#------------------------------------------------------------------------------
#$Date: 2016-03-24 01:57:54 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179548 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/17/4501723.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_4501723
loop_
_publ_author_name
'Martí-Rujas, Javier'
'Morte-Ródenas, Anabel'
'Guo, Fang'
'Thomas, Nigel'
'Fujii, Kotaro'
'Kariuki, Benson M.'
'Harris, Kenneth D. M.'
_publ_section_title
;
 A Solid-State Dehydration Process in an Organic Material Associated with
 Substantial Hydrogen-Bond Reorganization, Investigated by Powder X-ray
 Diffraction
;
_journal_issue                   7
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              3176
_journal_paper_doi               10.1021/cg100330c
_journal_volume                  10
_journal_year                    2010
_chemical_formula_moiety         'C4 H12 N, C2 H3 O2, H2 O'
_chemical_formula_sum            'C6 H17 N O3'
_chemical_formula_weight         151.21
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 98.572(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   7.6306(3)
_cell_length_b                   18.0943(7)
_cell_length_c                   14.2363(6)
_cell_measurement_reflns_used    2178
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.59
_cell_measurement_theta_min      4.33
_cell_volume                     1943.65(14)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       CCD
_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  0.0842
_diffrn_reflns_av_sigmaI/netI    0.0894
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            11381
_diffrn_reflns_theta_full        27.59
_diffrn_reflns_theta_max         27.59
_diffrn_reflns_theta_min         4.33
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  0.9699
_exptl_absorpt_correction_T_min  0.9683
_exptl_crystal_density_diffrn    1.033
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.38
_refine_diff_density_max         0.161
_refine_diff_density_min         -0.137
_refine_diff_density_rms         0.031
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         4417
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.1474
_refine_ls_R_factor_gt           0.0712
_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)+(0.0774P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1570
_refine_ls_wR_factor_ref         0.1872
_reflns_number_gt                2178
_reflns_number_total             4417
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg100330c_si_002.cif
_cod_data_source_block           kdm0726
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        1943.65(13)
_cod_original_sg_symbol_H-M      P21/n
_cod_database_code               4501723
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
C1 C -0.2487(3) -0.10238(13) 0.60396(17) 0.0611(6) Uani 1 1 d .
C2 C -0.1848(4) -0.06989(17) 0.5173(2) 0.0916(9) Uani 1 1 d .
H2A H -0.0690 -0.0888 0.5123 0.137 Uiso 1 1 calc R
H2B H -0.1793 -0.0170 0.5230 0.137 Uiso 1 1 calc R
H2C H -0.2654 -0.0831 0.4615 0.137 Uiso 1 1 calc R
C3 C -0.2722(4) -0.18497(14) 0.5941(2) 0.0784(7) Uani 1 1 d .
H3A H -0.3247 -0.2036 0.6465 0.118 Uiso 1 1 calc R
H3B H -0.1588 -0.2079 0.5937 0.118 Uiso 1 1 calc R
H3C H -0.3481 -0.1959 0.5357 0.118 Uiso 1 1 calc R
C4 C -0.1283(4) -0.08339(19) 0.6951(2) 0.0974(10) Uani 1 1 d .
H4A H -0.1775 -0.1028 0.7482 0.146 Uiso 1 1 calc R
H4B H -0.1176 -0.0307 0.7009 0.146 Uiso 1 1 calc R
H4C H -0.0133 -0.1046 0.6939 0.146 Uiso 1 1 calc R
C5 C 0.1664(3) 0.09564(12) 0.89131(17) 0.0610(6) Uani 1 1 d .
C6 C 0.1750(4) 0.01333(15) 0.9094(2) 0.0787(7) Uani 1 1 d .
H6A H 0.2141 0.0044 0.9757 0.118 Uiso 1 1 calc R
H6B H 0.2568 -0.0088 0.8726 0.118 Uiso 1 1 calc R
H6C H 0.0595 -0.0079 0.8914 0.118 Uiso 1 1 calc R
C7 C 0.1266(4) 0.11307(18) 0.7866(2) 0.0992(10) Uani 1 1 d .
H7A H 0.0107 0.0950 0.7616 0.149 Uiso 1 1 calc R
H7B H 0.2132 0.0897 0.7540 0.149 Uiso 1 1 calc R
H7C H 0.1308 0.1656 0.7775 0.149 Uiso 1 1 calc R
C8 C 0.0375(4) 0.13280(16) 0.9475(3) 0.0923(9) Uani 1 1 d .
H8A H -0.0802 0.1150 0.9260 0.138 Uiso 1 1 calc R
H8B H 0.0412 0.1853 0.9383 0.138 Uiso 1 1 calc R
H8C H 0.0698 0.1216 1.0137 0.138 Uiso 1 1 calc R
C9 C 0.6562(3) 0.13276(13) 0.61649(17) 0.0634(6) Uani 1 1 d .
C10 C 0.6853(5) 0.20447(15) 0.6693(2) 0.0984(10) Uani 1 1 d .
H10A H 0.7504 0.1956 0.7313 0.148 Uiso 1 1 calc R
H10B H 0.5728 0.2263 0.6753 0.148 Uiso 1 1 calc R
H10C H 0.7512 0.2375 0.6350 0.148 Uiso 1 1 calc R
C11 C 0.5575(3) 0.14342(13) 0.16763(16) 0.0593(6) Uani 1 1 d .
C12 C 0.6629(5) 0.19599(18) 0.1163(2) 0.0937(9) Uani 1 1 d .
H12A H 0.5840 0.2301 0.0796 0.141 Uiso 1 1 calc R
H12B H 0.7273 0.1687 0.0748 0.141 Uiso 1 1 calc R
H12C H 0.7447 0.2228 0.1616 0.141 Uiso 1 1 calc R
N1 N -0.4273(2) -0.06945(10) 0.61057(12) 0.0568(5) Uani 1 1 d .
H1A H -0.5013 -0.0795 0.5577 0.085 Uiso 1 1 calc R
H1B H -0.4168 -0.0207 0.6177 0.085 Uiso 1 1 calc R
H1C H -0.4695 -0.0887 0.6602 0.085 Uiso 1 1 calc R
N2 N 0.3469(2) 0.12713(10) 0.92694(12) 0.0549(5) Uani 1 1 d .
H2D H 0.3466 0.1755 0.9157 0.082 Uiso 1 1 calc R
H2E H 0.4274 0.1054 0.8970 0.082 Uiso 1 1 calc R
H2F H 0.3734 0.1191 0.9891 0.082 Uiso 1 1 calc R
O1 O 0.6824(3) 0.12935(11) 0.53250(12) 0.0847(6) Uani 1 1 d .
O2 O 0.6042(3) 0.07893(10) 0.65902(12) 0.0893(6) Uani 1 1 d .
O3 O 0.4403(2) 0.10477(9) 0.12053(11) 0.0666(5) Uani 1 1 d .
O4 O 0.5959(2) 0.14105(11) 0.25577(11) 0.0834(6) Uani 1 1 d .
O5 O 0.8079(2) 0.21773(9) 0.39915(13) 0.0711(5) Uani 1 1 d D
H1 H 0.748(3) 0.1967(14) 0.3502(12) 0.085 Uiso 1 1 d D
H2 H 0.769(3) 0.1976(14) 0.4469(13) 0.085 Uiso 1 1 d D
O6 O 0.6062(3) 0.04819(10) 0.84632(12) 0.0735(5) Uani 1 1 d D
H3 H 0.608(4) 0.0587(15) 0.7872(8) 0.088 Uiso 1 1 d D
H4 H 0.597(4) 0.0010(5) 0.8511(19) 0.088 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
N1 C1 C3 107.58(19)
N1 C1 C2 107.6(2)
C3 C1 C2 110.9(2)
N1 C1 C4 107.26(19)
C3 C1 C4 110.7(2)
C2 C1 C4 112.5(2)
N2 C5 C7 107.00(19)
N2 C5 C6 107.5(2)
C7 C5 C6 111.8(2)
N2 C5 C8 106.70(19)
C7 C5 C8 112.2(2)
C6 C5 C8 111.3(2)
O2 C9 O1 122.6(2)
O2 C9 C10 117.9(2)
O1 C9 C10 119.5(2)
O4 C11 O3 124.3(2)
O4 C11 C12 116.7(2)
O3 C11 C12 119.0(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N1 1.503(3)
C1 C3 1.509(3)
C1 C2 1.512(4)
C1 C4 1.513(4)
C5 N2 1.507(3)
C5 C7 1.510(4)
C5 C6 1.511(4)
C5 C8 1.514(4)
C9 O2 1.243(3)
C9 O1 1.243(3)
C9 C10 1.499(4)
C11 O4 1.246(3)
C11 O3 1.249(3)
C11 C12 1.504(4)
