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#$Date: 2022-11-23 11:04:27 +0200 (Wed, 23 Nov 2022) $
#$Revision: 279497 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/62/8106216.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_8106216
loop_
_publ_author_name
'Quan, Yan'
_publ_section_title
;
 Crystal structure of
 6-amino-8-(2-methoxy-phenyl)-2-methyl-2,3,8,8a-tetrahydro-1H-iso-quinoline-5,7,7-tricarbonitrile
 monohydrate, C20H21N5O2
;
_journal_issue                   4
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              559
_journal_page_last               560
_journal_paper_doi               10.1515/ncrs-2017-0317
_journal_volume                  233
_journal_year                    2018
_chemical_formula_moiety         'C20 H19 N5 O, H2 O'
_chemical_formula_sum            'C20 H21 N5 O2'
_chemical_formula_weight         363.42
_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
_atom_sites_solution_primary     dual
_cell_angle_alpha                90
_cell_angle_beta                 93.749(18)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.594(4)
_cell_length_b                   9.366(5)
_cell_length_c                   14.147(4)
_cell_measurement_reflns_used    1947
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.73
_cell_measurement_theta_min      2.64
_cell_volume                     1929.6(13)
_computing_cell_refinement       'SAINT v7.60A (Bruker, 2009)'
_computing_data_collection       'Bruker SMART Apex-II'
_computing_data_reduction        'SAINT v7.60A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_solution    'Olex2 (Dolomanov et al., 2009)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.953
_diffrn_measurement_device_type  'Bruker Apex-II CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0580
_diffrn_reflns_av_unetI/netI     0.0799
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.953
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            11291
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.953
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.907
_diffrn_reflns_theta_min         2.586
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.9850
_exptl_absorpt_correction_T_min  0.9784
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.251
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.238
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.953
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     252
_refine_ls_number_reflns         4406
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      0.953
_refine_ls_R_factor_all          0.1112
_refine_ls_R_factor_gt           0.0607
_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)+(0.1196P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1760
_refine_ls_wR_factor_ref         0.2131
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2384
_reflns_number_total             4406
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2017-0317_suppl.cif
_cod_data_source_block           a
_cod_original_cell_volume        1929.6(12)
_cod_database_code               8106216
_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_max   0.985
_shelx_estimated_absorpt_t_min   0.978
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 H1WB-O1W = H1WA-O1W
 0.83 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C8(H8), C9(H9)
3.b Secondary CH2 refined with riding coordinates:
 C18(H18B,H18A), C19(H19A,H19B)
3.c Me refined with riding coordinates:
 C7(H7B,H7A,H7C), C20(H20B,H20C,H20A)
3.d Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C17(H17)
3.e X=CH2 refined with riding coordinates:
 N3(H3B,H3A)
;
_olex2_submission_special_instructions 'No special instructions were received'
_publcif_funding_html
;
;
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_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 0.44937(11) 0.7916(2) 0.52297(14) 0.0677(6) Uani 1 1 d . . . . .
N1 N 0.21574(12) 1.1754(2) 0.71135(15) 0.0470(5) Uani 1 1 d . . . . .
N2 N 0.02070(14) 1.1087(2) 0.32157(18) 0.0631(6) Uani 1 1 d . . . . .
N3 N 0.10546(13) 0.7542(2) 0.35244(15) 0.0558(6) Uani 1 1 d . . . . .
H3B H 0.069953 0.795997 0.310111 0.067 Uiso 1 1 calc R . . . .
H3A H 0.119588 0.665815 0.345827 0.067 Uiso 1 1 calc R . . . .
N4 N 0.30992(14) 0.5610(3) 0.41960(18) 0.0673(7) Uani 1 1 d . . . . .
N5 N 0.09206(15) 0.6047(2) 0.61049(19) 0.0636(7) Uani 1 1 d . . . . .
C1 C 0.33464(14) 0.7584(2) 0.63136(17) 0.0393(5) Uani 1 1 d . . . . .
C2 C 0.30775(16) 0.7022(3) 0.71698(18) 0.0483(6) Uani 1 1 d . . . . .
H2 H 0.249533 0.723152 0.736230 0.058 Uiso 1 1 calc R . . . .
C3 C 0.36616(18) 0.6154(3) 0.7743(2) 0.0582(7) Uani 1 1 d . . . . .
H3 H 0.347369 0.580521 0.831444 0.070 Uiso 1 1 calc R . . . .
C4 C 0.45242(18) 0.5818(3) 0.7450(2) 0.0650(8) Uani 1 1 d . . . . .
H4 H 0.490618 0.520969 0.781508 0.078 Uiso 1 1 calc R . . . .
C5 C 0.48195(16) 0.6379(3) 0.6623(2) 0.0603(7) Uani 1 1 d . . . . .
H5 H 0.540528 0.616349 0.644310 0.072 Uiso 1 1 calc R . . . .
C6 C 0.42448(14) 0.7273(3) 0.60479(19) 0.0480(6) Uani 1 1 d . . . . .
C7 C 0.5339(2) 0.7496(5) 0.4850(3) 0.1236(18) Uani 1 1 d . . . . .
H7B H 0.542450 0.802795 0.428249 0.185 Uiso 1 1 calc R . . . .
H7A H 0.583993 0.768568 0.530737 0.185 Uiso 1 1 calc R . . . .
H7C H 0.532019 0.649465 0.470668 0.185 Uiso 1 1 calc R . . . .
C8 C 0.26883(13) 0.8446(2) 0.56429(16) 0.0371(5) Uani 1 1 d . . . . .
H8 H 0.306876 0.894833 0.520374 0.044 Uiso 1 1 calc R . . . .
C9 C 0.21083(13) 0.9596(2) 0.61114(16) 0.0378(5) Uani 1 1 d . . . . .
H9 H 0.166744 0.911557 0.649740 0.045 Uiso 1 1 calc R . . . .
C10 C 0.15770(14) 1.0459(2) 0.53468(17) 0.0421(6) Uani 1 1 d . . . . .
C11 C 0.12199(14) 0.9688(3) 0.44856(17) 0.0423(6) Uani 1 1 d . . . . .
C12 C 0.06474(15) 1.0455(3) 0.37805(19) 0.0472(6) Uani 1 1 d . . . . .
C13 C 0.13910(13) 0.8276(2) 0.42941(17) 0.0405(5) Uani 1 1 d . . . . .
C14 C 0.20240(13) 0.7427(2) 0.50190(16) 0.0374(5) Uani 1 1 d . . . . .
C15 C 0.26066(15) 0.6386(2) 0.45294(17) 0.0439(6) Uani 1 1 d . . . . .
C16 C 0.14140(15) 0.6611(2) 0.56299(18) 0.0427(6) Uani 1 1 d . . . . .
C17 C 0.14534(18) 1.1868(3) 0.5469(2) 0.0562(7) Uani 1 1 d . . . . .
H17 H 0.112636 1.236972 0.498977 0.067 Uiso 1 1 calc R . . . .
C18 C 0.1807(2) 1.2675(3) 0.6321(2) 0.0601(7) Uani 1 1 d . . . . .
H18B H 0.229685 1.330118 0.614543 0.072 Uiso 1 1 calc R . . . .
H18A H 0.131722 1.326890 0.653586 0.072 Uiso 1 1 calc R . . . .
C19 C 0.27131(14) 1.0585(2) 0.67573(18) 0.0437(6) Uani 1 1 d . . . . .
H19A H 0.298916 1.004212 0.728623 0.052 Uiso 1 1 calc R . . . .
H19B H 0.320313 1.097621 0.640499 0.052 Uiso 1 1 calc R . . . .
C20 C 0.26917(18) 1.2600(3) 0.7836(2) 0.0628(8) Uani 1 1 d . . . . .
H20B H 0.231516 1.335432 0.805710 0.094 Uiso 1 1 calc R . . . .
H20C H 0.288851 1.199413 0.835788 0.094 Uiso 1 1 calc R . . . .
H20A H 0.321900 1.300163 0.756328 0.094 Uiso 1 1 calc R . . . .
O1W O 0.10596(13) 1.0467(2) 0.85330(16) 0.0632(6) Uani 1 1 d D . . . .
H1WA H 0.131(3) 1.087(4) 0.806(2) 0.117(15) Uiso 1 1 d D . . . .
H1WB H 0.0511(13) 1.071(3) 0.848(2) 0.080(10) Uiso 1 1 d D . . . .
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_site_symmetry_1
_geom_angle_site_symmetry_3
C6 O1 C7 118.5(2) . .
C19 N1 C18 110.22(19) . .
C19 N1 C20 111.03(17) . .
C20 N1 C18 110.66(19) . .
H3B N3 H3A 120.0 . .
C13 N3 H3B 120.0 . .
C13 N3 H3A 120.0 . .
C2 C1 C6 118.0(2) . .
C2 C1 C8 122.22(19) . .
C6 C1 C8 119.7(2) . .
C1 C2 H2 119.2 . .
C3 C2 C1 121.7(2) . .
C3 C2 H2 119.2 . .
C2 C3 H3 120.3 . .
C4 C3 C2 119.3(3) . .
C4 C3 H3 120.3 . .
C3 C4 H4 119.7 . .
C5 C4 C3 120.5(2) . .
C5 C4 H4 119.7 . .
C4 C5 H5 119.6 . .
C4 C5 C6 120.7(2) . .
C6 C5 H5 119.6 . .
O1 C6 C1 115.7(2) . .
O1 C6 C5 124.6(2) . .
C5 C6 C1 119.7(2) . .
O1 C7 H7B 109.5 . .
O1 C7 H7A 109.5 . .
O1 C7 H7C 109.5 . .
H7B C7 H7A 109.5 . .
H7B C7 H7C 109.5 . .
H7A C7 H7C 109.5 . .
C1 C8 H8 106.7 . .
C1 C8 C9 116.09(19) . .
C1 C8 C14 111.21(17) . .
C9 C8 H8 106.7 . .
C9 C8 C14 109.01(15) . .
C14 C8 H8 106.7 . .
C8 C9 H9 108.5 . .
C10 C9 C8 109.47(18) . .
C10 C9 H9 108.5 . .
C10 C9 C19 110.38(17) . .
C19 C9 C8 111.41(16) . .
C19 C9 H9 108.5 . .
C11 C10 C9 117.45(19) . .
C17 C10 C9 119.8(2) . .
C17 C10 C11 122.8(2) . .
C12 C11 C10 118.7(2) . .
C13 C11 C10 124.9(2) . .
C13 C11 C12 116.4(2) . .
N2 C12 C11 178.5(2) . .
N3 C13 C11 125.9(2) . .
N3 C13 C14 116.12(19) . .
C11 C13 C14 118.0(2) . .
C13 C14 C8 111.99(17) . .
C15 C14 C8 107.77(16) . .
C15 C14 C13 111.11(19) . .
C16 C14 C8 110.62(18) . .
C16 C14 C13 107.05(16) . .
C16 C14 C15 108.27(18) . .
N4 C15 C14 175.5(2) . .
N5 C16 C14 176.5(2) . .
C10 C17 H17 118.0 . .
C10 C17 C18 124.1(2) . .
C18 C17 H17 118.0 . .
N1 C18 C17 113.77(19) . .
N1 C18 H18B 108.8 . .
N1 C18 H18A 108.8 . .
C17 C18 H18B 108.8 . .
C17 C18 H18A 108.8 . .
H18B C18 H18A 107.7 . .
N1 C19 C9 110.11(17) . .
N1 C19 H19A 109.6 . .
N1 C19 H19B 109.6 . .
C9 C19 H19A 109.6 . .
C9 C19 H19B 109.6 . .
H19A C19 H19B 108.2 . .
N1 C20 H20B 109.5 . .
N1 C20 H20C 109.5 . .
N1 C20 H20A 109.5 . .
H20B C20 H20C 109.5 . .
H20B C20 H20A 109.5 . .
H20C C20 H20A 109.5 . .
H1WA O1W H1WB 105(4) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C6 1.374(3) .
O1 C7 1.432(3) .
N1 C18 1.479(3) .
N1 C19 1.471(3) .
N1 C20 1.475(3) .
N2 C12 1.155(3) .
N3 H3B 0.8600 .
N3 H3A 0.8600 .
N3 C13 1.352(3) .
N4 C15 1.145(3) .
N5 C16 1.146(3) .
C1 C2 1.400(3) .
C1 C6 1.417(3) .
C1 C8 1.535(3) .
C2 H2 0.9300 .
C2 C3 1.398(4) .
C3 H3 0.9300 .
C3 C4 1.387(4) .
C4 H4 0.9300 .
C4 C5 1.377(4) .
C5 H5 0.9300 .
C5 C6 1.407(4) .
C7 H7B 0.9600 .
C7 H7A 0.9600 .
C7 H7C 0.9600 .
C8 H8 0.9800 .
C8 C9 1.545(3) .
C8 C14 1.587(3) .
C9 H9 0.9800 .
C9 C10 1.522(3) .
C9 C19 1.538(3) .
C10 C11 1.481(3) .
C10 C17 1.345(3) .
C11 C12 1.449(3) .
C11 C13 1.376(3) .
C13 C14 1.554(3) .
C14 C15 1.494(3) .
C14 C16 1.491(3) .
C17 H17 0.9300 .
C17 C18 1.486(4) .
C18 H18B 0.9700 .
C18 H18A 0.9700 .
C19 H19A 0.9700 .
C19 H19B 0.9700 .
C20 H20B 0.9600 .
C20 H20C 0.9600 .
C20 H20A 0.9600 .
O1W H1WA 0.866(19) .
O1W H1WB 0.832(18) .
