#------------------------------------------------------------------------------
#$Date: 2017-10-13 02:32:00 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201954 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/49/1504960.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_1504960
loop_
_publ_author_name
'Liu, Yuxiu'
'Yan, Wuming'
'Chen, Yunfeng'
'Petersen, Jeffrey L.'
'Shi, Xiaodong'
_publ_section_title
;
 Efficient synthesis of N-2-aryl-1,2,3-triazole fluorophores via
 post-triazole arylation.
;
_journal_issue                   23
_journal_name_full               'Organic letters'
_journal_page_first              5389
_journal_page_last               5392
_journal_paper_doi               10.1021/ol802246q
_journal_volume                  10
_journal_year                    2008
_chemical_formula_sum            'C20 H14 N4 O'
_chemical_formula_weight         326.35
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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            8
_cell_length_a                   38.946(3)
_cell_length_b                   10.7963(8)
_cell_length_c                   7.8297(6)
_cell_measurement_reflns_used    9658
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.44
_cell_measurement_theta_min      2.45
_cell_volume                     3292.2(4)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_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  0.0429
_diffrn_reflns_av_sigmaI/netI    0.0485
_diffrn_reflns_limit_h_max       50
_diffrn_reflns_limit_h_min       -50
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            20926
_diffrn_reflns_theta_full        27.58
_diffrn_reflns_theta_max         27.58
_diffrn_reflns_theta_min         2.09
_diffrn_standards_decay_%        none
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.9766
_exptl_absorpt_correction_T_min  0.9668
_exptl_absorpt_correction_type   semi-empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1360
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.229
_refine_diff_density_min         -0.152
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3753
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0724
_refine_ls_R_factor_gt           0.0521
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0734P)²+0.7613P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1432
_refine_ls_wR_factor_ref         0.1620
_reflns_number_gt                2691
_reflns_number_total             3753
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol802246q_si_004.cif
_cod_data_source_block           ms58ccd
_cod_original_sg_symbol_H-M      Pbca
_cod_database_code               1504960
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, 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
O1 O 0.68630(3) 0.24502(13) 0.0684(2) 0.0772(5) Uani 1 1 d .
N1 N 0.58015(3) 0.22402(13) 0.19341(19) 0.0522(4) Uani 1 1 d .
N2 N 0.58372(3) 0.10112(13) 0.18445(19) 0.0506(4) Uani 1 1 d .
N3 N 0.61585(3) 0.05934(13) 0.17094(19) 0.0511(4) Uani 1 1 d .
N4 N 0.52872(4) 0.04996(17) 0.2763(2) 0.0720(5) Uani 1 1 d .
C1 C 0.61238(4) 0.26640(16) 0.1834(2) 0.0480(4) Uani 1 1 d .
C2 C 0.63467(4) 0.16319(15) 0.1715(2) 0.0478(4) Uani 1 1 d .
C3 C 0.67231(4) 0.15798(16) 0.1393(2) 0.0536(4) Uani 1 1 d .
C4 C 0.69181(4) 0.04315(16) 0.1834(2) 0.0494(4) Uani 1 1 d .
C5 C 0.68250(4) -0.03611(17) 0.3148(2) 0.0550(4) Uani 1 1 d .
H5 H 0.6629 -0.0199 0.3792 0.066 Uiso 1 1 calc R
C6 C 0.70229(5) -0.13905(18) 0.3500(3) 0.0653(5) Uani 1 1 d .
H6 H 0.6963 -0.1910 0.4399 0.078 Uiso 1 1 calc R
C7 C 0.73093(5) -0.16560(19) 0.2530(3) 0.0724(6) Uani 1 1 d .
H7 H 0.7437 -0.2367 0.2751 0.087 Uiso 1 1 calc R
C8 C 0.74061(5) -0.0866(2) 0.1233(3) 0.0752(6) Uani 1 1 d .
H8 H 0.7602 -0.1034 0.0591 0.090 Uiso 1 1 calc R
C9 C 0.72124(4) 0.0174(2) 0.0890(3) 0.0639(5) Uani 1 1 d .
H9 H 0.7279 0.0709 0.0020 0.077 Uiso 1 1 calc R
C10 C 0.61869(4) 0.40145(16) 0.1827(2) 0.0504(4) Uani 1 1 d .
C11 C 0.64786(5) 0.45420(18) 0.2539(3) 0.0642(5) Uani 1 1 d .
H11 H 0.6647 0.4038 0.3011 0.077 Uiso 1 1 calc R
C12 C 0.65195(7) 0.5813(2) 0.2548(3) 0.0795(6) Uani 1 1 d .
H12 H 0.6713 0.6157 0.3057 0.095 Uiso 1 1 calc R
C13 C 0.62810(7) 0.6568(2) 0.1822(3) 0.0870(8) Uani 1 1 d .
H13 H 0.6311 0.7423 0.1833 0.104 Uiso 1 1 calc R
C14 C 0.59918(7) 0.6053(2) 0.1064(4) 0.0863(7) Uani 1 1 d .
H14 H 0.5830 0.6564 0.0548 0.104 Uiso 1 1 calc R
C15 C 0.59426(5) 0.47829(18) 0.1072(3) 0.0657(5) Uani 1 1 d .
H15 H 0.5747 0.4443 0.0575 0.079 Uiso 1 1 calc R
C16 C 0.55491(4) 0.01808(16) 0.1794(2) 0.0504(4) Uani 1 1 d .
C17 C 0.55641(5) -0.08388(18) 0.0746(3) 0.0740(6) Uani 1 1 d .
H17 H 0.5756 -0.1011 0.0080 0.089 Uiso 1 1 calc R
C18 C 0.52742(6) -0.1602(2) 0.0742(4) 0.0933(8) Uani 1 1 d .
H18 H 0.5268 -0.2306 0.0059 0.112 Uiso 1 1 calc R
C19 C 0.49985(6) -0.1303(2) 0.1754(4) 0.0854(8) Uani 1 1 d .
H19 H 0.4805 -0.1805 0.1782 0.102 Uiso 1 1 calc R
C20 C 0.50153(6) -0.0266(3) 0.2703(3) 0.0851(7) Uani 1 1 d .
H20 H 0.4825 -0.0065 0.3366 0.102 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
N2 N1 C1 103.81(13)
N3 N2 N1 115.96(12)
N3 N2 C16 121.28(14)
N1 N2 C16 122.66(13)
N2 N3 C2 103.29(13)
C16 N4 C20 115.4(2)
N1 C1 C2 108.06(15)
N1 C1 C10 119.56(15)
C2 C1 C10 132.37(15)
N3 C2 C1 108.87(14)
N3 C2 C3 120.44(15)
C1 C2 C3 130.15(15)
O1 C3 C2 119.20(16)
O1 C3 C4 121.16(15)
C2 C3 C4 119.51(14)
C5 C4 C9 119.10(17)
C5 C4 C3 123.41(15)
C9 C4 C3 117.48(16)
C6 C5 C4 119.93(18)
C7 C6 C5 120.6(2)
C8 C7 C6 119.88(19)
C7 C8 C9 119.82(19)
C8 C9 C4 120.7(2)
C11 C10 C15 119.00(17)
C11 C10 C1 122.66(16)
C15 C10 C1 118.34(16)
C12 C11 C10 120.3(2)
C13 C12 C11 121.0(2)
C12 C13 C14 119.5(2)
C15 C14 C13 120.5(2)
C14 C15 C10 119.8(2)
N4 C16 C17 125.89(17)
N4 C16 N2 115.22(16)
C17 C16 N2 118.88(16)
C16 C17 C18 116.1(2)
C19 C18 C17 119.5(2)
C20 C19 C18 118.5(2)
N4 C20 C19 124.7(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C3 1.220(2)
N1 N2 1.336(2)
N1 C1 1.338(2)
N2 N3 1.3343(18)
N2 C16 1.437(2)
N3 C2 1.340(2)
N4 C16 1.317(2)
N4 C20 1.344(3)
C1 C2 1.416(2)
C1 C10 1.479(2)
C2 C3 1.489(2)
C3 C4 1.494(2)
C4 C5 1.387(3)
C4 C9 1.392(2)
C5 C6 1.380(3)
C6 C7 1.379(3)
C7 C8 1.379(3)
C8 C9 1.379(3)
C10 C11 1.387(3)
C10 C15 1.394(3)
C11 C12 1.381(3)
C12 C13 1.360(4)
C13 C14 1.389(4)
C14 C15 1.384(3)
C16 C17 1.374(3)
C17 C18 1.398(3)
C18 C19 1.373(4)
C19 C20 1.345(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30651523
