data_dgbicyclicnboc_1_0m
_audit_creation_date               2021-05-18
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_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-AXS (2016). APEX3. Version 2016.5-0. Madison, Wisconsin, USA. 
Dolomanov, O.V., Bourhis, L.J., Gildea, R.J, Howard, J.A.K. & Puschmann, H. 
"OLEX2: a complete structure solution, refinement and analysis program". 
(2009), J. Appl. Cryst. 42, 339-341. 
Krause, L., Herbst-Irmer, R., Sheldrick, G. M. & Stalke, D. (2015). 
J. Appl. Crystallogr. 48, 3-10. 
Sheldrick, G.M. (2015a). "SHELXT - Integrated space-group and crystal-structure 
determination". Acta Cryst. A71, 3-8. 
Sheldrick, G.M. (2015b). "Crystal structure refinement with SHELXL". 
Acta Cryst. C71, 3-8. 

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.
;
_chemical_name_common              ?
_chemical_name_systematic          ?
_chemical_formula_moiety           'C15 H21 N O3'
_chemical_formula_sum              'C15 H21 N O3'
_chemical_formula_weight           263.33
_chemical_absolute_configuration   unk
_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'
 '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        'monoclinic'
_space_group_IT_number             4
_space_group_name_H-M_alt          'P 1 21 1'
_space_group_name_Hall             'P 2yb'
loop_
  _space_group_symop_operation_xyz
 'x, y, z'
 '-x, y+1/2, -z'

_cell_length_a                     6.144(2)
_cell_length_b                     6.122(2)
_cell_length_c                     19.583(4)
_cell_angle_alpha                  90.00(3)
_cell_angle_beta                   98.95(3)
_cell_angle_gamma                  90.00(3)
_cell_volume                       727.7(4)
_cell_formula_units_Z              2
_cell_measurement_reflns_used      5361
_cell_measurement_temperature      172.92
_cell_measurement_theta_max        26.11
_cell_measurement_theta_min        3.16
_shelx_estimated_absorpt_T_max     0.993
_shelx_estimated_absorpt_T_min     0.973
_exptl_absorpt_coefficient_mu      0.083
_exptl_absorpt_correction_T_max    0.7454
_exptl_absorpt_correction_T_min    0.6666
_exptl_absorpt_correction_type     none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0529 before and 0.0455 after correction.
The Ratio of minimum to maximum transmission is 0.8943.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details     ?
_exptl_crystal_colour              colourless
_exptl_crystal_colour_primary      colourless
_exptl_crystal_density_diffrn      1.202
_exptl_crystal_density_meas        ?
_exptl_crystal_density_method      'not measured'
_exptl_crystal_description         spear
_exptl_crystal_F_000               284
_exptl_crystal_size_max            0.33
_exptl_crystal_size_mid            0.09
_exptl_crystal_size_min            0.09
_exptl_transmission_factor_max     ?
_exptl_transmission_factor_min     ?
_diffrn_reflns_av_R_equivalents    ?
_diffrn_reflns_av_unetI/netI       0.0184
_diffrn_reflns_Laue_measured_fraction_full  0.980
_diffrn_reflns_Laue_measured_fraction_max  0.981
_diffrn_reflns_limit_h_max         7
_diffrn_reflns_limit_h_min         -7
_diffrn_reflns_limit_k_max         7
_diffrn_reflns_limit_k_min         -7
_diffrn_reflns_limit_l_max         24
_diffrn_reflns_limit_l_min         -6
_diffrn_reflns_number              2723
_diffrn_reflns_point_group_measured_fraction_full  0.914
_diffrn_reflns_point_group_measured_fraction_max  0.911
_diffrn_reflns_theta_full          25.242
_diffrn_reflns_theta_max           26.416
_diffrn_reflns_theta_min           3.357
_diffrn.ambient_temp_esd           2.0
_diffrn_ambient_temperature        172.92
_diffrn_detector                   'charge-coupled device (CCD) area detector'
_diffrn_detector_area_resol_mean   7.9
_diffrn_detector_type              'Bruker Photon 50'
_diffrn_measured_fraction_theta_full  0.980
_diffrn_measured_fraction_theta_max  0.981
_diffrn_measurement_device         'three-circle diffractometer'
_diffrn_measurement_device_type    'Bruker APEX-II CCD'
_diffrn_measurement_method         'φ and ω scans'
_diffrn_radiation_collimation      'focusing mirrors'
_diffrn_radiation_detector         'Bruker Photon 50'
_diffrn_radiation_monochromator    'curved graphite'
_diffrn_radiation_probe            x-ray
_diffrn_radiation_type             'Mo K\a'
_diffrn_radiation_wavelength       0.71073
_diffrn_radiation_xray_symbol      K-L~3~
_diffrn_source                     'sealed X-ray tube'
_diffrn_source_current             20.0
_diffrn_source_power               1.0
_diffrn_source_type                'Siemens KFFMO2K--90C'
_diffrn_source_voltage             50.0
_diffrn_standards_number           0
_reflns_Friedel_coverage           0.692
_reflns_Friedel_fraction_full      0.833
_reflns_Friedel_fraction_max       0.826
_reflns_number_gt                  2647
_reflns_number_total               2723
_reflns_special_details
;
 _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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression       'I > 2σ(I)'
_computing_cell_refinement         'SAINT V8.40A (Bruker, 2019)'
_computing_data_collection         'APEX3 Ver. 2016.5-0 (Bruker-AXS, 2016)'
_computing_data_reduction          'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics      'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement    'XL  (Sheldrick, 2008)'
_computing_structure_solution      'XT  (Sheldrick, 2015)'
_refine_diff_density_max           0.171
_refine_diff_density_min           -0.160
_refine_diff_density_rms           0.035
_refine_ls_abs_structure_details
;
 Flack x determined using 1054 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack     0.2(7)
_refine_ls_extinction_coef         .
_refine_ls_extinction_method       none
_refine_ls_goodness_of_fit_ref     1.102
_refine_ls_hydrogen_treatment      constr
_refine_ls_matrix_type             full
_refine_ls_number_parameters       176
_refine_ls_number_reflns           2723
_refine_ls_number_restraints       1
_refine_ls_R_factor_all            0.0378
_refine_ls_R_factor_gt             0.0355
_refine_ls_restrained_S_all        1.102
_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)+(0.0210P)²+0.3293P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme        calc
_refine_ls_wR_factor_gt            0.0803
_refine_ls_wR_factor_ref           0.0826
_refine_special_details
;
 Refined as a 2-component twin.
;
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.503(2)
 0.497(2)
2. 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
3.a Ternary CH refined with riding coordinates:
 C00E(H00J), C00H(H00N)
3.b Secondary CH2 refined with riding coordinates:
 C005(H00A,H00B), C00B(H00F,H00G), C00C(H00H,H00I)
3.c Aromatic/amide H refined with riding coordinates:
 C008(H008), C00G(H00M)
3.d X=CH2 refined with riding coordinates:
 C00F(H00K,H00L)
3.e Idealised Me refined as rotating group:
 C007(H00C,H00D,H00E), C00I(H00O,H00P,H00Q), C00J(H00R,H00S,H00T)
;
_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
 N001 N -0.6597(4) -0.5382(5) -0.72253(14) 0.0268(6) Uani 1 1 d . . . . .
 O002 O -0.7581(4) -0.3862(5) -0.82560(12) 0.0314(6) Uani 1 1 d . . . . .
 C003 C -0.6823(7) -0.5220(7) -0.55774(18) 0.0368(9) Uani 1 1 d . . . . .
 O004 O -0.3951(4) -0.4170(5) -0.78310(13) 0.0368(6) Uani 1 1 d . . . . .
 C005 C -0.4913(6) -0.5160(6) -0.59846(17) 0.0302(8) Uani 1 1 d . . . . .
 H00A H -0.360437 -0.571713 -0.567443 0.036 Uiso 1 1 calc R U . . .
 H00B H -0.462231 -0.360258 -0.607232 0.036 Uiso 1 1 calc R U . . .
 O006 O -0.7177(6) -0.3570(6) -0.52590(15) 0.0579(9) Uani 1 1 d . . . . .
 C007 C -0.6096(8) -0.0667(7) -0.8771(2) 0.0454(11) Uani 1 1 d . . . . .
 H00C H -0.454481 -0.091247 -0.857867 0.068 Uiso 1 1 calc R U . . .
 H00D H -0.680764 0.016649 -0.843975 0.068 Uiso 1 1 calc R U . . .
 H00E H -0.618919 0.015340 -0.920397 0.068 Uiso 1 1 calc R U . . .
 C008 C -0.8168(6) -0.7159(7) -0.55114(18) 0.0359(9) Uani 1 1 d . . . . .
 H008 H -0.884731 -0.718727 -0.510760 0.043 Uiso 1 1 calc R U . . .
 C009 C -0.5887(6) -0.4452(6) -0.77766(16) 0.0247(7) Uani 1 1 d . . . . .
 C00A C -0.7240(6) -0.2831(6) -0.89087(17) 0.0307(8) Uani 1 1 d . . . . .
 C00B C -0.5400(6) -0.8813(6) -0.66247(17) 0.0274(7) Uani 1 1 d . . . . .
 H00F H -0.445970 -0.938752 -0.620672 0.033 Uiso 1 1 calc R U . . .
 H00G H -0.494243 -0.953890 -0.703136 0.033 Uiso 1 1 calc R U . . .
 C00C C -0.8934(5) -0.5835(6) -0.71909(18) 0.0262(8) Uani 1 1 d . . . . .
 H00H H -0.987025 -0.521322 -0.760195 0.031 Uiso 1 1 calc R U . . .
 H00I H -0.935336 -0.514006 -0.677384 0.031 Uiso 1 1 calc R U . . .
 C C -0.9297(6) -0.8263(6) -0.71645(17) 0.0257(7) Uani 1 1 d . . . . .
 C00E C -0.4999(6) -0.6354(6) -0.66738(16) 0.0248(8) Uani 1 1 d . . . . .
 H00J H -0.351437 -0.617811 -0.681574 0.030 Uiso 1 1 calc R U . . .
 C00F C -1.0827(6) -0.9253(8) -0.7603(2) 0.0399(9) Uani 1 1 d . . . . .
 H00K H -1.173572 -0.843174 -0.794793 0.048 Uiso 1 1 calc R U . . .
 H00L H -1.102111 -1.078844 -0.757524 0.048 Uiso 1 1 calc R U . . .
 C00G C -0.8600(6) -0.8887(7) -0.59205(18) 0.0332(8) Uani 1 1 d . . . . .
 H00M H -0.954913 -0.994394 -0.576766 0.040 Uiso 1 1 calc R U . . .
 C00H C -0.7805(6) -0.9414(6) -0.65918(18) 0.0280(7) Uani 1 1 d . . . . .
 H00N H -0.797442 -1.102230 -0.667167 0.034 Uiso 1 1 calc R U . . .
 C00I C -0.6005(7) -0.4371(8) -0.9318(2) 0.0469(11) Uani 1 1 d . . . . .
 H00O H -0.676102 -0.578426 -0.936815 0.070 Uiso 1 1 calc R U . . .
 H00P H -0.450017 -0.457353 -0.907458 0.070 Uiso 1 1 calc R U . . .
 H00Q H -0.595442 -0.374941 -0.977669 0.070 Uiso 1 1 calc R U . . .
 C00J C -0.9584(7) -0.2519(9) -0.9260(2) 0.0477(11) Uani 1 1 d . . . . .
 H00R H -1.034948 -0.392878 -0.929419 0.071 Uiso 1 1 calc R U . . .
 H00S H -0.958565 -0.192357 -0.972465 0.071 Uiso 1 1 calc R U . . .
 H00T H -1.034066 -0.150257 -0.898965 0.071 Uiso 1 1 calc R U . . .


_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
 N001 C009 1.352(4) . ?
 N001 C00C 1.474(4) . ?
 N001 C00E 1.468(4) . ?
 O002 C009 1.338(4) . ?
 O002 C00A 1.469(4) . ?
 C003 C005 1.518(6) . ?
 C003 O006 1.225(5) . ?
 C003 C008 1.464(6) . ?
 O004 C009 1.223(4) . ?
 C005 H00A 0.9900 . ?
 C005 H00B 0.9900 . ?
 C005 C00E 1.529(5) . ?
 C007 H00C 0.9800 . ?
 C007 H00D 0.9800 . ?
 C007 H00E 0.9800 . ?
 C007 C00A 1.504(6) . ?
 C008 H008 0.9500 . ?
 C008 C00G 1.328(6) . ?
 C00A C00I 1.515(5) . ?
 C00A C00J 1.509(5) . ?
 C00B H00F 0.9900 . ?
 C00B H00G 0.9900 . ?
 C00B C00E 1.531(5) . ?
 C00B C00H 1.534(5) . ?
 C00C H00H 0.9900 . ?
 C00C H00I 0.9900 . ?
 C00C C 1.505(5) . ?
 C C00F 1.319(5) . ?
 C C00H 1.508(5) . ?
 C00E H00J 1.0000 . ?
 C00F H00K 0.9500 . ?
 C00F H00L 0.9500 . ?
 C00G H00M 0.9500 . ?
 C00G C00H 1.507(5) . ?
 C00H H00N 1.0000 . ?
 C00I H00O 0.9800 . ?
 C00I H00P 0.9800 . ?
 C00I H00Q 0.9800 . ?
 C00J H00R 0.9800 . ?
 C00J H00S 0.9800 . ?
 C00J H00T 0.9800 . ?

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
 C009 N001 C00C 123.6(3) . . ?
 C009 N001 C00E 119.8(3) . . ?
 C00E N001 C00C 115.8(3) . . ?
 C009 O002 C00A 121.7(3) . . ?
 O006 C003 C005 117.4(4) . . ?
 O006 C003 C008 118.5(4) . . ?
 C008 C003 C005 124.0(3) . . ?
 C003 C005 H00A 106.9 . . ?
 C003 C005 H00B 106.9 . . ?
 C003 C005 C00E 121.9(3) . . ?
 H00A C005 H00B 106.7 . . ?
 C00E C005 H00A 106.9 . . ?
 C00E C005 H00B 106.9 . . ?
 H00C C007 H00D 109.5 . . ?
 H00C C007 H00E 109.5 . . ?
 H00D C007 H00E 109.5 . . ?
 C00A C007 H00C 109.5 . . ?
 C00A C007 H00D 109.5 . . ?
 C00A C007 H00E 109.5 . . ?
 C003 C008 H008 114.5 . . ?
 C00G C008 C003 130.9(3) . . ?
 C00G C008 H008 114.5 . . ?
 O002 C009 N001 111.2(3) . . ?
 O004 C009 N001 124.6(3) . . ?
 O004 C009 O002 124.2(3) . . ?
 O002 C00A C007 110.4(3) . . ?
 O002 C00A C00I 110.1(3) . . ?
 O002 C00A C00J 101.3(3) . . ?
 C007 C00A C00I 112.6(4) . . ?
 C007 C00A C00J 110.9(4) . . ?
 C00J C00A C00I 111.0(3) . . ?
 H00F C00B H00G 107.7 . . ?
 C00E C00B H00F 108.8 . . ?
 C00E C00B H00G 108.8 . . ?
 C00E C00B C00H 113.8(3) . . ?
 C00H C00B H00F 108.8 . . ?
 C00H C00B H00G 108.8 . . ?
 N001 C00C H00H 109.7 . . ?
 N001 C00C H00I 109.7 . . ?
 N001 C00C C 109.8(3) . . ?
 H00H C00C H00I 108.2 . . ?
 C C00C H00H 109.7 . . ?
 C C00C H00I 109.7 . . ?
 C00C C C00H 114.2(3) . . ?
 C00F C C00C 121.7(4) . . ?
 C00F C C00H 124.0(4) . . ?
 N001 C00E C005 112.5(3) . . ?
 N001 C00E C00B 110.4(3) . . ?
 N001 C00E H00J 106.6 . . ?
 C005 C00E C00B 113.5(3) . . ?
 C005 C00E H00J 106.6 . . ?
 C00B C00E H00J 106.6 . . ?
 C C00F H00K 120.0 . . ?
 C C00F H00L 120.0 . . ?
 H00K C00F H00L 120.0 . . ?
 C008 C00G H00M 115.3 . . ?
 C008 C00G C00H 129.4(3) . . ?
 C00H C00G H00M 115.3 . . ?
 C00B C00H H00N 107.9 . . ?
 C C00H C00B 109.6(3) . . ?
 C C00H H00N 107.9 . . ?
 C00G C00H C00B 115.5(3) . . ?
 C00G C00H C 107.8(3) . . ?
 C00G C00H H00N 107.9 . . ?
 C00A C00I H00O 109.5 . . ?
 C00A C00I H00P 109.5 . . ?
 C00A C00I H00Q 109.5 . . ?
 H00O C00I H00P 109.5 . . ?
 H00O C00I H00Q 109.5 . . ?
 H00P C00I H00Q 109.5 . . ?
 C00A C00J H00R 109.5 . . ?
 C00A C00J H00S 109.5 . . ?
 C00A C00J H00T 109.5 . . ?
 H00R C00J H00S 109.5 . . ?
 H00R C00J H00T 109.5 . . ?
 H00S C00J H00T 109.5 . . ?

loop_
  _geom_torsion_atom_site_label_1
  _geom_torsion_atom_site_label_2
  _geom_torsion_atom_site_label_3
  _geom_torsion_atom_site_label_4
  _geom_torsion
  _geom_torsion_site_symmetry_1
  _geom_torsion_site_symmetry_2
  _geom_torsion_site_symmetry_3
  _geom_torsion_site_symmetry_4
  _geom_torsion_publ_flag
 N001 C00C C C00F -126.8(4) . . . . ?
 N001 C00C C C00H 54.3(4) . . . . ?
 C003 C005 C00E N001 68.4(4) . . . . ?
 C003 C005 C00E C00B -58.0(4) . . . . ?
 C003 C008 C00G C00H 0.7(7) . . . . ?
 C005 C003 C008 C00G -25.5(6) . . . . ?
 O006 C003 C005 C00E -144.9(4) . . . . ?
 O006 C003 C008 C00G 158.3(4) . . . . ?
 C008 C003 C005 C00E 38.8(5) . . . . ?
 C008 C00G C00H C00B 38.9(5) . . . . ?
 C008 C00G C00H C -84.0(5) . . . . ?
 C009 N001 C00C C 114.4(4) . . . . ?
 C009 N001 C00E C005 115.3(4) . . . . ?
 C009 N001 C00E C00B -116.8(4) . . . . ?
 C009 O002 C00A C007 -63.0(4) . . . . ?
 C009 O002 C00A C00I 61.9(4) . . . . ?
 C009 O002 C00A C00J 179.5(4) . . . . ?
 C00A O002 C009 N001 -179.4(3) . . . . ?
 C00A O002 C009 O004 1.0(6) . . . . ?
 C00C N001 C009 O002 4.6(5) . . . . ?
 C00C N001 C009 O004 -175.9(4) . . . . ?
 C00C N001 C00E C005 -74.9(4) . . . . ?
 C00C N001 C00E C00B 53.1(4) . . . . ?
 C00C C C00H C00B -52.4(4) . . . . ?
 C00C C C00H C00G 74.1(4) . . . . ?
 C00E N001 C009 O002 173.5(3) . . . . ?
 C00E N001 C009 O004 -6.9(6) . . . . ?
 C00E N001 C00C C -54.9(4) . . . . ?
 C00E C00B C00H C 49.8(4) . . . . ?
 C00E C00B C00H C00G -72.2(4) . . . . ?
 C00F C C00H C00B 128.8(4) . . . . ?
 C00F C C00H C00G -104.7(4) . . . . ?
 C00H C00B C00E N001 -50.0(4) . . . . ?
 C00H C00B C00E C005 77.4(4) . . . . ?


_olex2_submission_special_instructions  'No special instructions were received'
loop_
  _twin_individual_id
  _twin_individual_mass_fraction_refined
 1 0.503(2)
 2 0.497(2)

