Preparation and Characterization of a Small Library of Thermally-Labile End-Caps for Variable-Temperature Triggering of Self-Immolative Polymers.
Taimoory, S. Maryamdokht; Sadraei, S. Iraj; Fayoumi, Rose Anne; Nasri, Sarah; Revington, Matthew; Trant, John F.; The Journal of organic chemistry 83 (2018) 4427–4440; doi:10.1021/acs.joc.8b00135

data_4034949
_publ_section_title
;
 Preparation and Characterization of a Small Library of Thermally-Labile
 End-Caps for Variable-Temperature Triggering of Self-Immolative Polymers.
;
_journal_issue                   8
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              4427
_journal_page_last               4440
_journal_paper_doi               10.1021/acs.joc.8b00135
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C16 H14 N2 O6'
_chemical_formula_sum            'C16 H14 N2 O6'
_chemical_formula_weight         330.29
_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
_atom_sites_solution_primary     direct
_audit_creation_date             2017-11-22
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   32.259(6)
_cell_length_b                   7.365(2)
_cell_length_c                   6.107(2)
_cell_measurement_reflns_used    9920
_cell_measurement_temperature    170.0
_cell_measurement_theta_max      27.06
_cell_measurement_theta_min      3.03
_cell_volume                     1450.9(7)
_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  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      170.0
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71076
_diffrn_reflns_av_R_equivalents  0.0192
_diffrn_reflns_av_unetI/netI     0.0161
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       41
_diffrn_reflns_limit_h_min       -40
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            13128
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.243
_diffrn_reflns_theta_max         27.141
_diffrn_reflns_theta_min         3.041
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.118
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.7003
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0686 before and 0.0332 after correction. The Ratio of minimum to maximum transmission is 0.9394. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.512
_exptl_crystal_description       plate
_exptl_crystal_F_000             688
_exptl_crystal_recrystallization_method
'crystallized slow evaporation diethyl ether from methanol'
_exptl_crystal_size_max          0.508
_exptl_crystal_size_mid          0.311
_exptl_crystal_size_min          0.082
_refine_diff_density_max         0.182
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3220
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0300
_refine_ls_R_factor_gt           0.0292
_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^)+(0.0434P)^2^+0.3253P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0750
_refine_ls_wR_factor_ref         0.0755
_reflns_Friedel_coverage         0.828
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                3152
_reflns_number_total             3220
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b00135_si_002.cif
_cod_data_source_block           mo_he_nt_22_01exo_0m_a
_cod_original_cell_volume        1451.0(7)
_cod_database_code               4034949
_shelxl_version_number           2013-3
_shelx_estimated_absorpt_t_max   0.990
_shelx_estimated_absorpt_t_min   0.943
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 1.3(9)
 -0.3(9)
2. 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
3.a Ternary CH refined with riding coordinates:
 C5(H5), C6(H6)
3.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B)
3.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C12(H12), C13(H13), C14(H14), C15(H15), C16(H16)
3.d Idealised tetrahedral OH refined as rotating group:
 O4(H4)
;
_olex2_exptl_crystal_mounting_method mounted
_olex2_submission_special_instructions 'No special instructions were received'