#------------------------------------------------------------------------------
#$Date: 2021-06-10 03:49:21 +0300 (Thu, 10 Jun 2021) $
#$Revision: 266329 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/32/1563267.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_1563267
loop_
_publ_author_name
'Schulz, Emmanuelle'
'Abi Fayssal, Sandra'
'Naret, Timothée'
'Huc, Vincent'
'Buendia, Julien'
'Martini, Cyril'
_publ_section_title
;
 Benzyloxycalix[8]arene supported Pd-NHC cinnamyl complexes for
 Buchwald-Hartwig C-N cross-couplings
;
_journal_name_full               'Catalysis Science & Technology'
_journal_paper_doi               10.1039/D1CY00669J
_journal_year                    2021
_chemical_formula_moiety         'C17 H22 N2 O2 S'
_chemical_formula_sum            'C17 H22 N2 O2 S'
_chemical_formula_weight         318.42
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2021-03-30 deposited with the CCDC.	2021-06-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 105.3960(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.3118(3)
_cell_length_b                   9.8749(3)
_cell_length_c                   16.4567(5)
_cell_measurement_reflns_used    9722
_cell_measurement_temperature    100(1)
_cell_measurement_theta_max      33.21
_cell_measurement_theta_min      2.43
_cell_volume                     1615.62(8)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(1)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0251
_diffrn_reflns_av_unetI/netI     0.0125
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            57631
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         33.226
_diffrn_reflns_theta_min         2.109
_exptl_absorpt_coefficient_mu    0.209
_exptl_absorpt_correction_T_max  0.9465
_exptl_absorpt_correction_T_min  0.8858
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker APEX2'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_description       block
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.310
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.210
_refine_diff_density_max         0.479
_refine_diff_density_min         -0.285
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         6152
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0332
_refine_ls_R_factor_gt           0.0294
_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/[σ²(Fo²)+(0.0414P)²+0.4923P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0803
_refine_ls_wR_factor_ref         0.0834
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5567
_reflns_number_total             6152
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1cy00669j2.cif
_cod_data_source_block           2768_GuillotICMMO
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               1563267
_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_min   0.949
_shelx_estimated_absorpt_t_max   0.965
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
C1 C 0.05448(8) 0.47666(8) 0.24018(5) 0.01805(13) Uani 1 1 d . . . . .
H1 H 0.013583 0.524430 0.276967 0.022 Uiso 1 1 calc R U . . .
C2 C 0.11585(7) 0.53832(7) 0.18657(4) 0.01489(12) Uani 1 1 d . . . . .
H2 H 0.122789 0.633790 0.181969 0.018 Uiso 1 1 calc R U . . .
C3 C 0.16901(6) 0.44364(7) 0.13771(4) 0.01184(11) Uani 1 1 d . . . . .
C4 C 0.14685(7) 0.30881(7) 0.15809(4) 0.01343(12) Uani 1 1 d . . . . .
C5 C 0.19690(8) 0.19848(7) 0.12226(5) 0.01719(13) Uani 1 1 d . . . . .
H5 H 0.180439 0.107980 0.136384 0.021 Uiso 1 1 calc R U . . .
C6 C 0.27103(8) 0.22623(8) 0.06568(5) 0.01888(13) Uani 1 1 d . . . . .
H6 H 0.307990 0.153489 0.041353 0.023 Uiso 1 1 calc R U . . .
C7 C 0.29293(7) 0.36023(8) 0.04329(5) 0.01632(12) Uani 1 1 d . . . . .
H7 H 0.343750 0.375899 0.003766 0.020 Uiso 1 1 calc R U . . .
C8 C 0.24205(6) 0.46998(7) 0.07759(4) 0.01193(11) Uani 1 1 d . . . . .
C9 C 0.13830(7) 0.67259(8) 0.00738(4) 0.01519(12) Uani 1 1 d . . . . .
H9A H 0.063761 0.655262 0.033499 0.018 Uiso 1 1 calc R U . . .
H9B H 0.113116 0.633740 -0.050136 0.018 Uiso 1 1 calc R U . . .
C10 C 0.15994(7) 0.82399(8) 0.00246(5) 0.01793(13) Uani 1 1 d . . . . .
H10A H 0.078046 0.866572 -0.033938 0.022 Uiso 1 1 calc R U . . .
H10B H 0.177153 0.864240 0.059426 0.022 Uiso 1 1 calc R U . . .
C11 C 0.37194(7) 0.63110(8) 0.01888(4) 0.01498(12) Uani 1 1 d . . . . .
H11A H 0.348991 0.591420 -0.038410 0.018 Uiso 1 1 calc R U . . .
H11B H 0.454671 0.586402 0.052681 0.018 Uiso 1 1 calc R U . . .
C12 C 0.39709(7) 0.78237(8) 0.01359(5) 0.01736(13) Uani 1 1 d . . . . .
H12A H 0.428426 0.820581 0.071097 0.021 Uiso 1 1 calc R U . . .
H12B H 0.468166 0.797619 -0.015719 0.021 Uiso 1 1 calc R U . . .
C13 C 0.27260(7) 0.93051(7) -0.09896(4) 0.01385(12) Uani 1 1 d . . . . .
C14 C 0.12317(7) 1.08055(7) -0.20105(4) 0.01306(11) Uani 1 1 d . . . . .
C15 C 0.15404(9) 1.02121(10) -0.27895(5) 0.02358(16) Uani 1 1 d . . . . .
H15A H 0.251683 1.014069 -0.269671 0.035 Uiso 1 1 calc R U . . .
H15B H 0.116861 1.080219 -0.327416 0.035 Uiso 1 1 calc R U . . .
H15C H 0.113513 0.931037 -0.290037 0.035 Uiso 1 1 calc R U . . .
C16 C 0.20018(9) 1.21022(8) -0.17292(6) 0.02564(17) Uani 1 1 d . . . . .
H16A H 0.175863 1.246397 -0.123492 0.038 Uiso 1 1 calc R U . . .
H16B H 0.177585 1.276710 -0.218729 0.038 Uiso 1 1 calc R U . . .
H16C H 0.296959 1.191549 -0.158317 0.038 Uiso 1 1 calc R U . . .
C17 C -0.02714(7) 1.10354(8) -0.21820(5) 0.01874(13) Uani 1 1 d . . . . .
H17A H -0.074865 1.018604 -0.236986 0.028 Uiso 1 1 calc R U . . .
H17B H -0.055731 1.172390 -0.262217 0.028 Uiso 1 1 calc R U . . .
H17C H -0.047933 1.134472 -0.166491 0.028 Uiso 1 1 calc R U . . .
N1 N 0.26191(6) 0.60707(6) 0.05772(4) 0.01200(10) Uani 1 1 d . . . . .
N2 N 0.27405(6) 0.85001(7) -0.03197(4) 0.01743(12) Uani 1 1 d . . . . .
O1 O 0.37066(6) 0.95224(7) -0.12522(4) 0.02178(12) Uani 1 1 d . . . . .
O2 O 0.14891(5) 0.98234(6) -0.13166(3) 0.01579(10) Uani 1 1 d . . . . .
S1 S 0.05874(2) 0.30209(2) 0.23429(2) 0.01794(5) Uani 1 1 d . . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0031 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 0.0109 0.0061 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1250 0.1239 '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
C2 C1 S1 112.80(6) . . ?
C1 C2 C3 112.66(7) . . ?
C4 C3 C8 119.35(6) . . ?
C4 C3 C2 111.91(6) . . ?
C8 C3 C2 128.68(6) . . ?
C5 C4 C3 122.31(6) . . ?
C5 C4 S1 126.65(6) . . ?
C3 C4 S1 110.98(5) . . ?
C6 C5 C4 117.49(7) . . ?
C5 C6 C7 121.29(7) . . ?
C8 C7 C6 121.55(7) . . ?
C7 C8 C3 117.97(6) . . ?
C7 C8 N1 123.88(6) . . ?
C3 C8 N1 118.12(6) . . ?
N1 C9 C10 110.20(6) . . ?
N2 C10 C9 109.87(6) . . ?
N1 C11 C12 110.37(6) . . ?
N2 C12 C11 109.98(6) . . ?
O1 C13 O2 125.30(6) . . ?
O1 C13 N2 124.06(6) . . ?
O2 C13 N2 110.64(6) . . ?
O2 C14 C16 110.45(6) . . ?
O2 C14 C17 102.03(5) . . ?
C16 C14 C17 110.95(6) . . ?
O2 C14 C15 111.52(6) . . ?
C16 C14 C15 111.99(7) . . ?
C17 C14 C15 109.49(6) . . ?
C8 N1 C11 115.56(6) . . ?
C8 N1 C9 113.08(5) . . ?
C11 N1 C9 109.82(5) . . ?
C13 N2 C12 120.56(6) . . ?
C13 N2 C10 125.69(6) . . ?
C12 N2 C10 113.74(6) . . ?
C13 O2 C14 121.22(5) . . ?
C1 S1 C4 91.63(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
C1 C2 1.3587(10) . ?
C1 S1 1.7278(8) . ?
C2 C3 1.4336(9) . ?
C3 C4 1.4064(9) . ?
C3 C8 1.4176(9) . ?
C4 C5 1.4010(10) . ?
C4 S1 1.7341(7) . ?
C5 C6 1.3800(11) . ?
C6 C7 1.4078(11) . ?
C7 C8 1.3877(10) . ?
C8 N1 1.4203(9) . ?
C9 N1 1.4727(9) . ?
C9 C10 1.5170(11) . ?
C10 N2 1.4579(9) . ?
C11 N1 1.4619(9) . ?
C11 C12 1.5225(11) . ?
C12 N2 1.4536(9) . ?
C13 O1 1.2196(9) . ?
C13 O2 1.3468(8) . ?
C13 N2 1.3560(9) . ?
C14 O2 1.4678(8) . ?
C14 C16 1.5130(11) . ?
C14 C17 1.5171(10) . ?
C14 C15 1.5181(10) . ?
