#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/58/4505830.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_4505830
loop_
_publ_author_name
'Price, Christopher P.'
'Grzesiak, Adam L.'
'Lang, Meidong'
'Matzger, Adam J.'
_publ_contact_author_address
;
Department of Chemistry and Department of Macromolecular Science 
and Engineering, 
The University of Michigan, Ann Arbor, Michigan 48109-1055
;
_publ_contact_author_name        'Adam J. Matzger'
_publ_section_title
;
 Polymorphism of Nabumetone
;
_journal_issue                   6
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              501
_journal_paper_doi               10.1021/cg0255568
_journal_volume                  2
_journal_year                    2002
_chemical_formula_sum            'C15 H16 O2'
_chemical_formula_weight         228.28
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 91.860(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   26.902(6)
_cell_length_b                   5.8844(13)
_cell_length_c                   7.8965(18)
_cell_measurement_reflns_used    6960
_cell_measurement_temperature    158(2)
_cell_measurement_theta_max      28.29
_cell_measurement_theta_min      3.54
_cell_volume                     1249.4(5)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      158(2)
_diffrn_detector_area_resol_mean 0.75
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0339
_diffrn_reflns_av_sigmaI/netI    0.0234
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            16033
_diffrn_reflns_theta_full        28.32
_diffrn_reflns_theta_max         28.32
_diffrn_reflns_theta_min         3.54
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.214
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.04
_exptl_crystal_size_mid          0.68
_exptl_crystal_size_min          0.68
_refine_diff_density_max         0.373
_refine_diff_density_min         -0.175
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3107
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0531
_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)+(0.0724P)²+0.2238P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1156
_refine_ls_wR_factor_ref         0.1246
_reflns_number_gt                2528
_reflns_number_total             3107
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg0255568-2_s2.cif
_cod_data_source_block           formII
_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 

Obvious syntax errors fixed at the publ_contact_author area miguel
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               4505830
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
O1 O 0.05061(3) 0.45180(13) 0.39668(10) 0.0277(2) Uani 1 1 d
O2 O 0.42360(4) 0.6223(3) -0.00436(18) 0.0789(4) Uani 1 1 d
C1 C 0.02632(4) 0.2489(2) 0.34074(16) 0.0325(3) Uani 1 1 d
H1A H 0.0248(5) 0.240(3) 0.217(2) 0.042(4) Uiso 1 1 d
H1B H -0.0080(6) 0.262(2) 0.3837(18) 0.038(4) Uiso 1 1 d
H1C H 0.0431(5) 0.113(3) 0.3885(19) 0.042(4) Uiso 1 1 d
C2 C 0.09802(4) 0.48726(17) 0.34402(12) 0.0220(2) Uani 1 1 d
C3 C 0.12478(4) 0.33714(17) 0.24976(11) 0.0211(2) Uani 1 1 d
H3A H 0.1107(4) 0.191(2) 0.2126(15) 0.025(3) Uiso 1 1 d
C4 C 0.17415(4) 0.39393(16) 0.20592(11) 0.0201(2) Uani 1 1 d
C5 C 0.20374(4) 0.24311(17) 0.11167(12) 0.0228(2) Uani 1 1 d
H5A H 0.1902(5) 0.096(2) 0.0768(16) 0.029(3) Uiso 1 1 d
C6 C 0.25083(4) 0.30294(18) 0.06830(13) 0.0264(2) Uani 1 1 d
H6A H 0.2701(5) 0.193(2) 0.0016(18) 0.036(3) Uiso 1 1 d
C7 C 0.27168(4) 0.51507(18) 0.11602(13) 0.0264(2) Uani 1 1 d
C8 C 0.24374(4) 0.66229(17) 0.20942(12) 0.0241(2) Uani 1 1 d
H8A H 0.2569(5) 0.809(2) 0.2435(16) 0.027(3) Uiso 1 1 d
C9 C 0.19489(4) 0.60578(16) 0.25614(11) 0.0209(2) Uani 1 1 d
C10 C 0.16565(4) 0.75653(16) 0.35201(12) 0.0228(2) Uani 1 1 d
H10A H 0.1788(5) 0.903(2) 0.3872(16) 0.027(3) Uiso 1 1 d
C11 C 0.11888(4) 0.69791(17) 0.39618(12) 0.0238(2) Uani 1 1 d
H11A H 0.0982(5) 0.800(2) 0.4622(17) 0.031(3) Uiso 1 1 d
C12 C 0.32347(4) 0.5770(2) 0.06495(16) 0.0344(3) Uani 1 1 d
H12A H 0.3280(6) 0.747(3) 0.0738(19) 0.046(4) Uiso 1 1 d
H12B H 0.3279(6) 0.532(3) -0.055(2) 0.047(4) Uiso 1 1 d
C13 C 0.36363(5) 0.4645(3) 0.17525(18) 0.0409(3) Uani 1 1 d
H13A H 0.3623(7) 0.518(3) 0.293(2) 0.057(5) Uiso 1 1 d
H13B H 0.3590(6) 0.299(3) 0.175(2) 0.059(5) Uiso 1 1 d
C14 C 0.41582(5) 0.5099(3) 0.1193(2) 0.0495(4) Uani 1 1 d
C15 C 0.45696(6) 0.4096(4) 0.2268(3) 0.0709(6) Uani 1 1 d
H15A H 0.4878(9) 0.418(4) 0.177(3) 0.075(6) Uiso 1 1 d
H15B H 0.4486(8) 0.250(4) 0.246(3) 0.087(7) Uiso 1 1 d
H15C H 0.4601(13) 0.492(7) 0.338(5) 0.062(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 0.0016 '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
C2 O1 C1 117.11(8)
O1 C2 C3 125.15(9)
O1 C2 C11 114.13(8)
C3 C2 C11 120.72(9)
C2 C3 C4 119.36(9)
C9 C4 C5 118.32(9)
C9 C4 C3 120.04(9)
C5 C4 C3 121.64(9)
C6 C5 C4 120.65(9)
C5 C6 C7 121.49(10)
C8 C7 C6 118.64(10)
C8 C7 C12 121.10(10)
C6 C7 C12 120.26(10)
C7 C8 C9 121.28(10)
C8 C9 C4 119.61(9)
C8 C9 C10 121.80(9)
C4 C9 C10 118.60(9)
C11 C10 C9 120.73(9)
C10 C11 C2 120.54(9)
C7 C12 C13 112.82(10)
C14 C13 C12 113.98(12)
O2 C14 C15 122.21(14)
O2 C14 C13 121.53(14)
C15 C14 C13 116.25(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C2 1.3703(12)
O1 C1 1.4243(14)
O2 C14 1.203(2)
C2 C3 1.3738(14)
C2 C11 1.4162(14)
C3 C4 1.4231(14)
C4 C9 1.4172(14)
C4 C5 1.4190(13)
C5 C6 1.3692(15)
C6 C7 1.4146(15)
C7 C8 1.3768(15)
C7 C12 1.5076(15)
C8 C9 1.4161(14)
C9 C10 1.4204(14)
C10 C11 1.3611(15)
C12 C13 1.5177(18)
C13 C14 1.5092(18)
C14 C15 1.495(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 4256
