#------------------------------------------------------------------------------
#$Date: 2016-03-24 01:35:18 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179537 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/06/4500629.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_4500629
loop_
_publ_author_name
'Kennedy, Alan R.'
'Morrison, Catriona A.'
'Briggs, Naomi E. B.'
'Arbuckle, William'
_publ_section_title
;
 Density and Stability Differences Between Enantiopure and Racemic Salts:
 Construction and Structural Analysis of a Systematic Series of
 Crystalline Salt Forms of Methylephedrine
;
_journal_issue                   5
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              1821
_journal_paper_doi               10.1021/cg200030s
_journal_volume                  11
_journal_year                    2011
_chemical_formula_sum            'C15 H21 N O5'
_chemical_formula_weight         295.33
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 100.111(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.6674(7)
_cell_length_b                   24.5551(18)
_cell_length_c                   5.9212(3)
_cell_measurement_reflns_used    5504
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      73.2728
_cell_measurement_theta_min      4.2038
_cell_volume                     1526.91(17)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Oxford Diffraction Gemini S'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54180
_diffrn_reflns_av_R_equivalents  0.0890
_diffrn_reflns_av_sigmaI/netI    0.0599
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            14976
_diffrn_reflns_theta_full        70.00
_diffrn_reflns_theta_max         70.00
_diffrn_reflns_theta_min         4.21
_exptl_absorpt_coefficient_mu    0.800
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.285
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.193
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.897
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     205
_refine_ls_number_reflns         2885
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.897
_refine_ls_R_factor_all          0.0715
_refine_ls_R_factor_gt           0.0421
_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)+(0.0597P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0984
_refine_ls_wR_factor_ref         0.1062
_reflns_number_gt                1883
_reflns_number_total             2885
_reflns_threshold_expression     I>2/s(I)
_cod_data_source_file            cg200030s_si_001.cif
_cod_data_source_block           rmepdmale
_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 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               4500629
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
O1 O 0.64920(12) 0.38885(6) 0.0786(2) 0.0309(3) Uani 1 1 d .
O2 O 0.97027(14) 0.33866(7) 0.1750(2) 0.0475(4) Uani 1 1 d .
O3 O 0.81178(14) 0.33041(8) -0.1159(3) 0.0655(6) Uani 1 1 d .
O4 O 1.19840(14) 0.33064(6) 0.2384(2) 0.0422(4) Uani 1 1 d .
O5 O 1.34864(12) 0.30675(6) 0.0442(2) 0.0336(3) Uani 1 1 d .
N1 N 0.51993(15) 0.34017(6) 0.4255(3) 0.0262(4) Uani 1 1 d .
C1 C 0.75103(16) 0.45701(8) 0.3557(3) 0.0257(4) Uani 1 1 d .
C2 C 0.81528(17) 0.47067(8) 0.5735(3) 0.0286(4) Uani 1 1 d .
H2 H 0.8210 0.4448 0.6943 0.034 Uiso 1 1 calc R
C3 C 0.87080(18) 0.52119(8) 0.6163(3) 0.0328(5) Uani 1 1 d .
H3 H 0.9145 0.5299 0.7659 0.039 Uiso 1 1 calc R
C4 C 0.86311(18) 0.55935(8) 0.4420(3) 0.0347(5) Uani 1 1 d .
H4 H 0.9009 0.5942 0.4716 0.042 Uiso 1 1 calc R
C5 C 0.80011(19) 0.54627(8) 0.2251(3) 0.0356(5) Uani 1 1 d .
H5 H 0.7950 0.5722 0.1048 0.043 Uiso 1 1 calc R
C6 C 0.74421(19) 0.49547(8) 0.1816(3) 0.0316(5) Uani 1 1 d .
H6 H 0.7009 0.4869 0.0316 0.038 Uiso 1 1 calc R
C7 C 0.69009(17) 0.40131(7) 0.3141(3) 0.0254(4) Uani 1 1 d .
H7 H 0.7534 0.3732 0.3824 0.030 Uiso 1 1 calc R
C8 C 0.57330(17) 0.39731(7) 0.4314(3) 0.0259(4) Uani 1 1 d .
H8 H 0.5995 0.4083 0.5955 0.031 Uiso 1 1 calc R
C9 C 0.46751(18) 0.43546(8) 0.3207(3) 0.0344(5) Uani 1 1 d .
H9A H 0.4387 0.4247 0.1606 0.052 Uiso 1 1 calc R
H9B H 0.4997 0.4729 0.3264 0.052 Uiso 1 1 calc R
H9C H 0.3960 0.4333 0.4041 0.052 Uiso 1 1 calc R
C10 C 0.61319(18) 0.29496(8) 0.4315(3) 0.0322(5) Uani 1 1 d .
H10A H 0.6786 0.2983 0.5694 0.048 Uiso 1 1 calc R
H10B H 0.6533 0.2968 0.2950 0.048 Uiso 1 1 calc R
H10C H 0.5691 0.2600 0.4342 0.048 Uiso 1 1 calc R
C11 C 0.44645(19) 0.33245(8) 0.6168(3) 0.0333(5) Uani 1 1 d .
H11A H 0.4076 0.2962 0.6053 0.050 Uiso 1 1 calc R
H11B H 0.3796 0.3602 0.6060 0.050 Uiso 1 1 calc R
H11C H 0.5041 0.3359 0.7644 0.050 Uiso 1 1 calc R
C12 C 1.01317(18) 0.30948(9) -0.1927(3) 0.0357(5) Uani 1 1 d .
H12 H 0.9720 0.3002 -0.3433 0.043 Uiso 1 1 calc R
C13 C 1.13901(18) 0.30459(8) -0.1559(3) 0.0301(4) Uani 1 1 d .
H13 H 1.1734 0.2928 -0.2852 0.036 Uiso 1 1 calc R
C016 C 1.23553(18) 0.31451(8) 0.0555(3) 0.0275(4) Uani 1 1 d .
C021 C 0.9259(2) 0.32722(9) -0.0349(3) 0.0390(5) Uani 1 1 d .
H1H H 0.713(3) 0.3691(11) 0.029(5) 0.079(9) Uiso 1 1 d .
H1N H 0.458(2) 0.3355(8) 0.296(4) 0.042(6) Uiso 1 1 d .
H4H H 1.085(3) 0.3365(11) 0.217(5) 0.102(10) Uiso 1 1 d .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
O O 0.0492 0.0322 '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'
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C7 O1 H1H 107.9(17)
C021 O2 H4H 112.3(14)
C016 O4 H4H 113.8(14)
C10 N1 C11 108.90(14)
C10 N1 C8 116.40(14)
C11 N1 C8 110.17(14)
C10 N1 H1N 107.7(13)
C11 N1 H1N 102.5(13)
C8 N1 H1N 110.2(13)
C6 C1 C2 118.48(18)
C6 C1 C7 121.82(16)
C2 C1 C7 119.70(16)
C3 C2 C1 120.89(18)
C3 C2 H2 119.6
C1 C2 H2 119.6
C2 C3 C4 120.25(18)
C2 C3 H3 119.9
C4 C3 H3 119.9
C5 C4 C3 119.46(19)
C5 C4 H4 120.3
C3 C4 H4 120.3
C4 C5 C6 120.39(19)
C4 C5 H5 119.8
C6 C5 H5 119.8
C5 C6 C1 120.53(18)
C5 C6 H6 119.7
C1 C6 H6 119.7
O1 C7 C1 113.77(15)
O1 C7 C8 107.29(14)
C1 C7 C8 110.12(14)
O1 C7 H7 108.5
C1 C7 H7 108.5
C8 C7 H7 108.5
N1 C8 C9 108.26(15)
N1 C8 C7 112.45(14)
C9 C8 C7 111.44(15)
N1 C8 H8 108.2
C9 C8 H8 108.2
C7 C8 H8 108.2
C8 C9 H9A 109.5
C8 C9 H9B 109.5
H9A C9 H9B 109.5
C8 C9 H9C 109.5
H9A C9 H9C 109.5
H9B C9 H9C 109.5
N1 C10 H10A 109.5
N1 C10 H10B 109.5
H10A C10 H10B 109.5
N1 C10 H10C 109.5
H10A C10 H10C 109.5
H10B C10 H10C 109.5
N1 C11 H11A 109.5
N1 C11 H11B 109.5
H11A C11 H11B 109.5
N1 C11 H11C 109.5
H11A C11 H11C 109.5
H11B C11 H11C 109.5
C13 C12 C021 130.28(18)
C13 C12 H12 114.9
C021 C12 H12 114.9
C12 C13 C016 130.63(17)
C12 C13 H13 114.7
C016 C13 H13 114.7
O5 C016 O4 122.97(17)
O5 C016 C13 117.75(16)
O4 C016 C13 119.28(17)
O3 C021 O2 122.37(18)
O3 C021 C12 117.22(17)
O2 C021 C12 120.41(18)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C7 1.420(2)
O1 H1H 0.93(3)
O2 C021 1.281(2)
O2 H4H 1.21(3)
O3 C021 1.231(2)
O4 C016 1.279(2)
O4 H4H 1.20(3)
O5 C016 1.235(2)
N1 C10 1.487(2)
N1 C11 1.498(2)
N1 C8 1.512(2)
N1 H1N 0.93(2)
C1 C6 1.390(2)
C1 C2 1.391(2)
C1 C7 1.516(2)
C2 C3 1.379(3)
C2 H2 0.9500
C3 C4 1.386(3)
C3 H3 0.9500
C4 C5 1.379(3)
C4 H4 0.9500
C5 C6 1.387(3)
C5 H5 0.9500
C6 H6 0.9500
C7 C8 1.532(2)
C7 H7 1.0000
C8 C9 1.523(3)
C8 H8 1.0000
C9 H9A 0.9800
C9 H9B 0.9800
C9 H9C 0.9800
C10 H10A 0.9800
C10 H10B 0.9800
C10 H10C 0.9800
C11 H11A 0.9800
C11 H11B 0.9800
C11 H11C 0.9800
C12 C13 1.327(3)
C12 C021 1.494(3)
C12 H12 0.9500
C13 C016 1.494(3)
C13 H13 0.9500
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
C6 C1 C2 C3 0.1(3)
C7 C1 C2 C3 -179.55(16)
C1 C2 C3 C4 0.1(3)
C2 C3 C4 C5 -0.4(3)
C3 C4 C5 C6 0.3(3)
C4 C5 C6 C1 -0.1(3)
C2 C1 C6 C5 -0.1(3)
C7 C1 C6 C5 179.53(16)
C6 C1 C7 O1 11.7(2)
C2 C1 C7 O1 -168.68(15)
C6 C1 C7 C8 -108.81(18)
C2 C1 C7 C8 70.8(2)
C10 N1 C8 C9 155.20(14)
C11 N1 C8 C9 -80.22(18)
C10 N1 C8 C7 31.6(2)
C11 N1 C8 C7 156.22(15)
O1 C7 C8 N1 64.09(19)
C1 C7 C8 N1 -171.60(14)
O1 C7 C8 C9 -57.68(19)
C1 C7 C8 C9 66.63(18)
C021 C12 C13 C016 0.8(4)
C12 C13 C016 O5 180.0(2)
C12 C13 C016 O4 -0.3(3)
C13 C12 C021 O3 177.0(2)
C13 C12 C021 O2 -2.7(4)
