data_global
_audit_creation_method                  'APEX3 v2017.3-0'

_publ_requested_journal                 ?

_publ_contact_author_name               ?
_publ_contact_author_address            
;
;
_publ_contact_author_email              ?
_publ_contact_author_fax                ?
_publ_contact_author_phone              ?

_publ_section_title                     
;
;
_publ_section_abstract                  
;
;
_publ_section_references                
;
;
_publ_section_comment                   
;
;

data_LHQ6
_chemical_name_systematic               ?
_chemical_name_common                   ?
_chemical_formula_moiety                ?
_chemical_formula_sum                   'C19 H21 N O2'
_chemical_formula_iupac                 ?
_chemical_formula_weight                295.37

_chemical_melting_point                 ?

_space_group_crystal_system             monoclinic
_space_group_name_H-M_alt               'P 1 21/n 1'
_space_group_name_Hall                  '-P 2yn'
loop_
    _space_group_symop_operation_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                          9.1378(3)
_cell_length_b                          13.0875(4)
_cell_length_c                          14.4181(4)
_cell_angle_alpha                       90
_cell_angle_beta                        108.3250(10)
_cell_angle_gamma                       90
_cell_volume                            1636.83(9)
_cell_formula_units_Z                   4
_cell_measurement_reflns_used           9867
_cell_measurement_theta_min             4.6748
_cell_measurement_theta_max             79.2322
_cell_measurement_temperature           150.(2)

_exptl_crystal_description              Block
_exptl_crystal_colour                   'light colourless'
_exptl_crystal_size_max                 0.200
_exptl_crystal_size_mid                 0.189
_exptl_crystal_size_min                 0.156
_exptl_crystal_density_diffrn           1.199
_exptl_crystal_density_meas             ?
_exptl_crystal_density_method           'not measured'
_exptl_crystal_F_000                    632

_exptl_absorpt_coefficient_mu           0.612
_exptl_absorpt_correction_type          Multi-Scan
_exptl_absorpt_process_details          
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min         0.81
_exptl_absorpt_correction_T_max         0.91

_exptl_special_details                  
;
; 

_diffrn_ambient_temperature             150.(2)

_diffrn_source                          ?
_diffrn_source_type                     ?

_diffrn_radiation_type                  'Cu K\a'
_diffrn_radiation_wavelength            1.54178
_diffrn_radiation_monochromator         ?

_diffrn_measurement_device_type         'Bruker APEX-II CCD'
_diffrn_measurement_method              'φ and ω scans' 

_diffrn_detector_area_resol_mean        7.3910

_diffrn_reflns_number                   39082
_diffrn_reflns_av_R_equivalents         0.0464
_diffrn_reflns_av_unetI/netI            0.0244
_diffrn_reflns_theta_min                4.67
_diffrn_reflns_theta_max                79.36
_diffrn_reflns_theta_full               79.36
_diffrn_measured_fraction_theta_max     0.997
_diffrn_measured_fraction_theta_full    0.997
_diffrn_reflns_limit_h_min              -11
_diffrn_reflns_limit_h_max              11
_diffrn_reflns_limit_k_min              -16
_diffrn_reflns_limit_k_max              16
_diffrn_reflns_limit_l_min              -18
_diffrn_reflns_limit_l_max              17

_refine_special_details                 
;
;

_reflns_number_total                    3551
_reflns_number_gt                       3243
_reflns_threshold_expression            'I > 2σ(I)'

_refine_ls_structure_factor_coef        Fsqd
_refine_ls_matrix_type                  full
_refine_ls_R_factor_all                 0.0424
_refine_ls_R_factor_gt                  0.0391
_refine_ls_wR_factor_gt                 0.0960
_refine_ls_wR_factor_ref                0.0989
_refine_ls_goodness_of_fit_ref          1.039
_refine_ls_restrained_S_all             1.039
_refine_ls_number_reflns                3551
_refine_ls_number_parameters            203
_refine_ls_number_restraints            0
_refine_ls_number_constraints           ?
_refine_ls_hydrogen_treatment           constr
_refine_ls_weighting_scheme             calc
_refine_ls_weighting_details            
    'w=1/[σ²(Fo²)+(0.0467P)²+0.4395P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens          geom
_atom_sites_solution_primary            ?
_atom_sites_solution_secondary          ?

_refine_ls_shift/su_max                 0.001
_refine_ls_shift/su_mean                0.000
_refine_diff_density_max                0.229
_refine_diff_density_min                -0.203
_refine_ls_extinction_method            none
_refine_ls_extinction_coef              ?

loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection              ?
_computing_cell_refinement              'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_reduction               'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution           'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement         'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics           'shelXle (C.B. Huebschle, rev 833)'
_computing_publication_material         ?

loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_refinement_flags_adp
    _atom_site_refinement_flags_occupancy
    _atom_site_refinement_flags_posn
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    O O1 0.20824(9) 0.40256(6) 0.57133(5) 0.02720(17) Uani d . . . 1 . .
    N N1 0.37839(10) 0.75633(7) 0.61904(6) 0.02449(19) Uani d . . . 1 . .
    H H1 0.326325 0.785154 0.563282 0.029 Uiso calc U . R 1 . .
    O O2 0.70832(10) 0.68677(6) 0.92439(5) 0.03349(19) Uani d . . . 1 . .
    C C2 0.48332(12) 0.80502(8) 0.69401(7) 0.0241(2) Uani d . . . 1 . .
    C C3 0.54071(12) 0.73476(8) 0.77030(7) 0.0250(2) Uani d . . . 1 . .
    C C5 0.38513(12) 0.46221(8) 0.72401(7) 0.0257(2) Uani d . . . 1 . .
    C C6 0.29252(12) 0.48100(8) 0.62619(7) 0.0250(2) Uani d . . . 1 . .
    C C8 0.36470(12) 0.65480(8) 0.64260(7) 0.0241(2) Uani d . . . 1 . .
    C C19 0.41880(14) 0.30192(9) 0.54985(9) 0.0353(3) Uani d . . . 1 . .
    H H19A 0.382073 0.313858 0.479169 0.053 Uiso calc U . R 1 . .
    H H19B 0.470988 0.235598 0.563308 0.053 Uiso calc U . R 1 . .
    H H19C 0.491141 0.356096 0.581797 0.053 Uiso calc U . R 1 . .
    C C18 0.28180(13) 0.30226(8) 0.58926(8) 0.0284(2) Uani d . . . 1 . .
    C C9 0.46303(12) 0.63852(8) 0.73835(7) 0.0243(2) Uani d . . . 1 . .
    C C20 0.15664(14) 0.22888(9) 0.53229(9) 0.0337(2) Uani d . . . 1 . .
    H H20A 0.121579 0.248505 0.463193 0.051 Uiso calc U . R 1 . .
    H H20B 0.069629 0.231606 0.558234 0.051 Uiso calc U . R 1 . .
    H H20C 0.198082 0.159244 0.538741 0.051 Uiso calc U . R 1 . .
    C C10 0.66113(13) 0.75221(9) 0.85996(7) 0.0279(2) Uani d . . . 1 . .
    H H10 0.707693 0.81789 0.870761 0.033 Uiso calc U . R 1 . .
    C C16 0.38649(13) 0.35775(9) 0.76035(8) 0.0297(2) Uani d . . . 1 . .
    H H16 0.423946 0.344598 0.828568 0.036 Uiso calc U . R 1 . .
    C C4 0.46909(12) 0.54179(8) 0.78002(7) 0.0258(2) Uani d . . . 1 . .
    H H4 0.529901 0.530363 0.845948 0.031 Uiso calc U . R 1 . .
    C C7 0.27665(12) 0.57724(8) 0.58495(7) 0.0259(2) Uani d . . . 1 . .
    H H7 0.209461 0.589964 0.520829 0.031 Uiso calc U . R 1 . .
    C C17 0.33520(14) 0.28107(9) 0.69781(8) 0.0316(2) Uani d . . . 1 . .
    H H17 0.332212 0.213526 0.721269 0.038 Uiso calc U . R 1 . .
    C C15 0.39721(15) 0.97088(9) 0.60543(9) 0.0370(3) Uani d . . . 1 . .
    H H15A 0.42562 1.042654 0.601986 0.056 Uiso calc U . R 1 . .
    H H15B 0.300588 0.967033 0.621226 0.056 Uiso calc U . R 1 . .
    H H15C 0.38362 0.937894 0.542247 0.056 Uiso calc U . R 1 . .
    C C13 0.52582(13) 0.91592(8) 0.68533(7) 0.0262(2) Uani d . . . 1 . .
    C C12 0.54195(15) 0.97229(9) 0.78001(8) 0.0333(2) Uani d . . . 1 . .
    H H12 0.465192 0.95978 0.810317 0.04 Uiso calc U . R 1 . .
    C C14 0.67423(15) 0.91876(10) 0.65703(9) 0.0364(3) Uani d . . . 1 . .
    H H14A 0.659568 0.878941 0.597228 0.055 Uiso calc U . R 1 . .
    H H14B 0.759216 0.889476 0.710005 0.055 Uiso calc U . R 1 . .
    H H14C 0.698669 0.989681 0.645789 0.055 Uiso calc U . R 1 . .
    C C11 0.6527(2) 1.03712(11) 0.82422(10) 0.0498(4) Uani d . . . 1 . .
    H H11A 0.732017 1.052064 0.796679 0.06 Uiso calc U . R 1 . .
    H H11B 0.652999 1.068798 0.883567 0.06 Uiso calc U . R 1 . .


_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_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    O1 C6 . 1.3746(13) ?
    O1 C18 . 1.4603(13) ?
    N1 C2 . 1.3572(13) ?
    N1 C8 . 1.3868(14) ?
    N1 H1 . 0.88 ?
    O2 C10 . 1.2371(14) ?
    C2 C3 . 1.4028(14) ?
    C2 C13 . 1.5178(14) ?
    C3 C10 . 1.4282(14) ?
    C3 C9 . 1.4481(15) ?
    C5 C4 . 1.3914(15) ?
    C5 C6 . 1.4195(14) ?
    C5 C16 . 1.4627(15) ?
    C6 C7 . 1.3809(15) ?
    C8 C7 . 1.3958(15) ?
    C8 C9 . 1.4067(14) ?
    C19 C18 . 1.5288(16) ?
    C19 H19A . 0.98 ?
    C19 H19B . 0.98 ?
    C19 H19C . 0.98 ?
    C18 C17 . 1.5114(15) ?
    C18 C20 . 1.5214(15) ?
    C9 C4 . 1.3949(15) ?
    C20 H20A . 0.98 ?
    C20 H20B . 0.98 ?
    C20 H20C . 0.98 ?
    C10 H10 . 0.95 ?
    C16 C17 . 1.3319(17) ?
    C16 H16 . 0.95 ?
    C4 H4 . 0.95 ?
    C7 H7 . 0.95 ?
    C17 H17 . 0.95 ?
    C15 C13 . 1.5409(15) ?
    C15 H15A . 0.98 ?
    C15 H15B . 0.98 ?
    C15 H15C . 0.98 ?
    C13 C12 . 1.5175(14) ?
    C13 C14 . 1.5345(16) ?
    C12 C11 . 1.321(2) ?
    C12 H12 . 0.95 ?
    C14 H14A . 0.98 ?
    C14 H14B . 0.98 ?
    C14 H14C . 0.98 ?
    C11 H11A . 0.95 ?
    C11 H11B . 0.95 ?

loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    C6 O1 C18 . . 115.22(8) ?
    C2 N1 C8 . . 110.51(8) ?
    C2 N1 H1 . . 124.7 ?
    C8 N1 H1 . . 124.7 ?
    N1 C2 C3 . . 108.25(9) ?
    N1 C2 C13 . . 121.22(9) ?
    C3 C2 C13 . . 130.48(9) ?
    C2 C3 C10 . . 126.63(10) ?
    C2 C3 C9 . . 107.20(9) ?
    C10 C3 C9 . . 126.02(9) ?
    C4 C5 C6 . . 119.65(10) ?
    C4 C5 C16 . . 123.41(9) ?
    C6 C5 C16 . . 116.94(9) ?
    O1 C6 C7 . . 118.00(9) ?
    O1 C6 C5 . . 119.57(9) ?
    C7 C6 C5 . . 122.34(10) ?
    N1 C8 C7 . . 129.08(9) ?
    N1 C8 C9 . . 107.86(9) ?
    C7 C8 C9 . . 123.02(10) ?
    C18 C19 H19A . . 109.5 ?
    C18 C19 H19B . . 109.5 ?
    H19A C19 H19B . . 109.5 ?
    C18 C19 H19C . . 109.5 ?
    H19A C19 H19C . . 109.5 ?
    H19B C19 H19C . . 109.5 ?
    O1 C18 C17 . . 109.21(9) ?
    O1 C18 C20 . . 104.23(9) ?
    C17 C18 C20 . . 112.73(9) ?
    O1 C18 C19 . . 108.78(9) ?
    C17 C18 C19 . . 110.42(10) ?
    C20 C18 C19 . . 111.22(9) ?
    C4 C9 C8 . . 119.13(9) ?
    C4 C9 C3 . . 134.69(9) ?
    C8 C9 C3 . . 106.16(9) ?
    C18 C20 H20A . . 109.5 ?
    C18 C20 H20B . . 109.5 ?
    H20A C20 H20B . . 109.5 ?
    C18 C20 H20C . . 109.5 ?
    H20A C20 H20C . . 109.5 ?
    H20B C20 H20C . . 109.5 ?
    O2 C10 C3 . . 123.81(10) ?
    O2 C10 H10 . . 118.1 ?
    C3 C10 H10 . . 118.1 ?
    C17 C16 C5 . . 120.01(10) ?
    C17 C16 H16 . . 120.0 ?
    C5 C16 H16 . . 120.0 ?
    C5 C4 C9 . . 119.30(9) ?
    C5 C4 H4 . . 120.4 ?
    C9 C4 H4 . . 120.4 ?
    C6 C7 C8 . . 116.37(9) ?
    C6 C7 H7 . . 121.8 ?
    C8 C7 H7 . . 121.8 ?
    C16 C17 C18 . . 119.55(10) ?
    C16 C17 H17 . . 120.2 ?
    C18 C17 H17 . . 120.2 ?
    C13 C15 H15A . . 109.5 ?
    C13 C15 H15B . . 109.5 ?
    H15A C15 H15B . . 109.5 ?
    C13 C15 H15C . . 109.5 ?
    H15A C15 H15C . . 109.5 ?
    H15B C15 H15C . . 109.5 ?
    C12 C13 C2 . . 110.23(9) ?
    C12 C13 C14 . . 112.54(10) ?
    C2 C13 C14 . . 108.39(9) ?
    C12 C13 C15 . . 106.33(9) ?
    C2 C13 C15 . . 110.68(9) ?
    C14 C13 C15 . . 108.66(9) ?
    C11 C12 C13 . . 126.12(12) ?
    C11 C12 H12 . . 116.9 ?
    C13 C12 H12 . . 116.9 ?
    C13 C14 H14A . . 109.5 ?
    C13 C14 H14B . . 109.5 ?
    H14A C14 H14B . . 109.5 ?
    C13 C14 H14C . . 109.5 ?
    H14A C14 H14C . . 109.5 ?
    H14B C14 H14C . . 109.5 ?
    C12 C11 H11A . . 120.0 ?
    C12 C11 H11B . . 120.0 ?
    H11A C11 H11B . . 120.0 ?

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_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    C8 N1 C2 C3 . . . . -0.54(12) ?
    C8 N1 C2 C13 . . . . 177.09(9) ?
    N1 C2 C3 C10 . . . . 175.22(10) ?
    C13 C2 C3 C10 . . . . -2.11(18) ?
    N1 C2 C3 C9 . . . . -0.62(12) ?
    C13 C2 C3 C9 . . . . -177.96(10) ?
    C18 O1 C6 C7 . . . . 147.84(9) ?
    C18 O1 C6 C5 . . . . -35.68(13) ?
    C4 C5 C6 O1 . . . . -179.24(9) ?
    C16 C5 C6 O1 . . . . 0.87(15) ?
    C4 C5 C6 C7 . . . . -2.92(16) ?
    C16 C5 C6 C7 . . . . 177.20(10) ?
    C2 N1 C8 C7 . . . . -176.27(10) ?
    C2 N1 C8 C9 . . . . 1.52(12) ?
    C6 O1 C18 C17 . . . . 50.88(12) ?
    C6 O1 C18 C20 . . . . 171.57(9) ?
    C6 O1 C18 C19 . . . . -69.70(11) ?
    N1 C8 C9 C4 . . . . 179.26(9) ?
    C7 C8 C9 C4 . . . . -2.78(16) ?
    N1 C8 C9 C3 . . . . -1.83(11) ?
    C7 C8 C9 C3 . . . . 176.13(10) ?
    C2 C3 C9 C4 . . . . -179.83(11) ?
    C10 C3 C9 C4 . . . . 4.29(19) ?
    C2 C3 C9 C8 . . . . 1.51(11) ?
    C10 C3 C9 C8 . . . . -174.37(10) ?
    C2 C3 C10 O2 . . . . -179.15(11) ?
    C9 C3 C10 O2 . . . . -4.06(18) ?
    C4 C5 C16 C17 . . . . -163.75(11) ?
    C6 C5 C16 C17 . . . . 16.13(16) ?
    C6 C5 C4 C9 . . . . -1.20(15) ?
    C16 C5 C4 C9 . . . . 178.68(10) ?
    C8 C9 C4 C5 . . . . 3.90(15) ?
    C3 C9 C4 C5 . . . . -174.63(11) ?
    O1 C6 C7 C8 . . . . -179.63(9) ?
    C5 C6 C7 C8 . . . . 4.00(16) ?
    N1 C8 C7 C6 . . . . 176.34(10) ?
    C9 C8 C7 C6 . . . . -1.15(16) ?
    C5 C16 C17 C18 . . . . 2.43(17) ?
    O1 C18 C17 C16 . . . . -34.72(14) ?
    C20 C18 C17 C16 . . . . -150.07(11) ?
    C19 C18 C17 C16 . . . . 84.86(13) ?
    N1 C2 C13 C12 . . . . 139.47(10) ?
    C3 C2 C13 C12 . . . . -43.49(15) ?
    N1 C2 C13 C14 . . . . -96.95(11) ?
    C3 C2 C13 C14 . . . . 80.09(13) ?
    N1 C2 C13 C15 . . . . 22.12(14) ?
    C3 C2 C13 C15 . . . . -160.84(11) ?
    C2 C13 C12 C11 . . . . 136.27(14) ?
    C14 C13 C12 C11 . . . . 15.14(18) ?
    C15 C13 C12 C11 . . . . -103.72(15) ?



