#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/42/1514200.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_1514200
loop_
_publ_author_name
'Vekariya, Rakesh H'
'Liu, Ruzhang'
'Aubé, Jeffrey'
_publ_section_title
;
 A concomitant allylic azide rearrangement/intramolecular azide-alkyne
 cycloaddition sequence.
;
_journal_issue                   7
_journal_name_full               'Organic letters'
_journal_page_first              1844
_journal_page_last               1847
_journal_paper_doi               10.1021/ol500011f
_journal_volume                  16
_journal_year                    2014
_chemical_formula_sum            'C16 H19 N3 O'
_chemical_formula_weight         269.34
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXTL
_cell_angle_alpha                90.00
_cell_angle_beta                 93.587(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.6165(5)
_cell_length_b                   18.9916(11)
_cell_length_c                   11.2416(7)
_cell_measurement_reflns_used    4288
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      69.66
_cell_measurement_theta_min      4.58
_cell_volume                     1409.83(16)
_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  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.961
_diffrn_measured_fraction_theta_max 0.942
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'Helios multilayer optics'
_diffrn_radiation_source         'Bruker MicroStar microfocus rotating anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0537
_diffrn_reflns_av_sigmaI/netI    0.0400
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            13195
_diffrn_reflns_theta_full        66.00
_diffrn_reflns_theta_max         69.83
_diffrn_reflns_theta_min         4.58
_diffrn_standards_decay_%        0.00
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.645
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.779
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.269
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Needle
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.222
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       0.0053(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     258
_refine_ls_number_reflns         2509
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0522
_refine_ls_R_factor_gt           0.0439
_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)+(0.0731P)²+0.2266P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1123
_refine_ls_wR_factor_ref         0.1172
_reflns_number_gt                2131
_reflns_number_total             2509
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol500011f_si_001.cif
_cod_data_source_block           18a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 

 Adding full bibliography for
 ./tmp-cod-update-bibliographies-8800/cifs/1514200.cif.
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               1514200
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
O1 O 0.33540(17) 0.04908(5) 0.35994(9) 0.0282(3) Uani 1 1 d
N1 N 0.01622(19) 0.12811(6) 0.27741(11) 0.0246(3) Uani 1 1 d
N2 N -0.1425(2) 0.16266(6) 0.22242(11) 0.0262(3) Uani 1 1 d
N3 N -0.08678(19) 0.18010(6) 0.11597(11) 0.0258(3) Uani 1 1 d
C1 C -0.2406(3) 0.12593(10) 0.54603(16) 0.0376(4) Uani 1 1 d
H1A H -0.299(4) 0.1579(14) 0.601(2) 0.056(6) Uiso 1 1 d
H1B H -0.289(3) 0.0761(13) 0.5478(19) 0.050(6) Uiso 1 1 d
C2 C -0.0985(3) 0.14827(8) 0.47830(14) 0.0288(4) Uani 1 1 d
H2 H -0.057(3) 0.1965(12) 0.4808(18) 0.040(5) Uiso 1 1 d
C3 C 0.0126(2) 0.10054(8) 0.39954(13) 0.0257(3) Uani 1 1 d
H3 H -0.050(3) 0.0533(11) 0.3950(16) 0.030(5) Uiso 1 1 d
C4 C 0.2360(3) 0.09208(8) 0.44138(14) 0.0282(4) Uani 1 1 d
H4A H 0.247(3) 0.0678(10) 0.5192(18) 0.033(5) Uiso 1 1 d
H4B H 0.303(3) 0.1383(10) 0.4487(16) 0.031(5) Uiso 1 1 d
C5 C 0.3628(2) 0.08357(7) 0.24815(13) 0.0240(3) Uani 1 1 d
H5 H 0.477(3) 0.1185(9) 0.2611(15) 0.021(4) Uiso 1 1 d
C6 C 0.4170(2) 0.02679(7) 0.15821(13) 0.0253(3) Uani 1 1 d
H6 H 0.445(3) 0.0520(9) 0.0821(16) 0.025(4) Uiso 1 1 d
C7 C 0.2454(3) -0.02621(8) 0.13462(16) 0.0317(4) Uani 1 1 d
H7A H 0.216(3) -0.0521(11) 0.2110(19) 0.042(5) Uiso 1 1 d
H7B H 0.284(3) -0.0611(11) 0.0727(17) 0.034(5) Uiso 1 1 d
H7C H 0.127(3) -0.0015(11) 0.1017(19) 0.037(5) Uiso 1 1 d
C8 C 0.6137(3) -0.01016(8) 0.19993(16) 0.0323(4) Uani 1 1 d
H8A H 0.595(3) -0.0359(11) 0.279(2) 0.042(5) Uiso 1 1 d
H8B H 0.725(3) 0.0250(12) 0.2111(19) 0.044(6) Uiso 1 1 d
H8C H 0.656(3) -0.0459(12) 0.1393(19) 0.042(5) Uiso 1 1 d
C9 C 0.1733(2) 0.12306(7) 0.20717(13) 0.0234(3) Uani 1 1 d
C10 C 0.1069(2) 0.15726(7) 0.10300(13) 0.0236(3) Uani 1 1 d
C11 C 0.2103(2) 0.17369(7) -0.00555(13) 0.0232(3) Uani 1 1 d
C12 C 0.0998(2) 0.17669(7) -0.11578(13) 0.0261(3) Uani 1 1 d
H12 H -0.043(3) 0.1637(11) -0.1204(17) 0.038(5) Uiso 1 1 d
C13 C 0.1932(3) 0.19583(8) -0.21785(14) 0.0305(4) Uani 1 1 d
H13 H 0.116(3) 0.1970(12) -0.294(2) 0.048(6) Uiso 1 1 d
C14 C 0.3977(3) 0.21263(8) -0.21171(15) 0.0326(4) Uani 1 1 d
H14 H 0.464(3) 0.2283(11) -0.2875(19) 0.044(5) Uiso 1 1 d
C15 C 0.5091(3) 0.20924(8) -0.10305(15) 0.0295(4) Uani 1 1 d
H15 H 0.649(3) 0.2224(11) -0.0984(18) 0.041(5) Uiso 1 1 d
C16 C 0.4173(2) 0.18944(7) -0.00068(14) 0.0256(3) Uani 1 1 d
H16 H 0.496(3) 0.1877(9) 0.0731(17) 0.026(4) Uiso 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
C4 O1 C5 112.97(11)
C9 N1 N2 111.81(12)
C9 N1 C3 125.45(12)
N2 N1 C3 122.74(13)
N3 N2 N1 106.47(12)
N2 N3 C10 109.52(12)
C2 C1 H1A 119.9(15)
C2 C1 H1B 124.0(13)
H1A C1 H1B 116.1(19)
C1 C2 C3 122.91(15)
C1 C2 H2 120.5(13)
C3 C2 H2 116.5(13)
N1 C3 C2 112.02(12)
N1 C3 C4 104.60(13)
C2 C3 C4 112.53(13)
N1 C3 H3 107.9(11)
C2 C3 H3 111.2(11)
C4 C3 H3 108.3(11)
O1 C4 C3 109.86(12)
O1 C4 H4A 107.1(11)
C3 C4 H4A 109.5(11)
O1 C4 H4B 110.0(11)
C3 C4 H4B 110.7(11)
H4A C4 H4B 109.6(15)
O1 C5 C9 110.22(12)
O1 C5 C6 107.61(11)
C9 C5 C6 111.84(12)
O1 C5 H5 107.9(10)
C9 C5 H5 108.6(10)
C6 C5 H5 110.5(10)
C8 C6 C7 111.14(13)
C8 C6 C5 110.51(12)
C7 C6 C5 112.03(13)
C8 C6 H6 106.2(10)
C7 C6 H6 109.9(10)
C5 C6 H6 106.8(10)
C6 C7 H7A 110.6(12)
C6 C7 H7B 109.6(11)
H7A C7 H7B 109.7(16)
C6 C7 H7C 108.7(12)
H7A C7 H7C 111.3(17)
H7B C7 H7C 106.8(16)
C6 C8 H8A 109.8(12)
C6 C8 H8B 109.9(13)
H8A C8 H8B 109.7(17)
C6 C8 H8C 111.5(12)
H8A C8 H8C 108.3(17)
H8B C8 H8C 107.5(17)
N1 C9 C10 104.25(13)
N1 C9 C5 120.89(13)
C10 C9 C5 134.81(14)
N3 C10 C9 107.94(14)
N3 C10 C11 120.57(13)
C9 C10 C11 131.41(14)
C16 C11 C12 118.78(14)
C16 C11 C10 121.22(13)
C12 C11 C10 119.95(14)
C13 C12 C11 120.54(15)
C13 C12 H12 120.2(11)
C11 C12 H12 119.2(12)
C12 C13 C14 120.23(15)
C12 C13 H13 120.0(14)
C14 C13 H13 119.7(14)
C13 C14 C15 119.71(16)
C13 C14 H14 119.4(12)
C15 C14 H14 120.9(12)
C16 C15 C14 120.45(16)
C16 C15 H15 119.9(13)
C14 C15 H15 119.7(12)
C15 C16 C11 120.27(14)
C15 C16 H16 119.4(11)
C11 C16 H16 120.3(11)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C4 1.4190(19)
O1 C5 1.4387(18)
N1 C9 1.348(2)
N1 N2 1.3544(18)
N1 C3 1.4710(19)
N2 N3 1.3164(18)
N3 C10 1.369(2)
C1 C2 1.316(2)
C1 H1A 0.97(3)
C1 H1B 1.00(2)
C2 C3 1.492(2)
C2 H2 0.96(2)
C3 C4 1.532(2)
C3 H3 0.99(2)
C4 H4A 0.99(2)
C4 H4B 0.99(2)
C5 C9 1.508(2)
C5 C6 1.536(2)
C5 H5 1.012(18)
C6 C8 1.527(2)
C6 C7 1.528(2)
C6 H6 1.008(18)
C7 H7A 1.02(2)
C7 H7B 1.01(2)
C7 H7C 0.96(2)
C8 H8A 1.02(2)
C8 H8B 1.00(2)
C8 H8C 1.01(2)
C9 C10 1.386(2)
C10 C11 1.469(2)
C11 C16 1.400(2)
C11 C12 1.400(2)
C12 C13 1.386(2)
C12 H12 0.98(2)
C13 C14 1.387(3)
C13 H13 0.97(2)
C14 C15 1.388(2)
C14 H14 1.03(2)
C15 C16 1.386(2)
C15 H15 0.96(2)
C16 H16 0.951(19)
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
C9 N1 N2 N3 -0.12(15)
C3 N1 N2 N3 179.51(12)
N1 N2 N3 C10 -0.35(15)
C9 N1 C3 C2 142.59(14)
N2 N1 C3 C2 -36.99(18)
C9 N1 C3 C4 20.43(18)
N2 N1 C3 C4 -159.16(12)
C1 C2 C3 N1 130.44(16)
C1 C2 C3 C4 -112.03(18)
C5 O1 C4 C3 71.36(16)
N1 C3 C4 O1 -55.29(15)
C2 C3 C4 O1 -177.13(12)
C4 O1 C5 C9 -42.78(16)
C4 O1 C5 C6 -164.98(12)
O1 C5 C6 C8 -61.05(16)
C9 C5 C6 C8 177.75(13)
O1 C5 C6 C7 63.47(15)
C9 C5 C6 C7 -57.73(16)
N2 N1 C9 C10 0.53(15)
C3 N1 C9 C10 -179.09(12)
N2 N1 C9 C5 -177.07(12)
C3 N1 C9 C5 3.3(2)
O1 C5 C9 N1 6.05(18)
C6 C5 C9 N1 125.73(14)
O1 C5 C9 C10 -170.66(15)
C6 C5 C9 C10 -51.0(2)
N2 N3 C10 C9 0.69(16)
N2 N3 C10 C11 -176.35(12)
N1 C9 C10 N3 -0.72(15)
C5 C9 C10 N3 176.37(14)
N1 C9 C10 C11 175.88(14)
C5 C9 C10 C11 -7.0(3)
N3 C10 C11 C16 142.55(14)
C9 C10 C11 C16 -33.7(2)
N3 C10 C11 C12 -34.77(19)
C9 C10 C11 C12 148.99(15)
C16 C11 C12 C13 -0.9(2)
C10 C11 C12 C13 176.51(13)
C11 C12 C13 C14 -0.3(2)
C12 C13 C14 C15 0.9(2)
C13 C14 C15 C16 -0.2(2)
C14 C15 C16 C11 -1.0(2)
C12 C11 C16 C15 1.5(2)
C10 C11 C16 C15 -175.82(13)
