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#$Date: 2025-08-18 18:33:07 +0300 (Mon, 18 Aug 2025) $
#$Revision: 301779 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/23/1542369.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1542369
loop_
_publ_author_name
'Manjappa, Kiran B.'
'Syu, Jia-Ru'
'Yang, Ding-Yah'
_publ_section_title
;
 Visible-Light-Promoted and Yb(OTf)3-Catalyzed Constructions of
 Coumarin-Pyrrole-(Iso)quinoline-Fused Pentacycles: Synthesis of
 Lamellarin Core, Lamellarin D Trimethyl Ether, and Lamellarin H.
;
_journal_issue                   2
_journal_name_full               'Organic letters'
_journal_page_first              332
_journal_page_last               335
_journal_paper_doi               10.1021/acs.orglett.5b03524
_journal_volume                  18
_journal_year                    2016
_chemical_formula_moiety         'C25 H15 N O2'
_chemical_formula_sum            'C25 H15 N O2'
_chemical_formula_weight         361.38
_space_group_IT_number           62
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      62
_symmetry_space_group_name_Hall  '-P 2ac 2n'
_symmetry_space_group_name_H-M   'P n m a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   23.3899(8)
_cell_length_b                   6.7857(3)
_cell_length_c                   11.1470(5)
_cell_measurement_reflns_used    9990
_cell_measurement_temperature    299(2)
_cell_measurement_theta_max      26.24
_cell_measurement_theta_min      3.13
_cell_volume                     1769.22(13)
_computing_cell_refinement       'SAINT V7.34A (Bruker AXS, 2006)'
_computing_data_collection       'APEX2 (Bruker AXS, 2010)'
_computing_data_reduction        'SAINT V7.34A (Bruker AXS, 2006)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      299(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω 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  0.0407
_diffrn_reflns_av_sigmaI/netI    0.0120
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            44862
_diffrn_reflns_theta_full        26.39
_diffrn_reflns_theta_max         26.39
_diffrn_reflns_theta_min         3.19
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  0.9889
_exptl_absorpt_correction_T_min  0.9696
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.357
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       parallelepiped
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.769
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       0.007(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         1971
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.086
_refine_ls_R_factor_all          0.0759
_refine_ls_R_factor_gt           0.0612
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0956P)²+1.0967P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1806
_refine_ls_wR_factor_ref         0.1989
_reflns_number_gt                1584
_reflns_number_total             1971
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol5b03524_si_004.cif
_cod_data_source_block           bmk2270
_cod_database_code               1542369
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z'
'-x-1/2, y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
O1 O 0.19074(11) 0.2500 0.4688(2) 0.0580(7) Uani 1 2 d S
O2 O 0.28460(11) 0.2500 0.4385(2) 0.0701(8) Uani 1 2 d S
N N 0.26041(11) 0.2500 0.1746(2) 0.0429(6) Uani 1 2 d S
C1 C 0.13431(14) 0.2500 0.4291(3) 0.0493(8) Uani 1 2 d S
C2 C 0.09284(18) 0.2500 0.5172(4) 0.0680(10) Uani 1 2 d S
H2A H 0.1031 0.2500 0.5978 0.082 Uiso 1 2 calc SR
C3 C 0.0363(2) 0.2500 0.4847(4) 0.0880(14) Uani 1 2 d S
H3A H 0.0081 0.2500 0.5434 0.106 Uiso 1 2 calc SR
C4 C 0.02130(18) 0.2500 0.3646(4) 0.0864(14) Uani 1 2 d S
H4A H -0.0171 0.2500 0.3432 0.104 Uiso 1 2 calc SR
C5 C 0.06275(14) 0.2500 0.2759(4) 0.0652(10) Uani 1 2 d S
H5A H 0.0521 0.2500 0.1955 0.078 Uiso 1 2 calc SR
C6 C 0.12031(13) 0.2500 0.3069(3) 0.0451(7) Uani 1 2 d S
C7 C 0.16756(12) 0.2500 0.2228(3) 0.0403(7) Uani 1 2 d S
C8 C 0.22212(12) 0.2500 0.2684(3) 0.0407(7) Uani 1 2 d S
C9 C 0.23660(14) 0.2500 0.3927(3) 0.0490(8) Uani 1 2 d S
C10 C 0.32006(14) 0.2500 0.1800(3) 0.0563(9) Uani 1 2 d S
H10A H 0.3391 0.2500 0.2532 0.068 Uiso 1 2 calc SR
C11 C 0.34885(14) 0.2500 0.0765(3) 0.0582(9) Uani 1 2 d S
H11A H 0.3886 0.2500 0.0791 0.070 Uiso 1 2 calc SR
C12 C 0.32156(15) 0.2500 -0.0372(3) 0.0510(8) Uani 1 2 d S
C13 C 0.35296(17) 0.2500 -0.1452(4) 0.0653(10) Uani 1 2 d S
H13A H 0.3927 0.2500 -0.1423 0.078 Uiso 1 2 calc SR
C14 C 0.3260(2) 0.2500 -0.2537(4) 0.0684(11) Uani 1 2 d S
H14A H 0.3475 0.2500 -0.3239 0.082 Uiso 1 2 calc SR
C15 C 0.2667(2) 0.2500 -0.2601(3) 0.0649(10) Uani 1 2 d S
H15A H 0.2486 0.2500 -0.3343 0.078 Uiso 1 2 calc SR
C16 C 0.23526(16) 0.2500 -0.1573(3) 0.0537(8) Uani 1 2 d S
H16A H 0.1956 0.2500 -0.1623 0.064 Uiso 1 2 calc SR
C17 C 0.26132(14) 0.2500 -0.0438(3) 0.0445(7) Uani 1 2 d S
C18 C 0.22958(13) 0.2500 0.0678(3) 0.0400(7) Uani 1 2 d S
C19 C 0.17130(12) 0.2500 0.0966(3) 0.0412(7) Uani 1 2 d S
C20 C 0.12307(13) 0.2500 0.0100(3) 0.0481(8) Uani 1 2 d S
C21 C 0.10040(13) 0.0760(5) -0.0314(3) 0.0807(9) Uani 1 1 d .
H21A H 0.1157 -0.0433 -0.0058 0.097 Uiso 1 1 calc R
C22 C 0.05495(15) 0.0773(7) -0.1109(3) 0.1063(13) Uani 1 1 d .
H22A H 0.0402 -0.0415 -0.1387 0.128 Uiso 1 1 calc R
C23 C 0.0316(2) 0.2500 -0.1490(4) 0.0998(19) Uani 1 2 d S
H23A H 0.0002 0.2500 -0.2002 0.120 Uiso 1 2 calc SR
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
C1 O1 C9 123.1(3) .
C8 N C18 108.2(2) .
C8 N C10 128.2(3) .
C18 N C10 123.7(3) .
C2 C1 O1 116.1(3) .
C2 C1 C6 121.8(3) .
O1 C1 C6 122.0(3) .
C1 C2 C3 119.3(4) .
C1 C2 H2A 120.3 .
C3 C2 H2A 120.3 .
C4 C3 C2 120.0(4) .
C4 C3 H3A 120.0 .
C2 C3 H3A 120.0 .
C3 C4 C5 120.8(4) .
C3 C4 H4A 119.6 .
C5 C4 H4A 119.6 .
C4 C5 C6 120.1(4) .
C4 C5 H5A 120.0 .
C6 C5 H5A 120.0 .
C5 C6 C1 117.9(3) .
C5 C6 C7 125.3(3) .
C1 C6 C7 116.8(3) .
C8 C7 C19 108.2(3) .
C8 C7 C6 118.0(3) .
C19 C7 C6 133.9(3) .
N C8 C7 108.9(3) .
N C8 C9 125.7(3) .
C7 C8 C9 125.5(3) .
O2 C9 O1 117.2(3) .
O2 C9 C8 128.2(3) .
O1 C9 C8 114.6(3) .
C11 C10 N 117.8(3) .
C11 C10 H10A 121.1 .
N C10 H10A 121.1 .
C10 C11 C12 123.0(3) .
C10 C11 H11A 118.5 .
C12 C11 H11A 118.5 .
C17 C12 C13 118.4(3) .
C17 C12 C11 119.7(3) .
C13 C12 C11 121.9(3) .
C14 C13 C12 121.1(4) .
C14 C13 H13A 119.5 .
C12 C13 H13A 119.5 .
C13 C14 C15 120.5(3) .
C13 C14 H14A 119.8 .
C15 C14 H14A 119.8 .
C16 C15 C14 119.7(4) .
C16 C15 H15A 120.1 .
C14 C15 H15A 120.1 .
C15 C16 C17 121.6(4) .
C15 C16 H16A 119.2 .
C17 C16 H16A 119.2 .
C12 C17 C16 118.7(3) .
C12 C17 C18 117.8(3) .
C16 C17 C18 123.4(3) .
N C18 C19 107.9(3) .
N C18 C17 118.0(3) .
C19 C18 C17 134.1(3) .
C18 C19 C7 106.8(2) .
C18 C19 C20 126.2(3) .
C7 C19 C20 127.0(3) .
C21 C20 C21 118.5(3) 7_565
C21 C20 C19 120.77(16) 7_565
C21 C20 C19 120.77(16) .
C20 C21 C22 120.4(3) .
C20 C21 H21A 119.8 .
C22 C21 H21A 119.8 .
C23 C22 C21 120.9(4) .
C23 C22 H22A 119.6 .
C21 C22 H22A 119.6 .
C22 C23 C22 119.0(4) 7_565
C22 C23 H23A 120.5 7_565
C22 C23 H23A 120.5 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C1 1.392(4) .
O1 C9 1.368(4) .
O2 C9 1.233(4) .
N C8 1.376(4) .
N C18 1.392(4) .
N C10 1.396(4) .
C1 C2 1.380(5) .
C1 C6 1.401(4) .
C2 C3 1.370(6) .
C2 H2A 0.9300 .
C3 C4 1.385(7) .
C3 H3A 0.9300 .
C4 C5 1.384(5) .
C4 H4A 0.9300 .
C5 C6 1.390(5) .
C5 H5A 0.9300 .
C6 C7 1.449(4) .
C7 C8 1.374(4) .
C7 C19 1.409(4) .
C8 C9 1.426(4) .
C10 C11 1.336(5) .
C10 H10A 0.9300 .
C11 C12 1.419(5) .
C11 H11A 0.9300 .
C12 C17 1.411(5) .
C12 C13 1.410(5) .
C13 C14 1.365(6) .
C13 H13A 0.9300 .
C14 C15 1.388(6) .
C14 H14A 0.9300 .
C15 C16 1.363(5) .
C15 H15A 0.9300 .
C16 C17 1.404(4) .
C16 H16A 0.9300 .
C17 C18 1.449(4) .
C18 C19 1.400(4) .
C19 C20 1.485(4) .
C20 C21 1.374(3) 7_565
C20 C21 1.374(3) .
C21 C22 1.385(4) .
C21 H21A 0.9300 .
C22 C23 1.360(5) .
C22 H22A 0.9300 .
C23 C22 1.360(5) 7_565
C23 H23A 0.9300 .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 9928878
