Mechanically Triggered Small Molecule Release from a Masked Furfuryl Carbonate.
Hu, Xiaoran; Zeng, Tian; Husic, Corey C.; Robb, Maxwell J.; Journal of the American Chemical Society 141 (2019) 15018–15023; doi:10.1021/jacs.9b08663

data_4129017
_publ_section_title
;
 Mechanically Triggered Small Molecule Release from a Masked Furfuryl
 Carbonate.
;
_journal_issue                   38
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              15018
_journal_page_last               15023
_journal_paper_doi               10.1021/jacs.9b08663
_journal_volume                  141
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C17 H22 Br N O7, 0.5(H2 O)'
_chemical_formula_sum            'C17 H23 Br N O7.5'
_chemical_formula_weight         441.27
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2019-07-04
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506),
 SHELXL-2018/3, and manual edit
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   12.858(2)
_cell_length_b                   10.2977(15)
_cell_length_c                   29.000(4)
_cell_measurement_reflns_used    9938
_cell_measurement_temperature    200
_cell_measurement_theta_max      79.57
_cell_measurement_theta_min      3.05
_cell_volume                     3839.8(10)
_computing_cell_refinement       'SAINT V8.38A (Bruker-AXS, 2016)'
_computing_data_collection
'BIS V6.2.9/2018-03-16 & APEX3 v2018.7-2 (Bruker-AXS, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker-AXS, 2016)'
_computing_molecular_graphics    'DIAMOND 3 (Crystal Impact, 1999)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2013)'
_diffrn_ambient_temperature      200
_diffrn_detector                 'CPAD Area Detector'
_diffrn_detector_area_resol_mean 7.69
_diffrn_detector_type            'Bruker PHOTON II'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  'multilayer mirrors'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0720
_diffrn_reflns_av_unetI/netI     0.0670
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            31123
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         81.319
_diffrn_reflns_theta_min         3.048
_diffrn_source                   'microfocus sealed tube'
_diffrn_source_current           1
_diffrn_source_power             0.05
_diffrn_source_type              'Incoatec I\mS HB'
_diffrn_source_voltage           50
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.291
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7949
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. 
wR2(int) was 0.1449 before and 0.0943 after correction. 
The Ratio of minimum to maximum transmission is 0.7949. 
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.527
_exptl_crystal_description       Block
_exptl_crystal_F_000             1816
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.713
_refine_diff_density_min         -0.691
_refine_diff_density_rms         0.079
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.45(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     500
_refine_ls_number_reflns         8177
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0870
_refine_ls_R_factor_gt           0.0667
_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^)+(0.1210P)^2^+0.1640P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1871
_refine_ls_wR_factor_ref         0.2044
_reflns_Friedel_coverage         0.927
_reflns_Friedel_fraction_full    0.990
_reflns_Friedel_fraction_max     0.945
_reflns_number_gt                6056
_reflns_number_total             8177
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b08663_si_002.cif
_cod_data_source_block           v19226
_cod_original_formula_sum        'C17 H23 Br N O7.50'
_cod_database_code               4129017
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.734
_shelx_estimated_absorpt_t_min   0.493
_refine_ls_abs_structure_hooft   0.46(1)
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.55(4)
 0.45(4)
2. 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, All O(H,H) groups
3. Restrained distances
 C15B-C17B
 1.55 with sigma of 0.001
 Br1B-C15B = Br1C-C15B
 1.96 with sigma of 0.001
 C15B-C17B = C17C-C15B
 1.55 with sigma of 0.001
4. Uiso/Uaniso restraints and constraints
Uanis(Br1C) = Uanis(C17C)
Uanis(C17B) = Uanis(Br1B)
5. Others
 Sof(Br1C)=Sof(C17C)=Sof(H17D)=Sof(H17E)=Sof(H17F)=1-FVAR(1)
 Sof(Br1B)=Sof(C17B)=Sof(H17G)=Sof(H17H)=Sof(H17I)=FVAR(1)
6.a Free rotating group:
 O8(H8A,H8C)
6.b Ternary CH refined with riding coordinates:
 C2(H2A), C5(H5), C9(H9), C2B(H2BA), C5B(H5B), C9B(H9B)
6.c Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C12(H12A,H12B), C13(H13A,H13B), C11B(H11C,H11D), C12B(H12C,
 H12D), C13B(H13C,H13D)
6.d Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C7B(H7B), C8B(H8B)
6.e Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C10B(H10D,H10E,
 H10F), C16B(H16D,H16E,H16F), C17B(H17G,H17H,H17I), C17C(H17D,H17E,H17F)
6.f Idealised tetrahedral OH refined as rotating group:
 O2(H2), O4(H4), O2B(H2B), O4B(H4B)
;
_shelx_res_checksum              85484
_shelx_hkl_checksum              78354
_olex2_submission_special_instructions 'No special instructions were received'