#------------------------------------------------------------------------------
#$Date: 2020-09-26 00:37:00 +0300 (Sat, 26 Sep 2020) $
#$Revision: 256765 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/80/4518090.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_4518090
loop_
_publ_author_name
'Núñez Alonso, David'
'Pérez-Torralba, Marta'
'Claramunt, Rosa M.'
'Torralba, M. Carmen'
'Delgado-Martínez, Patricia'
'Alkorta, Ibon'
'Elguero, José'
'Roussel, Christian'
_publ_section_title
;
 Regiospecific Synthesis and Structural Studies of
 3,5-Dihydro-4H-pyrido[2,3-b][1,4]diazepin-4-ones and Comparison with
 1,3-Dihydro-2H-benzo[b][1,4]diazepin-2-ones
;
_journal_name_full               'ACS Omega'
_journal_paper_doi               10.1021/acsomega.0c03843
_journal_year                    2020
_chemical_formula_moiety         'C15 H13 N3 O'
_chemical_formula_sum            'C15 H13 N3 O'
_chemical_formula_weight         251.28
_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   geom
_audit_creation_date             2020-05-12
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 126.527(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   21.088(3)
_cell_length_b                   8.6190(13)
_cell_length_c                   17.432(3)
_cell_measurement_reflns_used    3433
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.9440
_cell_measurement_theta_min      2.4037
_cell_volume                     2546.0(7)
_computing_cell_refinement       'SAINT v6.28A (Bruker, 2002)'
_computing_data_reduction        'SAINT v6.28A (Bruker, 2002)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.939
_diffrn_measurement_device_type  'BRUKER CCD area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0390
_diffrn_reflns_av_unetI/netI     0.0367
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.939
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            12819
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.939
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.805
_diffrn_reflns_theta_min         2.404
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            clear
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_description       block
_exptl_crystal_F_000             1056
_exptl_crystal_size_max          0.57
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.171
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         3127
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0910
_refine_ls_R_factor_gt           0.0526
_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)+(0.0722P)²+0.5811P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1378
_refine_ls_wR_factor_ref         0.1559
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1858
_reflns_number_total             3127
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ao0c03843_si_002.cif
_cod_data_source_block           C15H13N3O
_cod_database_code               4518090
_shelx_shelxl_version_number     2018/1
_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.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C15(H15), C11(H11), C14(H14), C12(H12), C13(H13)
2.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C)
;
_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
N5 N 0.34928(8) 0.70508(17) 0.48739(10) 0.0442(4) Uani 1 1 d . . . . .
O1 O 0.17541(9) 0.45790(18) 0.25311(11) 0.0760(5) Uani 1 1 d . . . . .
N1 N 0.17850(8) 0.68733(17) 0.31900(10) 0.0453(4) Uani 1 1 d . . . . .
N9 N 0.17083(10) 0.95247(19) 0.33343(11) 0.0528(4) Uani 1 1 d . . . . .
C5A C 0.29775(11) 0.8327(2) 0.44405(13) 0.0416(4) Uani 1 1 d . . . . .
C4 C 0.34845(10) 0.5978(2) 0.43555(12) 0.0393(4) Uani 1 1 d . . . . .
C10 C 0.40199(10) 0.4637(2) 0.48370(13) 0.0415(4) Uani 1 1 d . . . . .
C9A C 0.21720(10) 0.8274(2) 0.36573(12) 0.0403(4) Uani 1 1 d . . . . .
C3 C 0.29366(10) 0.6085(2) 0.32801(12) 0.0450(5) Uani 1 1 d . . . . .
H3A H 0.296470 0.711272 0.307546 0.054 Uiso 1 1 calc R . . . .
H3B H 0.308845 0.533333 0.300244 0.054 Uiso 1 1 calc R . . . .
C2 C 0.21105(11) 0.5761(2) 0.29584(12) 0.0476(5) Uani 1 1 d . . . . .
C6 C 0.32789(13) 0.9778(2) 0.48565(15) 0.0564(5) Uani 1 1 d . . . . .
H6 H 0.380632 0.987044 0.537669 0.068 Uiso 1 1 calc R . . . .
C7 C 0.28064(15) 1.1074(2) 0.45074(18) 0.0634(6) Uani 1 1 d . . . . .
H7 H 0.300731 1.204657 0.477504 0.076 Uiso 1 1 calc R . . . .
C8 C 0.20277(14) 1.0884(2) 0.37502(16) 0.0612(6) Uani 1 1 d . . . . .
H8 H 0.170466 1.175629 0.351439 0.073 Uiso 1 1 calc R . . . .
C16 C 0.09544(11) 0.6711(3) 0.28110(15) 0.0650(6) Uani 1 1 d . . . . .
H16A H 0.087343 0.716546 0.324933 0.098 Uiso 1 1 calc GR . . . .
H16B H 0.081715 0.563085 0.272918 0.098 Uiso 1 1 calc GR . . . .
H16C H 0.062827 0.723018 0.220622 0.098 Uiso 1 1 calc GR . . . .
C15 C 0.41298(12) 0.3530(2) 0.43485(15) 0.0562(5) Uani 1 1 d . . . . .
H15 H 0.384390 0.360288 0.368868 0.067 Uiso 1 1 calc R . . . .
C11 C 0.44591(12) 0.4479(3) 0.58267(14) 0.0599(6) Uani 1 1 d . . . . .
H11 H 0.439621 0.519570 0.617528 0.072 Uiso 1 1 calc R . . . .
C14 C 0.46564(13) 0.2320(3) 0.48238(17) 0.0675(6) Uani 1 1 d . . . . .
H14 H 0.471787 0.158749 0.448075 0.081 Uiso 1 1 calc R . . . .
C12 C 0.49846(13) 0.3271(3) 0.62921(17) 0.0728(7) Uani 1 1 d . . . . .
H12 H 0.527371 0.318652 0.695183 0.087 Uiso 1 1 calc R . . . .
C13 C 0.50875(12) 0.2191(3) 0.57947(18) 0.0675(6) Uani 1 1 d . . . . .
H13 H 0.544562 0.138258 0.611418 0.081 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
C4 N5 C5A 120.07(15) . . ?
C9A N1 C16 117.83(15) . . ?
C2 N1 C9A 123.25(15) . . ?
C2 N1 C16 118.27(16) . . ?
C8 N9 C9A 118.39(17) . . ?
N5 C5A C9A 126.42(16) . . ?
C6 C5A N5 117.00(17) . . ?
C6 C5A C9A 116.48(17) . . ?
N5 C4 C10 118.48(15) . . ?
N5 C4 C3 120.62(16) . . ?
C10 C4 C3 120.91(15) . . ?
C15 C10 C4 122.64(16) . . ?
C15 C10 C11 117.44(18) . . ?
C11 C10 C4 119.88(17) . . ?
N9 C9A N1 114.87(16) . . ?
N9 C9A C5A 122.67(16) . . ?
C5A C9A N1 122.37(16) . . ?
C4 C3 H3A 110.1 . . ?
C4 C3 H3B 110.1 . . ?
H3A C3 H3B 108.4 . . ?
C2 C3 C4 108.19(13) . . ?
C2 C3 H3A 110.1 . . ?
C2 C3 H3B 110.1 . . ?
O1 C2 N1 121.89(18) . . ?
O1 C2 C3 122.53(17) . . ?
N1 C2 C3 115.57(16) . . ?
C5A C6 H6 119.6 . . ?
C7 C6 C5A 120.8(2) . . ?
C7 C6 H6 119.6 . . ?
C6 C7 H7 121.1 . . ?
C8 C7 C6 117.8(2) . . ?
C8 C7 H7 121.1 . . ?
N9 C8 C7 123.8(2) . . ?
N9 C8 H8 118.1 . . ?
C7 C8 H8 118.1 . . ?
N1 C16 H16A 109.5 . . ?
N1 C16 H16B 109.5 . . ?
N1 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C10 C15 H15 119.4 . . ?
C14 C15 C10 121.27(19) . . ?
C14 C15 H15 119.4 . . ?
C10 C11 H11 119.6 . . ?
C12 C11 C10 120.7(2) . . ?
C12 C11 H11 119.6 . . ?
C15 C14 H14 119.7 . . ?
C13 C14 C15 120.5(2) . . ?
C13 C14 H14 119.7 . . ?
C11 C12 H12 119.5 . . ?
C13 C12 C11 120.9(2) . . ?
C13 C12 H12 119.5 . . ?
C14 C13 C12 119.1(2) . . ?
C14 C13 H13 120.4 . . ?
C12 C13 H13 120.4 . . ?
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
N5 C5A 1.409(2) . ?
N5 C4 1.285(2) . ?
O1 C2 1.221(2) . ?
N1 C9A 1.412(2) . ?
N1 C2 1.372(2) . ?
N1 C16 1.465(2) . ?
N9 C9A 1.334(2) . ?
N9 C8 1.331(3) . ?
C5A C9A 1.411(3) . ?
C5A C6 1.395(3) . ?
C4 C10 1.479(2) . ?
C4 C3 1.510(2) . ?
C10 C15 1.387(3) . ?
C10 C11 1.397(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C2 1.505(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.374(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.373(3) . ?
C8 H8 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C15 H15 0.9300 . ?
C15 C14 1.383(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.378(3) . ?
C14 H14 0.9300 . ?
C14 C13 1.368(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.375(3) . ?
C13 H13 0.9300 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N5 C5A C9A N1 -1.6(3) . . . . ?
N5 C5A C9A N9 174.71(15) . . . . ?
N5 C5A C6 C7 -176.87(17) . . . . ?
N5 C4 C10 C15 -171.28(17) . . . . ?
N5 C4 C10 C11 6.5(2) . . . . ?
N5 C4 C3 C2 -73.3(2) . . . . ?
C5A N5 C4 C10 -178.45(14) . . . . ?
C5A N5 C4 C3 1.2(2) . . . . ?
C5A C6 C7 C8 1.2(3) . . . . ?
C4 N5 C5A C9A 43.4(2) . . . . ?
C4 N5 C5A C6 -140.40(17) . . . . ?
C4 C10 C15 C14 177.61(18) . . . . ?
C4 C10 C11 C12 -177.35(18) . . . . ?
C4 C3 C2 O1 -110.2(2) . . . . ?
C4 C3 C2 N1 68.8(2) . . . . ?
C10 C4 C3 C2 106.35(17) . . . . ?
C10 C15 C14 C13 -0.4(3) . . . . ?
C10 C11 C12 C13 -0.3(3) . . . . ?
C9A N1 C2 O1 -177.98(18) . . . . ?
C9A N1 C2 C3 3.0(2) . . . . ?
C9A N9 C8 C7 -1.3(3) . . . . ?
C9A C5A C6 C7 -0.3(3) . . . . ?
C3 C4 C10 C15 9.1(2) . . . . ?
C3 C4 C10 C11 -173.11(17) . . . . ?
C2 N1 C9A N9 139.75(17) . . . . ?
C2 N1 C9A C5A -43.6(2) . . . . ?
C6 C5A C9A N1 -177.84(16) . . . . ?
C6 C5A C9A N9 -1.5(3) . . . . ?
C6 C7 C8 N9 -0.4(3) . . . . ?
C8 N9 C9A N1 178.86(16) . . . . ?
C8 N9 C9A C5A 2.3(3) . . . . ?
C16 N1 C9A N9 -30.9(2) . . . . ?
C16 N1 C9A C5A 145.72(17) . . . . ?
C16 N1 C2 O1 -7.4(3) . . . . ?
C16 N1 C2 C3 173.60(16) . . . . ?
C15 C10 C11 C12 0.6(3) . . . . ?
C15 C14 C13 C12 0.7(3) . . . . ?
C11 C10 C15 C14 -0.2(3) . . . . ?
C11 C12 C13 C14 -0.4(4) . . . . ?
