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#$Date: 2025-08-21 02:19:08 +0200 (Thu 21 de Aug de 2025) $
#$Revision: 301842 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/43/4504367.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_4504367
loop_
_publ_author_name
'Solchinger, Alexander'
'Wurst, Klaus'
'Kopacka, Holger'
'Bildstein, Benno'
_publ_section_title
;
 Supramolecular Stabilization of Hemiacetals ofN-Alkyl(Benz)Imidazole
 Aldehydes
;
_journal_issue                   12
_journal_name_full               'Crystal Growth &amp; Design'
_journal_page_first              2380
_journal_paper_doi               10.1021/cg070377h
_journal_volume                  7
_journal_year                    2007
_chemical_formula_sum            'C10 H12 N2 O2'
_chemical_formula_weight         192.22
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 107.008(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.8472(6)
_cell_length_b                   11.6962(9)
_cell_length_c                   9.7839(4)
_cell_measurement_reflns_used    4506
_cell_measurement_temperature    233(2)
_cell_measurement_theta_max      25.0
_cell_measurement_theta_min      1.0
_cell_volume                     968.15(11)
_computing_data_collection       COLLECT
_computing_data_reduction        'DENZO and SCALEPACK'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      233(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'phi- and omega-scan'
_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  0.0355
_diffrn_reflns_av_sigmaI/netI    0.0392
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4445
_diffrn_reflns_theta_full        24.00
_diffrn_reflns_theta_max         24.00
_diffrn_reflns_theta_min         2.41
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.248
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       0.014(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    'constr.; refined at O1 with bond restraint'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     133
_refine_ls_number_reflns         1517
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0572
_refine_ls_R_factor_gt           0.0393
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0486P)^2^+0.1684P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0917
_refine_ls_wR_factor_ref         0.0981
_reflns_number_gt                1187
_reflns_number_total             1517
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg070377h-file003.cif
_cod_data_source_block           3a
_cod_original_cell_volume        968.14(11)
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               4504367
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
O1 O 0.19270(16) 0.12970(12) 0.22051(12) 0.0406(4) Uani 1 1 d D
H1O H 0.128(3) 0.068(2) 0.225(3) 0.103(10) Uiso 1 1 d D
O2 O 0.31796(14) 0.08828(11) 0.04736(13) 0.0385(4) Uani 1 1 d .
N1 N 0.08842(17) 0.33870(12) 0.07812(14) 0.0305(4) Uani 1 1 d .
N2 N -0.04168(18) 0.44714(13) 0.19514(14) 0.0358(4) Uani 1 1 d .
C1 C -0.0672(2) 0.34245(14) -0.00723(17) 0.0293(4) Uani 1 1 d .
C2 C -0.1418(2) 0.29562(16) -0.14087(18) 0.0385(5) Uani 1 1 d .
H2 H -0.0863 0.2515 -0.1907 0.046 Uiso 1 1 calc .
C3 C -0.3007(2) 0.31736(17) -0.19605(19) 0.0442(5) Uani 1 1 d .
H3 H -0.3555 0.2877 -0.2862 0.053 Uiso 1 1 calc .
C4 C -0.3826(2) 0.38227(19) -0.1216(2) 0.0489(6) Uani 1 1 d .
H4 H -0.4917 0.3942 -0.1620 0.059 Uiso 1 1 calc .
C5 C -0.3078(2) 0.42936(18) 0.0096(2) 0.0438(5) Uani 1 1 d .
H5 H -0.3637 0.4737 0.0587 0.053 Uiso 1 1 calc .
C6 C -0.1466(2) 0.40928(15) 0.06742(18) 0.0317(4) Uani 1 1 d .
C7 C 0.0941(2) 0.40243(15) 0.19539(17) 0.0325(5) Uani 1 1 d .
H7 H 0.1876 0.4136 0.2704 0.039 Uiso 1 1 calc .
C8 C 0.2141(2) 0.26984(16) 0.05379(17) 0.0337(5) Uani 1 1 d .
H8A H 0.3157 0.2953 0.1179 0.040 Uiso 1 1 calc .
H8B H 0.2169 0.2808 -0.0448 0.040 Uiso 1 1 calc .
C9 C 0.1914(2) 0.14407(15) 0.07916(17) 0.0303(4) Uani 1 1 d .
H9 H 0.0896 0.1171 0.0141 0.036 Uiso 1 1 calc .
C10 C 0.3104(3) -0.03302(17) 0.0560(2) 0.0525(6) Uani 1 1 d .
H10A H 0.3996 -0.0666 0.0319 0.079 Uiso 1 1 calc R
H10B H 0.2128 -0.0601 -0.0105 0.079 Uiso 1 1 calc R
H10C H 0.3138 -0.0550 0.1524 0.079 Uiso 1 1 calc R
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0517(9) 0.0412(9) 0.0301(7) 0.0024(6) 0.0139(6) -0.0041(7)
O2 0.0383(8) 0.0359(8) 0.0442(8) 0.0035(6) 0.0163(6) 0.0078(6)
N1 0.0326(9) 0.0312(9) 0.0277(8) 0.0028(6) 0.0085(6) 0.0017(7)
N2 0.0418(10) 0.0358(9) 0.0303(8) -0.0012(7) 0.0114(7) 0.0014(8)
C1 0.0324(10) 0.0278(10) 0.0273(9) 0.0048(7) 0.0079(8) 0.0026(8)
C2 0.0448(12) 0.0355(12) 0.0351(10) -0.0049(8) 0.0114(9) 0.0038(9)
C3 0.0432(12) 0.0443(12) 0.0372(11) -0.0069(9) -0.0006(9) 0.0012(10)
C4 0.0345(12) 0.0539(14) 0.0514(13) -0.0023(10) 0.0016(9) 0.0064(10)
C5 0.0410(12) 0.0460(13) 0.0453(11) -0.0042(9) 0.0142(9) 0.0099(10)
C6 0.0365(11) 0.0287(10) 0.0295(9) 0.0013(7) 0.0092(8) 0.0016(8)
C7 0.0391(11) 0.0314(11) 0.0253(9) 0.0012(7) 0.0069(8) -0.0038(9)
C8 0.0321(11) 0.0373(11) 0.0327(10) 0.0053(8) 0.0111(8) 0.0042(8)
C9 0.0280(10) 0.0364(11) 0.0265(9) 0.0010(7) 0.0081(7) 0.0024(8)
C10 0.0646(15) 0.0372(13) 0.0591(13) 0.0014(10) 0.0236(11) 0.0104(11)
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
H1O O1 C9 108.2(18)
C9 O2 C10 113.25(14)
C7 N1 C1 106.07(14)
C7 N1 C8 127.17(14)
C1 N1 C8 126.41(14)
C7 N2 C6 104.18(14)
N1 C1 C6 105.46(14)
N1 C1 C2 131.86(16)
C6 C1 C2 122.67(16)
C3 C2 C1 116.44(17)
C2 C3 C4 121.62(17)
C5 C4 C3 121.62(18)
C4 C5 C6 117.89(18)
C5 C6 C1 119.74(16)
C5 C6 N2 130.21(17)
C1 C6 N2 110.05(15)
N2 C7 N1 114.24(15)
N1 C8 C9 111.59(14)
O1 C9 O2 112.85(13)
O1 C9 C8 108.52(14)
O2 C9 C8 105.16(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 H1O 0.93(2)
O1 C9 1.390(2)
O2 C9 1.407(2)
O2 C10 1.424(2)
N1 C7 1.357(2)
N1 C1 1.386(2)
N1 C8 1.448(2)
N2 C7 1.310(2)
N2 C6 1.393(2)
C1 C6 1.392(3)
C1 C2 1.393(2)
C2 C3 1.375(3)
C3 C4 1.393(3)
C4 C5 1.376(3)
C5 C6 1.391(3)
C8 C9 1.515(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 97112459
