#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/69/2206911.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_2206911
loop_
_publ_author_name
'Ma, Ying-Ying'
'Yu, Yan'
'Wu, Yong-Fei'
'Xiao, Feng-Ping'
'Jin, Long-Fei'
_publ_section_title
;
 2-(Methoxycarbonyl)anilinium chloride monohydrate
;
_journal_coeditor_code           CI6646
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3497
_journal_page_last               o3499
_journal_paper_doi               10.1107/S1600536805030771
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C8 H10 N O2 +, Cl -, H2 O'
_chemical_formula_moiety         'C8 H10 N O2 +, Cl -, H2 O'
_chemical_formula_sum            'C8 H12 Cl N O3'
_chemical_formula_weight         205.64
_chemical_name_systematic
;
2-(Methoxycarbonyl)anilinium chloride monohydrate
;
_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
_cell_angle_alpha                96.299(2)
_cell_angle_beta                 101.097(2)
_cell_angle_gamma                106.844(2)
_cell_formula_units_Z            4
_cell_length_a                   7.4709(9)
_cell_length_b                   11.6988(14)
_cell_length_c                   12.3883(15)
_cell_measurement_reflns_used    3522
_cell_measurement_temperature    292(2)
_cell_measurement_theta_max      25.67
_cell_measurement_theta_min      2.40
_cell_volume                     1001.0(2)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Bruker, 2001)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      292(2)
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_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  0.0161
_diffrn_reflns_av_sigmaI/netI    0.0313
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5444
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.70
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.357
_exptl_absorpt_correction_T_max  0.9003
_exptl_absorpt_correction_T_min  0.8942
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.334
_refine_diff_density_min         -0.226
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         3867
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0450
_refine_ls_R_factor_gt           0.0406
_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/[σ²(Fo²)+(0.0779P)²+0.2162P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1218
_refine_ls_wR_factor_ref         0.1283
_reflns_number_gt                3433
_reflns_number_total             3867
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ci6646.cif
_cod_data_source_block           I
_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.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

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.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2206911
_cod_database_fobs_code          2206911
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_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_type_symbol
C1 0.2657(3) 0.61200(15) 0.98457(15) 0.0406(4) Uani d . 1 C
C2 0.2930(3) 0.72975(15) 1.03841(15) 0.0383(4) Uani d . 1 C
C3 0.3387(3) 0.75805(18) 1.15351(16) 0.0483(5) Uani d . 1 C
H3 0.3569 0.8364 1.1884 0.058 Uiso calc R 1 H
C4 0.3576(4) 0.6709(2) 1.21686(17) 0.0572(5) Uani d . 1 C
H4 0.3901 0.6909 1.2944 0.069 Uiso calc R 1 H
C5 0.3283(4) 0.5540(2) 1.16565(18) 0.0598(6) Uani d . 1 C
H5 0.3392 0.4948 1.2085 0.072 Uiso calc R 1 H
C6 0.2827(3) 0.52545(18) 1.05041(18) 0.0538(5) Uani d . 1 C
H6 0.2631 0.4465 1.0163 0.065 Uiso calc R 1 H
C7 0.2256(3) 0.58225(16) 0.86061(16) 0.0434(4) Uani d . 1 C
C8 0.1460(5) 0.4297(2) 0.7027(2) 0.0825(9) Uani d . 1 C
H8A 0.0414 0.4547 0.6667 0.124 Uiso calc R 1 H
H8B 0.1136 0.3433 0.6836 0.124 Uiso calc R 1 H
H8C 0.2596 0.4684 0.6784 0.124 Uiso calc R 1 H
C9 0.2314(2) 1.00752(15) 0.61787(14) 0.0343(4) Uani d . 1 C
C10 0.2491(2) 0.89784(15) 0.57108(14) 0.0350(4) Uani d . 1 C
C11 0.2631(3) 0.87781(16) 0.46209(15) 0.0412(4) Uani d . 1 C
H11 0.2732 0.8043 0.4318 0.049 Uiso calc R 1 H
C12 0.2621(3) 0.96682(18) 0.39747(15) 0.0442(4) Uani d . 1 C
H12 0.2693 0.9525 0.3233 0.053 Uiso calc R 1 H
C13 0.2505(3) 1.07669(17) 0.44253(15) 0.0426(4) Uani d . 1 C
H13 0.2539 1.1374 0.3996 0.051 Uiso calc R 1 H
C14 0.2338(3) 1.09663(16) 0.55155(15) 0.0391(4) Uani d . 1 C
H14 0.2241 1.1706 0.5812 0.047 Uiso calc R 1 H
C15 0.1997(2) 1.02604(16) 0.73273(14) 0.0378(4) Uani d . 1 C
C16 0.1489(4) 1.1601(2) 0.87130(18) 0.0608(6) Uani d . 1 C
H16A 0.0366 1.0982 0.8778 0.091 Uiso calc R 1 H
H16B 0.1287 1.2376 0.8814 0.091 Uiso calc R 1 H
H16C 0.2579 1.1611 0.9274 0.091 Uiso calc R 1 H
Cl1 0.37394(7) 0.07755(4) 0.14253(4) 0.04657(16) Uani d . 1 Cl
Cl2 0.18067(8) 0.36339(4) 0.40175(5) 0.05799(18) Uani d . 1 Cl
H5A 0.880(4) 0.720(3) 0.803(3) 0.070(9) Uiso d . 1 H
H6A 0.500(6) 0.641(3) 0.544(3) 0.109(13) Uiso d . 1 H
H5B 0.826(5) 0.797(3) 0.859(2) 0.083(9) Uiso d . 1 H
H6B 0.326(5) 0.572(3) 0.492(3) 0.080(9) Uiso d . 1 H
N1 0.2718(2) 0.82504(13) 0.97525(13) 0.0424(4) Uani d . 1 N
H1A 0.2942 0.8935 1.0224 0.064 Uiso calc R 1 H
H1B 0.1528 0.8030 0.9327 0.064 Uiso calc R 1 H
H1C 0.3557 0.8368 0.9321 0.064 Uiso calc R 1 H
N2 0.2535(2) 0.80099(13) 0.63524(13) 0.0405(3) Uani d . 1 N
H2A 0.1347 0.7618 0.6400 0.061 Uiso calc R 1 H
H2B 0.3276 0.8327 0.7036 0.061 Uiso calc R 1 H
H2C 0.3010 0.7494 0.6013 0.061 Uiso calc R 1 H
O1 0.1814(3) 0.46450(12) 0.82347(12) 0.0658(5) Uani d . 1 O
O2 0.2325(3) 0.65573(12) 0.80063(12) 0.0618(4) Uani d . 1 O
O3 0.1842(2) 1.13512(11) 0.76149(11) 0.0493(3) Uani d . 1 O
O4 0.1858(3) 0.95180(13) 0.79200(12) 0.0587(4) Uani d . 1 O
O5 0.8866(3) 0.74624(16) 0.86478(16) 0.0589(4) Uani d . 1 O
O6 0.3892(3) 0.63930(16) 0.51649(17) 0.0646(5) Uani d . 1 O
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
_geom_angle_publ_flag
C6 C1 C2 118.00(17) ?
C6 C1 C7 121.18(16) ?
C2 C1 C7 120.79(16) ?
C3 C2 C1 120.48(17) ?
C3 C2 N1 118.09(16) ?
C1 C2 N1 121.43(15) ?
C4 C3 C2 120.33(18) ?
C4 C3 H3 119.8 ?
C2 C3 H3 119.8 ?
C3 C4 C5 120.17(19) ?
C3 C4 H4 119.9 ?
C5 C4 H4 119.9 ?
C4 C5 C6 119.63(19) ?
C4 C5 H5 120.2 ?
C6 C5 H5 120.2 ?
C5 C6 C1 121.37(19) ?
C5 C6 H6 119.3 ?
C1 C6 H6 119.3 ?
O2 C7 O1 123.30(17) yes
O2 C7 C1 124.10(16) ?
O1 C7 C1 112.60(16) y
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 ?
C14 C9 C10 118.03(15) ?
C14 C9 C15 120.77(15) ?
C10 C9 C15 121.12(15) ?
C11 C10 C9 120.79(16) ?
C11 C10 N2 117.42(15) ?
C9 C10 N2 121.79(15) ?
C10 C11 C12 120.09(16) ?
C10 C11 H11 120.0 ?
C12 C11 H11 120.0 ?
C13 C12 C11 120.21(16) ?
C13 C12 H12 119.9 ?
C11 C12 H12 119.9 ?
C12 C13 C14 119.89(16) ?
C12 C13 H13 120.1 ?
C14 C13 H13 120.1 ?
C13 C14 C9 120.96(16) ?
C13 C14 H14 119.5 ?
C9 C14 H14 119.5 ?
O4 C15 O3 123.32(16) yes
O4 C15 C9 124.57(16) ?
O3 C15 C9 112.10(15) y
O3 C16 H16A 109.5 ?
O3 C16 H16B 109.5 ?
H16A C16 H16B 109.5 ?
O3 C16 H16C 109.5 ?
H16A C16 H16C 109.5 ?
H16B C16 H16C 109.5 ?
C2 N1 H1A 109.5 ?
C2 N1 H1B 109.5 ?
H1A N1 H1B 109.5 ?
C2 N1 H1C 109.5 ?
H1A N1 H1C 109.5 ?
H1B N1 H1C 109.5 ?
C10 N2 H2A 109.5 ?
C10 N2 H2B 109.5 ?
H2A N2 H2B 109.5 ?
C10 N2 H2C 109.5 ?
H2A N2 H2C 109.5 ?
H2B N2 H2C 109.5 ?
C7 O1 C8 115.31(17) yes
C15 O3 C16 115.88(15) yes
H5A O5 H5B 104(3) ?
H6A O6 H6B 109(3) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C6 1.387(3) ?
C1 C2 1.403(2) ?
C1 C7 1.488(3) yes
C2 C3 1.379(3) ?
C2 N1 1.458(2) yes
C3 C4 1.375(3) ?
C3 H3 0.93 ?
C4 C5 1.380(3) ?
C4 H4 0.93 ?
C5 C6 1.381(3) ?
C5 H5 0.93 ?
C6 H6 0.93 ?
C7 O2 1.193(2) yes
C7 O1 1.326(2) yes
C8 O1 1.457(3) yes
C8 H8A 0.96 ?
C8 H8B 0.96 ?
C8 H8C 0.96 ?
C9 C14 1.395(2) ?
C9 C10 1.402(2) ?
C9 C15 1.490(2) yes
C10 C11 1.374(2) ?
C10 N2 1.458(2) yes
C11 C12 1.382(3) ?
C11 H11 0.93 ?
C12 C13 1.377(3) ?
C12 H12 0.93 ?
C13 C14 1.381(3) ?
C13 H13 0.93 ?
C14 H14 0.93 ?
C15 O4 1.192(2) yes
C15 O3 1.330(2) yes
C16 O3 1.450(2) yes
C16 H16A 0.96 ?
C16 H16B 0.96 ?
C16 H16C 0.96 ?
N1 H1A 0.89 ?
N1 H1B 0.89 ?
N1 H1C 0.89 ?
N2 H2A 0.89 ?
N2 H2B 0.89 ?
N2 H2C 0.89 ?
O5 H5A 0.78(3) ?
O5 H5B 0.84(3) ?
O6 H6A 0.83(4) ?
O6 H6B 0.78(3) ?
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
_geom_hbond_publ_flag
N1 H1A Cl1 1_566 0.89 2.33 3.2163(16) 176 y
N1 H1B O4 . 0.89 2.59 2.915(2) 102 y
N1 H1B O5 1_455 0.89 1.89 2.770(3) 170 y
N1 H1C O2 . 0.89 2.35 2.677(2) 102 y
N1 H1C Cl1 2_666 0.89 2.38 3.2459(17) 163 y
N2 H2A Cl2 2_566 0.89 2.31 3.1700(17) 163 y
N2 H2B O2 . 0.89 2.50 2.801(2) 100 y
N2 H2B O4 . 0.89 2.29 2.699(2) 108 y
N2 H2B Cl1 2_666 0.89 2.51 3.3534(17) 159 y
N2 H2C O6 . 0.89 1.91 2.801(3) 175 y
O5 H5A Cl2 2_666 0.78(4) 2.52(4) 3.295(2) 173(3) y
O5 H5B Cl1 2_666 0.85(4) 2.38(4) 3.216(2) 172(3) y
O6 H6A Cl2 2_666 0.83(5) 2.37(5) 3.188(2) 172(4) y
O6 H6B Cl2 . 0.78(3) 2.41(3) 3.177(2) 169(4) y
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_publ_flag
C6 C1 C2 C3 1.1(3) ?
C7 C1 C2 C3 -177.05(18) ?
C6 C1 C2 N1 -178.11(18) ?
C7 C1 C2 N1 3.7(3) ?
C1 C2 C3 C4 -0.2(3) ?
N1 C2 C3 C4 179.07(19) ?
C2 C3 C4 C5 -0.9(3) ?
C3 C4 C5 C6 0.9(4) ?
C4 C5 C6 C1 0.0(4) ?
C2 C1 C6 C5 -1.0(3) ?
C7 C1 C6 C5 177.1(2) ?
C6 C1 C7 O2 -170.5(2) ?
C2 C1 C7 O2 7.6(3) yes
C6 C1 C7 O1 9.4(3) y
C2 C1 C7 O1 -172.55(18) ?
C14 C9 C10 C11 -1.8(2) ?
C15 C9 C10 C11 174.81(16) ?
C14 C9 C10 N2 178.21(15) ?
C15 C9 C10 N2 -5.2(2) ?
C9 C10 C11 C12 0.8(3) ?
N2 C10 C11 C12 -179.20(16) ?
C10 C11 C12 C13 1.1(3) ?
C11 C12 C13 C14 -2.0(3) ?
C12 C13 C14 C9 1.0(3) ?
C10 C9 C14 C13 0.9(3) ?
C15 C9 C14 C13 -175.69(16) ?
C14 C9 C15 O4 175.95(18) ?
C10 C9 C15 O4 -0.5(3) y
C14 C9 C15 O3 -2.7(2) y
C10 C9 C15 O3 -179.19(15) ?
O2 C7 O1 C8 1.6(3) y
C1 C7 O1 C8 -178.3(2) ?
O4 C15 O3 C16 0.0(3) ?
C9 C15 O3 C16 178.72(17) y
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30654854
