#------------------------------------------------------------------------------
#$Date: 2021-12-07 05:38:17 +0200 (Tue, 07 Dec 2021) $
#$Revision: 271187 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/10/7061020.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_7061020
loop_
_publ_author_name
'Capozzi, Maria Annunziata M.'
'Alvarez-Larena, Angel'
'Piniella Febrer, Joan F.'
'Cardellicchio, Cosimo'
_publ_section_title
;
 A combined structural and computational investigation of
 aminobenzylnaphthol compounds derived from the Betti reaction using
 valine methyl ester
;
_journal_issue                   44
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              20735
_journal_page_last               20742
_journal_paper_doi               10.1039/D1NJ03538J
_journal_volume                  45
_journal_year                    2021
_chemical_formula_moiety         'C23 H25 N O3'
_chemical_formula_sum            'C23 H25 N O3'
_chemical_formula_weight         363.44
_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   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2021-03-22 deposited with the CCDC.	2021-10-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.831(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.1174(7)
_cell_length_b                   13.0496(11)
_cell_length_c                   16.4573(13)
_cell_measurement_reflns_used    1603
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      43.51
_cell_measurement_theta_min      5.27
_cell_volume                     1939.8(3)
_computing_cell_refinement       'SAINT 5.0 (Bruker)'
_computing_data_collection       'SMART 5.6 (Bruker)'
_computing_data_reduction        'SAINT 5.0 (Bruker)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXTL-NT 6.1 (Bruker)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 8.13
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.923
_diffrn_measurement_device_type  'Bruker SMART-APEX diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0564
_diffrn_reflns_av_unetI/netI     0.0603
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.923
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            15332
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.923
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         28.809
_diffrn_reflns_theta_min         1.999
_diffrn_source                   'sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.856
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, 2.05'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.244
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.300
_refine_diff_density_max         0.158
_refine_diff_density_min         -0.160
_refine_diff_density_rms         0.034
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         4686
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.1205
_refine_ls_R_factor_gt           0.0575
_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)+(0.0525P)²+0.1622P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1175
_refine_ls_wR_factor_ref         0.1393
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2562
_reflns_number_total             4686
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1nj03538j2.cif
_cod_data_source_block           vi33
_cod_depositor_comments
'Adding full bibliography for 7061017--7061021.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7061020
_shelx_shelxl_version_number     2016/6
_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   0.968
_shelx_estimated_absorpt_t_max   0.976
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
N1 N 0.77315(17) 0.81530(12) 0.18790(10) 0.0394(4) Uani 1 1 d . . . . .
H1N H 0.704(2) 0.8181(14) 0.2231(12) 0.050(6) Uiso 1 1 d . . . . .
O1 O 0.79789(17) 0.94823(11) 0.06750(10) 0.0591(4) Uani 1 1 d . . . . .
H1O H 0.777(3) 0.9227(19) 0.1155(15) 0.083(9) Uiso 1 1 d . . . . .
C12 C 0.81788(19) 0.68313(15) -0.00832(11) 0.0411(5) Uani 1 1 d . . . . .
O2 O 1.02822(15) 0.63066(10) 0.29052(9) 0.0565(4) Uani 1 1 d . . . . .
C13 C 0.78815(19) 0.76643(14) 0.04371(11) 0.0373(4) Uani 1 1 d . . . . .
C1 C 0.5441(2) 0.76052(13) 0.10403(11) 0.0369(4) Uani 1 1 d . . . . .
C14 C 0.8263(2) 0.86443(16) 0.02308(12) 0.0441(5) Uani 1 1 d . . . . .
C19 C 0.8990(2) 0.67984(15) 0.27614(11) 0.0430(5) Uani 1 1 d . . . . .
C18 C 0.91532(19) 0.78004(14) 0.23097(11) 0.0389(4) Uani 1 1 d . . . . .
H18 H 0.980959 0.767182 0.189619 0.047 Uiso 1 1 calc R U . . .
C2 C 0.4617(2) 0.72538(16) 0.16278(12) 0.0464(5) Uani 1 1 d . . . . .
H2 H 0.509078 0.692417 0.209176 0.056 Uiso 1 1 calc R U . . .
O3 O 0.78666(17) 0.64888(12) 0.29691(10) 0.0688(5) Uani 1 1 d . . . . .
C17 C 0.71180(19) 0.74649(14) 0.11863(11) 0.0375(4) Uani 1 1 d . . . . .
H17 H 0.732427 0.675510 0.135993 0.045 Uiso 1 1 calc R U . . .
C21 C 0.9895(2) 0.86187(16) 0.29027(13) 0.0515(5) Uani 1 1 d . . . . .
H21 H 1.078641 0.830581 0.320194 0.062 Uiso 1 1 calc R U . . .
C11 C 0.8918(2) 0.70305(18) -0.07752(12) 0.0500(5) Uani 1 1 d . . . . .
C16 C 0.9301(2) 0.8047(2) -0.09402(13) 0.0603(6) Uani 1 1 d . . . . .
H16 H 0.978999 0.818124 -0.138914 0.072 Uiso 1 1 calc R U . . .
C15 C 0.8975(2) 0.88305(18) -0.04633(13) 0.0561(6) Uani 1 1 d . . . . .
H15 H 0.922117 0.949708 -0.059222 0.067 Uiso 1 1 calc R U . . .
C6 C 0.4705(2) 0.80758(16) 0.03502(12) 0.0507(5) Uani 1 1 d . . . . .
H6 H 0.523740 0.830913 -0.005660 0.061 Uiso 1 1 calc R U . . .
C5 C 0.3183(2) 0.82036(17) 0.02578(13) 0.0566(6) Uani 1 1 d . . . . .
H5 H 0.270042 0.852736 -0.020671 0.068 Uiso 1 1 calc R U . . .
C4 C 0.2389(2) 0.78543(17) 0.08488(14) 0.0546(6) Uani 1 1 d . . . . .
H4 H 0.136677 0.793574 0.078383 0.066 Uiso 1 1 calc R U . . .
C3 C 0.3101(2) 0.73837(17) 0.15377(14) 0.0550(6) Uani 1 1 d . . . . .
H3 H 0.256272 0.715297 0.194287 0.066 Uiso 1 1 calc R U . . .
C7 C 0.7753(2) 0.58089(16) 0.00416(13) 0.0543(6) Uani 1 1 d . . . . .
H7 H 0.723862 0.566010 0.047798 0.065 Uiso 1 1 calc R U . . .
C8 C 0.8076(3) 0.50334(19) -0.04620(15) 0.0731(7) Uani 1 1 d . . . . .
H8 H 0.779074 0.436613 -0.036145 0.088 Uiso 1 1 calc R U . . .
C10 C 0.9238(3) 0.6205(2) -0.12793(14) 0.0683(7) Uani 1 1 d . . . . .
H10 H 0.973736 0.633288 -0.172513 0.082 Uiso 1 1 calc R U . . .
C9 C 0.8833(3) 0.5237(2) -0.11280(15) 0.0780(8) Uani 1 1 d . . . . .
H9 H 0.905825 0.470481 -0.146637 0.094 Uiso 1 1 calc R U . . .
C20 C 1.0302(3) 0.53490(17) 0.33510(15) 0.0719(7) Uani 1 1 d . . . . .
H20A H 0.987789 0.545101 0.384783 0.108 Uiso 1 1 calc R U . . .
H20B H 1.130454 0.511587 0.348257 0.108 Uiso 1 1 calc R U . . .
H20C H 0.973539 0.484530 0.301818 0.108 Uiso 1 1 calc R U . . .
C22 C 1.0399(3) 0.95368(18) 0.24441(16) 0.0765(8) Uani 1 1 d . . . . .
H22A H 1.101074 0.930775 0.204940 0.115 Uiso 1 1 calc R U . . .
H22B H 1.095407 0.999448 0.282609 0.115 Uiso 1 1 calc R U . . .
H22C H 0.954899 0.988802 0.216723 0.115 Uiso 1 1 calc R U . . .
C23 C 0.8921(3) 0.8938(2) 0.35363(15) 0.0848(8) Uani 1 1 d . . . . .
H23A H 0.946579 0.938801 0.392920 0.127 Uiso 1 1 calc R U . . .
H23B H 0.861922 0.834149 0.381147 0.127 Uiso 1 1 calc R U . . .
H23C H 0.806169 0.928800 0.326891 0.127 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
C18 N1 C17 113.21(14) . . ?
C7 C12 C11 117.27(19) . . ?
C7 C12 C13 123.48(17) . . ?
C11 C12 C13 119.23(18) . . ?
C19 O2 C20 117.04(16) . . ?
C14 C13 C12 118.79(17) . . ?
C14 C13 C17 121.15(17) . . ?
C12 C13 C17 120.03(16) . . ?
C2 C1 C6 118.26(18) . . ?
C2 C1 C17 118.62(16) . . ?
C6 C1 C17 123.12(17) . . ?
O1 C14 C13 122.70(17) . . ?
O1 C14 C15 116.07(19) . . ?
C13 C14 C15 121.2(2) . . ?
O3 C19 O2 123.91(19) . . ?
O3 C19 C18 125.14(18) . . ?
O2 C19 C18 110.95(16) . . ?
N1 C18 C19 111.58(15) . . ?
N1 C18 C21 111.86(15) . . ?
C19 C18 C21 110.49(15) . . ?
C3 C2 C1 121.08(19) . . ?
N1 C17 C13 110.49(14) . . ?
N1 C17 C1 108.06(14) . . ?
C13 C17 C1 114.33(14) . . ?
C23 C21 C22 111.7(2) . . ?
C23 C21 C18 112.24(18) . . ?
C22 C21 C18 111.61(17) . . ?
C16 C11 C10 121.9(2) . . ?
C16 C11 C12 118.88(19) . . ?
C10 C11 C12 119.2(2) . . ?
C15 C16 C11 121.53(19) . . ?
C16 C15 C14 120.3(2) . . ?
C1 C6 C5 120.69(19) . . ?
C4 C5 C6 120.08(19) . . ?
C5 C4 C3 120.05(19) . . ?
C4 C3 C2 119.8(2) . . ?
C8 C7 C12 121.7(2) . . ?
C7 C8 C9 120.4(2) . . ?
C9 C10 C11 121.5(2) . . ?
C10 C9 C8 119.9(2) . . ?
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
N1 C18 1.464(2) . ?
N1 C17 1.498(2) . ?
O1 C14 1.360(2) . ?
C12 C7 1.412(3) . ?
C12 C11 1.424(3) . ?
C12 C13 1.432(2) . ?
O2 C19 1.334(2) . ?
O2 C20 1.448(2) . ?
C13 C14 1.380(3) . ?
C13 C17 1.519(2) . ?
C1 C2 1.381(3) . ?
C1 C6 1.382(3) . ?
C1 C17 1.526(2) . ?
C14 C15 1.410(3) . ?
C19 O3 1.194(2) . ?
C19 C18 1.521(3) . ?
C18 C21 1.540(3) . ?
C2 C3 1.380(3) . ?
C21 C23 1.517(3) . ?
C21 C22 1.520(3) . ?
C11 C16 1.408(3) . ?
C11 C10 1.414(3) . ?
C16 C15 1.346(3) . ?
C6 C5 1.386(3) . ?
C5 C4 1.367(3) . ?
C4 C3 1.372(3) . ?
C7 C8 1.366(3) . ?
C8 C9 1.398(3) . ?
C10 C9 1.349(3) . ?
