The Synthesis of a New Class of Highly Fluorescent Chromones via an Inverse-Demand Hetero-Diels-Alder Reaction.
Zimmerman, Jake R.; Johntony, Olivia; Steigerwald, Daniel; Criss, Cody; Myers, Brian J.; Kinder, David H.; Organic letters 17 (2015) 3256–3259; doi:10.1021/acs.orglett.5b01417

data_1520655
_publ_section_title
;
 The Synthesis of a New Class of Highly Fluorescent Chromones via an
 Inverse-Demand Hetero-Diels-Alder Reaction.
;
_journal_issue                   13
_journal_name_full               'Organic letters'
_journal_page_first              3256
_journal_page_last               3259
_journal_paper_doi               10.1021/acs.orglett.5b01417
_journal_volume                  17
_journal_year                    2015
_chemical_formula_moiety         'C32 H38 O5 Si2'
_chemical_formula_sum            'C32 H38 O5 Si2'
_chemical_formula_weight         558.80
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2014-11-04
_audit_creation_method
;
Olex2 1.2
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 92.2660(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.2692(7)
_cell_length_b                   9.7098(7)
_cell_length_c                   34.752(3)
_cell_measurement_reflns_used    9172
_cell_measurement_temperature    173.0
_cell_measurement_theta_max      25.350
_cell_measurement_theta_min      2.178
_cell_volume                     3125.3(4)
_computing_cell_refinement       'SAINT v8.27A (Bruker, 2012)'
_computing_data_reduction        'SAINT v8.27A (Bruker, 2012)'
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      173.0
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0443
_diffrn_reflns_av_unetI/netI     0.0367
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_number            25358
_diffrn_reflns_theta_full        25.37
_diffrn_reflns_theta_max         25.37
_diffrn_reflns_theta_min         2.18
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.150
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6772
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.1508 before and 0.0485 after correction.
The Ratio of minimum to maximum transmission is 0.9087.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.188
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1192
_exptl_crystal_size_max          0.357
_exptl_crystal_size_mid          0.191
_exptl_crystal_size_min          0.106
_refine_diff_density_max         0.337
_refine_diff_density_min         -0.293
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     358
_refine_ls_number_reflns         5727
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0631
_refine_ls_R_factor_gt           0.0429
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0452P)^2^+1.3761P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0984
_refine_ls_wR_factor_ref         0.1091
_reflns_number_gt                4277
_reflns_number_total             5727
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol5b01417_si_002.cif
_cod_data_source_block           jz1114a
_cod_depositor_comments
'Adding full bibliography for 1520655--1520656.cif.'
_cod_database_code               1520655
_olex2_refinement_description
;
1. 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
2.a Ternary CH refined with riding coordinates:
 C1(H1), C18(H18)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C19(H19A,H19B)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C9(H9), C13(H13), C14(H14), C15(H15), C16(H16),
 C17(H17), C22(H22), C23(H23), C24(H24), C25(H25), C26(H26)
2.d Idealised Me refined as rotating group:
 C27(H27A,H27B,H27C), C28(H28A,H28B,H28C), C29(H29A,H29B,H29C), C30(H30A,H30B,
 H30C), C31(H31A,H31B,H31C), C32(H32A,H32B,H32C)
;
_olex2_submission_original_sample_id JZ-28D
_olex2_submission_special_instructions 'No special instructions were received'