#------------------------------------------------------------------------------
#$Date: 2016-03-26 19:23:19 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180432 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/01/7210110.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_7210110
loop_
_publ_author_name
'Cunha, Anna C.'
'Ferreira, Vitor F.'
'Jordão, Alessandro K.'
'de Souza, Maria C. B. V.'
'Wardell, Solange M. S. V.'
'Wardell, James L.'
'Tan, Peiyu Amelia'
'Bettens, Ryan P. A.'
'Seth, Saikat Kumar'
'Tiekink, Edward R. T.'
_publ_section_title
;
 Aryl-substituents moderate the nature of hydrogen bonds, N--H⋯N
 versus N--H⋯O, leading to supramolecular chains in the crystal
 structures of N-arylamino 1,2,3-triazole esters
;
_journal_issue                   24
_journal_name_full               CrystEngComm
_journal_page_first              4917
_journal_paper_doi               10.1039/c3ce40102b
_journal_volume                  15
_journal_year                    2013
_chemical_formula_moiety         'C12 H13 Br N4 O2'
_chemical_formula_sum            'C12 H13 Br N4 O2'
_chemical_formula_weight         325.17
_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                 105.3049(13)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.7435(3)
_cell_length_b                   9.9927(2)
_cell_length_c                   11.1150(3)
_cell_measurement_reflns_used    3306
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.9
_cell_volume                     1365.21(6)
_computing_cell_refinement       'DENZO (Otwinowski & Minor, 1997) & COLLECT'
_computing_data_collection       'COLLECT (Hooft, 1998)'
_computing_data_reduction        'DENZO & COLLECT'
_computing_molecular_graphics
'ORTEP-3 (Farrugia, 1997), DIAMOND (Brandenburg, 2006)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Enraf Nonius KappaCCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  '10 cm confocal mirrors'
_diffrn_radiation_source         'Enraf Nonius FR591 rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.047
_diffrn_reflns_av_sigmaI/netI    0.029
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            20395
_diffrn_reflns_theta_full        27.5
_diffrn_reflns_theta_max         27.5
_diffrn_reflns_theta_min         2.8
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.015
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.727
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2007)'
_exptl_crystal_colour            light-brown
_exptl_crystal_density_diffrn    1.582
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.28
_refine_diff_density_min         -0.54
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.02
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     177
_refine_ls_number_reflns         3126
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.02
_refine_ls_R_factor_all          0.041
_refine_ls_R_factor_gt           0.028
_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)+(0.0359P)²+0.6692P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.066
_refine_ls_wR_factor_ref         0.071
_reflns_number_gt                2583
_reflns_number_total             3126
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            c3ce40102b.txt
_cod_data_source_block           1093
_cod_original_cell_volume        1365.17(6)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7210110
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
Br1 Br 0.463339(18) -0.19594(2) 0.36752(2) 0.03058(9) Uani 1 1 d .
O1 O 1.09506(13) 0.15841(15) 1.10667(13) 0.0263(3) Uani 1 1 d .
O2 O 1.19335(11) 0.07073(14) 0.98360(12) 0.0242(3) Uani 1 1 d .
N1 N 0.91861(13) 0.13520(15) 0.70082(14) 0.0176(3) Uani 1 1 d .
N2 N 0.85771(14) 0.19102(16) 0.77185(15) 0.0209(3) Uani 1 1 d .
N3 N 0.91996(14) 0.19067(15) 0.88615(15) 0.0209(3) Uani 1 1 d .
N4 N 0.87846(14) 0.12177(17) 0.57279(14) 0.0208(4) Uani 1 1 d D
H4N H 0.8888(19) 0.1940(15) 0.5335(19) 0.025 Uiso 1 1 d D
C1 C 1.01889(16) 0.10036(18) 0.76792(17) 0.0181(4) Uani 1 1 d .
C2 C 1.01876(16) 0.13758(18) 0.88788(17) 0.0184(4) Uani 1 1 d .
C3 C 1.10050(17) 0.0374(2) 0.71176(19) 0.0254(4) Uani 1 1 d .
H3A H 1.0647 0.0076 0.6268 0.038 Uiso 1 1 calc R
H3B H 1.1334 -0.0397 0.7623 0.038 Uiso 1 1 calc R
H3C H 1.1572 0.1027 0.7091 0.038 Uiso 1 1 calc R
C4 C 1.10424(16) 0.12520(18) 1.00502(18) 0.0201(4) Uani 1 1 d .
C5 C 1.28557(17) 0.0463(2) 1.08981(19) 0.0262(4) Uani 1 1 d .
H5A H 1.2635 -0.0066 1.1544 0.031 Uiso 1 1 calc R
H5B H 1.3181 0.1316 1.1271 0.031 Uiso 1 1 calc R
C6 C 1.3645(2) -0.0309(3) 1.0371(2) 0.0404(6) Uani 1 1 d .
H6A H 1.3302 -0.1140 0.9994 0.061 Uiso 1 1 calc R
H6B H 1.4295 -0.0521 1.1042 0.061 Uiso 1 1 calc R
H6C H 1.3852 0.0232 0.9735 0.061 Uiso 1 1 calc R
C7 C 0.78099(16) 0.04918(19) 0.52988(17) 0.0185(4) Uani 1 1 d .
C8 C 0.70862(16) 0.0870(2) 0.41745(18) 0.0218(4) Uani 1 1 d .
H8 H 0.7234 0.1638 0.3742 0.026 Uiso 1 1 calc R
C9 C 0.61543(17) 0.0130(2) 0.36897(19) 0.0237(4) Uani 1 1 d .
H9 H 0.5666 0.0379 0.2919 0.028 Uiso 1 1 calc R
C10 C 0.59352(17) -0.0979(2) 0.43332(18) 0.0230(4) Uani 1 1 d .
C11 C 0.66483(18) -0.1364(2) 0.54499(18) 0.0237(4) Uani 1 1 d .
H11 H 0.6491 -0.2124 0.5885 0.028 Uiso 1 1 calc R
C12 C 0.75892(17) -0.06389(19) 0.59287(18) 0.0213(4) Uani 1 1 d .
H12 H 0.8086 -0.0910 0.6687 0.026 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'
Br Br -0.2901 2.4595 '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
C4 O2 C5 117.89(15)
C1 N1 N2 112.81(15)
C1 N1 N4 125.71(16)
N2 N1 N4 121.45(16)
N3 N2 N1 105.62(15)
N2 N3 C2 109.64(15)
N1 N4 C7 116.82(15)
N1 N4 H4N 111.8(16)
C7 N4 H4N 119.6(16)
N1 C1 C2 102.83(16)
N1 C1 C3 123.00(17)
C2 C1 C3 134.17(18)
N3 C2 C1 109.10(17)
N3 C2 C4 120.86(16)
C1 C2 C4 130.03(18)
C1 C3 H3A 109.5
C1 C3 H3B 109.5
H3A C3 H3B 109.5
C1 C3 H3C 109.5
H3A C3 H3C 109.5
H3B C3 H3C 109.5
O1 C4 O2 124.98(19)
O1 C4 C2 124.94(18)
O2 C4 C2 110.08(16)
O2 C5 C6 104.54(17)
O2 C5 H5A 110.8
C6 C5 H5A 110.8
O2 C5 H5B 110.8
C6 C5 H5B 110.8
H5A C5 H5B 108.9
C5 C6 H6A 109.5
C5 C6 H6B 109.5
H6A C6 H6B 109.5
C5 C6 H6C 109.5
H6A C6 H6C 109.5
H6B C6 H6C 109.5
C8 C7 C12 119.70(18)
C8 C7 N4 118.62(17)
C12 C7 N4 121.56(18)
C9 C8 C7 120.04(18)
C9 C8 H8 120.0
C7 C8 H8 120.0
C8 C9 C10 119.74(19)
C8 C9 H9 120.1
C10 C9 H9 120.1
C11 C10 C9 120.68(19)
C11 C10 Br1 120.11(15)
C9 C10 Br1 119.20(16)
C12 C11 C10 119.79(19)
C12 C11 H11 120.1
C10 C11 H11 120.1
C11 C12 C7 120.03(19)
C11 C12 H12 120.0
C7 C12 H12 120.0
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C10 1.899(2)
O1 C4 1.213(2)
O2 C4 1.336(2)
O2 C5 1.450(2)
N1 C1 1.344(2)
N1 N2 1.364(2)
N1 N4 1.386(2)
N2 N3 1.308(2)
N3 C2 1.362(3)
N4 C7 1.408(3)
N4 H4N 0.872(9)
C1 C2 1.385(3)
C1 C3 1.487(3)
C2 C4 1.466(3)
C3 H3A 0.9800
C3 H3B 0.9800
C3 H3C 0.9800
C5 C6 1.503(3)
C5 H5A 0.9900
C5 H5B 0.9900
C6 H6A 0.9800
C6 H6B 0.9800
C6 H6C 0.9800
C7 C8 1.395(3)
C7 C12 1.396(3)
C8 C9 1.382(3)
C8 H8 0.9500
C9 C10 1.387(3)
C9 H9 0.9500
C10 C11 1.385(3)
C11 C12 1.382(3)
C11 H11 0.9500
C12 H12 0.9500
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
C1 N1 N2 N3 -0.5(2)
N4 N1 N2 N3 -178.77(15)
N1 N2 N3 C2 0.80(19)
C1 N1 N4 C7 125.0(2)
N2 N1 N4 C7 -57.0(2)
N2 N1 C1 C2 0.0(2)
N4 N1 C1 C2 178.18(16)
N2 N1 C1 C3 179.89(17)
N4 N1 C1 C3 -1.9(3)
N2 N3 C2 C1 -0.8(2)
N2 N3 C2 C4 -179.90(16)
N1 C1 C2 N3 0.5(2)
C3 C1 C2 N3 -179.4(2)
N1 C1 C2 C4 179.43(18)
C3 C1 C2 C4 -0.4(4)
C5 O2 C4 O1 1.5(3)
C5 O2 C4 C2 -177.86(16)
N3 C2 C4 O1 0.7(3)
C1 C2 C4 O1 -178.18(19)
N3 C2 C4 O2 -179.97(16)
C1 C2 C4 O2 1.2(3)
C4 O2 C5 C6 172.61(17)
N1 N4 C7 C8 146.72(17)
N1 N4 C7 C12 -37.4(2)
C12 C7 C8 C9 0.2(3)
N4 C7 C8 C9 176.09(17)
C7 C8 C9 C10 0.8(3)
C8 C9 C10 C11 -0.9(3)
C8 C9 C10 Br1 178.44(15)
C9 C10 C11 C12 -0.1(3)
Br1 C10 C11 C12 -179.42(15)
C10 C11 C12 C7 1.1(3)
C8 C7 C12 C11 -1.1(3)
N4 C7 C12 C11 -176.95(18)
