Building Strain with Large Macrocycles and Using It To Tune the Thermal Half-Lives of Hydrazone Photochromes.
Li, Quan; Qian, Hai; Shao, Baihao; Hughes, Russell P.; Aprahamian, Ivan; Journal of the American Chemical Society 140 (2018) 11829–11835; doi:10.1021/jacs.8b07612

data_4132962
_publ_section_title
;
 Building Strain with Large Macrocycles and Using It To Tune the Thermal
 Half-Lives of Hydrazone Photochromes.
;
_journal_issue                   37
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              11829
_journal_page_last               11835
_journal_paper_doi               10.1021/jacs.8b07612
_journal_volume                  140
_journal_year                    2018
_chemical_formula_moiety         'C20 H20 N2 O4'
_chemical_formula_sum            'C20 H20 N2 O4'
_chemical_formula_weight         352.38
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2017-10-09
_audit_creation_method
;
Olex2 1.2-alpha
(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            8
_cell_length_a                   18.041(3)
_cell_length_b                   8.9247(17)
_cell_length_c                   21.595(4)
_cell_measurement_reflns_used    5649
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      23.58
_cell_measurement_theta_min      2.20
_cell_volume                     3477.0(11)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'COSMO (BRUKER, V1.61, 2009)'
_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  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 8.36
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0966
_diffrn_reflns_av_unetI/netI     0.0463
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            33389
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.577
_diffrn_reflns_theta_min         1.886
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6363
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0673 before and 0.0543 after correction. The Ratio of minimum to maximum transmission is 0.8539. The \l/2 correction factor is 0.00150.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.346
_exptl_crystal_description       needle
_exptl_crystal_F_000             1488
_exptl_crystal_recrystallization_method 'used as received'
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.172
_exptl_crystal_size_min          0.102
_refine_diff_density_max         0.255
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         3249
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.1091
_refine_ls_R_factor_gt           0.0577
_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^)+(0.0696P)^2^+1.8636P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1367
_refine_ls_wR_factor_ref         0.1657
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1912
_reflns_number_total             3249
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja8b07612_si_006.cif
_cod_data_source_block           ia917a
_cod_original_cell_volume        3476.9(11)
_cod_database_code               4132962
_shelxl_version_number           2014/6
_shelx_estimated_absorpt_t_max   0.990
_shelx_estimated_absorpt_t_min   0.964
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 C13-O3
 1.43 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C4A) = Uanis(C4)
Uanis(C2) = Uanis(C2A)
Uanis(C1A) = Uanis(C1)
Uanis(C5) = Uanis(C5A)
Uanis(C3) = Uanis(C3A)
Uanis(C1) = Uanis(C5)
Uanis(C1A) = Uanis(C5A)
Uanis(O1) = Uanis(O1A)
Uanis(O3) = Uanis(O3A)
4. Others
 Sof(O1A)=Sof(O3A)=Sof(C5A)=Sof(H5AA)=Sof(H5AB)=Sof(C4A)=Sof(H4AA)=Sof(H4AB)=
 Sof(C2A)=Sof(H2AA)=Sof(H2AB)=Sof(C3A)=Sof(H3AA)=Sof(H3AB)=Sof(C1A)=Sof(H1AA)=
 Sof(H1AB)=1-FVAR(1)
 Sof(C3)=Sof(H3A)=Sof(H3B)=Sof(C1)=Sof(H1A)=Sof(H1B)=Sof(C2)=Sof(H2A)=Sof(H2B)=
 Sof(C4)=Sof(H4A)=Sof(H4B)=Sof(C5)=Sof(H5A)=Sof(H5B)=Sof(O3)=Sof(O1)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C5A(H5AA,H5AB), C1(H1A,H1B), C4A(H4AA,H4AB), C2A(H2AA,H2AB),
 C2(H2A,H2B), C4(H4A,H4B), C5(H5A,H5B), C3A(H3AA,H3AB), C1A(H1AA,H1AB)
5.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C20(H20), C16(H16), C12(H12), C11(H11), C17(H17), C10(H10), C19(H19),
 C18(H18)
;
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a nylon loop with paratone oil'
_olex2_submission_original_sample_id 'Iq-C5 E NMR tube'
_olex2_submission_special_instructions 'No special instructions were received'