#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/18/1501879.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_1501879
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         'C28 H29 N3 O3'
_chemical_formula_sum            'C28 H29 N3 O3'
_chemical_formula_weight         455.54
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           9
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 1'
_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                 102.8601(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.7182(13)
_cell_length_b                   15.0048(12)
_cell_length_c                   9.8096(8)
_cell_measurement_reflns_used    9276
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.39
_cell_measurement_theta_min      2.50
_cell_volume                     2399.0(3)
_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 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0148
_diffrn_reflns_av_sigmaI/netI    0.0121
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            10405
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         1.84
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.9882
_exptl_absorpt_correction_T_min  0.9599
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.261
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             968
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.175
_refine_diff_density_min         -0.153
_refine_diff_density_rms         0.027
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     309
_refine_ls_number_reflns         2764
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0291
_refine_ls_R_factor_gt           0.0280
_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)+(0.0469P)²+0.5360P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0756
_refine_ls_wR_factor_ref         0.0765
_reflns_number_gt                2685
_reflns_number_total             2764
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ol102651k_si_002.cif
_cod_data_source_block           3c
_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      'C c'
_cod_database_code               1501879
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, 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
O1 O 0.83596(9) 0.77324(10) 0.04983(16) 0.0432(3) Uani 1 1 d .
O2 O 0.34800(9) 0.97438(10) 0.07988(16) 0.0469(3) Uani 1 1 d .
O3 O 0.97802(8) 0.95103(9) 0.74515(12) 0.0359(3) Uani 1 1 d .
N1 N 0.63847(9) 0.76990(10) -0.00287(14) 0.0307(3) Uani 1 1 d .
N2 N 0.63558(10) 0.69597(10) 0.07253(16) 0.0345(3) Uani 1 1 d .
N3 N 0.68888(10) 0.67895(10) 0.18154(16) 0.0359(3) Uani 1 1 d .
C1 C 0.77769(10) 0.78423(11) 0.10164(18) 0.0307(3) Uani 1 1 d .
C2 C 0.70206(10) 0.84022(11) 0.04418(16) 0.0279(3) Uani 1 1 d .
C3 C 0.68719(10) 0.88754(10) 0.17770(15) 0.0268(3) Uani 1 1 d .
H3 H 0.7204 0.9436 0.1904 0.032 Uiso 1 1 calc R
C4 C 0.72540(10) 0.82314(11) 0.30261(16) 0.0277(3) Uani 1 1 d .
H4 H 0.6802 0.8006 0.3452 0.033 Uiso 1 1 calc R
C5 C 0.76015(11) 0.74340(11) 0.23160(18) 0.0310(3) Uani 1 1 d .
C6 C 0.82825(13) 0.68901(14) 0.3212(2) 0.0429(4) Uani 1 1 d .
H6A H 0.8762 0.7271 0.3547 0.052 Uiso 1 1 calc R
H6B H 0.8432 0.6401 0.2656 0.052 Uiso 1 1 calc R
H6C H 0.8095 0.6646 0.4013 0.052 Uiso 1 1 calc R
C7 C 0.71054(12) 0.90255(13) -0.07332(19) 0.0372(4) Uani 1 1 d .
H7A H 0.7194 0.8676 -0.1530 0.045 Uiso 1 1 calc R
H7B H 0.7573 0.9424 -0.0409 0.045 Uiso 1 1 calc R
H7C H 0.6603 0.9379 -0.1020 0.045 Uiso 1 1 calc R
C8 C 0.57311(11) 0.77673(13) -0.12787(19) 0.0361(4) Uani 1 1 d .
H8A H 0.5596 0.8405 -0.1462 0.043 Uiso 1 1 calc R
H8B H 0.5236 0.7470 -0.1100 0.043 Uiso 1 1 calc R
C9 C 0.59339(11) 0.73617(11) -0.25752(17) 0.0306(3) Uani 1 1 d .
C10 C 0.66641(11) 0.69213(12) -0.25531(19) 0.0347(4) Uani 1 1 d .
H10 H 0.7072 0.6887 -0.1708 0.042 Uiso 1 1 calc R
C11 C 0.68031(14) 0.65282(14) -0.3767(2) 0.0459(5) Uani 1 1 d .
H11 H 0.7305 0.6225 -0.3746 0.055 Uiso 1 1 calc R
C12 C 0.62159(18) 0.65776(15) -0.4995(2) 0.0537(6) Uani 1 1 d .
H12 H 0.6313 0.6313 -0.5823 0.064 Uiso 1 1 calc R
C13 C 0.54828(16) 0.70138(15) -0.5021(2) 0.0519(6) Uani 1 1 d .
H13 H 0.5076 0.7043 -0.5867 0.062 Uiso 1 1 calc R
C14 C 0.53401(13) 0.74062(13) -0.3825(2) 0.0405(4) Uani 1 1 d .
H14 H 0.4837 0.7707 -0.3851 0.049 Uiso 1 1 calc R
C15 C 0.59828(10) 0.91366(11) 0.16327(16) 0.0278(3) Uani 1 1 d .
C16 C 0.57037(11) 0.99455(11) 0.10023(18) 0.0340(4) Uani 1 1 d .
H16 H 0.6090 1.0354 0.0779 0.041 Uiso 1 1 calc R
C17 C 0.48746(12) 1.01724(12) 0.0690(2) 0.0388(4) Uani 1 1 d .
H17 H 0.4699 1.0722 0.0241 0.047 Uiso 1 1 calc R
C18 C 0.43083(11) 0.95902(12) 0.10402(19) 0.0359(4) Uani 1 1 d .
C19 C 0.45755(11) 0.87879(13) 0.16962(19) 0.0370(4) Uani 1 1 d .
H19 H 0.4191 0.8392 0.1955 0.044 Uiso 1 1 calc R
C20 C 0.53991(11) 0.85645(12) 0.19736(18) 0.0335(3) Uani 1 1 d .
H20 H 0.5571 0.8009 0.2406 0.040 Uiso 1 1 calc R
C21 C 0.31473(14) 1.04078(16) -0.0207(3) 0.0547(6) Uani 1 1 d .
H21A H 0.2548 1.0411 -0.0354 0.066 Uiso 1 1 calc R
H21B H 0.3302 1.0276 -0.1093 0.066 Uiso 1 1 calc R
H21C H 0.3364 1.0993 0.0133 0.066 Uiso 1 1 calc R
C22 C 0.79038(10) 0.86528(11) 0.41631(16) 0.0271(3) Uani 1 1 d .
C23 C 0.78840(10) 0.85188(11) 0.55649(17) 0.0311(3) Uani 1 1 d .
H23 H 0.7429 0.8218 0.5788 0.037 Uiso 1 1 calc R
C24 C 0.85138(11) 0.88150(12) 0.66360(17) 0.0331(3) Uani 1 1 d .
H24 H 0.8490 0.8715 0.7582 0.040 Uiso 1 1 calc R
C25 C 0.91812(10) 0.92586(11) 0.63261(17) 0.0290(3) Uani 1 1 d .
C26 C 0.92056(10) 0.94236(12) 0.49404(17) 0.0303(3) Uani 1 1 d .
H26 H 0.9652 0.9741 0.4721 0.036 Uiso 1 1 calc R
C27 C 0.85688(11) 0.91185(11) 0.38804(16) 0.0309(3) Uani 1 1 d .
H27 H 0.8588 0.9231 0.2935 0.037 Uiso 1 1 calc R
C28 C 1.04572(11) 1.00029(12) 0.71809(19) 0.0357(4) Uani 1 1 d .
H28A H 1.0823 1.0172 0.8069 0.043 Uiso 1 1 calc R
H28B H 1.0255 1.0541 0.6647 0.043 Uiso 1 1 calc R
H28C H 1.0759 0.9634 0.6640 0.043 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 '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
C18 O2 C21 117.41(17)
C25 O3 C28 117.50(13)
N2 N1 C8 114.29(14)
N2 N1 C2 121.60(13)
C8 N1 C2 124.05(14)
N3 N2 N1 122.15(14)
N2 N3 C5 119.96(14)
O1 C1 C5 129.12(17)
O1 C1 C2 127.10(16)
C5 C1 C2 103.72(13)
N1 C2 C7 112.39(14)
N1 C2 C1 101.54(13)
C7 C2 C1 114.38(14)
N1 C2 C3 110.21(12)
C7 C2 C3 114.69(14)
C1 C2 C3 102.45(13)
C15 C3 C2 112.13(13)
C15 C3 C4 116.76(13)
C2 C3 C4 105.11(13)
C22 C4 C5 111.86(13)
C22 C4 C3 114.62(13)
C5 C4 C3 104.44(13)
C1 C5 C6 116.71(16)
C1 C5 N3 105.73(14)
C6 C5 N3 106.10(14)
C1 C5 C4 103.23(13)
C6 C5 C4 117.46(15)
N3 C5 C4 106.71(14)
N1 C8 C9 114.42(14)
C10 C9 C14 119.26(17)
C10 C9 C8 122.69(15)
C14 C9 C8 117.99(16)
C9 C10 C11 120.19(19)
C12 C11 C10 120.2(2)
C11 C12 C13 119.84(19)
C14 C13 C12 120.4(2)
C13 C14 C9 120.1(2)
C16 C15 C20 117.32(16)
C16 C15 C3 119.45(15)
C20 C15 C3 122.90(15)
C17 C16 C15 121.89(17)
C18 C17 C16 119.50(16)
O2 C18 C17 124.78(17)
O2 C18 C19 115.68(17)
C17 C18 C19 119.54(16)
C20 C19 C18 120.24(17)
C19 C20 C15 121.48(16)
C27 C22 C23 117.59(14)
C27 C22 C4 122.52(14)
C23 C22 C4 119.70(14)
C24 C23 C22 121.33(15)
C23 C24 C25 119.97(15)
O3 C25 C24 115.76(14)
O3 C25 C26 124.33(15)
C24 C25 C26 119.90(15)
C27 C26 C25 119.23(15)
C26 C27 C22 121.94(15)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.206(2)
O2 C18 1.371(2)
O2 C21 1.425(3)
O3 C25 1.3682(19)
O3 C28 1.425(2)
N1 N2 1.340(2)
N1 C8 1.453(2)
N1 C2 1.496(2)
N2 N3 1.257(2)
N3 C5 1.528(2)
C1 C5 1.501(2)
C1 C2 1.518(2)
C2 C7 1.515(2)
C2 C3 1.558(2)
C3 C15 1.513(2)
C3 C4 1.579(2)
C4 C22 1.512(2)
C4 C5 1.560(2)
C5 C6 1.513(2)
C8 C9 1.515(2)
C9 C10 1.384(3)
C9 C14 1.397(2)
C10 C11 1.393(3)
C11 C12 1.377(3)
C12 C13 1.384(4)
C13 C14 1.381(3)
C15 C16 1.395(2)
C15 C20 1.395(2)
C16 C17 1.394(3)
C17 C18 1.386(3)
C18 C19 1.391(3)
C19 C20 1.384(3)
C22 C27 1.392(2)
C22 C23 1.397(2)
C23 C24 1.385(2)
C24 C25 1.390(2)
C25 C26 1.391(2)
C26 C27 1.390(2)
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 178.09(16)
C2 N1 N2 N3 -4.7(2)
N1 N2 N3 C5 -0.3(2)
N2 N1 C2 C7 162.75(15)
C8 N1 C2 C7 -20.3(2)
N2 N1 C2 C1 40.08(18)
C8 N1 C2 C1 -142.95(15)
N2 N1 C2 C3 -67.96(19)
C8 N1 C2 C3 109.01(17)
O1 C1 C2 N1 107.73(19)
C5 C1 C2 N1 -69.52(15)
O1 C1 C2 C7 -13.6(3)
C5 C1 C2 C7 169.18(14)
O1 C1 C2 C3 -138.30(18)
C5 C1 C2 C3 44.45(15)
N1 C2 C3 C15 -47.07(17)
C7 C2 C3 C15 80.97(17)
C1 C2 C3 C15 -154.50(13)
N1 C2 C3 C4 80.77(15)
C7 C2 C3 C4 -151.20(14)
C1 C2 C3 C4 -26.67(15)
C15 C3 C4 C22 -111.91(16)
C2 C3 C4 C22 123.12(14)
C15 C3 C4 C5 125.35(14)
C2 C3 C4 C5 0.38(16)
O1 C1 C5 C6 7.9(3)
C2 C1 C5 C6 -174.89(15)
O1 C1 C5 N3 -109.7(2)
C2 C1 C5 N3 67.45(15)
O1 C1 C5 C4 138.36(19)
C2 C1 C5 C4 -44.46(16)
N2 N3 C5 C1 -32.2(2)
N2 N3 C5 C6 -156.78(17)
N2 N3 C5 C4 77.22(19)
C22 C4 C5 C1 -98.06(15)
C3 C4 C5 C1 26.47(16)
C22 C4 C5 C6 31.9(2)
C3 C4 C5 C6 156.45(16)
C22 C4 C5 N3 150.76(13)
C3 C4 C5 N3 -84.71(15)
N2 N1 C8 C9 -90.21(18)
C2 N1 C8 C9 92.62(19)
N1 C8 C9 C10 3.3(2)
N1 C8 C9 C14 -179.48(16)
C14 C9 C10 C11 0.0(3)
C8 C9 C10 C11 177.26(17)
C9 C10 C11 C12 0.2(3)
C10 C11 C12 C13 -0.5(3)
C11 C12 C13 C14 0.6(3)
C12 C13 C14 C9 -0.3(3)
C10 C9 C14 C13 0.0(3)
C8 C9 C14 C13 -177.31(17)
C2 C3 C15 C16 -85.65(17)
C4 C3 C15 C16 152.99(14)
C2 C3 C15 C20 87.60(18)
C4 C3 C15 C20 -33.7(2)
C20 C15 C16 C17 -1.5(3)
C3 C15 C16 C17 172.17(16)
C15 C16 C17 C18 1.5(3)
C21 O2 C18 C17 18.4(3)
C21 O2 C18 C19 -162.11(17)
C16 C17 C18 O2 179.36(17)
C16 C17 C18 C19 -0.1(3)
O2 C18 C19 C20 179.29(16)
C17 C18 C19 C20 -1.2(3)
C18 C19 C20 C15 1.2(3)
C16 C15 C20 C19 0.1(2)
C3 C15 C20 C19 -173.27(16)
C5 C4 C22 C27 67.7(2)
C3 C4 C22 C27 -51.0(2)
C5 C4 C22 C23 -107.12(17)
C3 C4 C22 C23 134.24(16)
C27 C22 C23 C24 -1.8(2)
C4 C22 C23 C24 173.20(16)
C22 C23 C24 C25 0.3(3)
C28 O3 C25 C24 -177.19(16)
C28 O3 C25 C26 2.5(2)
C23 C24 C25 O3 -178.75(16)
C23 C24 C25 C26 1.6(3)
O3 C25 C26 C27 178.59(16)
C24 C25 C26 C27 -1.8(3)
C25 C26 C27 C22 0.1(3)
C23 C22 C27 C26 1.6(2)
C4 C22 C27 C26 -173.25(16)
