#------------------------------------------------------------------------------
#$Date: 2022-03-18 10:29:56 +0200 (Fri, 18 Mar 2022) $
#$Revision: 273790 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/47/8104790.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_8104790
loop_
_publ_author_name
'Xu, Qin-Juan'
_publ_section_title
;
 Crystal structure of
 N-(5-(2-(benzyl(1-(4-methoxyphenyl)propan-2-yl)amino)-1-hydroxyethyl)-2-(benzyloxy)phenyl)formamide,
 C33H36N2O4
;
_journal_issue                   3
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              647
_journal_page_last               649
_journal_paper_doi               10.1515/ncrs-2021-0012
_journal_volume                  236
_journal_year                    2021
_chemical_formula_sum            'C33 H36 N2 O4'
_chemical_formula_weight         524.64
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   15.3543(17)
_cell_length_b                   14.7958(17)
_cell_length_c                   25.496(3)
_cell_measurement_reflns_used    8879
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.49
_cell_measurement_theta_min      2.49
_cell_volume                     5792.2(11)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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_sigmaI/netI    0.0240
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            26962
_diffrn_reflns_theta_full        27.02
_diffrn_reflns_theta_max         27.02
_diffrn_reflns_theta_min         3.07
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.203
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       sheet
_exptl_crystal_F_000             2240
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.186
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     364
_refine_ls_number_reflns         6305
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0745
_refine_ls_R_factor_gt           0.0490
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0631P)²+1.4075P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1219
_refine_ls_wR_factor_ref         0.1402
_reflns_number_gt                4395
_reflns_number_total             6305
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            suppl_j_ncrs-2021-0012_suppl.cif
_cod_data_source_block           a
_cod_original_cell_volume        5792.1(11)
_cod_original_sg_symbol_H-M      Pbca
_cod_database_code               8104790
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, 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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.46246(8) 0.12243(8) 0.83595(5) 0.0406(3) Uani 1 1 d . . .
N2 N 0.09567(9) 0.27618(9) 0.98248(5) 0.0464(3) Uani 1 1 d . . .
O1 O 0.10064(8) 0.14121(8) 1.04744(5) 0.0613(3) Uani 1 1 d . . .
O2 O 0.87256(10) 0.16534(14) 0.87061(8) 0.1029(6) Uani 1 1 d . . .
O3 O 0.13010(9) 0.39210(10) 0.92729(6) 0.0751(4) Uani 1 1 d . . .
O4 O 0.46809(7) 0.18781(9) 0.93622(5) 0.0563(3) Uani 1 1 d . . .
C1 C 0.38441(9) 0.11814(11) 0.86881(6) 0.0418(3) Uani 1 1 d . . .
H1A H 0.3813 0.0595 0.8857 0.050 Uiso 1 1 calc R . .
H1B H 0.3331 0.1252 0.8470 0.050 Uiso 1 1 calc R . .
C2 C 0.38579(9) 0.19203(10) 0.91047(6) 0.0426(3) Uani 1 1 d . . .
H2B H 0.3795 0.2511 0.8935 0.051 Uiso 1 1 calc R . .
C3 C 0.49060(11) 0.03357(10) 0.81525(6) 0.0479(4) Uani 1 1 d . . .
H3A H 0.5270 0.0459 0.7845 0.058 Uiso 1 1 calc R . .
C4 C 0.54882(12) -0.01433(12) 0.85524(7) 0.0599(5) Uani 1 1 d . . .
H4B H 0.5191 -0.0161 0.8888 0.072 Uiso 1 1 calc R . .
H4C H 0.5580 -0.0762 0.8440 0.072 Uiso 1 1 calc R . .
C5 C 0.45420(10) 0.19040(11) 0.79426(6) 0.0500(4) Uani 1 1 d . . .
H5A H 0.4279 0.2445 0.8087 0.060 Uiso 1 1 calc R . .
H5B H 0.4156 0.1674 0.7673 0.060 Uiso 1 1 calc R . .
C6 C 0.41669(13) -0.02737(13) 0.79671(7) 0.0641(5) Uani 1 1 d . . .
H6A H 0.3817 0.0045 0.7715 0.096 Uiso 1 1 calc R . .
H6B H 0.3813 -0.0443 0.8261 0.096 Uiso 1 1 calc R . .
H6C H 0.4405 -0.0807 0.7808 0.096 Uiso 1 1 calc R . .
C7 C 0.31346(9) 0.17943(10) 0.94947(6) 0.0418(3) Uani 1 1 d . . .
C8 C 0.24075(9) 0.23555(10) 0.94766(5) 0.0402(3) Uani 1 1 d . . .
H8A H 0.2390 0.2828 0.9237 0.048 Uiso 1 1 calc R . .
C9 C 0.17098(9) 0.22176(10) 0.98123(5) 0.0400(3) Uani 1 1 d . . .
C10 C 0.17362(10) 0.15047(11) 1.01712(6) 0.0464(4) Uani 1 1 d . . .
C11 C 0.24661(11) 0.09621(12) 1.01994(6) 0.0548(4) Uani 1 1 d . . .
H11A H 0.2493 0.0499 1.0445 0.066 Uiso 1 1 calc R . .
C12 C 0.31582(10) 0.11084(11) 0.98608(6) 0.0511(4) Uani 1 1 d . . .
H12A H 0.3646 0.0738 0.9881 0.061 Uiso 1 1 calc R . .
C13 C 0.09412(12) 0.06297(13) 1.08000(7) 0.0603(5) Uani 1 1 d . . .
H13A H 0.1346 0.0676 1.1091 0.072 Uiso 1 1 calc R . .
H13B H 0.1085 0.0093 1.0600 0.072 Uiso 1 1 calc R . .
C14 C 0.08184(12) 0.35480(12) 0.95767(7) 0.0527(4) Uani 1 1 d . . .
C15 C 0.00311(11) 0.05635(12) 1.10022(7) 0.0547(4) Uani 1 1 d . . .
C16 C -0.06654(16) 0.0518(2) 1.06691(10) 0.0966(8) Uani 1 1 d . . .
H16A H -0.0574 0.0550 1.0309 0.116 Uiso 1 1 calc R . .
C17 C -0.15039(18) 0.0426(2) 1.08605(18) 0.1218(12) Uani 1 1 d . . .
H17A H -0.1972 0.0378 1.0630 0.146 Uiso 1 1 calc R . .
C18 C -0.1640(2) 0.0407(2) 1.13904(19) 0.1232(13) Uani 1 1 d . . .
H18A H -0.2201 0.0344 1.1523 0.148 Uiso 1 1 calc R . .
C19 C -0.0951(2) 0.0480(3) 1.17226(14) 0.1300(13) Uani 1 1 d . . .
H19A H -0.1045 0.0480 1.2083 0.156 Uiso 1 1 calc R . .
C20 C -0.01182(15) 0.05523(18) 1.15302(9) 0.0873(7) Uani 1 1 d . . .
H20A H 0.0348 0.0594 1.1762 0.105 Uiso 1 1 calc R . .
C21 C 0.54001(12) 0.21462(11) 0.76982(7) 0.0564(4) Uani 1 1 d . . .
C22 C 0.55370(18) 0.20232(16) 0.71676(9) 0.0865(7) Uani 1 1 d . . .
H22A H 0.5097 0.1784 0.6959 0.104 Uiso 1 1 calc R . .
C23 C 0.6331(3) 0.2257(2) 0.69471(15) 0.1281(14) Uani 1 1 d . . .
H23A H 0.6420 0.2166 0.6590 0.154 Uiso 1 1 calc R . .
C24 C 0.6976(2) 0.2613(2) 0.7238(2) 0.1343(16) Uani 1 1 d . . .
H24A H 0.7501 0.2778 0.7083 0.161 Uiso 1 1 calc R . .
C25 C 0.68524(16) 0.27284(19) 0.77621(17) 0.1163(12) Uani 1 1 d . . .
H25A H 0.7299 0.2964 0.7967 0.140 Uiso 1 1 calc R . .
C26 C 0.60637(13) 0.24967(15) 0.79948(10) 0.0787(6) Uani 1 1 d . . .
H26A H 0.5986 0.2580 0.8353 0.094 Uiso 1 1 calc R . .
C27 C 0.63538(11) 0.03058(11) 0.86225(7) 0.0525(4) Uani 1 1 d . . .
C28 C 0.65541(13) 0.08140(13) 0.90562(7) 0.0608(5) Uani 1 1 d . . .
H28A H 0.6151 0.0849 0.9328 0.073 Uiso 1 1 calc R . .
C29 C 0.73312(14) 0.12755(14) 0.91056(7) 0.0678(5) Uani 1 1 d . . .
H29A H 0.7444 0.1615 0.9405 0.081 Uiso 1 1 calc R . .
C30 C 0.79341(12) 0.12296(14) 0.87107(8) 0.0668(5) Uani 1 1 d . . .
C31 C 0.77609(13) 0.07094(15) 0.82747(8) 0.0696(5) Uani 1 1 d . . .
H31A H 0.8172 0.0663 0.8008 0.084 Uiso 1 1 calc R . .
C32 C 0.69846(12) 0.02608(14) 0.82328(7) 0.0631(5) Uani 1 1 d . . .
H32A H 0.6876 -0.0084 0.7935 0.076 Uiso 1 1 calc R . .
C33 C 0.8949(2) 0.2210(3) 0.91319(16) 0.1465(14) Uani 1 1 d . . .
H33A H 0.9522 0.2453 0.9079 0.220 Uiso 1 1 calc R . .
H33B H 0.8940 0.1861 0.9449 0.220 Uiso 1 1 calc R . .
H33C H 0.8537 0.2695 0.9159 0.220 Uiso 1 1 calc R . .
H1 H 0.0248(12) 0.3816(12) 0.9669(6) 0.056(5) Uiso 1 1 d . . .
H4 H 0.5056(16) 0.1731(16) 0.9129(9) 0.092(8) Uiso 1 1 d . . .
H2 H 0.0570(12) 0.2609(13) 1.0066(8) 0.065(6) Uiso 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
C1 N1 C5 111.92(12) . .
C1 N1 C3 113.85(11) . .
C5 N1 C3 112.02(12) . .
C14 N2 C9 127.93(14) . .
C10 O1 C13 117.84(12) . .
C30 O2 C33 118.6(2) . .
N1 C1 C2 110.87(12) . .
O4 C2 C7 110.20(12) . .
O4 C2 C1 107.57(12) . .
C7 C2 C1 111.21(12) . .
N1 C3 C6 114.72(14) . .
N1 C3 C4 110.13(13) . .
C6 C3 C4 111.56(14) . .
C27 C4 C3 113.12(14) . .
N1 C5 C21 112.84(13) . .
C12 C7 C8 118.83(14) . .
C12 C7 C2 121.32(13) . .
C8 C7 C2 119.81(13) . .
C9 C8 C7 120.77(13) . .
C8 C9 C10 119.54(13) . .
C8 C9 N2 124.33(13) . .
C10 C9 N2 116.12(13) . .
O1 C10 C11 125.26(14) . .
O1 C10 C9 114.96(13) . .
C11 C10 C9 119.79(14) . .
C10 C11 C12 119.94(15) . .
C7 C12 C11 121.08(14) . .
O1 C13 C15 108.64(14) . .
O3 C14 N2 127.07(16) . .
C20 C15 C16 118.7(2) . .
C20 C15 C13 119.89(18) . .
C16 C15 C13 121.40(18) . .
C15 C16 C17 120.9(3) . .
C18 C17 C16 119.5(3) . .
C19 C18 C17 119.7(3) . .
C18 C19 C20 120.5(3) . .
C15 C20 C19 120.6(3) . .
C26 C21 C22 118.50(19) . .
C26 C21 C5 120.92(18) . .
C22 C21 C5 120.6(2) . .
C21 C22 C23 119.9(3) . .
C24 C23 C22 121.4(3) . .
C23 C24 C25 119.2(3) . .
C24 C25 C26 120.6(3) . .
C21 C26 C25 120.3(3) . .
C28 C27 C32 116.51(17) . .
C28 C27 C4 122.58(16) . .
C32 C27 C4 120.83(17) . .
C27 C28 C29 122.57(17) . .
C30 C29 C28 119.51(18) . .
O2 C30 C29 125.75(19) . .
O2 C30 C31 114.88(19) . .
C29 C30 C31 119.37(19) . .
C32 C31 C30 120.13(18) . .
C31 C32 C27 121.89(18) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C1 1.4635(17) .
N1 C5 1.4689(19) .
N1 C3 1.4812(19) .
N2 C14 1.341(2) .
N2 C9 1.4094(18) .
O1 C10 1.3682(18) .
O1 C13 1.428(2) .
O2 C30 1.368(2) .
O2 C33 1.405(3) .
O3 C14 1.206(2) .
O4 C2 1.4254(18) .
C1 C2 1.524(2) .
C2 C7 1.502(2) .
C3 C6 1.525(2) .
C3 C4 1.530(2) .
C4 C27 1.497(3) .
C5 C21 1.501(2) .
C7 C12 1.379(2) .
C7 C8 1.392(2) .
C8 C9 1.386(2) .
C9 C10 1.397(2) .
C10 C11 1.380(2) .
C11 C12 1.386(2) .
C13 C15 1.493(2) .
C15 C20 1.366(3) .
C15 C16 1.367(3) .
C16 C17 1.384(4) .
C17 C18 1.367(5) .
C18 C19 1.359(5) .
C19 C20 1.374(3) .
C21 C26 1.371(3) .
C21 C22 1.381(3) .
C22 C23 1.387(4) .
C23 C24 1.345(5) .
C24 C25 1.360(5) .
C25 C26 1.391(3) .
C27 C28 1.372(3) .
C27 C32 1.389(2) .
C28 C29 1.380(3) .
C29 C30 1.369(3) .
C30 C31 1.378(3) .
C31 C32 1.368(3) .
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
C5 N1 C1 C2 -82.15(15) . . . .
C3 N1 C1 C2 149.55(13) . . . .
N1 C1 C2 O4 -50.38(16) . . . .
N1 C1 C2 C7 -171.14(12) . . . .
C1 N1 C3 C6 41.01(18) . . . .
C5 N1 C3 C6 -87.24(16) . . . .
C1 N1 C3 C4 -85.84(15) . . . .
C5 N1 C3 C4 145.92(13) . . . .
N1 C3 C4 C27 -68.78(18) . . . .
C6 C3 C4 C27 162.63(15) . . . .
C1 N1 C5 C21 164.02(14) . . . .
C3 N1 C5 C21 -66.72(18) . . . .
O4 C2 C7 C12 -47.02(19) . . . .
C1 C2 C7 C12 72.18(18) . . . .
O4 C2 C7 C8 135.48(14) . . . .
C1 C2 C7 C8 -105.32(16) . . . .
C12 C7 C8 C9 -1.4(2) . . . .
C2 C7 C8 C9 176.16(13) . . . .
C7 C8 C9 C10 -0.3(2) . . . .
C7 C8 C9 N2 179.00(14) . . . .
C14 N2 C9 C8 -9.1(2) . . . .
C14 N2 C9 C10 170.21(16) . . . .
C13 O1 C10 C11 -8.4(3) . . . .
C13 O1 C10 C9 171.95(15) . . . .
C8 C9 C10 O1 -178.32(14) . . . .
N2 C9 C10 O1 2.4(2) . . . .
C8 C9 C10 C11 2.0(2) . . . .
N2 C9 C10 C11 -177.34(15) . . . .
O1 C10 C11 C12 178.30(16) . . . .
C9 C10 C11 C12 -2.0(3) . . . .
C8 C7 C12 C11 1.4(2) . . . .
C2 C7 C12 C11 -176.16(15) . . . .
C10 C11 C12 C7 0.4(3) . . . .
C10 O1 C13 C15 -167.87(15) . . . .
C9 N2 C14 O3 3.9(3) . . . .
O1 C13 C15 C20 -122.0(2) . . . .
O1 C13 C15 C16 57.6(3) . . . .
C20 C15 C16 C17 -2.6(4) . . . .
C13 C15 C16 C17 177.8(2) . . . .
C15 C16 C17 C18 1.9(5) . . . .
C16 C17 C18 C19 0.2(5) . . . .
C17 C18 C19 C20 -1.5(5) . . . .
C16 C15 C20 C19 1.2(4) . . . .
C13 C15 C20 C19 -179.1(2) . . . .
C18 C19 C20 C15 0.8(5) . . . .
N1 C5 C21 C26 -59.3(2) . . . .
N1 C5 C21 C22 120.96(19) . . . .
C26 C21 C22 C23 -0.3(3) . . . .
C5 C21 C22 C23 179.5(2) . . . .
C21 C22 C23 C24 -0.7(4) . . . .
C22 C23 C24 C25 1.4(5) . . . .
C23 C24 C25 C26 -1.1(4) . . . .
C22 C21 C26 C25 0.5(3) . . . .
C5 C21 C26 C25 -179.23(18) . . . .
C24 C25 C26 C21 0.2(4) . . . .
C3 C4 C27 C28 105.17(19) . . . .
C3 C4 C27 C32 -71.7(2) . . . .
C32 C27 C28 C29 1.2(3) . . . .
C4 C27 C28 C29 -175.74(16) . . . .
C27 C28 C29 C30 -0.2(3) . . . .
C33 O2 C30 C29 -1.9(4) . . . .
C33 O2 C30 C31 179.0(3) . . . .
C28 C29 C30 O2 179.71(19) . . . .
C28 C29 C30 C31 -1.2(3) . . . .
O2 C30 C31 C32 -179.3(2) . . . .
C29 C30 C31 C32 1.5(3) . . . .
C30 C31 C32 C27 -0.4(3) . . . .
C28 C27 C32 C31 -0.9(3) . . . .
C4 C27 C32 C31 176.11(18) . . . .
