#------------------------------------------------------------------------------
#$Date: 2022-05-21 05:03:08 +0300 (Sat, 21 May 2022) $
#$Revision: 275593 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/41/2244102.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2244102
loop_
_publ_author_name
'Hebishy, Ali M. S.'
'Elgemeie, Galal H.'
'Ali, Rasha A. E.'
'Jones, Peter G.'
_publ_section_title
;
 Crystal structure of
 2-amino-5,6,7,8-tetrahydro-7,7-dimethyl-4-(naphthalen-2-yl)-5-oxo-4H-chromene-3-carbonitrile
;
_journal_coeditor_code           HB8021
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S2056989022005199
_journal_volume                  78
_journal_year                    2022
_chemical_formula_iupac          'C22 H20 N2 O2'
_chemical_formula_moiety         'C22 H20 N2 O2'
_chemical_formula_sum            'C22 H20 N2 O2'
_chemical_formula_weight         344.40
_chemical_name_systematic
2-Amino-5,6,7,8-tetrahydro-7,7-dimethyl-4-(naphthalen-2-yl)-5-oxo-4H-chromene-3-carbonitrile
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 97.8724(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   25.3144(3)
_cell_length_b                   9.25765(11)
_cell_length_c                   15.6778(2)
_cell_measurement_reflns_used    35871
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      77.4450
_cell_measurement_theta_min      3.5260
_cell_volume                     3639.49(8)
_computing_cell_refinement
;
CrysAlisPro (Rigaku OD, 2021)
;
_computing_data_collection
;
CrysAlisPro (Rigaku OD, 2021)
;
_computing_data_reduction
;
CrysAlisPro (Rigaku OD, 2021)
;
_computing_molecular_graphics
;
XP (Siemens, 1994)
;
_computing_publication_material
;
SHELXL2018/3 (Sheldrick, 2015b)
;
_computing_structure_refinement
;
SHELXL2018/3 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'XtaLAB Synergy, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0303
_diffrn_reflns_av_unetI/netI     0.0113
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            61093
_diffrn_reflns_theta_full        77.000
_diffrn_reflns_theta_max         77.623
_diffrn_reflns_theta_min         3.525
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.647
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82558
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysalisPro; Rigaku OD, 2021)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.257
_exptl_crystal_description       lath
_exptl_crystal_F_000             1456
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.217
_refine_diff_density_min         -0.204
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3856
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0373
_refine_ls_R_factor_gt           0.0355
_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)+(0.0362P)²+2.6486P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0848
_refine_ls_wR_factor_ref         0.0860
_reflns_number_gt                3694
_reflns_number_total             3856
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            hb8021sup1.cif
_cod_data_source_block           I
_cod_original_cell_volume        3639.51(8)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2244102
_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   0.950
_shelx_estimated_absorpt_t_max   0.987
loop_
_space_group_symop_operation_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'
'-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_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.42046(3) 0.54277(7) 0.46059(4) 0.01878(16) Uani d 1 . .
C C2 0.44459(4) 0.67304(10) 0.48220(6) 0.01719(19) Uani d 1 . .
N N1 0.45324(4) 0.74447(10) 0.41141(6) 0.02197(19) Uani d 1 . .
H H01 0.4646(6) 0.8361(15) 0.4146(9) 0.038(4) Uiso d 1 . .
H H02 0.4446(6) 0.7028(15) 0.3594(8) 0.036(4) Uiso d 1 . .
C C3 0.45648(4) 0.71509(10) 0.56594(6) 0.0174(2) Uani d 1 . .
C C4 0.43643(4) 0.63303(11) 0.63906(6) 0.0175(2) Uani d 1 . .
H H4 0.465617 0.629568 0.688927 0.021 Uiso calc 1 . .
C C4A 0.42383(4) 0.48120(10) 0.60884(6) 0.0172(2) Uani d 1 . .
C C5 0.42044(4) 0.36809(11) 0.67350(6) 0.0198(2) Uani d 1 . .
O O2 0.42982(3) 0.39810(8) 0.75024(5) 0.02716(18) Uani d 1 . .
C C6 0.40710(4) 0.21643(11) 0.64222(7) 0.0231(2) Uani d 1 . .
H H6A 0.389602 0.164811 0.686041 0.028 Uiso calc 1 . .
H H6B 0.440604 0.164729 0.636056 0.028 Uiso calc 1 . .
C C7 0.37033(4) 0.21205(11) 0.55576(7) 0.0223(2) Uani d 1 . .
C C8 0.39608(4) 0.30239(11) 0.49014(6) 0.0204(2) Uani d 1 . .
H H8A 0.426832 0.248784 0.473153 0.025 Uiso calc 1 . .
H H8B 0.369856 0.316614 0.437883 0.025 Uiso calc 1 . .
C C8A 0.41454(4) 0.44589(10) 0.52524(6) 0.01697(19) Uani d 1 . .
C C9 0.48381(4) 0.84661(11) 0.58446(6) 0.0183(2) Uani d 1 . .
N N2 0.50703(4) 0.95261(10) 0.60116(6) 0.0238(2) Uani d 1 . .
C C10 0.36359(5) 0.05655(12) 0.52270(8) 0.0311(3) Uani d 1 . .
H H10A 0.338967 0.055087 0.468724 0.047 Uiso calc 1 . .
H H10B 0.349210 -0.003296 0.565660 0.047 Uiso calc 1 . .
H H10C 0.398300 0.018361 0.512555 0.047 Uiso calc 1 . .
C C11 0.31556(4) 0.27340(14) 0.56747(8) 0.0312(3) Uani d 1 . .
H H11A 0.320032 0.368819 0.594563 0.047 Uiso calc 1 . .
H H11B 0.298005 0.208440 0.604174 0.047 Uiso calc 1 . .
H H11C 0.293616 0.282185 0.511149 0.047 Uiso calc 1 . .
C C12 0.33761(4) 0.68876(11) 0.62556(6) 0.0203(2) Uani d 1 . .
H H12 0.332117 0.622111 0.579111 0.024 Uiso calc 1 . .
C C13 0.38823(4) 0.70882(11) 0.66778(6) 0.0189(2) Uani d 1 . .
C C14 0.39613(5) 0.80926(12) 0.73650(7) 0.0265(2) Uani d 1 . .
H H14 0.430947 0.823540 0.766542 0.032 Uiso calc 1 . .
C C15 0.35431(5) 0.88596(13) 0.76020(7) 0.0330(3) Uani d 1 . .
H H15 0.360637 0.953461 0.806098 0.040 Uiso calc 1 . .
C C16 0.30184(5) 0.86665(13) 0.71766(7) 0.0308(3) Uani d 1 . .
C C17 0.25720(6) 0.94476(16) 0.73986(9) 0.0462(4) Uani d 1 . .
H H17 0.262423 1.014310 0.784776 0.055 Uiso calc 1 . .
C C18 0.20725(6) 0.92164(18) 0.69796(10) 0.0517(4) Uani d 1 . .
H H18 0.178037 0.975221 0.713572 0.062 Uiso calc 1 . .
C C19 0.19874(5) 0.81873(17) 0.63165(10) 0.0460(4) Uani d 1 . .
H H19 0.163632 0.801759 0.603416 0.055 Uiso calc 1 . .
C C20 0.24071(5) 0.74252(14) 0.60733(8) 0.0336(3) Uani d 1 . .
H H20 0.234466 0.674176 0.561864 0.040 Uiso calc 1 . .
C C21 0.29329(4) 0.76481(12) 0.64938(7) 0.0249(2) Uani d 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 O1 C8A . . 118.69(7) ?
N1 C2 C3 . . 128.28(9) ?
N1 C2 O1 . . 110.35(8) ?
C3 C2 O1 . . 121.37(9) ?
C2 C3 C9 . . 118.82(9) ?
C2 C3 C4 . . 122.11(9) ?
C9 C3 C4 . . 118.77(8) ?
C4A C4 C3 . . 107.94(8) ?
C4A C4 C13 . . 112.25(8) ?
C3 C4 C13 . . 110.83(8) ?
C8A C4A C5 . . 118.84(9) ?
C8A C4A C4 . . 122.52(9) ?
C5 C4A C4 . . 118.63(8) ?
O2 C5 C4A . . 119.62(9) ?
O2 C5 C6 . . 122.28(9) ?
C4A C5 C6 . . 118.07(9) ?
C5 C6 C7 . . 113.12(8) ?
C10 C7 C11 . . 109.17(9) ?
C10 C7 C6 . . 110.45(9) ?
C11 C7 C6 . . 109.48(9) ?
C10 C7 C8 . . 108.80(9) ?
C11 C7 C8 . . 110.60(9) ?
C6 C7 C8 . . 108.34(8) ?
C8A C8 C7 . . 112.23(8) ?
C4A C8A O1 . . 122.61(9) ?
C4A C8A C8 . . 125.70(9) ?
O1 C8A C8 . . 111.69(8) ?
N2 C9 C3 . . 178.34(11) ?
C13 C12 C21 . . 121.76(10) ?
C12 C13 C14 . . 118.75(10) ?
C12 C13 C4 . . 121.77(9) ?
C14 C13 C4 . . 119.37(9) ?
C15 C14 C13 . . 120.90(11) ?
C14 C15 C16 . . 121.22(11) ?
C15 C16 C21 . . 118.42(10) ?
C15 C16 C17 . . 123.10(12) ?
C21 C16 C17 . . 118.48(13) ?
C18 C17 C16 . . 121.23(14) ?
C17 C18 C19 . . 120.17(12) ?
C20 C19 C18 . . 120.53(14) ?
C19 C20 C21 . . 120.63(13) ?
C20 C21 C12 . . 122.14(11) ?
C20 C21 C16 . . 118.93(11) ?
C12 C21 C16 . . 118.93(10) ?
C2 N1 H01 . . 120.8(9) ?
C2 N1 H02 . . 119.5(9) ?
H01 N1 H02 . . 119.5(13) ?
C4A C4 H4 . . 108.6 ?
C3 C4 H4 . . 108.6 ?
C13 C4 H4 . . 108.6 ?
C5 C6 H6A . . 109.0 ?
C7 C6 H6A . . 109.0 ?
C5 C6 H6B . . 109.0 ?
C7 C6 H6B . . 109.0 ?
H6A C6 H6B . . 107.8 ?
C8A C8 H8A . . 109.2 ?
C7 C8 H8A . . 109.2 ?
C8A C8 H8B . . 109.2 ?
C7 C8 H8B . . 109.2 ?
H8A C8 H8B . . 107.9 ?
C7 C10 H10A . . 109.5 ?
C7 C10 H10B . . 109.5 ?
H10A C10 H10B . . 109.5 ?
C7 C10 H10C . . 109.5 ?
H10A C10 H10C . . 109.5 ?
H10B C10 H10C . . 109.5 ?
C7 C11 H11A . . 109.5 ?
C7 C11 H11B . . 109.5 ?
H11A C11 H11B . . 109.5 ?
C7 C11 H11C . . 109.5 ?
H11A C11 H11C . . 109.5 ?
H11B C11 H11C . . 109.5 ?
C13 C12 H12 . . 119.1 ?
C21 C12 H12 . . 119.1 ?
C15 C14 H14 . . 119.5 ?
C13 C14 H14 . . 119.5 ?
C14 C15 H15 . . 119.4 ?
C16 C15 H15 . . 119.4 ?
C18 C17 H17 . . 119.4 ?
C16 C17 H17 . . 119.4 ?
C17 C18 H18 . . 119.9 ?
C19 C18 H18 . . 119.9 ?
C20 C19 H19 . . 119.7 ?
C18 C19 H19 . . 119.7 ?
C19 C20 H20 . . 119.7 ?
C21 C20 H20 . . 119.7 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C2 . 1.3733(11) ?
O1 C8A . 1.3769(11) ?
C2 N1 . 1.3355(13) ?
C2 C3 . 1.3628(13) ?
C3 C9 . 1.4109(13) ?
C3 C4 . 1.5193(13) ?
C4 C4A . 1.5035(13) ?
C4 C13 . 1.5278(14) ?
C4A C8A . 1.3400(14) ?
C4A C5 . 1.4681(13) ?
C5 O2 . 1.2259(13) ?
C5 C6 . 1.5101(14) ?
C6 C7 . 1.5362(15) ?
C7 C10 . 1.5316(15) ?
C7 C11 . 1.5323(15) ?
C7 C8 . 1.5384(14) ?
C8 C8A . 1.4885(13) ?
C9 N2 . 1.1553(13) ?
C12 C13 . 1.3721(14) ?
C12 C21 . 1.4173(14) ?
C13 C14 . 1.4164(14) ?
C14 C15 . 1.3678(17) ?
C15 C16 . 1.4135(18) ?
C16 C21 . 1.4206(17) ?
C16 C17 . 1.4244(17) ?
C17 C18 . 1.359(2) ?
C18 C19 . 1.405(2) ?
C19 C20 . 1.3724(18) ?
C20 C21 . 1.4172(17) ?
N1 H01 . 0.895(13) ?
N1 H02 . 0.901(13) ?
C4 H4 . 1.0000 ?
C6 H6A . 0.9900 ?
C6 H6B . 0.9900 ?
C8 H8A . 0.9900 ?
C8 H8B . 0.9900 ?
C10 H10A . 0.9800 ?
C10 H10B . 0.9800 ?
C10 H10C . 0.9800 ?
C11 H11A . 0.9800 ?
C11 H11B . 0.9800 ?
C11 H11C . 0.9800 ?
C12 H12 . 0.9500 ?
C14 H14 . 0.9500 ?
C15 H15 . 0.9500 ?
C17 H17 . 0.9500 ?
C18 H18 . 0.9500 ?
C19 H19 . 0.9500 ?
C20 H20 . 0.9500 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1 H01 N2 5_676 0.895(13) 2.110(13) 2.9948(12) 169.9(13) yes
N1 H02 O2 6_565 0.901(13) 1.941(13) 2.8404(11) 175.8(14) yes
C6 H6B N2 1_545 0.99 2.69 3.6366(14) 160 yes
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C8A O1 C2 N1 . . . . 171.82(8) ?
C8A O1 C2 C3 . . . . -8.36(13) y
N1 C2 C3 C9 . . . . -3.54(16) ?
O1 C2 C3 C9 . . . . 176.67(9) ?
N1 C2 C3 C4 . . . . 170.13(10) ?
O1 C2 C3 C4 . . . . -9.65(14) y
C2 C3 C4 C4A . . . . 22.65(13) y
C9 C3 C4 C4A . . . . -163.67(8) ?
C2 C3 C4 C13 . . . . -100.65(11) ?
C9 C3 C4 C13 . . . . 73.03(11) ?
C3 C4 C4A C8A . . . . -20.86(12) y
C13 C4 C4A C8A . . . . 101.57(11) ?
C3 C4 C4A C5 . . . . 160.51(8) ?
C13 C4 C4A C5 . . . . -77.05(11) ?
C8A C4A C5 O2 . . . . 178.62(9) ?
C4 C4A C5 O2 . . . . -2.71(14) ?
C8A C4A C5 C6 . . . . 0.61(14) y
C4 C4A C5 C6 . . . . 179.28(8) ?
O2 C5 C6 C7 . . . . 150.21(10) ?
C4A C5 C6 C7 . . . . -31.83(13) y
C5 C6 C7 C10 . . . . 173.48(9) ?
C5 C6 C7 C11 . . . . -66.28(11) ?
C5 C6 C7 C8 . . . . 54.40(11) y
C10 C7 C8 C8A . . . . -167.89(9) ?
C11 C7 C8 C8A . . . . 72.21(11) ?
C6 C7 C8 C8A . . . . -47.78(11) y
C5 C4A C8A O1 . . . . -175.40(8) ?
C4 C4A C8A O1 . . . . 5.99(15) y
C5 C4A C8A C8 . . . . 5.73(15) y
C4 C4A C8A C8 . . . . -172.89(9) ?
C2 O1 C8A C4A . . . . 10.40(13) y
C2 O1 C8A C8 . . . . -170.59(8) ?
C7 C8 C8A C4A . . . . 19.52(14) y
C7 C8 C8A O1 . . . . -159.46(8) ?
C21 C12 C13 C14 . . . . -0.51(15) ?
C21 C12 C13 C4 . . . . -176.64(9) ?
C4A C4 C13 C12 . . . . -37.80(12) ?
C3 C4 C13 C12 . . . . 82.98(11) ?
C4A C4 C13 C14 . . . . 146.09(9) ?
C3 C4 C13 C14 . . . . -93.12(11) ?
C12 C13 C14 C15 . . . . -0.50(16) ?
C4 C13 C14 C15 . . . . 175.72(10) ?
C13 C14 C15 C16 . . . . 0.66(17) ?
C14 C15 C16 C21 . . . . 0.19(17) ?
C14 C15 C16 C17 . . . . -179.62(12) ?
C15 C16 C17 C18 . . . . -179.19(13) ?
C21 C16 C17 C18 . . . . 0.99(19) ?
C16 C17 C18 C19 . . . . 0.3(2) ?
C17 C18 C19 C20 . . . . -1.2(2) ?
C18 C19 C20 C21 . . . . 0.8(2) ?
C19 C20 C21 C12 . . . . -179.56(11) ?
C19 C20 C21 C16 . . . . 0.47(17) ?
C13 C12 C21 C20 . . . . -178.63(10) ?
C13 C12 C21 C16 . . . . 1.34(15) ?
C15 C16 C21 C20 . . . . 178.82(10) ?
C17 C16 C21 C20 . . . . -1.36(16) ?
C15 C16 C21 C12 . . . . -1.16(16) ?
C17 C16 C21 C12 . . . . 178.66(10) ?

_cod_database_fobs_code 2244102
