# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_JMK213_123K
_database_code_depnum_ccdc_archive 'CCDC 1435291'
_audit_update_record             
;
2015-11-05 deposited with the CCDC.
2016-02-02 downloaded from the CCDC.
;
_audit_creation_date             2015-08-17
_audit_creation_method           CRYSTALS_ver_14.61_build_5555

_oxford_structure_analysis_title 'alex in P2(1)/c'
_chemical_name_systematic        ?
_chemical_melting_point          ?
_chemical_compound_source        'Max Klein'
#end of refcif 
_cell_length_a                   18.3697(12)
_cell_length_b                   9.6176(6)
_cell_length_c                   8.7340(6)
_cell_angle_alpha                90
_cell_angle_beta                 102.202(3)
_cell_angle_gamma                90
_cell_volume                     1508.20(17)

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1 '
_symmetry_space_group_name_Hall  '-P 2ybc'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
-x,y+1/2,-z+1/2
x,-y+1/2,z+1/2

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0181 0.0091 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0311 0.0180 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0492 0.0322 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
P 0.2955 0.4335 6.4345 1.9067 4.1791 27.1570 1.7800 0.5260 1.4908 68.1645
1.1149 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
S 0.3331 0.5567 6.9053 1.4679 5.2034 22.2151 1.4379 0.2536 1.5863 56.1720
0.8669 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            2

# Given Formula = C28 H34 N2 O6 P2 S2 
# Dc =      1.37 Fooo =    652.00 Mu =     29.72 M =    620.67
# Found Formula = C28 H34 N2 O6 P2 S2 
# Dc =      1.37 FOOO =    652.00 Mu =     29.72 M =    620.67

_chemical_formula_sum            'C28 H34 N2 O6 P2 S2'
_chemical_formula_moiety         'C28 H34 N2 O6 P2 S2'
_chemical_formula_weight         620.67


_cell_measurement_reflns_used    8992
_cell_measurement_theta_min      5
_cell_measurement_theta_max      68
_cell_measurement_temperature    123

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.030
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_max          0.090

_exptl_crystal_density_diffrn    1.367
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             652
_exptl_absorpt_coefficient_mu    2.972

# Sheldrick geometric approximatio 0.77 0.79 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_absorpt_correction_T_min  0.67
_exptl_absorpt_correction_T_max  0.79
_diffrn_measurement_device_type  'Bruker Kappa Apex2'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_measurement_method       'φ & ω scans'

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'Apex2 (Bruker AXS, 2006)'
_computing_cell_refinement       'Apex2 (Bruker AXS, 2006)'
_computing_data_reduction        'Apex2 (Bruker AXS, 2006)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        ?

_diffrn_ambient_temperature      123
_diffrn_reflns_number            11840
_reflns_number_total             2723
_diffrn_reflns_av_R_equivalents  0.036
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 2723 
# Theoretical number of reflections is about 5704 


_diffrn_reflns_theta_min         2.461
_diffrn_reflns_theta_max         69.840
_diffrn_measured_fraction_theta_max 0.955

_diffrn_reflns_theta_full        69.840
_diffrn_measured_fraction_theta_full 0.955


_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       8
_reflns_limit_h_min              -21
_reflns_limit_h_max              21
_reflns_limit_k_min              0
_reflns_limit_k_max              11
_reflns_limit_l_min              0
_reflns_limit_l_max              10

_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00

_atom_sites_solution_primary     direct #heavy,direct,difmap,geom,iterative
# _atom_sites_solution_secondary  difmap
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.30
_refine_diff_density_max         0.50


# The current dictionary definitions do not cover the 
# situation where the reflections used for refinement were 
# selected by a user-defined sigma threshold 


# The values actually used during refinement 
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_refine_ls_number_reflns         2713
_refine_ls_number_restraints     0
_refine_ls_number_parameters     181
_oxford_refine_ls_R_factor_ref   0.0473
_refine_ls_wR_factor_ref         0.0988
_refine_ls_goodness_of_fit_ref   0.9296
_refine_ls_shift/su_max          0.0005157
_refine_ls_shift/su_mean         0.0000354


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        2713
_refine_ls_R_factor_all          0.0473
_refine_ls_wR_factor_all         0.0988

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                2268
_refine_ls_R_factor_gt           0.0382
_refine_ls_wR_factor_gt          0.0931

# choose from: rm (reference molecule of known chirality), 
# ad (anomolous dispersion - Flack), rmad (rm and ad), 
# syn (from synthesis), unk (unknown) or . (not applicable). 
_chemical_absolute_configuration .


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)] 
 where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)²]² 
 Ai are: 
 4.68 6.81 3.11 0.793 
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3

# Replace last . with number of unfound hydrogen atoms attached to an atom.

# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint


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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
S1 S 0.29248(3) 0.32130(6) 0.51350(7) 0.0235 1.0000 Uani . . . . . .
C2 C 0.35685(13) 0.3645(2) 0.4025(3) 0.0220 1.0000 Uani . . . . . .
C3 C 0.33424(13) 0.4793(2) 0.3119(3) 0.0228 1.0000 Uani . . . . . .
C4 C 0.26530(13) 0.5328(3) 0.3327(3) 0.0240 1.0000 Uani . . . . . .
C5 C 0.23587(13) 0.4580(2) 0.4384(3) 0.0221 1.0000 Uani . . . . . .
P6 P 0.15299(3) 0.49895(6) 0.50395(7) 0.0216 1.0000 Uani . . . . . .
O7 O 0.11440(9) 0.35670(17) 0.52948(19) 0.0240 1.0000 Uani . . . . . .
C8 C 0.06799(14) 0.2886(3) 0.3945(3) 0.0281 1.0000 Uani . . . . . .
C9 C 0.02127(15) 0.1810(3) 0.4533(3) 0.0329 1.0000 Uani . . . . . .
O10 O 0.10555(10) 0.59780(18) 0.4007(2) 0.0303 1.0000 Uani . . . . . .
O11 O 0.18562(9) 0.54599(19) 0.6773(2) 0.0296 1.0000 Uani . . . . . .
C12 C 0.13606(14) 0.5871(3) 0.7800(3) 0.0292 1.0000 Uani . . . . . .
C13 C 0.17989(16) 0.5772(3) 0.9451(3) 0.0376 1.0000 Uani . . . . . .
C14 C 0.42477(13) 0.2825(2) 0.4117(3) 0.0198 1.0000 Uani . . . . . .
C15 C 0.48741(13) 0.3407(2) 0.3687(3) 0.0212 1.0000 Uani . . . . . .
C16 C 0.55082(13) 0.2610(2) 0.3748(3) 0.0201 1.0000 Uani . . . . . .
N17 N 0.55524(11) 0.1286(2) 0.4249(2) 0.0204 1.0000 Uani . . . . . .
C18 C 0.49569(13) 0.0732(2) 0.4703(2) 0.0189 1.0000 Uani . . . . . .
C19 C 0.42965(13) 0.1448(2) 0.4633(3) 0.0218 1.0000 Uani . . . . . .
C20 C 0.61834(13) 0.3192(2) 0.3263(3) 0.0239 1.0000 Uani . . . . . .
H31 H 0.3628 0.5167 0.2407 0.0298 1.0000 Uiso R . . . . .
H41 H 0.2414 0.6136 0.2789 0.0313 1.0000 Uiso R . . . . .
H81 H 0.0351 0.3568 0.3307 0.0353 1.0000 Uiso R . . . . .
H82 H 0.1016 0.2437 0.3357 0.0356 1.0000 Uiso R . . . . .
H91 H -0.0091 0.1363 0.3631 0.0513 1.0000 Uiso R . . . . .
H92 H -0.0111 0.2230 0.5145 0.0521 1.0000 Uiso R . . . . .
H93 H 0.0550 0.1151 0.5162 0.0511 1.0000 Uiso R . . . . .
H121 H 0.1195 0.6820 0.7545 0.0384 1.0000 Uiso R . . . . .
H122 H 0.0919 0.5250 0.7646 0.0381 1.0000 Uiso R . . . . .
H133 H 0.1478 0.6055 1.0146 0.0596 1.0000 Uiso R . . . . .
H132 H 0.2239 0.6375 0.9578 0.0587 1.0000 Uiso R . . . . .
H131 H 0.1966 0.4825 0.9651 0.0592 1.0000 Uiso R . . . . .
H151 H 0.4861 0.4352 0.3361 0.0276 1.0000 Uiso R . . . . .
H191 H 0.3886 0.1007 0.4914 0.0272 1.0000 Uiso R . . . . .
H201 H 0.6622 0.2868 0.3952 0.0389 1.0000 Uiso R . . . . .
H202 H 0.6166 0.4170 0.3294 0.0398 1.0000 Uiso R . . . . .
H203 H 0.6169 0.2905 0.2220 0.0397 1.0000 Uiso 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 0.0248(3) 0.0175(3) 0.0305(3) 0.0065(2) 0.0113(2) 0.0040(2)
C2 0.0289(13) 0.0167(11) 0.0216(11) -0.0020(9) 0.0082(9) 0.0005(9)
C3 0.0283(12) 0.0183(11) 0.0230(11) 0.0003(9) 0.0084(9) 0.0020(10)
C4 0.0277(12) 0.0201(12) 0.0240(12) 0.0005(9) 0.0051(10) 0.0042(10)
C5 0.0227(11) 0.0160(11) 0.0272(12) -0.0009(9) 0.0044(9) 0.0026(9)
P6 0.0211(3) 0.0179(3) 0.0264(3) 0.0007(2) 0.0067(2) 0.0013(2)
O7 0.0262(9) 0.0215(8) 0.0243(8) 0.0015(7) 0.0055(7) -0.0018(7)
C8 0.0320(13) 0.0252(13) 0.0262(12) -0.0029(10) 0.0043(10) -0.0031(10)
C9 0.0301(13) 0.0278(13) 0.0419(15) -0.0043(12) 0.0101(11) -0.0060(11)
O10 0.0293(9) 0.0228(9) 0.0396(10) 0.0060(8) 0.0092(8) 0.0051(7)
O11 0.0257(9) 0.0324(10) 0.0324(10) -0.0084(8) 0.0097(7) -0.0030(7)
C12 0.0324(14) 0.0255(13) 0.0316(13) -0.0039(11) 0.0111(11) 0.0026(11)
C13 0.0392(15) 0.0412(16) 0.0320(14) -0.0048(12) 0.0067(12) 0.0038(13)
C14 0.0246(11) 0.0167(11) 0.0185(11) -0.0011(8) 0.0054(9) 0.0004(9)
C15 0.0294(12) 0.0142(11) 0.0204(11) 0.0005(9) 0.0058(9) 0.0020(9)
C16 0.0264(12) 0.0170(11) 0.0171(10) -0.0005(9) 0.0051(9) -0.0018(9)
N17 0.0259(10) 0.0158(9) 0.0199(9) -0.0012(7) 0.0056(8) 0.0011(8)
C18 0.0254(11) 0.0169(12) 0.0148(10) -0.0013(9) 0.0052(9) 0.0006(9)
C19 0.0275(12) 0.0174(11) 0.0216(11) 0.0016(9) 0.0078(9) 0.0002(9)
C20 0.0258(12) 0.0187(12) 0.0274(12) 0.0018(10) 0.0065(10) -0.0002(10)

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.17303(12)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1 . C2 . 1.731(2) yes
S1 . C5 . 1.718(2) yes
C2 . C3 . 1.370(3) yes
C2 . C14 . 1.464(3) yes
C3 . C4 . 1.414(3) yes
C3 . H31 . 0.964 no
C4 . C5 . 1.369(3) yes
C4 . H41 . 0.965 no
C5 . P6 . 1.780(2) yes
P6 . O7 . 1.5782(17) yes
P6 . O10 . 1.4644(18) yes
P6 . O11 . 1.5726(18) yes
O7 . C8 . 1.456(3) yes
C8 . C9 . 1.503(4) yes
C8 . H81 . 0.982 no
C8 . H82 . 0.983 no
C9 . H91 . 0.965 no
C9 . H92 . 0.968 no
C9 . H93 . 0.971 no
O11 . C12 . 1.461(3) yes
C12 . C13 . 1.499(4) yes
C12 . H121 . 0.973 no
C12 . H122 . 0.993 no
C13 . H133 . 0.971 no
C13 . H132 . 0.983 no
C13 . H131 . 0.965 no
C14 . C15 . 1.401(3) yes
C14 . C19 . 1.395(3) yes
C15 . C16 . 1.386(3) yes
C15 . H151 . 0.952 no
C16 . N17 . 1.343(3) yes
C16 . C20 . 1.501(3) yes
N17 . C18 . 1.350(3) yes
C18 . C18 2_656 1.497(4) yes
C18 . C19 . 1.385(3) yes
C19 . H191 . 0.942 no
C20 . H201 . 0.951 no
C20 . H202 . 0.942 no
C20 . H203 . 0.946 no
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 . S1 . C5 . 91.86(11) yes
S1 . C2 . C3 . 110.95(18) yes
S1 . C2 . C14 . 120.99(17) yes
C3 . C2 . C14 . 128.1(2) yes
C2 . C3 . C4 . 112.9(2) yes
C2 . C3 . H31 . 122.3 no
C4 . C3 . H31 . 124.8 no
C3 . C4 . C5 . 112.8(2) yes
C3 . C4 . H41 . 124.0 no
C5 . C4 . H41 . 123.2 no
S1 . C5 . C4 . 111.49(18) yes
S1 . C5 . P6 . 122.45(14) yes
C4 . C5 . P6 . 125.93(18) yes
C5 . P6 . O7 . 107.07(10) yes
C5 . P6 . O10 . 112.57(11) yes
O7 . P6 . O10 . 115.04(10) yes
C5 . P6 . O11 . 101.27(10) yes
O7 . P6 . O11 . 101.80(9) yes
O10 . P6 . O11 . 117.54(10) yes
P6 . O7 . C8 . 118.63(15) yes
O7 . C8 . C9 . 108.2(2) yes
O7 . C8 . H81 . 110.1 no
C9 . C8 . H81 . 109.1 no
O7 . C8 . H82 . 107.2 no
C9 . C8 . H82 . 110.1 no
H81 . C8 . H82 . 112.1 no
C8 . C9 . H91 . 107.5 no
C8 . C9 . H92 . 111.3 no
H91 . C9 . H92 . 108.7 no
C8 . C9 . H93 . 107.5 no
H91 . C9 . H93 . 111.1 no
H92 . C9 . H93 . 110.7 no
P6 . O11 . C12 . 120.58(15) yes
O11 . C12 . C13 . 107.2(2) yes
O11 . C12 . H121 . 108.6 no
C13 . C12 . H121 . 111.0 no
O11 . C12 . H122 . 110.6 no
C13 . C12 . H122 . 110.4 no
H121 . C12 . H122 . 109.1 no
C12 . C13 . H133 . 108.0 no
C12 . C13 . H132 . 109.4 no
H133 . C13 . H132 . 111.0 no
C12 . C13 . H131 . 108.6 no
H133 . C13 . H131 . 111.4 no
H132 . C13 . H131 . 108.4 no
C2 . C14 . C15 . 120.6(2) yes
C2 . C14 . C19 . 121.7(2) yes
C15 . C14 . C19 . 117.8(2) yes
C14 . C15 . C16 . 120.0(2) yes
C14 . C15 . H151 . 119.5 no
C16 . C15 . H151 . 120.5 no
C15 . C16 . N17 . 122.0(2) yes
C15 . C16 . C20 . 121.4(2) yes
N17 . C16 . C20 . 116.7(2) yes
C16 . N17 . C18 . 118.2(2) yes
C18 2_656 C18 . N17 . 116.1(2) yes
C18 2_656 C18 . C19 . 120.7(3) yes
N17 . C18 . C19 . 123.2(2) yes
C14 . C19 . C18 . 118.8(2) yes
C14 . C19 . H191 . 120.8 no
C18 . C19 . H191 . 120.4 no
C16 . C20 . H201 . 109.8 no
C16 . C20 . H202 . 109.2 no
H201 . C20 . H202 . 109.8 no
C16 . C20 . H203 . 107.8 no
H201 . C20 . H203 . 111.2 no
H202 . C20 . H203 . 108.9 no


_iucr_refine_instructions_details 
;
#
# Punched on 17/08/15 at 10:48:50
#
#LIST     12                                                                    
BLOCK SCALE X'S  U'S 
RIDE C   (   3,X'S) H   (  31,X'S) 
RIDE C   (   4,X'S) H   (  41,X'S) 
RIDE C   (   8,X'S) H   (  81,X'S) H   (  82,X'S) 
RIDE C   (   9,X'S) H   (  91,X'S) H   (  92,X'S) H   (  93,X'S) 
RIDE C   (  12,X'S) H   ( 121,X'S) H   ( 122,X'S) 
RIDE C   (  13,X'S) H   ( 133,X'S) H   ( 132,X'S) H   ( 131,X'S) 
RIDE C   (  15,X'S) H   ( 151,X'S) 
RIDE C   (  19,X'S) H   ( 191,X'S) 
RIDE C   (  20,X'S) H   ( 201,X'S) H   ( 202,X'S) H   ( 203,X'S) 
END                                                                             
#
# Punched on 17/08/15 at 10:48:50
#
#LIST     16                                                                    
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;
####################################################################### 
# 
# 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_JMK251_123K
_database_code_depnum_ccdc_archive 'CCDC 1436307'
_audit_update_record             
;
2015-11-11 deposited with the CCDC.
2016-02-02 downloaded from the CCDC.
;
_audit_creation_date             2015-11-06
_audit_creation_method           CRYSTALS_ver_14.61_build_5555

_oxford_structure_analysis_title 'jmk251_123k_0m in P2(1)/n'
_chemical_name_systematic        ?
_chemical_melting_point          ?
_chemical_compound_source        'Max Klein'
#end of refcif 
_cell_length_a                   9.9744(10)
_cell_length_b                   4.7410(5)
_cell_length_c                   17.6632(17)
_cell_angle_alpha                90
_cell_angle_beta                 91.664(4)
_cell_angle_gamma                90
_cell_volume                     834.92(15)

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n '
_symmetry_space_group_name_Hall  '-P 2yn'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
x+1/2,-y+1/2,z+1/2
-x+1/2,y+1/2,-z+1/2

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0181 0.0091 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0311 0.0180 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
S 0.3331 0.5567 6.9053 1.4679 5.2034 22.2151 1.4379 0.2536 1.5863 56.1720
0.8669 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            2

# Given Formula = C20 H14 N2 S2 
# Dc =      1.38 Fooo =    360.00 Mu =     28.97 M =    346.48
# Found Formula = C20 H16 N2 S2 
# Dc =      1.39 FOOO =    364.00 Mu =     28.97 M =    348.49

_chemical_formula_sum            'C20 H16 N2 S2'
_chemical_formula_moiety         'C20 H16 N2 S2'
_chemical_formula_weight         348.49



_cell_measurement_reflns_used    7478
_cell_measurement_theta_min      4
_cell_measurement_theta_max      69
_cell_measurement_temperature    123

_exptl_crystal_description       block
_exptl_crystal_colour            'light yellow'
_exptl_crystal_size_min          0.050
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_max          0.100

_exptl_crystal_density_diffrn    1.386
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             364
_exptl_absorpt_coefficient_mu    2.897

# Sheldrick geometric approximatio 0.82 0.87 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_absorpt_correction_T_min  0.72
_exptl_absorpt_correction_T_max  0.87
_diffrn_measurement_device_type  'Bruker Kappa Apex2'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_measurement_method       'φ & ω scans'

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'Apex2 (Bruker AXS, 2006)'
_computing_cell_refinement       'Apex2 (Bruker AXS, 2006)'
_computing_data_reduction        'Apex2 (Bruker AXS, 2006)'
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        ?

_diffrn_ambient_temperature      123
_diffrn_reflns_number            9340
_reflns_number_total             1509
_diffrn_reflns_av_R_equivalents  0.023
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 1509 
# Theoretical number of reflections is about 3089 


_diffrn_reflns_theta_min         5.010
_diffrn_reflns_theta_max         68.737
_diffrn_measured_fraction_theta_max 0.976

_diffrn_reflns_theta_full        67.000
_diffrn_measured_fraction_theta_full 0.995


_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_reflns_limit_h_min              -11
_reflns_limit_h_max              11
_reflns_limit_k_min              0
_reflns_limit_k_max              5
_reflns_limit_l_min              0
_reflns_limit_l_max              20

_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00

_atom_sites_solution_primary     Other #heavy,direct,difmap,geom,iterative
# _atom_sites_solution_secondary  difmap
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.44
_refine_diff_density_max         0.48


# The current dictionary definitions do not cover the 
# situation where the reflections used for refinement were 
# selected by a user-defined sigma threshold 


# The values actually used during refinement 
_oxford_reflns_threshold_expression_ref I>2.0\s(I)
_refine_ls_number_reflns         1482
_refine_ls_number_restraints     113
_refine_ls_number_parameters     116
_oxford_refine_ls_R_factor_ref   0.0487
_refine_ls_wR_factor_ref         0.0541
_refine_ls_goodness_of_fit_ref   1.0670
_refine_ls_shift/su_max          0.0002373
_refine_ls_shift/su_mean         0.0000294


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        1508
_refine_ls_R_factor_all          0.0493
_refine_ls_wR_factor_all         0.0563

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                1482
_refine_ls_R_factor_gt           0.0487
_refine_ls_wR_factor_gt          0.0541

# choose from: rm (reference molecule of known chirality), 
# ad (anomolous dispersion - Flack), rmad (rm and ad), 
# syn (from synthesis), unk (unknown) or . (not applicable). 
_chemical_absolute_configuration .


_refine_ls_structure_factor_coef F
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)] 
 where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)²]² 
 Ai are: 
 0.224 0.170 0.439E-01 
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3

# Replace last . with number of unfound hydrogen atoms attached to an atom.

# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint


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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
C2 C 0.48158(16) 0.4093(4) 0.27908(9) 0.0280 1.0000 Uani . U . . . .
C4 C 0.59967(19) 0.4135(4) 0.16412(10) 0.0386 1.0000 Uani . U . . . .
C5 C 0.4955(2) 0.5833(5) 0.15042(11) 0.0434 1.0000 Uani . U . . . .
C6 C 0.44028(16) 0.3527(4) 0.35670(9) 0.0259 1.0000 Uani . U . . . .
C7 C 0.33499(15) 0.5006(4) 0.38885(9) 0.0271 1.0000 Uani . U . . . .
C8 C 0.29945(15) 0.4416(3) 0.46258(9) 0.0267 1.0000 Uani . U . . . .
N9 N 0.36278(13) 0.2479(3) 0.50583(7) 0.0264 1.0000 Uani . U . . . .
C11 C 0.50533(16) 0.1494(4) 0.40122(9) 0.0260 1.0000 Uani . U . . . .
C12 C 0.18763(17) 0.6011(4) 0.49902(10) 0.0329 1.0000 Uani . U . . . .
S30 S 0.61415(17) 0.2483(4) 0.24251(10) 0.0445 0.4000 Uani . U . . 1 .
C31 C 0.5875(7) 0.3136(16) 0.2427(4) 0.0576 0.6000 Uani . . . . 2 .
C10 C 0.4248(8) 0.598(2) 0.2286(5) 0.0530 0.4000 Uani . U . . 1 .
S11 S 0.38645(8) 0.6189(2) 0.21858(5) 0.0321 0.6000 Uani . . . . 2 .
C1 C 0.46479(16) 0.1054(3) 0.47517(9) 0.0250 1.0000 Uani . . . . . .
H41 H 0.6661 0.3910 0.1271 0.0460 1.0000 Uiso R . . . . .
H51 H 0.4691 0.6674 0.1035 0.0517 1.0000 Uiso R . . . . .
H71 H 0.2879 0.6406 0.3603 0.0327 1.0000 Uiso R . . . . .
H111 H 0.5765 0.0414 0.3815 0.0313 1.0000 Uiso R . . . . .
H121 H 0.1772 0.5340 0.5492 0.0402 1.0000 Uiso R . . . . .
H122 H 0.2087 0.7965 0.5004 0.0402 1.0000 Uiso R . . . . .
H123 H 0.1065 0.5732 0.4705 0.0402 1.0000 Uiso R . . . . .
H311 H 0.6531 0.1960 0.2668 0.0683 0.6000 Uiso R . . . 2 .
H101 H 0.3570 0.7303 0.2403 0.0514 0.4000 Uiso R . . . 1 .
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
C2 0.0292(8) 0.0309(8) 0.0238(8) 0.0010(6) -0.0023(6) -0.0062(6)
C4 0.0405(9) 0.0451(11) 0.0307(9) -0.0005(7) 0.0069(7) -0.0065(7)
C5 0.0430(10) 0.0537(12) 0.0336(9) 0.0132(9) 0.0011(7) -0.0055(8)
C6 0.0256(7) 0.0293(8) 0.0227(7) -0.0010(6) -0.0025(6) -0.0079(6)
C7 0.0257(7) 0.0294(8) 0.0258(8) 0.0022(6) -0.0046(6) -0.0048(6)
C8 0.0232(7) 0.0296(8) 0.0272(8) -0.0008(6) -0.0020(6) -0.0065(6)
N9 0.0260(7) 0.0299(7) 0.0231(6) 0.0000(5) -0.0008(5) -0.0063(5)
C11 0.0261(8) 0.0287(8) 0.0231(7) -0.0017(6) -0.0007(6) -0.0051(6)
C12 0.0273(8) 0.0398(10) 0.0316(9) 0.0026(7) 0.0026(6) -0.0012(7)
S30 0.0428(9) 0.0581(10) 0.0332(7) 0.0081(7) 0.0097(6) 0.0035(6)
C31 0.0422(11) 0.0900(11) 0.0407(11) 0.0242(11) 0.0017(11) 0.0144(11)
C10 0.0391(11) 0.0869(11) 0.0331(11) 0.0232(11) 0.0033(11) 0.0171(11)
S11 0.0303(5) 0.0447(5) 0.0213(4) 0.0125(3) 0.0013(3) 0.0051(4)
C1 0.0255(7) 0.0263(8) 0.0231(8) -0.0004(6) -0.0029(6) -0.0068(6)

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.2568(7)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C2 . C6 . 1.468(2) yes
C2 . S30 . 1.673(2) yes
C2 . C10 . 1.374(8) yes
C4 . C5 . 1.331(3) yes
C4 . S30 . 1.594(3) yes
C4 . H41 . 0.950 no
C5 . C10 . 1.570(9) yes
C5 . H51 . 0.950 no
C6 . C7 . 1.397(2) yes
C6 . C11 . 1.393(2) yes
C7 . C8 . 1.388(2) yes
C7 . H71 . 0.950 no
C8 . N9 . 1.341(2) yes
C8 . C12 . 1.507(2) yes
N9 . C1 . 1.348(2) yes
C11 . C1 . 1.394(2) yes
C11 . H111 . 0.950 no
C12 . H121 . 0.950 no
C12 . H122 . 0.950 no
C12 . H123 . 0.950 no
C31 . H311 . 0.950 no
C10 . H101 . 0.950 no
C1 . C1 2_656 1.492(3) yes
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C6 . C2 . S30 . 121.58(14) yes
C6 . C2 . C10 . 127.2(4) yes
S30 . C2 . C10 . 111.2(4) yes
C5 . C4 . S30 . 120.39(16) yes
C5 . C4 . H41 . 119.9 no
S30 . C4 . H41 . 119.7 no
C4 . C5 . C10 . 103.6(3) yes
C4 . C5 . H51 . 127.4 no
C10 . C5 . H51 . 128.9 no
C2 . C6 . C7 . 121.51(15) yes
C2 . C6 . C11 . 121.02(15) yes
C7 . C6 . C11 . 117.47(15) yes
C6 . C7 . C8 . 119.72(15) yes
C6 . C7 . H71 . 120.0 no
C8 . C7 . H71 . 120.2 no
C7 . C8 . N9 . 122.92(15) yes
C7 . C8 . C12 . 120.79(15) yes
N9 . C8 . C12 . 116.27(14) yes
C8 . N9 . C1 . 117.59(14) yes
C6 . C11 . C1 . 119.31(16) yes
C6 . C11 . H111 . 120.4 no
C1 . C11 . H111 . 120.2 no
C8 . C12 . H121 . 109.5 no
C8 . C12 . H122 . 109.5 no
H121 . C12 . H122 . 109.5 no
C8 . C12 . H123 . 109.4 no
H121 . C12 . H123 . 109.5 no
H122 . C12 . H123 . 109.5 no
C2 . S30 . C4 . 93.36(12) yes
C4 . C31 . C2 . 115.6(4) yes
C4 . C31 . H311 . 122.4 no
C2 . C31 . H311 . 122.0 no
C5 . C10 . C2 . 110.8(6) yes
C5 . C10 . H101 . 124.2 no
C2 . C10 . H101 . 124.8 no
C2 . S11 . C5 . 91.76(10) yes
C1 2_656 C1 . C11 . 120.44(19) yes
C1 2_656 C1 . N9 . 116.58(18) yes
C11 . C1 . N9 . 122.97(15) yes


_iucr_refine_instructions_details 
;
#
# Punched on 06/11/15 at 11:50:13
#
#LIST     12                                                                    
BLOCK SCALE X'S  U'S 
EQUIVALENCE C(10,U'S) C(31, U'S) 
RIDE C   (   4,X'S) H   (  41,X'S) 
RIDE C   (   5,X'S) H   (  51,X'S) 
RIDE C   (   7,X'S) H   (  71,X'S) 
RIDE C   (  11,X'S) H   ( 111,X'S) 
RIDE C   (  12,X'S) H   ( 121,X'S) H   ( 122,X'S) H   ( 123,X'S) 
RIDE C   (  31,X'S) H   ( 311,X'S) 
RIDE C   (  10,X'S) H   ( 101,X'S) 
END                                                                             
#
# Punched on 06/11/15 at 11:50:13
#
#LIST     16                                                                    
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
REM   SHIFTLIMIT   START (DO NOT REMOVE THIS LINE) 
REM   SHIFTLIMIT   END (DO NOT REMOVE THIS LINE) 
REM   DELU   START (DO NOT REMOVE THIS LINE) 
VIBR .0, 0.00200 = C(2) TO C(6) 
VIBR .0, 0.00200 = C(2) TO S(30) 
VIBR .0, 0.00200 = C(2) TO C(10) 
VIBR .0, 0.00500 = S(30) TO C(6) 
VIBR .0, 0.00500 = C(10) TO C(6) 
VIBR .0, 0.00500 = C(10) TO S(30) 
VIBR .0, 0.00200 = C(4) TO C(5) 
VIBR .0, 0.00200 = C(4) TO S(30) 
VIBR .0, 0.00500 = S(30) TO C(5) 
VIBR .0, 0.00200 = C(5) TO C(10) 
VIBR .0, 0.00500 = C(10) TO C(4) 
VIBR .0, 0.00200 = C(6) TO C(7) 
VIBR .0, 0.00200 = C(6) TO C(11) 
VIBR .0, 0.00500 = C(7) TO C(2) 
VIBR .0, 0.00500 = C(11) TO C(2) 
VIBR .0, 0.00500 = C(11) TO C(7) 
VIBR .0, 0.00200 = C(7) TO C(8) 
VIBR .0, 0.00500 = C(8) TO C(6) 
VIBR .0, 0.00200 = C(8) TO N(9) 
VIBR .0, 0.00200 = C(8) TO C(12) 
VIBR .0, 0.00500 = N(9) TO C(7) 
VIBR .0, 0.00500 = C(12) TO C(7) 
VIBR .0, 0.00500 = C(12) TO N(9) 
VIBR .0, 0.00200 = N(9) TO C(10) 
VIBR .0, 0.00500 = C(10) TO C(8) 
VIBR .0, 0.00200 = C(10) TO C(10,-1,1,1,0,1) 
VIBR .0, 0.00200 = C(10) TO C(11) 
VIBR .0, 0.00500 = N(9) TO C(10,-1,1,1,0,1) 
VIBR .0, 0.00500 = C(11) TO C(10,-1,1,1,0,1) 
VIBR .0, 0.00500 = C(11) TO N(9) 
VIBR .0, 0.00500 = C(6) TO C(10) 
VIBR .0, 0.00500 = C(4) TO C(2) 
VIBR .0, 0.00500 = C(2) TO C(4) 
VIBR .0, 0.00500 = C(2) TO C(5) 
VIBR .0, 0.00500 = C(5) TO C(2) 
REM   DELU   END (DO NOT REMOVE THIS LINE) 
REM   THERMSIM   START (DO NOT REMOVE THIS LINE) 
U(IJ) .0, 0.04000 = C(2) TO C(6) 
U(IJ) .0, 0.04000 = C(2) TO S(30) 
U(IJ) .0, 0.04000 = C(2) TO C(10) 
U(IJ) .0, 0.04000 = C(4) TO C(5) 
U(IJ) .0, 0.04000 = C(4) TO S(30) 
U(IJ) .0, 0.04000 = C(5) TO C(10) 
U(IJ) .0, 0.04000 = C(6) TO C(7) 
U(IJ) .0, 0.04000 = C(6) TO C(11) 
U(IJ) .0, 0.04000 = C(7) TO C(8) 
U(IJ) .0, 0.04000 = C(8) TO N(9) 
U(IJ) .0, 0.08000 = C(8) TO C(12) 
U(IJ) .0, 0.04000 = N(9) TO C(10) 
U(IJ) .0, 0.04000 = C(10) TO C(10,-1,1,1,0,1) 
U(IJ) .0, 0.04000 = C(10) TO C(11) 
REM   THERMSIM   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;

# Manually omitted reflections

loop_
_oxford_refln_omitted_index_h
_oxford_refln_omitted_index_k
_oxford_refln_omitted_index_l
_oxford_refln_omitted_flag
_oxford_refln_omitted_details
1 2 3 x .
