#------------------------------------------------------------------------------
#$Date: 2025-08-18 17:20:24 +0300 (Mon, 18 Aug 2025) $
#$Revision: 301776 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/51/43/1514343.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_1514343
loop_
_publ_author_name
'Wu, Yen-Ku'
'West, F. G.'
_publ_section_title
;
 Formal Homologous Aldol Reactions: Interrupting the Nazarov Cyclization
 via Carboalkoxylation of Alkynes.
;
_journal_issue                   9
_journal_name_full               'Organic letters'
_journal_page_first              2534
_journal_page_last               2537
_journal_paper_doi               10.1021/ol500914a
_journal_volume                  16
_journal_year                    2014
_chemical_formula_moiety         'C28 H28 O2'
_chemical_formula_sum            'C28 H28 O2'
_chemical_formula_weight         396.50
_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                 102.0320(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.23690(10)
_cell_length_b                   10.9853(2)
_cell_length_c                   19.9009(3)
_cell_measurement_reflns_used    9970
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      68.07
_cell_measurement_theta_min      4.42
_cell_volume                     2188.80(6)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_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      173(2)
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0123
_diffrn_reflns_av_sigmaI/netI    0.0103
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            14096
_diffrn_reflns_theta_full        67.80
_diffrn_reflns_theta_max         69.07
_diffrn_reflns_theta_min         4.42
_exptl_absorpt_coefficient_mu    0.574
_exptl_absorpt_correction_T_max  0.9343
_exptl_absorpt_correction_T_min  0.8721
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.203
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       fragment
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.234
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     274
_refine_ls_number_reflns         3961
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0375
_refine_ls_R_factor_gt           0.0362
_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)+(0.0492P)²+0.5525P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0940
_refine_ls_wR_factor_ref         0.0952
_reflns_number_gt                3766
_reflns_number_total             3961
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ol500914a_si_001.cif
_cod_data_source_block           compound10
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 

 Adding full bibliography for 1514343.cif.
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               1514343
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
O1 O 0.29891(8) 0.28507(7) 0.07022(4) 0.0374(2) Uani 1 1 d .
O2 O 0.30773(10) -0.35879(8) 0.09246(6) 0.0542(3) Uani 1 1 d .
C1 C 0.33623(11) 0.30091(10) 0.19688(6) 0.0300(2) Uani 1 1 d .
C2 C 0.22324(10) 0.38128(9) 0.21550(5) 0.0289(2) Uani 1 1 d .
H2 H 0.2218 0.4585 0.1888 0.035 Uiso 1 1 calc R
C3 C 0.09161(10) 0.31089(9) 0.18317(5) 0.0281(2) Uani 1 1 d .
H3 H 0.0575 0.2709 0.2213 0.034 Uiso 1 1 calc R
C4 C 0.13954(10) 0.20803(9) 0.13862(5) 0.0286(2) Uani 1 1 d .
C5 C 0.20719(11) 0.10984(10) 0.19212(5) 0.0304(2) Uani 1 1 d .
H5 H 0.1479 0.0953 0.2254 0.036 Uiso 1 1 calc R
C6 C 0.33720(11) 0.17525(10) 0.23108(6) 0.0324(2) Uani 1 1 d .
H6A H 0.3363 0.1839 0.2805 0.039 Uiso 1 1 calc R
H6B H 0.4176 0.1285 0.2265 0.039 Uiso 1 1 calc R
C7 C 0.26457(11) 0.26786(9) 0.12399(5) 0.0289(2) Uani 1 1 d .
C8 C 0.47075(11) 0.36198(11) 0.20466(6) 0.0387(3) Uani 1 1 d .
H8A H 0.5303 0.3104 0.1842 0.046 Uiso 1 1 calc R
H8B H 0.5094 0.3742 0.2535 0.046 Uiso 1 1 calc R
H8C H 0.4598 0.4410 0.1813 0.046 Uiso 1 1 calc R
C9 C 0.03733(11) 0.16050(10) 0.07815(6) 0.0351(3) Uani 1 1 d .
H9A H 0.0800 0.1023 0.0522 0.042 Uiso 1 1 calc R
H9B H 0.0008 0.2285 0.0482 0.042 Uiso 1 1 calc R
H9C H -0.0350 0.1199 0.0949 0.042 Uiso 1 1 calc R
C10 C 0.24210(11) 0.41767(10) 0.29007(6) 0.0310(2) Uani 1 1 d .
C11 C 0.21236(12) 0.34131(11) 0.34087(6) 0.0368(3) Uani 1 1 d .
H11 H 0.1745 0.2635 0.3286 0.044 Uiso 1 1 calc R
C12 C 0.23746(13) 0.37769(13) 0.40931(6) 0.0440(3) Uani 1 1 d .
H12 H 0.2173 0.3244 0.4434 0.053 Uiso 1 1 calc R
C13 C 0.29163(14) 0.49086(13) 0.42792(7) 0.0480(3) Uani 1 1 d .
H13 H 0.3095 0.5153 0.4747 0.058 Uiso 1 1 calc R
C14 C 0.31982(13) 0.56843(12) 0.37822(7) 0.0463(3) Uani 1 1 d .
H14 H 0.3562 0.6467 0.3908 0.056 Uiso 1 1 calc R
C15 C 0.29521(12) 0.53232(11) 0.31001(6) 0.0376(3) Uani 1 1 d .
H15 H 0.3148 0.5865 0.2762 0.045 Uiso 1 1 calc R
C16 C -0.01712(10) 0.39315(9) 0.14458(5) 0.0287(2) Uani 1 1 d .
C17 C -0.14696(12) 0.38208(11) 0.15457(6) 0.0379(3) Uani 1 1 d .
H17 H -0.1668 0.3223 0.1855 0.045 Uiso 1 1 calc R
C18 C -0.24817(12) 0.45710(13) 0.12011(7) 0.0460(3) Uani 1 1 d .
H18 H -0.3362 0.4486 0.1279 0.055 Uiso 1 1 calc R
C19 C -0.22173(12) 0.54385(11) 0.07466(6) 0.0399(3) Uani 1 1 d .
H19 H -0.2910 0.5954 0.0513 0.048 Uiso 1 1 calc R
C20 C -0.09390(12) 0.55515(11) 0.06352(6) 0.0358(3) Uani 1 1 d .
H20 H -0.0752 0.6143 0.0320 0.043 Uiso 1 1 calc R
C21 C 0.00762(11) 0.48067(10) 0.09809(6) 0.0325(2) Uani 1 1 d .
H21 H 0.0953 0.4895 0.0899 0.039 Uiso 1 1 calc R
C22 C 0.23408(11) -0.01116(10) 0.16120(6) 0.0307(2) Uani 1 1 d .
C23 C 0.15392(12) -0.11107(11) 0.16724(7) 0.0402(3) Uani 1 1 d .
H23 H 0.0794 -0.1007 0.1882 0.048 Uiso 1 1 calc R
C24 C 0.17965(13) -0.22487(12) 0.14355(8) 0.0475(3) Uani 1 1 d .
H24 H 0.1238 -0.2917 0.1489 0.057 Uiso 1 1 calc R
C25 C 0.28722(12) -0.24157(11) 0.11192(6) 0.0393(3) Uani 1 1 d .
C26 C 0.36585(11) -0.14299(11) 0.10294(6) 0.0352(3) Uani 1 1 d .
H26 H 0.4380 -0.1529 0.0802 0.042 Uiso 1 1 calc R
C27 C 0.33848(11) -0.02918(10) 0.12751(6) 0.0331(2) Uani 1 1 d .
H27 H 0.3928 0.0381 0.1211 0.040 Uiso 1 1 calc R
C28 C 0.41886(15) -0.37924(13) 0.06201(8) 0.0532(4) Uani 1 1 d .
H28A H 0.4249 -0.4661 0.0519 0.064 Uiso 1 1 calc R
H28B H 0.5006 -0.3532 0.0937 0.064 Uiso 1 1 calc R
H28C H 0.4080 -0.3325 0.0193 0.064 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 0.0181 0.0091 '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 0.0492 0.0322 '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
C25 O2 C28 116.98(11)
C8 C1 C7 116.77(9)
C8 C1 C6 115.57(9)
C7 C1 C6 99.47(8)
C8 C1 C2 115.44(9)
C7 C1 C2 97.30(8)
C6 C1 C2 109.85(9)
C10 C2 C1 115.73(9)
C10 C2 C3 117.13(9)
C1 C2 C3 103.85(8)
C16 C3 C2 113.05(8)
C16 C3 C4 115.15(8)
C2 C3 C4 104.02(8)
C9 C4 C7 117.84(9)
C9 C4 C5 115.85(9)
C7 C4 C5 99.02(8)
C9 C4 C3 116.73(9)
C7 C4 C3 99.85(8)
C5 C4 C3 104.82(8)
C22 C5 C6 113.32(9)
C22 C5 C4 114.78(9)
C6 C5 C4 103.25(8)
C1 C6 C5 105.42(8)
O1 C7 C4 130.47(10)
O1 C7 C1 129.28(10)
C4 C7 C1 100.25(8)
C11 C10 C15 117.85(11)
C11 C10 C2 123.40(10)
C15 C10 C2 118.72(10)
C12 C11 C10 120.87(12)
C13 C12 C11 120.23(13)
C12 C13 C14 119.73(12)
C13 C14 C15 120.16(12)
C14 C15 C10 121.14(12)
C17 C16 C21 117.83(10)
C17 C16 C3 119.97(10)
C21 C16 C3 122.20(9)
C18 C17 C16 121.00(11)
C19 C18 C17 120.40(11)
C20 C19 C18 119.39(11)
C19 C20 C21 120.37(11)
C20 C21 C16 121.00(10)
C27 C22 C23 117.15(10)
C27 C22 C5 123.01(10)
C23 C22 C5 119.83(10)
C24 C23 C22 121.82(11)
C23 C24 C25 119.98(11)
O2 C25 C26 124.79(11)
O2 C25 C24 115.69(11)
C26 C25 C24 119.51(11)
C25 C26 C27 119.52(11)
C22 C27 C26 121.94(10)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C7 1.2089(13)
O2 C25 1.3733(14)
O2 C28 1.4140(17)
C1 C8 1.5104(15)
C1 C7 1.5265(15)
C1 C6 1.5383(15)
C1 C2 1.5600(15)
C2 C10 1.5100(15)
C2 C3 1.5705(14)
C3 C16 1.5129(14)
C3 C4 1.5763(14)
C4 C9 1.5135(15)
C4 C7 1.5200(15)
C4 C5 1.5714(14)
C5 C22 1.5138(15)
C5 C6 1.5679(15)
C10 C11 1.3952(16)
C10 C15 1.3962(16)
C11 C12 1.3909(17)
C12 C13 1.380(2)
C13 C14 1.381(2)
C14 C15 1.3858(18)
C16 C17 1.3897(16)
C16 C21 1.3937(15)
C17 C18 1.3881(17)
C18 C19 1.3789(18)
C19 C20 1.3776(17)
C20 C21 1.3873(16)
C22 C27 1.3892(16)
C22 C23 1.3905(16)
C23 C24 1.3806(18)
C24 C25 1.3899(18)
C25 C26 1.3830(17)
C26 C27 1.3920(16)
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C8 C1 C2 C10 -65.92(13)
C7 C1 C2 C10 169.76(9)
C6 C1 C2 C10 66.90(11)
C8 C1 C2 C3 164.28(9)
C7 C1 C2 C3 39.96(9)
C6 C1 C2 C3 -62.90(10)
C10 C2 C3 C16 96.46(11)
C1 C2 C3 C16 -134.59(9)
C10 C2 C3 C4 -137.93(9)
C1 C2 C3 C4 -8.98(10)
C16 C3 C4 C9 -29.70(13)
C2 C3 C4 C9 -153.96(9)
C16 C3 C4 C7 98.48(10)
C2 C3 C4 C7 -25.78(10)
C16 C3 C4 C5 -159.36(9)
C2 C3 C4 C5 76.38(9)
C9 C4 C5 C22 36.76(13)
C7 C4 C5 C22 -90.28(10)
C3 C4 C5 C22 166.94(9)
C9 C4 C5 C6 160.58(9)
C7 C4 C5 C6 33.54(10)
C3 C4 C5 C6 -69.24(10)
C8 C1 C6 C5 -157.13(9)
C7 C1 C6 C5 -31.26(10)
C2 C1 C6 C5 70.11(10)
C22 C5 C6 C1 123.43(10)
C4 C5 C6 C1 -1.34(11)
C9 C4 C7 O1 -0.11(17)
C5 C4 C7 O1 125.56(12)
C3 C4 C7 O1 -127.55(12)
C9 C4 C7 C1 179.89(9)
C5 C4 C7 C1 -54.45(9)
C3 C4 C7 C1 52.44(9)
C8 C1 C7 O1 -1.22(17)
C6 C1 C7 O1 -126.27(12)
C2 C1 C7 O1 122.12(12)
C8 C1 C7 C4 178.78(9)
C6 C1 C7 C4 53.74(9)
C2 C1 C7 C4 -57.87(9)
C1 C2 C10 C11 -80.63(13)
C3 C2 C10 C11 42.42(15)
C1 C2 C10 C15 97.67(12)
C3 C2 C10 C15 -139.28(10)
C15 C10 C11 C12 -1.26(17)
C2 C10 C11 C12 177.05(11)
C10 C11 C12 C13 0.45(19)
C11 C12 C13 C14 0.6(2)
C12 C13 C14 C15 -0.7(2)
C13 C14 C15 C10 -0.13(19)
C11 C10 C15 C14 1.10(17)
C2 C10 C15 C14 -177.29(11)
C2 C3 C16 C17 -133.98(11)
C4 C3 C16 C17 106.65(12)
C2 C3 C16 C21 46.56(14)
C4 C3 C16 C21 -72.82(13)
C21 C16 C17 C18 -0.96(18)
C3 C16 C17 C18 179.54(11)
C16 C17 C18 C19 0.5(2)
C17 C18 C19 C20 0.3(2)
C18 C19 C20 C21 -0.53(19)
C19 C20 C21 C16 0.04(18)
C17 C16 C21 C20 0.69(16)
C3 C16 C21 C20 -179.83(10)
C6 C5 C22 C27 -42.17(14)
C4 C5 C22 C27 76.11(13)
C6 C5 C22 C23 136.46(11)
C4 C5 C22 C23 -105.26(12)
C27 C22 C23 C24 2.72(19)
C5 C22 C23 C24 -175.99(12)
C22 C23 C24 C25 -0.8(2)
C28 O2 C25 C26 0.99(19)
C28 O2 C25 C24 -178.15(12)
C23 C24 C25 O2 177.61(12)
C23 C24 C25 C26 -1.6(2)
O2 C25 C26 C27 -177.23(11)
C24 C25 C26 C27 1.88(18)
C23 C22 C27 C26 -2.40(17)
C5 C22 C27 C26 176.26(10)
C25 C26 C27 C22 0.15(18)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 102126010
