#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:19:01 +0100 (lun 21 de mar de 2016) $
#$Revision: 178465 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/86/4028652.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_4028652
loop_
_publ_author_name
'Anthony J. Pearson'
'Santanu Panda'
'Scott D. Bunge'
_publ_contact_author_address
;Kent State University 
Chemistry Department 
PO Box 5190 
Kent, OH 44242, USA 
;
_publ_contact_author_email       sbunge@kent.edu
_publ_contact_author_fax         '330 672 3816'
_publ_contact_author_name        'Scott D. Bunge'
_publ_contact_author_phone       '330 672 9445'
_publ_section_title
;
 Synthesis of a Potential Intermediate for TMC-95A via an Organocatalyzed
 Aldol Reaction
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              9921
_journal_page_last               9928
_journal_paper_doi               10.1021/jo4017315
_journal_volume                  78
_journal_year                    2013
_chemical_formula_moiety         'C14 H14 I N O5'
_chemical_formula_sum            'C14 H14 I N O5'
_chemical_formula_weight         403.16
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_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
_audit_update_record
;
2013-07-11 # Formatted by publCIF
;
_cell_angle_alpha                90.00
_cell_angle_beta                 103.569(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.026(3)
_cell_length_b                   13.368(3)
_cell_length_c                   8.2002(16)
_cell_measurement_reflns_used    7435
_cell_measurement_temperature    185(2)
_cell_measurement_theta_max      29.85
_cell_measurement_theta_min      2.98
_cell_volume                     1494.6(5)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      185(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω 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  0.0297
_diffrn_reflns_av_sigmaI/netI    0.0242
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            11468
_diffrn_reflns_theta_full        25.05
_diffrn_reflns_theta_max         25.05
_diffrn_reflns_theta_min         1.49
_exptl_absorpt_coefficient_mu    2.163
_exptl_absorpt_correction_T_max  0.8127
_exptl_absorpt_correction_T_min  0.7374
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.792
_exptl_crystal_description       irregular
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         3.863
_refine_diff_density_min         -1.513
_refine_diff_density_rms         0.200
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.873
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2627
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.873
_refine_ls_R_factor_all          0.0628
_refine_ls_R_factor_gt           0.0592
_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)+(0.1000P)²+0.0709P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2111
_refine_ls_wR_factor_ref         0.2162
_reflns_number_gt                2419
_reflns_number_total             2627
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo4017315_si_002.cif
_cod_data_source_block           panda_mono
_cod_original_cell_volume        1494.5(5)
_cod_database_code               4028652
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 0.07268(3) 0.25696(3) 0.56562(6) 0.0323(3) Uani 1 1 d .
N1 N 0.2827(4) 0.3656(4) 0.5110(6) 0.0253(11) Uani 1 1 d .
H1 H 0.2869 0.3122 0.5751 0.030 Uiso 1 1 calc R
O1 O 0.4470(3) 0.3912(3) 0.5342(6) 0.0337(11) Uani 1 1 d .
O2 O 0.3551(4) 0.5945(3) 0.4583(7) 0.0304(11) Uani 1 1 d .
H2 H 0.4164 0.5993 0.4752 0.046 Uiso 1 1 calc R
O3 O 0.3116(3) 0.5836(3) 0.1036(6) 0.0343(11) Uani 1 1 d .
O4 O 0.3615(5) 0.5018(5) -0.1165(8) 0.0572(17) Uani 1 1 d .
O5 O 0.3265(3) 0.3265(3) 0.1713(6) 0.0362(11) Uani 1 1 d .
C1 C 0.1001(5) 0.3810(5) 0.4293(7) 0.0286(13) Uani 1 1 d .
C2 C 0.0226(4) 0.4383(5) 0.3368(7) 0.0302(14) Uani 1 1 d .
H2A H -0.0432 0.4198 0.3342 0.036 Uiso 1 1 calc R
C3 C 0.0408(5) 0.5209(5) 0.2498(9) 0.0357(15) Uani 1 1 d .
H3 H -0.0129 0.5589 0.1882 0.043 Uiso 1 1 calc R
C4 C 0.1364(4) 0.5510(5) 0.2491(8) 0.0326(14) Uani 1 1 d .
H4 H 0.1482 0.6077 0.1870 0.039 Uiso 1 1 calc R
C5 C 0.2129(5) 0.4946(4) 0.3425(7) 0.0241(12) Uani 1 1 d .
C6 C 0.1945(4) 0.4104(4) 0.4313(7) 0.0223(12) Uani 1 1 d .
C7 C 0.3236(5) 0.5062(5) 0.3676(8) 0.0244(14) Uani 1 1 d .
C8 C 0.3606(5) 0.4132(4) 0.4788(7) 0.0255(13) Uani 1 1 d .
C9 C 0.3576(4) 0.5032(4) 0.2026(8) 0.0241(12) Uani 1 1 d .
H9 H 0.4305 0.5112 0.2264 0.029 Uiso 1 1 calc R
C10 C 0.3432(7) 0.5981(6) -0.0478(11) 0.046(2) Uani 1 1 d .
C11 C 0.2989(8) 0.4244(7) -0.0794(10) 0.060(3) Uani 1 1 d .
H11A H 0.3073 0.3623 -0.1403 0.072 Uiso 1 1 calc R
H11B H 0.2293 0.4452 -0.1141 0.072 Uiso 1 1 calc R
C12 C 0.3274(5) 0.4068(5) 0.1059(8) 0.0285(14) Uani 1 1 d .
C13 C 0.4367(6) 0.6518(7) -0.0222(13) 0.059(2) Uani 1 1 d .
H13A H 0.4544 0.6602 -0.1302 0.088 Uiso 1 1 calc R
H13B H 0.4880 0.6135 0.0542 0.088 Uiso 1 1 calc R
H13C H 0.4303 0.7177 0.0265 0.088 Uiso 1 1 calc R
C14 C 0.2597(7) 0.6547(8) -0.1630(10) 0.063(3) Uani 1 1 d .
H14A H 0.1992 0.6154 -0.1791 0.094 Uiso 1 1 calc R
H14B H 0.2756 0.6658 -0.2717 0.094 Uiso 1 1 calc R
H14C H 0.2505 0.7193 -0.1123 0.094 Uiso 1 1 calc R
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
C8 N1 C6 112.2(5)
C8 N1 H1 123.9
C6 N1 H1 123.9
C7 O2 H2 109.5
C9 O3 C10 114.3(5)
C11 O4 C10 112.6(7)
C6 C1 C2 118.2(6)
C6 C1 I1 121.2(5)
C2 C1 I1 120.6(5)
C3 C2 C1 120.5(6)
C3 C2 H2A 119.8
C1 C2 H2A 119.8
C2 C3 C4 122.0(6)
C2 C3 H3 119.0
C4 C3 H3 119.0
C5 C4 C3 117.4(6)
C5 C4 H4 121.3
C3 C4 H4 121.3
C4 C5 C6 120.8(6)
C4 C5 C7 130.7(6)
C6 C5 C7 108.5(5)
C1 C6 N1 128.9(5)
C1 C6 C5 121.2(6)
N1 C6 C5 109.8(5)
O2 C7 C5 109.8(5)
O2 C7 C9 111.3(5)
C5 C7 C9 113.3(5)
O2 C7 C8 109.8(5)
C5 C7 C8 100.7(5)
C9 C7 C8 111.4(5)
O1 C8 N1 126.4(6)
O1 C8 C7 124.9(6)
N1 C8 C7 108.6(5)
O3 C9 C12 108.1(5)
O3 C9 C7 107.0(5)
C12 C9 C7 112.0(5)
O3 C9 H9 109.8
C12 C9 H9 109.8
C7 C9 H9 109.8
O3 C10 O4 109.7(6)
O3 C10 C13 113.1(8)
O4 C10 C13 104.8(8)
O3 C10 C14 104.9(7)
O4 C10 C14 112.3(8)
C13 C10 C14 112.2(7)
O4 C11 C12 107.3(6)
O4 C11 H11A 110.3
C12 C11 H11A 110.3
O4 C11 H11B 110.3
C12 C11 H11B 110.3
H11A C11 H11B 108.5
O5 C12 C11 124.4(6)
O5 C12 C9 123.7(6)
C11 C12 C9 111.9(6)
C10 C13 H13A 109.5
C10 C13 H13B 109.5
H13A C13 H13B 109.5
C10 C13 H13C 109.5
H13A C13 H13C 109.5
H13B C13 H13C 109.5
C10 C14 H14A 109.5
C10 C14 H14B 109.5
H14A C14 H14B 109.5
C10 C14 H14C 109.5
H14A C14 H14C 109.5
H14B C14 H14C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
I1 C1 2.085(6)
N1 C8 1.342(8)
N1 C6 1.391(8)
N1 H1 0.8800
O1 C8 1.226(8)
O2 C7 1.410(8)
O2 H2 0.8400
O3 C9 1.409(7)
O3 C10 1.425(10)
O4 C11 1.436(11)
O4 C10 1.452(11)
O5 C12 1.202(8)
C1 C6 1.378(9)
C1 C2 1.399(9)
C2 C3 1.371(10)
C2 H2A 0.9500
C3 C4 1.400(10)
C3 H3 0.9500
C4 C5 1.386(9)
C4 H4 0.9500
C5 C6 1.398(8)
C5 C7 1.525(9)
C7 C9 1.537(9)
C7 C8 1.558(8)
C9 C12 1.520(8)
C9 H9 1.0000
C10 C13 1.467(12)
C10 C14 1.522(12)
C11 C12 1.496(10)
C11 H11A 0.9900
C11 H11B 0.9900
C13 H13A 0.9800
C13 H13B 0.9800
C13 H13C 0.9800
C14 H14A 0.9800
C14 H14B 0.9800
C14 H14C 0.9800
