#------------------------------------------------------------------------------
#$Date: 2016-03-26 16:19:04 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180332 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/01/7200194.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_7200194
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                 103.305(18)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.388(13)
_cell_length_b                   8.051(9)
_cell_length_c                   14.256(15)
_cell_measurement_reflns_used    1834
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      22.37
_cell_measurement_theta_min      2.95
_cell_volume                     1384(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 0.994
_diffrn_measured_fraction_theta_max 0.994
_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  0.0517
_diffrn_reflns_av_sigmaI/netI    0.0648
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6344
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.93
_exptl_absorpt_coefficient_mu    2.981
_exptl_absorpt_correction_T_max  0.2959
_exptl_absorpt_correction_T_min  0.2074
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'BRUKER SADABS'
_exptl_crystal_colour            ORANGE
_exptl_crystal_density_diffrn    1.657
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.77
_exptl_crystal_size_mid          0.68
_exptl_crystal_size_min          0.54
_refine_diff_density_max         0.923
_refine_diff_density_min         -0.280
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.960
_refine_ls_hydrogen_treatment    RIDING
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2419
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.960
_refine_ls_R_factor_all          0.0699
_refine_ls_R_factor_gt           0.0466
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0830P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1245
_refine_ls_wR_factor_ref         0.1376
_reflns_number_gt                1685
_reflns_number_total             2419
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b809985e.txt
_cod_data_source_block           9
_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_cell_volume        1384(2)
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               7200194
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 0.78644(5) 1.01839(6) 0.43023(4) 0.0829(3) Uani 1 1 d . . .
O1 O 0.6820(3) 0.8034(5) 0.8341(2) 0.0966(10) Uani 1 1 d . . .
O2 O 0.5582(3) 0.8225(6) 0.9164(3) 0.1144(13) Uani 1 1 d . . .
N1 N 0.5919(3) 0.9578(4) 0.6590(2) 0.0592(8) Uani 1 1 d . . .
N2 N 0.5227(3) 0.8285(5) 0.6439(3) 0.0887(12) Uani 1 1 d . . .
N3 N 0.5497(3) 0.7372(5) 0.5769(3) 0.0823(11) Uani 1 1 d . . .
N4 N 0.6073(3) 0.8757(5) 0.8584(3) 0.0761(10) Uani 1 1 d . . .
C1 C 0.6632(3) 0.9479(5) 0.6007(3) 0.0552(9) Uani 1 1 d . . .
H1 H 0.7190 1.0231 0.5968 0.066 Uiso 1 1 calc R . .
C2 C 0.6375(3) 0.8074(5) 0.5491(2) 0.0559(9) Uani 1 1 d . . .
C3 C 0.6843(3) 0.7187(5) 0.4778(2) 0.0546(9) Uani 1 1 d . . .
C4 C 0.6628(4) 0.5499(5) 0.4635(3) 0.0653(11) Uani 1 1 d . . .
H4 H 0.6194 0.4973 0.4999 0.078 Uiso 1 1 calc R . .
C5 C 0.7027(4) 0.4584(6) 0.3988(4) 0.0791(14) Uani 1 1 d . . .
H5 H 0.6854 0.3462 0.3906 0.095 Uiso 1 1 calc R . .
C6 C 0.7689(4) 0.5329(6) 0.3452(4) 0.0797(14) Uani 1 1 d . . .
H6 H 0.7984 0.4704 0.3022 0.096 Uiso 1 1 calc R . .
C7 C 0.7908(4) 0.6981(6) 0.3555(3) 0.0707(11) Uani 1 1 d . . .
H7 H 0.8339 0.7494 0.3184 0.085 Uiso 1 1 calc R . .
C8 C 0.7492(3) 0.7897(5) 0.4210(2) 0.0595(10) Uani 1 1 d . . .
C9 C 0.5802(3) 1.0819(5) 0.7253(3) 0.0550(9) Uani 1 1 d . . .
C10 C 0.5635(3) 1.2447(5) 0.6959(3) 0.0673(11) Uani 1 1 d . . .
H10 H 0.5654 1.2735 0.6331 0.081 Uiso 1 1 calc R . .
C11 C 0.5438(3) 1.3654(6) 0.7585(4) 0.0806(13) Uani 1 1 d . . .
H11 H 0.5347 1.4754 0.7384 0.097 Uiso 1 1 calc R . .
C12 C 0.5378(3) 1.3234(7) 0.8497(4) 0.0866(14) Uani 1 1 d . . .
H12 H 0.5218 1.4047 0.8908 0.104 Uiso 1 1 calc R . .
C13 C 0.5554(3) 1.1608(7) 0.8820(3) 0.0767(13) Uani 1 1 d . . .
H13 H 0.5515 1.1327 0.9444 0.092 Uiso 1 1 calc R . .
C14 C 0.5784(3) 1.0429(5) 0.8206(3) 0.0601(10) 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
N2 N1 C1 110.0(3) . . ?
N2 N1 C9 120.1(3) . . ?
C1 N1 C9 129.8(3) . . ?
N3 N2 N1 107.0(3) . . ?
N2 N3 C2 109.6(3) . . ?
O1 N4 O2 124.2(4) . . ?
O1 N4 C14 118.4(4) . . ?
O2 N4 C14 117.2(4) . . ?
C2 C1 N1 106.3(3) . . ?
C1 C2 N3 107.1(3) . . ?
C1 C2 C3 134.9(4) . . ?
N3 C2 C3 118.0(3) . . ?
C8 C3 C4 115.7(4) . . ?
C8 C3 C2 125.3(3) . . ?
C4 C3 C2 119.0(4) . . ?
C5 C4 C3 122.8(4) . . ?
C4 C5 C6 119.7(5) . . ?
C7 C6 C5 119.6(4) . . ?
C6 C7 C8 120.0(4) . . ?
C7 C8 C3 122.1(4) . . ?
C7 C8 Br1 116.3(3) . . ?
C3 C8 Br1 121.6(3) . . ?
C10 C9 C14 118.3(4) . . ?
C10 C9 N1 120.2(4) . . ?
C14 C9 N1 121.4(4) . . ?
C9 C10 C11 120.7(4) . . ?
C12 C11 C10 120.0(5) . . ?
C11 C12 C13 120.8(5) . . ?
C14 C13 C12 118.9(4) . . ?
C13 C14 C9 121.3(4) . . ?
C13 C14 N4 118.3(4) . . ?
C9 C14 N4 120.4(4) . . ?
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 C8 1.895(4) . ?
O1 N4 1.209(4) . ?
O2 N4 1.212(4) . ?
N1 N2 1.334(5) . ?
N1 C1 1.348(5) . ?
N1 C9 1.405(5) . ?
N2 N3 1.308(5) . ?
N3 C2 1.363(5) . ?
N4 C14 1.463(6) . ?
C1 C2 1.347(5) . ?
C2 C3 1.467(5) . ?
C3 C8 1.388(5) . ?
C3 C4 1.391(5) . ?
C4 C5 1.359(6) . ?
C5 C6 1.381(7) . ?
C6 C7 1.358(6) . ?
C7 C8 1.380(5) . ?
C9 C10 1.377(6) . ?
C9 C14 1.400(6) . ?
C10 C11 1.378(6) . ?
C11 C12 1.363(7) . ?
C12 C13 1.388(7) . ?
C13 C14 1.365(6) . ?
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
C5 H5 Br1 0.93 2.92 3.690(6) 141.1 1_545
C13 H13 O2 0.93 2.68 3.482(6) 145.4 3_677
C1 H1 O1 0.93 2.65 3.451(6) 145.0 2_656
