The Crystalline Sponge Method: A Solvent-Based Strategy to Facilitate Noncovalent Ordered Trapping of Solid and Liquid Organic Compounds
Ramadhar, Timothy R.; Zheng, Shao-Liang; Chen, Yu-Sheng; Clardy, Jon; CrystEngComm  (2017) –; doi:10.1039/C7CE00885F

data_7228690
_publ_section_title
;
 The Crystalline Sponge Method: A Solvent-Based Strategy to Facilitate
 Noncovalent Ordered Trapping of Solid and Liquid Organic Compounds
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/C7CE00885F
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety
'C72 H48 I12 N24 Zn6, 0.93(C15 H22 O5), 0.62(C5 H12 O)'
_chemical_formula_sum            'C89.08 H75.94 I12 N24 O5.28 Zn6'
_chemical_formula_weight         3482.07
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2017-04-20
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_audit_update_record
;
2017-04-24 deposited with the CCDC.
2017-07-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 108.1167(11)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   35.252(2)
_cell_length_b                   14.8612(8)
_cell_length_c                   35.233(2)
_cell_measurement_reflns_used    9932
_cell_measurement_temperature    100
_cell_measurement_theta_max      14.082
_cell_measurement_theta_min      2.301
_cell_volume                     17543.1(17)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXTL XT-2014/5 (Sheldrick, 2015)'
_diffrn_ambient_temperature      100
_diffrn_detector                 'Pilatus 1M CdTe Pixel Array Detector'
_diffrn_detector_type            'Pilatus 1M CdTe Pixel Array Detector'
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device
'Huber three-circle goniometer with free kappa'
_diffrn_measurement_device_type
'Huber three-circle goniometer with free kappa'
_diffrn_measurement_method       'phi scans'
_diffrn_radiation_monochromator  'Si 1 1 1'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.41328
_diffrn_reflns_av_R_equivalents  0.0708
_diffrn_reflns_av_unetI/netI     0.0622
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       41
_diffrn_reflns_limit_h_min       -42
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_number            181019
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        14.281
_diffrn_reflns_theta_max         14.281
_diffrn_reflns_theta_min         0.707
_diffrn_source                   synchrotron
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.680
_exptl_absorpt_correction_T_max  0.9611
_exptl_absorpt_correction_T_min  0.8222
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.1028 before and 0.0728 after correction. The Ratio of minimum to maximum transmission is 0.8555. The \l/2 correction factor is 0.00150.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.318
_exptl_crystal_description       prism
_exptl_crystal_F_000             6547
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_refine_diff_density_max         2.623
_refine_diff_density_min         -1.224
_refine_diff_density_rms         0.276
_refine_ls_abs_structure_details
;
 Flack x determined using 10229 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
 Hooft y (Hooft, Straver and Spek, J. Appl. Cryst. (2008) 96-103.).
 A three-hypothesis model based on Bayesian statistical analysis
 on Bijvoet pairs using a Student's t-distribution was employed 
 to determine absolute configuration.
 p3(true) = 1.000, p3(false) = 0.0E+00, p3(rac-twin) = 0.3E-37
;
_refine_ls_abs_structure_Flack   0.18(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1310
_refine_ls_number_reflns         30760
_refine_ls_number_restraints     156
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0820
_refine_ls_R_factor_gt           0.0700
_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^)+(0.1379P)^2^+110.1000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2199
_refine_ls_wR_factor_ref         0.2336
_reflns_Friedel_coverage         0.899
_reflns_Friedel_fraction_full    0.973
_reflns_Friedel_fraction_max     0.973
_reflns_number_gt                25384
_reflns_number_total             30760
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ce00885f2.cif
_cod_data_source_block           tim83-artemisinin-c2_c
_cod_database_code               7228690
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.967
_shelx_estimated_absorpt_t_min   0.899
_refine_ls_abs_structure_hooft   0.15(2)
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C19-C20 \\sim C22-C23
 with sigma of 0.02
 N7-C19 \\sim N8-C28
 with sigma of 0.02
 C21-C34 \\sim C31-C36
 with sigma of 0.02
 N7-C23 \\sim N8-C24
 with sigma of 0.02
 C60-C61 \\sim C63-C64
 with sigma of 0.02
 C65-C66 \\sim C68-C69
 with sigma of 0.02
 C78-C79 \\sim C80-C81
 with sigma of 0.02
 C88-O6 \\sim C89-O6
 with sigma of 0.02
 C89-C90 \\sim C89-C91 \\sim C89-C92
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
N7 \\sim C23 \\sim C22 \\sim C21: within 2A with sigma of 0.04 and sigma for
terminal atoms of 0.08
C60 \\sim N20: within 2A with sigma of 0.04 and sigma for terminal atoms of 0.08
C66 \\sim C67 \\sim C68: within 2A with sigma of 0.04 and sigma for terminal
atoms of 0.08
Uanis(Zn2) = Uanis(Zn2A)
Uanis(I3) = Uanis(I3A)
Uanis(I4) = Uanis(I4A)
Uanis(Zn3) = Uanis(Zn3A)
Uanis(I5) = Uanis(I5A)
Uanis(I6) = Uanis(I6A)
Uanis(Zn4) = Uanis(Zn4A)
Uanis(I7) = Uanis(I7A)
Uanis(I8) = Uanis(I8A)
Uanis(Zn6) = Uanis(Zn6A)
Uanis(I11) = Uanis(I11A)
Uanis(I12) = Uanis(I12A)
4. Rigid body (RIGU) restrains
 N7, C19, C20, C21, C22, C23
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C62, C61, C60, N20
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 N21, C69, C68, C67, C66
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C88, O6, C89, C90, C91, C92
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(Zn2A)=Sof(I3A)=Sof(I4A)=1-FVAR(1)
 Sof(Zn2)=Sof(I3)=Sof(I4)=FVAR(1)
 Sof(Zn3A)=Sof(I6A)=Sof(I5A)=1-FVAR(2)
 Sof(Zn3)=Sof(I5)=Sof(I6)=FVAR(2)
 Sof(Zn4A)=Sof(I7A)=Sof(I8A)=1-FVAR(3)
 Sof(Zn4)=Sof(I7)=Sof(I8)=FVAR(3)
 Sof(Zn6A)=Sof(I11A)=Sof(I12A)=1-FVAR(4)
 Sof(Zn6)=Sof(I11)=Sof(I12)=FVAR(4)
 Sof(O1)=Sof(O2)=Sof(O3)=Sof(O4)=Sof(O5)=Sof(C73)=Sof(H73A)=Sof(H73B)=
 Sof(H73C)=Sof(C74)=Sof(H74)=Sof(C75)=Sof(H75)=Sof(C76)=Sof(C77)=Sof(H77)=
 Sof(C78)=Sof(H78A)=Sof(H78B)=Sof(C79)=Sof(H79A)=Sof(H79B)=Sof(C80)=Sof(H80A)=
 Sof(H80B)=Sof(C81)=Sof(H81A)=Sof(H81B)=Sof(C82)=Sof(C83)=Sof(H83A)=Sof(H83B)=
 Sof(H83C)=Sof(C84)=Sof(H84)=Sof(C85)=Sof(C86)=Sof(H86)=Sof(C87)=Sof(H87A)=
 Sof(H87B)=Sof(H87C)=FVAR(5)
 Sof(O6)=Sof(C89)=Sof(C92)=Sof(H92A)=Sof(H92B)=Sof(H92C)=Sof(C88)=Sof(H88A)=
 Sof(H88B)=Sof(H88C)=Sof(C90)=Sof(H90A)=Sof(H90B)=Sof(H90C)=Sof(C91)=Sof(H91A)=
 Sof(H91B)=Sof(H91C)=FVAR(6)
6.a Ternary CH refined with riding coordinates:
 C74(H74), C75(H75), C77(H77), C84(H84), C86(H86)
6.b Secondary CH2 refined with riding coordinates:
 C78(H78A,H78B), C79(H79A,H79B), C80(H80A,H80B), C81(H81A,H81B)
6.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5), C6(H6), C7(H7), C9(H9), C10(H10), C11(H11),
 C12(H12), C14(H14), C15(H15), C19(H19), C20(H20), C22(H22), C23(H23), C24(H24),
  C25(H25), C27(H27), C28(H28), C29(H29), C30(H30), C32(H32), C33(H33),
 C37(H37), C38(H38), C40(H40), C41(H41), C42(H42), C43(H43), C45(H45), C46(H46),
  C47(H47), C48(H48), C50(H50), C51(H51), C55(H55), C56(H56), C58(H58),
 C59(H59), C60(H60), C61(H61), C63(H63), C64(H64), C65(H65), C66(H66), C68(H68),
  C69(H69)
6.d Idealised Me refined as rotating group:
 C73(H73A,H73B,H73C), C83(H83A,H83B,H83C), C87(H87A,H87B,H87C), C92(H92A,H92B,
 H92C), C88(H88A,H88B,H88C), C90(H90A,H90B,H90C), C91(H91A,H91B,H91C)
;
_shelx_res_checksum              74091
_olex2_submission_special_instructions 'No special instructions were received'