#------------------------------------------------------------------------------
#$Date: 2022-11-08 12:06:01 +0200 (Tue, 08 Nov 2022) $
#$Revision: 279091 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/60/8106012.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_8106012
loop_
_publ_author_name
'Qin, Yu-Mei'
'Zou, Xue'
'Long, Dan'
'Ji, Chun'
'Zhao, Chun-Shen'
_publ_section_title
;
 The crystal structure of methyl 2-(benzylamino)-5-(benzyloxy)benzoate,
 C22H21NO3
;
_journal_issue                   6
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              1295
_journal_page_last               1296
_journal_paper_doi               10.1515/ncrs-2019-0420
_journal_volume                  234
_journal_year                    2019
_chemical_formula_sum            'C22 H21 N O3'
_chemical_formula_weight         347.40
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                93.725(12)
_cell_angle_beta                 92.508(15)
_cell_angle_gamma                102.282(14)
_cell_formula_units_Z            2
_cell_length_a                   5.757(3)
_cell_length_b                   12.106(5)
_cell_length_c                   13.139(6)
_cell_measurement_reflns_used    1470
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.23
_cell_measurement_theta_min      2.41
_cell_volume                     891.3(7)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  CCD
_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  0.0250
_diffrn_reflns_av_sigmaI/netI    0.0416
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5850
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.56
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  0.9847
_exptl_absorpt_correction_T_min  0.9813
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.209
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.960
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3142
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.960
_refine_ls_R_factor_all          0.0691
_refine_ls_R_factor_gt           0.0474
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0845P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1289
_refine_ls_wR_factor_ref         0.1429
_reflns_number_gt                2178
_reflns_number_total             3142
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            suppl_ncrs-2019-0420_suppl.cif
_cod_data_source_block           1
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Triclinic' was changed to
'triclinic' in accordance with the built-in table derived from the
CIF Core dictionary named 'cif_core.dic' version 2.4.5 last updated
on 2014-11-21.

Automatic conversion script
Id: cif_fix_values 8738 2021-04-28 16:35:53Z antanas 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               8106012
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.6365(4) 0.64603(16) -0.00613(14) 0.0515(5) Uani 1 1 d . . .
H1 H -0.7911 0.6060 0.0010 0.062 Uiso 1 1 calc R . .
C2 C -0.5857(5) 0.70763(17) -0.09043(15) 0.0600(6) Uani 1 1 d . . .
H2 H -0.7065 0.7089 -0.1395 0.072 Uiso 1 1 calc R . .
C3 C -0.3609(5) 0.76633(19) -0.10219(16) 0.0654(6) Uani 1 1 d . . .
H3 H -0.3279 0.8085 -0.1585 0.078 Uiso 1 1 calc R . .
C4 C -0.1841(5) 0.76298(19) -0.03083(16) 0.0656(6) Uani 1 1 d . . .
H4 H -0.0297 0.8024 -0.0391 0.079 Uiso 1 1 calc R . .
C5 C -0.2325(4) 0.70136(17) 0.05397(14) 0.0530(5) Uani 1 1 d . . .
H5 H -0.1098 0.6994 0.1018 0.064 Uiso 1 1 calc R . .
C6 C -0.4590(3) 0.64331(15) 0.06803(13) 0.0423(5) Uani 1 1 d . . .
C7 C -0.5213(4) 0.57879(17) 0.16102(14) 0.0512(5) Uani 1 1 d . . .
H7A H -0.6156 0.6191 0.2029 0.061 Uiso 1 1 calc R . .
H7B H -0.6206 0.5052 0.1386 0.061 Uiso 1 1 calc R . .
C8 C -0.2030(3) 0.63532(15) 0.29992(12) 0.0424(5) Uani 1 1 d . . .
C9 C -0.2605(4) 0.74157(16) 0.32312(13) 0.0480(5) Uani 1 1 d . . .
H9 H -0.3829 0.7613 0.2847 0.058 Uiso 1 1 calc R . .
C10 C -0.1423(4) 0.81595(16) 0.39994(14) 0.0482(5) Uani 1 1 d . . .
H10 H -0.1869 0.8846 0.4139 0.058 Uiso 1 1 calc R . .
C11 C 0.0445(4) 0.79020(15) 0.45772(13) 0.0441(5) Uani 1 1 d . . .
C12 C 0.1088(4) 0.68876(15) 0.43560(13) 0.0438(5) Uani 1 1 d . . .
H12 H 0.2362 0.6720 0.4730 0.053 Uiso 1 1 calc R . .
C13 C -0.0120(3) 0.61027(14) 0.35853(12) 0.0406(4) Uani 1 1 d . . .
C14 C 0.0593(3) 0.50104(16) 0.34136(13) 0.0440(5) Uani 1 1 d . . .
C15 C 0.3336(4) 0.84049(16) 0.59599(14) 0.0528(5) Uani 1 1 d . . .
H15A H 0.4702 0.8388 0.5557 0.063 Uiso 1 1 calc R . .
H15B H 0.2789 0.7658 0.6199 0.063 Uiso 1 1 calc R . .
C16 C 0.4030(4) 0.92601(15) 0.68491(13) 0.0459(5) Uani 1 1 d . . .
C17 C 0.6250(4) 0.99605(17) 0.69514(16) 0.0603(6) Uani 1 1 d . . .
H17 H 0.7307 0.9938 0.6439 0.072 Uiso 1 1 calc R . .
C18 C 0.6925(5) 1.06991(19) 0.78103(19) 0.0730(7) Uani 1 1 d . . .
H18 H 0.8434 1.1171 0.7874 0.088 Uiso 1 1 calc R . .
C19 C 0.5383(5) 1.07381(19) 0.85661(17) 0.0706(7) Uani 1 1 d . . .
H19 H 0.5849 1.1227 0.9149 0.085 Uiso 1 1 calc R . .
C20 C 0.3159(5) 1.0057(2) 0.84629(16) 0.0689(7) Uani 1 1 d . . .
H20 H 0.2097 1.0091 0.8972 0.083 Uiso 1 1 calc R . .
C21 C 0.2485(4) 0.93227(17) 0.76092(16) 0.0585(6) Uani 1 1 d . . .
H21 H 0.0963 0.8862 0.7544 0.070 Uiso 1 1 calc R . .
C22 C 0.3417(4) 0.39306(16) 0.38666(17) 0.0620(6) Uani 1 1 d . . .
H22A H 0.2195 0.3290 0.3997 0.093 Uiso 1 1 calc R . .
H22B H 0.4765 0.3982 0.4338 0.093 Uiso 1 1 calc R . .
H22C H 0.3893 0.3841 0.3180 0.093 Uiso 1 1 calc R . .
N1 N -0.3232(3) 0.56148(13) 0.22361(11) 0.0512(4) Uani 1 1 d . . .
H1A H -0.2768 0.4991 0.2117 0.061 Uiso 1 1 calc R . .
O1 O 0.2515(3) 0.49495(11) 0.39942(10) 0.0557(4) Uani 1 1 d . . .
O2 O 0.1484(3) 0.86967(11) 0.53476(9) 0.0568(4) Uani 1 1 d . . .
O3 O -0.0365(3) 0.42349(12) 0.28202(11) 0.0662(5) Uani 1 1 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
C2 C1 C6 120.6(2) . .
C3 C2 C1 120.5(2) . .
C2 C3 C4 119.5(2) . .
C3 C4 C5 120.6(2) . .
C6 C5 C4 120.71(19) . .
C5 C6 C1 118.03(18) . .
C5 C6 C7 122.48(17) . .
C1 C6 C7 119.49(19) . .
N1 C7 C6 115.82(18) . .
N1 C8 C13 121.49(16) . .
N1 C8 C9 121.57(17) . .
C13 C8 C9 116.93(16) . .
C10 C9 C8 122.07(17) . .
C9 C10 C11 120.58(17) . .
O2 C11 C12 125.09(17) . .
O2 C11 C10 116.03(16) . .
C12 C11 C10 118.88(17) . .
C11 C12 C13 121.68(17) . .
C12 C13 C8 119.84(16) . .
C12 C13 C14 119.06(16) . .
C8 C13 C14 121.09(16) . .
O3 C14 O1 120.99(17) . .
O3 C14 C13 126.28(17) . .
O1 C14 C13 112.73(16) . .
O2 C15 C16 109.22(15) . .
C17 C16 C21 118.68(19) . .
C17 C16 C15 120.95(19) . .
C21 C16 C15 120.30(19) . .
C16 C17 C18 120.4(2) . .
C19 C18 C17 120.2(2) . .
C20 C19 C18 119.8(2) . .
C19 C20 C21 120.1(2) . .
C20 C21 C16 120.8(2) . .
C8 N1 C7 125.46(16) . .
C14 O1 C22 117.51(15) . .
C11 O2 C15 115.55(14) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.383(3) .
C1 C6 1.388(2) .
C2 C3 1.358(3) .
C3 C4 1.362(3) .
C4 C5 1.386(3) .
C5 C6 1.370(3) .
C6 C7 1.508(3) .
C7 N1 1.436(2) .
C8 N1 1.357(2) .
C8 C13 1.412(3) .
C8 C9 1.413(3) .
C9 C10 1.362(3) .
C10 C11 1.390(3) .
C11 O2 1.372(2) .
C11 C12 1.373(3) .
C12 C13 1.394(2) .
C13 C14 1.473(3) .
C14 O3 1.200(2) .
C14 O1 1.334(2) .
C15 O2 1.425(2) .
C15 C16 1.491(3) .
C16 C17 1.371(3) .
C16 C21 1.375(3) .
C17 C18 1.381(3) .
C18 C19 1.366(4) .
C19 C20 1.363(3) .
C20 C21 1.373(3) .
C22 O1 1.440(2) .
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
C6 C1 C2 C3 0.2(3) . . . .
C1 C2 C3 C4 0.9(3) . . . .
C2 C3 C4 C5 -0.7(3) . . . .
C3 C4 C5 C6 -0.5(3) . . . .
C4 C5 C6 C1 1.5(3) . . . .
C4 C5 C6 C7 -177.69(18) . . . .
C2 C1 C6 C5 -1.3(3) . . . .
C2 C1 C6 C7 177.85(17) . . . .
C5 C6 C7 N1 -12.6(3) . . . .
C1 C6 C7 N1 168.30(16) . . . .
N1 C8 C9 C10 179.53(18) . . . .
C13 C8 C9 C10 -1.6(3) . . . .
C8 C9 C10 C11 1.2(3) . . . .
C9 C10 C11 O2 -178.60(17) . . . .
C9 C10 C11 C12 0.4(3) . . . .
O2 C11 C12 C13 177.36(17) . . . .
C10 C11 C12 C13 -1.6(3) . . . .
C11 C12 C13 C8 1.1(3) . . . .
C11 C12 C13 C14 -177.50(17) . . . .
N1 C8 C13 C12 179.33(17) . . . .
C9 C8 C13 C12 0.4(3) . . . .
N1 C8 C13 C14 -2.1(3) . . . .
C9 C8 C13 C14 179.03(16) . . . .
C12 C13 C14 O3 175.61(19) . . . .
C8 C13 C14 O3 -3.0(3) . . . .
C12 C13 C14 O1 -5.1(2) . . . .
C8 C13 C14 O1 176.27(16) . . . .
O2 C15 C16 C17 -114.3(2) . . . .
O2 C15 C16 C21 68.8(2) . . . .
C21 C16 C17 C18 1.1(3) . . . .
C15 C16 C17 C18 -175.87(19) . . . .
C16 C17 C18 C19 0.0(3) . . . .
C17 C18 C19 C20 -1.0(3) . . . .
C18 C19 C20 C21 1.0(3) . . . .
C19 C20 C21 C16 0.1(3) . . . .
C17 C16 C21 C20 -1.1(3) . . . .
C15 C16 C21 C20 175.85(18) . . . .
C13 C8 N1 C7 179.08(17) . . . .
C9 C8 N1 C7 -2.1(3) . . . .
C6 C7 N1 C8 86.3(2) . . . .
O3 C14 O1 C22 1.2(3) . . . .
C13 C14 O1 C22 -178.11(16) . . . .
C12 C11 O2 C15 -1.2(3) . . . .
C10 C11 O2 C15 177.71(16) . . . .
C16 C15 O2 C11 -171.57(16) . . . .
