#------------------------------------------------------------------------------
#$Date: 2025-08-18 17:33:07 +0200 (Mon 18 de Aug de 2025) $
#$Revision: 301779 $
#$URL: svn://www.crystallography.net/cod/cif/1/54/55/1545575.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_1545575
loop_
_publ_author_name
'Li, Jian Long'
'Shi, Hong Wei'
'Wang, Qi'
'Chai, Yong Hai'
'Yang, Jun'
_publ_section_title
;
 Synthesis of the ABC Tricyclic System of Daphnicyclidin A.
;
_journal_issue                   7
_journal_name_full               'Organic letters'
_journal_page_first              1497
_journal_page_last               1499
_journal_paper_doi               10.1021/acs.orglett.7b00230
_journal_volume                  19
_journal_year                    2017
_chemical_absolute_configuration unk
_chemical_formula_sum            'C14 H19 N O2'
_chemical_formula_weight         233.30
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 91.285(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   6.399(3)
_cell_length_b                   11.401(6)
_cell_length_c                   8.532(4)
_cell_measurement_reflns_used    1207
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      23.08
_cell_measurement_theta_min      3.18
_cell_volume                     622.3(5)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0208
_diffrn_reflns_av_sigmaI/netI    0.0388
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            3117
_diffrn_reflns_theta_full        25.10
_diffrn_reflns_theta_max         25.10
_diffrn_reflns_theta_min         2.39
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.9811
_exptl_absorpt_correction_T_min  0.9693
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS; (Sheldrick, 2003)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.245
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             252
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.141
_refine_diff_density_min         -0.165
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         1821
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.011
_refine_ls_R_factor_all          0.0516
_refine_ls_R_factor_gt           0.0493
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0200P)²+0.3699P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0967
_refine_ls_wR_factor_ref         0.0982
_reflns_number_gt                1731
_reflns_number_total             1821
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol7b00230_si_004.cif
_cod_data_source_block           xb8946_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 

 Adding full bibliography for 1545574--1545575.cif.
;
_cod_original_sg_symbol_H-M      P2(1)
_cod_database_code               1545575
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
N1 N 0.3703(4) 0.1721(2) 0.9242(3) 0.0369(6) Uani 1 1 d .
O1 O 0.3071(5) 0.4648(3) 1.2434(3) 0.0822(10) Uani 1 1 d .
O2 O 0.1747(4) 0.0999(2) 1.1167(3) 0.0588(7) Uani 1 1 d .
C1 C 0.3637(5) 0.4194(3) 1.1236(4) 0.0451(8) Uani 1 1 d .
C2 C 0.2484(5) 0.4498(3) 0.9774(4) 0.0432(8) Uani 1 1 d .
H2 H 0.1454 0.5061 0.9915 0.052 Uiso 1 1 calc R
C3 C 0.2609(4) 0.4135(3) 0.8292(4) 0.0402(7) Uani 1 1 d .
H3 H 0.1641 0.4497 0.7622 0.048 Uiso 1 1 calc R
C4 C 0.3976(4) 0.3266(3) 0.7467(3) 0.0366(7) Uani 1 1 d .
C5 C 0.5284(4) 0.2515(3) 0.8595(3) 0.0362(7) Uani 1 1 d .
H5 H 0.6224 0.2039 0.7965 0.043 Uiso 1 1 calc R
C6 C 0.6620(5) 0.3153(3) 0.9820(4) 0.0457(8) Uani 1 1 d .
H6A H 0.7869 0.2696 1.0049 0.055 Uiso 1 1 calc R
H6B H 0.7054 0.3903 0.9400 0.055 Uiso 1 1 calc R
C7 C 0.5454(5) 0.3356(3) 1.1330(3) 0.0440(8) Uani 1 1 d .
H7 H 0.6461 0.3669 1.2105 0.053 Uiso 1 1 calc R
C8 C 0.4709(5) 0.2161(3) 1.1935(4) 0.0472(8) Uani 1 1 d .
H8A H 0.5909 0.1661 1.2146 0.057 Uiso 1 1 calc R
H8B H 0.3984 0.2271 1.2911 0.057 Uiso 1 1 calc R
C9 C 0.3265(5) 0.1572(3) 1.0757(3) 0.0410(7) Uani 1 1 d .
C10 C 0.2105(5) 0.1464(3) 0.8029(3) 0.0433(8) Uani 1 1 d .
H10A H 0.0716 0.1622 0.8409 0.052 Uiso 1 1 calc R
H10B H 0.2178 0.0651 0.7702 0.052 Uiso 1 1 calc R
C11 C 0.2627(4) 0.2286(3) 0.6676(3) 0.0392(7) Uani 1 1 d .
H11 H 0.3543 0.1851 0.5977 0.047 Uiso 1 1 calc R
C12 C 0.0717(5) 0.2654(3) 0.5709(4) 0.0524(9) Uani 1 1 d .
H12A H 0.1133 0.3215 0.4920 0.063 Uiso 1 1 calc R
H12B H -0.0271 0.3038 0.6385 0.063 Uiso 1 1 calc R
C13 C -0.0350(6) 0.1610(4) 0.4903(4) 0.0674(11) Uani 1 1 d .
H13A H 0.0622 0.1228 0.4231 0.101 Uiso 1 1 calc R
H13B H -0.1532 0.1880 0.4291 0.101 Uiso 1 1 calc R
H13C H -0.0811 0.1066 0.5682 0.101 Uiso 1 1 calc R
C14 C 0.5277(5) 0.3931(3) 0.6270(4) 0.0532(9) Uani 1 1 d .
H14A H 0.4361 0.4346 0.5557 0.080 Uiso 1 1 calc R
H14B H 0.6105 0.3384 0.5696 0.080 Uiso 1 1 calc R
H14C H 0.6178 0.4479 0.6808 0.080 Uiso 1 1 calc R
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C9 N1 C10 119.8(2)
C9 N1 C5 126.8(2)
C10 N1 C5 109.4(2)
O1 C1 C2 117.5(3)
O1 C1 C7 118.2(3)
C2 C1 C7 124.3(3)
C3 C2 C1 133.5(3)
C3 C2 H2 113.3
C1 C2 H2 113.3
C2 C3 C4 134.0(3)
C2 C3 H3 113.0
C4 C3 H3 113.0
C3 C4 C5 113.0(2)
C3 C4 C14 108.4(3)
C5 C4 C14 113.6(2)
C3 C4 C11 110.6(2)
C5 C4 C11 99.3(2)
C14 C4 C11 111.8(2)
N1 C5 C6 114.6(2)
N1 C5 C4 102.1(2)
C6 C5 C4 117.2(2)
N1 C5 H5 107.4
C6 C5 H5 107.4
C4 C5 H5 107.4
C7 C6 C5 112.1(3)
C7 C6 H6A 109.2
C5 C6 H6A 109.2
C7 C6 H6B 109.2
C5 C6 H6B 109.2
H6A C6 H6B 107.9
C1 C7 C6 116.4(3)
C1 C7 C8 109.6(3)
C6 C7 C8 108.2(3)
C1 C7 H7 107.4
C6 C7 H7 107.4
C8 C7 H7 107.4
C9 C8 C7 111.2(2)
C9 C8 H8A 109.4
C7 C8 H8A 109.4
C9 C8 H8B 109.4
C7 C8 H8B 109.4
H8A C8 H8B 108.0
O2 C9 N1 121.8(3)
O2 C9 C8 121.6(3)
N1 C9 C8 116.7(3)
N1 C10 C11 104.5(2)
N1 C10 H10A 110.9
C11 C10 H10A 110.9
N1 C10 H10B 110.9
C11 C10 H10B 110.9
H10A C10 H10B 108.9
C12 C11 C10 113.1(3)
C12 C11 C4 118.0(3)
C10 C11 C4 104.0(2)
C12 C11 H11 107.1
C10 C11 H11 107.1
C4 C11 H11 107.1
C11 C12 C13 112.0(3)
C11 C12 H12A 109.2
C13 C12 H12A 109.2
C11 C12 H12B 109.2
C13 C12 H12B 109.2
H12A C12 H12B 107.9
C12 C13 H13A 109.5
C12 C13 H13B 109.5
H13A C13 H13B 109.5
C12 C13 H13C 109.5
H13A C13 H13C 109.5
H13B C13 H13C 109.5
C4 C14 H14A 109.5
C4 C14 H14B 109.5
H14A C14 H14B 109.5
C4 C14 H14C 109.5
H14A C14 H14C 109.5
H14B C14 H14C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C9 1.340(4)
N1 C10 1.467(4)
N1 C5 1.474(4)
O1 C1 1.208(4)
O2 C9 1.228(4)
C1 C2 1.477(4)
C1 C7 1.506(4)
C2 C3 1.335(4)
C2 H2 0.9300
C3 C4 1.506(4)
C3 H3 0.9300
C4 C5 1.525(4)
C4 C14 1.532(4)
C4 C11 1.557(4)
C5 C6 1.521(4)
C5 H5 0.9800
C6 C7 1.520(4)
C6 H6A 0.9700
C6 H6B 0.9700
C7 C8 1.537(4)
C7 H7 0.9800
C8 C9 1.508(4)
C8 H8A 0.9700
C8 H8B 0.9700
C10 C11 1.529(4)
C10 H10A 0.9700
C10 H10B 0.9700
C11 C12 1.519(4)
C11 H11 0.9800
C12 C13 1.527(5)
C12 H12A 0.9700
C12 H12B 0.9700
C13 H13A 0.9600
C13 H13B 0.9600
C13 H13C 0.9600
C14 H14A 0.9600
C14 H14B 0.9600
C14 H14C 0.9600
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
O1 C1 C2 C3 -176.4(4)
C7 C1 C2 C3 3.3(6)
C1 C2 C3 C4 -0.3(6)
C2 C3 C4 C5 10.4(5)
C2 C3 C4 C14 -116.4(4)
C2 C3 C4 C11 120.7(4)
C9 N1 C5 C6 4.4(4)
C10 N1 C5 C6 161.6(2)
C9 N1 C5 C4 -123.4(3)
C10 N1 C5 C4 33.8(3)
C3 C4 C5 N1 73.0(3)
C14 C4 C5 N1 -163.0(3)
C11 C4 C5 N1 -44.2(3)
C3 C4 C5 C6 -53.1(4)
C14 C4 C5 C6 70.9(4)
C11 C4 C5 C6 -170.4(2)
N1 C5 C6 C7 -29.4(4)
C4 C5 C6 C7 90.3(3)
O1 C1 C7 C6 -158.3(3)
C2 C1 C7 C6 22.0(4)
O1 C1 C7 C8 78.5(4)
C2 C1 C7 C8 -101.1(3)
C5 C6 C7 C1 -67.2(3)
C5 C6 C7 C8 56.6(3)
C1 C7 C8 C9 67.7(3)
C6 C7 C8 C9 -60.2(3)
C10 N1 C9 O2 15.7(5)
C5 N1 C9 O2 170.8(3)
C10 N1 C9 C8 -163.2(3)
C5 N1 C9 C8 -8.2(4)
C7 C8 C9 O2 -142.7(3)
C7 C8 C9 N1 36.3(4)
C9 N1 C10 C11 151.2(3)
C5 N1 C10 C11 -7.9(3)
N1 C10 C11 C12 -149.8(3)
N1 C10 C11 C4 -20.6(3)
C3 C4 C11 C12 47.2(3)
C5 C4 C11 C12 166.2(2)
C14 C4 C11 C12 -73.7(3)
C3 C4 C11 C10 -79.0(3)
C5 C4 C11 C10 40.0(3)
C14 C4 C11 C10 160.1(3)
C10 C11 C12 C13 -62.9(3)
C4 C11 C12 C13 175.5(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 132486686
