#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/57/4025721.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_4025721
loop_
_publ_author_name
'Micah J. Niphakis'
'Brandon J. Turunen'
'Gunda I. Georg'
_publ_section_title
;
 Synthesis of 6- and 7-Membered Cyclic Enaminones: Scope and Mechanism
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6793
_journal_page_last               6805
_journal_paper_doi               10.1021/jo100907u
_journal_volume                  75
_journal_year                    2010
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C8 H13 I N O, I'
_chemical_formula_sum            'C8 H13 I2 N O'
_chemical_formula_weight         392.99
_chemical_name_common            08053a
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 96.339(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.7128(13)
_cell_length_b                   7.4839(11)
_cell_length_c                   9.3223(13)
_cell_measurement_reflns_used    2533
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.24
_cell_measurement_theta_min      2.35
_cell_volume                     604.15(15)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0252
_diffrn_reflns_av_sigmaI/netI    0.0283
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            6149
_diffrn_reflns_theta_full        27.46
_diffrn_reflns_theta_max         27.46
_diffrn_reflns_theta_min         2.20
_exptl_absorpt_coefficient_mu    5.168
_exptl_absorpt_correction_T_max  0.7821
_exptl_absorpt_correction_T_min  0.2045
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2003)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    2.160
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             364
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.570
_refine_diff_density_min         -0.438
_refine_diff_density_rms         0.078
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     109
_refine_ls_number_reflns         2704
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0203
_refine_ls_R_factor_gt           0.0192
_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)+(0.0250P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0479
_refine_ls_wR_factor_ref         0.0483
_reflns_number_gt                2619
_reflns_number_total             2704
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo100907u_si_002.cif
_cod_data_source_block           08053a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to the built-in table from CIF Core 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 the built-in table from CIF Core
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_database_code               4025721
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, 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
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.6388(3) 0.3088(3) 0.4160(3) 0.0235(5) Uani 1 1 d . . .
H1A H 0.5842 0.2152 0.3713 0.028 Uiso 1 1 calc R . .
H1B H 0.5938 0.3394 0.4973 0.028 Uiso 1 1 calc R . .
C1 C 0.8059(4) 0.2548(5) 0.4568(4) 0.0338(8) Uani 1 1 d . . .
H1C H 0.8277 0.2380 0.5624 0.041 Uiso 1 1 calc R . .
H1D H 0.8299 0.1425 0.4078 0.041 Uiso 1 1 calc R . .
C2 C 0.8981(4) 0.4079(6) 0.4066(4) 0.0425(10) Uani 1 1 d . . .
H2A H 1.0020 0.3683 0.3866 0.051 Uiso 1 1 calc R . .
H2B H 0.9091 0.5051 0.4791 0.051 Uiso 1 1 calc R . .
C3 C 0.8007(3) 0.4677(7) 0.2684(4) 0.0380(8) Uani 1 1 d . . .
H3A H 0.8097 0.3827 0.1884 0.046 Uiso 1 1 calc R . .
H3B H 0.8312 0.5884 0.2385 0.046 Uiso 1 1 calc R . .
C4 C 0.6372(3) 0.4679(5) 0.3141(3) 0.0283(7) Uani 1 1 d . . .
H4A H 0.6217 0.5799 0.3693 0.034 Uiso 1 1 calc R . .
C5 C 0.5083(3) 0.4517(6) 0.1903(3) 0.0273(6) Uani 1 1 d . . .
H5A H 0.5162 0.5514 0.1217 0.033 Uiso 1 1 calc R . .
H5B H 0.5206 0.3384 0.1379 0.033 Uiso 1 1 calc R . .
C6 C 0.3522(3) 0.4553(6) 0.2435(3) 0.0315(7) Uani 1 1 d . . .
O1 O 0.3376(2) 0.4524(5) 0.3716(2) 0.0400(5) Uani 1 1 d . . .
C7 C 0.2115(3) 0.4615(7) 0.1377(3) 0.0346(7) Uani 1 1 d . . .
H7A H 0.1149 0.4667 0.1759 0.042 Uiso 1 1 calc R . .
C8 C 0.2079(3) 0.4606(6) -0.0025(3) 0.0317(6) Uani 1 1 d . . .
H8A H 0.3014 0.4570 -0.0461 0.038 Uiso 1 1 calc R . .
I1 I -0.00430(2) 0.46676(5) -0.13112(2) 0.03622(7) Uani 1 1 d . . .
I2 I 0.43456(2) -0.05064(2) 0.240205(18) 0.02900(6) 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
N1 0.0217(13) 0.0271(13) 0.0221(12) -0.0006(10) 0.0037(10) -0.0025(10)
C1 0.0211(16) 0.043(2) 0.0372(18) 0.0058(15) 0.0033(14) 0.0042(14)
C2 0.0263(17) 0.062(3) 0.0387(17) 0.0104(18) 0.0028(15) -0.0079(17)
C3 0.0235(14) 0.048(2) 0.0436(16) 0.014(2) 0.0074(13) -0.0057(19)
C4 0.0253(14) 0.0290(18) 0.0303(14) 0.0045(17) 0.0021(11) -0.0002(17)
C5 0.0273(14) 0.0300(15) 0.0252(13) 0.0016(16) 0.0052(11) 0.0046(17)
C6 0.0269(14) 0.0374(18) 0.0300(13) -0.0029(18) 0.0023(11) 0.0077(19)
O1 0.0318(11) 0.0638(16) 0.0250(10) 0.0022(16) 0.0060(9) 0.0082(17)
C7 0.0216(14) 0.050(2) 0.0324(14) 0.000(2) 0.0050(11) 0.004(2)
C8 0.0274(14) 0.0323(16) 0.0351(14) 0.0006(17) 0.0014(12) -0.0020(18)
I1 0.03198(12) 0.04260(14) 0.03239(11) 0.00090(12) -0.00395(8) 0.00032(12)
I2 0.03245(11) 0.02933(11) 0.02517(9) 0.00064(10) 0.00295(7) -0.00572(11)
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'
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 N1 C1 107.9(2) . . ?
C4 N1 H1A 110.1 . . ?
C1 N1 H1A 110.1 . . ?
C4 N1 H1B 110.1 . . ?
C1 N1 H1B 110.1 . . ?
H1A N1 H1B 108.4 . . ?
C2 C1 N1 104.5(3) . . ?
C2 C1 H1C 110.9 . . ?
N1 C1 H1C 110.9 . . ?
C2 C1 H1D 110.9 . . ?
N1 C1 H1D 110.9 . . ?
H1C C1 H1D 108.9 . . ?
C1 C2 C3 102.7(3) . . ?
C1 C2 H2A 111.2 . . ?
C3 C2 H2A 111.2 . . ?
C1 C2 H2B 111.2 . . ?
C3 C2 H2B 111.2 . . ?
H2A C2 H2B 109.1 . . ?
C2 C3 C4 102.3(3) . . ?
C2 C3 H3A 111.3 . . ?
C4 C3 H3A 111.3 . . ?
C2 C3 H3B 111.3 . . ?
C4 C3 H3B 111.3 . . ?
H3A C3 H3B 109.2 . . ?
N1 C4 C5 111.4(3) . . ?
N1 C4 C3 103.2(3) . . ?
C5 C4 C3 114.8(3) . . ?
N1 C4 H4A 109.1 . . ?
C5 C4 H4A 109.1 . . ?
C3 C4 H4A 109.1 . . ?
C6 C5 C4 111.6(2) . . ?
C6 C5 H5A 109.3 . . ?
C4 C5 H5A 109.3 . . ?
C6 C5 H5B 109.3 . . ?
C4 C5 H5B 109.3 . . ?
H5A C5 H5B 108.0 . . ?
O1 C6 C7 119.0(3) . . ?
O1 C6 C5 121.5(3) . . ?
C7 C6 C5 119.5(3) . . ?
C8 C7 C6 126.3(3) . . ?
C8 C7 H7A 116.9 . . ?
C6 C7 H7A 116.9 . . ?
C7 C8 I1 119.8(2) . . ?
C7 C8 H8A 120.1 . . ?
I1 C8 H8A 120.1 . . ?
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 C4 1.522(4) . ?
N1 C1 1.519(4) . ?
N1 H1A 0.9200 . ?
N1 H1B 0.9200 . ?
C1 C2 1.503(5) . ?
C1 H1C 0.9900 . ?
C1 H1D 0.9900 . ?
C2 C3 1.530(5) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.532(4) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.524(4) . ?
C4 H4A 1.0000 . ?
C5 C6 1.498(4) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 O1 1.215(3) . ?
C6 C7 1.487(4) . ?
C7 C8 1.304(4) . ?
C7 H7A 0.9500 . ?
C8 I1 2.090(3) . ?
C8 H8A 0.9500 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1B I2 0.92 2.62 3.498(2) 160.2 2_656
N1 H1A I2 0.92 2.61 3.528(3) 178.6 .
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C4 N1 C1 C2 12.8(3) . . . . ?
N1 C1 C2 C3 -35.3(4) . . . . ?
C1 C2 C3 C4 44.7(4) . . . . ?
C1 N1 C4 C5 138.4(3) . . . . ?
C1 N1 C4 C3 14.7(3) . . . . ?
C2 C3 C4 N1 -36.0(4) . . . . ?
C2 C3 C4 C5 -157.5(4) . . . . ?
N1 C4 C5 C6 63.9(4) . . . . ?
C3 C4 C5 C6 -179.3(4) . . . . ?
C4 C5 C6 O1 -7.2(6) . . . . ?
C4 C5 C6 C7 173.2(4) . . . . ?
O1 C6 C7 C8 -178.1(5) . . . . ?
C5 C6 C7 C8 1.5(8) . . . . ?
C6 C7 C8 I1 179.2(4) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30659283
