data_exp_1391
_audit_creation_date               2020-09-01
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number       '2017/1'
_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. (2015). Acta Cryst. A71, 3-8.

Sheldrick, G.M. (2015). Acta Cryst. C71, 3-8.
;
_chemical_name_common              ?
_chemical_name_systematic          ?
_chemical_formula_moiety           'C40 H46 N2 O2'
_chemical_formula_sum              'C40 H46 N2 O2'
_chemical_formula_weight           586.79
_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' 0.0181 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'

_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             14
_space_group_name_H-M_alt          'P 1 21/n 1'
_space_group_name_Hall             '-P 2yn'
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                     6.0491(3)
_cell_length_b                     18.1428(5)
_cell_length_c                     15.3109(5)
_cell_angle_alpha                  90
_cell_angle_beta                   97.068(4)
_cell_angle_gamma                  90
_cell_volume                       1667.57(11)
_cell_formula_units_Z              2
_cell_measurement_reflns_used      3766
_cell_measurement_temperature      100.01(10)
_cell_measurement_theta_max        74.1200
_cell_measurement_theta_min        3.7780
_shelx_estimated_absorpt_T_max     0.957
_shelx_estimated_absorpt_T_min     0.844
_exptl_absorpt_coefficient_mu      0.549
_exptl_absorpt_correction_T_max    1.00000
_exptl_absorpt_correction_T_min    0.58524
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.32a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details     ?
_exptl_crystal_colour              'clear dark green'
_exptl_crystal_colour_lustre       clear
_exptl_crystal_colour_modifier     dark
_exptl_crystal_colour_primary      green
_exptl_crystal_density_diffrn      1.169
_exptl_crystal_density_meas        ?
_exptl_crystal_density_method      ?
_exptl_crystal_description         needle
_exptl_crystal_F_000               632
_exptl_crystal_size_max            0.32
_exptl_crystal_size_mid            0.12
_exptl_crystal_size_min            0.08
_exptl_transmission_factor_max     ?
_exptl_transmission_factor_min     ?
_diffrn_reflns_av_R_equivalents    0.1332
_diffrn_reflns_av_unetI/netI       0.0823
_diffrn_reflns_Laue_measured_fraction_full  0.995
_diffrn_reflns_Laue_measured_fraction_max  0.995
_diffrn_reflns_limit_h_max         7
_diffrn_reflns_limit_h_min         -5
_diffrn_reflns_limit_k_max         21
_diffrn_reflns_limit_k_min         -18
_diffrn_reflns_limit_l_max         18
_diffrn_reflns_limit_l_min         -17
_diffrn_reflns_number              14335
_diffrn_reflns_point_group_measured_fraction_full  0.995
_diffrn_reflns_point_group_measured_fraction_max  0.995
_diffrn_reflns_theta_full          67.058
_diffrn_reflns_theta_max           67.058
_diffrn_reflns_theta_min           3.795
_diffrn_ambient_environment        N~2~
_diffrn_ambient_temperature        100.01(10)
_diffrn_detector                   'CCD plate'
_diffrn_detector_area_resol_mean   ?
_diffrn_measured_fraction_theta_full  0.995
_diffrn_measured_fraction_theta_max  0.995
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω    -87.00 -60.00   1.00    2.00    --    0.00 -57.00 120.00   27
  2  ω     -3.00  62.00   1.00    2.00    --    0.00  19.00-120.00   65
  3  ω    -29.00  -3.00   1.00    2.00    --    0.00 -77.00-120.00   26
  4  ω    -19.00  23.00   1.00    2.00    --    0.00 -57.00 120.00   42
  5  ω    -87.00 -47.00   1.00    2.00    --    0.00 -77.00-120.00   40
  6  ω    -88.00  21.00   1.00    2.00    --    0.00 -57.00 -90.00  109
  7  ω      6.00  65.00   1.00    2.00    --   95.80 -15.00 150.00   59
  8  ω      9.00 119.00   1.00    2.00    --   95.80 -61.00 150.00  110
  9  ω     76.00 181.00   1.00    2.00    --   95.80  45.00  90.00  105
 10  ω     87.00 127.00   1.00    2.00    --   95.80 -82.00 -30.00   40
 11  ω      9.00 128.00   1.00    2.00    --   95.80 -82.00 -90.00  119
 12  ω      6.00 119.00   1.00    2.00    --   95.80 -61.00 -90.00  113
 13  ω     27.00  53.00   1.00    2.00    --   95.80 -61.00  30.00   26
 14  ω     85.00 111.00   1.00    2.00    --   95.80 -61.00  30.00   26
 15  ω     69.00 109.00   1.00    2.00    --   95.80 -82.00  60.00   40
 16  ω     75.00 179.00   1.00    2.00    --   95.80  45.00 120.00  104
 17  ω     76.00 101.00   1.00    2.00    --   95.80 -82.00 -60.00   25
 18  ω     82.00 109.00   1.00    2.00    --   95.80 -82.00-180.00   27
 19  ω     32.00 105.00   1.00    2.00    --   95.80 -82.00 150.00   73
 20  ω     12.00 113.00   1.00    2.00    --   95.80 -15.00 -60.00  101
;
_diffrn_measurement_device         'four-circle diffractometer'
_diffrn_measurement_device_type    'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method         'ω scans'
_diffrn_orient_matrix_type        
 'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11        -0.1200463000
_diffrn_orient_matrix_UB_12        0.0222631000
_diffrn_orient_matrix_UB_13        0.0790886000
_diffrn_orient_matrix_UB_21        0.0046693000
_diffrn_orient_matrix_UB_22        -0.0808567000
_diffrn_orient_matrix_UB_23        0.0309376000
_diffrn_orient_matrix_UB_31        0.2266525000
_diffrn_orient_matrix_UB_32        0.0134628000
_diffrn_orient_matrix_UB_33        0.0554111000
_diffrn_radiation_monochromator    graphite
_diffrn_radiation_probe            x-ray
_diffrn_radiation_type             CuK\a
_diffrn_radiation_wavelength       1.54184
_diffrn_source                     'fine-focus sealed X-ray tube'
_diffrn_source_type                'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage           0.000
_reflns_Friedel_fraction_full      .
_reflns_Friedel_fraction_max       .
_reflns_number_gt                  2029
_reflns_number_total               2965
_reflns_odcompleteness_completeness  99.90
_reflns_odcompleteness_iscentric   1
_reflns_odcompleteness_theta       66.97
_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 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_collection         'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_reduction          'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_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      'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max           0.348
_refine_diff_density_min           -0.451
_refine_diff_density_rms           0.080
_refine_ls_extinction_coef         .
_refine_ls_extinction_method       none
_refine_ls_goodness_of_fit_ref     1.033
_refine_ls_hydrogen_treatment      constr
_refine_ls_matrix_type             full
_refine_ls_number_parameters       205
_refine_ls_number_reflns           2965
_refine_ls_number_restraints       6
_refine_ls_R_factor_all            0.1024
_refine_ls_R_factor_gt             0.0758
_refine_ls_restrained_S_all        1.115
_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)+(0.1505P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme        calc
_refine_ls_wR_factor_gt            0.2092
_refine_ls_wR_factor_ref           0.2387
_refine_special_details            ?
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C16) \\sim Ueq: with sigma of 0.002 and sigma for terminal atoms of 0.004
3.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C8(H8), C9(H9), C11(H11)
3.b Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C18(H18A,H18B,
 H18C), C19(H19A,H19B,H19C), C20(H20A,H20B,H20C)
;
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary       dual
_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
 C1 C 0.7616(5) 0.64306(12) 0.35340(17) 0.0255(6) Uani 1 1 d . . . . .
 C2 C 0.6261(5) 0.65488(12) 0.27335(17) 0.0257(6) Uani 1 1 d . . . . .
 C3 C 0.4808(5) 0.71438(12) 0.27171(17) 0.0277(6) Uani 1 1 d . . . . .
 H3 H 0.389153 0.723777 0.219569 0.033 Uiso 1 1 calc R . . . .
 C4 C 0.4633(5) 0.76104(13) 0.34323(17) 0.0286(7) Uani 1 1 d . . . . .
 C5 C 0.5977(5) 0.74651(13) 0.42065(17) 0.0306(7) Uani 1 1 d . . . . .
 H5 H 0.585869 0.775754 0.469751 0.037 Uiso 1 1 calc R . . . .
 C6 C 0.7519(5) 0.68851(13) 0.42684(17) 0.0275(6) Uani 1 1 d . . . . .
 C7 C 1.0578(5) 0.63206(13) 0.50156(17) 0.0281(7) Uani 1 1 d . . . . .
 C8 C 1.2332(5) 0.62561(13) 0.57311(17) 0.0311(7) Uani 1 1 d . . . . .
 H8 H 1.232061 0.656164 0.621824 0.037 Uiso 1 1 calc R . . . .
 C9 C 1.4002(5) 0.57627(13) 0.57167(17) 0.0295(7) Uani 1 1 d . . . . .
 H9 H 1.512212 0.574896 0.619036 0.035 Uiso 1 1 calc R . . . .
 C10 C 1.4117(5) 0.52600(12) 0.50018(17) 0.0277(7) Uani 1 1 d . . . . .
 C11 C 1.2368(5) 0.53221(12) 0.42886(17) 0.0277(7) Uani 1 1 d . . . . .
 H11 H 1.235549 0.500816 0.380795 0.033 Uiso 1 1 calc R . . . .
 C12 C 1.0728(5) 0.58284(12) 0.42979(17) 0.0278(7) Uani 1 1 d . . . . .
 C13 C 0.3109(5) 0.82913(13) 0.33183(18) 0.0318(7) Uani 1 1 d . . . . .
 C14 C 0.4181(6) 0.88496(15) 0.2762(3) 0.0601(11) Uani 1 1 d . . . . .
 H14A H 0.324972 0.927830 0.267623 0.090 Uiso 1 1 calc GR . . . .
 H14B H 0.435825 0.863540 0.220183 0.090 Uiso 1 1 calc GR . . . .
 H14C H 0.561357 0.898796 0.305758 0.090 Uiso 1 1 calc GR . . . .
 C15 C 0.0839(6) 0.80964(16) 0.2837(3) 0.0572(11) Uani 1 1 d . . . . .
 H15A H -0.011301 0.852111 0.281394 0.086 Uiso 1 1 calc GR . . . .
 H15B H 0.019308 0.770497 0.314296 0.086 Uiso 1 1 calc GR . . . .
 H15C H 0.100107 0.793979 0.224919 0.086 Uiso 1 1 calc GR . . . .
 C16 C 0.2803(8) 0.8629(2) 0.4195(3) 0.0880(15) Uani 1 1 d . U . . .
 H16A H 0.422336 0.878236 0.448814 0.132 Uiso 1 1 calc GR . . . .
 H16B H 0.215682 0.827225 0.455037 0.132 Uiso 1 1 calc GR . . . .
 H16C H 0.183515 0.904894 0.410412 0.132 Uiso 1 1 calc GR . . . .
 C17 C 0.6432(5) 0.60626(12) 0.19242(17) 0.0260(6) Uani 1 1 d . . . . .
 C18 C 0.8774(5) 0.61171(14) 0.16455(18) 0.0325(7) Uani 1 1 d . . . . .
 H18A H 0.905331 0.661566 0.147983 0.049 Uiso 1 1 calc GR . . . .
 H18B H 0.888137 0.579615 0.115399 0.049 Uiso 1 1 calc GR . . . .
 H18C H 0.985412 0.597367 0.212791 0.049 Uiso 1 1 calc GR . . . .
 C19 C 0.5901(5) 0.52558(12) 0.21378(18) 0.0332(7) Uani 1 1 d . . . . .
 H19A H 0.698108 0.507938 0.260279 0.050 Uiso 1 1 calc GR . . . .
 H19B H 0.595115 0.495711 0.162304 0.050 Uiso 1 1 calc GR . . . .
 H19C H 0.444110 0.522880 0.232046 0.050 Uiso 1 1 calc GR . . . .
 C20 C 0.4758(5) 0.62946(13) 0.11392(17) 0.0322(7) Uani 1 1 d . . . . .
 H20A H 0.327452 0.626549 0.129897 0.048 Uiso 1 1 calc GR . . . .
 H20B H 0.488763 0.597181 0.065127 0.048 Uiso 1 1 calc GR . . . .
 H20C H 0.506197 0.679173 0.097556 0.048 Uiso 1 1 calc GR . . . .
 N1 N 0.8987(4) 0.68155(11) 0.50389(14) 0.0298(6) Uani 1 1 d . . . . .
 O1 O 0.9122(3) 0.58586(8) 0.35794(11) 0.0284(5) 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 C2 1.405(3) . ?
 C1 C6 1.402(4) . ?
 C1 O1 1.377(3) . ?
 C2 C3 1.390(3) . ?
 C2 C17 1.535(3) . ?
 C3 H3 0.9300 . ?
 C3 C4 1.398(4) . ?
 C4 C5 1.378(4) . ?
 C4 C13 1.538(3) . ?
 C5 H5 0.9300 . ?
 C5 C6 1.401(4) . ?
 C6 N1 1.392(3) . ?
 C7 C8 1.433(3) . ?
 C7 C12 1.428(4) . ?
 C7 N1 1.320(3) . ?
 C8 H8 0.9300 . ?
 C8 C9 1.352(4) . ?
 C9 H9 0.9300 . ?
 C9 C10 1.433(4) . ?
 C10 C10 1.426(5) 3_866 ?
 C10 C11 1.428(4) . ?
 C11 H11 0.9300 . ?
 C11 C12 1.353(4) . ?
 C12 O1 1.376(3) . ?
 C13 C14 1.519(4) . ?
 C13 C15 1.518(4) . ?
 C13 C16 1.507(5) . ?
 C14 H14A 0.9600 . ?
 C14 H14B 0.9600 . ?
 C14 H14C 0.9600 . ?
 C15 H15A 0.9600 . ?
 C15 H15B 0.9600 . ?
 C15 H15C 0.9600 . ?
 C16 H16A 0.9600 . ?
 C16 H16B 0.9600 . ?
 C16 H16C 0.9600 . ?
 C17 C18 1.532(4) . ?
 C17 C19 1.542(3) . ?
 C17 C20 1.532(3) . ?
 C18 H18A 0.9600 . ?
 C18 H18B 0.9600 . ?
 C18 H18C 0.9600 . ?
 C19 H19A 0.9600 . ?
 C19 H19B 0.9600 . ?
 C19 H19C 0.9600 . ?
 C20 H20A 0.9600 . ?
 C20 H20B 0.9600 . ?
 C20 H20C 0.9600 . ?

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
 C6 C1 C2 122.2(2) . . ?
 O1 C1 C2 118.1(2) . . ?
 O1 C1 C6 119.7(2) . . ?
 C1 C2 C17 121.8(2) . . ?
 C3 C2 C1 115.7(2) . . ?
 C3 C2 C17 122.5(2) . . ?
 C2 C3 H3 117.8 . . ?
 C2 C3 C4 124.4(2) . . ?
 C4 C3 H3 117.8 . . ?
 C3 C4 C13 120.0(2) . . ?
 C5 C4 C3 117.7(2) . . ?
 C5 C4 C13 122.2(2) . . ?
 C4 C5 H5 119.4 . . ?
 C4 C5 C6 121.3(2) . . ?
 C6 C5 H5 119.4 . . ?
 C1 C6 C5 118.8(2) . . ?
 N1 C6 C1 122.7(2) . . ?
 N1 C6 C5 118.4(2) . . ?
 C12 C7 C8 115.2(2) . . ?
 N1 C7 C8 120.6(2) . . ?
 N1 C7 C12 124.2(2) . . ?
 C7 C8 H8 119.1 . . ?
 C9 C8 C7 121.7(2) . . ?
 C9 C8 H8 119.1 . . ?
 C8 C9 H9 118.6 . . ?
 C8 C9 C10 122.7(2) . . ?
 C10 C9 H9 118.6 . . ?
 C10 C10 C9 122.1(3) 3_866 . ?
 C10 C10 C11 122.3(3) 3_866 . ?
 C11 C10 C9 115.6(2) . . ?
 C10 C11 H11 119.3 . . ?
 C12 C11 C10 121.4(2) . . ?
 C12 C11 H11 119.3 . . ?
 C11 C12 C7 123.3(2) . . ?
 C11 C12 O1 117.7(2) . . ?
 O1 C12 C7 119.0(2) . . ?
 C14 C13 C4 107.9(3) . . ?
 C15 C13 C4 111.2(2) . . ?
 C15 C13 C14 107.8(3) . . ?
 C16 C13 C4 111.3(2) . . ?
 C16 C13 C14 109.6(3) . . ?
 C16 C13 C15 108.9(3) . . ?
 C13 C14 H14A 109.5 . . ?
 C13 C14 H14B 109.5 . . ?
 C13 C14 H14C 109.5 . . ?
 H14A C14 H14B 109.5 . . ?
 H14A C14 H14C 109.5 . . ?
 H14B C14 H14C 109.5 . . ?
 C13 C15 H15A 109.5 . . ?
 C13 C15 H15B 109.5 . . ?
 C13 C15 H15C 109.5 . . ?
 H15A C15 H15B 109.5 . . ?
 H15A C15 H15C 109.5 . . ?
 H15B C15 H15C 109.5 . . ?
 C13 C16 H16A 109.5 . . ?
 C13 C16 H16B 109.5 . . ?
 C13 C16 H16C 109.5 . . ?
 H16A C16 H16B 109.5 . . ?
 H16A C16 H16C 109.5 . . ?
 H16B C16 H16C 109.5 . . ?
 C2 C17 C19 109.7(2) . . ?
 C18 C17 C2 110.1(2) . . ?
 C18 C17 C19 110.1(2) . . ?
 C18 C17 C20 108.0(2) . . ?
 C20 C17 C2 111.8(2) . . ?
 C20 C17 C19 107.0(2) . . ?
 C17 C18 H18A 109.5 . . ?
 C17 C18 H18B 109.5 . . ?
 C17 C18 H18C 109.5 . . ?
 H18A C18 H18B 109.5 . . ?
 H18A C18 H18C 109.5 . . ?
 H18B C18 H18C 109.5 . . ?
 C17 C19 H19A 109.5 . . ?
 C17 C19 H19B 109.5 . . ?
 C17 C19 H19C 109.5 . . ?
 H19A C19 H19B 109.5 . . ?
 H19A C19 H19C 109.5 . . ?
 H19B C19 H19C 109.5 . . ?
 C17 C20 H20A 109.5 . . ?
 C17 C20 H20B 109.5 . . ?
 C17 C20 H20C 109.5 . . ?
 H20A C20 H20B 109.5 . . ?
 H20A C20 H20C 109.5 . . ?
 H20B C20 H20C 109.5 . . ?
 C7 N1 C6 115.5(2) . . ?
 C12 O1 C1 117.89(19) . . ?

_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  2.411
_oxdiff_exptl_absorpt_empirical_full_min  0.401
