#------------------------------------------------------------------------------
#$Date: 2016-03-26 20:59:30 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180459 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/28/7212870.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_7212870
loop_
_publ_author_name
'Braga, Dario'
'Dichiarante, Elena'
'Palladino, Giuseppe'
'Grepioni, Fabrizia'
'Chierotti, Michele R.'
'Gobetto, Roberto'
'Pellegrino, Luca'
_publ_section_title
;
 Remarkable reversal of melting point alternation by co-crystallization
;
_journal_issue                   11
_journal_name_full               CrystEngComm
_journal_page_first              3534
_journal_paper_doi               10.1039/c0ce00253d
_journal_volume                  12
_journal_year                    2010
_chemical_formula_sum            'C19 H24 N2 O4'
_chemical_formula_weight         344.40
_chemical_name_systematic
;
?
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 95.597(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.7629(8)
_cell_length_b                   5.3869(4)
_cell_length_c                   24.640(2)
_cell_measurement_temperature    293(2)
_cell_volume                     1818.1(2)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_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  0.0294
_diffrn_reflns_av_sigmaI/netI    0.0470
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            4312
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         2.97
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.258
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.190
_refine_diff_density_min         -0.143
_refine_diff_density_rms         0.033
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     114
_refine_ls_number_reflns         1586
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.099
_refine_ls_R_factor_all          0.1162
_refine_ls_R_factor_gt           0.0647
_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)+(0.0621P)²+0.4972P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1266
_refine_ls_wR_factor_ref         0.1429
_reflns_number_gt                1044
_reflns_number_total             1586
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c0ce00253d.txt
_cod_data_source_block           2.C6
_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 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               7212870
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'
'-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
O2 O 0.55411(12) 0.0338(4) 0.41482(8) 0.0682(6) Uani 1 1 d .
C3 C 0.15956(17) 0.2172(5) 0.31189(9) 0.0443(6) Uani 1 1 d .
N1 N 0.31423(14) -0.0313(4) 0.37030(9) 0.0567(6) Uani 1 1 d .
C10 C 0.71355(15) -0.1748(5) 0.48199(9) 0.0486(7) Uani 1 1 d .
H10A H 0.7352 -0.1648 0.4457 0.058 Uiso 1 1 calc R
H10B H 0.7116 -0.0074 0.4963 0.058 Uiso 1 1 calc R
C8 C 0.53938(17) -0.1526(5) 0.43912(10) 0.0501(7) Uani 1 1 d .
C4 C 0.14517(17) 0.0061(5) 0.34175(10) 0.0487(7) Uani 1 1 d .
H4 H 0.0825 -0.0567 0.3430 0.058 Uiso 1 1 calc R
C2 C 0.25468(18) 0.2991(5) 0.31251(10) 0.0539(7) Uani 1 1 d .
H2 H 0.2688 0.4397 0.2928 0.065 Uiso 1 1 calc R
C9 C 0.61157(16) -0.2836(5) 0.47785(9) 0.0529(7) Uani 1 1 d .
H9A H 0.6150 -0.4558 0.4667 0.063 Uiso 1 1 calc R
H9B H 0.5883 -0.2810 0.5138 0.063 Uiso 1 1 calc R
C7 C 0.0000 0.2054(7) 0.2500 0.0597(10) Uani 1 2 d S
H7A H -0.0313 0.0992 0.2749 0.072 Uiso 0.50 1 calc PR
H7B H 0.0313 0.0992 0.2251 0.072 Uiso 0.50 1 calc PR
O1 O 0.45453(12) -0.2671(4) 0.43318(9) 0.0842(7) Uani 1 1 d .
H100 H 0.4167 -0.1892 0.4117 0.126 Uiso 1 1 calc R
C6 C 0.07644(18) 0.3569(5) 0.28197(11) 0.0598(8) Uani 1 1 d .
H6A H 0.0449 0.4543 0.3084 0.072 Uiso 1 1 calc R
H6B H 0.1033 0.4724 0.2572 0.072 Uiso 1 1 calc R
C5 C 0.22340(17) -0.1115(5) 0.36966(10) 0.0511(7) Uani 1 1 d .
H5 H 0.2118 -0.2548 0.3891 0.061 Uiso 1 1 calc R
C1 C 0.32807(18) 0.1733(6) 0.34209(11) 0.0616(8) Uani 1 1 d .
H1 H 0.3913 0.2346 0.3425 0.074 Uiso 1 1 calc R
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C4 C3 C2 116.3(2) . .
C4 C3 C6 122.2(2) . .
C2 C3 C6 121.5(2) . .
C5 N1 C1 116.7(2) . .
C10 C10 C9 113.0(3) 7_646 .
C10 C10 H10A 109.0 7_646 .
C9 C10 H10A 109.0 . .
C10 C10 H10B 109.0 7_646 .
C9 C10 H10B 109.0 . .
H10A C10 H10B 107.8 . .
O2 C8 O1 122.0(2) . .
O2 C8 C9 125.7(2) . .
O1 C8 C9 112.3(2) . .
C5 C4 C3 120.0(2) . .
C5 C4 H4 120.0 . .
C3 C4 H4 120.0 . .
C1 C2 C3 119.9(3) . .
C1 C2 H2 120.0 . .
C3 C2 H2 120.0 . .
C8 C9 C10 114.6(2) . .
C8 C9 H9A 108.6 . .
C10 C9 H9A 108.6 . .
C8 C9 H9B 108.6 . .
C10 C9 H9B 108.6 . .
H9A C9 H9B 107.6 . .
C6 C7 C6 113.8(3) . 2
C6 C7 H7A 108.8 . .
C6 C7 H7A 108.8 2 .
C6 C7 H7B 108.8 . .
C6 C7 H7B 108.8 2 .
H7A C7 H7B 107.7 . .
C8 O1 H100 109.5 . .
C7 C6 C3 116.7(2) . .
C7 C6 H6A 108.1 . .
C3 C6 H6A 108.1 . .
C7 C6 H6B 108.1 . .
C3 C6 H6B 108.1 . .
H6A C6 H6B 107.3 . .
N1 C5 C4 123.3(2) . .
N1 C5 H5 118.3 . .
C4 C5 H5 118.3 . .
N1 C1 C2 123.7(2) . .
N1 C1 H1 118.1 . .
C2 C1 H1 118.1 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O2 C8 1.197(3) .
C3 C4 1.379(3) .
C3 C2 1.380(3) .
C3 C6 1.501(3) .
N1 C5 1.321(3) .
N1 C1 1.327(3) .
C10 C10 1.509(4) 7_646
C10 C9 1.515(3) .
C10 H10A 0.9700 .
C10 H10B 0.9700 .
C8 O1 1.316(3) .
C8 C9 1.487(3) .
C4 C5 1.375(3) .
C4 H4 0.9300 .
C2 C1 1.366(4) .
C2 H2 0.9300 .
C9 H9A 0.9700 .
C9 H9B 0.9700 .
C7 C6 1.494(3) .
C7 C6 1.494(3) 2
C7 H7A 0.9700 .
C7 H7B 0.9700 .
O1 H100 0.8200 .
C6 H6A 0.9700 .
C6 H6B 0.9700 .
C5 H5 0.9300 .
C1 H1 0.9300 .
