Synthesis of coumarin/pyrrole-fused heterocycles and their photochemical and redox-switching properties.
Lin, Chi-Hui; Yang, Ding-Yah; Organic letters 15 (2013) 2802–2805; doi:10.1021/ol401138q

data_1512102
_publ_section_title
;
 Synthesis of coumarin/pyrrole-fused heterocycles and their photochemical
 and redox-switching properties.
;
_journal_issue                   11
_journal_name_full               'Organic letters'
_journal_page_first              2802
_journal_page_last               2805
_journal_paper_doi               10.1021/ol401138q
_journal_volume                  15
_journal_year                    2013
_chemical_formula_moiety         'C22 H20 N2 O3'
_chemical_formula_sum            'C22 H20 N2 O3'
_chemical_formula_weight         360.40
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
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_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
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                88.316(5)
_cell_angle_beta                 82.179(5)
_cell_angle_gamma                66.985(7)
_cell_formula_units_Z            2
_cell_length_a                   8.3832(6)
_cell_length_b                   10.2607(7)
_cell_length_c                   11.7781(6)
_cell_measurement_reflns_used    2463
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      29.0356
_cell_measurement_theta_min      2.6589
_cell_volume                     923.49(11)
_computing_cell_refinement
; 
CrysAlis RED, Oxford Diffraction Ltd., 
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) 
(compiled Jun 10 2008,16:49:55) 
;
_computing_data_collection
; 
CrysAlis CCD, Oxford Diffraction Ltd., 
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) 
(compiled Jun 10 2008,16:49:55) 
;
_computing_data_reduction
; 
CrysAlis RED, Oxford Diffraction Ltd., 
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) 
(compiled Jun 10 2008,16:49:55) 
;
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      110(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.854
_diffrn_measurement_device_type  'CCD detector'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0206
_diffrn_reflns_av_sigmaI/netI    0.0371
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8200
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         29.10
_diffrn_reflns_theta_min         2.66
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.99076
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) 
(compiled Oct 27 2011,15:02:11) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       parallelepiped
_exptl_crystal_F_000             380
_exptl_crystal_size_max          0.66
_exptl_crystal_size_mid          0.46
_exptl_crystal_size_min          0.28
_refine_diff_density_max         1.270
_refine_diff_density_min         -0.375
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     268
_refine_ls_number_reflns         4241
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0806
_refine_ls_R_factor_gt           0.0661
_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^)+(0.0917P)^2^+0.9121P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1752
_refine_ls_wR_factor_ref         0.1875
_reflns_number_gt                3397
_reflns_number_total             4241
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol401138q_si_006.cif
_cod_data_source_block           ch342
_cod_original_cell_volume        923.49(10)
_cod_database_code               1512102