#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/10/7151011.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_7151011
loop_
_publ_author_name
'Jones, Paul B.'
'Brinson, Robert G.'
'Sarma, Saurav J.'
'Elkazaz, Salwa'
_publ_section_title
;
 Observation of heavy atom effects in the development of water soluble
 caged 4-hydroxy-trans-2-nonenal
;
_journal_issue                   22
_journal_name_full               'Organic & Biomolecular Chemistry'
_journal_page_first              4204
_journal_page_last               4211
_journal_paper_doi               10.1039/B810954k
_journal_volume                  6
_journal_year                    2008
_chemical_formula_sum            'C15 H6 Br N O3'
_chemical_formula_weight         328.12
_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
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXTL
_cell_angle_alpha                69.902(6)
_cell_angle_beta                 78.323(7)
_cell_angle_gamma                80.933(7)
_cell_formula_units_Z            2
_cell_length_a                   5.835(3)
_cell_length_b                   8.910(4)
_cell_length_c                   12.876(5)
_cell_measurement_reflns_used    1373
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      25.306
_cell_measurement_theta_min      3.925
_cell_volume                     612.8(5)
_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  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      193(2)
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'Bruker APEX 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  0.0295
_diffrn_reflns_av_sigmaI/netI    0.0536
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            5743
_diffrn_reflns_theta_full        28.28
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         3.93
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    3.359
_exptl_absorpt_correction_T_max  0.9059
_exptl_absorpt_correction_T_min  0.4994
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Data were corrected for absorption effects using the
multi-scan technique (SADABS). The ratio of minimum
to maximum apparent transmission: 0.782445
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.778
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             324
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.705
_refine_diff_density_min         -0.365
_refine_diff_density_rms         0.090
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         2979
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.005
_refine_ls_R_factor_all          0.0602
_refine_ls_R_factor_gt           0.0428
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0501P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0924
_refine_ls_wR_factor_ref         0.0999
_reflns_number_gt                2314
_reflns_number_total             2979
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            B810954k.txt
_cod_data_source_block           a01i2f
_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               7151011
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
Br Br 0.34439(6) 0.19863(4) 0.55894(2) 0.04218(14) Uani 1 1 d . . .
O1 O 0.1725(4) 0.1033(3) 0.80444(18) 0.0302(5) Uani 1 1 d . . .
H1 H 0.133(8) 0.077(6) 0.880(4) 0.088(16) Uiso 1 1 d . . .
O2 O 0.1721(4) 0.0792(3) 1.00854(16) 0.0332(5) Uani 1 1 d . . .
O3 O 0.9079(4) 0.4272(3) 0.89229(18) 0.0383(5) Uani 1 1 d . . .
N N 1.0698(5) 0.5646(4) 0.6343(2) 0.0392(6) Uani 1 1 d . . .
C1 C 0.4615(5) 0.2481(4) 0.6683(2) 0.0272(6) Uani 1 1 d . . .
C2 C 0.3548(5) 0.1910(3) 0.7805(2) 0.0251(6) Uani 1 1 d . . .
C3 C 0.4417(5) 0.2287(3) 0.8625(2) 0.0224(6) Uani 1 1 d . . .
C4 C 0.3321(5) 0.1676(3) 0.9806(2) 0.0229(6) Uani 1 1 d . . .
C5 C 0.4195(5) 0.2095(3) 1.0662(2) 0.0244(6) Uani 1 1 d . . .
C6 C 0.3087(5) 0.1583(4) 1.1772(2) 0.0280(6) Uani 1 1 d . . .
H6 H 0.1744 0.1003 1.1971 0.034 Uiso 1 1 calc R . .
C7 C 0.3950(6) 0.1923(4) 1.2585(2) 0.0332(7) Uani 1 1 d . . .
H7 H 0.3199 0.1570 1.3343 0.040 Uiso 1 1 calc R . .
C8 C 0.5916(6) 0.2781(4) 1.2296(3) 0.0343(7) Uani 1 1 d . . .
H8 H 0.6505 0.3002 1.2859 0.041 Uiso 1 1 calc R . .
C9 C 0.7011(5) 0.3309(4) 1.1195(2) 0.0292(6) Uani 1 1 d . . .
H9 H 0.8349 0.3892 1.1004 0.035 Uiso 1 1 calc R . .
C10 C 0.6152(5) 0.2986(3) 1.0362(2) 0.0242(6) Uani 1 1 d . . .
C11 C 0.7330(5) 0.3558(3) 0.9183(2) 0.0254(6) Uani 1 1 d . . .
C12 C 0.6336(5) 0.3222(3) 0.8307(2) 0.0225(6) Uani 1 1 d . . .
C13 C 0.7336(5) 0.3793(3) 0.7182(2) 0.0268(6) Uani 1 1 d . . .
C14 C 0.6453(5) 0.3415(4) 0.6368(2) 0.0293(6) Uani 1 1 d . . .
H14 H 0.7133 0.3808 0.5601 0.035 Uiso 1 1 calc R . .
C15 C 0.9241(5) 0.4824(4) 0.6769(2) 0.0306(7) Uani 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'
N N 0.0061 0.0033 '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
C2 O1 H1 103(3) . . ?
C14 C1 C2 121.2(2) . . ?
C14 C1 Br 119.8(2) . . ?
C2 C1 Br 119.0(2) . . ?
O1 C2 C1 117.7(2) . . ?
O1 C2 C3 123.2(2) . . ?
C1 C2 C3 119.0(2) . . ?
C12 C3 C2 119.9(2) . . ?
C12 C3 C4 120.7(2) . . ?
C2 C3 C4 119.3(2) . . ?
O2 C4 C3 120.4(2) . . ?
O2 C4 C5 120.2(2) . . ?
C3 C4 C5 119.5(2) . . ?
C6 C5 C10 120.2(3) . . ?
C6 C5 C4 119.5(3) . . ?
C10 C5 C4 120.3(2) . . ?
C7 C6 C5 119.8(3) . . ?
C7 C6 H6 120.1 . . ?
C5 C6 H6 120.1 . . ?
C6 C7 C8 120.3(3) . . ?
C6 C7 H7 119.8 . . ?
C8 C7 H7 119.8 . . ?
C9 C8 C7 120.3(3) . . ?
C9 C8 H8 119.9 . . ?
C7 C8 H8 119.9 . . ?
C8 C9 C10 120.2(3) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 H9 119.9 . . ?
C9 C10 C5 119.3(3) . . ?
C9 C10 C11 119.9(2) . . ?
C5 C10 C11 120.8(2) . . ?
O3 C11 C10 121.2(3) . . ?
O3 C11 C12 120.2(3) . . ?
C10 C11 C12 118.6(2) . . ?
C13 C12 C3 119.6(2) . . ?
C13 C12 C11 120.4(2) . . ?
C3 C12 C11 119.9(2) . . ?
C12 C13 C14 120.1(3) . . ?
C12 C13 C15 123.6(3) . . ?
C14 C13 C15 116.3(3) . . ?
C1 C14 C13 120.1(3) . . ?
C1 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
N C15 C13 173.2(3) . . ?
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
Br C1 1.886(3) . ?
O1 C2 1.342(3) . ?
O1 H1 0.91(5) . ?
O2 C4 1.234(3) . ?
O3 C11 1.216(3) . ?
N C15 1.137(4) . ?
C1 C14 1.371(4) . ?
C1 C2 1.402(4) . ?
C2 C3 1.414(4) . ?
C3 C12 1.411(4) . ?
C3 C4 1.472(4) . ?
C4 C5 1.477(4) . ?
C5 C6 1.392(4) . ?
C5 C10 1.407(4) . ?
C6 C7 1.386(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.396(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.381(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.401(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.481(4) . ?
C11 C12 1.499(4) . ?
C12 C13 1.395(4) . ?
C13 C14 1.411(4) . ?
C13 C15 1.452(4) . ?
C14 H14 0.9500 . ?
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
O1 H1 O2 0.91(5) 1.72(5) 2.562(3) 152(5) .
O1 H1 O2 0.91(5) 2.35(5) 2.977(3) 126(4) 2_557
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
C14 C1 C2 O1 178.6(3) . . . . ?
Br C1 C2 O1 -0.1(4) . . . . ?
C14 C1 C2 C3 -1.0(4) . . . . ?
Br C1 C2 C3 -179.7(2) . . . . ?
O1 C2 C3 C12 -179.7(3) . . . . ?
C1 C2 C3 C12 -0.2(4) . . . . ?
O1 C2 C3 C4 1.1(4) . . . . ?
C1 C2 C3 C4 -179.3(3) . . . . ?
C12 C3 C4 O2 -176.3(3) . . . . ?
C2 C3 C4 O2 2.8(4) . . . . ?
C12 C3 C4 C5 2.0(4) . . . . ?
C2 C3 C4 C5 -178.8(2) . . . . ?
O2 C4 C5 C6 -4.8(4) . . . . ?
C3 C4 C5 C6 176.9(3) . . . . ?
O2 C4 C5 C10 174.4(3) . . . . ?
C3 C4 C5 C10 -3.9(4) . . . . ?
C10 C5 C6 C7 -1.5(4) . . . . ?
C4 C5 C6 C7 177.7(3) . . . . ?
C5 C6 C7 C8 0.3(5) . . . . ?
C6 C7 C8 C9 0.5(5) . . . . ?
C7 C8 C9 C10 0.0(5) . . . . ?
C8 C9 C10 C5 -1.2(4) . . . . ?
C8 C9 C10 C11 179.9(3) . . . . ?
C6 C5 C10 C9 1.9(4) . . . . ?
C4 C5 C10 C9 -177.3(3) . . . . ?
C6 C5 C10 C11 -179.2(3) . . . . ?
C4 C5 C10 C11 1.7(4) . . . . ?
C9 C10 C11 O3 2.0(4) . . . . ?
C5 C10 C11 O3 -177.0(3) . . . . ?
C9 C10 C11 C12 -178.7(3) . . . . ?
C5 C10 C11 C12 2.3(4) . . . . ?
C2 C3 C12 C13 1.2(4) . . . . ?
C4 C3 C12 C13 -179.7(2) . . . . ?
C2 C3 C12 C11 -177.2(2) . . . . ?
C4 C3 C12 C11 2.0(4) . . . . ?
O3 C11 C12 C13 -3.2(4) . . . . ?
C10 C11 C12 C13 177.5(3) . . . . ?
O3 C11 C12 C3 175.1(3) . . . . ?
C10 C11 C12 C3 -4.2(4) . . . . ?
C3 C12 C13 C14 -1.0(4) . . . . ?
C11 C12 C13 C14 177.3(3) . . . . ?
C3 C12 C13 C15 177.1(3) . . . . ?
C11 C12 C13 C15 -4.6(4) . . . . ?
C2 C1 C14 C13 1.2(4) . . . . ?
Br C1 C14 C13 179.9(2) . . . . ?
C12 C13 C14 C1 -0.2(4) . . . . ?
C15 C13 C14 C1 -178.4(3) . . . . ?
C12 C13 C15 N -172(3) . . . . ?
C14 C13 C15 N 6(3) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30653440
