#------------------------------------------------------------------------------
#$Date: 2016-03-21 02:43:10 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178403 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/24/4022417.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_4022417
loop_
_publ_author_name
'Howard E. Zimmerman'
'Tibor Novak'
_publ_contact_author
; 
   Prof. Howard E. Zimmerman 
   Department of Chemistry 
   University of Wisconsin 
   1101 University Ave. 
   Madison, WI  53706-1396  USA 
;
_publ_contact_author_email       zimmerman@chem.wisc.edu
_publ_contact_author_fax         1(608)2620381
_publ_contact_author_phone       1(608)2621502
_publ_section_title
;
 Regioselectivity of the Tri-π-methane Rearrangement:
 Mechanistic and Exploratory Organic Photochemistry
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5056
_journal_page_last               5066
_journal_paper_doi               10.1021/jo034189j
_journal_volume                  68
_journal_year                    2003
_chemical_formula_moiety         'C52 H38 N2'
_chemical_formula_sum            'C52 H38 N2'
_chemical_formula_weight         690.84
_chemical_melting_point          233.5(5)
_chemical_name_common            25
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           62
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2n'
_symmetry_space_group_name_H-M   'P n m a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_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                   21.146(3)
_cell_length_b                   17.623(3)
_cell_length_c                   10.657(2)
_cell_measurement_temperature    100(2)
_cell_volume                     3971.4(12)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  Bruker
_diffrn_measurement_method       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  0.0590
_diffrn_reflns_av_sigmaI/netI    0.0355
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            27222
_diffrn_reflns_theta_full        26.54
_diffrn_reflns_theta_max         26.54
_diffrn_reflns_theta_min         1.93
_diffrn_standards_decay_%        <1%
_exptl_absorpt_coefficient_mu    0.067
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.155
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             1456
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.43
_exptl_crystal_size_min          0.38
_refine_diff_density_max         0.314
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     287
_refine_ls_number_reflns         4194
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0634
_refine_ls_R_factor_gt           0.0539
_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)+(0.0764P)²+1.0262P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1365
_refine_ls_wR_factor_ref         0.1431
_reflns_number_gt                3544
_reflns_number_total             4194
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo034189jsi20030218_024243_3.cif
_cod_data_source_block           25
_cod_depositor_comments
;
The following automatic conversions were performed:
'_exptl_absorpt_correction_type' value 'None' changed to 'none' 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 

The following automatic conversions were performed:

'_chemical_melting_point' value '233-234' was changed to '233.5(5)' -
the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_database_code               4022417
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z+1/2'
'-x, y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z-1/2'
'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
N1 N 0.63111(8) 0.2500 0.4083(2) 0.0465(5) Uani 1 2 d S
N2 N 0.10744(13) 0.2500 0.6116(3) 0.0815(9) Uani 1 2 d S
C1 C 0.33441(8) 0.2500 0.14723(17) 0.0248(4) Uani 1 2 d S
C2 C 0.32564(6) 0.20676(9) 0.02424(14) 0.0350(4) Uani 1 1 d .
H2 H 0.3558(19) 0.177(2) 0.000(4) 0.045 Uiso 0.50 1 d P
C3 C 0.26656(6) 0.16423(9) 0.00115(13) 0.0348(3) Uani 1 1 d .
H3 H 0.2292 0.1906 0.0157 0.045 Uiso 1 1 calc R
C4 C 0.26016(6) 0.09243(9) -0.03815(13) 0.0321(3) Uani 1 1 d .
C5 C 0.31521(6) 0.04051(9) -0.05622(13) 0.0329(3) Uani 1 1 d .
C6 C 0.34772(7) 0.01025(9) 0.04573(14) 0.0358(3) Uani 1 1 d .
H6 H 0.3335 0.0200 0.1267 0.047 Uiso 1 1 calc R
C7 C 0.40104(8) -0.03429(10) 0.02810(17) 0.0470(4) Uani 1 1 d .
H7 H 0.4225 -0.0539 0.0971 0.061 Uiso 1 1 calc R
C8 C 0.42222(8) -0.04948(13) -0.0911(2) 0.0594(5) Uani 1 1 d .
H8 H 0.4586 -0.0783 -0.1027 0.077 Uiso 1 1 calc R
C9 C 0.38953(9) -0.02202(13) -0.19351(19) 0.0633(6) Uani 1 1 d .
H9 H 0.4033 -0.0335 -0.2742 0.082 Uiso 1 1 calc R
C10 C 0.33615(8) 0.02269(11) -0.17666(16) 0.0491(4) Uani 1 1 d .
H10 H 0.3143 0.0409 -0.2461 0.064 Uiso 1 1 calc R
C11 C 0.19588(7) 0.06155(9) -0.06336(13) 0.0352(3) Uani 1 1 d .
C12 C 0.14895(7) 0.10764(10) -0.11651(17) 0.0464(4) Uani 1 1 d .
H12 H 0.1587 0.1568 -0.1418 0.060 Uiso 1 1 calc R
C13 C 0.08773(8) 0.07991(13) -0.1314(2) 0.0600(6) Uani 1 1 d .
H13 H 0.0566 0.1111 -0.1653 0.078 Uiso 1 1 calc R
C14 C 0.07293(8) 0.00728(13) -0.0968(2) 0.0615(6) Uani 1 1 d .
H14 H 0.0319 -0.0107 -0.1070 0.080 Uiso 1 1 calc R
C15 C 0.11900(9) -0.03951(12) -0.04653(19) 0.0551(5) Uani 1 1 d .
H15 H 0.1090 -0.0889 -0.0231 0.072 Uiso 1 1 calc R
C16 C 0.18018(7) -0.01261(10) -0.03114(15) 0.0423(4) Uani 1 1 d .
H16 H 0.2111 -0.0446 0.0012 0.055 Uiso 1 1 calc R
C17 C 0.39903(8) 0.2500 0.20636(16) 0.0259(4) Uani 1 2 d S
C18 C 0.42897(6) 0.18193(9) 0.23480(14) 0.0329(3) Uani 1 1 d .
H18 H 0.4088 0.1362 0.2178 0.043(5) Uiso 1 1 calc R
C19 C 0.48881(6) 0.18166(9) 0.28835(14) 0.0345(3) Uani 1 1 d .
H19 H 0.5086 0.1360 0.3076 0.045 Uiso 1 1 calc R
C20 C 0.51886(8) 0.2500 0.31299(17) 0.0287(4) Uani 1 2 d S
C21 C 0.58146(9) 0.2500 0.36609(19) 0.0339(5) Uani 1 2 d S
C22 C 0.28207(8) 0.2500 0.24471(17) 0.0282(4) Uani 1 2 d S
C23 C 0.25932(6) 0.31803(9) 0.29239(13) 0.0343(3) Uani 1 1 d .
H23 H 0.2750 0.3637 0.2617 0.045 Uiso 1 1 calc R
C24 C 0.21321(7) 0.31846(10) 0.38593(15) 0.0420(4) Uani 1 1 d .
H24 H 0.1978 0.3641 0.4171 0.055 Uiso 1 1 calc R
C25 C 0.19063(10) 0.2500 0.4320(2) 0.0428(6) Uani 1 2 d S
C26 C 0.14356(12) 0.2500 0.5314(3) 0.0595(7) Uani 1 2 d S
C27 C 0.38997(12) 0.19107(18) -0.0487(3) 0.0297(6) Uani 0.50 1 d P
H27A H 0.4235 0.2180 -0.0055 0.039 Uiso 0.50 1 calc PR
H27B H 0.3993 0.1373 -0.0423 0.039 Uiso 0.50 1 calc PR
C28 C 0.39240(12) 0.21298(16) -0.1866(2) 0.0272(5) Uani 0.50 1 d P
C29 C 0.45139(13) 0.21694(18) -0.2439(3) 0.0378(7) Uani 0.50 1 d P
H29 H 0.4874 0.2024 -0.2000 0.049 Uiso 0.50 1 calc PR
C30 C 0.45666(14) 0.2430(13) -0.3686(3) 0.065(3) Uani 0.50 1 d P
H30 H 0.4960 0.2552 -0.4020 0.085 Uiso 0.50 1 calc PR
C31 C 0.40386(11) 0.2500 -0.43866(19) 0.0417(5) Uani 1 2 d S
H31 H 0.4072 0.2549 -0.5253 0.054 Uiso 0.50 1 calc PR
C32 C 0.34535(10) 0.2500 -0.3831(2) 0.0416(5) Uani 1 2 d S
H32 H 0.3097 0.2631 -0.4294 0.054 Uiso 0.50 1 calc PR
C33 C 0.33967(13) 0.2303(2) -0.2579(3) 0.0437(14) Uani 0.50 1 d P
H33 H 0.2998 0.2287 -0.2211 0.057 Uiso 0.50 1 calc PR
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'
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
C17 C1 C22 112.05(14) . .
C17 C1 C2 118.02(12) . .
C22 C1 C2 119.91(12) . .
C17 C1 C2 118.02(12) . 8_565
C22 C1 C2 119.91(12) . 8_565
C2 C1 C2 59.86(14) . 8_565
C3 C2 C2 120.49(8) . 8_565
C3 C2 C1 119.92(13) . .
C2 C2 C1 60.07(7) 8_565 .
C3 C2 C27 123.60(16) . .
C2 C2 C27 100.00(13) 8_565 .
C1 C2 C27 113.70(15) . .
C4 C3 C2 128.07(13) . .
C3 C4 C11 119.60(12) . .
C3 C4 C5 122.71(13) . .
C11 C4 C5 117.68(13) . .
C6 C5 C10 118.40(14) . .
C6 C5 C4 121.28(13) . .
C10 C5 C4 120.31(13) . .
C7 C6 C5 120.84(15) . .
C8 C7 C6 120.06(16) . .
C7 C8 C9 120.01(16) . .
C8 C9 C10 120.27(17) . .
C9 C10 C5 120.36(16) . .
C16 C11 C12 118.36(14) . .
C16 C11 C4 121.11(14) . .
C12 C11 C4 120.50(15) . .
C13 C12 C11 120.05(18) . .
C14 C13 C12 120.65(18) . .
C13 C14 C15 120.05(17) . .
C14 C15 C16 119.90(19) . .
C15 C16 C11 120.94(16) . .
C18 C17 C18 119.33(17) 8_565 .
C18 C17 C1 120.33(8) 8_565 .
C18 C17 C1 120.33(8) . .
C19 C18 C17 120.52(14) . .
C20 C19 C18 119.51(14) . .
C19 C20 C19 120.56(17) 8_565 .
C19 C20 C21 119.72(9) 8_565 .
C19 C20 C21 119.72(9) . .
N1 C21 C20 180.0(2) . .
C23 C22 C23 119.45(18) 8_565 .
C23 C22 C1 120.22(9) 8_565 .
C23 C22 C1 120.22(9) . .
C22 C23 C24 120.58(15) . .
C25 C24 C23 119.26(16) . .
C24 C25 C24 120.85(19) . 8_565
C24 C25 C26 119.57(10) . .
C24 C25 C26 119.57(10) 8_565 .
N2 C26 C25 178.6(3) . .
C28 C27 C2 117.19(19) . .
C28 C28 C33 77.25(19) 8_565 .
C28 C28 C29 87.13(17) 8_565 .
C33 C28 C29 118.1(3) . .
C28 C28 C27 104.72(16) 8_565 .
C33 C28 C27 124.0(2) . .
C29 C28 C27 117.9(2) . .
C28 C28 C33 53.47(15) 8_565 8_565
C33 C28 C33 23.8(3) . 8_565
C29 C28 C33 111.5(2) . 8_565
C27 C28 C33 124.5(2) . 8_565
C28 C28 C29 48.36(12) 8_565 8_565
C33 C28 C29 102.3(2) . 8_565
C29 C28 C29 38.8(2) . 8_565
C27 C28 C29 120.6(2) . 8_565
C33 C28 C29 84.34(19) 8_565 8_565
C28 C29 C30 120.1(3) . .
C31 C30 C29 119.1(5) . .
C30 C31 C32 120.5(2) . .
C31 C32 C33 119.6(2) . .
C28 C33 C32 121.0(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C21 1.142(3) .
N2 C26 1.147(3) .
C1 C17 1.505(2) .
C1 C22 1.518(2) .
C1 C2 1.527(2) .
C1 C2 1.527(2) 8_565
C2 C3 1.477(2) .
C2 C2 1.524(3) 8_565
C2 C27 1.591(3) .
C3 C4 1.340(2) .
C4 C11 1.4887(19) .
C4 C5 1.4931(19) .
C5 C6 1.392(2) .
C5 C10 1.394(2) .
C6 C7 1.387(2) .
C7 C8 1.373(3) .
C8 C9 1.380(3) .
C9 C10 1.388(2) .
C11 C16 1.391(2) .
C11 C12 1.402(2) .
C12 C13 1.393(2) .
C13 C14 1.368(3) .
C14 C15 1.384(3) .
C15 C16 1.388(2) .
C17 C18 1.3899(17) 8_565
C17 C18 1.3899(17) .
C18 C19 1.3881(19) .
C19 C20 1.3868(17) .
C20 C19 1.3868(17) 8_565
C20 C21 1.440(3) .
C22 C23 1.3881(18) 8_565
C22 C23 1.3881(18) .
C23 C24 1.394(2) .
C24 C25 1.387(2) .
C25 C24 1.387(2) 8_565
C25 C26 1.454(3) .
C27 C28 1.520(4) .
C28 C28 1.305(6) 8_565
C28 C33 1.383(4) .
C28 C29 1.391(4) .
C28 C33 1.679(4) 8_565
C28 C29 1.859(4) 8_565
C29 C30 1.410(8) .
C30 C31 1.349(4) .
C31 C32 1.372(3) .
C32 C33 1.385(4) .
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
C17 C1 C2 C3 142.04(13) . .
C22 C1 C2 C3 -0.78(18) . .
C2 C1 C2 C3 -110.13(13) 8_565 .
C17 C1 C2 C2 -107.84(11) . 8_565
C22 C1 C2 C2 109.34(11) . 8_565
C17 C1 C2 C27 -19.8(2) . .
C22 C1 C2 C27 -162.60(15) . .
C2 C1 C2 C27 88.06(16) 8_565 .
C2 C2 C3 C4 158.60(12) 8_565 .
C1 C2 C3 C4 -130.62(16) . .
C27 C2 C3 C4 29.3(3) . .
C2 C3 C4 C11 -176.19(14) . .
C2 C3 C4 C5 4.9(2) . .
C3 C4 C5 C6 72.8(2) . .
C11 C4 C5 C6 -106.16(16) . .
C3 C4 C5 C10 -105.65(19) . .
C11 C4 C5 C10 75.4(2) . .
C10 C5 C6 C7 2.3(2) . .
C4 C5 C6 C7 -176.16(15) . .
C5 C6 C7 C8 -0.4(3) . .
C6 C7 C8 C9 -1.6(3) . .
C7 C8 C9 C10 1.7(4) . .
C8 C9 C10 C5 0.2(3) . .
C6 C5 C10 C9 -2.2(3) . .
C4 C5 C10 C9 176.27(18) . .
C3 C4 C11 C16 -141.04(15) . .
C5 C4 C11 C16 37.95(19) . .
C3 C4 C11 C12 36.8(2) . .
C5 C4 C11 C12 -144.22(15) . .
C16 C11 C12 C13 2.5(2) . .
C4 C11 C12 C13 -175.38(15) . .
C11 C12 C13 C14 -1.2(3) . .
C12 C13 C14 C15 -0.1(3) . .
C13 C14 C15 C16 0.1(3) . .
C14 C15 C16 C11 1.2(3) . .
C12 C11 C16 C15 -2.5(2) . .
C4 C11 C16 C15 175.36(15) . .
C22 C1 C17 C18 -89.52(14) . 8_565
C2 C1 C17 C18 124.89(14) . 8_565
C2 C1 C17 C18 56.06(19) 8_565 8_565
C22 C1 C17 C18 89.52(14) . .
C2 C1 C17 C18 -56.06(19) . .
C2 C1 C17 C18 -124.89(14) 8_565 .
C18 C17 C18 C19 -1.5(3) 8_565 .
C1 C17 C18 C19 179.44(14) . .
C17 C18 C19 C20 -0.3(2) . .
C18 C19 C20 C19 2.1(3) . 8_565
C18 C19 C20 C21 -178.71(15) . .
C19 C20 C21 N1 90(100) 8_565 .
C19 C20 C21 N1 -90(100) . .
C17 C1 C22 C23 -88.03(15) . 8_565
C2 C1 C22 C23 56.8(2) . 8_565
C2 C1 C22 C23 127.11(14) 8_565 8_565
C17 C1 C22 C23 88.03(15) . .
C2 C1 C22 C23 -127.11(14) . .
C2 C1 C22 C23 -56.8(2) 8_565 .
C23 C22 C23 C24 -1.1(3) 8_565 .
C1 C22 C23 C24 -177.17(15) . .
C22 C23 C24 C25 0.6(2) . .
C23 C24 C25 C24 -0.1(3) . 8_565
C23 C24 C25 C26 178.67(19) . .
C24 C25 C26 N2 -89.41(19) . .
C24 C25 C26 N2 89.42(19) 8_565 .
C3 C2 C27 C28 69.7(3) . .
C2 C2 C27 C28 -67.6(2) 8_565 .
C1 C2 C27 C28 -129.2(2) . .
C2 C27 C28 C28 70.3(2) . 8_565
C2 C27 C28 C33 -14.1(4) . .
C2 C27 C28 C29 164.9(2) . .
C2 C27 C28 C33 14.8(4) . 8_565
C2 C27 C28 C29 120.3(2) . 8_565
C28 C28 C29 C30 -69.6(11) 8_565 .
C33 C28 C29 C30 4.3(11) . .
C27 C28 C29 C30 -174.8(11) . .
C33 C28 C29 C30 -21.0(11) 8_565 .
C29 C28 C29 C30 -69.6(11) 8_565 .
C28 C29 C30 C31 -13(2) . .
C29 C30 C31 C32 16(2) . .
C30 C31 C32 C33 -10.7(12) . .
C28 C28 C33 C32 80.6(3) 8_565 .
C29 C28 C33 C32 0.9(5) . .
C27 C28 C33 C32 179.9(3) . .
C33 C28 C33 C32 80.6(3) 8_565 .
C29 C28 C33 C32 38.9(4) 8_565 .
C31 C32 C33 C28 2.1(4) . .
