Alkyl-templated cocrystallization of long-chain 1-bromoalkanes by lipid-like ionic liquids.
Musozoda, Muhammadiqboli; Muller, 2nd, Joseph E; Anderson, Grace I.; Boucher, Mairead; Zeller, Matthias; Raymond, Casey C.; Hillesheim, Patrick C.; Mirjafari, Arsalan; Chemical communications (Cambridge, England) 60 (2024) 1723–1726; doi:10.1039/d3cc04834a

data_7132641
_publ_section_title
;
 Alkyl-templated cocrystallization of long-chain 1-bromoalkanes by
 lipid-like ionic liquids.
;
_journal_issue                   13
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              1723
_journal_page_last               1726
_journal_paper_doi               10.1039/d3cc04834a
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'Br, C16 H33 Br, C19 H36 N S2'
_chemical_formula_sum            'C35 H69 Br2 N S2'
_chemical_formula_weight         727.85
_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
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2023-09-01
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2023-09-12 deposited with the CCDC.	2024-01-15 downloaded from the CCDC.
;
_cell_angle_alpha                93.301(2)
_cell_angle_beta                 91.998(2)
_cell_angle_gamma                106.020(2)
_cell_formula_units_Z            2
_cell_length_a                   8.7215(5)
_cell_length_b                   9.0562(6)
_cell_length_c                   25.5173(16)
_cell_measurement_reflns_used    9188
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      79.6012
_cell_measurement_theta_min      3.4760
_cell_volume                     1931.3(2)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2016)'
_computing_data_collection       'Apex3 v2017.3-0 (Bruker, 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement
; 
Olex2 1.5 (Dolomanov et al., 2009) 
SHELXL-2018/3 (Sheldrick, 2015, 2018), 
SHELXLE Rev937 (H\"ubschle et al., 2011)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150.00
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.911
_diffrn_measurement_device_type  'Bruker AXS D8 Quest CMOS diffractometer'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0658
_diffrn_reflns_av_unetI/netI     0.0592
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.911
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            22819
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.911
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         80.788
_diffrn_reflns_theta_min         3.475
_diffrn_source                   'I-mu-S microsource X-ray tube'
_exptl_absorpt_coefficient_mu    3.822
_exptl_absorpt_correction_T_max  0.7543
_exptl_absorpt_correction_T_min  0.4650
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.252
_exptl_crystal_description       plate
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.667
_refine_diff_density_min         -0.492
_refine_diff_density_rms         0.084
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     377
_refine_ls_number_reflns         7739
_refine_ls_number_restraints     38
_refine_ls_restrained_S_all      3.806
_refine_ls_R_factor_all          0.0538
_refine_ls_R_factor_gt           0.0486
_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/[\s^2^(Fo^2^)+(0.0317P)^2^+3.2934P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1218
_refine_ls_wR_factor_ref         0.1283
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6982
_reflns_number_total             7739
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc04834a2.cif
_cod_data_source_block           jm_toot_c116x2_mt_0m
_cod_depositor_comments
'Adding full bibliography for 7132640--7132643.cif.'
_cod_database_code               7132641
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_max   0.832
_shelx_estimated_absorpt_t_min   0.310
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C36-C37A = C22-C28
 1.53 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Br2A \\sim Br2B \\sim C22 \\sim C36 \\sim C37A \\sim C37B: within 2A with sigma
of 0.01 and sigma for terminal atoms of 0.01 within 2A
Uanis(Br2A) = Uanis(C37B)
4. Others
 Sof(Br2B)=Sof(H22C)=Sof(H22D)=Sof(H36C)=Sof(H36D)=Sof(C37B)=Sof(H37D)=
 Sof(H37E)=Sof(H37F)=1-FVAR(1)
 Sof(Br2A)=Sof(H22A)=Sof(H22B)=Sof(H36A)=Sof(H36B)=Sof(C37A)=Sof(H37A)=
 Sof(H37B)=Sof(H37C)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C22(H22A,H22B), C22(H22C,H22D), C23(H23A,H23B), C24(H24A,H24B), C25(H25A,
 H25B), C26(H26A,H26B), C27(H27A,H27B), C28(H28A,H28B), C29(H29A,H29B),
 C30(H30A,H30B), C31(H31A,H31B), C32(H32A,H32B), C33(H33A,H33B), C34(H34A,H34B),
  C35(H35A,H35B), C36(H36A,H36B), C36(H36C,H36D), C6(H6A,H6B), C7(H7A,H7B),
 C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B), C12(H12A,H12B),
 C13(H13A,H13B), C14(H14A,H14B), C15(H15A,H15B), C16(H16A,H16B), C17(H17A,H17B),
  C18(H18A,H18B), C19(H19A,H19B), C20(H20A,H20B)
5.b Aromatic/amide H refined with riding coordinates:
 N3(H3), C4(H4), C5(H5)
5.c Idealised Me refined as rotating group:
 C37A(H37A,H37B,H37C), C37B(H37D,H37E,H37F), C21(H21A,H21B,H21C)
;
_shelx_res_checksum              10731
_shelx_hkl_checksum              14293
_olex2_submission_special_instructions 'No special instructions were received'