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_4132959
_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         'C21 H22 N2 O4'
_chemical_formula_sum            'C21 H22 N2 O4'
_chemical_formula_weight         366.40
_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             2017-10-23
_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            16
_cell_length_a                   10.6043(3)
_cell_length_b                   21.8901(7)
_cell_length_c                   32.5434(8)
_cell_measurement_reflns_used    3496
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      63.99
_cell_measurement_theta_min      4.04
_cell_volume                     7554.3(4)
_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 0.997
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\w and \f'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.1343
_diffrn_reflns_av_unetI/netI     0.0943
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            35828
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.071
_diffrn_reflns_theta_min         4.039
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.734
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_correction_T_min  0.6285
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2012/1 (Bruker,2012) was used for absorption correction. wR2(int) was 0.0666 before and 0.0567 after correction. The Ratio of minimum to maximum transmission is 0.8343. The \l/2 correction factor is 0.0015.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_description       needle
_exptl_crystal_F_000             3104
_exptl_crystal_recrystallization_method 'used as received'
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.121
_exptl_crystal_size_min          0.047
_refine_diff_density_max         0.604
_refine_diff_density_min         -0.434
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.996
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     495
_refine_ls_number_reflns         7118
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.996
_refine_ls_R_factor_all          0.1536
_refine_ls_R_factor_gt           0.0676
_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^)+(0.0808P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1474
_refine_ls_wR_factor_ref         0.1894
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3517
_reflns_number_total             7118
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja8b07612_si_009.cif
_cod_data_source_block           ia1017d
_cod_database_code               4132959
_shelxl_version_number           2014/6
_shelx_estimated_absorpt_t_max   0.966
_shelx_estimated_absorpt_t_min   0.738
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C1A(H1AA,H1AB), C2A(H2AA,H2AB), C3A(H3AA,H3AB), C4A(H4AA,H4AB), C5A(H5AA,
 H5AB), C6A(H6AA,H6AB), C1B(H1BA,H1BB), C2B(H2BA,H2BB), C3B(H3BA,H3BB),
 C4B(H4BA,H4BB), C5B(H5BA,H5BB), C6B(H6BA,H6BB)
2.b Aromatic/amide H refined with riding coordinates:
 C10A(H10A), C11A(H11A), C12A(H12A), C13A(H13A), C17A(H17A), C18A(H18A),
 C19A(H19A), C20A(H20A), C21A(H21A), C10B(H10B), C11B(H11B), C12B(H12B),
 C13B(H13B), C17B(H17B), C18B(H18B), C19B(H19B), C20B(H20B), C21B(H21B)
;
_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 '1q-C6 E'
_olex2_submission_special_instructions 'No special instructions were received'