#------------------------------------------------------------------------------
#$Date: 2020-09-18 03:28:35 +0200 (vie 18 de sep de 2020) $
#$Revision: 256515 $
#$URL: svn://www.crystallography.net/cod/cif/7/24/12/7241270.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_7241270
loop_
_publ_author_name
'Bristow, Jonathan'
'Naftalin, Isaac'
'Cliff, Stacey V. A.'
'Yang, Songjie'
'Wallis, John D.'
'Carravetta, Marina'
'Heinmaa, Ivo'
'Stern, Raivo'
_publ_section_title
;
 Modelling of an Aza-Michael Reaction from Crystalline Naphthalene
 Derivatives Containing Peri-Peri Interactions: Very Long N-C
 Bonds?
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/D0CE01137A
_journal_year                    2020
_chemical_formula_moiety         'C17 H16 N2 O2'
_chemical_formula_sum            'C17 H16 N2 O2'
_chemical_formula_weight         280.32
_chemical_melting_point          373-340
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-09-26
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-07-28 deposited with the CCDC.	2020-09-17 downloaded from the CCDC.
;
_cell_angle_alpha                102.971(7)
_cell_angle_beta                 101.832(7)
_cell_angle_gamma                113.041(8)
_cell_formula_units_Z            2
_cell_length_a                   8.6964(8)
_cell_length_b                   9.2214(7)
_cell_length_c                   10.4886(8)
_cell_measurement_reflns_used    2531
_cell_measurement_temperature    150.01(10)
_cell_measurement_theta_max      30.3790
_cell_measurement_theta_min      2.5540
_cell_volume                     712.90(13)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9832
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -87.00  -1.00   1.00    2.50    --  -19.89 -62.00  38.11   86
  2  ω    -86.00   0.00   1.00    2.50    --  -19.89 -64.00-134.56   86
  3  ω      3.00  84.00   1.00    2.50    --   20.05  57.00   0.00   81
  4  ω     10.00  56.00   1.00    2.50    --   20.05  57.00-180.00   46
  5  ω      1.00  53.00   1.00    2.50    --   20.05  65.00 -94.72   52
  6  ω    -44.00  17.00   1.00    2.50    --   20.05 -57.00-180.00   61
  7  ω    -41.00   9.00   1.00    2.50    --   20.05 -19.00-120.00   50
  8  ω      0.00  87.00   1.00    2.50    --   20.05  65.00  76.57   87
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0419341000
_diffrn_orient_matrix_UB_12      -0.0679048000
_diffrn_orient_matrix_UB_13      -0.0635006000
_diffrn_orient_matrix_UB_21      -0.0467113000
_diffrn_orient_matrix_UB_22      0.0401171000
_diffrn_orient_matrix_UB_23      -0.0275926000
_diffrn_orient_matrix_UB_31      0.0696690000
_diffrn_orient_matrix_UB_32      0.0408587000
_diffrn_orient_matrix_UB_33      -0.0244404000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0298
_diffrn_reflns_av_unetI/netI     0.0429
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            8910
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.274
_diffrn_reflns_theta_min         2.551
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.757
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_description       block
_exptl_crystal_F_000             296
_exptl_crystal_recrystallization_method
'Slow evaporation from a diethyl ether solution.'
_exptl_crystal_size_max          0.475
_exptl_crystal_size_mid          0.406
_exptl_crystal_size_min          0.286
_refine_diff_density_max         0.266
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         3523
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0656
_refine_ls_R_factor_gt           0.0472
_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)+(0.0428P)²+0.1525P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1024
_refine_ls_wR_factor_ref         0.1135
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2719
_reflns_number_total             3523
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ce01137a2.cif
_cod_data_source_block           jb423absbeam
_cod_original_cell_volume        712.90(11)
_cod_database_code               7241270
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'C17 H16 O2 N2'
_chemical_oxdiff_usercomment     'Yellow Block'
_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.
;
_reflns_odcompleteness_completeness 99.80
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.22
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C6(H6), C7(H7), C8(H8), C13(H13)
2.b Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C17(H17A,H17B,H17C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.061
_oxdiff_exptl_absorpt_empirical_full_min 0.934
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O -0.24112(13) 0.23208(13) 0.02615(11) 0.0369(3) Uani 1 1 d . . . . .
O2 O -0.05826(13) 0.14764(12) 0.13419(10) 0.0292(2) Uani 1 1 d . . . . .
N1 N 0.45886(15) 0.53890(14) 0.26254(11) 0.0234(3) Uani 1 1 d . . . . .
N2 N -0.04716(17) 0.66686(16) 0.15325(14) 0.0364(3) Uani 1 1 d . . . . .
C1 C 0.55707(17) 0.67175(16) 0.39203(13) 0.0218(3) Uani 1 1 d . . . . .
C2 C 0.73888(18) 0.75332(18) 0.44243(15) 0.0288(3) Uani 1 1 d . . . . .
H2 H 0.803156 0.718685 0.393214 0.035 Uiso 1 1 calc R . . . .
C3 C 0.82846(19) 0.88915(19) 0.56826(16) 0.0339(4) Uani 1 1 d . . . . .
H3 H 0.951317 0.941050 0.602627 0.041 Uiso 1 1 calc R . . . .
C4 C 0.73769(19) 0.94493(18) 0.63965(15) 0.0316(4) Uani 1 1 d . . . . .
H4 H 0.798946 1.036786 0.720973 0.038 Uiso 1 1 calc R . . . .
C5 C 0.55035(19) 0.86471(17) 0.59165(14) 0.0257(3) Uani 1 1 d . . . . .
C6 C 0.4537(2) 0.92213(18) 0.66417(15) 0.0311(3) Uani 1 1 d . . . . .
H6 H 0.513598 1.014827 0.744926 0.037 Uiso 1 1 calc R . . . .
C7 C 0.2735(2) 0.84313(19) 0.61704(15) 0.0324(3) Uani 1 1 d . . . . .
H7 H 0.211335 0.884741 0.663608 0.039 Uiso 1 1 calc R . . . .
C8 C 0.18135(19) 0.69882(18) 0.49813(15) 0.0277(3) Uani 1 1 d . . . . .
H8 H 0.058406 0.645220 0.467933 0.033 Uiso 1 1 calc R . . . .
C9 C 0.26902(17) 0.63513(16) 0.42545(13) 0.0216(3) Uani 1 1 d . . . . .
C10 C 0.45825(17) 0.72172(16) 0.46830(13) 0.0212(3) Uani 1 1 d . . . . .
C11 C 0.5374(2) 0.42917(19) 0.22354(17) 0.0346(4) Uani 1 1 d . . . . .
H11A H 0.635345 0.485971 0.194486 0.052 Uiso 1 1 calc GR . . . .
H11B H 0.450468 0.329266 0.148891 0.052 Uiso 1 1 calc GR . . . .
H11C H 0.578095 0.400055 0.301588 0.052 Uiso 1 1 calc GR . . . .
C12 C 0.4120(2) 0.59985(19) 0.15047(15) 0.0312(3) Uani 1 1 d . . . . .
H12A H 0.357914 0.669363 0.177471 0.047 Uiso 1 1 calc GR . . . .
H12B H 0.330600 0.506324 0.068703 0.047 Uiso 1 1 calc GR . . . .
H12C H 0.516800 0.663832 0.131755 0.047 Uiso 1 1 calc GR . . . .
C13 C 0.16377(17) 0.47063(17) 0.31412(14) 0.0224(3) Uani 1 1 d . . . . .
H13 H 0.196775 0.386739 0.317786 0.027 Uiso 1 1 calc R . . . .
C14 C 0.02271(17) 0.43474(17) 0.20749(14) 0.0234(3) Uani 1 1 d . . . . .
C15 C -0.01583(17) 0.56486(17) 0.17870(14) 0.0266(3) Uani 1 1 d . . . . .
C16 C -0.10636(18) 0.26336(18) 0.11141(14) 0.0253(3) Uani 1 1 d . . . . .
C17 C -0.1847(2) -0.02357(18) 0.04995(17) 0.0355(4) Uani 1 1 d . . . . .
H17A H -0.194175 -0.038941 -0.045465 0.053 Uiso 1 1 calc GR . . . .
H17B H -0.297997 -0.046619 0.060694 0.053 Uiso 1 1 calc GR . . . .
H17C H -0.145588 -0.098605 0.078784 0.053 Uiso 1 1 calc GR . . . .
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_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 10 4 0.1570
-1 -10 -3 0.1160
-9 0 11 0.2063
9 0 -12 0.1871
-9 7 -7 0.2113
5 -9 11 0.2234
-1 9 -13 0.1465
7 -12 -2 0.0901
12 -4 0 0.2495
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
C16 O2 C17 114.87(11) . . ?
C1 N1 C11 115.60(11) . . ?
C1 N1 C12 111.86(11) . . ?
C11 N1 C12 110.93(12) . . ?
C2 C1 N1 123.15(13) . . ?
C2 C1 C10 120.01(13) . . ?
C10 C1 N1 116.82(11) . . ?
C1 C2 H2 119.8 . . ?
C1 C2 C3 120.44(14) . . ?
C3 C2 H2 119.8 . . ?
C2 C3 H3 119.6 . . ?
C4 C3 C2 120.81(14) . . ?
C4 C3 H3 119.6 . . ?
C3 C4 H4 119.7 . . ?
C3 C4 C5 120.66(14) . . ?
C5 C4 H4 119.7 . . ?
C4 C5 C10 119.00(14) . . ?
C6 C5 C4 121.39(13) . . ?
C6 C5 C10 119.61(13) . . ?
C5 C6 H6 119.7 . . ?
C7 C6 C5 120.69(14) . . ?
C7 C6 H6 119.7 . . ?
C6 C7 H7 119.9 . . ?
C6 C7 C8 120.19(14) . . ?
C8 C7 H7 119.9 . . ?
C7 C8 H8 119.3 . . ?
C9 C8 C7 121.49(14) . . ?
C9 C8 H8 119.3 . . ?
C8 C9 C10 119.31(13) . . ?
C8 C9 C13 117.89(12) . . ?
C10 C9 C13 122.53(12) . . ?
C1 C10 C5 118.90(12) . . ?
C1 C10 C9 122.56(12) . . ?
C5 C10 C9 118.54(13) . . ?
N1 C11 H11A 109.5 . . ?
N1 C11 H11B 109.5 . . ?
N1 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N1 C12 H12A 109.5 . . ?
N1 C12 H12B 109.5 . . ?
N1 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C9 C13 H13 118.0 . . ?
C14 C13 C9 123.96(12) . . ?
C14 C13 H13 118.0 . . ?
C13 C14 C15 121.31(13) . . ?
C13 C14 C16 124.71(12) . . ?
C15 C14 C16 113.98(11) . . ?
N2 C15 C14 178.73(16) . . ?
O1 C16 O2 124.10(13) . . ?
O1 C16 C14 123.68(13) . . ?
O2 C16 C14 112.18(11) . . ?
O2 C17 H17A 109.5 . . ?
O2 C17 H17B 109.5 . . ?
O2 C17 H17C 109.5 . . ?
H17A C17 H17B 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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C16 1.2026(16) . ?
O2 C16 1.3393(16) . ?
O2 C17 1.4487(17) . ?
N1 C1 1.4259(17) . ?
N1 C11 1.4586(18) . ?
N1 C12 1.4639(17) . ?
N2 C15 1.1462(18) . ?
C1 C2 1.3759(18) . ?
C1 C10 1.4203(19) . ?
C2 H2 0.9300 . ?
C2 C3 1.411(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.355(2) . ?
C4 H4 0.9300 . ?
C4 C5 1.417(2) . ?
C5 C6 1.413(2) . ?
C5 C10 1.4271(19) . ?
C6 H6 0.9300 . ?
C6 C7 1.363(2) . ?
C7 H7 0.9300 . ?
C7 C8 1.407(2) . ?
C8 H8 0.9300 . ?
C8 C9 1.377(2) . ?
C9 C10 1.4334(18) . ?
C9 C13 1.4772(19) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13 0.9300 . ?
C13 C14 1.3485(18) . ?
C14 C15 1.4420(18) . ?
C14 C16 1.4851(19) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 176.98(12) . . . . ?
N1 C1 C10 C5 -173.86(11) . . . . ?
N1 C1 C10 C9 5.45(18) . . . . ?
C1 C2 C3 C4 -2.0(2) . . . . ?
C2 C1 C10 C5 4.62(18) . . . . ?
C2 C1 C10 C9 -176.07(12) . . . . ?
C2 C3 C4 C5 2.0(2) . . . . ?
C3 C4 C5 C6 -179.44(13) . . . . ?
C3 C4 C5 C10 1.3(2) . . . . ?
C4 C5 C6 C7 -179.68(13) . . . . ?
C4 C5 C10 C1 -4.57(18) . . . . ?
C4 C5 C10 C9 176.09(11) . . . . ?
C5 C6 C7 C8 2.6(2) . . . . ?
C6 C5 C10 C1 176.19(12) . . . . ?
C6 C5 C10 C9 -3.15(18) . . . . ?
C6 C7 C8 C9 -1.0(2) . . . . ?
C7 C8 C9 C10 -2.72(19) . . . . ?
C7 C8 C9 C13 171.48(12) . . . . ?
C8 C9 C10 C1 -174.62(12) . . . . ?
C8 C9 C10 C5 4.70(18) . . . . ?
C8 C9 C13 C14 55.15(18) . . . . ?
C9 C13 C14 C15 12.5(2) . . . . ?
C9 C13 C14 C16 -166.72(13) . . . . ?
C10 C1 C2 C3 -1.4(2) . . . . ?
C10 C5 C6 C7 -0.5(2) . . . . ?
C10 C9 C13 C14 -130.85(14) . . . . ?
C11 N1 C1 C2 34.45(18) . . . . ?
C11 N1 C1 C10 -147.12(12) . . . . ?
C12 N1 C1 C2 -93.79(15) . . . . ?
C12 N1 C1 C10 84.64(14) . . . . ?
C13 C9 C10 C1 11.46(19) . . . . ?
C13 C9 C10 C5 -169.23(11) . . . . ?
C13 C14 C16 O1 171.91(14) . . . . ?
C13 C14 C16 O2 -5.9(2) . . . . ?
C15 C14 C16 O1 -7.4(2) . . . . ?
C15 C14 C16 O2 174.82(12) . . . . ?
C17 O2 C16 O1 -1.7(2) . . . . ?
C17 O2 C16 C14 176.05(12) . . . . ?
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.0000 10.0000 4.0000 -0.9331 0.2908 0.3108
-1.0000 -10.0000 -3.0000 0.9115 -0.2717 -0.4049
-9.0000 -0.0000 11.0000 -0.3211 0.1169 -0.8959
9.0000 0.0000 -12.0000 0.3846 -0.0893 0.9203
-9.0000 7.0000 -7.0000 0.3466 0.8944 -0.1699
5.0000 -9.0000 11.0000 -0.2970 -0.8981 -0.2882
-1.0000 9.0000 -13.0000 0.2563 0.7665 0.6158
7.0000 -12.0000 -2.0000 0.6483 -0.7532 0.0463
12.0000 -4.0000 -0.0000 -0.2316 -0.7210 0.6726
