#------------------------------------------------------------------------------
#$Date: 2016-03-21 05:27:59 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178479 $
#$URL: svn://www.crystallography.net/cod/cif/4/03/00/4030029.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_4030029
loop_
_publ_author_name
'Panmand, Deepak S.'
'Jishkariani, Davit'
'Hall, C. Dennis'
'Steel, Peter J.'
'Asiri, Abdullah M.'
'Katritzky, Alan R.'
_publ_section_title
;
 Synthesis and Direct C2 Functionalization of Imidazolium and
 1,2,4-Triazolium N-Imides.
;
_journal_issue                   21
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              10593
_journal_paper_doi               10.1021/jo501746u
_journal_volume                  79
_journal_year                    2014
_chemical_formula_moiety         'C23 H18 N4 O3'
_chemical_formula_sum            'C23 H18 N4 O3'
_chemical_formula_weight         398.41
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 96.9849(16)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.87321(10)
_cell_length_b                   16.3775(3)
_cell_length_c                   19.4994(3)
_cell_measurement_reflns_used    9719
_cell_measurement_temperature    120(1)
_cell_measurement_theta_max      73.7818
_cell_measurement_theta_min      2.6958
_cell_volume                     1861.70(6)
_computing_cell_refinement
; 
?
;
_computing_data_collection
; 
?
;
_computing_data_reduction
; 
?
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      120(1)
_diffrn_detector_area_resol_mean 10.6501
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0573
_diffrn_reflns_av_sigmaI/netI    0.0291
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            20377
_diffrn_reflns_theta_full        67.47
_diffrn_reflns_theta_max         67.47
_diffrn_reflns_theta_min         3.54
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85225
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) 
(compiled Sep 14 2012,17:21:16) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_crystal_colour
; 
colorless
;
_exptl_crystal_density_diffrn    1.421
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description
; 
block
;
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.208
_refine_diff_density_min         -0.295
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         3349
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0468
_refine_ls_R_factor_gt           0.0409
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0720P)²+0.4800P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1077
_refine_ls_wR_factor_ref         0.1141
_reflns_number_gt                2933
_reflns_number_total             3349
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo501746u_si_003.cif
_cod_data_source_block           dsp41
_cod_depositor_comments
'Adding full bibliography for 4030029--4030031.cif.'
_cod_database_code               4030029
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
_atom_site_refinement_flags
N1 N 0.96628(19) 0.47163(7) 0.36192(6) 0.0205(3) Uani 1 1 d .
C2 C 0.9145(2) 0.54958(8) 0.37684(7) 0.0194(3) Uani 1 1 d .
N3 N 1.05755(19) 0.57262(7) 0.43269(6) 0.0193(3) Uani 1 1 d .
C4 C 1.1462(2) 0.44565(9) 0.40871(7) 0.0224(3) Uani 1 1 d .
H4A H 1.2158 0.3946 0.4096 0.027 Uiso 1 1 calc R
C5 C 1.2032(2) 0.50773(9) 0.45300(7) 0.0220(3) Uani 1 1 d .
H5A H 1.3185 0.5072 0.4902 0.026 Uiso 1 1 calc R
N6 N 1.0410(2) 0.65144(7) 0.45846(6) 0.0206(3) Uani 1 1 d .
C7 C 1.2081(2) 0.67343(9) 0.50768(7) 0.0217(3) Uani 1 1 d .
O8 O 1.3771(2) 0.63302(7) 0.53434(6) 0.0354(3) Uani 1 1 d .
C9 C 1.1816(2) 0.76070(9) 0.52982(7) 0.0212(3) Uani 1 1 d .
C10 C 0.9756(2) 0.80346(9) 0.51671(7) 0.0242(3) Uani 1 1 d .
H10A H 0.8461 0.7773 0.4949 0.029 Uiso 1 1 calc R
C11 C 0.9621(3) 0.88458(9) 0.53593(8) 0.0268(3) Uani 1 1 d .
H11A H 0.8237 0.9125 0.5272 0.032 Uiso 1 1 calc R
C12 C 1.1550(3) 0.92445(9) 0.56825(7) 0.0270(3) Uani 1 1 d .
H12A H 1.1467 0.9792 0.5803 0.032 Uiso 1 1 calc R
C13 C 1.3594(3) 0.88217(10) 0.58239(8) 0.0282(3) Uani 1 1 d .
H13A H 1.4883 0.9084 0.6046 0.034 Uiso 1 1 calc R
C14 C 1.3724(3) 0.80070(10) 0.56350(7) 0.0261(3) Uani 1 1 d .
H14A H 1.5100 0.7726 0.5735 0.031 Uiso 1 1 calc R
C15 C 0.7337(2) 0.60044(8) 0.33918(7) 0.0197(3) Uani 1 1 d .
C16 C 0.5640(2) 0.63508(9) 0.37444(7) 0.0217(3) Uani 1 1 d .
H16A H 0.5657 0.6261 0.4216 0.026 Uiso 1 1 calc R
C17 C 0.3934(2) 0.68268(9) 0.33921(7) 0.0219(3) Uani 1 1 d .
H17A H 0.2765 0.7045 0.3617 0.026 Uiso 1 1 calc R
C18 C 0.4012(2) 0.69696(8) 0.26955(7) 0.0207(3) Uani 1 1 d .
C19 C 0.5670(2) 0.66435(9) 0.23318(7) 0.0228(3) Uani 1 1 d .
H19A H 0.5674 0.6753 0.1864 0.027 Uiso 1 1 calc R
C20 C 0.7334(2) 0.61463(9) 0.26874(7) 0.0220(3) Uani 1 1 d .
H20A H 0.8452 0.5907 0.2453 0.026 Uiso 1 1 calc R
C21 C 0.8537(2) 0.42216(9) 0.30521(7) 0.0230(3) Uani 1 1 d .
H21A H 0.6976 0.4414 0.2935 0.028 Uiso 1 1 calc R
H21B H 0.8464 0.3660 0.3206 0.028 Uiso 1 1 calc R
C22 C 0.9757(2) 0.42483(8) 0.24107(7) 0.0203(3) Uani 1 1 d .
C23 C 0.8805(3) 0.38211(9) 0.18261(7) 0.0239(3) Uani 1 1 d .
H23A H 0.7427 0.3543 0.1833 0.029 Uiso 1 1 calc R
C24 C 0.9903(3) 0.38093(9) 0.12350(8) 0.0274(3) Uani 1 1 d .
H24A H 0.9255 0.3522 0.0848 0.033 Uiso 1 1 calc R
C25 C 1.1957(3) 0.42215(9) 0.12151(7) 0.0268(3) Uani 1 1 d .
H25A H 1.2696 0.4208 0.0820 0.032 Uiso 1 1 calc R
C26 C 1.2896(2) 0.46539(9) 0.17941(7) 0.0248(3) Uani 1 1 d .
H26A H 1.4264 0.4937 0.1784 0.030 Uiso 1 1 calc R
C27 C 1.1812(2) 0.46669(9) 0.23868(7) 0.0225(3) Uani 1 1 d .
H27A H 1.2461 0.4957 0.2772 0.027 Uiso 1 1 calc R
N28 N 0.2287(2) 0.75172(8) 0.23256(6) 0.0243(3) Uani 1 1 d .
O29 O 0.06110(18) 0.77031(7) 0.26070(6) 0.0349(3) Uani 1 1 d .
O30 O 0.26465(19) 0.77686(7) 0.17541(5) 0.0313(3) Uani 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
C2 N1 C4 108.89(12)
C2 N1 C21 126.35(12)
C4 N1 C21 124.75(12)
N3 C2 N1 107.70(12)
N3 C2 C15 125.87(12)
N1 C2 C15 126.43(12)
C2 N3 C5 108.53(12)
C2 N3 N6 119.17(11)
C5 N3 N6 132.29(11)
C5 C4 N1 107.57(12)
C4 C5 N3 107.30(12)
C7 N6 N3 115.55(11)
O8 C7 N6 129.19(14)
O8 C7 C9 119.13(12)
N6 C7 C9 111.65(12)
C14 C9 C10 118.75(14)
C14 C9 C7 118.45(13)
C10 C9 C7 122.79(13)
C11 C10 C9 120.60(14)
C10 C11 C12 120.18(14)
C13 C12 C11 119.64(14)
C12 C13 C14 120.13(14)
C13 C14 C9 120.68(14)
C20 C15 C16 120.15(13)
C20 C15 C2 119.99(13)
C16 C15 C2 119.86(12)
C17 C16 C15 120.04(13)
C16 C17 C18 118.27(13)
C19 C18 C17 123.27(13)
C19 C18 N28 118.02(13)
C17 C18 N28 118.68(13)
C18 C19 C20 117.87(13)
C19 C20 C15 120.36(13)
N1 C21 C22 113.08(11)
C27 C22 C23 118.83(13)
C27 C22 C21 122.70(12)
C23 C22 C21 118.46(13)
C24 C23 C22 120.32(14)
C23 C24 C25 120.67(13)
C26 C25 C24 119.09(14)
C27 C26 C25 120.57(14)
C26 C27 C22 120.52(13)
O29 N28 O30 124.01(13)
O29 N28 C18 118.35(12)
O30 N28 C18 117.63(12)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C2 1.3523(19)
N1 C4 1.3768(18)
N1 C21 1.4624(18)
C2 N3 1.3462(18)
C2 C15 1.4735(19)
N3 C5 1.3913(18)
N3 N6 1.3929(17)
C4 C5 1.350(2)
N6 C7 1.3362(18)
C7 O8 1.2522(18)
C7 C9 1.507(2)
C9 C14 1.392(2)
C9 C10 1.394(2)
C10 C11 1.385(2)
C11 C12 1.390(2)
C12 C13 1.384(2)
C13 C14 1.389(2)
C15 C20 1.393(2)
C15 C16 1.398(2)
C16 C17 1.384(2)
C17 C18 1.384(2)
C18 C19 1.380(2)
C18 N28 1.4740(18)
C19 C20 1.391(2)
C21 C22 1.516(2)
C22 C27 1.394(2)
C22 C23 1.395(2)
C23 C24 1.388(2)
C24 C25 1.387(2)
C25 C26 1.389(2)
C26 C27 1.386(2)
N28 O29 1.2225(17)
N28 O30 1.2300(17)
