#------------------------------------------------------------------------------
#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/32/4023238.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_4023238
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_moiety         'C22 H30 Br1 N5 O3 Si1'
_chemical_formula_sum            'C22 H30 Br N5 O3 Si'
_chemical_formula_weight         520.51
_chemical_name_systematic        ' ?'
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_type_scat_source
'International Tables for Crystallography (Vol C)'
_audit_creation_date             13-06-02
_audit_creation_method           from_MolEN_and_SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 92.2500(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.4226(2)
_cell_length_b                   26.7406(5)
_cell_length_c                   9.9586(2)
_cell_measurement_reflns_used    16209
_cell_measurement_temperature    150
_cell_measurement_theta_max      27
_cell_measurement_theta_min      2
_cell_volume                     2507.29(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_full 0.9522
_diffrn_measured_fraction_theta_max 0.9348
_diffrn_measurement_device_type  Nonius_KappaCCD
_diffrn_radiation_type           MO-K\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.061
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            16209
_diffrn_reflns_theta_full        26.7
_diffrn_reflns_theta_max         27.89
_diffrn_reflns_theta_min         2.05
_exptl_absorpt_coefficient_mu    1.699
_exptl_absorpt_correction_T_max  0.5756
_exptl_absorpt_correction_T_min  0.3306
_exptl_absorpt_correction_type   refined_empirical_(Otwinowski_&_Minor,_1996)
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.38
_exptl_crystal_description       chunk
_exptl_crystal_F_000             1080
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.33
_refine_diff_density_max         0.36
_refine_diff_density_min         -0.64
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    H_atoms_riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     296
_refine_ls_number_reflns         5920
_refine_ls_number_restraints     0
_refine_ls_R_factor_gt           0.039
_refine_ls_shift/su_max          0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'1/[σ²(Fo²)+(0.0408P)²+0.0000P] where P=(Fo²+2Fc²)/3  '
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.091
_reflns_number_gt                4551
_reflns_number_total             5935
_reflns_threshold_expression     >2.0σ(I)
_cod_data_source_file            jo7021422-File008.cif
_cod_data_source_block           D228A
_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_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 (51 time).

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_original_formula_sum        'C22 H30 Br1 N5 O3 Si1'
_cod_database_code               4023238
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x+1/2, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
Br(6) Br 0.21536(2) 0.193154(11) 0.42912(2) 0.05626(11) Uani 1 1 d . . .
Si(1) Si -0.70129(6) -0.24564(2) 0.51065(6) 0.03809(15) Uani 1 1 d . . .
O(11) O -0.50994(15) -0.10662(6) 0.50448(13) 0.0432(4) Uani 1 1 d . . .
O(32) O -0.32813(14) -0.11258(7) -0.07771(14) 0.0446(4) Uani 1 1 d . . .
O(33) O -0.49806(13) -0.08356(6) 0.05541(13) 0.0452(4) Uani 1 1 d . . .
N(2) N -0.39189(16) -0.08986(7) 0.30987(15) 0.0341(4) Uani 1 1 d . . .
N(4) N -0.22688(15) -0.02104(6) 0.30077(15) 0.0319(4) Uani 1 1 d . . .
N(6) N -0.19543(16) 0.02256(7) 0.51456(15) 0.0347(4) Uani 1 1 d . . .
N(7) N -0.25061(19) 0.01865(8) 0.64158(16) 0.0447(5) Uani 1 1 d . . .
N(31) N -0.26897(16) -0.07139(7) 0.11582(15) 0.0346(4) Uani 1 1 d . . .
C(1) C -0.4190(2) -0.07950(8) 0.4362(2) 0.0362(5) Uani 1 1 d . . .
C(2) C -0.5699(2) -0.15181(9) 0.4423(2) 0.0403(5) Uani 1 1 d . . .
C(3) C -0.29915(19) -0.05965(8) 0.24937(18) 0.0317(4) Uani 1 1 d . . .
C(5) C -0.25430(19) -0.01297(8) 0.43131(18) 0.0322(4) Uani 1 1 d . . .
C(8) C -0.3415(2) -0.01870(9) 0.6351(2) 0.0468(6) Uani 1 1 d . . .
C(9) C -0.3493(2) -0.04022(8) 0.50514(19) 0.0363(5) Uani 1 1 d . . .
C(13) C -0.6400(2) -0.18020(9) 0.5523(2) 0.0411(5) Uani 1 1 d . . .
C(14) C -0.7859(3) -0.27009(10) 0.6631(2) 0.0536(6) Uani 1 1 d . . .
C(15) C -0.8324(2) -0.24455(9) 0.3659(2) 0.0477(6) Uani 1 1 d . . .
C(16) C -0.5463(2) -0.28498(10) 0.4717(3) 0.0575(7) Uani 1 1 d . . .
C(31) C -0.1273(2) -0.06130(11) 0.0683(2) 0.0506(6) Uani 1 1 d . . .
C(32) C -0.3659(2) -0.09233(8) 0.0223(2) 0.0346(5) Uani 1 1 d . . .
C(34) C -0.6193(2) -0.10654(10) -0.0212(2) 0.0403(5) Uani 1 1 d . . .
C(35) C -0.7438(2) -0.08672(15) 0.0535(3) 0.0840(12) Uani 1 1 d . . .
C(36) C -0.6091(3) -0.16246(11) -0.0110(3) 0.0736(9) Uani 1 1 d . . .
C(37) C -0.6241(3) -0.08831(11) -0.1625(2) 0.0595(7) Uani 1 1 d . . .
C(61) C -0.09612(19) 0.06098(8) 0.49220(19) 0.0325(4) Uani 1 1 d . . .
C(62) C -0.0358(2) 0.06733(9) 0.3685(2) 0.0393(5) Uani 1 1 d . . .
C(63) C 0.0585(2) 0.10615(9) 0.3497(2) 0.0434(5) Uani 1 1 d . . .
C(64) C 0.0920(2) 0.13818(9) 0.4555(2) 0.0402(5) Uani 1 1 d . . .
C(65) C 0.0366(2) 0.13131(8) 0.5797(2) 0.0387(5) Uani 1 1 d . . .
C(66) C -0.0578(2) 0.09297(8) 0.5977(2) 0.0377(5) Uani 1 1 d . . .
H(8) H -0.3950 -0.0298 0.7082 0.056 Uiso 1 1 calc R . .
H(2A) H -0.4941 -0.1723 0.4034 0.048 Uiso 1 1 calc R . .
H(2B) H -0.6404 -0.1430 0.3698 0.048 Uiso 1 1 calc R . .
H(62) H -0.0593 0.0450 0.2967 0.047 Uiso 1 1 calc R . .
H(63) H 0.0999 0.1108 0.2651 0.052 Uiso 1 1 calc R . .
H(65) H 0.0632 0.1528 0.6523 0.046 Uiso 1 1 calc R . .
H(66) H -0.0973 0.0882 0.6831 0.045 Uiso 1 1 calc R . .
H(13A) H -0.7232 -0.1607 0.5800 0.049 Uiso 1 1 calc R . .
H(13B) H -0.5723 -0.1820 0.6308 0.049 Uiso 1 1 calc R . .
H(14A) H -0.8058 -0.3058 0.6516 0.080 Uiso 1 1 calc R . .
H(14B) H -0.8749 -0.2521 0.6763 0.080 Uiso 1 1 calc R . .
H(14C) H -0.7215 -0.2652 0.7417 0.080 Uiso 1 1 calc R . .
H(15A) H -0.7953 -0.2241 0.2936 0.072 Uiso 1 1 calc R . .
H(15B) H -0.9220 -0.2303 0.3947 0.072 Uiso 1 1 calc R . .
H(15C) H -0.8488 -0.2787 0.3333 0.072 Uiso 1 1 calc R . .
H(16A) H -0.5780 -0.3193 0.4529 0.086 Uiso 1 1 calc R . .
H(16B) H -0.4783 -0.2850 0.5487 0.086 Uiso 1 1 calc R . .
H(16C) H -0.5005 -0.2714 0.3928 0.086 Uiso 1 1 calc R . .
H(31A) H -0.0818 -0.0929 0.0445 0.076 Uiso 1 1 calc R . .
H(31B) H -0.0701 -0.0446 0.1394 0.076 Uiso 1 1 calc R . .
H(31C) H -0.1347 -0.0396 -0.0110 0.076 Uiso 1 1 calc R . .
H(35A) H -0.7314 -0.0950 0.1490 0.126 Uiso 1 1 calc R . .
H(35B) H -0.8317 -0.1019 0.0169 0.126 Uiso 1 1 calc R . .
H(35C) H -0.7491 -0.0503 0.0429 0.126 Uiso 1 1 calc R . .
H(36A) H -0.5289 -0.1742 -0.0622 0.110 Uiso 1 1 calc R . .
H(36B) H -0.6972 -0.1775 -0.0476 0.110 Uiso 1 1 calc R . .
H(36C) H -0.5946 -0.1721 0.0835 0.110 Uiso 1 1 calc R . .
H(37A) H -0.6187 -0.0517 -0.1631 0.089 Uiso 1 1 calc R . .
H(37B) H -0.7132 -0.0990 -0.2077 0.089 Uiso 1 1 calc R . .
H(37C) H -0.5437 -0.1022 -0.2096 0.089 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_publ_flag
C(16) Si(1) C(14) 109.75(12) yes
C(16) Si(1) C(15) 110.56(11) yes
C(14) Si(1) C(15) 110.17(11) yes
C(16) Si(1) C(13) 109.62(11) yes
C(14) Si(1) C(13) 106.51(11) yes
C(15) Si(1) C(13) 110.14(11) yes
C(1) O(11) C(2) 118.72(16) yes
C(1) N(2) C(3) 116.86(17) yes
C(3) N(4) C(5) 112.33(17) yes
C(5) N(6) N(7) 110.05(16) yes
C(5) N(6) C(61) 131.80(16) yes
N(7) N(6) C(61) 118.14(16) yes
C(8) N(7) N(6) 106.15(16) yes
C(32) N(31) C(3) 124.71(16) yes
C(32) N(31) C(31) 116.16(16) yes
C(3) N(31) C(31) 119.13(16) yes
N(2) C(1) O(11) 121.62(19) yes
N(2) C(1) C(9) 121.18(19) yes
O(11) C(1) C(9) 117.17(18) yes
O(11) C(2) C(13) 106.36(16) yes
N(4) C(3) N(2) 128.65(17) yes
N(4) C(3) N(31) 114.73(18) yes
N(2) C(3) N(31) 116.56(17) yes
N(4) C(5) N(6) 127.34(18) yes
N(4) C(5) C(9) 125.26(19) yes
N(6) C(5) C(9) 107.40(17) yes
N(7) C(8) C(9) 111.35(19) yes
C(5) C(9) C(1) 115.66(18) yes
C(5) C(9) C(8) 105.05(18) yes
C(1) C(9) C(8) 139.3(2) yes
C(2) C(13) Si(1) 116.57(15) yes
O(32) C(32) O(33) 126.92(19) yes
O(32) C(32) N(31) 121.81(18) yes
O(33) C(32) N(31) 111.12(17) yes
C(32) O(33) C(34) 120.84(16) yes
O(33) C(34) C(37) 110.21(19) yes
O(33) C(34) C(36) 109.42(18) yes
C(37) C(34) C(36) 112.9(2) yes
O(33) C(34) C(35) 101.51(17) yes
C(37) C(34) C(35) 110.8(2) yes
C(36) C(34) C(35) 111.4(2) yes
C(62) C(61) C(66) 119.48(19) yes
C(62) C(61) N(6) 121.72(18) yes
C(66) C(61) N(6) 118.80(17) yes
C(63) C(62) C(61) 120.0(2) yes
C(64) C(63) C(62) 119.3(2) yes
C(65) C(64) C(63) 121.3(2) yes
C(65) C(64) Br(6) 118.97(16) yes
C(63) C(64) Br(6) 119.78(17) yes
C(66) C(65) C(64) 119.2(2) yes
C(65) C(66) C(61) 120.68(19) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Br(6) C(64) 1.898(2) yes
Si(1) C(16) 1.854(2) yes
Si(1) C(14) 1.861(2) yes
Si(1) C(15) 1.861(2) yes
Si(1) C(13) 1.884(2) yes
O(11) C(1) 1.330(2) yes
O(11) C(2) 1.461(2) yes
O(32) C(32) 1.200(2) yes
N(2) C(1) 1.323(2) yes
N(2) C(3) 1.349(2) yes
N(4) C(3) 1.328(2) yes
N(4) C(5) 1.353(2) yes
N(6) C(5) 1.364(2) yes
N(6) N(7) 1.390(2) yes
N(6) C(61) 1.413(3) yes
N(7) C(8) 1.316(3) yes
N(31) C(32) 1.396(3) yes
N(31) C(3) 1.406(2) yes
N(31) C(31) 1.459(3) yes
C(1) C(9) 1.404(3) yes
C(2) C(13) 1.506(3) yes
C(5) C(9) 1.387(3) yes
C(8) C(9) 1.415(3) yes
C(32) O(33) 1.322(2) yes
O(33) C(34) 1.482(2) yes
C(34) C(37) 1.488(3) yes
C(34) C(36) 1.502(4) yes
C(34) C(35) 1.510(3) yes
C(61) C(62) 1.387(3) yes
C(61) C(66) 1.392(3) yes
C(62) C(63) 1.384(3) yes
C(63) C(64) 1.384(3) yes
C(64) C(65) 1.374(3) yes
C(65) C(66) 1.374(3) yes
