 
data_20230510_BL_0m_a
 
_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
 'C21 H15 N O' 
_chemical_formula_weight          297.34

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       orthorhombic
_space_group_IT_number            61
_space_group_name_H-M_alt         'P b c a'
_space_group_name_Hall            '-P 2ac 2ab'
 
_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, z+1/2'
 '-x, y+1/2, -z+1/2'
 'x+1/2, -y+1/2, -z'
 '-x, -y, -z'
 'x-1/2, y, -z-1/2'
 'x, -y-1/2, z-1/2'
 '-x-1/2, y-1/2, z'
 
_cell_length_a                    7.3527(2)
_cell_length_b                    16.9695(6)
_cell_length_c                    24.5823(9)
_cell_angle_alpha                 90
_cell_angle_beta                  90
_cell_angle_gamma                 90
_cell_volume                      3067.17(18)
_cell_formula_units_Z             8
_cell_measurement_temperature     200(2)
_cell_measurement_reflns_used    8910
_cell_measurement_theta_min        3.13
_cell_measurement_theta_max       56.54
 
_exptl_crystal_description        block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_density_diffrn     1.288          
_exptl_crystal_F_000              1248
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           0.32
_exptl_crystal_size_mid           0.24
_exptl_crystal_size_min           0.17
_exptl_absorpt_coefficient_mu     0.394
_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       200(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             30863
_diffrn_reflns_av_unetI/netI      0.0283
_diffrn_reflns_av_R_equivalents   0.0487
_diffrn_reflns_limit_h_min        -8
_diffrn_reflns_limit_h_max        9
_diffrn_reflns_limit_k_min        -20
_diffrn_reflns_limit_k_max        21
_diffrn_reflns_limit_l_min        -30
_diffrn_reflns_limit_l_max        29
_diffrn_reflns_theta_min          3.128
_diffrn_reflns_theta_max          57.087
_diffrn_reflns_theta_full         53.594
_diffrn_measured_fraction_theta_max   0.999
_diffrn_measured_fraction_theta_full  1.000
_diffrn_reflns_Laue_measured_fraction_max    0.999
_diffrn_reflns_Laue_measured_fraction_full   1.000
_diffrn_reflns_point_group_measured_fraction_max   0.999
_diffrn_reflns_point_group_measured_fraction_full  1.000
_reflns_number_total              3148
_reflns_number_gt                 2413
_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+0.2148P] 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      'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef        0.0037(4)
_refine_ls_extinction_expression
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_number_reflns          3148
_refine_ls_number_parameters      210
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0613
_refine_ls_R_factor_gt            0.0444
_refine_ls_wR_factor_ref          0.1403
_refine_ls_wR_factor_gt           0.1244
_refine_ls_goodness_of_fit_ref    0.970
_refine_ls_restrained_S_all       0.970
_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 0.38234(15) 0.41436(7) 0.79186(5) 0.0327(3) Uani 1 1 d . . . . .
C2 C 0.41692(15) 0.45411(7) 0.74089(5) 0.0318(3) Uani 1 1 d . . . . .
C3 C 0.39177(16) 0.41835(7) 0.68965(5) 0.0342(3) Uani 1 1 d . . . . .
H3 H 0.3418 0.3668 0.6879 0.041 Uiso 1 1 calc R U . . .
C4 C 0.43792(16) 0.45630(8) 0.64199(5) 0.0372(3) Uani 1 1 d . . . . .
C5 C 0.41671(18) 0.41591(8) 0.58886(5) 0.0399(3) Uani 1 1 d . . . . .
C6 C 0.2608(2) 0.37296(8) 0.57723(6) 0.0473(4) Uani 1 1 d . . . . .
H6 H 0.1658 0.3702 0.6033 0.057 Uiso 1 1 calc R U . . .
C7 C 0.2421(3) 0.33412(10) 0.52806(6) 0.0597(4) Uani 1 1 d . . . . .
H7 H 0.1348 0.3048 0.5208 0.072 Uiso 1 1 calc R U . . .
C8 C 0.3777(3) 0.33759(11) 0.48974(7) 0.0668(5) Uani 1 1 d . . . . .
H8 H 0.3646 0.3107 0.4561 0.080 Uiso 1 1 calc R U . . .
C9 C 0.5326(3) 0.38031(13) 0.50049(7) 0.0701(6) Uani 1 1 d . . . . .
H9 H 0.6265 0.3831 0.4740 0.084 Uiso 1 1 calc R U . . .
C10 C 0.5527(2) 0.41932(10) 0.54962(6) 0.0568(4) Uani 1 1 d . . . . .
H10 H 0.6602 0.4487 0.5566 0.068 Uiso 1 1 calc R U . . .
C11 C 0.50897(18) 0.53329(9) 0.64530(6) 0.0431(4) Uani 1 1 d . . . . .
H11 H 0.5412 0.5603 0.6128 0.052 Uiso 1 1 calc R U . . .
C12 C 0.53229(18) 0.56975(8) 0.69416(6) 0.0423(3) Uani 1 1 d . . . . .
H12 H 0.5791 0.6219 0.6950 0.051 Uiso 1 1 calc R U . . .
C13 C 0.48852(16) 0.53181(7) 0.74341(5) 0.0344(3) Uani 1 1 d . . . . .
C14 C 0.51593(16) 0.56773(8) 0.79598(6) 0.0368(3) Uani 1 1 d . . . . .
C15 C 0.57956(19) 0.64536(8) 0.80327(7) 0.0486(4) Uani 1 1 d . . . . .
H15 H 0.6087 0.6766 0.7724 0.058 Uiso 1 1 calc R U . . .
C16 C 0.5998(2) 0.67612(9) 0.85435(7) 0.0540(4) Uani 1 1 d . . . . .
H16 H 0.6419 0.7287 0.8586 0.065 Uiso 1 1 calc R U . . .
C17 C 0.55942(19) 0.63135(9) 0.90026(7) 0.0531(4) Uani 1 1 d . . . . .
H17 H 0.5730 0.6536 0.9355 0.064 Uiso 1 1 calc R U . . .
C18 C 0.50000(19) 0.55501(9) 0.89472(6) 0.0465(4) Uani 1 1 d . . . . .
H18 H 0.4742 0.5242 0.9261 0.056 Uiso 1 1 calc R U . . .
C19 C 0.47744(16) 0.52253(8) 0.84255(6) 0.0370(3) Uani 1 1 d . . . . .
C20 C 0.30461(16) 0.33170(7) 0.79492(5) 0.0354(3) Uani 1 1 d . . . . .
C21 C 0.3391(2) 0.28611(9) 0.84607(6) 0.0504(4) Uani 1 1 d . . . . .
H21A H 0.2656 0.2379 0.8459 0.076 Uiso 1 1 calc R U . . .
H21B H 0.3060 0.3184 0.8776 0.076 Uiso 1 1 calc R U . . .
H21C H 0.4682 0.2722 0.8482 0.076 Uiso 1 1 calc R U . . .
N1 N 0.41376(14) 0.44558(6) 0.83972(4) 0.0361(3) Uani 1 1 d . . . . .
O1 O 0.21519(13) 0.30370(5) 0.75816(4) 0.0448(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 N1 1.3108(15) . ?
C1 C2 1.4454(17) . ?
C1 C20 1.5166(18) . ?
C2 C3 1.4103(17) . ?
C2 C13 1.4211(18) . ?
C3 C4 1.3794(17) . ?
C4 C11 1.409(2) . ?
C4 C5 1.4831(18) . ?
C5 C6 1.388(2) . ?
C5 C10 1.3904(19) . ?
C6 C7 1.384(2) . ?
C7 C8 1.372(2) . ?
C8 C9 1.376(3) . ?
C9 C10 1.385(2) . ?
C11 C12 1.362(2) . ?
C12 C13 1.4087(19) . ?
C13 C14 1.4429(18) . ?
C14 C19 1.407(2) . ?
C14 C15 1.4095(19) . ?
C15 C16 1.368(2) . ?
C16 C17 1.392(2) . ?
C17 C18 1.374(2) . ?
C18 C19 1.4056(19) . ?
C19 N1 1.3889(17) . ?
C20 O1 1.2145(15) . ?
C20 C21 1.4979(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
N1 C1 C2 123.94(11) . . ?
N1 C1 C20 113.31(11) . . ?
C2 C1 C20 122.75(11) . . ?
C3 C2 C13 119.13(11) . . ?
C3 C2 C1 123.39(11) . . ?
C13 C2 C1 117.40(11) . . ?
C4 C3 C2 121.70(12) . . ?
C3 C4 C11 118.36(12) . . ?
C3 C4 C5 120.41(12) . . ?
C11 C4 C5 121.22(11) . . ?
C6 C5 C10 118.21(13) . . ?
C6 C5 C4 120.72(12) . . ?
C10 C5 C4 121.07(13) . . ?
C7 C6 C5 120.79(14) . . ?
C8 C7 C6 120.48(17) . . ?
C7 C8 C9 119.46(16) . . ?
C8 C9 C10 120.50(16) . . ?
C9 C10 C5 120.56(16) . . ?
C12 C11 C4 121.25(12) . . ?
C11 C12 C13 121.45(13) . . ?
C12 C13 C2 118.11(12) . . ?
C12 C13 C14 123.01(12) . . ?
C2 C13 C14 118.87(11) . . ?
C19 C14 C15 118.22(13) . . ?
C19 C14 C13 118.06(12) . . ?
C15 C14 C13 123.72(13) . . ?
C16 C15 C14 120.63(15) . . ?
C15 C16 C17 120.83(14) . . ?
C18 C17 C16 120.13(14) . . ?
C17 C18 C19 119.85(15) . . ?
N1 C19 C18 117.01(13) . . ?
N1 C19 C14 122.65(12) . . ?
C18 C19 C14 120.32(13) . . ?
O1 C20 C21 120.96(12) . . ?
O1 C20 C1 121.93(12) . . ?
C21 C20 C1 117.10(11) . . ?
C1 N1 C19 118.98(11) . . ?
 
_refine_diff_density_max    0.247
_refine_diff_density_min   -0.180
_refine_diff_density_rms    0.060



