#------------------------------------------------------------------------------
#$Date: 2016-03-26 16:19:04 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180332 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/01/7200195.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_7200195
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 H9 Br N4 O2'
_chemical_formula_sum            'C14 H9 Br N4 O2'
_chemical_formula_weight         345.16
_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                 97.444(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.2835(11)
_cell_length_b                   7.2943(9)
_cell_length_c                   20.794(2)
_cell_measurement_reflns_used    2171
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      22.20
_cell_measurement_theta_min      2.29
_cell_volume                     1396.2(3)
_computing_cell_refinement       'BRUKER SAINT'
_computing_data_collection       'BRUKER SMART'
_computing_data_reduction        'BRUKER SAINT'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      297(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0238
_diffrn_reflns_av_sigmaI/netI    0.0248
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            8147
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.30
_exptl_absorpt_coefficient_mu    2.954
_exptl_absorpt_correction_T_max  0.7001
_exptl_absorpt_correction_T_min  0.3142
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'BRUKER SADABS'
_exptl_crystal_colour            ORANGE
_exptl_crystal_density_diffrn    1.642
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       PLATE
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.51
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.568
_refine_diff_density_min         -0.389
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    RIDING
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2448
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0518
_refine_ls_R_factor_gt           0.0369
_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)+(0.0449P)²+0.6717P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0876
_refine_ls_wR_factor_ref         0.0942
_reflns_number_gt                1881
_reflns_number_total             2448
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b809985e.txt
_cod_data_source_block           10
_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.

'_exptl_absorpt_correction_type' value 'MULTI-SCAN' changed
to 'multi-scan' 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      'P 21/n'
_cod_database_code               7200195
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
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br -0.35384(4) 0.67164(6) 0.017641(17) 0.08172(19) Uani 1 1 d . . .
O1 O 0.3640(3) 0.8414(4) 0.31455(17) 0.1016(10) Uani 1 1 d . . .
O2 O 0.4556(3) 0.8569(3) 0.41448(19) 0.0994(10) Uani 1 1 d . . .
N1 N 0.0863(2) 0.6940(3) 0.31547(11) 0.0459(5) Uani 1 1 d . . .
N2 N 0.0615(3) 0.8586(3) 0.34212(12) 0.0540(6) Uani 1 1 d . . .
N3 N -0.0251(3) 0.9486(3) 0.29872(12) 0.0544(6) Uani 1 1 d . . .
N4 N 0.3809(3) 0.7831(4) 0.36969(19) 0.0671(8) Uani 1 1 d . . .
C1 C 0.0155(3) 0.6812(4) 0.25556(14) 0.0493(7) Uani 1 1 d . . .
H1 H 0.0148 0.5822 0.2273 0.059 Uiso 1 1 calc R . .
C2 C -0.0559(3) 0.8441(4) 0.24450(13) 0.0454(6) Uani 1 1 d . . .
C3 C -0.1491(3) 0.9078(4) 0.18638(14) 0.0453(6) Uani 1 1 d . . .
C4 C -0.1827(3) 1.0923(4) 0.17716(16) 0.0536(7) Uani 1 1 d . . .
H4 H -0.1512 1.1769 0.2094 0.064 Uiso 1 1 calc R . .
C5 C -0.2632(3) 1.1503(4) 0.11997(17) 0.0615(8) Uani 1 1 d . . .
H5 H -0.2838 1.2744 0.1139 0.074 Uiso 1 1 calc R . .
C6 C -0.3129(3) 1.0275(5) 0.07226(16) 0.0610(8) Uani 1 1 d . . .
H6 H -0.3664 1.0674 0.0339 0.073 Uiso 1 1 calc R . .
C7 C -0.2821(3) 0.8436(4) 0.08212(14) 0.0543(7) Uani 1 1 d . . .
C8 C -0.2015(3) 0.7824(4) 0.13845(14) 0.0500(7) Uani 1 1 d . . .
H8 H -0.1823 0.6580 0.1444 0.060 Uiso 1 1 calc R . .
C9 C 0.1769(3) 0.5613(4) 0.35132(13) 0.0432(6) Uani 1 1 d . . .
C10 C 0.1269(3) 0.3857(4) 0.35846(15) 0.0532(7) Uani 1 1 d . . .
H10 H 0.0352 0.3524 0.3384 0.064 Uiso 1 1 calc R . .
C11 C 0.2115(4) 0.2590(4) 0.39510(16) 0.0600(8) Uani 1 1 d . . .
H11 H 0.1773 0.1403 0.3991 0.072 Uiso 1 1 calc R . .
C12 C 0.3467(4) 0.3071(4) 0.42597(15) 0.0572(8) Uani 1 1 d . . .
H12 H 0.4028 0.2218 0.4514 0.069 Uiso 1 1 calc R . .
C13 C 0.3981(3) 0.4816(4) 0.41901(14) 0.0539(7) Uani 1 1 d . . .
H13 H 0.4889 0.5153 0.4399 0.065 Uiso 1 1 calc R . .
C14 C 0.3151(3) 0.6055(4) 0.38121(14) 0.0459(7) 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'
Br Br -0.2901 2.4595 '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 110.8(2) . . ?
C1 N1 C9 128.7(2) . . ?
N2 N1 C9 120.5(2) . . ?
N3 N2 N1 106.6(2) . . ?
N2 N3 C2 109.6(2) . . ?
O2 N4 O1 124.2(3) . . ?
O2 N4 C14 118.4(3) . . ?
O1 N4 C14 117.3(3) . . ?
N1 C1 C2 105.4(2) . . ?
N3 C2 C1 107.6(2) . . ?
N3 C2 C3 122.9(2) . . ?
C1 C2 C3 129.4(3) . . ?
C4 C3 C8 119.0(3) . . ?
C4 C3 C2 121.2(3) . . ?
C8 C3 C2 119.7(3) . . ?
C5 C4 C3 120.1(3) . . ?
C6 C5 C4 121.0(3) . . ?
C5 C6 C7 118.9(3) . . ?
C8 C7 C6 121.3(3) . . ?
C8 C7 Br1 119.3(2) . . ?
C6 C7 Br1 119.4(2) . . ?
C7 C8 C3 119.7(3) . . ?
C10 C9 C14 118.2(3) . . ?
C10 C9 N1 120.2(3) . . ?
C14 C9 N1 121.6(2) . . ?
C11 C10 C9 120.5(3) . . ?
C10 C11 C12 120.5(3) . . ?
C13 C12 C11 119.6(3) . . ?
C14 C13 C12 119.7(3) . . ?
C13 C14 C9 121.5(3) . . ?
C13 C14 N4 117.6(3) . . ?
C9 C14 N4 120.8(3) . . ?
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
Br1 C7 1.893(3) . ?
O1 N4 1.214(4) . ?
O2 N4 1.213(4) . ?
N1 C1 1.335(4) . ?
N1 N2 1.354(3) . ?
N1 C9 1.427(3) . ?
N2 N3 1.306(3) . ?
N3 C2 1.360(3) . ?
N4 C14 1.465(4) . ?
C1 C2 1.366(4) . ?
C2 C3 1.467(4) . ?
C3 C4 1.389(4) . ?
C3 C8 1.393(4) . ?
C4 C5 1.386(4) . ?
C5 C6 1.372(5) . ?
C6 C7 1.381(4) . ?
C7 C8 1.380(4) . ?
C9 C10 1.378(4) . ?
C9 C14 1.389(4) . ?
C10 C11 1.377(4) . ?
C11 C12 1.379(5) . ?
C12 C13 1.374(4) . ?
C13 C14 1.368(4) . ?
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 2.32 3.153(4) 149.6 2_545
C11 H11 N2 0.93 2.54 3.360(4) 147.3 1_545
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 0.0(3) . . . . ?
C9 N1 N2 N3 -179.4(2) . . . . ?
N1 N2 N3 C2 -0.2(3) . . . . ?
N2 N1 C1 C2 0.1(3) . . . . ?
C9 N1 C1 C2 179.5(2) . . . . ?
N2 N3 C2 C1 0.2(3) . . . . ?
N2 N3 C2 C3 -179.1(3) . . . . ?
N1 C1 C2 N3 -0.2(3) . . . . ?
N1 C1 C2 C3 179.0(3) . . . . ?
N3 C2 C3 C4 15.9(4) . . . . ?
C1 C2 C3 C4 -163.3(3) . . . . ?
N3 C2 C3 C8 -166.1(3) . . . . ?
C1 C2 C3 C8 14.7(4) . . . . ?
C8 C3 C4 C5 -2.2(4) . . . . ?
C2 C3 C4 C5 175.8(3) . . . . ?
C3 C4 C5 C6 1.1(5) . . . . ?
C4 C5 C6 C7 0.3(5) . . . . ?
C5 C6 C7 C8 -0.7(5) . . . . ?
C5 C6 C7 Br1 178.5(2) . . . . ?
C6 C7 C8 C3 -0.4(4) . . . . ?
Br1 C7 C8 C3 -179.6(2) . . . . ?
C4 C3 C8 C7 1.8(4) . . . . ?
C2 C3 C8 C7 -176.2(3) . . . . ?
C1 N1 C9 C10 -52.4(4) . . . . ?
N2 N1 C9 C10 126.9(3) . . . . ?
C1 N1 C9 C14 129.3(3) . . . . ?
N2 N1 C9 C14 -51.3(4) . . . . ?
C14 C9 C10 C11 0.9(4) . . . . ?
N1 C9 C10 C11 -177.4(3) . . . . ?
C9 C10 C11 C12 1.0(5) . . . . ?
C10 C11 C12 C13 -1.3(5) . . . . ?
C11 C12 C13 C14 -0.4(5) . . . . ?
C12 C13 C14 C9 2.4(4) . . . . ?
C12 C13 C14 N4 -173.6(3) . . . . ?
C10 C9 C14 C13 -2.6(4) . . . . ?
N1 C9 C14 C13 175.7(2) . . . . ?
C10 C9 C14 N4 173.2(3) . . . . ?
N1 C9 C14 N4 -8.5(4) . . . . ?
O2 N4 C14 C13 -40.6(4) . . . . ?
O1 N4 C14 C13 134.9(3) . . . . ?
O2 N4 C14 C9 143.4(3) . . . . ?
O1 N4 C14 C9 -41.1(4) . . . . ?
