#------------------------------------------------------------------------------
#$Date: 2025-08-22 00:26:11 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301853 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/10/86/7108664.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_7108664
loop_
_publ_author_name
'Vjekoslav Strukil'
'Boris Bartolec'
'Tomislav Portada'
'Ivica Dilovic'
'Ivan Halasz'
'Davor Margetic'
_publ_section_title
;
 One-pot mechanosynthesis of aromatic amides and dipeptides from
 carboxylic acids and amines
;
_journal_name_full               Chem.Commun.
_journal_page_first              12100
_journal_paper_doi               10.1039/c2cc36613d
_journal_volume                  48
_journal_year                    2012
_chemical_compound_source        'chemical synthesis'
_chemical_formula_moiety         'C16 H16 N2 O2'
_chemical_formula_sum            'C16 H16 N2 O2'
_chemical_formula_weight         268.31
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      15
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 91.721(19)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   17.179(4)
_cell_length_b                   5.0906(7)
_cell_length_c                   29.764(6)
_cell_measurement_reflns_used    1441
_cell_measurement_temperature    293
_cell_measurement_theta_max      26.3797
_cell_measurement_theta_min      4.1529
_cell_volume                     2601.7(9)
_computing_cell_refinement
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
;
_computing_data_collection
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
;
_computing_data_reduction
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    SIR-2004
_diffrn_ambient_temperature      293
_diffrn_detector_area_resol_mean 16.3426
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0160875000
_diffrn_orient_matrix_UB_12      -0.0637132000
_diffrn_orient_matrix_UB_13      -0.0192357000
_diffrn_orient_matrix_UB_21      0.0377323000
_diffrn_orient_matrix_UB_22      -0.0169109000
_diffrn_orient_matrix_UB_23      -0.0083515000
_diffrn_orient_matrix_UB_31      0.0032801000
_diffrn_orient_matrix_UB_32      -0.1224925000
_diffrn_orient_matrix_UB_33      0.0111552000
_diffrn_radiation_collimation    '1.0 mm'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.1918
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            2626
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         4.18
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73655
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.370
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1136
_exptl_crystal_size_max          0.80
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.379
_refine_diff_density_min         -0.391
_refine_diff_density_rms         0.101
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.145
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2626
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.145
_refine_ls_R_factor_all          0.1720
_refine_ls_R_factor_gt           0.1129
_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)+(0.1661P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3349
_refine_ls_wR_factor_ref         0.3593
_reflns_number_gt                1421
_reflns_number_total             2626
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            c2cc36613d.txt
_cod_data_source_block           4
_cod_database_code               7108664
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
O1 O 0.2442(4) 0.2270(10) 0.39591(19) 0.0506(18) Uani 1 1 d .
O2 O 0.3857(4) 0.7222(10) 0.52167(19) 0.0480(17) Uani 1 1 d .
N2 N 0.4182(3) 0.2931(12) 0.5353(2) 0.0326(16) Uani 1 1 d .
H2 H 0.4109 0.1356 0.5256 0.039 Uiso 1 1 calc R
N1 N 0.2255(4) 0.6600(12) 0.3784(2) 0.0358(16) Uani 1 1 d .
H1 H 0.2314 0.8171 0.3885 0.043 Uiso 1 1 calc R
C6 C 0.1358(5) 0.4437(17) 0.3251(3) 0.042(2) Uani 1 1 d .
H6 H 0.1233 0.3191 0.3466 0.051 Uiso 1 1 calc R
C2 C 0.2939(4) 0.5517(15) 0.4466(3) 0.0321(18) Uani 1 1 d .
H2A H 0.3305 0.6850 0.4374 0.039 Uiso 1 1 calc R
H2B H 0.2562 0.6396 0.4650 0.039 Uiso 1 1 calc R
C12 C 0.5251(4) 0.1260(17) 0.5806(3) 0.041(2) Uani 1 1 d .
H12 H 0.5290 -0.0129 0.5605 0.049 Uiso 1 1 calc R
C5 C 0.1895(4) 0.6344(14) 0.3351(2) 0.0272(17) Uani 1 1 d .
C4 C 0.3804(5) 0.4857(14) 0.5123(2) 0.0319(19) Uani 1 1 d .
C16 C 0.4612(5) 0.5237(17) 0.6036(3) 0.040(2) Uani 1 1 d .
H16 H 0.4236 0.6529 0.5987 0.048 Uiso 1 1 calc R
C14 C 0.5669(5) 0.3422(19) 0.6484(3) 0.052(3) Uani 1 1 d .
H14 H 0.5994 0.3475 0.6739 0.062 Uiso 1 1 calc R
C10 C 0.2083(5) 0.8236(16) 0.3039(3) 0.043(2) Uani 1 1 d .
H10 H 0.2439 0.9557 0.3111 0.051 Uiso 1 1 calc R
C3 C 0.3325(4) 0.3911(15) 0.4731(2) 0.0326(18) Uani 1 1 d .
H3A H 0.3670 0.2912 0.4543 0.039 Uiso 1 1 calc R
H3B H 0.2951 0.2675 0.4846 0.039 Uiso 1 1 calc R
C11 C 0.4686(4) 0.3211(15) 0.5737(3) 0.0338(19) Uani 1 1 d .
C15 C 0.5113(5) 0.5332(19) 0.6417(3) 0.047(2) Uani 1 1 d .
H15 H 0.5068 0.6687 0.6625 0.057 Uiso 1 1 calc R
C9 C 0.1721(5) 0.8106(18) 0.2614(3) 0.049(2) Uani 1 1 d .
H9 H 0.1842 0.9340 0.2396 0.059 Uiso 1 1 calc R
C7 C 0.1002(5) 0.4377(18) 0.2828(3) 0.051(2) Uani 1 1 d .
H7 H 0.0632 0.3093 0.2759 0.061 Uiso 1 1 calc R
C13 C 0.5747(5) 0.1429(17) 0.6176(3) 0.046(2) Uani 1 1 d .
H13 H 0.6140 0.0187 0.6218 0.055 Uiso 1 1 calc R
C1 C 0.2514(5) 0.4631(14) 0.4053(2) 0.0341(19) Uani 1 1 d .
C8 C 0.1187(5) 0.6158(19) 0.2514(3) 0.051(2) Uani 1 1 d .
H8 H 0.0953 0.6074 0.2229 0.061 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
C4 N2 C11 127.4(6)
C4 N2 H2 116.3
C11 N2 H2 116.3
C1 N1 C5 126.8(6)
C1 N1 H1 116.6
C5 N1 H1 116.6
C5 C6 C7 119.3(8)
C5 C6 H6 120.3
C7 C6 H6 120.3
C3 C2 C1 122.7(7)
C3 C2 H2A 106.7
C1 C2 H2A 106.7
C3 C2 H2B 106.7
C1 C2 H2B 106.7
H2A C2 H2B 106.6
C13 C12 C11 118.9(8)
C13 C12 H12 120.5
C11 C12 H12 120.5
C6 C5 C10 121.3(7)
C6 C5 N1 122.4(7)
C10 C5 N1 116.2(7)
O2 C4 N2 124.1(7)
O2 C4 C3 121.7(7)
N2 C4 C3 114.1(6)
C11 C16 C15 119.0(8)
C11 C16 H16 120.5
C15 C16 H16 120.5
C15 C14 C13 120.6(7)
C15 C14 H14 119.7
C13 C14 H14 119.7
C5 C10 C9 118.0(7)
C5 C10 H10 121.0
C9 C10 H10 121.0
C2 C3 C4 122.0(7)
C2 C3 H3A 106.8
C4 C3 H3A 106.8
C2 C3 H3B 106.8
C4 C3 H3B 106.8
H3A C3 H3B 106.7
C16 C11 C12 121.1(7)
C16 C11 N2 122.1(7)
C12 C11 N2 116.8(7)
C14 C15 C16 119.9(9)
C14 C15 H15 120.1
C16 C15 H15 120.1
C8 C9 C10 120.3(8)
C8 C9 H9 119.8
C10 C9 H9 119.8
C8 C7 C6 120.6(8)
C8 C7 H7 119.7
C6 C7 H7 119.7
C12 C13 C14 120.5(8)
C12 C13 H13 119.7
C14 C13 H13 119.7
O1 C1 N1 123.8(7)
O1 C1 C2 121.8(7)
N1 C1 C2 114.3(6)
C7 C8 C9 120.4(8)
C7 C8 H8 119.8
C9 C8 H8 119.8
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.239(9)
O2 C4 1.239(9)
N2 C4 1.351(9)
N2 C11 1.419(9)
N2 H2 0.8600
N1 C1 1.351(9)
N1 C5 1.419(9)
N1 H1 0.8600
C6 C5 1.365(10)
C6 C7 1.386(11)
C6 H6 0.9300
C2 C3 1.302(10)
C2 C1 1.481(10)
C2 H2A 0.9700
C2 H2B 0.9700
C12 C13 1.375(10)
C12 C11 1.399(10)
C12 H12 0.9300
C5 C10 1.382(10)
C4 C3 1.488(10)
C16 C11 1.371(11)
C16 C15 1.405(10)
C16 H16 0.9300
C14 C15 1.372(12)
C14 C13 1.377(13)
C14 H14 0.9300
C10 C9 1.395(11)
C10 H10 0.9300
C3 H3A 0.9700
C3 H3B 0.9700
C15 H15 0.9300
C9 C8 1.377(12)
C9 H9 0.9300
C7 C8 1.345(13)
C7 H7 0.9300
C13 H13 0.9300
C8 H8 0.9300
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 270325
#BEGIN Loops that were not found in dictionaries:
loop_
_cell_oxdiff_twin_id
_cell_oxdiff_twin_matrix_11
_cell_oxdiff_twin_matrix_12
_cell_oxdiff_twin_matrix_13
_cell_oxdiff_twin_matrix_21
_cell_oxdiff_twin_matrix_22
_cell_oxdiff_twin_matrix_23
_cell_oxdiff_twin_matrix_31
_cell_oxdiff_twin_matrix_32
_cell_oxdiff_twin_matrix_33
1 1.0000 0.0000 0.0000 0.0000 1.0000 0.0000 0.0000 0.0000 1.0000
2 -0.9931 0.0065 -0.0005 -0.0003 -0.9939 -0.0001 0.1118 0.0084 0.9949
loop_
_diffrn_oxdiff_twin_id
_diffrn_oxdiff_twin_ratio
_diffrn_oxdiff_twin_reflns_isolated
_diffrn_oxdiff_twin_reflns_overlapped
1 0.6841 175 6343
2 0.3159 171 6343
#END Loops that were not found in dictionaries
