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#$Date: 2025-08-18 16:30:32 +0300 (Mon, 18 Aug 2025) $
#$Revision: 301775 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/62/1506221.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_1506221
loop_
_publ_author_name
'Moorthy, Jarugu Narasimha'
'Venkatakrishnan, Parthasarathy'
'Sengupta, Sanchita'
'Baidya, Mahiuddin'
_publ_section_title
;
 Facile synthesis, fluorescence, and photochromism of novel helical
 pyrones and chromenes.
;
_journal_issue                   21
_journal_name_full               'Organic letters'
_journal_page_first              4891
_journal_page_last               4894
_journal_paper_doi               10.1021/ol0619260
_journal_volume                  8
_journal_year                    2006
_chemical_compound_source        synthetic
_chemical_formula_moiety         'C21 H12 O2'
_chemical_formula_sum            'C21 H12 O2'
_chemical_formula_weight         296.31
_chemical_melting_point          192
_chemical_name_systematic
;
 2-pyranone-annulated tetrahelicenes RI-1
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 104.03
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.559(5)
_cell_length_b                   5.626(5)
_cell_length_c                   19.945(5)
_cell_measurement_reflns_used    165
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25
_cell_measurement_theta_min      2.5
_cell_volume                     1367.2(14)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0745
_diffrn_reflns_av_sigmaI/netI    0.1047
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            8552
_diffrn_reflns_theta_full        28.32
_diffrn_reflns_theta_max         28.32
_diffrn_reflns_theta_min         2.10
_exptl_absorpt_coefficient_mu    0.092
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.440
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prisms
_exptl_crystal_F_000             616
_exptl_crystal_recrystallization_method Evaporation
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.9
_exptl_crystal_size_min          0.6
_refine_diff_density_max         0.695
_refine_diff_density_min         -0.366
_refine_diff_density_rms         0.117
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.127
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         3368
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.127
_refine_ls_R_factor_all          0.1751
_refine_ls_R_factor_gt           0.1327
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1355P)²+9.5136P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3673
_refine_ls_wR_factor_ref         0.3935
_reflns_number_gt                2205
_reflns_number_total             3368
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol0619260si20060904_021321.cif
_cod_data_source_block           1
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               1506221
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
O001 O 0.8914(3) 0.2610(7) 0.5246(3) 0.0339(11) Uani 1 1 d .
O002 O 0.8689(4) 0.2853(9) 0.6304(3) 0.0448(13) Uani 1 1 d .
C003 C 0.7072(5) -0.3299(10) 0.3489(3) 0.0224(12) Uani 1 1 d .
C004 C 0.7777(4) -0.1567(10) 0.5008(3) 0.0241(12) Uani 1 1 d .
H004 H 0.7416 -0.3022 0.4942 0.029 Uiso 1 1 calc R
C005 C 0.6070(4) -0.3675(9) 0.3721(3) 0.0195(11) Uani 1 1 d .
C006 C 0.5745(6) -0.7319(11) 0.3006(3) 0.0323(15) Uani 1 1 d .
H006 H 0.5374 -0.8749 0.2892 0.039 Uiso 1 1 calc R
C007 C 0.7993(5) -0.0549(11) 0.5647(3) 0.0281(13) Uani 1 1 d .
H007 H 0.7785 -0.1332 0.6006 0.034 Uiso 1 1 calc R
C008 C 0.5435(5) -0.5731(10) 0.3496(3) 0.0248(12) Uani 1 1 d .
C009 C 0.4662(5) -0.2349(10) 0.4274(3) 0.0231(12) Uani 1 1 d .
H009 H 0.4386 -0.1191 0.4519 0.028 Uiso 1 1 calc R
C010 C 0.8085(4) -0.0482(10) 0.4444(3) 0.0236(12) Uani 1 1 d .
C011 C 0.8741(5) 0.1547(11) 0.4598(4) 0.0320(14) Uani 1 1 d .
C012 C 0.6567(6) -0.6735(13) 0.2716(3) 0.0405(18) Uani 1 1 d .
H012 H 0.6707 -0.7694 0.2367 0.049 Uiso 1 1 calc R
C013 C 0.4459(5) -0.6108(10) 0.3717(3) 0.0289(13) Uani 1 1 d .
H013 H 0.4071 -0.7515 0.3597 0.035 Uiso 1 1 calc R
C014 C 0.4078(5) -0.4487(12) 0.4096(3) 0.0303(14) Uani 1 1 d .
H014 H 0.3437 -0.4773 0.4239 0.036 Uiso 1 1 calc R
C015 C 0.7886(4) -0.1472(10) 0.3754(3) 0.0254(13) Uani 1 1 d .
C016 C 0.7234(5) -0.4679(12) 0.2928(3) 0.0331(15) Uani 1 1 d .
C017 C 0.8032(6) -0.3983(15) 0.2568(3) 0.0402(18) Uani 1 1 d .
H017 H 0.8150 -0.4933 0.2211 0.048 Uiso 1 1 calc R
C018 C 0.5631(4) -0.1952(10) 0.4092(3) 0.0194(11) Uani 1 1 d .
H018 H 0.6005 -0.0528 0.4215 0.023 Uiso 1 1 calc R
C019 C 0.9257(5) 0.1385(13) 0.3551(4) 0.0402(19) Uani 1 1 d .
H019 H 0.9680 0.1961 0.3263 0.048 Uiso 1 1 calc R
C020 C 0.9303(5) 0.2520(12) 0.4153(4) 0.0382(16) Uani 1 1 d .
H020 H 0.9703 0.3917 0.4263 0.046 Uiso 1 1 calc R
C021 C 0.8532(5) 0.1696(11) 0.5775(4) 0.0318(14) Uani 1 1 d .
C022 C 0.8580(5) -0.0690(13) 0.3334(4) 0.0363(16) Uani 1 1 d .
C023 C 0.8621(6) -0.1971(15) 0.2733(4) 0.0433(19) Uani 1 1 d .
H023 H 0.9058 -0.1426 0.2450 0.052 Uiso 1 1 calc R
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'
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
C021 O001 C011 123.5(5)
C016 C003 C015 116.8(5)
C016 C003 C005 118.2(6)
C015 C003 C005 124.9(5)
C007 C004 C010 122.1(6)
C018 C005 C008 117.9(5)
C018 C005 C003 122.9(5)
C008 C005 C003 118.8(5)
C012 C006 C008 120.1(6)
C004 C007 C021 121.2(6)
C005 C008 C013 119.2(5)
C005 C008 C006 119.8(6)
C013 C008 C006 120.9(6)
C018 C009 C014 121.0(5)
C011 C010 C004 116.0(6)
C011 C010 C015 118.6(6)
C004 C010 C015 124.9(5)
C020 C011 O001 116.1(6)
C020 C011 C010 123.4(7)
O001 C011 C010 120.4(6)
C006 C012 C016 121.8(6)
C014 C013 C008 121.8(5)
C013 C014 C009 119.1(5)
C022 C015 C010 116.9(6)
C022 C015 C003 118.9(6)
C010 C015 C003 124.1(5)
C003 C016 C017 120.2(7)
C003 C016 C012 119.3(6)
C017 C016 C012 120.5(6)
C023 C017 C016 121.3(6)
C009 C018 C005 120.8(5)
C020 C019 C022 123.0(6)
C019 C020 C011 117.9(7)
O002 C021 O001 117.2(6)
O002 C021 C007 126.9(7)
O001 C021 C007 115.9(6)
C023 C022 C015 119.9(7)
C023 C022 C019 121.8(6)
C015 C022 C019 118.3(6)
C017 C023 C022 120.4(6)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O001 C021 1.361(8)
O001 C011 1.394(8)
O002 C021 1.213(8)
C003 C016 1.418(8)
C003 C015 1.456(9)
C003 C005 1.458(8)
C004 C007 1.362(8)
C004 C010 1.414(8)
C005 C018 1.410(7)
C005 C008 1.415(8)
C006 C012 1.341(10)
C006 C008 1.445(8)
C007 C021 1.427(9)
C008 C013 1.415(9)
C009 C018 1.370(7)
C009 C014 1.409(9)
C010 C011 1.397(8)
C010 C015 1.449(9)
C011 C020 1.375(9)
C012 C016 1.431(10)
C013 C014 1.344(9)
C015 C022 1.418(8)
C016 C017 1.422(9)
C017 C023 1.349(12)
C019 C020 1.348(11)
C019 C022 1.447(10)
C022 C023 1.409(11)
loop_
_cod_related_entry_id
_cod_related_entry_code
_cod_related_entry_database
1 21151923 ChemSpider
2 101416325 PubChem
