#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/58/4025895.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_4025895
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         'C21 H13 N3'
_chemical_formula_sum            'C21 H13 N3'
_chemical_formula_weight         307.34
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           29
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.8926(10)
_cell_length_b                   20.0670(19)
_cell_length_c                   7.3933(7)
_cell_measurement_reflns_used    5290
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      25.13
_cell_measurement_theta_min      3.05
_cell_volume                     1616.0(3)
_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 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0352
_diffrn_reflns_av_sigmaI/netI    0.0190
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            11984
_diffrn_reflns_theta_full        26.38
_diffrn_reflns_theta_max         26.38
_diffrn_reflns_theta_min         1.01
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  0.9947
_exptl_absorpt_correction_T_min  0.9592
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.263
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.169
_refine_diff_density_min         -0.148
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.188
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         1796
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.188
_refine_ls_R_factor_all          0.0412
_refine_ls_R_factor_gt           0.0332
_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)+(0.0663P)²+0.0600P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0902
_refine_ls_wR_factor_ref         0.1070
_reflns_number_gt                1621
_reflns_number_total             1796
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            jo101870y_si_010.cif
_cod_data_source_block           12b
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' 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_database_code               4025895
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.15882(17) -0.03513(9) 0.1178(3) 0.0321(4) Uani 1 1 d . . .
N2 N 0.28110(17) -0.03252(8) 0.1397(3) 0.0366(5) Uani 1 1 d . . .
N3 N 0.30716(16) 0.02570(8) 0.2126(3) 0.0352(5) Uani 1 1 d . . .
C1 C 0.19960(19) 0.05981(10) 0.2363(3) 0.0303(5) Uani 1 1 d . . .
C2 C 0.1051(2) 0.02111(10) 0.1749(4) 0.0333(5) Uani 1 1 d . . .
H2 H 0.0201 0.0317 0.1732 0.040 Uiso 1 1 calc R . .
C3 C 0.1008(2) -0.09417(11) 0.0361(4) 0.0413(6) Uani 1 1 d . . .
H3A H 0.1475 -0.1069 -0.0734 0.050 Uiso 1 1 calc R . .
H3B H 0.0165 -0.0823 -0.0024 0.050 Uiso 1 1 calc R . .
C4 C 0.1952(2) 0.12472(11) 0.3142(4) 0.0342(5) Uani 1 1 d . . .
C5 C 0.1886(2) 0.17923(11) 0.3813(4) 0.0356(5) Uani 1 1 d . . .
C6 C 0.1818(2) 0.24139(11) 0.4565(4) 0.0383(6) Uani 1 1 d . . .
C7 C 0.1739(2) 0.29591(12) 0.5237(4) 0.0388(6) Uani 1 1 d . . .
C8 C 0.1619(2) 0.35864(11) 0.5951(4) 0.0369(5) Uani 1 1 d . . .
C9 C 0.1483(2) 0.41410(11) 0.6521(3) 0.0358(5) Uani 1 1 d . . .
C11 C 0.09443(19) -0.15313(11) 0.1608(3) 0.0321(5) Uani 1 1 d . . .
C12 C 0.0308(2) -0.14997(13) 0.3214(4) 0.0470(7) Uani 1 1 d . . .
H12 H -0.0049 -0.1090 0.3589 0.056 Uiso 1 1 calc R . .
C13 C 0.0184(3) -0.20596(15) 0.4285(5) 0.0575(8) Uani 1 1 d . . .
H13 H -0.0250 -0.2033 0.5397 0.069 Uiso 1 1 calc R . .
C14 C 0.0688(3) -0.26561(14) 0.3744(5) 0.0578(9) Uani 1 1 d . . .
H14 H 0.0593 -0.3043 0.4473 0.069 Uiso 1 1 calc R . .
C15 C 0.1325(3) -0.26895(12) 0.2157(5) 0.0581(8) Uani 1 1 d . . .
H15 H 0.1677 -0.3100 0.1782 0.070 Uiso 1 1 calc R . .
C16 C 0.1459(2) -0.21280(12) 0.1094(4) 0.0452(6) Uani 1 1 d . . .
H16 H 0.1911 -0.2154 -0.0002 0.054 Uiso 1 1 calc R . .
C21 C 0.13049(19) 0.48165(10) 0.7080(3) 0.0301(5) Uani 1 1 d . . .
C22 C 0.2186(2) 0.51430(11) 0.8123(3) 0.0331(5) Uani 1 1 d . . .
H22 H 0.2905 0.4913 0.8495 0.040 Uiso 1 1 calc R . .
C23 C 0.2014(2) 0.58007(12) 0.8616(4) 0.0371(6) Uani 1 1 d . . .
H23 H 0.2614 0.6020 0.9335 0.045 Uiso 1 1 calc R . .
C24 C 0.0976(2) 0.61424(11) 0.8070(4) 0.0399(6) Uani 1 1 d . . .
H24 H 0.0866 0.6595 0.8407 0.048 Uiso 1 1 calc R . .
C25 C 0.0094(2) 0.58225(11) 0.7028(4) 0.0386(6) Uani 1 1 d . . .
H25 H -0.0620 0.6057 0.6653 0.046 Uiso 1 1 calc R . .
C26 C 0.0254(2) 0.51648(11) 0.6537(3) 0.0351(5) Uani 1 1 d . . .
H26 H -0.0352 0.4947 0.5826 0.042 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'
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
C2 N1 N2 111.23(18) . . ?
C2 N1 C3 128.3(2) . . ?
N2 N1 C3 120.4(2) . . ?
N3 N2 N1 107.32(17) . . ?
N2 N3 C1 108.15(17) . . ?
C2 C1 N3 108.54(19) . . ?
C2 C1 C4 128.9(2) . . ?
N3 C1 C4 122.53(19) . . ?
N1 C2 C1 104.8(2) . . ?
N1 C3 C11 113.7(2) . . ?
C5 C4 C1 178.4(2) . . ?
C4 C5 C6 179.5(3) . . ?
C7 C6 C5 178.9(3) . . ?
C6 C7 C8 177.8(3) . . ?
C9 C8 C7 177.5(3) . . ?
C8 C9 C21 176.2(3) . . ?
C16 C11 C12 118.9(2) . . ?
C16 C11 C3 119.8(2) . . ?
C12 C11 C3 121.1(2) . . ?
C11 C12 C13 120.4(2) . . ?
C14 C13 C12 120.2(3) . . ?
C15 C14 C13 119.7(3) . . ?
C14 C15 C16 120.2(3) . . ?
C11 C16 C15 120.7(3) . . ?
C22 C21 C26 119.1(2) . . ?
C22 C21 C9 120.8(2) . . ?
C26 C21 C9 120.1(2) . . ?
C23 C22 C21 120.1(2) . . ?
C22 C23 C24 120.5(2) . . ?
C23 C24 C25 119.9(2) . . ?
C26 C25 C24 120.0(2) . . ?
C25 C26 C21 120.3(2) . . ?
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
N1 C2 1.340(3) . ?
N1 N2 1.343(3) . ?
N1 C3 1.472(3) . ?
N2 N3 1.318(2) . ?
N3 C1 1.368(3) . ?
C1 C2 1.367(3) . ?
C1 C4 1.425(3) . ?
C3 C11 1.501(3) . ?
C4 C5 1.203(3) . ?
C5 C6 1.368(3) . ?
C6 C7 1.205(3) . ?
C7 C8 1.371(3) . ?
C8 C9 1.199(3) . ?
C9 C21 1.430(3) . ?
C11 C16 1.376(3) . ?
C11 C12 1.377(4) . ?
C12 C13 1.381(4) . ?
C13 C14 1.376(4) . ?
C14 C15 1.365(5) . ?
C15 C16 1.381(4) . ?
C21 C22 1.394(3) . ?
C21 C26 1.400(3) . ?
C22 C23 1.382(3) . ?
C23 C24 1.383(4) . ?
C24 C25 1.389(3) . ?
C25 C26 1.380(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
_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 0.3(3) . . . . ?
C3 N1 N2 N3 179.1(2) . . . . ?
N1 N2 N3 C1 0.0(3) . . . . ?
N2 N3 C1 C2 -0.3(3) . . . . ?
N2 N3 C1 C4 179.4(2) . . . . ?
N2 N1 C2 C1 -0.5(3) . . . . ?
C3 N1 C2 C1 -179.2(2) . . . . ?
N3 C1 C2 N1 0.5(3) . . . . ?
C4 C1 C2 N1 -179.2(2) . . . . ?
C2 N1 C3 C11 -106.2(3) . . . . ?
N2 N1 C3 C11 75.2(3) . . . . ?
C2 C1 C4 C5 24(11) . . . . ?
N3 C1 C4 C5 -155(10) . . . . ?
C1 C4 C5 C6 -151(36) . . . . ?
C4 C5 C6 C7 155(36) . . . . ?
C5 C6 C7 C8 -74(19) . . . . ?
C6 C7 C8 C9 -1(12) . . . . ?
C7 C8 C9 C21 -27(9) . . . . ?
N1 C3 C11 C16 -123.5(3) . . . . ?
N1 C3 C11 C12 60.8(3) . . . . ?
C16 C11 C12 C13 -0.3(4) . . . . ?
C3 C11 C12 C13 175.4(3) . . . . ?
C11 C12 C13 C14 -0.6(5) . . . . ?
C12 C13 C14 C15 0.9(5) . . . . ?
C13 C14 C15 C16 -0.3(4) . . . . ?
C12 C11 C16 C15 1.0(4) . . . . ?
C3 C11 C16 C15 -174.8(2) . . . . ?
C14 C15 C16 C11 -0.7(4) . . . . ?
C8 C9 C21 C22 -128(3) . . . . ?
C8 C9 C21 C26 50(4) . . . . ?
C26 C21 C22 C23 0.3(3) . . . . ?
C9 C21 C22 C23 178.4(2) . . . . ?
C21 C22 C23 C24 -0.5(4) . . . . ?
C22 C23 C24 C25 0.4(4) . . . . ?
C23 C24 C25 C26 -0.1(4) . . . . ?
C24 C25 C26 C21 -0.1(4) . . . . ?
C22 C21 C26 C25 0.0(3) . . . . ?
C9 C21 C26 C25 -178.1(2) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30659328
