#------------------------------------------------------------------------------
#$Date: 2023-02-08 11:44:56 +0200 (Wed, 08 Feb 2023) $
#$Revision: 280815 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/67/8106714.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_8106714
loop_
_publ_author_name
'Mao, Pan-Dong'
'Yan, Ling-Ling'
'Wu, Wei-Na'
'Cai, Hong-Xin'
_publ_section_title
;
 N′-(5-ethoxycarbonyl-3,4-dimethyl-pyrrol-2-yl-methylidene)-4-hydroxybenzohydrazide
 monohydrate, C17H21N3O5
;
_journal_issue                   6
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              899
_journal_page_last               900
_journal_paper_doi               10.1515/ncrs-2017-0057
_journal_volume                  232
_journal_year                    2017
_chemical_formula_sum            'C17 H21 N3 O5'
_chemical_formula_weight         347.37
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 105.195(12)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.2278(16)
_cell_length_b                   15.093(3)
_cell_length_c                   12.698(2)
_cell_measurement_reflns_used    1898
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.87
_cell_measurement_theta_min      2.45
_cell_volume                     1706.7(5)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_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 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω 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  0.0459
_diffrn_reflns_av_sigmaI/netI    0.0388
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            12944
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.14
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  0.9850
_exptl_absorpt_correction_T_min  0.9792
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.352
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.474
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3000
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0842
_refine_ls_R_factor_gt           0.0553
_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)+(0.0805P)²+0.5316P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1459
_refine_ls_wR_factor_ref         0.1662
_reflns_number_gt                2016
_reflns_number_total             3000
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            suppl_ncrs-2017-0057_suppl.cif
_cod_data_source_block           z
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               8106714
_publcif_info_exptl_table_max_cols 4
_publcif_info_exptl_table_use_headnotes n
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N2 N 0.6348(2) 0.02933(14) 0.93676(16) 0.0445(5) Uani 1 1 d . . .
N1 N 0.8876(2) -0.06095(13) 1.05922(16) 0.0426(5) Uani 1 1 d . . .
H1A H 0.8379 -0.0924 1.0052 0.051 Uiso 1 1 calc R . .
N3 N 0.5149(2) 0.07672(14) 0.87624(16) 0.0463(6) Uani 1 1 d . . .
H3A H 0.5003 0.1306 0.8929 0.056 Uiso 1 1 calc R . .
O3 O 0.4397(2) -0.04019(14) 0.76629(16) 0.0633(6) Uani 1 1 d . . .
C12 C 0.2949(3) 0.09113(17) 0.72426(19) 0.0418(6) Uani 1 1 d . . .
O4 O -0.0472(2) 0.23575(14) 0.51712(15) 0.0651(6) Uani 1 1 d . . .
H4A H -0.0879 0.2690 0.5517 0.098 Uiso 1 1 calc R . .
C10 C 0.7236(3) 0.06866(17) 1.0172(2) 0.0426(6) Uani 1 1 d . . .
H10A H 0.7049 0.1269 1.0337 0.051 Uiso 1 1 calc R . .
C14 C 0.1387(3) 0.22183(18) 0.6892(2) 0.0472(7) Uani 1 1 d . . .
H14A H 0.1123 0.2767 0.7120 0.057 Uiso 1 1 calc R . .
C16 C 0.1013(3) 0.1067(2) 0.5556(2) 0.0547(7) Uani 1 1 d . . .
H16A H 0.0500 0.0840 0.4881 0.066 Uiso 1 1 calc R . .
C15 C 0.0637(3) 0.18871(19) 0.5880(2) 0.0465(6) Uani 1 1 d . . .
O5 O 0.6797(2) -0.15668(13) 0.87010(16) 0.0598(6) Uani 1 1 d D . .
C11 C 0.4201(3) 0.03682(18) 0.7897(2) 0.0443(6) Uani 1 1 d . . .
C13 C 0.2526(3) 0.17317(17) 0.7559(2) 0.0442(6) Uani 1 1 d . . .
H13A H 0.3025 0.1958 0.8239 0.053 Uiso 1 1 calc R . .
C7 C 0.8525(3) 0.02272(16) 1.08231(19) 0.0402(6) Uani 1 1 d . . .
C4 C 1.0142(3) -0.08758(18) 1.1352(2) 0.0442(6) Uani 1 1 d . . .
O2 O 1.1826(3) -0.20519(16) 1.2033(2) 0.0844(7) Uani 1 1 d . . .
C6 C 0.9603(3) 0.05104(17) 1.1745(2) 0.0435(6) Uani 1 1 d . . .
C17 C 0.2150(3) 0.05843(19) 0.6233(2) 0.0519(7) Uani 1 1 d . . .
H17A H 0.2388 0.0028 0.6010 0.062 Uiso 1 1 calc R . .
C5 C 1.0615(3) -0.01860(18) 1.2083(2) 0.0439(6) Uani 1 1 d . . .
C9 C 0.9659(4) 0.1397(2) 1.2290(3) 0.0688(9) Uani 1 1 d . . .
H9A H 1.0513 0.1419 1.2913 0.103 Uiso 1 1 calc R . .
H9B H 0.8758 0.1483 1.2520 0.103 Uiso 1 1 calc R . .
H9C H 0.9743 0.1855 1.1784 0.103 Uiso 1 1 calc R . .
O1 O 1.0057(3) -0.21960(15) 1.0479(2) 0.0994(9) Uani 1 1 d D . .
C3 C 1.0783(4) -0.1743(2) 1.1351(3) 0.0621(8) Uani 1 1 d . A .
C8 C 1.1961(3) -0.0185(2) 1.3039(2) 0.0631(8) Uani 1 1 d . . .
H8A H 1.2039 0.0377 1.3403 0.095 Uiso 1 1 calc R . .
H8B H 1.2847 -0.0285 1.2793 0.095 Uiso 1 1 calc R . .
H8C H 1.1865 -0.0647 1.3536 0.095 Uiso 1 1 calc R . .
C1 C 0.9520(14) -0.3628(9) 1.0424(15) 0.110(5) Uani 0.464(18) 1 d PD A 1
H1B H 0.9868 -0.3626 1.1206 0.165 Uiso 0.464(18) 1 calc PR A 1
H1C H 0.9545 -0.4221 1.0158 0.165 Uiso 0.464(18) 1 calc PR A 1
H1D H 0.8509 -0.3407 1.0207 0.165 Uiso 0.464(18) 1 calc PR A 1
C1A C 0.9574(12) -0.3590(6) 0.9697(12) 0.090(4) Uani 0.536(18) 1 d PD A 2
H1A1 H 0.8638 -0.3672 0.9881 0.135 Uiso 0.536(18) 1 calc PR A 2
H1A2 H 0.9984 -0.4157 0.9589 0.135 Uiso 0.536(18) 1 calc PR A 2
H1A3 H 0.9408 -0.3248 0.9038 0.135 Uiso 0.536(18) 1 calc PR A 2
C2A C 1.0609(13) -0.3130(5) 1.0569(11) 0.079(4) Uani 0.536(18) 1 d PD A 2
H2A1 H 1.1622 -0.3160 1.0483 0.095 Uiso 0.536(18) 1 calc PR A 2
H2A2 H 1.0602 -0.3381 1.1271 0.095 Uiso 0.536(18) 1 calc PR A 2
C2 C 1.050(2) -0.3054(8) 0.9965(16) 0.118(7) Uani 0.464(18) 1 d PD A 1
H2A H 1.0216 -0.3042 0.9173 0.141 Uiso 0.464(18) 1 calc PR A 1
H2B H 1.1559 -0.3199 1.0236 0.141 Uiso 0.464(18) 1 calc PR A 1
H5B H 0.685(6) -0.188(3) 0.815(3) 0.177 Uiso 1 1 d D . .
H5A H 0.626(5) -0.111(2) 0.845(4) 0.177 Uiso 1 1 d 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
C10 N2 N3 117.4(2) . .
C7 N1 C4 109.3(2) . .
C7 N1 H1A 125.4 . .
C4 N1 H1A 125.4 . .
C11 N3 N2 118.6(2) . .
C11 N3 H3A 120.7 . .
N2 N3 H3A 120.7 . .
C13 C12 C17 117.5(2) . .
C13 C12 C11 124.6(2) . .
C17 C12 C11 117.9(2) . .
C15 O4 H4A 109.5 . .
N2 C10 C7 119.8(2) . .
N2 C10 H10A 120.1 . .
C7 C10 H10A 120.1 . .
C13 C14 C15 119.6(3) . .
C13 C14 H14A 120.2 . .
C15 C14 H14A 120.2 . .
C15 C16 C17 120.0(3) . .
C15 C16 H16A 120.0 . .
C17 C16 H16A 120.0 . .
O4 C15 C16 118.2(2) . .
O4 C15 C14 121.9(3) . .
C16 C15 C14 119.9(2) . .
H5B O5 H5A 107(3) . .
O3 C11 N3 120.9(2) . .
O3 C11 C12 122.2(2) . .
N3 C11 C12 116.9(2) . .
C14 C13 C12 121.6(2) . .
C14 C13 H13A 119.2 . .
C12 C13 H13A 119.2 . .
N1 C7 C6 108.1(2) . .
N1 C7 C10 122.3(2) . .
C6 C7 C10 129.7(2) . .
N1 C4 C5 108.2(2) . .
N1 C4 C3 122.9(3) . .
C5 C4 C3 128.9(3) . .
C7 C6 C5 107.5(2) . .
C7 C6 C9 126.4(2) . .
C5 C6 C9 126.1(2) . .
C16 C17 C12 121.3(3) . .
C16 C17 H17A 119.3 . .
C12 C17 H17A 119.3 . .
C4 C5 C6 107.0(2) . .
C4 C5 C8 126.4(2) . .
C6 C5 C8 126.6(3) . .
C6 C9 H9A 109.5 . .
C6 C9 H9B 109.5 . .
H9A C9 H9B 109.5 . .
C6 C9 H9C 109.5 . .
H9A C9 H9C 109.5 . .
H9B C9 H9C 109.5 . .
C3 O1 C2A 109.6(4) . .
C3 O1 C2 130.6(9) . .
C2A O1 C2 28.7(4) . .
O2 C3 O1 122.2(3) . .
O2 C3 C4 127.1(3) . .
O1 C3 C4 110.7(3) . .
C5 C8 H8A 109.5 . .
C5 C8 H8B 109.5 . .
H8A C8 H8B 109.5 . .
C5 C8 H8C 109.5 . .
H8A C8 H8C 109.5 . .
H8B C8 H8C 109.5 . .
C2A C1A H1A1 109.5 . .
C2A C1A H1A2 109.5 . .
H1A1 C1A H1A2 109.5 . .
C2A C1A H1A3 109.5 . .
H1A1 C1A H1A3 109.5 . .
H1A2 C1A H1A3 109.5 . .
C1A C2A O1 104.6(7) . .
C1A C2A H2A1 110.8 . .
O1 C2A H2A1 110.8 . .
C1A C2A H2A2 110.8 . .
O1 C2A H2A2 110.8 . .
H2A1 C2A H2A2 108.9 . .
C1 C2 O1 93.7(10) . .
C1 C2 H2A 113.0 . .
O1 C2 H2A 113.0 . .
C1 C2 H2B 113.0 . .
O1 C2 H2B 113.0 . .
H2A C2 H2B 110.4 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N2 C10 1.276(3) .
N2 N3 1.371(3) .
N1 C7 1.355(3) .
N1 C4 1.366(3) .
N1 H1A 0.8600 .
N3 C11 1.354(3) .
N3 H3A 0.8600 .
O3 C11 1.225(3) .
C12 C13 1.389(4) .
C12 C17 1.391(3) .
C12 C11 1.481(3) .
O4 C15 1.371(3) .
O4 H4A 0.8200 .
C10 C7 1.436(3) .
C10 H10A 0.9300 .
C14 C13 1.377(3) .
C14 C15 1.383(4) .
C14 H14A 0.9300 .
C16 C15 1.377(4) .
C16 C17 1.378(4) .
C16 H16A 0.9300 .
O5 H5B 0.853(19) .
O5 H5A 0.859(19) .
C13 H13A 0.9300 .
C7 C6 1.390(3) .
C4 C5 1.387(4) .
C4 C3 1.436(4) .
O2 C3 1.208(3) .
C6 C5 1.397(3) .
C6 C9 1.501(4) .
C17 H17A 0.9300 .
C5 C8 1.493(4) .
C9 H9A 0.9600 .
C9 H9B 0.9600 .
C9 H9C 0.9600 .
O1 C3 1.325(4) .
O1 C2A 1.493(8) .
O1 C2 1.553(13) .
C8 H8A 0.9600 .
C8 H8B 0.9600 .
C8 H8C 0.9600 .
C1 C2 1.480(16) .
C1 H1B 0.9600 .
C1 H1C 0.9600 .
C1 H1D 0.9600 .
C1A C2A 1.438(13) .
C1A H1A1 0.9600 .
C1A H1A2 0.9600 .
C1A H1A3 0.9600 .
C2A H2A1 0.9700 .
C2A H2A2 0.9700 .
C2 H2A 0.9700 .
C2 H2B 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
O4 H4A O5 0.82 1.84 2.665(3) 179.7 2_556
N1 H1A O5 0.86 2.17 3.020(3) 169.9 .
O5 H5A O3 0.859(19) 2.05(3) 2.864(3) 159(5) .
O5 H5B O2 0.853(19) 2.15(2) 2.977(3) 164(5) 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
C10 N2 N3 C11 179.3(2) . . . .
N3 N2 C10 C7 -178.9(2) . . . .
C17 C16 C15 O4 178.2(2) . . . .
C17 C16 C15 C14 -1.0(4) . . . .
C13 C14 C15 O4 -177.9(2) . . . .
C13 C14 C15 C16 1.3(4) . . . .
N2 N3 C11 O3 0.7(4) . . . .
N2 N3 C11 C12 -178.0(2) . . . .
C13 C12 C11 O3 169.2(3) . . . .
C17 C12 C11 O3 -11.7(4) . . . .
C13 C12 C11 N3 -12.1(4) . . . .
C17 C12 C11 N3 167.0(2) . . . .
C15 C14 C13 C12 0.1(4) . . . .
C17 C12 C13 C14 -1.7(4) . . . .
C11 C12 C13 C14 177.4(2) . . . .
C4 N1 C7 C6 0.8(3) . . . .
C4 N1 C7 C10 -179.4(2) . . . .
N2 C10 C7 N1 2.5(4) . . . .
N2 C10 C7 C6 -177.8(2) . . . .
C7 N1 C4 C5 -0.4(3) . . . .
C7 N1 C4 C3 178.3(2) . . . .
N1 C7 C6 C5 -0.9(3) . . . .
C10 C7 C6 C5 179.3(2) . . . .
N1 C7 C6 C9 180.0(3) . . . .
C10 C7 C6 C9 0.2(4) . . . .
C15 C16 C17 C12 -0.7(4) . . . .
C13 C12 C17 C16 2.0(4) . . . .
C11 C12 C17 C16 -177.2(2) . . . .
N1 C4 C5 C6 -0.2(3) . . . .
C3 C4 C5 C6 -178.8(3) . . . .
N1 C4 C5 C8 -179.4(2) . . . .
C3 C4 C5 C8 2.0(5) . . . .
C7 C6 C5 C4 0.7(3) . . . .
C9 C6 C5 C4 179.8(3) . . . .
C7 C6 C5 C8 179.9(2) . . . .
C9 C6 C5 C8 -1.0(4) . . . .
C2A O1 C3 O2 6.7(8) . . . .
C2 O1 C3 O2 -16.2(8) . . . .
C2A O1 C3 C4 -172.6(7) . . . .
C2 O1 C3 C4 164.5(6) . . . .
N1 C4 C3 O2 -174.1(3) . . . .
C5 C4 C3 O2 4.3(5) . . . .
N1 C4 C3 O1 5.2(4) . . . .
C5 C4 C3 O1 -176.4(3) . . . .
C3 O1 C2A C1A 169.9(12) . . . .
C2 O1 C2A C1A -48.2(15) . . . .
C3 O1 C2 C1 102.0(14) . . . .
C2A O1 C2 C1 52.2(13) . . . .
loop_
_publcif_info_datablock.id
_publcif_info_datablock.publ_exptl
_publcif_info_datablock.publ_geom
_publcif_info_datablock.structure
{7a99efa6-2ccb-4b62-b118-11feb1453cfc} ? ? ?
{454db460-f8f9-4834-9c5f-6a17f2ff8385} y y y
loop_
_publcif_info_exptl_table_extra_item
sin_theta_over_lambda_max
loop_
_publcif_info_tables.block_id
_publcif_info_tables.reference_item
{7a99efa6-2ccb-4b62-b118-11feb1453cfc} '_publcif_info_datablock.publ_exptl'
{454db460-f8f9-4834-9c5f-6a17f2ff8385} '_geom_hbond_atom_site_label_D'
