 
data_shelx
 
_audit_creation_method            'SHELXL-2014/7'
_shelx_SHELXL_version_number      '2014/7'
_chemical_name_systematic         ?
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          'C17 H17 N O2'
_chemical_formula_sum
 'C17 H17 N O2' 
_chemical_formula_weight          267.31

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       monoclinic
_space_group_IT_number            15
_space_group_name_H-M_alt         'C 2/c'
_space_group_name_Hall            '-C 2yc'
 
_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, -z+1/2'
 'x+1/2, y+1/2, z'
 '-x+1/2, y+1/2, -z+1/2'
 '-x, -y, -z'
 'x, -y, z-1/2'
 '-x+1/2, -y+1/2, -z'
 'x+1/2, -y+1/2, z-1/2'
 
_cell_length_a                    62.025(4)
_cell_length_b                    5.3766(3)
_cell_length_c                    8.2455(5)
_cell_angle_alpha                 90
_cell_angle_beta                  92.464(2)
_cell_angle_gamma                 90
_cell_volume                      2747.2(3)
_cell_formula_units_Z             8
_cell_measurement_temperature     298(2)
_cell_measurement_reflns_used     12191
_cell_measurement_theta_min       2.6
_cell_measurement_theta_max       28.3
 
_exptl_crystal_description        'block'
_exptl_crystal_colour             'yellow'
_exptl_crystal_density_meas       1.29
_exptl_crystal_density_method     'not measured'
_exptl_crystal_density_diffrn     1.293          
_exptl_crystal_F_000              1136
_exptl_transmission_factor_min    0.6504
_exptl_transmission_factor_max    0.7457
_exptl_crystal_size_max           0.360
_exptl_crystal_size_mid           0.340
_exptl_crystal_size_min           0.250
_exptl_absorpt_coefficient_mu     0.085
_shelx_estimated_absorpt_T_min    0.970
_shelx_estimated_absorpt_T_max    0.979
_exptl_absorpt_correction_type    'multi-scan' 
_exptl_absorpt_correction_T_min   0.6519 
_exptl_absorpt_correction_T_max   0.7457 
_exptl_absorpt_process_details    'SADABS'
_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature       298(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_source                    'fine-focus sealed tube'                       
_diffrn_measurement_device_type   'Bruker D8 Venture PHOTON 100 CMOS' 
_diffrn_measurement_method        'phi and omega scan' 
_diffrn_detector_area_resol_mean  10.233
_diffrn_reflns_number             12191
_diffrn_reflns_av_unetI/netI      0.0244
_diffrn_reflns_av_R_equivalents   0.0227
_diffrn_reflns_limit_h_min        -81
_diffrn_reflns_limit_h_max        82
_diffrn_reflns_limit_k_min        -7
_diffrn_reflns_limit_k_max        7
_diffrn_reflns_limit_l_min        -9
_diffrn_reflns_limit_l_max        10
_diffrn_reflns_theta_min          2.630
_diffrn_reflns_theta_max          28.269
_diffrn_reflns_theta_full         25.242
_diffrn_measured_fraction_theta_max   0.947
_diffrn_measured_fraction_theta_full  0.994
_diffrn_reflns_Laue_measured_fraction_max    0.947
_diffrn_reflns_Laue_measured_fraction_full   0.994
_diffrn_reflns_point_group_measured_fraction_max   0.947
_diffrn_reflns_point_group_measured_fraction_full  0.994
_reflns_number_total              3219
_reflns_number_gt                 2554
_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        'APEX2 (Bruker, 2014)'
_computing_cell_refinement        'APEX2 (Bruker, 2014); SAINT (Bruker, 2014)'
_computing_data_reduction         'SAINT (Bruker, 2014);XPREP(Sheldrick,2014)'
_computing_structure_solution     'SHELXS-2014 (Sheldrick, 2014)'
_computing_structure_refinement   'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics     'Ortep, Platon, mercury'
_computing_publication_material   ?
_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)+(0.0367P)²+2.8841P] 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      none
_refine_ls_extinction_coef        .
_refine_ls_number_reflns          3219
_refine_ls_number_parameters      181
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0757
_refine_ls_R_factor_gt            0.0576
_refine_ls_wR_factor_ref          0.1326
_refine_ls_wR_factor_gt           0.1225
_refine_ls_goodness_of_fit_ref    1.084
_refine_ls_restrained_S_all       1.084
_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 0.05380(2) 0.3972(2) -0.00313(15) 0.0459(3) Uani 1 1 d . . . . .
O2 O 0.15252(2) 0.2684(3) 0.00386(16) 0.0546(4) Uani 1 1 d . . . . .
N1 N 0.03117(2) 0.4327(3) -0.0005(2) 0.0531(4) Uani 1 1 d . . . . .
C12 C 0.08723(3) 0.2471(3) 0.10007(19) 0.0365(4) Uani 1 1 d . . . . .
C13 C 0.10101(3) 0.4305(3) 0.1621(2) 0.0460(4) Uani 1 1 d . . . . .
H13 H 0.0956 0.5552 0.2271 0.055 Uiso 1 1 calc R U . . .
C16 C 0.05209(3) 0.0142(3) 0.1497(2) 0.0428(4) Uani 1 1 d . . . . .
H16A H 0.0588 -0.0823 0.2377 0.051 Uiso 1 1 calc R U . . .
H16B H 0.0528 -0.0809 0.0501 0.051 Uiso 1 1 calc R U . . .
C11 C 0.09592(3) 0.0626(3) 0.0060(2) 0.0427(4) Uani 1 1 d . . . . .
H11 H 0.0870 -0.0638 -0.0348 0.051 Uiso 1 1 calc R U . . .
C8 C 0.16176(3) 0.0901(4) -0.1012(2) 0.0512(5) Uani 1 1 d . . . . .
H8A H 0.1535 0.0829 -0.2036 0.061 Uiso 1 1 calc R U . . .
H8B H 0.1617 -0.0736 -0.0518 0.061 Uiso 1 1 calc R U . . .
C1 C 0.02075(3) 0.2861(4) 0.0869(2) 0.0501(5) Uani 1 1 d . . . . .
H1 H 0.0060 0.3179 0.0905 0.060 Uiso 1 1 calc R U . . .
C15 C 0.06358(3) 0.2587(3) 0.13347(19) 0.0372(4) Uani 1 1 d . . . . .
H15 H 0.0618 0.3552 0.2329 0.045 Uiso 1 1 calc R U . . .
C14 C 0.12256(3) 0.4307(4) 0.1291(2) 0.0487(5) Uani 1 1 d . . . . .
H14 H 0.1316 0.5545 0.1724 0.058 Uiso 1 1 calc R U . . .
C2 C 0.18452(3) 0.1691(4) -0.1289(2) 0.0443(4) Uani 1 1 d . . . . .
C9 C 0.13094(3) 0.2475(3) 0.0317(2) 0.0400(4) Uani 1 1 d . . . . .
C10 C 0.11759(3) 0.0609(3) -0.0293(2) 0.0438(4) Uani 1 1 d . . . . .
H10 H 0.1231 -0.0646 -0.0933 0.053 Uiso 1 1 calc R U . . .
C17 C 0.02871(3) 0.0704(4) 0.1845(2) 0.0481(4) Uani 1 1 d . . . . .
H17A H 0.0199 -0.0741 0.1586 0.058 Uiso 1 1 calc R U . . .
H17B H 0.0276 0.1066 0.2991 0.058 Uiso 1 1 calc R U . . .
C3 C 0.20168(3) 0.0294(4) -0.0685(3) 0.0558(5) Uani 1 1 d . . . . .
H3 H 0.1991 -0.1123 -0.0076 0.067 Uiso 1 1 calc R U . . .
C5 C 0.22650(4) 0.3071(5) -0.1859(3) 0.0697(7) Uani 1 1 d . . . . .
H5 H 0.2406 0.3535 -0.2053 0.084 Uiso 1 1 calc R U . . .
C4 C 0.22265(3) 0.0980(5) -0.0975(3) 0.0676(6) Uani 1 1 d . . . . .
H4 H 0.2341 0.0019 -0.0569 0.081 Uiso 1 1 calc R U . . .
C6 C 0.20966(4) 0.4479(5) -0.2458(3) 0.0693(6) Uani 1 1 d . . . . .
H6 H 0.2123 0.5904 -0.3057 0.083 Uiso 1 1 calc R U . . .
C7 C 0.18868(3) 0.3797(4) -0.2178(3) 0.0580(5) Uani 1 1 d . . . . .
H7 H 0.1773 0.4763 -0.2592 0.070 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 N1 1.4178(18) . ?
O1 C15 1.4603(19) . ?
O2 C9 1.3718(19) . ?
O2 C8 1.428(2) . ?
N1 C1 1.265(2) . ?
C12 C11 1.383(2) . ?
C12 C13 1.388(2) . ?
C12 C15 1.505(2) . ?
C13 C14 1.376(2) . ?
C16 C15 1.504(2) . ?
C16 C17 1.520(2) . ?
C11 C10 1.387(2) . ?
C8 C2 1.501(2) . ?
C1 C17 1.484(3) . ?
C14 C9 1.386(2) . ?
C2 C3 1.378(3) . ?
C2 C7 1.379(3) . ?
C9 C10 1.382(2) . ?
C3 C4 1.383(3) . ?
C5 C6 1.365(3) . ?
C5 C4 1.367(3) . ?
C6 C7 1.381(3) . ?
 
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
N1 O1 C15 115.83(12) . . ?
C9 O2 C8 117.78(14) . . ?
C1 N1 O1 117.11(15) . . ?
C11 C12 C13 117.86(15) . . ?
C11 C12 C15 122.61(15) . . ?
C13 C12 C15 119.52(15) . . ?
C14 C13 C12 121.07(16) . . ?
C15 C16 C17 107.61(15) . . ?
C12 C11 C10 121.80(16) . . ?
O2 C8 C2 107.89(15) . . ?
N1 C1 C17 129.03(17) . . ?
O1 C15 C16 109.36(13) . . ?
O1 C15 C12 104.82(12) . . ?
C16 C15 C12 116.70(14) . . ?
C13 C14 C9 120.39(17) . . ?
C3 C2 C7 118.72(18) . . ?
C3 C2 C8 120.50(18) . . ?
C7 C2 C8 120.77(18) . . ?
O2 C9 C10 124.93(16) . . ?
O2 C9 C14 115.55(15) . . ?
C10 C9 C14 119.52(16) . . ?
C9 C10 C11 119.34(16) . . ?
C1 C17 C16 110.54(15) . . ?
C2 C3 C4 120.7(2) . . ?
C6 C5 C4 120.0(2) . . ?
C5 C4 C3 119.9(2) . . ?
C5 C6 C7 120.3(2) . . ?
C2 C7 C6 120.4(2) . . ?
 
_refine_diff_density_max    0.216
_refine_diff_density_min   -0.165
_refine_diff_density_rms    0.036



