#------------------------------------------------------------------------------
#$Date: 2022-02-04 21:58:07 +0200 (Fri, 04 Feb 2022) $
#$Revision: 272746 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/11/7061111.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_7061111
loop_
_publ_author_name
'Todorova, Stanislava E.'
'Rusew, Rusi I.'
'Petkova, Zhanina S.'
'Shivachev, Boris L.'
'Nikolova, Rositsa P.'
'Kurteva, Vanya B.'
_publ_section_title
;
 Acylpyrazolones possessing a heterocyclic moiety in the acyl fragment:
 intramolecular vs. intermolecular zwitterionic structures
;
_journal_issue                   3
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              1080
_journal_page_last               1086
_journal_paper_doi               10.1039/D1NJ05458A
_journal_volume                  46
_journal_year                    2022
_chemical_formula_moiety         'C16 H19 N3 O2'
_chemical_formula_sum            'C16 H19 N3 O2'
_chemical_formula_weight         285.34
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2021-10-14
_audit_creation_method
;
Olex2 1.5
(compiled 2021.08.20 svn.r13c46975 for OlexSys, GUI svn.r6405)
;
_audit_update_record
;
2021-11-02 deposited with the CCDC.	2021-12-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.3400(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.3849(4)
_cell_length_b                   9.9562(4)
_cell_length_c                   13.2945(5)
_cell_measurement_reflns_used    9934
_cell_measurement_temperature    290
_cell_measurement_theta_max      26.112
_cell_measurement_theta_min      2.741
_cell_volume                     1477.52(10)
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      290
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0531
_diffrn_reflns_av_unetI/netI     0.0275
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            25571
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.167
_diffrn_reflns_theta_min         2.741
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.6180
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1080 before and 0.0667 after correction.
The Ratio of minimum to maximum transmission is 0.8292.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_description       block
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.366
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     195
_refine_ls_number_reflns         2916
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0556
_refine_ls_R_factor_gt           0.0475
_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)+(0.0582P)²+0.5756P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1218
_refine_ls_wR_factor_ref         0.1294
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2508
_reflns_number_total             2916
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1nj05458a2.cif
_cod_data_source_block           mo_b_0130_0m
_cod_depositor_comments
'Adding full bibliography for 7061108--7061121.cif.'
_cod_database_code               7061111
_shelx_shelxl_version_number     2018/3
_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.
;
_shelx_estimated_absorpt_t_max   0.975
_shelx_estimated_absorpt_t_min   0.958
_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:
 C12(H12A,H12B), C13(H13A,H13B), C16(H16A,H16B), C15(H15A,H15B), C14(H14A,H14B)
2.b Aromatic/amide H refined with riding coordinates:
 C10(H10), C9(H9), C6(H6), C8(H8), C7(H7)
2.c Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
O1 O 0.58676(9) 0.25126(10) 0.63262(9) 0.0381(3) Uani 1 1 d . . . . .
O11 O 0.64334(10) 0.67644(12) 0.70536(12) 0.0533(4) Uani 1 1 d . . . . .
N1 N 0.39005(11) 0.32911(12) 0.59411(10) 0.0345(3) Uani 1 1 d . . . . .
N2 N 0.32637(11) 0.44855(12) 0.59613(11) 0.0372(3) Uani 1 1 d . . . . .
N3 N 0.85740(11) 0.56181(13) 0.71311(10) 0.0340(3) Uani 1 1 d . . . . .
C2 C 0.52586(12) 0.48618(15) 0.64714(11) 0.0314(3) Uani 1 1 d . . . . .
C1 C 0.51252(12) 0.34617(15) 0.62547(11) 0.0301(3) Uani 1 1 d . . . . .
C5 C 0.32530(13) 0.20843(15) 0.57136(11) 0.0332(3) Uani 1 1 d . . . . .
C3 C 0.40781(13) 0.53993(15) 0.62658(12) 0.0334(3) Uani 1 1 d . . . . .
C11 C 0.63531(13) 0.55661(15) 0.68223(12) 0.0355(3) Uani 1 1 d . . . . .
C10 C 0.36229(15) 0.11094(16) 0.51046(12) 0.0402(4) Uani 1 1 d . . . . .
H10 H 0.431790 0.123323 0.484711 0.048 Uiso 1 1 calc R U . . .
C12 C 0.74969(13) 0.47457(16) 0.69291(14) 0.0405(4) Uani 1 1 d . . . . .
H12A H 0.753594 0.411046 0.748789 0.049 Uiso 1 1 calc R U . . .
H12B H 0.748455 0.423974 0.630356 0.049 Uiso 1 1 calc R U . . .
C13 C 0.97136(14) 0.48148(17) 0.74403(16) 0.0480(4) Uani 1 1 d . . . . .
H13A H 1.009165 0.501200 0.814415 0.058 Uiso 1 1 calc R U . . .
H13B H 0.954382 0.386021 0.738123 0.058 Uiso 1 1 calc R U . . .
C9 C 0.29558(18) -0.00509(18) 0.48794(15) 0.0513(5) Uani 1 1 d . . . . .
H9 H 0.321002 -0.071416 0.447833 0.062 Uiso 1 1 calc R U . . .
C6 C 0.22105(16) 0.19010(18) 0.60887(15) 0.0487(4) Uani 1 1 d . . . . .
H6 H 0.195859 0.255395 0.649960 0.058 Uiso 1 1 calc R U . . .
C4 C 0.37069(15) 0.68301(16) 0.63121(16) 0.0485(4) Uani 1 1 d . . . . .
H4A H 0.402344 0.734423 0.581531 0.073 Uiso 1 1 calc R U . . .
H4B H 0.400991 0.718081 0.698579 0.073 Uiso 1 1 calc R U . . .
H4C H 0.284842 0.688684 0.616497 0.073 Uiso 1 1 calc R U . . .
C16 C 0.87275(16) 0.6469(2) 0.62335(14) 0.0495(4) Uani 1 1 d . . . . .
H16A H 0.835248 0.605000 0.559176 0.059 Uiso 1 1 calc R U . . .
H16B H 0.838079 0.735267 0.627307 0.059 Uiso 1 1 calc R U . . .
C8 C 0.19174(19) -0.02286(19) 0.52460(19) 0.0636(6) Uani 1 1 d . . . . .
H8 H 0.146642 -0.100592 0.508591 0.076 Uiso 1 1 calc R U . . .
C7 C 0.15480(18) 0.0739(2) 0.5847(2) 0.0670(6) Uani 1 1 d . . . . .
H7 H 0.084643 0.061488 0.609426 0.080 Uiso 1 1 calc R U . . .
C15 C 1.0059(2) 0.6560(3) 0.6320(2) 0.0718(6) Uani 1 1 d . . . . .
H15A H 1.026249 0.672203 0.565489 0.086 Uiso 1 1 calc R U . . .
H15B H 1.039534 0.727355 0.678563 0.086 Uiso 1 1 calc R U . . .
C14 C 1.0502(2) 0.5217(3) 0.6732(2) 0.0886(9) Uani 1 1 d . . . . .
H14A H 1.045361 0.457028 0.617936 0.106 Uiso 1 1 calc R U . . .
H14B H 1.132799 0.527599 0.709350 0.106 Uiso 1 1 calc R U . . .
H3 H 0.8546(18) 0.623(2) 0.7620(16) 0.055(6) 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_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 N1 C5 118.57(11) . . ?
C1 N1 N2 112.69(12) . . ?
C1 N1 C5 128.42(12) . . ?
C3 N2 N1 105.06(12) . . ?
C12 N3 C13 111.99(12) . . ?
C12 N3 C16 114.06(13) . . ?
C12 N3 H3 112.6(13) . . ?
C13 N3 H3 108.3(13) . . ?
C16 N3 C13 106.68(13) . . ?
C16 N3 H3 102.5(13) . . ?
C1 C2 C11 126.76(13) . . ?
C3 C2 C1 105.67(12) . . ?
C3 C2 C11 127.58(14) . . ?
O1 C1 N1 123.50(13) . . ?
O1 C1 C2 132.49(13) . . ?
N1 C1 C2 103.98(12) . . ?
C10 C5 N1 121.15(14) . . ?
C10 C5 C6 119.95(15) . . ?
C6 C5 N1 118.87(14) . . ?
N2 C3 C2 112.59(13) . . ?
N2 C3 C4 119.28(14) . . ?
C2 C3 C4 128.06(14) . . ?
O11 C11 C2 125.14(14) . . ?
O11 C11 C12 118.51(13) . . ?
C2 C11 C12 116.35(13) . . ?
C5 C10 H10 120.1 . . ?
C5 C10 C9 119.74(16) . . ?
C9 C10 H10 120.1 . . ?
N3 C12 C11 111.40(12) . . ?
N3 C12 H12A 109.3 . . ?
N3 C12 H12B 109.3 . . ?
C11 C12 H12A 109.3 . . ?
C11 C12 H12B 109.3 . . ?
H12A C12 H12B 108.0 . . ?
N3 C13 H13A 110.5 . . ?
N3 C13 H13B 110.5 . . ?
H13A C13 H13B 108.7 . . ?
C14 C13 N3 106.25(16) . . ?
C14 C13 H13A 110.5 . . ?
C14 C13 H13B 110.5 . . ?
C10 C9 H9 119.9 . . ?
C8 C9 C10 120.29(18) . . ?
C8 C9 H9 119.9 . . ?
C5 C6 H6 120.3 . . ?
C7 C6 C5 119.50(18) . . ?
C7 C6 H6 120.3 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N3 C16 H16A 110.9 . . ?
N3 C16 H16B 110.9 . . ?
H16A C16 H16B 108.9 . . ?
C15 C16 N3 104.32(15) . . ?
C15 C16 H16A 110.9 . . ?
C15 C16 H16B 110.9 . . ?
C9 C8 H8 120.0 . . ?
C7 C8 C9 119.99(17) . . ?
C7 C8 H8 120.0 . . ?
C6 C7 H7 119.7 . . ?
C8 C7 C6 120.52(19) . . ?
C8 C7 H7 119.7 . . ?
C16 C15 H15A 111.0 . . ?
C16 C15 H15B 111.0 . . ?
H15A C15 H15B 109.0 . . ?
C14 C15 C16 103.68(19) . . ?
C14 C15 H15A 111.0 . . ?
C14 C15 H15B 111.0 . . ?
C13 C14 C15 105.81(18) . . ?
C13 C14 H14A 110.6 . . ?
C13 C14 H14B 110.6 . . ?
C15 C14 H14A 110.6 . . ?
C15 C14 H14B 110.6 . . ?
H14A C14 H14B 108.7 . . ?
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
O1 C1 1.2589(17) . ?
O11 C11 1.2310(19) . ?
N1 N2 1.3957(17) . ?
N1 C1 1.3850(18) . ?
N1 C5 1.4110(19) . ?
N2 C3 1.3053(19) . ?
N3 C12 1.4835(19) . ?
N3 C13 1.5107(19) . ?
N3 C16 1.501(2) . ?
N3 H3 0.90(2) . ?
C2 C1 1.426(2) . ?
C2 C3 1.422(2) . ?
C2 C11 1.426(2) . ?
C5 C10 1.382(2) . ?
C5 C6 1.387(2) . ?
C3 C4 1.491(2) . ?
C11 C12 1.520(2) . ?
C10 H10 0.9300 . ?
C10 C9 1.383(2) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.479(3) . ?
C9 H9 0.9300 . ?
C9 C8 1.376(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.384(3) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C15 1.501(3) . ?
C8 H8 0.9300 . ?
C8 C7 1.370(3) . ?
C7 H7 0.9300 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C14 1.495(4) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
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
C12 H12A O11 0.97 2.63 3.3875(19) 135.0 2_646 yes
C13 H13B O11 0.97 2.55 3.424(2) 150.5 2_646 yes
C16 H16A N2 0.97 2.54 3.458(2) 158.3 3_666 yes
N3 H3 O1 0.90(2) 1.91(2) 2.7669(17) 158.0(19) 2_656 yes
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
O11 C11 C12 N3 -10.3(2) . . . . ?
N1 N2 C3 C2 -0.93(17) . . . . ?
N1 N2 C3 C4 176.26(14) . . . . ?
N1 C5 C10 C9 -178.74(14) . . . . ?
N1 C5 C6 C7 178.14(17) . . . . ?
N2 N1 C1 O1 177.75(13) . . . . ?
N2 N1 C1 C2 -0.80(16) . . . . ?
N2 N1 C5 C10 140.71(15) . . . . ?
N2 N1 C5 C6 -37.5(2) . . . . ?
N3 C13 C14 C15 21.5(3) . . . . ?
N3 C16 C15 C14 35.0(2) . . . . ?
C2 C11 C12 N3 170.65(13) . . . . ?
C1 N1 N2 C3 1.09(17) . . . . ?
C1 N1 C5 C10 -46.2(2) . . . . ?
C1 N1 C5 C6 135.57(17) . . . . ?
C1 C2 C3 N2 0.47(17) . . . . ?
C1 C2 C3 C4 -176.42(16) . . . . ?
C1 C2 C11 O11 -176.01(16) . . . . ?
C1 C2 C11 C12 3.0(2) . . . . ?
C5 N1 N2 C3 175.19(13) . . . . ?
C5 N1 C1 O1 4.4(2) . . . . ?
C5 N1 C1 C2 -174.18(14) . . . . ?
C5 C10 C9 C8 1.0(3) . . . . ?
C5 C6 C7 C8 0.3(3) . . . . ?
C3 C2 C1 O1 -178.14(16) . . . . ?
C3 C2 C1 N1 0.21(15) . . . . ?
C3 C2 C11 O11 3.9(3) . . . . ?
C3 C2 C11 C12 -177.11(15) . . . . ?
C11 C2 C1 O1 1.8(3) . . . . ?
C11 C2 C1 N1 -179.85(14) . . . . ?
C11 C2 C3 N2 -179.47(15) . . . . ?
C11 C2 C3 C4 3.6(3) . . . . ?
C10 C5 C6 C7 -0.1(3) . . . . ?
C10 C9 C8 C7 -0.8(3) . . . . ?
C12 N3 C13 C14 125.92(19) . . . . ?
C12 N3 C16 C15 -146.21(16) . . . . ?
C13 N3 C12 C11 168.99(14) . . . . ?
C13 N3 C16 C15 -22.0(2) . . . . ?
C9 C8 C7 C6 0.1(4) . . . . ?
C6 C5 C10 C9 -0.6(2) . . . . ?
C16 N3 C12 C11 -69.72(18) . . . . ?
C16 N3 C13 C14 0.5(2) . . . . ?
C16 C15 C14 C13 -35.3(3) . . . . ?
