#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:51:30 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180319 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/33/7153315.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_7153315
loop_
_publ_author_name
'Venturoni, Francesco'
'Nikbin, Nikzad'
'Ley, Steven V.'
'Baxendale, Ian R.'
_publ_section_title
;
 The application of flow microreactors to the preparation of a family of
 casein kinase I inhibitors.
;
_journal_issue                   8
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              1798
_journal_page_last               1806
_journal_paper_doi               10.1039/b925327k
_journal_volume                  8
_journal_year                    2010
_chemical_formula_moiety         'C13 H10 Br F N O 1+, Br 1-'
_chemical_formula_sum            'C13 H10 Br2 F N O'
_chemical_formula_weight         375.04
_chemical_name_systematic
;
?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                83.177(1)
_cell_angle_beta                 85.689(1)
_cell_angle_gamma                61.994(1)
_cell_formula_units_Z            2
_cell_length_a                   7.8896(2)
_cell_length_b                   8.2318(2)
_cell_length_c                   12.0308(3)
_cell_measurement_reflns_used    7555
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      32.03
_cell_measurement_theta_min      1.00
_cell_volume                     684.80(3)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius B.V. 1998)'
_computing_data_reduction
;
HKL Denzo and Scalepack (Otwinowski & Minor 1997)
;
_computing_publication_material  'SHELXL-97 (Sheldrick 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick 1997)'
_computing_structure_solution    'SIR-92 (Altomare et al. 1994)'
_diffrn_ambient_temperature      180(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       'Thin slice ω and φ scans'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0568
_diffrn_reflns_av_sigmaI/netI    0.0467
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            9948
_diffrn_reflns_theta_full        32.03
_diffrn_reflns_theta_max         32.03
_diffrn_reflns_theta_min         3.59
_exptl_absorpt_coefficient_mu    5.917
_exptl_absorpt_correction_T_max  0.821
_exptl_absorpt_correction_T_min  0.462
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
multi-scan from symmetry-related measurements
Sortav (Blessing 1995)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.819
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             364
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.07
_refine_diff_density_max         1.326
_refine_diff_density_min         -1.511
_refine_diff_density_rms         0.188
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         4729
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0540
_refine_ls_R_factor_gt           0.0443
_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)+(0.0555P)²+0.8954P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1113
_refine_ls_wR_factor_ref         0.1188
_reflns_number_gt                4002
_reflns_number_total             4729
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b925327k.txt
_cod_data_source_block           sl0941
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7153315
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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 0.22350(4) 0.00492(4) -0.11772(2) 0.02908(9) Uani 1 1 d .
Br2 Br 0.17430(4) 0.19522(4) 0.13589(3) 0.03022(9) Uani 1 1 d .
O1 O 0.2102(4) -0.1806(4) -0.3744(2) 0.0410(6) Uani 1 1 d .
N1 N 0.2754(3) -0.3976(3) -0.1587(2) 0.0246(4) Uani 1 1 d .
H1 H 0.1579 -0.3070 -0.1678 0.030 Uiso 1 1 calc R
F1 F 0.2712(4) 0.5313(3) -0.5806(2) 0.0514(6) Uani 1 1 d .
C1 C 0.2767(5) 0.3779(4) -0.5213(3) 0.0354(6) Uani 1 1 d .
C2 C 0.3881(5) 0.3061(5) -0.4283(3) 0.0360(7) Uani 1 1 d .
H2 H 0.4604 0.3616 -0.4060 0.043 Uiso 1 1 calc R
C3 C 0.3924(5) 0.1494(4) -0.3673(3) 0.0305(6) Uani 1 1 d .
H3 H 0.4680 0.0969 -0.3023 0.037 Uiso 1 1 calc R
C4 C 0.2858(4) 0.0690(4) -0.4015(2) 0.0260(5) Uani 1 1 d .
C5 C 0.1776(4) 0.1455(4) -0.4980(3) 0.0323(6) Uani 1 1 d .
H5 H 0.1063 0.0903 -0.5221 0.039 Uiso 1 1 calc R
C6 C 0.1728(5) 0.3011(5) -0.5590(3) 0.0370(7) Uani 1 1 d .
H6 H 0.0998 0.3532 -0.6250 0.044 Uiso 1 1 calc R
C7 C 0.2861(4) -0.0983(4) -0.3399(2) 0.0260(5) Uani 1 1 d .
C8 C 0.3855(4) -0.1679(4) -0.2265(2) 0.0237(5) Uani 1 1 d .
H8 H 0.5112 -0.1651 -0.2345 0.028 Uiso 1 1 calc R
C9 C 0.4231(4) -0.3597(4) -0.1846(2) 0.0220(4) Uani 1 1 d .
C10 C 0.6078(4) -0.5029(4) -0.1723(3) 0.0280(5) Uani 1 1 d .
H10 H 0.7148 -0.4801 -0.1890 0.034 Uiso 1 1 calc R
C11 C 0.6365(4) -0.6808(4) -0.1352(3) 0.0315(6) Uani 1 1 d .
H11 H 0.7632 -0.7801 -0.1283 0.038 Uiso 1 1 calc R
C12 C 0.4799(4) -0.7123(4) -0.1084(3) 0.0298(5) Uani 1 1 d .
H12 H 0.4975 -0.8328 -0.0826 0.036 Uiso 1 1 calc R
C13 C 0.2979(4) -0.5654(4) -0.1199(3) 0.0282(5) Uani 1 1 d .
H13 H 0.1886 -0.5835 -0.1003 0.034 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'
F F 0.0171 0.0103 '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
C13 N1 C9 123.5(2)
C13 N1 H1 118.3
C9 N1 H1 118.3
F1 C1 C2 118.3(3)
F1 C1 C6 118.2(3)
C2 C1 C6 123.5(3)
C1 C2 C3 118.1(3)
C1 C2 H2 121.0
C3 C2 H2 121.0
C2 C3 C4 120.2(3)
C2 C3 H3 119.9
C4 C3 H3 119.9
C5 C4 C3 119.4(3)
C5 C4 C7 118.2(3)
C3 C4 C7 122.3(3)
C6 C5 C4 120.7(3)
C6 C5 H5 119.7
C4 C5 H5 119.7
C1 C6 C5 118.1(3)
C1 C6 H6 120.9
C5 C6 H6 120.9
O1 C7 C4 123.2(3)
O1 C7 C8 118.9(3)
C4 C7 C8 117.9(2)
C9 C8 C7 114.1(2)
C9 C8 Br1 109.94(18)
C7 C8 Br1 107.84(18)
C9 C8 H8 108.3
C7 C8 H8 108.3
Br1 C8 H8 108.3
N1 C9 C10 118.2(2)
N1 C9 C8 120.1(2)
C10 C9 C8 121.7(2)
C9 C10 C11 119.8(3)
C9 C10 H10 120.1
C11 C10 H10 120.1
C12 C11 C10 119.8(3)
C12 C11 H11 120.1
C10 C11 H11 120.1
C13 C12 C11 118.7(3)
C13 C12 H12 120.7
C11 C12 H12 120.7
N1 C13 C12 119.9(3)
N1 C13 H13 120.0
C12 C13 H13 120.0
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C8 1.963(3)
O1 C7 1.214(3)
N1 C13 1.337(3)
N1 C9 1.347(3)
N1 H1 0.8800
F1 C1 1.358(3)
C1 C2 1.370(5)
C1 C6 1.374(5)
C2 C3 1.394(4)
C2 H2 0.9500
C3 C4 1.397(4)
C3 H3 0.9500
C4 C5 1.394(4)
C4 C7 1.484(4)
C5 C6 1.384(4)
C5 H5 0.9500
C6 H6 0.9500
C7 C8 1.536(4)
C8 C9 1.493(4)
C8 H8 1.0000
C9 C10 1.383(4)
C10 C11 1.394(4)
C10 H10 0.9500
C11 C12 1.386(4)
C11 H11 0.9500
C12 C13 1.379(4)
C12 H12 0.9500
C13 H13 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
F1 C1 C2 C3 179.6(3)
C6 C1 C2 C3 -1.6(5)
C1 C2 C3 C4 0.3(5)
C2 C3 C4 C5 0.9(5)
C2 C3 C4 C7 179.7(3)
C3 C4 C5 C6 -0.9(5)
C7 C4 C5 C6 -179.7(3)
F1 C1 C6 C5 -179.6(3)
C2 C1 C6 C5 1.6(5)
C4 C5 C6 C1 -0.4(5)
C5 C4 C7 O1 6.4(5)
C3 C4 C7 O1 -172.4(3)
C5 C4 C7 C8 -172.8(3)
C3 C4 C7 C8 8.4(4)
O1 C7 C8 C9 15.6(4)
C4 C7 C8 C9 -165.2(2)
O1 C7 C8 Br1 -106.8(3)
C4 C7 C8 Br1 72.4(3)
C13 N1 C9 C10 1.2(4)
C13 N1 C9 C8 -179.4(3)
C7 C8 C9 N1 -64.4(3)
Br1 C8 C9 N1 56.9(3)
C7 C8 C9 C10 115.0(3)
Br1 C8 C9 C10 -123.7(2)
N1 C9 C10 C11 0.8(4)
C8 C9 C10 C11 -178.6(3)
C9 C10 C11 C12 -1.5(5)
C10 C11 C12 C13 0.4(5)
C9 N1 C13 C12 -2.3(5)
C11 C12 C13 N1 1.5(5)
