Insights into the structural patterns of the antileishmanial activity of bi- and tricyclic N-heterocycles.
Herrera, Lizzi; Stephens, David E.; D'Avila, Abigail; George, Kathryn G.; Arman, Hadi; Zhang, Yu; Perry, George; Lleonart, Ricardo; Larionov, Oleg V.; Fernández, Patricia L; Organic & biomolecular chemistry 14 (2016) 7053–7060; doi:10.1039/c6ob01149g

data_7155175
_publ_section_title
;
 Insights into the structural patterns of the antileishmanial activity of
 bi- and tricyclic N-heterocycles.
;
_journal_issue                   29
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              7053
_journal_page_last               7060
_journal_paper_doi               10.1039/c6ob01149g
_journal_volume                  14
_journal_year                    2016
_chemical_formula_moiety         'C8 H8 Cl N O'
_chemical_formula_sum            'C8 H8 Cl N O'
_chemical_formula_weight         169.60
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_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
_audit_creation_date             2016-01-06
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2016-03-03 deposited with the CCDC.
2016-06-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.770(4)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   11.461(3)
_cell_length_b                   18.171(5)
_cell_length_c                   7.917(2)
_cell_measurement_reflns_used    7742
_cell_measurement_temperature    98
_cell_measurement_theta_max      40.2
_cell_measurement_theta_min      2.2
_cell_volume                     1578.7(7)
_computing_cell_refinement
;
CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_data_collection
;
CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_data_reduction
;
CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      98
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
scan:
    Number of images: 246
               Slice: -68.0000 - 55.0000
         Image width: 0.5000
            Exp time: 25.0000
       Rotation axis: Omega
               Omega: 0.0000
               Kappa: 70.0000
                 Phi: 270.0000
                 XTD: 34.4856
              2theta: -34.7367
scan:
    Number of images: 164
               Slice: -49.0000 - 33.0000
         Image width: 0.5000
            Exp time: 25.0000
       Rotation axis: Omega
               Omega: 0.0000
               Kappa: 70.0000
                 Phi: 90.0000
                 XTD: 34.4856
              2theta: -34.7367
scan:
    Number of images: 136
               Slice: -88.0000 - -20.0000
         Image width: 0.5000
            Exp time: 25.0000
       Rotation axis: Omega
               Omega: 0.0000
               Kappa: 0.0000
                 Phi: 270.0000
                 XTD: 34.4856
              2theta: -34.7367
scan:
    Number of images: 92
               Slice: -61.0000 - -15.0000
         Image width: 0.5000
            Exp time: 25.0000
       Rotation axis: Omega
               Omega: 0.0000
               Kappa: 70.0000
                 Phi: 0.0000
                 XTD: 34.4856
              2theta: -34.7367
scan:
    Number of images: 62
               Slice: -115.0000 - -84.0000
         Image width: 0.5000
            Exp time: 25.0000
       Rotation axis: Omega
               Omega: 0.0000
               Kappa: 0.0000
                 Phi: 180.0000
                 XTD: 34.4856
              2theta: -34.7367
;
_diffrn_measurement_device
;
AFC12 (Right): Kappa 3 circle
;
_diffrn_measurement_device_type
;
Rigaku Saturn724 (2x2 bin mode)
;
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_measurement_specimen_support Fiber
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      -0.103867
_diffrn_orient_matrix_UB_12      0.081254
_diffrn_orient_matrix_UB_13      0.003521
_diffrn_orient_matrix_UB_21      -0.020832
_diffrn_orient_matrix_UB_22      -0.024699
_diffrn_orient_matrix_UB_23      -0.044549
_diffrn_orient_matrix_UB_31      -0.063160
_diffrn_orient_matrix_UB_32      -0.040298
_diffrn_orient_matrix_UB_33      0.051877
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0453
_diffrn_reflns_av_unetI/netI     0.0350
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            12469
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_min         1.856
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           40.0
_diffrn_source_power             2.0
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.419
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.916
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Higashi, 1995)'
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.427
_exptl_crystal_description       block
_exptl_crystal_F_000             704
_exptl_crystal_recrystallization_method 'vapor diffusion of hexane into toluene'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.345
_refine_diff_density_min         -0.281
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         3617
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0341
_refine_ls_R_factor_gt           0.0328
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0320P)^2^+0.7660P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0803
_refine_ls_wR_factor_ref         0.0816
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3489
_reflns_number_total             3617
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6ob01149g2.cif
_cod_data_source_block           cd1399a
_cod_depositor_comments
'Adding full bibliography for 7155174--7155178.cif.'
_cod_database_code               7155175
_shelx_estimated_absorpt_t_max   0.921
_shelx_estimated_absorpt_t_min   0.921
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C1(H1A,H1B)
2.b Aromatic/amide H refined with riding coordinates:
 C12(H12), C8(H8), C4(H4), C16(H16), C14(H14), C7(H7), C13(H13), C15(H15),
 C6(H6), C5(H5)
2.c Idealised tetrahedral OH refined as rotating group:
 O2(H2), O1(H1)
;
_shelx_shelxl_version_number     2014/7
_olex2_exptl_crystal_mounting_method 'cryo loop'
_olex2_submission_special_instructions 'No special instructions were received'