#------------------------------------------------------------------------------
#$Date: 2024-12-06 16:55:39 +0200 (Fri, 06 Dec 2024) $
#$Revision: 296258 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/38/7133809.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_7133809
loop_
_publ_author_name
'Barik, Dinabandhu'
'Chakraborty, Nikita'
'Sahoo, Ashish K.'
'Dhara, Hirendra Nath'
'Patel, Bhisma K.'
_publ_section_title
;
 Electron-donor-acceptor (EDA) complex-driven regioselective vicinal and
 oxidative geminal functionalization of alkynes.
;
_journal_issue                   86
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              12577
_journal_page_last               12580
_journal_paper_doi               10.1039/d4cc04610b
_journal_volume                  60
_journal_year                    2024
_chemical_formula_sum            'C3.5 H2.83 Cl0.17 N0 O0.5 S0.33'
_chemical_formula_weight         69.49
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2024-07-23 deposited with the CCDC.	2024-10-01 downloaded from the CCDC.
;
_cell_angle_alpha                117.3240(10)
_cell_angle_beta                 97.055(2)
_cell_angle_gamma                94.082(2)
_cell_formula_units_Z            12
_cell_length_a                   8.2512(5)
_cell_length_b                   11.5639(8)
_cell_length_c                   11.6055(8)
_cell_measurement_reflns_used    9978
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      26.38
_cell_measurement_theta_min      2.93
_cell_volume                     966.08(11)
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0259
_diffrn_reflns_av_unetI/netI     0.0186
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            20908
_diffrn_reflns_point_group_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        25.027
_diffrn_reflns_theta_max         25.027
_diffrn_reflns_theta_min         2.929
_exptl_absorpt_coefficient_mu    0.433
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.433
_exptl_crystal_description       block
_exptl_crystal_F_000             432
_refine_diff_density_max         0.397
_refine_diff_density_min         -0.321
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.421
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3336
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.421
_refine_ls_R_factor_all          0.0506
_refine_ls_R_factor_gt           0.0433
_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)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1605
_refine_ls_wR_factor_ref         0.1735
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2935
_reflns_number_total             3336
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4cc04610b2.cif
_cod_data_source_block           BKP_ALTS_0ma_a
_cod_depositor_comments
'Adding full bibliography for 7133809--7133810.cif.'
_cod_original_formula_sum        'C3.50 H2.83 Cl0.17 N0 O0.50 S0.33'
_cod_database_code               7133809
_shelx_shelxl_version_number     2018/3
_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.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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
Cl2 Cl -0.03956(9) 0.35539(8) 1.09903(7) 0.0711(3) Uani 1 1 d . . . . .
S1 S 0.52251(7) 0.33693(5) 0.77581(5) 0.0406(2) Uani 1 1 d . . . . .
S2 S 0.34165(9) 0.49836(7) 0.66697(6) 0.0532(3) Uani 1 1 d . . . . .
O1 O 0.1817(2) 0.2340(2) 0.55862(17) 0.0732(6) Uani 1 1 d . . . . .
O2 O 0.4688(2) 0.21896(17) 0.78136(17) 0.0537(5) Uani 1 1 d . . . . .
O3 O 0.6339(2) 0.43978(16) 0.88591(15) 0.0553(5) Uani 1 1 d . . . . .
C1 C 0.0799(3) 0.2490(2) 0.7452(2) 0.0452(6) Uani 1 1 d . . . . .
C2 C 0.0805(3) 0.3161(2) 0.8806(2) 0.0463(6) Uani 1 1 d . . . . .
H2 H 0.156697 0.390771 0.935230 0.056 Uiso 1 1 calc R U . . .
C3 C -0.0342(3) 0.2692(2) 0.9312(3) 0.0491(6) Uani 1 1 d . . . . .
C4 C -0.1475(3) 0.1590(3) 0.8542(3) 0.0590(7) Uani 1 1 d . . . . .
H4 H -0.223521 0.129624 0.891291 0.071 Uiso 1 1 calc R U . . .
C5 C -0.1468(4) 0.0924(3) 0.7208(3) 0.0672(8) Uani 1 1 d . . . . .
H5 H -0.222247 0.016924 0.667431 0.081 Uiso 1 1 calc R U . . .
C6 C -0.0360(3) 0.1366(3) 0.6664(3) 0.0582(7) Uani 1 1 d . . . . .
H6 H -0.037596 0.091536 0.576023 0.070 Uiso 1 1 calc R U . . .
C7 C 0.1945(3) 0.2903(2) 0.6774(2) 0.0487(6) Uani 1 1 d . . . . .
C8 C 0.3350(3) 0.4057(2) 0.7568(2) 0.0407(5) Uani 1 1 d . . . . .
H8 H 0.308783 0.461471 0.843984 0.049 Uiso 1 1 calc R U . . .
C9 C 0.6083(3) 0.2937(2) 0.6333(2) 0.0383(5) Uani 1 1 d . . . . .
C10 C 0.7334(3) 0.3792(2) 0.6318(3) 0.0485(6) Uani 1 1 d . . . . .
H10 H 0.767627 0.462083 0.703750 0.058 Uiso 1 1 calc R U . . .
C11 C 0.8065(3) 0.3385(3) 0.5205(3) 0.0561(7) Uani 1 1 d . . . . .
H11 H 0.889423 0.395655 0.517911 0.067 Uiso 1 1 calc R U . . .
C12 C 0.7591(3) 0.2150(3) 0.4135(3) 0.0552(7) Uani 1 1 d . . . . .
C13 C 0.6330(4) 0.1318(3) 0.4180(3) 0.0552(7) Uani 1 1 d . . . . .
H13 H 0.599030 0.048692 0.346331 0.066 Uiso 1 1 calc R U . . .
C14 C 0.5581(3) 0.1700(2) 0.5257(2) 0.0469(6) Uani 1 1 d . . . . .
H14 H 0.473527 0.113148 0.527041 0.056 Uiso 1 1 calc R U . . .
C15 C 0.4868(3) 0.6399(2) 0.7700(2) 0.0485(6) Uani 1 1 d . . . . .
C16 C 0.5867(4) 0.6852(3) 0.7062(3) 0.0649(8) Uani 1 1 d . . . . .
H16 H 0.579102 0.638189 0.615326 0.078 Uiso 1 1 calc R U . . .
C17 C 0.6964(4) 0.7994(4) 0.7780(4) 0.0810(10) Uani 1 1 d . . . . .
H17 H 0.761766 0.829662 0.734769 0.097 Uiso 1 1 calc R U . . .
C18 C 0.7108(5) 0.8691(3) 0.9120(4) 0.0816(10) Uani 1 1 d . . . . .
H18 H 0.785277 0.946191 0.959958 0.098 Uiso 1 1 calc R U . . .
C19 C 0.6135(5) 0.8232(3) 0.9744(3) 0.0788(10) Uani 1 1 d . . . . .
H19 H 0.624059 0.869231 1.065591 0.095 Uiso 1 1 calc R U . . .
C20 C 0.5017(4) 0.7116(3) 0.9053(3) 0.0607(7) Uani 1 1 d . . . . .
H20 H 0.435101 0.683618 0.949351 0.073 Uiso 1 1 calc R U . . .
C21 C 0.8409(5) 0.1734(4) 0.2948(3) 0.0899(11) Uani 1 1 d . . . . .
H21A H 0.862735 0.084655 0.265023 0.135 Uiso 1 1 calc R U . . .
H21B H 0.942789 0.230708 0.317532 0.135 Uiso 1 1 calc R U . . .
H21C H 0.769364 0.178300 0.225851 0.135 Uiso 1 1 calc R U . . .
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'
Cl Cl 0.1484 0.1585 '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
O3 S1 O2 118.87(11) . . ?
O3 S1 C9 108.91(11) . . ?
O2 S1 C9 108.59(10) . . ?
O3 S1 C8 106.84(10) . . ?
O2 S1 C8 105.49(11) . . ?
C9 S1 C8 107.60(10) . . ?
C15 S2 C8 104.81(10) . . ?
C2 C1 C6 119.1(3) . . ?
C2 C1 C7 124.0(2) . . ?
C6 C1 C7 116.9(2) . . ?
C3 C2 C1 118.4(2) . . ?
C4 C3 C2 122.5(3) . . ?
C4 C3 Cl2 118.6(2) . . ?
C2 C3 Cl2 118.86(19) . . ?
C3 C4 C5 118.9(3) . . ?
C6 C5 C4 120.4(3) . . ?
C5 C6 C1 120.6(3) . . ?
O1 C7 C1 121.4(2) . . ?
O1 C7 C8 117.9(2) . . ?
C1 C7 C8 120.7(2) . . ?
C7 C8 S2 105.99(15) . . ?
C7 C8 S1 107.63(15) . . ?
S2 C8 S1 115.20(12) . . ?
C10 C9 C14 120.4(2) . . ?
C10 C9 S1 119.94(18) . . ?
C14 C9 S1 119.49(17) . . ?
C9 C10 C11 118.6(2) . . ?
C12 C11 C10 121.5(2) . . ?
C11 C12 C13 118.5(2) . . ?
C11 C12 C21 120.3(3) . . ?
C13 C12 C21 121.2(3) . . ?
C14 C13 C12 121.1(2) . . ?
C13 C14 C9 119.9(2) . . ?
C20 C15 C16 118.6(3) . . ?
C20 C15 S2 125.4(2) . . ?
C16 C15 S2 115.9(2) . . ?
C17 C16 C15 119.9(3) . . ?
C18 C17 C16 120.9(3) . . ?
C17 C18 C19 118.9(3) . . ?
C20 C19 C18 121.3(3) . . ?
C19 C20 C15 120.3(3) . . ?
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
Cl2 C3 1.742(3) . ?
S1 O3 1.4327(17) . ?
S1 O2 1.4364(17) . ?
S1 C9 1.751(2) . ?
S1 C8 1.824(2) . ?
S2 C15 1.766(3) . ?
S2 C8 1.808(2) . ?
O1 C7 1.211(3) . ?
C1 C2 1.396(3) . ?
C1 C6 1.399(4) . ?
C1 C7 1.485(4) . ?
C2 C3 1.376(3) . ?
C3 C4 1.369(4) . ?
C4 C5 1.378(4) . ?
C5 C6 1.367(4) . ?
C7 C8 1.537(3) . ?
C9 C10 1.385(3) . ?
C9 C14 1.388(3) . ?
C10 C11 1.389(4) . ?
C11 C12 1.381(4) . ?
C12 C13 1.387(4) . ?
C12 C21 1.501(4) . ?
C13 C14 1.365(3) . ?
C15 C20 1.382(4) . ?
C15 C16 1.394(4) . ?
C16 C17 1.376(5) . ?
C17 C18 1.368(5) . ?
C18 C19 1.373(5) . ?
C19 C20 1.363(4) . ?
