#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:16:33 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178428 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/49/4024914.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_4024914
loop_
_publ_author_name
'Paul A. Clarke'
'Andrew P. Cridland'
'Gabriele A. Rolla'
'Mudassar Iqbal'
'Nigel P. Bainbridge'
'Adrian C. Whitwood'
'Claire Wilson'
_publ_section_title
;
Studies on the Synthesis of the ABC Rings of (\+-)-Hexacyclinic Acid
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7812
_journal_page_last               7821
_journal_paper_doi               10.1021/jo901547k
_journal_volume                  74
_journal_year                    2009
_chemical_formula_sum            'C18 H21 Br O3'
_chemical_formula_weight         365.26
_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 & difmap (OH)'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                92.441(1)
_cell_angle_beta                 103.293(1)
_cell_angle_gamma                101.566(1)
_cell_formula_units_Z            2
_cell_length_a                   6.1238(5)
_cell_length_b                   11.6675(9)
_cell_length_c                   11.9189(9)
_cell_measurement_reflns_used    4285
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.4
_cell_volume                     808.43(11)
_computing_cell_refinement       'Bruker SAINT version 6.36a (Bruker, 2000)'
_computing_data_collection       'Bruker SMART version 5.625 (Bruker, 2001)'
_computing_data_reduction        'Bruker SAINT; Bruker SHELXTL (Bruker, 2001)'
_computing_publication_material  'enCIFer (CCDC, 2003); PLATON (Spek, 2003)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.960
_diffrn_measured_fraction_theta_max 0.954
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area detector'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.014
_diffrn_reflns_av_sigmaI/netI    0.0227
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6790
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.63
_diffrn_reflns_theta_min         2.39
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.552
_exptl_absorpt_correction_T_max  .700
_exptl_absorpt_correction_T_min  0.498
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'bruker SADABS v2.05'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.500
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       column
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.544
_refine_diff_density_min         -0.319
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         3575
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0258
_refine_ls_R_factor_gt           0.0236
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0310P)²+0.4189P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0603
_refine_ls_wR_factor_ref         0.0615
_reflns_number_gt                3359
_reflns_number_total             3575
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            jo901547k_si_002.cif
_cod_data_source_block           bzoxbr
_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               4024914
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
Br1 Br 0.10491(3) 0.806250(14) 0.549328(13) 0.02366(6) Uani 1 1 d . . .
O1 O 0.3067(2) 0.94204(12) 0.07852(10) 0.0267(3) Uani 1 1 d . . .
C1 C 0.2431(3) 0.84500(14) 0.42316(13) 0.0182(3) Uani 1 1 d . . .
O2 O 0.6702(2) 1.06378(11) 0.15410(11) 0.0266(3) Uani 1 1 d . . .
H2 H 0.7026 1.0774 0.0905 0.040 Uiso 1 1 calc R . .
C2 C 0.2033(3) 0.93869(14) 0.37040(14) 0.0204(3) Uani 1 1 d . . .
H2A H 0.0969 0.9794 0.3915 0.024 Uiso 1 1 calc R . .
O3 O 0.08413(19) 0.60070(10) 0.32848(10) 0.0217(2) Uani 1 1 d . . .
C3 C 0.3209(3) 0.98285(14) 0.27817(14) 0.0196(3) Uani 1 1 d . . .
H3A H 0.3899 1.0686 0.2984 0.024 Uiso 1 1 calc R . .
C4 C 0.5120(3) 0.91986(14) 0.26486(14) 0.0182(3) Uani 1 1 d . . .
H4A H 0.6574 0.9539 0.3246 0.022 Uiso 1 1 calc R . .
C5 C 0.4363(3) 0.78713(13) 0.27316(13) 0.0173(3) Uani 1 1 d . . .
H5A H 0.2870 0.7571 0.2148 0.021 Uiso 1 1 calc R . .
C6 C 0.3969(3) 0.76666(13) 0.39531(13) 0.0179(3) Uani 1 1 d . . .
H6A H 0.5492 0.7914 0.4524 0.021 Uiso 1 1 calc R . .
C7 C 0.1649(3) 0.96590(16) 0.15446(15) 0.0245(3) Uani 1 1 d . . .
H7A H 0.0321 0.8993 0.1470 0.029 Uiso 1 1 calc R . .
H7B H 0.1068 1.0378 0.1354 0.029 Uiso 1 1 calc R . .
C8 C 0.5369(3) 0.94967(14) 0.14501(14) 0.0205(3) Uani 1 1 d . . .
H8A H 0.6098 0.8920 0.1107 0.025 Uiso 1 1 calc R . .
C9 C 0.6089(3) 0.72137(15) 0.24714(15) 0.0231(3) Uani 1 1 d . . .
H9A H 0.7614 0.7424 0.2942 0.028 Uiso 1 1 calc R . .
C10 C 0.5622(4) 0.63620(18) 0.16305(17) 0.0350(4) Uani 1 1 d . . .
H10A H 0.4113 0.6130 0.1144 0.042 Uiso 1 1 calc R . .
H10B H 0.6794 0.5981 0.1512 0.042 Uiso 1 1 calc R . .
C11 C 0.3063(3) 0.63674(14) 0.40423(14) 0.0202(3) Uani 1 1 d . . .
H11A H 0.4111 0.5900 0.3826 0.024 Uiso 1 1 calc R . .
H11B H 0.2980 0.6238 0.4848 0.024 Uiso 1 1 calc R . .
C12 C -0.0066(3) 0.47701(14) 0.32638(16) 0.0252(3) Uani 1 1 d . . .
H12A H -0.1762 0.4609 0.2994 0.030 Uiso 1 1 calc R . .
H12B H 0.0324 0.4529 0.4059 0.030 Uiso 1 1 calc R . .
C13 C 0.0873(3) 0.40539(14) 0.24800(15) 0.0224(3) Uani 1 1 d . . .
C14 C -0.0104(3) 0.39030(17) 0.12963(17) 0.0320(4) Uani 1 1 d . . .
H14A H -0.1414 0.4215 0.0991 0.038 Uiso 1 1 calc R . .
C15 C 0.0816(4) 0.3301(2) 0.05548(18) 0.0416(5) Uani 1 1 d . . .
H15A H 0.0133 0.3202 -0.0254 0.050 Uiso 1 1 calc R . .
C16 C 0.2726(4) 0.28463(18) 0.09903(19) 0.0379(5) Uani 1 1 d . . .
H16A H 0.3366 0.2445 0.0480 0.045 Uiso 1 1 calc R . .
C17 C 0.3702(3) 0.29747(16) 0.21639(18) 0.0316(4) Uani 1 1 d . . .
H17A H 0.5008 0.2658 0.2465 0.038 Uiso 1 1 calc R . .
C18 C 0.2766(3) 0.35696(15) 0.29068(16) 0.0256(3) Uani 1 1 d . . .
H18A H 0.3427 0.3646 0.3717 0.031 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'
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
C8 O1 C7 109.56(12) . . ?
C2 C1 C6 125.52(14) . . ?
C2 C1 Br1 118.04(12) . . ?
C6 C1 Br1 116.40(11) . . ?
C1 C2 C3 122.07(14) . . ?
C11 O3 C12 112.07(12) . . ?
C2 C3 C4 113.38(13) . . ?
C2 C3 C7 115.16(13) . . ?
C4 C3 C7 102.65(13) . . ?
C8 C4 C3 100.83(12) . . ?
C8 C4 C5 113.24(13) . . ?
C3 C4 C5 110.40(12) . . ?
C9 C5 C4 111.55(13) . . ?
C9 C5 C6 111.03(13) . . ?
C4 C5 C6 109.25(12) . . ?
C1 C6 C11 113.75(13) . . ?
C1 C6 C5 109.17(12) . . ?
C11 C6 C5 110.78(12) . . ?
O1 C7 C3 105.96(12) . . ?
O2 C8 O1 111.50(13) . . ?
O2 C8 C4 108.61(13) . . ?
O1 C8 C4 104.86(12) . . ?
C10 C9 C5 124.18(16) . . ?
O3 C11 C6 108.82(12) . . ?
O3 C12 C13 111.93(13) . . ?
C14 C13 C18 118.51(16) . . ?
C14 C13 C12 119.85(16) . . ?
C18 C13 C12 121.60(16) . . ?
C15 C14 C13 120.63(18) . . ?
C16 C15 C14 120.13(19) . . ?
C17 C16 C15 120.06(18) . . ?
C16 C17 C18 119.72(17) . . ?
C17 C18 C13 120.93(17) . . ?
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
Br1 C1 1.9163(15) . ?
O1 C8 1.4330(19) . ?
O1 C7 1.444(2) . ?
C1 C2 1.321(2) . ?
C1 C6 1.515(2) . ?
O2 C8 1.401(2) . ?
C2 C3 1.502(2) . ?
O3 C11 1.4199(19) . ?
O3 C12 1.436(2) . ?
C3 C4 1.535(2) . ?
C3 C7 1.542(2) . ?
C4 C8 1.519(2) . ?
C4 C5 1.539(2) . ?
C5 C9 1.503(2) . ?
C5 C6 1.550(2) . ?
C6 C11 1.523(2) . ?
C9 C10 1.320(3) . ?
C12 C13 1.508(2) . ?
C13 C14 1.388(3) . ?
C13 C18 1.392(2) . ?
C14 C15 1.388(3) . ?
C15 C16 1.383(3) . ?
C16 C17 1.378(3) . ?
C17 C18 1.391(3) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2 O1 0.84 2.00 2.8071(17) 159.7 2_675
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -3.6(3) . . . . ?
Br1 C1 C2 C3 174.18(12) . . . . ?
C1 C2 C3 C4 -8.1(2) . . . . ?
C1 C2 C3 C7 109.69(18) . . . . ?
C2 C3 C4 C8 161.15(13) . . . . ?
C7 C3 C4 C8 36.28(15) . . . . ?
C2 C3 C4 C5 41.16(18) . . . . ?
C7 C3 C4 C5 -83.71(15) . . . . ?
C8 C4 C5 C9 61.39(17) . . . . ?
C3 C4 C5 C9 173.60(13) . . . . ?
C8 C4 C5 C6 -175.47(12) . . . . ?
C3 C4 C5 C6 -63.26(16) . . . . ?
C2 C1 C6 C11 -142.54(16) . . . . ?
Br1 C1 C6 C11 39.68(16) . . . . ?
C2 C1 C6 C5 -18.3(2) . . . . ?
Br1 C1 C6 C5 163.97(10) . . . . ?
C9 C5 C6 C1 173.65(13) . . . . ?
C4 C5 C6 C1 50.21(16) . . . . ?
C9 C5 C6 C11 -60.33(17) . . . . ?
C4 C5 C6 C11 176.22(12) . . . . ?
C8 O1 C7 C3 -3.21(17) . . . . ?
C2 C3 C7 O1 -145.15(14) . . . . ?
C4 C3 C7 O1 -21.45(16) . . . . ?
C7 O1 C8 O2 -90.22(16) . . . . ?
C7 O1 C8 C4 27.13(17) . . . . ?
C3 C4 C8 O2 79.99(14) . . . . ?
C5 C4 C8 O2 -162.07(12) . . . . ?
C3 C4 C8 O1 -39.31(15) . . . . ?
C5 C4 C8 O1 78.63(15) . . . . ?
C4 C5 C9 C10 -121.18(19) . . . . ?
C6 C5 C9 C10 116.71(19) . . . . ?
C12 O3 C11 C6 176.16(13) . . . . ?
C1 C6 C11 O3 57.71(17) . . . . ?
C5 C6 C11 O3 -65.71(16) . . . . ?
C11 O3 C12 C13 -80.97(17) . . . . ?
O3 C12 C13 C14 -82.4(2) . . . . ?
O3 C12 C13 C18 95.17(19) . . . . ?
C18 C13 C14 C15 -1.2(3) . . . . ?
C12 C13 C14 C15 176.46(19) . . . . ?
C13 C14 C15 C16 -0.1(3) . . . . ?
C14 C15 C16 C17 0.9(3) . . . . ?
C15 C16 C17 C18 -0.4(3) . . . . ?
C16 C17 C18 C13 -0.9(3) . . . . ?
C14 C13 C18 C17 1.7(3) . . . . ?
C12 C13 C18 C17 -175.88(16) . . . . ?
