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#$Date: 2023-01-23 12:26:03 +0200 (Mon, 23 Jan 2023) $
#$Revision: 280533 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/65/8106557.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_8106557
loop_
_publ_author_name
'Samipillai, Marivel'
'Govender, Thavendran'
'Kruger, Hendrik G.'
'Tricia, Naicker'
_publ_section_title
;
 Crystal structure of (S)-benzyl
 3-(benzylcarba-moyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate,
 C25H24N2O3
;
_journal_issue                   3
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              425
_journal_page_last               426
_journal_paper_doi               10.1515/ncrs-2016-0299
_journal_volume                  232
_journal_year                    2017
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C25 H24 N2 O3'
_chemical_formula_sum            'C25 H24 N2 O3'
_chemical_formula_weight         400.46
_chemical_name_common            'Hydroisoquinolinium derivative'
_chemical_name_systematic
;
(S)-benzyl 3-(benzylcarbamoyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                90
_cell_angle_beta                 98.328(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.7404(5)
_cell_length_b                   10.0985(5)
_cell_length_c                   10.7520(5)
_cell_measurement_reflns_used    8282
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.49
_cell_measurement_theta_min      2.64
_cell_volume                     1046.45(9)
_computing_cell_refinement
'SAINT (Bruker AXS Inc., Madison, WI, USA, 2006)'
_computing_data_collection
'SAINT (Bruker AXS Inc., Madison, WI, USA, 2006)'
_computing_data_reduction        'SAINT-Plus and XPREP (Bruker, 2008)'
_computing_molecular_graphics    'X-Seed (Barbour, 2001)'
_computing_publication_material  'ORTEP-3 '
_computing_structure_refinement  'SHELXS-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0223
_diffrn_reflns_av_unetI/netI     0.0203
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            14817
_diffrn_reflns_point_group_measured_fraction_full 0.970
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.491
_diffrn_reflns_theta_min         1.914
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.965
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_description       block
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.430
_exptl_crystal_size_mid          0.311
_exptl_crystal_size_min          0.214
_refine_diff_density_max         0.131
_refine_diff_density_min         -0.140
_refine_diff_density_rms         0.029
_refine_ls_abs_structure_details
;
 Flack x determined using 1571 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.911
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         3736
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.911
_refine_ls_R_factor_all          0.0269
_refine_ls_R_factor_gt           0.0252
_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)+(0.0291P)²+0.2969P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0588
_refine_ls_wR_factor_ref         0.0600
_reflns_Friedel_coverage         0.823
_reflns_Friedel_fraction_full    0.936
_reflns_Friedel_fraction_max     0.923
_reflns_number_gt                3597
_reflns_number_total             3736
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2016-0299_suppl.cif
_cod_data_source_block           1
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               8106557
_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   0.965
_shelx_estimated_absorpt_t_max   0.982
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -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
N1 N 0.24447(15) 0.79032(15) 0.46300(14) 0.0175(3) Uani 1 1 d . . . . .
C2 C 0.2072(2) 0.70771(19) 0.56613(17) 0.0201(4) Uani 1 1 d . . . . .
H2A H 0.2510 0.6196 0.5625 0.024 Uiso 1 1 calc R U . . .
H2B H 0.1054 0.6947 0.5536 0.024 Uiso 1 1 calc R U . . .
C3 C 0.25126(17) 0.76658(19) 0.69426(17) 0.0183(4) Uani 1 1 d . . . . .
C4 C 0.27324(19) 0.6836(2) 0.79887(17) 0.0210(4) Uani 1 1 d . . . . .
H4 H 0.2679 0.5903 0.7881 0.025 Uiso 1 1 calc R U . . .
C5 C 0.3028(2) 0.7368(2) 0.91867(19) 0.0252(4) Uani 1 1 d . . . . .
H5 H 0.3159 0.6800 0.9898 0.030 Uiso 1 1 calc R U . . .
C6 C 0.3135(2) 0.8733(2) 0.93466(19) 0.0269(5) Uani 1 1 d . . . . .
H6 H 0.3337 0.9097 1.0167 0.032 Uiso 1 1 calc R U . . .
C7 C 0.2946(2) 0.9560(2) 0.83093(19) 0.0249(4) Uani 1 1 d . . . . .
H7 H 0.3039 1.0491 0.8420 0.030 Uiso 1 1 calc R U . . .
C8 C 0.26214(18) 0.90333(19) 0.70997(18) 0.0195(4) Uani 1 1 d . . . . .
C9 C 0.2339(2) 0.98892(19) 0.59474(19) 0.0222(4) Uani 1 1 d . . . . .
H9A H 0.2763 1.0772 0.6132 0.027 Uiso 1 1 calc R U . . .
H9B H 0.1326 1.0012 0.5721 0.027 Uiso 1 1 calc R U . . .
C10 C 0.29266(19) 0.92722(17) 0.48345(17) 0.0186(4) Uani 1 1 d . . . . .
H10 H 0.2532 0.9785 0.4070 0.022 Uiso 1 1 calc R U . . .
C11 C 0.45097(19) 0.94378(19) 0.49808(16) 0.0181(4) Uani 1 1 d . . . . .
O12 O 0.50034(15) 1.05623(13) 0.50978(15) 0.0277(3) Uani 1 1 d . . . . .
N13 N 0.52719(14) 0.83506(16) 0.49343(13) 0.0167(3) Uani 1 1 d . . . . .
H13 H 0.4865 0.7571 0.4909 0.020 Uiso 1 1 calc R U . . .
C14 C 0.67582(17) 0.8419(2) 0.49237(15) 0.0175(4) Uani 1 1 d . . . . .
H14A H 0.7203 0.7651 0.5391 0.021 Uiso 1 1 calc R U . . .
H14B H 0.7122 0.9232 0.5371 0.021 Uiso 1 1 calc R U . . .
C15 C 0.71644(18) 0.84300(19) 0.36108(16) 0.0171(3) Uani 1 1 d . . . . .
C16 C 0.85645(18) 0.85572(19) 0.34930(17) 0.0204(4) Uani 1 1 d . . . . .
H16 H 0.9231 0.8655 0.4225 0.024 Uiso 1 1 calc R U . . .
C17 C 0.89966(18) 0.8543(2) 0.23207(18) 0.0230(4) Uani 1 1 d . . . . .
H17 H 0.9953 0.8636 0.2252 0.028 Uiso 1 1 calc R U . . .
C18 C 0.80309(19) 0.8395(2) 0.12451(17) 0.0234(4) Uani 1 1 d . . . . .
H18 H 0.8325 0.8369 0.0441 0.028 Uiso 1 1 calc R U . . .
C19 C 0.66364(19) 0.8284(2) 0.13547(16) 0.0229(4) Uani 1 1 d . . . . .
H19 H 0.5971 0.8195 0.0621 0.028 Uiso 1 1 calc R U . . .
C20 C 0.62022(17) 0.8302(2) 0.25312(16) 0.0199(4) Uani 1 1 d . . . . .
H20 H 0.5243 0.8226 0.2596 0.024 Uiso 1 1 calc R U . . .
C21 C 0.22325(18) 0.74605(19) 0.34245(17) 0.0184(4) Uani 1 1 d . . . . .
O22 O 0.25571(12) 0.80741(14) 0.25357(11) 0.0238(3) Uani 1 1 d . . . . .
O23 O 0.15980(13) 0.62682(13) 0.33411(11) 0.0215(3) Uani 1 1 d . . . . .
C24 C 0.1187(2) 0.5739(2) 0.20776(18) 0.0254(4) Uani 1 1 d . . . . .
H24A H 0.1591 0.6286 0.1458 0.030 Uiso 1 1 calc R U . . .
H24B H 0.0164 0.5763 0.1862 0.030 Uiso 1 1 calc R U . . .
C25 C 0.16945(19) 0.43361(19) 0.20340(16) 0.0200(4) Uani 1 1 d . . . . .
C26 C 0.3097(2) 0.4065(2) 0.20439(17) 0.0248(4) Uani 1 1 d . . . . .
H26 H 0.3741 0.4775 0.2071 0.030 Uiso 1 1 calc R U . . .
C27 C 0.3561(2) 0.2778(2) 0.20147(18) 0.0308(5) Uani 1 1 d . . . . .
H27 H 0.4522 0.2607 0.2031 0.037 Uiso 1 1 calc R U . . .
C28 C 0.2633(2) 0.1734(2) 0.19619(18) 0.0337(5) Uani 1 1 d . . . . .
H28 H 0.2955 0.0847 0.1940 0.040 Uiso 1 1 calc R U . . .
C29 C 0.1232(2) 0.1989(2) 0.19407(19) 0.0313(5) Uani 1 1 d . . . . .
H29 H 0.0591 0.1277 0.1901 0.038 Uiso 1 1 calc R U . . .
C30 C 0.07657(19) 0.3286(2) 0.19769(16) 0.0234(4) Uani 1 1 d . . . . .
H30 H -0.0196 0.3457 0.1963 0.028 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_site_symmetry_1
_geom_angle_site_symmetry_3
C21 N1 C10 117.04(15) . .
C21 N1 C2 120.76(15) . .
C10 N1 C2 121.94(15) . .
N1 C2 C3 113.34(15) . .
N1 C2 H2A 108.9 . .
C3 C2 H2A 108.9 . .
N1 C2 H2B 108.9 . .
C3 C2 H2B 108.9 . .
H2A C2 H2B 107.7 . .
C8 C3 C4 119.85(18) . .
C8 C3 C2 120.61(17) . .
C4 C3 C2 119.44(17) . .
C5 C4 C3 120.25(18) . .
C5 C4 H4 119.9 . .
C3 C4 H4 119.9 . .
C4 C5 C6 120.02(19) . .
C4 C5 H5 120.0 . .
C6 C5 H5 120.0 . .
C7 C6 C5 119.97(19) . .
C7 C6 H6 120.0 . .
C5 C6 H6 120.0 . .
C6 C7 C8 120.37(19) . .
C6 C7 H7 119.8 . .
C8 C7 H7 119.8 . .
C3 C8 C7 119.52(18) . .
C3 C8 C9 117.93(17) . .
C7 C8 C9 122.53(18) . .
C8 C9 C10 111.46(15) . .
C8 C9 H9A 109.3 . .
C10 C9 H9A 109.3 . .
C8 C9 H9B 109.3 . .
C10 C9 H9B 109.3 . .
H9A C9 H9B 108.0 . .
N1 C10 C9 110.67(15) . .
N1 C10 C11 114.38(15) . .
C9 C10 C11 111.02(15) . .
N1 C10 H10 106.8 . .
C9 C10 H10 106.8 . .
C11 C10 H10 106.8 . .
O12 C11 N13 123.54(17) . .
O12 C11 C10 118.80(17) . .
N13 C11 C10 117.63(16) . .
C11 N13 C14 121.58(16) . .
C11 N13 H13 119.2 . .
C14 N13 H13 119.2 . .
N13 C14 C15 113.69(14) . .
N13 C14 H14A 108.8 . .
C15 C14 H14A 108.8 . .
N13 C14 H14B 108.8 . .
C15 C14 H14B 108.8 . .
H14A C14 H14B 107.7 . .
C20 C15 C16 118.91(16) . .
C20 C15 C14 122.74(15) . .
C16 C15 C14 118.34(15) . .
C17 C16 C15 120.79(17) . .
C17 C16 H16 119.6 . .
C15 C16 H16 119.6 . .
C16 C17 C18 120.01(16) . .
C16 C17 H17 120.0 . .
C18 C17 H17 120.0 . .
C19 C18 C17 119.48(16) . .
C19 C18 H18 120.3 . .
C17 C18 H18 120.3 . .
C18 C19 C20 120.50(17) . .
C18 C19 H19 119.8 . .
C20 C19 H19 119.8 . .
C15 C20 C19 120.29(16) . .
C15 C20 H20 119.9 . .
C19 C20 H20 119.9 . .
O22 C21 O23 124.72(17) . .
O22 C21 N1 124.06(17) . .
O23 C21 N1 111.21(15) . .
C21 O23 C24 116.69(15) . .
O23 C24 C25 109.07(15) . .
O23 C24 H24A 109.9 . .
C25 C24 H24A 109.9 . .
O23 C24 H24B 109.9 . .
C25 C24 H24B 109.9 . .
H24A C24 H24B 108.3 . .
C30 C25 C26 118.87(18) . .
C30 C25 C24 120.36(17) . .
C26 C25 C24 120.77(18) . .
C27 C26 C25 120.63(19) . .
C27 C26 H26 119.7 . .
C25 C26 H26 119.7 . .
C26 C27 C28 120.38(18) . .
C26 C27 H27 119.8 . .
C28 C27 H27 119.8 . .
C29 C28 C27 119.6(2) . .
C29 C28 H28 120.2 . .
C27 C28 H28 120.2 . .
C28 C29 C30 120.1(2) . .
C28 C29 H29 120.0 . .
C30 C29 H29 120.0 . .
C29 C30 C25 120.47(18) . .
C29 C30 H30 119.8 . .
C25 C30 H30 119.8 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C21 1.358(2) .
N1 C10 1.466(2) .
N1 C2 1.475(2) .
C2 C3 1.505(3) .
C2 H2A 0.9900 .
C2 H2B 0.9900 .
C3 C8 1.394(3) .
C3 C4 1.394(3) .
C4 C5 1.387(3) .
C4 H4 0.9500 .
C5 C6 1.391(3) .
C5 H5 0.9500 .
C6 C7 1.384(3) .
C6 H6 0.9500 .
C7 C8 1.398(3) .
C7 H7 0.9500 .
C8 C9 1.503(3) .
C9 C10 1.532(3) .
C9 H9A 0.9900 .
C9 H9B 0.9900 .
C10 C11 1.536(2) .
C10 H10 1.0000 .
C11 O12 1.233(2) .
C11 N13 1.330(2) .
N13 C14 1.451(2) .
N13 H13 0.8800 .
C14 C15 1.520(2) .
C14 H14A 0.9900 .
C14 H14B 0.9900 .
C15 C20 1.388(2) .
C15 C16 1.394(2) .
C16 C17 1.386(3) .
C16 H16 0.9500 .
C17 C18 1.389(3) .
C17 H17 0.9500 .
C18 C19 1.385(3) .
C18 H18 0.9500 .
C19 C20 1.391(2) .
C19 H19 0.9500 .
C20 H20 0.9500 .
C21 O22 1.219(2) .
C21 O23 1.350(2) .
O23 C24 1.461(2) .
C24 C25 1.503(3) .
C24 H24A 0.9900 .
C24 H24B 0.9900 .
C25 C30 1.389(3) .
C25 C26 1.392(3) .
C26 C27 1.378(3) .
C26 H26 0.9500 .
C27 C28 1.385(3) .
C27 H27 0.9500 .
C28 C29 1.386(3) .
C28 H28 0.9500 .
C29 C30 1.389(3) .
C29 H29 0.9500 .
C30 H30 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
N13 H13 O12 0.88 2.03 2.828(2) 149.8 2_646
