#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/56/2225695.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_2225695
loop_
_publ_author_name
'Yu, Hai-Tao'
'Wei, Yi'
'Zhang, Yan'
_publ_section_title
;
 7-Pivaloyl-5,6-dihydro-4H-naphtho[3,2,1-de]isoquinoline-4,6-dione
;
_journal_coeditor_code           XU2713
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o836
_journal_paper_doi               10.1107/S1600536810008378
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C21 H17 N O3'
_chemical_formula_moiety         'C21 H17 N O3'
_chemical_formula_sum            'C21 H17 N O3'
_chemical_formula_weight         331.36
_chemical_name_systematic
;
7-Pivaloyl-5,6-dihydro-4H-naphtho[3,2,1-de]isoquinoline-4,6-dione
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 101.12(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.569(2)
_cell_length_b                   9.1150(18)
_cell_length_c                   15.746(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      12
_cell_measurement_theta_min      9
_cell_volume                     1629.3(6)
_computing_cell_refinement       'CAD-4 EXPRESS (Enraf--Nonius, 1994)'
_computing_data_collection       'CAD-4 EXPRESS (Enraf--Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       ω/2θ
_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  0.0563
_diffrn_reflns_av_sigmaI/netI    0.1188
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            3103
_diffrn_reflns_theta_full        25.26
_diffrn_reflns_theta_max         25.26
_diffrn_reflns_theta_min         1.79
_diffrn_standards_decay_%        1
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  0.9955
_exptl_absorpt_correction_T_min  0.9910
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(CAD-4 EXPRESS; Enraf--Nonius, 1994)'
_exptl_crystal_colour            light-yellow
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.185
_refine_diff_density_min         -0.185
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.998
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         2950
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.998
_refine_ls_R_factor_all          0.1702
_refine_ls_R_factor_gt           0.0660
_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)+(0.0010P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0627
_refine_ls_wR_factor_ref         0.0767
_reflns_number_gt                1264
_reflns_number_total             2950
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            xu2713.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2225695
_cod_database_fobs_code          2225695
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N N 0.9224(2) 0.3212(3) 0.52319(16) 0.0380(8) Uani d . 1 . .
H H0A 0.9433 0.4046 0.5467 0.046 Uiso calc R 1 . .
O O1 0.7998(2) -0.0308(3) 0.72692(14) 0.0517(7) Uani d . 1 . .
O O2 0.9979(2) 0.3921(2) 0.40785(14) 0.0494(7) Uani d . 1 . .
O O3 0.8470(2) 0.2652(2) 0.64021(14) 0.0508(7) Uani d . 1 . .
C C1 0.5388(3) -0.0139(4) 0.6829(2) 0.0769(14) Uani d . 1 . .
H H1A 0.5228 -0.0812 0.6352 0.115 Uiso calc R 1 . .
H H1B 0.4670 0.0333 0.6897 0.115 Uiso calc R 1 . .
H H1C 0.5713 -0.0664 0.7349 0.115 Uiso calc R 1 . .
C C2 0.5766(3) 0.1815(4) 0.5817(2) 0.0675(13) Uani d . 1 . .
H H2A 0.5630 0.1123 0.5349 0.101 Uiso calc R 1 . .
H H2B 0.6310 0.2552 0.5704 0.101 Uiso calc R 1 . .
H H2C 0.5035 0.2271 0.5870 0.101 Uiso calc R 1 . .
C C3 0.6483(3) 0.2081(4) 0.7420(2) 0.0781(15) Uani d . 1 . .
H H3A 0.7027 0.2832 0.7326 0.117 Uiso calc R 1 . .
H H3B 0.6803 0.1551 0.7939 0.117 Uiso calc R 1 . .
H H3C 0.5750 0.2524 0.7478 0.117 Uiso calc R 1 . .
C C4 0.6277(3) 0.1027(4) 0.6652(2) 0.0461(10) Uani d . 1 . .
C C5 0.7422(3) 0.0215(4) 0.6623(2) 0.0358(9) Uani d . 1 . .
C C6 0.7748(3) -0.0144(4) 0.5757(2) 0.0337(9) Uani d . 1 . .
C C7 0.7494(3) -0.1610(4) 0.5410(2) 0.0358(9) Uani d . 1 . .
C C8 0.7003(3) -0.2677(4) 0.5887(2) 0.0504(11) Uani d . 1 . .
H H8A 0.6861 -0.2445 0.6433 0.061 Uiso calc R 1 . .
C C9 0.6734(3) -0.4046(4) 0.5553(3) 0.0584(12) Uani d . 1 . .
H H9A 0.6409 -0.4736 0.5874 0.070 Uiso calc R 1 . .
C C10 0.6942(3) -0.4420(4) 0.4742(2) 0.0560(12) Uani d . 1 . .
H H10A 0.6738 -0.5346 0.4514 0.067 Uiso calc R 1 . .
C C11 0.7448(3) -0.3419(4) 0.4277(2) 0.0457(11) Uani d . 1 . .
H H11A 0.7606 -0.3690 0.3742 0.055 Uiso calc R 1 . .
C C12 0.7736(3) -0.1988(4) 0.4589(2) 0.0351(9) Uani d . 1 . .
C C13 0.8287(3) -0.0921(4) 0.4115(2) 0.0361(9) Uani d . 1 . .
C C14 0.8587(3) 0.0469(4) 0.4492(2) 0.0314(9) Uani d . 1 . .
C C15 0.8305(3) 0.0825(4) 0.5310(2) 0.0320(9) Uani d . 1 . .
C C16 0.8571(3) -0.1202(4) 0.3306(2) 0.0430(10) Uani d . 1 . .
H H16A 0.8379 -0.2110 0.3048 0.052 Uiso calc R 1 . .
C C17 0.9120(3) -0.0188(4) 0.2882(2) 0.0480(11) Uani d . 1 . .
H H17A 0.9299 -0.0415 0.2346 0.058 Uiso calc R 1 . .
C C18 0.9412(3) 0.1181(4) 0.3250(2) 0.0417(10) Uani d . 1 . .
H H18A 0.9782 0.1872 0.2959 0.050 Uiso calc R 1 . .
C C19 0.9154(3) 0.1513(4) 0.4046(2) 0.0324(9) Uani d . 1 . .
C C20 0.9491(3) 0.2966(4) 0.4427(2) 0.0358(9) Uani d . 1 . .
C C21 0.8659(3) 0.2269(4) 0.5700(2) 0.0364(9) 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 0.0033 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C21 N C20 . . 127.1(3) ?
C21 N H0A . . 116.4 ?
C20 N H0A . . 116.4 ?
C4 C1 H1A . . 109.5 ?
C4 C1 H1B . . 109.5 ?
H1A C1 H1B . . 109.5 ?
C4 C1 H1C . . 109.5 ?
H1A C1 H1C . . 109.5 ?
H1B C1 H1C . . 109.5 ?
C4 C2 H2A . . 109.5 ?
C4 C2 H2B . . 109.5 ?
H2A C2 H2B . . 109.5 ?
C4 C2 H2C . . 109.5 ?
H2A C2 H2C . . 109.5 ?
H2B C2 H2C . . 109.5 ?
C4 C3 H3A . . 109.5 ?
C4 C3 H3B . . 109.5 ?
H3A C3 H3B . . 109.5 ?
C4 C3 H3C . . 109.5 ?
H3A C3 H3C . . 109.5 ?
H3B C3 H3C . . 109.5 ?
C2 C4 C5 . . 113.6(3) ?
C2 C4 C3 . . 111.3(3) ?
C5 C4 C3 . . 108.9(3) ?
C2 C4 C1 . . 108.8(3) ?
C5 C4 C1 . . 106.5(3) ?
C3 C4 C1 . . 107.4(3) ?
O1 C5 C6 . . 118.8(3) ?
O1 C5 C4 . . 120.7(3) ?
C6 C5 C4 . . 119.9(3) ?
C15 C6 C7 . . 118.9(3) ?
C15 C6 C5 . . 123.1(3) ?
C7 C6 C5 . . 117.9(3) ?
C8 C7 C12 . . 119.2(3) ?
C8 C7 C6 . . 120.4(3) ?
C12 C7 C6 . . 120.4(3) ?
C9 C8 C7 . . 120.6(4) ?
C9 C8 H8A . . 119.7 ?
C7 C8 H8A . . 119.7 ?
C8 C9 C10 . . 120.8(4) ?
C8 C9 H9A . . 119.6 ?
C10 C9 H9A . . 119.6 ?
C11 C10 C9 . . 119.7(4) ?
C11 C10 H10A . . 120.1 ?
C9 C10 H10A . . 120.1 ?
C10 C11 C12 . . 121.8(4) ?
C10 C11 H11A . . 119.1 ?
C12 C11 H11A . . 119.1 ?
C11 C12 C7 . . 117.8(3) ?
C11 C12 C13 . . 122.7(3) ?
C7 C12 C13 . . 119.4(3) ?
C16 C13 C14 . . 117.7(3) ?
C16 C13 C12 . . 123.4(3) ?
C14 C13 C12 . . 118.9(3) ?
C13 C14 C19 . . 119.6(3) ?
C13 C14 C15 . . 120.2(3) ?
C19 C14 C15 . . 120.2(3) ?
C6 C15 C14 . . 122.1(3) ?
C6 C15 C21 . . 118.9(3) ?
C14 C15 C21 . . 119.0(3) ?
C17 C16 C13 . . 122.3(3) ?
C17 C16 H16A . . 118.8 ?
C13 C16 H16A . . 118.8 ?
C16 C17 C18 . . 120.1(3) ?
C16 C17 H17A . . 120.0 ?
C18 C17 H17A . . 120.0 ?
C19 C18 C17 . . 119.9(3) ?
C19 C18 H18A . . 120.0 ?
C17 C18 H18A . . 120.0 ?
C18 C19 C14 . . 120.4(3) ?
C18 C19 C20 . . 118.7(3) ?
C14 C19 C20 . . 120.9(3) ?
O2 C20 N . . 120.0(3) ?
O2 C20 C19 . . 124.4(3) ?
N C20 C19 . . 115.5(3) ?
O3 C21 N . . 119.6(3) ?
O3 C21 C15 . . 123.3(3) ?
N C21 C15 . . 117.2(3) ?
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
N C21 . 1.376(4) ?
N C20 . 1.379(3) ?
N H0A . 0.8600 ?
O1 C5 . 1.201(3) ?
O2 C20 . 1.224(3) ?
O3 C21 . 1.219(3) ?
C1 C4 . 1.541(4) ?
C1 H1A . 0.9600 ?
C1 H1B . 0.9600 ?
C1 H1C . 0.9600 ?
C2 C4 . 1.514(4) ?
C2 H2A . 0.9600 ?
C2 H2B . 0.9600 ?
C2 H2C . 0.9600 ?
C3 C4 . 1.527(4) ?
C3 H3A . 0.9600 ?
C3 H3B . 0.9600 ?
C3 H3C . 0.9600 ?
C4 C5 . 1.526(4) ?
C5 C6 . 1.520(4) ?
C6 C15 . 1.365(4) ?
C6 C7 . 1.452(4) ?
C7 C8 . 1.413(4) ?
C7 C12 . 1.417(4) ?
C8 C9 . 1.366(4) ?
C8 H8A . 0.9300 ?
C9 C10 . 1.387(4) ?
C9 H9A . 0.9300 ?
C10 C11 . 1.369(4) ?
C10 H10A . 0.9300 ?
C11 C12 . 1.410(4) ?
C11 H11A . 0.9300 ?
C12 C13 . 1.447(4) ?
C13 C16 . 1.399(4) ?
C13 C14 . 1.413(4) ?
C14 C19 . 1.416(4) ?
C14 C15 . 1.426(4) ?
C15 C21 . 1.476(4) ?
C16 C17 . 1.366(4) ?
C16 H16A . 0.9300 ?
C17 C18 . 1.390(4) ?
C17 H17A . 0.9300 ?
C18 C19 . 1.378(4) ?
C18 H18A . 0.9300 ?
C19 C20 . 1.475(4) ?
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
N H0A O2 3_766 0.86 2.05 2.911(3) 174 y
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
C2 C4 C5 O1 . . . . 170.9(3) ?
C3 C4 C5 O1 . . . . 46.3(4) ?
C1 C4 C5 O1 . . . . -69.3(4) ?
C2 C4 C5 C6 . . . . -18.5(5) ?
C3 C4 C5 C6 . . . . -143.2(3) ?
C1 C4 C5 C6 . . . . 101.2(4) ?
O1 C5 C6 C15 . . . . -105.0(4) ?
C4 C5 C6 C15 . . . . 84.3(4) ?
O1 C5 C6 C7 . . . . 72.5(4) ?
C4 C5 C6 C7 . . . . -98.2(4) ?
C15 C6 C7 C8 . . . . 175.1(3) ?
C5 C6 C7 C8 . . . . -2.5(5) ?
C15 C6 C7 C12 . . . . -4.9(5) ?
C5 C6 C7 C12 . . . . 177.5(3) ?
C12 C7 C8 C9 . . . . -1.7(6) ?
C6 C7 C8 C9 . . . . 178.3(4) ?
C7 C8 C9 C10 . . . . 0.2(6) ?
C8 C9 C10 C11 . . . . 1.6(6) ?
C9 C10 C11 C12 . . . . -2.0(6) ?
C10 C11 C12 C7 . . . . 0.5(5) ?
C10 C11 C12 C13 . . . . 179.0(4) ?
C8 C7 C12 C11 . . . . 1.3(5) ?
C6 C7 C12 C11 . . . . -178.7(3) ?
C8 C7 C12 C13 . . . . -177.3(3) ?
C6 C7 C12 C13 . . . . 2.7(5) ?
C11 C12 C13 C16 . . . . 0.7(5) ?
C7 C12 C13 C16 . . . . 179.3(3) ?
C11 C12 C13 C14 . . . . -177.6(3) ?
C7 C12 C13 C14 . . . . 1.0(5) ?
C16 C13 C14 C19 . . . . 0.0(5) ?
C12 C13 C14 C19 . . . . 178.4(3) ?
C16 C13 C14 C15 . . . . 179.1(3) ?
C12 C13 C14 C15 . . . . -2.5(5) ?
C7 C6 C15 C14 . . . . 3.4(5) ?
C5 C6 C15 C14 . . . . -179.1(3) ?
C7 C6 C15 C21 . . . . -174.6(3) ?
C5 C6 C15 C21 . . . . 2.9(5) ?
C13 C14 C15 C6 . . . . 0.2(5) ?
C19 C14 C15 C6 . . . . 179.3(3) ?
C13 C14 C15 C21 . . . . 178.3(3) ?
C19 C14 C15 C21 . . . . -2.7(5) ?
C14 C13 C16 C17 . . . . 0.1(5) ?
C12 C13 C16 C17 . . . . -178.2(3) ?
C13 C16 C17 C18 . . . . -0.3(6) ?
C16 C17 C18 C19 . . . . 0.4(5) ?
C17 C18 C19 C14 . . . . -0.3(5) ?
C17 C18 C19 C20 . . . . 179.0(3) ?
C13 C14 C19 C18 . . . . 0.1(5) ?
C15 C14 C19 C18 . . . . -179.0(3) ?
C13 C14 C19 C20 . . . . -179.2(3) ?
C15 C14 C19 C20 . . . . 1.7(5) ?
C21 N C20 O2 . . . . 178.6(3) ?
C21 N C20 C19 . . . . -1.6(5) ?
C18 C19 C20 O2 . . . . 0.9(6) ?
C14 C19 C20 O2 . . . . -179.8(3) ?
C18 C19 C20 N . . . . -178.9(3) ?
C14 C19 C20 N . . . . 0.4(5) ?
C20 N C21 O3 . . . . -179.0(3) ?
C20 N C21 C15 . . . . 0.6(5) ?
C6 C15 C21 O3 . . . . -0.7(5) ?
C14 C15 C21 O3 . . . . -178.8(3) ?
C6 C15 C21 N . . . . 179.6(3) ?
C14 C15 C21 N . . . . 1.6(5) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24744644
