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_7155178
_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         'C26 H25 Br N2 O'
_chemical_formula_sum            'C26 H25 Br N2 O'
_chemical_formula_weight         461.39
_chemical_name_systematic
(4aR,9aR)-6-bromo-4a-ethyl-9-(2-methylbenzyl)-3-phenyl-4,4a,9,9a-tetrahydro-[1,2]oxazino[6,5-b]indole
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   difmap
_audit_creation_date             2016-04-01
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2016-05-22 deposited with the CCDC.
2016-06-27 downloaded from the CCDC.
;
_cell_angle_alpha                84.992(11)
_cell_angle_beta                 72.078(11)
_cell_angle_gamma                74.256(11)
_cell_formula_units_Z            2
_cell_length_a                   9.1842(15)
_cell_length_b                   10.542(2)
_cell_length_c                   11.953(2)
_cell_measurement_reflns_used    4684
_cell_measurement_temperature    98
_cell_measurement_theta_max      40.2
_cell_measurement_theta_min      2.8
_cell_volume                     1059.8(3)
_computing_cell_refinement
;
CrystalClear-SM Expert 2.0 r5 (Rigaku, 2010)
;
_computing_data_collection
;
CrystalClear-SM Expert 2.0 r5 (Rigaku, 2010)
;
_computing_data_reduction
;
CrystalClear-SM Expert 2.0 r5 (Rigaku, 2010)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_diffrn_ambient_temperature      98
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_details
;
scan:
    Number of images: 240
               Slice: -125.0000 - -5.0000
         Image width: 0.5000
            Exp time: 30.0000
       Rotation axis: Omega
               Omega: 0.0000
               Kappa: 0.0000
                 Phi: 270.0000
                 XTD: 34.8119
              2theta: -35.1803
scan:
    Number of images: 150
               Slice: -106.0000 - -31.0000
         Image width: 0.5000
            Exp time: 30.0000
       Rotation axis: Omega
               Omega: 0.0000
               Kappa: 0.0000
                 Phi: 0.0000
                 XTD: 34.8119
              2theta: -35.1803
scan:
    Number of images: 106
               Slice: -65.0000 - -12.0000
         Image width: 0.5000
            Exp time: 30.0000
       Rotation axis: Omega
               Omega: 0.0000
               Kappa: 70.0000
                 Phi: 180.0000
                 XTD: 34.8119
              2theta: -35.1803
scan:
    Number of images: 100
               Slice: -65.0000 - -15.0000
         Image width: 0.5000
            Exp time: 30.0000
       Rotation axis: Omega
               Omega: 0.0000
               Kappa: 70.0000
                 Phi: 0.0000
                 XTD: 34.8119
              2theta: -35.1803
;
_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      0.107699
_diffrn_orient_matrix_UB_12      -0.045291
_diffrn_orient_matrix_UB_13      0.019456
_diffrn_orient_matrix_UB_21      0.009597
_diffrn_orient_matrix_UB_22      0.054172
_diffrn_orient_matrix_UB_23      -0.081777
_diffrn_orient_matrix_UB_31      -0.006549
_diffrn_orient_matrix_UB_32      0.073252
_diffrn_orient_matrix_UB_33      0.048195
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0392
_diffrn_reflns_av_unetI/netI     0.0511
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7087
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_min         2.412
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           40.0
_diffrn_source_power             2.0
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    1.960
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.364
_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    1.446
_exptl_crystal_description       plank
_exptl_crystal_F_000             476
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.725
_refine_diff_density_min         -0.770
_refine_diff_density_rms         0.076
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     346
_refine_ls_number_reflns         4807
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0416
_refine_ls_R_factor_gt           0.0377
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0400P)^2^+0.4500P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0867
_refine_ls_wR_factor_ref         0.0885
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4223
_reflns_number_total             4807
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6ob01149g2.cif
_cod_data_source_block           cd0965a
_cod_depositor_comments
'Adding full bibliography for 7155174--7155178.cif.'
_cod_database_code               7155178
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H,H,H,H,H,H,H,H,H,H,H,H,H,H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H,H,H,H) groups
;
_shelx_shelxl_version_number     2014/7
_olex2_exptl_crystal_mounting_method 'glass fiber'
_olex2_submission_special_instructions 'No special instructions were received'