#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/18/1501878.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_1501878
loop_
_publ_author_name
'Scadeng, Owen'
'Ferguson, Michael J.'
'West, F. G.'
_publ_section_title
;
 Intermolecular [3 + 3]-cycloadditions of azides with the Nazarov
 intermediate.
;
_journal_issue                   1
_journal_name_full               'Organic letters'
_journal_page_first              114
_journal_page_last               117
_journal_paper_doi               10.1021/ol102651k
_journal_volume                  13
_journal_year                    2011
_chemical_formula_moiety         'C26 H25 N3 O'
_chemical_formula_sum            'C26 H25 N3 O'
_chemical_formula_weight         395.49
_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                84.4292(3)
_cell_angle_beta                 72.2128(3)
_cell_angle_gamma                66.9269(3)
_cell_formula_units_Z            2
_cell_length_a                   9.5322(3)
_cell_length_b                   10.3847(3)
_cell_length_c                   12.3527(3)
_cell_measurement_reflns_used    9950
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.55
_cell_measurement_theta_min      2.43
_cell_volume                     1070.83(5)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω 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  0.0096
_diffrn_reflns_av_sigmaI/netI    0.0141
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9467
_diffrn_reflns_theta_full        26.40
_diffrn_reflns_theta_max         27.55
_diffrn_reflns_theta_min         1.73
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  0.9745
_exptl_absorpt_correction_T_min  0.9537
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.227
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       fragment
_exptl_crystal_F_000             420
_exptl_crystal_size_max          0.63
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.34
_refine_diff_density_max         0.281
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         4876
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0411
_refine_ls_R_factor_gt           0.0386
_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)+(0.0541P)²+0.2358P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1032
_refine_ls_wR_factor_ref         0.1054
_reflns_number_gt                4497
_reflns_number_total             4876
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ol102651k_si_002.cif
_cod_data_source_block           3a
_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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               1501878
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
O O 0.58552(9) 0.09115(8) 0.05503(6) 0.03500(18) Uani 1 1 d .
N1 N 0.30933(10) 0.28723(8) 0.26646(7) 0.02756(18) Uani 1 1 d .
N2 N 0.40777(11) 0.28148(9) 0.32620(7) 0.0317(2) Uani 1 1 d .
N3 N 0.53113(11) 0.17432(9) 0.32451(8) 0.0333(2) Uani 1 1 d .
C1 C 0.51122(12) 0.09527(10) 0.15430(8) 0.0267(2) Uani 1 1 d .
C2 C 0.33137(12) 0.16026(10) 0.20552(8) 0.0252(2) Uani 1 1 d .
C3 C 0.29933(11) 0.04793(10) 0.29223(8) 0.02423(19) Uani 1 1 d .
H3 H 0.2858 -0.0218 0.2500 0.029 Uiso 1 1 calc R
C4 C 0.45898(11) -0.02971(10) 0.32562(8) 0.02477(19) Uani 1 1 d .
H4 H 0.4369 -0.0111 0.4083 0.030 Uiso 1 1 calc R
C5 C 0.57216(12) 0.04326(10) 0.25534(8) 0.0278(2) Uani 1 1 d .
C6 C 0.74942(13) -0.03694(12) 0.23095(11) 0.0375(2) Uani 1 1 d .
H6A H 0.8061 0.0193 0.1839 0.045 Uiso 1 1 calc R
H6B H 0.7805 -0.1249 0.1903 0.045 Uiso 1 1 calc R
H6C H 0.7768 -0.0573 0.3027 0.045 Uiso 1 1 calc R
C7 C 0.23891(13) 0.19704(11) 0.11909(8) 0.0316(2) Uani 1 1 d .
H7A H 0.2675 0.2664 0.0673 0.038 Uiso 1 1 calc R
H7B H 0.1243 0.2360 0.1585 0.038 Uiso 1 1 calc R
H7C H 0.2650 0.1125 0.0755 0.038 Uiso 1 1 calc R
C8 C 0.16379(12) 0.41404(10) 0.28652(9) 0.0304(2) Uani 1 1 d .
H8A H 0.1488 0.4621 0.3570 0.037 Uiso 1 1 calc R
H8B H 0.0715 0.3871 0.2985 0.037 Uiso 1 1 calc R
C9 C 0.16650(12) 0.51504(10) 0.18956(8) 0.0277(2) Uani 1 1 d .
C10 C 0.29138(15) 0.56073(13) 0.15118(11) 0.0398(3) Uani 1 1 d .
H10 H 0.3769 0.5256 0.1840 0.048 Uiso 1 1 calc R
C11 C 0.29267(18) 0.65708(15) 0.06540(12) 0.0501(3) Uani 1 1 d .
H11 H 0.3783 0.6884 0.0404 0.060 Uiso 1 1 calc R
C12 C 0.17000(18) 0.70761(13) 0.01628(11) 0.0476(3) Uani 1 1 d .
H12 H 0.1710 0.7734 -0.0427 0.057 Uiso 1 1 calc R
C13 C 0.04625(16) 0.66214(14) 0.05336(11) 0.0469(3) Uani 1 1 d .
H13 H -0.0381 0.6963 0.0194 0.056 Uiso 1 1 calc R
C14 C 0.04363(13) 0.56655(12) 0.14021(11) 0.0387(3) Uani 1 1 d .
H14 H -0.0430 0.5365 0.1658 0.046 Uiso 1 1 calc R
C15 C 0.14645(11) 0.11055(10) 0.38742(8) 0.0259(2) Uani 1 1 d .
C16 C 0.00359(12) 0.11738(11) 0.37323(9) 0.0310(2) Uani 1 1 d .
H16 H 0.0059 0.0747 0.3077 0.037 Uiso 1 1 calc R
C17 C -0.14176(13) 0.18563(12) 0.45352(10) 0.0376(2) Uani 1 1 d .
H17 H -0.2378 0.1905 0.4420 0.045 Uiso 1 1 calc R
C18 C -0.14677(13) 0.24634(12) 0.55008(10) 0.0387(3) Uani 1 1 d .
H18 H -0.2461 0.2935 0.6048 0.046 Uiso 1 1 calc R
C19 C -0.00604(14) 0.23792(11) 0.56663(9) 0.0350(2) Uani 1 1 d .
H19 H -0.0089 0.2777 0.6337 0.042 Uiso 1 1 calc R
C20 C 0.13946(12) 0.17151(10) 0.48552(8) 0.0291(2) Uani 1 1 d .
H20 H 0.2350 0.1677 0.4972 0.035 Uiso 1 1 calc R
C21 C 0.52737(11) -0.18676(10) 0.30430(8) 0.02497(19) Uani 1 1 d .
C22 C 0.56375(12) -0.27710(11) 0.39166(9) 0.0310(2) Uani 1 1 d .
H22 H 0.5456 -0.2397 0.4641 0.037 Uiso 1 1 calc R
C23 C 0.62640(14) -0.42172(12) 0.37382(11) 0.0390(3) Uani 1 1 d .
H23 H 0.6497 -0.4822 0.4343 0.047 Uiso 1 1 calc R
C24 C 0.65475(13) -0.47748(11) 0.26836(11) 0.0393(3) Uani 1 1 d .
H24 H 0.6967 -0.5761 0.2564 0.047 Uiso 1 1 calc R
C25 C 0.62162(13) -0.38881(11) 0.18023(10) 0.0342(2) Uani 1 1 d .
H25 H 0.6430 -0.4267 0.1073 0.041 Uiso 1 1 calc R
C26 C 0.55713(12) -0.24451(11) 0.19828(9) 0.0294(2) Uani 1 1 d .
H26 H 0.5330 -0.1845 0.1377 0.035 Uiso 1 1 calc R
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
N2 N1 C8 115.00(8)
N2 N1 C2 120.89(8)
C8 N1 C2 122.76(8)
N3 N2 N1 122.09(9)
N2 N3 C5 120.59(8)
O C1 C5 129.06(10)
O C1 C2 127.03(9)
C5 C1 C2 103.88(8)
N1 C2 C7 111.94(8)
N1 C2 C1 102.22(8)
C7 C2 C1 114.27(8)
N1 C2 C3 110.51(7)
C7 C2 C3 114.77(8)
C1 C2 C3 102.06(7)
C15 C3 C2 111.94(7)
C15 C3 C4 117.73(8)
C2 C3 C4 105.22(7)
C21 C4 C5 113.46(8)
C21 C4 C3 112.98(8)
C5 C4 C3 104.45(7)
C1 C5 C6 116.60(9)
C1 C5 N3 105.65(8)
C6 C5 N3 106.50(8)
C1 C5 C4 103.02(8)
C6 C5 C4 117.98(8)
N3 C5 C4 106.07(8)
N1 C8 C9 113.21(8)
C14 C9 C10 118.84(10)
C14 C9 C8 121.20(10)
C10 C9 C8 119.94(9)
C11 C10 C9 120.64(11)
C12 C11 C10 120.20(12)
C13 C12 C11 119.51(11)
C12 C13 C14 120.49(11)
C9 C14 C13 120.31(11)
C20 C15 C16 118.15(9)
C20 C15 C3 122.77(9)
C16 C15 C3 118.89(9)
C17 C16 C15 121.02(10)
C18 C17 C16 120.11(10)
C17 C18 C19 119.59(10)
C18 C19 C20 120.41(10)
C19 C20 C15 120.69(10)
C22 C21 C26 118.46(9)
C22 C21 C4 119.82(9)
C26 C21 C4 121.71(8)
C23 C22 C21 120.69(10)
C24 C23 C22 120.21(10)
C23 C24 C25 119.68(10)
C24 C25 C26 120.19(10)
C25 C26 C21 120.76(10)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O C1 1.2096(12)
N1 N2 1.3413(12)
N1 C8 1.4634(13)
N1 C2 1.4928(12)
N2 N3 1.2591(13)
N3 C5 1.5295(13)
C1 C5 1.5010(13)
C1 C2 1.5193(14)
C2 C7 1.5148(13)
C2 C3 1.5615(13)
C3 C15 1.5126(13)
C3 C4 1.5790(13)
C4 C21 1.5163(13)
C4 C5 1.5598(13)
C5 C6 1.5080(14)
C8 C9 1.5144(14)
C9 C14 1.3826(15)
C9 C10 1.3861(16)
C10 C11 1.3856(17)
C11 C12 1.3789(19)
C12 C13 1.374(2)
C13 C14 1.3904(18)
C15 C20 1.3929(14)
C15 C16 1.3994(14)
C16 C17 1.3903(15)
C17 C18 1.3820(18)
C18 C19 1.3860(17)
C19 C20 1.3923(15)
C21 C22 1.3935(13)
C21 C26 1.3956(14)
C22 C23 1.3934(16)
C23 C24 1.3835(18)
C24 C25 1.3858(17)
C25 C26 1.3901(14)
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
C8 N1 N2 N3 174.34(9)
C2 N1 N2 N3 7.24(15)
N1 N2 N3 C5 -1.43(15)
N2 N1 C2 C7 -164.44(9)
C8 N1 C2 C7 29.49(12)
N2 N1 C2 C1 -41.72(11)
C8 N1 C2 C1 152.22(9)
N2 N1 C2 C3 66.30(11)
C8 N1 C2 C3 -99.77(10)
O C1 C2 N1 -108.51(11)
C5 C1 C2 N1 69.70(8)
O C1 C2 C7 12.63(14)
C5 C1 C2 C7 -169.17(8)
O C1 C2 C3 137.11(10)
C5 C1 C2 C3 -44.68(9)
N1 C2 C3 C15 47.51(10)
C7 C2 C3 C15 -80.21(10)
C1 C2 C3 C15 155.63(8)
N1 C2 C3 C4 -81.51(9)
C7 C2 C3 C4 150.77(8)
C1 C2 C3 C4 26.62(9)
C15 C3 C4 C21 110.59(9)
C2 C3 C4 C21 -123.92(8)
C15 C3 C4 C5 -125.65(8)
C2 C3 C4 C5 -0.16(9)
O C1 C5 C6 -6.03(16)
C2 C1 C5 C6 175.82(8)
O C1 C5 N3 112.01(11)
C2 C1 C5 N3 -66.14(9)
O C1 C5 C4 -136.90(11)
C2 C1 C5 C4 44.94(9)
N2 N3 C5 C1 32.16(12)
N2 N3 C5 C6 156.77(10)
N2 N3 C5 C4 -76.75(11)
C21 C4 C5 C1 96.65(9)
C3 C4 C5 C1 -26.81(9)
C21 C4 C5 C6 -33.39(12)
C3 C4 C5 C6 -156.84(9)
C21 C4 C5 N3 -152.58(8)
C3 C4 C5 N3 83.97(8)
N2 N1 C8 C9 105.57(10)
C2 N1 C8 C9 -87.61(11)
N1 C8 C9 C14 127.79(11)
N1 C8 C9 C10 -54.21(13)
C14 C9 C10 C11 0.44(18)
C8 C9 C10 C11 -177.61(11)
C9 C10 C11 C12 -0.7(2)
C10 C11 C12 C13 0.3(2)
C11 C12 C13 C14 0.4(2)
C10 C9 C14 C13 0.22(17)
C8 C9 C14 C13 178.24(10)
C12 C13 C14 C9 -0.64(19)
C2 C3 C15 C20 -86.22(11)
C4 C3 C15 C20 35.88(13)
C2 C3 C15 C16 88.81(10)
C4 C3 C15 C16 -149.09(9)
C20 C15 C16 C17 1.34(15)
C3 C15 C16 C17 -173.93(9)
C15 C16 C17 C18 -0.97(16)
C16 C17 C18 C19 -0.42(17)
C17 C18 C19 C20 1.42(16)
C18 C19 C20 C15 -1.03(16)
C16 C15 C20 C19 -0.34(14)
C3 C15 C20 C19 174.73(9)
C5 C4 C21 C22 114.41(10)
C3 C4 C21 C22 -126.94(9)
C5 C4 C21 C26 -64.85(12)
C3 C4 C21 C26 53.80(12)
C26 C21 C22 C23 -0.84(15)
C4 C21 C22 C23 179.88(9)
C21 C22 C23 C24 0.62(17)
C22 C23 C24 C25 0.47(17)
C23 C24 C25 C26 -1.32(17)
C24 C25 C26 C21 1.11(16)
C22 C21 C26 C25 -0.03(15)
C4 C21 C26 C25 179.24(9)
