# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2017
#######################################################################
#
# 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_odjp5
_database_code_depnum_ccdc_archive 'CCDC 1570504'
_audit_update_record
;
2017-08-24 deposited with the CCDC.
2017-11-17 downloaded from the CCDC.
;
_audit_creation_date 2017-05-31
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelxl_version_number 2014/6
_chemical_name_common ?
_chemical_name_systematic '2-Allyl-3-(allylsulfinyl)-1H-indole '
_chemical_formula_moiety '2(C14 H15 N O S)'
_chemical_formula_sum 'C28 H30 N2 O2 S2'
_chemical_formula_weight 490.66
_chemical_melting_point ?
_chemical_oxdiff_formula C14H15NOS
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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system monoclinic
_space_group_IT_number 14
_space_group_name_H-M_alt 'P 1 21/c 1'
_space_group_name_Hall '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
_cell_length_a 17.7719(16)
_cell_length_b 8.1203(7)
_cell_length_c 19.0328(19)
_cell_angle_alpha 90
_cell_angle_beta 110.633(11)
_cell_angle_gamma 90
_cell_volume 2570.5(4)
_cell_formula_units_Z 4
_cell_measurement_reflns_used 3373
_cell_measurement_temperature 150
_cell_measurement_theta_max 25.0250
_cell_measurement_theta_min 3.5250
_shelx_estimated_absorpt_T_max ?
_shelx_estimated_absorpt_T_min ?
_exptl_absorpt_coefficient_mu 0.235
_exptl_absorpt_correction_T_max 1.00000
_exptl_absorpt_correction_T_min 0.93232
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.27b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details ?
_exptl_crystal_colour 'clear grayish colourless'
_exptl_crystal_colour_lustre clear
_exptl_crystal_colour_modifier grayish
_exptl_crystal_colour_primary colourless
_exptl_crystal_density_diffrn 1.268
_exptl_crystal_density_meas ?
_exptl_crystal_density_method ?
_exptl_crystal_description needle
_exptl_crystal_F_000 1040
_exptl_crystal_preparation ?
_exptl_crystal_size_max 0.276
_exptl_crystal_size_mid 0.049
_exptl_crystal_size_min 0.043
_exptl_transmission_factor_max ?
_exptl_transmission_factor_min ?
_diffrn_reflns_av_R_equivalents 0.0941
_diffrn_reflns_av_unetI/netI 0.0930
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max 21
_diffrn_reflns_limit_h_min -21
_diffrn_reflns_limit_k_max 9
_diffrn_reflns_limit_k_min -9
_diffrn_reflns_limit_l_max 22
_diffrn_reflns_limit_l_min -22
_diffrn_reflns_number 22982
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full 25.242
_diffrn_reflns_theta_max 25.349
_diffrn_reflns_theta_min 3.325
_diffrn_ambient_temperature 150
_diffrn_detector 'CCD plate'
_diffrn_detector_area_resol_mean 5.1636
_diffrn_detector_type Atlas
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):
# Type Start End Width t~exp~ \w \q \k \f Frames
#--------------------------------------------------------------------------
1 \w 24.00 76.00 1.00 40.00 -- 11.54 77.00 -30.00 52
2 \w -66.00 -32.00 1.00 40.00 -- 11.54 178.00-150.00 34
3 \w -76.00 34.00 1.00 40.00 -- -12.00 -19.00 60.00 110
4 \w -101.00 -54.00 1.00 40.00 -- -12.00-178.00 -30.00 47
5 \w -41.00 77.00 1.00 40.00 -- -12.00 0.00-150.00 118
6 \w -87.00 -57.00 1.00 40.00 -- -12.00-178.00-120.00 30
;
_diffrn_measurement_device 'four-circle diffractometer'
_diffrn_measurement_device_type 'Xcalibur, Atlas'
_diffrn_measurement_method '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11 0.0126996000
_diffrn_orient_matrix_UB_12 -0.0817549000
_diffrn_orient_matrix_UB_13 -0.0028362000
_diffrn_orient_matrix_UB_21 -0.0319146000
_diffrn_orient_matrix_UB_22 -0.0093171000
_diffrn_orient_matrix_UB_23 -0.0348938000
_diffrn_orient_matrix_UB_31 0.0252814000
_diffrn_orient_matrix_UB_32 0.0293340000
_diffrn_orient_matrix_UB_33 -0.0189619000
_diffrn_radiation_monochromator graphite
_diffrn_radiation_probe x-ray
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_source 'fine-focus sealed X-ray tube'
_diffrn_source_type 'Enhance (Mo) X-ray Source'
_diffrn_special_details ?
_reflns_Friedel_coverage 0.000
_reflns_Friedel_fraction_full .
_reflns_Friedel_fraction_max .
_reflns_number_gt 3004
_reflns_number_total 4690
_reflns_odcompleteness_completeness 99.63
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta 26.32
_reflns_special_details
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.
_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.
;
_reflns_threshold_expression 'I > 2\s(I)'
_computing_cell_refinement 'CrysAlisPro 1.171.39.27b (Rigaku OD, 2015)'
_computing_data_collection 'CrysAlisPro 1.171.39.27b (Rigaku OD, 2015)'
_computing_data_reduction 'CrysAlisPro 1.171.39.27b (Rigaku OD, 2015)'
_computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material 'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement 'ShelXL (Sheldrick, 2015)'
_computing_structure_solution 'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max 0.289
_refine_diff_density_min -0.336
_refine_diff_density_rms 0.063
_refine_ls_extinction_coef .
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.037
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 307
_refine_ls_number_reflns 4690
_refine_ls_number_restraints 66
_refine_ls_R_factor_all 0.1032
_refine_ls_R_factor_gt 0.0532
_refine_ls_restrained_S_all 1.029
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0259P)^2^+0.4696P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.0889
_refine_ls_wR_factor_ref 0.1068
_refine_special_details ?
_olex2_refinement_description
;
1. Fixed Uiso
At 1.2 times of:
All C(H) groups, All C(H,H) groups, All N(H) groups
2. Restrained distances
C27-H00X \\sim C28-HA \\sim C28-H00Z \\sim C24-H00V \\sim C25-H \\sim C25-H00Y
\\sim C14-H00M \\sim C14-
H00J \\sim C13-H00N \\sim C11-H00F \\sim C11-H00H \\sim C10-H00G
with sigma of 0.02
3.a Secondary CH2 refined with riding coordinates:
C9(H00B,H00C), C12(H00D,H00E), C23(H00P,H00Q), C26(H00S,H00T)
3.b Aromatic/amide H refined with riding coordinates:
N1(H005), N2(H006), C5(H00A), C10(H00G), C4(H00I), C2(H00K), C3(H00L),
C19(H00O), C13(H00N), C16(H00R), C17(H00U), C24(H00V), C18(H00W), C27(H00X)
3.c X=CH2 refined with riding coordinates:
C11(H00F,H00H), C14(H00J,H00M), C25(H00Y,H), C28(H00Z,HA)
;
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary dual
_atom_sites_solution_secondary ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S001 S 0.62853(4) 0.64352(9) 0.68973(4) 0.0240(2) Uani 1 1 d . . . . .
S002 S 0.85935(4) 0.69795(10) 0.61262(4) 0.0289(2) Uani 1 1 d . . . . .
O003 O 0.61643(11) 0.8148(2) 0.65603(11) 0.0304(5) Uani 1 1 d . . . . .
O004 O 0.81997(11) 0.5465(3) 0.63051(11) 0.0366(6) Uani 1 1 d . . . . .
N005 N 0.46724(13) 0.5012(3) 0.77182(12) 0.0223(6) Uani 1 1 d . . . . .
H005 H 0.4536 0.4704 0.8089 0.027 Uiso 1 1 calc R . . . .
N006 N 1.04613(13) 0.8547(3) 0.77915(13) 0.0273(6) Uani 1 1 d . . . . .
H006 H 1.0955 0.8855 0.7979 0.033 Uiso 1 1 calc R . . . .
C007 C 0.45964(16) 0.5753(3) 0.65526(16) 0.0196(7) Uani 1 1 d . . . . .
C008 C 0.54363(16) 0.5380(3) 0.77648(15) 0.0198(7) Uani 1 1 d . . . . .
C009 C 0.41479(16) 0.5207(3) 0.69895(16) 0.0210(7) Uani 1 1 d . . . . .
C00A C 0.41873(16) 0.6081(4) 0.57934(16) 0.0244(7) Uani 1 1 d . . . . .
H00A H 0.4464 0.6452 0.5491 0.029 Uiso 1 1 calc R . . . .
C00B C 0.54175(15) 0.5837(3) 0.70600(15) 0.0197(7) Uani 1 1 d . . . . .
C00C C 0.61166(16) 0.5270(4) 0.84967(15) 0.0256(7) Uani 1 1 d . . . . .
H00B H 0.6602 0.5677 0.8434 0.031 Uiso 1 1 calc R . . . .
H00C H 0.6204 0.4124 0.8649 0.031 Uiso 1 1 calc R . . . .
C00D C 0.99465(17) 0.8378(4) 0.81877(16) 0.0258(7) Uani 1 1 d . . . . .
C00E C 0.91956(17) 0.7840(4) 0.76844(16) 0.0253(7) Uani 1 1 d . . . . .
C00F C 1.00650(16) 0.8147(4) 0.70562(16) 0.0242(7) Uani 1 1 d . . . . .
C00G C 0.59616(16) 0.6239(4) 0.91022(15) 0.0247(7) Uani 1 1 d D . . . .
H00G H 0.5930 0.7378 0.9050 0.030 Uiso 1 1 calc DR . . . .
C00H C 0.92914(16) 0.7699(4) 0.69655(16) 0.0254(7) Uani 1 1 d . . . . .
C00I C 0.33665(17) 0.5847(4) 0.54979(16) 0.0285(7) Uani 1 1 d . . . . .
H00I H 0.3092 0.6065 0.4992 0.034 Uiso 1 1 calc R . . . .
C00J C 0.62300(17) 0.5112(4) 0.61139(16) 0.0262(7) Uani 1 1 d . . . . .
H00D H 0.5776 0.5449 0.5679 0.031 Uiso 1 1 calc R . . . .
H00E H 0.6713 0.5260 0.5995 0.031 Uiso 1 1 calc R . . . .
C00K C 0.33200(17) 0.4966(4) 0.66912(17) 0.0275(8) Uani 1 1 d . . . . .
H00K H 0.3036 0.4599 0.6989 0.033 Uiso 1 1 calc R . . . .
C00L C 0.29388(18) 0.5289(4) 0.59431(17) 0.0297(8) Uani 1 1 d . . . . .
H00L H 0.2386 0.5134 0.5727 0.036 Uiso 1 1 calc R . . . .
C00M C 0.85712(18) 0.7561(4) 0.79560(18) 0.0327(8) Uani 1 1 d . . . . .
H00O H 0.8072 0.7202 0.7635 0.039 Uiso 1 1 calc R . . . .
C00N C 0.61423(19) 0.3333(4) 0.62616(17) 0.0343(8) Uani 1 1 d D . . . .
H00N H 0.5645 0.2973 0.6259 0.041 Uiso 1 1 calc DR . . . .
C00O C 1.04706(17) 0.8283(4) 0.64912(17) 0.0331(8) Uani 1 1 d . . . . .
H00P H 1.0132 0.7773 0.6026 0.040 Uiso 1 1 calc R . . . .
H00Q H 1.0525 0.9438 0.6389 0.040 Uiso 1 1 calc R . . . .
C00P C 1.00840(18) 0.8644(4) 0.89456(17) 0.0327(8) Uani 1 1 d . . . . .
H00R H 1.0582 0.8995 0.9273 0.039 Uiso 1 1 calc R . . . .
C00Q C 0.58678(17) 0.5607(4) 0.96964(17) 0.0365(8) Uani 1 1 d D . . . .
H00F H 0.5896 0.4473 0.9768 0.044 Uiso 1 1 calc DR . . . .
H00H H 0.5773 0.6291 1.0048 0.044 Uiso 1 1 calc DR . . . .
C00R C 0.78542(17) 0.8611(4) 0.59390(18) 0.0360(8) Uani 1 1 d . . . . .
H00S H 0.7394 0.8342 0.5497 0.043 Uiso 1 1 calc R . . . .
H00T H 0.7671 0.8724 0.6360 0.043 Uiso 1 1 calc R . . . .
C00S C 0.9454(2) 0.8365(4) 0.91889(18) 0.0376(9) Uani 1 1 d . . . . .
H00U H 0.9528 0.8542 0.9692 0.045 Uiso 1 1 calc R . . . .
C00T C 1.12823(18) 0.7495(4) 0.67361(17) 0.0346(8) Uani 1 1 d D . . . .
H00V H 1.1317 0.6382 0.6859 0.042 Uiso 1 1 calc DR . . . .
C00U C 0.8705(2) 0.7825(4) 0.87045(19) 0.0387(9) Uani 1 1 d . . . . .
H00W H 0.8292 0.7641 0.8889 0.046 Uiso 1 1 calc R . . . .
C00V C 0.6711(2) 0.2257(4) 0.63931(17) 0.0432(9) Uani 1 1 d D . . . .
H00J H 0.7216 0.2576 0.6400 0.052 Uiso 1 1 calc DR . . . .
H00M H 0.6615 0.1164 0.6481 0.052 Uiso 1 1 calc DR . . . .
C00W C 0.82186(19) 1.0185(4) 0.5817(2) 0.0412(9) Uani 1 1 d D . . . .
H00X H 0.8530 1.0784 0.6235 0.049 Uiso 1 1 calc DR . . . .
C00X C 1.19430(19) 0.8255(4) 0.67895(18) 0.0437(9) Uani 1 1 d D . . . .
H00Y H 1.1931 0.9368 0.6671 0.052 Uiso 1 1 calc DR . . . .
H H 1.2428 0.7686 0.6946 0.052 Uiso 1 1 calc DR . . . .
C00Y C 0.8122(2) 1.0767(5) 0.5152(2) 0.0632(12) Uani 1 1 d D . . . .
H00Z H 0.7813 1.0191 0.4725 0.076 Uiso 1 1 calc DR . . . .
HA H 0.8362 1.1758 0.5104 0.076 Uiso 1 1 calc DR . . . .
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
S001 0.0266(4) 0.0216(5) 0.0276(5) -0.0027(3) 0.0143(4) -0.0028(3)
S002 0.0236(4) 0.0274(5) 0.0309(5) 0.0006(4) 0.0035(4) -0.0005(3)
O003 0.0437(13) 0.0202(12) 0.0386(13) -0.0022(10) 0.0285(11) -0.0033(10)
O004 0.0269(12) 0.0292(14) 0.0447(14) 0.0060(11) 0.0015(11) -0.0050(10)
N005 0.0249(13) 0.0264(16) 0.0188(14) 0.0018(11) 0.0118(12) -0.0014(11)
N006 0.0183(13) 0.0310(17) 0.0271(15) -0.0018(12) 0.0010(12) -0.0038(11)
C007 0.0284(16) 0.0114(16) 0.0204(17) -0.0012(13) 0.0103(14) 0.0012(13)
C008 0.0233(16) 0.0126(16) 0.0246(18) -0.0033(13) 0.0098(14) -0.0006(12)
C009 0.0269(16) 0.0147(17) 0.0230(18) -0.0001(13) 0.0107(15) 0.0024(13)
C00A 0.0300(18) 0.0227(19) 0.0229(18) 0.0005(14) 0.0123(15) 0.0031(14)
C00B 0.0232(16) 0.0159(17) 0.0210(17) -0.0018(13) 0.0091(14) -0.0002(13)
C00C 0.0242(16) 0.0249(19) 0.0260(18) 0.0046(14) 0.0068(15) 0.0008(14)
C00D 0.0301(17) 0.0190(18) 0.0271(19) 0.0015(14) 0.0087(15) 0.0030(14)
C00E 0.0273(17) 0.0165(18) 0.0314(19) 0.0011(14) 0.0095(15) 0.0014(13)
C00F 0.0211(16) 0.0206(18) 0.0265(19) 0.0020(14) 0.0031(14) 0.0036(13)
C00G 0.0268(16) 0.0197(18) 0.0261(18) -0.0003(14) 0.0075(15) -0.0016(14)
C00H 0.0217(16) 0.0226(19) 0.0277(18) 0.0002(14) 0.0036(14) 0.0007(13)
C00I 0.0333(18) 0.028(2) 0.0205(17) -0.0006(14) 0.0050(15) 0.0056(15)
C00J 0.0305(17) 0.0252(19) 0.0273(18) -0.0034(14) 0.0157(15) -0.0012(14)
C00K 0.0273(17) 0.027(2) 0.033(2) 0.0007(15) 0.0167(16) 0.0019(14)
C00L 0.0262(17) 0.030(2) 0.031(2) -0.0040(15) 0.0079(16) 0.0025(15)
C00M 0.0282(18) 0.029(2) 0.041(2) 0.0025(16) 0.0131(16) 0.0002(15)
C00N 0.041(2) 0.029(2) 0.042(2) -0.0111(16) 0.0247(17) -0.0061(17)
C00O 0.0302(18) 0.035(2) 0.034(2) -0.0020(16) 0.0122(16) -0.0034(15)
C00P 0.0356(19) 0.027(2) 0.030(2) -0.0001(15) 0.0047(16) 0.0004(15)
C00Q 0.039(2) 0.036(2) 0.036(2) -0.0048(17) 0.0147(17) -0.0030(16)
C00R 0.0249(17) 0.037(2) 0.040(2) 0.0071(17) 0.0043(16) 0.0104(16)
C00S 0.059(2) 0.028(2) 0.030(2) 0.0005(16) 0.0221(19) 0.0046(18)
C00T 0.037(2) 0.026(2) 0.047(2) -0.0025(16) 0.0226(18) 0.0030(16)
C00U 0.048(2) 0.029(2) 0.049(2) 0.0043(17) 0.029(2) 0.0043(17)
C00V 0.058(2) 0.034(2) 0.046(2) -0.0002(18) 0.028(2) 0.0020(19)
C00W 0.037(2) 0.031(2) 0.048(2) 0.0010(18) 0.0053(18) 0.0038(17)
C00X 0.036(2) 0.041(2) 0.059(2) -0.0086(19) 0.0225(19) 0.0038(17)
C00Y 0.056(3) 0.055(3) 0.070(3) 0.017(2) 0.011(2) -0.013(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
S001 O003 1.515(2) . ?
S001 C00B 1.746(3) . ?
S001 C00J 1.812(3) . ?
S002 O004 1.512(2) . ?
S002 C00H 1.742(3) . ?
S002 C00R 1.811(3) . ?
N005 H005 0.8600 . ?
N005 C008 1.362(3) . ?
N005 C009 1.381(3) . ?
N006 H006 0.8600 . ?
N006 C00D 1.382(3) . ?
N006 C00F 1.366(3) . ?
C007 C009 1.411(3) . ?
C007 C00A 1.396(4) . ?
C007 C00B 1.440(4) . ?
C008 C00B 1.381(4) . ?
C008 C00C 1.491(4) . ?
C009 C00K 1.392(4) . ?
C00A H00A 0.9300 . ?
C00A C00I 1.379(4) . ?
C00C H00B 0.9700 . ?
C00C H00C 0.9700 . ?
C00C C00G 1.499(4) . ?
C00D C00E 1.410(4) . ?
C00D C00P 1.392(4) . ?
C00E C00H 1.442(4) . ?
C00E C00M 1.398(4) . ?
C00F C00H 1.373(4) . ?
C00F C00O 1.495(4) . ?
C00G H00G 0.9300 . ?
C00G C00Q 1.305(4) . ?
C00I H00I 0.9300 . ?
C00I C00L 1.398(4) . ?
C00J H00D 0.9700 . ?
C00J H00E 0.9700 . ?
C00J C00N 1.491(4) . ?
C00K H00K 0.9300 . ?
C00K C00L 1.369(4) . ?
C00L H00L 0.9300 . ?
C00M H00O 0.9300 . ?
C00M C00U 1.376(4) . ?
C00N H00N 0.9300 . ?
C00N C00V 1.292(4) . ?
C00O H00P 0.9700 . ?
C00O H00Q 0.9700 . ?
C00O C00T 1.495(4) . ?
C00P H00R 0.9300 . ?
C00P C00S 1.374(4) . ?
C00Q H00F 0.9300 . ?
C00Q H00H 0.9300 . ?
C00R H00S 0.9700 . ?
C00R H00T 0.9700 . ?
C00R C00W 1.488(4) . ?
C00S H00U 0.9300 . ?
C00S C00U 1.396(4) . ?
C00T H00V 0.9300 . ?
C00T C00X 1.299(4) . ?
C00U H00W 0.9300 . ?
C00V H00J 0.9300 . ?
C00V H00M 0.9300 . ?
C00W H00X 0.9300 . ?
C00W C00Y 1.305(4) . ?
C00X H00Y 0.9300 . ?
C00X H 0.9300 . ?
C00Y H00Z 0.9300 . ?
C00Y HA 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
O003 S001 C00B 109.15(12) . . ?
O003 S001 C00J 103.74(12) . . ?
C00B S001 C00J 100.71(13) . . ?
O004 S002 C00H 107.62(13) . . ?
O004 S002 C00R 106.14(13) . . ?
C00H S002 C00R 99.67(15) . . ?
C008 N005 H005 124.9 . . ?
C008 N005 C009 110.2(2) . . ?
C009 N005 H005 124.9 . . ?
C00D N006 H006 125.2 . . ?
C00F N006 H006 125.2 . . ?
C00F N006 C00D 109.5(2) . . ?
C009 C007 C00B 105.6(2) . . ?
C00A C007 C009 118.3(3) . . ?
C00A C007 C00B 136.1(2) . . ?
N005 C008 C00B 108.3(2) . . ?
N005 C008 C00C 120.6(2) . . ?
C00B C008 C00C 131.1(2) . . ?
N005 C009 C007 107.8(2) . . ?
N005 C009 C00K 129.5(2) . . ?
C00K C009 C007 122.6(3) . . ?
C007 C00A H00A 120.5 . . ?
C00I C00A C007 119.1(3) . . ?
C00I C00A H00A 120.5 . . ?
C007 C00B S001 130.1(2) . . ?
C008 C00B S001 121.8(2) . . ?
C008 C00B C007 108.1(2) . . ?
C008 C00C H00B 109.2 . . ?
C008 C00C H00C 109.2 . . ?
C008 C00C C00G 112.2(2) . . ?
H00B C00C H00C 107.9 . . ?
C00G C00C H00B 109.2 . . ?
C00G C00C H00C 109.2 . . ?
N006 C00D C00E 108.1(2) . . ?
N006 C00D C00P 129.9(3) . . ?
C00P C00D C00E 122.0(3) . . ?
C00D C00E C00H 105.6(2) . . ?
C00M C00E C00D 118.9(3) . . ?
C00M C00E C00H 135.5(3) . . ?
N006 C00F C00H 108.9(2) . . ?
N006 C00F C00O 121.0(2) . . ?
C00H C00F C00O 130.1(3) . . ?
C00C C00G H00G 117.5 . . ?
C00Q C00G C00C 125.0(3) . . ?
C00Q C00G H00G 117.5 . . ?
C00E C00H S002 127.8(2) . . ?
C00F C00H S002 124.2(2) . . ?
C00F C00H C00E 107.9(3) . . ?
C00A C00I H00I 119.3 . . ?
C00A C00I C00L 121.3(3) . . ?
C00L C00I H00I 119.3 . . ?
S001 C00J H00D 108.9 . . ?
S001 C00J H00E 108.9 . . ?
H00D C00J H00E 107.7 . . ?
C00N C00J S001 113.5(2) . . ?
C00N C00J H00D 108.9 . . ?
C00N C00J H00E 108.9 . . ?
C009 C00K H00K 121.2 . . ?
C00L C00K C009 117.5(3) . . ?
C00L C00K H00K 121.2 . . ?
C00I C00L H00L 119.4 . . ?
C00K C00L C00I 121.1(3) . . ?
C00K C00L H00L 119.4 . . ?
C00E C00M H00O 120.4 . . ?
C00U C00M C00E 119.2(3) . . ?
C00U C00M H00O 120.4 . . ?
C00J C00N H00N 117.8 . . ?
C00V C00N C00J 124.4(3) . . ?
C00V C00N H00N 117.8 . . ?
C00F C00O H00P 108.8 . . ?
C00F C00O H00Q 108.8 . . ?
H00P C00O H00Q 107.7 . . ?
C00T C00O C00F 113.7(3) . . ?
C00T C00O H00P 108.8 . . ?
C00T C00O H00Q 108.8 . . ?
C00D C00P H00R 121.4 . . ?
C00S C00P C00D 117.2(3) . . ?
C00S C00P H00R 121.4 . . ?
C00G C00Q H00F 120.0 . . ?
C00G C00Q H00H 120.0 . . ?
H00F C00Q H00H 120.0 . . ?
S002 C00R H00S 109.8 . . ?
S002 C00R H00T 109.8 . . ?
H00S C00R H00T 108.2 . . ?
C00W C00R S002 109.5(2) . . ?
C00W C00R H00S 109.8 . . ?
C00W C00R H00T 109.8 . . ?
C00P C00S H00U 119.0 . . ?
C00P C00S C00U 122.0(3) . . ?
C00U C00S H00U 119.0 . . ?
C00O C00T H00V 117.7 . . ?
C00X C00T C00O 124.6(3) . . ?
C00X C00T H00V 117.7 . . ?
C00M C00U C00S 120.6(3) . . ?
C00M C00U H00W 119.7 . . ?
C00S C00U H00W 119.7 . . ?
C00N C00V H00J 120.0 . . ?
C00N C00V H00M 120.0 . . ?
H00J C00V H00M 120.0 . . ?
C00R C00W H00X 118.4 . . ?
C00Y C00W C00R 123.1(3) . . ?
C00Y C00W H00X 118.4 . . ?
C00T C00X H00Y 120.0 . . ?
C00T C00X H 120.0 . . ?
H00Y C00X H 120.0 . . ?
C00W C00Y H00Z 120.0 . . ?
C00W C00Y HA 120.0 . . ?
H00Z C00Y HA 120.0 . . ?
_shelx_res_file
;
TITL odjp5_a.res in P2(1)/c
REM Old TITL odjp5 in P2(1)/c
REM SHELXT solution in P2(1)/c
REM R1 0.180, Rweak 0.020, Alpha 0.036, Orientation as input
REM Formula found by SHELXT: C24 N2 O6 S2
CELL 0.71073 17.7719 8.1203 19.0328 90 110.633 90
ZERR 4 0.0016 0.0007 0.0019 0 0.011 0
LATT 1
SYMM -X,0.5+Y,0.5-Z
SFAC C H N O S
UNIT 112 120 8 8 8
SADI C00W H00x C00Y Ha C00Y H00z C00T H00v C00X H C00X H00y C00V H00m C00V =
H00J C00N H00N C00Q H00F C00Q H00H C00G H00G
L.S. 10
PLAN 20
BOND $H
list 4
fmap 2
acta
SHEL 100 0.83
OMIT 0 1 7
OMIT -2 1 3
OMIT -5 1 1
OMIT 8 0 0
REM
REM
REM
WGHT 0.025900 0.469600
FVAR 0.70101
S001 5 0.628534 0.643524 0.689725 11.00000 0.02660 0.02160 =
0.02759 -0.00267 0.01432 -0.00278
S002 5 0.859354 0.697954 0.612622 11.00000 0.02360 0.02739 =
0.03088 0.00056 0.00346 -0.00047
O003 4 0.616433 0.814804 0.656033 11.00000 0.04367 0.02021 =
0.03864 -0.00219 0.02849 -0.00329
O004 4 0.819968 0.546506 0.630511 11.00000 0.02694 0.02925 =
0.04471 0.00596 0.00148 -0.00499
N005 3 0.467245 0.501228 0.771819 11.00000 0.02493 0.02637 =
0.01883 0.00175 0.01182 -0.00143
AFIX 43
H005 2 0.453645 0.470383 0.808905 11.00000 -1.20000
AFIX 0
N006 3 1.046126 0.854663 0.779155 11.00000 0.01830 0.03095 =
0.02714 -0.00177 0.00102 -0.00384
AFIX 43
H006 2 1.095502 0.885549 0.797918 11.00000 -1.20000
AFIX 0
C007 1 0.459636 0.575255 0.655263 11.00000 0.02836 0.01143 =
0.02038 -0.00121 0.01026 0.00120
C008 1 0.543630 0.537951 0.776484 11.00000 0.02334 0.01263 =
0.02456 -0.00329 0.00983 -0.00060
C009 1 0.414793 0.520668 0.698952 11.00000 0.02690 0.01472 =
0.02300 -0.00014 0.01072 0.00241
C00A 1 0.418733 0.608101 0.579336 11.00000 0.03002 0.02268 =
0.02293 0.00046 0.01234 0.00314
AFIX 43
H00A 2 0.446442 0.645244 0.549081 11.00000 -1.20000
AFIX 0
C00B 1 0.541746 0.583722 0.706003 11.00000 0.02316 0.01594 =
0.02102 -0.00181 0.00914 -0.00015
C00C 1 0.611661 0.526950 0.849667 11.00000 0.02421 0.02492 =
0.02602 0.00462 0.00679 0.00080
AFIX 23
H00B 2 0.660215 0.567663 0.843385 11.00000 -1.20000
H00C 2 0.620435 0.412431 0.864858 11.00000 -1.20000
AFIX 0
C00D 1 0.994649 0.837817 0.818773 11.00000 0.03006 0.01898 =
0.02712 0.00147 0.00869 0.00301
C00E 1 0.919562 0.783952 0.768444 11.00000 0.02735 0.01649 =
0.03136 0.00109 0.00946 0.00137
C00F 1 1.006504 0.814708 0.705624 11.00000 0.02114 0.02064 =
0.02651 0.00199 0.00308 0.00355
C00G 1 0.596162 0.623911 0.910217 11.00000 0.02679 0.01966 =
0.02611 -0.00028 0.00749 -0.00164
AFIX 43
H00G 2 0.592986 0.737843 0.905035 11.00000 -1.20000
AFIX 0
C00H 1 0.929139 0.769871 0.696548 11.00000 0.02175 0.02262 =
0.02769 0.00023 0.00356 0.00067
C00I 1 0.336648 0.584716 0.549786 11.00000 0.03331 0.02799 =
0.02045 -0.00061 0.00499 0.00564
AFIX 43
H00I 2 0.309181 0.606544 0.499218 11.00000 -1.20000
AFIX 0
C00J 1 0.622996 0.511248 0.611390 11.00000 0.03047 0.02517 =
0.02729 -0.00344 0.01570 -0.00116
AFIX 23
H00D 2 0.577600 0.544905 0.567861 11.00000 -1.20000
H00E 2 0.671336 0.525964 0.599483 11.00000 -1.20000
AFIX 0
C00K 1 0.331999 0.496568 0.669116 11.00000 0.02731 0.02666 =
0.03335 0.00069 0.01669 0.00193
AFIX 43
H00K 2 0.303626 0.459906 0.698872 11.00000 -1.20000
AFIX 0
C00L 1 0.293879 0.528854 0.594310 11.00000 0.02620 0.02968 =
0.03146 -0.00404 0.00791 0.00247
AFIX 43
H00L 2 0.238610 0.513370 0.572750 11.00000 -1.20000
AFIX 0
C00M 1 0.857122 0.756118 0.795603 11.00000 0.02818 0.02942 =
0.04108 0.00246 0.01309 0.00021
AFIX 43
H00O 2 0.807152 0.720224 0.763468 11.00000 -1.20000
AFIX 0
C00N 1 0.614231 0.333283 0.626158 11.00000 0.04084 0.02853 =
0.04182 -0.01112 0.02470 -0.00606
AFIX 43
H00N 2 0.564454 0.297268 0.625885 11.00000 -1.20000
AFIX 0
C00O 1 1.047064 0.828253 0.649123 11.00000 0.03023 0.03530 =
0.03428 -0.00200 0.01215 -0.00342
AFIX 23
H00P 2 1.013171 0.777317 0.602645 11.00000 -1.20000
H00Q 2 1.052535 0.943811 0.638930 11.00000 -1.20000
AFIX 0
C00P 1 1.008405 0.864360 0.894558 11.00000 0.03564 0.02709 =
0.02998 -0.00012 0.00475 0.00037
AFIX 43
H00R 2 1.058209 0.899482 0.927344 11.00000 -1.20000
AFIX 0
C00Q 1 0.586784 0.560702 0.969637 11.00000 0.03886 0.03628 =
0.03555 -0.00477 0.01474 -0.00300
AFIX 93
H00F 2 0.589554 0.447252 0.976783 11.00000 -1.20000
H00H 2 0.577330 0.629107 1.004836 11.00000 -1.20000
AFIX 0
C00R 1 0.785419 0.861083 0.593904 11.00000 0.02492 0.03749 =
0.03974 0.00705 0.00426 0.01044
AFIX 23
H00S 2 0.739362 0.834243 0.549657 11.00000 -1.20000
H00T 2 0.767119 0.872425 0.636031 11.00000 -1.20000
AFIX 0
C00S 1 0.945363 0.836518 0.918893 11.00000 0.05939 0.02823 =
0.03025 0.00050 0.02206 0.00459
AFIX 43
H00U 2 0.952788 0.854216 0.969174 11.00000 -1.20000
AFIX 0
C00T 1 1.128232 0.749457 0.673611 11.00000 0.03726 0.02572 =
0.04711 -0.00245 0.02255 0.00301
AFIX 43
H00V 2 1.131660 0.638170 0.685884 11.00000 -1.20000
AFIX 0
C00U 1 0.870478 0.782460 0.870448 11.00000 0.04811 0.02877 =
0.04872 0.00432 0.02887 0.00429
AFIX 43
H00W 2 0.829243 0.764088 0.888938 11.00000 -1.20000
AFIX 0
C00V 1 0.671099 0.225715 0.639307 11.00000 0.05769 0.03408 =
0.04606 -0.00024 0.02837 0.00203
AFIX 93
H00J 2 0.721614 0.257588 0.639987 11.00000 -1.20000
H00M 2 0.661525 0.116402 0.648093 11.00000 -1.20000
AFIX 0
C00W 1 0.821857 1.018537 0.581727 11.00000 0.03716 0.03062 =
0.04799 0.00102 0.00528 0.00382
AFIX 43
H00X 2 0.852997 1.078354 0.623530 11.00000 -1.20000
AFIX 0
C00X 1 1.194303 0.825488 0.678952 11.00000 0.03573 0.04149 =
0.05866 -0.00859 0.02246 0.00376
AFIX 93
H00Y 2 1.193088 0.936809 0.667120 11.00000 -1.20000
H 2 1.242838 0.768621 0.694610 11.00000 -1.20000
AFIX 0
C00Y 1 0.812217 1.076739 0.515192 11.00000 0.05606 0.05547 =
0.06951 0.01726 0.01137 -0.01282
AFIX 93
H00Z 2 0.781337 1.019130 0.472546 11.00000 -1.20000
HA 2 0.836227 1.175821 0.510428 11.00000 -1.20000
AFIX 0
HKLF 4
REM odjp5_a.res in P2(1)/c
REM R1 = 0.0532 for 3004 Fo > 4sig(Fo) and 0.1032 for all 4690 data
REM 307 parameters refined using 66 restraints
END
WGHT 0.0262 0.4477
REM Highest difference peak 0.289, deepest hole -0.336, 1-sigma level 0.063
Q1 1 0.5927 0.6907 0.6302 11.00000 0.05 0.29
Q2 1 0.6964 0.6050 0.8424 11.00000 0.05 0.27
Q3 1 0.3533 0.6927 0.6480 11.00000 0.05 0.26
Q4 1 0.5497 0.5150 0.7367 11.00000 0.05 0.25
Q5 1 0.8113 0.6393 0.6379 11.00000 0.05 0.25
Q6 1 0.8978 0.7433 0.6626 11.00000 0.05 0.25
Q7 1 0.5739 0.6463 0.7059 11.00000 0.05 0.25
Q8 1 0.6316 0.8103 0.6206 11.00000 0.05 0.24
Q9 1 0.3822 0.5150 0.5622 11.00000 0.05 0.24
Q10 1 0.8783 0.9915 0.5385 11.00000 0.05 0.24
Q11 1 1.0813 0.8680 1.0336 11.00000 0.05 0.23
Q12 1 1.0671 0.7726 0.8282 11.00000 0.05 0.23
Q13 1 0.4513 0.5294 0.6133 11.00000 0.05 0.23
Q14 1 0.6297 0.7595 0.6855 11.00000 0.05 0.22
Q15 1 0.6845 0.2038 0.5463 11.00000 0.05 0.22
Q16 1 0.5069 0.5415 0.7786 11.00000 0.05 0.22
Q17 1 1.0395 0.7969 0.7406 11.00000 0.05 0.22
Q18 1 0.5920 0.8625 0.6955 11.00000 0.05 0.22
Q19 1 0.6377 0.5366 0.6610 11.00000 0.05 0.22
Q20 1 0.4343 0.5571 0.7302 11.00000 0.05 0.22
;
_shelx_res_checksum 52967
_olex2_date_sample_data_collection 2017-05-30
_olex2_submission_original_sample_id
'Sulfenylation Product - diallylsulfoxide/indole'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.077
_oxdiff_exptl_absorpt_empirical_full_min 0.937
#######################################################################
#
# 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_odjp11
_database_code_depnum_ccdc_archive 'CCDC 1570698'
_audit_update_record
;
2017-08-24 deposited with the CCDC.
2017-11-17 downloaded from the CCDC.
;
_audit_creation_date 2017-08-24
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelxl_version_number 2014/6
_chemical_name_common ?
_chemical_name_systematic 2-Allyl-3-(allylsulfinyl)-1-methyl-1H-indole
_chemical_formula_moiety 'C15 H17 N O S'
_chemical_formula_sum 'C15 H17 N O S'
_chemical_formula_weight 259.35
_chemical_melting_point ?
_chemical_oxdiff_formula C15H17NSO
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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system triclinic
_space_group_IT_number 2
_space_group_name_H-M_alt 'P -1'
_space_group_name_Hall '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
_cell_length_a 8.2973(5)
_cell_length_b 9.1320(6)
_cell_length_c 9.7066(5)
_cell_angle_alpha 104.937(5)
_cell_angle_beta 100.291(5)
_cell_angle_gamma 100.461(5)
_cell_volume 678.86(7)
_cell_formula_units_Z 2
_cell_measurement_reflns_used 2819
_cell_measurement_temperature 150
_cell_measurement_theta_max 29.2800
_cell_measurement_theta_min 4.3850
_shelx_estimated_absorpt_T_max ?
_shelx_estimated_absorpt_T_min ?
_exptl_absorpt_coefficient_mu 0.226
_exptl_absorpt_correction_T_max 1.00000
_exptl_absorpt_correction_T_min 0.79657
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.27b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details ?
_exptl_crystal_colour 'clear light colourless'
_exptl_crystal_colour_lustre clear
_exptl_crystal_colour_modifier light
_exptl_crystal_colour_primary colourless
_exptl_crystal_density_diffrn 1.269
_exptl_crystal_density_meas ?
_exptl_crystal_density_method ?
_exptl_crystal_description block
_exptl_crystal_F_000 276
_exptl_crystal_preparation ?
_exptl_crystal_size_max 0.42676
_exptl_crystal_size_mid 0.27785
_exptl_crystal_size_min 0.22233
_exptl_transmission_factor_max ?
_exptl_transmission_factor_min ?
_diffrn_reflns_av_R_equivalents 0.0194
_diffrn_reflns_av_unetI/netI 0.0382
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max 9
_diffrn_reflns_limit_h_min -9
_diffrn_reflns_limit_k_max 7
_diffrn_reflns_limit_k_min -11
_diffrn_reflns_limit_l_max 11
_diffrn_reflns_limit_l_min -11
_diffrn_reflns_number 4526
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full 25.242
_diffrn_reflns_theta_max 25.349
_diffrn_reflns_theta_min 3.721
_diffrn_ambient_temperature 150
_diffrn_detector 'CCD plate'
_diffrn_detector_area_resol_mean 5.1636
_diffrn_detector_type Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):
# Type Start End Width t~exp~ \w \q \k \f Frames
#--------------------------------------------------------------------------
1 \w -17.00 79.00 1.00 1.00 -- 11.69 57.00 -90.00 96
2 \w -16.00 71.00 1.00 1.00 -- 11.69 77.00 30.00 87
3 \w -60.00 33.00 1.00 1.00 -- 11.69 -57.00 120.00 93
;
_diffrn_measurement_device 'four-circle diffractometer'
_diffrn_measurement_device_type 'Xcalibur, Atlas'
_diffrn_measurement_method '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11 0.0527020000
_diffrn_orient_matrix_UB_12 0.0164039000
_diffrn_orient_matrix_UB_13 0.0709267000
_diffrn_orient_matrix_UB_21 0.0395682000
_diffrn_orient_matrix_UB_22 -0.0602305000
_diffrn_orient_matrix_UB_23 -0.0275945000
_diffrn_orient_matrix_UB_31 0.0605360000
_diffrn_orient_matrix_UB_32 0.0543909000
_diffrn_orient_matrix_UB_33 -0.0164037000
_diffrn_radiation_monochromator graphite
_diffrn_radiation_probe x-ray
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_source 'fine-focus sealed X-ray tube'
_diffrn_source_type 'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage 0.000
_reflns_Friedel_fraction_full .
_reflns_Friedel_fraction_max .
_reflns_number_gt 2102
_reflns_number_total 2471
_reflns_odcompleteness_completeness 99.14
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta 26.32
_reflns_special_details
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.
_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.
;
_reflns_threshold_expression 'I > 2\s(I)'
_computing_cell_refinement 'CrysAlisPro 1.171.39.27b (Rigaku OD, 2015)'
_computing_data_collection 'CrysAlisPro 1.171.39.27b (Rigaku OD, 2015)'
_computing_data_reduction 'CrysAlisPro 1.171.39.27b (Rigaku OD, 2015)'
_computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material 'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement 'ShelXL (Sheldrick, 2015)'
_computing_structure_solution 'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max 0.268
_refine_diff_density_min -0.313
_refine_diff_density_rms 0.044
_refine_ls_extinction_coef .
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.053
_refine_ls_hydrogen_treatment mixed
_refine_ls_matrix_type full
_refine_ls_number_parameters 180
_refine_ls_number_reflns 2471
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0455
_refine_ls_R_factor_gt 0.0366
_refine_ls_restrained_S_all 1.053
_refine_ls_shift/su_max 0.001
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0424P)^2^+0.1692P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.0890
_refine_ls_wR_factor_ref 0.0942
_refine_special_details ?
_olex2_refinement_description
;
1. Fixed Uiso
At 1.2 times of:
All C(H) groups, All C(H,H) groups
At 1.5 times of:
All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
C00A(H00A,H00B), C00C(H00D,H00E)
2.b Aromatic/amide H refined with riding coordinates:
C008(H008), C009(H009), C00B(H00C), C00D(H00F), C00F(H00J), C00G(H00K)
2.c Idealised Me refined as rotating group:
C00E(H00G,H00H,H00I)
;
_atom_sites_solution_hydrogens mixed
_atom_sites_solution_primary dual
_atom_sites_solution_secondary ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S001 S 0.75939(5) 0.83841(5) 0.42402(5) 0.02707(16) Uani 1 1 d . . . . .
O002 O 0.87637(16) 0.83766(16) 0.56069(14) 0.0393(4) Uani 1 1 d . . . . .
N003 N 0.35693(17) 0.49218(18) 0.28439(15) 0.0243(3) Uani 1 1 d . . . . .
C004 C 0.4366(2) 0.6465(2) 0.32133(18) 0.0230(4) Uani 1 1 d . . . . .
C005 C 0.4755(2) 0.4056(2) 0.30036(18) 0.0232(4) Uani 1 1 d . . . . .
C006 C 0.6084(2) 0.6608(2) 0.35909(18) 0.0235(4) Uani 1 1 d . . . . .
C007 C 0.6361(2) 0.5085(2) 0.34750(17) 0.0229(4) Uani 1 1 d . . . . .
C008 C 0.7787(2) 0.4486(2) 0.37521(18) 0.0263(4) Uani 1 1 d . . . . .
H008 H 0.8885 0.5160 0.4092 0.032 Uiso 1 1 calc R . . . .
C009 C 0.4531(2) 0.2463(2) 0.27837(19) 0.0295(4) Uani 1 1 d . . . . .
H009 H 0.3436 0.1783 0.2475 0.035 Uiso 1 1 calc R . . . .
C00A C 0.3429(2) 0.7697(2) 0.31515(19) 0.0282(4) Uani 1 1 d . . . . .
H00A H 0.4188 0.8722 0.3738 0.034 Uiso 1 1 calc R . . . .
H00B H 0.2473 0.7521 0.3619 0.034 Uiso 1 1 calc R . . . .
C00B C 0.5958(2) 0.1905(2) 0.3030(2) 0.0317(4) Uani 1 1 d . . . . .
H00C H 0.5845 0.0815 0.2861 0.038 Uiso 1 1 calc R . . . .
C00C C 0.8791(2) 0.8090(2) 0.2832(2) 0.0328(5) Uani 1 1 d . . . . .
H00D H 0.9891 0.8865 0.3187 0.039 Uiso 1 1 calc R . . . .
H00E H 0.9014 0.7036 0.2646 0.039 Uiso 1 1 calc R . . . .
C00D C 0.7567(2) 0.2909(2) 0.35234(19) 0.0297(4) Uani 1 1 d . . . . .
H00F H 0.8526 0.2493 0.3703 0.036 Uiso 1 1 calc R . . . .
C00E C 0.1754(2) 0.4244(2) 0.2385(2) 0.0331(5) Uani 1 1 d . . . . .
H00G H 0.1153 0.5081 0.2516 0.050 Uiso 1 1 calc GR . . . .
H00H H 0.1437 0.3571 0.2981 0.050 Uiso 1 1 calc GR . . . .
H00I H 0.1452 0.3624 0.1348 0.050 Uiso 1 1 calc GR . . . .
C00F C 0.2753(2) 0.7771(3) 0.1635(2) 0.0371(5) Uani 1 1 d . . . . .
H00J H 0.2107 0.8519 0.1560 0.044 Uiso 1 1 calc R . . . .
C00G C 0.7865(3) 0.8252(3) 0.1443(2) 0.0402(5) Uani 1 1 d . . . . .
H00K H 0.6946 0.7421 0.0838 0.048 Uiso 1 1 calc R . . . .
C00H C 0.2962(3) 0.6912(3) 0.0411(3) 0.0502(6) Uani 1 1 d . . . . .
C00I C 0.8258(4) 0.9483(3) 0.1016(3) 0.0574(7) Uani 1 1 d . . . . .
H00N H 0.921(4) 1.031(4) 0.156(3) 0.073(9) Uiso 1 1 d . . . . .
H00L H 0.362(3) 0.614(3) 0.040(3) 0.061(8) Uiso 1 1 d . . . . .
H00O H 0.762(3) 0.960(3) 0.017(3) 0.072(8) Uiso 1 1 d . . . . .
H00M H 0.253(3) 0.701(3) -0.049(3) 0.063(8) Uiso 1 1 d . . . . .
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
S001 0.0278(3) 0.0234(3) 0.0280(3) 0.00699(19) 0.00346(18) 0.00524(19)
O002 0.0353(7) 0.0386(9) 0.0348(8) 0.0131(6) -0.0065(6) -0.0019(6)
N003 0.0206(7) 0.0269(9) 0.0264(8) 0.0094(6) 0.0051(6) 0.0065(6)
C004 0.0264(9) 0.0259(10) 0.0198(8) 0.0083(7) 0.0074(7) 0.0102(7)
C005 0.0249(9) 0.0263(10) 0.0210(9) 0.0082(7) 0.0065(7) 0.0095(7)
C006 0.0248(9) 0.0246(10) 0.0229(9) 0.0084(7) 0.0057(7) 0.0087(7)
C007 0.0260(9) 0.0262(10) 0.0179(8) 0.0075(7) 0.0055(7) 0.0086(7)
C008 0.0246(9) 0.0313(11) 0.0244(9) 0.0090(8) 0.0049(7) 0.0102(8)
C009 0.0321(10) 0.0270(11) 0.0295(10) 0.0087(8) 0.0089(8) 0.0058(8)
C00A 0.0274(9) 0.0309(11) 0.0310(10) 0.0120(8) 0.0085(7) 0.0128(8)
C00B 0.0446(11) 0.0238(11) 0.0323(10) 0.0110(8) 0.0144(8) 0.0133(9)
C00C 0.0278(10) 0.0295(11) 0.0433(11) 0.0114(9) 0.0131(8) 0.0066(8)
C00D 0.0344(10) 0.0355(12) 0.0275(10) 0.0139(8) 0.0104(8) 0.0191(9)
C00E 0.0212(9) 0.0380(12) 0.0395(11) 0.0127(9) 0.0058(8) 0.0055(8)
C00F 0.0340(11) 0.0458(13) 0.0415(12) 0.0270(10) 0.0082(9) 0.0153(9)
C00G 0.0398(11) 0.0448(14) 0.0313(11) 0.0029(10) 0.0130(9) 0.0064(10)
C00H 0.0554(14) 0.0669(19) 0.0329(13) 0.0238(12) 0.0053(11) 0.0180(13)
C00I 0.087(2) 0.0550(18) 0.0358(13) 0.0161(12) 0.0179(13) 0.0250(16)
_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
S001 O002 1.4996(13) . ?
S001 C006 1.7464(18) . ?
S001 C00C 1.8218(19) . ?
N003 C004 1.367(2) . ?
N003 C005 1.382(2) . ?
N003 C00E 1.460(2) . ?
C004 C006 1.380(2) . ?
C004 C00A 1.487(3) . ?
C005 C007 1.405(2) . ?
C005 C009 1.387(3) . ?
C006 C007 1.430(3) . ?
C007 C008 1.403(2) . ?
C008 H008 0.9500 . ?
C008 C00D 1.371(3) . ?
C009 H009 0.9500 . ?
C009 C00B 1.378(3) . ?
C00A H00A 0.9900 . ?
C00A H00B 0.9900 . ?
C00A C00F 1.502(3) . ?
C00B H00C 0.9500 . ?
C00B C00D 1.398(3) . ?
C00C H00D 0.9900 . ?
C00C H00E 0.9900 . ?
C00C C00G 1.485(3) . ?
C00D H00F 0.9500 . ?
C00E H00G 0.9800 . ?
C00E H00H 0.9800 . ?
C00E H00I 0.9800 . ?
C00F H00J 0.9500 . ?
C00F C00H 1.304(3) . ?
C00G H00K 0.9500 . ?
C00G C00I 1.303(3) . ?
C00H H00L 0.96(3) . ?
C00H H00M 0.91(3) . ?
C00I H00N 0.95(3) . ?
C00I H00O 0.94(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
O002 S001 C006 107.72(8) . . ?
O002 S001 C00C 105.01(9) . . ?
C006 S001 C00C 99.50(8) . . ?
C004 N003 C005 109.49(14) . . ?
C004 N003 C00E 126.97(15) . . ?
C005 N003 C00E 123.52(16) . . ?
N003 C004 C006 108.46(16) . . ?
N003 C004 C00A 122.40(15) . . ?
C006 C004 C00A 129.12(16) . . ?
N003 C005 C007 108.02(16) . . ?
N003 C005 C009 129.73(16) . . ?
C009 C005 C007 122.24(17) . . ?
C004 C006 S001 124.41(14) . . ?
C004 C006 C007 107.94(15) . . ?
C007 C006 S001 127.44(13) . . ?
C005 C007 C006 106.07(15) . . ?
C008 C007 C005 118.96(17) . . ?
C008 C007 C006 134.94(16) . . ?
C007 C008 H008 120.6 . . ?
C00D C008 C007 118.84(17) . . ?
C00D C008 H008 120.6 . . ?
C005 C009 H009 121.3 . . ?
C00B C009 C005 117.44(17) . . ?
C00B C009 H009 121.3 . . ?
C004 C00A H00A 108.5 . . ?
C004 C00A H00B 108.5 . . ?
C004 C00A C00F 114.94(16) . . ?
H00A C00A H00B 107.5 . . ?
C00F C00A H00A 108.5 . . ?
C00F C00A H00B 108.5 . . ?
C009 C00B H00C 119.3 . . ?
C009 C00B C00D 121.34(19) . . ?
C00D C00B H00C 119.3 . . ?
S001 C00C H00D 109.3 . . ?
S001 C00C H00E 109.3 . . ?
H00D C00C H00E 108.0 . . ?
C00G C00C S001 111.40(13) . . ?
C00G C00C H00D 109.3 . . ?
C00G C00C H00E 109.3 . . ?
C008 C00D C00B 121.14(18) . . ?
C008 C00D H00F 119.4 . . ?
C00B C00D H00F 119.4 . . ?
N003 C00E H00G 109.5 . . ?
N003 C00E H00H 109.5 . . ?
N003 C00E H00I 109.5 . . ?
H00G C00E H00H 109.5 . . ?
H00G C00E H00I 109.5 . . ?
H00H C00E H00I 109.5 . . ?
C00A C00F H00J 116.7 . . ?
C00H C00F C00A 126.5(2) . . ?
C00H C00F H00J 116.7 . . ?
C00C C00G H00K 118.6 . . ?
C00I C00G C00C 122.9(2) . . ?
C00I C00G H00K 118.6 . . ?
C00F C00H H00L 121.7(15) . . ?
C00F C00H H00M 123.2(17) . . ?
H00L C00H H00M 115(2) . . ?
C00G C00I H00N 120.8(17) . . ?
C00G C00I H00O 121.9(17) . . ?
H00N C00I H00O 117(2) . . ?
_shelx_res_file
;
TITL odjp11_a.res in P-1
REM Old TITL
REM SHELXT solution in P-1
REM R1 0.129, Rweak 0.008, Alpha 0.037, Orientation as input
REM Formula found by SHELXT: C14 N O2 S
CELL 0.71073 8.2973 9.132 9.7066 104.937 100.291 100.461
ZERR 2 0.0005 0.0006 0.0005 0.005 0.005 0.005
LATT 1
SFAC C H N O S
UNIT 30 34 2 2 2
L.S. 10
PLAN 20
TEMP -123.15
BOND $H
list 4
fmap 2
acta
SHEL 100 0.83
REM
REM
REM
WGHT 0.042400 0.169200
FVAR 11.63199
S001 5 0.759388 0.838407 0.424023 11.00000 0.02782 0.02340 =
0.02795 0.00699 0.00346 0.00524
O002 4 0.876365 0.837664 0.560690 11.00000 0.03535 0.03864 =
0.03476 0.01309 -0.00653 -0.00191
N003 3 0.356930 0.492178 0.284390 11.00000 0.02061 0.02688 =
0.02644 0.00940 0.00513 0.00651
C004 1 0.436589 0.646523 0.321334 11.00000 0.02643 0.02594 =
0.01978 0.00834 0.00740 0.01017
C005 1 0.475509 0.405574 0.300364 11.00000 0.02490 0.02628 =
0.02100 0.00823 0.00647 0.00952
C006 1 0.608407 0.660817 0.359086 11.00000 0.02478 0.02456 =
0.02288 0.00838 0.00568 0.00865
C007 1 0.636077 0.508475 0.347502 11.00000 0.02604 0.02625 =
0.01791 0.00755 0.00546 0.00859
C008 1 0.778656 0.448572 0.375214 11.00000 0.02462 0.03127 =
0.02437 0.00895 0.00487 0.01017
AFIX 43
H008 2 0.888461 0.516040 0.409232 11.00000 -1.20000
AFIX 0
C009 1 0.453106 0.246332 0.278371 11.00000 0.03212 0.02702 =
0.02952 0.00867 0.00888 0.00581
AFIX 43
H009 2 0.343625 0.178341 0.247517 11.00000 -1.20000
AFIX 0
C00A 1 0.342855 0.769738 0.315155 11.00000 0.02736 0.03088 =
0.03101 0.01203 0.00846 0.01276
AFIX 23
H00A 2 0.418782 0.872241 0.373786 11.00000 -1.20000
H00B 2 0.247301 0.752098 0.361887 11.00000 -1.20000
AFIX 0
C00B 1 0.595770 0.190465 0.302991 11.00000 0.04462 0.02377 =
0.03232 0.01100 0.01439 0.01328
AFIX 43
H00C 2 0.584501 0.081494 0.286091 11.00000 -1.20000
AFIX 0
C00C 1 0.879098 0.809018 0.283228 11.00000 0.02776 0.02947 =
0.04328 0.01141 0.01313 0.00664
AFIX 23
H00D 2 0.989101 0.886527 0.318719 11.00000 -1.20000
H00E 2 0.901368 0.703616 0.264576 11.00000 -1.20000
AFIX 0
C00D 1 0.756749 0.290928 0.352337 11.00000 0.03442 0.03545 =
0.02751 0.01388 0.01041 0.01908
AFIX 43
H00F 2 0.852608 0.249255 0.370329 11.00000 -1.20000
AFIX 0
C00E 1 0.175365 0.424389 0.238460 11.00000 0.02122 0.03805 =
0.03950 0.01268 0.00579 0.00554
AFIX 137
H00G 2 0.115277 0.508121 0.251625 11.00000 -1.50000
H00H 2 0.143721 0.357142 0.298113 11.00000 -1.50000
H00I 2 0.145196 0.362391 0.134805 11.00000 -1.50000
AFIX 0
C00F 1 0.275260 0.777087 0.163512 11.00000 0.03401 0.04584 =
0.04154 0.02705 0.00817 0.01530
AFIX 43
H00J 2 0.210747 0.851857 0.156000 11.00000 -1.20000
AFIX 0
C00G 1 0.786518 0.825164 0.144284 11.00000 0.03977 0.04478 =
0.03126 0.00287 0.01300 0.00638
AFIX 43
H00K 2 0.694581 0.742055 0.083828 11.00000 -1.20000
AFIX 0
C00H 1 0.296217 0.691167 0.041139 11.00000 0.05543 0.06690 =
0.03288 0.02380 0.00533 0.01800
C00I 1 0.825814 0.948297 0.101621 11.00000 0.08744 0.05503 =
0.03584 0.01614 0.01795 0.02500
H00N 2 0.920701 1.030865 0.156441 11.00000 0.07324
H00L 2 0.361970 0.614344 0.039704 11.00000 0.06079
H00O 2 0.761717 0.959642 0.016651 11.00000 0.07159
H00M 2 0.253175 0.700862 -0.048591 11.00000 0.06316
HKLF 4
REM odjp11_a.res in P-1
REM R1 = 0.0366 for 2102 Fo > 4sig(Fo) and 0.0455 for all 2471 data
REM 180 parameters refined using 0 restraints
END
WGHT 0.0415 0.1839
REM Highest difference peak 0.268, deepest hole -0.313, 1-sigma level 0.044
Q1 1 0.8165 0.8161 0.3353 11.00000 0.05 0.27
Q2 1 0.6708 0.7458 0.3700 11.00000 0.05 0.25
Q3 1 0.6459 0.5944 0.3284 11.00000 0.05 0.19
Q4 1 0.5319 0.6695 0.3908 11.00000 0.05 0.19
Q5 1 0.9301 0.7142 0.3154 11.00000 0.05 0.18
Q6 1 0.5381 0.6633 0.3300 11.00000 0.05 0.18
Q7 1 0.9700 0.9375 0.3504 11.00000 0.05 0.18
Q8 1 0.1116 0.4724 0.3258 11.00000 0.05 0.18
Q9 1 0.1307 0.4660 0.1555 11.00000 0.05 0.18
Q10 1 0.6884 0.9276 0.4149 11.00000 0.05 0.17
Q11 1 0.6959 0.4829 0.3384 11.00000 0.05 0.17
Q12 1 0.3939 0.7065 0.3316 11.00000 0.05 0.16
Q13 1 0.4172 0.4434 0.2804 11.00000 0.05 0.16
Q14 1 0.5592 0.4539 0.3332 11.00000 0.05 0.15
Q15 1 0.4634 0.3272 0.2666 11.00000 0.05 0.15
Q16 1 0.2689 0.4646 0.2638 11.00000 0.05 0.15
Q17 1 0.3416 0.7819 0.1169 11.00000 0.05 0.14
Q18 1 0.1404 0.2957 0.1814 11.00000 0.05 0.13
Q19 1 0.3981 0.5720 0.3213 11.00000 0.05 0.13
Q20 1 0.2290 0.7986 0.4528 11.00000 0.05 0.12
;
_shelx_res_checksum 66396
_olex2_date_sample_data_collection 2017-06-07
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.337
_oxdiff_exptl_absorpt_empirical_full_min 0.736