 
data_cu_har1703s_a 
  
_audit_creation_method            SHELXL-2014/6 
_chemical_name_systematic         ? 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          'C13 H19 N O' 
_chemical_formula_sum 
 'C13 H19 N O' 
_chemical_formula_weight          205.29 
  
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/n' 
_space_group_name_Hall            '-P 2yn' 
  
_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+1/2, y+1/2, -z+1/2' 
 '-x, -y, -z' 
 'x-1/2, -y-1/2, z-1/2' 
  
_cell_length_a                    9.4220(3) 
_cell_length_b                    9.3471(3) 
_cell_length_c                    12.8767(5) 
_cell_angle_alpha                 90 
_cell_angle_beta                  99.966(2) 
_cell_angle_gamma                 90 
_cell_volume                      1116.92(7) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     100(2) 
_cell_measurement_reflns_used     4015 
_cell_measurement_theta_min       5.40 
_cell_measurement_theta_max       69.69 
  
_exptl_crystal_description        block 
_exptl_crystal_colour             yellow 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_method     ? 
_exptl_crystal_density_diffrn     1.221 
_exptl_crystal_F_000              448 
_exptl_transmission_factor_min    ? 
_exptl_transmission_factor_max    ? 
_exptl_crystal_size_max           .4 
_exptl_crystal_size_mid           .3 
_exptl_crystal_size_min           .1 
_exptl_absorpt_coefficient_mu     0.594 
_shelx_estimated_absorpt_T_min    ? 
_shelx_estimated_absorpt_T_max    ? 
_exptl_absorpt_correction_type    'multi-scan' 
_exptl_absorpt_correction_T_min   0.68 
_exptl_absorpt_correction_T_max   0.75 
_exptl_absorpt_process_details    'SADABS V2014/2 (Bruker AXS Inc.)' 
_exptl_absorpt_special_details    ? 
_diffrn_ambient_temperature       100(2) 
_diffrn_radiation_wavelength      1.54178 
_diffrn_radiation_type            CuK\a 
_diffrn_source                    'I\mS micro--focus source' 
_diffrn_measurement_device_type   'Bruker APEX-II CCD' 
_diffrn_measurement_method        'φ and ω scans' 
_diffrn_detector_area_resol_mean  8.3333 
_diffrn_reflns_number             8386 
_diffrn_reflns_av_unetI/netI      0.0205 
_diffrn_reflns_av_R_equivalents   0.0213 
_diffrn_reflns_limit_h_min        -11 
_diffrn_reflns_limit_h_max        11 
_diffrn_reflns_limit_k_min        -11 
_diffrn_reflns_limit_k_max        11 
_diffrn_reflns_limit_l_min        -15 
_diffrn_reflns_limit_l_max        12 
_diffrn_reflns_theta_min          5.397 
_diffrn_reflns_theta_max          69.880 
_diffrn_reflns_theta_full         67.679 
_diffrn_measured_fraction_theta_max   0.975 
_diffrn_measured_fraction_theta_full  0.992 
_diffrn_reflns_Laue_measured_fraction_max    0.975 
_diffrn_reflns_Laue_measured_fraction_full   0.992 
_diffrn_reflns_point_group_measured_fraction_max   0.975 
_diffrn_reflns_point_group_measured_fraction_full  0.992 
_reflns_number_total              2062 
_reflns_number_gt                 1878 
_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        'Bruker APEX2' 
_computing_cell_refinement        'Bruker SAINT' 
_computing_data_reduction         'Bruker SAINT' 
_computing_structure_solution     'SHELXS-97 (Sheldrick 2008)' 
_computing_structure_refinement 'SHELXL-2014/6 (Sheldrick, 2014)' 
_computing_molecular_graphics     'Bruker SHELXTL' 
_computing_publication_material   'Bruker SHELXTL' 
_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)+(0.0319P)²+0.6000P] where P=(Fo²+2Fc²)/3' 
_atom_sites_solution_primary      ? 
_atom_sites_solution_secondary    ? 
_atom_sites_solution_hydrogens    mixed 
_refine_ls_hydrogen_treatment     mixed 
_refine_ls_extinction_method      none 
_refine_ls_extinction_coef        . 
_refine_ls_number_reflns          2062 
_refine_ls_number_parameters      145 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.0420 
_refine_ls_R_factor_gt            0.0389 
_refine_ls_wR_factor_ref          0.0934 
_refine_ls_wR_factor_gt           0.0921 
_refine_ls_goodness_of_fit_ref    1.098 
_refine_ls_restrained_S_all       1.098 
_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 0.57015(11) 0.25424(11) 0.83472(8) 0.0317(3) Uani 1 1 d . . . . . 
N1 N 0.27027(13) 0.22418(12) 0.52366(9) 0.0216(3) Uani 1 1 d . . . . . 
H1N H 0.2020(18) 0.2497(17) 0.4702(14) 0.026 Uiso 1 1 d . U . . . 
C1 C 0.28947(14) 0.32077(15) 0.60339(10) 0.0200(3) Uani 1 1 d . . . . . 
C2 C 0.36475(15) 0.11089(15) 0.54543(11) 0.0225(3) Uani 1 1 d . . . . . 
H2 H 0.3643(17) 0.0311(18) 0.4937(13) 0.027 Uiso 1 1 d . U . . . 
C3 C 0.44548(14) 0.13437(14) 0.64106(11) 0.0199(3) Uani 1 1 d . . . . . 
H3 H 0.5172(17) 0.0801(17) 0.6840(13) 0.024 Uiso 1 1 d . U . . . 
C4 C 0.40111(14) 0.26753(14) 0.67997(10) 0.0195(3) Uani 1 1 d . . . . . 
C5 C 0.46943(15) 0.32251(15) 0.78233(11) 0.0221(3) Uani 1 1 d . . . . . 
C6 C 0.41903(14) 0.45795(15) 0.82868(10) 0.0218(3) Uani 1 1 d . . . . . 
H6A H 0.3679 0.4326 0.8853 0.026 Uiso 1 1 calc R U . . . 
H6B H 0.3516 0.5067 0.7748 0.026 Uiso 1 1 calc R U . . . 
C7 C 0.54178(15) 0.56113(15) 0.87182(11) 0.0234(3) Uani 1 1 d . . . . . 
H7A H 0.5016 0.6398 0.9063 0.028 Uiso 1 1 calc R U . . . 
H7B H 0.6090 0.5112 0.9252 0.028 Uiso 1 1 calc R U . . . 
C8 C 0.62622(15) 0.62348(16) 0.79104(12) 0.0266(3) Uani 1 1 d . . . . . 
H8A H 0.6388 0.5489 0.7410 0.032 Uiso 1 1 calc R U . . . 
H8B H 0.7213 0.6505 0.8275 0.032 Uiso 1 1 calc R U . . . 
C9 C 0.55762(16) 0.75371(16) 0.72938(12) 0.0263(3) Uani 1 1 d . . . . . 
H9A H 0.5488 0.8293 0.7795 0.032 Uiso 1 1 calc R U . . . 
H9B H 0.6234 0.7874 0.6845 0.032 Uiso 1 1 calc R U . . . 
C10 C 0.40998(15) 0.73125(15) 0.66069(11) 0.0237(3) Uani 1 1 d . . . . . 
H10A H 0.3751 0.8225 0.6307 0.028 Uiso 1 1 calc R U . . . 
H10B H 0.3432 0.6985 0.7051 0.028 Uiso 1 1 calc R U . . . 
C11 C 0.40969(15) 0.62390(15) 0.57104(11) 0.0241(3) Uani 1 1 d . . . . . 
H11A H 0.4530 0.6687 0.5162 0.029 Uiso 1 1 calc R U . . . 
H11B H 0.4695 0.5429 0.5977 0.029 Uiso 1 1 calc R U . . . 
C12 C 0.26039(16) 0.56893(16) 0.52230(11) 0.0267(3) Uani 1 1 d . . . . . 
H12A H 0.2652 0.5287 0.4536 0.032 Uiso 1 1 calc R U . . . 
H12B H 0.1943 0.6493 0.5117 0.032 Uiso 1 1 calc R U . . . 
C13 C 0.19883(14) 0.45466(15) 0.58890(11) 0.0225(3) Uani 1 1 d . . . . . 
H13A H 0.1928 0.4945 0.6576 0.027 Uiso 1 1 calc R U . . . 
H13B H 0.1020 0.4300 0.5547 0.027 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 C5 1.2415(17) . ? 
N1 C1 1.3556(18) . ? 
N1 C2 1.3806(18) . ? 
N1 H1N 0.890(18) . ? 
C1 C4 1.4027(19) . ? 
C1 C13 1.5084(19) . ? 
C2 C3 1.349(2) . ? 
C2 H2 0.999(17) . ? 
C3 C4 1.4309(19) . ? 
C3 H3 0.944(16) . ? 
C4 C5 1.4567(19) . ? 
C5 C6 1.5107(19) . ? 
C6 C7 1.5343(19) . ? 
C6 H6A 0.9700 . ? 
C6 H6B 0.9700 . ? 
C7 C8 1.530(2) . ? 
C7 H7A 0.9700 . ? 
C7 H7B 0.9700 . ? 
C8 C9 1.534(2) . ? 
C8 H8A 0.9700 . ? 
C8 H8B 0.9700 . ? 
C9 C10 1.528(2) . ? 
C9 H9A 0.9700 . ? 
C9 H9B 0.9700 . ? 
C10 C11 1.5292(19) . ? 
C10 H10A 0.9700 . ? 
C10 H10B 0.9700 . ? 
C11 C12 1.527(2) . ? 
C11 H11A 0.9700 . ? 
C11 H11B 0.9700 . ? 
C12 C13 1.5443(19) . ? 
C12 H12A 0.9700 . ? 
C12 H12B 0.9700 . ? 
C13 H13A 0.9700 . ? 
C13 H13B 0.9700 . ? 
  
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 C2 111.12(12) . . ? 
C1 N1 H1N 113.1(11) . . ? 
C2 N1 H1N 135.8(11) . . ? 
N1 C1 C4 106.36(12) . . ? 
N1 C1 C13 117.41(12) . . ? 
C4 C1 C13 136.14(12) . . ? 
C3 C2 N1 107.61(12) . . ? 
C3 C2 H2 131.8(9) . . ? 
N1 C2 H2 120.6(9) . . ? 
C2 C3 C4 107.97(12) . . ? 
C2 C3 H3 133.0(10) . . ? 
C4 C3 H3 119.0(10) . . ? 
C1 C4 C3 106.94(12) . . ? 
C1 C4 C5 132.15(13) . . ? 
C3 C4 C5 120.90(12) . . ? 
O1 C5 C4 119.13(13) . . ? 
O1 C5 C6 118.62(12) . . ? 
C4 C5 C6 122.22(12) . . ? 
C5 C6 C7 113.64(11) . . ? 
C5 C6 H6A 108.8 . . ? 
C7 C6 H6A 108.8 . . ? 
C5 C6 H6B 108.8 . . ? 
C7 C6 H6B 108.8 . . ? 
H6A C6 H6B 107.7 . . ? 
C8 C7 C6 116.19(11) . . ? 
C8 C7 H7A 108.2 . . ? 
C6 C7 H7A 108.2 . . ? 
C8 C7 H7B 108.2 . . ? 
C6 C7 H7B 108.2 . . ? 
H7A C7 H7B 107.4 . . ? 
C7 C8 C9 115.60(12) . . ? 
C7 C8 H8A 108.4 . . ? 
C9 C8 H8A 108.4 . . ? 
C7 C8 H8B 108.4 . . ? 
C9 C8 H8B 108.4 . . ? 
H8A C8 H8B 107.4 . . ? 
C10 C9 C8 116.77(12) . . ? 
C10 C9 H9A 108.1 . . ? 
C8 C9 H9A 108.1 . . ? 
C10 C9 H9B 108.1 . . ? 
C8 C9 H9B 108.1 . . ? 
H9A C9 H9B 107.3 . . ? 
C9 C10 C11 114.18(12) . . ? 
C9 C10 H10A 108.7 . . ? 
C11 C10 H10A 108.7 . . ? 
C9 C10 H10B 108.7 . . ? 
C11 C10 H10B 108.7 . . ? 
H10A C10 H10B 107.6 . . ? 
C12 C11 C10 114.35(12) . . ? 
C12 C11 H11A 108.7 . . ? 
C10 C11 H11A 108.7 . . ? 
C12 C11 H11B 108.7 . . ? 
C10 C11 H11B 108.7 . . ? 
H11A C11 H11B 107.6 . . ? 
C11 C12 C13 114.35(11) . . ? 
C11 C12 H12A 108.7 . . ? 
C13 C12 H12A 108.7 . . ? 
C11 C12 H12B 108.7 . . ? 
C13 C12 H12B 108.7 . . ? 
H12A C12 H12B 107.6 . . ? 
C1 C13 C12 112.55(11) . . ? 
C1 C13 H13A 109.1 . . ? 
C12 C13 H13A 109.1 . . ? 
C1 C13 H13B 109.1 . . ? 
C12 C13 H13B 109.1 . . ? 
H13A C13 H13B 107.8 . . ? 
  
_refine_diff_density_max    0.330 
_refine_diff_density_min   -0.198 
_refine_diff_density_rms    0.038 
  
_shelxl_version_number 2014/6 
  
  
  
