#------------------------------------------------------------------------------
#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/32/4023236.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_4023236
loop_
_publ_author_name
'Rachel L. Beingessner'
'Bo-Liang Deng'
'Phillip E. Fanwick'
'Hicham Fenniri'
_publ_contact_author_address
;    Department of Chemistry
     Purdue University
     560 Oval Drive 
     West Lafayette, IN 47907-2084
     USA
;
_publ_contact_author_email       fanwick@.xray.chem.purdue.edu
_publ_contact_author_fax         1(765)4940239
_publ_contact_author_name        'Phillip E. Fanwick'
_publ_contact_author_phone       1(765)4944572
_publ_section_title
;
 A Regioselective Approach to Trisubstituted
 2 (or 6)-Arylaminopyrimidine-5-carbaldehydes and Their Application in
 the Synthesis of Structurally and Electronically Unique
 G-C Base Precursors
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              931
_journal_page_last               939
_journal_paper_doi               10.1021/jo7021422
_journal_volume                  73
_journal_year                    2008
_chemical_formula_sum            'C22 H31 I N4 O4 Si'
_chemical_formula_weight         570.51
_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_type_scat_source
'International Tables for Crystallography (Vol C)'
_audit_creation_date             4-06-01
_audit_creation_method           from_MolEN_and_SHELXL
_cell_angle_alpha                71.8355(14)
_cell_angle_beta                 77.8408(17)
_cell_angle_gamma                62.847(3)
_cell_formula_units_Z            2
_cell_length_a                   10.3329(4)
_cell_length_b                   10.5854(4)
_cell_length_c                   14.1306(7)
_cell_measurement_reflns_used    9388
_cell_measurement_temperature    199
_cell_measurement_theta_max      27
_cell_measurement_theta_min      5
_cell_volume                     1302.42(12)
_computing_cell_refinement       DENZO/SCALEPACK_(Otwinowski,_1996)"
_computing_data_collection       Collect_(Nonius,_1998)"
_computing_data_reduction        DENZO/SCALEPACK_(Otwinowski,_1996)"
_computing_molecular_graphics
;
"    ORTEP (Johnson, 1976)"
"    PLUTON (Spek, 1991)"
;
_computing_publication_material  CIF_VAX_MolEN_(Fair,_1990)
_computing_structure_refinement  SHELX97_(Sheldrick,_1997)"
_computing_structure_solution    PATTY_(DIRDIF92,_Beurskins,_1992)"
_diffrn_ambient_temperature      199
_diffrn_measured_fraction_theta_max 0.8980
_diffrn_measurement_device_type  Nonius_KappaCCD
_diffrn_radiation_type           MO-K\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.029
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            9388
_diffrn_reflns_theta_max         27.88
_diffrn_reflns_theta_min         5.00
_exptl_absorpt_coefficient_mu    1.291
_exptl_absorpt_correction_T_max  0.8510
_exptl_absorpt_correction_T_min  0.4834
_exptl_absorpt_correction_type   refined_empirical_(Otwinowski_&_Minor,_1996)
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.45
_exptl_crystal_description       plate
_exptl_crystal_F_000             580
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.48
_refine_diff_density_min         -0.95
_refine_ls_extinction_coef       0.26E-01
_refine_ls_extinction_method     SHELXL97_(Sheldrick_1997)
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment
;
Chemically significant hydrogens refined isotropically
Others riding
;
_refine_ls_matrix_type           full
_refine_ls_number_parameters     301
_refine_ls_number_reflns         5587
_refine_ls_number_restraints     0
_refine_ls_R_factor_gt           0.039
_refine_ls_shift/su_max          0.005
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'1/[σ²(Fo²)+(0.0589P)²+0.0000P] where P=(Fo²+2Fc²)/3  '
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.098
_reflns_number_gt                4857
_reflns_number_total             5589
_reflns_threshold_expression     >2.0σ(I)
_cod_data_source_file            jo7021422-File006.cif
_cod_data_source_block           D90
_cod_depositor_comments
;
The following automatic conversions were performed:
'_refine_ls_weighting_scheme' value 'calc ' changed to 'calc' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

'_geom_bond_publ_flag'
value 'YES' changed to 'yes' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (34
times).

'_geom_bond_publ_flag' value 'NO' changed to 'no' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (2
times).

'_geom_angle_publ_flag' value 'YES' changed to 'yes' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (50
times).

'_geom_angle_publ_flag' value 'NO' changed to 'no' 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_formula_sum        'C22 H31 I1 N4 O4 Si1'
_cod_database_code               4023236
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
I(54) 0.14514(2) 0.06078(2) 0.386228(16) 0.05772(11) Uani ?
Si(34) 1.05888(9) -0.71436(8) -0.32678(6) 0.0417(3) Uani ?
O(12) 0.5351(3) -0.7000(2) 0.15270(16) 0.0513(9) Uani ?
O(13) 0.6479(2) -0.60254(19) 0.20999(13) 0.0385(7) Uani ?
O(31) 1.0009(2) -0.4255(2) -0.16051(14) 0.0397(7) Uani ?
O(41) 0.8563(3) -0.0718(2) -0.05420(17) 0.0538(9) Uani ?
N(2) 0.8404(2) -0.5135(2) -0.05801(15) 0.0325(7) Uani ?
N(6) 0.6650(2) -0.3793(2) 0.05580(16) 0.0314(7) Uani ?
N(11) 0.6806(2) -0.6008(2) 0.04560(17) 0.0364(8) Uani ?
N(50) 0.6556(2) -0.1582(2) 0.06218(17) 0.0346(8) Uani ?
C(1) 0.7317(3) -0.4923(3) 0.01455(18) 0.0310(8) Uani ?
C(3) 0.8898(3) -0.4100(3) -0.08958(18) 0.0323(8) Uani ?
C(4) 0.8348(3) -0.2869(3) -0.05137(18) 0.0327(8) Uani ?
C(5) 0.7173(3) -0.2760(2) 0.02345(18) 0.0303(8) Uani ?
C(11) 0.7019(4) -0.6896(3) -0.0233(2) 0.0481(12) Uani ?
C(12) 0.6124(3) -0.6369(3) 0.1399(2) 0.0358(9) Uani ?
C(14) 0.5974(3) -0.6490(3) 0.3162(2) 0.0418(10) Uani ?
C(15) 0.6636(4) -0.5906(4) 0.3687(2) 0.0611(14) Uani ?
C(16) 0.4324(4) -0.5782(4) 0.3295(3) 0.0557(13) Uani ?
C(17) 0.6599(4) -0.8152(3) 0.3497(3) 0.0646(13) Uani ?
C(32) 1.0625(3) -0.5574(3) -0.1985(2) 0.0386(10) Uani ?
C(33) 0.9808(3) -0.5439(3) -0.2794(2) 0.0401(10) Uani ?
C(35) 1.0554(5) -0.8710(4) -0.2205(3) 0.0652(16) Uani ?
C(36) 0.9440(4) -0.6813(4) -0.4254(3) 0.0555(13) Uani ?
C(37) 1.2495(4) -0.7536(4) -0.3823(3) 0.0572(13) Uani ?
C(41) 0.8978(3) -0.1811(3) -0.0844(2) 0.0432(11) Uani ?
C(51) 0.5425(3) -0.1191(2) 0.13757(19) 0.0326(8) Uani ?
C(52) 0.5069(3) 0.0128(3) 0.1590(2) 0.0378(10) Uani ?
C(53) 0.3960(3) 0.0642(3) 0.2299(2) 0.0405(10) Uani ?
C(54) 0.3192(3) -0.0187(3) 0.2816(2) 0.0388(9) Uani ?
C(55) 0.3545(3) -0.1509(3) 0.2620(2) 0.0444(11) Uani ?
C(56) 0.4665(3) -0.2029(3) 0.1905(2) 0.0405(10) Uani ?
H(41) 0.9763 -0.1982 -0.1326 0.0520 Uiso calc
H(50) 0.689(3) -0.108(3) 0.039(2) 0.034(8) Uiso ?
H(52) 0.5590 0.0679 0.1248 0.0450 Uiso calc
H(53) 0.3729 0.1533 0.2430 0.0490 Uiso calc
H(55) 0.3028 -0.2061 0.2971 0.0530 Uiso calc
H(56) 0.4903 -0.2927 0.1783 0.0490 Uiso calc
H(11A) 0.7874 -0.7799 -0.0085 0.0720 Uiso calc
H(11B) 0.7137 -0.6364 -0.0909 0.0720 Uiso calc
H(11C) 0.6183 -0.7102 -0.0155 0.0720 Uiso calc
H(15A) 0.7677 -0.6326 0.3551 0.0920 Uiso calc
H(15B) 0.6395 -0.6162 0.4394 0.0920 Uiso calc
H(15C) 0.6255 -0.4859 0.3449 0.0920 Uiso calc
H(16A) 0.3972 -0.4760 0.2959 0.0840 Uiso calc
H(16B) 0.4013 -0.5889 0.3994 0.0840 Uiso calc
H(16C) 0.3941 -0.6249 0.3017 0.0840 Uiso calc
H(17A) 0.6216 -0.8507 0.3125 0.0970 Uiso calc
H(17B) 0.6333 -0.8446 0.4196 0.0970 Uiso calc
H(17C) 0.7643 -0.8553 0.3381 0.0970 Uiso calc
H(32A) 1.0627 -0.6399 -0.1437 0.0460 Uiso calc
H(32B) 1.1630 -0.5779 -0.2241 0.0460 Uiso calc
H(33A) 0.9817 -0.4622 -0.3347 0.0480 Uiso calc
H(33B) 0.8799 -0.5221 -0.2542 0.0480 Uiso calc
H(35A) 0.9601 -0.8433 -0.1855 0.0970 Uiso calc
H(35B) 1.1264 -0.8965 -0.1755 0.0970 Uiso calc
H(35C) 1.0781 -0.9538 -0.2457 0.0970 Uiso calc
H(36A) 0.9724 -0.7713 -0.4434 0.0830 Uiso calc
H(36B) 0.9573 -0.6097 -0.4832 0.0830 Uiso calc
H(36C) 0.8432 -0.6459 -0.4004 0.0830 Uiso calc
H(37A) 1.3104 -0.7769 -0.3310 0.0860 Uiso calc
H(37B) 1.2510 -0.6689 -0.4328 0.0860 Uiso calc
H(37C) 1.2851 -0.8351 -0.4117 0.0860 Uiso calc
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C(37) Si(34) C(35) 110.24(17) yes
C(37) Si(34) C(36) 109.07(16) yes
C(35) Si(34) C(36) 110.48(18) yes
C(37) Si(34) C(33) 110.08(15) yes
C(35) Si(34) C(33) 108.87(15) yes
C(36) Si(34) C(33) 108.07(14) yes
C(12) O(13) C(14) 119.7(2) yes
C(3) O(31) C(32) 117.90(18) yes
C(3) N(2) C(1) 115.3(2) yes
C(1) N(6) C(5) 115.9(2) yes
C(1) N(11) C(12) 125.0(2) yes
C(1) N(11) C(11) 119.1(2) yes
C(12) N(11) C(11) 115.9(2) yes
H(50) N(50) C(5) 112(3) yes
H(50) N(50) C(51) 116(3) yes
C(5) N(50) C(51) 131.9(2) yes
N(6) C(1) N(2) 128.0(2) yes
N(6) C(1) N(11) 117.6(2) yes
N(2) C(1) N(11) 114.3(2) yes
N(2) C(3) O(31) 118.6(2) yes
N(2) C(3) C(4) 123.7(2) yes
O(31) C(3) C(4) 117.7(2) yes
C(3) C(4) C(5) 115.3(2) yes
C(3) C(4) C(41) 121.7(2) yes
C(5) C(4) C(41) 123.1(2) yes
N(50) C(5) N(6) 119.4(2) yes
N(50) C(5) C(4) 118.8(2) yes
N(6) C(5) C(4) 121.8(2) yes
O(12) C(12) O(13) 125.9(2) yes
O(12) C(12) N(11) 120.7(2) yes
O(13) C(12) N(11) 113.3(2) yes
O(13) C(14) C(15) 101.9(2) yes
O(13) C(14) C(16) 110.0(2) yes
C(15) C(14) C(16) 111.5(3) yes
O(13) C(14) C(17) 109.9(2) yes
C(15) C(14) C(17) 110.6(3) yes
C(16) C(14) C(17) 112.4(3) yes
O(31) C(32) C(33) 113.4(2) yes
C(32) C(33) Si(34) 113.24(19) yes
O(41) C(41) C(4) 125.4(3) yes
C(52) C(51) C(56) 119.1(2) yes
C(52) C(51) N(50) 116.2(2) yes
C(56) C(51) N(50) 124.7(2) yes
C(53) C(52) C(51) 121.5(2) yes
C(52) C(53) C(54) 119.2(2) yes
C(55) C(54) C(53) 120.0(2) yes
C(55) C(54) I(54) 120.17(19) yes
C(53) C(54) I(54) 119.80(19) yes
C(54) C(55) C(56) 120.9(2) yes
C(55) C(56) C(51) 119.3(2) yes
O(41) H(50) N(50) 147(3) no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
I(54) C(54) 2.098(3) yes
Si(34) C(37) 1.864(3) yes
Si(34) C(35) 1.867(3) yes
Si(34) C(36) 1.868(4) yes
Si(34) C(33) 1.885(3) yes
O(12) C(12) 1.211(3) yes
O(13) C(12) 1.322(3) yes
O(13) C(14) 1.486(3) yes
O(31) C(3) 1.339(3) yes
O(31) C(32) 1.468(3) yes
O(41) C(41) 1.218(4) yes
N(2) C(3) 1.331(3) yes
N(2) C(1) 1.339(3) yes
N(6) C(1) 1.326(3) yes
N(6) C(5) 1.350(3) yes
N(11) C(1) 1.390(3) yes
N(11) C(12) 1.396(3) yes
N(11) C(11) 1.473(3) yes
N(50) H(50) 0.72(3) yes
N(50) C(5) 1.347(3) yes
N(50) C(51) 1.407(3) yes
C(3) C(4) 1.394(4) yes
C(4) C(5) 1.419(3) yes
C(4) C(41) 1.451(3) yes
C(14) C(15) 1.511(5) yes
C(14) C(16) 1.513(4) yes
C(14) C(17) 1.520(4) yes
C(32) C(33) 1.494(4) yes
C(51) C(52) 1.388(3) yes
C(51) C(56) 1.392(4) yes
C(52) C(53) 1.378(4) yes
C(53) C(54) 1.387(4) yes
C(54) C(55) 1.379(4) yes
C(55) C(56) 1.391(4) yes
H(50) O(41) 2.05(3) no
H(50) N(50) 0.72(3) no
