#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/58/4025894.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_4025894
loop_
_publ_author_name
'Thanh Luu'
'Boris J. Medos'
'Erin R. Graham'
'Danielle M. Vallee'
'Robert McDonald'
'Michael J. Ferguson'
'Rik R. Tykwinski'
_publ_contact_author_address
; Friedrich-Alexander-Universitat Erlangen
  Department Chemie und Pharmazie
  Geschaftsstelle
  Egerlandstr. 3
  91058 Erlangen
  Germany
;
_publ_contact_author_email       rik.tykwinski@chemie.uni-erlangen.de
_publ_contact_author_fax         +49(9131)8522540
_publ_contact_author_name        'Dr. Rik R. Tykwinski'
_publ_contact_author_phone       +49(9131)8526865
_publ_section_title
;
 Reactions of Terminal Polyynes with Benzyl Azide
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              8498
_journal_page_last               8507
_journal_paper_doi               10.1021/jo101870y
_journal_volume                  75
_journal_year                    2010
_chemical_formula_moiety         'C20 H15 N3 O'
_chemical_formula_sum            'C20 H15 N3 O'
_chemical_formula_weight         313.35
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 108.6532(13)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.7789(10)
_cell_length_b                   5.6104(5)
_cell_length_c                   14.1828(13)
_cell_measurement_reflns_used    4785
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      26.37
_cell_measurement_theta_min      2.87
_cell_volume                     812.64(13)
_computing_cell_refinement       'Bruker SAINT (Bruker, 1997)'
_computing_data_collection       'Bruker SMART (Bruker, 1997)'
_computing_data_reduction        'Bruker SAINT (Bruker, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL (Bruker, 1997)'
_computing_publication_material  'Bruker SHELXTL (Bruker, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      193(2)
_diffrn_detector_area_resol_mean 8.192
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type
'Bruker PLATFORM diffractometer/SMART 1000 CCD area detector'
_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  0.0167
_diffrn_reflns_av_sigmaI/netI    0.0248
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            6447
_diffrn_reflns_theta_full        26.39
_diffrn_reflns_theta_max         26.39
_diffrn_reflns_theta_min         1.52
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  0.9903
_exptl_absorpt_correction_T_min  0.9558
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             328
_exptl_crystal_size_max          0.56
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.143
_refine_diff_density_min         -0.167
_refine_diff_density_rms         0.028
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.2(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3302
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0343
_refine_ls_R_factor_gt           0.0306
_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)+(0.0408P)²+0.0744P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0789
_refine_ls_wR_factor_ref         0.0817
_reflns_number_gt                3069
_reflns_number_total             3302
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            jo101870y_si_009.cif
_cod_data_source_block           10f
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4025894
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -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
O O 1.06036(10) -0.0336(2) 0.67291(8) 0.0409(3) Uani 1 1 d . . .
N1 N -0.10065(11) 0.3571(2) 0.07262(9) 0.0293(3) Uani 1 1 d . . .
N2 N -0.10709(13) 0.1181(2) 0.06690(11) 0.0383(3) Uani 1 1 d . . .
N3 N 0.00664(12) 0.0351(2) 0.12278(10) 0.0381(3) Uani 1 1 d . . .
C1 C 0.08554(13) 0.2230(3) 0.16415(10) 0.0301(3) Uani 1 1 d . . .
C2 C 0.01664(14) 0.4294(3) 0.13186(10) 0.0307(3) Uani 1 1 d . . .
H2 H 0.0458 0.5885 0.1480 0.037 Uiso 1 1 calc R . .
C3 C -0.21674(13) 0.5006(3) 0.02142(10) 0.0336(3) Uani 1 1 d . . .
H3A H -0.2633 0.4260 -0.0435 0.040 Uiso 1 1 calc R . .
H3B H -0.1884 0.6616 0.0083 0.040 Uiso 1 1 calc R . .
C4 C 0.21547(14) 0.1884(3) 0.22997(11) 0.0336(3) Uani 1 1 d . . .
C5 C 0.32323(14) 0.1520(3) 0.28637(12) 0.0352(3) Uani 1 1 d . . .
C6 C 0.44604(14) 0.1089(3) 0.35226(12) 0.0361(3) Uani 1 1 d . . .
C7 C 0.55188(14) 0.0665(3) 0.41086(11) 0.0363(3) Uani 1 1 d . . .
C11 C -0.31014(12) 0.5237(3) 0.08125(10) 0.0289(3) Uani 1 1 d . . .
C12 C -0.40364(13) 0.3496(3) 0.07621(10) 0.0325(3) Uani 1 1 d . . .
H12 H -0.4094 0.2141 0.0349 0.039 Uiso 1 1 calc R . .
C13 C -0.48868(14) 0.3728(3) 0.13121(11) 0.0374(4) Uani 1 1 d . . .
H13 H -0.5519 0.2526 0.1280 0.045 Uiso 1 1 calc R . .
C14 C -0.48141(15) 0.5714(3) 0.19084(11) 0.0397(4) Uani 1 1 d . . .
H14 H -0.5398 0.5876 0.2284 0.048 Uiso 1 1 calc R . .
C15 C -0.38943(15) 0.7450(3) 0.19555(11) 0.0385(3) Uani 1 1 d . . .
H15 H -0.3847 0.8813 0.2363 0.046 Uiso 1 1 calc R . .
C16 C -0.30348(14) 0.7221(3) 0.14114(10) 0.0344(3) Uani 1 1 d . . .
H16 H -0.2400 0.8424 0.1449 0.041 Uiso 1 1 calc R . .
C21 C 0.68035(13) 0.0275(3) 0.48001(10) 0.0327(3) Uani 1 1 d . . .
C22 C 0.75364(14) -0.1727(3) 0.47428(11) 0.0350(3) Uani 1 1 d . . .
H22 H 0.7160 -0.2920 0.4261 0.042 Uiso 1 1 calc R . .
C23 C 0.88087(14) -0.2013(3) 0.53780(11) 0.0338(3) Uani 1 1 d . . .
H23 H 0.9299 -0.3389 0.5330 0.041 Uiso 1 1 calc R . .
C24 C 0.93594(13) -0.0274(3) 0.60845(10) 0.0311(3) Uani 1 1 d . . .
C25 C 0.86257(15) 0.1712(3) 0.61611(11) 0.0381(4) Uani 1 1 d . . .
H25 H 0.8997 0.2890 0.6652 0.046 Uiso 1 1 calc R . .
C26 C 0.73661(14) 0.1980(3) 0.55302(11) 0.0379(4) Uani 1 1 d . . .
H26 H 0.6872 0.3339 0.5591 0.045 Uiso 1 1 calc R . .
C27 C 1.13810(15) -0.2365(4) 0.67105(12) 0.0466(4) Uani 1 1 d . . .
H27A H 1.1497 -0.2497 0.6055 0.056 Uiso 1 1 calc R . .
H27B H 1.0945 -0.3800 0.6842 0.056 Uiso 1 1 calc R . .
H27C H 1.2239 -0.2200 0.7222 0.056 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C24 O C27 117.98(12) . . ?
C2 N1 N2 111.13(12) . . ?
C2 N1 C3 128.96(13) . . ?
N2 N1 C3 119.82(13) . . ?
N3 N2 N1 107.29(13) . . ?
N2 N3 C1 108.58(13) . . ?
N3 C1 C2 108.19(11) . . ?
N3 C1 C4 121.55(14) . . ?
C2 C1 C4 130.26(14) . . ?
N1 C2 C1 104.82(13) . . ?
N1 C3 C11 112.54(11) . . ?
C5 C4 C1 177.69(16) . . ?
C4 C5 C6 179.06(16) . . ?
C7 C6 C5 178.27(17) . . ?
C6 C7 C21 177.14(17) . . ?
C16 C11 C12 119.35(13) . . ?
C16 C11 C3 119.85(13) . . ?
C12 C11 C3 120.80(13) . . ?
C13 C12 C11 120.30(14) . . ?
C14 C13 C12 120.02(14) . . ?
C15 C14 C13 119.85(13) . . ?
C14 C15 C16 120.41(15) . . ?
C11 C16 C15 120.06(14) . . ?
C22 C21 C26 118.43(13) . . ?
C22 C21 C7 121.67(14) . . ?
C26 C21 C7 119.85(14) . . ?
C23 C22 C21 121.14(14) . . ?
C24 C23 C22 119.51(13) . . ?
O C24 C23 124.68(13) . . ?
O C24 C25 115.52(13) . . ?
C23 C24 C25 119.80(13) . . ?
C26 C25 C24 120.30(14) . . ?
C25 C26 C21 120.79(14) . . ?
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
O C24 1.3606(16) . ?
O C27 1.419(2) . ?
N1 C2 1.3376(18) . ?
N1 N2 1.3440(17) . ?
N1 C3 1.4695(18) . ?
N2 N3 1.3139(18) . ?
N3 C1 1.364(2) . ?
C1 C2 1.373(2) . ?
C1 C4 1.4262(18) . ?
C3 C11 1.5156(19) . ?
C4 C5 1.199(2) . ?
C5 C6 1.376(2) . ?
C6 C7 1.201(2) . ?
C7 C21 1.4347(19) . ?
C11 C16 1.388(2) . ?
C11 C12 1.389(2) . ?
C12 C13 1.387(2) . ?
C13 C14 1.386(2) . ?
C14 C15 1.376(2) . ?
C15 C16 1.388(2) . ?
C21 C22 1.391(2) . ?
C21 C26 1.397(2) . ?
C22 C23 1.3885(19) . ?
C23 C24 1.388(2) . ?
C24 C25 1.391(2) . ?
C25 C26 1.375(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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 N1 N2 N3 0.03(18) . . . . ?
C3 N1 N2 N3 -176.87(11) . . . . ?
N1 N2 N3 C1 0.02(17) . . . . ?
N2 N3 C1 C2 -0.06(16) . . . . ?
N2 N3 C1 C4 179.15(12) . . . . ?
N2 N1 C2 C1 -0.06(16) . . . . ?
C3 N1 C2 C1 176.47(13) . . . . ?
N3 C1 C2 N1 0.07(14) . . . . ?
C4 C1 C2 N1 -179.05(13) . . . . ?
C2 N1 C3 C11 -93.59(17) . . . . ?
N2 N1 C3 C11 82.68(17) . . . . ?
N3 C1 C4 C5 -31(4) . . . . ?
C2 C1 C4 C5 148(4) . . . . ?
C1 C4 C5 C6 -41(14) . . . . ?
C4 C5 C6 C7 30(15) . . . . ?
C5 C6 C7 C21 -160(4) . . . . ?
N1 C3 C11 C16 95.50(16) . . . . ?
N1 C3 C11 C12 -85.17(16) . . . . ?
C16 C11 C12 C13 -0.6(2) . . . . ?
C3 C11 C12 C13 -179.93(12) . . . . ?
C11 C12 C13 C14 0.6(2) . . . . ?
C12 C13 C14 C15 -0.2(2) . . . . ?
C13 C14 C15 C16 -0.2(2) . . . . ?
C12 C11 C16 C15 0.2(2) . . . . ?
C3 C11 C16 C15 179.55(13) . . . . ?
C14 C15 C16 C11 0.2(2) . . . . ?
C6 C7 C21 C22 -129(3) . . . . ?
C6 C7 C21 C26 48(3) . . . . ?
C26 C21 C22 C23 -1.5(2) . . . . ?
C7 C21 C22 C23 176.05(13) . . . . ?
C21 C22 C23 C24 0.1(2) . . . . ?
C27 O C24 C23 -2.8(2) . . . . ?
C27 O C24 C25 177.63(14) . . . . ?
C22 C23 C24 O -178.40(13) . . . . ?
C22 C23 C24 C25 1.1(2) . . . . ?
O C24 C25 C26 178.53(13) . . . . ?
C23 C24 C25 C26 -1.1(2) . . . . ?
C24 C25 C26 C21 -0.3(2) . . . . ?
C22 C21 C26 C25 1.6(2) . . . . ?
C7 C21 C26 C25 -176.00(14) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30659327
