data_scd17_85_0m
#=============================================================
_audit_creation_date               2019-03-09
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.18 svn.r3508 for OlexSys, GUI svn.r5497)
;
_shelx_SHELXL_version_number      '2016/6'

#=============================================================
# 1. SUBMISSION DETAILS

_audit_contact_author_name           'Dr. Antonio Galdámez'
_audit_contact_author_address    
;     Universidad de Chile   
      Facultad de Ciencias
      Departamento de Química 
      Casilla 653
      Santiago Chile
;
_publ_contact_author_phone        '056 02 29787267'
_publ_contact_author_fax          '056 02 22713888'
_publ_contact_author_email         agaldamez@uchile.cl
_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.
;

#=====================================================================
# 2. Chemical Data

_chemical_formula_moiety           'C21 H25 N3 O2'
_chemical_formula_sum              'C21 H25 N3 O2'
_chemical_formula_weight           351.44

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        'triclinic'
_space_group_IT_number             2
_space_group_name_H-M_alt          'P -1'
_space_group_name_Hall             '-P 1'
loop_
  _space_group_symop_operation_xyz
 'x, y, z'
 '-x, -y, -z'

_cell_length_a                     10.1338(11)
_cell_length_b                     10.2076(10)
_cell_length_c                     10.6911(12)
_cell_angle_alpha                  96.723(5)
_cell_angle_beta                   113.639(5)
_cell_angle_gamma                  93.417(5)
_cell_volume                       999.22(19)
_cell_formula_units_Z              2
_cell_measurement_reflns_used      4190
_cell_measurement_temperature      293(2)
_cell_measurement_theta_max        21.614
_cell_measurement_theta_min        2.209
_shelx_estimated_absorpt_T_max     ?
_shelx_estimated_absorpt_T_min     ?
_exptl_absorpt_coefficient_mu      0.076
_exptl_absorpt_correction_T_max    0.4932
_exptl_absorpt_correction_T_min    0.3835
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.1316 before and 0.0542 after correction.
The Ratio of minimum to maximum transmission is 0.7776.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details     ?
_exptl_crystal_colour              yellow
_exptl_crystal_density_diffrn      1.168
_exptl_crystal_density_meas        ?
_exptl_crystal_density_method      ?
_exptl_crystal_description         block
_exptl_crystal_F_000               376
_exptl_crystal_size_max            0.25
_exptl_crystal_size_mid            0.20
_exptl_crystal_size_min            0.16
_diffrn_reflns_av_R_equivalents    0.0459
_diffrn_reflns_av_unetI/netI       0.0324
_diffrn_reflns_Laue_measured_fraction_full  1.000
_diffrn_reflns_Laue_measured_fraction_max  1.000
_diffrn_reflns_limit_h_max         12
_diffrn_reflns_limit_h_min         -12
_diffrn_reflns_limit_k_max         12
_diffrn_reflns_limit_k_min         -12
_diffrn_reflns_limit_l_max         12
_diffrn_reflns_limit_l_min         -12
_diffrn_reflns_number              21130
_diffrn_reflns_point_group_measured_fraction_full  1.000
_diffrn_reflns_point_group_measured_fraction_max  1.000
_diffrn_reflns_theta_full          25.097
_diffrn_reflns_theta_max           25.097
_diffrn_reflns_theta_min           2.023
_diffrn_ambient_temperature        296.15
_diffrn_detector_area_resol_mean   ?
_diffrn_measured_fraction_theta_full  1.000
_diffrn_measured_fraction_theta_max  1.000
_diffrn_measurement_device_type    'Bruker CCD area detector'
_diffrn_measurement_method         'phi and omega scans'
_diffrn_radiation_monochromator   'graphite'
_diffrn_radiation_type             MoK\a
_diffrn_radiation_wavelength       0.71073

#=========================================================================

# 3. Refinement Data

_reflns_Friedel_coverage           0.000
_reflns_number_gt                  2698
_reflns_number_total               3562
_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)'
_refine_diff_density_max           0.158
_refine_diff_density_min           -0.206
_refine_diff_density_rms           0.037
_refine_ls_extinction_method       none
_refine_ls_goodness_of_fit_ref     1.015
_refine_ls_hydrogen_treatment      mixed
_refine_ls_matrix_type             full
_refine_ls_number_parameters       243
_refine_ls_number_reflns           3562
_refine_ls_number_restraints       0
_refine_ls_R_factor_all            0.0643
_refine_ls_R_factor_gt             0.0460
_refine_ls_restrained_S_all        1.015
_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)+(0.0499P)²+0.3109P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme        calc
_refine_ls_wR_factor_gt            0.1074
_refine_ls_wR_factor_ref           0.1207
_refine_special_details            ?
_computing_cell_refinement         'APEX3 (Bruker, 2015); SAINT (Bruker, 2014)'
_computing_data_collection         'SAINT (Bruker, 2014)'
_computing_data_reduction          'SAINT (Bruker, 2014)'
_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)'

#=========================================================================
# 4. Atomic Coordinates and Displacement Parameters

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 0.65641(14) 0.53237(14) 0.92938(13) 0.0562(4) Uani 1 1 d . . . . .
 O2 O 0.61553(16) 0.41337(14) 0.72689(14) 0.0610(4) Uani 1 1 d . . . . .
 N1 N 0.5651(3) 0.7987(2) 1.0971(2) 0.0969(8) Uani 1 1 d . . . . .
 N2 N 0.31769(15) 0.80453(13) 0.62003(14) 0.0386(4) Uani 1 1 d . . . . .
 N3 N 0.25499(17) 0.57808(14) 0.49009(15) 0.0418(4) Uani 1 1 d . . . . .
 H3 H 0.263(2) 0.604(2) 0.419(2) 0.055(6) Uiso 1 1 d . . . . .
 C1 C 0.38848(19) 0.85884(17) 0.75625(18) 0.0447(5) Uani 1 1 d . . . . .
 H1 H 0.402013 0.948839 0.790975 0.054 Uiso 1 1 calc R . . . .
 C2 C 0.43614(19) 0.75990(17) 0.83321(18) 0.0425(4) Uani 1 1 d . . . . .
 C3 C 0.39450(18) 0.63773(16) 0.74099(17) 0.0357(4) Uani 1 1 d . . . . .
 C4 C 0.41475(19) 0.49724(16) 0.76632(17) 0.0377(4) Uani 1 1 d . . . . .
 H4 H 0.391171 0.483018 0.844454 0.045 Uiso 1 1 calc R . . . .
 C5 C 0.3088(2) 0.40393(16) 0.63787(17) 0.0425(4) Uani 1 1 d . . . . .
 H5A H 0.336800 0.314829 0.643279 0.051 Uiso 1 1 calc R . . . .
 H5B H 0.212493 0.401742 0.636719 0.051 Uiso 1 1 calc R . . . .
 C6 C 0.30345(19) 0.44496(15) 0.50337(16) 0.0374(4) Uani 1 1 d . . . . .
 H6 H 0.401497 0.448935 0.506220 0.045 Uiso 1 1 calc R . . . .
 C7 C 0.32258(17) 0.66860(15) 0.61167(17) 0.0350(4) Uani 1 1 d . . . . .
 C8 C 0.5089(2) 0.78049(19) 0.9796(2) 0.0590(6) Uani 1 1 d . . . . .
 C9 C 0.2439(2) 0.88028(17) 0.50458(19) 0.0438(4) Uani 1 1 d . . . . .
 C10 C 0.2608(2) 1.02661(18) 0.5626(2) 0.0602(6) Uani 1 1 d . . . . .
 H10A H 0.219670 1.036927 0.629378 0.090 Uiso 1 1 calc GR . . . .
 H10B H 0.211543 1.075222 0.488890 0.090 Uiso 1 1 calc GR . . . .
 H10C H 0.361916 1.060074 0.606041 0.090 Uiso 1 1 calc GR . . . .
 C11 C 0.0832(2) 0.8290(2) 0.4368(2) 0.0680(6) Uani 1 1 d . . . . .
 H11A H 0.071242 0.735820 0.402889 0.102 Uiso 1 1 calc GR . . . .
 H11B H 0.034754 0.875852 0.361293 0.102 Uiso 1 1 calc GR . . . .
 H11C H 0.042181 0.843067 0.503442 0.102 Uiso 1 1 calc GR . . . .
 C12 C 0.3139(3) 0.8651(2) 0.4024(3) 0.0757(7) Uani 1 1 d . . . . .
 H12A H 0.417298 0.883399 0.451434 0.113 Uiso 1 1 calc GR . . . .
 H12B H 0.279262 0.926403 0.337999 0.113 Uiso 1 1 calc GR . . . .
 H12C H 0.289149 0.776001 0.353276 0.113 Uiso 1 1 calc GR . . . .
 C13 C 0.2041(2) 0.34753(16) 0.37886(17) 0.0402(4) Uani 1 1 d . . . . .
 C14 C 0.2611(2) 0.26205(17) 0.30903(19) 0.0509(5) Uani 1 1 d . . . . .
 H14 H 0.361052 0.266731 0.337648 0.061 Uiso 1 1 calc R . . . .
 C15 C 0.1714(3) 0.1696(2) 0.1971(2) 0.0713(7) Uani 1 1 d . . . . .
 H15 H 0.211022 0.112953 0.150546 0.086 Uiso 1 1 calc R . . . .
 C16 C 0.0242(3) 0.1615(2) 0.1549(2) 0.0825(8) Uani 1 1 d . . . . .
 H16 H -0.036038 0.098612 0.080173 0.099 Uiso 1 1 calc R . . . .
 C17 C -0.0344(3) 0.2456(3) 0.2223(3) 0.0793(7) Uani 1 1 d . . . . .
 H17 H -0.134485 0.240241 0.193198 0.095 Uiso 1 1 calc R . . . .
 C18 C 0.0550(2) 0.3385(2) 0.3337(2) 0.0581(5) Uani 1 1 d . . . . .
 H18 H 0.014504 0.395699 0.378917 0.070 Uiso 1 1 calc R . . . .
 C19 C 0.5711(2) 0.47347(16) 0.80251(17) 0.0410(4) Uani 1 1 d . . . . .
 C20 C 0.8115(2) 0.5262(3) 0.9728(2) 0.0716(7) Uani 1 1 d . . . . .
 H20A H 0.842126 0.554007 0.903916 0.086 Uiso 1 1 calc R . . . .
 H20B H 0.833764 0.436086 0.984091 0.086 Uiso 1 1 calc R . . . .
 C21 C 0.8870(3) 0.6155(4) 1.1048(3) 0.1129(12) Uani 1 1 d . . . . .
 H21A H 0.855586 0.702056 1.095084 0.169 Uiso 1 1 calc GR . . . .
 H21B H 0.989682 0.621595 1.130595 0.169 Uiso 1 1 calc GR . . . .
 H21C H 0.864907 0.581079 1.174880 0.169 Uiso 1 1 calc GR . . . .


_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.
;

#=========================================================================

# 6. Molecular Geometry

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 C19 1.325(2) . ?
 O1 C20 1.457(2) . ?
 O2 C19 1.201(2) . ?
 N1 C8 1.139(3) . ?
 N2 C1 1.367(2) . ?
 N2 C7 1.385(2) . ?
 N2 C9 1.494(2) . ?
 N3 C6 1.475(2) . ?
 N3 C7 1.393(2) . ?
 C1 C2 1.365(3) . ?
 C2 C3 1.422(2) . ?
 C2 C8 1.420(3) . ?
 C3 C4 1.501(2) . ?
 C3 C7 1.365(2) . ?
 C4 C5 1.528(2) . ?
 C4 C19 1.515(2) . ?
 C5 C6 1.525(2) . ?
 C6 C13 1.507(2) . ?
 C9 C10 1.521(2) . ?
 C9 C11 1.521(3) . ?
 C9 C12 1.521(3) . ?
 C13 C14 1.380(3) . ?
 C13 C18 1.382(3) . ?
 C14 C15 1.382(3) . ?
 C15 C16 1.368(4) . ?
 C16 C17 1.367(4) . ?
 C17 C18 1.381(3) . ?
 C20 C21 1.468(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
 C19 O1 C20 116.44(15) . . ?
 C1 N2 C7 107.43(14) . . ?
 C1 N2 C9 125.07(14) . . ?
 C7 N2 C9 127.44(14) . . ?
 C7 N3 C6 113.20(14) . . ?
 C2 C1 N2 109.14(15) . . ?
 C1 C2 C3 107.65(15) . . ?
 C1 C2 C8 124.15(16) . . ?
 C8 C2 C3 128.16(17) . . ?
 C2 C3 C4 131.53(15) . . ?
 C7 C3 C2 106.28(15) . . ?
 C7 C3 C4 122.17(14) . . ?
 C3 C4 C5 108.37(13) . . ?
 C3 C4 C19 110.19(14) . . ?
 C19 C4 C5 112.44(14) . . ?
 C6 C5 C4 113.13(14) . . ?
 N3 C6 C5 109.90(14) . . ?
 N3 C6 C13 109.43(14) . . ?
 C13 C6 C5 112.03(13) . . ?
 N2 C7 N3 124.42(15) . . ?
 C3 C7 N2 109.49(14) . . ?
 C3 C7 N3 125.95(15) . . ?
 N1 C8 C2 178.6(2) . . ?
 N2 C9 C10 109.29(15) . . ?
 N2 C9 C11 108.63(15) . . ?
 N2 C9 C12 109.50(15) . . ?
 C10 C9 C11 108.66(16) . . ?
 C10 C9 C12 108.84(16) . . ?
 C11 C9 C12 111.87(19) . . ?
 C14 C13 C6 120.18(17) . . ?
 C14 C13 C18 118.29(17) . . ?
 C18 C13 C6 121.51(16) . . ?
 C13 C14 C15 120.8(2) . . ?
 C16 C15 C14 120.0(2) . . ?
 C17 C16 C15 120.1(2) . . ?
 C16 C17 C18 120.0(2) . . ?
 C17 C18 C13 120.8(2) . . ?
 O1 C19 C4 111.03(14) . . ?
 O2 C19 O1 123.18(17) . . ?
 O2 C19 C4 125.75(16) . . ?
 O1 C20 C21 107.59(18) . . ?
