Dynamic flow synthesis of porous organic cages.
Briggs, Michael E.; Slater, Anna G.; Lunt, Neil; Jiang, Shan; Little, Marc A.; Greenaway, Rebecca L.; Hasell, Tom; Battilocchio, Claudio; Ley, Steven V.; Cooper, Andrew I.; Chemical communications (Cambridge, England) 51 (2015) 17390–17393; doi:10.1039/c5cc07447a

data_7118125
_publ_section_title
;
 Dynamic flow synthesis of porous organic cages.
;
_journal_issue                   98
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              17390
_journal_page_last               17393
_journal_paper_doi               10.1039/c5cc07447a
_journal_volume                  51
_journal_year                    2015
_chemical_absolute_configuration R
_chemical_formula_moiety         'C68 H78 N12, 4.5(C H4 O), 2.88(H2 O)'
_chemical_formula_sum            'C72.5 H101.76 N12 O7.38'
_chemical_formula_weight         1259.41
_chemical_name_systematic        11.35
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'I 2y'
_space_group_name_H-M_alt        'I 1 2 1'
_symmetry_space_group_name_Hall  'I 2y'
_symmetry_space_group_name_H-M   'I 1 2 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2015-07-07
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2015-07-07 deposited with the CCDC.
2015-10-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.0482(19)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   21.656(2)
_cell_length_b                   19.8282(19)
_cell_length_c                   22.267(3)
_cell_measurement_reflns_used    7868
_cell_measurement_temperature    100
_cell_measurement_theta_max      21.299
_cell_measurement_theta_min      2.322
_cell_volume                     9188.8(17)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.0
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku Saturn724+'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'AFC12 (Right): Kappa 3 circle'
_diffrn_measurement_device_type  'Rigaku Saturn724+ (2x2 bin mode)'
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0701
_diffrn_reflns_av_unetI/netI     0.1004
_diffrn_reflns_laue_measured_fraction_full 0.999
_diffrn_reflns_laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            21476
_diffrn_reflns_point_group_measured_fraction_full 0.890
_diffrn_reflns_point_group_measured_fraction_max 0.888
_diffrn_reflns_theta_full        21.900
_diffrn_reflns_theta_max         21.966
_diffrn_reflns_theta_min         1.161
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           24.0
_diffrn_source_power             1.2
_diffrn_source_target            Mo
_diffrn_source_type              'Rotating Anode'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.060
_exptl_absorpt_correction_T_max  0.9571
_exptl_absorpt_correction_T_min  0.6572
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1145 before and 0.0808 after correction.
The Ratio of minimum to maximum transmission is 0.6867.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    0.910
_exptl_crystal_description       needle
_exptl_crystal_F_000             2719
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: CH2Cl2 MeOH'
_exptl_crystal_size_max          0.309
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.089
_refine_diff_density_max         0.671
_refine_diff_density_min         -0.440
_refine_diff_density_rms         0.160
_refine_ls_abs_structure_details
;
 Flack x determined using 2091 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.8(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.683
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     878
_refine_ls_number_reflns         9999
_refine_ls_number_restraints     229
_refine_ls_restrained_S_all      1.674
_refine_ls_R_factor_all          0.1878
_refine_ls_R_factor_gt           0.1310
_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^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2925
_refine_ls_wR_factor_ref         0.3209
_reflns_Friedel_coverage         0.717
_reflns_friedel_fraction_full    0.773
_reflns_friedel_fraction_max     0.769
_reflns_number_gt                6175
_reflns_number_total             9999
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5cc07447a2.cif
_cod_data_source_block           sj_11_35_meoh
_cod_original_cell_volume        9188.8(19)
_cod_original_formula_sum        'C72.50 H101.76 N12 O7.38'
_cod_database_code               7118125
_shelxl_version_number           2014/6
_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, All O(H) groups
2. Restrained distances
 O1-C73
 1.43 with sigma of 0.01
 O2-C74
 1.43 with sigma of 0.01
 C76-O4
 1.43 with sigma of 0.01
 C79-O7
 1.43 with sigma of 0.01
 C80-O8
 1.43 with sigma of 0.01
 O10-C82
 1.43 with sigma of 0.01
 O6-C78
 1.43 with sigma of 0.01
 O5-C77
 1.43 with sigma of 0.01
 O9-C81
 1.43 with sigma of 0.01
 O3-C75
 1.43 with sigma of 0.01
 C7-C1
 1.45 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
Uiso(O4) = Uiso(C76)
4. Rigid body (RIGU) restrains
 N6, C50, C51, C52, C53, C54, C49, N5
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 N8, C48, C47, C46, C45, C44, C43, N7
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 N3, C37, C38, C39, C40, C41, C42, N4
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 N12, C66, C65, C64, C63, C62, C61, N11
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 1*[Sof(H49B)+Sof(H50B)+Sof(C51)+Sof(H51A)+Sof(H51B)+Sof(C52)+Sof(H52A)+
 Sof(H52B)+Sof(C53)+Sof(H53A)+Sof(H53B)+Sof(C54)+Sof(H54A)+Sof(H54B)]+1*
 [Sof(H43B)+Sof(C44)+Sof(H44A)+Sof(H44B)+Sof(C45)+Sof(H45A)+Sof(H45B)+Sof(C46)+
 Sof(H46A)+Sof(H46B)+Sof(C47)+Sof(H47A)+Sof(H47B)+Sof(H48B)]+1*[Sof(H61B)+
 Sof(C62)+Sof(H62A)+Sof(H62B)+Sof(C63)+Sof(H63A)+Sof(H63B)+Sof(C64)+Sof(H64A)+
 Sof(H64B)+Sof(C65)+Sof(H65A)+Sof(H65B)+Sof(H66A)]+1*[Sof(H37B)+Sof(C38)+
 Sof(H38A)+Sof(H38B)+Sof(C39)+Sof(H39A)+Sof(H39B)+Sof(C40)+Sof(H40A)+Sof(H40B)+
 Sof(C41)+Sof(H41A)+Sof(H41B)+Sof(H42B)]=3 with esd of 0.001
 Sof(H49B)=Sof(H50B)=1-FVAR(1)
 Sof(C51)=Sof(H51A)=Sof(H51B)=Sof(C52)=Sof(H52A)=Sof(H52B)=Sof(C53)=Sof(H53A)=
 Sof(H53B)=Sof(C54)=Sof(H54A)=Sof(H54B)=FVAR(1)
 Sof(H43B)=Sof(H48B)=1-FVAR(2)
 Sof(C44)=Sof(H44A)=Sof(H44B)=Sof(C45)=Sof(H45A)=Sof(H45B)=Sof(C46)=Sof(H46A)=
 Sof(H46B)=Sof(C47)=Sof(H47A)=Sof(H47B)=FVAR(2)
 Sof(H61B)=Sof(H66A)=1-FVAR(3)
 Sof(C62)=Sof(H62A)=Sof(H62B)=Sof(C63)=Sof(H63A)=Sof(H63B)=Sof(C64)=Sof(H64A)=
 Sof(H64B)=Sof(C65)=Sof(H65A)=Sof(H65B)=FVAR(3)
 Sof(H37B)=Sof(H42B)=1-FVAR(4)
 Sof(C38)=Sof(H38A)=Sof(H38B)=Sof(C39)=Sof(H39A)=Sof(H39B)=Sof(C40)=Sof(H40A)=
 Sof(H40B)=Sof(C41)=Sof(H41A)=Sof(H41B)=FVAR(4)
 Fixed Sof: O2(0.5) H2A(0.5) C74(0.5) H74A(0.5) H74B(0.5) H74C(0.5) C73(0.5)
 H73A(0.5) H73B(0.5) H73C(0.5) O1(0.5) H1(0.5) O8(0.5) H8A(0.5) C80(0.5)
 H80A(0.5) H80B(0.5) H80C(0.5) O3(0.25) H3(0.25) C75(0.25) H75A(0.25)
 H75B(0.25) H75C(0.25) O7(0.5) H7A(0.5) C79(0.5) H79A(0.5) H79B(0.5) H79C(0.5)
 O4(0.5) H4A(0.5) C76(0.5) H76A(0.5) H76B(0.5) H76C(0.5) O9(0.25) H9A(0.25)
 C81(0.25) H81A(0.25) H81B(0.25) H81C(0.25) O5(0.5) H5(0.5) C77(0.5) H77A(0.5)
 H77B(0.5) H77C(0.5) O6(0.5) H6A(0.5) C78(0.5) H78A(0.5) H78B(0.5) H78C(0.5)
 O10(0.5) H10(0.5) C82(0.5) H82A(0.5) H82B(0.5) H82C(0.5) O11(0.25) O12(0.25)
 O13(0.5) O14(0.5) O15(0.25) O16(0.25) O17(0.125) O18(0.25) O19(0.5)
 Fixed X: H75A(0.275209) H75B(0.339089) H75C(0.341941) H81A(0.50148)
 H81B(0.541101) H81C(0.46537) H77A(0.240129) H77B(0.30333) H77C(0.3095)
 H78A(0.29072) H78B(0.3423) H78C(0.313181)
 Fixed Y: H75A(0.776029) H75B(0.732059) H75C(0.812221) H81A(0.80428)
 H81B(0.74142) H81C(0.746439) H77A(0.87392) H77B(0.87183) H77C(0.88081)
 H78A(1.01531) H78B(1.00795) H78C(1.08038)
 Fixed Z: H75A(0.09434) H75B(0.11949) H75C(0.127621) H81A(0.49202)
 H81B(0.528291) H81C(0.51929) H77A(0.105101) H77B(0.163081) H77C(0.09347)
 H78A(0.10559) H78B(0.172469) H78C(0.148581)
6.a Ternary CH refined with riding coordinates:
 C55(H55), C60(H60), C67(H67), C72(H72)
6.b Secondary CH2 refined with riding coordinates:
 C37(H37A,H37B), C38(H38A,H38B), C39(H39A,H39B), C40(H40A,H40B), C41(H41A,
 H41B), C42(H42A,H42B), C43(H43A,H43B), C44(H44A,H44B), C45(H45A,H45B),
 C46(H46A,H46B), C47(H47A,H47B), C48(H48A,H48B), C49(H49A,H49B), C50(H50A,H50B),
  C51(H51A,H51B), C52(H52A,H52B), C53(H53A,H53B), C54(H54A,H54B), C56(H56A,
 H56B), C57(H57A,H57B), C58(H58A,H58B), C59(H59A,H59B), C61(H61A,H61B),
 C62(H62A,H62B), C63(H63A,H63B), C64(H64A,H64B), C65(H65A,H65B), C66(H66A,H66B),
  C68(H68A,H68B), C69(H69A,H69B), C70(H70A,H70B), C71(H71A,H71B)
6.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C6(H6), C7(H7), C8(H8), C9(H9), C11(H11), C13(H13), C15(H15),
 C16(H16), C17(H17), C18(H18), C20(H20), C22(H22), C24(H24), C25(H25), C26(H26),
  C27(H27), C29(H29), C31(H31), C33(H33), C34(H34), C35(H35), C36(H36)
6.d Tetrahedral OH refined with riding coordinates:
 O2(H2A), O1(H1), O8(H8A), O3(H3), O7(H7A), O4(H4A), O9(H9A), O5(H5), O6(H6A),
 O10(H10)
6.e Idealised Me refined as rotating group:
 C74(H74A,H74B,H74C), C73(H73A,H73B,H73C), C80(H80A,H80B,H80C), C79(H79A,H79B,
 H79C), C76(H76A,H76B,H76C), C82(H82A,H82B,H82C)
;
_shelx_res_checksum              28186
_shelx_hkl_checksum              3873
_olex2_submission_special_instructions 'No special instructions were received'