 
data_ic22917 
  
_audit_creation_method            'SHELXL-2019/3' 
_shelx_SHELXL_version_number      '2019/3' 
_chemical_name_systematic         ? 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          ? 
_chemical_formula_sum 
 'C29 H20 N2 O' 
_chemical_formula_weight          412.47 
  
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                    9.3731(7) 
_cell_length_b                    8.0865(5) 
_cell_length_c                    26.5071(19) 
_cell_angle_alpha                 90 
_cell_angle_beta                  99.172(3) 
_cell_angle_gamma                 90 
_cell_volume                      1983.4(2) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     100(2) 
_cell_measurement_reflns_used     9939 
_cell_measurement_theta_min       3.38 
_cell_measurement_theta_max       70.16 
  
_exptl_crystal_description        plate 
_exptl_crystal_colour             yellow 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_method     ? 
_exptl_crystal_density_diffrn     1.381 
_exptl_crystal_F_000              864 
_exptl_transmission_factor_min    ? 
_exptl_transmission_factor_max    ? 
_exptl_crystal_size_max           0.100 
_exptl_crystal_size_mid           0.100 
_exptl_crystal_size_min           0.050 
_exptl_absorpt_coefficient_mu     0.660 
_shelx_estimated_absorpt_T_min    0.937 
_shelx_estimated_absorpt_T_max    0.968 
_exptl_absorpt_correction_type    Multi-Scan 
_exptl_absorpt_correction_T_min   0.8555 
_exptl_absorpt_correction_T_max   1.0000 
_exptl_absorpt_process_details     
; 
SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015). 
"Comparison of silver and molybdenum microfocus X-ray sources for 
single-crystal structure determination" 
J. Appl. Cryst. 48, 3-10. 
doi:10.1107/S1600576714022985 
; 
_exptl_absorpt_special_details    ? 
_diffrn_ambient_temperature       100(2) 
_diffrn_radiation_wavelength      1.54178 
_diffrn_radiation_type            CuK\a 
_diffrn_source                    'I-mu-S microfocus sealed tube' 
_diffrn_measurement_device_type   'Bruker AXS D8 VENTURE, PhotonIII_C28' 
_diffrn_measurement_method        'ω and φ scans' 
_diffrn_detector_area_resol_mean  ? 
_diffrn_reflns_number             26255 
_diffrn_reflns_av_unetI/netI      0.0357 
_diffrn_reflns_av_R_equivalents   0.0503 
_diffrn_reflns_limit_h_min        -11 
_diffrn_reflns_limit_h_max        11 
_diffrn_reflns_limit_k_min        -9 
_diffrn_reflns_limit_k_max        9 
_diffrn_reflns_limit_l_min        -31 
_diffrn_reflns_limit_l_max        32 
_diffrn_reflns_theta_min          3.378 
_diffrn_reflns_theta_max          70.151 
_diffrn_reflns_theta_full         67.679 
_diffrn_measured_fraction_theta_max   0.991 
_diffrn_measured_fraction_theta_full  0.996 
_diffrn_reflns_Laue_measured_fraction_max    0.991 
_diffrn_reflns_Laue_measured_fraction_full   0.996 
_diffrn_reflns_point_group_measured_fraction_max   0.991 
_diffrn_reflns_point_group_measured_fraction_full  0.996 
_reflns_number_total              3734 
_reflns_number_gt                 3418 
_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 APEX5' 
_computing_cell_refinement        'SAINT V8.40B (Bruker AXS LLC, 2019)' 
_computing_data_reduction         'SAINT V8.40B (Bruker AXS LLC, 2019)' 
_computing_structure_solution     'SHELXT 2018/2 (Sheldrick, 2018)' 
_computing_structure_refinement 'SHELXL-2019/2 (Sheldrick, 2019)' 
_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)+(0.0667P)²+1.1790P] 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          3734 
_refine_ls_number_parameters      293 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.0487 
_refine_ls_R_factor_gt            0.0452 
_refine_ls_wR_factor_ref          0.1257 
_refine_ls_wR_factor_gt           0.1215 
_refine_ls_goodness_of_fit_ref    1.007 
_refine_ls_restrained_S_all       1.007 
_refine_ls_shift/su_max           0.002 
_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 0.06074(13) 0.09362(13) 0.75295(4) 0.0297(3) Uani 1 1 d . . . . . 
N1 N -0.07272(16) 0.34436(17) 0.78031(5) 0.0299(3) Uani 1 1 d . . . . . 
N2 N 0.63758(14) 0.11351(16) 0.42749(5) 0.0283(3) Uani 1 1 d . . . . . 
C1 C -0.1522(2) 0.4139(2) 0.81240(6) 0.0363(4) Uani 1 1 d . . . . . 
H1A H -0.192394 0.344671 0.835471 0.044 Uiso 1 1 calc R U . . . 
C2 C -0.1781(2) 0.5811(2) 0.81334(6) 0.0348(4) Uani 1 1 d . . . . . 
H2 H -0.235890 0.626513 0.836247 0.042 Uiso 1 1 calc R U . . . 
C3 C -0.11779(18) 0.6816(2) 0.78009(6) 0.0285(4) Uani 1 1 d . . . . . 
H3 H -0.132617 0.797747 0.780452 0.034 Uiso 1 1 calc R U . . . 
C4 C -0.03597(16) 0.61313(19) 0.74630(6) 0.0233(3) Uani 1 1 d . . . . . 
C5 C -0.01631(15) 0.44157(18) 0.74690(5) 0.0210(3) Uani 1 1 d . . . . . 
C6 C 0.06614(14) 0.35976(17) 0.71099(5) 0.0192(3) Uani 1 1 d . . . . . 
C7 C 0.09941(15) 0.18917(18) 0.71522(5) 0.0215(3) Uani 1 1 d . . . . . 
C8 C 0.17674(16) 0.11536(18) 0.68067(6) 0.0235(3) Uani 1 1 d . . . . . 
H8 H 0.201165 0.001427 0.683986 0.028 Uiso 1 1 calc R U . . . 
C9 C 0.21816(15) 0.20721(18) 0.64154(6) 0.0213(3) Uani 1 1 d . . . . . 
H9 H 0.270402 0.154946 0.618070 0.026 Uiso 1 1 calc R U . . . 
C10 C 0.18500(14) 0.37521(17) 0.63566(5) 0.0188(3) Uani 1 1 d . . . . . 
C11 C 0.11072(14) 0.45211(17) 0.67106(5) 0.0185(3) Uani 1 1 d . . . . . 
C12 C 0.06854(17) 0.63249(18) 0.66503(6) 0.0255(3) Uani 1 1 d . . . . . 
H12A H 0.145945 0.692524 0.651240 0.031 Uiso 1 1 calc R U . . . 
H12B H -0.020518 0.641042 0.639476 0.031 Uiso 1 1 calc R U . . . 
C13 C 0.04266(18) 0.71734(19) 0.71331(6) 0.0304(4) Uani 1 1 d . . . . . 
H13A H 0.136972 0.750094 0.733158 0.036 Uiso 1 1 calc R U . . . 
H13B H -0.013665 0.819527 0.704095 0.036 Uiso 1 1 calc R U . . . 
C14 C 0.22583(16) 0.47456(18) 0.59132(6) 0.0225(3) Uani 1 1 d . . . . . 
H14A H 0.135995 0.513163 0.569739 0.027 Uiso 1 1 calc R U . . . 
H14B H 0.280288 0.573725 0.605268 0.027 Uiso 1 1 calc R U . . . 
C15 C 0.31524(15) 0.38249(17) 0.55792(5) 0.0202(3) Uani 1 1 d . . . . . 
C16 C 0.24752(15) 0.28935(17) 0.51570(5) 0.0202(3) Uani 1 1 d . . . . . 
C17 C 0.09395(16) 0.26672(19) 0.50479(6) 0.0243(3) Uani 1 1 d . . . . . 
H17 H 0.034644 0.319362 0.525899 0.029 Uiso 1 1 calc R U . . . 
C18 C 0.03100(16) 0.1720(2) 0.46505(6) 0.0270(3) Uani 1 1 d . . . . . 
H18 H -0.071026 0.158897 0.458915 0.032 Uiso 1 1 calc R U . . . 
C19 C 0.11660(16) 0.09231(19) 0.43261(6) 0.0256(3) Uani 1 1 d . . . . . 
H19 H 0.071940 0.025325 0.405118 0.031 Uiso 1 1 calc R U . . . 
C20 C 0.26290(16) 0.11210(18) 0.44098(5) 0.0221(3) Uani 1 1 d . . . . . 
H20 H 0.319377 0.059508 0.418897 0.027 Uiso 1 1 calc R U . . . 
C21 C 0.33247(15) 0.21040(17) 0.48232(5) 0.0195(3) Uani 1 1 d . . . . . 
C22 C 0.48340(15) 0.22959(17) 0.49186(5) 0.0186(3) Uani 1 1 d . . . . . 
C23 C 0.55347(15) 0.31393(17) 0.53541(5) 0.0190(3) Uani 1 1 d . . . . . 
C24 C 0.70721(15) 0.32378(18) 0.54701(6) 0.0222(3) Uani 1 1 d . . . . . 
H24 H 0.764326 0.276789 0.524131 0.027 Uiso 1 1 calc R U . . . 
C25 C 0.77301(16) 0.39927(19) 0.59024(6) 0.0262(3) Uani 1 1 d . . . . . 
H25 H 0.875505 0.403485 0.597648 0.031 Uiso 1 1 calc R U . . . 
C26 C 0.68895(17) 0.47192(19) 0.62438(6) 0.0260(3) Uani 1 1 d . . . . . 
H26 H 0.735812 0.524043 0.654664 0.031 Uiso 1 1 calc R U . . . 
C27 C 0.54208(16) 0.46787(18) 0.61430(6) 0.0233(3) Uani 1 1 d . . . . . 
H27 H 0.487961 0.518311 0.637534 0.028 Uiso 1 1 calc R U . . . 
C28 C 0.46738(15) 0.38889(16) 0.56926(5) 0.0198(3) Uani 1 1 d . . . . . 
C29 C 0.56946(15) 0.16223(17) 0.45591(6) 0.0208(3) Uani 1 1 d . . . . . 
H1 H -0.003(3) 0.170(4) 0.7702(10) 0.070(7) Uiso 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 
O1 C7 1.3580(18) . ? 
N1 C1 1.341(2) . ? 
N1 C5 1.353(2) . ? 
N2 C29 1.1331(19) . ? 
C1 C2 1.374(2) . ? 
C2 C3 1.384(2) . ? 
C3 C4 1.384(2) . ? 
C4 C5 1.399(2) . ? 
C4 C13 1.491(2) . ? 
C5 C6 1.4749(19) . ? 
C6 C11 1.412(2) . ? 
C6 C7 1.415(2) . ? 
C7 C8 1.390(2) . ? 
C8 C9 1.381(2) . ? 
C9 C10 1.397(2) . ? 
C10 C11 1.4000(19) . ? 
C10 C14 1.522(2) . ? 
C11 C12 1.513(2) . ? 
C12 C13 1.506(2) . ? 
C14 C15 1.5090(19) . ? 
C15 C28 1.411(2) . ? 
C15 C16 1.413(2) . ? 
C16 C21 1.431(2) . ? 
C16 C17 1.434(2) . ? 
C17 C18 1.359(2) . ? 
C18 C19 1.421(2) . ? 
C19 C20 1.363(2) . ? 
C20 C21 1.425(2) . ? 
C21 C22 1.406(2) . ? 
C22 C23 1.410(2) . ? 
C22 C29 1.4493(19) . ? 
C23 C24 1.427(2) . ? 
C23 C28 1.4333(19) . ? 
C24 C25 1.357(2) . ? 
C25 C26 1.419(2) . ? 
C26 C27 1.360(2) . ? 
C27 C28 1.434(2) . ? 
  
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 C5 119.10(14) . . ? 
N1 C1 C2 122.78(16) . . ? 
C1 C2 C3 118.36(15) . . ? 
C4 C3 C2 120.12(15) . . ? 
C3 C4 C5 118.34(14) . . ? 
C3 C4 C13 122.02(14) . . ? 
C5 C4 C13 119.37(13) . . ? 
N1 C5 C4 121.26(13) . . ? 
N1 C5 C6 117.48(13) . . ? 
C4 C5 C6 121.26(13) . . ? 
C11 C6 C7 119.16(13) . . ? 
C11 C6 C5 119.65(13) . . ? 
C7 C6 C5 121.18(13) . . ? 
O1 C7 C8 117.99(13) . . ? 
O1 C7 C6 122.13(13) . . ? 
C8 C7 C6 119.86(13) . . ? 
C9 C8 C7 120.17(13) . . ? 
C8 C9 C10 121.52(13) . . ? 
C9 C10 C11 118.87(13) . . ? 
C9 C10 C14 121.37(12) . . ? 
C11 C10 C14 119.75(12) . . ? 
C10 C11 C6 120.38(13) . . ? 
C10 C11 C12 120.45(13) . . ? 
C6 C11 C12 119.05(12) . . ? 
C13 C12 C11 115.10(13) . . ? 
C4 C13 C12 113.75(13) . . ? 
C15 C14 C10 115.10(11) . . ? 
C28 C15 C16 119.98(13) . . ? 
C28 C15 C14 119.60(13) . . ? 
C16 C15 C14 120.42(13) . . ? 
C15 C16 C21 120.22(13) . . ? 
C15 C16 C17 122.52(13) . . ? 
C21 C16 C17 117.24(13) . . ? 
C18 C17 C16 121.75(14) . . ? 
C17 C18 C19 120.50(14) . . ? 
C20 C19 C18 119.93(14) . . ? 
C19 C20 C21 121.05(14) . . ? 
C22 C21 C20 121.60(13) . . ? 
C22 C21 C16 118.87(13) . . ? 
C20 C21 C16 119.52(13) . . ? 
C21 C22 C23 121.66(13) . . ? 
C21 C22 C29 119.34(12) . . ? 
C23 C22 C29 119.00(12) . . ? 
C22 C23 C24 121.74(13) . . ? 
C22 C23 C28 118.81(13) . . ? 
C24 C23 C28 119.43(13) . . ? 
C25 C24 C23 120.98(14) . . ? 
C24 C25 C26 120.08(14) . . ? 
C27 C26 C25 120.82(14) . . ? 
C26 C27 C28 121.25(14) . . ? 
C15 C28 C23 120.13(13) . . ? 
C15 C28 C27 122.45(13) . . ? 
C23 C28 C27 117.42(13) . . ? 
N2 C29 C22 178.27(15) . . ? 
  
_refine_diff_density_max    0.754 
_refine_diff_density_min   -0.348 
_refine_diff_density_rms    0.054 
  
  
  
