#------------------------------------------------------------------------------
#$Date: 2018-09-26 06:29:44 +0300 (Wed, 26 Sep 2018) $
#$Revision: 211175 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/25/8102542.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_8102542
loop_
_publ_author_name
'Yuan Wang'
'Wei-Na Wu'
'Rui-Qi Zhao'
'Qiu-Fen Wang'
'Bao-Feng Qin'
_publ_section_title
;
 Crystal structure of ethyl
 5-[(3,4-dimethyl-1H-pyrrole-2-carboxylimino)methyl]-3,4-dimethyl-1H-pyrrole-2-carboxylate
 monohydrate, C17H22N4O3 · H2O
;
_journal_issue                   4
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              625
_journal_volume                  224
_journal_year                    2009
_chemical_formula_sum            'C17 H24 N4 O4'
_chemical_formula_weight         348.40
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2009-08-31 # Formatted by publCIF
;
_cell_angle_alpha                109.3370(10)
_cell_angle_beta                 95.6690(10)
_cell_angle_gamma                105.2850(10)
_cell_formula_units_Z            2
_cell_length_a                   6.4444(6)
_cell_length_b                   12.1465(11)
_cell_length_c                   12.6768(11)
_cell_measurement_reflns_used    4404
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      0.00
_cell_measurement_theta_min      0.00
_cell_volume                     884.13(14)
_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 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_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  0.0172
_diffrn_reflns_av_sigmaI/netI    0.0177
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8785
_diffrn_reflns_theta_full        25.22
_diffrn_reflns_theta_max         25.22
_diffrn_reflns_theta_min         2.03
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_correction_T_min  0.974
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             372
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.239
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       0.023(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         3187
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0464
_refine_ls_R_factor_gt           0.0399
_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)+(0.0652P)²+0.1897P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1119
_refine_ls_wR_factor_ref         0.1185
_reflns_number_gt                2715
_reflns_number_total             3187
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            1267-2754.cff
_cod_data_source_block           z
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'Multi-scan' changed
to 'multi-scan' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1555 2011-01-17 13:19:09Z saulius 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               8102542
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
N1 N 0.24778(19) 0.27862(11) 0.35253(11) 0.0435(3) Uani 1 1 d . . .
H1 H 0.1664 0.2212 0.3697 0.052 Uiso 1 1 calc R . .
N2 N 0.4901(2) 0.22825(11) 0.51833(11) 0.0448(3) Uani 1 1 d . . .
N3 N 0.6192(2) 0.19475(12) 0.58676(11) 0.0464(3) Uani 1 1 d . . .
H3 H 0.7601 0.2199 0.5965 0.056 Uiso 1 1 calc R . .
C11 C 0.5169(2) 0.12032(13) 0.63869(13) 0.0425(3) Uani 1 1 d . . .
N4 N 0.5646(2) -0.00447(12) 0.74767(12) 0.0497(3) Uani 1 1 d . . .
H4 H 0.4294 -0.0501 0.7257 0.060 Uiso 1 1 calc R . .
C7 C 0.4658(2) 0.33555(13) 0.39537(12) 0.0412(3) Uani 1 1 d . . .
C12 C 0.6570(2) 0.09081(13) 0.71473(13) 0.0422(3) Uani 1 1 d . . .
C6 C 0.5384(2) 0.42384(13) 0.34869(13) 0.0419(3) Uani 1 1 d . . .
C13 C 0.8757(2) 0.14248(14) 0.77121(13) 0.0434(4) Uani 1 1 d . . .
C5 C 0.3561(2) 0.41877(13) 0.27425(13) 0.0420(3) Uani 1 1 d . . .
C4 C 0.1774(2) 0.32653(13) 0.27784(12) 0.0414(3) Uani 1 1 d . . .
C14 C 0.9127(3) 0.07313(15) 0.83676(14) 0.0493(4) Uani 1 1 d . . .
C10 C 0.5895(2) 0.30065(14) 0.47300(13) 0.0450(4) Uani 1 1 d . . .
H10 H 0.7421 0.3311 0.4900 0.054 Uiso 1 1 calc R . .
C15 C 0.7183(3) -0.01563(15) 0.81987(14) 0.0539(4) Uani 1 1 d . . .
H15 H 0.6956 -0.0745 0.8530 0.065 Uiso 1 1 calc R . .
C16 C 1.0437(3) 0.25508(15) 0.77266(15) 0.0548(4) Uani 1 1 d . . .
H16A H 1.1295 0.2317 0.7164 0.082 Uiso 1 1 calc R . .
H16B H 1.1383 0.2971 0.8469 0.082 Uiso 1 1 calc R . .
H16C H 0.9711 0.3086 0.7557 0.082 Uiso 1 1 calc R . .
C9 C 0.7669(3) 0.51042(15) 0.37489(16) 0.0543(4) Uani 1 1 d . . .
H9A H 0.8609 0.4925 0.4261 0.081 Uiso 1 1 calc R . .
H9B H 0.7659 0.5934 0.4099 0.081 Uiso 1 1 calc R . .
H9C H 0.8204 0.5008 0.3054 0.081 Uiso 1 1 calc R . .
C8 C 0.3578(3) 0.49908(16) 0.20661(16) 0.0576(4) Uani 1 1 d . . .
H8A H 0.3286 0.4500 0.1266 0.086 Uiso 1 1 calc R . .
H8B H 0.4991 0.5607 0.2276 0.086 Uiso 1 1 calc R . .
H8C H 0.2466 0.5381 0.2221 0.086 Uiso 1 1 calc R . .
C17 C 1.1269(3) 0.0956(2) 0.91189(17) 0.0696(5) Uani 1 1 d . . .
H17A H 1.1541 0.1674 0.9796 0.104 Uiso 1 1 calc R . .
H17B H 1.2438 0.1080 0.8714 0.104 Uiso 1 1 calc R . .
H17C H 1.1198 0.0258 0.9328 0.104 Uiso 1 1 calc R . .
O1 O -0.08714(17) 0.32076(11) 0.13762(10) 0.0548(3) Uani 1 1 d . . .
O2 O -0.18837(19) 0.19564(11) 0.23241(12) 0.0639(4) Uani 1 1 d . . .
C3 C -0.0496(2) 0.27340(14) 0.21614(13) 0.0452(4) Uani 1 1 d . . .
C2 C -0.3067(3) 0.27497(17) 0.06878(15) 0.0577(4) Uani 1 1 d . . .
H2A H -0.4140 0.2819 0.1171 0.069 Uiso 1 1 calc R . .
H2B H -0.3409 0.1893 0.0199 0.069 Uiso 1 1 calc R . .
O3 O 0.31492(17) 0.08238(11) 0.62298(11) 0.0579(3) Uani 1 1 d . . .
C1 C -0.3098(3) 0.3524(2) -0.00158(17) 0.0727(6) Uani 1 1 d . . .
H1A H -0.2796 0.4365 0.0479 0.109 Uiso 1 1 calc R . .
H1B H -0.4518 0.3237 -0.0506 0.109 Uiso 1 1 calc R . .
H1C H -0.1998 0.3465 -0.0472 0.109 Uiso 1 1 calc R . .
O1W O 0.00234(18) -0.14613(11) 0.52306(11) 0.0571(3) Uani 1 1 d D . .
H1WA H 0.093(3) -0.0682(11) 0.5600(16) 0.086 Uiso 1 1 d D . .
H1WB H -0.123(2) -0.1384(17) 0.4933(17) 0.086 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
_geom_angle_publ_flag
C7 N1 C4 109.41(12) . . ?
C7 N1 H1 125.3 . . ?
C4 N1 H1 125.3 . . ?
C10 N2 N3 116.70(13) . . ?
C11 N3 N2 117.73(12) . . ?
C11 N3 H3 121.1 . . ?
N2 N3 H3 121.1 . . ?
O3 C11 N3 121.11(14) . . ?
O3 C11 C12 122.15(14) . . ?
N3 C11 C12 116.73(13) . . ?
C15 N4 C12 109.43(14) . . ?
C15 N4 H4 125.3 . . ?
C12 N4 H4 125.3 . . ?
N1 C7 C6 108.40(13) . . ?
N1 C7 C10 122.28(13) . . ?
C6 C7 C10 129.28(14) . . ?
N4 C12 C13 107.32(13) . . ?
N4 C12 C11 118.21(13) . . ?
C13 C12 C11 134.38(14) . . ?
C7 C6 C5 107.30(13) . . ?
C7 C6 C9 126.36(14) . . ?
C5 C6 C9 126.33(14) . . ?
C12 C13 C14 106.94(14) . . ?
C12 C13 C16 128.79(14) . . ?
C14 C13 C16 124.13(14) . . ?
C4 C5 C6 106.64(13) . . ?
C4 C5 C8 127.66(14) . . ?
C6 C5 C8 125.70(14) . . ?
N1 C4 C5 108.25(12) . . ?
N1 C4 C3 118.72(13) . . ?
C5 C4 C3 132.95(14) . . ?
C15 C14 C13 107.11(14) . . ?
C15 C14 C17 127.21(16) . . ?
C13 C14 C17 125.68(16) . . ?
N2 C10 C7 120.22(13) . . ?
N2 C10 H10 119.9 . . ?
C7 C10 H10 119.9 . . ?
N4 C15 C14 109.18(14) . . ?
N4 C15 H15 125.4 . . ?
C14 C15 H15 125.4 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
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 . . ?
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 . . ?
C14 C17 H17A 109.5 . . ?
C14 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C14 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C3 O1 C2 117.52(13) . . ?
O2 C3 O1 123.54(14) . . ?
O2 C3 C4 124.82(14) . . ?
O1 C3 C4 111.64(13) . . ?
O1 C2 C1 106.42(15) . . ?
O1 C2 H2A 110.4 . . ?
C1 C2 H2A 110.4 . . ?
O1 C2 H2B 110.4 . . ?
C1 C2 H2B 110.4 . . ?
H2A C2 H2B 108.6 . . ?
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 . . ?
H1WA O1W H1WB 104.9(12) . . ?
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
N1 C7 1.3551(18) . ?
N1 C4 1.3638(18) . ?
N1 H1 0.8600 . ?
N2 C10 1.2744(19) . ?
N2 N3 1.3714(17) . ?
N3 C11 1.3606(19) . ?
N3 H3 0.8600 . ?
C11 O3 1.2320(17) . ?
C11 C12 1.449(2) . ?
N4 C15 1.346(2) . ?
N4 C12 1.3689(19) . ?
N4 H4 0.8600 . ?
C7 C6 1.389(2) . ?
C7 C10 1.443(2) . ?
C12 C13 1.389(2) . ?
C6 C5 1.407(2) . ?
C6 C9 1.497(2) . ?
C13 C14 1.410(2) . ?
C13 C16 1.497(2) . ?
C5 C4 1.395(2) . ?
C5 C8 1.496(2) . ?
C4 C3 1.453(2) . ?
C14 C15 1.364(2) . ?
C14 C17 1.502(2) . ?
C10 H10 0.9300 . ?
C15 H15 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
O1 C3 1.3362(18) . ?
O1 C2 1.4466(19) . ?
O2 C3 1.2060(19) . ?
C2 C1 1.497(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
O1W H1WA 0.904(9) . ?
O1W H1WB 0.897(9) . ?
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 O1W 0.86 2.11 2.9139(17) 155.5 2_556
O1W H1WA O3 0.904(9) 1.860(9) 2.7542(17) 170.0(19) .
O1W H1WB O3 0.897(9) 2.217(13) 3.0403(16) 152.3(19) 2_556
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
C10 N2 N3 C11 178.16(13) . . . . ?
N2 N3 C11 O3 1.4(2) . . . . ?
N2 N3 C11 C12 -177.22(13) . . . . ?
C4 N1 C7 C6 0.88(17) . . . . ?
C4 N1 C7 C10 -177.13(13) . . . . ?
C15 N4 C12 C13 -1.48(18) . . . . ?
C15 N4 C12 C11 -178.49(13) . . . . ?
O3 C11 C12 N4 16.1(2) . . . . ?
N3 C11 C12 N4 -165.28(13) . . . . ?
O3 C11 C12 C13 -159.88(17) . . . . ?
N3 C11 C12 C13 18.7(3) . . . . ?
N1 C7 C6 C5 -0.41(17) . . . . ?
C10 C7 C6 C5 177.42(15) . . . . ?
N1 C7 C6 C9 178.24(15) . . . . ?
C10 C7 C6 C9 -3.9(3) . . . . ?
N4 C12 C13 C14 1.46(17) . . . . ?
C11 C12 C13 C14 177.76(16) . . . . ?
N4 C12 C13 C16 -174.45(15) . . . . ?
C11 C12 C13 C16 1.9(3) . . . . ?
C7 C6 C5 C4 -0.19(16) . . . . ?
C9 C6 C5 C4 -178.84(15) . . . . ?
C7 C6 C5 C8 179.07(14) . . . . ?
C9 C6 C5 C8 0.4(2) . . . . ?
C7 N1 C4 C5 -1.00(16) . . . . ?
C7 N1 C4 C3 176.22(13) . . . . ?
C6 C5 C4 N1 0.72(16) . . . . ?
C8 C5 C4 N1 -178.52(15) . . . . ?
C6 C5 C4 C3 -175.94(16) . . . . ?
C8 C5 C4 C3 4.8(3) . . . . ?
C12 C13 C14 C15 -0.92(18) . . . . ?
C16 C13 C14 C15 175.23(16) . . . . ?
C12 C13 C14 C17 179.88(16) . . . . ?
C16 C13 C14 C17 -4.0(3) . . . . ?
N3 N2 C10 C7 176.92(13) . . . . ?
N1 C7 C10 N2 -11.5(2) . . . . ?
C6 C7 C10 N2 170.97(15) . . . . ?
C12 N4 C15 C14 0.91(19) . . . . ?
C13 C14 C15 N4 0.02(19) . . . . ?
C17 C14 C15 N4 179.21(17) . . . . ?
C2 O1 C3 O2 -0.3(2) . . . . ?
C2 O1 C3 C4 179.35(13) . . . . ?
N1 C4 C3 O2 6.4(2) . . . . ?
C5 C4 C3 O2 -177.18(16) . . . . ?
N1 C4 C3 O1 -173.17(12) . . . . ?
C5 C4 C3 O1 3.2(2) . . . . ?
C3 O1 C2 C1 173.76(14) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30653971
