Dual Chalcogen-Chalcogen Bonding Catalysis.
Wang, Wei; Zhu, Haofu; Feng, Lei; Yu, Qun; Hao, Jing-Cheng; Zhu, Rongxiu; Wang, Yao; Journal of the American Chemical Society  (2020) –; doi:10.1021/jacs.9b12610

data_4134091
_publ_section_title
;
 Dual Chalcogen-Chalcogen Bonding Catalysis.
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.9b12610
_journal_year                    2020
_chemical_formula_moiety
'C51 H42 O P2 Se2, 0.5(C0.5 F2 O1.5 S0.5), 0.5(C F3 O3 S), 0.25(C F2 O3 S)'
_chemical_formula_sum            'C52 H42 F3 O4 P2 S Se2'
_chemical_formula_weight         1039.77
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2019-04-05
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 106.330(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   20.6736(4)
_cell_length_b                   15.6007(4)
_cell_length_c                   36.5467(6)
_cell_measurement_reflns_used    20126
_cell_measurement_temperature    172.98(10)
_cell_measurement_theta_max      75.4860
_cell_measurement_theta_min      3.7090
_cell_volume                     11311.6(4)
_computing_cell_refinement
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_data_collection
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_data_reduction
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      172.98(10)
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku Saturn724+'
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.990
_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   -120.00 -95.00   1.00    0.18    --  -48.45-122.00 161.00   25
  2  \w    -89.00 -10.00   1.00    0.18    --  -48.45 122.00-116.00   79
  3  \w   -120.00 -53.00   1.00    0.18    --  -48.45-150.00   0.00   67
  4  \w     37.00  63.00   1.00    0.18    --   48.45-122.00 161.00   26
  5  \w    -99.00 -53.00   1.00    1.25    --  -86.25-150.00   0.00   46
  6  \w     53.00 134.00   1.00    1.25    --  106.49-150.00   0.00   81
  7  \w     35.00 114.00   1.00    1.25    --  106.49-122.00 161.00   79
  8  \w     99.00 126.00   1.00    1.25    --  106.49 150.00  44.00   27
  9  \w   -120.00 -33.00   1.00    0.18    --  -48.45 -77.00   0.00   87
 10  \w   -158.00 -74.00   1.00    1.25    --  -86.25 -45.00  60.00   84
 11  \w     35.00 123.00   1.00    1.25    --  106.49 -61.00 150.00   88
 12  \w     34.00 108.00   1.00    1.25    --  106.49 -94.00 -30.00   74
 13  \w     32.00  99.00   1.00    1.25    --  106.49 -30.00   0.00   67
 14  \w     35.00 118.00   1.00    1.25    --  106.49 -45.00 -60.00   83
;
_diffrn_measurement_device       'AFC12 (Right): Kappa 3 circle'
_diffrn_measurement_device_type  'Rigaku Saturn724+ (2x2 bin mode)'
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0095770000
_diffrn_orient_matrix_UB_12      0.0909174000
_diffrn_orient_matrix_UB_13      -0.0141523000
_diffrn_orient_matrix_UB_21      -0.0404391000
_diffrn_orient_matrix_UB_22      0.0373550000
_diffrn_orient_matrix_UB_23      0.0258404000
_diffrn_orient_matrix_UB_31      0.0655797000
_diffrn_orient_matrix_UB_32      0.0098273000
_diffrn_orient_matrix_UB_33      0.0325456000
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0710
_diffrn_reflns_av_unetI/netI     0.0610
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       43
_diffrn_reflns_limit_l_min       -43
_diffrn_reflns_number            68185
_diffrn_reflns_point_group_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         67.061
_diffrn_reflns_theta_min         2.855
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           24.0
_diffrn_source_power             1.2
_diffrn_source_target            Mo
_diffrn_source_type              'Rotating Anode'
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    2.910
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.53613
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.25a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.221
_exptl_crystal_description       block
_exptl_crystal_F_000             4216
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_refine_diff_density_max         3.032
_refine_diff_density_min         -0.961
_refine_diff_density_rms         0.106
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1293
_refine_ls_number_reflns         19992
_refine_ls_number_restraints     514
_refine_ls_restrained_S_all      1.128
_refine_ls_R_factor_all          0.1081
_refine_ls_R_factor_gt           0.0859
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1231P)^2^+30.6731P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2335
_refine_ls_wR_factor_ref         0.2578
_reflns_Friedel_coverage         0.000
_reflns_number_gt                14679
_reflns_number_total             19992
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b12610_si_002.cif
_cod_data_source_block           180329f
_cod_database_code               4134091
_shelxl_version_number           2013-4
_chemical_oxdiff_formula         CSeP
_reflns_odcompleteness_completeness 99.03
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C101-S1AA
 1.85 with sigma of 0.01
 C102-S3
 1.85 with sigma of 0.01
 F2-C101 = F5-C101 = F3-C101 = F8-C102 = F7-C102 = F9-C102
 1.45 with sigma of 0.01
 C102-O11
 2.65 with sigma of 0.01
 O9-C102
 2.65 with sigma of 0.01
 S3-O9 = S3-O11 = S3-O10 = S1AA-O8 = S1AA-O6 = S1AA-O5
 1.45 with sigma of 0.01
 O10-C102
 2.65 with sigma of 0.01
 C100-F4
 1.45 with sigma of 0.01
 F6-C100
 1.45 with sigma of 0.01
 C100-F1
 1.45 with sigma of 0.01
 S0AA-O4
 1.45 with sigma of 0.01
 S0AA-O7
 1.45 with sigma of 0.01
 F4-F6
 2.35 with sigma of 0.01
 F6-F1
 2.35 with sigma of 0.01
 F1-F4
 2.35 with sigma of 0.01
 S0AA-O3
 1.45 with sigma of 0.01
 S0AA-C100
 1.85 with sigma of 0.01
 O3-O4
 2.35 with sigma of 0.01
 O3-O7
 2.35 with sigma of 0.01
 O4-O7
 2.35 with sigma of 0.01
 C100-O4
 2.75 with sigma of 0.01
 O7-C100
 2.75 with sigma of 0.01
 O3-C100
 2.75 with sigma of 0.01
 C101-F2 \\sim C102-F8
 with sigma of 0.02
 C101-F3 \\sim C102-F7
 with sigma of 0.02
 C101-F5 \\sim C102-F9
 with sigma of 0.02
 F2-F3 \\sim F8-F7
 with sigma of 0.04
 F2-F5 \\sim F8-F9
 with sigma of 0.04
 F3-F5 \\sim F7-F9
 with sigma of 0.04
 S1AA-C101 \\sim S3-C102
 with sigma of 0.02
 S1AA-F2 \\sim S3-F8
 with sigma of 0.04
 S1AA-F3 \\sim S3-F7
 with sigma of 0.04
 S1AA-F5 \\sim S3-F9
 with sigma of 0.04
 C101-O5 \\sim C102-O9
 with sigma of 0.04
 C101-O6 \\sim C102-O11
 with sigma of 0.04
 O5-O6 \\sim O9-O11
 with sigma of 0.04
 S1AA-O5 \\sim S3-O9
 with sigma of 0.02
 S1AA-O6 \\sim S3-O11
 with sigma of 0.02
 C101-O8 \\sim C102-O10
 with sigma of 0.04
 O5-O8 \\sim O9-O10
 with sigma of 0.04
 O6-O8 \\sim O11-O10
 with sigma of 0.04
 S1AA-O8 \\sim S3-O10
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
S1AA \\sim F2 \\sim F3 \\sim F5 \\sim O5 \\sim O6 \\sim O8 \\sim C101 \\sim S3
\\sim F7 \\sim F8 \\sim F9 \\sim O9 \\sim O10 \\sim O11 \\sim C102: within 1.7A
with sigma of 0.004 and sigma for terminal atoms of 0.008
S0AA \\sim F1 \\sim F4 \\sim F6 \\sim O3 \\sim O4 \\sim O7 \\sim C100: within
1.7A with sigma of 0.004 and sigma for terminal atoms of 0.008
F6 \\sim S0AA \\sim O3 \\sim O4 \\sim O7 \\sim C100 \\sim F1 \\sim F4: within
2A with sigma of 0.004 and sigma for terminal atoms of 0.004
F49 \\sim C0AA \\sim F36 \\sim O21 \\sim O30 \\sim O39 \\sim F1: within 2A with
sigma of 0.004 and sigma for terminal atoms of 0.008
C28 \\sim C29 \\sim C47 \\sim C45 \\sim C34 \\sim C48: within 2A with sigma of
0.004 and sigma for terminal atoms of 0.008
C38 \\sim C40 \\sim C31 \\sim C26 \\sim C25 \\sim C27: within 2A with sigma of
0.008 and sigma for terminal atoms of 0.004
C9 \\sim C5AA \\sim C7 \\sim C18 \\sim C15 \\sim C17: within 2A with sigma of
0.008 and sigma for terminal atoms of 0.004
C42 \\sim C33 \\sim C23 \\sim C105 \\sim C43 \\sim C36: within 2A with sigma of
0.008 and sigma for terminal atoms of 0.004
C49 \\sim C50 \\sim C44 \\sim C24: within 2A with sigma of 0.008 and sigma for
terminal atoms of 0.004
C76 \\sim C58 \\sim C80 \\sim C92 \\sim C83 \\sim C89 \\sim O2 \\sim C54:
within 2A with sigma of 0.008 and sigma for terminal atoms of 0.004
4. Others
 Sof(S3)=Sof(F7)=Sof(F8)=Sof(F9)=Sof(O9)=Sof(O10)=Sof(O11)=Sof(C102)=1-FVAR(1)
 Sof(S1AA)=Sof(F2)=Sof(F3)=Sof(F5)=Sof(O5)=Sof(O6)=Sof(O8)=Sof(C101)=FVAR(1)
 Fixed Sof: S0AA(0.5) F4(0.5) F6(0.5) O3(0.5) O4(0.5) O7(0.5) C100(0.5)
 S4(0.5) O21(0.5) O30(0.5) F36(0.5) O39(0.5) C0AA(0.5) F49(0.5)
5.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5), C6(H6), C7(H7), C8(H8), C9(H9), C10(H10), C11(H11), C12(H12),
 C13(H13), C14(H14), C15(H15), C16(H16), C17(H17), C18(H18), C21(H21), C25(H25),
  C26(H26), C29(H29), C30(H30), C31(H31), C32(H32), C34(H34), C35(H35),
 C36(H36), C37(H37), C38(H38), C39(H39), C40(H40), C41(H41), C42(H42), C43(H43),
  C45(H45), C46(H46), C47(H47), C48(H48), C52(H52), C57(H57), C59(H59),
 C61(H61), C62(H62), C63(H63), C64(H64), C65(H65), C66(H66), C68(H68), C69(H69),
  C70(H70), C71(H71), C72(H72), C74(H74), C77(H77), C79(H79), C81(H81),
 C82(H82), C83(H83), C84(H84), C85(H85), C86(H86), C87(H87), C88(H88), C89(H89),
  C91(H91), C92(H92), C93(H93), C94(H94), C95(H95), C96(H96), C98(H98),
 C99(H99), C103(H103), C104(H104)
5.b Idealised Me refined as rotating group:
 C49(H49A,H49B,H49C), C50(H50A,H50B,H50C), C90(H90A,H90B,H90C), C97(H97A,H97B,
 H97C)
;
_shelx_res_checksum              18082
_shelx_hkl_checksum              69265
_shelx_fab_checksum              93534
_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 1.516
_oxdiff_exptl_absorpt_empirical_full_min 0.594