#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/10/2211020.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2211020
loop_
_publ_author_name
'Oliveira-Campos, Ana Maria Ferreira'
'Rodrigues, Ligia M.'
'Kaja, Martin'
'Guilardi, Silvana'
'Franca, Eduardo de Faria'
'Ellena, Javier '
_publ_section_title
;
 7-Amino-1-(3-bromophenyl)-3-cyanopyrazolo[4,3-d]pyrimidine
;
_journal_coeditor_code           HB2161
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o5246
_journal_page_last               o5248
_journal_paper_doi               10.1107/S1600536806043005
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C12 H7 Br N6'
_chemical_formula_moiety         'C12 H7 Br N6'
_chemical_formula_sum            'C12 H7 Br N6'
_chemical_formula_weight         315.15
_chemical_name_systematic
;
7-Amino-1-(3-bromophenyl)-3-cyanopyrazolo[4,3-d]pyrimidine
;
_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'
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 95.560(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.7153(3)
_cell_length_b                   7.6270(4)
_cell_length_c                   20.3497(7)
_cell_measurement_reflns_used    8516
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      26.02
_cell_measurement_theta_min      2.91
_cell_volume                     1191.84(9)
_computing_cell_refinement       'SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 2000)'
_computing_data_reduction
'SCALEPACK and DENZO (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'φ scans and ω scans winth κ offsets'
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.062
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            7624
_diffrn_reflns_theta_full        26.06
_diffrn_reflns_theta_max         26.06
_diffrn_reflns_theta_min         2.93
_exptl_absorpt_coefficient_mu    3.443
_exptl_absorpt_correction_T_max  0.709
_exptl_absorpt_correction_T_min  0.548
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SORTAV; Blessing, 1995)'
_exptl_crystal_colour            Orange
_exptl_crystal_density_diffrn    1.756
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.764
_refine_diff_density_min         -0.979
_refine_ls_goodness_of_fit_ref   1.05
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2361
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.05
_refine_ls_R_factor_all          0.0501
_refine_ls_R_factor_gt           0.0334
_refine_ls_shift/su_max          0.026
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0505P)²+0.2909P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0814
_refine_ls_wR_factor_ref         0.0872
_reflns_number_gt                2000
_reflns_number_total             2361
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb2161.cif
_cod_data_source_block           IIIa
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2211020
_cod_database_fobs_code          2211020
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_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
N N6 0.1980(3) 0.4330(3) -0.03637(11) 0.0297(5) Uani d . 1
C C1' 0.4865(3) 0.1784(4) 0.14990(12) 0.0263(5) Uani d . 1
N N1 0.5115(3) 0.1960(3) 0.08155(11) 0.0273(5) Uani d . 1
C C9 0.5060(4) 0.2681(3) -0.02436(13) 0.0258(5) Uani d . 1
C C7 0.2458(3) 0.3602(3) 0.02250(13) 0.0277(5) Uani d . 1
N N4 0.4545(3) 0.3379(3) -0.08434(11) 0.0295(5) Uani d . 1
C C2' 0.5206(3) 0.0169(3) 0.17933(13) 0.0284(6) Uani d . 1
H H2' 0.5539 -0.0802 0.1541 0.034 Uiso calc R 1
C C3 0.6578(3) 0.1714(3) -0.00269(13) 0.0276(5) Uani d . 1
N N2 0.6607(3) 0.1295(3) 0.06115(11) 0.0292(5) Uani d . 1
C C4 0.7940(4) 0.1219(4) -0.04168(14) 0.0338(6) Uani d . 1
N N7 0.1352(3) 0.3695(3) 0.06892(11) 0.0347(5) Uani d . 1
H H7A 0.0342 0.4224 0.0604 0.042 Uiso calc R 1
H H7B 0.1634 0.3227 0.108 0.042 Uiso calc R 1
C C8 0.4134(4) 0.2793(3) 0.03087(13) 0.0257(5) Uani d . 1
C C5 0.3032(4) 0.4181(3) -0.08522(13) 0.0302(6) Uani d . 1
H H5 0.2627 0.4729 -0.1258 0.036 Uiso calc R 1
Br Br 0.55734(4) -0.22152(4) 0.285832(13) 0.03521(14) Uani d . 1
C C5' 0.4216(4) 0.2997(3) 0.25268(14) 0.0308(6) Uani d . 1
H H5' 0.3876 0.3964 0.2779 0.037 Uiso calc R 1
C C6' 0.4381(3) 0.3218(4) 0.18626(14) 0.0282(5) Uani d . 1
H H6' 0.4168 0.4327 0.1658 0.034 Uiso calc R 1
C C3' 0.5055(3) -0.0002(4) 0.24571(13) 0.0277(5) Uani d . 1
C C4' 0.4538(4) 0.1390(4) 0.28326(13) 0.0305(6) Uani d . 1
H H4' 0.4408 0.1244 0.3289 0.037 Uiso calc R 1
N N3 0.8941(4) 0.0828(4) -0.07707(14) 0.0516(7) Uani d . 1
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 0 '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'
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_publ_flag
C7 N6 C5 119.4(2) no
C2' C1' C6' 121.3(2) no
C2' C1' N1 117.8(2) no
C6' C1' N1 120.8(2) no
N2 N1 C8 111.4(2) n
N2 N1 C1' 117.4(2) y
C8 N1 C1' 131.1(2) y
N4 C9 C8 125.1(2) no
N4 C9 C3 130.2(2) n
C8 C9 C3 104.7(2) n
N7 C7 N6 118.1(2) y
N7 C7 C8 124.9(2) y
N6 C7 C8 117.0(2) no
C5 N4 C9 112.1(2) no
C3' C2' C1' 118.6(2) no
C3' C2' H2' 120.7 no
C1' C2' H2' 120.7 no
N2 C3 C9 111.2(2) n
N2 C3 C4 122.3(2) n
C9 C3 C4 126.5(2) n
C3 N2 N1 105.8(2) n
N3 C4 C3 174.8(3) no
C7 N7 H7A 120 no
C7 N7 H7B 120 no
H7A N7 H7B 120 no
N1 C8 C9 106.8(2) n
N1 C8 C7 135.7(2) n
C9 C8 C7 117.4(2) no
N4 C5 N6 128.7(2) no
N4 C5 H5 115.6 no
N6 C5 H5 115.6 no
C6' C5' C4' 121.2(2) no
C6' C5' H5' 119.4 no
C4' C5' H5' 119.4 no
C5' C6' C1' 118.7(2) no
C5' C6' H6' 120.7 no
C1' C6' H6' 120.7 no
C2' C3' C4' 121.7(2) no
C2' C3' Br 118.2(2) no
C4' C3' Br 120.1(2) no
C5' C4' C3' 118.5(2) no
C5' C4' H4' 120.7 no
C3' C4' H4' 120.7 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
N6 C7 1.339(3) no
N6 C5 1.348(3) no
C1' C2' 1.384(4) no
C1' C6' 1.392(4) no
C1' N1 1.429(3) n
N1 N2 1.359(3) n
N1 C8 1.374(3) n
C9 N4 1.355(3) no
C9 C8 1.392(4) n
C9 C3 1.418(4) n
C7 N7 1.335(3) n
C7 C8 1.428(4) no
N4 C5 1.317(4) no
C2' C3' 1.373(4) no
C2' H2' 0.95 no
C3 N2 1.336(3) n
C3 C4 1.427(4) n
C4 N3 1.145(4) n
N7 H7A 0.88 no
N7 H7B 0.88 no
C5 H5 0.95 no
Br C3' 1.901(3) n
C5' C6' 1.380(4) no
C5' C4' 1.386(4) no
C5' H5' 0.95 no
C6' H6' 0.95 no
C3' C4' 1.389(4) no
C4' H4' 0.95 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N7 H7A N6 3_565 0.88 2.12 2.998(3) 175
C2' H2' N4 3_655 0.95 2.42 3.342(3) 163
C6' H6' N4 3_665 0.95 2.67 3.472(3) 143
N7 H7B Br 2 0.88 2.9 3.504(2) 128
C5 H5 Br 4_565 0.95 2.96 3.857(3) 157
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_publ_flag
C2' C1' N1 N2 -45.9(3) no
C6' C1' N1 N2 130.9(3) no
C2' C1' N1 C8 138.2(3) no
C6' C1' N1 C8 -45.0(4) no
C5 N6 C7 N7 -176.7(2) no
C5 N6 C7 C8 3.8(4) no
C8 C9 N4 C5 -0.6(4) no
C3 C9 N4 C5 179.5(3) no
C6' C1' C2' C3' 0.2(4) no
N1 C1' C2' C3' 176.9(2) no
N4 C9 C3 N2 178.7(3) no
C8 C9 C3 N2 -1.2(3) no
N4 C9 C3 C4 -1.3(5) no
C8 C9 C3 C4 178.8(3) no
C9 C3 N2 N1 0.6(3) no
C4 C3 N2 N1 -179.5(2) no
C8 N1 N2 C3 0.3(3) no
C1' N1 N2 C3 -176.4(2) no
N2 N1 C8 C9 -1.1(3) no
C1' N1 C8 C9 175.0(2) no
N2 N1 C8 C7 175.1(3) no
C1' N1 C8 C7 -8.8(5) no
N4 C9 C8 N1 -178.5(2) no
C3 C9 C8 N1 1.4(3) no
N4 C9 C8 C7 4.5(4) no
C3 C9 C8 C7 -175.6(2) no
N7 C7 C8 N1 -1.2(5) no
N6 C7 C8 N1 178.2(3) no
N7 C7 C8 C9 174.7(3) no
N6 C7 C8 C9 -5.9(3) no
C9 N4 C5 N6 -2.0(4) no
C7 N6 C5 N4 0.3(4) no
C4' C5' C6' C1' 0.6(4) no
C2' C1' C6' C5' -1.1(4) no
N1 C1' C6' C5' -177.7(2) no
C1' C2' C3' C4' 1.3(4) no
C1' C2' C3' Br -178.8(2) no
C6' C5' C4' C3' 0.8(4) no
C2' C3' C4' C5' -1.7(4) no
Br C3' C4' C5' 178.3(2) no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21126193
