#------------------------------------------------------------------------------
#$Date: 2019-11-17 09:23:07 +0200 (Sun, 17 Nov 2019) $
#$Revision: 229082 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/09/7230991.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_7230991
loop_
_publ_author_name
'Pinter, Emily N.'
'Cantrell, Lee S.'
'Day, Graeme M.'
'Wheeler, Kraig A.'
_publ_section_title
;
 Pasteur's tartaramide/malamide quasiracemates: new entries and departures
 from near inversion symmetry
;
_journal_issue                   30
_journal_name_full               CrystEngComm
_journal_page_first              4213
_journal_paper_doi               10.1039/C8CE00791H
_journal_volume                  20
_journal_year                    2018
_chemical_formula_moiety         'C4 H8 N2 O3'
_chemical_formula_sum            'C4 H8 N2 O3'
_chemical_formula_weight         132.12
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2018-03-24 deposited with the CCDC.
2018-06-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.659(1)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.4044(2)
_cell_length_b                   8.2033(2)
_cell_length_c                   7.7750(2)
_cell_measurement_reflns_used    6297
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      68.30
_cell_measurement_theta_min      4.80
_cell_volume                     587.44(2)
_computing_cell_refinement       APEX2
_computing_data_collection       'APEX2 (Bruker, 2013)'
_computing_data_reduction
;
SADABS (Bruker, 2013) and XPREP (Bruker, 2013)
;
_computing_molecular_graphics    'XSEED (Barbour, 2001)'
_computing_publication_material  'XSEED (Barbour, 2001)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0227
_diffrn_reflns_av_unetI/netI     0.0125
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            8515
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.209
_diffrn_reflns_theta_min         4.801
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    1.105
_exptl_absorpt_correction_T_max  0.753
_exptl_absorpt_correction_T_min  0.677
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2014/7, Bruker AXS'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.494
_exptl_crystal_description       block
_exptl_crystal_F_000             280
_exptl_crystal_size_max          0.274
_exptl_crystal_size_mid          0.265
_exptl_crystal_size_min          0.136
_refine_diff_density_max         0.457
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.070
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     97
_refine_ls_number_reflns         1067
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      1.008
_refine_ls_R_factor_all          0.0332
_refine_ls_R_factor_gt           0.0329
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0555P)²+0.3136P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0882
_refine_ls_wR_factor_ref         0.0885
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1049
_reflns_number_total             1067
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8ce00791h2.cif
_cod_data_source_block           16kaw53
_cod_depositor_comments
'Adding full bibliography for 7230989--7230996.cif.'
_cod_database_code               7230991
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.739
_shelx_estimated_absorpt_t_max   0.860
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
O1 O 0.66371(9) -0.29208(11) 0.23699(13) 0.0183(3) Uani 1 1 d . .
O2 O 0.70083(10) 0.13074(11) 0.34681(13) 0.0193(3) Uani 1 1 d D .
H5 H 0.7694(17) 0.178(2) 0.422(2) 0.023 Uiso 1 1 d D U
O3 O 0.92622(10) 0.24640(11) 0.07696(12) 0.0180(3) Uani 1 1 d . .
N1 N 0.50135(12) -0.10324(15) 0.28600(15) 0.0190(3) Uani 1 1 d D .
H4B H 0.4839(18) -0.0051(19) 0.305(2) 0.023 Uiso 1 1 d D U
H4A H 0.4348(17) -0.177(2) 0.270(2) 0.023 Uiso 1 1 d D U
N2 N 1.06052(11) 0.05181(14) 0.23664(14) 0.0152(3) Uani 1 1 d D .
H7B H 1.1396(16) 0.1124(18) 0.247(2) 0.018 Uiso 1 1 d D U
H7A H 1.0622(17) -0.0448(18) 0.279(2) 0.018 Uiso 1 1 d D U
C1 C 0.63283(13) -0.15025(15) 0.27170(16) 0.0148(3) Uani 1 1 d . .
C2 C 0.75229(13) -0.02117(15) 0.29730(16) 0.0145(3) Uani 1 1 d . .
H2 H 0.8345 -0.0583 0.3917 0.017 Uiso 1 1 calc R U
C3 C 0.80654(13) -0.00501(16) 0.12462(16) 0.0160(3) Uani 1 1 d . .
H3A H 0.8338 -0.1140 0.0871 0.019 Uiso 1 1 calc R U
H3B H 0.7272 0.0378 0.0321 0.019 Uiso 1 1 calc R U
C4 C 0.93644(13) 0.10789(15) 0.14456(16) 0.0142(3) Uani 1 1 d . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
C2 O2 H5 108.9(11)
C1 N1 H4B 120.9(12)
C1 N1 H4A 116.6(12)
H4B N1 H4A 122.4(16)
C4 N2 H7B 119.3(11)
C4 N2 H7A 118.4(11)
H7B N2 H7A 122.2(15)
O1 C1 N1 123.75(12)
O1 C1 C2 118.67(11)
N1 C1 C2 117.58(11)
O2 C2 C1 111.24(10)
O2 C2 C3 110.70(10)
C1 C2 C3 108.15(10)
O2 C2 H2 108.9
C1 C2 H2 108.9
C3 C2 H2 108.9
C4 C3 C2 111.51(10)
C4 C3 H3A 109.3
C2 C3 H3A 109.3
C4 C3 H3B 109.3
C2 C3 H3B 109.3
H3A C3 H3B 108.0
O3 C4 N2 121.97(12)
O3 C4 C3 121.44(11)
N2 C4 C3 116.59(11)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.2420(16)
O2 C2 1.4179(15)
O2 H5 0.866(14)
O3 C4 1.2475(16)
N1 C1 1.3212(17)
N1 H4B 0.841(15)
N1 H4A 0.861(14)
N2 C4 1.3222(17)
N2 H7B 0.884(13)
N2 H7A 0.858(14)
C1 C2 1.5273(17)
C2 C3 1.5354(17)
C2 H2 1.0000
C3 C4 1.5158(17)
C3 H3A 0.9900
C3 H3B 0.9900
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H4B O1 0.841(15) 2.215(15) 2.9740(15) 150.3(15) 2_655
N1 H4A O2 0.861(14) 2.115(15) 2.9411(15) 160.8(16) 2_645
N2 H7B O1 0.884(13) 1.990(14) 2.8623(14) 168.7(15) 2_755
N2 H7A O3 0.858(14) 2.036(14) 2.8844(14) 169.8(16) 2_745
O2 H5 O3 0.866(14) 1.817(15) 2.6791(13) 173.0(16) 4_566
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
O1 C1 C2 O2 -176.29(10)
N1 C1 C2 O2 4.48(16)
O1 C1 C2 C3 61.94(14)
N1 C1 C2 C3 -117.29(12)
O2 C2 C3 C4 63.95(13)
C1 C2 C3 C4 -173.94(10)
C2 C3 C4 O3 -107.97(13)
C2 C3 C4 N2 72.17(14)
