#------------------------------------------------------------------------------
#$Date: 2025-08-18 17:33:07 +0200 (Mon 18 de Aug de 2025) $
#$Revision: 301779 $
#$URL: svn://www.crystallography.net/cod/cif/1/54/57/1545759.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_1545759
loop_
_publ_author_name
'Zheng, Kai-Lu'
'You, Min-Qi'
'Shu, Wen-Ming'
'Wu, Yan-Dong'
'Wu, An-Xin'
_publ_section_title
;
 Acid-Mediated Intermolecular [3 + 2] Cycloaddition toward
 Pyrrolo[2,1-a]isoquinolines: Total Synthesis of the Lamellarin Core and
 Lamellarin G Trimethyl Ether.
;
_journal_issue                   9
_journal_name_full               'Organic letters'
_journal_page_first              2262
_journal_page_last               2265
_journal_paper_doi               10.1021/acs.orglett.7b00769
_journal_volume                  19
_journal_year                    2017
_chemical_formula_sum            'C21 H19 N O2'
_chemical_formula_weight         317.37
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                100.58(5)
_cell_angle_beta                 101.15(5)
_cell_angle_gamma                94.63(5)
_cell_formula_units_Z            2
_cell_length_a                   8.078(14)
_cell_length_b                   8.370(15)
_cell_length_c                   12.380(19)
_cell_measurement_reflns_used    762
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      20.90
_cell_measurement_theta_min      2.49
_cell_volume                     801(2)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.969
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_device_type  CCD
_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  0.0642
_diffrn_reflns_av_sigmaI/netI    0.0961
_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       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5112
_diffrn_reflns_theta_full        25.51
_diffrn_reflns_theta_max         25.51
_diffrn_reflns_theta_min         1.71
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.9850
_exptl_absorpt_correction_T_min  0.9817
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             336
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.187
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.826
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         2897
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.826
_refine_ls_R_factor_all          0.1101
_refine_ls_R_factor_gt           0.0592
_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)+(0.1127P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1497
_refine_ls_wR_factor_ref         0.1945
_reflns_number_gt                1531
_reflns_number_total             2897
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol7b00769_si_001.cif
_cod_data_source_block           1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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 1545758--1545759.cif.
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1545759
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C 0.3400(4) 0.6697(3) 1.1555(2) 0.0466(7) Uani 1 1 d .
C2 C 0.4989(4) 0.6202(4) 1.1569(2) 0.0550(8) Uani 1 1 d .
H2 H 0.5465 0.6162 1.0940 0.066 Uiso 1 1 calc R
C3 C 0.5871(4) 0.5766(4) 1.2516(3) 0.0625(9) Uani 1 1 d .
H3 H 0.6942 0.5432 1.2521 0.075 Uiso 1 1 calc R
C4 C 0.5198(5) 0.5819(4) 1.3444(3) 0.0659(9) Uani 1 1 d .
H4 H 0.5809 0.5530 1.4082 0.079 Uiso 1 1 calc R
C5 C 0.3613(4) 0.6300(4) 1.3436(3) 0.0648(9) Uani 1 1 d .
H5 H 0.3152 0.6331 1.4072 0.078 Uiso 1 1 calc R
C6 C 0.2694(4) 0.6739(3) 1.2497(2) 0.0516(8) Uani 1 1 d .
C7 C 0.0987(4) 0.7328(4) 1.2461(2) 0.0576(8) Uani 1 1 d .
H7A H 0.1134 0.8513 1.2681 0.069 Uiso 1 1 calc R
H7B H 0.0450 0.6893 1.2999 0.069 Uiso 1 1 calc R
C8 C -0.0152(4) 0.6822(4) 1.1315(2) 0.0536(8) Uani 1 1 d .
H8A H -0.0487 0.5650 1.1150 0.064 Uiso 1 1 calc R
H8B H -0.1171 0.7364 1.1297 0.064 Uiso 1 1 calc R
C9 C 0.2416(4) 0.7165(3) 1.0569(2) 0.0460(7) Uani 1 1 d .
C10 C 0.2862(4) 0.7513(3) 0.9609(2) 0.0494(7) Uani 1 1 d .
H10 H 0.3948 0.7542 0.9459 0.059 Uiso 1 1 calc R
C11 C 0.1409(3) 0.7813(3) 0.8902(2) 0.0454(7) Uani 1 1 d .
C12 C 0.0081(3) 0.7641(3) 0.9446(2) 0.0455(7) Uani 1 1 d .
C13 C -0.1688(4) 0.7886(4) 0.9111(2) 0.0493(7) Uani 1 1 d .
C14 C -0.3684(4) 0.8547(4) 0.7646(3) 0.0652(9) Uani 1 1 d .
H14A H -0.3973 0.9593 0.7995 0.078 Uiso 1 1 calc R
H14B H -0.4470 0.7683 0.7756 0.078 Uiso 1 1 calc R
C15 C -0.3787(4) 0.8472(5) 0.6422(3) 0.0819(12) Uani 1 1 d .
H15A H -0.2958 0.9292 0.6323 0.123 Uiso 1 1 calc R
H15B H -0.4903 0.8666 0.6077 0.123 Uiso 1 1 calc R
H15C H -0.3565 0.7409 0.6077 0.123 Uiso 1 1 calc R
C16 C 0.1372(3) 0.8183(3) 0.7773(2) 0.0459(7) Uani 1 1 d .
C17 C 0.0508(4) 0.7124(4) 0.6820(3) 0.0627(9) Uani 1 1 d .
H17 H -0.0107 0.6166 0.6878 0.075 Uiso 1 1 calc R
C18 C 0.0534(5) 0.7459(5) 0.5770(3) 0.0719(10) Uani 1 1 d .
H18 H -0.0047 0.6716 0.5129 0.086 Uiso 1 1 calc R
C19 C 0.1405(5) 0.8867(5) 0.5666(3) 0.0731(11) Uani 1 1 d .
H19 H 0.1409 0.9101 0.4960 0.088 Uiso 1 1 calc R
C20 C 0.2264(5) 0.9918(4) 0.6609(3) 0.0700(10) Uani 1 1 d .
H20 H 0.2864 1.0882 0.6549 0.084 Uiso 1 1 calc R
C21 C 0.2261(4) 0.9582(4) 0.7655(3) 0.0560(8) Uani 1 1 d .
H21 H 0.2872 1.0316 0.8292 0.067 Uiso 1 1 calc R
N1 N 0.0733(3) 0.7260(3) 1.04706(18) 0.0457(6) Uani 1 1 d .
O1 O -0.2765(3) 0.7699(3) 0.96297(19) 0.0759(7) Uani 1 1 d .
O2 O -0.1980(3) 0.8349(3) 0.81298(18) 0.0649(6) Uani 1 1 d .
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
C2 C1 C6 119.6(3)
C2 C1 C9 121.9(3)
C6 C1 C9 118.5(3)
C3 C2 C1 120.0(3)
C4 C3 C2 120.8(3)
C3 C4 C5 119.7(3)
C4 C5 C6 120.8(3)
C5 C6 C1 119.1(3)
C5 C6 C7 122.8(3)
C1 C6 C7 118.0(3)
C6 C7 C8 112.3(3)
N1 C8 C7 109.9(3)
N1 C9 C10 107.9(2)
N1 C9 C1 120.4(3)
C10 C9 C1 131.7(3)
C9 C10 C11 108.3(3)
C12 C11 C10 106.8(3)
C12 C11 C16 129.0(3)
C10 C11 C16 124.1(3)
N1 C12 C11 107.7(3)
N1 C12 C13 122.2(3)
C11 C12 C13 129.9(3)
O1 C13 O2 123.3(3)
O1 C13 C12 125.8(3)
O2 C13 C12 110.9(3)
O2 C14 C15 107.3(3)
C17 C16 C21 118.0(3)
C17 C16 C11 121.5(3)
C21 C16 C11 120.5(3)
C16 C17 C18 120.8(3)
C19 C18 C17 120.6(3)
C20 C19 C18 118.7(3)
C19 C20 C21 121.0(4)
C20 C21 C16 120.9(3)
C9 N1 C12 109.2(2)
C9 N1 C8 121.0(2)
C12 N1 C8 129.5(3)
C13 O2 C14 118.1(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.378(5)
C1 C6 1.391(4)
C1 C9 1.458(4)
C2 C3 1.374(4)
C3 C4 1.358(5)
C4 C5 1.372(5)
C5 C6 1.380(4)
C6 C7 1.497(5)
C7 C8 1.500(4)
C8 N1 1.458(4)
C9 N1 1.351(4)
C9 C10 1.380(4)
C10 C11 1.393(4)
C11 C12 1.384(4)
C11 C16 1.481(4)
C12 N1 1.381(4)
C12 C13 1.452(5)
C13 O1 1.193(4)
C13 O2 1.326(4)
C14 O2 1.427(4)
C14 C15 1.491(5)
C16 C17 1.364(4)
C16 C21 1.370(4)
C17 C18 1.383(5)
C18 C19 1.363(5)
C19 C20 1.352(5)
C20 C21 1.375(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
C6 C1 C2 C3 -0.6(5)
C9 C1 C2 C3 -179.8(3)
C1 C2 C3 C4 -0.1(5)
C2 C3 C4 C5 0.5(5)
C3 C4 C5 C6 -0.3(5)
C4 C5 C6 C1 -0.4(5)
C4 C5 C6 C7 -177.8(3)
C2 C1 C6 C5 0.8(4)
C9 C1 C6 C5 -179.9(3)
C2 C1 C6 C7 178.3(3)
C9 C1 C6 C7 -2.4(4)
C5 C6 C7 C8 -146.9(3)
C1 C6 C7 C8 35.7(4)
C6 C7 C8 N1 -50.7(4)
C2 C1 C9 N1 163.9(3)
C6 C1 C9 N1 -15.3(4)
C2 C1 C9 C10 -13.4(5)
C6 C1 C9 C10 167.3(3)
N1 C9 C10 C11 -0.5(3)
C1 C9 C10 C11 177.0(3)
C9 C10 C11 C12 -0.1(3)
C9 C10 C11 C16 -178.1(3)
C10 C11 C12 N1 0.6(3)
C16 C11 C12 N1 178.6(3)
C10 C11 C12 C13 177.0(3)
C16 C11 C12 C13 -5.1(5)
N1 C12 C13 O1 -4.6(5)
C11 C12 C13 O1 179.4(3)
N1 C12 C13 O2 175.7(2)
C11 C12 C13 O2 -0.3(4)
C12 C11 C16 C17 -64.4(4)
C10 C11 C16 C17 113.2(4)
C12 C11 C16 C21 117.9(3)
C10 C11 C16 C21 -64.5(4)
C21 C16 C17 C18 0.1(5)
C11 C16 C17 C18 -177.7(3)
C16 C17 C18 C19 -1.0(5)
C17 C18 C19 C20 1.0(5)
C18 C19 C20 C21 -0.1(5)
C19 C20 C21 C16 -0.8(5)
C17 C16 C21 C20 0.8(4)
C11 C16 C21 C20 178.6(3)
C10 C9 N1 C12 0.9(3)
C1 C9 N1 C12 -176.9(2)
C10 C9 N1 C8 174.9(2)
C1 C9 N1 C8 -3.0(4)
C11 C12 N1 C9 -1.0(3)
C13 C12 N1 C9 -177.7(3)
C11 C12 N1 C8 -174.3(3)
C13 C12 N1 C8 9.0(4)
C7 C8 N1 C9 36.0(4)
C7 C8 N1 C12 -151.5(3)
O1 C13 O2 C14 -3.4(5)
C12 C13 O2 C14 176.3(3)
C15 C14 O2 C13 -160.1(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 72190167
