#------------------------------------------------------------------------------
#$Date: 2016-02-18 16:37:37 +0100 (jue 18 de feb de 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/60/1506049.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_1506049
loop_
_publ_author_name
'Hu, Tianshun'
'Shen, Meihua'
'Chen, Qian'
'Li, Chaozhong'
_publ_section_title
;
 Pushing radical cyclization from regioselective to regiospecific:
 cyclization of amidyl radicals controlled by vinylic halogen
 substitution.
;
_journal_issue                   12
_journal_name_full               'Organic letters'
_journal_page_first              2647
_journal_page_last               2650
_journal_paper_doi               10.1021/ol060983q
_journal_volume                  8
_journal_year                    2006
_chemical_formula_sum            'C7 H11 Br I N O'
_chemical_formula_weight         331.98
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   7.9917(13)
_cell_length_b                   10.5745(18)
_cell_length_c                   23.462(4)
_cell_measurement_reflns_used    2432
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      46.837
_cell_measurement_theta_min      6.169
_cell_volume                     1982.7(6)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_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      293(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  0.1575
_diffrn_reflns_av_sigmaI/netI    0.0877
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            10789
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         1.74
_exptl_absorpt_coefficient_mu    7.210
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.16312
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    2.224
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1248
_exptl_crystal_size_max          0.512
_exptl_crystal_size_mid          0.378
_exptl_crystal_size_min          0.153
_refine_diff_density_max         1.733
_refine_diff_density_min         -1.063
_refine_diff_density_rms         0.218
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.974
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     100
_refine_ls_number_reflns         2163
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.974
_refine_ls_R_factor_all          0.0943
_refine_ls_R_factor_gt           0.0738
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1247P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1971
_refine_ls_wR_factor_ref         0.2084
_reflns_number_gt                1459
_reflns_number_total             2163
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol060983qsi20060425_124034.cif
_cod_data_source_block           cd25108
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' 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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      Pbca
_cod_database_code               1506049
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, 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
I I 1.15437(9) 0.22271(9) 0.33323(3) 0.0600(4) Uani 0.75 1 d P
Br Br 1.00276(9) -0.06203(8) 0.29622(3) 0.0539(3) Uani 1 1 d .
N1 N 0.9640(7) 0.1341(7) 0.4551(3) 0.0502(16) Uani 1 1 d .
H1 H 1.0494 0.1743 0.4682 0.060 Uiso 1 1 calc R
O1 O 0.7924(9) 0.2618(6) 0.5034(2) 0.0626(16) Uani 1 1 d .
C1 C 0.8123(9) 0.1659(8) 0.4766(3) 0.0432(17) Uani 1 1 d .
C2 C 0.6687(9) 0.0770(8) 0.4661(4) 0.053(2) Uani 1 1 d .
H2 H 0.5943 0.0797 0.4988 0.064 Uiso 1 1 calc R
H3 H 0.7121 -0.0084 0.4631 0.064 Uiso 1 1 calc R
C3 C 0.5663(10) 0.1069(9) 0.4118(4) 0.062(2) Uani 1 1 d .
H4 H 0.4597 0.0635 0.4144 0.074 Uiso 1 1 calc R
H5 H 0.5432 0.1970 0.4111 0.074 Uiso 1 1 calc R
C4 C 0.6496(10) 0.0701(9) 0.3552(4) 0.061(2) Uani 1 1 d .
H7 H 0.6833 -0.0179 0.3572 0.074 Uiso 1 1 calc R
H6 H 0.5677 0.0777 0.3249 0.074 Uiso 1 1 calc R
C5 C 0.7987(11) 0.1480(9) 0.3401(3) 0.057(2) Uani 1 1 d .
H9 H 0.7924 0.2269 0.3611 0.068 Uiso 1 1 calc R
H8 H 0.7921 0.1686 0.2998 0.068 Uiso 1 1 calc R
C6 C 0.9688(9) 0.0887(7) 0.3514(3) 0.0431(17) Uani 1 1 d .
C7 C 0.9952(9) 0.0389(8) 0.4124(3) 0.0474(19) Uani 1 1 d .
H10 H 0.9210 -0.0322 0.4189 0.057 Uiso 1 1 calc R
H11 H 1.1093 0.0089 0.4163 0.057 Uiso 1 1 calc R
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
I 0.0528(5) 0.0732(7) 0.0541(5) 0.0105(3) 0.0074(3) -0.0107(3)
Br 0.0609(6) 0.0553(7) 0.0454(5) -0.0099(3) 0.0077(4) 0.0132(4)
N1 0.038(3) 0.059(4) 0.054(4) 0.001(3) -0.005(3) -0.008(3)
O1 0.054(3) 0.080(4) 0.054(4) -0.023(3) 0.001(3) -0.007(3)
C1 0.042(4) 0.049(5) 0.038(4) 0.004(3) 0.001(3) -0.004(3)
C2 0.051(5) 0.055(5) 0.053(5) 0.000(4) 0.011(4) -0.008(3)
C3 0.039(4) 0.083(6) 0.062(6) -0.016(5) 0.001(4) -0.011(4)
C4 0.048(5) 0.087(7) 0.049(5) -0.008(4) -0.008(4) 0.003(4)
C5 0.053(5) 0.071(6) 0.047(5) 0.003(4) -0.007(4) 0.007(4)
C6 0.041(4) 0.045(4) 0.043(4) 0.005(3) 0.001(3) 0.005(3)
C7 0.047(4) 0.058(5) 0.037(4) 0.006(3) 0.007(3) 0.007(4)
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'
I I -0.4742 1.8119 '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
C1 N1 C7 125.9(6)
C1 N1 H1 117.1
C7 N1 H1 117.1
O1 C1 N1 121.4(7)
O1 C1 C2 120.7(7)
N1 C1 C2 117.9(7)
C1 C2 C3 114.3(7)
C1 C2 H2 108.7
C3 C2 H2 108.7
C1 C2 H3 108.7
C3 C2 H3 108.7
H2 C2 H3 107.6
C4 C3 C2 115.5(7)
C4 C3 H4 108.4
C2 C3 H4 108.4
C4 C3 H5 108.4
C2 C3 H5 108.4
H4 C3 H5 107.5
C5 C4 C3 114.3(8)
C5 C4 H7 108.7
C3 C4 H7 108.7
C5 C4 H6 108.7
C3 C4 H6 108.7
H7 C4 H6 107.6
C4 C5 C6 116.4(8)
C4 C5 H9 108.2
C6 C5 H9 108.2
C4 C5 H8 108.2
C6 C5 H8 108.2
H9 C5 H8 107.3
C5 C6 C7 115.3(6)
C5 C6 Br 108.9(6)
C7 C6 Br 107.5(5)
C5 C6 I 108.5(6)
C7 C6 I 108.9(5)
Br C6 I 107.5(3)
N1 C7 C6 112.6(7)
N1 C7 H10 109.1
C6 C7 H10 109.1
N1 C7 H11 109.1
C6 C7 H11 109.1
H10 C7 H11 107.8
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
I C6 2.096(7)
Br C6 2.072(8)
N1 C1 1.355(9)
N1 C7 1.442(11)
N1 H1 0.8600
O1 C1 1.204(9)
C1 C2 1.504(10)
C2 C3 1.547(12)
C2 H2 0.9700
C2 H3 0.9700
C3 C4 1.537(11)
C3 H4 0.9700
C3 H5 0.9700
C4 C5 1.491(12)
C4 H7 0.9700
C4 H6 0.9700
C5 C6 1.521(11)
C5 H9 0.9700
C5 H8 0.9700
C6 C7 1.539(11)
C7 H10 0.9700
C7 H11 0.9700
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
C7 N1 C1 O1 -165.1(8)
C7 N1 C1 C2 15.1(12)
O1 C1 C2 C3 88.4(10)
N1 C1 C2 C3 -91.9(9)
C1 C2 C3 C4 75.3(10)
C2 C3 C4 C5 -69.2(11)
C3 C4 C5 C6 101.1(10)
C4 C5 C6 C7 -52.8(10)
C4 C5 C6 Br 68.1(8)
C4 C5 C6 I -175.2(6)
C1 N1 C7 C6 83.3(9)
C5 C6 C7 N1 -54.6(9)
Br C6 C7 N1 -176.2(5)
I C6 C7 N1 67.6(6)
