#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/62/4026259.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_4026259
loop_
_publ_author_name
'Subhendu Sekhar Bag'
'Rajen Kundu'
_publ_section_title
;
 Installation/Modulation of the Emission Response via Click Reaction
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3348
_journal_page_last               3356
_journal_paper_doi               10.1021/jo200231k
_journal_volume                  76
_journal_year                    2011
_chemical_formula_moiety         'C17 H18 N4 O'
_chemical_formula_sum            'C17 H18 N4 O'
_chemical_formula_weight         294.35
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 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                   5.7361(3)
_cell_length_b                   13.5039(6)
_cell_length_c                   19.7921(8)
_cell_measurement_reflns_used    2233
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.43
_cell_measurement_theta_min      2.32
_cell_volume                     1533.09(12)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0593
_diffrn_reflns_av_sigmaI/netI    0.0962
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            16621
_diffrn_reflns_theta_full        28.38
_diffrn_reflns_theta_max         28.38
_diffrn_reflns_theta_min         1.83
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.9877
_exptl_absorpt_correction_T_min  0.9637
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   multi-scan
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.275
_exptl_crystal_description       Rod
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.129
_refine_diff_density_min         -0.158
_refine_diff_density_rms         0.027
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -1.0(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.925
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         3850
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.925
_refine_ls_R_factor_all          0.1237
_refine_ls_R_factor_gt           0.0380
_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)+(0.0020P)²+0.0020P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0476
_refine_ls_wR_factor_ref         0.0531
_reflns_number_gt                1540
_reflns_number_total             3850
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo200231k_si_002.cif
_cod_data_source_block           rk-18_0m
_cod_database_code               4026259
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'
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 -0.0494(3) 0.78790(11) -0.13232(7) 0.0832(5) Uani 1 1 d .
C7 C 0.1762(4) 0.23386(14) 0.11874(9) 0.0495(5) Uani 1 1 d .
C12 C -0.0263(4) 0.17951(14) 0.11351(9) 0.0581(6) Uani 1 1 d .
H12 H -0.1366 0.1981 0.0815 0.070 Uiso 1 1 calc R
C4 C 0.1284(4) 0.53964(14) -0.02102(9) 0.0500(6) Uani 1 1 d .
C1 C -0.0014(5) 0.70309(16) -0.09690(10) 0.0615(6) Uani 1 1 d .
C11 C -0.0714(4) 0.09881(14) 0.15376(9) 0.0600(6) Uani 1 1 d .
H11 H -0.2100 0.0640 0.1482 0.072 Uiso 1 1 calc R
C9 C 0.2885(4) 0.12353(15) 0.20873(10) 0.0705(7) Uani 1 1 d .
H9 H 0.3971 0.1064 0.2416 0.085 Uiso 1 1 calc R
C3 C 0.2654(4) 0.62431(14) -0.02020(9) 0.0635(6) Uani 1 1 d .
H3 H 0.4012 0.6267 0.0054 0.076 Uiso 1 1 calc R
C10 C 0.0873(4) 0.06837(15) 0.20278(10) 0.0583(6) Uani 1 1 d .
C2 C 0.1964(4) 0.70512(14) -0.05813(10) 0.0680(6) Uani 1 1 d .
H2 H 0.2865 0.7623 -0.0573 0.082 Uiso 1 1 calc R
C5 C -0.0700(4) 0.53684(14) -0.05882(10) 0.0650(6) Uani 1 1 d .
H5 H -0.1613 0.4799 -0.0592 0.078 Uiso 1 1 calc R
C8 C 0.3332(4) 0.20362(15) 0.16711(10) 0.0662(6) Uani 1 1 d .
H8 H 0.4729 0.2379 0.1719 0.079 Uiso 1 1 calc R
C6 C -0.1373(4) 0.61898(16) -0.09703(9) 0.0688(7) Uani 1 1 d .
H6 H -0.2734 0.6169 -0.1225 0.083 Uiso 1 1 calc R
C15 C -0.2613(6) 0.79169(19) -0.16876(11) 0.1197(11) Uani 1 1 d .
H15A H -0.2625 0.7404 -0.2023 0.180 Uiso 1 1 calc R
H15B H -0.2756 0.8550 -0.1904 0.180 Uiso 1 1 calc R
H15C H -0.3895 0.7822 -0.1383 0.180 Uiso 1 1 calc R
C13 C -0.1596(5) -0.07007(15) 0.23621(10) 0.0999(9) Uani 1 1 d .
H13A H -0.2874 -0.0363 0.2574 0.150 Uiso 1 1 calc R
H13B H -0.1382 -0.1336 0.2571 0.150 Uiso 1 1 calc R
H13C H -0.1928 -0.0789 0.1891 0.150 Uiso 1 1 calc R
C14 C 0.1954(5) -0.03495(17) 0.30114(11) 0.1242(11) Uani 1 1 d .
H14A H 0.3516 -0.0467 0.2856 0.186 Uiso 1 1 calc R
H14B H 0.1386 -0.0928 0.3241 0.186 Uiso 1 1 calc R
H14C H 0.1947 0.0203 0.3317 0.186 Uiso 1 1 calc R
C17 C 0.0672(4) 0.38052(14) 0.04229(9) 0.0534(5) Uani 1 1 d .
H17 H -0.0920 0.3706 0.0365 0.064 Uiso 1 1 calc R
N2 N 0.4364(3) 0.36358(13) 0.07345(8) 0.0668(5) Uani 1 1 d .
N3 N 0.4235(4) 0.44539(13) 0.03733(8) 0.0709(6) Uani 1 1 d .
N4 N 0.1982(4) 0.45602(12) 0.01757(8) 0.0552(5) Uani 1 1 d .
C16 C 0.2203(4) 0.32164(14) 0.07785(9) 0.0499(5) Uani 1 1 d .
N1 N 0.0458(4) -0.01326(14) 0.24360(9) 0.0814(6) 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 0.0033 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
C1 O1 C15 117.6(2)
C8 C7 C12 116.48(19)
C8 C7 C16 120.9(2)
C12 C7 C16 122.5(2)
C11 C12 C7 122.5(2)
C5 C4 C3 120.14(19)
C5 C4 N4 120.6(2)
C3 C4 N4 119.3(2)
C2 C1 O1 115.9(2)
C2 C1 C6 119.1(2)
O1 C1 C6 125.0(2)
C12 C11 C10 121.0(2)
C10 C9 C8 121.8(2)
C2 C3 C4 118.82(19)
C9 C10 N1 121.5(2)
C9 C10 C11 116.6(2)
N1 C10 C11 121.9(2)
C1 C2 C3 121.7(2)
C4 C5 C6 120.4(2)
C7 C8 C9 121.6(2)
C1 C6 C5 119.8(2)
N4 C17 C16 105.35(19)
N3 N2 C16 109.36(18)
N2 N3 N4 107.34(17)
C17 N4 N3 110.09(17)
C17 N4 C4 129.4(2)
N3 N4 C4 120.46(19)
N2 C16 C17 107.85(18)
N2 C16 C7 122.0(2)
C17 C16 C7 130.0(2)
C10 N1 C13 120.9(2)
C10 N1 C14 121.0(2)
C13 N1 C14 117.59(19)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.371(2)
O1 C15 1.414(3)
C7 C8 1.376(2)
C7 C12 1.378(2)
C7 C16 1.458(2)
C12 C11 1.375(2)
C4 C5 1.363(2)
C4 C3 1.387(2)
C4 N4 1.421(2)
C1 C2 1.370(3)
C1 C6 1.378(2)
C11 C10 1.393(2)
C9 C10 1.379(3)
C9 C8 1.384(2)
C3 C2 1.382(2)
C10 N1 1.387(2)
C5 C6 1.397(2)
C13 N1 1.414(2)
C14 N1 1.456(2)
C17 N4 1.358(2)
C17 C16 1.378(2)
N2 N3 1.3180(19)
N2 C16 1.365(2)
N3 N4 1.358(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30659371
