data_140513a_0m
_audit_creation_date               2024-04-22
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number       '2018/1'
_audit_contact_author_address      ?
_audit_contact_author_email        ?
_audit_contact_author_name         ''
_audit_contact_author_phone        ?
_publ_contact_author_id_orcid      ?
_publ_section_references
;
Bourhis, L.J., Dolomanov, O.V., Gildea, R.J., Howard, J.A.K., Puschmann, H.
 (2015). Acta Cryst. A71, 59-75.

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. C71, 3-8.
;
_chemical_name_common              ?
_chemical_name_systematic
;
 ? 
;
_chemical_formula_moiety           'C20 H20 N2'
_chemical_formula_sum              'C20 H20 N2'
_chemical_formula_weight           288.38
_chemical_absolute_configuration   ad
_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'

_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        'orthorhombic'
_space_group_IT_number             19
_space_group_name_H-M_alt          'P 21 21 21'
_space_group_name_Hall             'P 2ac 2ab'
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'

_cell_length_a                     7.529(3)
_cell_length_b                     9.995(3)
_cell_length_c                     20.877(7)
_cell_angle_alpha                  90
_cell_angle_beta                   90
_cell_angle_gamma                  90
_cell_volume                       1571.1(9)
_cell_formula_units_Z              4
_cell_measurement_reflns_used      4086
_cell_measurement_temperature      100(2)
_cell_measurement_theta_max        56.397
_cell_measurement_theta_min        5.638
_shelx_estimated_absorpt_T_max     0.982
_shelx_estimated_absorpt_T_min     0.965
_exptl_absorpt_coefficient_mu      0.072
_exptl_absorpt_correction_T_max    0.7457
_exptl_absorpt_correction_T_min    0.6507
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0786 before and 0.0611 after correction.
The Ratio of minimum to maximum transmission is 0.8726.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details     ?
_exptl_crystal_colour              'clear light colourless'
_exptl_crystal_colour_lustre       clear
_exptl_crystal_colour_modifier     light
_exptl_crystal_colour_primary      colourless
_exptl_crystal_density_diffrn      1.219
_exptl_crystal_density_meas        ?
_exptl_crystal_density_method      ?
_exptl_crystal_description         plate
_exptl_crystal_F_000               616
_exptl_crystal_size_max            0.5
_exptl_crystal_size_mid            0.25
_exptl_crystal_size_min            0.25
_exptl_special_details
;
 ? 
;
_exptl_transmission_factor_max     ?
_exptl_transmission_factor_min     ?
_diffrn_reflns_av_R_equivalents    0.0425
_diffrn_reflns_av_unetI/netI       0.0478
_diffrn_reflns_Laue_measured_fraction_full  0.999
_diffrn_reflns_Laue_measured_fraction_max  0.997
_diffrn_reflns_limit_h_max         10
_diffrn_reflns_limit_h_min         -9
_diffrn_reflns_limit_k_max         13
_diffrn_reflns_limit_k_min         -9
_diffrn_reflns_limit_l_max         27
_diffrn_reflns_limit_l_min         -27
_diffrn_reflns_number              11202
_diffrn_reflns_point_group_measured_fraction_full  1.000
_diffrn_reflns_point_group_measured_fraction_max  0.995
_diffrn_reflns_theta_full          25.242
_diffrn_reflns_theta_max           28.304
_diffrn_reflns_theta_min           1.951
_diffrn_ambient_temperature        100.15
_diffrn_detector_area_resol_mean   ?
_diffrn_measured_fraction_theta_full  0.999
_diffrn_measured_fraction_theta_max  0.997
_diffrn_measurement_device_type    'Bruker APEX-II CCD'
_diffrn_measurement_method         'φ and ω scans'
_diffrn_radiation_type             MoK\a
_diffrn_radiation_wavelength       0.71073
_diffrn_source                     ?
_reflns_Friedel_coverage           0.734
_reflns_Friedel_fraction_full      1.000
_reflns_Friedel_fraction_max       0.993
_reflns_number_gt                  3488
_reflns_number_total               3882
_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         ?
_computing_data_collection         'Bruker APEX2'
_computing_data_reduction          ?
_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      'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max           0.354
_refine_diff_density_min           -0.177
_refine_diff_density_rms           0.041
_refine_ls_abs_structure_details
;
 Flack x determined using 1317 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack     -0.8(10)
_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       200
_refine_ls_number_reflns           3882
_refine_ls_number_restraints       0
_refine_ls_R_factor_all            0.0500
_refine_ls_R_factor_gt             0.0436
_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)+(0.0512P)²+0.2705P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme        calc
_refine_ls_wR_factor_gt            0.1062
_refine_ls_wR_factor_ref           0.1103
_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 Ternary CH refined with riding coordinates:
 C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B)
2.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C9(H9), C12(H12), C13(H13), C14(H14), C16(H16), C17(H17),
 C18(H18), C19(H19)
2.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary       iterative
_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 -0.3459(3) -0.9256(3) -0.28316(11) 0.0351(6) Uani 1 1 d . . . . .
 H1A H -0.243376 -0.979541 -0.270115 0.053 Uiso 1 1 calc GR . . . .
 H1B H -0.344928 -0.914356 -0.329785 0.053 Uiso 1 1 calc GR . . . .
 H1C H -0.455618 -0.970886 -0.270206 0.053 Uiso 1 1 calc GR . . . .
 C2 C -0.1725(3) -0.7232(2) -0.26911(11) 0.0293(5) Uani 1 1 d . . . . .
 H2A H -0.179343 -0.686099 -0.312994 0.035 Uiso 1 1 calc R . . . .
 H2B H -0.068219 -0.783312 -0.266234 0.035 Uiso 1 1 calc R . . . .
 C3 C -0.1610(3) -0.6117(2) -0.21951(13) 0.0360(6) Uani 1 1 d . . . . .
 H3A H -0.217273 -0.528839 -0.235696 0.043 Uiso 1 1 calc R . . . .
 H3B H -0.035759 -0.592355 -0.208421 0.043 Uiso 1 1 calc R . . . .
 C4 C -0.2625(3) -0.6666(2) -0.16090(11) 0.0250(5) Uani 1 1 d . . . . .
 H4A H -0.362681 -0.606994 -0.149463 0.030 Uiso 1 1 calc R . . . .
 H4B H -0.182607 -0.674893 -0.123454 0.030 Uiso 1 1 calc R . . . .
 C5 C -0.3311(3) -0.8053(2) -0.18219(9) 0.0169(4) Uani 1 1 d . . . . .
 H5 H -0.242474 -0.875130 -0.169714 0.020 Uiso 1 1 calc R . . . .
 C6 C -0.5111(3) -0.84182(19) -0.15451(9) 0.0159(4) Uani 1 1 d . . . . .
 C7 C -0.6657(3) -0.7938(2) -0.18323(9) 0.0196(4) Uani 1 1 d . . . . .
 H7 H -0.652836 -0.740128 -0.220507 0.024 Uiso 1 1 calc R . . . .
 C8 C -0.8465(3) -0.8931(2) -0.11002(11) 0.0256(5) Uani 1 1 d . . . . .
 H8 H -0.962379 -0.913744 -0.094969 0.031 Uiso 1 1 calc R . . . .
 C9 C -0.7019(3) -0.9435(2) -0.07632(11) 0.0278(5) Uani 1 1 d . . . . .
 H9 H -0.719583 -0.995561 -0.038802 0.033 Uiso 1 1 calc R . . . .
 C10 C -0.5299(3) -0.9166(2) -0.09831(10) 0.0205(4) Uani 1 1 d . . . . .
 C11 C -0.3738(3) -0.9634(2) -0.05933(10) 0.0214(4) Uani 1 1 d . . . . .
 C12 C -0.3213(3) -0.8897(3) -0.00736(11) 0.0288(5) Uani 1 1 d . . . . .
 H12 H -0.381145 -0.808345 0.002035 0.035 Uiso 1 1 calc R . . . .
 C13 C -0.1804(3) -0.9315(3) 0.03263(10) 0.0315(5) Uani 1 1 d . . . . .
 H13 H -0.146021 -0.878465 0.068285 0.038 Uiso 1 1 calc R . . . .
 C14 C -0.0936(3) -1.0491(3) 0.01971(11) 0.0331(6) Uani 1 1 d . . . . .
 H14 H 0.000744 -1.077379 0.046716 0.040 Uiso 1 1 calc R . . . .
 C15 C -0.1437(3) -1.1296(2) -0.03399(10) 0.0233(5) Uani 1 1 d . . . . .
 C16 C -0.0567(3) -1.2517(3) -0.04765(12) 0.0322(6) Uani 1 1 d . . . . .
 H16 H 0.038910 -1.280243 -0.021312 0.039 Uiso 1 1 calc R . . . .
 C17 C -0.1083(3) -1.3286(3) -0.09799(12) 0.0340(6) Uani 1 1 d . . . . .
 H17 H -0.048711 -1.410403 -0.106655 0.041 Uiso 1 1 calc R . . . .
 C18 C -0.2500(3) -1.2872(2) -0.13733(11) 0.0271(5) Uani 1 1 d . . . . .
 H18 H -0.285594 -1.342145 -0.172152 0.033 Uiso 1 1 calc R . . . .
 C19 C -0.3374(3) -1.1693(2) -0.12642(10) 0.0240(4) Uani 1 1 d . . . . .
 H19 H -0.432059 -1.143089 -0.153750 0.029 Uiso 1 1 calc R . . . .
 C20 C -0.2863(3) -1.0851(2) -0.07367(10) 0.0215(4) Uani 1 1 d . . . . .
 N1 N -0.3366(2) -0.79472(19) -0.25244(8) 0.0230(4) Uani 1 1 d . . . . .
 N2 N -0.8314(2) -0.81736(19) -0.16231(8) 0.0241(4) 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 H1A 0.9800 . ?
 C1 H1B 0.9800 . ?
 C1 H1C 0.9800 . ?
 C1 N1 1.459(3) . ?
 C2 H2A 0.9900 . ?
 C2 H2B 0.9900 . ?
 C2 C3 1.524(4) . ?
 C2 N1 1.469(3) . ?
 C3 H3A 0.9900 . ?
 C3 H3B 0.9900 . ?
 C3 C4 1.543(3) . ?
 C4 H4A 0.9900 . ?
 C4 H4B 0.9900 . ?
 C4 C5 1.545(3) . ?
 C5 H5 1.0000 . ?
 C5 C6 1.518(3) . ?
 C5 N1 1.471(2) . ?
 C6 C7 1.395(3) . ?
 C6 C10 1.398(3) . ?
 C7 H7 0.9500 . ?
 C7 N2 1.342(3) . ?
 C8 H8 0.9500 . ?
 C8 C9 1.391(3) . ?
 C8 N2 1.333(3) . ?
 C9 H9 0.9500 . ?
 C9 C10 1.400(3) . ?
 C10 C11 1.504(3) . ?
 C11 C12 1.370(3) . ?
 C11 C20 1.415(3) . ?
 C12 H12 0.9500 . ?
 C12 C13 1.413(3) . ?
 C13 H13 0.9500 . ?
 C13 C14 1.372(4) . ?
 C14 H14 0.9500 . ?
 C14 C15 1.431(3) . ?
 C15 C16 1.413(4) . ?
 C15 C20 1.427(3) . ?
 C16 H16 0.9500 . ?
 C16 C17 1.359(4) . ?
 C17 H17 0.9500 . ?
 C17 C18 1.409(3) . ?
 C18 H18 0.9500 . ?
 C18 C19 1.368(3) . ?
 C19 H19 0.9500 . ?
 C19 C20 1.439(3) . ?

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
 H1A C1 H1B 109.5 . . ?
 H1A C1 H1C 109.5 . . ?
 H1B C1 H1C 109.5 . . ?
 N1 C1 H1A 109.5 . . ?
 N1 C1 H1B 109.5 . . ?
 N1 C1 H1C 109.5 . . ?
 H2A C2 H2B 109.0 . . ?
 C3 C2 H2A 110.9 . . ?
 C3 C2 H2B 110.9 . . ?
 N1 C2 H2A 110.9 . . ?
 N1 C2 H2B 110.9 . . ?
 N1 C2 C3 104.03(17) . . ?
 C2 C3 H3A 110.8 . . ?
 C2 C3 H3B 110.8 . . ?
 C2 C3 C4 104.53(18) . . ?
 H3A C3 H3B 108.9 . . ?
 C4 C3 H3A 110.8 . . ?
 C4 C3 H3B 110.8 . . ?
 C3 C4 H4A 110.8 . . ?
 C3 C4 H4B 110.8 . . ?
 C3 C4 C5 104.84(18) . . ?
 H4A C4 H4B 108.9 . . ?
 C5 C4 H4A 110.8 . . ?
 C5 C4 H4B 110.8 . . ?
 C4 C5 H5 109.2 . . ?
 C6 C5 C4 113.86(17) . . ?
 C6 C5 H5 109.2 . . ?
 N1 C5 C4 103.40(16) . . ?
 N1 C5 H5 109.2 . . ?
 N1 C5 C6 111.82(16) . . ?
 C7 C6 C5 119.93(17) . . ?
 C7 C6 C10 117.38(18) . . ?
 C10 C6 C5 122.59(17) . . ?
 C6 C7 H7 117.4 . . ?
 N2 C7 C6 125.11(18) . . ?
 N2 C7 H7 117.4 . . ?
 C9 C8 H8 118.2 . . ?
 N2 C8 H8 118.2 . . ?
 N2 C8 C9 123.55(19) . . ?
 C8 C9 H9 120.4 . . ?
 C8 C9 C10 119.3(2) . . ?
 C10 C9 H9 120.4 . . ?
 C6 C10 C9 118.14(19) . . ?
 C6 C10 C11 122.75(18) . . ?
 C9 C10 C11 119.04(18) . . ?
 C12 C11 C10 119.1(2) . . ?
 C12 C11 C20 119.7(2) . . ?
 C20 C11 C10 121.12(19) . . ?
 C11 C12 H12 119.2 . . ?
 C11 C12 C13 121.7(2) . . ?
 C13 C12 H12 119.2 . . ?
 C12 C13 H13 120.2 . . ?
 C14 C13 C12 119.7(2) . . ?
 C14 C13 H13 120.2 . . ?
 C13 C14 H14 119.6 . . ?
 C13 C14 C15 120.7(2) . . ?
 C15 C14 H14 119.6 . . ?
 C16 C15 C14 121.4(2) . . ?
 C16 C15 C20 120.0(2) . . ?
 C20 C15 C14 118.5(2) . . ?
 C15 C16 H16 119.6 . . ?
 C17 C16 C15 120.8(2) . . ?
 C17 C16 H16 119.6 . . ?
 C16 C17 H17 120.0 . . ?
 C16 C17 C18 120.1(2) . . ?
 C18 C17 H17 120.0 . . ?
 C17 C18 H18 119.3 . . ?
 C19 C18 C17 121.4(2) . . ?
 C19 C18 H18 119.3 . . ?
 C18 C19 H19 119.9 . . ?
 C18 C19 C20 120.2(2) . . ?
 C20 C19 H19 119.9 . . ?
 C11 C20 C15 119.7(2) . . ?
 C11 C20 C19 122.70(19) . . ?
 C15 C20 C19 117.6(2) . . ?
 C1 N1 C2 111.87(18) . . ?
 C1 N1 C5 112.04(18) . . ?
 C2 N1 C5 104.32(17) . . ?
 C8 N2 C7 116.47(18) . . ?

_olex2_submission_special_instructions  'No special instructions were received'
