#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:11:33 +0100 (lun 21 de mar de 2016) $
#$Revision: 178461 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/82/4028220.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_4028220
loop_
_publ_author_name
'Fabrício F. Naciuk'
'Julio C. Milan'
'Almir Andreão'
'Paulo C. M. L. Miranda'
_publ_contact_author_address     'UNICAMP - Brazil'
_publ_contact_author_email       miranda@iqm.unicamp.br
_publ_contact_author_name        'Julio Milan'
_publ_contact_author_phone       +55.19.35.21.30.83
_publ_section_title
;
 Exploitation of a Tuned Oxidation with N-Haloimides in the Synthesis of
 Caulibugulones A-D
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5026
_journal_page_last               5030
_journal_paper_doi               10.1021/jo302772t
_journal_volume                  78
_journal_year                    2013
_chemical_compound_source        'total synthesis'
_chemical_formula_moiety         'C10 H7 Br N2 O2'
_chemical_formula_sum            'C10 H7 Br N2 O2'
_chemical_formula_weight         267.08
_chemical_melting_point          499
_chemical_name_common            'caulibugulone B'
_chemical_name_systematic        6-bromo-7-(methylamino)isoquinoline-5,8-dione
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2012-10-22
_audit_creation_method
;
  Olex2 1.2
  (compiled May  9 2012 12:37:22, GUI svn.r4230)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 105.997(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.8820(8)
_cell_length_b                   7.6896(6)
_cell_length_c                   11.7402(9)
_cell_measurement_reflns_used    4723
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.75
_cell_measurement_theta_min      2.26
_cell_volume                     944.36(12)
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0265
_diffrn_reflns_av_unetI/netI     0.0230
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            16283
_diffrn_reflns_theta_full        30.64
_diffrn_reflns_theta_max         30.64
_diffrn_reflns_theta_min         2.26
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.331
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.5752
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0599 before and 0.0341 after correction.
The Ratio of minimum to maximum transmission is 0.7709.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'dark red'
_exptl_crystal_density_diffrn    1.886
_exptl_crystal_description       monoclinic
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.292
_exptl_crystal_size_mid          0.262
_exptl_crystal_size_min          0.180
_refine_diff_density_max         0.311
_refine_diff_density_min         -0.411
_refine_diff_density_rms         0.070
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.925
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         2898
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.925
_refine_ls_R_factor_all          0.0493
_refine_ls_R_factor_gt           0.0280
_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)+(0.0409P)²+0.3916P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0673
_refine_ls_wR_factor_ref         0.0756
_reflns_number_gt                2112
_reflns_number_total             2898
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo302772t_si_003.cif
_cod_data_source_block           Caulibugulone_B
_cod_database_code               4028220
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x-1/2, -y-1/2, z-1/2'
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 0.39621(2) 0.15035(3) 0.04894(2) 0.04658(9) Uani 1 1 d .
O1 O 0.21677(15) -0.09746(18) 0.10973(14) 0.0434(4) Uani 1 1 d .
O2 O 0.04129(15) 0.54284(17) 0.14205(15) 0.0462(4) Uani 1 1 d .
N1 N -0.16481(17) 0.1298(2) 0.22397(17) 0.0414(4) Uani 1 1 d .
N2 N 0.24734(15) 0.5233(2) 0.07540(15) 0.0337(3) Uani 1 1 d .
H2 H 0.2095 0.6122 0.0946 0.040 Uiso 1 1 calc R
C1 C -0.1221(2) -0.0292(3) 0.20674(19) 0.0396(5) Uani 1 1 d .
H1 H -0.1695 -0.1245 0.2189 0.048 Uiso 1 1 calc R
C2 C -0.09579(19) 0.2629(3) 0.20296(18) 0.0365(4) Uani 1 1 d .
H2a H -0.1224 0.3749 0.2144 0.044 Uiso 1 1 calc R
C3 C 0.01374(17) 0.2445(2) 0.16489(16) 0.0284(4) Uani 1 1 d .
C4 C 0.08082(18) 0.3964(2) 0.13731(17) 0.0293(4) Uani 1 1 d .
C5 C 0.20151(17) 0.3707(2) 0.09758(16) 0.0276(4) Uani 1 1 d .
C6 C 0.3509(2) 0.5645(3) 0.0241(2) 0.0412(5) Uani 1 1 d .
H6a H 0.4309 0.5320 0.0784 0.062 Uiso 1 1 calc R
H6b H 0.3509 0.6871 0.0087 0.062 Uiso 1 1 calc R
H6c H 0.3393 0.5016 -0.0488 0.062 Uiso 1 1 calc R
C7 C 0.05770(18) 0.0784(2) 0.15093(16) 0.0280(4) Uani 1 1 d .
C8 C -0.01299(19) -0.0609(2) 0.17234(18) 0.0347(4) Uani 1 1 d .
H8 H 0.0127 -0.1743 0.1637 0.042 Uiso 1 1 calc R
C9 C 0.17795(18) 0.0519(2) 0.11531(16) 0.0299(4) Uani 1 1 d .
C10 C 0.24418(18) 0.2036(2) 0.09070(17) 0.0297(4) Uani 1 1 d .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br1 0.04137(14) 0.03801(12) 0.07076(18) -0.00216(10) 0.03288(12) 0.00591(9)
O1 0.0492(9) 0.0231(6) 0.0648(10) -0.0020(6) 0.0271(8) 0.0061(6)
O2 0.0495(9) 0.0223(6) 0.0767(11) -0.0017(7) 0.0337(8) 0.0053(6)
N1 0.0359(9) 0.0391(9) 0.0551(11) -0.0004(8) 0.0222(8) -0.0016(7)
N2 0.0337(8) 0.0248(7) 0.0475(9) 0.0005(7) 0.0192(7) -0.0011(7)
C1 0.0407(11) 0.0346(10) 0.0465(12) -0.0003(9) 0.0169(9) -0.0079(9)
C2 0.0348(10) 0.0300(9) 0.0490(12) -0.0011(8) 0.0187(9) 0.0031(8)
C3 0.0303(9) 0.0233(8) 0.0323(9) -0.0005(7) 0.0097(7) 0.0013(7)
C4 0.0306(9) 0.0226(7) 0.0363(10) -0.0027(7) 0.0120(8) 0.0015(7)
C5 0.0267(9) 0.0257(8) 0.0312(9) -0.0018(6) 0.0092(7) -0.0005(7)
C6 0.0417(11) 0.0359(11) 0.0527(12) 0.0061(9) 0.0242(10) -0.0026(9)
C7 0.0302(9) 0.0238(8) 0.0304(9) -0.0008(7) 0.0089(7) 0.0009(7)
C8 0.0410(11) 0.0229(8) 0.0418(11) 0.0000(7) 0.0138(9) -0.0008(8)
C9 0.0328(9) 0.0238(8) 0.0343(9) -0.0018(7) 0.0112(8) 0.0033(7)
C10 0.0285(9) 0.0270(8) 0.0362(10) -0.0009(7) 0.0133(8) 0.0026(7)
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
C2 N1 C1 115.79(17)
C5 N2 H2 114.7
C5 N2 C6 130.57(16)
C6 N2 H2 114.7
N1 C1 H1 117.7
N1 C1 C8 124.61(19)
C8 C1 H1 117.7
N1 C2 H2a 118.0
N1 C2 C3 123.91(17)
C3 C2 H2a 118.0
C2 C3 C4 120.96(16)
C7 C3 C2 119.03(17)
C7 C3 C4 120.00(16)
O2 C4 C3 121.84(17)
O2 C4 C5 118.80(16)
C3 C4 C5 119.33(15)
N2 C5 C4 110.32(14)
N2 C5 C10 131.47(17)
C10 C5 C4 118.21(15)
N2 C6 H6a 109.5
N2 C6 H6b 109.5
N2 C6 H6c 109.5
H6a C6 H6b 109.5
H6a C6 H6c 109.5
H6b C6 H6c 109.5
C3 C7 C9 121.01(16)
C8 C7 C3 117.65(17)
C8 C7 C9 121.34(16)
C1 C8 C7 118.97(18)
C1 C8 H8 120.5
C7 C8 H8 120.5
O1 C9 C7 118.82(17)
O1 C9 C10 123.09(17)
C10 C9 C7 118.09(15)
C5 C10 Br1 123.33(14)
C5 C10 C9 123.25(16)
C9 C10 Br1 113.42(13)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C10 1.8952(18)
O1 C9 1.231(2)
O2 C4 1.212(2)
N1 C1 1.343(3)
N1 C2 1.332(3)
N2 H2 0.8600
N2 C5 1.329(2)
N2 C6 1.452(2)
C1 H1 0.9300
C1 C8 1.377(3)
C2 H2a 0.9300
C2 C3 1.391(3)
C3 C4 1.461(2)
C3 C7 1.389(2)
C4 C5 1.523(3)
C5 C10 1.376(2)
C6 H6a 0.9600
C6 H6b 0.9600
C6 H6c 0.9600
C7 C8 1.381(2)
C7 C9 1.493(3)
C8 H8 0.9300
C9 C10 1.442(3)
