#------------------------------------------------------------------------------
#$Date: 2025-03-07 18:30:27 +0200 (Fri, 07 Mar 2025) $
#$Revision: 298328 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/77/7157736.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_7157736
loop_
_publ_author_name
'Liu, Siyuan'
'Wang, Hang'
'Wang, Baomin'
_publ_section_title
;
 Catalyst-free construction of spiro [benzoquinolizidine-chromanones]
 via a tandem condensation/1,5-hydride transfer/cyclization
 process.
;
_journal_issue                   43
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              8839
_journal_page_last               8843
_journal_paper_doi               10.1039/d0ob01887b
_journal_volume                  18
_journal_year                    2020
_chemical_formula_sum            'C25 H19 N O3'
_chemical_formula_weight         381.43
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2017-11-09 deposited with the CCDC.	2020-10-14 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   12.9152(18)
_cell_length_b                   15.907(2)
_cell_length_c                   18.038(3)
_cell_measurement_reflns_used    206
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      21.2595
_cell_measurement_theta_min      2.2645
_cell_volume                     3705.8(9)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0434
_diffrn_reflns_av_sigmaI/netI    0.0310
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            23064
_diffrn_reflns_theta_full        27.47
_diffrn_reflns_theta_max         27.47
_diffrn_reflns_theta_min         2.26
_exptl_absorpt_coefficient_mu    0.128
_exptl_crystal_colour            YELLOW
_exptl_crystal_density_diffrn    1.427
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             1628
_refine_diff_density_max         0.199
_refine_diff_density_min         -0.166
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.996
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         4243
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.996
_refine_ls_R_factor_all          0.0746
_refine_ls_R_factor_gt           0.0444
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0530P)²+0.8638P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1062
_refine_ls_wR_factor_ref         0.1244
_reflns_number_gt                2863
_reflns_number_total             4243
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d0ob01887b2.cif
_cod_data_source_block           345
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Orthorhombic' was changed
to 'orthorhombic' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 7157736.cif.

2025-03-05
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C H N O'
_cod_original_formula_weight         43.03
_cod_original_formula_units_Z            74
_cod_original_sg_symbol_H-M      'Pbca '
_cod_database_code               7157736
loop_
_symmetry_equiv_pos_as_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'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, 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
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O -0.04134(9) 0.19835(7) 0.58363(6) 0.0453(3) Uani 1 1 d . . .
O2 O 0.06739(11) 0.38706(8) 0.45143(6) 0.0568(4) Uani 1 1 d . . .
O3\ O -0.04775(10) 0.28375(8) 0.67801(7) 0.0581(4) Uani 1 1 d . . .
C4 C -0.03223(11) 0.18659(10) 0.50789(9) 0.0391(4) Uani 1 1 d . . .
C5 C 0.03648(12) 0.33000(10) 0.49050(9) 0.0394(4) Uani 1 1 d . . .
C6 C -0.00130(11) 0.24983(10) 0.46008(8) 0.0383(4) Uani 1 1 d . . .
N1 N 0.18600(11) 0.32662(9) 0.67077(7) 0.0452(4) Uani 1 1 d . . .
C8 C 0.16821(11) 0.31677(10) 0.59296(8) 0.0363(4) Uani 1 1 d . . .
H8A H 0.2089 0.3604 0.5680 0.044 Uiso 1 1 calc R . .
C9 C 0.23448(12) 0.22601(11) 0.48924(9) 0.0447(4) Uani 1 1 d . . .
H9A H 0.2343 0.2733 0.4589 0.054 Uiso 1 1 calc R . .
C10 C -0.01853(12) 0.27371(10) 0.61592(9) 0.0399(4) Uani 1 1 d . . .
C11 C 0.20562(11) 0.23349(10) 0.56325(9) 0.0389(4) Uani 1 1 d . . .
C12 C 0.04703(12) 0.33595(9) 0.57422(8) 0.0362(3) Uani 1 1 d . . .
C13 C 0.02615(13) 0.42574(10) 0.60113(9) 0.0445(4) Uani 1 1 d . . .
H13A H 0.0475 0.4645 0.5625 0.053 Uiso 1 1 calc R . .
H13B H -0.0479 0.4324 0.6078 0.053 Uiso 1 1 calc R . .
C14 C 0.07919(13) 0.45058(10) 0.67209(9) 0.0433(4) Uani 1 1 d . . .
C15 C 0.15841(13) 0.40257(11) 0.70321(9) 0.0437(4) Uani 1 1 d . . .
C16 C 0.21050(13) 0.16310(11) 0.60915(10) 0.0471(4) Uani 1 1 d . . .
C17 C 0.00031(13) 0.23301(12) 0.38452(9) 0.0499(4) Uani 1 1 d . . .
H17A H 0.0195 0.2751 0.3515 0.060 Uiso 1 1 calc R . .
C18 C -0.05931(14) 0.10767(11) 0.48204(11) 0.0537(5) Uani 1 1 d . . .
H18A H -0.0798 0.0656 0.5147 0.064 Uiso 1 1 calc R . .
C19 C 0.22664(14) 0.25783(11) 0.71625(9) 0.0520(5) Uani 1 1 d . . .
H19A H 0.2062 0.2663 0.7675 0.062 Uiso 1 1 calc R . .
H19B H 0.3017 0.2581 0.7141 0.062 Uiso 1 1 calc R . .
C20 C 0.18665(15) 0.17385(11) 0.68959(10) 0.0556(5) Uani 1 1 d . . .
H20A H 0.2188 0.1290 0.7178 0.067 Uiso 1 1 calc R . .
H20B H 0.1124 0.1708 0.6973 0.067 Uiso 1 1 calc R . .
C21 C -0.02600(15) 0.15519(13) 0.35798(10) 0.0583(5) Uani 1 1 d . . .
H21A H -0.0242 0.1445 0.3073 0.070 Uiso 1 1 calc R . .
C22 C 0.26332(14) 0.14926(13) 0.46053(11) 0.0581(5) Uani 1 1 d . . .
H22A H 0.2802 0.1444 0.4106 0.070 Uiso 1 1 calc R . .
C23 C 0.17668(18) 0.50457(14) 0.80108(11) 0.0680(6) Uani 1 1 d . . .
H23A H 0.2094 0.5226 0.8442 0.082 Uiso 1 1 calc R . .
C24 C -0.05521(15) 0.09272(12) 0.40688(12) 0.0608(5) Uani 1 1 d . . .
H24A H -0.0724 0.0398 0.3888 0.073 Uiso 1 1 calc R . .
C25 C 0.04925(16) 0.52407(12) 0.70757(10) 0.0566(5) Uani 1 1 d . . .
H25A H -0.0044 0.5558 0.6876 0.068 Uiso 1 1 calc R . .
C26 C 0.24259(15) 0.08682(12) 0.57961(13) 0.0617(5) Uani 1 1 d . . .
H26A H 0.2475 0.0399 0.6102 0.074 Uiso 1 1 calc R . .
C27 C 0.09707(19) 0.55125(13) 0.77165(11) 0.0681(6) Uani 1 1 d . . .
H27A H 0.0757 0.6006 0.7947 0.082 Uiso 1 1 calc R . .
C28 C 0.20837(16) 0.43144(12) 0.76724(10) 0.0575(5) Uani 1 1 d . . .
H28A H 0.2633 0.4010 0.7870 0.069 Uiso 1 1 calc R . .
C29 C 0.26716(16) 0.07973(13) 0.50582(14) 0.0689(6) Uani 1 1 d . . .
H29A H 0.2864 0.0279 0.4864 0.083 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 O1 C4 121.44(12) . . ?
O1 C4 C6 122.79(14) . . ?
O1 C4 C18 115.70(15) . . ?
C6 C4 C18 121.48(16) . . ?
O2 C5 C6 122.65(15) . . ?
O2 C5 C12 119.99(15) . . ?
C6 C5 C12 117.03(13) . . ?
C4 C6 C17 118.42(16) . . ?
C4 C6 C5 119.56(14) . . ?
C17 C6 C5 121.85(15) . . ?
C15 N1 C8 117.86(13) . . ?
C15 N1 C19 120.38(14) . . ?
C8 N1 C19 121.68(14) . . ?
N1 C8 C11 113.15(13) . . ?
N1 C8 C12 109.70(12) . . ?
C11 C8 C12 113.48(12) . . ?
C22 C9 C11 120.60(17) . . ?
O3\ C10 O1 116.75(15) . . ?
O3\ C10 C12 124.02(15) . . ?
O1 C10 C12 119.08(13) . . ?
C9 C11 C16 119.29(16) . . ?
C9 C11 C8 120.12(14) . . ?
C16 C11 C8 120.59(15) . . ?
C10 C12 C5 113.92(13) . . ?
C10 C12 C13 110.86(13) . . ?
C5 C12 C13 110.93(13) . . ?
C10 C12 C8 108.28(12) . . ?
C5 C12 C8 106.29(12) . . ?
C13 C12 C8 106.13(12) . . ?
C14 C13 C12 115.72(13) . . ?
C25 C14 C15 118.69(16) . . ?
C25 C14 C13 119.12(16) . . ?
C15 C14 C13 122.18(15) . . ?
N1 C15 C14 119.67(15) . . ?
N1 C15 C28 120.97(16) . . ?
C14 C15 C28 119.36(17) . . ?
C26 C16 C11 119.17(18) . . ?
C26 C16 C20 122.32(17) . . ?
C11 C16 C20 118.41(16) . . ?
C21 C17 C6 120.87(18) . . ?
C24 C18 C4 118.58(18) . . ?
N1 C19 C20 111.08(14) . . ?
C16 C20 C19 109.89(15) . . ?
C17 C21 C24 119.65(18) . . ?
C29 C22 C9 119.93(19) . . ?
C27 C23 C28 120.51(19) . . ?
C18 C24 C21 120.99(18) . . ?
C27 C25 C14 121.7(2) . . ?
C29 C26 C16 120.86(19) . . ?
C23 C27 C25 119.27(19) . . ?
C23 C28 C15 120.41(19) . . ?
C26 C29 C22 120.08(19) . . ?
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 C10 1.3650(19) . ?
O1 C4 1.3838(19) . ?
O2 C5 1.2165(18) . ?
O3\ C10 1.1926(18) . ?
C4 C6 1.384(2) . ?
C4 C18 1.384(2) . ?
C5 C6 1.472(2) . ?
C5 C12 1.519(2) . ?
C6 C17 1.389(2) . ?
N1 C15 1.389(2) . ?
N1 C8 1.4308(19) . ?
N1 C19 1.465(2) . ?
C8 C11 1.508(2) . ?
C8 C12 1.630(2) . ?
C9 C22 1.377(2) . ?
C9 C11 1.391(2) . ?
C10 C12 1.504(2) . ?
C11 C16 1.394(2) . ?
C12 C13 1.532(2) . ?
C13 C14 1.505(2) . ?
C14 C25 1.388(2) . ?
C14 C15 1.395(2) . ?
C15 C28 1.400(2) . ?
C16 C26 1.388(3) . ?
C16 C20 1.493(3) . ?
C17 C21 1.370(3) . ?
C18 C24 1.377(3) . ?
C19 C20 1.511(3) . ?
C21 C24 1.381(3) . ?
C22 C29 1.376(3) . ?
C23 C27 1.375(3) . ?
C23 C28 1.376(3) . ?
C25 C27 1.380(3) . ?
C26 C29 1.373(3) . ?
