#------------------------------------------------------------------------------
#$Date: 2025-08-22 12:33:34 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301861 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/08/7150810.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_7150810
loop_
_publ_author_name
'D'Souza, Daniel M.'
'Liao, Wei-Wei'
'Rominger, Frank'
'Müller, Thomas J. J.'
_publ_section_title
;
 Dichotomies in microwave-assisted propargyl-isomerization--Claisen
 domino sequences dependent on base strengths
;
_journal_issue                   3
_journal_name_full               'Organic &  Biomolecular Chemistry'
_journal_page_first              532
_journal_page_last               539
_journal_paper_doi               10.1039/b714351f
_journal_volume                  6
_journal_year                    2008
_chemical_formula_sum            'C29 H24 O'
_chemical_formula_weight         388.48
_chemical_name_common            'in paper 5e'
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_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                73.0570(11)
_cell_angle_beta                 86.7680(12)
_cell_angle_gamma                98.8770(9)
_cell_formula_units_Z            2
_cell_length_a                   8.5190(2)
_cell_length_b                   12.5850(3)
_cell_length_c                   10.24100(10)
_cell_measurement_reflns_used    3017
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      25.39
_cell_measurement_theta_min      2.27
_cell_volume                     1031.73(4)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_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  0.0436
_diffrn_reflns_av_sigmaI/netI    0.0718
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            14378
_diffrn_reflns_theta_full        24.73
_diffrn_reflns_theta_max         24.73
_diffrn_reflns_theta_min         1.72
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_max  0.9956
_exptl_absorpt_correction_T_min  0.9647
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Blessing, Acta Cryst. (1995) A51 33-38.'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.250
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       polyhedron
_exptl_crystal_F_000             412
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.167
_refine_diff_density_min         -0.181
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.996
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     285
_refine_ls_number_reflns         14378
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.996
_refine_ls_R_factor_all          0.0840
_refine_ls_R_factor_gt           0.0484
_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)+(0.0520P)²+0.0175P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1122
_refine_ls_wR_factor_ref         0.1307
_reflns_number_gt                9690
_reflns_number_total             14378
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b714351f.txt
_cod_data_source_block           dds53
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7150810
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.29646(14) 0.75626(9) 1.02636(12) 0.0292(3) Uani 1 1 d . . .
C2 C 0.17370(16) 0.65899(10) 1.00774(14) 0.0335(3) Uani 1 1 d . . .
H2A H 0.1079(15) 0.6177(10) 1.0931(13) 0.036(4) Uiso 1 1 d . . .
H2B H 0.2324(13) 0.6118(10) 0.9704(11) 0.032(3) Uiso 1 1 d . . .
C3 C 0.07346(15) 0.71316(10) 0.89658(13) 0.0307(3) Uani 1 1 d . . .
H3 H -0.0182(15) 0.7394(9) 0.9354(12) 0.036(3) Uiso 1 1 d . . .
C4 C 0.01726(15) 0.63813(10) 0.80886(13) 0.0336(3) Uani 1 1 d . . .
O4 O 0.09895(11) 0.57110(8) 0.79033(10) 0.0490(3) Uani 1 1 d . . .
C11 C 0.45098(14) 0.72122(10) 1.07991(12) 0.0301(3) Uani 1 1 d . . .
C12 C 0.56192(15) 0.79919(11) 1.11416(14) 0.0411(3) Uani 1 1 d . . .
H12 H 0.5400 0.8727 1.1042 0.049 Uiso 1 1 calc R . .
C13 C 0.70299(16) 0.77221(12) 1.16224(14) 0.0482(4) Uani 1 1 d . . .
H13 H 0.7774 0.8272 1.1842 0.058 Uiso 1 1 calc R . .
C14 C 0.73633(16) 0.66595(12) 1.17855(13) 0.0433(4) Uani 1 1 d . . .
H14 H 0.8338 0.6472 1.2111 0.052 Uiso 1 1 calc R . .
C15 C 0.62692(16) 0.58697(12) 1.14716(14) 0.0428(3) Uani 1 1 d . . .
H15 H 0.6485 0.5130 1.1594 0.051 Uiso 1 1 calc R . .
C16 C 0.48597(15) 0.61442(10) 1.09794(13) 0.0368(3) Uani 1 1 d . . .
H16 H 0.4120 0.5591 1.0762 0.044 Uiso 1 1 calc R . .
C21 C 0.21721(13) 0.80933(10) 1.12582(12) 0.0281(3) Uani 1 1 d . . .
C22 C 0.18560(15) 0.74872(11) 1.26443(13) 0.0383(3) Uani 1 1 d . . .
H22 H 0.2135 0.6760 1.2959 0.046 Uiso 1 1 calc R . .
C23 C 0.11454(16) 0.79195(12) 1.35732(14) 0.0472(4) Uani 1 1 d . . .
H23 H 0.0940 0.7488 1.4515 0.057 Uiso 1 1 calc R . .
C24 C 0.07331(16) 0.89718(12) 1.31428(15) 0.0463(4) Uani 1 1 d . . .
H24 H 0.0247 0.9271 1.3782 0.056 Uiso 1 1 calc R . .
C25 C 0.10325(15) 0.95808(11) 1.17829(14) 0.0418(3) Uani 1 1 d . . .
H25 H 0.0749 1.0308 1.1477 0.050 Uiso 1 1 calc R . .
C26 C 0.17448(14) 0.91504(10) 1.08452(13) 0.0334(3) Uani 1 1 d . . .
H26 H 0.1943 0.9587 0.9905 0.040 Uiso 1 1 calc R . .
C31 C 0.32121(14) 0.83757(9) 0.88066(12) 0.0299(3) Uani 1 1 d . . .
C32 C 0.44459(15) 0.92680(10) 0.81841(13) 0.0360(3) Uani 1 1 d . . .
H32 H 0.5346 0.9411 0.8655 0.043 Uiso 1 1 calc R . .
C33 C 0.43557(17) 0.99495(11) 0.68717(14) 0.0449(4) Uani 1 1 d . . .
H33 H 0.5204 1.0559 0.6436 0.054 Uiso 1 1 calc R . .
C34 C 0.30480(18) 0.97526(11) 0.61905(14) 0.0459(4) Uani 1 1 d . . .
H34 H 0.2989 1.0237 0.5296 0.055 Uiso 1 1 calc R . .
C35 C 0.18171(16) 0.88544(10) 0.67974(13) 0.0384(3) Uani 1 1 d . . .
H35 H 0.0922 0.8713 0.6320 0.046 Uiso 1 1 calc R . .
C36 C 0.19063(14) 0.81689(10) 0.81015(12) 0.0300(3) Uani 1 1 d . . .
C41 C -0.12987(14) 0.65068(10) 0.74019(12) 0.0306(3) Uani 1 1 d . . .
C42 C -0.15983(16) 0.59684(10) 0.64067(13) 0.0394(3) Uani 1 1 d . . .
H42 H -0.0870 0.5523 0.6204 0.047 Uiso 1 1 calc R . .
C43 C -0.29248(17) 0.60703(11) 0.57154(14) 0.0446(4) Uani 1 1 d . . .
H43 H -0.3090 0.5709 0.5027 0.054 Uiso 1 1 calc R . .
C44 C -0.40306(16) 0.66933(11) 0.60065(14) 0.0415(3) Uani 1 1 d . . .
C45 C -0.37503(17) 0.72141(12) 0.70016(15) 0.0470(4) Uani 1 1 d . . .
H45 H -0.4499 0.7640 0.7218 0.056 Uiso 1 1 calc R . .
C46 C -0.24086(16) 0.71323(11) 0.76916(14) 0.0423(3) Uani 1 1 d . . .
H46 H -0.2241 0.7505 0.8369 0.051 Uiso 1 1 calc R . .
C47 C -0.55051(18) 0.67855(13) 0.52700(16) 0.0605(4) Uani 1 1 d . . .
H47A H -0.5260 0.6784 0.4324 0.091 Uiso 1 1 calc R . .
H47B H -0.5866 0.7490 0.5261 0.091 Uiso 1 1 calc R . .
H47C H -0.6351 0.6143 0.5744 0.091 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C31 C1 C11 113.57(10) . . ?
C31 C1 C2 100.32(10) . . ?
C11 C1 C2 114.47(10) . . ?
C31 C1 C21 110.10(9) . . ?
C11 C1 C21 109.09(9) . . ?
C2 C1 C21 108.98(10) . . ?
C3 C2 C1 106.47(10) . . ?
C36 C3 C2 102.00(10) . . ?
C36 C3 C4 110.13(10) . . ?
C2 C3 C4 113.34(10) . . ?
O4 C4 C41 119.97(11) . . ?
O4 C4 C3 119.42(11) . . ?
C41 C4 C3 120.52(11) . . ?
C16 C11 C12 117.58(12) . . ?
C16 C11 C1 123.30(11) . . ?
C12 C11 C1 119.11(10) . . ?
C13 C12 C11 121.47(12) . . ?
C14 C13 C12 120.16(13) . . ?
C13 C14 C15 119.28(13) . . ?
C14 C15 C16 120.49(12) . . ?
C15 C16 C11 121.01(12) . . ?
C26 C21 C22 117.29(12) . . ?
C26 C21 C1 123.60(11) . . ?
C22 C21 C1 119.11(11) . . ?
C23 C22 C21 121.43(12) . . ?
C24 C23 C22 120.38(13) . . ?
C25 C24 C23 119.08(13) . . ?
C24 C25 C26 120.79(13) . . ?
C21 C26 C25 121.04(12) . . ?
C32 C31 C36 119.79(12) . . ?
C32 C31 C1 129.59(11) . . ?
C36 C31 C1 110.50(10) . . ?
C33 C32 C31 119.36(12) . . ?
C34 C33 C32 120.53(13) . . ?
C33 C34 C35 120.55(13) . . ?
C36 C35 C34 119.12(13) . . ?
C35 C36 C31 120.63(12) . . ?
C35 C36 C3 128.89(11) . . ?
C31 C36 C3 110.47(11) . . ?
C46 C41 C42 117.82(12) . . ?
C46 C41 C4 123.82(11) . . ?
C42 C41 C4 118.37(11) . . ?
C43 C42 C41 121.13(12) . . ?
C42 C43 C44 120.96(13) . . ?
C45 C44 C43 118.09(13) . . ?
C45 C44 C47 120.87(13) . . ?
C43 C44 C47 121.03(13) . . ?
C44 C45 C46 121.57(13) . . ?
C45 C46 C41 120.42(13) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C31 1.5252(16) . ?
C1 C11 1.5321(16) . ?
C1 C2 1.5466(16) . ?
C1 C21 1.5483(16) . ?
C2 C3 1.5255(17) . ?
C3 C36 1.5194(17) . ?
C3 C4 1.5268(16) . ?
C4 O4 1.2213(14) . ?
C4 C41 1.4786(17) . ?
C11 C16 1.3838(16) . ?
C11 C12 1.3895(16) . ?
C12 C13 1.3774(18) . ?
C13 C14 1.3746(19) . ?
C14 C15 1.3762(18) . ?
C15 C16 1.3820(17) . ?
C21 C26 1.3857(16) . ?
C21 C22 1.3899(17) . ?
C22 C23 1.3805(18) . ?
C23 C24 1.3755(19) . ?
C24 C25 1.3673(19) . ?
C25 C26 1.3867(17) . ?
C31 C32 1.3839(16) . ?
C31 C36 1.3919(17) . ?
C32 C33 1.3814(17) . ?
C33 C34 1.3756(19) . ?
C34 C35 1.3837(18) . ?
C35 C36 1.3762(17) . ?
C41 C46 1.3914(17) . ?
C41 C42 1.3933(16) . ?
C42 C43 1.3699(18) . ?
C43 C44 1.3869(19) . ?
C44 C45 1.3762(18) . ?
C44 C47 1.5037(19) . ?
C45 C46 1.3789(18) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21119789
2 PubChem 168352767
