#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/32/4023240.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_4023240
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 Dr.
     W. 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_moiety         'C35 H41 I1 N6 O8'
_chemical_formula_sum            'C35 H41 I N6 O8'
_chemical_formula_weight         800.66
_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             13-02-03
_audit_creation_method           from_MolEN_and_SHELXL
_cell_angle_alpha                94.683(3)
_cell_angle_beta                 102.470(2)
_cell_angle_gamma                92.102(2)
_cell_formula_units_Z            2
_cell_length_a                   10.3870(5)
_cell_length_b                   12.3968(6)
_cell_length_c                   14.6661(6)
_cell_measurement_reflns_used    17875
_cell_measurement_temperature    150
_cell_measurement_theta_max      27
_cell_measurement_theta_min      2
_cell_volume                     1834.92(15)
_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_(DIRDIF99,_Beurskins,_1999)
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_max 0.7019
_diffrn_measurement_device_type  Nonius_KappaCCD
_diffrn_measurement_method       ω
_diffrn_radiation_type           MO-K\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.032
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            17875
_diffrn_reflns_theta_max         27.88
_diffrn_reflns_theta_min         2.08
_exptl_absorpt_coefficient_mu    0.916
_exptl_absorpt_correction_T_max  0.7687
_exptl_absorpt_correction_T_min  0.1118
_exptl_absorpt_correction_type   multi-scan_(Otwinowski_&_Minor)
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.45
_exptl_crystal_description       chunk
_exptl_crystal_F_000             820
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.29
_refine_diff_density_max         0.41
_refine_diff_density_min         -0.80
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    H_atoms_riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     461
_refine_ls_number_reflns         8509
_refine_ls_number_restraints     0
_refine_ls_R_factor_gt           0.035
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'1/[σ²(Fo²)+(0.0412P)²+0.0000P] where P=(Fo²+2Fc²)/3  '
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.081
_reflns_number_gt                7035
_reflns_number_total             8531
_reflns_threshold_expression     >2.0σ(I)
_cod_data_source_file            jo7021422-File010.cif
_cod_data_source_block           D361
_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.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_formula_sum        'C35 H41 I1 N6 O8'
_cod_database_code               4023240
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
I(24) I 0.066640(15) 0.367826(15) 0.179940(11) 0.04448(8) Uani 1 1 d . . .
O(8) O 0.07576(14) 0.53255(12) -0.59641(10) 0.0301(3) Uani 1 1 d . . .
O(27) O 0.51388(15) 0.28088(12) -0.10245(11) 0.0327(4) Uani 1 1 d . . .
O(28) O 0.52320(14) 0.37557(12) -0.22724(10) 0.0267(3) Uani 1 1 d . . .
O(40) O 0.26293(15) 0.75955(11) -0.19313(10) 0.0275(3) Uani 1 1 d . . .
O(61) O 0.37412(16) 0.95994(14) -0.34138(14) 0.0472(5) Uani 1 1 d . . .
O(62) O 0.41302(14) 0.78399(12) -0.37376(11) 0.0314(4) Uani 1 1 d . . .
O(64) O -0.00672(14) 0.82500(12) -0.36340(11) 0.0308(3) Uani 1 1 d . . .
O(65) O 0.12495(14) 0.98060(11) -0.33859(11) 0.0298(3) Uani 1 1 d . . .
N(1) N 0.27246(16) 0.44686(13) -0.30224(12) 0.0222(4) Uani 1 1 d . . .
N(3) N 0.31501(16) 0.58401(13) -0.17311(12) 0.0236(4) Uani 1 1 d . . .
N(7) N 0.14578(16) 0.67543(14) -0.48674(12) 0.0234(4) Uani 1 1 d . . .
N(9) N 0.18765(16) 0.49210(13) -0.45269(12) 0.0224(4) Uani 1 1 d . . .
N(20) N 0.36456(17) 0.40674(13) -0.14888(12) 0.0234(4) Uani 1 1 d . . .
N(60) N 0.20786(16) 0.82211(13) -0.37474(12) 0.0224(4) Uani 1 1 d . . .
C(2) C 0.31489(19) 0.48328(16) -0.21355(14) 0.0215(4) Uani 1 1 d . . .
C(4) C 0.26801(19) 0.65876(16) -0.22966(14) 0.0217(4) Uani 1 1 d . . .
C(5) C 0.22480(19) 0.63340(16) -0.32737(14) 0.0206(4) Uani 1 1 d . . .
C(6) C 0.18831(19) 0.70674(16) -0.39874(14) 0.0213(4) Uani 1 1 d . . .
C(8) C 0.13126(19) 0.56494(17) -0.51656(14) 0.0233(4) Uani 1 1 d . . .
C(10) C 0.22843(18) 0.52463(16) -0.35923(14) 0.0212(4) Uani 1 1 d . . .
C(21) C 0.3005(2) 0.39958(16) -0.07149(14) 0.0216(4) Uani 1 1 d . . .
C(22) C 0.1634(2) 0.39003(17) -0.09209(15) 0.0261(5) Uani 1 1 d . . .
C(23) C 0.0962(2) 0.38353(17) -0.02025(16) 0.0291(5) Uani 1 1 d . . .
C(24) C 0.1664(2) 0.38568(17) 0.07194(15) 0.0262(5) Uani 1 1 d . . .
C(25) C 0.3044(2) 0.39671(17) 0.09213(15) 0.0262(5) Uani 1 1 d . . .
C(26) C 0.3710(2) 0.40368(16) 0.02041(15) 0.0250(5) Uani 1 1 d . . .
C(27) C 0.4726(2) 0.34684(16) -0.15625(15) 0.0251(5) Uani 1 1 d . . .
C(29) C 0.6192(2) 0.30606(18) -0.26281(16) 0.0312(5) Uani 1 1 d . . .
C(40) C 0.3082(3) 0.77812(18) -0.09024(15) 0.0366(6) Uani 1 1 d . . .
C(41) C 0.2824(2) 0.89140(17) -0.06128(15) 0.0276(5) Uani 1 1 d . . .
C(42) C 0.3494(2) 0.97859(19) -0.08706(18) 0.0387(6) Uani 1 1 d . . .
C(43) C 0.3289(3) 1.0830(2) -0.0571(2) 0.0505(7) Uani 1 1 d . . .
C(44) C 0.2433(3) 1.1025(2) 0.00073(19) 0.0517(7) Uani 1 1 d . . .
C(45) C 0.1761(3) 1.0173(2) 0.02756(18) 0.0516(7) Uani 1 1 d . . .
C(46) C 0.1949(3) 0.9119(2) -0.00373(17) 0.0411(6) Uani 1 1 d . . .
C(61) C 0.3381(2) 0.86760(19) -0.36058(16) 0.0292(5) Uani 1 1 d . . .
C(63) C 0.5590(2) 0.7944(2) -0.35111(17) 0.0380(6) Uani 1 1 d . . .
C(64) C 0.0968(2) 0.87579(17) -0.35801(14) 0.0244(5) Uani 1 1 d . . .
C(66) C 0.0248(2) 1.05623(18) -0.31696(16) 0.0313(5) Uani 1 1 d . . .
C(91) C 0.1814(2) 0.37594(17) -0.48444(16) 0.0292(5) Uani 1 1 d . . .
C(291) C 0.7483(2) 0.3120(2) -0.1912(2) 0.0461(7) Uani 1 1 d . . .
C(292) C 0.6334(3) 0.3593(2) -0.34966(19) 0.0461(7) Uani 1 1 d . . .
C(293) C 0.5594(3) 0.1912(2) -0.2875(2) 0.0506(7) Uani 1 1 d . . .
C(623) C 0.5919(2) 0.6771(2) -0.36348(19) 0.0468(7) Uani 1 1 d . . .
C(631) C 0.6081(3) 0.8420(3) -0.2506(2) 0.0535(7) Uani 1 1 d . . .
C(633) C 0.6055(3) 0.8613(3) -0.4210(2) 0.0596(8) Uani 1 1 d . . .
C(661) C -0.0266(3) 1.0216(2) -0.23434(17) 0.0431(6) Uani 1 1 d . . .
C(662) C -0.0845(3) 1.0597(2) -0.40485(18) 0.0440(6) Uani 1 1 d . . .
C(663) C 0.1059(3) 1.1635(2) -0.2934(2) 0.0503(7) Uani 1 1 d . . .
H(22) H 0.1156 0.3879 -0.1553 0.031 Uiso 1 1 calc R . .
H(23) H 0.0024 0.3776 -0.0342 0.035 Uiso 1 1 calc R . .
H(25) H 0.3525 0.3994 0.1553 0.031 Uiso 1 1 calc R . .
H(26) H 0.4648 0.4112 0.0342 0.030 Uiso 1 1 calc R . .
H(42) H 0.4104 0.9659 -0.1261 0.046 Uiso 1 1 calc R . .
H(43) H 0.3742 1.1419 -0.0765 0.061 Uiso 1 1 calc R . .
H(44) H 0.2303 1.1749 0.0223 0.062 Uiso 1 1 calc R . .
H(45) H 0.1167 1.0308 0.0676 0.062 Uiso 1 1 calc R . .
H(46) H 0.1475 0.8533 0.0144 0.049 Uiso 1 1 calc R . .
H(29A) H 0.7779 0.3881 -0.1723 0.069 Uiso 1 1 calc R . .
H(29B) H 0.8149 0.2752 -0.2186 0.069 Uiso 1 1 calc R . .
H(29C) H 0.7359 0.2765 -0.1362 0.069 Uiso 1 1 calc R . .
H(29D) H 0.5466 0.3596 -0.3923 0.069 Uiso 1 1 calc R . .
H(29E) H 0.6930 0.3187 -0.3812 0.069 Uiso 1 1 calc R . .
H(29F) H 0.6696 0.4340 -0.3317 0.069 Uiso 1 1 calc R . .
H(29G) H 0.5529 0.1585 -0.2299 0.076 Uiso 1 1 calc R . .
H(29H) H 0.6156 0.1484 -0.3205 0.076 Uiso 1 1 calc R . .
H(29I) H 0.4711 0.1924 -0.3279 0.076 Uiso 1 1 calc R . .
H(40A) H 0.4038 0.7666 -0.0716 0.044 Uiso 1 1 calc R . .
H(40B) H 0.2600 0.7268 -0.0594 0.044 Uiso 1 1 calc R . .
H(62A) H 0.5560 0.6358 -0.3195 0.070 Uiso 1 1 calc R . .
H(62B) H 0.6880 0.6724 -0.3511 0.070 Uiso 1 1 calc R . .
H(62C) H 0.5529 0.6471 -0.4279 0.070 Uiso 1 1 calc R . .
H(63A) H 0.5844 0.9176 -0.2447 0.080 Uiso 1 1 calc R . .
H(63B) H 0.7044 0.8388 -0.2329 0.080 Uiso 1 1 calc R . .
H(63C) H 0.5675 0.8003 -0.2092 0.080 Uiso 1 1 calc R . .
H(63D) H 0.5664 0.8296 -0.4848 0.089 Uiso 1 1 calc R . .
H(63E) H 0.7020 0.8619 -0.4103 0.089 Uiso 1 1 calc R . .
H(63F) H 0.5782 0.9357 -0.4130 0.089 Uiso 1 1 calc R . .
H(66A) H -0.0799 0.9533 -0.2528 0.065 Uiso 1 1 calc R . .
H(66B) H -0.0812 1.0776 -0.2141 0.065 Uiso 1 1 calc R . .
H(66C) H 0.0480 1.0115 -0.1826 0.065 Uiso 1 1 calc R . .
H(66D) H -0.0458 1.0811 -0.4565 0.066 Uiso 1 1 calc R . .
H(66E) H -0.1480 1.1124 -0.3924 0.066 Uiso 1 1 calc R . .
H(66F) H -0.1296 0.9877 -0.4221 0.066 Uiso 1 1 calc R . .
H(66G) H 0.1749 1.1595 -0.2367 0.075 Uiso 1 1 calc R . .
H(66H) H 0.0483 1.2219 -0.2827 0.075 Uiso 1 1 calc R . .
H(66I) H 0.1468 1.1783 -0.3457 0.075 Uiso 1 1 calc R . .
H(91A) H 0.2684 0.3470 -0.4637 0.044 Uiso 1 1 calc R . .
H(91B) H 0.1553 0.3662 -0.5530 0.044 Uiso 1 1 calc R . .
H(91C) H 0.1164 0.3372 -0.4577 0.044 Uiso 1 1 calc R . .
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
C(27) O(28) C(29) 119.90(16) . . ?
C(4) O(40) C(40) 115.68(15) . . ?
C(61) O(62) C(63) 122.68(18) . . ?
C(64) O(65) C(66) 121.72(16) . . ?
C(2) N(1) C(10) 113.99(17) . . ?
C(4) N(3) C(2) 116.34(17) . . ?
C(6) N(7) C(8) 119.78(17) . . ?
C(10) N(9) C(8) 120.83(17) . . ?
C(10) N(9) C(91) 119.33(16) . . ?
C(8) N(9) C(91) 119.01(17) . . ?
C(27) N(20) C(2) 122.57(16) . . ?
C(27) N(20) C(21) 121.37(16) . . ?
C(2) N(20) C(21) 115.97(15) . . ?
C(64) N(60) C(61) 126.58(17) . . ?
C(64) N(60) C(6) 115.95(15) . . ?
C(61) N(60) C(6) 117.09(16) . . ?
N(1) C(2) N(3) 128.85(18) . . ?
N(1) C(2) N(20) 117.59(17) . . ?
N(3) C(2) N(20) 113.54(17) . . ?
O(40) C(4) N(3) 118.99(18) . . ?
O(40) C(4) C(5) 119.48(17) . . ?
N(3) C(4) C(5) 121.53(18) . . ?
C(10) C(5) C(4) 115.62(17) . . ?
C(10) C(5) C(6) 116.01(18) . . ?
C(4) C(5) C(6) 128.14(18) . . ?
N(7) C(6) C(5) 123.65(19) . . ?
N(7) C(6) N(60) 116.16(17) . . ?
C(5) C(6) N(60) 120.03(18) . . ?
O(8) C(8) N(7) 121.21(18) . . ?
O(8) C(8) N(9) 120.72(19) . . ?
N(7) C(8) N(9) 118.02(18) . . ?
N(1) C(10) N(9) 116.54(18) . . ?
N(1) C(10) C(5) 123.57(18) . . ?
N(9) C(10) C(5) 119.89(17) . . ?
C(26) C(21) C(22) 120.44(19) . . ?
C(26) C(21) N(20) 122.14(18) . . ?
C(22) C(21) N(20) 117.41(19) . . ?
C(21) C(22) C(23) 120.0(2) . . ?
C(24) C(23) C(22) 119.8(2) . . ?
C(23) C(24) C(25) 119.77(19) . . ?
C(23) C(24) I(24) 120.16(15) . . ?
C(25) C(24) I(24) 120.05(16) . . ?
C(26) C(25) C(24) 120.2(2) . . ?
C(21) C(26) C(25) 119.71(19) . . ?
O(27) C(27) O(28) 126.81(18) . . ?
O(27) C(27) N(20) 122.80(18) . . ?
O(28) C(27) N(20) 110.36(17) . . ?
O(28) C(29) C(291) 109.95(18) . . ?
O(28) C(29) C(292) 101.56(17) . . ?
C(291) C(29) C(292) 111.5(2) . . ?
O(28) C(29) C(293) 109.41(18) . . ?
C(291) C(29) C(293) 112.5(2) . . ?
C(292) C(29) C(293) 111.4(2) . . ?
O(40) C(40) C(41) 108.05(17) . . ?
C(46) C(41) C(42) 118.5(2) . . ?
C(46) C(41) C(40) 120.3(2) . . ?
C(42) C(41) C(40) 121.2(2) . . ?
C(43) C(42) C(41) 121.0(2) . . ?
C(44) C(43) C(42) 120.2(2) . . ?
C(43) C(44) C(45) 119.9(2) . . ?
C(44) C(45) C(46) 120.1(2) . . ?
C(41) C(46) C(45) 120.3(2) . . ?
O(61) C(61) O(62) 127.0(2) . . ?
O(61) C(61) N(60) 127.4(2) . . ?
O(62) C(61) N(60) 105.63(18) . . ?
O(62) C(63) C(623) 100.99(19) . . ?
O(62) C(63) C(631) 109.69(19) . . ?
C(623) C(63) C(631) 111.4(2) . . ?
O(62) C(63) C(633) 109.3(2) . . ?
C(623) C(63) C(633) 111.9(2) . . ?
C(631) C(63) C(633) 112.9(2) . . ?
O(64) C(64) O(65) 129.04(19) . . ?
O(64) C(64) N(60) 120.13(19) . . ?
O(65) C(64) N(60) 110.83(17) . . ?
O(65) C(66) C(661) 109.86(17) . . ?
O(65) C(66) C(663) 101.69(18) . . ?
C(661) C(66) C(663) 112.0(2) . . ?
O(65) C(66) C(662) 108.89(18) . . ?
C(661) C(66) C(662) 112.8(2) . . ?
C(663) C(66) C(662) 111.0(2) . . ?
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
I(24) C(24) 2.093(2) . ?
O(8) C(8) 1.217(2) . ?
O(27) C(27) 1.208(2) . ?
O(28) C(27) 1.330(2) . ?
O(28) C(29) 1.491(2) . ?
O(40) C(4) 1.326(2) . ?
O(40) C(40) 1.477(3) . ?
O(61) C(61) 1.183(3) . ?
O(62) C(61) 1.345(3) . ?
O(62) C(63) 1.479(3) . ?
O(64) C(64) 1.210(2) . ?
O(65) C(64) 1.315(2) . ?
O(65) C(66) 1.493(3) . ?
N(1) C(2) 1.316(3) . ?
N(1) C(10) 1.355(3) . ?
N(3) C(4) 1.330(3) . ?
N(3) C(2) 1.338(3) . ?
N(7) C(6) 1.293(3) . ?
N(7) C(8) 1.396(3) . ?
N(9) C(10) 1.367(3) . ?
N(9) C(8) 1.406(3) . ?
N(9) C(91) 1.471(3) . ?
N(20) C(27) 1.387(3) . ?
N(20) C(2) 1.427(2) . ?
N(20) C(21) 1.441(3) . ?
N(60) C(64) 1.409(2) . ?
N(60) C(61) 1.412(3) . ?
N(60) C(6) 1.441(3) . ?
C(4) C(5) 1.412(3) . ?
C(5) C(10) 1.395(3) . ?
C(5) C(6) 1.441(3) . ?
C(21) C(26) 1.384(3) . ?
C(21) C(22) 1.389(3) . ?
C(22) C(23) 1.390(3) . ?
C(23) C(24) 1.388(3) . ?
C(24) C(25) 1.398(3) . ?
C(25) C(26) 1.385(3) . ?
C(29) C(291) 1.509(3) . ?
C(29) C(292) 1.513(3) . ?
C(29) C(293) 1.516(3) . ?
C(40) C(41) 1.485(3) . ?
C(41) C(46) 1.384(3) . ?
C(41) C(42) 1.386(3) . ?
C(42) C(43) 1.372(4) . ?
C(43) C(44) 1.370(4) . ?
C(44) C(45) 1.375(4) . ?
C(45) C(46) 1.385(4) . ?
C(63) C(623) 1.511(4) . ?
C(63) C(631) 1.514(4) . ?
C(63) C(633) 1.515(3) . ?
C(66) C(661) 1.511(3) . ?
C(66) C(663) 1.522(3) . ?
C(66) C(662) 1.527(3) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30658637
