

data_global

data_rasp15
#TrackingRef '17426_web_deposit_cif_file_0_SivappaRasapalli_1359776974.RASP15.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 4,5-dibromo-N-(3-(imidazo[1,2-a]pyrimidin-3-yl)-3-oxopropyl)-1H-pyrrole-2-carboxamide
?
;
_chemical_name_common            ?acyl
_chemical_melting_point          ?
_chemical_formula_moiety         ?C15
_chemical_formula_sum            'C15 H12 Br2 Cl3 N5 O2'
_chemical_formula_weight         560.47

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

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'

_cell_length_a                   10.979(4)
_cell_length_b                   10.814(4)
_cell_length_c                   16.912(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.916(5)
_cell_angle_gamma                90.00
_cell_volume                     1977.8(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7374
_cell_measurement_theta_min      2.42
_cell_measurement_theta_max      26.48

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.882
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1096
_exptl_absorpt_coefficient_mu    4.526
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3975
_exptl_absorpt_correction_T_max  0.6603
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;Will be reported soon.
?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13769
_diffrn_reflns_av_R_equivalents  0.0487
_diffrn_reflns_av_sigmaI/netI    0.0590
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.06
_diffrn_reflns_theta_max         26.52
_reflns_number_total             4002
_reflns_number_gt                3066
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0225P)²+3.0013P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4002
_refine_ls_number_parameters     250
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0684
_refine_ls_R_factor_gt           0.0449
_refine_ls_wR_factor_ref         0.0899
_refine_ls_wR_factor_gt          0.0799
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_restrained_S_all      1.093
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
C1 C 0.0517(4) 0.1549(4) 0.3291(3) 0.0194(9) Uani 1 1 d . . .
C2 C 0.0688(4) 0.2805(4) 0.3278(3) 0.0212(10) Uani 1 1 d . . .
C3 C 0.0753(4) 0.3258(4) 0.4062(3) 0.0203(10) Uani 1 1 d . . .
H3A H 0.0860 0.4094 0.4232 0.024 Uiso 1 1 calc R . .
C4 C 0.0629(4) 0.2239(4) 0.4538(3) 0.0179(9) Uani 1 1 d . . .
C5 C 0.0631(4) 0.2108(4) 0.5403(3) 0.0174(9) Uani 1 1 d . . .
C6 C 0.0934(4) 0.3132(4) 0.6707(3) 0.0233(10) Uani 1 1 d . . .
H6A H 0.0378 0.2481 0.6851 0.028 Uiso 1 1 calc R . .
H6B H 0.0632 0.3940 0.6870 0.028 Uiso 1 1 calc R . .
C7 C 0.2255(4) 0.2907(4) 0.7165(3) 0.0215(10) Uani 1 1 d . . .
H7A H 0.2468 0.2021 0.7135 0.026 Uiso 1 1 calc R . .
H7B H 0.2853 0.3393 0.6914 0.026 Uiso 1 1 calc R . .
C8 C 0.2339(4) 0.3287(4) 0.8032(3) 0.0189(9) Uani 1 1 d . . .
C9 C 0.2531(4) 0.2336(4) 0.8637(3) 0.0193(10) Uani 1 1 d . . .
C10 C 0.2743(4) 0.1075(4) 0.8574(3) 0.0240(10) Uani 1 1 d . . .
H10 H 0.2773 0.0665 0.8082 0.029 Uiso 1 1 calc R . .
C11 C 0.2790(4) 0.1381(4) 0.9837(3) 0.0220(10) Uani 1 1 d . . .
C12 C 0.2694(4) 0.2240(4) 1.1038(3) 0.0284(11) Uani 1 1 d . . .
H12 H 0.2729 0.2161 1.1601 0.034 Uiso 1 1 calc R . .
C13 C 0.2469(4) 0.3427(4) 1.0693(3) 0.0264(11) Uani 1 1 d . . .
H13 H 0.2358 0.4119 1.1020 0.032 Uiso 1 1 calc R . .
C14 C 0.2413(4) 0.3565(4) 0.9896(3) 0.0227(10) Uani 1 1 d . . .
H14 H 0.2267 0.4351 0.9648 0.027 Uiso 1 1 calc R . .
C15 C 0.1188(5) 0.7476(5) 0.0668(3) 0.0355(12) Uani 1 1 d . . .
H15 H 0.2073 0.7717 0.0844 0.043 Uiso 1 1 calc R . .
N1 N 0.0484(3) 0.1206(3) 0.4055(2) 0.0199(8) Uani 1 1 d D . .
H1N H 0.025(4) 0.053(3) 0.422(3) 0.024 Uiso 1 1 d D . .
N2 N 0.0891(3) 0.3127(3) 0.5846(2) 0.0205(8) Uani 1 1 d D . .
H2N H 0.125(4) 0.373(3) 0.566(3) 0.025 Uiso 1 1 d D . .
N3 N 0.2901(4) 0.0500(3) 0.9296(2) 0.0270(9) Uani 1 1 d . . .
N4 N 0.2857(3) 0.1242(3) 1.0628(2) 0.0267(9) Uani 1 1 d . . .
N5 N 0.2575(3) 0.2533(3) 0.9455(2) 0.0179(8) Uani 1 1 d . . .
O1 O 0.0378(3) 0.1102(3) 0.56912(18) 0.0281(8) Uani 1 1 d . . .
O2 O 0.2203(3) 0.4378(2) 0.81982(18) 0.0245(7) Uani 1 1 d . . .
Br1 Br 0.04233(4) 0.04004(4) 0.24560(3) 0.02645(13) Uani 1 1 d . . .
Br2 Br 0.07690(5) 0.37590(4) 0.23613(3) 0.03147(14) Uani 1 1 d . . .
Cl1 Cl 0.02837(14) 0.88110(11) 0.06159(8) 0.0439(4) Uani 1 1 d . . .
Cl2 Cl 0.07679(17) 0.64628(14) 0.13875(11) 0.0671(5) Uani 1 1 d . . .
Cl3 Cl 0.10488(13) 0.67593(13) -0.02731(9) 0.0479(4) Uani 1 1 d . . .


_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
C1 N1 1.350(6) . ?
C1 C2 1.371(5) . ?
C1 Br1 1.871(4) . ?
C2 C3 1.404(6) . ?
C2 Br2 1.877(4) . ?
C3 C4 1.384(6) . ?
C3 H3A 0.9500 . ?
C4 N1 1.376(5) . ?
C4 C5 1.470(6) . ?
C5 O1 1.243(5) . ?
C5 N2 1.335(5) . ?
C6 N2 1.448(5) . ?
C6 C7 1.541(6) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.510(6) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 O2 1.229(5) . ?
C8 C9 1.441(6) . ?
C9 C10 1.389(5) . ?
C9 N5 1.393(5) . ?
C10 N3 1.354(6) . ?
C10 H10 0.9500 . ?
C11 N4 1.336(6) . ?
C11 N3 1.341(6) . ?
C11 N5 1.404(5) . ?
C12 N4 1.312(6) . ?
C12 C13 1.414(6) . ?
C12 H12 0.9500 . ?
C13 C14 1.347(6) . ?
C13 H13 0.9500 . ?
C14 N5 1.370(5) . ?
C14 H14 0.9500 . ?
C15 Cl1 1.746(5) . ?
C15 Cl3 1.754(5) . ?
C15 Cl2 1.757(5) . ?
C15 H15 1.0000 . ?
N1 H1N 0.840(19) . ?
N2 H2N 0.846(19) . ?

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
N1 C1 C2 108.3(4) . . ?
N1 C1 Br1 122.2(3) . . ?
C2 C1 Br1 129.4(3) . . ?
C1 C2 C3 108.3(4) . . ?
C1 C2 Br2 125.7(3) . . ?
C3 C2 Br2 125.9(3) . . ?
C4 C3 C2 106.1(4) . . ?
C4 C3 H3A 127.0 . . ?
C2 C3 H3A 127.0 . . ?
N1 C4 C3 108.3(4) . . ?
N1 C4 C5 119.5(4) . . ?
C3 C4 C5 132.1(4) . . ?
O1 C5 N2 122.8(4) . . ?
O1 C5 C4 120.8(4) . . ?
N2 C5 C4 116.3(4) . . ?
N2 C6 C7 111.7(4) . . ?
N2 C6 H6A 109.3 . . ?
C7 C6 H6A 109.3 . . ?
N2 C6 H6B 109.3 . . ?
C7 C6 H6B 109.3 . . ?
H6A C6 H6B 107.9 . . ?
C8 C7 C6 109.9(4) . . ?
C8 C7 H7A 109.7 . . ?
C6 C7 H7A 109.7 . . ?
C8 C7 H7B 109.7 . . ?
C6 C7 H7B 109.7 . . ?
H7A C7 H7B 108.2 . . ?
O2 C8 C9 122.1(4) . . ?
O2 C8 C7 119.6(4) . . ?
C9 C8 C7 118.2(4) . . ?
C10 C9 N5 104.4(4) . . ?
C10 C9 C8 130.7(4) . . ?
N5 C9 C8 124.9(4) . . ?
N3 C10 C9 112.3(4) . . ?
N3 C10 H10 123.8 . . ?
C9 C10 H10 123.8 . . ?
N4 C11 N3 127.4(4) . . ?
N4 C11 N5 122.4(4) . . ?
N3 C11 N5 110.2(4) . . ?
N4 C12 C13 124.0(4) . . ?
N4 C12 H12 118.0 . . ?
C13 C12 H12 118.0 . . ?
C14 C13 C12 119.2(4) . . ?
C14 C13 H13 120.4 . . ?
C12 C13 H13 120.4 . . ?
C13 C14 N5 117.8(4) . . ?
C13 C14 H14 121.1 . . ?
N5 C14 H14 121.1 . . ?
Cl1 C15 Cl3 111.1(3) . . ?
Cl1 C15 Cl2 109.6(3) . . ?
Cl3 C15 Cl2 111.1(3) . . ?
Cl1 C15 H15 108.3 . . ?
Cl3 C15 H15 108.3 . . ?
Cl2 C15 H15 108.3 . . ?
C1 N1 C4 109.0(3) . . ?
C1 N1 H1N 128(3) . . ?
C4 N1 H1N 121(3) . . ?
C5 N2 C6 122.3(3) . . ?
C5 N2 H2N 119(3) . . ?
C6 N2 H2N 116(3) . . ?
C11 N3 C10 106.0(4) . . ?
C12 N4 C11 116.6(4) . . ?
C14 N5 C9 132.8(4) . . ?
C14 N5 C11 120.0(4) . . ?
C9 N5 C11 107.2(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
N1 H1N O1 0.840(19) 1.91(2) 2.730(5) 165(4) 3_556
N2 H2N N3 0.846(19) 2.13(3) 2.917(5) 155(4) 2_556

_diffrn_measured_fraction_theta_max 0.972
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.983
_refine_diff_density_max         0.633
_refine_diff_density_min         -0.600
_refine_diff_density_rms         0.117


