#------------------------------------------------------------------------------
#$Date: 2016-03-26 14:51:30 +0100 (Sat 26 de Mar de 2016) $
#$Revision: 180319 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/33/7153316.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_7153316
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         'C11 H7 Cl F N3 O'
_chemical_formula_sum            'C11 H7 Cl F N3 O'
_chemical_formula_weight         251.65
_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                105.020(3)
_cell_angle_beta                 93.976(3)
_cell_angle_gamma                104.710(2)
_cell_formula_units_Z            2
_cell_length_a                   5.5835(3)
_cell_length_b                   8.4844(4)
_cell_length_c                   11.9337(7)
_cell_measurement_reflns_used    8738
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      25.03
_cell_measurement_theta_min      1.00
_cell_volume                     522.56(5)
_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 0.988
_diffrn_measured_fraction_theta_max 0.988
_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  0.0522
_diffrn_reflns_av_sigmaI/netI    0.0463
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5552
_diffrn_reflns_theta_full        25.06
_diffrn_reflns_theta_max         25.06
_diffrn_reflns_theta_min         3.54
_exptl_absorpt_coefficient_mu    0.364
_exptl_absorpt_correction_T_max  0.982
_exptl_absorpt_correction_T_min  0.894
_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    1.599
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             256
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.534
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.081
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.224
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         1841
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.224
_refine_ls_R_factor_all          0.0642
_refine_ls_R_factor_gt           0.0545
_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)+(0.0529P)²+0.5592P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1444
_refine_ls_wR_factor_ref         0.1505
_reflns_number_gt                1572
_reflns_number_total             1841
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b925327k.txt
_cod_data_source_block           sl0970
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7153316
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
Cl1 Cl 0.07356(15) 0.68585(10) 0.60196(7) 0.0417(3) Uani 1 1 d .
F1 F 0.6981(4) 1.8811(3) 1.48024(19) 0.0594(7) Uani 1 1 d .
N2 N 0.1132(5) 1.0454(4) 0.8833(2) 0.0365(6) Uani 1 1 d .
O1 O 0.8362(4) 1.3316(3) 1.0437(2) 0.0478(7) Uani 1 1 d .
N1 N 0.4097(5) 1.2571(3) 1.0155(2) 0.0363(6) Uani 1 1 d .
H1 H 0.2796 1.2853 1.0431 0.044 Uiso 1 1 calc R
C9 C 0.5403(6) 1.0592(4) 0.8557(3) 0.0360(7) Uani 1 1 d .
H9 H 0.7140 1.1109 0.8821 0.043 Uiso 1 1 calc R
N3 N 0.0314(5) 0.9114(4) 0.7870(2) 0.0380(7) Uani 1 1 d .
C8 C 0.3584(6) 1.1175(4) 0.9158(3) 0.0313(7) Uani 1 1 d .
C4 C 0.6429(6) 1.4941(4) 1.1826(3) 0.0344(7) Uani 1 1 d .
C6 C 0.4629(7) 1.6237(5) 1.3467(3) 0.0499(9) Uani 1 1 d .
H6 H 0.3271 1.6235 1.3905 0.060 Uiso 1 1 calc R
C7 C 0.6414(6) 1.3556(4) 1.0753(3) 0.0350(7) Uani 1 1 d .
C10 C 0.4555(6) 0.9244(4) 0.7573(3) 0.0376(8) Uani 1 1 d .
H10 H 0.5676 0.8787 0.7115 0.045 Uiso 1 1 calc R
C3 C 0.8630(6) 1.6260(4) 1.2222(3) 0.0389(8) Uani 1 1 d .
H3 H 1.0008 1.6261 1.1798 0.047 Uiso 1 1 calc R
C5 C 0.4441(7) 1.4934(5) 1.2457(3) 0.0437(8) Uani 1 1 d .
H5 H 0.2938 1.4030 1.2196 0.052 Uiso 1 1 calc R
C1 C 0.6810(7) 1.7527(4) 1.3820(3) 0.0418(8) Uani 1 1 d .
C11 C 0.1965(6) 0.8567(4) 0.7271(3) 0.0343(7) Uani 1 1 d .
C2 C 0.8835(7) 1.7571(4) 1.3227(3) 0.0421(8) Uani 1 1 d .
H2 H 1.0334 1.8476 1.3499 0.051 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'
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'
F F 0.0171 0.0103 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C8 N2 N3 119.5(3)
C7 N1 C8 127.2(3)
C7 N1 H1 116.4
C8 N1 H1 116.4
C10 C9 C8 116.7(3)
C10 C9 H9 121.6
C8 C9 H9 121.6
C11 N3 N2 118.6(3)
N2 C8 N1 111.9(3)
N2 C8 C9 123.4(3)
N1 C8 C9 124.7(3)
C5 C4 C3 119.4(3)
C5 C4 C7 123.8(3)
C3 C4 C7 116.8(3)
C1 C6 C5 118.6(3)
C1 C6 H6 120.7
C5 C6 H6 120.7
O1 C7 N1 122.5(3)
O1 C7 C4 121.3(3)
N1 C7 C4 116.2(3)
C9 C10 C11 117.0(3)
C9 C10 H10 121.5
C11 C10 H10 121.5
C2 C3 C4 120.7(3)
C2 C3 H3 119.6
C4 C3 H3 119.6
C4 C5 C6 120.4(3)
C4 C5 H5 119.8
C6 C5 H5 119.8
F1 C1 C6 118.5(3)
F1 C1 C2 118.7(3)
C6 C1 C2 122.8(3)
N3 C11 C10 124.8(3)
N3 C11 Cl1 115.4(2)
C10 C11 Cl1 119.7(2)
C1 C2 C3 118.1(3)
C1 C2 H2 121.0
C3 C2 H2 121.0
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C11 1.742(3)
F1 C1 1.357(4)
N2 C8 1.333(4)
N2 N3 1.345(4)
O1 C7 1.223(4)
N1 C7 1.377(4)
N1 C8 1.396(4)
N1 H1 0.8800
C9 C10 1.364(5)
C9 C8 1.402(5)
C9 H9 0.9500
N3 C11 1.308(4)
C4 C5 1.384(5)
C4 C3 1.390(5)
C4 C7 1.495(5)
C6 C1 1.368(5)
C6 C5 1.385(5)
C6 H6 0.9500
C10 C11 1.396(5)
C10 H10 0.9500
C3 C2 1.383(5)
C3 H3 0.9500
C5 H5 0.9500
C1 C2 1.372(5)
C2 H2 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
C8 N2 N3 C11 -0.8(5)
N3 N2 C8 N1 178.5(3)
N3 N2 C8 C9 -1.1(5)
C7 N1 C8 N2 176.9(3)
C7 N1 C8 C9 -3.5(5)
C10 C9 C8 N2 1.8(5)
C10 C9 C8 N1 -177.7(3)
C8 N1 C7 O1 1.9(5)
C8 N1 C7 C4 -177.7(3)
C5 C4 C7 O1 -156.7(3)
C3 C4 C7 O1 20.5(5)
C5 C4 C7 N1 22.9(5)
C3 C4 C7 N1 -160.0(3)
C8 C9 C10 C11 -0.7(5)
C5 C4 C3 C2 -0.9(5)
C7 C4 C3 C2 -178.2(3)
C3 C4 C5 C6 0.7(5)
C7 C4 C5 C6 177.8(3)
C1 C6 C5 C4 0.3(6)
C5 C6 C1 F1 179.3(3)
C5 C6 C1 C2 -1.1(6)
N2 N3 C11 C10 1.9(5)
N2 N3 C11 Cl1 -178.6(2)
C9 C10 C11 N3 -1.1(5)
C9 C10 C11 Cl1 179.4(3)
F1 C1 C2 C3 -179.5(3)
C6 C1 C2 C3 0.8(6)
C4 C3 C2 C1 0.2(5)
