data_ra126
_audit_creation_date              2017-09-21
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number      '2017/1'
_publ_contact_author_address      ?
_publ_contact_author_email        ?
_publ_contact_author_id_orcid     ?
_publ_contact_author_name         ''
_publ_contact_author_phone        ?
_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. A71, 3-8.
;
_chemical_name_common             ?
_chemical_name_systematic         ?
_chemical_formula_moiety          'C17 H17 N O3'
_chemical_formula_sum             'C17 H17 N O3'
_chemical_formula_weight          283.31
_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, z+1/2'
 '-x, y+1/2, -z+1/2'
 'x+1/2, -y+1/2, -z'

_cell_length_a                    7.6392(7)
_cell_length_b                    8.9874(8)
_cell_length_c                    20.4621(17)
_cell_angle_alpha                 90
_cell_angle_beta                  90
_cell_angle_gamma                 90
_cell_volume                      1404.9(2)
_cell_formula_units_Z             4
_cell_measurement_reflns_used     6523
_cell_measurement_temperature     90(2)
_cell_measurement_theta_max       68.23
_cell_measurement_theta_min       4.32
_shelx_estimated_absorpt_T_max    0.936
_shelx_estimated_absorpt_T_min    0.903
_exptl_absorpt_coefficient_mu     0.747
_exptl_absorpt_correction_T_max   0.935
_exptl_absorpt_correction_T_min   0.841
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0726 before and 0.0595 after correction. The Ratio of minimum to maximum transmission is 0.8995. The λ/2 correction factor is 0.00150.'
_exptl_absorpt_special_details    ?
_exptl_crystal_colour             colourless
_exptl_crystal_colour_primary     colourless
_exptl_crystal_density_diffrn     1.340
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_description        'prism'
_exptl_crystal_F_000              600
_exptl_crystal_size_max           0.14
_exptl_crystal_size_mid           0.13
_exptl_crystal_size_min           0.09
_exptl_transmission_factor_max    ?
_exptl_transmission_factor_min    ?
_diffrn_reflns_av_R_equivalents   0.0445
_diffrn_reflns_av_unetI/netI      0.0417
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max        8
_diffrn_reflns_limit_h_min        -9
_diffrn_reflns_limit_k_max        10
_diffrn_reflns_limit_k_min        -10
_diffrn_reflns_limit_l_max        24
_diffrn_reflns_limit_l_min        -24
_diffrn_reflns_number             9367
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full         67.679
_diffrn_reflns_theta_max          68.220
_diffrn_reflns_theta_min          4.321
_diffrn_ambient_temperature       90(2)
_diffrn_detector                  'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean  7.9
_diffrn_detector_type             'CCD area detector'
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device        'Bruker-Nonius Kappa diffractometer'
_diffrn_measurement_device_type   'Bruker APEX II area detector'
_diffrn_measurement_method        'ω and φ scans'
_diffrn_radiation_monochromator   'mirror optics'
_diffrn_radiation_probe           X-ray
_diffrn_radiation_type            CuK\a
_diffrn_radiation_wavelength      1.54178
_diffrn_source                    'microfocus sealed X-ray tube'
_diffrn_source_type               'Incoatec I\ms'
_diffrn_standards_number          0
_reflns_Friedel_coverage          0.690
_reflns_Friedel_fraction_full     0.975
_reflns_Friedel_fraction_max      0.972
_reflns_number_gt                 2356
_reflns_number_total              2539
_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 v8.34A (Bruker, 2013)'
_computing_data_collection        ?
_computing_data_reduction         'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics     'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material   'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement   'XL (Sheldrick, 2008)'
_computing_structure_solution     'XT (Sheldrick, 2015)'
_refine_diff_density_max          0.140
_refine_diff_density_min          -0.206
_refine_diff_density_rms          0.042
_refine_ls_abs_structure_details
;
 Flack x determined using 925 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack    -0.09(15)
_refine_ls_extinction_coef        .
_refine_ls_extinction_method      none
_refine_ls_goodness_of_fit_ref    1.072
_refine_ls_hydrogen_treatment     mixed
_refine_ls_matrix_type            full
_refine_ls_number_parameters      194
_refine_ls_number_reflns          2539
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0365
_refine_ls_R_factor_gt            0.0328
_refine_ls_restrained_S_all       1.072
_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)+(0.0373P)²+0.3087P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme       calc
_refine_ls_wR_factor_gt           0.0809
_refine_ls_wR_factor_ref          0.0839
_refine_special_details           ?
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C8(H8A,H8B)
2.c Aromatic/amide H refined with riding coordinates:
 C2'(H2'), C3'(H3'), C5(H5), C5'(H5'), C6(H6), C6'(H6'), C7'(H7'), C8'(H8'),
 C9'(H9')
;
_atom_sites_solution_hydrogens    mixed
_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
 O1 O 0.5785(2) 0.25339(19) 0.68600(7) 0.0184(3) Uani 1 1 d . . . . .
 H1 H 0.493(5) 0.256(4) 0.7137(16) 0.048(9) Uiso 1 1 d . . . . .
 O2 O 0.8097(3) 0.4406(2) 0.91144(8) 0.0304(4) Uani 1 1 d . . . . .
 O3 O 0.6735(2) 0.76655(17) 0.72175(7) 0.0213(4) Uani 1 1 d . . . . .
 N1 N 0.7613(3) 0.5451(2) 0.68098(8) 0.0171(4) Uani 1 1 d . . . . .
 C1' C 0.7311(3) 0.6919(2) 0.67509(10) 0.0173(5) Uani 1 1 d . . . . .
 C2 C 0.8394(3) 0.4464(2) 0.63084(11) 0.0191(5) Uani 1 1 d . . . . .
 H2A H 0.947315 0.490386 0.612275 0.023 Uiso 1 1 calc R . . . .
 H2B H 0.755575 0.426157 0.595027 0.023 Uiso 1 1 calc R . . . .
 C2' C 0.7676(3) 0.7615(3) 0.61087(10) 0.0191(5) Uani 1 1 d . . . . .
 H2' H 0.826769 0.707002 0.577805 0.023 Uiso 1 1 calc R . . . .
 C3 C 0.8797(3) 0.3056(3) 0.66950(10) 0.0189(5) Uani 1 1 d . . . . .
 H3A H 0.995557 0.312460 0.690997 0.023 Uiso 1 1 calc R . . . .
 H3B H 0.877804 0.216781 0.640891 0.023 Uiso 1 1 calc R . . . .
 C3' C 0.7167(3) 0.9014(3) 0.59978(10) 0.0196(5) Uani 1 1 d . . . . .
 H3' H 0.658007 0.950642 0.634530 0.024 Uiso 1 1 calc R . . . .
 C4 C 0.7322(3) 0.2994(2) 0.72012(10) 0.0166(5) Uani 1 1 d . . . . .
 C4' C 0.7421(3) 0.9868(2) 0.53932(10) 0.0181(5) Uani 1 1 d . . . . .
 C5 C 0.7641(3) 0.1956(2) 0.77643(11) 0.0191(5) Uani 1 1 d . . . . .
 H5 H 0.760452 0.091780 0.767923 0.023 Uiso 1 1 calc R . . . .
 C5' C 0.8579(3) 0.9436(3) 0.48994(10) 0.0199(5) Uani 1 1 d . . . . .
 H5' H 0.923417 0.854277 0.494232 0.024 Uiso 1 1 calc R . . . .
 C6 C 0.7973(3) 0.2391(3) 0.83760(10) 0.0210(5) Uani 1 1 d . . . . .
 H6 H 0.811536 0.165970 0.870703 0.025 Uiso 1 1 calc R . . . .
 C6' C 0.8767(3) 1.0315(3) 0.43464(11) 0.0213(5) Uani 1 1 d . . . . .
 H6' H 0.955165 1.001713 0.401078 0.026 Uiso 1 1 calc R . . . .
 C7 C 0.8123(3) 0.3978(3) 0.85504(11) 0.0217(5) Uani 1 1 d . . . . .
 C7' C 0.7822(3) 1.1622(3) 0.42787(10) 0.0217(5) Uani 1 1 d . . . . .
 H7' H 0.796298 1.221562 0.389813 0.026 Uiso 1 1 calc R . . . .
 C8 C 0.8369(3) 0.5025(2) 0.79802(10) 0.0201(5) Uani 1 1 d . . . . .
 H8A H 0.960049 0.497862 0.783067 0.024 Uiso 1 1 calc R . . . .
 H8B H 0.812768 0.605668 0.812391 0.024 Uiso 1 1 calc R . . . .
 C8' C 0.6672(3) 1.2066(3) 0.47644(11) 0.0217(5) Uani 1 1 d . . . . .
 H8' H 0.601840 1.295934 0.471826 0.026 Uiso 1 1 calc R . . . .
 C9 C 0.7157(3) 0.4630(2) 0.74117(10) 0.0167(5) Uani 1 1 d . . . . .
 H9 H 0.591632 0.484819 0.753513 0.020 Uiso 1 1 calc R . . . .
 C9' C 0.6483(3) 1.1190(2) 0.53206(11) 0.0206(5) Uani 1 1 d . . . . .
 H9' H 0.570317 1.149610 0.565618 0.025 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 H1 0.87(4) . ?
 O1 C4 1.427(3) . ?
 O2 C7 1.217(3) . ?
 O3 C1' 1.247(3) . ?
 N1 C1' 1.345(3) . ?
 N1 C2 1.481(3) . ?
 N1 C9 1.477(3) . ?
 C1' C2' 1.482(3) . ?
 C2 H2A 0.9900 . ?
 C2 H2B 0.9900 . ?
 C2 C3 1.524(3) . ?
 C2' H2' 0.9500 . ?
 C2' C3' 1.335(3) . ?
 C3 H3A 0.9900 . ?
 C3 H3B 0.9900 . ?
 C3 C4 1.532(3) . ?
 C3' H3' 0.9500 . ?
 C3' C4' 1.469(3) . ?
 C4 C5 1.502(3) . ?
 C4 C9 1.537(3) . ?
 C4' C5' 1.398(3) . ?
 C4' C9' 1.395(3) . ?
 C5 H5 0.9500 . ?
 C5 C6 1.335(3) . ?
 C5' H5' 0.9500 . ?
 C5' C6' 1.387(3) . ?
 C6 H6 0.9500 . ?
 C6 C7 1.475(3) . ?
 C6' H6' 0.9500 . ?
 C6' C7' 1.386(3) . ?
 C7 C8 1.511(3) . ?
 C7' H7' 0.9500 . ?
 C7' C8' 1.385(3) . ?
 C8 H8A 0.9900 . ?
 C8 H8B 0.9900 . ?
 C8 C9 1.529(3) . ?
 C8' H8' 0.9500 . ?
 C8' C9' 1.392(3) . ?
 C9 H9 1.0000 . ?
 C9' H9' 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
 C4 O1 H1 107(2) . . ?
 C1' N1 C2 126.45(18) . . ?
 C1' N1 C9 121.62(18) . . ?
 C9 N1 C2 111.93(16) . . ?
 O3 C1' N1 121.31(19) . . ?
 O3 C1' C2' 121.19(19) . . ?
 N1 C1' C2' 117.50(19) . . ?
 N1 C2 H2A 111.2 . . ?
 N1 C2 H2B 111.2 . . ?
 N1 C2 C3 102.65(16) . . ?
 H2A C2 H2B 109.2 . . ?
 C3 C2 H2A 111.2 . . ?
 C3 C2 H2B 111.2 . . ?
 C1' C2' H2' 120.2 . . ?
 C3' C2' C1' 119.6(2) . . ?
 C3' C2' H2' 120.2 . . ?
 C2 C3 H3A 111.1 . . ?
 C2 C3 H3B 111.1 . . ?
 C2 C3 C4 103.43(18) . . ?
 H3A C3 H3B 109.0 . . ?
 C4 C3 H3A 111.1 . . ?
 C4 C3 H3B 111.1 . . ?
 C2' C3' H3' 116.7 . . ?
 C2' C3' C4' 126.6(2) . . ?
 C4' C3' H3' 116.7 . . ?
 O1 C4 C3 106.57(17) . . ?
 O1 C4 C5 109.20(17) . . ?
 O1 C4 C9 110.28(18) . . ?
 C3 C4 C9 102.42(17) . . ?
 C5 C4 C3 114.94(18) . . ?
 C5 C4 C9 113.09(18) . . ?
 C5' C4' C3' 123.2(2) . . ?
 C9' C4' C3' 117.8(2) . . ?
 C9' C4' C5' 119.0(2) . . ?
 C4 C5 H5 117.7 . . ?
 C6 C5 C4 124.6(2) . . ?
 C6 C5 H5 117.7 . . ?
 C4' C5' H5' 120.1 . . ?
 C6' C5' C4' 119.8(2) . . ?
 C6' C5' H5' 120.1 . . ?
 C5 C6 H6 119.2 . . ?
 C5 C6 C7 121.6(2) . . ?
 C7 C6 H6 119.2 . . ?
 C5' C6' H6' 119.7 . . ?
 C7' C6' C5' 120.7(2) . . ?
 C7' C6' H6' 119.7 . . ?
 O2 C7 C6 122.3(2) . . ?
 O2 C7 C8 122.5(2) . . ?
 C6 C7 C8 115.17(19) . . ?
 C6' C7' H7' 119.9 . . ?
 C8' C7' C6' 120.2(2) . . ?
 C8' C7' H7' 119.9 . . ?
 C7 C8 H8A 109.3 . . ?
 C7 C8 H8B 109.3 . . ?
 C7 C8 C9 111.56(19) . . ?
 H8A C8 H8B 108.0 . . ?
 C9 C8 H8A 109.3 . . ?
 C9 C8 H8B 109.3 . . ?
 C7' C8' H8' 120.3 . . ?
 C7' C8' C9' 119.3(2) . . ?
 C9' C8' H8' 120.3 . . ?
 N1 C9 C4 102.99(16) . . ?
 N1 C9 C8 112.04(18) . . ?
 N1 C9 H9 109.6 . . ?
 C4 C9 H9 109.6 . . ?
 C8 C9 C4 112.69(18) . . ?
 C8 C9 H9 109.6 . . ?
 C4' C9' H9' 119.5 . . ?
 C8' C9' C4' 121.1(2) . . ?
 C8' C9' H9' 119.5 . . ?

loop_
  _geom_hbond_atom_site_label_D
  _geom_hbond_atom_site_label_H
  _geom_hbond_atom_site_label_A
  _geom_hbond_distance_DH
  _geom_hbond_distance_HA
  _geom_hbond_distance_DA
  _geom_hbond_angle_DHA
  _geom_hbond_site_symmetry_A
  _geom_hbond_publ_flag
 O1 H1 O3 0.87(4) 1.83(4) 2.698(2) 175(3) 3_646 yes

_olex2_submission_special_instructions 'No special instructions were received'
