#------------------------------------------------------------------------------
#$Date: 2017-08-09 05:02:05 +0300 (Wed, 09 Aug 2017) $
#$Revision: 199653 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/22/88/7228865.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_7228865
loop_
_publ_author_name
'shukla, rahul'
'Saeed, Aamer'
'Simpson, Jim'
'Chopra, Deepak'
_publ_section_title
;
 Quantitative investigation of C-H…π and other intermolecular
 interactions in a series of crystalline N-(substituted
 phenyl)-2-naphthamide derivatives.
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/C7CE01310H
_journal_year                    2017
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C17 H13 N O'
_chemical_formula_sum            'C17 H13 N O'
_chemical_formula_weight         247.28
_chemical_name_systematic
;
N-phenyl-2-naphthamide
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2014-04-15 deposited with the CCDC.
2017-08-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.767(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   28.7372(16)
_cell_length_b                   5.4797(3)
_cell_length_c                   7.8381(5)
_cell_measurement_reflns_used    2651
_cell_measurement_temperature    89(2)
_cell_measurement_theta_max      31.46
_cell_measurement_theta_min      2.69
_cell_volume                     1193.51(12)
_computing_cell_refinement       'APEX2 and SAINT (Bruker, 2011)'
_computing_data_collection       'APEX2 (Bruker, 2011)'
_computing_data_reduction        'SAINT (Bruker, 2011)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2006)'
_computing_publication_material
;
SHELXL-2013 (Sheldrick, 2008), enCIFer (Allen et al., 2004), 
PLATON (Spek, 2009), PublCIF (Westrip 2010)
;
_computing_structure_refinement
;
SHELXL-2013 (Sheldrick, 2008) & TITAN (Hunter & Simpson, 1999)
;
_computing_structure_solution
;
SHELXS-97 (Sheldrick, 2008) & TITAN (Hunter & Simpson, 1999)
;
_diffrn_ambient_temperature      89(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0380
_diffrn_reflns_av_unetI/netI     0.0497
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       42
_diffrn_reflns_limit_h_min       -42
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            10441
_diffrn_reflns_point_group_measured_fraction_full 0.906
_diffrn_reflns_point_group_measured_fraction_max 0.855
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.988
_diffrn_reflns_theta_min         4.321
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7968
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2011)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.376
_exptl_crystal_description       plate
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.520
_exptl_crystal_size_mid          0.420
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.409
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.056
_refine_ls_abs_structure_details
;
 Flack x determined using 1131 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.6(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         3533
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0529
_refine_ls_R_factor_gt           0.0445
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0683P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1103
_refine_ls_wR_factor_ref         0.1152
_reflns_Friedel_coverage         0.724
_reflns_Friedel_fraction_full    0.814
_reflns_Friedel_fraction_max     0.719
_reflns_number_gt                3049
_reflns_number_total             3533
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c7ce01310h2.cif
_cod_data_source_block           RA105_Compound_1
_cod_database_code               7228865
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.957
_shelx_estimated_absorpt_t_max   0.997
_shelxl_version_number           2013-4
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
C1 C 0.48153(7) 0.4488(4) 0.3857(3) 0.0128(4) Uani 1 1 d . .
H1 H 0.4865 0.5996 0.3331 0.015 Uiso 1 1 calc R U
C2 C 0.52074(7) 0.3079(4) 0.4682(3) 0.0133(4) Uani 1 1 d . .
C3 C 0.51353(7) 0.0856(4) 0.5509(3) 0.0153(4) Uani 1 1 d . .
H3 H 0.5404 -0.0104 0.6090 0.018 Uiso 1 1 calc R U
C4 C 0.46761(7) 0.0086(4) 0.5474(3) 0.0149(4) Uani 1 1 d . .
H4 H 0.4633 -0.1392 0.6047 0.018 Uiso 1 1 calc R U
C5 C 0.37908(7) 0.0675(4) 0.4509(3) 0.0148(4) Uani 1 1 d . .
H5 H 0.3740 -0.0808 0.5062 0.018 Uiso 1 1 calc R U
C6 C 0.34047(7) 0.2041(4) 0.3634(3) 0.0167(4) Uani 1 1 d . .
H6 H 0.3087 0.1489 0.3572 0.020 Uiso 1 1 calc R U
C7 C 0.34750(7) 0.4267(4) 0.2821(3) 0.0168(4) Uani 1 1 d . .
H7 H 0.3205 0.5200 0.2214 0.020 Uiso 1 1 calc R U
C8 C 0.39319(7) 0.5089(4) 0.2904(3) 0.0147(4) Uani 1 1 d . .
H8 H 0.3975 0.6594 0.2364 0.018 Uiso 1 1 calc R U
C9 C 0.43396(7) 0.3708(4) 0.3789(3) 0.0118(4) Uani 1 1 d . .
C10 C 0.42684(7) 0.1464(4) 0.4596(3) 0.0125(4) Uani 1 1 d . .
C21 C 0.56977(7) 0.3941(4) 0.4614(3) 0.0143(4) Uani 1 1 d . .
O1 O 0.57957(6) 0.6108(3) 0.4515(2) 0.0207(3) Uani 1 1 d . .
N1 N 0.60174(6) 0.2082(3) 0.4619(2) 0.0147(3) Uani 1 1 d . .
H1N H 0.5903(10) 0.065(5) 0.455(4) 0.018 Uiso 1 1 d . U
C11 C 0.64998(7) 0.2332(4) 0.4517(3) 0.0127(4) Uani 1 1 d . .
C12 C 0.67892(7) 0.4299(4) 0.5267(3) 0.0145(4) Uani 1 1 d . .
H12 H 0.6662 0.5576 0.5832 0.017 Uiso 1 1 calc R U
C13 C 0.72670(7) 0.4367(4) 0.5180(3) 0.0156(4) Uani 1 1 d . .
H13 H 0.7465 0.5704 0.5685 0.019 Uiso 1 1 calc R U
C14 C 0.74578(7) 0.2503(4) 0.4362(3) 0.0158(4) Uani 1 1 d . .
H14 H 0.7784 0.2568 0.4310 0.019 Uiso 1 1 calc R U
C15 C 0.71694(7) 0.0544(4) 0.3620(3) 0.0160(4) Uani 1 1 d . .
H15 H 0.7298 -0.0728 0.3056 0.019 Uiso 1 1 calc R U
C16 C 0.66907(7) 0.0444(4) 0.3703(3) 0.0143(4) Uani 1 1 d . .
H16 H 0.6495 -0.0904 0.3209 0.017 Uiso 1 1 calc R U
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 C1 C9 120.74(18) ?
C2 C1 H1 119.6 ?
C9 C1 H1 119.6 ?
C1 C2 C3 119.74(18) ?
C1 C2 C21 117.94(18) ?
C3 C2 C21 122.29(17) ?
C4 C3 C2 120.24(19) ?
C4 C3 H3 119.9 ?
C2 C3 H3 119.9 ?
C3 C4 C10 121.06(19) ?
C3 C4 H4 119.5 ?
C10 C4 H4 119.5 ?
C6 C5 C10 120.43(19) ?
C6 C5 H5 119.8 ?
C10 C5 H5 119.8 ?
C5 C6 C7 120.43(18) ?
C5 C6 H6 119.8 ?
C7 C6 H6 119.8 ?
C8 C7 C6 120.38(19) ?
C8 C7 H7 119.8 ?
C6 C7 H7 119.8 ?
C7 C8 C9 120.57(19) ?
C7 C8 H8 119.7 ?
C9 C8 H8 119.7 ?
C8 C9 C1 121.65(17) ?
C8 C9 C10 118.98(16) ?
C1 C9 C10 119.36(17) ?
C4 C10 C9 118.83(17) ?
C4 C10 C5 121.98(18) ?
C9 C10 C5 119.19(17) ?
O1 C21 N1 123.69(18) y
O1 C21 C2 122.66(17) y
N1 C21 C2 113.62(17) y
C21 N1 C11 126.35(17) y
C21 N1 H1N 116.2(18) ?
C11 N1 H1N 117.0(18) ?
C12 C11 C16 120.15(17) ?
C12 C11 N1 122.53(17) ?
C16 C11 N1 117.23(17) ?
C13 C12 C11 119.26(18) ?
C13 C12 H12 120.4 ?
C11 C12 H12 120.4 ?
C14 C13 C12 120.8(2) ?
C14 C13 H13 119.6 ?
C12 C13 H13 119.6 ?
C15 C14 C13 119.81(19) ?
C15 C14 H14 120.1 ?
C13 C14 H14 120.1 ?
C14 C15 C16 120.06(19) ?
C14 C15 H15 120.0 ?
C16 C15 H15 120.0 ?
C15 C16 C11 119.89(18) ?
C15 C16 H16 120.1 ?
C11 C16 H16 120.1 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 1.383(3) ?
C1 C9 1.420(3) ?
C1 H1 0.9500 ?
C2 C3 1.420(3) ?
C2 C21 1.500(3) y
C3 C4 1.379(3) ?
C3 H3 0.9500 ?
C4 C10 1.416(3) ?
C4 H4 0.9500 ?
C5 C6 1.369(3) ?
C5 C10 1.424(3) ?
C5 H5 0.9500 ?
C6 C7 1.415(3) ?
C6 H6 0.9500 ?
C7 C8 1.374(3) ?
C7 H7 0.9500 ?
C8 C9 1.419(3) ?
C8 H8 0.9500 ?
C9 C10 1.421(3) ?
C21 O1 1.227(3) ?
C21 N1 1.371(3) y
N1 C11 1.416(2) y
N1 H1N 0.85(3) y
C11 C12 1.396(3) ?
C11 C16 1.399(3) ?
C12 C13 1.393(3) ?
C12 H12 0.9500 ?
C13 C14 1.391(3) ?
C13 H13 0.9500 ?
C14 C15 1.390(3) ?
C14 H14 0.9500 ?
C15 C16 1.395(3) ?
C15 H15 0.9500 ?
C16 H16 0.9500 ?
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
N1 H1N O1 0.85(3) 2.51(3) 3.332(2) 165(2) 1_545
C1 H1 Cg1 0.95 2.97 3.700(2) 135 2_564
C4 H4 Cg1 0.95 2.81 3.482(2) 129 2_555
C8 H8 Cg2 0.95 2.82 3.433(2) 123 2_564
C12 H12 Cg3 0.95 2.96 3.652(2) 131 2_565
C15 H15 Cg3 0.95 2.90 3.570(2) 129 2_554
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
C9 C1 C2 C3 -1.6(3) ?
C9 C1 C2 C21 176.51(18) ?
C1 C2 C3 C4 0.8(3) ?
C21 C2 C3 C4 -177.2(2) ?
C2 C3 C4 C10 0.9(3) ?
C10 C5 C6 C7 -0.7(3) ?
C5 C6 C7 C8 -0.2(3) ?
C6 C7 C8 C9 0.6(3) ?
C7 C8 C9 C1 178.48(19) ?
C7 C8 C9 C10 -0.2(3) ?
C2 C1 C9 C8 -178.0(2) ?
C2 C1 C9 C10 0.7(3) ?
C3 C4 C10 C9 -1.9(3) ?
C3 C4 C10 C5 178.6(2) ?
C8 C9 C10 C4 179.8(2) ?
C1 C9 C10 C4 1.1(3) ?
C8 C9 C10 C5 -0.6(3) ?
C1 C9 C10 C5 -179.4(2) ?
C6 C5 C10 C4 -179.3(2) ?
C6 C5 C10 C9 1.1(3) ?
C1 C2 C21 O1 29.1(3) y
C3 C2 C21 O1 -152.8(2) y
C1 C2 C21 N1 -149.0(2) y
C3 C2 C21 N1 29.0(3) y
O1 C21 N1 C11 0.1(4) y
C2 C21 N1 C11 178.20(19) y
C21 N1 C11 C12 33.8(3) y
C21 N1 C11 C16 -149.6(2) y
C16 C11 C12 C13 0.7(3) ?
N1 C11 C12 C13 177.21(19) ?
C11 C12 C13 C14 -0.2(3) ?
C12 C13 C14 C15 0.0(3) ?
C13 C14 C15 C16 -0.3(3) ?
C14 C15 C16 C11 0.7(3) ?
C12 C11 C16 C15 -0.9(3) ?
N1 C11 C16 C15 -177.65(18) ?
