#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/69/4026999.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_4026999
loop_
_publ_author_name
'Adele E. Pasqua'
'James J. Crawford'
'De-Liang Long'
'Rodolfo Marquez'
_publ_section_title
;
 Protecting Group Free, Stereocontrolled Synthesis of β-Halo-enamides
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2149
_journal_page_last               2158
_journal_paper_doi               10.1021/jo202130e
_journal_volume                  77
_journal_year                    2012
_chemical_formula_sum            'C8 H11 I2 N O'
_chemical_formula_weight         390.98
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 100.536(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.9197(2)
_cell_length_b                   14.4321(4)
_cell_length_c                   10.8204(4)
_cell_measurement_reflns_used    3980
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      25.9
_cell_measurement_theta_min      2.99
_cell_volume                     1062.37(6)
_computing_cell_refinement
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
;
_computing_data_collection
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
;
_computing_data_reduction
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXL-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 10.438
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini Ultra'
_diffrn_measurement_method       'ω & π 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  0.0456
_diffrn_reflns_av_sigmaI/netI    0.0409
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            8621
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.99
_diffrn_standards_decay_%        none
_exptl_absorpt_coefficient_mu    5.88
_exptl_absorpt_correction_T_max  0.828
_exptl_absorpt_correction_T_min  0.513
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
Analytical numeric absorption correction using a multifaceted crystal
            model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.444
_exptl_crystal_density_meas      ?
_exptl_crystal_description       block
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.62
_refine_diff_density_min         -0.60
_refine_diff_density_rms         0.14
_refine_ls_extinction_coef       none
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     109
_refine_ls_number_reflns         2085
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0345
_refine_ls_R_factor_gt           0.0248
_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)+(0.0091P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0407
_refine_ls_wR_factor_ref         0.0440
_reflns_number_gt                1763
_reflns_number_total             2085
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            jo202130e_si_002.cif
_cod_data_source_block           elisa205
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'none' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_database_code               4026999
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
I1 I 0.40143(3) 0.577470(18) 0.82491(3) 0.02305(9) Uani 1 1 d .
I2 I 0.75293(4) 0.402157(18) 0.78938(3) 0.02369(9) Uani 1 1 d .
O1 O 1.0647(4) 0.72170(19) 0.8360(3) 0.0241(7) Uani 1 1 d .
N1 N 0.8369(4) 0.6791(2) 0.9500(3) 0.0171(7) Uani 1 1 d .
C1 C 0.9728(5) 0.7401(3) 0.9193(4) 0.0186(9) Uani 1 1 d .
C2 C 0.9973(6) 0.8304(3) 0.9888(4) 0.0243(10) Uani 1 1 d .
H2A H 1.1121 0.8636 0.9676 0.029 Uiso 1 1 calc R
H2B H 1.0248 0.8178 1.0803 0.029 Uiso 1 1 calc R
C3 C 0.8148(6) 0.8931(3) 0.9578(4) 0.0259(10) Uani 1 1 d .
H3A H 0.8563 0.9587 0.9692 0.031 Uiso 1 1 calc R
H3B H 0.7534 0.8844 0.8684 0.031 Uiso 1 1 calc R
C4 C 0.6633(6) 0.8727(3) 1.0399(4) 0.0269(10) Uani 1 1 d .
H4A H 0.7255 0.8813 1.1291 0.032 Uiso 1 1 calc R
H4B H 0.5550 0.9182 1.0203 0.032 Uiso 1 1 calc R
C5 C 0.5772(5) 0.7757(3) 1.0235(4) 0.0251(10) Uani 1 1 d .
H5A H 0.5064 0.7691 0.9358 0.030 Uiso 1 1 calc R
H5B H 0.4793 0.7691 1.0792 0.030 Uiso 1 1 calc R
C6 C 0.7252(6) 0.6969(3) 1.0516(4) 0.0224(10) Uani 1 1 d .
H6A H 0.8191 0.7116 1.1297 0.027 Uiso 1 1 calc R
H6B H 0.6545 0.6396 1.0670 0.027 Uiso 1 1 calc R
C7 C 0.8442(5) 0.5885(3) 0.9008(4) 0.0171(9) Uani 1 1 d .
H7 H 0.9716 0.5635 0.9022 0.021 Uiso 1 1 calc R
C8 C 0.6941(5) 0.5344(3) 0.8529(4) 0.0176(9) 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
I1 0.01721(14) 0.02554(16) 0.02641(18) -0.00092(13) 0.00402(11) 0.00069(11)
I2 0.02680(15) 0.01804(15) 0.02569(18) -0.00252(12) 0.00338(12) 0.00268(11)
O1 0.0211(14) 0.0256(16) 0.0280(18) 0.0016(14) 0.0110(13) 0.0009(12)
N1 0.0179(16) 0.0159(18) 0.018(2) 0.0012(15) 0.0054(14) 0.0015(14)
C1 0.016(2) 0.019(2) 0.020(3) 0.0071(19) 0.0003(18) 0.0063(17)
C2 0.027(2) 0.021(2) 0.026(3) -0.002(2) 0.0067(19) -0.0072(18)
C3 0.034(2) 0.017(2) 0.027(3) 0.001(2) 0.005(2) 0.0020(19)
C4 0.032(2) 0.020(2) 0.029(3) -0.001(2) 0.008(2) 0.0006(19)
C5 0.025(2) 0.025(2) 0.027(3) 0.001(2) 0.0085(19) 0.0029(18)
C6 0.026(2) 0.024(2) 0.019(2) -0.002(2) 0.0084(18) -0.0020(18)
C7 0.0175(19) 0.018(2) 0.017(2) 0.0016(18) 0.0045(17) 0.0037(16)
C8 0.019(2) 0.016(2) 0.019(2) 0.0010(18) 0.0067(17) 0.0051(17)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
I I -0.4742 1.8119 '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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C1 N1 C7 115.4(3)
C1 N1 C6 122.9(3)
C7 N1 C6 120.0(3)
O1 C1 N1 120.7(4)
O1 C1 C2 122.1(4)
N1 C1 C2 117.1(4)
C1 C2 C3 112.8(3)
C4 C3 C2 112.6(3)
C5 C4 C3 114.1(4)
C4 C5 C6 115.5(3)
N1 C6 C5 113.9(3)
C8 C7 N1 127.7(3)
C7 C8 I1 123.4(3)
C7 C8 I2 118.7(3)
I1 C8 I2 117.76(18)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
I1 C8 2.087(4)
I2 C8 2.093(4)
O1 C1 1.223(5)
N1 C1 1.372(5)
N1 C7 1.416(5)
N1 C6 1.477(5)
C1 C2 1.499(5)
C2 C3 1.540(5)
C3 C4 1.522(6)
C4 C5 1.518(5)
C5 C6 1.524(5)
C7 C8 1.327(5)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30659476
