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_1557572
_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         'C8 H8 O5'
_chemical_formula_sum            'C8 H8 O5'
_chemical_formula_weight         184.14
_chemical_name_systematic
'exo,exo-7-oxa-5-norbornene-2,3-dicarboxylic acid'
_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
_audit_creation_date             2018-10-22
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-03-04 deposited with the CCDC.	2020-03-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.72(3)
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   9.2321(19)
_cell_length_b                   18.768(4)
_cell_length_c                   18.876(4)
_cell_measurement_reflns_used    6898
_cell_measurement_temperature    190(2)
_cell_measurement_theta_max      48.97
_cell_measurement_theta_min      6.128
_cell_volume                     3263.7(12)
_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      190.15
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Nonius APEX II Kappa'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0553
_diffrn_reflns_av_unetI/netI     0.0725
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            50626
_diffrn_reflns_point_group_measured_fraction_full 0.950
_diffrn_reflns_point_group_measured_fraction_max 0.928
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.432
_diffrn_reflns_theta_min         2.162
_exptl_absorpt_coefficient_mu    0.127
_exptl_absorpt_correction_T_max  0.7253
_exptl_absorpt_correction_T_min  0.6778
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0696 before and 0.0639 after correction.
The Ratio of minimum to maximum transmission is 0.9345.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.499
_exptl_crystal_description       prism
_exptl_crystal_F_000             1536
_exptl_crystal_recrystallization_method 'slow evaporation from ethyl acetate'
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.328
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details
;
 Flack x determined using 2575 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.5(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1156
_refine_ls_number_reflns         12483
_refine_ls_number_restraints     1296
_refine_ls_restrained_S_all      1.000
_refine_ls_R_factor_all          0.1096
_refine_ls_R_factor_gt           0.0584
_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^)+(0.0672P)^2^+1.6901P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1352
_refine_ls_wR_factor_ref         0.1632
_reflns_Friedel_coverage         0.811
_reflns_Friedel_fraction_full    0.897
_reflns_Friedel_fraction_max     0.859
_reflns_number_gt                7838
_reflns_number_total             12483
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9sc05823k1.cif
_cod_data_source_block           dalecorrectedmcg1797a_a
_cod_depositor_comments
;Adding full bibliography for 1557570--1557572.cif.

 Adding full bibliography for 1557570--1557572.cif.
;
_cod_original_cell_volume        3263.8(11)
_cod_database_code               1557572
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.984
_shelx_estimated_absorpt_t_min   0.965
_olex2_refinement_description
;
1. Fixed Uiso
 At 1 times of:
  All O(O,O) groups
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups, All O(H,H) groups
2. Restrained distances
 C6-C8 \\sim C6'-C8 \\sim C7-C9 \\sim C7'-C9
 with sigma of 0.01
 C16-C18 \\sim C16'-C18 \\sim C17-C19 \\sim C17'-C19
 with sigma of 0.01
 C26-C28 \\sim C26'-C28 \\sim C27-C29 \\sim C27'-C29
 with sigma of 0.02
 C36-C38 \\sim C36'-C38 \\sim C37-C39 \\sim C37'-C39
 with sigma of 0.01
 C69-O69A \\sim C69-O69C
 with sigma of 0.01
 C69-O69B \\sim C69-O69D
 with sigma of 0.01
 O69A-O69B \\sim O69C-O69D
 with sigma of 0.01
 C78-O78A \\sim C78-O78C
 with sigma of 0.01
 C78-O78B \\sim C78-O78B
 with sigma of 0.01
 O78A-O78B \\sim O78C-O78D
 with sigma of 0.01
3. Restrained planarity
 C67, C69, O69C, O69D
 with sigma of 0.1
 C76, C78, O78C, O78D
 with sigma of 0.1
4. Uiso/Uaniso restraints and constraints
Uanis(C6) = Uanis(C6')
Uanis(C7) = Uanis(C7')
Uanis(C16) = Uanis(C16')
Uanis(C17) = Uanis(C17')
Uanis(C27) = Uanis(C26')
Uanis(C27) = Uanis(C27')
Uanis(C36) = Uanis(C36')
Uanis(C37) = Uanis(C37')
5. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6. Same fragment restrains
{O1, C2, C3, C4, C5, C6, C7} sigma for 1-2: 0.02, 1-3: 0.04
as
{O1', C2', C3', C4', C5', C6', C7'}
{O11, C12, C13, C14, C15, C16, C17} sigma for 1-2: 0.02, 1-3: 0.04
as
{O11', C12', C13', C14', C15', C16', C17'}
{O21, C22, C23, C24, C25, C26, C27} sigma for 1-2: 0.02, 1-3: 0.04
as
{O21', C22', C23', C24', C25', C26', C27'}
{O31, C32, C33, C34, C35, C36, C37} sigma for 1-2: 0.02, 1-3: 0.04
as
{O31', C32', C33', C34', C35', C36', C37'}
7. Others
 Sof(O1')=Sof(C2')=Sof(H2')=Sof(C3')=Sof(H3')=Sof(C4')=Sof(H4')=Sof(C5')=
 Sof(H5')=Sof(C6')=Sof(H6')=Sof(C7')=Sof(H7')=Sof(O21')=Sof(C22')=Sof(H22')=
 Sof(C23')=Sof(H23')=Sof(C24')=Sof(H24')=Sof(C25')=Sof(H25')=Sof(C26')=
 Sof(H26')=Sof(C27')=Sof(H27')=1-FVAR(1)
 Sof(O1)=Sof(C2)=Sof(H2)=Sof(C3)=Sof(H3)=Sof(C4)=Sof(H4)=Sof(C5)=Sof(H5)=
 Sof(C6)=Sof(H6)=Sof(C7)=Sof(H7)=Sof(O21)=Sof(C22)=Sof(H22)=Sof(C23)=Sof(H23)=
 Sof(C24)=Sof(H24)=Sof(C25)=Sof(H25)=Sof(C26)=Sof(H26)=Sof(C27)=Sof(H27)=FVAR(1)
 Sof(O11')=Sof(C12')=Sof(H12')=Sof(C13')=Sof(H13')=Sof(C14')=Sof(H14')=
 Sof(C15')=Sof(H15')=Sof(C16')=Sof(H16')=Sof(C17')=Sof(H17')=Sof(O31')=
 Sof(C32')=Sof(H32')=Sof(C33')=Sof(H33')=Sof(C34')=Sof(H34')=Sof(C35')=
 Sof(H35')=Sof(C36')=Sof(H36')=Sof(C37')=Sof(H37')=1-FVAR(2)
 Sof(O11)=Sof(C12)=Sof(H12)=Sof(C13)=Sof(H13)=Sof(C14)=Sof(H14)=Sof(C15)=
 Sof(H15)=Sof(C16)=Sof(H16)=Sof(C17)=Sof(H17)=Sof(O31)=Sof(C32)=Sof(H32)=
 Sof(C33)=Sof(H33)=Sof(C34)=Sof(H34)=Sof(C35)=Sof(H35)=Sof(C36)=Sof(H36)=
 Sof(C37)=Sof(H37)=FVAR(2)
 Sof(O69C)=Sof(H69C)=Sof(O69D)=Sof(O78C)=Sof(H78C)=Sof(O78D)=1-FVAR(3)
 Sof(O69B)=Sof(O69A)=Sof(H69A)=Sof(O78B)=Sof(O78A)=Sof(H78A)=FVAR(3)
8.a Ternary CH refined with riding coordinates:
 C2(H2), C5(H5), C6(H6), C7(H7), C2'(H2'), C5'(H5'), C6'(H6'), C7'(H7'),
 C12(H12), C15(H15), C16(H16), C17(H17), C12'(H12'), C15'(H15'), C16'(H16'),
 C17'(H17'), C22(H22), C25(H25), C26(H26), C27(H27), C22'(H22'), C25'(H25'),
 C26'(H26'), C27'(H27'), C32(H32), C35(H35), C36(H36), C37(H37), C32'(H32'),
 C35'(H35'), C36'(H36'), C37'(H37'), C42(H42), C45(H45), C46(H46), C47(H47),
 C52(H52), C55(H55), C56(H56), C57(H57), C62(H62), C65(H65), C66(H66), C67(H67),
  C72(H72), C75(H75), C76(H76), C77(H77)
8.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C3'(H3'), C4'(H4'), C13(H13), C14(H14), C13'(H13'),
 C14'(H14'), C23(H23), C24(H24), C23'(H23'), C24'(H24'), C33(H33), C34(H34),
 C33'(H33'), C34'(H34'), C43(H43), C44(H44), C53(H53), C54(H54), C63(H63),
 C64(H64), C73(H73), C74(H74)
8.c Tetrahedral OH refined with riding coordinates:
 O8A(H8A), O9A(H9A), O18A(H18A), O19A(H19A), O28A(H28A), O29A(H29A),
 O38A(H38A), O39A(H39A), O48A(H48A), O49A(H49A), O58A(H58A), O59A(H59A),
 O68A(H68A), O69A(H69A), O69C(H69C), O78A(H78A), O78C(H78C), O79A(H79A)
;
_shelx_res_checksum              88686
_olex2_submission_original_sample_id mcg1797
_olex2_submission_special_instructions 'No special instructions were received'