#------------------------------------------------------------------------------
#$Date: 2019-11-25 12:43:40 +0100 (lun 25 de nov de 2019) $
#$Revision: 241003 $
#$URL: svn://www.crystallography.net/cod/cif/4/13/06/4130602.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_4130602
loop_
_publ_author_name
'Krishna, Gamidi Rama'
'Devarapalli, Ramesh'
'Lal, Garima'
'Reddy, C. Malla'
_publ_section_title
;
 Mechanically Flexible Organic Crystals Achieved by Introducing Weak
 Interactions in Structure: Supramolecular Shape Synthons.
;
_journal_issue                   41
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              13561
_journal_page_last               13567
_journal_paper_doi               10.1021/jacs.6b05118
_journal_volume                  138
_journal_year                    2016
_chemical_formula_moiety         'C16 H10 N2 O4'
_chemical_formula_sum            'C16 H10 N2 O4'
_chemical_formula_weight         294.26
_chemical_name_common            N,N'-bis(methyl)-1,4,5,8-naphthalenediimide
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_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
_cell_angle_beta                 93.990(8)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   4.6215(15)
_cell_length_b                   8.019(3)
_cell_length_c                   17.024(6)
_cell_measurement_reflns_used    1068
_cell_measurement_temperature    100
_cell_measurement_theta_max      25.52
_cell_measurement_theta_min      2.81
_cell_volume                     629.4(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker Kappa APEX-II CCD DUO'
_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  0.0365
_diffrn_reflns_av_sigmaI/netI    0.0324
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            6047
_diffrn_reflns_theta_full        27.99
_diffrn_reflns_theta_max         27.99
_diffrn_reflns_theta_min         2.40
_exptl_absorpt_coefficient_mu    0.114
_exptl_absorpt_correction_T_max  0.989
_exptl_absorpt_correction_T_min  0.982
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS; BRUKER, 2008'
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.553
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             304.0
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.098
_refine_diff_density_max         0.236
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       0.018(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     102
_refine_ls_number_reflns         1507
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.0759
_refine_ls_R_factor_gt           0.0441
_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)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1354
_refine_ls_wR_factor_ref         0.1636
_reflns_number_gt                977
_reflns_number_total             1507
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja6b05118_si_006.cif
_cod_data_source_block           1a
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Monoclinic' was changed to
'monoclinic' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/ACS/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_H-M      'P2(1)/c  '
_cod_database_code               4130602
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_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
C1 C 0.7347(4) 0.3317(2) 0.14466(10) 0.0377(5) Uani 1 1 d .
C2 C 1.0872(4) 0.1524(2) 0.08226(10) 0.0376(5) Uani 1 1 d .
C3 C 1.1249(4) 0.28360(19) 0.02256(10) 0.0327(4) Uani 1 1 d .
C4 C 1.3051(4) 0.2569(2) -0.03677(11) 0.0395(5) Uani 1 1 d .
H4 H 1.3988 0.1549 -0.0405 0.047 Uiso 1 1 calc R
C5 C 0.9776(3) 0.43700(19) 0.02803(9) 0.0311(4) Uani 1 1 d .
C6 C 0.7881(4) 0.4662(2) 0.08767(9) 0.0345(4) Uani 1 1 d .
C7 C 0.6511(4) 0.6178(2) 0.09182(10) 0.0401(5) Uani 1 1 d .
H7 H 0.5278 0.6373 0.1317 0.048 Uiso 1 1 calc R
C8 C 0.8552(5) 0.0577(3) 0.19957(11) 0.0574(6) Uani 1 1 d .
H8A H 0.9912 -0.0312 0.1937 0.086 Uiso 1 1 calc R
H8B H 0.6613 0.0144 0.1935 0.086 Uiso 1 1 calc R
H8C H 0.8882 0.1065 0.2509 0.086 Uiso 1 1 calc R
N1 N 0.8935(3) 0.18582(18) 0.13898(8) 0.0392(4) Uani 1 1 d .
O1 O 1.2186(3) 0.02155(16) 0.08213(8) 0.0525(4) Uani 1 1 d .
O2 O 0.5599(3) 0.34704(17) 0.19412(8) 0.0545(5) Uani 1 1 d .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0373(11) 0.0419(9) 0.0345(9) -0.0053(7) 0.0071(8) -0.0059(8)
C2 0.0343(10) 0.0356(9) 0.0425(10) -0.0021(7) 0.0001(8) 0.0002(7)
C3 0.0277(9) 0.0325(8) 0.0380(9) -0.0037(6) 0.0030(7) -0.0015(7)
C4 0.0371(11) 0.0337(9) 0.0484(10) -0.0056(7) 0.0085(8) 0.0039(7)
C5 0.0264(9) 0.0323(8) 0.0349(8) -0.0057(6) 0.0037(7) -0.0013(7)
C6 0.0342(10) 0.0363(9) 0.0332(9) -0.0059(7) 0.0044(7) -0.0038(7)
C7 0.0386(11) 0.0413(9) 0.0418(9) -0.0076(7) 0.0145(8) 0.0013(8)
C8 0.0724(16) 0.0542(12) 0.0467(12) 0.0173(9) 0.0122(11) 0.0034(11)
N1 0.0415(10) 0.0394(8) 0.0372(8) 0.0058(6) 0.0058(7) -0.0014(6)
O1 0.0560(10) 0.0408(7) 0.0615(10) 0.0073(6) 0.0105(7) 0.0118(6)
O2 0.0640(10) 0.0541(9) 0.0485(8) -0.0013(6) 0.0269(7) -0.0024(7)
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
_geom_angle_site_symmetry_3
O2 C1 N1 120.97(16) .
O2 C1 C6 122.00(16) .
N1 C1 C6 117.04(14) .
O1 C2 N1 121.05(16) .
O1 C2 C3 122.02(16) .
N1 C2 C3 116.94(15) .
C4 C3 C5 120.35(15) .
C4 C3 C2 120.11(15) .
C5 C3 C2 119.53(15) .
C3 C4 C7 120.38(15) 3_765
C6 C5 C3 121.33(15) .
C6 C5 C5 119.74(18) 3_765
C3 C5 C5 118.94(17) 3_765
C7 C6 C5 119.76(15) .
C7 C6 C1 120.75(15) .
C5 C6 C1 119.48(15) .
C6 C7 C4 120.82(15) 3_765
C2 N1 C1 125.51(14) .
C2 N1 C8 117.82(15) .
C1 N1 C8 116.66(15) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 O2 1.213(2) .
C1 N1 1.388(2) .
C1 C6 1.482(2) .
C2 O1 1.213(2) .
C2 N1 1.387(2) .
C2 C3 1.481(2) .
C3 C4 1.370(2) .
C3 C5 1.412(2) .
C4 C7 1.398(2) 3_765
C5 C6 1.406(2) .
C5 C5 1.415(3) 3_765
C6 C7 1.375(2) .
C7 C4 1.398(2) 3_765
C8 N1 1.475(2) .
