Building Covalent Molecular Capsules by Thiol-Michael Addition Click Reaction.
Perretti, Marcelle D.; Pérez-Márquez, Lidia A; García-Rodríguez, Raúl; Carrillo, Romen; The Journal of organic chemistry 84 (2019) 840–850; doi:10.1021/acs.joc.8b02677

data_4036005
_publ_section_title
;
 Building Covalent Molecular Capsules by Thiol-Michael Addition Click
 Reaction.
;
_journal_issue                   2
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              840
_journal_page_last               850
_journal_paper_doi               10.1021/acs.joc.8b02677
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C39 H56 O12 S3, 0.5(C H2 Cl2)'
_chemical_formula_sum            'C39.5 H57 Cl O12 S3'
_chemical_formula_weight         855.48
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-06-03
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 109.755(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.1404(2)
_cell_length_b                   22.9172(3)
_cell_length_c                   14.4095(2)
_cell_measurement_reflns_used    16169
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      75.8890
_cell_measurement_theta_min      3.8430
_cell_volume                     4394.70(12)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.5953
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w   -116.00 -17.00   1.00    3.00    --  -41.86 -38.00 150.00   99
  2  \w    -50.00  32.00   1.00    3.00    --  -41.86  38.00 -30.00   82
  3  \w    -50.00  32.00   1.00    3.00    --  -41.86  38.00 -60.00   82
  4  \w     23.00  98.00   1.00    3.00    --   41.86-125.00 -90.00   75
  5  \w     39.00  98.00   1.00   12.00    --  112.00 -45.00  60.00   59
  6  \w     29.00 109.00   1.00   12.00    --  112.00 -94.00  30.00   80
  7  \w     36.00 116.00   1.00   12.00    --  112.00-111.00-180.00   80
  8  \w     36.00  91.00   1.00   12.00    --  112.00 -30.00  30.00   55
  9  \w     29.00 109.00   1.00   12.00    --  112.00 -94.00 -30.00   80
 10  \w     39.00  98.00   1.00   12.00    --  112.00 -45.00 120.00   59
 11  \w    100.00 178.00   1.00   12.00    --  112.00 111.00-150.00   78
 12  \w     39.00  98.00   1.00   12.00    --  112.00 -45.00-150.00   59
 13  \w     57.00 151.00   1.00   12.00    --  112.00 178.00   0.00   94
 14  \w    100.00 178.00   1.00   12.00    --  112.00 111.00 120.00   78
 15  \w     84.00 178.00   1.00   12.00    --  112.00  30.00-150.00   94
 16  \w     36.00 116.00   1.00   12.00    --  112.00-111.00 150.00   80
 17  \w     39.00  98.00   1.00   12.00    --  112.00 -45.00 150.00   59
 18  \w     39.00  98.00   1.00   12.00    --  112.00 -45.00   0.00   59
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0890964000
_diffrn_orient_matrix_UB_12      -0.0138815000
_diffrn_orient_matrix_UB_13      -0.0941175000
_diffrn_orient_matrix_UB_21      0.0689298000
_diffrn_orient_matrix_UB_22      0.0072565000
_diffrn_orient_matrix_UB_23      -0.0622515000
_diffrn_orient_matrix_UB_31      0.0265524000
_diffrn_orient_matrix_UB_32      -0.0653844000
_diffrn_orient_matrix_UB_33      0.0130958000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0251
_diffrn_reflns_av_unetI/netI     0.0221
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            36760
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.195
_diffrn_reflns_theta_min         3.787
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.584
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.165
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
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    1.293
_exptl_crystal_description       block
_exptl_crystal_F_000             1820
_exptl_crystal_recrystallization_method DCM
_exptl_crystal_size_max          0.497
_exptl_crystal_size_mid          0.363
_exptl_crystal_size_min          0.184
_refine_diff_density_max         0.835
_refine_diff_density_min         -0.435
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.23(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1003
_refine_ls_number_reflns         12167
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0618
_refine_ls_R_factor_gt           0.0591
_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/[\s^2^(Fo^2^)+(0.1228P)^2^+1.1204P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1735
_refine_ls_wR_factor_ref         0.1793
_reflns_Friedel_coverage         0.951
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.991
_reflns_number_gt                11450
_reflns_number_total             12167
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b02677_si_002.cif
_cod_data_source_block           compound_5
_cod_original_sg_symbol_H-M      'P 21'
_cod_original_formula_sum        'C39.50 H57 Cl O12 S3'
_cod_database_code               4036005
_shelx_shelxl_version_number     2017/1
_chemical_oxdiff_formula         'C162 H238 O48 S12 Cl2'
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.77(2)
 0.23(2)
2. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Free rotating group:
 Cl2S(C1AA,C1S,Cl1S)
3.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C7(H7A,H7B), C14(H14A,
 H14B), C16(H16A,H16B), C18(H18A,H18B), C20(H20A,H20B), C21(H21A,H21B),
 C22(H22A,H22B), C23(H23A,H23B), C25(H25A,H25B), C27(H27A,H27B), C29(H29A,H29B),
  C30(H30A,H30B), C31(H31A,H31B), C32(H32A,H32B), C34(H34A,H34B), C35(H35A,
 H35B), C37(H37A,H37B), C41(H41A,H41B), C42(H42A,H42B), C43(H43A,H43B),
 C44(H44A,H44B), C46(H46A,H46B), C53(H53A,H53B), C55(H55A,H55B), C57(H57A,H57B),
  C59(H59A,H59B), C61(H61A,H61B), C62(H62A,H62B), C63(H63A,H63B), C64(H64A,
 H64B), C66(H66A,H66B), C68(H68A,H68B), C70(H70A,H70B), C71(H71A,H71B),
 C72(H72A,H72B), C73(H73A,H73B), C75(H75A,H75B), C76(H76A,H76B), C78(H78A,H78B),
  C1AA(H1AA,H1AB), C1S(H1SA,H1SB)
3.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C17(H17A,H17B,H17C), C36(H36A,H36B,H36C), C38(H38A,H38B,
 H38C), C54(H54A,H54B,H54C), C56(H56A,H56B,H56C), C58(H58A,H58B,H58C), C77(H77A,
 H77B,H77C)
;
_shelx_res_checksum              49713
_shelx_hkl_checksum              20357
_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 1.223
_oxdiff_exptl_absorpt_empirical_full_min 0.827