#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/20/55/7205534.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_7205534
loop_
_publ_author_name
'King, Matthew D.'
'Buchanan, William D.'
'Korter, Timothy M.'
_publ_section_title
;
 Application of London-type dispersion corrections to the solid-state
 density functional theory simulation of the terahertz spectra of
 crystalline pharmaceuticals.
;
_journal_issue                   10
_journal_name_full               'Physical chemistry chemical physics : PCCP'
_journal_page_first              4250
_journal_page_last               4259
_journal_paper_doi               10.1039/c0cp01595d
_journal_volume                  13
_journal_year                    2011
_chemical_formula_moiety         'C14 H14 O3'
_chemical_formula_sum            'C14 H14 O3'
_chemical_formula_weight         230.25
_chemical_name_common            Naproxen
_chemical_name_systematic
;
Naproxen
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 93.737(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   7.7354(11)
_cell_length_b                   5.7181(8)
_cell_length_c                   13.3641(18)
_cell_measurement_reflns_used    2824
_cell_measurement_temperature    102(2)
_cell_measurement_theta_max      28.31
_cell_measurement_theta_min      2.64
_cell_volume                     589.86(14)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      102(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0233
_diffrn_reflns_av_sigmaI/netI    0.0195
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6007
_diffrn_reflns_theta_full        28.32
_diffrn_reflns_theta_max         28.32
_diffrn_reflns_theta_min         2.64
_diffrn_standards_decay_%        NO
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  0.9812
_exptl_absorpt_correction_T_min  0.9690
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'R. Blessing, Acta Cryst. (1995) A51 33-38.'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             244
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.287
_refine_diff_density_min         -0.204
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     160
_refine_ls_number_reflns         1611
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.108
_refine_ls_R_factor_all          0.0367
_refine_ls_R_factor_gt           0.0343
_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)+(0.0648P)²+0.0465P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0941
_refine_ls_wR_factor_ref         0.0976
_reflns_number_gt                1519
_reflns_number_total             1611
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            C0CP01595D.TXT
_cod_data_source_block           S_naproxen
_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.

'_exptl_absorpt_correction_type' value 'MULTI-SCAN' changed
to 'multi-scan' 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_enum 1555 2011-01-17 13:19:09Z saulius 
;
_cod_original_sg_symbol_H-M      'P2(1) '
_cod_database_code               7205534
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
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
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.3736(2) 0.3214(3) 0.47711(11) 0.0382(4) Uani 1 1 d . . .
O2 O 0.32803(18) -0.0492(3) 0.42697(10) 0.0287(3) Uani 1 1 d . . .
C1 C 0.2895(2) 0.1762(3) 0.42915(12) 0.0234(4) Uani 1 1 d . . .
C2 C 0.1299(2) 0.2353(3) 0.36204(12) 0.0215(3) Uani 1 1 d . . .
H2 H 0.0512 0.0963 0.3590 0.026 Uiso 1 1 calc R . .
C3 C 0.1892(2) 0.2807(3) 0.25689(12) 0.0199(3) Uani 1 1 d . . .
C4 C 0.1493(2) 0.1239(3) 0.18080(12) 0.0199(3) Uani 1 1 d . . .
H4 H 0.0901 -0.0166 0.1949 0.024 Uiso 1 1 calc R . .
C6 C 0.1955(2) 0.1692(3) 0.08149(11) 0.0187(3) Uani 1 1 d . . .
C7 C 0.14585(19) 0.0155(3) 0.00134(12) 0.0213(3) Uani 1 1 d . . .
H7 H 0.0920 -0.1294 0.0150 0.026 Uiso 1 1 calc R . .
C8 C 0.1749(2) 0.0741(3) -0.09522(12) 0.0235(3) Uani 1 1 d . . .
H8 H 0.1380 -0.0282 -0.1484 0.028 Uiso 1 1 calc R . .
C9 C 0.2597(2) 0.2865(3) -0.11676(12) 0.0215(3) Uani 1 1 d . . .
C10 C 0.3173(2) 0.4351(3) -0.04091(12) 0.0211(3) Uani 1 1 d . . .
H10 H 0.3787 0.5735 -0.0555 0.025 Uiso 1 1 calc R . .
C11 C 0.28364(19) 0.3792(3) 0.06019(12) 0.0184(3) Uani 1 1 d . . .
C12 C 0.3298(2) 0.5334(3) 0.14081(12) 0.0219(3) Uani 1 1 d . . .
H12 H 0.3935 0.6714 0.1286 0.026 Uiso 1 1 calc R . .
C13 C 0.2838(2) 0.4860(3) 0.23619(12) 0.0215(3) Uani 1 1 d . . .
H13 H 0.3156 0.5919 0.2890 0.026 Uiso 1 1 calc R . .
C14 C 0.0317(3) 0.4429(4) 0.40302(14) 0.0298(4) Uani 1 1 d . . .
H14A H -0.0079 0.4030 0.4691 0.045 Uiso 1 1 calc R . .
H14B H -0.0686 0.4796 0.3571 0.045 Uiso 1 1 calc R . .
H14C H 0.1086 0.5791 0.4091 0.045 Uiso 1 1 calc R . .
O3 O 0.27608(17) 0.3227(3) -0.21708(9) 0.0279(3) Uani 1 1 d . . .
C15 C 0.3576(2) 0.5343(4) -0.24564(14) 0.0311(4) Uani 1 1 d . . .
H15A H 0.2935 0.6685 -0.2213 0.047 Uiso 1 1 calc R . .
H15B H 0.3581 0.5415 -0.3189 0.047 Uiso 1 1 calc R . .
H15C H 0.4770 0.5382 -0.2163 0.047 Uiso 1 1 calc R . .
H1 H 0.428(3) -0.082(5) 0.4596(18) 0.041(7) 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
C C 0.0033 0.0000 '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'
O O 0.0106 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O2 H1 113(2) . . ?
O1 C1 O2 124.38(18) . . ?
O1 C1 C2 123.26(18) . . ?
O2 C1 C2 112.33(15) . . ?
C1 C2 C3 107.45(13) . . ?
C1 C2 C14 111.44(15) . . ?
C3 C2 C14 112.53(14) . . ?
C1 C2 H2 108.4 . . ?
C3 C2 H2 108.4 . . ?
C14 C2 H2 108.4 . . ?
C4 C3 C13 119.23(15) . . ?
C4 C3 C2 120.19(15) . . ?
C13 C3 C2 120.58(14) . . ?
C3 C4 C6 120.94(15) . . ?
C3 C4 H4 119.5 . . ?
C6 C4 H4 119.5 . . ?
C11 C6 C7 118.87(14) . . ?
C11 C6 C4 119.68(14) . . ?
C7 C6 C4 121.34(15) . . ?
C8 C7 C6 120.52(15) . . ?
C8 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
C7 C8 C9 120.56(15) . . ?
C7 C8 H8 119.7 . . ?
C9 C8 H8 119.7 . . ?
O3 C9 C10 125.58(16) . . ?
O3 C9 C8 113.66(15) . . ?
C10 C9 C8 120.77(15) . . ?
C9 C10 C11 119.25(15) . . ?
C9 C10 H10 120.4 . . ?
C11 C10 H10 120.4 . . ?
C6 C11 C12 118.29(14) . . ?
C6 C11 C10 119.92(14) . . ?
C12 C11 C10 121.74(15) . . ?
C13 C12 C11 120.94(15) . . ?
C13 C12 H12 119.5 . . ?
C11 C12 H12 119.5 . . ?
C12 C13 C3 120.82(15) . . ?
C12 C13 H13 119.6 . . ?
C3 C13 H13 119.6 . . ?
C2 C14 H14A 109.5 . . ?
C2 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C2 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C9 O3 C15 117.39(14) . . ?
O3 C15 H15A 109.5 . . ?
O3 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O3 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
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
O1 C1 1.212(2) . ?
O2 C1 1.324(2) . ?
O2 H1 0.88(3) . ?
C1 C2 1.516(2) . ?
C2 C3 1.529(2) . ?
C2 C14 1.530(2) . ?
C2 H2 1.0000 . ?
C3 C4 1.375(2) . ?
C3 C13 1.420(2) . ?
C4 C6 1.420(2) . ?
C4 H4 0.9500 . ?
C6 C11 1.419(2) . ?
C6 C7 1.419(2) . ?
C7 C8 1.366(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.419(3) . ?
C8 H8 0.9500 . ?
C9 O3 1.371(2) . ?
C9 C10 1.375(2) . ?
C10 C11 1.429(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.420(2) . ?
C12 C13 1.373(2) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
O3 C15 1.428(2) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H1 O1 0.88(3) 1.79(3) 2.6703(19) 174(3) 2_646
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 137720
