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#$Date: 2023-11-17 00:56:17 +0200 (Fri, 17 Nov 2023) $
#$Revision: 287653 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/23/7132353.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_7132353
loop_
_publ_author_name
'McMullen, Jacob'
'White, Andrew J. P.'
'Crimmin, Mark Richard'
_publ_section_title
;
 Ring-Expansion and Desulfurisation of Thiophenes with an Aluminium(I)
 Reagent
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D3CC04594C
_journal_year                    2023
_chemical_formula_moiety         'C34 H47 Al N2 S, C7 H8'
_chemical_formula_sum            'C41 H55 Al N2 S'
_chemical_formula_weight         634.91
_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
;
2023-09-05 deposited with the CCDC.	2023-11-16 downloaded from the CCDC.
;
_cell_angle_alpha                104.737(3)
_cell_angle_beta                 90.087(3)
_cell_angle_gamma                97.200(3)
_cell_formula_units_Z            2
_cell_length_a                   10.4074(4)
_cell_length_b                   10.9429(4)
_cell_length_c                   17.0594(6)
_cell_measurement_reflns_used    7611
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      73.4050
_cell_measurement_theta_min      4.2030
_cell_volume                     1862.99(12)
_computing_cell_refinement       'CrysAlisPro, Rigaku OD'
_computing_data_collection       'CrysAlisPro, Rigaku OD'
_computing_data_reduction        'CrysAlisPro, Rigaku OD'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'CIFTAB-2014 (Sheldrick, 2017)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2017)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 10.4115
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Agilent Xcalibur PX Ultra A'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0513
_diffrn_reflns_av_unetI/netI     0.0376
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            31624
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.949
_diffrn_reflns_theta_min         4.213
_diffrn_source                   'Enhance Ultra (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.209
_exptl_absorpt_correction_T_max  0.850
_exptl_absorpt_correction_T_min  0.759
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
; 
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015) 
Analytical numeric absorption correction using a multifaceted crystal 
model based on expressions derived by R.C. Clark & J.S. Reid. 
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) 
Empirical absorption correction using spherical harmonics, 
implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.132
_exptl_crystal_description       blocks
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.339
_exptl_crystal_size_mid          0.278
_exptl_crystal_size_min          0.194
_refine_diff_density_max         0.893
_refine_diff_density_min         -0.653
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     418
_refine_ls_number_reflns         7418
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0899
_refine_ls_R_factor_gt           0.0650
_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)+(0.0991P)²+1.4540P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1728
_refine_ls_wR_factor_ref         0.1973
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5452
_reflns_number_total             7418
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3cc04594c3.cif
_cod_data_source_block           2b
_cod_database_code               7132353
_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
Al1 Al 0.20584(7) 0.67193(7) 0.27430(4) 0.0309(2) Uani 1 1 d . . . . .
N1 N 0.3121(2) 0.6242(2) 0.18393(12) 0.0301(5) Uani 1 1 d . . . . .
C1 C 0.4414(3) 0.6389(2) 0.19481(16) 0.0333(6) Uani 1 1 d . . . . .
C2 C 0.5033(3) 0.6659(3) 0.27059(17) 0.0373(6) Uani 1 1 d . . . . .
H2A H 0.594026 0.692446 0.272660 0.045 Uiso 1 1 calc R U . . .
C3 C 0.4479(3) 0.6584(3) 0.34442(17) 0.0363(6) Uani 1 1 d . . . . .
N3 N 0.3201(2) 0.6462(2) 0.35429(13) 0.0329(5) Uani 1 1 d . . . . .
C4 C 0.5262(3) 0.6229(3) 0.12181(18) 0.0437(7) Uani 1 1 d . . . . .
H4A H 0.512157 0.533924 0.089800 0.066 Uiso 1 1 calc R U . . .
H4B H 0.617371 0.645889 0.140026 0.066 Uiso 1 1 calc R U . . .
H4C H 0.503871 0.678376 0.088330 0.066 Uiso 1 1 calc R U . . .
C5 C 0.5399(3) 0.6618(3) 0.41353(19) 0.0505(8) Uani 1 1 d . . . . .
H5A H 0.547948 0.746107 0.451963 0.076 Uiso 1 1 calc R U . . .
H5B H 0.625102 0.644779 0.392324 0.076 Uiso 1 1 calc R U . . .
H5C H 0.506387 0.596777 0.441205 0.076 Uiso 1 1 calc R U . . .
C6 C 0.2562(2) 0.5763(3) 0.10160(15) 0.0323(5) Uani 1 1 d . . . . .
C7 C 0.2330(3) 0.4441(3) 0.06785(17) 0.0383(6) Uani 1 1 d . . . . .
C8 C 0.1782(3) 0.3994(3) -0.01030(17) 0.0434(7) Uani 1 1 d . . . . .
H8A H 0.162161 0.310105 -0.033780 0.052 Uiso 1 1 calc R U . . .
C9 C 0.1466(3) 0.4815(3) -0.05450(17) 0.0465(7) Uani 1 1 d . . . . .
H9A H 0.108639 0.449305 -0.107608 0.056 Uiso 1 1 calc R U . . .
C10 C 0.1707(3) 0.6111(3) -0.02053(18) 0.0453(7) Uani 1 1 d . . . . .
H10A H 0.149697 0.667636 -0.051179 0.054 Uiso 1 1 calc R U . . .
C11 C 0.2252(3) 0.6615(3) 0.05760(16) 0.0377(6) Uani 1 1 d . . . . .
C12 C 0.2669(4) 0.3474(3) 0.11220(18) 0.0482(8) Uani 1 1 d . . . . .
H12A H 0.303065 0.395117 0.167391 0.058 Uiso 1 1 calc R U . . .
C13 C 0.1472(4) 0.2585(4) 0.1226(3) 0.0722(12) Uani 1 1 d . . . . .
H13A H 0.081414 0.308817 0.150378 0.108 Uiso 1 1 calc R U . . .
H13B H 0.170610 0.201647 0.154849 0.108 Uiso 1 1 calc R U . . .
H13C H 0.112536 0.207605 0.069180 0.108 Uiso 1 1 calc R U . . .
C14 C 0.3699(4) 0.2687(3) 0.0684(2) 0.0572(9) Uani 1 1 d . . . . .
H14A H 0.335670 0.219245 0.014624 0.086 Uiso 1 1 calc R U . . .
H14B H 0.392285 0.210643 0.100053 0.086 Uiso 1 1 calc R U . . .
H14C H 0.447544 0.326021 0.062646 0.086 Uiso 1 1 calc R U . . .
C15 C 0.2484(3) 0.8053(3) 0.09087(18) 0.0430(7) Uani 1 1 d . . . . .
H15A H 0.288813 0.824043 0.146567 0.052 Uiso 1 1 calc R U . . .
C16 C 0.3414(4) 0.8692(3) 0.0395(2) 0.0580(9) Uani 1 1 d . . . . .
H16A H 0.424644 0.835613 0.037871 0.087 Uiso 1 1 calc R U . . .
H16B H 0.354776 0.961430 0.063471 0.087 Uiso 1 1 calc R U . . .
H16C H 0.304466 0.851405 -0.015719 0.087 Uiso 1 1 calc R U . . .
C17 C 0.1197(4) 0.8625(3) 0.0982(2) 0.0579(9) Uani 1 1 d . . . . .
H17A H 0.080506 0.849895 0.044023 0.087 Uiso 1 1 calc R U . . .
H17B H 0.136311 0.953874 0.124692 0.087 Uiso 1 1 calc R U . . .
H17C H 0.060494 0.820128 0.130628 0.087 Uiso 1 1 calc R U . . .
C18 C 0.2693(3) 0.6194(3) 0.42876(16) 0.0361(6) Uani 1 1 d . . . . .
C19 C 0.2555(3) 0.7202(3) 0.49734(17) 0.0431(7) Uani 1 1 d . . . . .
C20 C 0.2067(3) 0.6881(4) 0.56667(19) 0.0554(8) Uani 1 1 d . . . . .
H20A H 0.198025 0.754164 0.614023 0.066 Uiso 1 1 calc R U . . .
C21 C 0.1708(4) 0.5632(4) 0.5683(2) 0.0591(9) Uani 1 1 d . . . . .
H21A H 0.137635 0.543831 0.616180 0.071 Uiso 1 1 calc R U . . .
C22 C 0.1834(4) 0.4667(3) 0.5001(2) 0.0542(8) Uani 1 1 d . . . . .
H22A H 0.158260 0.380761 0.501436 0.065 Uiso 1 1 calc R U . . .
C23 C 0.2322(3) 0.4925(3) 0.42918(17) 0.0426(7) Uani 1 1 d . . . . .
C24 C 0.2891(4) 0.8597(3) 0.50033(19) 0.0532(8) Uani 1 1 d . . . . .
H24A H 0.323869 0.865749 0.446635 0.064 Uiso 1 1 calc R U . . .
C25 C 0.3951(5) 0.9255(4) 0.5661(2) 0.0752(12) Uani 1 1 d . . . . .
H25A H 0.362697 0.922210 0.619571 0.113 Uiso 1 1 calc R U . . .
H25B H 0.417703 1.014530 0.564731 0.113 Uiso 1 1 calc R U . . .
H25C H 0.472109 0.881395 0.555879 0.113 Uiso 1 1 calc R U . . .
C26 C 0.1696(5) 0.9284(4) 0.5139(2) 0.0763(12) Uani 1 1 d . . . . .
H26A H 0.100028 0.880669 0.475262 0.114 Uiso 1 1 calc R U . . .
H26B H 0.190640 1.014158 0.505904 0.114 Uiso 1 1 calc R U . . .
H26C H 0.141018 0.934787 0.569372 0.114 Uiso 1 1 calc R U . . .
C27 C 0.2448(4) 0.3817(3) 0.35672(19) 0.0527(8) Uani 1 1 d . . . . .
H27A H 0.255339 0.416274 0.307873 0.063 Uiso 1 1 calc R U . . .
C28 C 0.1266(4) 0.2814(4) 0.3408(3) 0.0693(10) Uani 1 1 d . . . . .
H28A H 0.118508 0.240043 0.385519 0.104 Uiso 1 1 calc R U . . .
H28B H 0.136128 0.217512 0.289934 0.104 Uiso 1 1 calc R U . . .
H28C H 0.048930 0.321842 0.336647 0.104 Uiso 1 1 calc R U . . .
C29 C 0.3654(4) 0.3198(4) 0.3663(3) 0.0803(13) Uani 1 1 d . . . . .
H29A H 0.441553 0.384849 0.376715 0.120 Uiso 1 1 calc R U . . .
H29B H 0.376540 0.254467 0.316403 0.120 Uiso 1 1 calc R U . . .
H29C H 0.355457 0.280426 0.411842 0.120 Uiso 1 1 calc R U . . .
S30 S 0.01694(8) 0.55051(8) 0.26081(5) 0.0491(2) Uani 1 1 d . . . . .
C31 C -0.0882(4) 0.6599(3) 0.2866(2) 0.0574(9) Uani 1 1 d . . . . .
H31A H -0.175453 0.623199 0.288276 0.069 Uiso 1 1 calc R U . . .
C32 C -0.0730(4) 0.7870(4) 0.3049(3) 0.0694(10) Uani 1 1 d . . . . .
H32A H -0.149994 0.825697 0.316314 0.083 Uiso 1 1 calc R U . . .
C33 C 0.0431(4) 0.8718(4) 0.3096(2) 0.0648(10) Uani 1 1 d . . . . .
H33A H 0.033027 0.959664 0.322304 0.078 Uiso 1 1 calc R U . . .
C34 C 0.1625(3) 0.8460(3) 0.29893(18) 0.0448(7) Uani 1 1 d . . . . .
C35 C 0.2689(4) 0.9600(3) 0.3088(2) 0.0646(10) Uani 1 1 d . . . . .
H35A H 0.353136 0.933394 0.317395 0.097 Uiso 1 1 calc R U . . .
H35B H 0.251201 1.028275 0.355514 0.097 Uiso 1 1 calc R U . . .
H35C H 0.270208 0.990964 0.259665 0.097 Uiso 1 1 calc R U . . .
C40 C 0.6491(4) 0.3443(4) 0.2220(3) 0.0666(10) Uani 1 1 d . . . . .
H40A H 0.555508 0.340458 0.212782 0.100 Uiso 1 1 calc R U . . .
H40B H 0.695568 0.386418 0.184083 0.100 Uiso 1 1 calc R U . . .
H40C H 0.673473 0.392764 0.277776 0.100 Uiso 1 1 calc R U . . .
C41 C 0.6842(3) 0.2100(3) 0.20844(18) 0.0486(7) Uani 1 1 d . . . . .
C42 C 0.5905(3) 0.1082(3) 0.2046(2) 0.0540(8) Uani 1 1 d . . . . .
H42A H 0.502047 0.121522 0.209522 0.065 Uiso 1 1 calc R U . . .
C43 C 0.6238(4) -0.0143(4) 0.1937(2) 0.0654(10) Uani 1 1 d . . . . .
H43A H 0.558276 -0.083708 0.192172 0.079 Uiso 1 1 calc R U . . .
C44 C 0.7508(4) -0.0348(4) 0.1852(3) 0.0742(11) Uani 1 1 d . . . . .
H44A H 0.774437 -0.118183 0.176844 0.089 Uiso 1 1 calc R U . . .
C45 C 0.8441(4) 0.0691(5) 0.1890(3) 0.0824(13) Uani 1 1 d . . . . .
H45A H 0.932691 0.056656 0.183243 0.099 Uiso 1 1 calc R U . . .
C46 C 0.8104(4) 0.1894(4) 0.2009(2) 0.0646(10) Uani 1 1 d . . . . .
H46A H 0.875979 0.259338 0.204014 0.078 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 0.0181 0.0091 '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'
Al Al 0.2130 0.2455 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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
N1 Al1 N3 97.19(10) . . ?
N1 Al1 C34 116.11(11) . . ?
N3 Al1 C34 112.59(12) . . ?
N1 Al1 S30 112.80(8) . . ?
N3 Al1 S30 113.84(8) . . ?
C34 Al1 S30 104.67(11) . . ?
C1 N1 C6 118.7(2) . . ?
C1 N1 Al1 119.97(18) . . ?
C6 N1 Al1 121.25(16) . . ?
N1 C1 C2 123.3(2) . . ?
N1 C1 C4 119.5(2) . . ?
C2 C1 C4 117.2(2) . . ?
C1 C2 C3 127.7(2) . . ?
N3 C3 C2 122.9(2) . . ?
N3 C3 C5 120.3(2) . . ?
C2 C3 C5 116.8(2) . . ?
C3 N3 C18 119.4(2) . . ?
C3 N3 Al1 120.21(18) . . ?
C18 N3 Al1 120.30(17) . . ?
C11 C6 C7 120.8(3) . . ?
C11 C6 N1 120.3(2) . . ?
C7 C6 N1 118.9(2) . . ?
C8 C7 C6 118.5(3) . . ?
C8 C7 C12 118.5(3) . . ?
C6 C7 C12 123.1(3) . . ?
C9 C8 C7 121.6(3) . . ?
C10 C9 C8 119.1(3) . . ?
C9 C10 C11 121.9(3) . . ?
C10 C11 C6 118.1(3) . . ?
C10 C11 C15 118.7(3) . . ?
C6 C11 C15 123.2(3) . . ?
C13 C12 C7 111.2(3) . . ?
C13 C12 C14 109.5(3) . . ?
C7 C12 C14 111.8(2) . . ?
C11 C15 C16 112.1(3) . . ?
C11 C15 C17 111.0(3) . . ?
C16 C15 C17 110.2(3) . . ?
C23 C18 C19 121.5(3) . . ?
C23 C18 N3 118.2(2) . . ?
C19 C18 N3 120.3(3) . . ?
C20 C19 C18 117.4(3) . . ?
C20 C19 C24 118.2(3) . . ?
C18 C19 C24 124.4(3) . . ?
C21 C20 C19 121.8(3) . . ?
C22 C21 C20 119.6(3) . . ?
C21 C22 C23 121.3(3) . . ?
C22 C23 C18 118.4(3) . . ?
C22 C23 C27 118.6(3) . . ?
C18 C23 C27 123.1(3) . . ?
C19 C24 C26 111.2(3) . . ?
C19 C24 C25 111.5(3) . . ?
C26 C24 C25 110.4(3) . . ?
C23 C27 C28 113.2(3) . . ?
C23 C27 C29 110.9(3) . . ?
C28 C27 C29 109.6(3) . . ?
C31 S30 Al1 102.17(14) . . ?
C32 C31 S30 133.0(3) . . ?
C31 C32 C33 128.4(4) . . ?
C34 C33 C32 129.1(4) . . ?
C33 C34 C35 116.8(3) . . ?
C33 C34 Al1 122.3(3) . . ?
C35 C34 Al1 120.9(2) . . ?
C46 C41 C42 119.0(3) . . ?
C46 C41 C40 120.0(3) . . ?
C42 C41 C40 121.0(3) . . ?
C41 C42 C43 120.7(3) . . ?
C44 C43 C42 120.1(4) . . ?
C43 C44 C45 118.4(4) . . ?
C46 C45 C44 121.0(4) . . ?
C41 C46 C45 120.9(4) . . ?
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
Al1 N1 1.901(2) . ?
Al1 N3 1.905(2) . ?
Al1 C34 1.954(3) . ?
Al1 S30 2.2072(11) . ?
N1 C1 1.342(3) . ?
N1 C6 1.460(3) . ?
C1 C2 1.389(4) . ?
C1 C4 1.514(3) . ?
C2 C3 1.403(4) . ?
C3 N3 1.335(3) . ?
C3 C5 1.508(4) . ?
N3 C18 1.460(3) . ?
C6 C11 1.403(4) . ?
C6 C7 1.404(4) . ?
C7 C8 1.392(4) . ?
C7 C12 1.522(4) . ?
C8 C9 1.380(4) . ?
C9 C10 1.379(5) . ?
C10 C11 1.396(4) . ?
C11 C15 1.519(4) . ?
C12 C13 1.522(5) . ?
C12 C14 1.534(5) . ?
C15 C16 1.529(5) . ?
C15 C17 1.540(4) . ?
C18 C23 1.396(4) . ?
C18 C19 1.411(4) . ?
C19 C20 1.396(4) . ?
C19 C24 1.510(5) . ?
C20 C21 1.378(5) . ?
C21 C22 1.377(5) . ?
C22 C23 1.393(4) . ?
C23 C27 1.515(4) . ?
C24 C26 1.521(5) . ?
C24 C25 1.543(5) . ?
C27 C28 1.516(5) . ?
C27 C29 1.526(6) . ?
S30 C31 1.699(4) . ?
C31 C32 1.334(5) . ?
C32 C33 1.417(6) . ?
C33 C34 1.311(5) . ?
C34 C35 1.535(5) . ?
C40 C41 1.520(5) . ?
C41 C46 1.361(5) . ?
C41 C42 1.374(5) . ?
C42 C43 1.394(5) . ?
C43 C44 1.371(6) . ?
C44 C45 1.388(6) . ?
C45 C46 1.370(6) . ?
