#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/84/2228473.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_2228473
loop_
_publ_author_name
'Fei, Zhuan'
'Cai, Qun'
'Li, Lin'
_publ_section_title
;
 2-(Dimethylamino)anthraquinone
;
_journal_coeditor_code           NG5045
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3091
_journal_paper_doi               10.1107/S1600536810044636
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C16 H13 N O2'
_chemical_formula_moiety         'C16 H13 N O2'
_chemical_formula_sum            'C16 H13 N O2'
_chemical_formula_weight         251.27
_chemical_name_systematic
;
2-(Dimethylamino)anthraquinone
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 95.979(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   4.8614(6)
_cell_length_b                   19.945(2)
_cell_length_c                   12.8624(15)
_cell_measurement_reflns_used    4567
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      28.06
_cell_measurement_theta_min      2.59
_cell_volume                     1240.4(2)
_computing_cell_refinement       'SAINT (Bruker, 1999)'
_computing_data_collection       'SMART (Bruker, 1997)'
_computing_data_reduction        'SAINT (Bruker, 1999)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'phi and omega 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  0.0223
_diffrn_reflns_av_sigmaI/netI    0.0175
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            14833
_diffrn_reflns_theta_full        28.29
_diffrn_reflns_theta_max         28.29
_diffrn_reflns_theta_min         2.59
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.346
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.299
_refine_diff_density_min         -0.172
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         3050
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0716
_refine_ls_R_factor_gt           0.0549
_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)+(0.0842P)²+0.2178P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1484
_refine_ls_wR_factor_ref         0.1612
_reflns_number_gt                2267
_reflns_number_total             3050
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            ng5045.cif
_cod_data_source_block           I
_cod_original_cell_volume        1240.3(3)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2228473
_cod_database_fobs_code          2228473
loop_
_symmetry_equiv_pos_as_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_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
C C1 0.6324(3) -0.00602(7) 0.25988(10) 0.0429(3) Uani d . 1 . .
C C2 0.6624(3) 0.00659(8) 0.36860(11) 0.0478(3) Uani d . 1 . .
H H2 0.5603 -0.0184 0.4120 0.057 Uiso calc R 1 . .
C C3 0.8390(3) 0.05496(8) 0.41090(10) 0.0478(4) Uani d . 1 . .
H H3 0.8533 0.0623 0.4827 0.057 Uiso calc R 1 . .
C C4 0.9988(3) 0.09367(7) 0.34945(10) 0.0426(3) Uani d . 1 . .
C C5 1.1903(3) 0.14348(8) 0.39853(11) 0.0505(4) Uani d . 1 . .
C C6 1.3534(3) 0.18380(7) 0.32916(12) 0.0473(3) Uani d . 1 . .
C C7 1.5374(4) 0.23222(9) 0.37330(14) 0.0618(4) Uani d . 1 . .
H H7 1.5556 0.2395 0.4451 0.074 Uiso calc R 1 . .
C C8 1.6923(4) 0.26926(9) 0.30989(17) 0.0708(5) Uani d . 1 . .
H H8 1.8159 0.3012 0.3395 0.085 Uiso calc R 1 . .
C C9 1.6661(4) 0.25959(9) 0.20389(17) 0.0677(5) Uani d . 1 . .
H H9 1.7712 0.2850 0.1621 0.081 Uiso calc R 1 . .
C C10 1.4840(3) 0.21210(8) 0.15899(14) 0.0580(4) Uani d . 1 . .
H H10 1.4665 0.2057 0.0870 0.070 Uiso calc R 1 . .
C C11 1.3265(3) 0.17382(7) 0.22145(11) 0.0461(3) Uani d . 1 . .
C C12 1.1329(3) 0.12237(8) 0.17157(11) 0.0471(3) Uani d . 1 . .
C C13 0.9685(3) 0.08246(7) 0.24153(10) 0.0407(3) Uani d . 1 . .
C C14 0.7881(3) 0.03404(7) 0.19746(10) 0.0438(3) Uani d . 1 . .
H H14 0.7694 0.0279 0.1254 0.053 Uiso calc R 1 . .
C C15 0.3016(4) -0.09571(9) 0.28401(14) 0.0622(4) Uani d . 1 . .
H H15A 0.4210 -0.1127 0.3422 0.093 Uiso calc R 1 . .
H H15B 0.2182 -0.1325 0.2443 0.093 Uiso calc R 1 . .
H H15C 0.1597 -0.0685 0.3092 0.093 Uiso calc R 1 . .
C C16 0.3996(4) -0.06205(9) 0.10626(13) 0.0647(5) Uani d . 1 . .
H H16A 0.3266 -0.0204 0.0778 0.097 Uiso calc R 1 . .
H H16B 0.2655 -0.0970 0.0911 0.097 Uiso calc R 1 . .
H H16C 0.5656 -0.0730 0.0755 0.097 Uiso calc R 1 . .
N N1 0.4616(3) -0.05562(7) 0.21809(10) 0.0534(3) Uani d . 1 . .
O O1 1.2204(3) 0.15165(7) 0.49310(9) 0.0779(4) Uani d . 1 . .
O O2 1.1100(3) 0.11368(7) 0.07767(8) 0.0725(4) 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
N1 C1 C14 . . 121.85(12) ?
N1 C1 C2 . . 120.95(13) ?
C14 C1 C2 . . 117.20(13) ?
C3 C2 C1 . . 121.02(13) ?
C3 C2 H2 . . 119.5 ?
C1 C2 H2 . . 119.5 ?
C2 C3 C4 . . 121.89(12) ?
C2 C3 H3 . . 119.1 ?
C4 C3 H3 . . 119.1 ?
C3 C4 C13 . . 117.77(13) ?
C3 C4 C5 . . 119.92(12) ?
C13 C4 C5 . . 122.31(13) ?
O1 C5 C4 . . 121.78(14) ?
O1 C5 C6 . . 120.58(14) ?
C4 C5 C6 . . 117.64(12) ?
C11 C6 C7 . . 119.56(14) ?
C11 C6 C5 . . 121.20(13) ?
C7 C6 C5 . . 119.23(14) ?
C8 C7 C6 . . 119.71(17) ?
C8 C7 H7 . . 120.1 ?
C6 C7 H7 . . 120.1 ?
C9 C8 C7 . . 120.86(17) ?
C9 C8 H8 . . 119.6 ?
C7 C8 H8 . . 119.6 ?
C8 C9 C10 . . 120.12(16) ?
C8 C9 H9 . . 119.9 ?
C10 C9 H9 . . 119.9 ?
C9 C10 C11 . . 120.08(17) ?
C9 C10 H10 . . 120.0 ?
C11 C10 H10 . . 120.0 ?
C6 C11 C10 . . 119.66(14) ?
C6 C11 C12 . . 121.08(13) ?
C10 C11 C12 . . 119.26(14) ?
O2 C12 C11 . . 120.97(13) ?
O2 C12 C13 . . 121.60(14) ?
C11 C12 C13 . . 117.43(12) ?
C14 C13 C4 . . 120.94(12) ?
C14 C13 C12 . . 118.73(12) ?
C4 C13 C12 . . 120.33(13) ?
C13 C14 C1 . . 121.15(12) ?
C13 C14 H14 . . 119.4 ?
C1 C14 H14 . . 119.4 ?
N1 C15 H15A . . 109.5 ?
N1 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
N1 C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 109.5 ?
N1 C16 H16A . . 109.5 ?
N1 C16 H16B . . 109.5 ?
H16A C16 H16B . . 109.5 ?
N1 C16 H16C . . 109.5 ?
H16A C16 H16C . . 109.5 ?
H16B C16 H16C . . 109.5 ?
C1 N1 C16 . . 120.78(13) ?
C1 N1 C15 . . 120.72(12) ?
C16 N1 C15 . . 117.68(13) ?
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
C1 N1 . 1.3651(19) ?
C1 C14 . 1.4079(19) ?
C1 C2 . 1.4133(19) ?
C2 C3 . 1.366(2) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.3970(19) ?
C3 H3 . 0.9300 ?
C4 C13 . 1.3987(18) ?
C4 C5 . 1.459(2) ?
C5 O1 . 1.2208(17) ?
C5 C6 . 1.490(2) ?
C6 C11 . 1.392(2) ?
C6 C7 . 1.396(2) ?
C7 C8 . 1.380(3) ?
C7 H7 . 0.9300 ?
C8 C9 . 1.370(3) ?
C8 H8 . 0.9300 ?
C9 C10 . 1.381(3) ?
C9 H9 . 0.9300 ?
C10 C11 . 1.394(2) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.491(2) ?
C12 O2 . 1.2138(17) ?
C12 C13 . 1.4939(19) ?
C13 C14 . 1.385(2) ?
C14 H14 . 0.9300 ?
C15 N1 . 1.449(2) ?
C15 H15A . 0.9600 ?
C15 H15B . 0.9600 ?
C15 H15C . 0.9600 ?
C16 N1 . 1.444(2) ?
C16 H16A . 0.9600 ?
C16 H16B . 0.9600 ?
C16 H16C . 0.9600 ?
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
C9 H9 O1 4_665 0.93 2.50 3.272(2) 140.1 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
N1 C1 C2 C3 . . . . 178.16(13) ?
C14 C1 C2 C3 . . . . -1.1(2) ?
C1 C2 C3 C4 . . . . -0.5(2) ?
C2 C3 C4 C13 . . . . 1.3(2) ?
C2 C3 C4 C5 . . . . -178.30(14) ?
C3 C4 C5 O1 . . . . 1.6(2) ?
C13 C4 C5 O1 . . . . -178.05(14) ?
C3 C4 C5 C6 . . . . -179.42(12) ?
C13 C4 C5 C6 . . . . 1.0(2) ?
O1 C5 C6 C11 . . . . 178.32(15) ?
C4 C5 C6 C11 . . . . -0.7(2) ?
O1 C5 C6 C7 . . . . -1.4(2) ?
C4 C5 C6 C7 . . . . 179.60(13) ?
C11 C6 C7 C8 . . . . -0.5(2) ?
C5 C6 C7 C8 . . . . 179.16(15) ?
C6 C7 C8 C9 . . . . 0.6(3) ?
C7 C8 C9 C10 . . . . -0.3(3) ?
C8 C9 C10 C11 . . . . -0.1(3) ?
C7 C6 C11 C10 . . . . 0.2(2) ?
C5 C6 C11 C10 . . . . -179.49(13) ?
C7 C6 C11 C12 . . . . 179.74(13) ?
C5 C6 C11 C12 . . . . 0.0(2) ?
C9 C10 C11 C6 . . . . 0.1(2) ?
C9 C10 C11 C12 . . . . -179.45(14) ?
C6 C11 C12 O2 . . . . -179.89(14) ?
C10 C11 C12 O2 . . . . -0.4(2) ?
C6 C11 C12 C13 . . . . 0.4(2) ?
C10 C11 C12 C13 . . . . 179.92(13) ?
C3 C4 C13 C14 . . . . -0.7(2) ?
C5 C4 C13 C14 . . . . 178.97(13) ?
C3 C4 C13 C12 . . . . 179.82(12) ?
C5 C4 C13 C12 . . . . -0.5(2) ?
O2 C12 C13 C14 . . . . 0.6(2) ?
C11 C12 C13 C14 . . . . -179.66(12) ?
O2 C12 C13 C4 . . . . -179.87(14) ?
C11 C12 C13 C4 . . . . -0.14(19) ?
C4 C13 C14 C1 . . . . -0.9(2) ?
C12 C13 C14 C1 . . . . 178.63(12) ?
N1 C1 C14 C13 . . . . -177.49(13) ?
C2 C1 C14 C13 . . . . 1.7(2) ?
C14 C1 N1 C16 . . . . -10.0(2) ?
C2 C1 N1 C16 . . . . 170.79(14) ?
C14 C1 N1 C15 . . . . -179.41(14) ?
C2 C1 N1 C15 . . . . 1.4(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 2117105
