 
data_P24042O_014
 
_audit_creation_method            'SHELXL-2019/3'
_shelx_SHELXL_version_number      '2019/3'
_chemical_name_systematic         ?
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          'C26 H36 N2 O2'
_chemical_formula_sum
 'C26 H36 N2 O2' 
_chemical_formula_weight          408.57

loop_
 _atom_type_symbol
 _atom_type_description
 _atom_type_scat_dispersion_real
 _atom_type_scat_dispersion_imag
 _atom_type_scat_source
 'C'  'C'   0.0030   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'   0.0059   0.0032
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O'  'O'   0.0105   0.0059
 '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                    5.2650(11)
_cell_length_b                    9.1090(18)
_cell_length_c                    24.390(5)
_cell_angle_alpha                 90
_cell_angle_beta                  95.74(3)
_cell_angle_gamma                 90
_cell_volume                      1163.9(4)
_cell_formula_units_Z             2
_cell_measurement_temperature     173(2)
_cell_measurement_reflns_used     24463
_cell_measurement_theta_min       0.401
_cell_measurement_theta_max       29.535
 
_exptl_crystal_description        'needle'
_exptl_crystal_colour             'colorless'
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_density_diffrn     1.166          
_exptl_crystal_F_000              444
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           0.092
_exptl_crystal_size_mid           0.019
_exptl_crystal_size_min           0.017
_exptl_absorpt_coefficient_mu     0.070
_shelx_estimated_absorpt_T_min    0.994
_shelx_estimated_absorpt_T_max    0.999
_exptl_absorpt_correction_type    'empirical'
_exptl_absorpt_correction_T_min   0.943
_exptl_absorpt_correction_T_max   1.000
_exptl_absorpt_process_details    'HKL3000sm Scalepack'
_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature       173(2)
_diffrn_radiation_wavelength      0.700
_diffrn_radiation_type            synchrotron
_diffrn_source                    'PLSII 2D bending magnet'
_diffrn_measurement_device_type   'Rayonix MX225HS CCD area detector'
_diffrn_measurement_method        'omega scan'
_diffrn_detector_area_resol_mean  ?
_diffrn_reflns_number             9673
_diffrn_reflns_av_unetI/netI      0.0549
_diffrn_reflns_av_R_equivalents   0.0721
_diffrn_reflns_limit_h_min        -6
_diffrn_reflns_limit_h_max        6
_diffrn_reflns_limit_k_min        -11
_diffrn_reflns_limit_k_max        11
_diffrn_reflns_limit_l_min        -31
_diffrn_reflns_limit_l_max        31
_diffrn_reflns_theta_min          1.653
_diffrn_reflns_theta_max          27.036
_diffrn_reflns_theta_full         24.835
_diffrn_measured_fraction_theta_max   0.977
_diffrn_measured_fraction_theta_full  0.982
_diffrn_reflns_Laue_measured_fraction_max    0.977
_diffrn_reflns_Laue_measured_fraction_full   0.982
_diffrn_reflns_point_group_measured_fraction_max   0.977
_diffrn_reflns_point_group_measured_fraction_full  0.982
_reflns_number_total              2608
_reflns_number_gt                 1767
_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        'PAL BL2D-SMDC Program'
_computing_cell_refinement        'HKL3000sm'
_computing_data_reduction         'HKL3000sm'
_computing_structure_solution     'SHELXS-2013/1 (Sheldrick, 2013)'
_computing_structure_refinement   'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics     ORTEP
_computing_publication_material   CIFTAB
_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)+(0.0411P)²+0.1422P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      direct
_atom_sites_solution_secondary    ?
_atom_sites_solution_hydrogens    mixed
_refine_ls_hydrogen_treatment     mixed
_refine_ls_extinction_method      'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_extinction_coef        0.076(5)
_refine_ls_extinction_expression
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_number_reflns          2608
_refine_ls_number_parameters      141
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0758
_refine_ls_R_factor_gt            0.0448
_refine_ls_wR_factor_ref          0.1126
_refine_ls_wR_factor_gt           0.1010
_refine_ls_goodness_of_fit_ref    1.025
_refine_ls_restrained_S_all       1.025
_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 1.0827(4) 0.4719(2) 0.17255(8) 0.0608(5) Uani 1 1 d . . . . .
H1A H 1.138738 0.436685 0.137750 0.091 Uiso 1 1 calc R U . . .
H1B H 1.228865 0.474707 0.200760 0.091 Uiso 1 1 calc R U . . .
H1C H 1.010951 0.570784 0.167296 0.091 Uiso 1 1 calc R U . . .
O2 O 0.8942(3) 0.37597(14) 0.18964(5) 0.0581(4) Uani 1 1 d . . . . .
C3 C 0.7571(3) 0.54616(17) 0.32096(6) 0.0371(4) Uani 1 1 d . . . . .
H3 H 0.795761 0.632427 0.342050 0.045 Uiso 1 1 calc R U . . .
C4 C 0.8602(3) 0.52880(17) 0.27118(6) 0.0391(4) Uani 1 1 d . . . . .
H4 H 0.969194 0.602154 0.258767 0.047 Uiso 1 1 calc R U . . .
C5 C 0.8043(3) 0.40518(18) 0.23981(6) 0.0419(4) Uani 1 1 d . . . . .
C6 C 0.6443(3) 0.29981(19) 0.25841(7) 0.0471(4) Uani 1 1 d . . . . .
H6 H 0.603450 0.214821 0.236724 0.056 Uiso 1 1 calc R U . . .
C7 C 0.5429(3) 0.31679(17) 0.30826(7) 0.0411(4) Uani 1 1 d . . . . .
H7 H 0.433885 0.243045 0.320424 0.049 Uiso 1 1 calc R U . . .
C8 C 0.5985(3) 0.44047(16) 0.34083(6) 0.0332(3) Uani 1 1 d . . . . .
N9 N 0.5081(2) 0.45731(13) 0.39250(5) 0.0351(3) Uani 1 1 d . . . . .
C10 C 0.4146(3) 0.60056(17) 0.41080(6) 0.0414(4) Uani 1 1 d . . . . .
H10A H 0.338194 0.663227 0.380335 0.050 Uiso 1 1 calc R U . . .
H10B H 0.542068 0.655817 0.435285 0.050 Uiso 1 1 calc R U . . .
C11 C 0.2165(3) 0.51780(17) 0.44168(7) 0.0404(4) Uani 1 1 d . . . . .
H11A H 0.039642 0.554417 0.433769 0.048 Uiso 1 1 calc R U . . .
H11B H 0.264266 0.508229 0.481827 0.048 Uiso 1 1 calc R U . . .
C12 C 0.2772(3) 0.38052(16) 0.40799(6) 0.0349(4) Uani 1 1 d . . . . .
H12 H 0.148(3) 0.3654(19) 0.3745(7) 0.052 Uiso 1 1 d . U . . .
C13 C 0.3227(3) 0.23699(17) 0.43857(6) 0.0375(4) Uani 1 1 d . . . . .
H13A H 0.457600 0.251302 0.469406 0.045 Uiso 1 1 calc R U . . .
H13B H 0.384734 0.163045 0.413303 0.045 Uiso 1 1 calc R U . . .
C14 C 0.0830(3) 0.17904(16) 0.46125(7) 0.0371(4) Uani 1 1 d . . . . .
H14A H 0.027606 0.250515 0.488228 0.045 Uiso 1 1 calc R U . . .
H14B H -0.055016 0.171368 0.430685 0.045 Uiso 1 1 calc R U . . .
C15 C 0.1196(3) 0.02987(17) 0.48907(7) 0.0406(4) Uani 1 1 d . . . . .
H15A H 0.178141 -0.041062 0.462264 0.049 Uiso 1 1 calc R U . . .
H15B H 0.255698 0.038082 0.520012 0.049 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
C1 O2 1.416(2) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
O2 C5 1.3813(18) . ?
C3 C4 1.387(2) . ?
C3 C8 1.393(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.377(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.383(2) . ?
C6 C7 1.385(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.393(2) . ?
C7 H7 0.9500 . ?
C8 N9 1.3993(18) . ?
N9 C10 1.4794(19) . ?
N9 C12 1.4841(18) . ?
C10 C11 1.543(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.547(2) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.512(2) . ?
C12 H12 1.019(19) . ?
C13 C14 1.523(2) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.522(2) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C15 1.517(3) 3_556 ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
 
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
O2 C1 H1A 109.5 . . ?
O2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C5 O2 C1 117.02(14) . . ?
C4 C3 C8 121.74(15) . . ?
C4 C3 H3 119.1 . . ?
C8 C3 H3 119.1 . . ?
C5 C4 C3 119.95(15) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C4 C5 O2 125.23(15) . . ?
C4 C5 C6 119.24(14) . . ?
O2 C5 C6 115.52(15) . . ?
C5 C6 C7 120.76(15) . . ?
C5 C6 H6 119.6 . . ?
C7 C6 H6 119.6 . . ?
C6 C7 C8 120.91(15) . . ?
C6 C7 H7 119.5 . . ?
C8 C7 H7 119.5 . . ?
C7 C8 C3 117.39(14) . . ?
C7 C8 N9 122.09(13) . . ?
C3 C8 N9 120.48(14) . . ?
C8 N9 C10 121.46(12) . . ?
C8 N9 C12 122.60(13) . . ?
C10 N9 C12 91.89(11) . . ?
N9 C10 C11 88.73(11) . . ?
N9 C10 H10A 113.9 . . ?
C11 C10 H10A 113.9 . . ?
N9 C10 H10B 113.9 . . ?
C11 C10 H10B 113.9 . . ?
H10A C10 H10B 111.1 . . ?
C10 C11 C12 87.15(11) . . ?
C10 C11 H11A 114.1 . . ?
C12 C11 H11A 114.1 . . ?
C10 C11 H11B 114.1 . . ?
C12 C11 H11B 114.1 . . ?
H11A C11 H11B 111.3 . . ?
N9 C12 C13 116.06(13) . . ?
N9 C12 C11 88.40(11) . . ?
C13 C12 C11 117.89(13) . . ?
N9 C12 H12 111.0(9) . . ?
C13 C12 H12 109.8(10) . . ?
C11 C12 H12 112.2(10) . . ?
C12 C13 C14 112.49(13) . . ?
C12 C13 H13A 109.1 . . ?
C14 C13 H13A 109.1 . . ?
C12 C13 H13B 109.1 . . ?
C14 C13 H13B 109.1 . . ?
H13A C13 H13B 107.8 . . ?
C15 C14 C13 113.49(12) . . ?
C15 C14 H14A 108.9 . . ?
C13 C14 H14A 108.9 . . ?
C15 C14 H14B 108.9 . . ?
C13 C14 H14B 108.9 . . ?
H14A C14 H14B 107.7 . . ?
C15 C15 C14 113.83(17) 3_556 . ?
C15 C15 H15A 108.8 3_556 . ?
C14 C15 H15A 108.8 . . ?
C15 C15 H15B 108.8 3_556 . ?
C14 C15 H15B 108.8 . . ?
H15A C15 H15B 107.7 . . ?
 
loop_
 _geom_torsion_atom_site_label_1
 _geom_torsion_atom_site_label_2
 _geom_torsion_atom_site_label_3
 _geom_torsion_atom_site_label_4
 _geom_torsion
 _geom_torsion_site_symmetry_1
 _geom_torsion_site_symmetry_2
 _geom_torsion_site_symmetry_3
 _geom_torsion_site_symmetry_4
 _geom_torsion_publ_flag
C8 C3 C4 C5 0.6(2) . . . . ?
C3 C4 C5 O2 179.73(15) . . . . ?
C3 C4 C5 C6 0.3(2) . . . . ?
C1 O2 C5 C4 8.1(2) . . . . ?
C1 O2 C5 C6 -172.41(16) . . . . ?
C4 C5 C6 C7 -0.7(3) . . . . ?
O2 C5 C6 C7 179.78(15) . . . . ?
C5 C6 C7 C8 0.3(3) . . . . ?
C6 C7 C8 C3 0.6(2) . . . . ?
C6 C7 C8 N9 -177.04(15) . . . . ?
C4 C3 C8 C7 -1.1(2) . . . . ?
C4 C3 C8 N9 176.63(14) . . . . ?
C7 C8 N9 C10 -139.70(16) . . . . ?
C3 C8 N9 C10 42.7(2) . . . . ?
C7 C8 N9 C12 -23.8(2) . . . . ?
C3 C8 N9 C12 158.63(14) . . . . ?
C8 N9 C10 C11 145.76(14) . . . . ?
C12 N9 C10 C11 15.06(12) . . . . ?
N9 C10 C11 C12 -14.44(11) . . . . ?
C8 N9 C12 C13 94.63(17) . . . . ?
C10 N9 C12 C13 -135.50(14) . . . . ?
C8 N9 C12 C11 -144.88(14) . . . . ?
C10 N9 C12 C11 -15.02(12) . . . . ?
C10 C11 C12 N9 14.40(11) . . . . ?
C10 C11 C12 C13 133.24(15) . . . . ?
N9 C12 C13 C14 170.29(13) . . . . ?
C11 C12 C13 C14 67.36(18) . . . . ?
C12 C13 C14 C15 176.35(14) . . . . ?
C13 C14 C15 C15 -179.01(18) . . . 3_556 ?
 
_refine_diff_density_max    0.157
_refine_diff_density_min   -0.126
_refine_diff_density_rms    0.033



