data_spandan1_0m
_publcif_datablock.id '{d61cf108-1210-4be2-9910-c8874c726c18}'
loop_
_publcif_info_datablock.id
_publcif_info_datablock.publ_exptl
_publcif_info_datablock.publ_geom
_publcif_info_datablock.structure
'{d61cf108-1210-4be2-9910-c8874c726c18}' y y y


_diffrn_radiation_monochromator   Montel
#Added by publCIF



_audit_update_record
;
2018-08-31 # Formatted by publCIF

;

_audit_creation_date               2018-08-31
_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
;
Bruker (2009). SAINT. Bruker Analytical X-ray Instruments Inc., Madison,
Wisconsin, USA.

Bruker (2009). APEX3. Bruker Analytical X-ray Instruments Inc., Madison,
Wisconsin, USA.

Bruker (2008). SADABS. Bruker Analytical X-ray Instruments Inc., Madison,
Wisconsin, USA.

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           'C22 H24 N2 O2'
_chemical_formula_sum              'C22 H24 N2 O2'
_chemical_formula_weight           348.43
_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' 0.0181 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        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+1/2, -z'
 '-x, y+1/2, -z+1/2'
 '-x+1/2, -y, z+1/2'

_cell_length_a                     6.5750(3)
_cell_length_b                     9.8384(6)
_cell_length_c                     28.6228(15)
_cell_angle_alpha                  90
_cell_angle_beta                   90
_cell_angle_gamma                  90
_cell_volume                       1851.54(17)
_cell_formula_units_Z              4
_cell_measurement_reflns_used      9476
_cell_measurement_temperature      100(2)
_cell_measurement_theta_max        65.503
_cell_measurement_theta_min        4.753
_shelx_estimated_absorpt_T_max     ?
_shelx_estimated_absorpt_T_min     ?
_exptl_absorpt_coefficient_mu      0.637
_exptl_absorpt_correction_T_max    0.7527
_exptl_absorpt_correction_T_min    0.6871
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0807 before and 0.0571 after correction.
The Ratio of minimum to maximum transmission is 0.9128.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details     ?
_exptl_crystal_description        block 
_exptl_crystal_colour             'colorless' 
_exptl_crystal_size_max           0.144 
_exptl_crystal_size_mid           0.088 
_exptl_crystal_size_min           0.081 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.250 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              744 
_exptl_transmission_factor_max     ?
_exptl_transmission_factor_min     ?
_diffrn_reflns_av_R_equivalents    0.0415
_diffrn_reflns_av_unetI/netI       0.0127
_diffrn_reflns_Laue_measured_fraction_full  0.999
_diffrn_reflns_Laue_measured_fraction_max  0.999
_diffrn_reflns_limit_h_max         7
_diffrn_reflns_limit_h_min         -7
_diffrn_reflns_limit_k_max         10
_diffrn_reflns_limit_k_min         -11
_diffrn_reflns_limit_l_max         33
_diffrn_reflns_limit_l_min         -33
_diffrn_reflns_number              86745
_diffrn_reflns_point_group_measured_fraction_full  0.997
_diffrn_reflns_point_group_measured_fraction_max  0.997
_diffrn_reflns_theta_full          66.005
_diffrn_reflns_theta_max           66.005
_diffrn_reflns_theta_min           4.753
_diffrn_ambient_temperature        99.99
_diffrn_detector_area_resol_mean   ?
_diffrn_measured_fraction_theta_full  0.999
_diffrn_measured_fraction_theta_max  0.999
_diffrn_measurement_device_type    'Bruker X8 Proteum-R'
_diffrn_measurement_method         'ω and φ scans'
_diffrn_radiation_type             CuK\a
_diffrn_radiation_wavelength       1.54178
_diffrn_source                     'rotating anode'
_reflns_Friedel_coverage           0.701
_reflns_Friedel_fraction_full      0.994
_reflns_Friedel_fraction_max       0.994
_reflns_number_gt                  3189
_reflns_number_total               3214
_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         'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection         'APEX3 (Bruker, 2009)'
_computing_data_reduction          'SAINT v7.68A (Bruker, 2009)'
_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           0.135
_refine_diff_density_min           -0.145
_refine_diff_density_rms           0.029
_refine_ls_abs_structure_details
;
 Flack x determined using 1301 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack     0.01(4)
_refine_ls_extinction_coef         .
_refine_ls_extinction_method       none
_refine_ls_goodness_of_fit_ref     1.029
_refine_ls_hydrogen_treatment      mixed
_refine_ls_matrix_type             full
_refine_ls_number_parameters       239
_refine_ls_number_reflns           3214
_refine_ls_number_restraints       0
_refine_ls_R_factor_all            0.0284
_refine_ls_R_factor_gt             0.0282
_refine_ls_restrained_S_all        1.029
_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)+(0.0279P)²+0.6802P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme        calc
_refine_ls_wR_factor_gt            0.0693
_refine_ls_wR_factor_ref           0.0695
_refine_special_details            ?
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C5(H5), C7(H7), C15(H15), C17(H17)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C16(H16A,H16B), C19(H19A,H19B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2A), C3(H3), C10(H10), C11(H11), C12(H12), C13(H13), C14(H14),
 C21(H21), C22(H22)
2.d Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C)
;
_atom_sites_solution_hydrogens     mixed
_atom_sites_solution_primary       ?
_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 0.6767(2) 0.27836(13) 0.04526(4) 0.0239(3) Uani 1 1 d . . . . .
 O2 O 1.2840(2) 0.56579(15) 0.02101(5) 0.0349(4) Uani 1 1 d . . . . .
 N1 N 0.7311(3) 0.49113(16) 0.07226(5) 0.0212(3) Uani 1 1 d . . . . .
 N2 N 1.0013(3) 0.47346(17) -0.00986(5) 0.0221(3) Uani 1 1 d . . . . .
 H2 H 1.075(4) 0.408(2) -0.0187(8) 0.027 Uiso 1 1 d R . . . .
 C1 C 1.0912(4) 0.2772(2) 0.21215(7) 0.0351(5) Uani 1 1 d . . . . .
 H1 H 1.186749 0.239257 0.233346 0.042 Uiso 1 1 calc R . . . .
 C2 C 1.1548(3) 0.3623(3) 0.17682(8) 0.0376(5) Uani 1 1 d . . . . .
 H2A H 1.295470 0.382288 0.173663 0.045 Uiso 1 1 calc R . . . .
 C3 C 1.0171(3) 0.4192(2) 0.14578(7) 0.0300(5) Uani 1 1 d . . . . .
 H3 H 1.064345 0.476294 0.121326 0.036 Uiso 1 1 calc R . . . .
 C4 C 0.8112(3) 0.39309(19) 0.15026(6) 0.0219(4) Uani 1 1 d . . . . .
 C5 C 0.6541(3) 0.4598(2) 0.11924(6) 0.0216(4) Uani 1 1 d . . . . .
 H5 H 0.533448 0.398426 0.116451 0.026 Uiso 1 1 calc R . . . .
 C6 C 0.7211(3) 0.39796(18) 0.03782(6) 0.0203(4) Uani 1 1 d . . . . .
 C7 C 0.7806(3) 0.45199(19) -0.01025(6) 0.0212(4) Uani 1 1 d . . . . .
 H7 H 0.712211 0.541656 -0.015149 0.025 Uiso 1 1 calc R . . . .
 C8 C 0.7165(3) 0.3558(2) -0.04958(6) 0.0229(4) Uani 1 1 d . . . . .
 H8A H 0.801436 0.272757 -0.048419 0.027 Uiso 1 1 calc R . . . .
 H8B H 0.573075 0.328373 -0.044863 0.027 Uiso 1 1 calc R . . . .
 C9 C 0.7384(3) 0.42167(19) -0.09703(6) 0.0225(4) Uani 1 1 d . . . . .
 C10 C 0.9244(3) 0.4220(2) -0.12064(7) 0.0249(4) Uani 1 1 d . . . . .
 H10 H 1.039274 0.378919 -0.107018 0.030 Uiso 1 1 calc R . . . .
 C11 C 0.9425(3) 0.4851(2) -0.16403(7) 0.0299(5) Uani 1 1 d . . . . .
 H11 H 1.069774 0.485302 -0.179720 0.036 Uiso 1 1 calc R . . . .
 C12 C 0.7758(4) 0.5474(2) -0.18437(7) 0.0313(5) Uani 1 1 d . . . . .
 H12 H 0.788169 0.590096 -0.214007 0.038 Uiso 1 1 calc R . . . .
 C13 C 0.8864(3) 0.2478(2) 0.21636(7) 0.0309(5) Uani 1 1 d . . . . .
 H13 H 0.840787 0.188136 0.240245 0.037 Uiso 1 1 calc R . . . .
 C14 C 0.7476(3) 0.3054(2) 0.18574(6) 0.0260(4) Uani 1 1 d . . . . .
 H14 H 0.607040 0.284995 0.188952 0.031 Uiso 1 1 calc R . . . .
 C15 C 0.7624(3) 0.63776(19) 0.06359(6) 0.0239(4) Uani 1 1 d . . . . .
 H15 H 0.653605 0.671522 0.042125 0.029 Uiso 1 1 calc R . . . .
 C16 C 0.7298(3) 0.6987(2) 0.11209(7) 0.0283(4) Uani 1 1 d . . . . .
 H16A H 0.859861 0.703863 0.129419 0.034 Uiso 1 1 calc R . . . .
 H16B H 0.671078 0.791069 0.109774 0.034 Uiso 1 1 calc R . . . .
 C17 C 0.5823(3) 0.6022(2) 0.13631(7) 0.0269(4) Uani 1 1 d . . . . .
 H17 H 0.442754 0.619185 0.123677 0.032 Uiso 1 1 calc R . . . .
 C18 C 0.5767(4) 0.6220(2) 0.18930(7) 0.0358(5) Uani 1 1 d . . . . .
 H18A H 0.713504 0.609012 0.202137 0.054 Uiso 1 1 calc GR . . . .
 H18B H 0.483676 0.555555 0.203226 0.054 Uiso 1 1 calc GR . . . .
 H18C H 0.529378 0.714113 0.196477 0.054 Uiso 1 1 calc GR . . . .
 C19 C 0.9735(3) 0.6731(2) 0.04260(7) 0.0282(5) Uani 1 1 d . . . . .
 H19A H 0.952893 0.748958 0.020388 0.034 Uiso 1 1 calc R . . . .
 H19B H 1.058516 0.708599 0.068392 0.034 Uiso 1 1 calc R . . . .
 C20 C 1.0979(3) 0.5652(2) 0.01743(7) 0.0244(4) Uani 1 1 d . . . . .
 C21 C 0.5730(3) 0.4856(2) -0.11785(7) 0.0292(5) Uani 1 1 d . . . . .
 H21 H 0.445754 0.487137 -0.102138 0.035 Uiso 1 1 calc R . . . .
 C22 C 0.5913(4) 0.5471(2) -0.16127(7) 0.0328(5) Uani 1 1 d . . . . .
 H22 H 0.476335 0.589292 -0.175188 0.039 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 C6 1.231(2) . ?
 O2 C20 1.227(3) . ?
 N1 C5 1.470(2) . ?
 N1 C6 1.348(2) . ?
 N1 C15 1.478(2) . ?
 N2 H2 0.85(2) . ?
 N2 C7 1.467(2) . ?
 N2 C20 1.352(3) . ?
 C1 H1 0.9500 . ?
 C1 C2 1.378(3) . ?
 C1 C13 1.382(3) . ?
 C2 H2A 0.9500 . ?
 C2 C3 1.386(3) . ?
 C3 H3 0.9500 . ?
 C3 C4 1.384(3) . ?
 C4 C5 1.512(3) . ?
 C4 C14 1.397(3) . ?
 C5 H5 1.0000 . ?
 C5 C17 1.557(3) . ?
 C6 C7 1.526(3) . ?
 C7 H7 1.0000 . ?
 C7 C8 1.530(3) . ?
 C8 H8A 0.9900 . ?
 C8 H8B 0.9900 . ?
 C8 C9 1.512(3) . ?
 C9 C10 1.397(3) . ?
 C9 C21 1.390(3) . ?
 C10 H10 0.9500 . ?
 C10 C11 1.393(3) . ?
 C11 H11 0.9500 . ?
 C11 C12 1.384(3) . ?
 C12 H12 0.9500 . ?
 C12 C22 1.381(3) . ?
 C13 H13 0.9500 . ?
 C13 C14 1.387(3) . ?
 C14 H14 0.9500 . ?
 C15 H15 1.0000 . ?
 C15 C16 1.527(3) . ?
 C15 C19 1.551(3) . ?
 C16 H16A 0.9900 . ?
 C16 H16B 0.9900 . ?
 C16 C17 1.524(3) . ?
 C17 H17 1.0000 . ?
 C17 C18 1.530(3) . ?
 C18 H18A 0.9800 . ?
 C18 H18B 0.9800 . ?
 C18 H18C 0.9800 . ?
 C19 H19A 0.9900 . ?
 C19 H19B 0.9900 . ?
 C19 C20 1.521(3) . ?
 C21 H21 0.9500 . ?
 C21 C22 1.388(3) . ?
 C22 H22 0.9500 . ?

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
 C5 N1 C15 113.98(15) . . ?
 C6 N1 C5 120.62(15) . . ?
 C6 N1 C15 123.23(15) . . ?
 C7 N2 H2 117.0(16) . . ?
 C20 N2 H2 114.4(16) . . ?
 C20 N2 C7 124.44(17) . . ?
 C2 C1 H1 120.4 . . ?
 C2 C1 C13 119.1(2) . . ?
 C13 C1 H1 120.4 . . ?
 C1 C2 H2A 119.4 . . ?
 C1 C2 C3 121.2(2) . . ?
 C3 C2 H2A 119.4 . . ?
 C2 C3 H3 119.8 . . ?
 C4 C3 C2 120.3(2) . . ?
 C4 C3 H3 119.8 . . ?
 C3 C4 C5 122.26(17) . . ?
 C3 C4 C14 118.36(18) . . ?
 C14 C4 C5 119.35(18) . . ?
 N1 C5 C4 113.14(15) . . ?
 N1 C5 H5 109.1 . . ?
 N1 C5 C17 101.69(15) . . ?
 C4 C5 H5 109.1 . . ?
 C4 C5 C17 114.41(15) . . ?
 C17 C5 H5 109.1 . . ?
 O1 C6 N1 122.38(17) . . ?
 O1 C6 C7 123.34(16) . . ?
 N1 C6 C7 114.20(15) . . ?
 N2 C7 C6 107.27(15) . . ?
 N2 C7 H7 108.6 . . ?
 N2 C7 C8 111.54(15) . . ?
 C6 C7 H7 108.6 . . ?
 C6 C7 C8 112.18(15) . . ?
 C8 C7 H7 108.6 . . ?
 C7 C8 H8A 109.3 . . ?
 C7 C8 H8B 109.3 . . ?
 H8A C8 H8B 107.9 . . ?
 C9 C8 C7 111.68(15) . . ?
 C9 C8 H8A 109.3 . . ?
 C9 C8 H8B 109.3 . . ?
 C10 C9 C8 121.27(17) . . ?
 C21 C9 C8 120.28(18) . . ?
 C21 C9 C10 118.44(17) . . ?
 C9 C10 H10 119.8 . . ?
 C11 C10 C9 120.46(19) . . ?
 C11 C10 H10 119.8 . . ?
 C10 C11 H11 119.8 . . ?
 C12 C11 C10 120.3(2) . . ?
 C12 C11 H11 119.8 . . ?
 C11 C12 H12 120.2 . . ?
 C22 C12 C11 119.52(18) . . ?
 C22 C12 H12 120.2 . . ?
 C1 C13 H13 120.0 . . ?
 C1 C13 C14 120.1(2) . . ?
 C14 C13 H13 120.0 . . ?
 C4 C14 H14 119.5 . . ?
 C13 C14 C4 121.0(2) . . ?
 C13 C14 H14 119.5 . . ?
 N1 C15 H15 109.1 . . ?
 N1 C15 C16 102.17(14) . . ?
 N1 C15 C19 114.08(16) . . ?
 C16 C15 H15 109.1 . . ?
 C16 C15 C19 112.96(17) . . ?
 C19 C15 H15 109.1 . . ?
 C15 C16 H16A 110.7 . . ?
 C15 C16 H16B 110.7 . . ?
 H16A C16 H16B 108.8 . . ?
 C17 C16 C15 104.99(16) . . ?
 C17 C16 H16A 110.7 . . ?
 C17 C16 H16B 110.7 . . ?
 C5 C17 H17 108.4 . . ?
 C16 C17 C5 102.97(15) . . ?
 C16 C17 H17 108.4 . . ?
 C16 C17 C18 112.76(18) . . ?
 C18 C17 C5 115.66(17) . . ?
 C18 C17 H17 108.4 . . ?
 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 . . ?
 C15 C19 H19A 107.2 . . ?
 C15 C19 H19B 107.2 . . ?
 H19A C19 H19B 106.8 . . ?
 C20 C19 C15 120.56(16) . . ?
 C20 C19 H19A 107.2 . . ?
 C20 C19 H19B 107.2 . . ?
 O2 C20 N2 121.3(2) . . ?
 O2 C20 C19 119.57(18) . . ?
 N2 C20 C19 119.09(17) . . ?
 C9 C21 H21 119.6 . . ?
 C22 C21 C9 120.9(2) . . ?
 C22 C21 H21 119.6 . . ?
 C12 C22 C21 120.4(2) . . ?
 C12 C22 H22 119.8 . . ?
 C21 C22 H22 119.8 . . ?

_olex2_submission_special_instructions  'No special instructions were received'
loop_
_publcif_info_cif.paper_type
 ?



_publcif_funding_html
;
;
