#------------------------------------------------------------------------------
#$Date: 2022-02-04 22:04:33 +0200 (Fri, 04 Feb 2022) $
#$Revision: 272787 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/41/7244104.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_7244104
loop_
_publ_author_name
'Delledonne, Andrea'
'Orlandini, Martina'
'Mazzeo, Paolo P.'
'Sissa, Cristina'
'Bacchi, Alessia'
'Terenziani, Francesca'
'Pelagatti, Paolo'
_publ_section_title
;
 Bis-isonicotinoyl linkers containing polyaromatic scaffolds: synthesis,
 structure and spectroscopic properties.
;
_journal_issue                   2
_journal_name_full               'Physical chemistry chemical physics : PCCP'
_journal_page_first              1191
_journal_page_last               1201
_journal_paper_doi               10.1039/d1cp04438a
_journal_volume                  24
_journal_year                    2022
_chemical_formula_moiety         'C25 H16 N4 O3, 2(H2 O)'
_chemical_formula_sum            'C25 H20 N4 O5'
_chemical_formula_weight         456.45
_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
_audit_creation_date             2021-05-21
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-07-22 deposited with the CCDC.	2021-12-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.382(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.5492(10)
_cell_length_b                   7.4023(5)
_cell_length_c                   21.4841(16)
_cell_measurement_reflns_used    2197
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      26.548
_cell_measurement_theta_min      1.927
_cell_volume                     2119.5(3)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_temperature      200.0
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker D8 Venture, Photon II'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0590
_diffrn_reflns_av_unetI/netI     0.0482
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            11535
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.548
_diffrn_reflns_theta_min         1.927
_diffrn_source                   ?\~A^1^
_exptl_absorpt_coefficient_mu    0.102
_exptl_crystal_density_diffrn    1.430
_exptl_crystal_description       prism
_exptl_crystal_F_000             952
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.386
_refine_diff_density_min         -0.264
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.124
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     158
_refine_ls_number_reflns         2197
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.124
_refine_ls_R_factor_all          0.1008
_refine_ls_R_factor_gt           0.0733
_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)+(0.0456P)²+5.8115P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1461
_refine_ls_wR_factor_ref         0.1582
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1660
_reflns_number_total             2197
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1cp04438a2.cif
_cod_data_source_block           3
_cod_depositor_comments
'Adding full bibliography for 7244101--7244105.cif.'
_cod_database_code               7244104
_shelx_shelxl_version_number     2014/7
_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.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All O(H,H) groups
2.a Free rotating group:
 O004(H00C,H00F)
2.b Aromatic/amide H refined with riding coordinates:
 N003(H003), C00A(H00A), C00B(H00B), C00D(H00D), C00E(H00E), C00G(H00G),
 C00H(H00H), C00I(H00I)
;
_olex2_submission_special_instructions 'No special instructions were received'
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_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O001 O 0.26962(17) 0.9477(3) 0.61628(11) 0.0378(6) Uani 1 1 d . . . . .
O002 O 0.0000 1.0068(4) 0.7500 0.0374(8) Uani 1 2 d S T P . .
N003 N 0.28478(18) 0.6478(3) 0.64030(12) 0.0279(6) Uani 1 1 d . . . . .
H003 H 0.3226 0.5528 0.6370 0.033 Uiso 1 1 calc R . . . .
O004 O 0.6530(2) 0.6959(3) 0.40118(15) 0.0622(9) Uani 1 1 d . . . . .
H00C H 0.6764 0.8048 0.3990 0.093 Uiso 1 1 d G . . . .
H00F H 0.6216 0.6994 0.4331 0.093 Uiso 1 1 d G . . . .
N5 N 0.5304(2) 0.7325(4) 0.49468(13) 0.0349(7) Uani 1 1 d . . . . .
C006 C 0.0707(2) 0.7207(4) 0.72385(13) 0.0213(6) Uani 1 1 d . . . . .
C007 C 0.0449(2) 0.5412(4) 0.73468(13) 0.0212(6) Uani 1 1 d . . . . .
C008 C 0.2050(2) 0.6230(4) 0.67468(13) 0.0236(6) Uani 1 1 d . . . . .
C009 C 0.3084(2) 0.7978(4) 0.61272(14) 0.0256(7) Uani 1 1 d . . . . .
C00A C 0.1496(2) 0.7653(4) 0.69408(13) 0.0246(7) Uani 1 1 d . . . . .
H00A H 0.1657 0.8877 0.6871 0.030 Uiso 1 1 calc R . . . .
C00B C 0.1814(2) 0.4444(4) 0.68725(14) 0.0268(7) Uani 1 1 d . . . . .
H00B H 0.2208 0.3493 0.6748 0.032 Uiso 1 1 calc R . . . .
C00C C 0.0000 0.8418(5) 0.7500 0.0250(9) Uani 1 2 d S T P . .
C00D C 0.1021(2) 0.4023(4) 0.71726(14) 0.0261(7) Uani 1 1 d . . . . .
H00D H 0.0874 0.2802 0.7257 0.031 Uiso 1 1 calc R . . . .
C00E C 0.4743(2) 0.6725(4) 0.59194(15) 0.0299(7) Uani 1 1 d . . . . .
H00E H 0.4853 0.6145 0.6320 0.036 Uiso 1 1 calc R . . . .
C00F C 0.3879(2) 0.7735(4) 0.57175(15) 0.0280(7) Uani 1 1 d . . . . .
C00G C 0.3744(2) 0.8536(5) 0.51276(15) 0.0330(7) Uani 1 1 d . . . . .
H00G H 0.3168 0.9254 0.4979 0.040 Uiso 1 1 calc R . . . .
C00H C 0.5441(2) 0.6585(4) 0.55237(17) 0.0355(8) Uani 1 1 d . . . . .
H00H H 0.6043 0.5934 0.5668 0.043 Uiso 1 1 calc R . . . .
C00I C 0.4467(2) 0.8268(5) 0.47593(16) 0.0361(8) Uani 1 1 d . . . . .
H00I H 0.4361 0.8786 0.4348 0.043 Uiso 1 1 calc R . . . .
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_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C008 N003 H003 116.4 . . ?
C009 N003 H003 116.4 . . ?
C009 N003 C008 127.3(2) . . ?
H00C O004 H00F 104.5 . . ?
C00I N5 C00H 117.6(3) . . ?
C007 C006 C00C 108.1(2) . . ?
C00A C006 C007 122.6(2) . . ?
C00A C006 C00C 129.3(3) . . ?
C006 C007 C007 108.77(15) . 2_556 ?
C00D C007 C006 119.4(2) . . ?
C00D C007 C007 131.78(16) . 2_556 ?
C00A C008 N003 123.7(3) . . ?
C00B C008 N003 116.3(2) . . ?
C00B C008 C00A 120.0(2) . . ?
O001 C009 N003 125.8(3) . . ?
O001 C009 C00F 119.7(3) . . ?
N003 C009 C00F 114.4(3) . . ?
C006 C00A C008 117.4(3) . . ?
C006 C00A H00A 121.3 . . ?
C008 C00A H00A 121.3 . . ?
C008 C00B H00B 119.1 . . ?
C00D C00B C008 121.8(3) . . ?
C00D C00B H00B 119.1 . . ?
O002 C00C C006 126.89(16) . . ?
O002 C00C C006 126.89(16) . 2_556 ?
C006 C00C C006 106.2(3) . 2_556 ?
C007 C00D C00B 118.7(3) . . ?
C007 C00D H00D 120.7 . . ?
C00B C00D H00D 120.7 . . ?
C00F C00E H00E 120.7 . . ?
C00H C00E H00E 120.7 . . ?
C00H C00E C00F 118.6(3) . . ?
C00E C00F C009 121.9(3) . . ?
C00G C00F C009 119.4(3) . . ?
C00G C00F C00E 118.8(3) . . ?
C00F C00G H00G 120.8 . . ?
C00I C00G C00F 118.3(3) . . ?
C00I C00G H00G 120.8 . . ?
N5 C00H C00E 122.9(3) . . ?
N5 C00H H00H 118.6 . . ?
C00E C00H H00H 118.6 . . ?
N5 C00I C00G 123.8(3) . . ?
N5 C00I H00I 118.1 . . ?
C00G C00I H00I 118.1 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O001 C009 1.236(4) . ?
O002 C00C 1.221(5) . ?
N003 H003 0.8800 . ?
N003 C008 1.426(3) . ?
N003 C009 1.324(4) . ?
O004 H00C 0.8701 . ?
O004 H00F 0.8701 . ?
N5 C00H 1.337(4) . ?
N5 C00I 1.331(4) . ?
C006 C007 1.404(4) . ?
C006 C00A 1.382(4) . ?
C006 C00C 1.493(3) . ?
C007 C007 1.484(5) 2_556 ?
C007 C00D 1.380(4) . ?
C008 C00A 1.400(4) . ?
C008 C00B 1.399(4) . ?
C009 C00F 1.519(4) . ?
C00A H00A 0.9500 . ?
C00B H00B 0.9500 . ?
C00B C00D 1.384(4) . ?
C00C C006 1.493(4) 2_556 ?
C00D H00D 0.9500 . ?
C00E H00E 0.9500 . ?
C00E C00F 1.392(4) . ?
C00E C00H 1.384(4) . ?
C00F C00G 1.381(4) . ?
C00G H00G 0.9500 . ?
C00G C00I 1.380(4) . ?
C00H H00H 0.9500 . ?
C00I H00I 0.9500 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N003 H003 O004 0.88 2.07 2.872(3) 151.7 5_666
