#------------------------------------------------------------------------------
#$Date: 2016-03-26 03:40:22 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180191 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/87/7108751.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_7108751
loop_
_publ_author_name
'Ping Cheng'
'Derrick L. J. Clive'
'Shimal Fernandopulle'
'Zhenhua Chen'
_publ_section_title
;
 Racemic marinopyrrole B by total synthesis
;
_journal_name_full               Chem.Commun.
_journal_page_first              558
_journal_paper_doi               10.1039/c2cc37110c
_journal_volume                  49
_journal_year                    2013
_chemical_formula_moiety         'C12 H9 Br Cl2 N2 O4'
_chemical_formula_sum            'C12 H9 Br Cl2 N2 O4'
_chemical_formula_weight         396.02
_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                77.0064(6)
_cell_angle_beta                 75.9683(6)
_cell_angle_gamma                65.5279(6)
_cell_formula_units_Z            2
_cell_length_a                   7.5864(4)
_cell_length_b                   9.0677(5)
_cell_length_c                   12.2844(7)
_cell_measurement_reflns_used    3886
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.46
_cell_measurement_theta_min      2.83
_cell_volume                     738.75(7)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'DIRDIF-2008 (Beurskens et al., 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω 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  0.0130
_diffrn_reflns_av_sigmaI/netI    0.0204
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6270
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         1.73
_exptl_absorpt_coefficient_mu    3.159
_exptl_absorpt_correction_T_max  0.5595
_exptl_absorpt_correction_T_min  0.4027
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.780
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.385
_refine_diff_density_min         -0.447
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         3328
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0276
_refine_ls_R_factor_gt           0.0246
_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)+(0.0348P)²+0.3700P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0647
_refine_ls_wR_factor_ref         0.0662
_reflns_number_gt                3064
_reflns_number_total             3328
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            c2cc37110c.txt
_cod_data_source_block           11
_cod_database_code               7108751
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
Br Br -0.34614(3) 0.64188(2) 0.439868(17) 0.02827(8) Uani 1 1 d .
Cl1 Cl -0.14220(7) 0.21947(6) 0.49567(4) 0.02939(12) Uani 1 1 d .
Cl2 Cl 0.33044(8) 0.08185(6) 0.35324(5) 0.03577(14) Uani 1 1 d .
O1 O 0.1642(2) 0.73059(19) 0.16260(13) 0.0364(4) Uani 1 1 d .
O2 O -0.0943(2) 0.83092(17) 0.29530(13) 0.0317(3) Uani 1 1 d .
O3 O 0.1656(2) 0.2974(3) 0.08639(16) 0.0469(5) Uani 1 1 d .
O4 O 0.4443(2) 0.2140(2) -0.03875(13) 0.0361(4) Uani 1 1 d .
N1 N 0.2117(2) 0.4056(2) 0.28636(13) 0.0217(3) Uani 1 1 d .
N2 N 0.6312(2) 0.3252(2) 0.06604(14) 0.0249(3) Uani 1 1 d .
H2N H 0.6998 0.2916 0.0013 0.030 Uiso 1 1 calc R
C1 C 0.0512(3) 0.5500(2) 0.30564(16) 0.0208(4) Uani 1 1 d .
C2 C -0.0939(3) 0.5078(2) 0.38115(15) 0.0212(4) Uani 1 1 d .
C3 C -0.0220(3) 0.3368(2) 0.40738(16) 0.0233(4) Uani 1 1 d .
C4 C 0.1660(3) 0.2782(2) 0.34889(17) 0.0235(4) Uani 1 1 d .
C5 C 0.4463(3) 0.3283(2) 0.11048(16) 0.0229(4) Uani 1 1 d .
C6 C 0.3929(3) 0.3881(2) 0.21211(16) 0.0219(4) Uani 1 1 d .
C7 C 0.5480(3) 0.4208(2) 0.23004(18) 0.0267(4) Uani 1 1 d .
H7 H 0.5523 0.4617 0.2937 0.032 Uiso 1 1 calc R
C8 C 0.6927(3) 0.3819(3) 0.13679(18) 0.0284(4) Uani 1 1 d .
H8 H 0.8155 0.3929 0.1241 0.034 Uiso 1 1 calc R
C9 C 0.0505(3) 0.7098(2) 0.24597(16) 0.0227(4) Uani 1 1 d .
C10 C -0.1067(4) 0.9946(3) 0.2458(2) 0.0394(5) Uani 1 1 d .
H10A H -0.2186 1.0741 0.2883 0.047 Uiso 1 1 calc R
H10B H -0.1247 1.0143 0.1667 0.047 Uiso 1 1 calc R
H10C H 0.0146 1.0063 0.2488 0.047 Uiso 1 1 calc R
C11 C 0.3347(3) 0.2802(3) 0.05412(17) 0.0278(4) Uani 1 1 d .
C12 C 0.3428(5) 0.1757(4) -0.1067(2) 0.0560(8) Uani 1 1 d .
H12A H 0.4348 0.1302 -0.1732 0.067 Uiso 1 1 calc R
H12B H 0.2355 0.2756 -0.1315 0.067 Uiso 1 1 calc R
H12C H 0.2889 0.0953 -0.0617 0.067 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'
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
C9 O2 C10 116.24(17)
C11 O4 C12 115.8(2)
C4 N1 C1 108.38(15)
C4 N1 C6 124.18(16)
C1 N1 C6 127.41(16)
C8 N2 C5 109.70(17)
C2 C1 N1 107.28(16)
C2 C1 C9 130.89(18)
N1 C1 C9 121.74(16)
C1 C2 C3 107.97(17)
C1 C2 Br 129.27(15)
C3 C2 Br 122.74(14)
C4 C3 C2 107.00(17)
C4 C3 Cl1 125.52(16)
C2 C3 Cl1 127.49(15)
N1 C4 C3 109.37(17)
N1 C4 Cl2 122.25(15)
C3 C4 Cl2 128.32(15)
N2 C5 C6 106.71(17)
N2 C5 C11 123.84(18)
C6 C5 C11 129.43(18)
C5 C6 C7 108.70(17)
C5 C6 N1 124.05(17)
C7 C6 N1 127.20(18)
C8 C7 C6 106.10(19)
N2 C8 C7 108.78(18)
O1 C9 O2 123.58(18)
O1 C9 C1 125.28(18)
O2 C9 C1 111.14(16)
O3 C11 O4 124.1(2)
O3 C11 C5 124.6(2)
O4 C11 C5 111.35(18)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br C2 1.8594(19)
Cl1 C3 1.7158(19)
Cl2 C4 1.697(2)
O1 C9 1.203(2)
O2 C9 1.326(2)
O2 C10 1.445(3)
O3 C11 1.201(3)
O4 C11 1.337(3)
O4 C12 1.441(3)
N1 C4 1.360(2)
N1 C1 1.390(2)
N1 C6 1.423(2)
N2 C8 1.353(3)
N2 C5 1.367(2)
C1 C2 1.383(3)
C1 C9 1.468(3)
C2 C3 1.402(3)
C3 C4 1.371(3)
C5 C6 1.376(3)
C5 C11 1.454(3)
C6 C7 1.401(3)
C7 C8 1.376(3)
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
C4 N1 C1 C2 -0.2(2)
C6 N1 C1 C2 177.99(18)
C4 N1 C1 C9 -176.99(17)
C6 N1 C1 C9 1.2(3)
N1 C1 C2 C3 -0.4(2)
C9 C1 C2 C3 175.98(19)
N1 C1 C2 Br -178.77(14)
C9 C1 C2 Br -2.3(3)
C1 C2 C3 C4 0.9(2)
Br C2 C3 C4 179.34(14)
C1 C2 C3 Cl1 -179.27(15)
Br C2 C3 Cl1 -0.8(3)
C1 N1 C4 C3 0.7(2)
C6 N1 C4 C3 -177.50(18)
C1 N1 C4 Cl2 -176.57(15)
C6 N1 C4 Cl2 5.2(3)
C2 C3 C4 N1 -1.0(2)
Cl1 C3 C4 N1 179.14(15)
C2 C3 C4 Cl2 176.10(16)
Cl1 C3 C4 Cl2 -3.8(3)
C8 N2 C5 C6 -0.3(2)
C8 N2 C5 C11 178.07(18)
N2 C5 C6 C7 -0.4(2)
C11 C5 C6 C7 -178.60(19)
N2 C5 C6 N1 -178.08(17)
C11 C5 C6 N1 3.7(3)
C4 N1 C6 C5 71.3(3)
C1 N1 C6 C5 -106.6(2)
C4 N1 C6 C7 -105.9(2)
C1 N1 C6 C7 76.2(3)
C5 C6 C7 C8 0.9(2)
N1 C6 C7 C8 178.48(19)
C5 N2 C8 C7 0.8(2)
C6 C7 C8 N2 -1.0(2)
C10 O2 C9 O1 -2.2(3)
C10 O2 C9 C1 178.36(18)
C2 C1 C9 O1 -160.9(2)
N1 C1 C9 O1 15.1(3)
C2 C1 C9 O2 18.5(3)
N1 C1 C9 O2 -165.47(17)
C12 O4 C11 O3 5.4(3)
C12 O4 C11 C5 -174.6(2)
N2 C5 C11 O3 -172.2(2)
C6 C5 C11 O3 5.7(4)
N2 C5 C11 O4 7.7(3)
C6 C5 C11 O4 -174.34(19)
