#------------------------------------------------------------------------------
#$Date: 2023-11-06 09:57:45 +0200 (Mon, 06 Nov 2023) $
#$Revision: 287368 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/27/7062788.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7062788
loop_
_publ_author_name
'Shukla, Jyoti'
'Gangwar, Manoj Kumar'
'Koley, Dipankar'
_publ_section_title
;
 Total synthesis of (−)-δ-lycorane
;
_journal_issue                   41
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              18900
_journal_page_last               18904
_journal_paper_doi               10.1039/D3NJ03567K
_journal_volume                  47
_journal_year                    2023
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C21 H25 N O3'
_chemical_formula_sum            'C21 H25 N O3'
_chemical_formula_weight         339.44
_chemical_name_systematic        DK-CP-504
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_symmetry_Int_Tables_number      1
_audit_creation_date             2022-10-01
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-10-01 deposited with the CCDC.	2023-09-28 downloaded from the CCDC.
;
_cell_angle_alpha                108.948(3)
_cell_angle_beta                 94.920(4)
_cell_angle_gamma                93.497(4)
_cell_formula_units_Z            1
_cell_length_a                   5.8887(8)
_cell_length_b                   8.3187(12)
_cell_length_c                   9.4843(13)
_cell_measurement_reflns_used    6414
_cell_measurement_temperature    423.15
_cell_measurement_theta_max      28.40
_cell_measurement_theta_min      2.84
_cell_volume                     435.86(11)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_diffrn_ambient_temperature      423.15
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.9899
_diffrn_measured_fraction_theta_max 0.9778
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0372
_diffrn_reflns_av_unetI/netI     0.0574
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6414
_diffrn_reflns_theta_full        25.0000
_diffrn_reflns_theta_max         28.40
_diffrn_reflns_theta_min         2.84
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  0.983
_exptl_absorpt_correction_T_min  0.970
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2016/2 (Bruker,2016/2)'
_exptl_crystal_colour            'metallic light colourless'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.2931
_exptl_crystal_description       block
_exptl_crystal_F_000             182.0889
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.2111
_refine_diff_density_min         -0.2464
_refine_diff_density_rms         0.0501
_refine_ls_abs_structure_details
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   -0.4(6)
_refine_ls_d_res_high            0.7471
_refine_ls_d_res_low             7.1833
_refine_ls_goodness_of_fit_ref   1.0570
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    43
_refine_ls_number_parameters     228
_refine_ls_number_reflns         4263
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.0570
_refine_ls_R_factor_all          0.0481
_refine_ls_R_factor_gt           0.0419
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0349P)²+0.1133P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0981
_refine_ls_wR_factor_ref         0.1049
_reflns_Friedel_coverage         0.959
_reflns_limit_h_max              7
_reflns_limit_h_min              -7
_reflns_limit_k_max              11
_reflns_limit_k_min              -11
_reflns_limit_l_max              12
_reflns_limit_l_min              -12
_reflns_number_gt                3925
_reflns_number_total             4263
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d3nj03567k2.cif
_cod_data_source_block           DK-CP-504
_cod_depositor_comments          'Adding full bibliography for 7062788.cif.'
_cod_original_sg_symbol_Hall     ' P 1'
_cod_database_code               7062788
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8), C10(H10), C14(H14)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1a,H1b), C9(H9a,H9b), C11(H11a,H11b), C12(H12a,H12b), C13(H13a,H13b)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C4(H4), C3(H3a), C21(H21), C20(H20), C19(H19), C18(H18), C17(H17)
2.d Idealised Me refined as rotating group:
 C15(H15a,H15b,H15c)
2.e Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_olex2_submission_original_sample_id DK-CP-504
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
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_refinement_flags_posn
O1 O 0.9320(2) 0.10874(16) 0.90356(14) 0.0240(3) Uani 1.000000 .
O2 O 0.6031(2) 0.22616(17) 0.99545(14) 0.0269(3) Uani 1.000000 .
O3 O 0.1103(2) 0.34879(16) 0.33390(14) 0.0251(3) Uani 1.000000 .
H3 H 0.1452(16) 0.4489(9) 0.343(2) 0.0377(4) Uiso 1.000000 GR
N1 N 0.4066(2) 0.64171(17) 0.43446(15) 0.0160(3) Uani 1.000000 .
C1 C 0.7831(3) 0.1245(2) 1.0190(2) 0.0231(4) Uani 1.000000 .
H1a H 0.7184(3) 0.0125(2) 1.0141(2) 0.0277(4) Uiso 1.000000 R
H1b H 0.8683(3) 0.1790(2) 1.1171(2) 0.0277(4) Uiso 1.000000 R
C2 C 0.8180(3) 0.1694(2) 0.80089(18) 0.0173(3) Uani 1.000000 .
C3 C 0.8829(3) 0.1737(2) 0.66638(19) 0.0186(3) Uani 1.000000 .
H3a H 1.0144(3) 0.1271(2) 0.63000(19) 0.0224(4) Uiso 1.000000 R
C4 C 0.7409(3) 0.2521(2) 0.58615(19) 0.0183(3) Uani 1.000000 .
H4 H 0.7799(3) 0.2572(2) 0.49462(19) 0.0219(4) Uiso 1.000000 R
C5 C 0.5432(3) 0.3225(2) 0.64014(18) 0.0164(3) Uani 1.000000 .
C6 C 0.4822(3) 0.3156(2) 0.77861(19) 0.0178(3) Uani 1.000000 .
H6 H 0.3510(3) 0.3611(2) 0.81656(19) 0.0214(4) Uiso 1.000000 R
C7 C 0.6232(3) 0.2393(2) 0.85566(18) 0.0178(3) Uani 1.000000 .
C8 C 0.3928(3) 0.4083(2) 0.55331(18) 0.0168(3) Uani 1.000000 .
H8 H 0.2625(3) 0.4439(2) 0.61001(18) 0.0201(4) Uiso 1.000000 R
C9 C 0.2957(3) 0.2840(2) 0.39896(19) 0.0204(3) Uani 1.000000 .
H9a H 0.2430(3) 0.1758(2) 0.40871(19) 0.0245(4) Uiso 1.000000 R
H9b H 0.4159(3) 0.2638(2) 0.33313(19) 0.0245(4) Uiso 1.000000 R
C10 C 0.5241(3) 0.5727(2) 0.54595(18) 0.0171(3) Uani 1.000000 .
H10 H 0.6795(3) 0.5491(2) 0.52112(18) 0.0205(4) Uiso 1.000000 R
C11 C 0.5360(3) 0.7183(2) 0.69765(19) 0.0223(4) Uani 1.000000 .
H11a H 0.5211(3) 0.6738(2) 0.77943(19) 0.0268(4) Uiso 1.000000 R
H11b H 0.6783(3) 0.7912(2) 0.71809(19) 0.0268(4) Uiso 1.000000 R
C12 C 0.3313(3) 0.8142(2) 0.67393(19) 0.0228(4) Uani 1.000000 .
H12a H 0.1882(3) 0.7535(2) 0.67950(19) 0.0273(4) Uiso 1.000000 R
H12b H 0.3442(3) 0.9286(2) 0.74629(19) 0.0273(4) Uiso 1.000000 R
C13 C 0.3514(3) 0.8172(2) 0.51640(18) 0.0182(3) Uani 1.000000 .
H13a H 0.4725(3) 0.9016(2) 0.51629(18) 0.0218(4) Uiso 1.000000 R
H13b H 0.2086(3) 0.8419(2) 0.47231(18) 0.0218(4) Uiso 1.000000 R
C14 C 0.5323(3) 0.6280(2) 0.30132(18) 0.0182(3) Uani 1.000000 .
H14 H 0.5529(3) 0.5068(2) 0.25461(18) 0.0218(4) Uiso 1.000000 R
C15 C 0.7720(3) 0.7244(3) 0.3397(2) 0.0254(4) Uani 1.000000 .
H15a H 0.7606(4) 0.8428(4) 0.3930(15) 0.0380(6) Uiso 1.000000 GR
H15b H 0.8659(8) 0.6771(13) 0.4012(15) 0.0380(6) Uiso 1.000000 GR
H15c H 0.8395(11) 0.7136(17) 0.2488(2) 0.0380(6) Uiso 1.000000 GR
C16 C 0.3803(3) 0.6787(2) 0.18805(17) 0.0173(3) Uani 1.000000 .
C17 C 0.3982(3) 0.8444(2) 0.18050(19) 0.0207(4) Uani 1.000000 .
H17 H 0.5090(3) 0.9259(2) 0.24453(19) 0.0248(4) Uiso 1.000000 R
C18 C 0.2515(3) 0.8889(2) 0.0779(2) 0.0233(4) Uani 1.000000 .
H18 H 0.2641(3) 0.9996(2) 0.0745(2) 0.0279(4) Uiso 1.000000 R
C19 C 0.0876(3) 0.7676(2) -0.01844(18) 0.0207(3) Uani 1.000000 .
H19 H -0.0101(3) 0.7966(2) -0.08685(18) 0.0248(4) Uiso 1.000000 R
C20 C 0.0692(3) 0.6030(2) -0.01300(19) 0.0209(4) Uani 1.000000 .
H20 H -0.0408(3) 0.5216(2) -0.07795(19) 0.0251(4) Uiso 1.000000 R
C21 C 0.2149(3) 0.5589(2) 0.08938(18) 0.0192(3) Uani 1.000000 .
H21 H 0.2014(3) 0.4479(2) 0.09185(18) 0.0230(4) Uiso 1.000000 R
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
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
C2 O1 C1 105.43(13) . . ?
C7 O2 C1 105.13(13) . . ?
C9 O3 H3 109.5 . . ?
C13 N1 C10 108.00(12) . . ?
C14 N1 C10 114.13(12) . . ?
C14 N1 C13 114.33(13) . . ?
O2 C1 O1 107.97(13) . . ?
H1a C1 O1 110.11(9) . . ?
H1a C1 O2 110.11(10) . . ?
H1b C1 O1 110.11(9) . . ?
H1b C1 O2 110.11(9) . . ?
H1b C1 H1a 108.4 . . ?
C3 C2 O1 128.25(15) . . ?
C7 C2 O1 109.92(14) . . ?
C7 C2 C3 121.73(15) . . ?
H3a C3 C2 121.58(10) . . ?
C4 C3 C2 116.85(15) . . ?
C4 C3 H3a 121.58(10) . . ?
H4 C4 C3 119.06(10) . . ?
C5 C4 C3 121.88(15) . . ?
C5 C4 H4 119.06(10) . . ?
C6 C5 C4 119.61(14) . . ?
C8 C5 C4 121.37(14) . . ?
C8 C5 C6 119.02(14) . . ?
H6 C6 C5 121.13(9) . . ?
C7 C6 C5 117.74(15) . . ?
C7 C6 H6 121.13(10) . . ?
C2 C7 O2 110.26(14) . . ?
C6 C7 O2 127.50(15) . . ?
C6 C7 C2 122.18(15) . . ?
H8 C8 C5 107.13(9) . . ?
C9 C8 C5 111.55(13) . . ?
C9 C8 H8 107.13(9) . . ?
C10 C8 C5 110.33(13) . . ?
C10 C8 H8 107.13(9) . . ?
C10 C8 C9 113.22(13) . . ?
C8 C9 O3 111.54(14) . . ?
H9a C9 O3 109.32(9) . . ?
H9a C9 C8 109.32(9) . . ?
H9b C9 O3 109.32(9) . . ?
H9b C9 C8 109.32(9) . . ?
H9b C9 H9a 108.0 . . ?
C8 C10 N1 112.82(13) . . ?
H10 C10 N1 109.57(8) . . ?
H10 C10 C8 109.57(9) . . ?
C11 C10 N1 104.67(13) . . ?
C11 C10 C8 110.52(14) . . ?
C11 C10 H10 109.57(10) . . ?
H11a C11 C10 111.26(9) . . ?
H11b C11 C10 111.26(10) . . ?
H11b C11 H11a 109.2 . . ?
C12 C11 C10 102.52(13) . . ?
C12 C11 H11a 111.26(10) . . ?
C12 C11 H11b 111.26(9) . . ?
H12a C12 C11 111.55(10) . . ?
H12b C12 C11 111.55(9) . . ?
H12b C12 H12a 109.4 . . ?
C13 C12 C11 101.10(14) . . ?
C13 C12 H12a 111.55(10) . . ?
C13 C12 H12b 111.55(9) . . ?
C12 C13 N1 103.38(13) . . ?
H13a C13 N1 111.09(9) . . ?
H13a C13 C12 111.09(10) . . ?
H13b C13 N1 111.09(8) . . ?
H13b C13 C12 111.09(10) . . ?
H13b C13 H13a 109.1 . . ?
H14 C14 N1 106.76(8) . . ?
C15 C14 N1 114.21(14) . . ?
C15 C14 H14 106.76(10) . . ?
C16 C14 N1 108.62(13) . . ?
C16 C14 H14 106.76(9) . . ?
C16 C14 C15 113.26(14) . . ?
H15a C15 C14 109.5 . . ?
H15b C15 C14 109.5 . . ?
H15b C15 H15a 109.5 . . ?
H15c C15 C14 109.5 . . ?
H15c C15 H15a 109.5 . . ?
H15c C15 H15b 109.5 . . ?
C17 C16 C14 122.10(15) . . ?
C21 C16 C14 119.66(15) . . ?
C21 C16 C17 118.23(15) . . ?
H17 C17 C16 119.56(10) . . ?
C18 C17 C16 120.88(15) . . ?
C18 C17 H17 119.56(10) . . ?
H18 C18 C17 120.14(10) . . ?
C19 C18 C17 119.72(16) . . ?
C19 C18 H18 120.14(10) . . ?
H19 C19 C18 120.00(10) . . ?
C20 C19 C18 120.01(15) . . ?
C20 C19 H19 120.00(10) . . ?
H20 C20 C19 119.87(10) . . ?
C21 C20 C19 120.26(16) . . ?
C21 C20 H20 119.87(10) . . ?
C20 C21 C16 120.89(16) . . ?
H21 C21 C16 119.56(10) . . ?
H21 C21 C20 119.56(10) . . ?
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 C1 1.439(2) . ?
O1 C2 1.3790(19) . ?
O2 C1 1.442(2) . ?
O2 C7 1.380(2) . ?
O3 H3 0.8200 . ?
O3 C9 1.427(2) . ?
N1 C10 1.4980(19) . ?
N1 C13 1.485(2) . ?
N1 C14 1.494(2) . ?
C1 H1a 0.9700 . ?
C1 H1b 0.9700 . ?
C2 C3 1.373(2) . ?
C2 C7 1.383(2) . ?
C3 H3a 0.9300 . ?
C3 C4 1.408(2) . ?
C4 H4 0.9300 . ?
C4 C5 1.397(2) . ?
C5 C6 1.409(2) . ?
C5 C8 1.519(2) . ?
C6 H6 0.9300 . ?
C6 C7 1.373(2) . ?
C8 H8 0.9800 . ?
C8 C9 1.530(2) . ?
C8 C10 1.554(2) . ?
C9 H9a 0.9700 . ?
C9 H9b 0.9700 . ?
C10 H10 0.9800 . ?
C10 C11 1.544(2) . ?
C11 H11a 0.9700 . ?
C11 H11b 0.9700 . ?
C11 C12 1.525(2) . ?
C12 H12a 0.9700 . ?
C12 H12b 0.9700 . ?
C12 C13 1.517(2) . ?
C13 H13a 0.9700 . ?
C13 H13b 0.9700 . ?
C14 H14 0.9800 . ?
C14 C15 1.534(3) . ?
C14 C16 1.519(2) . ?
C15 H15a 0.9600 . ?
C15 H15b 0.9600 . ?
C15 H15c 0.9600 . ?
C16 C17 1.402(2) . ?
C16 C21 1.392(2) . ?
C17 H17 0.9300 . ?
C17 C18 1.400(2) . ?
C18 H18 0.9300 . ?
C18 C19 1.384(2) . ?
C19 H19 0.9300 . ?
C19 C20 1.385(2) . ?
C20 H20 0.9300 . ?
C20 C21 1.393(2) . ?
C21 H21 0.9300 . ?
