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#$Date: 2022-11-17 10:22:26 +0200 (Thu, 17 Nov 2022) $
#$Revision: 279345 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/61/8106125.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_8106125
loop_
_publ_author_name
'Wu, Hao'
'Hu, Qiang'
'Wang, Yuan'
_publ_section_title
;
 Crystal Structure of ethyl
 (E)-3,4-dimethyl-5-((2-(4-methylbenzoyl)hydrazono)methyl)-1H-pyrrole-2-carboxylate
 --- water --- ethanol (1/1/1), C20H29N3O5
;
_journal_issue                   2
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              279
_journal_page_last               280
_journal_paper_doi               10.1515/ncrs-2017-0278
_journal_volume                  233
_journal_year                    2018
_chemical_formula_sum            'C20 H29 N3 O5'
_chemical_formula_weight         391.46
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                94.509(4)
_cell_angle_beta                 92.570(4)
_cell_angle_gamma                102.312(3)
_cell_formula_units_Z            2
_cell_length_a                   9.1571(18)
_cell_length_b                   10.505(2)
_cell_length_c                   11.576(2)
_cell_measurement_reflns_used    1132
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      20.35
_cell_measurement_theta_min      1.96
_cell_volume                     1082.4(4)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0209
_diffrn_reflns_av_sigmaI/netI    0.0517
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5720
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.77
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.9871
_exptl_absorpt_correction_T_min  0.9846
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.201
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             420
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.170
_refine_diff_density_min         -0.139
_refine_diff_density_rms         0.033
_refine_ls_extinction_coef       0.009(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         3789
_refine_ls_number_restraints     18
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.1120
_refine_ls_R_factor_gt           0.0543
_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)+(0.0748P)²+0.0429P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1385
_refine_ls_wR_factor_ref         0.1704
_reflns_number_gt                1996
_reflns_number_total             3789
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            suppl_ncrs-2017-0278_suppl.cif
_cod_data_source_block           z
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               8106125
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.6973(4) -0.3007(4) -0.1146(3) 0.1081(12) Uani 1 1 d . . .
H1A H 0.8044 -0.2888 -0.1080 0.162 Uiso 1 1 calc R . .
H1B H 0.6672 -0.2726 -0.1871 0.162 Uiso 1 1 calc R . .
H1C H 0.6521 -0.3916 -0.1114 0.162 Uiso 1 1 calc R . .
C2 C 0.6476(3) -0.2210(3) -0.0160(3) 0.0759(9) Uani 1 1 d . . .
C3 C 0.5550(4) -0.2782(3) 0.0644(3) 0.0799(9) Uani 1 1 d . . .
H3 H 0.5225 -0.3687 0.0580 0.096 Uiso 1 1 calc R . .
C4 C 0.5087(3) -0.2052(3) 0.1545(3) 0.0731(8) Uani 1 1 d . . .
H4 H 0.4458 -0.2470 0.2073 0.088 Uiso 1 1 calc R . .
C5 C 0.5550(3) -0.0704(3) 0.1668(2) 0.0611(7) Uani 1 1 d . . .
C6 C 0.6489(3) -0.0125(3) 0.0867(3) 0.0788(9) Uani 1 1 d . . .
H6 H 0.6827 0.0780 0.0930 0.095 Uiso 1 1 calc R . .
C7 C 0.6928(4) -0.0872(4) -0.0021(3) 0.0864(10) Uani 1 1 d . . .
H7 H 0.7556 -0.0456 -0.0551 0.104 Uiso 1 1 calc R . .
C8 C 0.5087(3) 0.0163(3) 0.2594(2) 0.0635(7) Uani 1 1 d . . .
C9 C 0.2654(3) -0.0104(3) 0.4852(2) 0.0635(8) Uani 1 1 d . . .
H9A H 0.2278 -0.1004 0.4776 0.076 Uiso 1 1 calc R . .
C10 C 0.2160(3) 0.0708(2) 0.5739(2) 0.0573(7) Uani 1 1 d . . .
C11 C 0.1095(3) 0.0388(3) 0.6547(2) 0.0607(7) Uani 1 1 d . . .
C12 C 0.0996(3) 0.1554(3) 0.7186(2) 0.0587(7) Uani 1 1 d . . .
C13 C 0.2010(3) 0.2558(2) 0.6753(2) 0.0576(7) Uani 1 1 d . . .
C14 C 0.0272(3) -0.0968(3) 0.6740(3) 0.0788(9) Uani 1 1 d . . .
H14A H 0.0270 -0.1543 0.6052 0.118 Uiso 1 1 calc R . .
H14B H -0.0741 -0.0954 0.6910 0.118 Uiso 1 1 calc R . .
H14C H 0.0760 -0.1275 0.7380 0.118 Uiso 1 1 calc R . .
C15 C -0.0009(3) 0.1667(3) 0.8165(3) 0.0774(9) Uani 1 1 d . . .
H15A H 0.0192 0.2556 0.8501 0.116 Uiso 1 1 calc R . .
H15B H 0.0176 0.1107 0.8746 0.116 Uiso 1 1 calc R . .
H15C H -0.1036 0.1409 0.7872 0.116 Uiso 1 1 calc R . .
C16 C 0.2545(3) 0.3946(3) 0.7084(3) 0.0659(8) Uani 1 1 d . . .
C17 C 0.2332(4) 0.5827(3) 0.8263(3) 0.0974(11) Uani 1 1 d . . .
H17A H 0.2193 0.6328 0.7614 0.117 Uiso 1 1 calc R . .
H17B H 0.3390 0.6019 0.8506 0.117 Uiso 1 1 calc R . .
C18 C 0.1455(5) 0.6178(4) 0.9236(4) 0.1216(14) Uani 1 1 d . . .
H18A H 0.0412 0.5998 0.8983 0.182 Uiso 1 1 calc R . .
H18B H 0.1788 0.7092 0.9484 0.182 Uiso 1 1 calc R . .
H18C H 0.1594 0.5671 0.9871 0.182 Uiso 1 1 calc R . .
C19 C 0.7716(8) 0.4277(6) 0.6831(6) 0.1037(18) Uani 0.609(5) 1 d PD A 1
H19A H 0.8344 0.4125 0.7481 0.124 Uiso 0.609(5) 1 calc PR A 1
H19B H 0.6936 0.4672 0.7145 0.124 Uiso 0.609(5) 1 calc PR A 1
C19B C 0.8388(13) 0.3907(9) 0.6039(10) 0.1037(18) Uani 0.391(5) 1 d PD A 2
H19C H 0.8604 0.3794 0.5229 0.124 Uiso 0.391(5) 1 calc PR A 2
H19D H 0.9199 0.3706 0.6509 0.124 Uiso 0.391(5) 1 calc PR A 2
C20 C 0.865(4) 0.5226(11) 0.612(3) 0.133(4) Uani 0.609(5) 1 d PDU A 1
H20A H 0.9146 0.5987 0.6613 0.200 Uiso 0.609(5) 1 calc PR A 1
H20B H 0.8012 0.5479 0.5536 0.200 Uiso 0.609(5) 1 calc PR A 1
H20C H 0.9375 0.4825 0.5755 0.200 Uiso 0.609(5) 1 calc PR A 1
C20B C 0.827(6) 0.5281(16) 0.635(4) 0.133(4) Uani 0.391(5) 1 d PDU A 2
H20D H 0.9019 0.5862 0.5970 0.200 Uiso 0.391(5) 1 calc PR A 2
H20E H 0.8428 0.5480 0.7173 0.200 Uiso 0.391(5) 1 calc PR A 2
H20F H 0.7296 0.5389 0.6097 0.200 Uiso 0.391(5) 1 calc PR A 2
O1 O 0.5606(2) 0.1357(2) 0.26954(18) 0.0844(7) Uani 1 1 d . . .
O2 O 0.3604(3) 0.46048(19) 0.6665(2) 0.0937(8) Uani 1 1 d . . .
O3 O 0.1807(2) 0.44304(18) 0.79201(19) 0.0782(6) Uani 1 1 d . . .
O4 O 0.5070(2) 0.32191(18) 0.44231(18) 0.0882(7) Uani 1 1 d D . .
H4A H 0.5395 0.3927 0.4095 0.132 Uiso 1 1 d RD . .
H4B H 0.5095 0.2574 0.3903 0.132 Uiso 1 1 d RD . .
O5 O 0.7044(3) 0.3066(2) 0.6231(2) 0.0943(7) Uani 1 1 d D . .
H5 H 0.640(4) 0.310(4) 0.568(3) 0.141 Uiso 1 1 d D . .
N1 N 0.4064(3) -0.0386(2) 0.3319(2) 0.0636(6) Uani 1 1 d . . .
H1 H 0.367(3) -0.128(3) 0.331(2) 0.076 Uiso 1 1 d . . .
N2 N 0.3618(2) 0.0419(2) 0.4165(2) 0.0629(6) Uani 1 1 d . . .
N3 N 0.2698(2) 0.2020(2) 0.58752(19) 0.0605(6) Uani 1 1 d . . .
H3A H 0.3369 0.2449 0.5471 0.073 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
C2 C1 H1A 109.5 . .
C2 C1 H1B 109.5 . .
H1A C1 H1B 109.5 . .
C2 C1 H1C 109.5 . .
H1A C1 H1C 109.5 . .
H1B C1 H1C 109.5 . .
C7 C2 C3 116.6(3) . .
C7 C2 C1 121.5(3) . .
C3 C2 C1 121.9(3) . .
C2 C3 C4 121.9(3) . .
C2 C3 H3 119.0 . .
C4 C3 H3 119.0 . .
C3 C4 C5 120.6(3) . .
C3 C4 H4 119.7 . .
C5 C4 H4 119.7 . .
C6 C5 C4 117.8(3) . .
C6 C5 C8 117.9(3) . .
C4 C5 C8 124.3(3) . .
C7 C6 C5 120.5(3) . .
C7 C6 H6 119.8 . .
C5 C6 H6 119.8 . .
C6 C7 C2 122.6(3) . .
C6 C7 H7 118.7 . .
C2 C7 H7 118.7 . .
O1 C8 N1 120.6(3) . .
O1 C8 C5 121.2(3) . .
N1 C8 C5 118.2(3) . .
N2 C9 C10 119.4(2) . .
N2 C9 H9A 120.3 . .
C10 C9 H9A 120.3 . .
N3 C10 C11 108.1(2) . .
N3 C10 C9 121.6(2) . .
C11 C10 C9 130.3(2) . .
C10 C11 C12 107.4(2) . .
C10 C11 C14 126.0(3) . .
C12 C11 C14 126.5(3) . .
C13 C12 C11 106.9(2) . .
C13 C12 C15 127.4(3) . .
C11 C12 C15 125.6(2) . .
N3 C13 C12 108.0(2) . .
N3 C13 C16 116.9(2) . .
C12 C13 C16 134.9(3) . .
C11 C14 H14A 109.5 . .
C11 C14 H14B 109.5 . .
H14A C14 H14B 109.5 . .
C11 C14 H14C 109.5 . .
H14A C14 H14C 109.5 . .
H14B C14 H14C 109.5 . .
C12 C15 H15A 109.5 . .
C12 C15 H15B 109.5 . .
H15A C15 H15B 109.5 . .
C12 C15 H15C 109.5 . .
H15A C15 H15C 109.5 . .
H15B C15 H15C 109.5 . .
O2 C16 O3 122.5(3) . .
O2 C16 C13 122.9(3) . .
O3 C16 C13 114.5(3) . .
O3 C17 C18 107.9(3) . .
O3 C17 H17A 110.1 . .
C18 C17 H17A 110.1 . .
O3 C17 H17B 110.1 . .
C18 C17 H17B 110.1 . .
H17A C17 H17B 108.4 . .
C17 C18 H18A 109.5 . .
C17 C18 H18B 109.5 . .
H18A C18 H18B 109.5 . .
C17 C18 H18C 109.5 . .
H18A C18 H18C 109.5 . .
H18B C18 H18C 109.5 . .
O5 C19 C20 115.0(12) . .
O5 C19 H19A 108.5 . .
C20 C19 H19A 108.5 . .
O5 C19 H19B 108.5 . .
C20 C19 H19B 108.5 . .
H19A C19 H19B 107.5 . .
O5 C19B C20B 109.4(17) . .
O5 C19B H19C 109.8 . .
C20B C19B H19C 109.8 . .
O5 C19B H19D 109.8 . .
C20B C19B H19D 109.8 . .
H19C C19B H19D 108.2 . .
C19B C20B H20D 109.5 . .
C19B C20B H20E 109.5 . .
H20D C20B H20E 109.5 . .
C19B C20B H20F 109.5 . .
H20D C20B H20F 109.5 . .
H20E C20B H20F 109.5 . .
C16 O3 C17 115.2(2) . .
H4A O4 H4B 105.8 . .
C19B O5 C19 51.3(5) . .
C19B O5 H5 108(3) . .
C19 O5 H5 115(3) . .
C8 N1 N2 118.2(2) . .
C8 N1 H1 124.3(17) . .
N2 N1 H1 117.5(17) . .
C9 N2 N1 118.0(2) . .
C10 N3 C13 109.6(2) . .
C10 N3 H3A 125.2 . .
C13 N3 H3A 125.2 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.506(4) .
C1 H1A 0.9600 .
C1 H1B 0.9600 .
C1 H1C 0.9600 .
C2 C7 1.373(4) .
C2 C3 1.374(4) .
C3 C4 1.381(4) .
C3 H3 0.9300 .
C4 C5 1.382(4) .
C4 H4 0.9300 .
C5 C6 1.381(4) .
C5 C8 1.488(4) .
C6 C7 1.371(4) .
C6 H6 0.9300 .
C7 H7 0.9300 .
C8 O1 1.238(3) .
C8 N1 1.353(3) .
C9 N2 1.279(3) .
C9 C10 1.434(4) .
C9 H9A 0.9300 .
C10 N3 1.355(3) .
C10 C11 1.389(4) .
C11 C12 1.403(4) .
C11 C14 1.502(4) .
C12 C13 1.391(3) .
C12 C15 1.504(4) .
C13 N3 1.366(3) .
C13 C16 1.450(4) .
C14 H14A 0.9600 .
C14 H14B 0.9600 .
C14 H14C 0.9600 .
C15 H15A 0.9600 .
C15 H15B 0.9600 .
C15 H15C 0.9600 .
C16 O2 1.209(3) .
C16 O3 1.335(3) .
C17 O3 1.460(3) .
C17 C18 1.480(5) .
C17 H17A 0.9700 .
C17 H17B 0.9700 .
C18 H18A 0.9600 .
C18 H18B 0.9600 .
C18 H18C 0.9600 .
C19 O5 1.404(6) .
C19 C20 1.491(10) .
C19 H19A 0.9700 .
C19 H19B 0.9700 .
C19B O5 1.392(10) .
C19B C20B 1.486(10) .
C19B H19C 0.9700 .
C19B H19D 0.9700 .
C20 H20A 0.9600 .
C20 H20B 0.9600 .
C20 H20C 0.9600 .
C20B H20D 0.9600 .
C20B H20E 0.9600 .
C20B H20F 0.9600 .
O4 H4A 0.8641 .
O4 H4B 0.8753 .
O5 H5 0.856(10) .
N1 N2 1.376(3) .
N1 H1 0.93(3) .
N3 H3A 0.8600 .
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
N1 H1 O5 0.93(3) 1.97(3) 2.878(3) 163(2) 2_656
N3 H3A O4 0.86 2.08 2.937(3) 171.5 .
O4 H4A O2 0.86 1.92 2.774(3) 171.0 2_666
O4 H4B O1 0.88 1.96 2.819(3) 167.1 .
O4 H4B N2 0.88 2.43 2.944(3) 118.3 .
O5 H5 O4 0.856(10) 1.886(11) 2.741(3) 177(4) .
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
C7 C2 C3 C4 0.3(5) . . . .
C1 C2 C3 C4 -179.6(3) . . . .
C2 C3 C4 C5 -0.1(5) . . . .
C3 C4 C5 C6 -0.3(4) . . . .
C3 C4 C5 C8 178.8(3) . . . .
C4 C5 C6 C7 0.5(4) . . . .
C8 C5 C6 C7 -178.6(3) . . . .
C5 C6 C7 C2 -0.4(5) . . . .
C3 C2 C7 C6 0.0(5) . . . .
C1 C2 C7 C6 179.9(3) . . . .
C6 C5 C8 O1 -5.0(4) . . . .
C4 C5 C8 O1 176.0(3) . . . .
C6 C5 C8 N1 174.2(3) . . . .
C4 C5 C8 N1 -4.8(4) . . . .
N2 C9 C10 N3 -0.5(4) . . . .
N2 C9 C10 C11 177.0(3) . . . .
N3 C10 C11 C12 0.1(3) . . . .
C9 C10 C11 C12 -177.7(3) . . . .
N3 C10 C11 C14 -176.8(2) . . . .
C9 C10 C11 C14 5.5(5) . . . .
C10 C11 C12 C13 -0.2(3) . . . .
C14 C11 C12 C13 176.6(3) . . . .
C10 C11 C12 C15 -179.3(2) . . . .
C14 C11 C12 C15 -2.5(4) . . . .
C11 C12 C13 N3 0.3(3) . . . .
C15 C12 C13 N3 179.4(2) . . . .
C11 C12 C13 C16 -173.6(3) . . . .
C15 C12 C13 C16 5.5(5) . . . .
N3 C13 C16 O2 -4.2(4) . . . .
C12 C13 C16 O2 169.2(3) . . . .
N3 C13 C16 O3 178.1(2) . . . .
C12 C13 C16 O3 -8.5(4) . . . .
O2 C16 O3 C17 2.3(4) . . . .
C13 C16 O3 C17 -180.0(3) . . . .
C18 C17 O3 C16 -176.8(3) . . . .
C20B C19B O5 C19 -32(2) . . . .
C20 C19 O5 C19B 30.2(16) . . . .
O1 C8 N1 N2 0.2(4) . . . .
C5 C8 N1 N2 -179.0(2) . . . .
C10 C9 N2 N1 -179.7(2) . . . .
C8 N1 N2 C9 -179.8(2) . . . .
C11 C10 N3 C13 0.1(3) . . . .
C9 C10 N3 C13 178.1(2) . . . .
C12 C13 N3 C10 -0.2(3) . . . .
C16 C13 N3 C10 174.9(2) . . . .
