 
data_shelxl
 
_audit_creation_method            SHELXL-2013
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C20 H23 N O2' 
_chemical_formula_weight          309.39

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'
 
_space_group_crystal_system       monoclinic
_space_group_IT_number            14
_space_group_name_H-M_alt         'P 21/c'
_space_group_name_Hall            '-P 2ybc'
 
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
 
loop_
 _space_group_symop_operation_xyz
 'x, y, z'
 '-x, y+1/2, -z+1/2'
 '-x, -y, -z'
 'x, -y-1/2, z-1/2'
 
_cell_length_a                    7.63800(10)
_cell_length_b                    11.3062(2)
_cell_length_c                    20.7899(3)
_cell_angle_alpha                 90
_cell_angle_beta                  95.2350(10)
_cell_angle_gamma                 90
_cell_volume                      1787.86(5)
_cell_formula_units_Z             4
_cell_measurement_temperature     291(2)
_cell_measurement_reflns_used     4059
_cell_measurement_theta_min       5.7990
_cell_measurement_theta_max       73.5640
 
_exptl_crystal_description        block 
_exptl_crystal_colour             ? 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_method     ?              
_exptl_crystal_density_diffrn     1.149          
_exptl_crystal_F_000              664
_exptl_transmission_factor_min    ?                                             
_exptl_transmission_factor_max    ?                                             
_exptl_crystal_size_max           0.240
_exptl_crystal_size_mid           0.220
_exptl_crystal_size_min           0.210
_exptl_absorpt_coefficient_mu     0.580
_shelx_estimated_absorpt_T_min    0.873
_shelx_estimated_absorpt_T_max    0.888
_exptl_absorpt_correction_T_min   0.75844
_exptl_absorpt_correction_T_max   1.00000
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
 
_exptl_special_details
;
 ?
;
 
_diffrn_ambient_temperature       291(2)
_diffrn_radiation_wavelength      1.54184
_diffrn_radiation_type            CuK\a
_diffrn_source                    'micro-focus sealed X-ray tube' 
_diffrn_measurement_device_type   'SuperNova, Dual, Cu at zero, AtlasS2' 
_diffrn_measurement_method        'ω scans' 
_diffrn_detector_area_resol_mean  5.2169 
_diffrn_reflns_number             6975
_diffrn_reflns_av_unetI/netI      0.0173
_diffrn_reflns_av_R_equivalents   0.0153
_diffrn_reflns_limit_h_min        -9
_diffrn_reflns_limit_h_max        8
_diffrn_reflns_limit_k_min        -11
_diffrn_reflns_limit_k_max        13
_diffrn_reflns_limit_l_min        -25
_diffrn_reflns_limit_l_max        24
_diffrn_reflns_theta_min          4.271
_diffrn_reflns_theta_max          73.836
_diffrn_reflns_theta_full         67.684
_diffrn_measured_fraction_theta_max   0.975
_diffrn_measured_fraction_theta_full  1.000
_diffrn_reflns_Laue_measured_fraction_max    0.975
_diffrn_reflns_Laue_measured_fraction_full   1.000
_diffrn_reflns_point_group_measured_fraction_max   0.975
_diffrn_reflns_point_group_measured_fraction_full  1.000
_reflns_number_total              3523
_reflns_number_gt                 3088
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.000
_reflns_Friedel_fraction_max      .
_reflns_Friedel_fraction_full     .
 
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
 
_computing_data_collection        'CrysAlisPro (Rigaku OD, 2015)'
_computing_cell_refinement        'CrysAlisPro (Rigaku OD, 2015)'
_computing_data_reduction         'CrysAlisPro (Rigaku OD, 2015)'
_computing_structure_solution     'SHELXS-2013 (Sheldrick, 1997)'
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics     'Ortep-3 (L. J. Farrugia, 2001)'
_computing_publication_material   SHELXL-97
 
_refine_special_details
;
 ?
;
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0745P)²+0.2397P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      ?
_atom_sites_solution_secondary    ?
_atom_sites_solution_hydrogens    geom
_refine_ls_hydrogen_treatment     constr
_refine_ls_extinction_method      SHELXL
_refine_ls_extinction_coef        0.0039(5)
_refine_ls_extinction_expression
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_number_reflns          3523
_refine_ls_number_parameters      213
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0516
_refine_ls_R_factor_gt            0.0463
_refine_ls_wR_factor_ref          0.1384
_refine_ls_wR_factor_gt           0.1311
_refine_ls_goodness_of_fit_ref    1.030
_refine_ls_restrained_S_all       1.030
_refine_ls_shift/su_max           0.000
_refine_ls_shift/su_mean          0.000
 
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_site_symmetry_order  
 _atom_site_calc_flag
 _atom_site_refinement_flags_posn
 _atom_site_refinement_flags_adp
 _atom_site_refinement_flags_occupancy
 _atom_site_disorder_assembly
 _atom_site_disorder_group
O1 O 0.51159(17) 0.70156(10) 0.64610(5) 0.0740(4) Uani 1 1 d . . . . .
O2 O 0.08490(16) 0.29042(11) 0.49499(6) 0.0779(4) Uani 1 1 d . . . . .
N1 N 0.37878(16) 0.62303(10) 0.72945(5) 0.0541(3) Uani 1 1 d . . . . .
C14 C 0.39127(16) 0.57714(11) 0.84004(6) 0.0471(3) Uani 1 1 d . . . . .
C9 C 0.59536(16) 0.47017(11) 0.76535(6) 0.0456(3) Uani 1 1 d . . . . .
H9A H 0.5949 0.4548 0.7194 0.055 Uiso 1 1 calc R U . . .
H9B H 0.5649 0.3967 0.7857 0.055 Uiso 1 1 calc R U . . .
C8 C 0.45267(16) 0.55935(10) 0.77481(6) 0.0448(3) Uani 1 1 d . . . . .
C4 C 0.32533(17) 0.53725(11) 0.62109(6) 0.0487(3) Uani 1 1 d . . . . .
C7 C 0.41753(19) 0.62427(12) 0.66553(7) 0.0530(3) Uani 1 1 d . . . . .
C1 C 0.16587(19) 0.37480(13) 0.53344(7) 0.0576(3) Uani 1 1 d . . . . .
C10 C 0.78504(18) 0.50370(12) 0.79156(7) 0.0534(3) Uani 1 1 d . . . . .
C3 C 0.3350(2) 0.55020(13) 0.55528(7) 0.0564(3) Uani 1 1 d . . . . .
H3 H 0.3962 0.6141 0.5402 0.068 Uiso 1 1 calc R U . . .
C15 C 0.37132(18) 0.48419(13) 0.88222(7) 0.0552(3) Uani 1 1 d . . . . .
H15 H 0.3988 0.4075 0.8704 0.066 Uiso 1 1 calc R U . . .
C2 C 0.2558(2) 0.47048(14) 0.51153(7) 0.0603(4) Uani 1 1 d . . . . .
H2 H 0.2630 0.4812 0.4675 0.072 Uiso 1 1 calc R U . . .
C5 C 0.2325(2) 0.44095(14) 0.64237(7) 0.0585(4) Uani 1 1 d . . . . .
H5 H 0.2233 0.4308 0.6863 0.070 Uiso 1 1 calc R U . . .
C19 C 0.3503(2) 0.69084(13) 0.85919(7) 0.0649(4) Uani 1 1 d . . . . .
H19 H 0.3627 0.7543 0.8315 0.078 Uiso 1 1 calc R U . . .
C6 C 0.1544(2) 0.36092(15) 0.59925(8) 0.0654(4) Uani 1 1 d . . . . .
H6 H 0.0934 0.2969 0.6142 0.078 Uiso 1 1 calc R U . . .
C16 C 0.3105(2) 0.50539(17) 0.94193(8) 0.0703(4) Uani 1 1 d . . . . .
H16 H 0.2960 0.4426 0.9698 0.084 Uiso 1 1 calc R U . . .
C13 C 0.8055(2) 0.51049(18) 0.86523(8) 0.0751(5) Uani 1 1 d . . . . .
H13A H 0.7350 0.5742 0.8793 0.113 Uiso 1 1 calc R U . . .
H13B H 0.9266 0.5242 0.8799 0.113 Uiso 1 1 calc R U . . .
H13C H 0.7676 0.4373 0.8829 0.113 Uiso 1 1 calc R U . . .
C11 C 0.9050(2) 0.40472(18) 0.77095(10) 0.0797(5) Uani 1 1 d . . . . .
H11A H 0.8666 0.3304 0.7870 0.120 Uiso 1 1 calc R U . . .
H11B H 1.0237 0.4199 0.7883 0.120 Uiso 1 1 calc R U . . .
H11C H 0.8997 0.4019 0.7247 0.120 Uiso 1 1 calc R U . . .
C18 C 0.2916(3) 0.71008(17) 0.91902(8) 0.0838(6) Uani 1 1 d . . . . .
H18 H 0.2652 0.7865 0.9315 0.101 Uiso 1 1 calc R U . . .
C12 C 0.8379(3) 0.62149(18) 0.76336(10) 0.0846(6) Uani 1 1 d . . . . .
H12A H 0.8299 0.6160 0.7171 0.127 Uiso 1 1 calc R U . . .
H12B H 0.9566 0.6401 0.7793 0.127 Uiso 1 1 calc R U . . .
H12C H 0.7606 0.6826 0.7759 0.127 Uiso 1 1 calc R U . . .
C17 C 0.2716(3) 0.6176(2) 0.96021(8) 0.0819(6) Uani 1 1 d . . . . .
H17 H 0.2317 0.6312 1.0005 0.098 Uiso 1 1 calc R U . . .
C20 C 0.0924(3) 0.30018(19) 0.42705(9) 0.0839(5) Uani 1 1 d . . . . .
H20A H 0.0291 0.2357 0.4058 0.126 Uiso 1 1 calc R U . . .
H20B H 0.2128 0.2978 0.4173 0.126 Uiso 1 1 calc R U . . .
H20C H 0.0403 0.3737 0.4122 0.126 Uiso 1 1 calc R U . . .
 
 
_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_distance
 _geom_bond_site_symmetry_2
 _geom_bond_publ_flag
O1 C7 1.2231(17) . ?
O2 C1 1.3570(18) . ?
O2 C20 1.423(2) . ?
N1 C8 1.2765(16) . ?
N1 C7 1.3875(17) . ?
C14 C15 1.3861(19) . ?
C14 C19 1.3899(19) . ?
C14 C8 1.4883(16) . ?
C9 C8 1.5107(17) . ?
C9 C10 1.5477(18) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C4 C3 1.3845(18) . ?
C4 C5 1.3935(19) . ?
C4 C7 1.483(2) . ?
C1 C2 1.381(2) . ?
C1 C6 1.388(2) . ?
C10 C12 1.524(2) . ?
C10 C13 1.527(2) . ?
C10 C11 1.532(2) . ?
C3 C2 1.380(2) . ?
C3 H3 0.9300 . ?
C15 C16 1.385(2) . ?
C15 H15 0.9300 . ?
C2 H2 0.9300 . ?
C5 C6 1.371(2) . ?
C5 H5 0.9300 . ?
C19 C18 1.378(2) . ?
C19 H19 0.9300 . ?
C6 H6 0.9300 . ?
C16 C17 1.365(3) . ?
C16 H16 0.9300 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C18 C17 1.368(3) . ?
C18 H18 0.9300 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C17 H17 0.9300 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
 
loop_
 _geom_angle_atom_site_label_1
 _geom_angle_atom_site_label_2
 _geom_angle_atom_site_label_3
 _geom_angle
 _geom_angle_site_symmetry_1
 _geom_angle_site_symmetry_3
 _geom_angle_publ_flag
C1 O2 C20 118.21(14) . . ?
C8 N1 C7 126.50(11) . . ?
C15 C14 C19 118.65(12) . . ?
C15 C14 C8 122.41(11) . . ?
C19 C14 C8 118.93(12) . . ?
C8 C9 C10 116.99(10) . . ?
C8 C9 H9A 108.0 . . ?
C10 C9 H9A 108.0 . . ?
C8 C9 H9B 108.0 . . ?
C10 C9 H9B 108.0 . . ?
H9A C9 H9B 107.3 . . ?
N1 C8 C14 116.24(11) . . ?
N1 C8 C9 123.77(11) . . ?
C14 C8 C9 119.99(11) . . ?
C3 C4 C5 118.09(13) . . ?
C3 C4 C7 118.72(12) . . ?
C5 C4 C7 123.17(12) . . ?
O1 C7 N1 120.44(13) . . ?
O1 C7 C4 121.87(12) . . ?
N1 C7 C4 117.35(12) . . ?
O2 C1 C2 124.77(14) . . ?
O2 C1 C6 115.78(13) . . ?
C2 C1 C6 119.45(14) . . ?
C12 C10 C13 109.60(14) . . ?
C12 C10 C11 110.15(14) . . ?
C13 C10 C11 107.95(13) . . ?
C12 C10 C9 110.55(13) . . ?
C13 C10 C9 111.84(11) . . ?
C11 C10 C9 106.68(11) . . ?
C2 C3 C4 121.51(13) . . ?
C2 C3 H3 119.2 . . ?
C4 C3 H3 119.2 . . ?
C16 C15 C14 120.06(14) . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C3 C2 C1 119.69(13) . . ?
C3 C2 H2 120.2 . . ?
C1 C2 H2 120.2 . . ?
C6 C5 C4 120.76(13) . . ?
C6 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
C18 C19 C14 120.33(15) . . ?
C18 C19 H19 119.8 . . ?
C14 C19 H19 119.8 . . ?
C5 C6 C1 120.49(13) . . ?
C5 C6 H6 119.8 . . ?
C1 C6 H6 119.8 . . ?
C17 C16 C15 120.63(16) . . ?
C17 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?
C10 C13 H13A 109.5 . . ?
C10 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C10 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C17 C18 C19 120.57(16) . . ?
C17 C18 H18 119.7 . . ?
C19 C18 H18 119.7 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C16 C17 C18 119.75(14) . . ?
C16 C17 H17 120.1 . . ?
C18 C17 H17 120.1 . . ?
O2 C20 H20A 109.5 . . ?
O2 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O2 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
 
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
 _geom_torsion_site_symmetry_1
 _geom_torsion_site_symmetry_2
 _geom_torsion_site_symmetry_3
 _geom_torsion_site_symmetry_4
 _geom_torsion_publ_flag
C7 N1 C8 C14 178.07(13) . . . . ?
C7 N1 C8 C9 -1.7(2) . . . . ?
C15 C14 C8 N1 141.36(14) . . . . ?
C19 C14 C8 N1 -37.86(19) . . . . ?
C15 C14 C8 C9 -38.86(18) . . . . ?
C19 C14 C8 C9 141.92(13) . . . . ?
C10 C9 C8 N1 106.17(15) . . . . ?
C10 C9 C8 C14 -73.59(15) . . . . ?
C8 N1 C7 O1 -99.32(17) . . . . ?
C8 N1 C7 C4 87.26(18) . . . . ?
C3 C4 C7 O1 -5.4(2) . . . . ?
C5 C4 C7 O1 173.04(14) . . . . ?
C3 C4 C7 N1 167.97(12) . . . . ?
C5 C4 C7 N1 -13.6(2) . . . . ?
C20 O2 C1 C2 0.0(2) . . . . ?
C20 O2 C1 C6 180.00(15) . . . . ?
C8 C9 C10 C12 -55.49(16) . . . . ?
C8 C9 C10 C13 66.93(16) . . . . ?
C8 C9 C10 C11 -175.25(13) . . . . ?
C5 C4 C3 C2 -0.1(2) . . . . ?
C7 C4 C3 C2 178.33(13) . . . . ?
C19 C14 C15 C16 0.5(2) . . . . ?
C8 C14 C15 C16 -178.77(13) . . . . ?
C4 C3 C2 C1 -0.5(2) . . . . ?
O2 C1 C2 C3 -179.25(15) . . . . ?
C6 C1 C2 C3 0.8(2) . . . . ?
C3 C4 C5 C6 0.6(2) . . . . ?
C7 C4 C5 C6 -177.82(14) . . . . ?
C15 C14 C19 C18 0.1(2) . . . . ?
C8 C14 C19 C18 179.39(15) . . . . ?
C4 C5 C6 C1 -0.3(2) . . . . ?
O2 C1 C6 C5 179.67(15) . . . . ?
C2 C1 C6 C5 -0.4(2) . . . . ?
C14 C15 C16 C17 -0.8(3) . . . . ?
C14 C19 C18 C17 -0.4(3) . . . . ?
C15 C16 C17 C18 0.5(3) . . . . ?
C19 C18 C17 C16 0.1(3) . . . . ?
 
_refine_diff_density_max    0.192
_refine_diff_density_min   -0.141
_refine_diff_density_rms    0.032

_shelxl_version_number 2013-4



