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_1520656
_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         'C16 H17 Cl O5'
_chemical_formula_sum            'C16 H17 Cl O5'
_chemical_formula_weight         324.74
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2014-05-02
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_cell_angle_alpha                76.228(2)
_cell_angle_beta                 76.658(2)
_cell_angle_gamma                84.002(2)
_cell_formula_units_Z            2
_cell_length_a                   6.9648(10)
_cell_length_b                   7.7685(11)
_cell_length_c                   14.728(2)
_cell_measurement_reflns_used    3121
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.301
_cell_measurement_theta_min      2.773
_cell_volume                     752.04(18)
_computing_cell_refinement       'APEX2 v2012.10-0 (BRUKER, 2012)'
_computing_data_collection       'COSMO v1.61 (BRUKER, 2009)'
_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      173.15
_diffrn_detector                 'Bruker APEX-II CCD area detector'
_diffrn_detector_area_resol_mean 8
_diffrn_detector_type            'Bruker APEX-II CCD area detector'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_collimation    Monocap
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0346
_diffrn_reflns_av_unetI/netI     0.0423
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            7294
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.313
_diffrn_reflns_theta_min         2.703
_diffrn_source                   'sealed X-ray tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.275
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6625
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0597 before and 0.0424 after correction.
The Ratio of minimum to maximum transmission is 0.8890.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.434
_exptl_crystal_description       chunk
_exptl_crystal_F_000             340
_exptl_crystal_size_max          0.409
_exptl_crystal_size_mid          0.243
_exptl_crystal_size_min          0.114
_refine_diff_density_max         0.247
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     204
_refine_ls_number_reflns         2742
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.096
_refine_ls_R_factor_all          0.0551
_refine_ls_R_factor_gt           0.0399
_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^)+(0.0469P)^2^+0.0842P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0950
_refine_ls_wR_factor_ref         0.1039
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2096
_reflns_number_total             2742
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol5b01417_si_002.cif
_cod_data_source_block           jz414b
_cod_depositor_comments
'Adding full bibliography for 1520655--1520656.cif.'
_cod_original_cell_volume        752.02(19)
_cod_database_code               1520656
_shelxl_version_number           2013-4
_shelx_estimated_absorpt_t_max   0.969
_shelx_estimated_absorpt_t_min   0.896
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C8(H8), C10(H10)
2.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C16(H16A,H16B,
 H16C)
2.d Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_shelx_res_checksum              76915
_shelx_hkl_checksum              97008
_contact_crystallographer_email  staples@chemistry.msu.com
_contact_crystallographer_name   'Richard Staples'