 
data_mo_d8v19724_0m 
  
_audit_creation_method            SHELXL-2013 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          ? 
_chemical_formula_sum 
 'C21 H21 N O' 
_chemical_formula_weight          303.39 
  
loop_ 
 _atom_type_symbol 
 _atom_type_description 
 _atom_type_scat_dispersion_real 
 _atom_type_scat_dispersion_imag 
 _atom_type_scat_source 
 'C'  'C'   0.0033   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' 
  
_space_group_crystal_system       tetragonal 
_space_group_IT_number            92 
_space_group_name_H-M_alt         'P 41 21 2' 
_space_group_name_Hall            'P 4abw 2nw' 
  
_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' 
 '-y+1/2, x+1/2, z+1/4' 
 '-x, -y, z+1/2' 
 'y+1/2, -x+1/2, z+3/4' 
 'x+1/2, -y+1/2, -z+3/4' 
 'y, x, -z' 
 '-x+1/2, y+1/2, -z+1/4' 
 '-y, -x, -z+1/2' 
  
_cell_length_a                    7.4865(2) 
_cell_length_b                    7.4865(2) 
_cell_length_c                    59.2740(19) 
_cell_angle_alpha                 90 
_cell_angle_beta                  90 
_cell_angle_gamma                 90 
_cell_volume                      3322.2(2) 
_cell_formula_units_Z             8 
_cell_measurement_temperature     293(2) 
_cell_measurement_reflns_used     9922 
_cell_measurement_theta_min       4.810 
_cell_measurement_theta_max       48.683 
  
_exptl_crystal_description        prismatic 
_exptl_crystal_colour             colorless 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_method     ? 
_exptl_crystal_density_diffrn     1.213 
_exptl_crystal_F_000              1296 
_exptl_transmission_factor_min    ? 
_exptl_transmission_factor_max    ? 
_exptl_crystal_size_max           0.190 
_exptl_crystal_size_mid           0.150 
_exptl_crystal_size_min           0.100 
_exptl_absorpt_coefficient_mu     0.074 
_shelx_estimated_absorpt_T_min    0.986 
_shelx_estimated_absorpt_T_max    0.993 
_exptl_absorpt_correction_type    multi-scan 
_exptl_absorpt_correction_T_min   0.5602 
_exptl_absorpt_correction_T_max   0.7456 
_exptl_absorpt_process_details    sadabs 
  
_exptl_special_details 
; 
 ? 
; 
  
_diffrn_ambient_temperature       293(2) 
_diffrn_radiation_wavelength      0.71073 
_diffrn_radiation_type            MoK\a 
_diffrn_source                    ? 
_diffrn_measurement_device_type   'Bruker APEX-II CCD' 
_diffrn_measurement_method        'φ and ω scans' 
_diffrn_detector_area_resol_mean  ? 
_diffrn_reflns_number             29434 
_diffrn_reflns_av_unetI/netI      0.0393 
_diffrn_reflns_av_R_equivalents   0.0772 
_diffrn_reflns_limit_h_min        -9 
_diffrn_reflns_limit_h_max        9 
_diffrn_reflns_limit_k_min        -9 
_diffrn_reflns_limit_k_max        9 
_diffrn_reflns_limit_l_min        -72 
_diffrn_reflns_limit_l_max        73 
_diffrn_reflns_theta_min          2.806 
_diffrn_reflns_theta_max          25.996 
_diffrn_reflns_theta_full         25.242 
_diffrn_measured_fraction_theta_max   0.995 
_diffrn_measured_fraction_theta_full  0.994 
_diffrn_reflns_Laue_measured_fraction_max    0.995 
_diffrn_reflns_Laue_measured_fraction_full   0.994 
_diffrn_reflns_point_group_measured_fraction_max   0.997 
_diffrn_reflns_point_group_measured_fraction_full  0.996 
_reflns_number_total              3253 
_reflns_number_gt                 2766 
_reflns_threshold_expression      'I > 2σ(I)' 
_reflns_Friedel_coverage          0.577 
_reflns_Friedel_fraction_max      1.000 
_reflns_Friedel_fraction_full     1.000 
  
_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        'Bruker APEX2' 
_computing_cell_refinement        'Bruker SAINT' 
_computing_data_reduction         'Bruker SAINT' 
_computing_structure_solution     'SHELXS-97 (Sheldrick 2008)' 
_computing_structure_refinement   'SHELXL-2013 (Sheldrick, 2013)' 
_computing_molecular_graphics     'Bruker SHELXTL' 
_computing_publication_material   'Bruker SHELXTL' 
  
_refine_special_details 
; 
 Refined as a 2-component inversion twin. 
; 
_refine_ls_structure_factor_coef  Fsqd 
_refine_ls_matrix_type            full 
_refine_ls_weighting_scheme       calc 
_refine_ls_weighting_details 
'w=1/[σ²(Fo²)+(0.0614P)²+2.2655P] 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        0.031(5) 
_refine_ls_extinction_expression 
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^' 
_refine_ls_abs_structure_details 
; 
 Refined as an inversion twin. 
; 
_refine_ls_abs_structure_Flack    0(6) 
_chemical_absolute_configuration  unk 
_refine_ls_number_reflns          3253 
_refine_ls_number_parameters      212 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.0786 
_refine_ls_R_factor_gt            0.0684 
_refine_ls_wR_factor_ref          0.1823 
_refine_ls_wR_factor_gt           0.1750 
_refine_ls_goodness_of_fit_ref    1.098 
_refine_ls_restrained_S_all       1.098 
_refine_ls_shift/su_max           0.005 
_refine_ls_shift/su_mean          0.002 
  
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 -0.1361(6) 0.2394(6) 0.98747(5) 0.0916(13) Uani 1 1 d . . . . . 
N1 N 0.0709(6) 0.4163(5) 0.97285(6) 0.0699(12) Uani 1 1 d . . . . . 
C1 C -0.0231(7) 0.2629(6) 0.97307(6) 0.0612(12) Uani 1 1 d . . . . . 
C2 C 0.0088(6) 0.1261(5) 0.95427(6) 0.0491(9) Uani 1 1 d . . . . . 
C3 C -0.1356(7) -0.0205(6) 0.95615(7) 0.0628(12) Uani 1 1 d . . . . . 
H3A H -0.0934 -0.1315 0.9496 0.075 Uiso 1 1 calc R U . . . 
H3B H -0.1665 -0.0416 0.9718 0.075 Uiso 1 1 calc R U . . . 
C4 C -0.2956(7) 0.0497(7) 0.94322(8) 0.0723(14) Uani 1 1 d . . . . . 
H4A H -0.3630 0.1349 0.9521 0.087 Uiso 1 1 calc R U . . . 
H4B H -0.3739 -0.0467 0.9386 0.087 Uiso 1 1 calc R U . . . 
C5 C -0.2074(6) 0.1392(7) 0.92299(7) 0.0637(12) Uani 1 1 d . . . . . 
H5A H -0.1817 0.0525 0.9113 0.076 Uiso 1 1 calc R U . . . 
H5B H -0.2841 0.2315 0.9168 0.076 Uiso 1 1 calc R U . . . 
C6 C -0.0378(5) 0.2186(5) 0.93210(6) 0.0466(9) Uani 1 1 d . . . . . 
C7 C 0.0518(5) 0.3585(5) 0.92349(6) 0.0471(9) Uani 1 1 d . . . . . 
C8 C 0.2081(6) 0.4364(6) 0.93478(7) 0.0525(10) Uani 1 1 d . . . . . 
C9 C 0.3539(6) 0.4901(6) 0.92224(8) 0.0630(12) Uani 1 1 d . . . . . 
H9 H 0.3483 0.4797 0.9066 0.076 Uiso 1 1 calc R U . . . 
C10 C 0.5069(7) 0.5583(8) 0.93173(12) 0.0883(18) Uani 1 1 d . . . . . 
H10 H 0.6039 0.5908 0.9228 0.106 Uiso 1 1 calc R U . . . 
C11 C 0.5119(9) 0.5771(9) 0.95517(13) 0.109(3) Uani 1 1 d . . . . . 
H11 H 0.6137 0.6229 0.9621 0.131 Uiso 1 1 calc R U . . . 
C12 C 0.3703(9) 0.5295(8) 0.96785(9) 0.0887(19) Uani 1 1 d . . . . . 
H12 H 0.3765 0.5452 0.9834 0.106 Uiso 1 1 calc R U . . . 
C13 C 0.2162(7) 0.4582(6) 0.95868(7) 0.0635(13) Uani 1 1 d . . . . . 
C14 C 0.0276(11) 0.5431(8) 0.99147(8) 0.103(2) Uani 1 1 d . . . . . 
H14A H 0.1070 0.5226 1.0039 0.155 Uiso 1 1 calc R U . . . 
H14B H -0.0935 0.5248 0.9963 0.155 Uiso 1 1 calc R U . . . 
H14C H 0.0416 0.6635 0.9862 0.155 Uiso 1 1 calc R U . . . 
C15 C 0.1949(7) 0.0428(7) 0.95541(8) 0.0670(13) Uani 1 1 d . . . . . 
H15A H 0.2053 -0.0484 0.9441 0.101 Uiso 1 1 calc R U . . . 
H15B H 0.2130 -0.0089 0.9701 0.101 Uiso 1 1 calc R U . . . 
H15C H 0.2833 0.1333 0.9528 0.101 Uiso 1 1 calc R U . . . 
C16 C -0.0062(5) 0.4433(5) 0.90191(6) 0.0462(9) Uani 1 1 d . . . . . 
C17 C -0.0283(7) 0.3443(6) 0.88216(7) 0.0587(11) Uani 1 1 d . . . . . 
H17 H -0.0008 0.2232 0.8821 0.070 Uiso 1 1 calc R U . . . 
C18 C -0.0907(7) 0.4253(7) 0.86276(7) 0.0638(12) Uani 1 1 d . . . . . 
H18 H -0.1042 0.3577 0.8497 0.077 Uiso 1 1 calc R U . . . 
C19 C -0.1326(8) 0.6014(7) 0.86237(7) 0.0695(14) Uani 1 1 d . . . . . 
H19 H -0.1770 0.6541 0.8493 0.083 Uiso 1 1 calc R U . . . 
C20 C -0.1081(9) 0.7013(7) 0.88170(8) 0.0799(16) Uani 1 1 d . . . . . 
H20 H -0.1342 0.8227 0.8816 0.096 Uiso 1 1 calc R U . . . 
C21 C -0.0456(7) 0.6224(6) 0.90099(7) 0.0630(12) Uani 1 1 d . . . . . 
H21 H -0.0293 0.6920 0.9138 0.076 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 C1 1.214(5) . ? 
N1 C1 1.347(6) . ? 
N1 C13 1.410(6) . ? 
N1 C14 1.491(6) . ? 
C1 C2 1.532(6) . ? 
C2 C6 1.526(5) . ? 
C2 C15 1.528(6) . ? 
C2 C3 1.544(6) . ? 
C3 C4 1.516(7) . ? 
C3 H3A 0.9700 . ? 
C3 H3B 0.9700 . ? 
C4 C5 1.524(6) . ? 
C4 H4A 0.9700 . ? 
C4 H4B 0.9700 . ? 
C5 C6 1.503(6) . ? 
C5 H5A 0.9700 . ? 
C5 H5B 0.9700 . ? 
C6 C7 1.344(6) . ? 
C7 C8 1.469(6) . ? 
C7 C16 1.493(5) . ? 
C8 C9 1.380(6) . ? 
C8 C13 1.427(6) . ? 
C9 C10 1.374(7) . ? 
C9 H9 0.9300 . ? 
C10 C11 1.397(9) . ? 
C10 H10 0.9300 . ? 
C11 C12 1.348(9) . ? 
C11 H11 0.9300 . ? 
C12 C13 1.382(7) . ? 
C12 H12 0.9300 . ? 
C14 H14A 0.9600 . ? 
C14 H14B 0.9600 . ? 
C14 H14C 0.9600 . ? 
C15 H15A 0.9600 . ? 
C15 H15B 0.9600 . ? 
C15 H15C 0.9600 . ? 
C16 C21 1.374(6) . ? 
C16 C17 1.395(5) . ? 
C17 C18 1.381(6) . ? 
C17 H17 0.9300 . ? 
C18 C19 1.356(7) . ? 
C18 H18 0.9300 . ? 
C19 C20 1.380(7) . ? 
C19 H19 0.9300 . ? 
C20 C21 1.369(6) . ? 
C20 H20 0.9300 . ? 
C21 H21 0.9300 . ? 
  
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 N1 C13 126.8(4) . . ? 
C1 N1 C14 115.0(4) . . ? 
C13 N1 C14 117.8(4) . . ? 
O1 C1 N1 119.6(4) . . ? 
O1 C1 C2 121.5(4) . . ? 
N1 C1 C2 118.8(4) . . ? 
C6 C2 C15 115.6(3) . . ? 
C6 C2 C1 106.7(3) . . ? 
C15 C2 C1 112.5(4) . . ? 
C6 C2 C3 103.0(3) . . ? 
C15 C2 C3 110.2(4) . . ? 
C1 C2 C3 108.3(3) . . ? 
C4 C3 C2 105.7(4) . . ? 
C4 C3 H3A 110.6 . . ? 
C2 C3 H3A 110.6 . . ? 
C4 C3 H3B 110.6 . . ? 
C2 C3 H3B 110.6 . . ? 
H3A C3 H3B 108.7 . . ? 
C3 C4 C5 102.0(4) . . ? 
C3 C4 H4A 111.4 . . ? 
C5 C4 H4A 111.4 . . ? 
C3 C4 H4B 111.4 . . ? 
C5 C4 H4B 111.4 . . ? 
H4A C4 H4B 109.2 . . ? 
C6 C5 C4 104.9(4) . . ? 
C6 C5 H5A 110.8 . . ? 
C4 C5 H5A 110.8 . . ? 
C6 C5 H5B 110.8 . . ? 
C4 C5 H5B 110.8 . . ? 
H5A C5 H5B 108.8 . . ? 
C7 C6 C5 126.4(4) . . ? 
C7 C6 C2 124.5(4) . . ? 
C5 C6 C2 108.8(3) . . ? 
C6 C7 C8 122.3(3) . . ? 
C6 C7 C16 120.8(4) . . ? 
C8 C7 C16 117.0(4) . . ? 
C9 C8 C13 117.9(4) . . ? 
C9 C8 C7 120.0(4) . . ? 
C13 C8 C7 122.1(4) . . ? 
C10 C9 C8 123.1(5) . . ? 
C10 C9 H9 118.4 . . ? 
C8 C9 H9 118.4 . . ? 
C9 C10 C11 117.8(5) . . ? 
C9 C10 H10 121.1 . . ? 
C11 C10 H10 121.1 . . ? 
C12 C11 C10 120.4(5) . . ? 
C12 C11 H11 119.8 . . ? 
C10 C11 H11 119.8 . . ? 
C11 C12 C13 122.6(5) . . ? 
C11 C12 H12 118.7 . . ? 
C13 C12 H12 118.7 . . ? 
C12 C13 N1 119.7(4) . . ? 
C12 C13 C8 118.0(5) . . ? 
N1 C13 C8 122.2(4) . . ? 
N1 C14 H14A 109.5 . . ? 
N1 C14 H14B 109.5 . . ? 
H14A C14 H14B 109.5 . . ? 
N1 C14 H14C 109.5 . . ? 
H14A C14 H14C 109.5 . . ? 
H14B C14 H14C 109.5 . . ? 
C2 C15 H15A 109.5 . . ? 
C2 C15 H15B 109.5 . . ? 
H15A C15 H15B 109.5 . . ? 
C2 C15 H15C 109.5 . . ? 
H15A C15 H15C 109.5 . . ? 
H15B C15 H15C 109.5 . . ? 
C21 C16 C17 117.4(4) . . ? 
C21 C16 C7 120.8(4) . . ? 
C17 C16 C7 121.9(4) . . ? 
C18 C17 C16 120.4(4) . . ? 
C18 C17 H17 119.8 . . ? 
C16 C17 H17 119.8 . . ? 
C19 C18 C17 121.3(4) . . ? 
C19 C18 H18 119.4 . . ? 
C17 C18 H18 119.4 . . ? 
C18 C19 C20 118.8(4) . . ? 
C18 C19 H19 120.6 . . ? 
C20 C19 H19 120.6 . . ? 
C21 C20 C19 120.3(5) . . ? 
C21 C20 H20 119.8 . . ? 
C19 C20 H20 119.8 . . ? 
C20 C21 C16 121.8(4) . . ? 
C20 C21 H21 119.1 . . ? 
C16 C21 H21 119.1 . . ? 
  
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 
C13 N1 C1 O1 174.0(5) . . . . ? 
C14 N1 C1 O1 1.8(7) . . . . ? 
C13 N1 C1 C2 -9.2(7) . . . . ? 
C14 N1 C1 C2 178.6(5) . . . . ? 
O1 C1 C2 C6 116.3(5) . . . . ? 
N1 C1 C2 C6 -60.4(5) . . . . ? 
O1 C1 C2 C15 -116.0(5) . . . . ? 
N1 C1 C2 C15 67.3(5) . . . . ? 
O1 C1 C2 C3 6.1(6) . . . . ? 
N1 C1 C2 C3 -170.7(4) . . . . ? 
C6 C2 C3 C4 -27.3(5) . . . . ? 
C15 C2 C3 C4 -151.1(4) . . . . ? 
C1 C2 C3 C4 85.5(4) . . . . ? 
C2 C3 C4 C5 39.3(5) . . . . ? 
C3 C4 C5 C6 -35.9(5) . . . . ? 
C4 C5 C6 C7 -155.0(4) . . . . ? 
C4 C5 C6 C2 19.6(5) . . . . ? 
C15 C2 C6 C7 -60.6(5) . . . . ? 
C1 C2 C6 C7 65.3(5) . . . . ? 
C3 C2 C6 C7 179.2(4) . . . . ? 
C15 C2 C6 C5 124.7(4) . . . . ? 
C1 C2 C6 C5 -109.4(4) . . . . ? 
C3 C2 C6 C5 4.5(4) . . . . ? 
C5 C6 C7 C8 174.4(4) . . . . ? 
C2 C6 C7 C8 0.6(6) . . . . ? 
C5 C6 C7 C16 -4.7(6) . . . . ? 
C2 C6 C7 C16 -178.5(4) . . . . ? 
C6 C7 C8 C9 139.7(4) . . . . ? 
C16 C7 C8 C9 -41.0(6) . . . . ? 
C6 C7 C8 C13 -39.8(6) . . . . ? 
C16 C7 C8 C13 139.4(4) . . . . ? 
C13 C8 C9 C10 1.9(7) . . . . ? 
C7 C8 C9 C10 -177.7(5) . . . . ? 
C8 C9 C10 C11 -1.5(8) . . . . ? 
C9 C10 C11 C12 0.0(10) . . . . ? 
C10 C11 C12 C13 1.0(11) . . . . ? 
C11 C12 C13 N1 -178.1(6) . . . . ? 
C11 C12 C13 C8 -0.6(9) . . . . ? 
C1 N1 C13 C12 -131.9(6) . . . . ? 
C14 N1 C13 C12 40.2(8) . . . . ? 
C1 N1 C13 C8 50.7(7) . . . . ? 
C14 N1 C13 C8 -137.2(5) . . . . ? 
C9 C8 C13 C12 -0.8(7) . . . . ? 
C7 C8 C13 C12 178.7(5) . . . . ? 
C9 C8 C13 N1 176.6(4) . . . . ? 
C7 C8 C13 N1 -3.9(7) . . . . ? 
C6 C7 C16 C21 123.4(5) . . . . ? 
C8 C7 C16 C21 -55.8(6) . . . . ? 
C6 C7 C16 C17 -54.5(6) . . . . ? 
C8 C7 C16 C17 126.3(4) . . . . ? 
C21 C16 C17 C18 -1.2(7) . . . . ? 
C7 C16 C17 C18 176.8(4) . . . . ? 
C16 C17 C18 C19 -0.3(8) . . . . ? 
C17 C18 C19 C20 1.5(8) . . . . ? 
C18 C19 C20 C21 -1.2(9) . . . . ? 
C19 C20 C21 C16 -0.3(9) . . . . ? 
C17 C16 C21 C20 1.5(8) . . . . ? 
C7 C16 C21 C20 -176.5(5) . . . . ? 
  
_refine_diff_density_max    0.219 
_refine_diff_density_min   -0.200 
_refine_diff_density_rms    0.045 
  
_shelxl_version_number 2013-4 
  
  
  
