#------------------------------------------------------------------------------
#$Date: 2016-02-16 03:10:39 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176453 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/08/7150829.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_7150829
loop_
_publ_author_name
'Pearson, Emma L.'
'Willis, Anthony C.'
'Sherburn, Michael S.'
'Paddon-Row, Michael N.'
_publ_section_title
;
 Controlling cis/trans-selectivity in intramolecular Diels--Alder
 reactions of benzo-tethered, ester linked 1,3,9-decatrienes
;
_journal_issue                   3
_journal_name_full               'Organic &  Biomolecular Chemistry'
_journal_page_first              513
_journal_page_last               522
_journal_paper_doi               10.1039/b716910h
_journal_volume                  6
_journal_year                    2008
_chemical_compound_source
;
?
;
_chemical_formula_moiety         ' C15 H13 Br O4 '
_chemical_formula_sum            'C15 H13 Br O4'
_chemical_formula_weight         337.17
_chemical_name_systematic
; 
? 
;
_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
_audit_creation_date             05-09-05
_audit_creation_method           CRYSTALS_ver_12-03-99
_audit_update_record
;
2005-05-09 - Report on  C15 H13 Br O4 
             by Anthony C. Willis
             for Craig Turner and Mick Sherburn
2005-05-10 - passes checkcif tests with minor warnings
;
_cell_angle_alpha                103.9603(17)
_cell_angle_beta                 93.8881(18)
_cell_angle_gamma                109.0036(18)
_cell_formula_units_Z            2
_cell_length_a                   6.7091(2)
_cell_length_b                   8.0770(2)
_cell_length_c                   13.7233(4)
_cell_measurement_reflns_used    7773
_cell_measurement_temperature    200
_cell_measurement_theta_max      27
_cell_measurement_theta_min      3
_cell_volume                     673.62(3)
_computing_cell_refinement
; 
 Denzo/Scalepack (Otwinowski & Minor, 1996) 
;
_computing_data_collection
; 
 COLLECT (Nonius BV, 1997) 
;
_computing_data_reduction
; 
 Denzo/Scalepack (Otwinowski & Minor, 1996) 
;
_computing_molecular_graphics
; 
ORTEP-II (Johnson 1976) in teXsan (MSC, 1992-1997)
;
_computing_publication_material
; 
 CRYSTALS (Watkin et al 2003) 
;
_computing_structure_refinement
; 
 CRYSTALS (Watkin et al 2003) 
;
_computing_structure_solution
; 
 SIR92 (Altomare et al, 1994) 
;
_diffrn_ambient_temperature      200
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type
; 
Nonius Kappa CCD 
;
_diffrn_measurement_method       ' φ and ω scans with CCD '
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.03
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            11941
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.778
_diffrn_standards_decay_%        0.00
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.061
_exptl_absorpt_correction_T_max  0.803
_exptl_absorpt_correction_T_min  0.497
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details
;
Gaussian integration (Coppens, 1970)
;
_exptl_crystal_colour            ' colourless '
_exptl_crystal_density_diffrn    1.662
_exptl_crystal_density_meas      ?
_exptl_crystal_description       ' block '
_exptl_crystal_F_000             340
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.27
_refine_diff_density_min         -0.64
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.0615
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2507
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0345
_refine_ls_R_factor_gt           0.0272
_refine_ls_shift/su_max          0.000821
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)] 
 where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)²]² 
 Ai are: 
 1.05 0.191 0.722 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0356
_refine_ls_wR_factor_gt          0.0321
_refine_ls_wR_factor_ref         0.0321
_reflns_limit_h_max              8
_reflns_limit_h_min              -8
_reflns_limit_k_max              10
_reflns_limit_k_min              -10
_reflns_limit_l_max              17
_reflns_limit_l_min              0
_reflns_number_gt                2507
_reflns_number_total             3101
_reflns_threshold_expression     I>3.00u(I)
_cod_data_source_file            b716910h.txt
_cod_data_source_block
;
;
_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_original_formula_sum        ' C15 H13 Br O4 '
_cod_database_code               7150829
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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
Br1 Br 0.55757(4) 0.81720(3) 0.234293(17) 0.0380 1.0000 Uani . . . . . .
O1 O 1.0645(2) 0.5919(2) 0.35489(12) 0.0358 1.0000 Uani . . . . . .
O2 O 1.0929(2) 0.3853(2) 0.22568(13) 0.0433 1.0000 Uani . . . . . .
O3 O 0.3292(3) 0.1305(2) 0.02360(12) 0.0435 1.0000 Uani . . . . . .
O4 O 0.3482(2) 0.07961(18) 0.17621(11) 0.0306 1.0000 Uani . . . . . .
C1 C 0.6418(3) 0.6090(2) 0.20050(15) 0.0266 1.0000 Uani . . . . . .
C2 C 0.6247(3) 0.5032(2) 0.27903(14) 0.0239 1.0000 Uani . . . . . .
C3 C 0.7237(3) 0.6214(2) 0.38577(14) 0.0264 1.0000 Uani . . . . . .
C4 C 0.6092(3) 0.6920(3) 0.45465(16) 0.0353 1.0000 Uani . . . . . .
C5 C 0.7087(4) 0.8006(3) 0.55186(17) 0.0431 1.0000 Uani . . . . . .
C6 C 0.9246(4) 0.8393(3) 0.58126(17) 0.0450 1.0000 Uani . . . . . .
C7 C 1.0409(4) 0.7682(3) 0.51500(17) 0.0398 1.0000 Uani . . . . . .
C8 C 0.9377(3) 0.6589(3) 0.41871(15) 0.0301 1.0000 Uani . . . . . .
C9 C 0.9755(3) 0.4445(3) 0.27259(16) 0.0299 1.0000 Uani . . . . . .
C10 C 0.7327(3) 0.3611(2) 0.24805(14) 0.0249 1.0000 Uani . . . . . .
C11 C 0.6695(3) 0.2596(2) 0.13444(14) 0.0268 1.0000 Uani . . . . . .
C12 C 0.7442(3) 0.3918(3) 0.07024(15) 0.0318 1.0000 Uani . . . . . .
C13 C 0.6958(3) 0.5631(3) 0.10938(15) 0.0299 1.0000 Uani . . . . . .
C14 C 0.4307(3) 0.1535(2) 0.10434(14) 0.0272 1.0000 Uani . . . . . .
C15 C 0.1262(3) -0.0402(3) 0.14887(19) 0.0389 1.0000 Uani . . . . . .
H21 H 0.4690 0.4441 0.28027 0.0281 1.0000 Uiso R . . . . .
H41 H 0.4534 0.6642 0.43395 0.0406 1.0000 Uiso R . . . . .
H51 H 0.6247 0.8509 0.60066 0.0493 1.0000 Uiso R . . . . .
H61 H 0.9963 0.9192 0.65094 0.0494 1.0000 Uiso R . . . . .
H71 H 1.1963 0.7950 0.53599 0.0444 1.0000 Uiso R . . . . .
H101 H 0.6806 0.2735 0.28918 0.0299 1.0000 Uiso R . . . . .
H111 H 0.7427 0.1684 0.12094 0.0318 1.0000 Uiso R . . . . .
H121 H 0.9018 0.4250 0.07206 0.0378 1.0000 Uiso R . . . . .
H122 H 0.6698 0.3307 -0.00147 0.0378 1.0000 Uiso R . . . . .
H131 H 0.7047 0.6457 0.06477 0.0347 1.0000 Uiso R . . . . .
H151 H 0.0791 -0.0886 0.20727 0.0426 1.0000 Uiso R . . . . .
H152 H 0.1106 -0.1441 0.08829 0.0426 1.0000 Uiso R . . . . .
H153 H 0.0360 0.0294 0.13221 0.0426 1.0000 Uiso R . . . . .
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
'C   ' 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 International_Tables_Vol_IV_Table_2.2B
'H   ' 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 International_Tables_Vol_IV_Table_2.2B
'Br  ' -0.2901 2.4595 17.1789 2.1723 5.2358 16.5796 5.6377 0.2609 3.9851
41.4328 2.9557 International_Tables_Vol_IV_Table_2.2B
'O   ' 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 International_Tables_Vol_IV_Table_2.2B
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
10 0 0 0.170
0 1 0 0.050
0 -1 0 0.030
1 4 0 0.052
0 1 -6 0.088
0 -1 6 0.106
-2 1 -1 0.158
2 -3 -3 0.110
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C8 . O1 . C9 . 121.07(15) yes
C14 . O4 . C15 . 115.39(16) yes
Br1 . C1 . C2 . 115.87(13) yes
Br1 . C1 . C13 . 117.94(14) yes
C2 . C1 . C13 . 126.03(17) yes
C1 . C2 . C3 . 113.77(15) yes
C1 . C2 . C10 . 108.78(15) yes
C3 . C2 . C10 . 109.17(14) yes
C1 . C2 . H21 . 106.912 no
C3 . C2 . H21 . 106.516 no
C10 . C2 . H21 . 111.714 no
C2 . C3 . C4 . 123.17(17) yes
C2 . C3 . C8 . 119.17(17) yes
C4 . C3 . C8 . 117.65(18) yes
C3 . C4 . C5 . 120.7(2) yes
C3 . C4 . H41 . 119.628 no
C5 . C4 . H41 . 119.630 no
C4 . C5 . C6 . 120.0(2) yes
C4 . C5 . H51 . 120.004 no
C6 . C5 . H51 . 120.007 no
C5 . C6 . C7 . 120.4(2) yes
C5 . C6 . H61 . 119.805 no
C7 . C6 . H61 . 119.807 no
C6 . C7 . C8 . 118.6(2) yes
C6 . C7 . H71 . 120.704 no
C8 . C7 . H71 . 120.705 no
O1 . C8 . C7 . 115.86(18) yes
O1 . C8 . C3 . 121.52(17) yes
C7 . C8 . C3 . 122.6(2) yes
O1 . C9 . O2 . 117.80(17) yes
O1 . C9 . C10 . 118.05(17) yes
O2 . C9 . C10 . 124.12(18) yes
C2 . C10 . C9 . 112.75(15) yes
C2 . C10 . C11 . 111.90(14) yes
C9 . C10 . C11 . 108.42(15) yes
C2 . C10 . H101 . 105.111 no
C9 . C10 . H101 . 108.829 no
C11 . C10 . H101 . 109.735 no
C10 . C11 . C12 . 110.53(15) yes
C10 . C11 . C14 . 112.55(15) yes
C12 . C11 . C14 . 110.49(15) yes
C10 . C11 . H111 . 106.952 no
C12 . C11 . H111 . 109.155 no
C14 . C11 . H111 . 106.991 no
C11 . C12 . C13 . 111.62(16) yes
C11 . C12 . H121 . 108.934 no
C13 . C12 . H121 . 108.932 no
C11 . C12 . H122 . 108.933 no
C13 . C12 . H122 . 108.934 no
H121 . C12 . H122 . 109.467 no
C12 . C13 . C1 . 122.77(18) yes
C12 . C13 . H131 . 118.613 no
C1 . C13 . H131 . 118.614 no
C11 . C14 . O4 . 112.01(15) yes
C11 . C14 . O3 . 124.45(18) yes
O4 . C14 . O3 . 123.44(18) yes
O4 . C15 . H151 . 109.466 no
O4 . C15 . H152 . 109.467 no
H151 . C15 . H152 . 109.476 no
O4 . C15 . H153 . 109.467 no
H151 . C15 . H153 . 109.476 no
H152 . C15 . H153 . 109.476 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Br1 . C1 . 1.9081(18) yes
O1 . C8 . 1.398(3) yes
O1 . C9 . 1.359(2) yes
O2 . C9 . 1.195(3) yes
O3 . C14 . 1.201(2) yes
O4 . C14 . 1.334(2) yes
O4 . C15 . 1.451(2) yes
C1 . C2 . 1.517(3) yes
C1 . C13 . 1.326(3) yes
C2 . C3 . 1.510(2) yes
C2 . C10 . 1.540(2) yes
C2 . H21 . 1.000 no
C3 . C4 . 1.390(3) yes
C3 . C8 . 1.386(3) yes
C4 . C5 . 1.389(3) yes
C4 . H41 . 1.000 no
C5 . C6 . 1.387(4) yes
C5 . H51 . 1.000 no
C6 . C7 . 1.379(4) yes
C6 . H61 . 1.000 no
C7 . C8 . 1.386(3) yes
C7 . H71 . 1.000 no
C9 . C10 . 1.524(2) yes
C10 . C11 . 1.533(3) yes
C10 . H101 . 1.000 no
C11 . C12 . 1.528(3) yes
C11 . C14 . 1.522(3) yes
C11 . H111 . 1.000 no
C12 . C13 . 1.505(3) yes
C12 . H121 . 1.000 no
C12 . H122 . 1.000 no
C13 . H131 . 1.000 no
C15 . H151 . 1.000 no
C15 . H152 . 1.000 no
C15 . H153 . 1.000 no
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
Br1 O4 3.115(2) . 1_565 no
O1 C4 3.570(2) . 1_655 no
O2 C2 3.357(2) . 1_655 no
O2 O4 3.405(2) . 1_655 no
O2 C15 3.429(3) . 1_655 no
O2 C6 3.542(3) . 2_766 no
O3 C11 3.370(2) . 2_655 no
O3 C14 3.433(3) . 2_655 no
O3 C13 3.448(3) . 2_665 no
O3 C15 3.493(3) . 2 no
O3 O3 3.578(4) . 2_655 no
C4 C4 3.531(5) . 2_666 no
C6 C9 3.572(4) . 2_766 no
C13 C15 3.438(3) . 1_665 no
C13 C13 3.559(4) . 2_665 no
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
Br1 C1 C2 C3 . . . . -48.8(2) no
Br1 C1 C2 C10 . . . . -170.7(1) no
Br1 C1 C13 C12 . . . . -173.9(1) no
O1 C8 C3 C2 . . . . 0.9(3) no
O1 C8 C3 C4 . . . . 179.3(2) no
O1 C8 C7 C6 . . . . 179.6(2) no
O1 C9 C10 C2 . . . . 31.3(3) no
O1 C9 C10 C11 . . . . 155.7(2) no
O2 C9 O1 C8 . . . . -174.3(2) no
O2 C9 C10 C2 . . . . -150.9(2) no
O2 C9 C10 C11 . . . . -26.5(3) no
O3 C14 O4 C15 . . . . 2.9(3) no
O3 C14 C11 C10 . . . . 146.5(2) no
O3 C14 C11 C12 . . . . 22.4(3) no
O4 C14 C11 C10 . . . . -37.0(2) no
O4 C14 C11 C12 . . . . -161.2(2) no
C1 C2 C3 C4 . . . . 92.5(2) no
C1 C2 C3 C8 . . . . -89.1(2) no
C1 C2 C10 C9 . . . . 77.7(2) no
C1 C2 C10 C11 . . . . -44.8(2) no
C1 C13 C12 C11 . . . . 14.5(2) no
C2 C1 C13 C12 . . . . 1.4(3) no
C2 C3 C4 C5 . . . . -179.8(2) no
C2 C3 C8 C7 . . . . 179.1(2) no
C2 C10 C11 C12 . . . . 62.7(2) no
C2 C10 C11 C14 . . . . -61.4(2) no
C3 C2 C1 C13 . . . . 135.9(2) no
C3 C2 C10 C9 . . . . -47.0(2) no
C3 C2 C10 C11 . . . . -169.6(1) no
C3 C4 C5 C6 . . . . -0.2(4) no
C3 C8 O1 C9 . . . . -21.4(3) no
C3 C8 C7 C6 . . . . 1.4(4) no
C4 C3 C2 C10 . . . . -145.7(2) no
C4 C3 C8 C7 . . . . -2.5(3) no
C4 C5 C6 C7 . . . . -1.0(4) no
C5 C4 C3 C8 . . . . 1.9(3) no
C5 C6 C7 C8 . . . . 0.4(4) no
C7 C8 O1 C9 . . . . 160.3(2) no
C8 O1 C9 C10 . . . . 3.6(3) no
C8 C3 C2 C10 . . . . 32.6(2) no
C9 C10 C11 C12 . . . . -62.2(2) no
C9 C10 C11 C14 . . . . 173.7(2) no
C10 C2 C1 C13 . . . . 13.9(2) no
C10 C11 C12 C13 . . . . -45.0(2) no
C11 C14 O4 C15 . . . . -173.6(2) no
C13 C12 C11 C14 . . . . 80.3(2) no
