#------------------------------------------------------------------------------
#$Date: 2019-09-19 12:31:39 +0300 (Thu, 19 Sep 2019) $
#$Revision: 218546 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/22/99/7229909.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_7229909
loop_
_publ_author_name
'Amombo Noa, Francoise M.'
'Mehlana, Gift'
_publ_section_title
;
 Co-crystals and Salts of Vanillic Acid and Vanillin with Amines
;
_journal_coden_ASTM              CRECF4
_journal_issue                   7
_journal_name_full               CrystEngComm
_journal_page_first              896
_journal_page_last               905
_journal_paper_doi               10.1039/c7ce02022h
_journal_volume                  20
_journal_year                    2018
_chemical_formula_sum            'C26 H20 N3 O4'
_chemical_formula_weight         438.45
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2017/1
_audit_update_record
;
2017-09-11 deposited with the CCDC.
2018-01-08 downloaded from the CCDC.
;
_cell_angle_alpha                98.3390(10)
_cell_angle_beta                 101.0090(10)
_cell_angle_gamma                108.2880(10)
_cell_formula_units_Z            2
_cell_length_a                   7.1376(4)
_cell_length_b                   9.5383(5)
_cell_length_c                   16.6511(9)
_cell_measurement_reflns_used    13988
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.345
_cell_measurement_theta_min      1.277
_cell_volume                     1030.69(10)
_computing_cell_refinement       'SAINT-Plus (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'SAINT-Plus and XPREP (Bruker 2004)'
_computing_molecular_graphics    'X-seed (Barbour, 1999)'
_computing_publication_material  'SHELXS-2017 (Sheldrick, 2017)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_structure_solution    'SHELXS-2017 (Sheldrick, 2017)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker Kappa Duo Apex II diffractometer'
_diffrn_measurement_method       '1.2° φ scans and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0201
_diffrn_reflns_av_unetI/netI     0.0242
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            13988
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.345
_diffrn_reflns_theta_min         1.277
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            'yellow orange'
_exptl_crystal_density_diffrn    1.413
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             458
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.49
_exptl_crystal_size_min          0.45
_exptl_transmission_factor_max   0.957
_exptl_transmission_factor_min   0.943
_refine_diff_density_max         0.308
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     307
_refine_ls_number_reflns         5128
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0501
_refine_ls_R_factor_gt           0.0399
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0524P)²+0.2137P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1025
_refine_ls_wR_factor_ref         0.1084
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4180
_reflns_number_total             5128
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c7ce02022h2.cif
_cod_data_source_block           vaphz
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'none' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 

 Updated bibliographic information.

 Antanas Vaitkus,
 2019-09-19
;
_cod_database_code               7229909
_shelx_shelxl_version_number     2017/1
_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.
;
_exptl_absorpt_special_details
'Absorption corrections were made using the program SADABS (Sheldrick, 1996)'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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
O3 O 0.16500(12) 0.58909(9) 0.29552(5) 0.02533(19) Uani 1 1 d . .
C5 C 0.32322(16) 0.45163(12) 0.22300(7) 0.0206(2) Uani 1 1 d . .
C4 C 0.14013(17) 0.46975(12) 0.23281(7) 0.0195(2) Uani 1 1 d . .
C6 C 0.31748(17) 0.33529(13) 0.16103(7) 0.0240(2) Uani 1 1 d . .
H6 H 0.440977 0.323095 0.154176 0.029 Uiso 1 1 calc R U
C3 C -0.04402(17) 0.37049(12) 0.18200(7) 0.0203(2) Uani 1 1 d . .
H3 H -0.167815 0.381402 0.189416 0.024 Uiso 1 1 calc R U
C2 C -0.04808(17) 0.25352(12) 0.11943(7) 0.0205(2) Uani 1 1 d . .
C7 C 0.13279(18) 0.23650(13) 0.10894(7) 0.0231(2) Uani 1 1 d . .
H7 H 0.129924 0.157517 0.066261 0.028 Uiso 1 1 calc R U
O4 O 0.50629(12) 0.54357(10) 0.27333(6) 0.0288(2) Uani 1 1 d . .
C23 C 0.6999(2) 0.57140(15) 0.03825(8) 0.0309(3) Uani 1 1 d . .
N3 N 0.65024(18) 0.43658(13) -0.01385(7) 0.0335(3) Uani 1 1 d . .
C24 C 0.4521(2) 0.36565(14) -0.05199(8) 0.0310(3) Uani 1 1 d . .
C1 C -0.24690(17) 0.14770(12) 0.06641(7) 0.0214(2) Uani 1 1 d . .
C26 C 0.1907(3) 0.14705(17) -0.14676(9) 0.0489(4) Uani 1 1 d . .
H26 H 0.151351 0.052016 -0.184469 0.059 Uiso 1 1 calc R U
C25 C 0.3896(3) 0.22202(16) -0.10766(9) 0.0421(4) Uani 1 1 d . .
H25 H 0.488370 0.178586 -0.117392 0.050 Uiso 1 1 calc R U
C22 C 0.9085(2) 0.65498(18) 0.07966(9) 0.0409(3) Uani 1 1 d . .
H22 H 1.011344 0.615468 0.070607 0.049 Uiso 1 1 calc R U
O1 O -0.40880(12) 0.14237(9) 0.08498(5) 0.0271(2) Uani 1 1 d . .
O2 O -0.24013(13) 0.05953(10) 0.00015(5) 0.0288(2) Uani 1 1 d . .
N2 N 0.61113(14) 0.80538(10) 0.39799(6) 0.0223(2) Uani 1 1 d . .
C8 C -0.01677(18) 0.60533(14) 0.31298(8) 0.0279(3) Uani 1 1 d . .
H8A H -0.098040 0.621912 0.263206 0.042 Uiso 1 1 calc R U
H8B H 0.019694 0.692013 0.359837 0.042 Uiso 1 1 calc R U
H8C H -0.096421 0.513171 0.327848 0.042 Uiso 1 1 calc R U
C21 C 0.9594(3) 0.79189(18) 0.13230(10) 0.0498(4) Uani 1 1 d . .
H21 H 1.098506 0.847409 0.159824 0.060 Uiso 1 1 calc R U
C9 C 0.71109(18) 0.66914(13) 0.49811(8) 0.0270(3) Uani 1 1 d . .
H9 H 0.653753 0.577332 0.456666 0.032 Uiso 1 1 calc R U
C18 C 0.5130(2) 0.94387(14) 0.29918(8) 0.0296(3) Uani 1 1 d . .
H18 H 0.453337 0.853896 0.256415 0.036 Uiso 1 1 calc R U
C20 C 0.70288(16) 0.80648(12) 0.47672(7) 0.0211(2) Uani 1 1 d . .
C19 C 0.60580(17) 0.93805(13) 0.38162(7) 0.0222(2) Uani 1 1 d . .
N1 N 0.78541(15) 1.07665(11) 0.52381(6) 0.0235(2) Uani 1 1 d . .
C13 C 0.79100(16) 0.94395(13) 0.54009(7) 0.0216(2) Uani 1 1 d . .
C11 C 0.8901(2) 0.80554(15) 0.64062(8) 0.0306(3) Uani 1 1 d . .
H11 H 0.953147 0.803274 0.695857 0.037 Uiso 1 1 calc R U
C12 C 0.88621(18) 0.93882(14) 0.62247(7) 0.0275(3) Uani 1 1 d . .
H12 H 0.947244 1.029229 0.664892 0.033 Uiso 1 1 calc R U
C15 C 0.68404(18) 1.21277(13) 0.42421(8) 0.0276(3) Uani 1 1 d . .
H15 H 0.740307 1.304184 0.465953 0.033 Uiso 1 1 calc R U
C17 C 0.5095(2) 1.07784(16) 0.28147(8) 0.0337(3) Uani 1 1 d . .
H17 H 0.449345 1.080880 0.226006 0.040 Uiso 1 1 calc R U
C10 C 0.8009(2) 0.66909(15) 0.57782(8) 0.0309(3) Uani 1 1 d . .
H10 H 0.804163 0.576637 0.591786 0.037 Uiso 1 1 calc R U
C14 C 0.69392(17) 1.07509(12) 0.44542(7) 0.0219(2) Uani 1 1 d . .
C16 C 0.5950(2) 1.21389(15) 0.34496(9) 0.0316(3) Uani 1 1 d . .
H16 H 0.589331 1.306194 0.331542 0.038 Uiso 1 1 calc R U
H5 H 0.495(3) 0.618(2) 0.3092(12) 0.058(5) Uiso 1 1 d . .
H2 H -0.377(4) -0.020(3) -0.0307(14) 0.087(7) Uiso 1 1 d . .
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
C4 O3 C8 116.73(8) .
O4 C5 C6 118.53(10) .
O4 C5 C4 121.85(10) .
C6 C5 C4 119.62(10) .
O3 C4 C3 125.57(10) .
O3 C4 C5 114.35(9) .
C3 C4 C5 120.08(9) .
C5 C6 C7 120.52(10) .
C4 C3 C2 119.83(10) .
C7 C2 C3 120.19(10) .
C7 C2 C1 120.91(10) .
C3 C2 C1 118.89(10) .
C6 C7 C2 119.75(10) .
N3 C23 C22 119.36(13) .
N3 C23 C24 121.42(12) 2_665
C22 C23 C24 119.21(12) 2_665
C24 N3 C23 116.23(12) .
N3 C24 C25 118.93(13) .
N3 C24 C23 122.36(11) 2_665
C25 C24 C23 118.72(13) 2_665
O1 C1 O2 122.73(10) .
O1 C1 C2 121.55(9) .
O2 C1 C2 115.71(10) .
C25 C26 C21 120.86(14) 2_665
C26 C25 C24 120.43(15) .
C21 C22 C23 119.49(15) .
C19 N2 C20 117.18(9) .
C22 C21 C26 121.29(15) 2_665
C10 C9 C20 120.06(11) .
C17 C18 C19 120.15(11) .
N2 C20 C9 119.76(10) .
N2 C20 C13 121.11(10) .
C9 C20 C13 119.13(11) .
N2 C19 C18 119.57(10) .
N2 C19 C14 121.39(10) .
C18 C19 C14 119.04(11) .
C14 N1 C13 116.96(9) .
N1 C13 C12 119.40(10) .
N1 C13 C20 121.76(10) .
C12 C13 C20 118.84(11) .
C12 C11 C10 120.69(12) .
C11 C12 C13 120.34(11) .
C16 C15 C14 120.41(11) .
C18 C17 C16 120.93(12) .
C9 C10 C11 120.93(12) .
N1 C14 C15 119.54(10) .
N1 C14 C19 121.61(10) .
C15 C14 C19 118.85(11) .
C15 C16 C17 120.62(12) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O3 C4 1.3695(12) .
O3 C8 1.4314(14) .
C5 O4 1.3521(13) .
C5 C6 1.3860(15) .
C5 C4 1.4069(15) .
C4 C3 1.3791(15) .
C6 C7 1.3873(16) .
C3 C2 1.4007(14) .
C2 C7 1.3903(16) .
C2 C1 1.4752(15) .
C23 N3 1.3435(16) .
C23 C22 1.4256(19) .
C23 C24 1.4326(19) 2_665
N3 C24 1.3393(18) .
C24 C25 1.4232(18) .
C1 O1 1.2401(14) .
C1 O2 1.3051(13) .
C26 C25 1.351(2) .
C26 C21 1.412(3) 2_665
C22 C21 1.362(2) .
N2 C19 1.3430(15) .
N2 C20 1.3459(15) .
C9 C10 1.3594(18) .
C9 C20 1.4220(16) .
C18 C17 1.3590(19) .
C18 C19 1.4226(17) .
C20 C13 1.4338(15) .
C19 C14 1.4348(15) .
N1 C14 1.3392(15) .
N1 C13 1.3432(15) .
C13 C12 1.4248(17) .
C11 C12 1.3560(18) .
C11 C10 1.4225(18) .
C15 C16 1.3541(18) .
C15 C14 1.4274(17) .
C17 C16 1.4257(19) .
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
_geom_hbond_publ_flag
C6 H6 O1 0.95 2.55 3.3663(14) 144.1 1_655 yes
C8 H8B N1 0.98 2.52 3.4735(15) 163.6 2_676 yes
O4 H5 N2 0.892(19) 1.976(19) 2.7992(12) 152.7(17) . yes
O2 H2 O1 1.01(2) 1.60(2) 2.6115(11) 176(2) 2_455 yes
