#------------------------------------------------------------------------------
#$Date: 2016-03-26 20:17:49 +0100 (Sat 26 de Mar de 2016) $
#$Revision: 180472 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/41/7214128.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_7214128
loop_
_publ_author_name
'Qi, Feng'
'Stein, Robin S.'
'Friščić, Tomislav'
_publ_section_title
;
 Mimicking mineral neogenesis for the clean synthesis of metal--organic
 materials from mineral feedstocks: coordination polymers, MOFs and metal
 oxide separation
;
_journal_issue                   1
_journal_name_full               'Green Chemistry'
_journal_page_first              121
_journal_paper_doi               10.1039/c3gc41370e
_journal_volume                  16
_journal_year                    2014
_chemical_formula_sum            'C8 H20 N2 O4'
_chemical_formula_weight         208.26
_chemical_name_common            (pa)2(ox)
_chemical_name_systematic
;
1-propylammonium oxalate
;
_space_group_IT_number           33
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.0906(3)
_cell_length_b                   14.6981(5)
_cell_length_c                   7.6029(8)
_cell_measurement_reflns_used    4563
_cell_measurement_temperature    250(2)
_cell_measurement_theta_max      26.02
_cell_measurement_theta_min      1.00
_cell_volume                     1239.35(14)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      250(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_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  0.0352
_diffrn_reflns_av_sigmaI/netI    0.0329
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            6064
_diffrn_reflns_theta_full        26.04
_diffrn_reflns_theta_max         26.04
_diffrn_reflns_theta_min         3.53
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.995
_exptl_absorpt_correction_T_min  0.898
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;

multi-scan from symmetry-related measurements

Sortav (Blessing 1995)

;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.116
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.370
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -2(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     130
_refine_ls_number_reflns         1310
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.1177
_refine_ls_R_factor_gt           0.0807
_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)+(0.1302P)²+0.8975P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2215
_refine_ls_wR_factor_ref         0.2622
_reflns_number_gt                856
_reflns_number_total             1310
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3gc41370e.txt
_cod_data_source_block           wj1045
_cod_original_sg_symbol_H-M      Pna21
_cod_database_code               7214128
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, 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
N1 N 0.0775(3) 0.9618(3) 0.7275(11) 0.0580(12) Uani 1 1 d .
H1N H 0.1013 0.9872 0.8294 0.070 Uiso 1 1 calc R
H2N H -0.0014 0.9731 0.7105 0.070 Uiso 1 1 calc R
H3N H 0.1203 0.9858 0.6381 0.070 Uiso 1 1 calc R
C1 C 0.2554(10) 0.7491(8) 0.719(3) 0.182(7) Uani 1 1 d .
H1C H 0.3421 0.7401 0.7165 0.273 Uiso 1 1 calc R
H1D H 0.2212 0.7297 0.6072 0.273 Uiso 1 1 calc R
H1E H 0.2206 0.7135 0.8132 0.273 Uiso 1 1 calc R
C2 C 0.2301(7) 0.8411(6) 0.745(2) 0.121(4) Uani 1 1 d .
H2A H 0.2740 0.8769 0.6576 0.146 Uiso 1 1 calc R
H2B H 0.2603 0.8588 0.8616 0.146 Uiso 1 1 calc R
C3 C 0.0971(5) 0.8652(5) 0.7344(19) 0.0885(18) Uani 1 1 d .
H3A H 0.0624 0.8370 0.6291 0.106 Uiso 1 1 calc R
H3B H 0.0553 0.8402 0.8371 0.106 Uiso 1 1 calc R
C5 C 0.4645(11) 0.6985(5) 0.242(3) 0.180(6) Uani 1 1 d .
H5A H 0.4319 0.6613 0.3357 0.271 Uiso 1 1 calc R
H5B H 0.5441 0.6765 0.2102 0.271 Uiso 1 1 calc R
H5C H 0.4119 0.6949 0.1399 0.271 Uiso 1 1 calc R
C6 C 0.4735(10) 0.8003(8) 0.3049(16) 0.126(3) Uani 1 1 d .
H6A H 0.3939 0.8284 0.2925 0.151 Uiso 1 1 calc R
H6B H 0.4938 0.8004 0.4304 0.151 Uiso 1 1 calc R
C7 C 0.5497(8) 0.8493(6) 0.225(3) 0.165(6) Uani 1 1 d .
H7A H 0.5414 0.8333 0.1003 0.198 Uiso 1 1 calc R
H7B H 0.6288 0.8265 0.2614 0.198 Uiso 1 1 calc R
C8 C 0.7516(5) 0.9821(5) -0.3707(9) 0.049(2) Uani 1 1 d .
C9 C 0.7515(6) 0.9810(6) -0.1662(8) 0.053(2) Uani 1 1 d .
O10 O 0.6517(6) 0.9918(5) -0.0936(5) 0.082(2) Uani 1 1 d .
O11 O 0.6541(6) 0.9886(5) -0.4429(5) 0.083(2) Uani 1 1 d .
N12 N 0.5601(3) 0.9481(3) 0.2284(11) 0.0549(10) Uani 1 1 d .
H4N H 0.4872 0.9731 0.2093 0.066 Uiso 1 1 calc R
H5N H 0.6115 0.9663 0.1439 0.066 Uiso 1 1 calc R
H6N H 0.5880 0.9658 0.3341 0.066 Uiso 1 1 calc R
O14 O 0.8493(6) 0.9730(4) -0.4440(5) 0.0658(16) Uani 1 1 d .
O13 O 0.8513(6) 0.9727(5) -0.0916(5) 0.0779(19) Uani 1 1 d .
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
N1 0.0363(17) 0.102(3) 0.0356(19) -0.010(4) 0.001(4) 0.0089(18)
C1 0.171(10) 0.159(10) 0.22(2) -0.083(16) -0.011(14) 0.068(8)
C2 0.105(5) 0.113(6) 0.146(9) -0.052(9) -0.001(8) 0.028(4)
C3 0.079(4) 0.105(5) 0.082(4) 0.013(7) 0.003(6) 0.012(3)
C5 0.234(12) 0.063(4) 0.244(17) -0.009(13) 0.045(17) -0.018(6)
C6 0.158(9) 0.134(8) 0.086(6) -0.015(6) 0.012(7) 0.001(7)
C7 0.105(6) 0.099(6) 0.290(19) 0.052(13) 0.059(12) -0.018(5)
C8 0.035(5) 0.081(5) 0.030(4) 0.001(4) -0.005(3) 0.004(3)
C9 0.045(5) 0.087(6) 0.028(4) 0.003(4) -0.004(3) -0.004(4)
O10 0.033(4) 0.178(6) 0.036(3) 0.009(4) 0.010(3) 0.008(4)
O11 0.048(4) 0.168(6) 0.031(3) -0.004(4) -0.004(3) 0.016(4)
N12 0.0390(17) 0.089(3) 0.0371(18) -0.001(4) 0.002(4) -0.0036(17)
O14 0.042(4) 0.125(5) 0.031(2) 0.013(3) 0.005(3) 0.014(3)
O13 0.041(4) 0.154(6) 0.038(3) -0.004(4) -0.010(3) 0.009(4)
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
C3 N1 H1N 109.5
C3 N1 H2N 109.5
H1N N1 H2N 109.5
C3 N1 H3N 109.5
H1N N1 H3N 109.5
H2N N1 H3N 109.5
C2 C1 H1C 109.5
C2 C1 H1D 109.5
H1C C1 H1D 109.5
C2 C1 H1E 109.5
H1C C1 H1E 109.5
H1D C1 H1E 109.5
C1 C2 C3 114.4(8)
C1 C2 H2A 108.7
C3 C2 H2A 108.7
C1 C2 H2B 108.7
C3 C2 H2B 108.7
H2A C2 H2B 107.6
N1 C3 C2 112.3(6)
N1 C3 H3A 109.1
C2 C3 H3A 109.1
N1 C3 H3B 109.1
C2 C3 H3B 109.1
H3A C3 H3B 107.9
C6 C5 H5A 109.5
C6 C5 H5B 109.5
H5A C5 H5B 109.5
C6 C5 H5C 109.5
H5A C5 H5C 109.5
H5B C5 H5C 109.5
C7 C6 C5 115.9(12)
C7 C6 H6A 108.3
C5 C6 H6A 108.3
C7 C6 H6B 108.3
C5 C6 H6B 108.3
H6A C6 H6B 107.4
C6 C7 N12 127.7(13)
C6 C7 H7A 105.4
N12 C7 H7A 105.4
C6 C7 H7B 105.4
N12 C7 H7B 105.4
H7A C7 H7B 106.0
O11 C8 O14 126.1(8)
O11 C8 C9 116.9(7)
O14 C8 C9 117.0(7)
O10 C9 O13 126.7(7)
O10 C9 C8 116.2(7)
O13 C9 C8 117.0(7)
C7 N12 H4N 109.5
C7 N12 H5N 109.5
H4N N12 H5N 109.5
C7 N12 H6N 109.5
H4N N12 H6N 109.5
H5N N12 H6N 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C3 1.438(8)
N1 H1N 0.9000
N1 H2N 0.9000
N1 H3N 0.9000
C1 C2 1.396(13)
C1 H1C 0.9700
C1 H1D 0.9700
C1 H1E 0.9700
C2 C3 1.519(9)
C2 H2A 0.9800
C2 H2B 0.9800
C3 H3A 0.9800
C3 H3B 0.9800
C5 C6 1.575(14)
C5 H5A 0.9700
C5 H5B 0.9700
C5 H5C 0.9700
C6 C7 1.266(14)
C6 H6A 0.9800
C6 H6B 0.9800
C7 N12 1.456(10)
C7 H7A 0.9800
C7 H7B 0.9800
C8 O11 1.216(8)
C8 O14 1.226(8)
C8 C9 1.555(6)
C9 O10 1.247(8)
C9 O13 1.249(8)
N12 H4N 0.9000
N12 H5N 0.9000
N12 H6N 0.9000
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
C1 C2 C3 N1 -168.3(17)
C5 C6 C7 N12 166.0(16)
O11 C8 C9 O10 -3.7(15)
O14 C8 C9 O10 178.8(6)
O11 C8 C9 O13 178.8(6)
O14 C8 C9 O13 1.3(15)
