#------------------------------------------------------------------------------
#$Date: 2016-03-26 03:40:22 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180191 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/87/7108752.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_7108752
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         'C13 H12 Br Cl2 N O5'
_chemical_formula_sum            'C13 H12 Br Cl2 N O5'
_chemical_formula_weight         413.05
_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                90.2868(7)
_cell_angle_beta                 94.2793(5)
_cell_angle_gamma                100.6247(5)
_cell_formula_units_Z            2
_cell_length_a                   5.38720(10)
_cell_length_b                   10.2210(2)
_cell_length_c                   14.5246(3)
_cell_measurement_reflns_used    9931
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      69.62
_cell_measurement_theta_min      3.05
_cell_volume                     783.72(3)
_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 0.954
_diffrn_measured_fraction_theta_max 0.943
_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           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0274
_diffrn_reflns_av_sigmaI/netI    0.0409
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            5241
_diffrn_reflns_theta_full        67.80
_diffrn_reflns_theta_max         70.02
_diffrn_reflns_theta_min         3.05
_exptl_absorpt_coefficient_mu    6.928
_exptl_absorpt_correction_T_max  0.5937
_exptl_absorpt_correction_T_min  0.1046
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.750
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             412
_exptl_crystal_size_max          0.59
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.698
_refine_diff_density_min         -1.012
_refine_diff_density_rms         0.208
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.161
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2820
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.161
_refine_ls_R_factor_all          0.0435
_refine_ls_R_factor_gt           0.0422
_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)+(0.0798P)²+0.4414P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1156
_refine_ls_wR_factor_ref         0.1221
_reflns_number_gt                2763
_reflns_number_total             2820
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            c2cc37110c.txt
_cod_data_source_block           17
_cod_database_code               7108752
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 -0.24951(5) 0.54166(3) 0.095756(19) 0.03169(17) Uani 1 1 d .
Cl1 Cl 0.15435(14) 0.68169(7) 0.28480(5) 0.0328(2) Uani 1 1 d .
Cl2 Cl 0.54803(13) 0.47246(7) 0.35195(5) 0.0324(2) Uani 1 1 d .
O1 O 0.1104(4) 0.1589(2) 0.05305(15) 0.0364(5) Uani 1 1 d .
O2 O -0.2327(4) 0.2543(2) 0.03028(13) 0.0298(4) Uani 1 1 d .
O3 O 0.2314(4) 0.1625(2) 0.35389(13) 0.0280(4) Uani 1 1 d .
O4 O 0.5166(5) -0.0436(2) 0.35466(15) 0.0393(5) Uani 1 1 d .
O5 O 0.6936(4) 0.0406(2) 0.22742(15) 0.0350(5) Uani 1 1 d .
N N 0.2696(4) 0.3353(2) 0.20907(15) 0.0230(5) Uani 1 1 d .
C1 C 0.0737(5) 0.3473(3) 0.14355(18) 0.0231(5) Uani 1 1 d .
C2 C 0.0002(5) 0.4664(3) 0.16080(17) 0.0233(5) Uani 1 1 d .
C3 C 0.1521(5) 0.5290(3) 0.23689(17) 0.0238(5) Uani 1 1 d .
C4 C 0.3147(5) 0.4452(3) 0.26533(17) 0.0235(5) Uani 1 1 d .
C5 C -0.0099(5) 0.2429(3) 0.07164(17) 0.0248(6) Uani 1 1 d .
C6 C -0.3273(6) 0.1612(4) -0.0464(2) 0.0373(7) Uani 1 1 d .
H6A H -0.4916 0.1780 -0.0721 0.045 Uiso 1 1 calc R
H6B H -0.3469 0.0698 -0.0241 0.045 Uiso 1 1 calc R
H6C H -0.2068 0.1734 -0.0943 0.045 Uiso 1 1 calc R
C7 C 0.4079(5) 0.2290(3) 0.21627(18) 0.0246(5) Uani 1 1 d .
H7 H 0.5092 0.2135 0.1680 0.030 Uiso 1 1 calc R
C8 C 0.3970(5) 0.1514(3) 0.28951(18) 0.0238(5) Uani 1 1 d .
C9 C 0.3040(6) 0.1488(3) 0.45070(19) 0.0319(6) Uani 1 1 d .
H9A H 0.4883 0.1812 0.4634 0.038 Uiso 1 1 calc R
H9B H 0.2648 0.0540 0.4679 0.038 Uiso 1 1 calc R
C10 C 0.1595(6) 0.2288(3) 0.5052(2) 0.0343(7) Uani 1 1 d .
H10 H 0.1839 0.2253 0.5705 0.041 Uiso 1 1 calc R
C11 C 0.0025(7) 0.3035(4) 0.4718(2) 0.0395(7) Uani 1 1 d .
H11A H -0.0282 0.3102 0.4069 0.047 Uiso 1 1 calc R
H11B H -0.0808 0.3509 0.5125 0.047 Uiso 1 1 calc R
C12 C 0.5419(5) 0.0393(3) 0.29622(18) 0.0268(6) Uani 1 1 d .
C13 C 0.8332(6) -0.0670(3) 0.2278(2) 0.0363(7) Uani 1 1 d .
H13A H 0.9393 -0.0585 0.1754 0.044 Uiso 1 1 calc R
H13B H 0.7144 -0.1522 0.2228 0.044 Uiso 1 1 calc R
H13C H 0.9409 -0.0635 0.2856 0.044 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 '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
C5 O2 C6 115.9(2)
C8 O3 C9 120.1(2)
C12 O5 C13 114.8(2)
C4 N C1 108.4(2)
C4 N C7 124.7(2)
C1 N C7 126.9(2)
C2 C1 N 107.4(2)
C2 C1 C5 132.7(3)
N C1 C5 119.9(2)
C1 C2 C3 108.3(2)
C1 C2 Br 128.3(2)
C3 C2 Br 123.4(2)
C4 C3 C2 106.8(2)
C4 C3 Cl1 124.7(2)
C2 C3 Cl1 128.5(2)
N C4 C3 109.2(2)
N C4 Cl2 123.3(2)
C3 C4 Cl2 127.4(2)
O1 C5 O2 124.9(3)
O1 C5 C1 124.1(3)
O2 C5 C1 110.9(2)
C8 C7 N 120.9(2)
C7 C8 O3 120.2(2)
C7 C8 C12 120.6(2)
O3 C8 C12 118.8(2)
O3 C9 C10 108.1(2)
C11 C10 C9 126.4(3)
O4 C12 O5 124.6(3)
O4 C12 C8 123.7(3)
O5 C12 C8 111.7(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br C2 1.869(3)
Cl1 C3 1.703(3)
Cl2 C4 1.695(3)
O1 C5 1.208(4)
O2 C5 1.327(3)
O2 C6 1.460(4)
O3 C8 1.358(3)
O3 C9 1.446(3)
O4 C12 1.200(4)
O5 C12 1.336(3)
O5 C13 1.443(3)
N C4 1.360(4)
N C1 1.391(4)
N C7 1.426(3)
C1 C2 1.375(4)
C1 C5 1.475(4)
C2 C3 1.402(4)
C3 C4 1.378(4)
C7 C8 1.328(4)
C8 C12 1.500(4)
C9 C10 1.491(4)
C10 C11 1.309(5)
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 N C1 C2 0.0(3)
C7 N C1 C2 -178.4(2)
C4 N C1 C5 178.3(2)
C7 N C1 C5 -0.1(4)
N C1 C2 C3 0.4(3)
C5 C1 C2 C3 -177.6(3)
N C1 C2 Br 178.71(18)
C5 C1 C2 Br 0.7(4)
C1 C2 C3 C4 -0.7(3)
Br C2 C3 C4 -179.08(17)
C1 C2 C3 Cl1 176.60(19)
Br C2 C3 Cl1 -1.8(3)
C1 N C4 C3 -0.4(3)
C7 N C4 C3 178.0(2)
C1 N C4 Cl2 -177.42(18)
C7 N C4 Cl2 1.0(4)
C2 C3 C4 N 0.7(3)
Cl1 C3 C4 N -176.72(18)
C2 C3 C4 Cl2 177.50(19)
Cl1 C3 C4 Cl2 0.1(3)
C6 O2 C5 O1 -3.4(4)
C6 O2 C5 C1 176.2(2)
C2 C1 C5 O1 162.4(3)
N C1 C5 O1 -15.4(4)
C2 C1 C5 O2 -17.3(4)
N C1 C5 O2 164.9(2)
C4 N C7 C8 65.8(4)
C1 N C7 C8 -116.0(3)
N C7 C8 O3 7.5(4)
N C7 C8 C12 179.6(2)
C9 O3 C8 C7 -142.3(3)
C9 O3 C8 C12 45.4(4)
C8 O3 C9 C10 151.7(3)
O3 C9 C10 C11 -2.8(5)
C13 O5 C12 O4 -0.6(4)
C13 O5 C12 C8 -178.2(2)
C7 C8 C12 O4 -170.7(3)
O3 C8 C12 O4 1.5(4)
C7 C8 C12 O5 6.8(4)
O3 C8 C12 O5 179.0(2)
