#------------------------------------------------------------------------------
#$Date: 2025-08-21 23:13:44 +0200 (Thu 21 de Aug de 2025) $
#$Revision: 301852 $
#$URL: svn://www.crystallography.net/cod/cif/7/06/01/7060154.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_7060154
loop_
_publ_author_name
'Puerto Galvis, Carlos E.'
'Granados, Cristian C.'
'Kouznetsov, Vladimir V.'
'Macías, Mario A.'
_publ_section_title
;
 Synthesis and X-ray crystallographic analysis of free base and
 hexafluorophosphate salts of 3,4-dihydroisoquinolines from the
 Bischler--Napieralski reaction
;
_journal_issue                   3
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              1565
_journal_page_last               1572
_journal_paper_doi               10.1039/D0NJ05235C
_journal_volume                  45
_journal_year                    2021
_chemical_formula_sum            'C20 H23 N O3'
_chemical_formula_weight         325.39
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2020-10-24 deposited with the CCDC.	2020-12-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.205(13)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.8343(16)
_cell_length_b                   12.4529(11)
_cell_length_c                   14.8774(18)
_cell_measurement_reflns_used    6366
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      26.7230
_cell_measurement_theta_min      3.3200
_cell_volume                     2105.4(4)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2015)'
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_diffrn_ambient_temperature      298(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3072
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0496
_diffrn_reflns_av_unetI/netI     0.0292
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            24600
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.101
_diffrn_reflns_theta_min         3.272
_exptl_absorpt_coefficient_mu    0.069
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88164
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            translucent
_exptl_crystal_density_diffrn    1.027
_exptl_crystal_description       parallelepiped
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.240
_refine_diff_density_max         0.498
_refine_diff_density_min         -0.397
_refine_diff_density_rms         0.075
_refine_ls_extinction_coef       0.012(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.757
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         4619
_refine_ls_number_restraints     23
_refine_ls_restrained_S_all      1.924
_refine_ls_R_factor_all          0.1077
_refine_ls_R_factor_gt           0.0852
_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)+(0.0900P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2501
_refine_ls_wR_factor_ref         0.2637
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3110
_reflns_number_total             4619
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0nj05235c2.cif
_cod_data_source_block           shelxs_sq_sq
_cod_depositor_comments
'Adding full bibliography for 7060153--7060154.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7060154
_shelx_shelxl_version_number     2018/3
_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.
;
_shelx_estimated_absorpt_t_min   0.976
_shelx_estimated_absorpt_t_max   0.984
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y+1/2, z+1/2'
'-x, -y, -z'
'-x-1/2, y-1/2, -z-1/2'
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
C1 C -0.1067(3) 0.6792(2) -0.21266(19) 0.0811(8) Uani 1 1 d . . . . .
H1A H -0.079580 0.657186 -0.264895 0.122 Uiso 1 1 calc R U . . .
H1B H -0.136909 0.751119 -0.222814 0.122 Uiso 1 1 calc R U . . .
H1C H -0.167838 0.631637 -0.206377 0.122 Uiso 1 1 calc R U . . .
O1 O -0.01150(16) 0.67599(11) -0.12951(11) 0.0691(5) Uani 1 1 d . . . . .
N1 N 0.1756(2) 0.20481(15) -0.02330(15) 0.0724(6) Uani 1 1 d . . . . .
C3 C 0.0082(2) 0.48386(17) -0.14759(15) 0.0613(6) Uani 1 1 d . . . . .
H3 H -0.054638 0.481358 -0.201536 0.074 Uiso 1 1 calc R U . . .
O3 O 0.8750(2) 0.3608(2) 0.3131(2) 0.1271(7) Uani 1 1 d . U . . .
C19 C 0.9093(5) 0.4540(4) 0.3700(3) 0.1492(14) Uani 1 1 d . U . . .
H19A H 0.932370 0.509536 0.334043 0.224 Uiso 1 1 calc R U . . .
H19B H 0.974323 0.436548 0.423005 0.224 Uiso 1 1 calc R U . . .
H19C H 0.844310 0.478498 0.391332 0.224 Uiso 1 1 calc R U . . .
C2 C 0.0418(2) 0.58141(16) -0.10328(14) 0.0571(6) Uani 1 1 d . . . . .
O2 O 0.16267(16) 0.68640(12) 0.01254(11) 0.0702(5) Uani 1 1 d . . . . .
C5 C 0.1643(2) 0.39583(17) -0.03218(15) 0.0582(6) Uani 1 1 d . . . . .
C4 C 0.0669(2) 0.39038(17) -0.11263(15) 0.0580(6) Uani 1 1 d . . . . .
C6 C 0.1986(2) 0.49475(16) 0.01109(16) 0.0607(6) Uani 1 1 d . . . . .
H6 H 0.262551 0.498329 0.064203 0.073 Uiso 1 1 calc R U . . .
C7 C 0.1387(2) 0.58653(16) -0.02417(15) 0.0574(6) Uani 1 1 d . . . . .
C8 C 0.0358(3) 0.28389(17) -0.15956(18) 0.0731(7) Uani 1 1 d . . . . .
H8A H 0.082056 0.272227 -0.203222 0.088 Uiso 1 1 calc R U . . .
H8B H -0.046679 0.283547 -0.194624 0.088 Uiso 1 1 calc R U . . .
C9 C 0.0592(3) 0.19434(19) -0.0880(2) 0.0774(8) Uani 1 1 d . . . . .
H9A H 0.000660 0.196490 -0.053574 0.093 Uiso 1 1 calc R U . . .
H9B H 0.052747 0.125617 -0.119706 0.093 Uiso 1 1 calc R U . . .
C14 C 0.5829(3) 0.4319(2) 0.1628(2) 0.0913(9) Uani 1 1 d . . . . .
H14 H 0.528280 0.487205 0.155444 0.110 Uiso 1 1 calc R U . . .
C13 C 0.5561(3) 0.3433(2) 0.1038(2) 0.0744(7) Uani 1 1 d . . . . .
C12 C 0.4402(3) 0.3340(3) 0.0309(2) 0.0844(8) Uani 1 1 d . . . . .
H12A H 0.446955 0.282729 -0.016435 0.101 Uiso 1 1 calc R U . . .
H12B H 0.419051 0.403019 0.000689 0.101 Uiso 1 1 calc R U . . .
C11 C 0.3439(3) 0.29742(19) 0.07438(19) 0.0706(7) Uani 1 1 d . . . . .
H11A H 0.361883 0.225649 0.099650 0.085 Uiso 1 1 calc R U . . .
H11B H 0.342540 0.344973 0.125714 0.085 Uiso 1 1 calc R U . . .
C10 C 0.2246(2) 0.29712(18) 0.00441(17) 0.0637(6) Uani 1 1 d . . . . .
C18 C 0.6407(3) 0.2627(2) 0.1193(2) 0.0813(8) Uani 1 1 d . . . . .
H18 H 0.626627 0.201547 0.081937 0.098 Uiso 1 1 calc R U . . .
C17 C 0.7447(3) 0.2719(2) 0.1887(2) 0.0871(8) Uani 1 1 d . . . . .
H17 H 0.800209 0.217119 0.197614 0.105 Uiso 1 1 calc R U . . .
C16 C 0.7675(3) 0.3607(3) 0.2447(3) 0.0973(7) Uani 1 1 d . U . . .
C15 C 0.6885(3) 0.4403(3) 0.2321(3) 0.0968(7) Uani 1 1 d . U . . .
H15 H 0.704497 0.501065 0.269801 0.116 Uiso 1 1 calc R U . . .
C20 C 0.2637(3) 0.6988(2) 0.0903(2) 0.0957(11) Uani 1 1 d . . . . .
H20A H 0.332217 0.675470 0.073241 0.144 Uiso 1 1 calc R U . . .
H20B H 0.254652 0.656411 0.141688 0.144 Uiso 1 1 calc R U . . .
H20C H 0.272368 0.773048 0.108355 0.144 Uiso 1 1 calc R U . . .
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
C2 O1 C1 118.16(18) . . ?
C10 N1 C9 123.1(2) . . ?
C4 C3 C2 120.8(2) . . ?
C16 O3 C19 119.1(3) . . ?
O1 C2 C3 125.6(2) . . ?
O1 C2 C7 114.45(18) . . ?
C3 C2 C7 119.98(19) . . ?
C7 O2 C20 117.49(18) . . ?
C6 C5 C4 119.7(2) . . ?
C6 C5 C10 121.7(2) . . ?
C4 C5 C10 118.5(2) . . ?
C3 C4 C5 118.97(19) . . ?
C3 C4 C8 122.6(2) . . ?
C5 C4 C8 118.3(2) . . ?
C7 C6 C5 120.4(2) . . ?
O2 C7 C6 125.7(2) . . ?
O2 C7 C2 114.28(18) . . ?
C6 C7 C2 120.01(19) . . ?
C4 C8 C9 110.6(2) . . ?
N1 C9 C8 110.8(2) . . ?
C15 C14 C13 122.0(3) . . ?
C14 C13 C18 116.2(3) . . ?
C14 C13 C12 121.4(3) . . ?
C18 C13 C12 122.4(3) . . ?
C13 C12 C11 110.9(2) . . ?
C10 C11 C12 112.0(2) . . ?
N1 C10 C5 120.1(2) . . ?
N1 C10 C11 118.1(2) . . ?
C5 C10 C11 121.8(2) . . ?
C17 C18 C13 121.2(3) . . ?
C16 C17 C18 120.6(3) . . ?
C15 C16 C17 120.1(3) . . ?
C15 C16 O3 124.3(3) . . ?
C17 C16 O3 115.6(3) . . ?
C16 C15 C14 119.9(3) . . ?
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
C1 O1 1.422(3) . ?
O1 C2 1.342(2) . ?
N1 C10 1.302(3) . ?
N1 C9 1.449(3) . ?
C3 C4 1.381(3) . ?
C3 C2 1.386(3) . ?
O3 C16 1.390(4) . ?
O3 C19 1.427(5) . ?
C2 C7 1.397(3) . ?
O2 C7 1.356(3) . ?
O2 C20 1.421(3) . ?
C5 C6 1.397(3) . ?
C5 C4 1.413(3) . ?
C5 C10 1.449(3) . ?
C4 C8 1.496(3) . ?
C6 C7 1.370(3) . ?
C8 C9 1.513(4) . ?
C14 C15 1.384(5) . ?
C14 C13 1.390(4) . ?
C13 C18 1.391(4) . ?
C13 C12 1.497(4) . ?
C12 C11 1.529(4) . ?
C11 C10 1.501(4) . ?
C18 C17 1.373(4) . ?
C17 C16 1.366(4) . ?
C16 C15 1.339(5) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 905120
