#------------------------------------------------------------------------------
#$Date: 2017-05-05 00:20:53 +0300 (Fri, 05 May 2017) $
#$Revision: 196071 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/59/1545937.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_1545937
loop_
_publ_author_name
'Jeanbourquin, Loïc N'
'Scopelliti, Rosario'
'Fadaei Tirani, Farzaneh'
'Severin, Kay'
_publ_section_title
;
 Synthesis and Reactivity of 1-Allenyltriazenes.
;
_journal_issue                   8
_journal_name_full               'Organic letters'
_journal_page_first              2070
_journal_page_last               2073
_journal_paper_doi               10.1021/acs.orglett.7b00671
_journal_volume                  19
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C16 H23 N3'
_chemical_formula_sum            'C16 H23 N3'
_chemical_formula_weight         257.37
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2016-11-25 # Formatted by publCIF

;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.4082(5)
_cell_length_b                   7.7785(3)
_cell_length_c                   19.6994(9)
_cell_measurement_reflns_used    5545
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      75.1150
_cell_measurement_theta_min      4.4480
_cell_volume                     1594.87(12)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Mercury 3.9 (CCDC, 2016)'
_computing_publication_material
'CIF Tools (WinGX 2014.1, L.J. Farruggia, 2012)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1333
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω    -67.00  26.00   1.00    5.00    --  -42.26  37.00   0.00   93
  2  ω   -114.00 -21.00   1.00    5.00    --  -42.26 -37.00-180.00   93
  3  ω   -112.00 -18.00   1.00    5.00    --  -42.26 -57.00  90.00   94
  4  ω      3.00  57.00   1.00    5.00    --   42.26 -99.00  60.00   54
  5  ω     52.00  79.00   1.00    5.00    --   42.26 -99.00 120.00   27
  6  ω     60.00  90.00   1.00    5.00    --   42.26-125.00 -60.00   30
  7  ω    136.00 162.00   1.00   30.00    --  109.26  77.00 -30.00   26
  8  ω     99.00 126.00   1.00   30.00    --  109.26  77.00 -30.00   27
  9  ω     37.00  90.00   1.00   30.00    --  109.26 -61.00 -60.00   53
 10  ω     84.00 178.00   1.00   30.00    --  109.26  30.00 150.00   94
 11  ω     57.00 116.00   1.00   30.00    --  109.26-111.00  60.00   59
 12  ω     40.00 138.00   1.00   30.00    --  109.26 -61.00-180.00   98
 13  ω     33.00 122.00   1.00   30.00    --  109.26 -30.00 -30.00   89
 14  ω     40.00 136.00   1.00   30.00    --  109.26 -61.00  60.00   96
 15  ω     79.00 114.00   1.00   30.00    --  109.26-111.00 -60.00   35
 16  ω     78.00 114.00   1.00   30.00    --  109.26-111.00-180.00   36
 17  ω     33.00 156.00   1.00   30.00    --  109.26 -15.00 150.00  123
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0334
_diffrn_reflns_av_unetI/netI     0.0310
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            10238
_diffrn_reflns_point_group_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.956
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.317
_diffrn_reflns_theta_min         4.489
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.495
_exptl_absorpt_correction_T_max  0.891
_exptl_absorpt_correction_T_min  0.840
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model.
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear pale yellow'
_exptl_crystal_density_diffrn    1.072
_exptl_crystal_description       plate
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.447
_exptl_crystal_size_mid          0.354
_exptl_crystal_size_min          0.239
_refine_diff_density_max         0.095
_refine_diff_density_min         -0.084
_refine_diff_density_rms         0.021
_refine_ls_abs_structure_details
;
 Flack x determined using 1286 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         3152
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0335
_refine_ls_R_factor_gt           0.0291
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0318P)²+0.0866P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0716
_refine_ls_wR_factor_ref         0.0743
_reflns_Friedel_coverage         0.872
_reflns_Friedel_fraction_full    0.946
_reflns_Friedel_fraction_max     0.919
_reflns_number_gt                2921
_reflns_number_total             3152
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ol7b00671_si_003.cif
_cod_data_source_block           shelx
_cod_database_code               1545937
_publcif_datablock.id            {751d6b01-a9d7-45b2-947a-c622e7b9566d}
_shelx_shelxl_version_number     2016/6
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.809
_shelx_estimated_absorpt_t_max   0.891
_publcif_info_exptl_table_max_cols 4
_publcif_info_exptl_table_use_headnotes n
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, 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_site_symmetry_order
_atom_site_calc_flag
N1 N 0.45967(14) 0.79604(18) 0.52301(8) 0.0341(3) Uani 1 1 d
N2 N 0.53721(15) 0.74554(18) 0.57241(8) 0.0349(3) Uani 1 1 d
N3 N 0.64408(15) 0.82605(19) 0.57663(8) 0.0363(3) Uani 1 1 d
C1 C 0.50109(18) 0.9185(2) 0.47039(10) 0.0355(4) Uani 1 1 d
H1 H 0.563(2) 0.992(3) 0.4933(12) 0.033(5) Uiso 1 1 d
C2 C 0.5688(2) 0.8241(3) 0.41295(11) 0.0426(4) Uani 1 1 d
H2A H 0.641(3) 0.754(4) 0.4301(15) 0.063(8) Uiso 1 1 d
H2B H 0.611(2) 0.905(4) 0.3801(14) 0.046(6) Uiso 1 1 d
H2C H 0.505(2) 0.754(3) 0.3877(14) 0.042(6) Uiso 1 1 d
C3 C 0.3891(2) 1.0266(3) 0.44474(11) 0.0448(4) Uani 1 1 d
H3A H 0.329(3) 0.961(4) 0.4130(15) 0.055(7) Uiso 1 1 d
H3B H 0.426(3) 1.126(4) 0.4189(15) 0.057(7) Uiso 1 1 d
H3C H 0.338(3) 1.071(4) 0.4830(16) 0.063(8) Uiso 1 1 d
C4 C 0.34834(18) 0.6809(2) 0.51270(10) 0.0394(4) Uani 1 1 d
H4 H 0.303(2) 0.725(3) 0.4710(14) 0.046(6) Uiso 1 1 d
C5 C 0.2535(2) 0.6995(3) 0.57031(15) 0.0519(5) Uani 1 1 d
H5A H 0.300(3) 0.664(3) 0.6146(14) 0.050(7) Uiso 1 1 d
H5B H 0.176(3) 0.628(4) 0.5609(17) 0.069(8) Uiso 1 1 d
H5C H 0.221(3) 0.822(4) 0.5735(18) 0.072(9) Uiso 1 1 d
C6 C 0.3903(2) 0.4949(3) 0.50284(12) 0.0459(4) Uani 1 1 d
H6A H 0.457(3) 0.488(4) 0.4669(15) 0.062(8) Uiso 1 1 d
H6B H 0.311(3) 0.422(4) 0.4924(15) 0.057(7) Uiso 1 1 d
H6C H 0.432(2) 0.450(3) 0.5445(13) 0.043(6) Uiso 1 1 d
C7 C 0.71911(19) 0.7616(2) 0.62915(10) 0.0374(4) Uani 1 1 d
H7 H 0.683(3) 0.663(4) 0.6557(14) 0.052(7) Uiso 1 1 d
C8 C 0.8366(2) 0.8244(3) 0.64158(9) 0.0388(4) Uani 1 1 d
H8 H 0.871(3) 0.923(4) 0.6147(15) 0.053(7) Uiso 1 1 d
C9 C 0.9234(2) 0.7518(2) 0.69070(9) 0.0379(4) Uani 1 1 d
H9 H 0.893(2) 0.650(3) 0.7172(13) 0.047(6) Uiso 1 1 d
C10 C 1.04225(19) 0.8114(3) 0.70238(10) 0.0397(4) Uani 1 1 d
H10 H 1.067(3) 0.912(4) 0.6780(15) 0.054(7) Uiso 1 1 d
C11 C 1.13739(19) 0.7365(3) 0.74857(9) 0.0378(4) Uani 1 1 d
C12 C 1.1231(2) 0.5729(3) 0.77716(11) 0.0451(4) Uani 1 1 d
H12 H 1.047(3) 0.501(4) 0.7652(15) 0.062(8) Uiso 1 1 d
C13 C 1.2139(2) 0.5087(3) 0.82157(11) 0.0530(5) Uani 1 1 d
H13 H 1.204(3) 0.394(4) 0.8399(17) 0.073(9) Uiso 1 1 d
C14 C 1.3218(2) 0.6019(3) 0.83726(11) 0.0534(5) Uani 1 1 d
H14 H 1.387(3) 0.558(4) 0.8661(15) 0.057(7) Uiso 1 1 d
C15 C 1.3403(2) 0.7609(3) 0.80769(12) 0.0537(6) Uani 1 1 d
H15 H 1.417(3) 0.825(4) 0.8138(17) 0.070(9) Uiso 1 1 d
C16 C 1.2486(2) 0.8280(3) 0.76393(11) 0.0463(4) Uani 1 1 d
H16 H 1.259(3) 0.940(4) 0.7441(15) 0.053(7) 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
N2 N1 C1 122.08(14)
N2 N1 C4 113.52(14)
C1 N1 C4 121.64(14)
N3 N2 N1 115.63(15)
N2 N3 C7 111.13(16)
N1 C1 C2 110.27(15)
N1 C1 C3 111.51(16)
C2 C1 C3 111.98(16)
N1 C1 H1 104.4(14)
C2 C1 H1 108.7(13)
C3 C1 H1 109.8(13)
C1 C2 H2A 111.4(17)
C1 C2 H2B 112.3(15)
H2A C2 H2B 103(2)
C1 C2 H2C 109.0(15)
H2A C2 H2C 112(2)
H2B C2 H2C 108(2)
C1 C3 H3A 113.1(15)
C1 C3 H3B 107.6(17)
H3A C3 H3B 108(2)
C1 C3 H3C 110.8(17)
H3A C3 H3C 108(2)
H3B C3 H3C 109(2)
N1 C4 C5 110.54(16)
N1 C4 C6 111.61(16)
C5 C4 C6 111.94(17)
N1 C4 H4 105.9(14)
C5 C4 H4 105.8(14)
C6 C4 H4 110.7(15)
C4 C5 H5A 107.6(15)
C4 C5 H5B 110(2)
H5A C5 H5B 113(2)
C4 C5 H5C 111(2)
H5A C5 H5C 111(2)
H5B C5 H5C 105(2)
C4 C6 H6A 110.0(18)
C4 C6 H6B 108.7(16)
H6A C6 H6B 113(2)
C4 C6 H6C 110.7(14)
H6A C6 H6C 106(2)
H6B C6 H6C 109(2)
C8 C7 N3 121.18(18)
C8 C7 H7 121.6(16)
N3 C7 H7 117.1(16)
C7 C8 C9 123.57(18)
C7 C8 H8 120.8(16)
C9 C8 H8 115.6(16)
C10 C9 C8 123.98(18)
C10 C9 H9 118.5(15)
C8 C9 H9 117.6(15)
C9 C10 C11 126.34(18)
C9 C10 H10 116.7(18)
C11 C10 H10 116.9(18)
C16 C11 C12 117.76(18)
C16 C11 C10 119.59(18)
C12 C11 C10 122.64(18)
C13 C12 C11 120.7(2)
C13 C12 H12 119.4(18)
C11 C12 H12 119.8(18)
C14 C13 C12 120.8(2)
C14 C13 H13 119.4(19)
C12 C13 H13 119.8(19)
C13 C14 C15 119.5(2)
C13 C14 H14 121.9(18)
C15 C14 H14 118.5(18)
C14 C15 C16 120.2(2)
C14 C15 H15 122(2)
C16 C15 H15 117(2)
C15 C16 C11 121.0(2)
C15 C16 H16 121.1(17)
C11 C16 H16 117.9(17)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 N2 1.324(2)
N1 C1 1.473(2)
N1 C4 1.479(2)
N2 N3 1.279(2)
N3 C7 1.390(3)
C1 C2 1.522(3)
C1 C3 1.523(3)
C1 H1 0.97(2)
C2 H2A 0.99(3)
C2 H2B 1.00(3)
C2 H2C 1.00(3)
C3 H3A 1.02(3)
C3 H3B 1.00(3)
C3 H3C 0.99(3)
C4 C5 1.511(3)
C4 C6 1.524(3)
C4 H4 1.01(3)
C5 H5A 1.04(3)
C5 H5B 0.99(3)
C5 H5C 1.01(3)
C6 H6A 0.99(3)
C6 H6B 1.03(3)
C6 H6C 0.99(3)
C7 C8 1.339(3)
C7 H7 1.00(3)
C8 C9 1.439(3)
C8 H8 1.00(3)
C9 C10 1.341(3)
C9 H9 1.00(3)
C10 C11 1.466(3)
C10 H10 0.95(3)
C11 C16 1.392(3)
C11 C12 1.400(3)
C12 C13 1.381(3)
C12 H12 1.00(3)
C13 C14 1.372(4)
C13 H13 0.97(3)
C14 C15 1.381(4)
C14 H14 0.95(3)
C15 C16 1.388(3)
C15 H15 0.95(3)
C16 H16 0.96(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
C1 N1 N2 N3 8.6(2)
C4 N1 N2 N3 170.07(15)
N1 N2 N3 C7 -178.98(15)
N2 N1 C1 C2 85.43(19)
C4 N1 C1 C2 -74.5(2)
N2 N1 C1 C3 -149.51(17)
C4 N1 C1 C3 50.5(2)
N2 N1 C4 C5 72.0(2)
C1 N1 C4 C5 -126.48(19)
N2 N1 C4 C6 -53.3(2)
C1 N1 C4 C6 108.24(19)
N2 N3 C7 C8 178.29(17)
N3 C7 C8 C9 -173.64(17)
C7 C8 C9 C10 178.40(19)
C8 C9 C10 C11 -175.98(19)
C9 C10 C11 C16 -169.4(2)
C9 C10 C11 C12 12.3(3)
C16 C11 C12 C13 3.0(3)
C10 C11 C12 C13 -178.67(19)
C11 C12 C13 C14 -1.7(3)
C12 C13 C14 C15 -0.7(3)
C13 C14 C15 C16 1.8(4)
C14 C15 C16 C11 -0.5(4)
C12 C11 C16 C15 -1.8(3)
C10 C11 C16 C15 179.7(2)
loop_
_publcif_info_datablock.id
_publcif_info_datablock.publ_exptl
_publcif_info_datablock.publ_geom
_publcif_info_datablock.structure
{751d6b01-a9d7-45b2-947a-c622e7b9566d} y y y
loop_
_publcif_info_exptl_table_extra_item
sin_theta_over_lambda_max
loop_
_publcif_info_tables.block_id
_publcif_info_tables.reference_item
{751d6b01-a9d7-45b2-947a-c622e7b9566d} '_publcif_info_datablock.publ_exptl'
