#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/65/2236572.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2236572
loop_
_publ_author_name
'Irrera, Simona'
'Portalone, Gustavo'
_publ_section_title
;
 4-Methoxybenzamidinium chloride monohydrate
;
_journal_coeditor_code           QM2085
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3083
_journal_paper_doi               10.1107/S1600536812041219
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C8 H11 N2 O 1+, Cl 1-, H2 O'
_chemical_formula_moiety         'C8 H11 N2 O 1+, Cl 1-, H2 O'
_chemical_formula_sum            'C8 H13 Cl N2 O2'
_chemical_formula_weight         204.65
_chemical_name_systematic
;
4-Methoxybenzamidinium chloride monohydrate
;
_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                 99.820(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.3029(7)
_cell_length_b                   9.3142(5)
_cell_length_c                   9.9983(6)
_cell_measurement_reflns_used    3182
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      32.1792
_cell_measurement_theta_min      2.8387
_cell_volume                     1037.17(11)
_computing_cell_refinement       'CrysAlis CCD (Oxford Diffraction, 2006)'
_computing_data_collection       'CrysAlis CCD (Oxford Diffraction, 2006)'
_computing_data_reduction        'CrysAlis RED (Oxford Diffraction, 2006)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      298(2)
_diffrn_detector_area_resol_mean 16.0696
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur S CCD'
_diffrn_measurement_method       'ω and φ'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0179
_diffrn_reflns_av_sigmaI/netI    0.0294
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7158
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         30.00
_diffrn_reflns_theta_min         2.85
_exptl_absorpt_coefficient_mu    0.340
_exptl_absorpt_correction_T_max  0.9680
_exptl_absorpt_correction_T_min  0.9048
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis RED; Oxford Diffraction, 2006)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       tablets
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.221
_refine_diff_density_min         -0.148
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.966
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     144
_refine_ls_number_reflns         2989
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.966
_refine_ls_R_factor_all          0.0771
_refine_ls_R_factor_gt           0.0429
_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)+(0.0667P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1029
_refine_ls_wR_factor_ref         0.1134
_reflns_number_gt                1947
_reflns_number_total             2989
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            qm2085.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2236572
_cod_database_fobs_code          2236572
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_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
Cl Cl1 0.59874(3) 0.29686(5) 0.19860(4) 0.06143(17) Uani d . 1 1
O O1 0.02187(9) 0.02872(12) 0.72746(11) 0.0585(3) Uani d . 1 1
N N1 0.37553(14) 0.36637(18) 0.40096(17) 0.0577(4) Uani d . 1 1
H H1A 0.4215(18) 0.391(3) 0.351(2) 0.087(7) Uiso d . 1 1
H H1B 0.3457(16) 0.424(2) 0.4357(19) 0.070(7) Uiso d . 1 1
N N2 0.40806(13) 0.1372(2) 0.34687(16) 0.0609(4) Uani d . 1 1
H H2A 0.4716(18) 0.167(2) 0.300(2) 0.082(6) Uiso d . 1 1
H H2B 0.3898(16) 0.052(3) 0.3475(19) 0.077(7) Uiso d . 1 1
C C1 0.26509(11) 0.18152(15) 0.49586(13) 0.0400(3) Uani d . 1 1
C C2 0.17291(12) 0.26955(17) 0.52024(16) 0.0499(4) Uani d . 1 1
H H2 0.1669 0.3620 0.4847 0.060 Uiso calc R 1 1
C C3 0.08913(12) 0.22277(17) 0.59666(16) 0.0497(4) Uani d . 1 1
H H3 0.0273 0.2832 0.6120 0.060 Uiso calc R 1 1
C C4 0.09816(11) 0.08562(16) 0.64994(14) 0.0425(3) Uani d . 1 1
C C5 0.19078(12) -0.00346(17) 0.62752(15) 0.0489(4) Uani d . 1 1
H H5 0.1974 -0.0953 0.6645 0.059 Uiso calc R 1 1
C C6 0.27322(12) 0.04365(16) 0.55054(14) 0.0460(3) Uani d . 1 1
H H6 0.3348 -0.0171 0.5350 0.055 Uiso calc R 1 1
C C7 0.35238(11) 0.22994(17) 0.41160(14) 0.0460(4) Uani d . 1 1
C C8 -0.07725(14) 0.1140(2) 0.75071(19) 0.0684(5) Uani d . 1 1
H H8A -0.0482(3) 0.2006(11) 0.7969(13) 0.103 Uiso calc R 1 1
H H8B -0.1241(9) 0.0612(8) 0.8055(12) 0.103 Uiso calc R 1 1
H H8C -0.1263(8) 0.1375(12) 0.6654(9) 0.103 Uiso calc R 1 1
O O2W 0.27853(14) 0.61140(16) 0.50438(18) 0.0783(4) Uani d . 1 1
H HWA 0.319(3) 0.631(4) 0.579(3) 0.155(14) Uiso d . 1 1
H HWB 0.3124(17) 0.667(2) 0.452(2) 0.077(6) Uiso d . 1 1
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'
Cl Cl 0.1484 0.1585 '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
C4 O1 C8 117.92(13)
C7 N1 H1A 119.0(17)
C7 N1 H1B 123.3(15)
H1A N1 H1B 118(2)
C7 N2 H2A 120.7(11)
C7 N2 H2B 119.6(14)
H2A N2 H2B 119.7(18)
C2 C1 C6 118.68(12)
C2 C1 C7 121.24(13)
C6 C1 C7 120.07(12)
C1 C2 C3 121.24(14)
C1 C2 H2 119.4
C3 C2 H2 119.4
C4 C3 C2 119.43(13)
C4 C3 H3 120.3
C2 C3 H3 120.3
O1 C4 C3 124.57(12)
O1 C4 C5 115.41(13)
C3 C4 C5 120.02(12)
C6 C5 C4 120.14(14)
C6 C5 H5 119.9
C4 C5 H5 119.9
C5 C6 C1 120.49(12)
C5 C6 H6 119.8
C1 C6 H6 119.8
N2 C7 N1 118.95(15)
N2 C7 C1 120.53(15)
N1 C7 C1 120.52(15)
O1 C8 H8A 109.5
O1 C8 H8B 109.5
H8A C8 H8B 109.5
O1 C8 H8C 109.5
H8A C8 H8C 109.5
H8B C8 H8C 109.5
HWA O2W HWB 100(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C4 1.3613(16)
O1 C8 1.4243(18)
N1 C7 1.305(2)
N1 H1A 0.81(2)
N1 H1B 0.75(2)
N2 C7 1.304(2)
N2 H2A 0.96(2)
N2 H2B 0.82(2)
C1 C2 1.3798(19)
C1 C6 1.3926(19)
C1 C7 1.4731(18)
C2 C3 1.385(2)
C2 H2 0.9300
C3 C4 1.381(2)
C3 H3 0.9300
C4 C5 1.3837(19)
C5 C6 1.3776(19)
C5 H5 0.9300
C6 H6 0.9300
C8 H8A 0.9596
C8 H8B 0.9596
C8 H8C 0.9596
O2W HWA 0.82(3)
O2W HWB 0.87(2)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N1 H1A Cl1 . 0.81(2) 2.85(2) 3.5523(18) 145(2)
N1 H1B O2W . 0.75(2) 2.06(2) 2.805(2) 168(2)
N2 H2A Cl1 . 0.96(2) 2.25(2) 3.1850(16) 164.4(16)
N2 H2B Cl1 2_645 0.82(2) 2.43(2) 3.201(2) 157.5(18)
O2W HWA Cl1 3_666 0.82(3) 2.36(3) 3.1731(18) 170(3)
O2W HWB Cl1 2_655 0.87(2) 2.29(2) 3.1603(17) 174.8(19)
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
C6 C1 C2 C3 -0.4(2)
C7 C1 C2 C3 178.39(14)
C1 C2 C3 C4 0.2(2)
C8 O1 C4 C3 2.8(2)
C8 O1 C4 C5 -178.22(14)
C2 C3 C4 O1 179.33(14)
C2 C3 C4 C5 0.4(2)
O1 C4 C5 C6 -179.90(14)
C3 C4 C5 C6 -0.9(2)
C4 C5 C6 C1 0.7(2)
C2 C1 C6 C5 -0.1(2)
C7 C1 C6 C5 -178.88(14)
C2 C1 C7 N2 -153.81(15)
C6 C1 C7 N2 25.0(2)
C2 C1 C7 N1 26.4(2)
C6 C1 C7 N1 -154.78(15)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30658147
