 
data_1
 
_audit_creation_method            'SHELXL-2014/7'
_shelx_SHELXL_version_number      '2014/7'
_chemical_name_systematic         ?
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C19 H13 N O' 
_chemical_formula_weight          271.30

loop_
 _atom_type_symbol
 _atom_type_description
 _atom_type_scat_dispersion_real
 _atom_type_scat_dispersion_imag
 _atom_type_scat_source
 'C'  'C'   0.0137   0.0067
 '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'   0.0241   0.0134
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O'  'O'   0.0389   0.0241
 '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                    9.4767(16)
_cell_length_b                    18.528(3)
_cell_length_c                    7.4466(12)
_cell_angle_alpha                 90
_cell_angle_beta                  92.516(6)
_cell_angle_gamma                 90
_cell_volume                      1306.2(4)
_cell_formula_units_Z             4
_cell_measurement_temperature     150(2)
_cell_measurement_reflns_used     5200
_cell_measurement_theta_min        4.06
_cell_measurement_theta_max       52.07
 
_exptl_crystal_description       block
_exptl_crystal_colour             colorless
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_density_diffrn     1.380          
_exptl_crystal_F_000              568
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           0.30
_exptl_crystal_size_mid           0.25
_exptl_crystal_size_min           0.18
_exptl_absorpt_coefficient_mu     0.427
_shelx_estimated_absorpt_T_min    ?
_shelx_estimated_absorpt_T_max    ?
_exptl_absorpt_correction_type     'none'
_exptl_absorpt_correction_T_min   ?
_exptl_absorpt_correction_T_max   ?
_exptl_absorpt_process_details    ?
_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature       150(2)
_diffrn_radiation_wavelength      1.34139
_diffrn_radiation_type            GaK\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             9557
_diffrn_reflns_av_unetI/netI      0.0436
_diffrn_reflns_av_R_equivalents   0.0531
_diffrn_reflns_limit_h_min        -10
_diffrn_reflns_limit_h_max        11
_diffrn_reflns_limit_k_min        -21
_diffrn_reflns_limit_k_max        20
_diffrn_reflns_limit_l_min        -8
_diffrn_reflns_limit_l_max        8
_diffrn_reflns_theta_min          4.062
_diffrn_reflns_theta_max          52.214
_diffrn_reflns_theta_full         52.214
_diffrn_measured_fraction_theta_max   0.984
_diffrn_measured_fraction_theta_full  0.984
_diffrn_reflns_Laue_measured_fraction_max    0.984
_diffrn_reflns_Laue_measured_fraction_full   0.984
_diffrn_reflns_point_group_measured_fraction_max   0.984
_diffrn_reflns_point_group_measured_fraction_full  0.984
_reflns_number_total              2205
_reflns_number_gt                 1788
_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-2014/7 (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)+(0.1000P)²+0.9645P] 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          2205
_refine_ls_number_parameters      191
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0752
_refine_ls_R_factor_gt            0.0609
_refine_ls_wR_factor_ref          0.1963
_refine_ls_wR_factor_gt           0.1869
_refine_ls_goodness_of_fit_ref    1.133
_refine_ls_restrained_S_all       1.133
_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
C1 C 0.7329(3) 0.83666(14) 0.3974(3) 0.0323(7) Uani 1 1 d . . . . .
C2 C 0.7685(3) 0.76102(14) 0.3977(3) 0.0303(6) Uani 1 1 d . . . . .
C3 C 0.9107(3) 0.73585(16) 0.3792(4) 0.0366(7) Uani 1 1 d . . . . .
H3 H 0.9850 0.7699 0.3690 0.044 Uiso 1 1 calc R U . . .
C4 C 0.9401(3) 0.66455(16) 0.3760(4) 0.0379(7) Uani 1 1 d . . . . .
H4 H 1.0359 0.6493 0.3775 0.045 Uiso 1 1 calc R U . . .
C5 C 0.8314(3) 0.61172(15) 0.3705(3) 0.0339(7) Uani 1 1 d . . . . .
C6 C 0.8638(3) 0.53802(16) 0.3430(4) 0.0376(7) Uani 1 1 d . . . . .
H6 H 0.9598 0.5233 0.3433 0.045 Uiso 1 1 calc R U . . .
C7 C 0.7597(3) 0.48753(15) 0.3160(4) 0.0388(7) Uani 1 1 d . . . . .
H7 H 0.7830 0.4381 0.3002 0.047 Uiso 1 1 calc R U . . .
C8 C 0.6185(3) 0.50951(15) 0.3119(3) 0.0366(7) Uani 1 1 d . . . . .
H8 H 0.5457 0.4752 0.2868 0.044 Uiso 1 1 calc R U . . .
C9 C 0.5839(3) 0.58039(14) 0.3439(3) 0.0328(7) Uani 1 1 d . . . . .
H9 H 0.4872 0.5940 0.3411 0.039 Uiso 1 1 calc R U . . .
C10 C 0.6890(3) 0.63364(14) 0.3810(3) 0.0302(6) Uani 1 1 d . . . . .
C11 C 0.6582(3) 0.70987(14) 0.4135(3) 0.0297(6) Uani 1 1 d . . . . .
C12 C 0.5227(3) 0.73662(14) 0.4646(3) 0.0291(6) Uani 1 1 d . . . . .
C13 C 0.4117(3) 0.69487(14) 0.5321(3) 0.0314(6) Uani 1 1 d . . . . .
H13 H 0.4246 0.6444 0.5473 0.038 Uiso 1 1 calc R U . . .
C14 C 0.2867(3) 0.72528(15) 0.5757(3) 0.0338(7) Uani 1 1 d . . . . .
H14 H 0.2142 0.6955 0.6196 0.041 Uiso 1 1 calc R U . . .
C15 C 0.2632(3) 0.79986(15) 0.5570(4) 0.0349(7) Uani 1 1 d . . . . .
H15 H 0.1742 0.8201 0.5827 0.042 Uiso 1 1 calc R U . . .
C16 C 0.3701(3) 0.84287(15) 0.5012(3) 0.0342(7) Uani 1 1 d . . . . .
H16 H 0.3559 0.8935 0.4911 0.041 Uiso 1 1 calc R U . . .
C17 C 0.5012(3) 0.81271(14) 0.4585(3) 0.0305(6) Uani 1 1 d . . . . .
C18 C 0.8378(3) 0.89770(16) 0.3748(4) 0.0397(7) Uani 1 1 d . . . . .
C19 C 0.7795(3) 0.97190(15) 0.3401(4) 0.0432(8) Uani 1 1 d . . . . .
H19A H 0.8540 1.0078 0.3642 0.065 Uiso 1 1 calc R U . . .
H19B H 0.7013 0.9808 0.4190 0.065 Uiso 1 1 calc R U . . .
H19C H 0.7452 0.9756 0.2144 0.065 Uiso 1 1 calc R U . . .
N1 N 0.6042(2) 0.86112(12) 0.4163(3) 0.0328(6) Uani 1 1 d . . . . .
O1 O 0.9642(3) 0.88833(13) 0.3885(4) 0.0746(9) Uani 1 1 d . . . . .
 
 
_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
C1 N1 1.314(4) . ?
C1 C2 1.441(4) . ?
C1 C18 1.520(4) . ?
C2 C11 1.419(4) . ?
C2 C3 1.439(4) . ?
C3 C4 1.350(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.420(4) . ?
C4 H4 0.9500 . ?
C5 C10 1.414(4) . ?
C5 C6 1.416(4) . ?
C6 C7 1.368(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.398(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.377(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.421(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.465(4) . ?
C11 C12 1.444(4) . ?
C12 C13 1.415(4) . ?
C12 C17 1.425(4) . ?
C13 C14 1.364(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.406(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.368(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.412(4) . ?
C16 H16 0.9500 . ?
C17 N1 1.372(3) . ?
C18 O1 1.211(4) . ?
C18 C19 1.500(4) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
 
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 C1 C2 123.6(2) . . ?
N1 C1 C18 111.7(2) . . ?
C2 C1 C18 124.7(2) . . ?
C11 C2 C3 119.2(2) . . ?
C11 C2 C1 118.5(2) . . ?
C3 C2 C1 122.3(2) . . ?
C4 C3 C2 120.9(3) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C3 C4 C5 121.7(3) . . ?
C3 C4 H4 119.2 . . ?
C5 C4 H4 119.2 . . ?
C10 C5 C6 119.9(3) . . ?
C10 C5 C4 119.5(3) . . ?
C6 C5 C4 120.5(3) . . ?
C7 C6 C5 121.4(3) . . ?
C7 C6 H6 119.3 . . ?
C5 C6 H6 119.3 . . ?
C6 C7 C8 119.2(3) . . ?
C6 C7 H7 120.4 . . ?
C8 C7 H7 120.4 . . ?
C9 C8 C7 120.6(3) . . ?
C9 C8 H8 119.7 . . ?
C7 C8 H8 119.7 . . ?
C8 C9 C10 121.7(3) . . ?
C8 C9 H9 119.1 . . ?
C10 C9 H9 119.1 . . ?
C5 C10 C9 116.9(2) . . ?
C5 C10 C11 118.9(2) . . ?
C9 C10 C11 124.0(2) . . ?
C2 C11 C12 117.3(2) . . ?
C2 C11 C10 118.5(2) . . ?
C12 C11 C10 124.1(2) . . ?
C13 C12 C17 116.4(2) . . ?
C13 C12 C11 126.1(2) . . ?
C17 C12 C11 117.3(2) . . ?
C14 C13 C12 121.7(3) . . ?
C14 C13 H13 119.2 . . ?
C12 C13 H13 119.2 . . ?
C13 C14 C15 121.2(3) . . ?
C13 C14 H14 119.4 . . ?
C15 C14 H14 119.4 . . ?
C16 C15 C14 119.1(3) . . ?
C16 C15 H15 120.4 . . ?
C14 C15 H15 120.4 . . ?
C15 C16 C17 120.6(2) . . ?
C15 C16 H16 119.7 . . ?
C17 C16 H16 119.7 . . ?
N1 C17 C16 115.8(2) . . ?
N1 C17 C12 123.5(2) . . ?
C16 C17 C12 120.7(2) . . ?
O1 C18 C19 120.1(3) . . ?
O1 C18 C1 122.3(3) . . ?
C19 C18 C1 117.6(3) . . ?
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 . . ?
C1 N1 C17 118.1(2) . . ?
 
_refine_diff_density_max    0.276
_refine_diff_density_min   -0.288
_refine_diff_density_rms    0.061



