Synthesis of Cryptophane-223-Type Derivatives with Dual Functionalization.
Baydoun, Orsola; De Rycke, Nicolas; Léonce, Estelle; Boutin, Céline; Berthault, Patrick; Jeanneau, Erwann; Brotin, Thierry; The Journal of organic chemistry 84 (2019) 9127–9137; doi:10.1021/acs.joc.9b01093

data_4034165
_publ_section_title
;
 Synthesis of Cryptophane-223-Type Derivatives with Dual
 Functionalization.
;
_journal_issue                   14
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              9127
_journal_page_last               9137
_journal_paper_doi               10.1021/acs.joc.9b01093
_journal_volume                  84
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C56 H58 O13'
_chemical_formula_sum            'C56 H58 O13'
_chemical_formula_weight         939.07
_space_group_IT_number           199
_space_group_name_Hall           'I 2b 2c 3'
_space_group_name_H-M_alt        'I 21 3'
_symmetry_cell_setting           cubic
_symmetry_space_group_name_Hall  'I 2b 2c 3'
_symmetry_space_group_name_H-M   'I 21 3'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     other
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            24
_cell_length_a                   33.5971(16)
_cell_length_b                   33.5971(16)
_cell_length_c                   33.5971(16)
_cell_measurement_reflns_used    3819
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      66.8568
_cell_measurement_theta_min      3.2199
_cell_volume                     37923(3)
_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    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4685
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.9878
_diffrn_measured_fraction_theta_max 0.9878
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.069
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -40
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            25070
_diffrn_reflns_theta_full        66.9682
_diffrn_reflns_theta_max         66.9682
_diffrn_reflns_theta_min         3.2221
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance Ultra (Cu) X-ray Source'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.571
_exptl_absorpt_correction_T_max  0.912
_exptl_absorpt_correction_T_min  0.863
_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            colorless
_exptl_crystal_density_diffrn    0.987
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             11952
_exptl_crystal_size_max          0.397
_exptl_crystal_size_mid          0.321
_exptl_crystal_size_min          0.187
_refine_diff_density_max         0.53
_refine_diff_density_min         -0.34
_refine_ls_abs_structure_details
; 
 Parsons, Flack & Wagner (2013), 
 3517 Friedel Pairs 
;
_refine_ls_abs_structure_Flack   0.473(13)
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.9952
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     645
_refine_ls_number_reflns         10391
_refine_ls_number_restraints     60
_refine_ls_R_factor_all          0.1103
_refine_ls_R_factor_gt           0.0778
_refine_ls_shift/su_max          0.0029027
_refine_ls_shift/su_mean         0.0000772
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] 
 where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ 
 A~i~ are: 
 347. 529. 246. 53.0 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1891
_refine_ls_wR_factor_gt          0.1422
_refine_ls_wR_factor_ref         0.1891
_reflns_limit_h_max              27
_reflns_limit_h_min              -27
_reflns_limit_k_max              28
_reflns_limit_k_min              0
_reflns_limit_l_max              40
_reflns_limit_l_min              2
_reflns_number_gt                6339
_reflns_number_total             10442
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   5.50
_oxford_diffrn_Wilson_scale      8.29
_oxford_refine_ls_r_factor_ref   0.1103
_oxford_refine_ls_scale          0.3794(4)
_oxford_reflns_number_all        10391
_cod_data_source_file            jo9b01093_si_002.cif
_cod_data_source_block           I
_cod_original_cell_volume        37923(5)
_cod_original_sg_symbol_H-M      'I 21 3 '
_cod_database_code               4034165
_oxdiff_exptl_absorpt_empirical_full_min 0.723
_oxdiff_exptl_absorpt_empirical_full_max 1.856
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxford_refine_reflns_threshold_expression_ref I>-10.0\s(I)
_oxford_hooft_y                  0.499(13)
_oxford_bijvoet_difference       0.473(13)
_oxford_refined_flack_x          0.005(5)
_platon_squeeze_void_probe_radius 1.20