#------------------------------------------------------------------------------
#$Date: 2022-05-07 04:18:16 +0300 (Sat, 07 May 2022) $
#$Revision: 275180 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/20/43/7204349.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_7204349
loop_
_publ_author_name
'Tanaka, Koichi'
'Harada, Naoyuki'
_publ_section_title
;
 A novel spiroketalization reaction of
 1,7-dihydroxyhepta-2,5-diyn-4-ones
;
_journal_issue                   6
_journal_name_full
'Journal of the Chemical Society, Perkin Transactions 1'
_journal_page_first              713
_journal_paper_doi               10.1039/b200215a
_journal_year                    2002
_chemical_formula_sum            'C31 H20 Br2 Cl2 O2'
_chemical_formula_weight         655.19
_chemical_melting_point          276.5(15)
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                   12.0964(14)
_cell_length_b                   13.5239(15)
_cell_length_c                   16.1906(19)
_cell_measurement_reflns_used    1010
_cell_measurement_temperature    100(1)
_cell_measurement_theta_max      31.263
_cell_measurement_theta_min      2.933
_cell_volume                     2648.6(5)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_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      100(1)
_diffrn_detector_area_resol_mean 83.66
_diffrn_measured_fraction_theta_full 0.939
_diffrn_measured_fraction_theta_max 0.939
_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  0.0223
_diffrn_reflns_av_sigmaI/netI    0.0514
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            22651
_diffrn_reflns_theta_full        31.54
_diffrn_reflns_theta_max         31.54
_diffrn_reflns_theta_min         1.96
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  293
_diffrn_standards_number         395
_exptl_absorpt_coefficient_mu    3.291
_exptl_absorpt_correction_T_max  0.767916
_exptl_absorpt_correction_T_min  0.704875
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            transparent
_exptl_crystal_density_diffrn    1.643
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'irregular block'
_exptl_crystal_F_000             1304
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.677
_refine_diff_density_min         -0.406
_refine_diff_density_rms         0.056
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.006(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.790
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     414
_refine_ls_number_reflns         8166
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.790
_refine_ls_R_factor_all          0.0276
_refine_ls_R_factor_gt           0.0215
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0098P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0327
_refine_ls_wR_factor_ref         0.0332
_reflns_number_gt                6871
_reflns_number_total             8166
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b200215a.txt
_cod_data_source_block           1
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
according to '/home/adriana/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'Empirical' changed to
'empirical' according to
'/home/adriana/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 1555 2011-01-17 13:19:09Z saulius 

The following automatic conversions were performed:

'_chemical_melting_point' value '275-278' was changed to '276.5(15)'
- the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1569 2011-02-09 13:29:24Z adriana 
;
_cod_original_sg_symbol_H-M      P212121
_cod_database_code               7204349
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -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 0.77390(13) 0.96242(12) 0.89425(10) 0.0146(4) Uani 1 1 d . . .
C2 C 0.78831(12) 0.88001(11) 0.83118(11) 0.0148(3) Uani 1 1 d . . .
C3 C 0.71852(14) 0.88770(12) 0.76942(11) 0.0180(4) Uani 1 1 d . . .
C4 C 0.64381(13) 0.97319(12) 0.78628(10) 0.0160(4) Uani 1 1 d . . .
C5 C 0.61055(14) 1.04394(12) 0.71957(10) 0.0165(4) Uani 1 1 d . . .
C6 C 0.50403(13) 1.06169(12) 0.72608(10) 0.0154(3) Uani 1 1 d . . .
C7 C 0.45258(13) 1.00291(12) 0.79652(10) 0.0150(4) Uani 1 1 d . . .
C8 C 0.71751(13) 0.92949(12) 0.97449(10) 0.0160(4) Uani 1 1 d . . .
C9 C 0.67683(13) 0.99838(12) 1.03146(10) 0.0170(4) Uani 1 1 d . . .
C10 C 0.62503(15) 0.96895(14) 1.10335(11) 0.0203(4) Uani 1 1 d . . .
C11 C 0.61466(15) 0.87035(14) 1.12193(11) 0.0234(4) Uani 1 1 d . . .
C12 C 0.65526(15) 0.80050(14) 1.06715(12) 0.0239(4) Uani 1 1 d . . .
C13 C 0.70417(14) 0.83035(13) 0.99448(11) 0.0192(4) Uani 1 1 d . . .
C14 C 0.88329(13) 1.01558(12) 0.90928(10) 0.0153(3) Uani 1 1 d . . .
C15 C 0.91984(14) 1.08766(11) 0.85481(10) 0.0166(3) Uani 1 1 d . . .
C16 C 1.02157(14) 1.13322(13) 0.86555(11) 0.0191(4) Uani 1 1 d . . .
C17 C 1.08854(14) 1.10710(13) 0.93158(11) 0.0201(4) Uani 1 1 d . . .
C18 C 1.05302(15) 1.03436(14) 0.98516(12) 0.0239(4) Uani 1 1 d . . .
C19 C 0.95163(14) 0.98929(14) 0.97502(11) 0.0215(4) Uani 1 1 d . . .
C20 C 0.42822(13) 1.06521(11) 0.87317(10) 0.0144(3) Uani 1 1 d . . .
C21 C 0.39385(14) 1.02246(11) 0.94749(10) 0.0176(3) Uani 1 1 d . . .
C22 C 0.37019(14) 1.07963(14) 1.01643(11) 0.0205(4) Uani 1 1 d . . .
C23 C 0.38041(15) 1.18132(13) 1.01201(11) 0.0225(4) Uani 1 1 d . . .
C24 C 0.41662(15) 1.22511(14) 0.94039(11) 0.0217(4) Uani 1 1 d . . .
C25 C 0.44004(14) 1.16738(12) 0.87215(11) 0.0187(4) Uani 1 1 d . . .
C26 C 0.35208(13) 0.94415(12) 0.76877(10) 0.0154(3) Uani 1 1 d . . .
C27 C 0.36524(15) 0.85186(13) 0.73237(12) 0.0218(4) Uani 1 1 d . . .
C28 C 0.27384(15) 0.79656(13) 0.70878(12) 0.0233(4) Uani 1 1 d . . .
C29 C 0.16894(15) 0.83372(13) 0.72201(11) 0.0202(4) Uani 1 1 d . . .
C30 C 0.15536(14) 0.92590(14) 0.75614(12) 0.0217(4) Uani 1 1 d . . .
C31 C 0.24657(14) 0.98107(13) 0.77896(11) 0.0197(4) Uani 1 1 d . . .
O1 O 0.70031(8) 1.02783(7) 0.84948(7) 0.0142(2) Uani 1 1 d . . .
O2 O 0.54140(8) 0.93484(8) 0.81575(7) 0.0150(3) Uani 1 1 d . . .
Br1 Br 0.898161(13) 0.782635(12) 0.842825(12) 0.02269(4) Uani 1 1 d . . .
Br2 Br 0.421642(14) 1.148277(12) 0.659597(12) 0.02224(4) Uani 1 1 d . . .
Cl1 Cl 0.68979(4) 1.12523(3) 1.01480(3) 0.02370(10) Uani 1 1 d . . .
Cl2 Cl 0.37933(4) 0.89512(3) 0.95818(3) 0.02472(10) Uani 1 1 d . . .
H3 H 0.7133(14) 0.8431(12) 0.7167(11) 0.020(5) Uiso 1 1 d . . .
H5 H 0.6564(13) 1.0667(12) 0.6870(10) 0.017(5) Uiso 1 1 d . . .
H10 H 0.5992(12) 1.0154(10) 1.1356(8) 0.004(4) Uiso 1 1 d . . .
H11 H 0.5784(13) 0.8514(11) 1.1707(10) 0.017(4) Uiso 1 1 d . . .
H12 H 0.6502(14) 0.7366(13) 1.0794(10) 0.019(5) Uiso 1 1 d . . .
H13 H 0.7328(13) 0.7837(13) 0.9595(10) 0.016(5) Uiso 1 1 d . . .
H15 H 0.8780(13) 1.1021(12) 0.8139(10) 0.018(5) Uiso 1 1 d . . .
H16 H 1.0422(12) 1.1788(11) 0.8261(10) 0.011(5) Uiso 1 1 d . . .
H17 H 1.1503(13) 1.1353(11) 0.9391(9) 0.006(4) Uiso 1 1 d . . .
H18 H 1.0950(14) 1.0152(11) 1.0266(9) 0.015(4) Uiso 1 1 d . . .
H19 H 0.9272(13) 0.9363(12) 1.0108(10) 0.018(4) Uiso 1 1 d . . .
H22 H 0.3498(13) 1.0501(11) 1.0624(9) 0.007(4) Uiso 1 1 d . . .
H23 H 0.3649(13) 1.2219(12) 1.0561(10) 0.019(5) Uiso 1 1 d . . .
H24 H 0.4241(15) 1.2924(13) 0.9378(11) 0.033(6) Uiso 1 1 d . . .
H25 H 0.4655(13) 1.1998(11) 0.8236(10) 0.015(5) Uiso 1 1 d . . .
H27 H 0.4324(14) 0.8301(11) 0.7252(10) 0.016(5) Uiso 1 1 d . . .
H28 H 0.2876(14) 0.7331(13) 0.6856(10) 0.024(5) Uiso 1 1 d . . .
H29 H 0.1119(13) 0.7976(11) 0.7063(9) 0.008(4) Uiso 1 1 d . . .
H30 H 0.0849(14) 0.9484(12) 0.7646(10) 0.024(5) Uiso 1 1 d . . .
H31 H 0.2369(13) 1.0408(11) 0.8048(9) 0.014(5) Uiso 1 1 d . . .
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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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
O1 C1 C2 100.47(12) . . ?
O1 C1 C14 108.97(13) . . ?
C2 C1 C14 110.67(13) . . ?
O1 C1 C8 109.13(13) . . ?
C2 C1 C8 114.00(14) . . ?
C14 C1 C8 112.80(14) . . ?
C3 C2 C1 112.30(14) . . ?
C3 C2 Br1 125.90(13) . . ?
C1 C2 Br1 121.78(12) . . ?
C2 C3 C4 108.14(15) . . ?
O2 C4 O1 111.26(13) . . ?
O2 C4 C3 107.80(13) . . ?
O1 C4 C3 103.93(13) . . ?
O2 C4 C5 103.91(13) . . ?
O1 C4 C5 108.24(13) . . ?
C3 C4 C5 121.70(15) . . ?
C6 C5 C4 108.79(15) . . ?
C5 C6 C7 111.42(14) . . ?
C5 C6 Br2 126.04(13) . . ?
C7 C6 Br2 122.55(11) . . ?
O2 C7 C26 108.93(13) . . ?
O2 C7 C6 100.92(12) . . ?
C26 C7 C6 112.23(14) . . ?
O2 C7 C20 108.58(13) . . ?
C26 C7 C20 111.96(13) . . ?
C6 C7 C20 113.52(13) . . ?
C13 C8 C9 116.62(16) . . ?
C13 C8 C1 121.98(15) . . ?
C9 C8 C1 121.41(15) . . ?
C10 C9 C8 121.54(16) . . ?
C10 C9 Cl1 117.06(13) . . ?
C8 C9 Cl1 121.40(13) . . ?
C11 C10 C9 120.41(17) . . ?
C10 C11 C12 119.32(17) . . ?
C13 C12 C11 119.94(17) . . ?
C12 C13 C8 122.14(17) . . ?
C15 C14 C19 118.42(16) . . ?
C15 C14 C1 120.41(15) . . ?
C19 C14 C1 121.07(15) . . ?
C14 C15 C16 121.01(16) . . ?
C15 C16 C17 120.11(17) . . ?
C18 C17 C16 118.96(17) . . ?
C17 C18 C19 121.13(18) . . ?
C18 C19 C14 120.36(17) . . ?
C25 C20 C21 116.88(15) . . ?
C25 C20 C7 121.24(15) . . ?
C21 C20 C7 121.88(14) . . ?
C22 C21 C20 121.54(15) . . ?
C22 C21 Cl2 116.79(13) . . ?
C20 C21 Cl2 121.67(13) . . ?
C23 C22 C21 119.61(17) . . ?
C24 C23 C22 120.07(17) . . ?
C23 C24 C25 119.77(17) . . ?
C24 C25 C20 122.09(17) . . ?
C31 C26 C27 118.79(16) . . ?
C31 C26 C7 120.99(15) . . ?
C27 C26 C7 120.22(15) . . ?
C28 C27 C26 120.63(17) . . ?
C29 C28 C27 119.52(17) . . ?
C30 C29 C28 120.16(17) . . ?
C29 C30 C31 120.14(17) . . ?
C26 C31 C30 120.71(16) . . ?
C4 O1 C1 109.56(11) . . ?
C4 O2 C7 109.97(12) . . ?
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 O1 1.4492(18) . ?
C1 C2 1.522(2) . ?
C1 C14 1.525(2) . ?
C1 C8 1.534(2) . ?
C2 C3 1.313(2) . ?
C2 Br1 1.8803(15) . ?
C3 C4 1.493(2) . ?
C4 O2 1.4251(18) . ?
C4 O1 1.4353(19) . ?
C4 C5 1.498(2) . ?
C5 C6 1.315(2) . ?
C6 C7 1.523(2) . ?
C6 Br2 1.8770(16) . ?
C7 O2 1.4487(18) . ?
C7 C26 1.520(2) . ?
C7 C20 1.529(2) . ?
C8 C13 1.389(2) . ?
C8 C9 1.400(2) . ?
C9 C10 1.380(2) . ?
C9 Cl1 1.7436(17) . ?
C10 C11 1.373(2) . ?
C11 C12 1.386(3) . ?
C12 C13 1.377(2) . ?
C14 C15 1.387(2) . ?
C14 C19 1.394(2) . ?
C15 C16 1.387(2) . ?
C16 C17 1.387(2) . ?
C17 C18 1.380(2) . ?
C18 C19 1.379(2) . ?
C20 C25 1.389(2) . ?
C20 C21 1.398(2) . ?
C21 C22 1.388(2) . ?
C21 Cl2 1.7397(16) . ?
C22 C23 1.383(2) . ?
C23 C24 1.374(2) . ?
C24 C25 1.382(2) . ?
C26 C31 1.380(2) . ?
C26 C27 1.389(2) . ?
C27 C28 1.388(2) . ?
C28 C29 1.381(2) . ?
C29 C30 1.373(2) . ?
C30 C31 1.382(2) . ?
loop_
_cod_changelog_entry_id
_cod_changelog_entry_author
_cod_changelog_entry_date
_cod_changelog_entry_text
1 'Vaitkus, Antanas' 2022-05-07T04:15:00+03:00
;
 Replaced the '&#x00A5;' sequences with backslash symbols ('\')
 in multiple data values.
;
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9942180
