#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:12:37 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178425 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/46/4024603.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_4024603
loop_
_publ_author_name
'Yuewen Xu'
'Mark D. Smith'
'Jeanette A. Krause'
'Linda S. Shimizu'
_publ_section_title
;
Control of the Intramolecular [2+2] Photocycloaddition in a Bis-Stilbene
Macrocycle
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              4874
_journal_page_last               4877
_journal_paper_doi               10.1021/jo900443e
_journal_volume                  74
_journal_year                    2009
_chemical_formula_moiety         'C34 H32 N4 O2, 2(C2 D6 O S)'
_chemical_formula_sum            'C38 H32 D12 N4 O4 S2'
_chemical_formula_weight         696.96
_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_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                82.598(4)
_cell_angle_beta                 73.657(4)
_cell_angle_gamma                89.266(4)
_cell_formula_units_Z            1
_cell_length_a                   7.934(2)
_cell_length_b                   9.003(3)
_cell_length_c                   12.354(3)
_cell_measurement_reflns_used    1326
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      24.822
_cell_measurement_theta_min      4.006
_cell_volume                     839.5(4)
_computing_cell_refinement       'Bruker SAINT v7.56A'
_computing_data_collection       'Bruker APEX2 v2008.5.0'
_computing_data_reduction        'Bruker SAINT v7.56A'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEXII'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  'Si-<111> channel cut crystal'
_diffrn_radiation_source         synchrotron
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.77490
_diffrn_reflns_av_R_equivalents  0.0404
_diffrn_reflns_av_sigmaI/netI    0.0485
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8374
_diffrn_reflns_theta_full        27.46
_diffrn_reflns_theta_max         27.46
_diffrn_reflns_theta_min         3.90
_exptl_absorpt_coefficient_mu    0.256
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.379
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             364
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.430
_refine_diff_density_min         -0.313
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         2965
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.006
_refine_ls_R_factor_all          0.0834
_refine_ls_R_factor_gt           0.0506
_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)+(0.0574P)²+0.6088P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1150
_refine_ls_wR_factor_ref         0.1312
_reflns_number_gt                2079
_reflns_number_total             2965
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo900443e_si_004.cif
_cod_data_source_block           usca002
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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_database_code               4024603
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
C1 C 0.0116(4) 0.2727(4) 0.1933(3) 0.0387(7) Uani 1 1 d . . .
C2 C 0.0195(4) 0.0525(4) 0.3282(3) 0.0426(8) Uani 1 1 d . . .
H2A H 0.0427 -0.0558 0.3281 0.051 Uiso 1 1 calc R . .
H2B H -0.1057 0.0633 0.3693 0.051 Uiso 1 1 calc R . .
C3 C 0.1341(4) 0.1208(3) 0.3892(2) 0.0355(7) Uani 1 1 d . . .
C4 C 0.0772(4) 0.2412(3) 0.4488(2) 0.0396(7) Uani 1 1 d . . .
H4 H -0.0411 0.2717 0.4612 0.048 Uiso 1 1 calc R . .
C5 C 0.1921(4) 0.3179(3) 0.4908(2) 0.0371(7) Uani 1 1 d . . .
H5 H 0.1504 0.3991 0.5323 0.045 Uiso 1 1 calc R . .
C6 C 0.3670(4) 0.2771(3) 0.4725(2) 0.0328(7) Uani 1 1 d . . .
C7 C 0.4183(4) 0.1517(3) 0.4193(2) 0.0380(7) Uani 1 1 d . . .
H7 H 0.5348 0.1179 0.4098 0.046 Uiso 1 1 calc R . .
C8 C 0.3035(4) 0.0737(3) 0.3792(2) 0.0383(7) Uani 1 1 d . . .
H8 H 0.3422 -0.0135 0.3444 0.046 Uiso 1 1 calc R . .
C9 C 0.5032(4) 0.3775(3) 0.4923(2) 0.0334(7) Uani 1 1 d . . .
H9 H 0.6127 0.3212 0.4925 0.040 Uiso 1 1 calc R . .
C10 C 0.5488(4) 0.5308(3) 0.4068(2) 0.0342(7) Uani 1 1 d . . .
H10 H 0.6785 0.5406 0.3704 0.041 Uiso 1 1 calc R . .
C11 C 0.4525(4) 0.5513(3) 0.3162(2) 0.0325(7) Uani 1 1 d . . .
C12 C 0.3046(4) 0.6367(3) 0.3208(2) 0.0396(7) Uani 1 1 d . . .
H12 H 0.2691 0.7017 0.3776 0.048 Uiso 1 1 calc R . .
C13 C 0.2066(4) 0.6290(3) 0.2432(3) 0.0388(7) Uani 1 1 d . . .
H13 H 0.1058 0.6888 0.2480 0.047 Uiso 1 1 calc R . .
C14 C 0.2545(4) 0.5359(3) 0.1603(2) 0.0341(7) Uani 1 1 d . . .
C15 C 0.4089(4) 0.4573(3) 0.1518(2) 0.0378(7) Uani 1 1 d . . .
H15 H 0.4477 0.3961 0.0928 0.045 Uiso 1 1 calc R . .
C16 C 0.5073(4) 0.4661(3) 0.2275(2) 0.0360(7) Uani 1 1 d . . .
H16 H 0.6136 0.4131 0.2184 0.043 Uiso 1 1 calc R . .
C17 C 0.1392(4) 0.5080(3) 0.0853(3) 0.0403(8) Uani 1 1 d . . .
H17A H 0.0272 0.5604 0.1101 0.048 Uiso 1 1 calc R . .
H17B H 0.1986 0.5501 0.0057 0.048 Uiso 1 1 calc R . .
N1 N 0.1021(4) 0.3489(3) 0.0898(2) 0.0373(6) Uani 1 1 d . . .
H1 H 0.184(4) 0.302(4) 0.051(3) 0.037(9) Uiso 1 1 d . . .
N2 N 0.0537(4) 0.1249(3) 0.2112(2) 0.0386(6) Uani 1 1 d . . .
H2 H 0.151(4) 0.104(4) 0.161(3) 0.046(10) Uiso 1 1 d . . .
O1 O -0.1014(3) 0.3311(3) 0.2625(2) 0.0510(6) Uani 1 1 d . . .
S1 S 0.39195(11) 0.06451(9) -0.11307(7) 0.0405(2) Uani 1 1 d . . .
C18 C 0.2980(5) -0.1198(4) -0.0813(3) 0.0515(9) Uani 1 1 d . . .
D18A H 0.3557 -0.1816 -0.0315 0.077 Uiso 1 1 calc R . .
D18B H 0.3143 -0.1637 -0.1520 0.077 Uiso 1 1 calc R . .
D18C H 0.1722 -0.1158 -0.0427 0.077 Uiso 1 1 calc R . .
C19 C 0.2437(5) 0.1494(4) -0.1863(3) 0.0512(9) Uani 1 1 d . . .
D19A H 0.1226 0.1264 -0.1399 0.077 Uiso 1 1 calc R . .
D19B H 0.2630 0.1101 -0.2592 0.077 Uiso 1 1 calc R . .
D19C H 0.2642 0.2582 -0.2002 0.077 Uiso 1 1 calc R . .
O2 O 0.3511(3) 0.1269(2) -0.00258(18) 0.0493(6) 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 -0.0020 0.0020 '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 -0.0031 0.0040 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O -0.0041 0.0074 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1206 0.1480 '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
_geom_angle_publ_flag
O1 C1 N2 122.5(3) . . ?
O1 C1 N1 122.3(3) . . ?
N2 C1 N1 115.1(3) . . ?
N2 C2 C3 111.1(2) . . ?
N2 C2 H2A 109.4 . . ?
C3 C2 H2A 109.4 . . ?
N2 C2 H2B 109.4 . . ?
C3 C2 H2B 109.4 . . ?
H2A C2 H2B 108.0 . . ?
C8 C3 C4 118.0(3) . . ?
C8 C3 C2 121.0(3) . . ?
C4 C3 C2 120.8(3) . . ?
C3 C4 C5 120.7(3) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C6 C5 C4 121.0(3) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C7 C6 C5 117.5(3) . . ?
C7 C6 C9 119.9(3) . . ?
C5 C6 C9 122.0(3) . . ?
C6 C7 C8 121.5(3) . . ?
C6 C7 H7 119.2 . . ?
C8 C7 H7 119.2 . . ?
C3 C8 C7 121.1(3) . . ?
C3 C8 H8 119.4 . . ?
C7 C8 H8 119.4 . . ?
C6 C9 C10 119.2(2) . 2_666 ?
C6 C9 C10 115.1(2) . . ?
C10 C9 C10 89.3(2) 2_666 . ?
C6 C9 H9 110.5 . . ?
C10 C9 H9 110.5 2_666 . ?
C10 C9 H9 110.5 . . ?
C11 C10 C9 119.9(2) . 2_666 ?
C11 C10 C9 115.3(2) . . ?
C9 C10 C9 90.7(2) 2_666 . ?
C11 C10 H10 109.9 . . ?
C9 C10 H10 109.9 2_666 . ?
C9 C10 H10 109.9 . . ?
C16 C11 C12 117.7(3) . . ?
C16 C11 C10 116.7(3) . . ?
C12 C11 C10 125.3(3) . . ?
C11 C12 C13 121.2(3) . . ?
C11 C12 H12 119.4 . . ?
C13 C12 H12 119.4 . . ?
C14 C13 C12 120.8(3) . . ?
C14 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
C13 C14 C15 117.7(3) . . ?
C13 C14 C17 122.4(3) . . ?
C15 C14 C17 119.7(3) . . ?
C16 C15 C14 121.5(3) . . ?
C16 C15 H15 119.2 . . ?
C14 C15 H15 119.2 . . ?
C11 C16 C15 120.8(3) . . ?
C11 C16 H16 119.6 . . ?
C15 C16 H16 119.6 . . ?
N1 C17 C14 112.0(2) . . ?
N1 C17 H17A 109.2 . . ?
C14 C17 H17A 109.2 . . ?
N1 C17 H17B 109.2 . . ?
C14 C17 H17B 109.2 . . ?
H17A C17 H17B 107.9 . . ?
C1 N1 C17 117.5(3) . . ?
C1 N1 H1 115(2) . . ?
C17 N1 H1 115(2) . . ?
C1 N2 C2 118.3(3) . . ?
C1 N2 H2 112(2) . . ?
C2 N2 H2 118(2) . . ?
O2 S1 C18 106.16(16) . . ?
O2 S1 C19 106.07(15) . . ?
C18 S1 C19 97.92(16) . . ?
S1 C18 D18A 109.5 . . ?
S1 C18 D18B 109.5 . . ?
D18A C18 D18B 109.5 . . ?
S1 C18 D18C 109.5 . . ?
D18A C18 D18C 109.5 . . ?
D18B C18 D18C 109.5 . . ?
S1 C19 D19A 109.5 . . ?
S1 C19 D19B 109.5 . . ?
D19A C19 D19B 109.5 . . ?
S1 C19 D19C 109.5 . . ?
D19A C19 D19C 109.5 . . ?
D19B C19 D19C 109.5 . . ?
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
C1 O1 1.218(4) . ?
C1 N2 1.373(4) . ?
C1 N1 1.375(4) . ?
C2 N2 1.459(4) . ?
C2 C3 1.514(4) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C8 1.381(4) . ?
C3 C4 1.388(4) . ?
C4 C5 1.397(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.394(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.379(4) . ?
C6 C9 1.509(4) . ?
C7 C8 1.388(4) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
C9 C10 1.540(4) 2_666 ?
C9 C10 1.604(4) . ?
C9 H9 1.0000 . ?
C10 C11 1.515(4) . ?
C10 C9 1.540(4) 2_666 ?
C10 H10 1.0000 . ?
C11 C16 1.385(4) . ?
C11 C12 1.386(4) . ?
C12 C13 1.403(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.375(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.391(4) . ?
C14 C17 1.517(4) . ?
C15 C16 1.386(4) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 N1 1.456(4) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
N1 H1 0.84(3) . ?
N2 H2 0.88(3) . ?
S1 O2 1.493(2) . ?
S1 C18 1.779(3) . ?
S1 C19 1.784(3) . ?
C18 D18B 0.9800 . ?
C18 D18C 0.9800 . ?
C18 D18A 0.9800 . ?
C19 D19B 0.9800 . ?
C19 D19A 0.9800 . ?
C19 D19C 0.9800 . ?
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
_geom_hbond_site_symmetry_A
N1 H1 O2 0.84(3) 2.10(3) 2.901(4) 161(3) .
N2 H2 O2 0.88(3) 2.18(3) 3.004(4) 156(3) .
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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N2 C2 C3 C8 -84.2(4) . . . . ?
N2 C2 C3 C4 90.2(3) . . . . ?
C8 C3 C4 C5 4.1(4) . . . . ?
C2 C3 C4 C5 -170.5(3) . . . . ?
C3 C4 C5 C6 0.9(4) . . . . ?
C4 C5 C6 C7 -4.8(4) . . . . ?
C4 C5 C6 C9 165.7(3) . . . . ?
C5 C6 C7 C8 3.7(4) . . . . ?
C9 C6 C7 C8 -167.0(3) . . . . ?
C4 C3 C8 C7 -5.2(4) . . . . ?
C2 C3 C8 C7 169.4(3) . . . . ?
C6 C7 C8 C3 1.3(5) . . . . ?
C7 C6 C9 C10 -152.5(3) . . . 2_666 ?
C5 C6 C9 C10 37.3(4) . . . 2_666 ?
C7 C6 C9 C10 103.3(3) . . . . ?
C5 C6 C9 C10 -67.0(4) . . . . ?
C6 C9 C10 C11 -1.6(4) . . . . ?
C10 C9 C10 C11 -123.8(3) 2_666 . . . ?
C6 C9 C10 C9 122.2(3) . . . 2_666 ?
C10 C9 C10 C9 0.0 2_666 . . 2_666 ?
C9 C10 C11 C16 179.4(3) 2_666 . . . ?
C9 C10 C11 C16 -73.9(3) . . . . ?
C9 C10 C11 C12 -7.1(4) 2_666 . . . ?
C9 C10 C11 C12 99.5(3) . . . . ?
C16 C11 C12 C13 4.5(4) . . . . ?
C10 C11 C12 C13 -168.9(3) . . . . ?
C11 C12 C13 C14 0.1(5) . . . . ?
C12 C13 C14 C15 -3.9(4) . . . . ?
C12 C13 C14 C17 171.4(3) . . . . ?
C13 C14 C15 C16 3.1(4) . . . . ?
C17 C14 C15 C16 -172.3(3) . . . . ?
C12 C11 C16 C15 -5.3(4) . . . . ?
C10 C11 C16 C15 168.7(3) . . . . ?
C14 C15 C16 C11 1.5(5) . . . . ?
C13 C14 C17 N1 -125.0(3) . . . . ?
C15 C14 C17 N1 50.2(4) . . . . ?
O1 C1 N1 C17 34.1(4) . . . . ?
N2 C1 N1 C17 -148.1(3) . . . . ?
C14 C17 N1 C1 62.0(4) . . . . ?
O1 C1 N2 C2 -25.4(4) . . . . ?
N1 C1 N2 C2 156.8(3) . . . . ?
C3 C2 N2 C1 -65.8(4) . . . . ?
