#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/49/4024912.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_4024912
loop_
_publ_author_name
'Manoj K. Agrawal'
'Pushpito K. Ghosh'
_publ_section_title
;
Halonium Ion-Assisted Deiodination of Styrene-Based Vicinal Iodohydrins
Followed by Rearrangement through Phenyl Migration
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7947
_journal_page_last               7950
_journal_paper_doi               10.1021/jo9013707
_journal_volume                  74
_journal_year                    2009
_chemical_formula_sum            'C15 H14 N4 O4'
_chemical_formula_weight         314.30
_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                99.212(10)
_cell_angle_beta                 94.034(9)
_cell_angle_gamma                96.202(10)
_cell_formula_units_Z            2
_cell_length_a                   7.703(4)
_cell_length_b                   9.545(5)
_cell_length_c                   10.342(5)
_cell_measurement_reflns_used    879
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      21.84
_cell_measurement_theta_min      2.67
_cell_volume                     743.2(7)
_computing_cell_refinement       'BRUKER SMART'
_computing_data_collection       'BRUKER SMART'
_computing_data_reduction        'BRUKER SAINT'
_computing_molecular_graphics    ORTEP
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'BRUKER SMART APEX CCD DIFFRACTOMETER'
_diffrn_measurement_method       'OMEGA-PHI SCAN'
_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  0.0466
_diffrn_reflns_av_sigmaI/netI    0.0762
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4647
_diffrn_reflns_theta_full        24.00
_diffrn_reflns_theta_max         24.00
_diffrn_reflns_theta_min         2.00
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_T_max  0.9948
_exptl_absorpt_correction_T_min  0.9642
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'BRUKER SADABS'
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.405
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       PLATES
_exptl_crystal_F_000             328
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.190
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.152
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     213
_refine_ls_number_reflns         2316
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.152
_refine_ls_R_factor_all          0.1584
_refine_ls_R_factor_gt           0.1072
_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)+(0.0622P)²+0.7206P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1866
_refine_ls_wR_factor_ref         0.2086
_reflns_number_gt                1560
_reflns_number_total             2316
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo9013707_si_001_3.cif
_cod_data_source_block           Table1;Entry10
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'MULTI-SCAN' changed
to 'multi-scan' 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_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4024912
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_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.1169(5) 0.9381(4) 0.7412(4) 0.0474(11) Uani 1 d . . .
N2 N 0.1952(7) 1.0192(5) 0.8578(4) 0.0495(13) Uani 1 d . . .
C14 C 0.1732(6) 1.2071(5) 1.0451(5) 0.0462(13) Uani 1 d . . .
C9 C 0.1121(7) 1.1232(5) 0.9217(5) 0.0437(13) Uani 1 d . . .
O4 O 0.4329(5) 1.1092(5) 1.0596(4) 0.0907(16) Uani 1 d . . .
N4 N 0.3356(6) 1.1865(5) 1.1148(4) 0.0598(13) Uani 1 d . . .
O2 O -0.1154(6) 1.5085(5) 1.2183(5) 0.0892(15) Uani 1 d . . .
O3 O 0.3699(5) 1.2470(5) 1.2283(4) 0.0898(15) Uani 1 d . . .
C11 C -0.1403(8) 1.2548(6) 0.9254(5) 0.0642(16) Uani 1 d . . .
H11 H -0.2465 1.2713 0.8856 0.077 Uiso 1 calc R . .
C8 C 0.1968(7) 0.8370(5) 0.6916(5) 0.0462(13) Uani 1 d . . .
H8 H 0.3026 0.8229 0.7338 0.055 Uiso 1 calc R . .
N3 N -0.1741(8) 1.4423(5) 1.1125(5) 0.0637(13) Uani 1 d . . .
C13 C 0.0802(7) 1.3105(5) 1.1054(5) 0.0486(14) Uani 1 d . . .
H13 H 0.1237 1.3641 1.1866 0.058 Uiso 1 calc R . .
C12 C -0.0748(7) 1.3347(5) 1.0472(5) 0.0492(13) Uani 1 d . . .
C10 C -0.0491(7) 1.1525(6) 0.8644(5) 0.0559(15) Uani 1 d . . .
H10 H -0.0943 1.1005 0.7830 0.067 Uiso 1 calc R . .
C7 C 0.1256(7) 0.7380(5) 0.5658(5) 0.0511(14) Uani 1 d . . .
H7 H 0.1049 0.6416 0.5873 0.061 Uiso 1 calc R . .
C1 C 0.3329(7) 0.8556(5) 0.4267(5) 0.0502(14) Uani 1 d . . .
H1 H 0.2898 0.9414 0.4557 0.060 Uiso 1 calc R . .
C6 C 0.2671(6) 0.7351(5) 0.4692(4) 0.0410(12) Uani 1 d . . .
O1 O -0.3130(7) 1.4578(5) 1.0574(5) 0.1069(18) Uani 1 d . . .
C5 C 0.3319(7) 0.6087(6) 0.4245(6) 0.0619(16) Uani 1 d . . .
H5 H 0.2883 0.5250 0.4526 0.074 Uiso 1 calc R . .
C3 C 0.5256(7) 0.7266(7) 0.2956(6) 0.0666(17) Uani 1 d . . .
H3 H 0.6112 0.7239 0.2363 0.080 Uiso 1 calc R . .
C2 C 0.4622(8) 0.8535(6) 0.3413(5) 0.0639(16) Uani 1 d . . .
H2 H 0.5070 0.9376 0.3145 0.077 Uiso 1 calc R . .
C15 C -0.0467(7) 0.7723(6) 0.5090(5) 0.0682(18) Uani 1 d . . .
H15A H -0.1315 0.7681 0.5725 0.102 Uiso 1 calc R . .
H15B H -0.0869 0.7040 0.4311 0.102 Uiso 1 calc R . .
H15C H -0.0319 0.8666 0.4871 0.102 Uiso 1 calc R . .
C4 C 0.4611(8) 0.6055(7) 0.3384(6) 0.0708(18) Uani 1 d . . .
H4 H 0.5043 0.5197 0.3095 0.085 Uiso 1 calc R . .
H2C H 0.284(6) 1.005(5) 0.888(5) 0.033(16) Uiso 1 d . . .
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 N1 N2 116.0(5) . . ?
C9 N2 N1 119.6(5) . . ?
C9 N2 H2C 119(4) . . ?
N1 N2 H2C 121(4) . . ?
C13 C14 C9 121.7(5) . . ?
C13 C14 N4 116.9(5) . . ?
C9 C14 N4 121.4(4) . . ?
N2 C9 C14 124.9(5) . . ?
N2 C9 C10 119.1(5) . . ?
C14 C9 C10 115.9(5) . . ?
O4 N4 O3 121.9(5) . . ?
O4 N4 C14 119.5(4) . . ?
O3 N4 C14 118.6(4) . . ?
C10 C11 C12 120.2(6) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
N1 C8 C7 121.9(5) . . ?
N1 C8 H8 119.1 . . ?
C7 C8 H8 119.1 . . ?
O2 N3 O1 124.0(5) . . ?
O2 N3 C12 118.4(6) . . ?
O1 N3 C12 117.5(5) . . ?
C12 C13 C14 120.4(5) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 H13 119.8 . . ?
C13 C12 C11 119.9(5) . . ?
C13 C12 N3 120.2(5) . . ?
C11 C12 N3 119.9(6) . . ?
C11 C10 C9 121.8(5) . . ?
C11 C10 H10 119.1 . . ?
C9 C10 H10 119.1 . . ?
C15 C7 C8 113.4(4) . . ?
C15 C7 C6 113.3(4) . . ?
C8 C7 C6 108.8(4) . . ?
C15 C7 H7 107.0 . . ?
C8 C7 H7 107.0 . . ?
C6 C7 H7 107.0 . . ?
C6 C1 C2 121.3(5) . . ?
C6 C1 H1 119.3 . . ?
C2 C1 H1 119.3 . . ?
C1 C6 C5 118.6(5) . . ?
C1 C6 C7 121.3(4) . . ?
C5 C6 C7 120.1(5) . . ?
C6 C5 C4 120.5(5) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C4 C3 C2 119.0(6) . . ?
C4 C3 H3 120.5 . . ?
C2 C3 H3 120.5 . . ?
C1 C2 C3 120.0(6) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
C7 C15 H15A 109.5 . . ?
C7 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C7 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C3 C4 C5 120.6(6) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C8 1.260(6) . ?
N1 N2 1.384(6) . ?
N2 C9 1.349(6) . ?
N2 H2C 0.76(4) . ?
C14 C13 1.376(6) . ?
C14 C9 1.413(6) . ?
C14 N4 1.448(6) . ?
C9 C10 1.413(7) . ?
O4 N4 1.215(5) . ?
N4 O3 1.219(5) . ?
O2 N3 1.203(6) . ?
C11 C10 1.363(7) . ?
C11 C12 1.394(7) . ?
C11 H11 0.9300 . ?
C8 C7 1.510(6) . ?
C8 H8 0.9300 . ?
N3 O1 1.211(6) . ?
N3 C12 1.455(6) . ?
C13 C12 1.358(7) . ?
C13 H13 0.9300 . ?
C10 H10 0.9300 . ?
C7 C15 1.503(7) . ?
C7 C6 1.529(7) . ?
C7 H7 0.9800 . ?
C1 C6 1.357(6) . ?
C1 C2 1.376(7) . ?
C1 H1 0.9300 . ?
C6 C5 1.380(7) . ?
C5 C4 1.381(7) . ?
C5 H5 0.9300 . ?
C3 C4 1.360(8) . ?
C3 C2 1.381(8) . ?
C3 H3 0.9300 . ?
C2 H2 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C4 H4 0.9300 . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 7844107
