#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/02/2200218.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_2200218
loop_
_publ_author_name
'Bond, Andrew D.'
'Clayden, J.'
'Wheatley, Andrew E. H.'
_publ_section_title
;
 N,N-Diisopropyl-1-naphthamide
;
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o292
_journal_page_last               o294
_journal_paper_doi               10.1107/S1600536801003580
_journal_volume                  57
_journal_year                    2001
_chemical_formula_moiety         'C17 H21 N O'
_chemical_formula_sum            'C17 H21 N O'
_chemical_formula_weight         255.35
_chemical_name_common            N,N-diisopropyl-1-naphthamide
_chemical_name_systematic        N,N-diisopropyl-1-naphthamide
_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'
_cell_angle_alpha                90.00
_cell_angle_beta                 101.958(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.5403(10)
_cell_length_b                   13.6498(19)
_cell_length_c                   14.4042(11)
_cell_measurement_reflns_used    13372
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      25.0
_cell_measurement_theta_min      1.0
_cell_volume                     1450.4(3)
_computing_cell_refinement       'HKL SCALEPACK (Otwinowski & Minor 1997)'
_computing_data_collection       'COLLECT (Nonius BV, 1998)'
_computing_data_reduction
;
HKL DENZO and SCALEPACK (Otwinowski & Minor 1997)
;
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick 1997)'
_diffrn_ambient_temperature      180(2)
_diffrn_measured_fraction_theta_full .98
_diffrn_measured_fraction_theta_max .98
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'Thin-slice ω and φ'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     .71073
_diffrn_reflns_av_R_equivalents  .0637
_diffrn_reflns_av_sigmaI/netI    .0698
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            8393
_diffrn_reflns_theta_full        24.9
_diffrn_reflns_theta_max         24.93
_diffrn_reflns_theta_min         3.56
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    .072
_exptl_absorpt_correction_T_max  .997
_exptl_absorpt_correction_T_min  .992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SORTAV; Blessing, 1995)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.169
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             552
_exptl_crystal_size_max          .21
_exptl_crystal_size_mid          .14
_exptl_crystal_size_min          .05
_refine_diff_density_max         .266
_refine_diff_density_min         -.205
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     176
_refine_ls_number_reflns         2494
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          .1025
_refine_ls_R_factor_gt           .0652
_refine_ls_shift/su_max          .026
_refine_ls_shift/su_mean         .003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0467P)²+0.8144P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         .1477
_reflns_number_gt                1725
_reflns_number_total             2494
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            om6007.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2200218
_cod_database_fobs_code          2200218
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
O1 .6333(2) .64758(14) .11239(14) .0524(5) Uani d . 1 . . O
N1 .9299(3) .60519(15) .15704(14) .0374(5) Uani d . 1 . . N
C1 .6901(3) .48566(19) .17037(17) .0376(6) Uani d . 1 . . C
C2 .6366(3) .41683(19) .10165(17) .0378(6) Uani d . 1 . . C
H2 .6462 .4308 .0383 .045 Uiso calc R 1 . . H
C3 .5673(3) .3252(2) .1226(2) .0465(7) Uani d . 1 . . C
H3 .5313 .2781 .0738 .056 Uiso calc R 1 . . H
C4 .5523(3) .3046(2) .21413(19) .0435(7) Uani d . 1 . . C
H4 .5060 .2429 .2286 .052 Uiso calc R 1 . . H
C5 .5937(3) .3556(2) .38114(19) .0466(7) Uani d . 1 . . C
H5 .5480 .2942 .3964 .056 Uiso calc R 1 . . H
C6 .6457(4) .4225(2) .4516(2) .0565(8) Uani d . 1 . . C
H6 .6385 .4073 .5150 .068 Uiso calc R 1 . . H
C7 .7099(4) .5135(2) .4295(2) .0547(8) Uani d . 1 . . C
H7 .7443 .5607 .4784 .066 Uiso calc R 1 . . H
C8 .7242(3) .5364(2) .33956(18) .0420(6) Uani d . 1 . . C
H8 .7680 .5991 .3265 .050 Uiso calc R 1 . . H
C9 .6744(3) .4673(2) .26480(18) .0404(6) Uani d . 1 . . C
C10 .6050(3) .37428(18) .28635(18) .0364(6) Uani d . 1 . . C
C11 .7507(3) .5863(2) .14439(17) .0401(6) Uani d . 1 . . C
C12 1.0706(3) .53121(19) .19379(17) .0390(6) Uani d . 1 . . C
H12 1.0062 .4682 .1998 .047 Uiso calc R 1 . . H
C13 1.1959(3) .5129(2) .12596(19) .0484(7) Uani d . 1 . . C
H13A 1.1238 .5016 .0620 .073 Uiso calc R 1 . . H
H13B 1.2710 .4552 .1467 .073 Uiso calc R 1 . . H
H13C 1.2741 .5702 .1252 .073 Uiso calc R 1 . . H
C14 1.1776(4) .5570(2) .29204(18) .0514(8) Uani d . 1 . . C
H14A 1.2410 .6192 .2893 .077 Uiso calc R 1 . . H
H14B 1.2663 .5052 .3143 .077 Uiso calc R 1 . . H
H14C 1.0947 .5631 .3359 .077 Uiso calc R 1 . . H
C15 .9942(3) .70360(19) .13482(19) .0438(7) Uani d . 1 . . C
H15 1.1296 .7013 .1522 .053 Uiso calc R 1 . . H
C16 .9362(4) .7839(2) .1954(3) .0667(9) Uani d . 1 . . C
H16A .8038 .7901 .1800 .100 Uiso calc R 1 . . H
H16B .9912 .8462 .1825 .100 Uiso calc R 1 . . H
H16C .9761 .7672 .2627 .100 Uiso calc R 1 . . H
C17 .9454(4) .7262(2) .0292(2) .0631(9) Uani d . 1 . . C
H17A .9901 .6736 -.0062 .095 Uiso calc R 1 . . H
H17B 1.0012 .7884 .0168 .095 Uiso calc R 1 . . H
H17C .8134 .7312 .0089 .095 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 .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O .0106 .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
C11 N1 C12 122.7(2) y
C11 N1 C15 120.4(2) y
C12 N1 C15 116.88(19) y
C2 C1 C9 120.4(2) y
C2 C1 C11 120.2(2) y
C9 C1 C11 119.2(2) y
C1 C2 C3 121.5(2) y
C1 C2 H2 119.3 ?
C3 C2 H2 119.3 ?
C4 C3 C2 119.6(2) y
C4 C3 H3 120.2 ?
C2 C3 H3 120.2 ?
C3 C4 C10 120.3(2) y
C3 C4 H4 119.9 ?
C10 C4 H4 119.9 ?
C6 C5 C10 122.4(3) y
C6 C5 H5 118.8 ?
C10 C5 H5 118.8 ?
C5 C6 C7 119.2(3) y
C5 C6 H6 120.4 ?
C7 C6 H6 120.4 ?
C8 C7 C6 121.5(3) y
C8 C7 H7 119.3 ?
C6 C7 H7 119.3 ?
C7 C8 C9 120.6(3) y
C7 C8 H8 119.7 ?
C9 C8 H8 119.7 ?
C1 C9 C8 123.4(2) y
C1 C9 C10 118.3(2) y
C8 C9 C10 118.4(2) y
C4 C10 C5 122.0(2) y
C4 C10 C9 120.0(2) y
C5 C10 C9 117.9(2) y
O1 C11 N1 122.7(2) y
O1 C11 C1 118.4(2) y
N1 C11 C1 118.9(2) y
N1 C12 C13 112.2(2) y
N1 C12 C14 112.2(2) y
C13 C12 C14 110.9(2) y
N1 C12 H12 107.0 ?
C13 C12 H12 107.0 ?
C14 C12 H12 107.0 ?
C12 C13 H13A 109.5 ?
C12 C13 H13B 109.5 ?
H13A C13 H13B 109.5 ?
C12 C13 H13C 109.5 ?
H13A C13 H13C 109.5 ?
H13B C13 H13C 109.5 ?
C12 C14 H14A 109.5 ?
C12 C14 H14B 109.5 ?
H14A C14 H14B 109.5 ?
C12 C14 H14C 109.5 ?
H14A C14 H14C 109.5 ?
H14B C14 H14C 109.5 ?
N1 C15 C16 112.5(2) y
N1 C15 C17 112.1(2) y
C16 C15 C17 112.9(2) y
N1 C15 H15 106.2 ?
C16 C15 H15 106.2 ?
C17 C15 H15 106.2 ?
C15 C16 H16A 109.5 ?
C15 C16 H16B 109.5 ?
H16A C16 H16B 109.5 ?
C15 C16 H16C 109.5 ?
H16A C16 H16C 109.5 ?
H16B C16 H16C 109.5 ?
C15 C17 H17A 109.5 ?
C15 C17 H17B 109.5 ?
H17A C17 H17B 109.5 ?
C15 C17 H17C 109.5 ?
H17A C17 H17C 109.5 ?
H17B C17 H17C 109.5 ?
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
O1 C11 . 1.236(3) y
N1 C11 . 1.351(3) y
N1 C12 . 1.481(3) y
N1 C15 . 1.485(3) y
C1 C2 . 1.364(3) y
C1 C9 . 1.412(3) y
C1 C11 . 1.519(4) y
C2 C3 . 1.411(4) y
C2 H2 . .9500 ?
C3 C4 . 1.376(4) y
C3 H3 . .9500 ?
C4 C10 . 1.405(4) y
C4 H4 . .9500 ?
C5 C6 . 1.360(4) y
C5 C10 . 1.409(4) y
C5 H5 . .9500 ?
C6 C7 . 1.394(4) y
C6 H6 . .9500 ?
C7 C8 . 1.358(4) y
C7 H7 . .9500 ?
C8 C9 . 1.422(3) y
C8 H8 . .9500 ?
C9 C10 . 1.432(4) y
C12 C13 . 1.514(4) y
C12 C14 . 1.518(3) y
C12 H12 . 1.0000 ?
C13 H13A . .9800 ?
C13 H13B . .9800 ?
C13 H13C . .9800 ?
C14 H14A . .9800 ?
C14 H14B . .9800 ?
C14 H14C . .9800 ?
C15 C16 . 1.521(4) y
C15 C17 . 1.521(4) y
C15 H15 . 1.0000 ?
C16 H16A . .9800 ?
C16 H16B . .9800 ?
C16 H16C . .9800 ?
C17 H17A . .9800 ?
C17 H17B . .9800 ?
C17 H17C . .9800 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C5 H5 O1 2_645 .95 2.41 3.327(3) 161.7
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
C9 C1 C2 C3 -1.1(4)
C11 C1 C2 C3 -175.4(2)
C1 C2 C3 C4 .3(4)
C2 C3 C4 C10 .2(4)
C10 C5 C6 C7 1.1(4)
C5 C6 C7 C8 -1.1(4)
C6 C7 C8 C9 -.2(4)
C2 C1 C9 C8 -178.8(2)
C11 C1 C9 C8 -4.5(3)
C2 C1 C9 C10 1.4(3)
C11 C1 C9 C10 175.7(2)
C7 C8 C9 C1 -178.4(2)
C7 C8 C9 C10 1.4(4)
C3 C4 C10 C5 -179.3(2)
C3 C4 C10 C9 .1(4)
C6 C5 C10 C4 179.5(2)
C6 C5 C10 C9 .1(4)
C1 C9 C10 C4 -.9(3)
C8 C9 C10 C4 179.3(2)
C1 C9 C10 C5 178.5(2)
C8 C9 C10 C5 -1.3(3)
C12 N1 C11 O1 -178.9(2)
C15 N1 C11 O1 1.7(4)
C12 N1 C11 C1 1.1(3)
C15 N1 C11 C1 -178.4(2)
C2 C1 C11 O1 80.6(3)
C9 C1 C11 O1 -93.8(3)
C2 C1 C11 N1 -99.4(3)
C9 C1 C11 N1 86.2(3)
C11 N1 C12 C13 122.4(2)
C15 N1 C12 C13 -58.1(3)
C11 N1 C12 C14 -111.8(3)
C15 N1 C12 C14 67.7(3)
C11 N1 C15 C16 61.7(3)
C12 N1 C15 C16 -117.7(2)
C11 N1 C15 C17 -66.8(3)
C12 N1 C15 C17 113.8(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 245733
