#------------------------------------------------------------------------------
#$Date: 2017-10-13 02:32:00 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201954 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/66/1506611.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_1506611
loop_
_publ_author_name
'Su, Shun'
'Acquilano, Dayle E.'
'Arumugasamy, Jeevanandam'
'Beeler, Aaron B.'
'Eastwood, Erin L.'
'Giguere, Joshua R.'
'Lan, Ping'
'Lei, Xiaoguang'
'Min, Geanna K.'
'Yeager, Adam R.'
'Zhou, Ya'
'Panek, James S.'
'Snyder, John K.'
'Schaus, Scott E.'
'Porco, Jr, John A'
_publ_section_title
;
 Convergent synthesis of a complex oxime library using chemical domain
 shuffling.
;
_journal_issue                   13
_journal_name_full               'Organic letters'
_journal_page_first              2751
_journal_page_last               2754
_journal_paper_doi               10.1021/ol051023r
_journal_volume                  7
_journal_year                    2005
_chemical_formula_sum            'C23 H23 Br O5'
_chemical_formula_weight         459.32
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 100.504(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.0462(7)
_cell_length_b                   5.3870(4)
_cell_length_c                   19.6191(14)
_cell_measurement_temperature    173(2)
_cell_volume                     1043.97(13)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  'Bruker 1K CCD area detector'
_diffrn_measurement_method       '0.3 deg. omega 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  0.0252
_diffrn_reflns_av_sigmaI/netI    0.0626
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            8041
_diffrn_reflns_theta_full        30.51
_diffrn_reflns_theta_max         30.51
_diffrn_reflns_theta_min         2.48
_exptl_absorpt_coefficient_mu    2.000
_exptl_absorpt_correction_T_max  0.7535
_exptl_absorpt_correction_T_min  0.2396
_exptl_absorpt_correction_type   SADABS
_exptl_crystal_colour            cololess
_exptl_crystal_density_diffrn    1.461
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             472
_exptl_crystal_size_max          1.00
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.567
_refine_diff_density_min         -0.503
_refine_diff_density_rms         0.065
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.055(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.964
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     343
_refine_ls_number_reflns         5322
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.964
_refine_ls_R_factor_all          0.0539
_refine_ls_R_factor_gt           0.0384
_refine_ls_shift/su_max          0.023
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0380P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0819
_refine_ls_wR_factor_ref         0.0869
_reflns_number_gt                4249
_reflns_number_total             5322
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol051023rsi20050504_124659.cif
_cod_data_source_block           porco29
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P2(1)
_cod_database_code               1506611
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -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
Br1 Br 0.09435(3) 0.26769(10) 0.419019(13) 0.04135(10) Uani 1 1 d .
O1 O -0.50186(17) 1.4447(4) 0.27787(9) 0.0266(4) Uani 1 1 d .
O2 O -0.81051(18) 1.1847(3) 0.18333(10) 0.0302(4) Uani 1 1 d .
O3 O -1.28556(17) 1.2867(6) -0.00909(9) 0.0362(4) Uani 1 1 d .
O4 O -0.40332(18) 0.9901(4) 0.24072(9) 0.0298(4) Uani 1 1 d .
O5 O -0.37831(17) 0.7402(5) 0.15239(8) 0.0330(5) Uani 1 1 d .
C1 C -0.5547(3) 1.5648(6) 0.33205(14) 0.0289(6) Uani 1 1 d .
H1 H -0.502(3) 1.701(6) 0.3393(14) 0.022(7) Uiso 1 1 d .
C2 C -0.6994(3) 1.6409(6) 0.30806(15) 0.0313(6) Uani 1 1 d .
H2 H -0.736(2) 1.740(7) 0.3401(12) 0.015(6) Uiso 1 1 d .
C3 C -0.7704(3) 1.5654(5) 0.24813(15) 0.0290(6) Uani 1 1 d .
H3 H -0.853(4) 1.648(8) 0.2332(19) 0.058(12) Uiso 1 1 d .
C4 C -0.7166(3) 1.3852(5) 0.20192(13) 0.0257(5) Uani 1 1 d .
H4 H -0.693(3) 1.482(6) 0.1573(14) 0.019(7) Uiso 1 1 d .
C5 C -0.5894(2) 1.2602(7) 0.24223(11) 0.0246(4) Uani 1 1 d .
H5 H -0.617(3) 1.149(6) 0.2741(15) 0.024(8) Uiso 1 1 d .
C6 C -0.5117(3) 1.1212(6) 0.19597(15) 0.0301(6) Uani 1 1 d .
H6B H -0.479(3) 1.250(9) 0.1638(15) 0.035(8) Uiso 1 1 d .
H6A H -0.568(3) 1.018(6) 0.1684(14) 0.019(7) Uiso 1 1 d .
C7 C -0.5341(3) 1.4054(7) 0.39831(16) 0.0339(7) Uani 1 1 d .
H7B H -0.584(4) 1.286(11) 0.3869(18) 0.050(10) Uiso 1 1 d .
H7A H -0.564(3) 1.489(7) 0.4336(16) 0.033(9) Uiso 1 1 d .
C8 C -0.3884(3) 1.3459(10) 0.42509(19) 0.0637(17) Uani 1 1 d .
H8 H -0.3410 1.2923 0.3900 0.076 Uiso 1 1 calc R
C9 C -0.3230(5) 1.3519(10) 0.4787(3) 0.0892(19) Uani 1 1 d .
H9B H -0.3610 1.4031 0.5174 0.107 Uiso 1 1 calc R
H9A H -0.2304 1.3056 0.4849 0.107 Uiso 1 1 calc R
C10 C -0.9526(3) 1.4298(5) 0.09122(14) 0.0258(5) Uani 1 1 d .
H10 H -0.893(4) 1.560(8) 0.0911(17) 0.046(10) Uiso 1 1 d .
C11 C -1.0738(3) 1.4430(6) 0.04395(13) 0.0273(6) Uani 1 1 d .
H11 H -1.089(3) 1.570(7) 0.0130(16) 0.033(9) Uiso 1 1 d .
C12 C -1.1707(2) 1.2573(8) 0.04074(11) 0.0254(5) Uani 1 1 d .
C13 C -1.1482(3) 1.0585(5) 0.08591(13) 0.0246(6) Uani 1 1 d .
H13 H -1.203(3) 0.934(6) 0.0829(14) 0.016(7) Uiso 1 1 d .
C14 C -1.0262(3) 1.0435(5) 0.13328(13) 0.0243(5) Uani 1 1 d .
H14 H -1.009(3) 0.896(6) 0.1596(15) 0.027(8) Uiso 1 1 d .
C15 C -0.9288(2) 1.2262(5) 0.13534(12) 0.0230(6) Uani 1 1 d .
C16 C -1.3857(3) 1.0966(8) -0.01190(18) 0.0405(8) Uani 1 1 d .
H16C H -1.349(3) 0.949(7) -0.0219(16) 0.029(8) Uiso 1 1 d .
H16B H -1.420(4) 1.085(8) 0.033(2) 0.057(12) Uiso 1 1 d .
H16A H -1.470(4) 1.144(8) -0.0501(19) 0.060(12) Uiso 1 1 d .
C17 C -0.3451(2) 0.8036(7) 0.21168(13) 0.0266(7) Uani 1 1 d .
C18 C -0.2340(2) 0.6859(5) 0.26192(13) 0.0238(5) Uani 1 1 d .
C19 C -0.1939(2) 0.7774(9) 0.32944(12) 0.0308(5) Uani 1 1 d .
H19 H -0.222(3) 0.939(7) 0.3442(16) 0.031(8) Uiso 1 1 d .
C20 C -0.0944(3) 0.6523(6) 0.37607(14) 0.0319(6) Uani 1 1 d .
H20 H -0.074(3) 0.723(8) 0.4223(15) 0.044(9) Uiso 1 1 d .
C21 C -0.0371(2) 0.4424(6) 0.35450(14) 0.0284(6) Uani 1 1 d .
C22 C -0.0721(3) 0.3513(6) 0.28777(15) 0.0305(6) Uani 1 1 d .
H22 H -0.034(3) 0.213(8) 0.2713(17) 0.045(11) Uiso 1 1 d .
C23 C -0.1715(3) 0.4776(6) 0.24128(14) 0.0285(6) Uani 1 1 d .
H23 H -0.194(4) 0.414(9) 0.200(2) 0.063(13) Uiso 1 1 d .
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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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
C5 O1 C1 113.72(19)
C15 O2 C4 119.4(2)
C12 O3 C16 116.0(3)
C17 O4 C6 116.4(2)
O1 C1 C2 111.2(2)
O1 C1 C7 111.4(2)
C2 C1 C7 113.0(2)
C3 C2 C1 122.0(3)
C2 C3 C4 122.8(3)
O2 C4 C3 110.4(2)
O2 C4 C5 104.3(2)
C3 C4 C5 109.4(2)
O1 C5 C6 107.6(2)
O1 C5 C4 109.2(3)
C6 C5 C4 112.60(19)
O4 C6 C5 107.0(2)
C8 C7 C1 112.8(3)
C9 C8 C7 133.1(5)
C15 C10 C11 119.0(3)
C12 C11 C10 121.0(3)
O3 C12 C13 124.1(3)
O3 C12 C11 116.0(3)
C13 C12 C11 119.8(2)
C12 C13 C14 119.4(3)
C15 C14 C13 120.5(2)
C14 C15 C10 120.2(2)
C14 C15 O2 114.7(2)
C10 C15 O2 125.1(2)
O5 C17 O4 124.0(3)
O5 C17 C18 124.3(3)
O4 C17 C18 111.7(2)
C23 C18 C19 119.7(3)
C23 C18 C17 118.5(2)
C19 C18 C17 121.8(3)
C20 C19 C18 119.8(3)
C21 C20 C19 119.1(3)
C20 C21 C22 122.5(3)
C20 C21 Br1 118.8(2)
C22 C21 Br1 118.7(2)
C21 C22 C23 118.2(3)
C18 C23 C22 120.8(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C21 1.903(3)
O1 C5 1.423(4)
O1 C1 1.427(3)
O2 C15 1.393(3)
O2 C4 1.437(3)
O3 C12 1.379(3)
O3 C16 1.429(4)
O4 C17 1.341(4)
O4 C6 1.451(3)
O5 C17 1.200(3)
C1 C2 1.501(4)
C1 C7 1.540(4)
C2 C3 1.323(4)
C3 C4 1.495(4)
C4 C5 1.531(3)
C5 C6 1.501(4)
C7 C8 1.497(4)
C8 C9 1.134(6)
C10 C15 1.391(4)
C10 C11 1.391(3)
C11 C12 1.389(5)
C12 C13 1.382(5)
C13 C14 1.399(3)
C14 C15 1.383(4)
C17 C18 1.489(3)
C18 C23 1.381(4)
C18 C19 1.402(4)
C19 C20 1.399(4)
C20 C21 1.371(4)
C21 C22 1.382(4)
C22 C23 1.400(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21199685
