#------------------------------------------------------------------------------
#$Date: 2020-06-27 07:51:42 +0300 (Sat, 27 Jun 2020) $
#$Revision: 253509 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/21/2022166.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_2022166
loop_
_publ_author_name
'Hillman, Zachary E.'
'Tanski, Joseph M.'
'Roberts, Andrea'
_publ_section_title
;
 Crystal and geometry-optimized structure of an anthracene-based
 Diels--Alder adduct
;
_journal_coeditor_code           QF3039
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S2053229620008128
_journal_volume                  76
_journal_year                    2020
_chemical_formula_iupac          'C21 H19 N O3'
_chemical_formula_moiety         'C21 H19 N O3'
_chemical_formula_sum            'C21 H19 N O3'
_chemical_formula_weight         333.37
_chemical_name_systematic
17-Ethyl-1-hydroxymethyl-17-azapentacyclo[6.6.5.0^2,7^.0^9,14^.0^15,19^]nonadeca-2,4,6,9,11,13-hexaene-16,18-dione
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_cell_angle_alpha                90
_cell_angle_beta                 109.430(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.2110(13)
_cell_length_b                   8.1447(9)
_cell_length_c                   17.6634(19)
_cell_measurement_reflns_used    9901
_cell_measurement_temperature    125.(2)
_cell_measurement_theta_max      31.5227
_cell_measurement_theta_min      2.7838
_cell_volume                     1656.7(3)
_computing_cell_refinement
;
SAINT (Bruker, 2013)
;
_computing_data_collection
;
APEX2 (Bruker, 2013)
;
_computing_data_reduction
;
SAINT (Bruker, 2013)
;
_computing_molecular_graphics
;
SHELXTL2014 (Sheldrick, 2008)
;
_computing_publication_material
;
SHELXTL2014 (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT2014 (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      125(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ and ω 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  0.0281
_diffrn_reflns_av_unetI/netI     0.0174
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            36543
_diffrn_reflns_theta_full        31.52
_diffrn_reflns_theta_max         31.52
_diffrn_reflns_theta_min         1.77
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.90
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2013)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.330
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.499
_refine_diff_density_min         -0.219
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         5486
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0450
_refine_ls_R_factor_gt           0.0386
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0633P)²+0.4753P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1043
_refine_ls_wR_factor_ref         0.1098
_reflns_number_gt                4784
_reflns_number_total             5486
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            qf3039sup1.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2022166
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_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_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.73973(6) 0.96692(8) 0.50764(4) 0.02254(15) Uani d 1 . .
O O2 0.85332(6) 0.43164(8) 0.53871(4) 0.01947(14) Uani d 1 . .
O O3 0.64094(6) 0.20767(8) 0.58591(4) 0.01919(14) Uani d 1 . .
H H3 0.6757(11) 0.1545(16) 0.5608(8) 0.023 Uiso d 1 . .
N N1 0.81304(6) 0.70584(9) 0.51418(4) 0.01427(14) Uani d 1 . .
C C1 0.68346(7) 0.48699(9) 0.63505(5) 0.01212(14) Uani d 1 . .
C C2 0.56498(7) 0.52050(10) 0.64336(5) 0.01331(14) Uani d 1 . .
C C3 0.49221(7) 0.40476(11) 0.66004(5) 0.01628(16) Uani d 1 . .
H H3B 0.515 0.2928 0.6681 0.02 Uiso calc 1 . .
C C4 0.38528(8) 0.45515(12) 0.66472(5) 0.01995(17) Uani d 1 . .
H H4A 0.3354 0.377 0.6764 0.024 Uiso calc 1 . .
C C5 0.35126(8) 0.61850(13) 0.65242(6) 0.02073(18) Uani d 1 . .
H H5A 0.2777 0.6508 0.6547 0.025 Uiso calc 1 . .
C C6 0.42446(7) 0.73570(11) 0.63676(5) 0.01791(16) Uani d 1 . .
H H6A 0.4014 0.8475 0.6288 0.021 Uiso calc 1 . .
C C7 0.53159(7) 0.68625(10) 0.63305(5) 0.01386(15) Uani d 1 . .
C C8 0.62088(7) 0.79749(10) 0.61719(5) 0.01353(14) Uani d 1 . .
H H8A 0.5972 0.9156 0.613 0.016 Uiso calc 1 . .
C C9 0.73581(7) 0.76794(10) 0.68294(5) 0.01299(14) Uani d 1 . .
C C10 0.80741(8) 0.88879(10) 0.72961(5) 0.01651(16) Uani d 1 . .
H H10A 0.7859 1.0012 0.7212 0.02 Uiso calc 1 . .
C C11 0.91105(8) 0.84398(12) 0.78889(5) 0.01926(17) Uani d 1 . .
H H11A 0.9597 0.9259 0.8215 0.023 Uiso calc 1 . .
C C12 0.94309(8) 0.67986(12) 0.80034(5) 0.01901(17) Uani d 1 . .
H H12A 1.0135 0.6501 0.841 0.023 Uiso calc 1 . .
C C13 0.87269(7) 0.55800(11) 0.75254(5) 0.01583(15) Uani d 1 . .
H H13A 0.8954 0.446 0.7602 0.019 Uiso calc 1 . .
C C14 0.76898(7) 0.60215(10) 0.69361(5) 0.01276(14) Uani d 1 . .
C C15 0.67343(7) 0.55010(9) 0.54881(5) 0.01195(14) Uani d 1 . .
H H15A 0.6158 0.4816 0.5073 0.014 Uiso calc 1 . .
C C16 0.63540(7) 0.73176(10) 0.53816(5) 0.01289(14) Uani d 1 . .
H H16A 0.5606 0.743 0.4927 0.015 Uiso calc 1 . .
C C17 0.73168(7) 0.81973(10) 0.51840(5) 0.01469(15) Uani d 1 . .
C C18 0.78911(7) 0.54773(10) 0.53426(5) 0.01320(14) Uani d 1 . .
C C19 0.91711(8) 0.74664(11) 0.49436(6) 0.01882(17) Uani d 1 . .
H H19A 0.899 0.8381 0.4552 0.023 Uiso calc 1 . .
H H19B 0.9399 0.6504 0.4687 0.023 Uiso calc 1 . .
C C20 1.01784(9) 0.79573(14) 0.56769(7) 0.0291(2) Uani d 1 . .
H H20A 1.0848 0.8246 0.5515 0.044 Uiso calc 1 . .
H H20B 1.0384 0.7038 0.6056 0.044 Uiso calc 1 . .
H H20C 0.9955 0.8906 0.5934 0.044 Uiso calc 1 . .
C C21 0.71934(7) 0.30681(10) 0.64652(5) 0.01569(15) Uani d 1 . .
H H21A 0.7988 0.2945 0.6442 0.019 Uiso calc 1 . .
H H21B 0.7202 0.2694 0.7 0.019 Uiso calc 1 . .
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C21 O3 H3 . . 111.2(9) ?
C17 N1 C18 . . 113.10(7) ?
C17 N1 C19 . . 123.94(7) ?
C18 N1 C19 . . 122.90(7) ?
C14 C1 C21 . . 113.59(7) ?
C14 C1 C2 . . 106.38(6) ?
C21 C1 C2 . . 113.50(7) ?
C14 C1 C15 . . 105.74(6) ?
C21 C1 C15 . . 111.67(6) ?
C2 C1 C15 . . 105.29(6) ?
C3 C2 C7 . . 120.00(7) ?
C3 C2 C1 . . 126.24(7) ?
C7 C2 C1 . . 113.76(7) ?
C2 C3 C4 . . 119.23(8) ?
C2 C3 H3B . . 120.4 ?
C4 C3 H3B . . 120.4 ?
C5 C4 C3 . . 120.58(8) ?
C5 C4 H4A . . 119.7 ?
C3 C4 H4A . . 119.7 ?
C4 C5 C6 . . 120.51(8) ?
C4 C5 H5A . . 119.7 ?
C6 C5 H5A . . 119.7 ?
C7 C6 C5 . . 119.03(8) ?
C7 C6 H6A . . 120.5 ?
C5 C6 H6A . . 120.5 ?
C6 C7 C2 . . 120.61(8) ?
C6 C7 C8 . . 125.59(8) ?
C2 C7 C8 . . 113.79(7) ?
C7 C8 C9 . . 107.68(7) ?
C7 C8 C16 . . 105.28(6) ?
C9 C8 C16 . . 106.25(6) ?
C7 C8 H8A . . 112.4 ?
C9 C8 H8A . . 112.4 ?
C16 C8 H8A . . 112.4 ?
C10 C9 C14 . . 120.31(8) ?
C10 C9 C8 . . 125.58(7) ?
C14 C9 C8 . . 114.09(7) ?
C9 C10 C11 . . 119.60(8) ?
C9 C10 H10A . . 120.2 ?
C11 C10 H10A . . 120.2 ?
C12 C11 C10 . . 120.13(8) ?
C12 C11 H11A . . 119.9 ?
C10 C11 H11A . . 119.9 ?
C11 C12 C13 . . 120.58(8) ?
C11 C12 H12A . . 119.7 ?
C13 C12 H12A . . 119.7 ?
C14 C13 C12 . . 119.45(8) ?
C14 C13 H13A . . 120.3 ?
C12 C13 H13A . . 120.3 ?
C13 C14 C9 . . 119.91(7) ?
C13 C14 C1 . . 126.58(7) ?
C9 C14 C1 . . 113.50(7) ?
C18 C15 C16 . . 104.53(6) ?
C18 C15 C1 . . 112.50(6) ?
C16 C15 C1 . . 110.76(6) ?
C18 C15 H15A . . 109.6 ?
C16 C15 H15A . . 109.6 ?
C1 C15 H15A . . 109.6 ?
C17 C16 C15 . . 104.87(6) ?
C17 C16 C8 . . 111.86(7) ?
C15 C16 C8 . . 109.83(6) ?
C17 C16 H16A . . 110.1 ?
C15 C16 H16A . . 110.1 ?
C8 C16 H16A . . 110.1 ?
O1 C17 N1 . . 123.67(8) ?
O1 C17 C16 . . 127.49(8) ?
N1 C17 C16 . . 108.84(7) ?
O2 C18 N1 . . 123.44(8) ?
O2 C18 C15 . . 128.05(8) ?
N1 C18 C15 . . 108.50(6) ?
N1 C19 C20 . . 112.22(8) ?
N1 C19 H19A . . 109.2 ?
C20 C19 H19A . . 109.2 ?
N1 C19 H19B . . 109.2 ?
C20 C19 H19B . . 109.2 ?
H19A C19 H19B . . 107.9 ?
C19 C20 H20A . . 109.5 ?
C19 C20 H20B . . 109.5 ?
H20A C20 H20B . . 109.5 ?
C19 C20 H20C . . 109.5 ?
H20A C20 H20C . . 109.5 ?
H20B C20 H20C . . 109.5 ?
O3 C21 C1 . . 110.71(7) ?
O3 C21 H21A . . 109.5 ?
C1 C21 H21A . . 109.5 ?
O3 C21 H21B . . 109.5 ?
C1 C21 H21B . . 109.5 ?
H21A C21 H21B . . 108.1 ?
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
O1 C17 . 1.2229(10) ?
O2 C18 . 1.2140(10) ?
O3 C21 . 1.4257(10) ?
O3 H3 . 0.830(12) ?
N1 C17 . 1.3792(10) ?
N1 C18 . 1.3923(11) ?
N1 C19 . 1.4643(11) ?
C1 C14 . 1.5237(11) ?
C1 C21 . 1.5256(11) ?
C1 C2 . 1.5266(11) ?
C1 C15 . 1.5734(11) ?
C2 C3 . 1.3926(11) ?
C2 C7 . 1.4044(11) ?
C3 C4 . 1.3971(12) ?
C3 H3B . 0.95 ?
C4 C5 . 1.3891(14) ?
C4 H4A . 0.95 ?
C5 C6 . 1.3969(13) ?
C5 H5A . 0.95 ?
C6 C7 . 1.3910(11) ?
C6 H6A . 0.95 ?
C7 C8 . 1.5137(11) ?
C8 C9 . 1.5139(11) ?
C8 C16 . 1.5592(11) ?
C8 H8A . 1.0 ?
C9 C10 . 1.3904(11) ?
C9 C14 . 1.4044(11) ?
C10 C11 . 1.3963(13) ?
C10 H10A . 0.95 ?
C11 C12 . 1.3886(13) ?
C11 H11A . 0.95 ?
C12 C13 . 1.3979(12) ?
C12 H12A . 0.95 ?
C13 C14 . 1.3926(11) ?
C13 H13A . 0.95 ?
C15 C18 . 1.5177(11) ?
C15 C16 . 1.5434(11) ?
C15 H15A . 1.0 ?
C16 C17 . 1.5134(11) ?
C16 H16A . 1.0 ?
C19 C20 . 1.5135(14) ?
C19 H19A . 0.99 ?
C19 H19B . 0.99 ?
C20 H20A . 0.98 ?
C20 H20B . 0.98 ?
C20 H20C . 0.98 ?
C21 H21A . 0.99 ?
C21 H21B . 0.99 ?
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
_geom_hbond_publ_flag
O3 H3 O1 1_545 0.830(12) 2.078(12) 2.8846(10) 164.0(13) ?
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C14 C1 C2 C3 . . . . -125.36(8) ?
C21 C1 C2 C3 . . . . 0.28(12) ?
C15 C1 C2 C3 . . . . 122.71(8) ?
C14 C1 C2 C7 . . . . 54.22(9) ?
C21 C1 C2 C7 . . . . 179.86(7) ?
C15 C1 C2 C7 . . . . -57.71(8) ?
C7 C2 C3 C4 . . . . 1.27(12) ?
C1 C2 C3 C4 . . . . -179.18(8) ?
C2 C3 C4 C5 . . . . 0.40(13) ?
C3 C4 C5 C6 . . . . -1.29(14) ?
C4 C5 C6 C7 . . . . 0.48(13) ?
C5 C6 C7 C2 . . . . 1.20(13) ?
C5 C6 C7 C8 . . . . -179.64(8) ?
C3 C2 C7 C6 . . . . -2.09(12) ?
C1 C2 C7 C6 . . . . 178.31(7) ?
C3 C2 C7 C8 . . . . 178.66(7) ?
C1 C2 C7 C8 . . . . -0.94(10) ?
C6 C7 C8 C9 . . . . 128.23(8) ?
C2 C7 C8 C9 . . . . -52.57(9) ?
C6 C7 C8 C16 . . . . -118.72(9) ?
C2 C7 C8 C16 . . . . 60.49(8) ?
C7 C8 C9 C10 . . . . -128.93(8) ?
C16 C8 C9 C10 . . . . 118.67(8) ?
C7 C8 C9 C14 . . . . 52.38(9) ?
C16 C8 C9 C14 . . . . -60.03(8) ?
C14 C9 C10 C11 . . . . -1.91(12) ?
C8 C9 C10 C11 . . . . 179.47(8) ?
C9 C10 C11 C12 . . . . 0.91(13) ?
C10 C11 C12 C13 . . . . 0.41(13) ?
C11 C12 C13 C14 . . . . -0.71(13) ?
C12 C13 C14 C9 . . . . -0.29(12) ?
C12 C13 C14 C1 . . . . 178.42(8) ?
C10 C9 C14 C13 . . . . 1.61(12) ?
C8 C9 C14 C13 . . . . -179.62(7) ?
C10 C9 C14 C1 . . . . -177.27(7) ?
C8 C9 C14 C1 . . . . 1.51(10) ?
C21 C1 C14 C13 . . . . 1.20(11) ?
C2 C1 C14 C13 . . . . 126.79(8) ?
C15 C1 C14 C13 . . . . -121.59(8) ?
C21 C1 C14 C9 . . . . 179.99(7) ?
C2 C1 C14 C9 . . . . -54.43(9) ?
C15 C1 C14 C9 . . . . 57.19(8) ?
C14 C1 C15 C18 . . . . 59.80(8) ?
C21 C1 C15 C18 . . . . -64.22(8) ?
C2 C1 C15 C18 . . . . 172.18(6) ?
C14 C1 C15 C16 . . . . -56.78(8) ?
C21 C1 C15 C16 . . . . 179.21(6) ?
C2 C1 C15 C16 . . . . 55.60(8) ?
C18 C15 C16 C17 . . . . -0.01(8) ?
C1 C15 C16 C17 . . . . 121.39(7) ?
C18 C15 C16 C8 . . . . -120.36(7) ?
C1 C15 C16 C8 . . . . 1.04(9) ?
C7 C8 C16 C17 . . . . -174.10(6) ?
C9 C8 C16 C17 . . . . -60.04(8) ?
C7 C8 C16 C15 . . . . -58.08(8) ?
C9 C8 C16 C15 . . . . 55.97(8) ?
C18 N1 C17 O1 . . . . 175.69(8) ?
C19 N1 C17 O1 . . . . -1.61(13) ?
C18 N1 C17 C16 . . . . -4.18(9) ?
C19 N1 C17 C16 . . . . 178.52(7) ?
C15 C16 C17 O1 . . . . -177.46(9) ?
C8 C16 C17 O1 . . . . -58.47(11) ?
C15 C16 C17 N1 . . . . 2.39(8) ?
C8 C16 C17 N1 . . . . 121.39(7) ?
C17 N1 C18 O2 . . . . -175.69(8) ?
C19 N1 C18 O2 . . . . 1.65(13) ?
C17 N1 C18 C15 . . . . 4.16(9) ?
C19 N1 C18 C15 . . . . -178.50(7) ?
C16 C15 C18 O2 . . . . 177.49(8) ?
C1 C15 C18 O2 . . . . 57.24(11) ?
C16 C15 C18 N1 . . . . -2.35(8) ?
C1 C15 C18 N1 . . . . -122.60(7) ?
C17 N1 C19 C20 . . . . 87.01(10) ?
C18 N1 C19 C20 . . . . -90.04(10) ?
C14 C1 C21 O3 . . . . -175.24(7) ?
C2 C1 C21 O3 . . . . 63.06(9) ?
C15 C1 C21 O3 . . . . -55.77(9) ?

_cod_database_fobs_code 2022166
