#------------------------------------------------------------------------------
#$Date: 2016-03-22 14:03:27 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178984 $
#$URL: svn://www.crystallography.net/cod/cif/4/12/07/4120765.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_4120765
loop_
_publ_author_name
'Wei Lin'
'Daniela Buccella'
'Stephen J. Lippard'
_publ_section_title
;
 Visualization of Peroxynitrite-Induced Changes of Labile Zn2+ in the
 Endoplasmic Reticulum with Benzoresorufin-Based Fluorescent Probes
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              13512
_journal_page_last               13520
_journal_paper_doi               10.1021/ja4059487
_journal_volume                  135
_journal_year                    2013
_chemical_formula_sum            'C29 H21 Br N4 O3'
_chemical_formula_weight         553.41
_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           SHELXL-97
_cell_angle_alpha                78.8360(10)
_cell_angle_beta                 81.9300(10)
_cell_angle_gamma                77.0540(10)
_cell_formula_units_Z            2
_cell_length_a                   9.1364(5)
_cell_length_b                   10.9864(6)
_cell_length_c                   12.3620(7)
_cell_measurement_reflns_used    9891
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      0.00
_cell_measurement_theta_min      0.00
_cell_volume                     1180.30(11)
_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      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0246
_diffrn_reflns_av_sigmaI/netI    0.0195
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            20974
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         1.93
_exptl_absorpt_coefficient_mu    1.783
_exptl_absorpt_correction_T_max  0.9485
_exptl_absorpt_correction_T_min  0.5742
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            RED
_exptl_crystal_density_diffrn    1.557
_exptl_crystal_description       PLATE
_exptl_crystal_F_000             564
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.439
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     335
_refine_ls_number_reflns         4842
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0280
_refine_ls_R_factor_gt           0.0256
_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)+(0.0353P)²+0.9460P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0693
_refine_ls_wR_factor_ref         0.0707
_reflns_number_gt                4535
_reflns_number_total             4842
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja4059487_si_002.cif
_cod_data_source_block           db5s10
_cod_database_code               4120765
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
Br1 Br 0.08218(2) -0.163462(16) 0.651416(14) 0.01821(7) Uani 1 1 d .
O1 O 0.11132(14) 0.10612(11) 0.58878(10) 0.0134(2) Uani 1 1 d .
O2 O -0.07616(15) 0.50489(11) 0.70722(11) 0.0179(3) Uani 1 1 d .
H1A H -0.1477 0.4695 0.7372 0.021 Uiso 1 1 calc R
O3 O 0.32080(15) -0.28975(12) 0.48499(11) 0.0207(3) Uani 1 1 d .
N1 N 0.33153(17) 0.21035(14) 0.44135(12) 0.0141(3) Uani 1 1 d .
N2 N -0.11731(16) 0.25478(14) 0.83766(12) 0.0135(3) Uani 1 1 d .
N3 N -0.34956(17) 0.45836(14) 0.80711(13) 0.0174(3) Uani 1 1 d .
N4 N 0.16787(17) 0.10510(15) 1.03225(13) 0.0183(3) Uani 1 1 d .
C1 C 0.0241(2) 0.42607(16) 0.64938(14) 0.0152(3) Uani 1 1 d .
C2 C 0.01004(19) 0.30066(16) 0.65048(14) 0.0132(3) Uani 1 1 d .
C3 C 0.1189(2) 0.23121(16) 0.58357(14) 0.0132(3) Uani 1 1 d .
C4 C 0.21400(19) 0.03356(16) 0.52472(14) 0.0122(3) Uani 1 1 d .
C5 C 0.21426(19) -0.09211(16) 0.53923(14) 0.0137(3) Uani 1 1 d .
C6 C 0.3165(2) -0.17560(16) 0.47069(14) 0.0148(3) Uani 1 1 d .
C7 C 0.41397(19) -0.11299(16) 0.37991(14) 0.0141(3) Uani 1 1 d .
C8 C 0.5046(2) -0.18628(17) 0.30488(15) 0.0179(4) Uani 1 1 d .
H8A H 0.5010 -0.2732 0.3117 0.022 Uiso 1 1 calc R
C9 C 0.5988(2) -0.13228(18) 0.22123(16) 0.0201(4) Uani 1 1 d .
H9A H 0.6571 -0.1815 0.1690 0.024 Uiso 1 1 calc R
C10 C 0.6092(2) -0.00571(18) 0.21283(16) 0.0195(4) Uani 1 1 d .
H10A H 0.6765 0.0302 0.1563 0.023 Uiso 1 1 calc R
C11 C 0.5212(2) 0.06742(17) 0.28693(15) 0.0161(3) Uani 1 1 d .
H11A H 0.5292 0.1532 0.2817 0.019 Uiso 1 1 calc R
C12 C 0.42050(19) 0.01522(16) 0.36973(14) 0.0133(3) Uani 1 1 d .
C13 C 0.32095(19) 0.09317(16) 0.44529(14) 0.0128(3) Uani 1 1 d .
C14 C 0.23411(19) 0.28043(16) 0.51302(14) 0.0134(3) Uani 1 1 d .
C15 C 0.2466(2) 0.40439(17) 0.51764(15) 0.0167(4) Uani 1 1 d .
H15A H 0.3258 0.4395 0.4735 0.020 Uiso 1 1 calc R
C16 C 0.1448(2) 0.47512(17) 0.58574(15) 0.0172(4) Uani 1 1 d .
H16A H 0.1559 0.5580 0.5899 0.021 Uiso 1 1 calc R
C17 C -0.11811(19) 0.24679(16) 0.71988(14) 0.0137(3) Uani 1 1 d .
H17A H -0.2155 0.2947 0.6935 0.016 Uiso 1 1 calc R
H17B H -0.1073 0.1572 0.7118 0.016 Uiso 1 1 calc R
C18 C -0.2617(2) 0.24209(16) 0.90186(15) 0.0162(3) Uani 1 1 d .
H18A H -0.2481 0.2259 0.9818 0.019 Uiso 1 1 calc R
H18B H -0.2936 0.1679 0.8852 0.019 Uiso 1 1 calc R
C19 C 0.0072(2) 0.16039(16) 0.88479(14) 0.0148(3) Uani 1 1 d .
H19A H 0.0928 0.1488 0.8265 0.018 Uiso 1 1 calc R
H19B H -0.0254 0.0784 0.9084 0.018 Uiso 1 1 calc R
C20 C -0.3851(2) 0.35808(16) 0.87790(14) 0.0154(3) Uani 1 1 d .
C21 C -0.5318(2) 0.35753(18) 0.92756(16) 0.0212(4) Uani 1 1 d .
H21A H -0.5538 0.2864 0.9794 0.025 Uiso 1 1 calc R
C22 C -0.6448(2) 0.4618(2) 0.90039(19) 0.0272(4) Uani 1 1 d .
H22A H -0.7455 0.4630 0.9331 0.033 Uiso 1 1 calc R
C23 C -0.6093(2) 0.56464(19) 0.82477(19) 0.0276(4) Uani 1 1 d .
H23A H -0.6850 0.6370 0.8037 0.033 Uiso 1 1 calc R
C24 C -0.4603(2) 0.55869(18) 0.78102(17) 0.0221(4) Uani 1 1 d .
H24A H -0.4352 0.6293 0.7299 0.027 Uiso 1 1 calc R
C30 C 0.06106(19) 0.19519(16) 0.98265(14) 0.0143(3) Uani 1 1 d .
C31 C 0.0076(2) 0.31138(17) 1.01696(15) 0.0184(4) Uani 1 1 d .
H31A H -0.0672 0.3733 0.9795 0.022 Uiso 1 1 calc R
C32 C 0.0647(2) 0.33606(18) 1.10679(16) 0.0209(4) Uani 1 1 d .
H32A H 0.0278 0.4142 1.1330 0.025 Uiso 1 1 calc R
C33 C 0.1764(2) 0.24515(19) 1.15775(15) 0.0205(4) Uani 1 1 d .
H33A H 0.2195 0.2601 1.2183 0.025 Uiso 1 1 calc R
C34 C 0.2235(2) 0.13154(18) 1.11768(16) 0.0208(4) Uani 1 1 d .
H34A H 0.2996 0.0689 1.1530 0.025 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'
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
C4 O1 C3 119.41(13)
C13 N1 C14 118.32(15)
C19 N2 C18 111.43(14)
C19 N2 C17 109.99(13)
C18 N2 C17 112.12(13)
C20 N3 C24 118.37(16)
C34 N4 C30 117.35(16)
O2 C1 C16 116.67(15)
O2 C1 C2 122.29(16)
C16 C1 C2 121.04(16)
C3 C2 C1 116.14(16)
C3 C2 C17 122.55(15)
C1 C2 C17 121.31(15)
O1 C3 C2 116.65(15)
O1 C3 C14 119.25(15)
C2 C3 C14 124.10(15)
C5 C4 O1 118.45(15)
C5 C4 C13 122.84(16)
O1 C4 C13 118.70(15)
C4 C5 C6 121.88(16)
C4 C5 Br1 119.98(13)
C6 C5 Br1 118.14(12)
O3 C6 C5 122.50(16)
O3 C6 C7 121.68(16)
C5 C6 C7 115.80(15)
C8 C7 C12 119.61(16)
C8 C7 C6 118.45(16)
C12 C7 C6 121.91(16)
C9 C8 C7 120.11(17)
C8 C9 C10 120.47(17)
C11 C10 C9 119.97(17)
C10 C11 C12 120.20(17)
C11 C12 C7 119.57(16)
C11 C12 C13 120.87(16)
C7 C12 C13 119.56(15)
N1 C13 C4 122.20(16)
N1 C13 C12 120.42(15)
C4 C13 C12 117.37(15)
N1 C14 C15 120.87(16)
N1 C14 C3 121.60(15)
C15 C14 C3 117.52(16)
C16 C15 C14 120.28(16)
C15 C16 C1 120.67(16)
N2 C17 C2 110.27(13)
N2 C18 C20 113.08(14)
N2 C19 C30 113.65(14)
N3 C20 C21 121.88(17)
N3 C20 C18 118.22(15)
C21 C20 C18 119.89(16)
C22 C21 C20 119.15(18)
C21 C22 C23 119.20(18)
C24 C23 C22 118.04(18)
N3 C24 C23 123.33(18)
N4 C30 C31 122.69(17)
N4 C30 C19 114.41(15)
C31 C30 C19 122.88(16)
C30 C31 C32 119.06(17)
C33 C32 C31 118.99(17)
C32 C33 C34 118.02(17)
N4 C34 C33 123.86(17)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C5 1.8780(17)
O1 C4 1.358(2)
O1 C3 1.380(2)
O2 C1 1.342(2)
O3 C6 1.225(2)
N1 C13 1.304(2)
N1 C14 1.380(2)
N2 C19 1.460(2)
N2 C18 1.462(2)
N2 C17 1.477(2)
N3 C20 1.339(2)
N3 C24 1.340(2)
N4 C34 1.339(2)
N4 C30 1.345(2)
C1 C16 1.408(3)
C1 C2 1.410(2)
C2 C3 1.389(2)
C2 C17 1.513(2)
C3 C14 1.406(2)
C4 C5 1.357(2)
C4 C13 1.455(2)
C5 C6 1.458(2)
C6 C7 1.490(2)
C7 C8 1.403(2)
C7 C12 1.404(2)
C8 C9 1.380(3)
C9 C10 1.398(3)
C10 C11 1.385(3)
C11 C12 1.403(2)
C12 C13 1.468(2)
C14 C15 1.404(2)
C15 C16 1.374(3)
C18 C20 1.512(2)
C19 C30 1.511(2)
C20 C21 1.395(3)
C21 C22 1.381(3)
C22 C23 1.388(3)
C23 C24 1.385(3)
C30 C31 1.386(3)
C31 C32 1.386(3)
C32 C33 1.384(3)
C33 C34 1.388(3)
