#------------------------------------------------------------------------------
#$Date: 2017-10-14 21:27:35 +0200 (Sat 14 de Oct de 2017) $
#$Revision: 202017 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/02/7200201.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_7200201
loop_
_publ_author_name
'Ramana, C. V.'
'Chatterjee, Soumitra'
'Durugkar, Kulbhushan A.'
'Gonnade, Rajesh G.'
_publ_section_title
;
 “Click” synthesis of isomeric compounds for assessing
 the efficiency of the bifurcated Br⋯NO2 synthon
;
_journal_issue                   1
_journal_name_full               CrystEngComm
_journal_page_first              143
_journal_paper_doi               10.1039/b809985e
_journal_volume                  11
_journal_year                    2009
_chemical_formula_moiety         'C14 H10 N4 O2'
_chemical_formula_sum            'C14 H10 N4 O2'
_chemical_formula_weight         266.26
_chemical_name_systematic
;
?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                101.081(6)
_cell_angle_beta                 99.217(6)
_cell_angle_gamma                90.859(6)
_cell_formula_units_Z            2
_cell_length_a                   5.757(2)
_cell_length_b                   7.198(3)
_cell_length_c                   14.862(6)
_cell_measurement_reflns_used    2295
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      27.74
_cell_measurement_theta_min      2.83
_cell_volume                     595.9(4)
_computing_cell_refinement       'SAINT (Bruker, 2003)'
_computing_data_collection       'SMART (Bruker, 2003)'
_computing_data_reduction        SAINT
_computing_molecular_graphics
'ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2006)'
_computing_publication_material  'SHELXTL (Bruker, 2003)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      297(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device       'Bruker Smart APEX'
_diffrn_measurement_device_type  'CCD Area Detector'
_diffrn_measurement_method       'Phi and Omega Scan'
_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  0.0181
_diffrn_reflns_av_sigmaI/netI    0.0227
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            4652
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.83
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_T_max  0.9917
_exptl_absorpt_correction_T_min  0.9315
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'bruker sadabs'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.484
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             276
_exptl_crystal_size_max          0.69
_exptl_crystal_size_mid          0.52
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.195
_refine_diff_density_min         -0.171
_refine_diff_density_rms         0.035
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         2296
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0414
_refine_ls_R_factor_gt           0.0363
_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)+(0.0543P)²+0.1231P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0996
_refine_ls_wR_factor_ref         0.1042
_reflns_number_gt                2006
_reflns_number_total             2296
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b809985e.txt
_cod_data_source_block           16
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_cell_volume        595.8(4)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7200201
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
O1 O 0.0476(2) -0.2112(2) 0.00540(8) 0.0689(4) Uani 1 1 d . . .
O2 O -0.2953(2) -0.1897(2) 0.04544(8) 0.0776(4) Uani 1 1 d . . .
N1 N 0.32113(18) 0.18190(15) 0.42594(7) 0.0320(3) Uani 1 1 d . . .
N2 N 0.55834(19) 0.19502(17) 0.45150(8) 0.0393(3) Uani 1 1 d . . .
N3 N 0.60249(19) 0.27687(17) 0.53911(8) 0.0391(3) Uani 1 1 d . . .
N4 N -0.0818(2) -0.16618(18) 0.06263(8) 0.0465(3) Uani 1 1 d . . .
C1 C 0.2148(2) 0.25638(18) 0.49866(9) 0.0329(3) Uani 1 1 d . . .
C2 C 0.3947(2) 0.31752(17) 0.57052(9) 0.0312(3) Uani 1 1 d . . .
C3 C 0.3868(2) 0.40877(17) 0.66732(8) 0.0312(3) Uani 1 1 d . . .
C4 C 0.5798(2) 0.40535(19) 0.73656(9) 0.0358(3) Uani 1 1 d . . .
C5 C 0.5715(3) 0.4882(2) 0.82794(10) 0.0413(3) Uani 1 1 d . . .
C6 C 0.3714(3) 0.5752(2) 0.85153(10) 0.0421(3) Uani 1 1 d . . .
C7 C 0.1791(2) 0.5797(2) 0.78347(10) 0.0403(3) Uani 1 1 d . . .
C8 C 0.1858(2) 0.49702(19) 0.69168(10) 0.0361(3) Uani 1 1 d . . .
C9 C 0.2188(2) 0.09372(17) 0.33377(8) 0.0308(3) Uani 1 1 d . . .
C10 C -0.0036(2) 0.00526(19) 0.31776(9) 0.0352(3) Uani 1 1 d . . .
C11 C -0.1025(2) -0.07915(19) 0.22806(9) 0.0361(3) Uani 1 1 d . . .
C12 C 0.0256(2) -0.07538(18) 0.15746(9) 0.0348(3) Uani 1 1 d . . .
C13 C 0.2481(2) 0.01044(19) 0.17242(9) 0.0373(3) Uani 1 1 d . . .
C14 C 0.3444(2) 0.09852(19) 0.26166(9) 0.0348(3) Uani 1 1 d . . .
H1 H 0.050(3) 0.2583(19) 0.4931(10) 0.038(4) Uiso 1 1 d . . .
H4 H 0.722(3) 0.344(2) 0.7209(10) 0.038(4) Uiso 1 1 d . . .
H5 H 0.708(3) 0.486(2) 0.8741(12) 0.049(4) Uiso 1 1 d . . .
H6 H 0.361(3) 0.631(2) 0.9145(12) 0.052(4) Uiso 1 1 d . . .
H7 H 0.036(3) 0.643(2) 0.7998(11) 0.046(4) Uiso 1 1 d . . .
H8 H 0.049(3) 0.499(2) 0.6445(11) 0.039(4) Uiso 1 1 d . . .
H10 H -0.090(3) 0.001(2) 0.3681(11) 0.046(4) Uiso 1 1 d . . .
H11 H -0.257(3) -0.141(2) 0.2156(11) 0.045(4) Uiso 1 1 d . . .
H13 H 0.334(3) 0.012(2) 0.1211(11) 0.048(4) Uiso 1 1 d . . .
H14 H 0.498(3) 0.163(2) 0.2743(11) 0.043(4) Uiso 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 N2 110.54(10) . . ?
C1 N1 C9 129.40(11) . . ?
N2 N1 C9 120.03(10) . . ?
N3 N2 N1 107.05(10) . . ?
N2 N3 C2 109.30(11) . . ?
O2 N4 O1 123.90(13) . . ?
O2 N4 C12 117.94(12) . . ?
O1 N4 C12 118.15(13) . . ?
N1 C1 C2 104.96(11) . . ?
C1 C2 N3 108.14(11) . . ?
C1 C2 C3 129.73(12) . . ?
N3 C2 C3 122.12(11) . . ?
C4 C3 C8 118.91(12) . . ?
C4 C3 C2 120.23(12) . . ?
C8 C3 C2 120.86(12) . . ?
C5 C4 C3 120.39(13) . . ?
C6 C5 C4 120.34(13) . . ?
C7 C6 C5 119.78(13) . . ?
C6 C7 C8 120.29(13) . . ?
C7 C8 C3 120.30(13) . . ?
C10 C9 C14 121.49(12) . . ?
C10 C9 N1 119.35(11) . . ?
C14 C9 N1 119.16(11) . . ?
C11 C10 C9 119.06(12) . . ?
C12 C11 C10 118.75(13) . . ?
C11 C12 C13 122.86(12) . . ?
C11 C12 N4 118.04(12) . . ?
C13 C12 N4 119.11(12) . . ?
C14 C13 C12 118.35(12) . . ?
C13 C14 C9 119.46(12) . . ?
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
O1 N4 1.2195(17) . ?
O2 N4 1.2172(18) . ?
N1 C1 1.3524(16) . ?
N1 N2 1.3542(16) . ?
N1 C9 1.4221(16) . ?
N2 N3 1.3045(16) . ?
N3 C2 1.3680(17) . ?
N4 C12 1.4663(18) . ?
C1 C2 1.3631(18) . ?
C2 C3 1.4704(18) . ?
C3 C4 1.3925(19) . ?
C3 C8 1.3931(18) . ?
C4 C5 1.383(2) . ?
C5 C6 1.382(2) . ?
C6 C7 1.380(2) . ?
C7 C8 1.386(2) . ?
C9 C10 1.3862(18) . ?
C9 C14 1.3905(18) . ?
C10 C11 1.3804(19) . ?
C11 C12 1.3795(19) . ?
C12 C13 1.380(2) . ?
C13 C14 1.3781(19) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C6 H6 O1 0.956(17) 2.575(17) 3.342(2) 137.3(13) 1_566
C6 H6 O2 0.956(17) 2.660(17) 3.333(2) 127.7(12) 1_666
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
C1 N1 N2 N3 -0.10(14) . . . . ?
C9 N1 N2 N3 -178.47(10) . . . . ?
N1 N2 N3 C2 -0.18(14) . . . . ?
N2 N1 C1 C2 0.33(14) . . . . ?
C9 N1 C1 C2 178.50(12) . . . . ?
N1 C1 C2 N3 -0.43(14) . . . . ?
N1 C1 C2 C3 -179.28(12) . . . . ?
N2 N3 C2 C1 0.39(15) . . . . ?
N2 N3 C2 C3 179.34(11) . . . . ?
C1 C2 C3 C4 159.14(13) . . . . ?
N3 C2 C3 C4 -19.57(18) . . . . ?
C1 C2 C3 C8 -19.8(2) . . . . ?
N3 C2 C3 C8 161.51(12) . . . . ?
C8 C3 C4 C5 0.0(2) . . . . ?
C2 C3 C4 C5 -178.90(12) . . . . ?
C3 C4 C5 C6 0.0(2) . . . . ?
C4 C5 C6 C7 -0.1(2) . . . . ?
C5 C6 C7 C8 0.1(2) . . . . ?
C6 C7 C8 C3 0.0(2) . . . . ?
C4 C3 C8 C7 0.0(2) . . . . ?
C2 C3 C8 C7 178.89(12) . . . . ?
C1 N1 C9 C10 -26.69(19) . . . . ?
N2 N1 C9 C10 151.33(12) . . . . ?
C1 N1 C9 C14 153.21(13) . . . . ?
N2 N1 C9 C14 -28.76(17) . . . . ?
C14 C9 C10 C11 -0.3(2) . . . . ?
N1 C9 C10 C11 179.64(11) . . . . ?
C9 C10 C11 C12 1.1(2) . . . . ?
C10 C11 C12 C13 -0.5(2) . . . . ?
C10 C11 C12 N4 179.83(12) . . . . ?
O2 N4 C12 C11 21.4(2) . . . . ?
O1 N4 C12 C11 -159.63(14) . . . . ?
O2 N4 C12 C13 -158.33(15) . . . . ?
O1 N4 C12 C13 20.7(2) . . . . ?
C11 C12 C13 C14 -1.0(2) . . . . ?
N4 C12 C13 C14 178.67(12) . . . . ?
C12 C13 C14 C9 1.8(2) . . . . ?
C10 C9 C14 C13 -1.2(2) . . . . ?
N1 C9 C14 C13 178.85(11) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 1229853
