Furosemide's one little hydrogen atom: NMR crystallography structure verification of powdered molecular organics
Cory M. Widdifield; Harry Robson; Paul Hodgkinson; Chem.Commun. 52 (2016) 6685–; doi:

data_7119123
_publ_section_title
;
 Furosemide's one little hydrogen atom: NMR crystallography structure
 verification of powdered molecular organics
;
_journal_name_full               Chem.Commun.
_journal_page_first              6685
_journal_volume                  52
_journal_year                    2016
_chemical_formula_moiety         'C12 H11 Cl N2 O5 S'
_chemical_formula_sum            'C12 H11 Cl N2 O5 S'
_chemical_formula_weight         330.74
_chemical_name_common            Furosemide
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_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_date             2016-02-03
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2015.11.20 svn.r3248 for OlexSys, GUI svn.r5133)
;
_audit_update_record
;
2016-03-07 deposited with the CCDC.
2016-04-18 downloaded from the CCDC.
;
_cell_angle_alpha                92.938(5)
_cell_angle_beta                 107.085(5)
_cell_angle_gamma                116.622(6)
_cell_formula_units_Z            4
_cell_length_a                   9.5347(5)
_cell_length_b                   10.4694(6)
_cell_length_c                   15.6057(9)
_cell_measurement_reflns_used    2809
_cell_measurement_temperature    120.0
_cell_measurement_theta_max      29.8050
_cell_measurement_theta_min      2.2170
_cell_volume                     1300.34(16)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      120.0
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1511
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
  1 omega  -34.00   44.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       28.9587  -57.0000 -180.0000 78

  2 omega   44.00   81.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       28.9587 -178.0000 -150.0000 37

  3 omega   14.00   68.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       28.9587 -100.0000  -60.0000 54

  4 omega   44.00   71.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       28.9587 -100.0000   60.0000 27

  5 omega   23.00   71.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       28.9587 -100.0000 -180.0000 48

  6 omega    9.00   98.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       28.9587   57.0000   60.0000 89

  7 omega  -44.00   67.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       28.9587  -19.0000 -120.0000 111

  8 omega    9.00   98.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       28.9587   57.0000  -30.0000 89

  9 omega   35.00   94.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       28.9587  178.0000  120.0000 59

 10 omega   -1.00   99.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       28.9587   77.0000 -120.0000 100
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0482803000
_diffrn_orient_matrix_UB_12      -0.0335980000
_diffrn_orient_matrix_UB_13      0.0196828000
_diffrn_orient_matrix_UB_21      -0.0228266000
_diffrn_orient_matrix_UB_22      -0.0408962000
_diffrn_orient_matrix_UB_23      -0.0441273000
_diffrn_orient_matrix_UB_31      0.0712004000
_diffrn_orient_matrix_UB_32      0.0567245000
_diffrn_orient_matrix_UB_33      -0.0059058000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0797
_diffrn_reflns_av_unetI/netI     0.1153
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            19564
_diffrn_reflns_theta_full        29.00
_diffrn_reflns_theta_max         29.00
_diffrn_reflns_theta_min         2.23
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.479
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_correction_T_min  0.956
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
Analytical numeric absorption correction using a multifaceted crystal
            model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.689
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.508
_refine_diff_density_min         -0.662
_refine_diff_density_rms         0.098
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.994
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     467
_refine_ls_number_reflns         6913
_refine_ls_number_restraints     43
_refine_ls_restrained_S_all      0.990
_refine_ls_R_factor_all          0.1193
_refine_ls_R_factor_gt           0.0561
_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/[\s^2^(Fo^2^)+(0.0240P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0935
_refine_ls_wR_factor_ref         0.1209
_reflns_number_gt                3893
_reflns_number_total             6913
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6cc02171a2.cif
_cod_data_source_block           fur_new_16srv043
_cod_original_cell_volume        1300.35(13)
_cod_database_code               7119123
_chemical_oxdiff_formula         'C12 H11 Cl1 N2 O5 S1'
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     31.44
_olex2_refinement_description
;
1. Restrained distances
 C10-H10 \\sim C11-H11 \\sim C12-H12 \\sim C12A-H12A \\sim C11A-H11A \\sim
C10A-H10A
 with sigma of 0.005
 C8-H8A \\sim C8-H8B \\sim C8A-H8AA \\sim C8A-H8AB
 with sigma of 0.005
 C3-H3 \\sim C6-H6 \\sim C3A-H3A \\sim C6A-H6A
 with sigma of 0.005
 N1-H1 \\sim N1A-H1A \\sim N2-H2B \\sim N2-H2A \\sim N2A-H2AC \\sim N2A-H2AB
 with sigma of 0.005
 O2A-H2AA \\sim O2-H2
 with sigma of 0.005
;