#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/75/2227599.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_2227599
loop_
_publ_author_name
'Zhao, Dan'
'Li, FeiFei'
'Zhang, AiYun'
_publ_section_title
;
 Naphthalene-1,8-dicarboxylic anhydride: a monoclinic polymorph
;
_journal_coeditor_code           HG2709
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2622
_journal_paper_doi               10.1107/S1600536810037608
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C12 H6 O3'
_chemical_formula_moiety         'C12 H6 O3'
_chemical_formula_sum            'C12 H6 O3'
_chemical_formula_weight         198.17
_chemical_name_systematic
;
Naphthalene-1,8-dicarboxylic anhydride
;
_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                 94.752(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   3.76870(10)
_cell_length_b                   14.5269(3)
_cell_length_c                   15.8083(3)
_cell_measurement_reflns_used    1938
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.89
_cell_measurement_theta_min      2.59
_cell_volume                     862.49(3)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_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      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_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  0.0269
_diffrn_reflns_av_sigmaI/netI    0.0308
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            7560
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         1.91
_exptl_absorpt_coefficient_mu    0.111
_exptl_absorpt_correction_T_max  0.982
_exptl_absorpt_correction_T_min  0.875
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.526
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.178
_refine_diff_density_min         -0.172
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         1964
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.999
_refine_ls_R_factor_all          0.0816
_refine_ls_R_factor_gt           0.0449
_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)+(0.0732P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1173
_refine_ls_wR_factor_ref         0.1313
_reflns_number_gt                1201
_reflns_number_total             1964
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            hg2709.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2227599
_cod_database_fobs_code          2227599
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
C C5 0.3898(4) 0.64036(9) 0.28567(8) 0.0399(4) Uani d . 1 . .
C C1 0.2469(4) 0.64100(10) 0.19687(9) 0.0486(4) Uani d . 1 . .
C C6 0.5444(4) 0.56205(10) 0.32018(9) 0.0503(4) Uani d . 1 . .
H H6 0.5618 0.5098 0.2868 0.060 Uiso calc R 1 . .
C C11 0.3060(5) 0.87580(12) 0.43612(10) 0.0588(5) Uani d . 1 . .
H H11 0.2878 0.9279 0.4696 0.071 Uiso calc R 1 . .
C C4 0.3603(3) 0.72008(9) 0.33538(8) 0.0356(4) Uani d . 1 . .
C C3 0.1982(4) 0.80075(10) 0.30145(8) 0.0397(4) Uani d . 1 . .
C C2 0.0514(4) 0.80154(11) 0.21286(9) 0.0478(4) Uani d . 1 . .
C C8 0.6540(4) 0.63636(11) 0.45452(10) 0.0544(5) Uani d . 1 . .
H H8 0.7441 0.6341 0.5111 0.065 Uiso calc R 1 . .
C C7 0.6755(4) 0.56069(12) 0.40523(10) 0.0571(5) Uani d . 1 . .
H H7 0.7788 0.5072 0.4284 0.068 Uiso calc R 1 . .
C C9 0.4972(4) 0.71882(10) 0.42179(8) 0.0429(4) Uani d . 1 . .
O O3 0.0835(3) 0.72159(7) 0.16646(6) 0.0557(3) Uani d . 1 . .
C C12 0.1693(4) 0.87738(11) 0.35104(9) 0.0504(4) Uani d . 1 . .
H H12 0.0594 0.9302 0.3283 0.061 Uiso calc R 1 . .
C C10 0.4642(4) 0.79925(12) 0.47005(9) 0.0555(4) Uani d . 1 . .
H H10 0.5534 0.7998 0.5267 0.067 Uiso calc R 1 . .
O O2 -0.1003(4) 0.86395(8) 0.17671(7) 0.0747(4) Uani d . 1 . .
O O1 0.2558(4) 0.57887(8) 0.14772(7) 0.0766(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'
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
C6 C5 C4 . . 120.72(13) ?
C6 C5 C1 . . 119.88(13) ?
C4 C5 C1 . . 119.39(12) ?
O1 C1 O3 . . 116.57(13) ?
O1 C1 C5 . . 126.36(15) ?
O3 C1 C5 . . 117.07(12) ?
C5 C6 C7 . . 120.05(14) ?
C5 C6 H6 . . 120.0 ?
C7 C6 H6 . . 120.0 ?
C10 C11 C12 . . 120.65(14) ?
C10 C11 H11 . . 119.7 ?
C12 C11 H11 . . 119.7 ?
C3 C4 C5 . . 121.58(12) ?
C3 C4 C9 . . 119.28(12) ?
C5 C4 C9 . . 119.13(12) ?
C12 C3 C4 . . 120.72(12) ?
C12 C3 C2 . . 119.96(13) ?
C4 C3 C2 . . 119.30(13) ?
O2 C2 O3 . . 116.33(13) ?
O2 C2 C3 . . 126.39(15) ?
O3 C2 C3 . . 117.26(13) ?
C7 C8 C9 . . 121.35(14) ?
C7 C8 H8 . . 119.3 ?
C9 C8 H8 . . 119.3 ?
C8 C7 C6 . . 120.70(14) ?
C8 C7 H7 . . 119.7 ?
C6 C7 H7 . . 119.7 ?
C10 C9 C8 . . 123.93(13) ?
C10 C9 C4 . . 118.02(13) ?
C8 C9 C4 . . 118.05(13) ?
C2 O3 C1 . . 125.38(11) ?
C3 C12 C11 . . 119.71(14) ?
C3 C12 H12 . . 120.1 ?
C11 C12 H12 . . 120.1 ?
C11 C10 C9 . . 121.62(14) ?
C11 C10 H10 . . 119.2 ?
C9 C10 H10 . . 119.2 ?
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
C5 C6 . 1.3706(19) ?
C5 C4 . 1.4090(18) ?
C5 C1 . 1.4613(19) ?
C1 O1 . 1.1931(16) ?
C1 O3 . 1.3900(17) ?
C6 C7 . 1.394(2) ?
C6 H6 . 0.9300 ?
C11 C10 . 1.351(2) ?
C11 C12 . 1.400(2) ?
C11 H11 . 0.9300 ?
C4 C3 . 1.4072(18) ?
C4 C9 . 1.4197(19) ?
C3 C12 . 1.3710(19) ?
C3 C2 . 1.463(2) ?
C2 O2 . 1.1922(17) ?
C2 O3 . 1.3844(17) ?
C8 C7 . 1.354(2) ?
C8 C9 . 1.4146(19) ?
C8 H8 . 0.9300 ?
C7 H7 . 0.9300 ?
C9 C10 . 1.407(2) ?
C12 H12 . 0.9300 ?
C10 H10 . 0.9300 ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 6438
