 
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          'C30 H22 N2 O'
_chemical_formula_sum             'C30 H22 N2 O' 
_chemical_formula_weight          426.49

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            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                    9.2331(3)
_cell_length_b                    7.8326(3)
_cell_length_c                    29.3232(12)
_cell_angle_alpha                 90
_cell_angle_beta                  93.4080(10)
_cell_angle_gamma                 90
_cell_volume                      2116.88(14)
_cell_formula_units_Z             4
_cell_measurement_temperature     200(2)
_cell_measurement_reflns_used     5123
_cell_measurement_theta_min       2.69
_cell_measurement_theta_max       24.72
 
_exptl_crystal_description        prism
_exptl_crystal_colour             yellow
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_density_diffrn     1.338          
_exptl_crystal_F_000              896
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           0.560
_exptl_crystal_size_mid           0.170
_exptl_crystal_size_min           0.030
_exptl_absorpt_coefficient_mu     0.081
_shelx_estimated_absorpt_T_min    0.956
_shelx_estimated_absorpt_T_max    0.998
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.956
_exptl_absorpt_correction_T_max   0.998
_exptl_absorpt_process_details    ?
_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature       200(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_source                    ?
_diffrn_measurement_device_type   'Bruker D8 Venture'
_diffrn_measurement_method        ?
_diffrn_detector_area_resol_mean  ?
_diffrn_reflns_number             23366
_diffrn_reflns_av_unetI/netI      0.0425
_diffrn_reflns_av_R_equivalents   0.0697
_diffrn_reflns_limit_h_min        -10
_diffrn_reflns_limit_h_max        10
_diffrn_reflns_limit_k_min        -9
_diffrn_reflns_limit_k_max        9
_diffrn_reflns_limit_l_min        -34
_diffrn_reflns_limit_l_max        34
_diffrn_reflns_theta_min          2.356
_diffrn_reflns_theta_max          25.041
_diffrn_reflns_theta_full         25.041
_diffrn_measured_fraction_theta_max   0.996
_diffrn_measured_fraction_theta_full  0.996
_diffrn_reflns_Laue_measured_fraction_max    0.996
_diffrn_reflns_Laue_measured_fraction_full   0.996
_diffrn_reflns_point_group_measured_fraction_max   0.996
_diffrn_reflns_point_group_measured_fraction_full  0.996
_reflns_number_total              3734
_reflns_number_gt                 3058
_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        ?
_computing_cell_refinement        ?
_computing_data_reduction         ?
_computing_structure_solution     ?
_computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics     ?
_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)+(0.0682P)²+0.3183P] 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          3734
_refine_ls_number_parameters      299
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0523
_refine_ls_R_factor_gt            0.0409
_refine_ls_wR_factor_ref          0.1190
_refine_ls_wR_factor_gt           0.1109
_refine_ls_goodness_of_fit_ref    1.017
_refine_ls_restrained_S_all       1.017
_refine_ls_shift/su_max           0.001
_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 0.86465(18) -0.0463(2) 0.76314(6) 0.0409(4) Uani 1 1 d . . . . .
H1A H 0.8970 -0.1266 0.7873 0.061 Uiso 1 1 calc R U . . .
H1B H 0.8044 -0.1066 0.7397 0.061 Uiso 1 1 calc R U . . .
H1C H 0.8078 0.0452 0.7763 0.061 Uiso 1 1 calc R U . . .
C2 C 0.95381(16) 0.13295(19) 0.70668(5) 0.0288(4) Uani 1 1 d . . . . .
C3 C 0.98182(15) 0.30904(19) 0.71007(5) 0.0259(3) Uani 1 1 d . . . . .
C4 C 1.02313(15) 0.39520(19) 0.75430(5) 0.0278(4) Uani 1 1 d . . . . .
C5 C 1.0065(2) 0.4128(2) 0.83171(6) 0.0453(5) Uani 1 1 d . . . . .
H5 H 0.9713 0.3684 0.8591 0.054 Uiso 1 1 calc R U . . .
C6 C 1.0875(2) 0.5607(2) 0.83441(6) 0.0501(5) Uani 1 1 d . . . . .
H6 H 1.1108 0.6136 0.8631 0.060 Uiso 1 1 calc R U . . .
C7 C 1.1337(2) 0.6298(2) 0.79493(6) 0.0433(5) Uani 1 1 d . . . . .
H7 H 1.1884 0.7326 0.7959 0.052 Uiso 1 1 calc R U . . .
C8 C 1.10032(17) 0.5491(2) 0.75358(5) 0.0316(4) Uani 1 1 d . . . . .
C9 C 1.13504(17) 0.6217(2) 0.70836(5) 0.0365(4) Uani 1 1 d . . . . .
H9A H 1.2215 0.5638 0.6972 0.044 Uiso 1 1 calc R U . . .
H9B H 1.1573 0.7449 0.7117 0.044 Uiso 1 1 calc R U . . .
C10 C 1.00582(17) 0.59712(19) 0.67392(5) 0.0323(4) Uani 1 1 d . . . . .
H10A H 0.9227 0.6656 0.6834 0.039 Uiso 1 1 calc R U . . .
H10B H 1.0317 0.6383 0.6435 0.039 Uiso 1 1 calc R U . . .
C11 C 0.96224(15) 0.41112(18) 0.67056(5) 0.0253(3) Uani 1 1 d . . . . .
C12 C 0.89940(15) 0.34245(19) 0.62987(5) 0.0267(3) Uani 1 1 d . . . . .
C13 C 0.86849(18) 0.1688(2) 0.62823(5) 0.0348(4) Uani 1 1 d . . . . .
H13 H 0.8265 0.1205 0.6008 0.042 Uiso 1 1 calc R U . . .
C14 C 0.89773(18) 0.0654(2) 0.66571(6) 0.0361(4) Uani 1 1 d . . . . .
H14 H 0.8792 -0.0536 0.6634 0.043 Uiso 1 1 calc R U . . .
C15 C 0.86197(16) 0.4559(2) 0.58847(5) 0.0304(4) Uani 1 1 d . . . . .
H15A H 0.8301 0.5689 0.5992 0.037 Uiso 1 1 calc R U . . .
H15B H 0.9504 0.4735 0.5715 0.037 Uiso 1 1 calc R U . . .
C16 C 0.74377(16) 0.38162(18) 0.55622(5) 0.0262(3) Uani 1 1 d . . . . .
C17 C 0.77815(15) 0.29394(19) 0.51624(5) 0.0275(3) Uani 1 1 d . . . . .
C18 C 0.92326(16) 0.2669(2) 0.50348(6) 0.0365(4) Uani 1 1 d . . . . .
H18 H 1.0013 0.3117 0.5224 0.044 Uiso 1 1 calc R U . . .
C19 C 0.95332(18) 0.1795(2) 0.46533(6) 0.0429(4) Uani 1 1 d . . . . .
H19 H 1.0513 0.1632 0.4581 0.052 Uiso 1 1 calc R U . . .
C20 C 0.83975(19) 0.1123(2) 0.43611(6) 0.0411(4) Uani 1 1 d . . . . .
H20 H 0.8617 0.0518 0.4093 0.049 Uiso 1 1 calc R U . . .
C21 C 0.69999(18) 0.1342(2) 0.44637(5) 0.0342(4) Uani 1 1 d . . . . .
H21 H 0.6246 0.0886 0.4265 0.041 Uiso 1 1 calc R U . . .
C22 C 0.66363(16) 0.22403(19) 0.48629(5) 0.0272(3) Uani 1 1 d . . . . .
C23 C 0.51901(15) 0.24482(18) 0.49783(5) 0.0261(3) Uani 1 1 d . . . . .
C24 C 0.48304(16) 0.32696(19) 0.53830(5) 0.0264(3) Uani 1 1 d . . . . .
C25 C 0.33682(17) 0.3428(2) 0.55084(6) 0.0336(4) Uani 1 1 d . . . . .
H25 H 0.2604 0.2971 0.5314 0.040 Uiso 1 1 calc R U . . .
C26 C 0.30544(18) 0.4226(2) 0.59027(6) 0.0395(4) Uani 1 1 d . . . . .
H26 H 0.2075 0.4312 0.5983 0.047 Uiso 1 1 calc R U . . .
C27 C 0.41744(18) 0.4927(2) 0.61931(6) 0.0390(4) Uani 1 1 d . . . . .
H27 H 0.3943 0.5497 0.6465 0.047 Uiso 1 1 calc R U . . .
C28 C 0.55794(18) 0.4791(2) 0.60862(5) 0.0333(4) Uani 1 1 d . . . . .
H28 H 0.6318 0.5260 0.6288 0.040 Uiso 1 1 calc R U . . .
C29 C 0.59781(16) 0.39620(19) 0.56779(5) 0.0269(3) Uani 1 1 d . . . . .
C30 C 0.40287(17) 0.1803(2) 0.46613(5) 0.0294(4) Uani 1 1 d . . . . .
N1 N 0.97448(15) 0.32826(17) 0.79281(4) 0.0353(3) Uani 1 1 d . . . . .
N2 N 0.31603(16) 0.13477(19) 0.44170(5) 0.0422(4) Uani 1 1 d . . . . .
O1 O 0.98850(11) 0.02566(14) 0.74301(4) 0.0338(3) 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 O1 1.4331(19) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 O1 1.3795(18) . ?
C2 C14 1.385(2) . ?
C2 C3 1.406(2) . ?
C3 C11 1.411(2) . ?
C3 C4 1.491(2) . ?
C4 N1 1.346(2) . ?
C4 C8 1.401(2) . ?
C5 N1 1.337(2) . ?
C5 C6 1.379(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.369(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.386(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.495(2) . ?
C9 C10 1.529(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.513(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.403(2) . ?
C12 C13 1.390(2) . ?
C12 C15 1.527(2) . ?
C13 C14 1.379(2) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 C16 1.517(2) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.411(2) . ?
C16 C29 1.414(2) . ?
C17 C18 1.428(2) . ?
C17 C22 1.442(2) . ?
C18 C19 1.354(2) . ?
C18 H18 0.9500 . ?
C19 C20 1.416(2) . ?
C19 H19 0.9500 . ?
C20 C21 1.353(2) . ?
C20 H20 0.9500 . ?
C21 C22 1.423(2) . ?
C21 H21 0.9500 . ?
C22 C23 1.406(2) . ?
C23 C24 1.407(2) . ?
C23 C30 1.467(2) . ?
C24 C25 1.426(2) . ?
C24 C29 1.434(2) . ?
C25 C26 1.360(2) . ?
C25 H25 0.9500 . ?
C26 C27 1.411(2) . ?
C26 H26 0.9500 . ?
C27 C28 1.357(2) . ?
C27 H27 0.9500 . ?
C28 C29 1.429(2) . ?
C28 H28 0.9500 . ?
C30 N2 1.1022(19) . ?
 
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
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 C14 119.67(14) . . ?
O1 C2 C3 120.65(13) . . ?
C14 C2 C3 119.60(14) . . ?
C2 C3 C11 118.94(13) . . ?
C2 C3 C4 122.82(13) . . ?
C11 C3 C4 118.13(13) . . ?
N1 C4 C8 122.89(14) . . ?
N1 C4 C3 118.19(14) . . ?
C8 C4 C3 118.70(13) . . ?
N1 C5 C6 123.82(17) . . ?
N1 C5 H5 118.1 . . ?
C6 C5 H5 118.1 . . ?
C7 C6 C5 118.63(16) . . ?
C7 C6 H6 120.7 . . ?
C5 C6 H6 120.7 . . ?
C6 C7 C8 119.67(16) . . ?
C6 C7 H7 120.2 . . ?
C8 C7 H7 120.2 . . ?
C7 C8 C4 117.80(15) . . ?
C7 C8 C9 123.64(15) . . ?
C4 C8 C9 118.48(13) . . ?
C8 C9 C10 109.74(13) . . ?
C8 C9 H9A 109.7 . . ?
C10 C9 H9A 109.7 . . ?
C8 C9 H9B 109.7 . . ?
C10 C9 H9B 109.7 . . ?
H9A C9 H9B 108.2 . . ?
C11 C10 C9 111.01(13) . . ?
C11 C10 H10A 109.4 . . ?
C9 C10 H10A 109.4 . . ?
C11 C10 H10B 109.4 . . ?
C9 C10 H10B 109.4 . . ?
H10A C10 H10B 108.0 . . ?
C12 C11 C3 120.52(14) . . ?
C12 C11 C10 121.30(13) . . ?
C3 C11 C10 118.15(13) . . ?
C13 C12 C11 118.57(14) . . ?
C13 C12 C15 120.38(13) . . ?
C11 C12 C15 121.03(13) . . ?
C14 C13 C12 121.13(14) . . ?
C14 C13 H13 119.4 . . ?
C12 C13 H13 119.4 . . ?
C13 C14 C2 120.85(15) . . ?
C13 C14 H14 119.6 . . ?
C2 C14 H14 119.6 . . ?
C16 C15 C12 113.11(12) . . ?
C16 C15 H15A 109.0 . . ?
C12 C15 H15A 109.0 . . ?
C16 C15 H15B 109.0 . . ?
C12 C15 H15B 109.0 . . ?
H15A C15 H15B 107.8 . . ?
C17 C16 C29 120.23(13) . . ?
C17 C16 C15 121.04(13) . . ?
C29 C16 C15 118.69(13) . . ?
C16 C17 C18 123.42(13) . . ?
C16 C17 C22 119.86(13) . . ?
C18 C17 C22 116.71(14) . . ?
C19 C18 C17 122.21(15) . . ?
C19 C18 H18 118.9 . . ?
C17 C18 H18 118.9 . . ?
C18 C19 C20 120.48(16) . . ?
C18 C19 H19 119.8 . . ?
C20 C19 H19 119.8 . . ?
C21 C20 C19 120.01(16) . . ?
C21 C20 H20 120.0 . . ?
C19 C20 H20 120.0 . . ?
C20 C21 C22 121.34(15) . . ?
C20 C21 H21 119.3 . . ?
C22 C21 H21 119.3 . . ?
C23 C22 C21 121.93(14) . . ?
C23 C22 C17 118.81(14) . . ?
C21 C22 C17 119.25(14) . . ?
C22 C23 C24 122.07(13) . . ?
C22 C23 C30 118.47(13) . . ?
C24 C23 C30 119.46(13) . . ?
C23 C24 C25 122.15(14) . . ?
C23 C24 C29 118.60(13) . . ?
C25 C24 C29 119.25(14) . . ?
C26 C25 C24 120.80(15) . . ?
C26 C25 H25 119.6 . . ?
C24 C25 H25 119.6 . . ?
C25 C26 C27 120.40(15) . . ?
C25 C26 H26 119.8 . . ?
C27 C26 H26 119.8 . . ?
C28 C27 C26 120.45(16) . . ?
C28 C27 H27 119.8 . . ?
C26 C27 H27 119.8 . . ?
C27 C28 C29 121.76(15) . . ?
C27 C28 H28 119.1 . . ?
C29 C28 H28 119.1 . . ?
C16 C29 C28 122.30(14) . . ?
C16 C29 C24 120.36(14) . . ?
C28 C29 C24 117.34(14) . . ?
N2 C30 C23 178.46(17) . . ?
C5 N1 C4 117.08(14) . . ?
C2 O1 C1 113.78(12) . . ?
 
_refine_diff_density_max    0.173
_refine_diff_density_min   -0.190
_refine_diff_density_rms    0.040



