# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is © The Royal Society of Chemistry 2012


data_global
_journal_name_full               Org.Biomol.Chem.
_journal_coden_cambridge         0177
_journal_year                    ?
_journal_volume                  ?
_journal_page_first              ?
_publ_author_name                'Jie Wu'
_publ_contact_author_name        'Jie Wu'
_publ_contact_author_email       jie_wu@fudan.edu.cn

data_a11117a
_database_code_depnum_ccdc_archive 'CCDC 892699'
#TrackingRef '- a11117a.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H20 Cl N3 O2 S'
_chemical_formula_weight         485.97

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'
S S 0.1246 0.1234 '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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)

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

_cell_length_a                   10.673(5)
_cell_length_b                   8.677(4)
_cell_length_c                   12.475(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.403(7)
_cell_angle_gamma                90.00
_cell_volume                     1155.2(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    950
_cell_measurement_theta_min      3.432
_cell_measurement_theta_max      26.463

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.397
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             504
_exptl_absorpt_coefficient_mu    0.287
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9317
_exptl_absorpt_correction_T_max  0.9502
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4044
_diffrn_reflns_av_R_equivalents  0.0349
_diffrn_reflns_av_sigmaI/netI    0.0315
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.63
_diffrn_reflns_theta_max         25.01
_reflns_number_total             2792
_reflns_number_gt                2545
_reflns_threshold_expression     >2sigma(I)

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

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.1029P)^2^+0.5000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.01(11)
_refine_ls_number_reflns         2792
_refine_ls_number_parameters     308
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0484
_refine_ls_R_factor_gt           0.0450
_refine_ls_wR_factor_ref         0.1346
_refine_ls_wR_factor_gt          0.1308
_refine_ls_goodness_of_fit_ref   0.914
_refine_ls_restrained_S_all      0.914
_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
S1 S 0.56030(9) 0.18037(12) 0.63402(7) 0.0434(3) Uani 1 1 d . . .
Cl1 Cl 0.86048(13) -0.32122(17) 0.94622(10) 0.0738(4) Uani 1 1 d . . .
N1 N 0.7341(4) -0.3487(5) 0.7693(3) 0.0617(10) Uani 1 1 d . . .
N2 N 0.6802(3) 0.1268(4) 0.7154(3) 0.0410(7) Uani 1 1 d . . .
C20 C 0.7350(3) 0.2515(5) 0.7857(3) 0.0422(9) Uani 1 1 d . . .
H20 H 0.7141 0.3531 0.7564 0.051 Uiso 1 1 calc R . .
O1 O 0.5404(3) 0.3398(4) 0.6581(3) 0.0586(8) Uani 1 1 d . . .
O2 O 0.5907(3) 0.1373(5) 0.5274(2) 0.0614(9) Uani 1 1 d . . .
C1 C 0.7818(4) -0.2450(6) 0.8333(4) 0.0498(10) Uani 1 1 d . . .
C2 C 0.7742(4) -0.0845(5) 0.8233(3) 0.0418(9) Uani 1 1 d . . .
C3 C 0.7054(4) -0.0297(5) 0.7324(3) 0.0406(9) Uani 1 1 d . . .
C4 C 0.6629(4) -0.1409(5) 0.6588(3) 0.0489(10) Uani 1 1 d . . .
H4 H 0.6244 -0.1114 0.5949 0.059 Uiso 1 1 calc R . .
C5 C 0.6795(5) -0.2956(6) 0.6831(4) 0.0608(12) Uani 1 1 d . . .
H5 H 0.6493 -0.3673 0.6339 0.073 Uiso 1 1 calc R . .
C6 C 0.4290(3) 0.0726(5) 0.6747(3) 0.0396(8) Uani 1 1 d . . .
C7 C 0.3790(4) 0.0949(5) 0.7757(3) 0.0478(10) Uani 1 1 d . . .
H7 H 0.4150 0.1650 0.8232 0.057 Uiso 1 1 calc R . .
C8 C 0.2743(4) 0.0106(6) 0.8045(3) 0.0529(11) Uani 1 1 d . . .
H8 H 0.2402 0.0240 0.8722 0.063 Uiso 1 1 calc R . .
C9 C 0.2191(4) -0.0939(6) 0.7336(4) 0.0523(10) Uani 1 1 d . . .
C10 C 0.2714(4) -0.1126(6) 0.6334(4) 0.0557(12) Uani 1 1 d . . .
H10 H 0.2353 -0.1819 0.5855 0.067 Uiso 1 1 calc R . .
C11 C 0.3759(4) -0.0308(6) 0.6030(3) 0.0496(10) Uani 1 1 d . . .
H11 H 0.4102 -0.0448 0.5353 0.060 Uiso 1 1 calc R . .
C12 C 0.1050(4) -0.1852(8) 0.7658(5) 0.0746(15) Uani 1 1 d . . .
H12A H 0.0355 -0.1571 0.7206 0.112 Uiso 1 1 calc R . .
H12B H 0.0852 -0.1632 0.8391 0.112 Uiso 1 1 calc R . .
H12C H 0.1220 -0.2932 0.7580 0.112 Uiso 1 1 calc R . .
C13 C 0.8358(4) 0.0261(6) 0.9034(3) 0.0500(10) Uani 1 1 d . . .
H13 H 0.8815 -0.0341 0.9574 0.060 Uiso 1 1 calc R . .
C14 C 0.7362(4) 0.1184(6) 0.9579(3) 0.0508(11) Uani 1 1 d . . .
C15 C 0.6904(5) 0.0903(7) 1.0614(4) 0.0677(14) Uani 1 1 d . . .
H15 H 0.7241 0.0113 1.1029 0.081 Uiso 1 1 calc R . .
C16 C 0.5955(5) 0.1803(10) 1.1005(4) 0.0805(18) Uani 1 1 d . . .
H16 H 0.5649 0.1616 1.1689 0.097 Uiso 1 1 calc R . .
C17 C 0.5448(5) 0.2983(9) 1.0400(5) 0.0800(19) Uani 1 1 d . . .
H17 H 0.4796 0.3571 1.0675 0.096 Uiso 1 1 calc R . .
C18 C 0.5903(4) 0.3294(7) 0.9390(4) 0.0590(12) Uani 1 1 d . . .
H18 H 0.5577 0.4104 0.8987 0.071 Uiso 1 1 calc R . .
C19 C 0.6861(4) 0.2374(5) 0.8982(3) 0.0478(10) Uani 1 1 d . . .
N3 N 0.9260(3) 0.1220(5) 0.8435(3) 0.0495(9) Uani 1 1 d . . .
C21 C 0.8774(3) 0.2275(5) 0.7842(3) 0.0430(9) Uani 1 1 d . . .
C22 C 0.9559(4) 0.3189(5) 0.7108(4) 0.0481(10) Uani 1 1 d . . .
C23 C 1.0861(4) 0.3188(7) 0.7248(5) 0.0708(14) Uani 1 1 d . . .
H23 H 1.1213 0.2675 0.7832 0.085 Uiso 1 1 calc R . .
C24 C 1.1626(5) 0.3936(8) 0.6534(5) 0.0791(18) Uani 1 1 d . . .
H24 H 1.2490 0.3907 0.6634 0.095 Uiso 1 1 calc R . .
C25 C 1.1126(6) 0.4734(8) 0.5664(5) 0.0768(16) Uani 1 1 d . . .
H25 H 1.1644 0.5237 0.5181 0.092 Uiso 1 1 calc R . .
C26 C 0.9847(6) 0.4760(8) 0.5539(4) 0.0757(16) Uani 1 1 d . . .
H26 H 0.9499 0.5292 0.4962 0.091 Uiso 1 1 calc R . .
C27 C 0.9059(4) 0.4009(7) 0.6254(4) 0.0598(12) Uani 1 1 d . . .
H27 H 0.8195 0.4059 0.6158 0.072 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S1 0.0454(5) 0.0348(5) 0.0499(5) 0.0080(4) -0.0019(3) -0.0003(5)
Cl1 0.0839(8) 0.0580(8) 0.0796(7) 0.0331(7) 0.0091(6) 0.0102(7)
N1 0.072(3) 0.032(2) 0.081(3) 0.004(2) 0.016(2) 0.0020(19)
N2 0.0371(16) 0.0290(17) 0.0569(18) -0.0017(14) -0.0015(13) 0.0015(14)
C20 0.0363(18) 0.0287(19) 0.062(2) -0.0031(18) -0.0004(16) 0.0005(17)
O1 0.0601(18) 0.0344(16) 0.081(2) 0.0080(16) -0.0106(15) 0.0039(15)
O2 0.0696(19) 0.068(2) 0.0470(14) 0.0119(16) 0.0061(13) -0.0150(18)
C1 0.046(2) 0.039(2) 0.064(2) 0.014(2) 0.0166(18) 0.005(2)
C2 0.040(2) 0.035(2) 0.051(2) 0.0051(18) 0.0125(16) 0.0008(18)
C3 0.0374(19) 0.030(2) 0.054(2) 0.0025(18) 0.0104(16) 0.0015(16)
C4 0.054(2) 0.034(2) 0.059(2) -0.0063(19) 0.0028(18) 0.0042(19)
C5 0.076(3) 0.035(3) 0.072(3) -0.010(2) 0.008(2) -0.002(2)
C6 0.0366(19) 0.037(2) 0.0451(18) 0.0031(17) -0.0022(14) 0.0038(17)
C7 0.048(2) 0.046(3) 0.049(2) -0.0107(19) -0.0017(17) 0.0029(19)
C8 0.050(2) 0.055(3) 0.055(2) -0.004(2) 0.0119(18) 0.006(2)
C9 0.042(2) 0.044(2) 0.071(3) -0.003(2) 0.0061(19) 0.006(2)
C10 0.047(2) 0.057(3) 0.063(2) -0.016(2) -0.0038(19) -0.005(2)
C11 0.052(2) 0.053(3) 0.0439(19) -0.012(2) 0.0022(16) 0.000(2)
C12 0.047(3) 0.063(4) 0.114(4) -0.007(3) 0.020(2) -0.003(3)
C13 0.046(2) 0.047(3) 0.057(2) 0.006(2) -0.0032(17) -0.003(2)
C14 0.049(2) 0.048(3) 0.055(2) -0.007(2) 0.0002(18) -0.013(2)
C15 0.078(3) 0.070(4) 0.055(2) -0.010(3) 0.005(2) -0.018(3)
C16 0.082(3) 0.096(5) 0.063(3) -0.028(4) 0.022(2) -0.028(4)
C17 0.062(3) 0.085(5) 0.093(4) -0.049(4) 0.023(3) -0.011(3)
C18 0.042(2) 0.055(3) 0.080(3) -0.025(3) 0.005(2) -0.005(2)
C19 0.0385(19) 0.041(2) 0.064(2) -0.011(2) 0.0032(17) -0.0065(19)
N3 0.0373(17) 0.043(2) 0.068(2) 0.0038(17) 0.0004(15) 0.0000(16)
C21 0.0373(19) 0.032(2) 0.059(2) -0.0061(18) 0.0017(17) -0.0008(17)
C22 0.042(2) 0.031(2) 0.071(3) -0.005(2) 0.0082(18) -0.0016(18)
C23 0.043(2) 0.061(3) 0.109(4) 0.016(3) 0.001(2) 0.000(2)
C24 0.044(3) 0.069(4) 0.125(5) 0.013(4) 0.018(3) -0.005(3)
C25 0.072(3) 0.065(4) 0.093(4) -0.005(3) 0.031(3) -0.015(3)
C26 0.078(4) 0.079(4) 0.070(3) 0.015(3) 0.007(3) -0.013(3)
C27 0.048(2) 0.059(3) 0.072(3) 0.005(3) 0.001(2) -0.005(2)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O2 1.421(3) . ?
S1 O1 1.432(4) . ?
S1 N2 1.693(3) . ?
S1 C6 1.762(4) . ?
Cl1 C1 1.763(5) . ?
N1 C5 1.303(7) . ?
N1 C1 1.304(6) . ?
N2 C3 1.400(5) . ?
N2 C20 1.509(5) . ?
C20 C19 1.505(6) . ?
C20 C21 1.534(5) . ?
C20 H20 0.9800 . ?
C1 C2 1.401(6) . ?
C2 C3 1.428(6) . ?
C2 C13 1.530(6) . ?
C3 C4 1.405(6) . ?
C4 C5 1.387(7) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C6 C7 1.385(5) . ?
C6 C11 1.386(6) . ?
C7 C8 1.385(7) . ?
C7 H7 0.9300 . ?
C8 C9 1.394(7) . ?
C8 H8 0.9300 . ?
C9 C10 1.383(7) . ?
C9 C12 1.508(7) . ?
C10 C11 1.377(7) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 N3 1.480(6) . ?
C13 C14 1.498(7) . ?
C13 H13 0.9800 . ?
C14 C19 1.379(6) . ?
C14 C15 1.405(6) . ?
C15 C16 1.372(9) . ?
C15 H15 0.9300 . ?
C16 C17 1.380(10) . ?
C16 H16 0.9300 . ?
C17 C18 1.381(8) . ?
C17 H17 0.9300 . ?
C18 C19 1.395(6) . ?
C18 H18 0.9300 . ?
N3 C21 1.284(5) . ?
C21 C22 1.476(6) . ?
C22 C27 1.385(7) . ?
C22 C23 1.399(6) . ?
C23 C24 1.376(8) . ?
C23 H23 0.9300 . ?
C24 C25 1.391(8) . ?
C24 H24 0.9300 . ?
C25 C26 1.373(8) . ?
C25 H25 0.9300 . ?
C26 C27 1.392(7) . ?
C26 H26 0.9300 . ?
C27 H27 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 S1 O1 119.0(2) . . ?
O2 S1 N2 108.20(18) . . ?
O1 S1 N2 104.63(18) . . ?
O2 S1 C6 108.51(19) . . ?
O1 S1 C6 109.4(2) . . ?
N2 S1 C6 106.30(17) . . ?
C5 N1 C1 115.5(4) . . ?
C3 N2 C20 122.3(3) . . ?
C3 N2 S1 120.1(3) . . ?
C20 N2 S1 116.1(3) . . ?
C19 C20 N2 110.4(3) . . ?
C19 C20 C21 110.6(3) . . ?
N2 C20 C21 106.0(3) . . ?
C19 C20 H20 109.9 . . ?
N2 C20 H20 109.9 . . ?
C21 C20 H20 109.9 . . ?
N1 C1 C2 127.5(4) . . ?
N1 C1 Cl1 114.3(4) . . ?
C2 C1 Cl1 118.1(4) . . ?
C1 C2 C3 115.5(4) . . ?
C1 C2 C13 122.7(4) . . ?
C3 C2 C13 121.7(4) . . ?
N2 C3 C4 120.4(4) . . ?
N2 C3 C2 122.7(4) . . ?
C4 C3 C2 116.9(4) . . ?
C5 C4 C3 118.8(4) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 H4 120.6 . . ?
N1 C5 C4 125.4(5) . . ?
N1 C5 H5 117.3 . . ?
C4 C5 H5 117.3 . . ?
C7 C6 C11 121.3(4) . . ?
C7 C6 S1 120.0(3) . . ?
C11 C6 S1 118.7(3) . . ?
C6 C7 C8 118.6(4) . . ?
C6 C7 H7 120.7 . . ?
C8 C7 H7 120.7 . . ?
C7 C8 C9 121.2(4) . . ?
C7 C8 H8 119.4 . . ?
C9 C8 H8 119.4 . . ?
C10 C9 C8 118.5(4) . . ?
C10 C9 C12 120.7(5) . . ?
C8 C9 C12 120.8(4) . . ?
C11 C10 C9 121.5(4) . . ?
C11 C10 H10 119.3 . . ?
C9 C10 H10 119.3 . . ?
C10 C11 C6 118.9(4) . . ?
C10 C11 H11 120.5 . . ?
C6 C11 H11 120.5 . . ?
C9 C12 H12A 109.5 . . ?
C9 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C9 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N3 C13 C14 113.3(4) . . ?
N3 C13 C2 107.5(3) . . ?
C14 C13 C2 109.2(3) . . ?
N3 C13 H13 108.9 . . ?
C14 C13 H13 108.9 . . ?
C2 C13 H13 108.9 . . ?
C19 C14 C15 119.4(5) . . ?
C19 C14 C13 115.4(4) . . ?
C15 C14 C13 125.2(5) . . ?
C16 C15 C14 119.4(6) . . ?
C16 C15 H15 120.3 . . ?
C14 C15 H15 120.3 . . ?
C15 C16 C17 121.0(5) . . ?
C15 C16 H16 119.5 . . ?
C17 C16 H16 119.5 . . ?
C16 C17 C18 120.3(5) . . ?
C16 C17 H17 119.8 . . ?
C18 C17 H17 119.8 . . ?
C17 C18 C19 119.0(6) . . ?
C17 C18 H18 120.5 . . ?
C19 C18 H18 120.5 . . ?
C14 C19 C18 120.9(4) . . ?
C14 C19 C20 115.3(4) . . ?
C18 C19 C20 123.6(4) . . ?
C21 N3 C13 115.5(3) . . ?
N3 C21 C22 120.7(3) . . ?
N3 C21 C20 119.1(4) . . ?
C22 C21 C20 120.1(4) . . ?
C27 C22 C23 118.2(4) . . ?
C27 C22 C21 122.4(4) . . ?
C23 C22 C21 119.3(4) . . ?
C24 C23 C22 120.8(5) . . ?
C24 C23 H23 119.6 . . ?
C22 C23 H23 119.6 . . ?
C23 C24 C25 120.9(5) . . ?
C23 C24 H24 119.5 . . ?
C25 C24 H24 119.5 . . ?
C26 C25 C24 118.2(5) . . ?
C26 C25 H25 120.9 . . ?
C24 C25 H25 120.9 . . ?
C25 C26 C27 121.6(6) . . ?
C25 C26 H26 119.2 . . ?
C27 C26 H26 119.2 . . ?
C22 C27 C26 120.2(5) . . ?
C22 C27 H27 119.9 . . ?
C26 C27 H27 119.9 . . ?

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         0.272
_refine_diff_density_min         -0.368
_refine_diff_density_rms         0.072