#------------------------------------------------------------------------------
#$Date: 2016-03-26 20:59:30 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180459 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/28/7212868.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_7212868
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            'C23 H32 N2 O4'
_chemical_formula_weight         400.51
_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                 93.130(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.661(3)
_cell_length_b                   10.1290(10)
_cell_length_c                   17.361(2)
_cell_measurement_temperature    293(2)
_cell_volume                     2223.1(6)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_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  0.0410
_diffrn_reflns_av_sigmaI/netI    0.0941
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5603
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.80
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.197
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.155
_refine_diff_density_min         -0.114
_refine_diff_density_rms         0.033
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     132
_refine_ls_number_reflns         1935
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.2667
_refine_ls_R_factor_gt           0.0934
_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)+(0.0999P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1766
_refine_ls_wR_factor_ref         0.2491
_reflns_number_gt                708
_reflns_number_total             1935
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c0ce00253d.txt
_cod_data_source_block           2.C10
_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               7212868
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
N1 N 0.1782(4) -0.0488(5) 1.0198(2) 0.0853(15) Uani 1 1 d .
C1 C 0.1670(5) 0.0787(7) 1.0133(4) 0.125(3) Uani 1 1 d .
H1 H 0.1907 0.1314 1.0545 0.150 Uiso 1 1 calc R
C2 C 0.1220(6) 0.1391(6) 0.9488(4) 0.148(3) Uani 1 1 d .
H2 H 0.1155 0.2306 0.9484 0.178 Uiso 1 1 calc R
C3 C 0.0874(4) 0.0715(6) 0.8869(3) 0.0755(16) Uani 1 1 d .
C4 C 0.1027(5) -0.0591(6) 0.8925(3) 0.103(2) Uani 1 1 d .
H4 H 0.0835 -0.1132 0.8508 0.123 Uiso 1 1 calc R
C5 C 0.1466(5) -0.1141(5) 0.9593(3) 0.116(3) Uani 1 1 d .
H5 H 0.1539 -0.2055 0.9608 0.139 Uiso 1 1 calc R
C6 C 0.0396(4) 0.1397(5) 0.8166(3) 0.0957(19) Uani 1 1 d .
H6A H 0.0921 0.1996 0.7977 0.115 Uiso 1 1 calc R
H6B H -0.0192 0.1930 0.8323 0.115 Uiso 1 1 calc R
C7 C 0.0000 0.0530(6) 0.7500 0.072(2) Uani 1 2 d S
H7A H -0.0568 -0.0031 0.7661 0.086 Uiso 0.50 1 calc PR
H7B H 0.0568 -0.0031 0.7339 0.086 Uiso 0.50 1 calc PR
O1 O -0.2640(3) -0.1433(3) 0.34821(17) 0.1184(17) Uani 1 1 d .
H100 H -0.2389 -0.1077 0.3873 0.178 Uiso 1 1 d R
O2 O -0.2924(4) 0.0607(4) 0.3136(2) 0.1184(17) Uani 1 1 d .
C8 C -0.2973(4) -0.0534(6) 0.2996(3) 0.0745(17) Uani 1 1 d .
C9 C -0.3450(4) -0.1088(5) 0.2266(2) 0.0808(17) Uani 1 1 d .
H9A H -0.4005 -0.1699 0.2392 0.097 Uiso 1 1 calc R
H9B H -0.2912 -0.1592 0.2019 0.097 Uiso 1 1 calc R
C10 C -0.3909(4) -0.0109(4) 0.1696(2) 0.0695(14) Uani 1 1 d .
H10A H -0.4482 0.0356 0.1926 0.083 Uiso 1 1 calc R
H10B H -0.3369 0.0536 0.1590 0.083 Uiso 1 1 calc R
C11 C -0.4318(4) -0.0700(5) 0.0950(2) 0.0735(15) Uani 1 1 d .
H11A H -0.3740 -0.1143 0.0713 0.088 Uiso 1 1 calc R
H11B H -0.4842 -0.1363 0.1058 0.088 Uiso 1 1 calc R
C12 C -0.4804(4) 0.0265(4) 0.0386(2) 0.0745(16) Uani 1 1 d .
H12A H -0.4285 0.0946 0.0300 0.089 Uiso 1 1 calc R
H12B H -0.5394 0.0685 0.0622 0.089 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
C5 N1 C1 114.3(5) . .
N1 C1 C2 123.5(5) . .
N1 C1 H1 118.3 . .
C2 C1 H1 118.3 . .
C3 C2 C1 122.2(6) . .
C3 C2 H2 118.9 . .
C1 C2 H2 118.9 . .
C2 C3 C4 114.3(5) . .
C2 C3 C6 121.4(6) . .
C4 C3 C6 124.3(5) . .
C3 C4 C5 120.7(5) . .
C3 C4 H4 119.6 . .
C5 C4 H4 119.6 . .
N1 C5 C4 125.0(5) . .
N1 C5 H5 117.5 . .
C4 C5 H5 117.5 . .
C3 C6 C7 117.1(5) . .
C3 C6 H6A 108.0 . .
C7 C6 H6A 108.0 . .
C3 C6 H6B 108.0 . .
C7 C6 H6B 108.0 . .
H6A C6 H6B 107.3 . .
C6 C7 C6 109.1(6) . 2_556
C6 C7 H7A 109.9 . .
C6 C7 H7A 109.9 2_556 .
C6 C7 H7B 109.9 . .
C6 C7 H7B 109.9 2_556 .
H7A C7 H7B 108.3 . .
C8 O1 H100 109.2 . .
O2 C8 O1 122.8(5) . .
O2 C8 C9 124.0(5) . .
O1 C8 C9 113.2(5) . .
C8 C9 C10 116.1(4) . .
C8 C9 H9A 108.3 . .
C10 C9 H9A 108.3 . .
C8 C9 H9B 108.3 . .
C10 C9 H9B 108.3 . .
H9A C9 H9B 107.4 . .
C11 C10 C9 114.3(4) . .
C11 C10 H10A 108.7 . .
C9 C10 H10A 108.7 . .
C11 C10 H10B 108.7 . .
C9 C10 H10B 108.7 . .
H10A C10 H10B 107.6 . .
C12 C11 C10 114.7(4) . .
C12 C11 H11A 108.6 . .
C10 C11 H11A 108.6 . .
C12 C11 H11B 108.6 . .
C10 C11 H11B 108.6 . .
H11A C11 H11B 107.6 . .
C11 C12 C12 117.1(5) . 5_455
C11 C12 H12A 108.0 . .
C12 C12 H12A 108.0 5_455 .
C11 C12 H12B 108.0 . .
C12 C12 H12B 108.0 5_455 .
H12A C12 H12B 107.3 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C5 1.286(5) .
N1 C1 1.303(7) .
C1 C2 1.372(7) .
C1 H1 0.9300 .
C2 C3 1.328(6) .
C2 H2 0.9300 .
C3 C4 1.340(7) .
C3 C6 1.501(6) .
C4 C5 1.375(6) .
C4 H4 0.9300 .
C5 H5 0.9300 .
C6 C7 1.515(5) .
C6 H6A 0.9700 .
C6 H6B 0.9700 .
C7 C6 1.515(5) 2_556
C7 H7A 0.9700 .
C7 H7B 0.9700 .
O1 C8 1.297(5) .
O1 H100 0.8175 .
O2 C8 1.181(5) .
C8 C9 1.484(6) .
C9 C10 1.496(5) .
C9 H9A 0.9700 .
C9 H9B 0.9700 .
C10 C11 1.493(5) .
C10 H10A 0.9700 .
C10 H10B 0.9700 .
C11 C12 1.491(6) .
C11 H11A 0.9700 .
C11 H11B 0.9700 .
C12 C12 1.503(8) 5_455
C12 H12A 0.9700 .
C12 H12B 0.9700 .
