H3 H 0.4090 0.6348 0.3559 0.026 Uiso 1 1 calc R . .
O4 O 0.2779(2) 0.91731(10) 1.24851(13) 0.0247(3) Uani 1 1 d . . .
O1 O 1.2204(2) 0.58720(10) 0.54022(14) 0.0270(3) Uani 1 1 d . . .
N1 N 0.6162(3) 0.87842(12) 0.52595(16) 0.0240(3) Uani 1 1 d . . .
O2 O 1.0910(2) 0.46796(9) 0.65269(13) 0.0232(3) Uani 1 1 d . . .
C6 C 0.8025(3) 0.71719(14) 0.12895(18) 0.0235(4) Uani 1 1 d . . .
H6 H 0.9026 0.7376 0.0710 0.028 Uiso 1 1 calc R . .
C4 C 0.7357(3) 0.69973(12) 0.36522(17) 0.0181(3) Uani 1 1 d . . .
O3 O 0.2376(3) 0.91843(12) 0.65178(14) 0.0371(3) Uani 1 1 d . . .
O6 O -0.0099(2) 0.94650(12) 0.78507(15) 0.0366(4) Uani 1 1 d . . .
C7 C 0.8224(3) 0.71496(12) 0.52876(18) 0.0192(3) Uani 1 1 d . . .
H7 H 0.9824 0.7501 0.5535 0.023 Uiso 1 1 calc R . .
C13 C 0.4279(3) 0.91860(13) 1.04514(17) 0.0207(3) Uani 1 1 d . . .
H13 H 0.5863 0.9092 1.1102 0.025 Uiso 1 1 calc R . .
C9 C 1.0696(3) 0.55747(13) 0.59610(16) 0.0201(3) Uani 1 1 d . . .
O5 O 0.0141(2) 0.95523(14) 1.03897(15) 0.0393(4) Uani 1 1 d . . .
C12 C 0.4170(3) 0.91848(14) 0.90445(18) 0.0228(3) Uani 1 1 d . . .
H12 H 0.5702 0.9107 0.8858 0.027 Uiso 1 1 calc R . .
C5 C 0.8798(3) 0.72974(13) 0.27915(18) 0.0211(3) Uani 1 1 d . . .
H5 H 1.0336 0.7593 0.3233 0.025 Uiso 1 1 calc R . .
C1 C 0.5779(3) 0.67456(13) 0.06606(17) 0.0224(4) Uani 1 1 d . . .
C2 C 0.4294(3) 0.64381(13) 0.14861(18) 0.0229(4) Uani 1 1 d . . .
H2 H 0.2754 0.6147 0.1036 0.028 Uiso 1 1 calc R . .
C8 C 0.8585(3) 0.61780(13) 0.61319(18) 0.0206(3) Uani 1 1 d . . .
H8A H 0.8857 0.6321 0.7173 0.025 Uiso 1 1 calc R . .
H8B H 0.7069 0.5787 0.5797 0.025 Uiso 1 1 calc R . .
C10 C 0.6419(3) 0.77630(12) 0.58335(19) 0.0220(3) Uani 1 1 d . . .
H10A H 0.4800 0.7442 0.5541 0.026 Uiso 1 1 calc R . .
H10B H 0.6981 0.7785 0.6906 0.026 Uiso 1 1 calc R . .
C14 C 0.2290(3) 0.93122(13) 1.11506(18) 0.0213(3) Uani 1 1 d . . .
C11 C 0.2048(3) 0.92853(14) 0.77197(19) 0.0256(4) Uani 1 1 d . . .
H11C H 0.558(5) 0.884(2) 0.428(3) 0.047(7) Uiso 1 1 d . . .
H11A H 0.513(4) 0.909(2) 0.576(3) 0.044(7) Uiso 1 1 d . . .
H11B H 0.772(5) 0.906(2) 0.554(3) 0.042(7) Uiso 1 1 d . . .
H9 H 0.974(5) 0.456(2) 0.693(3) 0.054(8) Uiso 1 1 d . . .
H14 H -0.003(8) 0.949(4) 0.912(4) 0.115(15) Uiso 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
Cl1 C1 1.7438(17) . ?
C3 C2 1.393(2) . ?
C3 C4 1.403(2) . ?
O4 C14 1.249(2) . ?
O1 C9 1.212(2) . ?
N1 C10 1.494(2) . ?
O2 C9 1.331(2) . ?
C6 C1 1.382(3) . ?
C6 C5 1.397(2) . ?
C4 C5 1.390(2) . ?
C4 C7 1.524(2) . ?
O3 C11 1.234(2) . ?
O6 C11 1.294(2) . ?
C7 C10 1.536(2) . ?
C7 C8 1.541(2) . ?
C13 C12 1.339(2) . ?
C13 C14 1.490(2) . ?
C9 C8 1.510(2) . ?
O5 C14 1.279(2) . ?
C12 C11 1.493(2) . ?
C1 C2 1.386(2) . ?

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 C3 C4 120.64(15) . . ?
C1 C6 C5 118.86(16) . . ?
C5 C4 C3 118.71(15) . . ?
C5 C4 C7 120.33(15) . . ?
C3 C4 C7 120.96(14) . . ?
C4 C7 C10 112.25(14) . . ?
C4 C7 C8 112.48(14) . . ?
C10 C7 C8 106.93(13) . . ?
C12 C13 C14 129.76(16) . . ?
O1 C9 O2 119.85(16) . . ?
O1 C9 C8 124.02(16) . . ?
O2 C9 C8 116.06(15) . . ?
C13 C12 C11 130.88(16) . . ?
C4 C5 C6 121.17(16) . . ?
C6 C1 C2 121.50(16) . . ?
C6 C1 Cl1 119.34(13) . . ?
C2 C1 Cl1 119.15(14) . . ?
C1 C2 C3 119.13(16) . . ?
C9 C8 C7 113.78(14) . . ?
N1 C10 C7 112.81(15) . . ?
O4 C14 O5 121.42(16) . . ?
O4 C14 C13 118.36(15) . . ?
O5 C14 C13 120.22(15) . . ?
O3 C11 O6 121.26(17) . . ?
O3 C11 C12 119.09(17) . . ?
O6 C11 C12 119.65(16) . . ?

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
C2 C3 C4 C5 -0.4(3) . . . . ?
C2 C3 C4 C7 179.03(16) . . . . ?
C5 C4 C7 C10 122.14(17) . . . . ?
C3 C4 C7 C10 -57.3(2) . . . . ?
C5 C4 C7 C8 -117.21(17) . . . . ?
C3 C4 C7 C8 63.3(2) . . . . ?
C14 C13 C12 C11 -1.6(3) . . . . ?
C3 C4 C5 C6 0.0(3) . . . . ?
C7 C4 C5 C6 -179.44(17) . . . . ?
C1 C6 C5 C4 0.3(3) . . . . ?
C5 C6 C1 C2 -0.3(3) . . . . ?
C5 C6 C1 Cl1 179.23(14) . . . . ?
C6 C1 C2 C3 -0.1(3) . . . . ?
Cl1 C1 C2 C3 -179.63(15) . . . . ?
C4 C3 C2 C1 0.5(3) . . . . ?
O1 C9 C8 C7 10.6(2) . . . . ?
O2 C9 C8 C7 -172.36(14) . . . . ?
C4 C7 C8 C9 68.50(18) . . . . ?
C10 C7 C8 C9 -167.84(14) . . . . ?
C4 C7 C10 N1 -64.31(19) . . . . ?
C8 C7 C10 N1 171.89(14) . . . . ?
C12 C13 C14 O4 171.8(2) . . . . ?
C12 C13 C14 O5 -7.9(3) . . . . ?
C13 C12 C11 O3 -174.3(2) . . . . ?
C13 C12 C11 O6 4.9(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        28.37
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.218
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.042

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethanol:water=1:1'
####################################################################### 
# 
# 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_bacoxalic
_database_code_depnum_ccdc_archive 'CCDC 1411561'
_audit_update_record             
;
2015-07-08 deposited with the CCDC.
2015-09-20 downloaded from the CCDC.
;


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          438-442
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H13 Cl N O4'
_chemical_formula_weight         258.67

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/c

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

_cell_length_a                   15.035(3)
_cell_length_b                   7.2113(14)
_cell_length_c                   11.025(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 106.86(3)
_cell_angle_gamma                90.00
_cell_volume                     1143.9(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    2054
_cell_measurement_theta_min      2.83
_cell_measurement_theta_max      27.48

_exptl_crystal_description       rod
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.09
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.502
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             540
_exptl_absorpt_coefficient_mu    0.336
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9236
_exptl_absorpt_correction_T_max  0.9703
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_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            5024
_diffrn_reflns_av_R_equivalents  0.0161
_diffrn_reflns_av_sigmaI/netI    0.0236
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.83
_diffrn_reflns_theta_max         27.48
_reflns_number_total             2618
_reflns_number_gt                2054
_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)+(0.0503P)²+0.4010P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    noref
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       ?
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2618
_refine_ls_number_parameters     171
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0508
_refine_ls_R_factor_gt           0.0353
_refine_ls_wR_factor_ref         0.0979
_refine_ls_wR_factor_gt          0.0886
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_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 0.48723(3) 0.09149(6) 0.67201(4) 0.03969(16) Uani 1 1 d . . .
O1 O 0.20106(8) 1.15828(15) 0.33122(10) 0.0310(3) Uani 1 1 d . . .
O2 O 0.14250(9) 1.03894(17) 0.47943(12) 0.0360(3) Uani 1 1 d . . .
O3 O -0.03442(8) 0.68985(16) 0.57386(11) 0.0338(3) Uani 1 1 d . . .
O4 O -0.01279(8) 0.66869(17) 0.38225(11) 0.0355(3) Uani 1 1 d . . .
N1 N 0.10420(10) 0.5019(2) 0.25057(13) 0.0262(3) Uani 1 1 d . . .
C1 C 0.40745(11) 0.2602(2) 0.59424(15) 0.0273(3) Uani 1 1 d . . .
C4 C 0.28301(10) 0.5352(2) 0.47483(14) 0.0230(3) Uani 1 1 d . . .
C5 C 0.27442(11) 0.4468(2) 0.58304(14) 0.0251(3) Uani 1 1 d . . .
H5 H 0.2249 0.4808 0.6160 0.030 Uiso 1 1 calc R . .
C6 C 0.33617(11) 0.3104(2) 0.64395(14) 0.0276(3) Uani 1 1 d . . .
H6 H 0.3298 0.2523 0.7183 0.033 Uiso 1 1 calc R . .
C12 C -0.01376(10) 0.6033(2) 0.48542(14) 0.0248(3) Uani 1 1 d . . .
C7 C 0.21655(10) 0.6903(2) 0.41488(13) 0.0230(3) Uani 1 1 d . . .
H7 H 0.1669 0.6944 0.4586 0.028 Uiso 1 1 calc R . .
C2 C 0.41787(11) 0.3434(2) 0.48624(15) 0.0274(3) Uani 1 1 d . . .
H2 H 0.4664 0.3061 0.4523 0.033 Uiso 1 1 calc R . .
C8 C 0.26698(11) 0.8785(2) 0.43671(16) 0.0295(4) Uani 1 1 d . . .
H8A H 0.3064 0.8856 0.5258 0.035 Uiso 1 1 calc R . .
H8B H 0.3082 0.8871 0.3813 0.035 Uiso 1 1 calc R . .
C10 C 0.16871(11) 0.6625(2) 0.27284(14) 0.0257(3) Uani 1 1 d . . .
H10A H 0.1337 0.7760 0.2375 0.031 Uiso 1 1 calc R . .
H10B H 0.2164 0.6417 0.2284 0.031 Uiso 1 1 calc R . .
C3 C 0.35616(11) 0.4825(2) 0.42807(14) 0.0256(3) Uani 1 1 d . . .
H3 H 0.3639 0.5428 0.3552 0.031 Uiso 1 1 calc R . .
C9 C 0.20048(11) 1.0402(2) 0.40974(15) 0.0270(3) Uani 1 1 d . . .
H11A H 0.1345(15) 0.390(3) 0.2806(19) 0.047(6) Uiso 1 1 d . . .
H11B H 0.0606(15) 0.522(3) 0.2894(19) 0.045(6) Uiso 1 1 d . . .
H11C H 0.0775(14) 0.484(3) 0.167(2) 0.042(5) Uiso 1 1 d . . .
H9 H 0.1002(18) 1.144(4) 0.457(2) 0.082(8) Uiso 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
Cl1 C1 1.7487(16) . ?
O1 C9 1.2161(19) . ?
O2 C9 1.319(2) . ?
O3 C12 1.2699(19) . ?
O4 C12 1.2353(19) . ?
N1 C10 1.485(2) . ?
C1 C2 1.382(2) . ?
C1 C6 1.386(2) . ?
C4 C5 1.391(2) . ?
C4 C3 1.396(2) . ?
C4 C7 1.518(2) . ?
C5 C6 1.385(2) . ?
C12 C12 1.555(3) 3_566 ?
C7 C10 1.535(2) . ?
C7 C8 1.539(2) . ?
C2 C3 1.390(2) . ?
C8 C9 1.509(2) . ?

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 C6 121.44(14) . . ?
C2 C1 Cl1 119.42(13) . . ?
C6 C1 Cl1 119.13(12) . . ?
C5 C4 C3 118.10(14) . . ?
C5 C4 C7 119.87(13) . . ?
C3 C4 C7 121.97(13) . . ?
C6 C5 C4 121.68(14) . . ?
C5 C6 C1 118.68(14) . . ?
O4 C12 O3 126.17(15) . . ?
O4 C12 C12 118.87(17) . 3_566 ?
O3 C12 C12 114.95(16) . 3_566 ?
C4 C7 C10 113.75(12) . . ?
C4 C7 C8 110.45(12) . . ?
C10 C7 C8 109.77(13) . . ?
C1 C2 C3 118.89(14) . . ?
C9 C8 C7 112.50(13) . . ?
N1 C10 C7 111.14(12) . . ?
C2 C3 C4 121.18(14) . . ?
O1 C9 O2 124.20(15) . . ?
O1 C9 C8 122.71(15) . . ?
O2 C9 C8 113.09(14) . . ?

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
C3 C4 C5 C6 0.1(2) . . . . ?
C7 C4 C5 C6 -177.06(14) . . . . ?
C4 C5 C6 C1 -0.7(2) . . . . ?
C2 C1 C6 C5 0.1(2) . . . . ?
Cl1 C1 C6 C5 178.74(11) . . . . ?
C5 C4 C7 C10 -127.38(15) . . . . ?
C3 C4 C7 C10 55.55(19) . . . . ?
C5 C4 C7 C8 108.66(16) . . . . ?
C3 C4 C7 C8 -68.41(18) . . . . ?
C6 C1 C2 C3 1.2(2) . . . . ?
Cl1 C1 C2 C3 -177.50(12) . . . . ?
C4 C7 C8 C9 -165.19(13) . . . . ?
C10 C7 C8 C9 68.59(17) . . . . ?
C4 C7 C10 N1 67.11(17) . . . . ?
C8 C7 C10 N1 -168.57(12) . . . . ?
C1 C2 C3 C4 -1.8(2) . . . . ?
C5 C4 C3 C2 1.2(2) . . . . ?
C7 C4 C3 C2 178.28(14) . . . . ?
C7 C8 C9 O1 -121.34(17) . . . . ?
C7 C8 C9 O2 58.52(18) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.214
_refine_diff_density_min         -0.279
_refine_diff_density_rms         0.048
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methanol:water=1:1'
####################################################################### 
# 
# 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_bacpta
_database_code_depnum_ccdc_archive 'CCDC 1411562'
_audit_update_record             
;
2015-07-08 deposited with the CCDC.
2015-09-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          439-444
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H20 Cl N O4'
_chemical_formula_weight         349.80

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   6.1768(12)
_cell_length_b                   7.5101(15)
_cell_length_c                   19.092(4)
_cell_angle_alpha                79.43(3)
_cell_angle_beta                 82.90(3)
_cell_angle_gamma                84.25(3)
_cell_volume                     861.2(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    3392
_cell_measurement_theta_min      2.18
_cell_measurement_theta_max      27.94

_exptl_crystal_description       rod
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.80
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.349
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             368
_exptl_absorpt_coefficient_mu    0.243
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8292
_exptl_absorpt_correction_T_max  0.9952
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_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            14071
_diffrn_reflns_av_R_equivalents  0.0351
_diffrn_reflns_av_sigmaI/netI    0.0304
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.18
_diffrn_reflns_theta_max         27.94
_reflns_number_total             4103
_reflns_number_gt                3392
_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)+(0.0453P)²+0.2624P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    noref
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       ?
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4103
_refine_ls_number_parameters     223
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0484
_refine_ls_R_factor_gt           0.0385
_refine_ls_wR_factor_ref         0.1045
_refine_ls_wR_factor_gt          0.0985
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_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 0.02361(9) 0.27702(8) 0.08235(2) 0.06258(17) Uani 1 1 d . . .
O2 O 0.31171(14) -0.26389(12) 0.49294(5) 0.0249(2) Uani 1 1 d . . .
O1 O 0.04533(15) -0.16994(13) 0.42386(5) 0.0295(2) Uani 1 1 d . . .
N1 N 0.25967(17) 0.37968(14) 0.48333(6) 0.0226(2) Uani 1 1 d . . .
O4 O -0.34161(18) -0.32411(16) 0.36127(5) 0.0408(3) Uani 1 1 d . . .
C10 C 0.2433(2) 0.37519(16) 0.40621(7) 0.0239(3) Uani 1 1 d . . .
H10A H 0.3882 0.3944 0.3786 0.029 Uiso 1 1 calc R . .
H10B H 0.1389 0.4762 0.3874 0.029 Uiso 1 1 calc R . .
C7 C 0.1676(2) 0.19529(16) 0.39478(7) 0.0217(3) Uani 1 1 d . . .
H7 H 0.0202 0.1807 0.4225 0.026 Uiso 1 1 calc R . .
O3 O -0.08408(19) -0.15803(16) 0.29618(6) 0.0440(3) Uani 1 1 d . . .
C9 C 0.2193(2) -0.14611(16) 0.44802(6) 0.0211(3) Uani 1 1 d . . .
C4 C 0.1375(2) 0.21129(16) 0.31589(7) 0.0229(3) Uani 1 1 d . . .
C18 C -0.2606(2) -0.24840(18) 0.30369(7) 0.0269(3) Uani 1 1 d . . .
C14 C -0.3482(2) -0.24822(18) 0.23454(7) 0.0259(3) Uani 1 1 d . . .
C8 C 0.3208(2) 0.03365(17) 0.42526(7) 0.0262(3) Uani 1 1 d . . .
H8A H 0.4462 0.0183 0.3886 0.031 Uiso 1 1 calc R . .
H8B H 0.3796 0.0638 0.4672 0.031 Uiso 1 1 calc R . .
C5 C -0.0621(2) 0.28577(19) 0.29227(7) 0.0296(3) Uani 1 1 d . . .
H5 H -0.1764 0.3228 0.3259 0.036 Uiso 1 1 calc R . .
C1 C 0.0693(3) 0.2525(2) 0.17231(8) 0.0365(3) Uani 1 1 d . . .
C3 C 0.3028(2) 0.1609(2) 0.26505(8) 0.0326(3) Uani 1 1 d . . .
H3 H 0.4414 0.1126 0.2797 0.039 Uiso 1 1 calc R . .
C6 C -0.0980(3) 0.3072(2) 0.22080(8) 0.0352(3) Uani 1 1 d . . .
H6 H -0.2348 0.3585 0.2055 0.042 Uiso 1 1 calc R . .
C13 C -0.2357(2) -0.1799(2) 0.16883(8) 0.0337(3) Uani 1 1 d . . .
H13 H -0.1008 -0.1279 0.1672 0.040 Uiso 1 1 calc R . .
C15 C -0.5476(2) -0.3205(2) 0.23583(8) 0.0326(3) Uani 1 1 d . . .
H15 H -0.6266 -0.3658 0.2804 0.039 Uiso 1 1 calc R . .
C2 C 0.2692(3) 0.1798(2) 0.19344(8) 0.0399(4) Uani 1 1 d . . .
H2 H 0.3827 0.1431 0.1595 0.048 Uiso 1 1 calc R . .
C16 C -0.6315(3) -0.3267(2) 0.17248(9) 0.0382(4) Uani 1 1 d . . .
H16 H -0.7676 -0.3768 0.1741 0.046 Uiso 1 1 calc R . .
C11 C -0.5200(3) -0.2608(2) 0.10653(8) 0.0406(4) Uani 1 1 d . . .
C12 C -0.3215(3) -0.1880(2) 0.10581(8) 0.0427(4) Uani 1 1 d . . .
H12 H -0.2428 -0.1428 0.0612 0.051 Uiso 1 1 calc R . .
C17 C -0.6162(4) -0.2657(3) 0.03810(10) 0.0654(6) Uani 1 1 d . . .
H17A H -0.7361 -0.1704 0.0316 0.098 Uiso 1 1 calc R . .
H17B H -0.6723 -0.3846 0.0408 0.098 Uiso 1 1 calc R . .
H17C H -0.5028 -0.2455 -0.0026 0.098 Uiso 1 1 calc R . .
H11A H 0.1452 0.3220 0.5137 0.038(4) Uiso 1 1 d R . .
H11B H 0.3900 0.3211 0.4966 0.035(4) Uiso 1 1 d R . .
H11C H 0.2588 0.5026 0.4891 0.042(5) Uiso 1 1 d R . .
H18 H -0.0464 -0.1582 0.3407 0.071(7) Uiso 1 1 d 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 1.7484(15) . ?
O2 C9 1.2592(15) . ?
O1 C9 1.2613(15) . ?
N1 C10 1.4950(16) . ?
O4 C18 1.2141(17) . ?
C10 C7 1.5335(17) . ?
C7 C4 1.5219(17) . ?
C7 C8 1.5346(18) . ?
O3 C18 1.3204(17) . ?
C9 C8 1.5139(17) . ?
C4 C3 1.393(2) . ?
C4 C5 1.3939(19) . ?
C18 C14 1.4872(18) . ?
C14 C15 1.3908(19) . ?
C14 C13 1.393(2) . ?
C5 C6 1.3871(19) . ?
C1 C2 1.376(2) . ?
C1 C6 1.383(2) . ?
C3 C2 1.388(2) . ?
C13 C12 1.387(2) . ?
C15 C16 1.383(2) . ?
C16 C11 1.389(2) . ?
C11 C12 1.389(2) . ?
C11 C17 1.509(2) . ?

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
N1 C10 C7 112.66(10) . . ?
C4 C7 C10 108.31(10) . . ?
C4 C7 C8 115.52(11) . . ?
C10 C7 C8 111.03(10) . . ?
O2 C9 O1 123.03(11) . . ?
O2 C9 C8 117.11(11) . . ?
O1 C9 C8 119.82(11) . . ?
C3 C4 C5 117.82(12) . . ?
C3 C4 C7 123.20(12) . . ?
C5 C4 C7 118.94(12) . . ?
O4 C18 O3 123.15(13) . . ?
O4 C18 C14 123.80(12) . . ?
O3 C18 C14 113.05(12) . . ?
C15 C14 C13 119.24(13) . . ?
C15 C14 C18 118.70(12) . . ?
C13 C14 C18 122.06(12) . . ?
C9 C8 C7 115.81(10) . . ?
C6 C5 C4 121.62(14) . . ?
C2 C1 C6 121.44(13) . . ?
C2 C1 Cl1 119.79(13) . . ?
C6 C1 Cl1 118.77(12) . . ?
C2 C3 C4 121.35(14) . . ?
C1 C6 C5 118.66(14) . . ?
C12 C13 C14 119.73(14) . . ?
C16 C15 C14 120.29(14) . . ?
C1 C2 C3 119.09(14) . . ?
C15 C16 C11 121.10(14) . . ?
C12 C11 C16 118.19(14) . . ?
C12 C11 C17 121.55(16) . . ?
C16 C11 C17 120.26(16) . . ?
C13 C12 C11 121.45(15) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C10 C7 C4 175.12(10) . . . . ?
N1 C10 C7 C8 -57.05(14) . . . . ?
C10 C7 C4 C3 91.40(15) . . . . ?
C8 C7 C4 C3 -33.82(17) . . . . ?
C10 C7 C4 C5 -86.25(14) . . . . ?
C8 C7 C4 C5 148.53(12) . . . . ?
O4 C18 C14 C15 7.6(2) . . . . ?
O3 C18 C14 C15 -172.65(13) . . . . ?
O4 C18 C14 C13 -171.71(14) . . . . ?
O3 C18 C14 C13 8.02(19) . . . . ?
O2 C9 C8 C7 -157.70(11) . . . . ?
O1 C9 C8 C7 19.94(18) . . . . ?
C4 C7 C8 C9 -82.67(14) . . . . ?
C10 C7 C8 C9 153.52(11) . . . . ?
C3 C4 C5 C6 0.9(2) . . . . ?
C7 C4 C5 C6 178.72(12) . . . . ?
C5 C4 C3 C2 -1.5(2) . . . . ?
C7 C4 C3 C2 -179.20(13) . . . . ?
C2 C1 C6 C5 -0.7(2) . . . . ?
Cl1 C1 C6 C5 179.32(11) . . . . ?
C4 C5 C6 C1 0.2(2) . . . . ?
C15 C14 C13 C12 -1.3(2) . . . . ?
C18 C14 C13 C12 178.04(14) . . . . ?
C13 C14 C15 C16 0.9(2) . . . . ?
C18 C14 C15 C16 -178.40(13) . . . . ?
C6 C1 C2 C3 0.1(2) . . . . ?
Cl1 C1 C2 C3 -179.89(12) . . . . ?
C4 C3 C2 C1 1.0(2) . . . . ?
C14 C15 C16 C11 -0.3(2) . . . . ?
C15 C16 C11 C12 -0.1(2) . . . . ?
C15 C16 C11 C17 -178.90(17) . . . . ?
C14 C13 C12 C11 1.0(3) . . . . ?
C16 C11 C12 C13 -0.3(3) . . . . ?
C17 C11 C12 C13 178.54(17) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        27.94
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.275
_refine_diff_density_min         -0.285
_refine_diff_density_rms         0.040
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethanol: water=1:1'
####################################################################### 
# 
# 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_bactolsulfacid
_database_code_depnum_ccdc_archive 'CCDC 1411563'
_audit_update_record             
;
2015-07-08 deposited with the CCDC.
2015-09-20 downloaded from the CCDC.
;


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          442-444
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H28 Cl N O6 S'
_chemical_formula_weight         445.94

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/c

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

_cell_length_a                   5.4900(11)
_cell_length_b                   13.400(3)
_cell_length_c                   28.910(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.90(3)
_cell_angle_gamma                90.00
_cell_volume                     2126.5(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    3301
_cell_measurement_theta_min      1.41
_cell_measurement_theta_max      28.83

_exptl_crystal_description       rod
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.54
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.393
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             944
_exptl_absorpt_coefficient_mu    0.315
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8485
_exptl_absorpt_correction_T_max  0.9844
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_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            14684
_diffrn_reflns_av_R_equivalents  0.0573
_diffrn_reflns_av_sigmaI/netI    0.0721
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_theta_min         1.41
_diffrn_reflns_theta_max         28.83
_reflns_number_total             5211
_reflns_number_gt                3301
_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)+(0.0318P)²+4.0855P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    noref
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0033(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5211
_refine_ls_number_parameters     284
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1152
_refine_ls_R_factor_gt           0.0680
_refine_ls_wR_factor_ref         0.1444
_refine_ls_wR_factor_gt          0.1291
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_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 0.3800(3) 0.22261(8) 0.24028(4) 0.0613(4) Uani 1 1 d . . .
S1 S 0.01067(14) 0.96227(6) 0.06749(3) 0.02161(19) Uani 1 1 d . . .
O1 O -0.0473(4) 0.43017(17) 0.05193(9) 0.0359(6) Uani 1 1 d . . .
N1 N 0.4683(5) 0.13118(18) 0.00528(9) 0.0232(6) Uani 1 1 d . . .
H11A H 0.4577 0.1038 0.0340 0.035 Uiso 1 1 calc R . .
H11B H 0.5868 0.0995 -0.0108 0.035 Uiso 1 1 calc R . .
H11C H 0.3231 0.1243 -0.0100 0.035 Uiso 1 1 calc R . .
C1 C 0.3730(7) 0.2388(3) 0.18136(13) 0.0351(9) Uani 1 1 d . . .
H1 H 0.079(11) 0.595(5) 0.065(2) 0.12(2) Uiso 1 1 d . . .
O2 O 0.2174(5) 0.55317(17) 0.05695(9) 0.0340(6) Uani 1 1 d . . .
C2 C 0.5573(7) 0.2886(3) 0.15983(13) 0.0372(9) Uani 1 1 d . . .
H2 H 0.6926 0.3125 0.1775 0.045 Uiso 1 1 calc R . .
O3 O -0.0613(4) 0.86375(16) 0.05188(8) 0.0280(5) Uani 1 1 d . . .
C3 C 0.5474(6) 0.3040(3) 0.11349(12) 0.0296(8) Uani 1 1 d . . .
H3 H 0.6764 0.3383 0.0988 0.036 Uiso 1 1 calc R . .
O4 O -0.1310(4) 1.03936(17) 0.04689(8) 0.0290(5) Uani 1 1 d . . .
C4 C 0.3537(6) 0.2706(2) 0.08786(11) 0.0238(7) Uani 1 1 d . . .
O5 O 0.2682(4) 0.97595(17) 0.06274(8) 0.0268(5) Uani 1 1 d . . .
C5 C 0.1753(6) 0.2189(2) 0.11062(12) 0.0292(8) Uani 1 1 d . . .
H5 H 0.0410 0.1934 0.0932 0.035 Uiso 1 1 calc R . .
O6 O -0.1233(5) 0.67369(18) 0.08427(10) 0.0448(8) Uani 1 1 d . . .
C6 C 0.1835(7) 0.2031(3) 0.15677(13) 0.0345(9) Uani 1 1 d . . .
H6 H 0.0571 0.1674 0.1715 0.041 Uiso 1 1 calc R . .
C7 C 0.3354(6) 0.2917(2) 0.03723(11) 0.0226(7) Uani 1 1 d . . .
H7 H 0.1718 0.2688 0.0259 0.027 Uiso 1 1 calc R . .
C8 C 0.3572(6) 0.4027(2) 0.02699(12) 0.0263(8) Uani 1 1 d . . .
H8A H 0.5139 0.4277 0.0398 0.032 Uiso 1 1 calc R . .
H8B H 0.3580 0.4128 -0.0069 0.032 Uiso 1 1 calc R . .
C9 C 0.1548(6) 0.4611(2) 0.04694(11) 0.0246(7) Uani 1 1 d . . .
C10 C 0.5287(6) 0.2378(2) 0.00949(12) 0.0255(7) Uani 1 1 d . . .
H10A H 0.5387 0.2678 -0.0217 0.031 Uiso 1 1 calc R . .
H10B H 0.6895 0.2453 0.0251 0.031 Uiso 1 1 calc R . .
C11 C -0.0500(6) 0.9666(2) 0.12630(11) 0.0226(7) Uani 1 1 d . . .
C12 C -0.2627(6) 1.0077(2) 0.14227(12) 0.0282(8) Uani 1 1 d . . .
H12 H -0.3785 1.0347 0.1210 0.034 Uiso 1 1 calc R . .
C13 C -0.3079(7) 1.0097(3) 0.18851(12) 0.0316(8) Uani 1 1 d . . .
H13 H -0.4559 1.0381 0.1989 0.038 Uiso 1 1 calc R . .
C14 C -0.1467(7) 0.9723(3) 0.21988(12) 0.0314(8) Uani 1 1 d . . .
C15 C 0.0619(7) 0.9306(3) 0.20343(13) 0.0370(9) Uani 1 1 d . . .
H15 H 0.1766 0.9030 0.2248 0.044 Uiso 1 1 calc R . .
C16 C 0.1110(6) 0.9272(3) 0.15723(12) 0.0303(8) Uani 1 1 d . . .
H16 H 0.2573 0.8974 0.1469 0.036 Uiso 1 1 calc R . .
C17 C -0.1955(8) 0.9798(3) 0.27047(13) 0.0483(11) Uani 1 1 d . . .
H17A H -0.1616 1.0479 0.2811 0.072 Uiso 1 1 calc R . .
H17B H -0.0904 0.9328 0.2874 0.072 Uiso 1 1 calc R . .
H17C H -0.3666 0.9635 0.2760 0.072 Uiso 1 1 calc R . .
C18 C -0.4490(8) 0.7329(3) 0.13117(15) 0.0450(11) Uani 1 1 d . . .
C19 C -0.307(3) 0.6388(15) 0.1127(7) 0.023(9) Uiso 0.107(10) 1 d P A 2
H19 H -0.4096 0.5830 0.1001 0.028 Uiso 0.107(10) 1 calc PR A 2
H6A H -0.0980 0.7307 0.0791 0.046(12) Uiso 1 1 d R . .
H18A H -0.4252 0.8073 0.1211 0.059(13) Uiso 1 1 d R . .
H18B H -0.5005 0.7338 0.1643 0.073(15) Uiso 1 1 d R . .
H18C H -0.5760 0.6991 0.1095 0.071(15) Uiso 1 1 d R . .
C20 C -0.2239(9) 0.6723(3) 0.12947(17) 0.0400(14) Uani 0.893(10) 1 d P A 1
H20 H -0.1017 0.7018 0.1515 0.048 Uiso 0.893(10) 1 calc PR A 1
C21 C -0.126(8) 0.612(3) 0.1535(14) 0.044(12) Uiso 0.107(10) 1 d P A 2
H21A H -0.0701 0.5426 0.1498 0.066 Uiso 0.107(10) 1 calc PR A 2
H21B H -0.2095 0.6184 0.1831 0.066 Uiso 0.107(10) 1 calc PR A 2
H21C H 0.0142 0.6568 0.1530 0.066 Uiso 0.107(10) 1 calc PR A 2
C22 C -0.2652(11) 0.5669(3) 0.14288(18) 0.0497(17) Uani 0.893(10) 1 d P A 1
H22A H -0.3976 0.5389 0.1238 0.075 Uiso 0.893(10) 1 calc PR A 1
H22B H -0.3093 0.5638 0.1756 0.075 Uiso 0.893(10) 1 calc PR A 1
H22C H -0.1159 0.5284 0.1381 0.075 Uiso 0.893(10) 1 calc PR A 1


_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 1.717(4) . ?
S1 O4 1.419(2) . ?
S1 O5 1.435(2) . ?
S1 O3 1.448(2) . ?
S1 C11 1.739(3) . ?
O1 C9 1.196(4) . ?
N1 C10 1.471(4) . ?
C1 C6 1.339(5) . ?
C1 C2 1.370(5) . ?
O2 C9 1.311(4) . ?
C2 C3 1.356(5) . ?
C3 C4 1.363(5) . ?
C4 C5 1.375(4) . ?
C4 C7 1.493(5) . ?
C5 C6 1.351(5) . ?
O6 C19 1.393(19) . ?
O6 C20 1.427(5) . ?
C7 C8 1.521(4) . ?
C7 C10 1.523(4) . ?
C8 C9 1.483(4) . ?
C11 C16 1.354(5) . ?
C11 C12 1.377(4) . ?
C12 C13 1.364(5) . ?
C13 C14 1.353(5) . ?
C14 C15 1.367(5) . ?
C14 C17 1.494(5) . ?
C15 C16 1.368(5) . ?
C18 C20 1.481(6) . ?
C18 C19 1.579(19) . ?
C19 C21 1.58(5) . ?
C20 C22 1.483(6) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O4 S1 O5 113.69(14) . . ?
O4 S1 O3 112.83(15) . . ?
O5 S1 O3 110.57(14) . . ?
O4 S1 C11 105.91(14) . . ?
O5 S1 C11 107.07(15) . . ?
O3 S1 C11 106.22(14) . . ?
C6 C1 C2 120.4(4) . . ?
C6 C1 Cl1 119.1(3) . . ?
C2 C1 Cl1 120.5(3) . . ?
C3 C2 C1 120.3(4) . . ?
C2 C3 C4 120.4(3) . . ?
C3 C4 C5 117.4(3) . . ?
C3 C4 C7 120.7(3) . . ?
C5 C4 C7 121.8(3) . . ?
C6 C5 C4 122.6(4) . . ?
C19 O6 C20 32.9(8) . . ?
C1 C6 C5 118.8(3) . . ?
C4 C7 C8 111.9(3) . . ?
C4 C7 C10 112.9(3) . . ?
C8 C7 C10 107.7(2) . . ?
C9 C8 C7 112.2(3) . . ?
O1 C9 O2 122.7(3) . . ?
O1 C9 C8 124.5(3) . . ?
O2 C9 C8 112.8(3) . . ?
N1 C10 C7 110.3(2) . . ?
C16 C11 C12 118.8(3) . . ?
C16 C11 S1 120.0(2) . . ?
C12 C11 S1 121.2(3) . . ?
C13 C12 C11 120.3(3) . . ?
C14 C13 C12 121.5(3) . . ?
C13 C14 C15 117.5(3) . . ?
C13 C14 C17 120.4(3) . . ?
C15 C14 C17 122.1(4) . . ?
C14 C15 C16 122.2(4) . . ?
C11 C16 C15 119.7(3) . . ?
C20 C18 C19 30.1(7) . . ?
O6 C19 C21 94(2) . . ?
O6 C19 C18 107.3(12) . . ?
C21 C19 C18 104(2) . . ?
O6 C20 C18 111.0(4) . . ?
O6 C20 C22 108.3(4) . . ?
C18 C20 C22 112.5(4) . . ?

_diffrn_measured_fraction_theta_max 0.934
_diffrn_reflns_theta_full        28.83
_diffrn_measured_fraction_theta_full 0.934
_refine_diff_density_max         0.340
_refine_diff_density_min         -0.396
_refine_diff_density_rms         0.078
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: isopropanol'
