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#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/67/1506742.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_1506742
loop_
_publ_author_name
'Lim, Yeon-Hee'
'Li, Tindy'
'Chen, Peiling'
'Schreiber, Patrick'
'Kuznetsova, Larissa'
'Carroll, Patrick J.'
'Lauher, Joseph W.'
'Sieburth, Scott McN'
_publ_section_title
;
 Asymmetry by electrophilic rearrangement of symmetric 2-pyridone
 photodimers.
;
_journal_issue                   24
_journal_name_full               'Organic letters'
_journal_page_first              5413
_journal_page_last               5415
_journal_paper_doi               10.1021/ol052071e
_journal_volume                  7
_journal_year                    2005
_chemical_formula_sum            'C24 H38 Cl2 N2 O2'
_chemical_formula_weight         457.46
_space_group_IT_number           33
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      33
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.8244(17)
_cell_length_b                   16.1213(18)
_cell_length_c                   12.0929(14)
_cell_measurement_temperature    143(1)
_cell_volume                     2500.2(5)
_computing_data_collection       'CrystalClear (Rigaku, 1999)'
_computing_data_reduction        'CrystalClear (Rigaku, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare, 1999)'
_diffrn_ambient_temperature      143(1)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device       'CCD Area Detector'
_diffrn_measurement_device_type  'Rigaku Mercury'
_diffrn_measurement_method       'phi and omega rotations'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0255
_diffrn_reflns_av_sigmaI/netI    0.0459
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7377
_diffrn_reflns_theta_full        25.34
_diffrn_reflns_theta_max         25.34
_diffrn_reflns_theta_min         2.53
_exptl_absorpt_coefficient_mu    0.282
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7856
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_density_diffrn    1.215
_exptl_crystal_F_000             984
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.739
_refine_diff_density_min         -0.429
_refine_diff_density_rms         0.100
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.08(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.116
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     275
_refine_ls_number_reflns         3501
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.116
_refine_ls_R_factor_all          0.0540
_refine_ls_R_factor_gt           0.0462
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1223P)²+0.1167P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1344
_refine_ls_wR_factor_ref         0.1706
_reflns_number_gt                3194
_reflns_number_total             3501
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol052071esi20050827_120718.cif
_cod_data_source_block           shelxl
_cod_original_sg_symbol_H-M      'P n a 21   '
_cod_database_code               1506742
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, z+1/2'
'x+1/2, -y+1/2, z'
'-x, -y, 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
C1 C 0.3782(3) 0.7015(2) 0.6107(3) 0.0256(9) Uani 1 1 d .
H1 H 0.4533 0.6932 0.6006 0.034 Uiso 1 1 calc R
C2 C 0.3245(3) 0.6169(2) 0.6172(4) 0.0235(9) Uani 1 1 d .
H2 H 0.3444 0.5931 0.6887 0.031 Uiso 1 1 calc R
C3 C 0.3503(3) 0.5489(2) 0.5279(3) 0.0229(9) Uani 1 1 d .
H3 H 0.3276 0.4973 0.5633 0.030 Uiso 1 1 calc R
C4 C 0.2877(3) 0.5506(3) 0.4214(4) 0.0266(9) Uani 1 1 d .
H4 H 0.2716 0.4983 0.3939 0.035 Uiso 1 1 calc R
C5 C 0.2522(3) 0.6115(3) 0.3611(4) 0.0307(10) Uani 1 1 d .
H5 H 0.2144 0.5959 0.2989 0.041 Uiso 1 1 calc R
C6 C 0.2638(3) 0.7029(3) 0.3781(4) 0.0290(9) Uani 1 1 d .
H6 H 0.2379 0.7340 0.3141 0.039 Uiso 1 1 calc R
C7 C 0.2236(3) 0.7412(3) 0.4887(4) 0.0263(10) Uani 1 1 d .
H7 H 0.1867 0.7934 0.4749 0.035 Uiso 1 1 calc R
C8 C 0.3382(3) 0.7577(3) 0.5208(4) 0.0244(9) Uani 1 1 d .
H8 H 0.3530 0.8165 0.5346 0.032 Uiso 1 1 calc R
C9 C 0.1590(3) 0.6846(3) 0.5592(4) 0.0272(9) Uani 1 1 d .
C10 C 0.1512(3) 0.5710(3) 0.6929(4) 0.0312(10) Uani 1 1 d .
H10A H 0.1868 0.5179 0.6943 0.041 Uiso 1 1 calc R
H10B H 0.0825 0.5622 0.6614 0.041 Uiso 1 1 calc R
C11 C 0.1395(4) 0.6030(3) 0.8111(5) 0.0444(13) Uani 1 1 d .
H11A H 0.2076 0.6190 0.8388 0.059 Uiso 1 1 calc R
H11B H 0.0960 0.6522 0.8104 0.059 Uiso 1 1 calc R
C12 C 0.0924(4) 0.5401(4) 0.8886(5) 0.0524(15) Uani 1 1 d .
H12A H 0.1372 0.4917 0.8911 0.070 Uiso 1 1 calc R
H12B H 0.0900 0.5636 0.9625 0.070 Uiso 1 1 calc R
C13 C -0.0155(5) 0.5134(4) 0.8563(6) 0.0623(17) Uani 1 1 d .
H13A H -0.0601 0.5611 0.8519 0.093 Uiso 1 1 calc R
H13B H -0.0423 0.4756 0.9107 0.093 Uiso 1 1 calc R
H13C H -0.0132 0.4864 0.7856 0.093 Uiso 1 1 calc R
C14 C 0.4682(3) 0.5337(2) 0.5060(3) 0.0241(9) Uani 1 1 d .
C15 C 0.5274(3) 0.5216(3) 0.6152(4) 0.0281(9) Uani 1 1 d .
H15A H 0.5217 0.5722 0.6580 0.037 Uiso 1 1 calc R
H15B H 0.4932 0.4779 0.6568 0.037 Uiso 1 1 calc R
C16 C 0.6412(4) 0.4999(3) 0.6043(4) 0.0369(11) Uani 1 1 d .
H16 H 0.6576 0.4476 0.5769 0.049 Uiso 1 1 calc R
C17 C 0.7188(4) 0.5489(4) 0.6306(5) 0.0460(12) Uani 1 1 d .
H17A H 0.7056 0.6017 0.6583 0.061 Uiso 1 1 calc R
H17B H 0.7872 0.5310 0.6215 0.061 Uiso 1 1 calc R
C18 C 0.4830(4) 0.4589(3) 0.4293(4) 0.0311(10) Uani 1 1 d .
H18A H 0.4520 0.4716 0.3581 0.041 Uiso 1 1 calc R
H18B H 0.5570 0.4504 0.4177 0.041 Uiso 1 1 calc R
C19 C 0.4358(4) 0.3789(3) 0.4722(4) 0.0384(11) Uani 1 1 d .
H19 H 0.4491 0.3641 0.5451 0.051 Uiso 1 1 calc R
C20 C 0.3769(5) 0.3291(3) 0.4123(5) 0.0536(15) Uani 1 1 d .
H20A H 0.3622 0.3423 0.3391 0.071 Uiso 1 1 calc R
H20B H 0.3502 0.2808 0.4433 0.071 Uiso 1 1 calc R
C21 C 0.4208(4) 0.7928(3) 0.3324(4) 0.0334(10) Uani 1 1 d .
H21A H 0.4803 0.8186 0.3680 0.044 Uiso 1 1 calc R
H21B H 0.3696 0.8355 0.3167 0.044 Uiso 1 1 calc R
C22 C 0.4551(5) 0.7512(3) 0.2248(4) 0.0503(15) Uani 1 1 d .
H22A H 0.4008 0.7134 0.2006 0.067 Uiso 1 1 calc R
H22B H 0.5174 0.7186 0.2388 0.067 Uiso 1 1 calc R
C23 C 0.4778(5) 0.8131(3) 0.1320(5) 0.0524(14) Uani 1 1 d .
H23A H 0.5117 0.8616 0.1629 0.070 Uiso 1 1 calc R
H23B H 0.5253 0.7880 0.0793 0.070 Uiso 1 1 calc R
C24 C 0.3829(7) 0.8383(6) 0.0751(9) 0.109(3) Uani 1 1 d .
H24A H 0.3536 0.7915 0.0372 0.163 Uiso 1 1 calc R
H24B H 0.3991 0.8811 0.0225 0.163 Uiso 1 1 calc R
H24C H 0.3335 0.8591 0.1280 0.163 Uiso 1 1 calc R
N1 N 0.2099(2) 0.6287(2) 0.6217(3) 0.0255(7) Uani 1 1 d .
N2 N 0.3744(3) 0.7284(2) 0.4075(3) 0.0278(8) Uani 1 1 d .
H2A H 0.4169 0.6834 0.4133 0.037 Uiso 1 1 calc R
O1 O 0.0632(2) 0.69017(19) 0.5586(3) 0.0369(8) Uani 1 1 d .
O2 O 0.5082(2) 0.60633(16) 0.4514(3) 0.0269(7) Uani 1 1 d .
H2B H 0.5504 0.5924 0.4040 0.040 Uiso 1 1 calc R
Cl1 Cl 0.35602(9) 0.75420(7) 0.74038(10) 0.0346(3) Uani 1 1 d .
Cl2 Cl 0.67380(7) 0.59564(7) 0.28012(10) 0.0324(3) Uani 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'
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'
Cl Cl 0.1484 0.1585 '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 C1 C2 114.9(3)
C8 C1 Cl1 106.9(3)
C2 C1 Cl1 107.7(3)
N1 C2 C1 109.5(3)
N1 C2 C3 108.9(3)
C1 C2 C3 119.4(3)
C4 C3 C14 111.9(3)
C4 C3 C2 117.3(3)
C14 C3 C2 115.6(3)
C5 C4 C3 132.2(4)
C4 C5 C6 129.1(4)
C5 C6 N2 113.1(4)
C5 C6 C7 118.3(4)
N2 C6 C7 90.1(3)
C9 C7 C8 119.3(4)
C9 C7 C6 115.4(3)
C8 C7 C6 88.2(3)
C1 C8 N2 111.0(3)
C1 C8 C7 113.7(3)
N2 C8 C7 90.6(3)
O1 C9 N1 122.4(4)
O1 C9 C7 120.2(4)
N1 C9 C7 117.4(3)
N1 C10 C11 112.5(4)
C12 C11 C10 113.2(4)
C13 C12 C11 113.6(5)
O2 C14 C18 108.5(3)
O2 C14 C15 108.8(3)
C18 C14 C15 111.0(3)
O2 C14 C3 107.3(3)
C18 C14 C3 110.3(3)
C15 C14 C3 110.8(3)
C16 C15 C14 115.7(4)
C17 C16 C15 125.1(5)
C19 C18 C14 114.4(4)
C20 C19 C18 124.0(5)
N2 C21 C22 109.0(4)
C21 C22 C23 113.1(4)
C24 C23 C22 111.7(6)
C9 N1 C10 120.2(3)
C9 N1 C2 123.1(3)
C10 N1 C2 116.5(3)
C21 N2 C6 114.6(3)
C21 N2 C8 116.7(3)
C6 N2 C8 90.5(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C8 1.505(6)
C1 C2 1.530(6)
C1 Cl1 1.806(4)
C2 N1 1.483(5)
C2 C3 1.574(6)
C3 C4 1.517(6)
C3 C14 1.554(5)
C4 C5 1.305(6)
C5 C6 1.494(6)
C6 N2 1.519(6)
C6 C7 1.561(6)
C7 C9 1.498(6)
C7 C8 1.544(6)
C8 N2 1.523(6)
C9 O1 1.232(5)
C9 N1 1.345(6)
C10 N1 1.474(6)
C10 C11 1.528(8)
C11 C12 1.508(8)
C12 C13 1.501(9)
C14 O2 1.439(5)
C14 C18 1.534(6)
C14 C15 1.535(6)
C15 C16 1.506(6)
C16 C17 1.311(7)
C18 C19 1.516(7)
C19 C20 1.318(8)
C21 N2 1.502(6)
C21 C22 1.529(7)
C22 C23 1.529(7)
C23 C24 1.457(10)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N2 H2A O2 0.91 1.77 2.663(5) 167.6
O2 H2B Cl2 0.82 2.18 2.972(3) 162.4
