 
data_Pnma
 
_audit_creation_method            'SHELXL-2014/7'
_shelx_SHELXL_version_number      '2014/7'
_chemical_name_systematic         ?
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          'C8 H16 Cl N O4'
_chemical_formula_sum
 'C8 H16 Cl N O4' 
_chemical_formula_weight          225.67

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'
 
_space_group_crystal_system       orthorhombic
_space_group_IT_number            62
_space_group_name_H-M_alt         'P n m a'
_space_group_name_Hall            '-P 2ac 2n'
 
_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.
;
 
loop_
 _space_group_symop_operation_xyz
 'x, y, z'
 '-x+1/2, -y, z+1/2'
 '-x, y+1/2, -z'
 'x+1/2, -y+1/2, -z+1/2'
 '-x, -y, -z'
 'x-1/2, y, -z-1/2'
 'x, -y-1/2, z'
 '-x-1/2, y-1/2, z-1/2'
 
_cell_length_a                    11.4473(7)
_cell_length_b                    8.1623(6)
_cell_length_c                    11.6646(7)
_cell_angle_alpha                 90
_cell_angle_beta                  90
_cell_angle_gamma                 90
_cell_volume                      1089.90(12)
_cell_formula_units_Z             4
_cell_measurement_temperature     298(2)
_cell_measurement_reflns_used     2540
_cell_measurement_theta_min       3.0300
_cell_measurement_theta_max       29.7830
 
_exptl_crystal_description        block
_exptl_crystal_colour             colourless
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_density_diffrn     1.375          
_exptl_crystal_F_000              480
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           0.220
_exptl_crystal_size_mid           0.210
_exptl_crystal_size_min           0.210
_exptl_absorpt_coefficient_mu     0.341
_shelx_estimated_absorpt_T_min    0.929
_shelx_estimated_absorpt_T_max    0.932
_exptl_absorpt_correction_type    'multi-scan'
_exptl_absorpt_correction_T_min   0.928
_exptl_absorpt_correction_T_max   0.931
_exptl_absorpt_process_details    'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature       298(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_source                    'Rotating-anode X-ray tube'
_diffrn_measurement_device_type   'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method        'four-circle diffractometer'
_diffrn_detector_area_resol_mean  ?
_diffrn_reflns_number             4911
_diffrn_reflns_av_unetI/netI      0.0130
_diffrn_reflns_av_R_equivalents   0.0128
_diffrn_reflns_limit_h_min        -13
_diffrn_reflns_limit_h_max        12
_diffrn_reflns_limit_k_min        -9
_diffrn_reflns_limit_k_max        8
_diffrn_reflns_limit_l_min        -13
_diffrn_reflns_limit_l_max        13
_diffrn_reflns_theta_min          2.493
_diffrn_reflns_theta_max          24.996
_diffrn_reflns_theta_full         24.996
_diffrn_measured_fraction_theta_max   0.999
_diffrn_measured_fraction_theta_full  0.999
_diffrn_reflns_Laue_measured_fraction_max    0.999
_diffrn_reflns_Laue_measured_fraction_full   0.999
_diffrn_reflns_point_group_measured_fraction_max   0.999
_diffrn_reflns_point_group_measured_fraction_full  0.999
_reflns_number_total              1032
_reflns_number_gt                 856
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.000
_reflns_Friedel_fraction_max      .
_reflns_Friedel_fraction_full     .
 
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
 
_computing_data_collection        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_cell_refinement        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction         'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_solution     'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement   'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics     'DIAMOND (Brandenburg & Putz, 2005)'
_computing_publication_material   'SHELXL-2014/7 (Sheldrick, 2014)'
_refine_special_details           ?
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.2000P)²+2.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      ?
_atom_sites_solution_secondary    ?
_atom_sites_solution_hydrogens    difmap
_refine_ls_hydrogen_treatment     constr
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        .
_refine_ls_number_reflns          1032
_refine_ls_number_parameters      127
_refine_ls_number_restraints      53
_refine_ls_R_factor_all           0.1297
_refine_ls_R_factor_gt            0.1208
_refine_ls_wR_factor_ref          0.3355
_refine_ls_wR_factor_gt           0.3244
_refine_ls_goodness_of_fit_ref    1.011
_refine_ls_restrained_S_all       1.117
_refine_ls_shift/su_max           0.000
_refine_ls_shift/su_mean          0.000
 
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
 _atom_site_refinement_flags_occupancy
 _atom_site_disorder_assembly
 _atom_site_disorder_group
Cl1 Cl 0.9555(2) 0.244(4) 0.3153(2) 0.0831(14) Uani 0.5 1 d D . P A -1
O1 O 0.8319(10) 0.292(2) 0.2940(11) 0.191(7) Uani 0.5 1 d D U P A -1
O2 O 0.9967(18) 0.168(2) 0.2121(13) 0.232(8) Uani 0.5 1 d D U P A -1
O3 O 0.9660(15) 0.131(2) 0.4135(12) 0.169(7) Uani 0.5 1 d D . P A -1
O4 O 1.0215(15) 0.3945(16) 0.3453(18) 0.167(7) Uani 0.5 1 d D . P A -1
N1 N 0.1934(7) 0.279(2) 0.5297(7) 0.085(5) Uani 0.5 1 d D . P B -1
H1A H 0.1295 0.3156 0.4929 0.102 Uiso 0.5 1 d R U P B -1
C1 C 0.1651(8) 0.259(4) 0.6545(8) 0.095(3) Uani 0.5 1 d D . P B -1
H1B H 0.0944 0.1975 0.6643 0.114 Uiso 0.5 1 d R U P B -1
H1C H 0.1540 0.3657 0.6876 0.114 Uiso 0.5 1 d R U P B -1
C4 C 0.2703(10) 0.1744(14) 0.7141(7) 0.087(3) Uani 0.5 1 d D . P B -1
H4A H 0.2488 0.0648 0.7355 0.104 Uiso 0.5 1 d R U P B -1
C8 C 0.3031(13) 0.278(3) 0.8200(9) 0.134(6) Uani 0.5 1 d D U P B -1
H8A H 0.3669 0.2266 0.8593 0.201 Uiso 0.5 1 d R U P B -1
H8B H 0.3262 0.3864 0.7964 0.201 Uiso 0.5 1 d R U P B -1
H8C H 0.2371 0.2860 0.8705 0.201 Uiso 0.5 1 d R U P B -1
C7 C 0.3724(11) 0.176(3) 0.6312(12) 0.118(7) Uani 0.5 1 d D . P B -1
H7A H 0.4405 0.1354 0.6702 0.142 Uiso 0.5 1 d R U P B -1
C6 C 0.3412(16) 0.058(3) 0.5345(17) 0.122(7) Uani 0.5 1 d D . P B -1
H6A H 0.3300 -0.0498 0.5654 0.146 Uiso 0.5 1 d R U P B -1
H6B H 0.4025 0.0532 0.4784 0.146 Uiso 0.5 1 d R U P B -1
C3 C 0.2258(14) 0.1131(19) 0.4826(14) 0.100(5) Uani 0.5 1 d D . P B -1
H3A H 0.2360 0.1209 0.4011 0.120 Uiso 0.5 1 d R U P B -1
H3B H 0.1639 0.0367 0.4975 0.120 Uiso 0.5 1 d R U P B -1
C5 C 0.3936(14) 0.343(3) 0.5935(15) 0.134(8) Uani 0.5 1 d D . P B -1
H5A H 0.4672 0.3500 0.5544 0.161 Uiso 0.5 1 d R U P B -1
H5B H 0.3972 0.4130 0.6597 0.161 Uiso 0.5 1 d R U P B -1
C2 C 0.2920(15) 0.402(2) 0.5166(15) 0.112(8) Uani 0.5 1 d D . P B -1
H2A H 0.2661 0.5091 0.5379 0.134 Uiso 0.5 1 d R U P B -1
H2B H 0.3184 0.4042 0.4385 0.134 Uiso 0.5 1 d R U P B -1
 
 
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
 
loop_
 _geom_bond_atom_site_label_1
 _geom_bond_atom_site_label_2
 _geom_bond_distance
 _geom_bond_site_symmetry_2
 _geom_bond_publ_flag
Cl1 O2 1.435(15) . ?
Cl1 O3 1.476(18) . ?
Cl1 O4 1.48(3) . ?
Cl1 O1 1.489(12) . ?
N1 C1 1.500(11) . ?
N1 C3 1.506(16) . ?
N1 C2 1.518(15) . ?
C1 C4 1.553(15) . ?
C4 C7 1.517(15) . ?
C4 C8 1.546(14) . ?
C7 C5 1.457(14) . ?
C7 C6 1.524(15) . ?
C6 C3 1.521(15) . ?
C5 C2 1.544(16) . ?
 
loop_
 _geom_angle_atom_site_label_1
 _geom_angle_atom_site_label_2
 _geom_angle_atom_site_label_3
 _geom_angle
 _geom_angle_site_symmetry_1
 _geom_angle_site_symmetry_3
 _geom_angle_publ_flag
O2 Cl1 O3 110.7(19) . . ?
O2 Cl1 O4 112.9(13) . . ?
O3 Cl1 O4 107.1(9) . . ?
O2 Cl1 O1 106.6(10) . . ?
O3 Cl1 O1 111.8(11) . . ?
O4 Cl1 O1 107.9(18) . . ?
C1 N1 C3 108.2(13) . . ?
C1 N1 C2 109.2(11) . . ?
C3 N1 C2 111.9(10) . . ?
N1 C1 C4 108.3(8) . . ?
C7 C4 C8 108.6(10) . . ?
C7 C4 C1 108.0(8) . . ?
C8 C4 C1 107.5(12) . . ?
C5 C7 C4 109.1(10) . . ?
C5 C7 C6 114.0(13) . . ?
C4 C7 C6 106.7(11) . . ?
C3 C6 C7 108.2(10) . . ?
N1 C3 C6 109.5(10) . . ?
C7 C5 C2 109.9(11) . . ?
N1 C2 C5 107.3(8) . . ?
 
_refine_diff_density_max    0.663
_refine_diff_density_min   -0.407
_refine_diff_density_rms    0.109



