#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/25/2202573.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2202573
loop_
_publ_author_name
'Thamotharan, S.'
'Parthasarathi, V.'
'Gupta, P.'
'Jindal, D.P.'
'Piplani, P.'
'Linden, Anthony'
_publ_section_title
;
 N-(2-Naphthyloxymethylcarbonyl)pyrrolidine
;
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1334
_journal_page_last               o1335
_journal_paper_doi               10.1107/S1600536803017987
_journal_volume                  59
_journal_year                    2003
_chemical_formula_moiety         'C16 H17 N O2'
_chemical_formula_sum            'C16 H17 N O2'
_chemical_formula_weight         255.31
_chemical_melting_point          397
_chemical_name_systematic
;
N-(2-naphthyloxymethylcarbonyl)pyrrolidine
;
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 110.9738(11)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.6427(2)
_cell_length_b                   8.8035(2)
_cell_length_c                   14.4306(2)
_cell_measurement_reflns_used    3899
_cell_measurement_temperature    160(2)
_cell_measurement_theta_max      30.0
_cell_measurement_theta_min      2.0
_cell_volume                     1262.47(4)
_computing_cell_refinement       'DENZO--SMN (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 2000)'
_computing_data_reduction
'DENZO--SMN and SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'SHELXL97 and PLATON (Spek, 2003)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      160(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Nonius KappaCCD diffractometer'
_diffrn_measurement_method       'φ and ω scans with κ offsets'
_diffrn_radiation_monochromator  'horizontally mounted graphite crystal'
_diffrn_radiation_source         'Nonius FR591 sealed tube generator'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0470
_diffrn_reflns_av_sigmaI/netI    0.0406
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            33348
_diffrn_reflns_theta_full        30.03
_diffrn_reflns_theta_max         30.03
_diffrn_reflns_theta_min         2.76
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.509
_refine_diff_density_min         -0.303
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         3685
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0719
_refine_ls_R_factor_gt           0.0516
_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)+(0.0765P)²+0.2090P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1307
_refine_ls_wR_factor_ref         0.1439
_reflns_number_gt                2775
_reflns_number_total             3686
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            cv6222.cif
_cod_data_source_block           I
_cod_original_cell_volume        1262.46(4)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2202573
_cod_database_fobs_code          2202573
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_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
O11 0.72111(8) 0.52679(10) 0.40282(6) 0.0258(2) Uani d . 1 . . O
O13 0.91728(9) 0.71575(11) 0.40863(6) 0.0329(2) Uani d . 1 . . O
N14 1.00984(10) 0.71437(12) 0.57646(7) 0.0250(2) Uani d . 1 . . N
C1 0.59653(11) 0.36322(13) 0.47607(8) 0.0225(3) Uani d . 1 . . C
H1 0.6561 0.3833 0.5418 0.027 Uiso calc R 1 . . H
C2 0.61699(11) 0.43114(13) 0.39705(8) 0.0223(2) Uani d . 1 . . C
C3 0.52769(12) 0.40350(14) 0.29858(8) 0.0252(3) Uani d . 1 . . C
H3 0.5418 0.4528 0.2446 0.030 Uiso calc R 1 . . H
C4 0.42181(12) 0.30663(13) 0.28106(8) 0.0247(3) Uani d . 1 . . C
H4 0.3633 0.2884 0.2148 0.030 Uiso calc R 1 . . H
C5 0.28892(12) 0.13087(14) 0.34436(9) 0.0255(3) Uani d . 1 . . C
H5 0.2297 0.1106 0.2785 0.031 Uiso calc R 1 . . H
C6 0.26823(13) 0.06134(14) 0.42287(9) 0.0272(3) Uani d . 1 . . C
H6 0.1954 -0.0074 0.4112 0.033 Uiso calc R 1 . . H
C7 0.35519(13) 0.09200(14) 0.52097(9) 0.0273(3) Uani d . 1 . . C
H7 0.3402 0.0439 0.5750 0.033 Uiso calc R 1 . . H
C8 0.46083(12) 0.19043(13) 0.53880(8) 0.0248(3) Uani d . 1 . . C
H8 0.5180 0.2105 0.6052 0.030 Uiso calc R 1 . . H
C9 0.48618(11) 0.26294(13) 0.45948(8) 0.0214(2) Uani d . 1 . . C
C10 0.39775(11) 0.23241(13) 0.36073(8) 0.0218(2) Uani d . 1 . . C
C12 0.81293(12) 0.56020(14) 0.49915(8) 0.0236(3) Uani d . 1 . . C
H121 0.8574 0.4659 0.5323 0.028 Uiso calc R 1 . . H
H122 0.7648 0.6060 0.5396 0.028 Uiso calc R 1 . . H
C13 0.91719(12) 0.67071(14) 0.48940(8) 0.0238(3) Uani d . 1 . . C
C15 1.01720(12) 0.66274(15) 0.67521(9) 0.0277(3) Uani d . 1 . . C
H151 1.0330 0.5518 0.6828 0.033 Uiso calc R 1 . . H
H152 0.9335 0.6876 0.6870 0.033 Uiso calc R 1 . . H
C16 1.13665(16) 0.75073(18) 0.74576(11) 0.0421(4) Uani d . 1 . . C
H161 1.1198 0.7810 0.8064 0.051 Uiso calc R 1 . . H
H162 1.2197 0.6887 0.7652 0.051 Uiso calc R 1 . . H
C17 1.14902(18) 0.88943(19) 0.68716(11) 0.0456(4) Uani d . 1 . . C
H171 1.0868 0.9708 0.6909 0.055 Uiso calc R 1 . . H
H172 1.2421 0.9294 0.7120 0.055 Uiso calc R 1 . . H
C18 1.11106(12) 0.83033(15) 0.58232(9) 0.0286(3) Uani d . 1 . . C
H181 1.0729 0.9121 0.5332 0.034 Uiso calc R 1 . . H
H182 1.1898 0.7855 0.5712 0.034 Uiso calc R 1 . . H
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_publ_flag
C2 O11 C12 116.52(9) ?
C13 N14 C18 122.07(10) ?
C13 N14 C15 125.67(10) ?
C18 N14 C15 112.12(9) ?
C2 C1 C9 119.91(10) ?
C2 C1 H1 120.0 ?
C9 C1 H1 120.0 ?
O11 C2 C1 125.64(10) yes
O11 C2 C3 113.79(10) ?
C1 C2 C3 120.57(11) ?
C4 C3 C2 120.40(11) ?
C4 C3 H3 119.8 ?
C2 C3 H3 119.8 ?
C3 C4 C10 120.89(10) ?
C3 C4 H4 119.6 ?
C10 C4 H4 119.6 ?
C6 C5 C10 120.50(11) ?
C6 C5 H5 119.8 ?
C10 C5 H5 119.8 ?
C5 C6 C7 120.04(11) ?
C5 C6 H6 120.0 ?
C7 C6 H6 120.0 ?
C8 C7 C6 120.58(11) ?
C8 C7 H7 119.7 ?
C6 C7 H7 119.7 ?
C7 C8 C9 120.92(10) ?
C7 C8 H8 119.5 ?
C9 C8 H8 119.5 ?
C8 C9 C1 121.92(10) ?
C8 C9 C10 118.30(11) ?
C1 C9 C10 119.78(10) ?
C5 C10 C4 121.91(10) ?
C5 C10 C9 119.65(11) ?
C4 C10 C9 118.44(11) ?
O11 C12 C13 108.21(9) ?
O11 C12 H121 110.1 ?
C13 C12 H121 110.1 ?
O11 C12 H122 110.1 ?
C13 C12 H122 110.1 ?
H121 C12 H122 108.4 ?
O13 C13 N14 122.89(11) ?
O13 C13 C12 122.80(10) ?
N14 C13 C12 114.31(10) ?
N14 C15 C16 103.44(10) ?
N14 C15 H151 111.1 ?
C16 C15 H151 111.1 ?
N14 C15 H152 111.1 ?
C16 C15 H152 111.1 ?
H151 C15 H152 109.0 ?
C17 C16 C15 104.74(11) ?
C17 C16 H161 110.8 ?
C15 C16 H161 110.8 ?
C17 C16 H162 110.8 ?
C15 C16 H162 110.8 ?
H161 C16 H162 108.9 ?
C18 C17 C16 103.61(12) ?
C18 C17 H171 111.0 ?
C16 C17 H171 111.0 ?
C18 C17 H172 111.0 ?
C16 C17 H172 111.0 ?
H171 C17 H172 109.0 ?
N14 C18 C17 103.02(11) ?
N14 C18 H181 111.2 ?
C17 C18 H181 111.2 ?
N14 C18 H182 111.2 ?
C17 C18 H182 111.2 ?
H181 C18 H182 109.1 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O11 C2 . 1.3703(14) ?
O11 C12 . 1.4147(14) ?
O13 C13 . 1.2315(15) ?
N14 C13 . 1.3459(15) ?
N14 C18 . 1.4643(16) ?
N14 C15 . 1.4709(15) ?
C1 C2 . 1.3723(16) ?
C1 C9 . 1.4194(17) ?
C1 H1 . 0.9500 ?
C2 C3 . 1.4194(16) ?
C3 C4 . 1.3626(17) ?
C3 H3 . 0.9500 ?
C4 C10 . 1.4231(16) ?
C4 H4 . 0.9500 ?
C5 C6 . 1.3732(18) ?
C5 C10 . 1.4144(17) ?
C5 H5 . 0.9500 ?
C6 C7 . 1.4126(17) ?
C6 H6 . 0.9500 ?
C7 C8 . 1.3690(17) ?
C7 H7 . 0.9500 ?
C8 C9 . 1.4182(16) ?
C8 H8 . 0.9500 ?
C9 C10 . 1.4243(16) ?
C12 C13 . 1.5197(17) ?
C12 H121 . 0.9900 ?
C12 H122 . 0.9900 ?
C15 C16 . 1.5252(19) ?
C15 H151 . 0.9900 ?
C15 H152 . 0.9900 ?
C16 C17 . 1.518(2) ?
C16 H161 . 0.9900 ?
C16 H162 . 0.9900 ?
C17 C18 . 1.512(2) ?
C17 H171 . 0.9900 ?
C17 H172 . 0.9900 ?
C18 H181 . 0.9900 ?
C18 H182 . 0.9900 ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_publ_flag
C12 O11 C2 C1 -1.55(17) ?
C12 O11 C2 C3 179.33(10) ?
C9 C1 C2 O11 -178.29(10) ?
C9 C1 C2 C3 0.77(18) ?
O11 C2 C3 C4 177.85(10) ?
C1 C2 C3 C4 -1.31(18) ?
C2 C3 C4 C10 0.58(18) ?
C10 C5 C6 C7 0.57(18) ?
C5 C6 C7 C8 -0.23(19) ?
C6 C7 C8 C9 -0.50(18) ?
C7 C8 C9 C1 -178.81(11) ?
C7 C8 C9 C10 0.88(17) ?
C2 C1 C9 C8 -179.84(11) ?
C2 C1 C9 C10 0.47(17) ?
C6 C5 C10 C4 -179.83(11) ?
C6 C5 C10 C9 -0.18(17) ?
C3 C4 C10 C5 -179.69(11) ?
C3 C4 C10 C9 0.65(17) ?
C8 C9 C10 C5 -0.53(16) ?
C1 C9 C10 C5 179.16(10) ?
C8 C9 C10 C4 179.13(10) ?
C1 C9 C10 C4 -1.17(16) ?
C2 O11 C12 C13 -178.34(9) yes
C18 N14 C13 O13 5.85(19) ?
C15 N14 C13 O13 -178.70(11) ?
C18 N14 C13 C12 -174.56(10) ?
C15 N14 C13 C12 0.90(17) ?
O11 C12 C13 O13 -1.60(16) ?
O11 C12 C13 N14 178.81(10) yes
C13 N14 C15 C16 -178.27(12) ?
C18 N14 C15 C16 -2.43(14) ?
N14 C15 C16 C17 23.52(15) ?
C15 C16 C17 C18 -35.72(16) ?
C13 N14 C18 C17 156.45(12) ?
C15 N14 C18 C17 -19.56(14) ?
C16 C17 C18 N14 33.41(15) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 764064
