Supramolecular chemistry under mechanochemical conditions: a small molecule template generated and integrated into a molecular-to-supramolecular and back-to-molecular cascade reaction
Yelgaonkar, Shweta P.; Swenson, Dale C.; MacGillivray, Leonard R.; Chemical Science 11 (2020) 3569–3573; doi:10.1039/C9SC05823K

data_1557571
_publ_section_title
;
 Supramolecular chemistry under mechanochemical conditions: a small
 molecule template generated and integrated into a
 molecular-to-supramolecular and back-to-molecular cascade reaction
;
_journal_issue                   13
_journal_name_full               'Chemical Science'
_journal_page_first              3569
_journal_page_last               3573
_journal_paper_doi               10.1039/C9SC05823K
_journal_volume                  11
_journal_year                    2020
_chemical_absolute_configuration unk
_chemical_formula_moiety         '2(C8 H8 O5), C24 H20 N4, C4 H8 O'
_chemical_formula_sum            'C44 H44 N4 O11'
_chemical_formula_weight         804.83
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2019-02-04
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-02-06 deposited with the CCDC.	2020-03-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.9162(11)
_cell_length_b                   11.3807(11)
_cell_length_c                   31.809(3)
_cell_measurement_reflns_used    8057
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      46.14
_cell_measurement_theta_min      4.401
_cell_volume                     3951.8(7)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_temperature      150.15
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Nonius APEX II Kappa'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0491
_diffrn_reflns_av_unetI/netI     0.0412
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            40673
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.996
_diffrn_reflns_theta_max         24.996
_diffrn_reflns_theta_min         1.280
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0567 before and 0.0511 after correction.
The Ratio of minimum to maximum transmission is 0.9375.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_description       plate
_exptl_crystal_F_000             1696
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.859
_refine_diff_density_min         -0.404
_refine_diff_density_rms         0.061
_refine_ls_abs_structure_details
;
 Flack x determined using 2140 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     584
_refine_ls_number_reflns         6949
_refine_ls_number_restraints     83
_refine_ls_restrained_S_all      1.077
_refine_ls_R_factor_all          0.0762
_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^)+(0.0920P)^2^+2.7214P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1526
_refine_ls_wR_factor_ref         0.1645
_reflns_Friedel_coverage         0.774
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                5696
_reflns_number_total             6949
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9sc05823k1.cif
_cod_data_source_block           mcg18136d
_cod_depositor_comments
;Adding full bibliography for 1557570--1557572.cif.

 Adding full bibliography for 1557570--1557572.cif.
;
_cod_database_code               1557571
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.995
_shelx_estimated_absorpt_t_min   0.984
_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 O(H) groups
2. Restrained distances
 O4-H4
 0.85 with sigma of 0.02
 H4-O4
 0.85 with sigma of 0.02
 C41-C42 = C42-C43 = C43-C44
 1.54 with sigma of 0.02
 C41-O9 = O9-C44
 1.46 with sigma of 0.02
 O9-C41 \\sim O9'-C41 \\sim O9-C44 \\sim O9'-C44
 with sigma of 0.02
3. Rigid body (RIGU) restrains
 O9, C41, C42, C43, C44, O9', C41', C42', C43', C44'
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Same fragment restrains
{O9, C41, C42, C43, C44} sigma for 1-2: 0.002, 1-3: 0.002
as
{O9', C41', C42', C43', C44'}
5. Others
 Sof(O9')=Sof(C41')=Sof(H41C)=Sof(H41D)=Sof(C42')=Sof(H42C)=Sof(H42D)=
 Sof(C43')=Sof(H43C)=Sof(H43D)=Sof(C44')=Sof(H44C)=Sof(H44D)=1-FVAR(1)
 Sof(O9)=Sof(C41)=Sof(H41A)=Sof(H41B)=Sof(C42)=Sof(H42A)=Sof(H42B)=Sof(C43)=
 Sof(H43A)=Sof(H43B)=Sof(C44)=Sof(H44A)=Sof(H44B)=FVAR(1)
6.a Ternary CH refined with riding coordinates:
 C29(H29), C35(H35), C23(H23), C22(H22), C4(H4A), C8(H8), C1(H1), C11(H11),
 C5(H5), C14(H14), C10(H10), C15(H15)
6.b Secondary CH2 refined with riding coordinates:
 C41(H41A,H41B), C42(H42A,H42B), C43(H43A,H43B), C44(H44A,H44B), C41'(H41C,
 H41D), C42'(H42C,H42D), C43'(H43C,H43D), C44'(H44C,H44D)
6.c Aromatic/amide H refined with riding coordinates:
 C37(H37), C20(H20), C40(H40), C21(H21), C3(H3), C38(H38), C18(H18), C31(H31),
 C34(H34), C2(H2A), C39(H39), C28(H28), C12(H12), C17(H17), C33(H33), C26(H26),
 C32(H32), C25(H25), C27(H27), C13(H13)
6.d Tetrahedral OH refined with riding coordinates:
 O6(H6)
6.e Idealised tetrahedral OH refined as rotating group:
 O2(H2), O8(H8A)
;
_shelx_res_checksum              77484
_olex2_submission_special_instructions 'No special instructions were received'