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#$Date: 2022-03-29 10:14:47 +0300 (Tue, 29 Mar 2022) $
#$Revision: 274061 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/49/8104907.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_8104907
loop_
_publ_author_name
'Wang, Wenxiang'
'Zhu, Chao'
_publ_section_title
;
 The crystal structure of
 4-((2-hydroxynaphthalen-1-yl)(pyrrolidin-1-yl)methyl)benzonitrile,
 C22H20N2O
;
_journal_issue                   1
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              151
_journal_page_last               153
_journal_paper_doi               10.1515/ncrs-2020-0415
_journal_volume                  236
_journal_year                    2021
_chemical_formula_moiety         'C22 H20 N2 O'
_chemical_formula_sum            'C22 H20 N2 O'
_chemical_formula_weight         328.40
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.677(2)
_cell_length_b                   13.999(3)
_cell_length_c                   11.171(2)
_cell_measurement_reflns_used    4179
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      31.6110
_cell_measurement_theta_min      2.9770
_cell_volume                     1826.1(6)
_computing_cell_refinement       'CrystalClear (Rigaku, 2005)[1]'
_computing_data_collection       'CrystalClear (Rigaku, 2005)[1]'
_computing_data_reduction        'CrystalClear (Rigaku, 2005)[1]'
_computing_molecular_graphics    'Diamond 4.0 [4]'
_computing_publication_material  'SHELXTL (Sheldrick, 2015)[3]'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2015)[3]'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2015)[2]'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Rigaku SCXmini'
_diffrn_measurement_method       '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  0.0829
_diffrn_reflns_av_sigmaI/netI    0.0451
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            18320
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.39
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_max  0.992
_exptl_absorpt_correction_T_min  0.934
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   '(CrystalClear; Rigaku, 2005)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.194
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.133
_refine_diff_density_min         -0.154
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_Flack   -10(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         2195
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0888
_refine_ls_R_factor_gt           0.0521
_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)+(0.0428P)²+0.1153P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0943
_refine_ls_wR_factor_ref         0.1078
_reflns_number_gt                1493
_reflns_number_total             2195
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            suppl_j_ncrs-2020-0415_suppl.cif
_cod_data_source_block           zh
_cod_original_cell_volume        1826.2(6)
_cod_original_sg_symbol_H-M      Pna21
_cod_database_code               8104907
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, 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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.9407(2) 0.0853(2) 0.2172(3) 0.0417(7) Uani 1 1 d . . .
H1 H 0.9262 0.0483 0.2901 0.050 Uiso 1 1 calc R . .
C2 C 1.0507(2) 0.0481(2) 0.1604(3) 0.0419(7) Uani 1 1 d . . .
C3 C 1.1225(3) 0.1072(2) 0.0954(3) 0.0512(8) Uani 1 1 d . . .
C4 C 1.2230(3) 0.0712(3) 0.0412(4) 0.0609(10) Uani 1 1 d . . .
H4 H 1.2701 0.1121 -0.0020 0.073 Uiso 1 1 calc R . .
C5 C 1.2512(3) -0.0215(3) 0.0515(4) 0.0641(10) Uani 1 1 d . . .
H5 H 1.3184 -0.0436 0.0163 0.077 Uiso 1 1 calc R . .
C6 C 1.1803(3) -0.0862(3) 0.1150(3) 0.0539(9) Uani 1 1 d . . .
C7 C 1.0777(3) -0.0513(2) 0.1686(3) 0.0458(8) Uani 1 1 d . . .
C8 C 1.0065(3) -0.1187(2) 0.2273(3) 0.0562(9) Uani 1 1 d . . .
H8 H 0.9378 -0.0983 0.2608 0.067 Uiso 1 1 calc R . .
C9 C 1.0363(4) -0.2121(3) 0.2358(4) 0.0722(12) Uani 1 1 d . . .
H9 H 0.9884 -0.2545 0.2757 0.087 Uiso 1 1 calc R . .
C10 C 1.1387(4) -0.2452(3) 0.1850(4) 0.0783(13) Uani 1 1 d . . .
H10 H 1.1589 -0.3093 0.1921 0.094 Uiso 1 1 calc R . .
C11 C 1.2086(4) -0.1835(3) 0.1253(4) 0.0697(11) Uani 1 1 d . . .
H11 H 1.2759 -0.2060 0.0908 0.084 Uiso 1 1 calc R . .
C12 C 0.8381(2) 0.0737(2) 0.1346(3) 0.0378(7) Uani 1 1 d . . .
C13 C 0.7371(2) 0.0343(2) 0.1760(3) 0.0450(8) Uani 1 1 d . . .
H13 H 0.7337 0.0106 0.2536 0.054 Uiso 1 1 calc R . .
C14 C 0.6411(3) 0.0296(2) 0.1044(3) 0.0453(8) Uani 1 1 d . . .
H14 H 0.5735 0.0035 0.1338 0.054 Uiso 1 1 calc R . .
C15 C 0.6461(3) 0.0636(2) -0.0107(3) 0.0415(7) Uani 1 1 d . . .
C16 C 0.7470(3) 0.1015(3) -0.0551(3) 0.0534(9) Uani 1 1 d . . .
H16 H 0.7504 0.1240 -0.1334 0.064 Uiso 1 1 calc R . .
C17 C 0.8423(3) 0.1057(2) 0.0170(3) 0.0520(9) Uani 1 1 d . . .
H17 H 0.9104 0.1303 -0.0133 0.062 Uiso 1 1 calc R . .
C18 C 0.5450(3) 0.0616(2) -0.0855(3) 0.0476(8) Uani 1 1 d . . .
C19 C 1.0281(3) 0.2010(3) 0.3569(3) 0.0546(9) Uani 1 1 d . . .
H19A H 1.1078 0.1899 0.3368 0.066 Uiso 1 1 calc R . .
H19B H 1.0064 0.1585 0.4216 0.066 Uiso 1 1 calc R . .
C20 C 1.0083(3) 0.3041(3) 0.3911(4) 0.0678(10) Uani 1 1 d . . .
H20A H 1.0652 0.3452 0.3543 0.081 Uiso 1 1 calc R . .
H20B H 1.0117 0.3121 0.4773 0.081 Uiso 1 1 calc R . .
C21 C 0.8885(3) 0.3270(3) 0.3439(4) 0.0722(12) Uani 1 1 d . . .
H21A H 0.8382 0.3460 0.4088 0.087 Uiso 1 1 calc R . .
H21B H 0.8916 0.3783 0.2855 0.087 Uiso 1 1 calc R . .
C22 C 0.8468(3) 0.2351(2) 0.2863(3) 0.0542(9) Uani 1 1 d . . .
H22A H 0.8035 0.1968 0.3428 0.065 Uiso 1 1 calc R . .
H22B H 0.7994 0.2483 0.2169 0.065 Uiso 1 1 calc R . .
N1 N 0.9536(2) 0.18689(17) 0.2516(2) 0.0435(7) Uani 1 1 d . . .
N2 N 0.4658(3) 0.0601(2) -0.1441(3) 0.0702(9) Uani 1 1 d . . .
O1 O 1.10309(19) 0.20191(16) 0.0794(3) 0.0652(7) Uani 1 1 d . . .
H1A H 1.0490 0.2187 0.1212 0.098 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 '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
N1 C1 C12 109.9(2) . .
N1 C1 C2 110.5(2) . .
C12 C1 C2 112.0(3) . .
N1 C1 H1 108.1 . .
C12 C1 H1 108.1 . .
C2 C1 H1 108.1 . .
C3 C2 C7 118.8(3) . .
C3 C2 C1 121.7(3) . .
C7 C2 C1 119.5(3) . .
O1 C3 C2 123.5(3) . .
O1 C3 C4 115.5(3) . .
C2 C3 C4 121.0(3) . .
C5 C4 C3 120.8(3) . .
C5 C4 H4 119.6 . .
C3 C4 H4 119.6 . .
C4 C5 C6 121.1(3) . .
C4 C5 H5 119.5 . .
C6 C5 H5 119.5 . .
C11 C6 C5 121.5(4) . .
C11 C6 C7 119.7(4) . .
C5 C6 C7 118.8(3) . .
C8 C7 C6 117.3(3) . .
C8 C7 C2 123.2(3) . .
C6 C7 C2 119.5(3) . .
C9 C8 C7 121.5(4) . .
C9 C8 H8 119.2 . .
C7 C8 H8 119.2 . .
C8 C9 C10 120.6(4) . .
C8 C9 H9 119.7 . .
C10 C9 H9 119.7 . .
C11 C10 C9 119.9(4) . .
C11 C10 H10 120.1 . .
C9 C10 H10 120.1 . .
C10 C11 C6 120.9(4) . .
C10 C11 H11 119.6 . .
C6 C11 H11 119.6 . .
C13 C12 C17 118.4(3) . .
C13 C12 C1 120.8(3) . .
C17 C12 C1 120.8(3) . .
C14 C13 C12 121.3(3) . .
C14 C13 H13 119.3 . .
C12 C13 H13 119.3 . .
C15 C14 C13 119.5(3) . .
C15 C14 H14 120.3 . .
C13 C14 H14 120.3 . .
C14 C15 C16 120.4(3) . .
C14 C15 C18 119.9(3) . .
C16 C15 C18 119.7(3) . .
C17 C16 C15 119.7(3) . .
C17 C16 H16 120.1 . .
C15 C16 H16 120.1 . .
C16 C17 C12 120.8(3) . .
C16 C17 H17 119.6 . .
C12 C17 H17 119.6 . .
N2 C18 C15 179.9(4) . .
N1 C19 C20 103.9(3) . .
N1 C19 H19A 111.0 . .
C20 C19 H19A 111.0 . .
N1 C19 H19B 111.0 . .
C20 C19 H19B 111.0 . .
H19A C19 H19B 109.0 . .
C19 C20 C21 104.6(3) . .
C19 C20 H20A 110.8 . .
C21 C20 H20A 110.8 . .
C19 C20 H20B 110.8 . .
C21 C20 H20B 110.8 . .
H20A C20 H20B 108.9 . .
C22 C21 C20 105.2(3) . .
C22 C21 H21A 110.7 . .
C20 C21 H21A 110.7 . .
C22 C21 H21B 110.7 . .
C20 C21 H21B 110.7 . .
H21A C21 H21B 108.8 . .
N1 C22 C21 103.2(3) . .
N1 C22 H22A 111.1 . .
C21 C22 H22A 111.1 . .
N1 C22 H22B 111.1 . .
C21 C22 H22B 111.1 . .
H22A C22 H22B 109.1 . .
C22 N1 C19 103.1(2) . .
C22 N1 C1 115.0(2) . .
C19 N1 C1 113.3(2) . .
C3 O1 H1A 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N1 1.480(4) .
C1 C12 1.521(4) .
C1 C2 1.525(4) .
C1 H1 0.9800 .
C2 C3 1.383(4) .
C2 C7 1.430(4) .
C3 O1 1.357(4) .
C3 C4 1.414(4) .
C4 C5 1.344(5) .
C4 H4 0.9300 .
C5 C6 1.419(5) .
C5 H5 0.9300 .
C6 C11 1.406(5) .
C6 C7 1.425(5) .
C7 C8 1.419(4) .
C8 C9 1.356(5) .
C8 H8 0.9300 .
C9 C10 1.402(6) .
C9 H9 0.9300 .
C10 C11 1.363(6) .
C10 H10 0.9300 .
C11 H11 0.9300 .
C12 C13 1.382(4) .
C12 C17 1.389(4) .
C13 C14 1.378(4) .
C13 H13 0.9300 .
C14 C15 1.372(4) .
C14 H14 0.9300 .
C15 C16 1.384(4) .
C15 C18 1.447(5) .
C16 C17 1.375(4) .
C16 H16 0.9300 .
C17 H17 0.9300 .
C18 N2 1.133(4) .
C19 N1 1.476(4) .
C19 C20 1.511(5) .
C19 H19A 0.9700 .
C19 H19B 0.9700 .
C20 C21 1.529(5) .
C20 H20A 0.9700 .
C20 H20B 0.9700 .
C21 C22 1.519(5) .
C21 H21A 0.9700 .
C21 H21B 0.9700 .
C22 N1 1.471(4) .
C22 H22A 0.9700 .
C22 H22B 0.9700 .
O1 H1A 0.8200 .
