#------------------------------------------------------------------------------
#$Date: 2016-03-26 16:19:04 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180332 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/01/7200197.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_7200197
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           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 95.564(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.502(3)
_cell_length_b                   5.3559(18)
_cell_length_c                   27.363(9)
_cell_measurement_reflns_used    2172
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      27.44
_cell_measurement_theta_min      2.41
_cell_volume                     1240.1(7)
_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 0.995
_diffrn_measured_fraction_theta_max 0.995
_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  0.0364
_diffrn_reflns_av_sigmaI/netI    0.0408
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            5402
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.71
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  0.9802
_exptl_absorpt_correction_T_min  0.9696
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'bruker sadabs'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.426
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.171
_refine_diff_density_min         -0.147
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2170
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0655
_refine_ls_R_factor_gt           0.0525
_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)+(0.0564P)²+0.4985P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1260
_refine_ls_wR_factor_ref         0.1328
_reflns_number_gt                1779
_reflns_number_total             2170
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b809985e.txt
_cod_data_source_block           12
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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_sg_symbol_H-M      P2(1)/c
_cod_database_code               7200197
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.0029(2) 1.0378(3) 0.44121(6) 0.0626(5) Uani 1 1 d . . .
O2 O 0.0521(2) 0.9861(4) 0.36626(7) 0.0679(5) Uani 1 1 d . . .
N1 N 0.2947(2) 0.3584(3) 0.53720(7) 0.0434(5) Uani 1 1 d . . .
N2 N 0.3655(2) 0.1365(4) 0.54893(8) 0.0573(6) Uani 1 1 d . . .
N3 N 0.3657(2) 0.1069(4) 0.59611(8) 0.0573(6) Uani 1 1 d . . .
N4 N 0.0679(2) 0.9265(4) 0.40952(7) 0.0464(5) Uani 1 1 d . . .
C1 C 0.2507(2) 0.4711(4) 0.57811(8) 0.0421(5) Uani 1 1 d . . .
H1 H 0.2004 0.6245 0.5801 0.051 Uiso 1 1 calc R . .
C2 C 0.2963(2) 0.3098(4) 0.61595(8) 0.0438(5) Uani 1 1 d . . .
C3 C 0.2794(2) 0.3287(4) 0.66883(8) 0.0451(5) Uani 1 1 d . . .
C4 C 0.3532(3) 0.1575(5) 0.70171(10) 0.0612(7) Uani 1 1 d . . .
H4 H 0.4150 0.0316 0.6901 0.073 Uiso 1 1 calc R . .
C5 C 0.3365(4) 0.1709(6) 0.75107(10) 0.0730(8) Uani 1 1 d . . .
H5 H 0.3870 0.0548 0.7724 0.088 Uiso 1 1 calc R . .
C6 C 0.2456(3) 0.3548(6) 0.76895(10) 0.0671(7) Uani 1 1 d . . .
H6 H 0.2339 0.3632 0.8024 0.081 Uiso 1 1 calc R . .
C7 C 0.1716(3) 0.5273(6) 0.73707(10) 0.0693(8) Uani 1 1 d . . .
H7 H 0.1101 0.6526 0.7491 0.083 Uiso 1 1 calc R . .
C8 C 0.1885(3) 0.5148(5) 0.68750(10) 0.0614(7) Uani 1 1 d . . .
H8 H 0.1384 0.6322 0.6663 0.074 Uiso 1 1 calc R . .
C9 C 0.2794(2) 0.4419(4) 0.48744(8) 0.0403(5) Uani 1 1 d . . .
C10 C 0.3627(2) 0.3174(4) 0.45310(9) 0.0474(6) Uani 1 1 d . . .
H10 H 0.4283 0.1836 0.4628 0.057 Uiso 1 1 calc R . .
C11 C 0.3468(3) 0.3946(5) 0.40495(9) 0.0527(6) Uani 1 1 d . . .
H11 H 0.4023 0.3118 0.3822 0.063 Uiso 1 1 calc R . .
C12 C 0.2501(3) 0.5929(5) 0.38968(8) 0.0496(6) Uani 1 1 d . . .
H12 H 0.2392 0.6438 0.3570 0.060 Uiso 1 1 calc R . .
C13 C 0.1700(2) 0.7130(4) 0.42458(8) 0.0403(5) Uani 1 1 d . . .
C14 C 0.1825(2) 0.6417(4) 0.47330(8) 0.0413(5) Uani 1 1 d . . .
H14 H 0.1273 0.7259 0.4960 0.050 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 N2 110.26(18) . . ?
C1 N1 C9 129.89(18) . . ?
N2 N1 C9 119.84(17) . . ?
N3 N2 N1 107.42(18) . . ?
N2 N3 C2 109.69(19) . . ?
O2 N4 O1 122.9(2) . . ?
O2 N4 C13 118.79(18) . . ?
O1 N4 C13 118.28(19) . . ?
N1 C1 C2 105.18(19) . . ?
N3 C2 C1 107.45(19) . . ?
N3 C2 C3 122.0(2) . . ?
C1 C2 C3 130.5(2) . . ?
C8 C3 C4 117.9(2) . . ?
C8 C3 C2 121.5(2) . . ?
C4 C3 C2 120.7(2) . . ?
C5 C4 C3 121.2(2) . . ?
C6 C5 C4 120.3(3) . . ?
C5 C6 C7 119.6(3) . . ?
C8 C7 C6 120.3(3) . . ?
C7 C8 C3 120.7(2) . . ?
C14 C9 C10 120.5(2) . . ?
C14 C9 N1 120.41(18) . . ?
C10 C9 N1 119.08(19) . . ?
C11 C10 C9 119.4(2) . . ?
C10 C11 C12 121.4(2) . . ?
C11 C12 C13 117.8(2) . . ?
C14 C13 C12 122.7(2) . . ?
C14 C13 N4 118.28(18) . . ?
C12 C13 N4 119.0(2) . . ?
C13 C14 C9 118.17(19) . . ?
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 1.227(2) . ?
O2 N4 1.221(2) . ?
N1 C1 1.356(3) . ?
N1 N2 1.357(3) . ?
N1 C9 1.427(3) . ?
N2 N3 1.300(3) . ?
N3 C2 1.373(3) . ?
N4 C13 1.471(3) . ?
C1 C2 1.375(3) . ?
C2 C3 1.471(3) . ?
C3 C8 1.389(3) . ?
C3 C4 1.391(3) . ?
C4 C5 1.374(4) . ?
C5 C6 1.371(4) . ?
C6 C7 1.380(4) . ?
C7 C8 1.379(4) . ?
C9 C14 1.383(3) . ?
C9 C10 1.399(3) . ?
C10 C11 1.375(3) . ?
C11 C12 1.383(3) . ?
C12 C13 1.384(3) . ?
C13 C14 1.381(3) . ?
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
C1 H1 O1 0.93 2.53 3.409(3) 157.6 3_576
C14 H14 O1 0.93 2.48 3.408(3) 176.2 3_576
C8 H8 O2 0.93 2.70 3.593(3) 160.1 3_576
C6 H6 O2 0.93 2.57 3.372(3) 144.2 4_576
C10 H10 N2 0.93 2.50 3.358(3) 154.4 3_656
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 0.5(2) . . . . ?
C9 N1 N2 N3 179.24(18) . . . . ?
N1 N2 N3 C2 -0.5(3) . . . . ?
N2 N1 C1 C2 -0.3(2) . . . . ?
C9 N1 C1 C2 -178.86(19) . . . . ?
N2 N3 C2 C1 0.3(3) . . . . ?
N2 N3 C2 C3 179.92(19) . . . . ?
N1 C1 C2 N3 0.0(2) . . . . ?
N1 C1 C2 C3 -179.6(2) . . . . ?
N3 C2 C3 C8 -170.1(2) . . . . ?
C1 C2 C3 C8 9.4(4) . . . . ?
N3 C2 C3 C4 9.1(3) . . . . ?
C1 C2 C3 C4 -171.4(2) . . . . ?
C8 C3 C4 C5 0.2(4) . . . . ?
C2 C3 C4 C5 -179.0(2) . . . . ?
C3 C4 C5 C6 0.1(4) . . . . ?
C4 C5 C6 C7 -0.3(4) . . . . ?
C5 C6 C7 C8 0.2(4) . . . . ?
C6 C7 C8 C3 0.2(4) . . . . ?
C4 C3 C8 C7 -0.4(4) . . . . ?
C2 C3 C8 C7 178.8(2) . . . . ?
C1 N1 C9 C14 -13.8(3) . . . . ?
N2 N1 C9 C14 167.76(19) . . . . ?
C1 N1 C9 C10 166.8(2) . . . . ?
N2 N1 C9 C10 -11.7(3) . . . . ?
C14 C9 C10 C11 -0.3(3) . . . . ?
N1 C9 C10 C11 179.08(19) . . . . ?
C9 C10 C11 C12 0.0(3) . . . . ?
C10 C11 C12 C13 0.4(3) . . . . ?
C11 C12 C13 C14 -0.4(3) . . . . ?
C11 C12 C13 N4 179.20(19) . . . . ?
O2 N4 C13 C14 -177.73(19) . . . . ?
O1 N4 C13 C14 2.6(3) . . . . ?
O2 N4 C13 C12 2.7(3) . . . . ?
O1 N4 C13 C12 -176.9(2) . . . . ?
C12 C13 C14 C9 0.0(3) . . . . ?
N4 C13 C14 C9 -179.58(18) . . . . ?
C10 C9 C14 C13 0.4(3) . . . . ?
N1 C9 C14 C13 -179.05(18) . . . . ?
