data_lly
_audit_creation_date               2019-08-27
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number       '2018/3'
_audit_contact_author_address      ?
_audit_contact_author_email        ?
_audit_contact_author_name         ''
_audit_contact_author_phone        ?
_publ_contact_author_id_orcid      ?
_publ_section_references
;
Dolomanov, O.V., Bourhis, L.J., Gildea, R.J, Howard, J.A.K. & Puschmann, H.
 (2009), J. Appl. Cryst. 42, 339-341.

Sheldrick, G.M. (2008). Acta Cryst. A64, 112-122.

Sheldrick, G.M. (2015). Acta Cryst. C71, 3-8.
;
_chemical_name_common              ?
_chemical_name_systematic          ?
_chemical_formula_moiety           'C21 H25 N O'
_chemical_formula_sum              'C21 H25 N O'
_chemical_formula_weight           307.42
_chemical_melting_point            ?
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'

_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.
;
_space_group_crystal_system        'monoclinic'
_space_group_IT_number             15
_space_group_name_H-M_alt          'C 1 2/c 1'
_space_group_name_Hall             '-C 2yc'
loop_
  _space_group_symop_operation_xyz
 'x, y, z'
 '-x, y, -z+1/2'
 'x+1/2, y+1/2, z'
 '-x+1/2, y+1/2, -z+1/2'
 '-x, -y, -z'
 'x, -y, z-1/2'
 '-x+1/2, -y+1/2, -z'
 'x+1/2, -y+1/2, z-1/2'

_cell_length_a                     18.3228(9)
_cell_length_b                     9.5884(5)
_cell_length_c                     19.9324(10)
_cell_angle_alpha                  90
_cell_angle_beta                   92.554(5)
_cell_angle_gamma                  90
_cell_volume                       3498.4(3)
_cell_formula_units_Z              8
_cell_measurement_reflns_used      4074
_cell_measurement_temperature      100.01(10)
_cell_measurement_theta_max        29.1950
_cell_measurement_theta_min        2.5850
_shelx_estimated_absorpt_T_max     ?
_shelx_estimated_absorpt_T_min     ?
_exptl_absorpt_coefficient_mu      0.071
_exptl_absorpt_correction_T_max    1.00000
_exptl_absorpt_correction_T_min    0.90406
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details     ?
_exptl_crystal_colour              colourless
_exptl_crystal_colour_primary      colourless
_exptl_crystal_density_diffrn      1.167
_exptl_crystal_density_meas        ?
_exptl_crystal_density_method      ?
_exptl_crystal_description         block
_exptl_crystal_F_000               1328
_exptl_crystal_size_max            0.12
_exptl_crystal_size_mid            0.11
_exptl_crystal_size_min            0.1
_exptl_transmission_factor_max     ?
_exptl_transmission_factor_min     ?
_diffrn_reflns_av_R_equivalents    0.0204
_diffrn_reflns_av_unetI/netI       0.0281
_diffrn_reflns_Laue_measured_fraction_full  1.000
_diffrn_reflns_Laue_measured_fraction_max  1.000
_diffrn_reflns_limit_h_max         21
_diffrn_reflns_limit_h_min         -17
_diffrn_reflns_limit_k_max         11
_diffrn_reflns_limit_k_min         -10
_diffrn_reflns_limit_l_max         23
_diffrn_reflns_limit_l_min         -23
_diffrn_reflns_number              7372
_diffrn_reflns_point_group_measured_fraction_full  1.000
_diffrn_reflns_point_group_measured_fraction_max  1.000
_diffrn_reflns_theta_full          24.998
_diffrn_reflns_theta_max           24.998
_diffrn_reflns_theta_min           2.045
_diffrn_ambient_environment        N~2~
_diffrn_ambient_temperature        100.01(10)
_diffrn_detector                   'CCD plate'
_diffrn_detector_area_resol_mean   5.2684
_diffrn_detector_type              AtlasS2
_diffrn_measured_fraction_theta_full  1.000
_diffrn_measured_fraction_theta_max  1.000
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω     34.00  91.00   1.00    6.50    --   11.74-178.00-120.00   57
  2  ω     20.00  47.00   1.00    6.50    --   11.74 -99.00 -90.00   27
  3  ω    -18.00  88.00   1.00    6.50    --   11.74  77.00  30.00  106
;
_diffrn_measurement_device         'four-circle diffractometer'
_diffrn_measurement_device_type    'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method         'ω scans'
_diffrn_orient_matrix_type        
 'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11        -0.0372257000
_diffrn_orient_matrix_UB_12        -0.0103769000
_diffrn_orient_matrix_UB_13        0.0069964000
_diffrn_orient_matrix_UB_21        -0.0035751000
_diffrn_orient_matrix_UB_22        0.0720762000
_diffrn_orient_matrix_UB_23        0.0071087000
_diffrn_orient_matrix_UB_31        -0.0101433000
_diffrn_orient_matrix_UB_32        0.0129882000
_diffrn_orient_matrix_UB_33        -0.0341989000
_diffrn_radiation_monochromator    mirror
_diffrn_radiation_probe            x-ray
_diffrn_radiation_type             MoK\a
_diffrn_radiation_wavelength       0.71073
_diffrn_source                     'micro-focus sealed X-ray tube'
_diffrn_source_type                'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage           0.000
_reflns_Friedel_fraction_full      .
_reflns_Friedel_fraction_max       .
_reflns_number_gt                  2751
_reflns_number_total               3089
_reflns_odcompleteness_completeness  99.97
_reflns_odcompleteness_iscentric   1
_reflns_odcompleteness_theta       26.32
_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.
;
_reflns_threshold_expression       'I > 2σ(I)'
_computing_cell_refinement         'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection         'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction          'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics      'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material    'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement    'ShelXL (Sheldrick, 2015)'
_computing_structure_solution      'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max           0.185
_refine_diff_density_min           -0.233
_refine_diff_density_rms           0.051
_refine_ls_extinction_coef         .
_refine_ls_extinction_method       none
_refine_ls_goodness_of_fit_ref     1.045
_refine_ls_hydrogen_treatment      constr
_refine_ls_matrix_type             full
_refine_ls_number_parameters       213
_refine_ls_number_reflns           3089
_refine_ls_number_restraints       0
_refine_ls_R_factor_all            0.0445
_refine_ls_R_factor_gt             0.0394
_refine_ls_restrained_S_all        1.045
_refine_ls_shift/su_max            0.000
_refine_ls_shift/su_mean           0.000
_refine_ls_structure_factor_coef   Fsqd
_refine_ls_weighting_details      
 'w=1/[σ²(Fo²)+(0.0462P)²+2.5006P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme        calc
_refine_ls_wR_factor_gt            0.0949
_refine_ls_wR_factor_ref           0.0986
_refine_special_details            ?
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
2.b Aromatic/amide H refined with riding coordinates:
 C14(H14), C3(H3), C4(H4), C10(H10), C5(H5), C13(H13), C12(H12), C11(H11)
2.c Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C18(H18A,H18B,H18C), C20(H20A,H20B,H20C), C19(H19A,H19B,
 H19C), C17(H17A,H17B,H17C)
;
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary       direct
_atom_sites_solution_secondary     ?
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 0.19996(5) 0.36262(9) 0.30321(5) 0.0196(2) Uani 1 1 d . . . . .
 N1 N 0.26978(6) 0.19793(11) 0.35672(5) 0.0140(2) Uani 1 1 d . . . . .
 C15 C 0.20709(7) 0.24157(13) 0.32125(6) 0.0146(3) Uani 1 1 d . . . . .
 C2 C 0.39342(7) 0.24573(14) 0.36533(6) 0.0156(3) Uani 1 1 d . . . . .
 C1 C 0.32422(7) 0.29493(13) 0.38036(6) 0.0147(3) Uani 1 1 d . . . . .
 C6 C 0.31480(7) 0.41813(14) 0.41637(6) 0.0161(3) Uani 1 1 d . . . . .
 C7 C 0.38551(7) 0.11391(14) 0.32336(6) 0.0163(3) Uani 1 1 d . . . . .
 C9 C 0.24279(7) 0.47380(14) 0.43534(6) 0.0164(3) Uani 1 1 d . . . . .
 C14 C 0.18936(7) 0.38750(15) 0.46090(6) 0.0182(3) Uani 1 1 d . . . . .
 H14 H 0.198753 0.292743 0.466291 0.022 Uiso 1 1 calc R . . . .
 C16 C 0.14440(7) 0.13620(14) 0.30880(7) 0.0172(3) Uani 1 1 d . . . . .
 C3 C 0.45555(7) 0.31829(14) 0.38581(7) 0.0186(3) Uani 1 1 d . . . . .
 H3 H 0.501617 0.285099 0.376180 0.022 Uiso 1 1 calc R . . . .
 C8 C 0.30848(7) 0.06634(13) 0.34147(7) 0.0162(3) Uani 1 1 d . . . . .
 H8A H 0.284115 0.017891 0.304075 0.019 Uiso 1 1 calc R . . . .
 H8B H 0.310850 0.005040 0.380215 0.019 Uiso 1 1 calc R . . . .
 C21 C 0.38514(7) 0.15546(15) 0.24882(7) 0.0196(3) Uani 1 1 d . . . . .
 H21A H 0.345800 0.219446 0.239010 0.029 Uiso 1 1 calc GR . . . .
 H21B H 0.378655 0.073685 0.221411 0.029 Uiso 1 1 calc GR . . . .
 H21C H 0.430722 0.199181 0.239512 0.029 Uiso 1 1 calc GR . . . .
 C4 C 0.44781(7) 0.44198(15) 0.42112(7) 0.0208(3) Uani 1 1 d . . . . .
 H4 H 0.489040 0.492761 0.434919 0.025 Uiso 1 1 calc R . . . .
 C10 C 0.22725(8) 0.61555(15) 0.42816(7) 0.0223(3) Uani 1 1 d . . . . .
 H10 H 0.262181 0.675095 0.411501 0.027 Uiso 1 1 calc R . . . .
 C5 C 0.37914(7) 0.49009(15) 0.43590(7) 0.0197(3) Uani 1 1 d . . . . .
 H5 H 0.375423 0.573110 0.459627 0.024 Uiso 1 1 calc R . . . .
 C13 C 0.12252(7) 0.44082(16) 0.47839(7) 0.0223(3) Uani 1 1 d . . . . .
 H13 H 0.087523 0.381872 0.495392 0.027 Uiso 1 1 calc R . . . .
 C18 C 0.14429(8) 0.09042(15) 0.23504(7) 0.0233(3) Uani 1 1 d . . . . .
 H18A H 0.140381 0.171043 0.206549 0.035 Uiso 1 1 calc GR . . . .
 H18B H 0.103517 0.029663 0.225393 0.035 Uiso 1 1 calc GR . . . .
 H18C H 0.188896 0.041906 0.227024 0.035 Uiso 1 1 calc GR . . . .
 C20 C 0.44254(7) 0.00222(14) 0.34009(7) 0.0212(3) Uani 1 1 d . . . . .
 H20A H 0.489983 0.036100 0.329563 0.032 Uiso 1 1 calc GR . . . .
 H20B H 0.431412 -0.080100 0.314200 0.032 Uiso 1 1 calc GR . . . .
 H20C H 0.442166 -0.019751 0.387066 0.032 Uiso 1 1 calc GR . . . .
 C19 C 0.07340(7) 0.21567(15) 0.32109(7) 0.0221(3) Uani 1 1 d . . . . .
 H19A H 0.073653 0.245847 0.367019 0.033 Uiso 1 1 calc GR . . . .
 H19B H 0.032320 0.155396 0.311924 0.033 Uiso 1 1 calc GR . . . .
 H19C H 0.069869 0.295400 0.291994 0.033 Uiso 1 1 calc GR . . . .
 C12 C 0.10769(8) 0.58200(16) 0.47060(7) 0.0259(3) Uani 1 1 d . . . . .
 H12 H 0.062788 0.617910 0.482104 0.031 Uiso 1 1 calc R . . . .
 C17 C 0.14735(7) 0.00980(15) 0.35576(7) 0.0229(3) Uani 1 1 d . . . . .
 H17A H 0.186851 -0.050093 0.344200 0.034 Uiso 1 1 calc GR . . . .
 H17B H 0.102115 -0.040553 0.351188 0.034 Uiso 1 1 calc GR . . . .
 H17C H 0.154931 0.040782 0.401335 0.034 Uiso 1 1 calc GR . . . .
 C11 C 0.16026(8) 0.66877(16) 0.44559(7) 0.0269(4) Uani 1 1 d . . . . .
 H11 H 0.150660 0.763496 0.440409 0.032 Uiso 1 1 calc R . . . .


_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 C15 1.2203(16) . ?
 N1 C15 1.3865(16) . ?
 N1 C1 1.4283(16) . ?
 N1 C8 1.4854(16) . ?
 C15 C16 1.5416(18) . ?
 C2 C1 1.3977(18) . ?
 C2 C7 1.5190(18) . ?
 C2 C3 1.3804(19) . ?
 C1 C6 1.3969(19) . ?
 C6 C9 1.4877(18) . ?
 C6 C5 1.4059(19) . ?
 C7 C8 1.5415(17) . ?
 C7 C21 1.5380(18) . ?
 C7 C20 1.5227(18) . ?
 C9 C14 1.3954(19) . ?
 C9 C10 1.3947(19) . ?
 C14 H14 0.9300 . ?
 C14 C13 1.3860(19) . ?
 C16 C18 1.5342(19) . ?
 C16 C19 1.5367(18) . ?
 C16 C17 1.5308(19) . ?
 C3 H3 0.9300 . ?
 C3 C4 1.390(2) . ?
 C8 H8A 0.9700 . ?
 C8 H8B 0.9700 . ?
 C21 H21A 0.9600 . ?
 C21 H21B 0.9600 . ?
 C21 H21C 0.9600 . ?
 C4 H4 0.9300 . ?
 C4 C5 1.3841(19) . ?
 C10 H10 0.9300 . ?
 C10 C11 1.388(2) . ?
 C5 H5 0.9300 . ?
 C13 H13 0.9300 . ?
 C13 C12 1.388(2) . ?
 C18 H18A 0.9600 . ?
 C18 H18B 0.9600 . ?
 C18 H18C 0.9600 . ?
 C20 H20A 0.9600 . ?
 C20 H20B 0.9600 . ?
 C20 H20C 0.9600 . ?
 C19 H19A 0.9600 . ?
 C19 H19B 0.9600 . ?
 C19 H19C 0.9600 . ?
 C12 H12 0.9300 . ?
 C12 C11 1.382(2) . ?
 C17 H17A 0.9600 . ?
 C17 H17B 0.9600 . ?
 C17 H17C 0.9600 . ?
 C11 H11 0.9300 . ?

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
 C15 N1 C1 121.49(11) . . ?
 C15 N1 C8 122.97(10) . . ?
 C1 N1 C8 106.74(10) . . ?
 O1 C15 N1 120.84(12) . . ?
 O1 C15 C16 120.45(11) . . ?
 N1 C15 C16 118.60(11) . . ?
 C1 C2 C7 109.50(11) . . ?
 C3 C2 C1 120.70(12) . . ?
 C3 C2 C7 129.74(12) . . ?
 C2 C1 N1 109.65(11) . . ?
 C6 C1 N1 128.29(11) . . ?
 C6 C1 C2 121.98(12) . . ?
 C1 C6 C9 124.42(12) . . ?
 C1 C6 C5 115.84(12) . . ?
 C5 C6 C9 119.73(12) . . ?
 C2 C7 C8 100.55(10) . . ?
 C2 C7 C21 108.22(11) . . ?
 C2 C7 C20 114.64(11) . . ?
 C21 C7 C8 109.76(11) . . ?
 C20 C7 C8 111.54(11) . . ?
 C20 C7 C21 111.55(11) . . ?
 C14 C9 C6 121.64(12) . . ?
 C10 C9 C6 120.20(12) . . ?
 C10 C9 C14 118.17(12) . . ?
 C9 C14 H14 119.5 . . ?
 C13 C14 C9 121.01(13) . . ?
 C13 C14 H14 119.5 . . ?
 C18 C16 C15 108.12(10) . . ?
 C18 C16 C19 109.25(11) . . ?
 C19 C16 C15 106.22(10) . . ?
 C17 C16 C15 114.50(11) . . ?
 C17 C16 C18 110.97(11) . . ?
 C17 C16 C19 107.59(11) . . ?
 C2 C3 H3 120.7 . . ?
 C2 C3 C4 118.58(12) . . ?
 C4 C3 H3 120.7 . . ?
 N1 C8 C7 104.30(10) . . ?
 N1 C8 H8A 110.9 . . ?
 N1 C8 H8B 110.9 . . ?
 C7 C8 H8A 110.9 . . ?
 C7 C8 H8B 110.9 . . ?
 H8A C8 H8B 108.9 . . ?
 C7 C21 H21A 109.5 . . ?
 C7 C21 H21B 109.5 . . ?
 C7 C21 H21C 109.5 . . ?
 H21A C21 H21B 109.5 . . ?
 H21A C21 H21C 109.5 . . ?
 H21B C21 H21C 109.5 . . ?
 C3 C4 H4 119.8 . . ?
 C5 C4 C3 120.43(12) . . ?
 C5 C4 H4 119.8 . . ?
 C9 C10 H10 119.6 . . ?
 C11 C10 C9 120.76(13) . . ?
 C11 C10 H10 119.6 . . ?
 C6 C5 H5 118.8 . . ?
 C4 C5 C6 122.45(13) . . ?
 C4 C5 H5 118.8 . . ?
 C14 C13 H13 119.9 . . ?
 C14 C13 C12 120.16(13) . . ?
 C12 C13 H13 119.9 . . ?
 C16 C18 H18A 109.5 . . ?
 C16 C18 H18B 109.5 . . ?
 C16 C18 H18C 109.5 . . ?
 H18A C18 H18B 109.5 . . ?
 H18A C18 H18C 109.5 . . ?
 H18B C18 H18C 109.5 . . ?
 C7 C20 H20A 109.5 . . ?
 C7 C20 H20B 109.5 . . ?
 C7 C20 H20C 109.5 . . ?
 H20A C20 H20B 109.5 . . ?
 H20A C20 H20C 109.5 . . ?
 H20B C20 H20C 109.5 . . ?
 C16 C19 H19A 109.5 . . ?
 C16 C19 H19B 109.5 . . ?
 C16 C19 H19C 109.5 . . ?
 H19A C19 H19B 109.5 . . ?
 H19A C19 H19C 109.5 . . ?
 H19B C19 H19C 109.5 . . ?
 C13 C12 H12 120.3 . . ?
 C11 C12 C13 119.42(13) . . ?
 C11 C12 H12 120.3 . . ?
 C16 C17 H17A 109.5 . . ?
 C16 C17 H17B 109.5 . . ?
 C16 C17 H17C 109.5 . . ?
 H17A C17 H17B 109.5 . . ?
 H17A C17 H17C 109.5 . . ?
 H17B C17 H17C 109.5 . . ?
 C10 C11 H11 119.8 . . ?
 C12 C11 C10 120.48(14) . . ?
 C12 C11 H11 119.8 . . ?


_olex2_submission_special_instructions  'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max  1.141
_oxdiff_exptl_absorpt_empirical_full_min  0.880
