#------------------------------------------------------------------------------
#$Date: 2016-03-26 16:44:30 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180353 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/22/7202263.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_7202263
loop_
_publ_author_name
'Mondal, Pallab'
'Karmakar, Anirban'
'Singh, W. Marjit'
'Baruah, Jubaraj B.'
_publ_section_title
;
 Crystal packing in some flexible carboxylic acids and esters attached
 to a naphthalene ring
;
_journal_issue                   11
_journal_name_full               CrystEngComm
_journal_page_first              1550
_journal_paper_doi               10.1039/b808399a
_journal_volume                  10
_journal_year                    2008
_chemical_formula_sum            'C16 H16 O6'
_chemical_formula_weight         304.29
_chemical_name_systematic
;
?
;
_space_group_IT_number           64
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-C 2ac 2'
_symmetry_space_group_name_H-M   'C m c a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   6.7148(3)
_cell_length_b                   16.6214(6)
_cell_length_c                   27.1596(10)
_cell_measurement_reflns_used    3697
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      0.00
_cell_measurement_theta_min      0.00
_cell_volume                     3031.3(2)
_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      296(2)
_diffrn_measured_fraction_theta_full 0.965
_diffrn_measured_fraction_theta_max 0.965
_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  0.0499
_diffrn_reflns_av_sigmaI/netI    0.0282
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            10265
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         1.50
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Brown
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Blocks
_exptl_crystal_F_000             1280
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.244
_refine_diff_density_min         -0.348
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.158
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         1485
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.158
_refine_ls_R_factor_all          0.1064
_refine_ls_R_factor_gt           0.0676
_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)+(0.0894P)²+8.2933P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1917
_refine_ls_wR_factor_ref         0.2404
_reflns_number_gt                919
_reflns_number_total             1485
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b808399a.txt
_cod_data_source_block           13diester_2
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
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 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      Cmca
_cod_database_code               7202263
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'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1, z+1/2'
'x+1/2, -y+1/2, -z'
'-x+1/2, y+1, -z+1/2'
'-x, -y, -z'
'x, y-1/2, -z-1/2'
'-x, y, z'
'x, -y-1/2, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, y, -z-1/2'
'-x+1/2, y+1/2, z'
'x+1/2, -y, 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
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.0000 0.1919(2) 0.14662(12) 0.0562(11) Uani 1 2 d S . .
O2 O 0.0000 -0.0073(2) 0.10314(14) 0.0772(15) Uani 1 2 d S . .
O3 O 0.0000 0.1085(2) 0.06116(15) 0.0824(16) Uani 1 2 d S . .
O4 O 0.0000 0.2042(2) 0.32137(12) 0.0548(11) Uani 1 2 d S . .
O5 O 0.0000 0.2357(2) 0.44968(14) 0.0751(14) Uani 1 2 d S . .
O6 O 0.0000 0.1213(3) 0.40713(16) 0.0942(19) Uani 1 2 d S . .
C1 C 0.0000 0.3574(3) 0.1381(2) 0.0536(15) Uani 1 2 d S . .
H1 H 0.0000 0.3269 0.1094 0.064 Uiso 1 2 calc SR . .
C2 C 0.0000 0.4391(4) 0.1349(2) 0.0667(17) Uani 1 2 d S . .
H2 H 0.0000 0.4636 0.1041 0.080 Uiso 1 2 calc SR . .
C3 C 0.0000 0.4865(3) 0.1774(2) 0.0604(16) Uani 1 2 d S . .
H3 H 0.0000 0.5423 0.1749 0.073 Uiso 1 2 calc SR . .
C4 C 0.0000 0.4505(4) 0.2228(2) 0.0593(16) Uani 1 2 d S . .
H4 H 0.0000 0.4826 0.2508 0.071 Uiso 1 2 d SR . .
C5 C 0.0000 0.3656(3) 0.22793(18) 0.0433(13) Uani 1 2 d S . .
C6 C 0.0000 0.3288(3) 0.27508(19) 0.0498(14) Uani 1 2 d S . .
H6 H 0.0000 0.3602 0.3034 0.060 Uiso 1 2 calc SR . .
C7 C 0.0000 0.2475(3) 0.27826(17) 0.0422(12) Uani 1 2 d S . .
C8 C 0.0000 0.1986(3) 0.23545(17) 0.0457(13) Uani 1 2 d S . .
H8 H 0.0000 0.1428 0.2382 0.055 Uiso 1 2 calc SR . .
C9 C 0.0000 0.2340(3) 0.19028(17) 0.0422(12) Uani 1 2 d S . .
C10 C 0.0000 0.3181(3) 0.18457(18) 0.0465(13) Uani 1 2 d S . .
C11 C 0.0000 0.1081(3) 0.1497(2) 0.0521(15) Uani 1 2 d S . .
C12 C 0.0000 0.0722(4) 0.0990(2) 0.0603(16) Uani 1 2 d S . .
C13 C 0.0000 -0.0498(6) 0.0569(3) 0.141(5) Uani 1 2 d S . .
C14 C 0.0000 0.2489(3) 0.3656(2) 0.0490(14) Uani 1 2 d S . .
C15 C 0.0000 0.1924(4) 0.40839(19) 0.0601(16) Uani 1 2 d S . .
C16 C 0.0000 0.1926(7) 0.4955(3) 0.116(4) Uani 1 2 d S . .
H14A H 0.112(5) 0.279(2) 0.3681(12) 0.049(10) Uiso 1 1 d . . .
H11A H -0.112(6) 0.088(2) 0.1659(14) 0.060(12) Uiso 1 1 d . . .
H16A H 0.0000 0.236(4) 0.524(3) 0.09(2) Uiso 1 2 d S . .
H17A H 0.071(9) 0.144(4) 0.495(2) 0.13(3) Uiso 1 1 d . . .
H13A H 0.057(9) -0.104(3) 0.0607(17) 0.12(2) Uiso 1 1 d . . .
H13B H 0.0000 -0.016(8) 0.027(4) 0.20(6) Uiso 1 2 d S . .
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'
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
_geom_angle_publ_flag
C9 O1 C11 117.1(4) . . ?
C12 O2 C13 114.5(5) . . ?
C7 O4 C14 116.6(4) . . ?
C15 O5 C16 117.3(6) . . ?
C2 C1 C10 121.0(5) . . ?
C2 C1 H1 119.5 . . ?
C10 C1 H1 119.5 . . ?
C1 C2 C3 120.7(6) . . ?
C1 C2 H2 119.6 . . ?
C3 C2 H2 119.6 . . ?
C4 C3 C2 119.7(5) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C3 C4 C5 121.6(5) . . ?
C3 C4 H4 119.1 . . ?
C5 C4 H4 119.4 . . ?
C4 C5 C10 118.2(5) . . ?
C4 C5 C6 121.2(5) . . ?
C10 C5 C6 120.6(5) . . ?
C7 C6 C5 119.2(5) . . ?
C7 C6 H6 120.4 . . ?
C5 C6 H6 120.4 . . ?
C6 C7 O4 125.3(4) . . ?
C6 C7 C8 121.3(5) . . ?
O4 C7 C8 113.4(4) . . ?
C9 C8 C7 119.4(5) . . ?
C9 C8 H8 120.3 . . ?
C7 C8 H8 120.3 . . ?
C8 C9 O1 123.8(5) . . ?
C8 C9 C10 121.9(5) . . ?
O1 C9 C10 114.2(4) . . ?
C9 C10 C5 117.5(4) . . ?
C9 C10 C1 123.7(5) . . ?
C5 C10 C1 118.8(5) . . ?
O1 C11 C12 110.0(5) . . ?
O1 C11 H11A 113(3) . . ?
C12 C11 H11A 107(2) . . ?
O3 C12 O2 125.3(5) . . ?
O3 C12 C11 126.1(6) . . ?
O2 C12 C11 108.5(5) . . ?
O2 C13 H13A 111(3) . . ?
O2 C13 H13B 116(7) . . ?
H13A C13 H13B 127(7) . . ?
O4 C14 C15 109.3(5) . . ?
O4 C14 H14A 111(2) . . ?
C15 C14 H14A 107(2) . . ?
O6 C15 O5 124.3(5) . . ?
O6 C15 C14 127.3(5) . . ?
O5 C15 C14 108.4(5) . . ?
O5 C16 H16A 108(4) . . ?
O5 C16 H17A 114(4) . . ?
H16A C16 H17A 127(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 C9 1.377(6) . ?
O1 C11 1.395(6) . ?
O2 C12 1.327(7) . ?
O2 C13 1.440(8) . ?
O3 C12 1.191(7) . ?
O4 C7 1.375(6) . ?
O4 C14 1.412(6) . ?
O5 C15 1.333(7) . ?
O5 C16 1.435(9) . ?
O6 C15 1.182(7) . ?
C1 C2 1.359(8) . ?
C1 C10 1.422(7) . ?
C1 H1 0.9300 . ?
C2 C3 1.398(8) . ?
C2 H2 0.9300 . ?
C3 C4 1.371(8) . ?
C3 H3 0.9300 . ?
C4 C5 1.417(8) . ?
C4 H4 0.9300 . ?
C5 C10 1.418(7) . ?
C5 C6 1.419(7) . ?
C6 C7 1.354(8) . ?
C6 H6 0.9300 . ?
C7 C8 1.419(7) . ?
C8 C9 1.361(7) . ?
C8 H8 0.9300 . ?
C9 C10 1.408(7) . ?
C11 C12 1.500(8) . ?
C11 H11A 0.94(4) . ?
C13 H13A 0.99(5) . ?
C13 H13B 0.99(10) . ?
C14 C15 1.495(8) . ?
C14 H14A 0.90(4) . ?
C16 H16A 1.06(7) . ?
C16 H17A 0.93(6) . ?
