#------------------------------------------------------------------------------
#$Date: 2020-10-03 04:22:08 +0300 (Sat, 03 Oct 2020) $
#$Revision: 256967 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/92/1559249.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1559249
loop_
_publ_author_name
'Maiti, Avijit'
'Chandra, Shubhadeep'
'Sarkar, Biprajit'
'Jana, Anukul'
_publ_section_title
;
 Acyclic Diaminocarbene-Based Thiele, Chichibabin, and Müller
 Hydrocarbons
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D0SC03622F
_journal_year                    2020
_chemical_formula_moiety         '2(C F3 O3 S), C30 H48 N4'
_chemical_formula_sum            'C32 H48 F6 N4 O6 S2'
_chemical_formula_weight         762.86
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-07-10
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-02-12 deposited with the CCDC.	2020-10-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.514(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.8834(7)
_cell_length_b                   9.6798(5)
_cell_length_c                   29.2643(14)
_cell_measurement_reflns_used    9112
_cell_measurement_temperature    293
_cell_measurement_theta_max      27.8920
_cell_measurement_theta_min      3.0500
_cell_volume                     3866.8(3)
_computing_cell_refinement       'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_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)'
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.895
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     50.00  83.00   0.50   47.25    --    7.10  77.00   0.00   66
  2  ω    -81.00  23.00   0.50   47.25    --    7.10 -57.00   0.00  208
  3  ω     -1.00  81.00   0.50   47.25    --   -7.50  38.00-120.00  164
  4  ω    -48.00 -19.00   0.50   47.25    --   -7.50  38.00-120.00   58
  5  ω    -11.00  15.00   0.50   47.25    --   -7.50 -77.00  30.00   52
  6  ω    -25.00  22.00   0.50   47.25    --   -7.50 -82.00 -60.00   94
  7  ω    -62.00   0.00   0.50   47.25    --   -7.50 -82.00  90.00  124
  8  ω    -24.00  31.00   0.50   47.25    --   -7.50 -77.00 120.00  110
  9  ω    -56.00  33.00   0.50   47.25    --   -7.50 -38.00-180.00  178
 10  ω    -63.00 -23.00   0.50   47.25    --   -7.50 -82.00 150.00   80
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0005759500
_diffrn_orient_matrix_UB_12      0.0337255500
_diffrn_orient_matrix_UB_13      0.0214637000
_diffrn_orient_matrix_UB_21      -0.0091028500
_diffrn_orient_matrix_UB_22      -0.0640785500
_diffrn_orient_matrix_UB_23      0.0101615000
_diffrn_orient_matrix_UB_31      0.0511624500
_diffrn_orient_matrix_UB_32      -0.0110335500
_diffrn_orient_matrix_UB_33      0.0066141000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0296
_diffrn_reflns_av_unetI/netI     0.0219
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.895
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            29846
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.895
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.060
_diffrn_reflns_theta_min         2.746
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.211
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90143
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.29d (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_description       block
_exptl_crystal_F_000             1608
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.508
_refine_diff_density_min         -0.450
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     232
_refine_ls_number_reflns         4630
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.0834
_refine_ls_R_factor_gt           0.0656
_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/[σ²(Fo²)+(0.1041P)²+3.7210P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1952
_refine_ls_wR_factor_ref         0.2073
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3461
_reflns_number_total             4630
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0sc03622f2.cif
_cod_data_source_block           aj0988
_cod_database_code               1559249
_shelx_shelxl_version_number     2017/1
_chemical_oxdiff_formula         CHNOFS
_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.
;
_shelx_estimated_absorpt_t_max   0.979
_shelx_estimated_absorpt_t_min   0.939
_reflns_odcompleteness_completeness 99.86
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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.a Ternary CH refined with riding coordinates:
 C9(H9), C13(H13)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C3(H3), C4(H4), C7(H7)
2.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C8(H8A,H8B,H8C), C15(H15A,H15B,H15C), C12(H12A,H12B,
 H12C), C10(H10A,H10B,H10C), C14(H14A,H14B,H14C)
;
_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 1.241
_oxdiff_exptl_absorpt_empirical_full_min 0.754
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
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
S1 S 0.25980(5) 0.97816(8) 0.39588(2) 0.0620(2) Uani 1 1 d . . . . .
N2 N 0.22878(14) 0.4995(2) 0.43445(7) 0.0476(5) Uani 1 1 d . . . . .
N1 N 0.35294(13) 0.4860(2) 0.39037(7) 0.0476(5) Uani 1 1 d . . . . .
F3 F 0.2742(2) 0.8507(2) 0.31805(7) 0.1050(8) Uani 1 1 d . . . . .
C2 C 0.18388(14) 0.4950(2) 0.35072(7) 0.0374(4) Uani 1 1 d . . . . .
C5 C 0.03915(14) 0.4915(2) 0.27089(7) 0.0375(4) Uani 1 1 d . . . . .
C1 C 0.25881(15) 0.4938(2) 0.39421(7) 0.0402(5) Uani 1 1 d . . . . .
C6 C 0.09770(16) 0.3759(2) 0.28362(7) 0.0438(5) Uani 1 1 d . . . . .
H6 H 0.087973 0.296409 0.265518 0.053 Uiso 1 1 calc R . . . .
O1 O 0.2615(2) 1.1208(3) 0.40663(9) 0.1014(9) Uani 1 1 d . . . . .
C3 C 0.12611(16) 0.6113(2) 0.33857(7) 0.0431(5) Uani 1 1 d . . . . .
H3 H 0.134853 0.689812 0.357162 0.052 Uiso 1 1 calc R . . . .
C4 C 0.05578(16) 0.6090(2) 0.29873(7) 0.0440(5) Uani 1 1 d . . . . .
H4 H 0.018481 0.687780 0.290213 0.053 Uiso 1 1 calc R . . . .
C7 C 0.17010(16) 0.3782(2) 0.32290(8) 0.0448(5) Uani 1 1 d . . . . .
H7 H 0.209687 0.301095 0.330681 0.054 Uiso 1 1 calc R . . . .
O2 O 0.1672(2) 0.9146(3) 0.39602(11) 0.1065(9) Uani 1 1 d . . . . .
C9 C 0.12604(17) 0.4640(3) 0.43867(8) 0.0526(6) Uani 1 1 d . . . . .
H9 H 0.091303 0.436649 0.407793 0.063 Uiso 1 1 calc R . . . .
C13 C 0.38746(17) 0.5406(3) 0.34899(9) 0.0539(6) Uani 1 1 d . . . . .
H13 H 0.331695 0.585971 0.329345 0.065 Uiso 1 1 calc R . . . .
F2 F 0.1909(3) 1.0347(3) 0.30982(9) 0.1509(14) Uani 1 1 d . . . . .
O3 O 0.3386(3) 0.8993(4) 0.41800(11) 0.1352(13) Uani 1 1 d . . . . .
C11 C 0.1260(2) 0.3414(3) 0.47061(10) 0.0664(7) Uani 1 1 d . . . . .
H11A H 0.160143 0.265825 0.459501 0.100 Uiso 1 1 calc GR . . . .
H11B H 0.059718 0.314462 0.471219 0.100 Uiso 1 1 calc GR . . . .
H11C H 0.158182 0.366014 0.501411 0.100 Uiso 1 1 calc GR . . . .
C16 C 0.2687(3) 0.9749(3) 0.33508(12) 0.0773(9) Uani 1 1 d . . . . .
C8 C 0.2916(2) 0.5510(4) 0.47716(9) 0.0699(8) Uani 1 1 d . . . . .
H8A H 0.323279 0.474420 0.494613 0.105 Uiso 1 1 calc GR . . . .
H8B H 0.252139 0.599706 0.495610 0.105 Uiso 1 1 calc GR . . . .
H8C H 0.340168 0.612260 0.469077 0.105 Uiso 1 1 calc GR . . . .
F1 F 0.3410(4) 1.0437(4) 0.32632(15) 0.203(2) Uani 1 1 d . . . . .
C15 C 0.4657(2) 0.6495(3) 0.36354(13) 0.0778(9) Uani 1 1 d . . . . .
H15A H 0.441354 0.718260 0.382187 0.117 Uiso 1 1 calc GR . . . .
H15B H 0.482110 0.692276 0.336375 0.117 Uiso 1 1 calc GR . . . .
H15C H 0.522986 0.606937 0.381258 0.117 Uiso 1 1 calc GR . . . .
C12 C 0.4268(2) 0.4195(4) 0.42577(12) 0.0810(10) Uani 1 1 d . . . . .
H12A H 0.458182 0.488010 0.447162 0.122 Uiso 1 1 calc GR . . . .
H12B H 0.474862 0.374989 0.411035 0.122 Uiso 1 1 calc GR . . . .
H12C H 0.395771 0.352067 0.442282 0.122 Uiso 1 1 calc GR . . . .
C10 C 0.0730(2) 0.5883(4) 0.45400(13) 0.0815(9) Uani 1 1 d . . . . .
H10A H 0.098518 0.608061 0.486071 0.122 Uiso 1 1 calc GR . . . .
H10B H 0.004233 0.568523 0.450260 0.122 Uiso 1 1 calc GR . . . .
H10C H 0.082690 0.666911 0.435343 0.122 Uiso 1 1 calc GR . . . .
C14 C 0.4226(3) 0.4265(4) 0.32038(13) 0.0854(10) Uani 1 1 d . . . . .
H14A H 0.481747 0.386899 0.337467 0.128 Uiso 1 1 calc GR . . . .
H14B H 0.435050 0.464129 0.291679 0.128 Uiso 1 1 calc GR . . . .
H14C H 0.373125 0.356257 0.313927 0.128 Uiso 1 1 calc GR . . . .
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'
F F 0.0171 0.0103 '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'
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
O1 S1 O2 113.50(18) . . ?
O1 S1 C16 103.57(16) . . ?
O2 S1 C16 102.65(17) . . ?
O3 S1 O1 116.8(2) . . ?
O3 S1 O2 113.2(2) . . ?
O3 S1 C16 105.05(18) . . ?
C1 N2 C9 121.73(19) . . ?
C1 N2 C8 122.4(2) . . ?
C8 N2 C9 115.7(2) . . ?
C1 N1 C13 121.14(19) . . ?
C1 N1 C12 122.4(2) . . ?
C12 N1 C13 116.5(2) . . ?
C3 C2 C1 120.33(18) . . ?
C7 C2 C1 119.72(18) . . ?
C7 C2 C3 119.93(19) . . ?
C6 C5 C5 121.72(14) . 2 ?
C6 C5 C4 118.21(19) . . ?
C4 C5 C5 120.07(14) . 2 ?
N2 C1 N1 123.4(2) . . ?
N2 C1 C2 118.48(18) . . ?
N1 C1 C2 118.07(19) . . ?
C5 C6 H6 119.7 . . ?
C7 C6 C5 120.67(19) . . ?
C7 C6 H6 119.7 . . ?
C2 C3 H3 120.3 . . ?
C4 C3 C2 119.37(19) . . ?
C4 C3 H3 120.3 . . ?
C5 C4 H4 119.2 . . ?
C3 C4 C5 121.60(19) . . ?
C3 C4 H4 119.2 . . ?
C2 C7 H7 119.9 . . ?
C6 C7 C2 120.19(19) . . ?
C6 C7 H7 119.9 . . ?
N2 C9 H9 107.6 . . ?
N2 C9 C11 109.9(2) . . ?
N2 C9 C10 111.3(2) . . ?
C11 C9 H9 107.6 . . ?
C11 C9 C10 112.6(2) . . ?
C10 C9 H9 107.6 . . ?
N1 C13 H13 107.5 . . ?
N1 C13 C15 109.9(2) . . ?
N1 C13 C14 112.1(2) . . ?
C15 C13 H13 107.5 . . ?
C15 C13 C14 112.0(2) . . ?
C14 C13 H13 107.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
F3 C16 S1 114.2(2) . . ?
F3 C16 F2 106.7(3) . . ?
F2 C16 S1 110.3(3) . . ?
F1 C16 S1 112.9(3) . . ?
F1 C16 F3 107.5(3) . . ?
F1 C16 F2 104.6(4) . . ?
N2 C8 H8A 109.5 . . ?
N2 C8 H8B 109.5 . . ?
N2 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N1 C12 H12A 109.5 . . ?
N1 C12 H12B 109.5 . . ?
N1 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O1 1.415(2) . ?
S1 O2 1.426(3) . ?
S1 O3 1.393(3) . ?
S1 C16 1.806(3) . ?
N2 C1 1.320(3) . ?
N2 C9 1.494(3) . ?
N2 C8 1.474(3) . ?
N1 C1 1.334(3) . ?
N1 C13 1.479(3) . ?
N1 C12 1.467(3) . ?
F3 C16 1.309(3) . ?
C2 C1 1.490(3) . ?
C2 C3 1.390(3) . ?
C2 C7 1.386(3) . ?
C5 C5 1.480(4) 2 ?
C5 C6 1.393(3) . ?
C5 C4 1.394(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.382(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.378(3) . ?
C4 H4 0.9300 . ?
C7 H7 0.9300 . ?
C9 H9 0.9800 . ?
C9 C11 1.511(4) . ?
C9 C10 1.521(4) . ?
C13 H13 0.9800 . ?
C13 C15 1.518(4) . ?
C13 C14 1.519(4) . ?
F2 C16 1.325(5) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C16 F1 1.269(4) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
