# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_riparin_I_delta
_database_code_depnum_ccdc_archive 'CCDC 1892485'
loop_
_audit_author_name
_audit_author_address
'Alejandro Pedro Ayala'
;Universidade Federal do Ceara
Brazil
;
_audit_update_record             
;
2020-04-14 deposited with the CCDC.	2020-10-12 downloaded from the CCDC.
;
_audit_creation_date             2020-04-14
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        'riparin I delta'
_chemical_formula_moiety         'C16 H17 N O2'
_chemical_formula_sum            'C16 H17 N O2'
_chemical_formula_weight         255.30
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.0074(9)
_cell_length_b                   5.1466(6)
_cell_length_c                   32.075(4)
_cell_angle_alpha                90
_cell_angle_beta                 96.538(4)
_cell_angle_gamma                90
_cell_volume                     1313.3(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9979
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      68.422
_cell_measurement_theta_min      2.775
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.679
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6233
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.291
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0470
_diffrn_reflns_av_unetI/netI     0.0202
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            35776
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.355
_diffrn_reflns_theta_min         2.773
_diffrn_ambient_temperature      99.99
_diffrn_detector                 'Photon II CPAD Area Detector'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'Bruker PHOTON II'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTON II CPAD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'multilayer mirrors'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'micro-focus sealed tube'
_diffrn_source_type              'Incoatech I\mS HB'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2286
_reflns_number_total             2412
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.182
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2412
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0396
_refine_ls_R_factor_gt           0.0373
_refine_ls_restrained_S_all      1.057
_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)+(0.0396P)²+0.6175P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0891
_refine_ls_wR_factor_ref         0.0909
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7'(H7'A,H7'B), C8'(H8'A,H8'B)
2.b Aromatic/amide H refined with riding coordinates:
 N8'(H8'), C3'(H3'), C2'(H2'), C6(H6), C5(H5), C4(H4), C5'(H5'), C6'(H6'),
 C2(H2), C3(H3)
2.c Idealised Me refined as rotating group:
 C9'(H9'A,H9'B,H9'C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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
O4' O 0.40014(11) 0.46294(17) 0.54561(2) 0.0238(2) Uani 1 1 d . . . . .
N8' N 0.57850(12) 0.3354(2) 0.78903(3) 0.0207(2) Uani 1 1 d . . . . .
H8' H 0.590100 0.175810 0.798790 0.025 Uiso 1 1 calc R U . . .
O7 O 0.55334(11) 0.76238(16) 0.80483(3) 0.0234(2) Uani 1 1 d . . . . .
C9' C 0.32022(16) 0.6852(3) 0.52568(4) 0.0270(3) Uani 1 1 d . . . . .
H9'A H 0.343028 0.691358 0.496318 0.040 Uiso 1 1 calc R U . . .
H9'B H 0.364048 0.842870 0.540172 0.040 Uiso 1 1 calc R U . . .
H9'C H 0.198664 0.674195 0.526851 0.040 Uiso 1 1 calc R U . . .
C4' C 0.39443(14) 0.4371(2) 0.58813(4) 0.0188(3) Uani 1 1 d . . . . .
C3' C 0.30720(14) 0.6010(2) 0.61236(4) 0.0204(3) Uani 1 1 d . . . . .
H3' H 0.246235 0.744919 0.599896 0.024 Uiso 1 1 calc R U . . .
C2' C 0.31007(14) 0.5519(2) 0.65518(4) 0.0217(3) Uani 1 1 d . . . . .
H2' H 0.251269 0.665325 0.671769 0.026 Uiso 1 1 calc R U . . .
C1' C 0.39660(14) 0.3416(2) 0.67423(4) 0.0200(3) Uani 1 1 d . . . . .
C7' C 0.40130(15) 0.2896(3) 0.72066(4) 0.0239(3) Uani 1 1 d . . . . .
H7'A H 0.386351 0.101301 0.725350 0.029 Uiso 1 1 calc R U . . .
H7'B H 0.307666 0.382855 0.731753 0.029 Uiso 1 1 calc R U . . .
C8' C 0.56699(15) 0.3782(3) 0.74387(3) 0.0222(3) Uani 1 1 d . . . . .
H8'A H 0.659776 0.283815 0.732584 0.027 Uiso 1 1 calc R U . . .
H8'B H 0.581889 0.565727 0.738524 0.027 Uiso 1 1 calc R U . . .
C7 C 0.57185(13) 0.5335(2) 0.81624(4) 0.0178(3) Uani 1 1 d . . . . .
C1 C 0.59161(14) 0.4633(2) 0.86200(4) 0.0175(2) Uani 1 1 d . . . . .
C6 C 0.68483(14) 0.2498(2) 0.87797(4) 0.0194(3) Uani 1 1 d . . . . .
H6 H 0.732795 0.134557 0.859491 0.023 Uiso 1 1 calc R U . . .
C5 C 0.70756(15) 0.2058(2) 0.92105(4) 0.0219(3) Uani 1 1 d . . . . .
H5 H 0.772734 0.061834 0.931976 0.026 Uiso 1 1 calc R U . . .
C4 C 0.63549(15) 0.3711(3) 0.94813(4) 0.0233(3) Uani 1 1 d . . . . .
H4 H 0.651276 0.340284 0.977518 0.028 Uiso 1 1 calc R U . . .
C5' C 0.48544(15) 0.2289(2) 0.60681(4) 0.0214(3) Uani 1 1 d . . . . .
H5' H 0.547505 0.119136 0.590413 0.026 Uiso 1 1 calc R U . . .
C6' C 0.48539(15) 0.1823(2) 0.64925(4) 0.0212(3) Uani 1 1 d . . . . .
H6' H 0.547018 0.038820 0.661674 0.025 Uiso 1 1 calc R U . . .
C2 C 0.51972(14) 0.6290(2) 0.88936(4) 0.0208(3) Uani 1 1 d . . . . .
H2 H 0.456272 0.775021 0.878600 0.025 Uiso 1 1 calc R U . . .
C3 C 0.54032(16) 0.5817(3) 0.93223(4) 0.0246(3) Uani 1 1 d . . . . .
H3 H 0.489301 0.693317 0.950682 0.030 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O4' C9' 1.4261(15) . ?
O4' C4' 1.3765(14) . ?
N8' H8' 0.8800 . ?
N8' C8' 1.4578(14) . ?
N8' C7 1.3471(16) . ?
O7 C7 1.2373(15) . ?
C9' H9'A 0.9800 . ?
C9' H9'B 0.9800 . ?
C9' H9'C 0.9800 . ?
C4' C3' 1.3881(17) . ?
C4' C5' 1.3921(17) . ?
C3' H3' 0.9500 . ?
C3' C2' 1.3943(17) . ?
C2' H2' 0.9500 . ?
C2' C1' 1.3886(18) . ?
C1' C7' 1.5093(16) . ?
C1' C6' 1.3964(17) . ?
C7' H7'A 0.9900 . ?
C7' H7'B 0.9900 . ?
C7' C8' 1.5158(17) . ?
C8' H8'A 0.9900 . ?
C8' H8'B 0.9900 . ?
C7 C1 1.5025(15) . ?
C1 C6 1.3926(17) . ?
C1 C2 1.3940(17) . ?
C6 H6 0.9500 . ?
C6 C5 1.3918(16) . ?
C5 H5 0.9500 . ?
C5 C4 1.3878(18) . ?
C4 H4 0.9500 . ?
C4 C3 1.3879(19) . ?
C5' H5' 0.9500 . ?
C5' C6' 1.3823(17) . ?
C6' H6' 0.9500 . ?
C2 H2 0.9500 . ?
C2 C3 1.3875(17) . ?
C3 H3 0.9500 . ?

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
_geom_angle_publ_flag
C4' O4' C9' 117.25(9) . . ?
C8' N8' H8' 119.1 . . ?
C7 N8' H8' 119.1 . . ?
C7 N8' C8' 121.78(10) . . ?
O4' C9' H9'A 109.5 . . ?
O4' C9' H9'B 109.5 . . ?
O4' C9' H9'C 109.5 . . ?
H9'A C9' H9'B 109.5 . . ?
H9'A C9' H9'C 109.5 . . ?
H9'B C9' H9'C 109.5 . . ?
O4' C4' C3' 124.86(11) . . ?
O4' C4' C5' 115.22(10) . . ?
C3' C4' C5' 119.92(11) . . ?
C4' C3' H3' 120.4 . . ?
C4' C3' C2' 119.25(11) . . ?
C2' C3' H3' 120.4 . . ?
C3' C2' H2' 119.1 . . ?
C1' C2' C3' 121.74(11) . . ?
C1' C2' H2' 119.1 . . ?
C2' C1' C7' 121.84(11) . . ?
C2' C1' C6' 117.81(11) . . ?
C6' C1' C7' 120.32(11) . . ?
C1' C7' H7'A 109.5 . . ?
C1' C7' H7'B 109.5 . . ?
C1' C7' C8' 110.70(9) . . ?
H7'A C7' H7'B 108.1 . . ?
C8' C7' H7'A 109.5 . . ?
C8' C7' H7'B 109.5 . . ?
N8' C8' C7' 113.30(10) . . ?
N8' C8' H8'A 108.9 . . ?
N8' C8' H8'B 108.9 . . ?
C7' C8' H8'A 108.9 . . ?
C7' C8' H8'B 108.9 . . ?
H8'A C8' H8'B 107.7 . . ?
N8' C7 C1 116.31(10) . . ?
O7 C7 N8' 122.77(11) . . ?
O7 C7 C1 120.90(10) . . ?
C6 C1 C7 122.77(10) . . ?
C6 C1 C2 119.57(11) . . ?
C2 C1 C7 117.57(10) . . ?
C1 C6 H6 120.1 . . ?
C5 C6 C1 119.84(11) . . ?
C5 C6 H6 120.1 . . ?
C6 C5 H5 119.8 . . ?
C4 C5 C6 120.33(11) . . ?
C4 C5 H5 119.8 . . ?
C5 C4 H4 120.0 . . ?
C5 C4 C3 119.91(11) . . ?
C3 C4 H4 120.0 . . ?
C4' C5' H5' 120.0 . . ?
C6' C5' C4' 119.92(11) . . ?
C6' C5' H5' 120.0 . . ?
C1' C6' H6' 119.3 . . ?
C5' C6' C1' 121.35(11) . . ?
C5' C6' H6' 119.3 . . ?
C1 C2 H2 119.8 . . ?
C3 C2 C1 120.37(11) . . ?
C3 C2 H2 119.8 . . ?
C4 C3 H3 120.0 . . ?
C2 C3 C4 119.97(11) . . ?
C2 C3 H3 120.0 . . ?

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
_geom_torsion_publ_flag
O4' C4' C3' C2' 179.34(10) . . . . ?
O4' C4' C5' C6' -178.71(10) . . . . ?
N8' C7 C1 C6 29.18(15) . . . . ?
N8' C7 C1 C2 -154.16(11) . . . . ?
O7 C7 C1 C6 -149.70(11) . . . . ?
O7 C7 C1 C2 26.96(16) . . . . ?
C9' O4' C4' C3' 4.66(17) . . . . ?
C9' O4' C4' C5' -175.04(10) . . . . ?
C4' C3' C2' C1' -0.66(18) . . . . ?
C4' C5' C6' C1' -0.58(18) . . . . ?
C3' C4' C5' C6' 1.57(17) . . . . ?
C3' C2' C1' C7' 179.39(11) . . . . ?
C3' C2' C1' C6' 1.62(17) . . . . ?
C2' C1' C7' C8' -101.64(13) . . . . ?
C2' C1' C6' C5' -1.00(17) . . . . ?
C1' C7' C8' N8' 179.41(10) . . . . ?
C7' C1' C6' C5' -178.81(11) . . . . ?
C8' N8' C7 O7 1.05(17) . . . . ?
C8' N8' C7 C1 -177.81(9) . . . . ?
C7 N8' C8' C7' -107.95(13) . . . . ?
C7 C1 C6 C5 175.64(10) . . . . ?
C7 C1 C2 C3 -176.93(10) . . . . ?
C1 C6 C5 C4 1.06(17) . . . . ?
C1 C2 C3 C4 1.18(18) . . . . ?
C6 C1 C2 C3 -0.16(17) . . . . ?
C6 C5 C4 C3 -0.04(18) . . . . ?
C5 C4 C3 C2 -1.08(18) . . . . ?
C5' C4' C3' C2' -0.97(17) . . . . ?
C6' C1' C7' C8' 76.08(15) . . . . ?
C2 C1 C6 C5 -0.96(17) . . . . ?

_olex2_submission_original_sample_id rip_I
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_mo_riparin_ii_300K
_database_code_depnum_ccdc_archive 'CCDC 1892486'
loop_
_audit_author_name
_audit_author_address
'Alejandro Pedro Ayala'
;Universidade Federal do Ceara
Brazil
;
_audit_update_record             
;
2020-04-15 deposited with the CCDC.	2020-10-12 downloaded from the CCDC.
;
_audit_creation_date             2020-04-14
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        'riparin II'
_chemical_formula_moiety         '4(C16 H17 N O3)'
_chemical_formula_sum            'C64 H68 N4 O12'
_chemical_formula_weight         1085.22
_chemical_absolute_configuration ad
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_H-M_alt        'C 1 c 1'
_space_group_name_Hall           'C -2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'

_cell_length_a                   6.452(2)
_cell_length_b                   29.288(10)
_cell_length_c                   14.875(8)
_cell_angle_alpha                90
_cell_angle_beta                 97.04(2)
_cell_angle_gamma                90
_cell_volume                     2790(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7645
_cell_measurement_temperature    300
_cell_measurement_theta_max      27.27
_cell_measurement_theta_min      2.76
_shelx_estimated_absorpt_T_max   0.989
_shelx_estimated_absorpt_T_min   0.950
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.7119
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1478 before and 0.0675 after correction.
The Ratio of minimum to maximum transmission is 0.9588.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.292
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Columnar
_exptl_crystal_F_000             1152
_exptl_crystal_size_max          0.577
_exptl_crystal_size_mid          0.136
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0809
_diffrn_reflns_av_unetI/netI     0.0450
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       39
_diffrn_reflns_limit_k_min       -39
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            52822
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.633
_diffrn_reflns_theta_min         2.759
_diffrn_ambient_temperature      300
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'Bruker PHOTON II'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTON II CPAD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.991
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.994
_reflns_number_gt                4336
_reflns_number_total             7128
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SIR2011 (Burla et al., 2007)'
_refine_diff_density_max         0.149
_refine_diff_density_min         -0.166
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details 
;
 Flack x determined using 1724 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.3(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     365
_refine_ls_number_reflns         7128
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1029
_refine_ls_R_factor_gt           0.0452
_refine_ls_restrained_S_all      1.056
_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)+(0.0590P)²+0.3687P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1024
_refine_ls_wR_factor_ref         0.1356
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C8B'(H8BA,H8BB), C7B'(H7BA,H7BB), C8A'(H8AA,H8AB), C0AA(H0AA,H0AB)
2.b Aromatic/amide H refined with riding coordinates:
 N8B'(H8B'), C5B'(H5B'), C3B'(H3B'), C6B'(H6B'), N8A'(H8A'), C6A'(H6A'),
 C5A'(H5A'), C6B(H6B), C2B'(H2B'), C5B(H5B), C2A'(H2A'), C3A(H3A), C4B(H4B),
 C6A(H6A), C3B(H3B), C3A'(H3A'), C4A(H4A), C5A(H5A)
2.c Idealised Me refined as rotating group:
 C9A'(H9AA,H9AB,H9AC), C9B'(H9BA,H9BB,H9BC)
2.d Idealised tetrahedral OH refined as rotating group:
 O2B(H2B), O2A(H2A)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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
O7B O 0.2874(4) 0.39028(9) 0.5771(2) 0.0676(8) Uani 1 1 d . . . . .
O4B' O 1.1245(4) 0.61971(9) 0.6094(2) 0.0659(7) Uani 1 1 d . . . . .
O4A' O -0.1124(4) -0.01574(9) 0.4090(2) 0.0716(8) Uani 1 1 d . . . . .
N8B' N 0.6305(4) 0.37587(10) 0.5937(2) 0.0503(7) Uani 1 1 d . . . . .
H8B' H 0.726170 0.355395 0.603292 0.060 Uiso 1 1 calc R U . . .
O2B O 0.0414(4) 0.33467(10) 0.6349(3) 0.0826(10) Uani 1 1 d . . . . .
H2B H 0.086480 0.359320 0.619713 0.124 Uiso 1 1 calc R U . . .
O7A O 0.6736(5) 0.21561(10) 0.4181(2) 0.0827(9) Uani 1 1 d . . . . .
C5B' C 1.1602(5) 0.53687(12) 0.6034(3) 0.0533(8) Uani 1 1 d . . . . .
H5B' H 1.287296 0.538604 0.580143 0.064 Uiso 1 1 calc R U . . .
C7B C 0.4341(5) 0.36260(11) 0.5929(2) 0.0459(8) Uani 1 1 d . . . . .
C4B' C 1.0568(5) 0.57618(11) 0.6226(2) 0.0490(8) Uani 1 1 d . . . . .
C3B' C 0.8682(5) 0.57264(13) 0.6571(3) 0.0543(8) Uani 1 1 d . . . . .
H3B' H 0.797438 0.598952 0.670562 0.065 Uiso 1 1 calc R U . . .
O2A O 0.9402(5) 0.27785(11) 0.4262(3) 0.0960(11) Uani 1 1 d . . . . .
H2A H 0.893539 0.251842 0.427328 0.144 Uiso 1 1 calc R U . . .
C4A' C -0.0531(6) 0.02770(12) 0.3891(2) 0.0526(8) Uani 1 1 d . . . . .
C1B C 0.3921(5) 0.31449(12) 0.6153(2) 0.0444(7) Uani 1 1 d . . . . .
C6B' C 1.0738(6) 0.49483(12) 0.6190(3) 0.0548(9) Uani 1 1 d . . . . .
H6B' H 1.145741 0.468530 0.606465 0.066 Uiso 1 1 calc R U . . .
N8A' N 0.3326(5) 0.23246(11) 0.4062(2) 0.0674(9) Uani 1 1 d . . . . .
H8A' H 0.238712 0.253308 0.396223 0.081 Uiso 1 1 calc R U . . .
C6A' C -0.1002(6) 0.10259(13) 0.3283(3) 0.0613(10) Uani 1 1 d . . . . .
H6A' H -0.187431 0.124184 0.297357 0.074 Uiso 1 1 calc R U . . .
C5A' C -0.1781(6) 0.05964(13) 0.3419(3) 0.0588(9) Uani 1 1 d . . . . .
H5A' H -0.314867 0.052368 0.319159 0.071 Uiso 1 1 calc R U . . .
C1A C 0.5780(5) 0.29213(12) 0.3820(2) 0.0518(8) Uani 1 1 d . . . . .
C1B' C 0.8844(5) 0.49052(12) 0.6526(2) 0.0503(8) Uani 1 1 d . . . . .
C1A' C 0.1030(6) 0.11458(13) 0.3589(2) 0.0584(9) Uani 1 1 d . . . . .
C6B C 0.5414(5) 0.28017(11) 0.6194(3) 0.0529(8) Uani 1 1 d . . . . .
H6B H 0.674226 0.286971 0.604957 0.063 Uiso 1 1 calc R U . . .
C2B C 0.1929(5) 0.30299(13) 0.6371(3) 0.0565(9) Uani 1 1 d . . . . .
C2B' C 0.7843(6) 0.53052(13) 0.6718(3) 0.0573(9) Uani 1 1 d . . . . .
H2B' H 0.657300 0.528878 0.695127 0.069 Uiso 1 1 calc R U . . .
C2A C 0.7843(6) 0.30700(14) 0.3971(3) 0.0626(10) Uani 1 1 d . . . . .
C8B' C 0.6961(5) 0.42235(11) 0.5795(2) 0.0529(8) Uani 1 1 d . . . . .
H8BA H 0.576494 0.440196 0.553963 0.064 Uiso 1 1 calc R U . . .
H8BB H 0.797368 0.422417 0.536371 0.064 Uiso 1 1 calc R U . . .
C7B' C 0.7916(6) 0.44411(13) 0.6667(3) 0.0610(9) Uani 1 1 d . . . . .
H7BA H 0.900050 0.424233 0.695772 0.073 Uiso 1 1 calc R U . . .
H7BB H 0.685258 0.447159 0.707093 0.073 Uiso 1 1 calc R U . . .
C8A' C 0.2652(7) 0.18637(14) 0.4262(3) 0.0693(11) Uani 1 1 d . . . . .
H8AA H 0.155405 0.188055 0.465173 0.083 Uiso 1 1 calc R U . . .
H8AB H 0.381607 0.169763 0.458347 0.083 Uiso 1 1 calc R U . . .
C5B C 0.4976(7) 0.23658(13) 0.6442(3) 0.0645(10) Uani 1 1 d . . . . .
H5B H 0.599508 0.214033 0.645977 0.077 Uiso 1 1 calc R U . . .
C2A' C 0.2265(6) 0.08149(14) 0.4059(3) 0.0617(10) Uani 1 1 d . . . . .
H2A' H 0.363933 0.088565 0.427789 0.074 Uiso 1 1 calc R U . . .
C9A' C -0.3223(7) -0.02855(16) 0.3833(4) 0.0755(12) Uani 1 1 d . . . . .
H9AA H -0.352310 -0.027680 0.318512 0.113 Uiso 1 1 calc R U . . .
H9AB H -0.412963 -0.007744 0.409543 0.113 Uiso 1 1 calc R U . . .
H9AC H -0.344356 -0.058932 0.404427 0.113 Uiso 1 1 calc R U . . .
C7A C 0.5301(6) 0.24405(13) 0.4025(3) 0.0593(9) Uani 1 1 d . . . . .
C3A C 0.8329(7) 0.35229(16) 0.3840(3) 0.0733(12) Uani 1 1 d . . . . .
H3A H 0.970550 0.362117 0.396376 0.088 Uiso 1 1 calc R U . . .
C4B C 0.3029(7) 0.22623(14) 0.6664(3) 0.0676(11) Uani 1 1 d . . . . .
H4B H 0.273628 0.196613 0.683500 0.081 Uiso 1 1 calc R U . . .
C6A C 0.4259(7) 0.32348(14) 0.3491(3) 0.0664(10) Uani 1 1 d . . . . .
H6A H 0.287594 0.314088 0.336836 0.080 Uiso 1 1 calc R U . . .
C3B C 0.1515(6) 0.25900(15) 0.6635(3) 0.0707(11) Uani 1 1 d . . . . .
H3B H 0.020434 0.251703 0.679367 0.085 Uiso 1 1 calc R U . . .
C3A' C 0.1519(6) 0.03867(13) 0.4210(3) 0.0593(9) Uani 1 1 d . . . . .
H3A' H 0.238341 0.017105 0.452511 0.071 Uiso 1 1 calc R U . . .
C0AA C 0.1866(9) 0.16133(15) 0.3414(3) 0.0769(12) Uani 1 1 d . . . . .
H0AA H 0.299385 0.158307 0.304316 0.092 Uiso 1 1 calc R U . . .
H0AB H 0.076772 0.179167 0.307592 0.092 Uiso 1 1 calc R U . . .
C4A C 0.6815(9) 0.38245(16) 0.3533(3) 0.0786(13) Uani 1 1 d . . . . .
H4A H 0.715883 0.412859 0.344930 0.094 Uiso 1 1 calc R U . . .
C9B' C 1.3146(7) 0.62534(15) 0.5729(3) 0.0756(12) Uani 1 1 d . . . . .
H9BA H 1.307719 0.609515 0.516093 0.113 Uiso 1 1 calc R U . . .
H9BB H 1.426872 0.613107 0.614224 0.113 Uiso 1 1 calc R U . . .
H9BC H 1.338707 0.657243 0.563547 0.113 Uiso 1 1 calc R U . . .
C5A C 0.4771(8) 0.36844(15) 0.3344(3) 0.0801(13) Uani 1 1 d . . . . .
H5A H 0.374141 0.389108 0.311966 0.096 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O7B C7B 1.246(4) . ?
O4B' C4B' 1.370(4) . ?
O4B' C9B' 1.410(5) . ?
O4A' C4A' 1.371(4) . ?
O4A' C9A' 1.412(5) . ?
N8B' H8B' 0.8600 . ?
N8B' C7B 1.324(4) . ?
N8B' C8B' 1.449(4) . ?
O2B H2B 0.8200 . ?
O2B C2B 1.345(4) . ?
O7A C7A 1.246(5) . ?
C5B' H5B' 0.9300 . ?
C5B' C4B' 1.378(5) . ?
C5B' C6B' 1.383(5) . ?
C7B C1B 1.481(5) . ?
C4B' C3B' 1.381(5) . ?
C3B' H3B' 0.9300 . ?
C3B' C2B' 1.375(5) . ?
O2A H2A 0.8200 . ?
O2A C2A 1.349(5) . ?
C4A' C5A' 1.371(5) . ?
C4A' C3A' 1.387(5) . ?
C1B C6B 1.388(5) . ?
C1B C2B 1.405(5) . ?
C6B' H6B' 0.9300 . ?
C6B' C1B' 1.382(5) . ?
N8A' H8A' 0.8600 . ?
N8A' C8A' 1.460(5) . ?
N8A' C7A 1.326(5) . ?
C6A' H6A' 0.9300 . ?
C6A' C5A' 1.379(5) . ?
C6A' C1A' 1.379(5) . ?
C5A' H5A' 0.9300 . ?
C1A C2A 1.392(5) . ?
C1A C7A 1.482(5) . ?
C1A C6A 1.389(5) . ?
C1B' C2B' 1.384(5) . ?
C1B' C7B' 1.510(5) . ?
C1A' C2A' 1.388(5) . ?
C1A' C0AA 1.506(6) . ?
C6B H6B 0.9300 . ?
C6B C5B 1.368(5) . ?
C2B C3B 1.383(5) . ?
C2B' H2B' 0.9300 . ?
C2A C3A 1.382(6) . ?
C8B' H8BA 0.9700 . ?
C8B' H8BB 0.9700 . ?
C8B' C7B' 1.508(5) . ?
C7B' H7BA 0.9700 . ?
C7B' H7BB 0.9700 . ?
C8A' H8AA 0.9700 . ?
C8A' H8AB 0.9700 . ?
C8A' C0AA 1.493(6) . ?
C5B H5B 0.9300 . ?
C5B C4B 1.371(6) . ?
C2A' H2A' 0.9300 . ?
C2A' C3A' 1.372(5) . ?
C9A' H9AA 0.9600 . ?
C9A' H9AB 0.9600 . ?
C9A' H9AC 0.9600 . ?
C3A H3A 0.9300 . ?
C3A C4A 1.354(7) . ?
C4B H4B 0.9300 . ?
C4B C3B 1.367(6) . ?
C6A H6A 0.9300 . ?
C6A C5A 1.381(6) . ?
C3B H3B 0.9300 . ?
C3A' H3A' 0.9300 . ?
C0AA H0AA 0.9700 . ?
C0AA H0AB 0.9700 . ?
C4A H4A 0.9300 . ?
C4A C5A 1.377(7) . ?
C9B' H9BA 0.9600 . ?
C9B' H9BB 0.9600 . ?
C9B' H9BC 0.9600 . ?
C5A H5A 0.9300 . ?

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
_geom_angle_publ_flag
C4B' O4B' C9B' 118.2(3) . . ?
C4A' O4A' C9A' 118.1(3) . . ?
C7B N8B' H8B' 117.6 . . ?
C7B N8B' C8B' 124.8(3) . . ?
C8B' N8B' H8B' 117.6 . . ?
C2B O2B H2B 109.5 . . ?
C4B' C5B' H5B' 120.2 . . ?
C4B' C5B' C6B' 119.6(3) . . ?
C6B' C5B' H5B' 120.2 . . ?
O7B C7B N8B' 121.0(3) . . ?
O7B C7B C1B 120.4(3) . . ?
N8B' C7B C1B 118.6(3) . . ?
O4B' C4B' C5B' 125.2(3) . . ?
O4B' C4B' C3B' 115.8(3) . . ?
C5B' C4B' C3B' 119.0(3) . . ?
C4B' C3B' H3B' 119.7 . . ?
C2B' C3B' C4B' 120.5(3) . . ?
C2B' C3B' H3B' 119.7 . . ?
C2A O2A H2A 109.5 . . ?
O4A' C4A' C3A' 114.9(3) . . ?
C5A' C4A' O4A' 125.6(3) . . ?
C5A' C4A' C3A' 119.6(3) . . ?
C6B C1B C7B 123.6(3) . . ?
C6B C1B C2B 117.8(3) . . ?
C2B C1B C7B 118.6(3) . . ?
C5B' C6B' H6B' 118.8 . . ?
C1B' C6B' C5B' 122.3(3) . . ?
C1B' C6B' H6B' 118.8 . . ?
C8A' N8A' H8A' 118.1 . . ?
C7A N8A' H8A' 118.1 . . ?
C7A N8A' C8A' 123.8(3) . . ?
C5A' C6A' H6A' 118.9 . . ?
C5A' C6A' C1A' 122.2(4) . . ?
C1A' C6A' H6A' 118.9 . . ?
C4A' C5A' C6A' 119.7(3) . . ?
C4A' C5A' H5A' 120.2 . . ?
C6A' C5A' H5A' 120.2 . . ?
C2A C1A C7A 118.9(3) . . ?
C6A C1A C2A 118.1(4) . . ?
C6A C1A C7A 123.0(3) . . ?
C6B' C1B' C2B' 116.9(3) . . ?
C6B' C1B' C7B' 121.0(3) . . ?
C2B' C1B' C7B' 122.0(3) . . ?
C6A' C1A' C2A' 116.9(4) . . ?
C6A' C1A' C0AA 121.4(4) . . ?
C2A' C1A' C0AA 121.8(4) . . ?
C1B C6B H6B 119.3 . . ?
C5B C6B C1B 121.5(3) . . ?
C5B C6B H6B 119.3 . . ?
O2B C2B C1B 120.8(3) . . ?
O2B C2B C3B 119.0(3) . . ?
C3B C2B C1B 120.2(3) . . ?
C3B' C2B' C1B' 121.6(3) . . ?
C3B' C2B' H2B' 119.2 . . ?
C1B' C2B' H2B' 119.2 . . ?
O2A C2A C1A 120.9(4) . . ?
O2A C2A C3A 118.6(4) . . ?
C3A C2A C1A 120.4(4) . . ?
N8B' C8B' H8BA 109.3 . . ?
N8B' C8B' H8BB 109.3 . . ?
N8B' C8B' C7B' 111.6(3) . . ?
H8BA C8B' H8BB 108.0 . . ?
C7B' C8B' H8BA 109.3 . . ?
C7B' C8B' H8BB 109.3 . . ?
C1B' C7B' H7BA 109.0 . . ?
C1B' C7B' H7BB 109.0 . . ?
C8B' C7B' C1B' 112.8(3) . . ?
C8B' C7B' H7BA 109.0 . . ?
C8B' C7B' H7BB 109.0 . . ?
H7BA C7B' H7BB 107.8 . . ?
N8A' C8A' H8AA 109.4 . . ?
N8A' C8A' H8AB 109.4 . . ?
N8A' C8A' C0AA 111.1(4) . . ?
H8AA C8A' H8AB 108.0 . . ?
C0AA C8A' H8AA 109.4 . . ?
C0AA C8A' H8AB 109.4 . . ?
C6B C5B H5B 120.1 . . ?
C6B C5B C4B 119.8(4) . . ?
C4B C5B H5B 120.1 . . ?
C1A' C2A' H2A' 119.0 . . ?
C3A' C2A' C1A' 122.0(3) . . ?
C3A' C2A' H2A' 119.0 . . ?
O4A' C9A' H9AA 109.5 . . ?
O4A' C9A' H9AB 109.5 . . ?
O4A' C9A' H9AC 109.5 . . ?
H9AA C9A' H9AB 109.5 . . ?
H9AA C9A' H9AC 109.5 . . ?
H9AB C9A' H9AC 109.5 . . ?
O7A C7A N8A' 121.1(4) . . ?
O7A C7A C1A 120.3(3) . . ?
N8A' C7A C1A 118.5(3) . . ?
C2A C3A H3A 119.8 . . ?
C4A C3A C2A 120.4(4) . . ?
C4A C3A H3A 119.8 . . ?
C5B C4B H4B 119.7 . . ?
C3B C4B C5B 120.7(4) . . ?
C3B C4B H4B 119.7 . . ?
C1A C6A H6A 119.6 . . ?
C5A C6A C1A 120.9(4) . . ?
C5A C6A H6A 119.6 . . ?
C2B C3B H3B 120.0 . . ?
C4B C3B C2B 120.1(4) . . ?
C4B C3B H3B 120.0 . . ?
C4A' C3A' H3A' 120.2 . . ?
C2A' C3A' C4A' 119.6(3) . . ?
C2A' C3A' H3A' 120.2 . . ?
C1A' C0AA H0AA 109.0 . . ?
C1A' C0AA H0AB 109.0 . . ?
C8A' C0AA C1A' 113.1(4) . . ?
C8A' C0AA H0AA 109.0 . . ?
C8A' C0AA H0AB 109.0 . . ?
H0AA C0AA H0AB 107.8 . . ?
C3A C4A H4A 119.7 . . ?
C3A C4A C5A 120.5(4) . . ?
C5A C4A H4A 119.7 . . ?
O4B' C9B' H9BA 109.5 . . ?
O4B' C9B' H9BB 109.5 . . ?
O4B' C9B' H9BC 109.5 . . ?
H9BA C9B' H9BB 109.5 . . ?
H9BA C9B' H9BC 109.5 . . ?
H9BB C9B' H9BC 109.5 . . ?
C6A C5A H5A 120.2 . . ?
C4A C5A C6A 119.6(4) . . ?
C4A C5A H5A 120.2 . . ?

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
_geom_torsion_publ_flag
O7B C7B C1B C6B 169.3(3) . . . . ?
O7B C7B C1B C2B -13.2(5) . . . . ?
O4B' C4B' C3B' C2B' 179.1(3) . . . . ?
O4A' C4A' C5A' C6A' 178.5(4) . . . . ?
O4A' C4A' C3A' C2A' -179.1(4) . . . . ?
N8B' C7B C1B C6B -13.5(5) . . . . ?
N8B' C7B C1B C2B 164.0(3) . . . . ?
N8B' C8B' C7B' C1B' 173.3(3) . . . . ?
O2B C2B C3B C4B -180.0(4) . . . . ?
C5B' C4B' C3B' C2B' -0.3(5) . . . . ?
C5B' C6B' C1B' C2B' -1.1(5) . . . . ?
C5B' C6B' C1B' C7B' 178.5(3) . . . . ?
C7B N8B' C8B' C7B' 106.1(4) . . . . ?
C7B C1B C6B C5B 177.2(3) . . . . ?
C7B C1B C2B O2B 2.1(5) . . . . ?
C7B C1B C2B C3B -176.3(4) . . . . ?
C4B' C5B' C6B' C1B' 0.7(5) . . . . ?
C4B' C3B' C2B' C1B' -0.1(6) . . . . ?
O2A C2A C3A C4A 178.9(4) . . . . ?
C1B C6B C5B C4B -0.5(6) . . . . ?
C1B C2B C3B C4B -1.6(6) . . . . ?
C6B' C5B' C4B' O4B' -179.3(3) . . . . ?
C6B' C5B' C4B' C3B' 0.0(5) . . . . ?
C6B' C1B' C2B' C3B' 0.8(5) . . . . ?
C6B' C1B' C7B' C8B' -76.4(5) . . . . ?
N8A' C8A' C0AA C1A' -176.5(4) . . . . ?
C6A' C1A' C2A' C3A' 0.4(6) . . . . ?
C6A' C1A' C0AA C8A' 121.5(4) . . . . ?
C5A' C4A' C3A' C2A' 0.8(6) . . . . ?
C5A' C6A' C1A' C2A' -1.0(6) . . . . ?
C5A' C6A' C1A' C0AA 178.6(4) . . . . ?
C1A C2A C3A C4A -2.3(6) . . . . ?
C1A C6A C5A C4A -0.5(7) . . . . ?
C1A' C6A' C5A' C4A' 1.5(6) . . . . ?
C1A' C2A' C3A' C4A' -0.3(6) . . . . ?
C6B C1B C2B O2B 179.7(4) . . . . ?
C6B C1B C2B C3B 1.4(5) . . . . ?
C6B C5B C4B C3B 0.3(7) . . . . ?
C2B C1B C6B C5B -0.3(5) . . . . ?
C2B' C1B' C7B' C8B' 103.2(4) . . . . ?
C2A C1A C7A O7A -12.1(6) . . . . ?
C2A C1A C7A N8A' 166.2(4) . . . . ?
C2A C1A C6A C5A -1.9(6) . . . . ?
C2A C3A C4A C5A -0.2(7) . . . . ?
C8B' N8B' C7B O7B 1.8(6) . . . . ?
C8B' N8B' C7B C1B -175.4(3) . . . . ?
C7B' C1B' C2B' C3B' -178.8(3) . . . . ?
C8A' N8A' C7A O7A -1.4(6) . . . . ?
C8A' N8A' C7A C1A -179.7(4) . . . . ?
C5B C4B C3B C2B 0.7(7) . . . . ?
C2A' C1A' C0AA C8A' -58.9(6) . . . . ?
C9A' O4A' C4A' C5A' -3.5(6) . . . . ?
C9A' O4A' C4A' C3A' 176.4(4) . . . . ?
C7A N8A' C8A' C0AA -98.8(5) . . . . ?
C7A C1A C2A O2A 2.8(6) . . . . ?
C7A C1A C2A C3A -176.0(4) . . . . ?
C7A C1A C6A C5A 177.4(4) . . . . ?
C3A C4A C5A C6A 1.6(7) . . . . ?
C6A C1A C2A O2A -177.9(4) . . . . ?
C6A C1A C2A C3A 3.3(6) . . . . ?
C6A C1A C7A O7A 168.7(4) . . . . ?
C6A C1A C7A N8A' -13.1(6) . . . . ?
C3A' C4A' C5A' C6A' -1.3(6) . . . . ?
C0AA C1A' C2A' C3A' -179.2(4) . . . . ?
C9B' O4B' C4B' C5B' 0.3(5) . . . . ?
C9B' O4B' C4B' C3B' -179.0(4) . . . . ?

_olex2_submission_original_sample_id riparin_II_300K
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_Riparin_III
_database_code_depnum_ccdc_archive 'CCDC 1892487'
loop_
_audit_author_name
_audit_author_address
'Alejandro Pedro Ayala'
;Universidade Federal do Cear?
Brazil
;
_audit_update_record             
;
2019-01-22 deposited with the CCDC.	2020-10-12 downloaded from the CCDC.
;
_audit_creation_date             2018-06-01
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        'Riparin III'
_chemical_formula_moiety         'C16 H17 N O4'
_chemical_formula_sum            'C16 H17 N O4'
_chemical_formula_weight         287.30
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_H-M_alt        'P 1 c 1'
_space_group_name_Hall           'P -2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'

_cell_length_a                   11.6479(3)
_cell_length_b                   4.86110(10)
_cell_length_c                   13.4222(3)
_cell_angle_alpha                90
_cell_angle_beta                 106.7930(10)
_cell_angle_gamma                90
_cell_volume                     727.58(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    255
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      3.96
_cell_measurement_theta_min      72.34
_shelx_estimated_absorpt_T_max   0.893
_shelx_estimated_absorpt_T_min   0.771
_exptl_absorpt_coefficient_mu    0.780
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.5748
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1435 before and 0.0865 after correction.
The Ratio of minimum to maximum transmission is 0.7371.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             304
_exptl_crystal_preparation       
'The crystal was prepared by recrystallization using solvent mixture of methanol:water.'
_exptl_crystal_recrystallization_method 
'The solution was left at room temperature for a couple of days'
_exptl_crystal_size_max          0.351
_exptl_crystal_size_mid          0.162
_exptl_crystal_size_min          0.148
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0540
_diffrn_reflns_av_unetI/netI     0.0376
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            27693
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.535
_diffrn_reflns_theta_min         6.888
_diffrn_ambient_temperature      295.85
_diffrn_detector                 'Photon II CPAD Area Detector'
_diffrn_detector_area_resol_mean 7.3910
_diffrn_detector_type            'Bruker PHOTON II'
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'multilayer mirrors'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'micro-focus sealed tube'
_diffrn_source_type              'Incoatech I\mS HB'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.965
_reflns_Friedel_fraction_full    0.970
_reflns_Friedel_fraction_max     0.960
_reflns_number_gt                2721
_reflns_number_total             2808
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.115
_refine_diff_density_min         -0.121
_refine_diff_density_rms         0.027
_refine_ls_abs_structure_details 
;
 Flack x determined using 1290 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.16(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         2808
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0331
_refine_ls_R_factor_gt           0.0323
_refine_ls_restrained_S_all      1.063
_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)+(0.0521P)²+0.0539P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0885
_refine_ls_wR_factor_ref         0.0895
_refine_special_details          ?
_olex2_refinement_description    
;
1. Others
 Fixed Uiso: H6(0.077) H2(0.095) H8'(0.061) H5'(0.07) H6'(0.069) H8'A(0.063)
 H8'B(0.063) H5(0.057) H3(0.063) H7'A(0.071) H7'B(0.071) H3'(0.083) H4(0.063)
 H2'(0.081) H9'A(0.127) H9'B(0.127) H9'C(0.127)
 Fixed X: H6(0.328054) H2(0.206257) H8'(0.416652) H5'(0.863283) H6'(0.771477)
 H8'A(0.420084) H8'B(0.491457) H5(0.180239) H3(0.040361) H7'A(0.567153)
 H7'B(0.63783) H3'(0.644152) H4(0.046318) H2'(0.551137) H9'A(0.932268)
 H9'B(0.880235) H9'C(0.974579)
 Fixed Y: H6(0.398731) H2(0.943978) H8'(0.354101) H5'(-0.239087) H6'(0.04405)
 H8'A(0.220572) H8'B(0.064165) H5(0.679953) H3(1.176331) H7'A(0.56729)
 H7'B(0.418664) H3'(0.04921) H4(1.016397) H2'(0.323498) H9'A(-0.560445) H9'B(-
 0.585801) H9'C(-0.356643)
 Fixed Z: H6(0.790597) H2(0.417472) H8'(0.626695) H5'(0.469161) H6'(0.560367)
 H8'A(0.431628) H8'B(0.532536) H5(0.801608) H3(0.559672) H7'A(0.465007)
 H7'B(0.568552) H3'(0.202523) H4(0.72258) H2'(0.294817) H9'A(0.261195)
 H9'B(0.356262) H9'C(0.355218)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
O6 O 0.33592(13) 0.4319(3) 0.73303(10) 0.0513(4) Uani 1 1 d . . . . .
H6 H 0.328054 0.398731 0.790597 0.077 Uiso 1 1 calc GR . . . .
O7 O 0.31187(15) 0.6696(3) 0.42900(10) 0.0553(4) Uani 1 1 d . . . . .
O4' O 0.8138(2) -0.2770(4) 0.26392(17) 0.0784(6) Uani 1 1 d . . . . .
O2 O 0.15626(16) 1.0174(4) 0.44098(12) 0.0633(4) Uani 1 1 d . . . . .
H2 H 0.206257 0.943978 0.417472 0.095 Uiso 1 1 calc GR . . . .
N8' N 0.40420(15) 0.3944(4) 0.56205(13) 0.0510(4) Uani 1 1 d . . . . .
H8' H 0.416652 0.354101 0.626695 0.061 Uiso 1 1 calc R . . . .
C6 C 0.25497(16) 0.6275(4) 0.68493(13) 0.0409(4) Uani 1 1 d . . . . .
C1 C 0.25129(16) 0.7120(4) 0.58308(13) 0.0406(4) Uani 1 1 d . . . . .
C2 C 0.16783(18) 0.9207(4) 0.53762(14) 0.0458(4) Uani 1 1 d . . . . .
C5' C 0.8007(2) -0.1253(5) 0.4336(2) 0.0587(5) Uani 1 1 d . . . . .
H5' H 0.863283 -0.239087 0.469161 0.070 Uiso 1 1 calc R . . . .
C7 C 0.32498(17) 0.5893(4) 0.52064(14) 0.0433(4) Uani 1 1 d . . . . .
C4' C 0.7631(2) -0.1250(5) 0.32632(19) 0.0570(5) Uani 1 1 d . . . . .
C6' C 0.7448(2) 0.0444(5) 0.48803(19) 0.0578(5) Uani 1 1 d . . . . .
H6' H 0.771477 0.044050 0.560367 0.069 Uiso 1 1 calc R . . . .
C1' C 0.65059(19) 0.2147(5) 0.43828(17) 0.0529(5) Uani 1 1 d . . . . .
C8' C 0.4713(2) 0.2453(5) 0.50220(17) 0.0523(5) Uani 1 1 d . . . . .
H8'A H 0.420084 0.220572 0.431628 0.063 Uiso 1 1 calc R . . . .
H8'B H 0.491457 0.064165 0.532536 0.063 Uiso 1 1 calc R . . . .
C5 C 0.17788(19) 0.7407(4) 0.73535(14) 0.0476(5) Uani 1 1 d . . . . .
H5 H 0.180239 0.679953 0.801608 0.057 Uiso 1 1 calc R . . . .
C3 C 0.0932(2) 1.0363(5) 0.59030(17) 0.0525(5) Uani 1 1 d . . . . .
H3 H 0.040361 1.176331 0.559672 0.063 Uiso 1 1 calc R . . . .
C7' C 0.5863(2) 0.3894(5) 0.4984(2) 0.0595(6) Uani 1 1 d . . . . .
H7'A H 0.567153 0.567290 0.465007 0.071 Uiso 1 1 calc R . . . .
H7'B H 0.637830 0.418664 0.568552 0.071 Uiso 1 1 calc R . . . .
C3' C 0.6696(3) 0.0460(6) 0.27488(19) 0.0688(7) Uani 1 1 d . . . . .
H3' H 0.644152 0.049210 0.202523 0.083 Uiso 1 1 calc R . . . .
C4 C 0.0979(2) 0.9425(5) 0.68805(17) 0.0527(5) Uani 1 1 d . . . . .
H4 H 0.046318 1.016397 0.722580 0.063 Uiso 1 1 calc R . . . .
C2' C 0.6143(2) 0.2113(6) 0.3305(2) 0.0671(6) Uani 1 1 d . . . . .
H2' H 0.551137 0.323498 0.294817 0.081 Uiso 1 1 calc R . . . .
C9' C 0.9078(3) -0.4597(6) 0.3131(3) 0.0847(9) Uani 1 1 d . . . . .
H9'A H 0.932268 -0.560445 0.261195 0.127 Uiso 1 1 calc GR . . . .
H9'B H 0.880235 -0.585801 0.356262 0.127 Uiso 1 1 calc GR . . . .
H9'C H 0.974579 -0.356643 0.355218 0.127 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O6 H6 0.8200 . ?
O6 C6 1.363(2) . ?
O7 C7 1.257(2) . ?
O4' C4' 1.372(3) . ?
O4' C9' 1.416(4) . ?
O2 H2 0.8200 . ?
O2 C2 1.349(2) . ?
N8' H8' 0.8600 . ?
N8' C7 1.327(3) . ?
N8' C8' 1.464(3) . ?
C6 C1 1.416(2) . ?
C6 C5 1.385(3) . ?
C1 C2 1.416(3) . ?
C1 C7 1.487(3) . ?
C2 C3 1.388(3) . ?
C5' H5' 0.9300 . ?
C5' C4' 1.378(4) . ?
C5' C6' 1.383(3) . ?
C4' C3' 1.385(4) . ?
C6' H6' 0.9300 . ?
C6' C1' 1.383(3) . ?
C1' C7' 1.511(3) . ?
C1' C2' 1.385(3) . ?
C8' H8'A 0.9700 . ?
C8' H8'B 0.9700 . ?
C8' C7' 1.526(3) . ?
C5 H5 0.9300 . ?
C5 C4 1.376(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.375(3) . ?
C7' H7'A 0.9700 . ?
C7' H7'B 0.9700 . ?
C3' H3' 0.9300 . ?
C3' C2' 1.377(4) . ?
C4 H4 0.9300 . ?
C2' H2' 0.9300 . ?
C9' H9'A 0.9600 . ?
C9' H9'B 0.9600 . ?
C9' H9'C 0.9600 . ?

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
_geom_angle_publ_flag
C6 O6 H6 109.5 . . ?
C4' O4' C9' 117.7(2) . . ?
C2 O2 H2 109.5 . . ?
C7 N8' H8' 118.6 . . ?
C7 N8' C8' 122.71(17) . . ?
C8' N8' H8' 118.6 . . ?
O6 C6 C1 118.91(16) . . ?
O6 C6 C5 120.21(16) . . ?
C5 C6 C1 120.88(18) . . ?
C6 C1 C7 124.49(18) . . ?
C2 C1 C6 116.71(16) . . ?
C2 C1 C7 118.75(16) . . ?
O2 C2 C1 121.97(18) . . ?
O2 C2 C3 116.45(19) . . ?
C3 C2 C1 121.59(17) . . ?
C4' C5' H5' 120.1 . . ?
C4' C5' C6' 119.7(2) . . ?
C6' C5' H5' 120.1 . . ?
O7 C7 N8' 120.30(17) . . ?
O7 C7 C1 120.03(19) . . ?
N8' C7 C1 119.68(16) . . ?
O4' C4' C5' 125.1(2) . . ?
O4' C4' C3' 115.7(2) . . ?
C5' C4' C3' 119.2(2) . . ?
C5' C6' H6' 119.0 . . ?
C1' C6' C5' 122.1(2) . . ?
C1' C6' H6' 119.0 . . ?
C6' C1' C7' 121.7(2) . . ?
C6' C1' C2' 117.2(2) . . ?
C2' C1' C7' 121.1(2) . . ?
N8' C8' H8'A 108.8 . . ?
N8' C8' H8'B 108.8 . . ?
N8' C8' C7' 113.83(17) . . ?
H8'A C8' H8'B 107.7 . . ?
C7' C8' H8'A 108.8 . . ?
C7' C8' H8'B 108.8 . . ?
C6 C5 H5 119.8 . . ?
C4 C5 C6 120.43(17) . . ?
C4 C5 H5 119.8 . . ?
C2 C3 H3 120.2 . . ?
C4 C3 C2 119.6(2) . . ?
C4 C3 H3 120.2 . . ?
C1' C7' C8' 109.60(17) . . ?
C1' C7' H7'A 109.7 . . ?
C1' C7' H7'B 109.7 . . ?
C8' C7' H7'A 109.7 . . ?
C8' C7' H7'B 109.7 . . ?
H7'A C7' H7'B 108.2 . . ?
C4' C3' H3' 119.9 . . ?
C2' C3' C4' 120.2(2) . . ?
C2' C3' H3' 119.9 . . ?
C5 C4 H4 119.6 . . ?
C3 C4 C5 120.76(19) . . ?
C3 C4 H4 119.6 . . ?
C1' C2' H2' 119.2 . . ?
C3' C2' C1' 121.6(2) . . ?
C3' C2' H2' 119.2 . . ?
O4' C9' H9'A 109.5 . . ?
O4' C9' H9'B 109.5 . . ?
O4' C9' H9'C 109.5 . . ?
H9'A C9' H9'B 109.5 . . ?
H9'A C9' H9'C 109.5 . . ?
H9'B C9' H9'C 109.5 . . ?

_olex2_submission_original_sample_id RIPIII
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_cu_riparin_II_300K
_database_code_depnum_ccdc_archive 'CCDC 2033369'
loop_
_audit_author_name
_audit_author_address
'Alejandro Pedro Ayala'
;Universidade Federal do Ceara
Brazil
;
_audit_update_record             
;
2020-09-22 deposited with the CCDC.	2020-10-12 downloaded from the CCDC.
;
_audit_creation_date             2020-09-17
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H17 N O3'
_chemical_formula_sum            'C16 H17 N O3'
_chemical_formula_weight         271.30
_chemical_absolute_configuration ad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_H-M_alt        'C 1 c 1'
_space_group_name_Hall           'C -2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'

_cell_length_a                   6.4597(2)
_cell_length_b                   29.3310(11)
_cell_length_c                   14.9015(5)
_cell_angle_alpha                90
_cell_angle_beta                 97.034(2)
_cell_angle_gamma                90
_cell_volume                     2802.13(17)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9996
_cell_measurement_temperature    274.0
_cell_measurement_theta_max      68.18
_cell_measurement_theta_min      4.25
_shelx_estimated_absorpt_T_max   0.948
_shelx_estimated_absorpt_T_min   0.795
_exptl_absorpt_coefficient_mu    0.724
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6391
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1399 before and 0.0603 after correction.
The Ratio of minimum to maximum transmission is 0.8486.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1152
_exptl_crystal_size_max          0.332
_exptl_crystal_size_mid          0.109
_exptl_crystal_size_min          0.074
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0505
_diffrn_reflns_av_unetI/netI     0.0342
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            33162
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.285
_diffrn_reflns_theta_min         3.013
_diffrn_ambient_temperature      274.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           1.1
_diffrn_source_power             0.055
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.979
_reflns_Friedel_fraction_full    0.987
_reflns_Friedel_fraction_max     0.985
_reflns_number_gt                4755
_reflns_number_total             5095
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.177
_refine_diff_density_min         -0.131
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details 
;
 Flack x determined using 2171 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.09(8)
_refine_ls_extinction_coef       0.00065(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     366
_refine_ls_number_reflns         5095
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0410
_refine_ls_R_factor_gt           0.0374
_refine_ls_restrained_S_all      1.051
_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)+(0.0534P)²+0.4838P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0926
_refine_ls_wR_factor_ref         0.0969
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C00P(H00A,H00B), C00R(H00I,H00J), C00T(H00D,H00E), C010(H01D,H01E)
2.b Aromatic/amide H refined with riding coordinates:
 N004(H004), C009(H009), N00B(H00F), C00C(H00C), C00G(H00G), C00H(H00H),
 C00L(H00L), C00M(H00M), C00O(H00O), C00Q(H00Q), C00S(H00S), C00U(H00U),
 C00V(H00V), C00W(H00W), C00X(H00X), C011(H011), C013(H013), C014(H014)
2.c Idealised Me refined as rotating group:
 C00Z(H00K,H00N,H00P), C012(H01A,H01B,H01C)
2.d Idealised tetrahedral OH refined as rotating group:
 O005(H005), O008(H008)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
O7B O 0.7124(3) 0.39039(6) 0.42163(16) 0.0669(5) Uani 1 1 d . . . . .
O4B' O -0.1246(3) 0.61961(6) 0.38936(16) 0.0651(5) Uani 1 1 d . . . . .
O4A' O 0.6125(3) 0.51574(7) 0.08952(17) 0.0715(6) Uani 1 1 d . . . . .
N8B' N 0.3696(3) 0.37570(7) 0.40530(15) 0.0493(5) Uani 1 1 d . . . . .
H8B' H 0.274401 0.355159 0.395905 0.059 Uiso 1 1 calc R U . . .
O2B O 0.9583(3) 0.33481(8) 0.3639(2) 0.0815(7) Uani 1 1 d . . . . .
H2B H 0.915584 0.359000 0.382191 0.122 Uiso 1 1 calc R U . . .
O7A O -0.1735(4) 0.28438(7) 0.08072(19) 0.0814(7) Uani 1 1 d . . . . .
C7B C 0.5654(4) 0.36266(8) 0.40599(16) 0.0448(5) Uani 1 1 d . . . . .
O2A O -0.4406(4) 0.22213(9) 0.0722(2) 0.0936(8) Uani 1 1 d . . . . .
H2A H -0.393449 0.247922 0.068538 0.140 Uiso 1 1 calc R U . . .
C5B' C -0.1613(4) 0.53678(9) 0.39523(19) 0.0531(6) Uani 1 1 d . . . . .
H5B' H -0.288755 0.538485 0.418112 0.064 Uiso 1 1 calc R U . . .
C1B C 0.6078(3) 0.31439(8) 0.38333(16) 0.0432(5) Uani 1 1 d . . . . .
N8A' N 0.1674(4) 0.26749(8) 0.09209(19) 0.0658(6) Uani 1 1 d . . . . .
H8A' H 0.260713 0.246566 0.101703 0.079 Uiso 1 1 calc R U . . .
C3B' C 0.1315(4) 0.57271(9) 0.34146(19) 0.0546(6) Uani 1 1 d . . . . .
H3B' H 0.201737 0.598987 0.327740 0.066 Uiso 1 1 calc R U . . .
C4B' C -0.0570(4) 0.57629(8) 0.37621(17) 0.0483(5) Uani 1 1 d . . . . .
C1B' C 0.1150(4) 0.49051(9) 0.34631(16) 0.0501(6) Uani 1 1 d . . . . .
C4A' C 0.5524(4) 0.47254(9) 0.10950(18) 0.0515(6) Uani 1 1 d . . . . .
C6A' C 0.5995(5) 0.39739(10) 0.17065(18) 0.0602(7) Uani 1 1 d . . . . .
H6A' H 0.686314 0.375830 0.201681 0.072 Uiso 1 1 calc R U . . .
C6B' C -0.0743(4) 0.49479(8) 0.37987(19) 0.0540(6) Uani 1 1 d . . . . .
H6B' H -0.145745 0.468505 0.392593 0.065 Uiso 1 1 calc R U . . .
C2B C 0.8070(4) 0.30314(9) 0.36153(19) 0.0551(6) Uani 1 1 d . . . . .
C1A C -0.0786(4) 0.20781(9) 0.11655(17) 0.0521(6) Uani 1 1 d . . . . .
C1A' C 0.3972(5) 0.38546(9) 0.13989(17) 0.0579(7) Uani 1 1 d . . . . .
C6B C 0.4574(4) 0.27999(8) 0.37950(18) 0.0523(6) Uani 1 1 d . . . . .
H6B H 0.324955 0.286755 0.394201 0.063 Uiso 1 1 calc R U . . .
C5A' C 0.6781(4) 0.44044(9) 0.15696(19) 0.0584(6) Uani 1 1 d . . . . .
H5A' H 0.814691 0.447670 0.179609 0.070 Uiso 1 1 calc R U . . .
C2A C -0.2845(4) 0.19315(10) 0.1013(2) 0.0615(7) Uani 1 1 d . . . . .
C2B' C 0.2161(4) 0.53056(9) 0.32695(18) 0.0550(6) Uani 1 1 d . . . . .
H2B' H 0.343242 0.528876 0.303792 0.066 Uiso 1 1 calc R U . . .
C8B' C 0.3032(4) 0.42231(8) 0.41930(18) 0.0527(6) Uani 1 1 d . . . . .
H8BB H 0.422302 0.440143 0.445095 0.063 Uiso 1 1 calc R U . . .
H8BA H 0.201444 0.422322 0.462079 0.063 Uiso 1 1 calc R U . . .
C5B C 0.5016(5) 0.23652(9) 0.3545(2) 0.0640(7) Uani 1 1 d . . . . .
H5B H 0.400016 0.213954 0.352726 0.077 Uiso 1 1 calc R U . . .
C8A' C 0.2351(5) 0.31352(10) 0.0725(2) 0.0676(7) Uani 1 1 d . . . . .
H8AB H 0.119372 0.330071 0.039920 0.081 Uiso 1 1 calc R U . . .
H8AA H 0.345743 0.311839 0.034080 0.081 Uiso 1 1 calc R U . . .
C6A C 0.0742(5) 0.17665(10) 0.1499(2) 0.0657(7) Uani 1 1 d . . . . .
H6A H 0.212112 0.186112 0.162491 0.079 Uiso 1 1 calc R U . . .
C7B' C 0.2086(5) 0.44417(9) 0.33223(19) 0.0606(7) Uani 1 1 d . . . . .
H7BA H 0.100959 0.424299 0.302833 0.073 Uiso 1 1 calc R U . . .
H7BB H 0.315525 0.447353 0.292258 0.073 Uiso 1 1 calc R U . . .
C4B C 0.6969(5) 0.22622(10) 0.3320(2) 0.0679(8) Uani 1 1 d . . . . .
H4B H 0.726025 0.196697 0.314504 0.081 Uiso 1 1 calc R U . . .
C2A' C 0.2730(4) 0.41856(10) 0.09281(19) 0.0618(7) Uani 1 1 d . . . . .
H2A' H 0.135477 0.411545 0.071248 0.074 Uiso 1 1 calc R U . . .
C3A C -0.3333(6) 0.14751(12) 0.1146(2) 0.0737(9) Uani 1 1 d . . . . .
H3A H -0.470624 0.137595 0.102421 0.088 Uiso 1 1 calc R U . . .
C3B C 0.8481(5) 0.25892(11) 0.3350(2) 0.0703(8) Uani 1 1 d . . . . .
H3B H 0.979010 0.251604 0.319230 0.084 Uiso 1 1 calc R U . . .
C7A C -0.0305(4) 0.25614(9) 0.09591(19) 0.0579(6) Uani 1 1 d . . . . .
C9A' C 0.8219(5) 0.52853(11) 0.1155(3) 0.0732(8) Uani 1 1 d . . . . .
H9AA H 0.912771 0.507480 0.090224 0.110 Uiso 1 1 calc R U . . .
H9AB H 0.850658 0.528122 0.180214 0.110 Uiso 1 1 calc R U . . .
H9AC H 0.844613 0.558685 0.093627 0.110 Uiso 1 1 calc R U . . .
C7A' C 0.3119(7) 0.33870(11) 0.1573(2) 0.0763(9) Uani 1 1 d . . . . .
H7AA H 0.420563 0.320869 0.191755 0.092 Uiso 1 1 calc R U . . .
H7AB H 0.198164 0.341906 0.193717 0.092 Uiso 1 1 calc R U . . .
C3A' C 0.3484(4) 0.46134(10) 0.0773(2) 0.0589(6) Uani 1 1 d . . . . .
H3A' H 0.262481 0.482739 0.045316 0.071 Uiso 1 1 calc R U . . .
C9B' C -0.3145(5) 0.62550(11) 0.4261(3) 0.0741(8) Uani 1 1 d . . . . .
H9BC H -0.426920 0.613083 0.385315 0.111 Uiso 1 1 calc R U . . .
H9BA H -0.338462 0.657407 0.434818 0.111 Uiso 1 1 calc R U . . .
H9BB H -0.307023 0.610005 0.483167 0.111 Uiso 1 1 calc R U . . .
C4A C -0.1805(7) 0.11750(11) 0.1454(2) 0.0766(10) Uani 1 1 d . . . . .
H4A H -0.214004 0.087058 0.153536 0.092 Uiso 1 1 calc R U . . .
C5A C 0.0226(7) 0.13167(11) 0.1646(2) 0.0781(9) Uani 1 1 d . . . . .
H5A H 0.125355 0.111097 0.187453 0.094 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O7B C7B 1.250(3) . ?
O4B' C4B' 1.366(3) . ?
O4B' C9B' 1.414(4) . ?
O4A' C4A' 1.369(3) . ?
O4A' C9A' 1.411(4) . ?
N8B' H8B' 0.8600 . ?
N8B' C7B 1.320(3) . ?
N8B' C8B' 1.456(3) . ?
O2B H2B 0.8200 . ?
O2B C2B 1.346(3) . ?
O7A C7A 1.241(4) . ?
C7B C1B 1.489(3) . ?
O2A H2A 0.8200 . ?
O2A C2A 1.349(4) . ?
C5B' H5B' 0.9300 . ?
C5B' C4B' 1.387(3) . ?
C5B' C6B' 1.385(4) . ?
C1B C2B 1.405(3) . ?
C1B C6B 1.397(3) . ?
N8A' H8A' 0.8600 . ?
N8A' C8A' 1.460(4) . ?
N8A' C7A 1.329(4) . ?
C3B' H3B' 0.9300 . ?
C3B' C4B' 1.384(4) . ?
C3B' C2B' 1.380(4) . ?
C1B' C6B' 1.382(4) . ?
C1B' C2B' 1.391(4) . ?
C1B' C7B' 1.513(3) . ?
C4A' C5A' 1.380(4) . ?
C4A' C3A' 1.385(4) . ?
C6A' H6A' 0.9300 . ?
C6A' C1A' 1.376(4) . ?
C6A' C5A' 1.385(4) . ?
C6B' H6B' 0.9300 . ?
C2B C3B 1.391(4) . ?
C1A C2A 1.390(4) . ?
C1A C6A 1.392(4) . ?
C1A C7A 1.491(4) . ?
C1A' C2A' 1.393(4) . ?
C1A' C7A' 1.512(4) . ?
C6B H6B 0.9300 . ?
C6B C5B 1.368(4) . ?
C5A' H5A' 0.9300 . ?
C2A C3A 1.395(4) . ?
C2B' H2B' 0.9300 . ?
C8B' H8BB 0.9700 . ?
C8B' H8BA 0.9700 . ?
C8B' C7B' 1.508(4) . ?
C5B H5B 0.9300 . ?
C5B C4B 1.378(5) . ?
C8A' H8AB 0.9700 . ?
C8A' H8AA 0.9700 . ?
C8A' C7A' 1.495(4) . ?
C6A H6A 0.9300 . ?
C6A C5A 1.385(4) . ?
C7B' H7BA 0.9700 . ?
C7B' H7BB 0.9700 . ?
C4B H4B 0.9300 . ?
C4B C3B 1.366(5) . ?
C2A' H2A' 0.9300 . ?
C2A' C3A' 1.376(4) . ?
C3A H3A 0.9300 . ?
C3A C4A 1.359(5) . ?
C3B H3B 0.9300 . ?
C9A' H9AA 0.9600 . ?
C9A' H9AB 0.9600 . ?
C9A' H9AC 0.9600 . ?
C7A' H7AA 0.9700 . ?
C7A' H7AB 0.9700 . ?
C3A' H3A' 0.9300 . ?
C9B' H9BC 0.9600 . ?
C9B' H9BA 0.9600 . ?
C9B' H9BB 0.9600 . ?
C4A H4A 0.9300 . ?
C4A C5A 1.373(6) . ?
C5A H5A 0.9300 . ?

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
_geom_angle_publ_flag
C4B' O4B' C9B' 118.5(2) . . ?
C4A' O4A' C9A' 118.3(2) . . ?
C7B N8B' H8B' 117.6 . . ?
C7B N8B' C8B' 124.7(2) . . ?
C8B' N8B' H8B' 117.6 . . ?
C2B O2B H2B 109.5 . . ?
O7B C7B N8B' 121.2(2) . . ?
O7B C7B C1B 120.3(2) . . ?
N8B' C7B C1B 118.4(2) . . ?
C2A O2A H2A 109.5 . . ?
C4B' C5B' H5B' 120.3 . . ?
C6B' C5B' H5B' 120.3 . . ?
C6B' C5B' C4B' 119.5(2) . . ?
C2B C1B C7B 118.4(2) . . ?
C6B C1B C7B 123.4(2) . . ?
C6B C1B C2B 118.2(2) . . ?
C8A' N8A' H8A' 118.2 . . ?
C7A N8A' H8A' 118.2 . . ?
C7A N8A' C8A' 123.6(3) . . ?
C4B' C3B' H3B' 119.6 . . ?
C2B' C3B' H3B' 119.6 . . ?
C2B' C3B' C4B' 120.7(2) . . ?
O4B' C4B' C5B' 125.2(2) . . ?
O4B' C4B' C3B' 115.8(2) . . ?
C3B' C4B' C5B' 119.0(2) . . ?
C6B' C1B' C2B' 117.2(2) . . ?
C6B' C1B' C7B' 121.2(2) . . ?
C2B' C1B' C7B' 121.6(2) . . ?
O4A' C4A' C5A' 125.3(2) . . ?
O4A' C4A' C3A' 115.3(2) . . ?
C5A' C4A' C3A' 119.4(2) . . ?
C1A' C6A' H6A' 118.9 . . ?
C1A' C6A' C5A' 122.2(3) . . ?
C5A' C6A' H6A' 118.9 . . ?
C5B' C6B' H6B' 118.8 . . ?
C1B' C6B' C5B' 122.4(2) . . ?
C1B' C6B' H6B' 118.8 . . ?
O2B C2B C1B 121.0(2) . . ?
O2B C2B C3B 119.2(2) . . ?
C3B C2B C1B 119.8(2) . . ?
C2A C1A C6A 118.5(3) . . ?
C2A C1A C7A 118.7(2) . . ?
C6A C1A C7A 122.8(3) . . ?
C6A' C1A' C2A' 117.1(3) . . ?
C6A' C1A' C7A' 121.6(3) . . ?
C2A' C1A' C7A' 121.3(3) . . ?
C1B C6B H6B 119.4 . . ?
C5B C6B C1B 121.1(3) . . ?
C5B C6B H6B 119.4 . . ?
C4A' C5A' C6A' 119.6(3) . . ?
C4A' C5A' H5A' 120.2 . . ?
C6A' C5A' H5A' 120.2 . . ?
O2A C2A C1A 121.4(3) . . ?
O2A C2A C3A 118.5(3) . . ?
C1A C2A C3A 120.2(3) . . ?
C3B' C2B' C1B' 121.2(2) . . ?
C3B' C2B' H2B' 119.4 . . ?
C1B' C2B' H2B' 119.4 . . ?
N8B' C8B' H8BB 109.3 . . ?
N8B' C8B' H8BA 109.3 . . ?
N8B' C8B' C7B' 111.8(2) . . ?
H8BB C8B' H8BA 107.9 . . ?
C7B' C8B' H8BB 109.3 . . ?
C7B' C8B' H8BA 109.3 . . ?
C6B C5B H5B 120.1 . . ?
C6B C5B C4B 119.9(3) . . ?
C4B C5B H5B 120.1 . . ?
N8A' C8A' H8AB 109.4 . . ?
N8A' C8A' H8AA 109.4 . . ?
N8A' C8A' C7A' 111.3(3) . . ?
H8AB C8A' H8AA 108.0 . . ?
C7A' C8A' H8AB 109.4 . . ?
C7A' C8A' H8AA 109.4 . . ?
C1A C6A H6A 119.7 . . ?
C5A C6A C1A 120.6(3) . . ?
C5A C6A H6A 119.7 . . ?
C1B' C7B' H7BA 109.0 . . ?
C1B' C7B' H7BB 109.0 . . ?
C8B' C7B' C1B' 112.9(2) . . ?
C8B' C7B' H7BA 109.0 . . ?
C8B' C7B' H7BB 109.0 . . ?
H7BA C7B' H7BB 107.8 . . ?
C5B C4B H4B 119.7 . . ?
C3B C4B C5B 120.7(3) . . ?
C3B C4B H4B 119.7 . . ?
C1A' C2A' H2A' 119.1 . . ?
C3A' C2A' C1A' 121.8(3) . . ?
C3A' C2A' H2A' 119.1 . . ?
C2A C3A H3A 119.9 . . ?
C4A C3A C2A 120.1(3) . . ?
C4A C3A H3A 119.9 . . ?
C2B C3B H3B 119.9 . . ?
C4B C3B C2B 120.2(3) . . ?
C4B C3B H3B 119.9 . . ?
O7A C7A N8A' 121.6(3) . . ?
O7A C7A C1A 120.2(3) . . ?
N8A' C7A C1A 118.2(2) . . ?
O4A' C9A' H9AA 109.5 . . ?
O4A' C9A' H9AB 109.5 . . ?
O4A' C9A' H9AC 109.5 . . ?
H9AA C9A' H9AB 109.5 . . ?
H9AA C9A' H9AC 109.5 . . ?
H9AB C9A' H9AC 109.5 . . ?
C1A' C7A' H7AA 109.0 . . ?
C1A' C7A' H7AB 109.0 . . ?
C8A' C7A' C1A' 113.1(3) . . ?
C8A' C7A' H7AA 109.0 . . ?
C8A' C7A' H7AB 109.0 . . ?
H7AA C7A' H7AB 107.8 . . ?
C4A' C3A' H3A' 120.0 . . ?
C2A' C3A' C4A' 120.0(2) . . ?
C2A' C3A' H3A' 120.0 . . ?
O4B' C9B' H9BC 109.5 . . ?
O4B' C9B' H9BA 109.5 . . ?
O4B' C9B' H9BB 109.5 . . ?
H9BC C9B' H9BA 109.5 . . ?
H9BC C9B' H9BB 109.5 . . ?
H9BA C9B' H9BB 109.5 . . ?
C3A C4A H4A 119.7 . . ?
C3A C4A C5A 120.7(3) . . ?
C5A C4A H4A 119.7 . . ?
C6A C5A H5A 120.1 . . ?
C4A C5A C6A 119.9(3) . . ?
C4A C5A H5A 120.1 . . ?

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
_geom_torsion_publ_flag
O7B C7B C1B C2B -13.1(4) . . . . ?
O7B C7B C1B C6B 169.3(3) . . . . ?
O4A' C4A' C5A' C6A' -178.3(3) . . . . ?
O4A' C4A' C3A' C2A' 179.2(3) . . . . ?
N8B' C7B C1B C2B 164.1(2) . . . . ?
N8B' C7B C1B C6B -13.6(4) . . . . ?
N8B' C8B' C7B' C1B' 173.1(2) . . . . ?
O2B C2B C3B C4B -179.9(3) . . . . ?
C7B N8B' C8B' C7B' 105.6(3) . . . . ?
C7B C1B C2B O2B 2.1(4) . . . . ?
C7B C1B C2B C3B -176.3(3) . . . . ?
C7B C1B C6B C5B 177.1(2) . . . . ?
O2A C2A C3A C4A -178.9(3) . . . . ?
C1B C2B C3B C4B -1.4(5) . . . . ?
C1B C6B C5B C4B -0.5(4) . . . . ?
N8A' C8A' C7A' C1A' 176.1(3) . . . . ?
C4B' C5B' C6B' C1B' 0.3(4) . . . . ?
C4B' C3B' C2B' C1B' 0.3(4) . . . . ?
C6A' C1A' C2A' C3A' 0.1(4) . . . . ?
C6A' C1A' C7A' C8A' -121.1(3) . . . . ?
C6B' C5B' C4B' O4B' -179.1(3) . . . . ?
C6B' C5B' C4B' C3B' 0.6(4) . . . . ?
C6B' C1B' C2B' C3B' 0.5(4) . . . . ?
C6B' C1B' C7B' C8B' -75.9(3) . . . . ?
C2B C1B C6B C5B -0.5(4) . . . . ?
C1A C2A C3A C4A 2.2(4) . . . . ?
C1A C6A C5A C4A 0.6(5) . . . . ?
C1A' C6A' C5A' C4A' -1.3(4) . . . . ?
C1A' C2A' C3A' C4A' -0.5(4) . . . . ?
C6B C1B C2B O2B 179.9(3) . . . . ?
C6B C1B C2B C3B 1.5(4) . . . . ?
C6B C5B C4B C3B 0.5(5) . . . . ?
C5A' C4A' C3A' C2A' 0.0(4) . . . . ?
C5A' C6A' C1A' C2A' 0.8(4) . . . . ?
C5A' C6A' C1A' C7A' -178.5(3) . . . . ?
C2A C1A C6A C5A 2.2(4) . . . . ?
C2A C1A C7A O7A 12.3(4) . . . . ?
C2A C1A C7A N8A' -166.0(3) . . . . ?
C2A C3A C4A C5A 0.7(5) . . . . ?
C2B' C3B' C4B' O4B' 178.9(3) . . . . ?
C2B' C3B' C4B' C5B' -0.8(4) . . . . ?
C2B' C1B' C6B' C5B' -0.8(4) . . . . ?
C2B' C1B' C7B' C8B' 103.4(3) . . . . ?
C8B' N8B' C7B O7B 1.9(4) . . . . ?
C8B' N8B' C7B C1B -175.2(2) . . . . ?
C5B C4B C3B C2B 0.4(5) . . . . ?
C8A' N8A' C7A O7A 1.7(5) . . . . ?
C8A' N8A' C7A C1A 179.9(3) . . . . ?
C6A C1A C2A O2A 177.5(3) . . . . ?
C6A C1A C2A C3A -3.6(4) . . . . ?
C6A C1A C7A O7A -168.1(3) . . . . ?
C6A C1A C7A N8A' 13.6(4) . . . . ?
C7B' C1B' C6B' C5B' 178.6(2) . . . . ?
C7B' C1B' C2B' C3B' -178.9(3) . . . . ?
C2A' C1A' C7A' C8A' 59.7(4) . . . . ?
C3A C4A C5A C6A -2.0(5) . . . . ?
C7A N8A' C8A' C7A' 98.0(4) . . . . ?
C7A C1A C2A O2A -2.8(4) . . . . ?
C7A C1A C2A C3A 176.1(3) . . . . ?
C7A C1A C6A C5A -177.4(3) . . . . ?
C9A' O4A' C4A' C5A' 3.0(4) . . . . ?
C9A' O4A' C4A' C3A' -176.3(3) . . . . ?
C7A' C1A' C2A' C3A' 179.4(3) . . . . ?
C3A' C4A' C5A' C6A' 0.9(4) . . . . ?
C9B' O4B' C4B' C5B' 0.7(4) . . . . ?
C9B' O4B' C4B' C3B' -179.0(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_riparin_i_beta_324k
_database_code_depnum_ccdc_archive 'CCDC 1996453'
loop_
_audit_author_name
_audit_author_address
'Alejandro Pedro Ayala'
;Universidade Federal do Ceara
Brazil
;
_audit_update_record             
;
2020-04-12 deposited with the CCDC.	2020-10-12 downloaded from the CCDC.
;
_audit_creation_date             2020-04-12
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        'Riparin I beta'
_chemical_formula_moiety         'C16 H17 N O2'
_chemical_formula_sum            'C16 H17 N O2'
_chemical_formula_weight         255.30
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.1846(2)
_cell_length_b                   8.2750(3)
_cell_length_c                   16.1461(5)
_cell_angle_alpha                94.869(2)
_cell_angle_beta                 92.574(2)
_cell_angle_gamma                90.232(2)
_cell_volume                     689.49(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2428
_cell_measurement_temperature    354.01
_cell_measurement_theta_max      69.601
_cell_measurement_theta_min      2.748
_shelx_estimated_absorpt_T_max   0.938
_shelx_estimated_absorpt_T_min   0.938
_exptl_absorpt_coefficient_mu    0.647
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.5884
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1381 before and 0.0575 after correction. The Ratio of minimum to maximum transmission is 0.7808.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.230
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             272
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method ?
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0395
_diffrn_reflns_av_unetI/netI     0.0462
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            6944
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         73.292
_diffrn_reflns_theta_min         2.749
_diffrn_ambient_temperature      354.01
_diffrn_detector                 'Bruker PHOTON II'
_diffrn_detector_area_resol_mean 7.4
_diffrn_detector_type            'CPAD Area Detector'
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTON II CPAD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'Incoatec I\ms 3.0'
_diffrn_source_type              'microfocus sealed X-ray tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1678
_reflns_number_total             2693
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.212
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2693
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0968
_refine_ls_R_factor_gt           0.0646
_refine_ls_restrained_S_all      1.058
_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)+(0.1080P)²+0.1170P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1837
_refine_ls_wR_factor_ref         0.2178
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C8'(H8'A,H8'B), C7'(H7'A,H7'B)
2.b Aromatic/amide H refined with riding coordinates:
 N8'(H8'), C6(H6), C2(H2), C5(H5), C5'(H5'), C3'(H3'), C2'(H2'), C6'(H6'),
 C4(H4), C3(H3)
2.c Idealised Me refined as rotating group:
 C9'(H9'A,H9'B,H9'C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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
O7 O 0.2952(3) 0.6785(3) 0.39860(12) 0.0872(6) Uani 1 1 d . . . . .
O4' O 0.9424(5) 0.8602(3) 0.90608(12) 0.1039(7) Uani 1 1 d . . . . .
N8' N 0.7248(4) 0.6883(3) 0.42211(13) 0.0842(7) Uani 1 1 d . . . . .
H8' H 0.872504 0.690760 0.399994 0.101 Uiso 1 1 calc R U . . .
C1 C 0.5539(4) 0.6716(3) 0.28099(14) 0.0611(6) Uani 1 1 d . . . . .
C7 C 0.5141(4) 0.6797(3) 0.37180(15) 0.0644(6) Uani 1 1 d . . . . .
C6 C 0.7510(5) 0.7537(3) 0.24710(15) 0.0711(7) Uani 1 1 d . . . . .
H6 H 0.869699 0.814274 0.281920 0.085 Uiso 1 1 calc R U . . .
C4' C 0.9373(5) 0.8413(3) 0.82059(16) 0.0730(7) Uani 1 1 d . . . . .
C1' C 0.8995(6) 0.8243(3) 0.64734(17) 0.0768(8) Uani 1 1 d . . . . .
C2 C 0.3816(5) 0.5816(4) 0.22789(17) 0.0787(8) Uani 1 1 d . . . . .
H2 H 0.246676 0.526370 0.249400 0.094 Uiso 1 1 calc R U . . .
C5 C 0.7728(6) 0.7464(4) 0.16253(17) 0.0815(8) Uani 1 1 d . . . . .
H5 H 0.904276 0.803518 0.140343 0.098 Uiso 1 1 calc R U . . .
C5' C 1.1085(6) 0.7495(4) 0.77517(18) 0.0832(8) Uani 1 1 d . . . . .
H5' H 1.237836 0.692865 0.801779 0.100 Uiso 1 1 calc R U . . .
C3' C 0.7461(6) 0.9209(4) 0.78070(18) 0.0835(8) Uani 1 1 d . . . . .
H3' H 0.627454 0.981618 0.811472 0.100 Uiso 1 1 calc R U . . .
C2' C 0.7271(6) 0.9123(4) 0.69544(18) 0.0845(8) Uani 1 1 d . . . . .
H2' H 0.594594 0.967236 0.669362 0.101 Uiso 1 1 calc R U . . .
C6' C 1.0871(6) 0.7420(4) 0.68920(19) 0.0872(9) Uani 1 1 d . . . . .
H6' H 1.203629 0.679039 0.658663 0.105 Uiso 1 1 calc R U . . .
C4 C 0.6025(6) 0.6557(4) 0.11073(18) 0.0903(9) Uani 1 1 d . . . . .
H4 H 0.618884 0.650289 0.053437 0.108 Uiso 1 1 calc R U . . .
C8' C 0.7203(6) 0.6939(4) 0.51251(17) 0.0911(9) Uani 1 1 d . . . . .
H8'A H 0.544069 0.709422 0.529124 0.109 Uiso 1 1 calc R U . . .
H8'B H 0.778951 0.590790 0.530494 0.109 Uiso 1 1 calc R U . . .
C3 C 0.4087(6) 0.5733(4) 0.14325(19) 0.0955(10) Uani 1 1 d . . . . .
H3 H 0.293706 0.510766 0.107951 0.115 Uiso 1 1 calc R U . . .
C7' C 0.8802(7) 0.8216(4) 0.55329(19) 0.1045(11) Uani 1 1 d . . . . .
H7'A H 0.812448 0.924840 0.538296 0.125 Uiso 1 1 calc R U . . .
H7'B H 1.052513 0.811035 0.532533 0.125 Uiso 1 1 calc R U . . .
C9' C 1.1602(8) 0.8044(5) 0.9502(2) 0.1234(14) Uani 1 1 d . . . . .
H9'A H 1.314158 0.846099 0.928587 0.185 Uiso 1 1 calc R U . . .
H9'B H 1.162416 0.687996 0.944044 0.185 Uiso 1 1 calc R U . . .
H9'C H 1.152384 0.841007 1.008065 0.185 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O7 C7 1.233(3) . ?
O4' C4' 1.375(3) . ?
O4' C9' 1.409(4) . ?
N8' H8' 0.8600 . ?
N8' C7 1.330(3) . ?
N8' C8' 1.458(3) . ?
C1 C7 1.486(3) . ?
C1 C6 1.383(3) . ?
C1 C2 1.381(3) . ?
C6 H6 0.9300 . ?
C6 C5 1.371(3) . ?
C4' C5' 1.368(4) . ?
C4' C3' 1.361(4) . ?
C1' C2' 1.380(4) . ?
C1' C6' 1.375(4) . ?
C1' C7' 1.516(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.376(4) . ?
C5 H5 0.9300 . ?
C5 C4 1.365(4) . ?
C5' H5' 0.9300 . ?
C5' C6' 1.384(4) . ?
C3' H3' 0.9300 . ?
C3' C2' 1.372(4) . ?
C2' H2' 0.9300 . ?
C6' H6' 0.9300 . ?
C4 H4 0.9300 . ?
C4 C3 1.361(5) . ?
C8' H8'A 0.9700 . ?
C8' H8'B 0.9700 . ?
C8' C7' 1.436(4) . ?
C3 H3 0.9300 . ?
C7' H7'A 0.9700 . ?
C7' H7'B 0.9700 . ?
C9' H9'A 0.9600 . ?
C9' H9'B 0.9600 . ?
C9' H9'C 0.9600 . ?

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
_geom_angle_publ_flag
C4' O4' C9' 118.2(3) . . ?
C7 N8' H8' 118.1 . . ?
C7 N8' C8' 123.9(2) . . ?
C8' N8' H8' 118.1 . . ?
C6 C1 C7 123.1(2) . . ?
C2 C1 C7 118.3(2) . . ?
C2 C1 C6 118.5(2) . . ?
O7 C7 N8' 122.1(2) . . ?
O7 C7 C1 121.1(2) . . ?
N8' C7 C1 116.8(2) . . ?
C1 C6 H6 119.7 . . ?
C5 C6 C1 120.5(2) . . ?
C5 C6 H6 119.7 . . ?
C5' C4' O4' 124.4(3) . . ?
C3' C4' O4' 115.9(3) . . ?
C3' C4' C5' 119.7(3) . . ?
C2' C1' C7' 120.7(3) . . ?
C6' C1' C2' 116.6(3) . . ?
C6' C1' C7' 122.7(3) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 C1 120.2(3) . . ?
C3 C2 H2 119.9 . . ?
C6 C5 H5 119.8 . . ?
C4 C5 C6 120.4(3) . . ?
C4 C5 H5 119.8 . . ?
C4' C5' H5' 120.4 . . ?
C4' C5' C6' 119.3(3) . . ?
C6' C5' H5' 120.4 . . ?
C4' C3' H3' 119.8 . . ?
C4' C3' C2' 120.5(3) . . ?
C2' C3' H3' 119.8 . . ?
C1' C2' H2' 119.1 . . ?
C3' C2' C1' 121.7(3) . . ?
C3' C2' H2' 119.1 . . ?
C1' C6' C5' 122.3(3) . . ?
C1' C6' H6' 118.9 . . ?
C5' C6' H6' 118.9 . . ?
C5 C4 H4 120.1 . . ?
C3 C4 C5 119.7(3) . . ?
C3 C4 H4 120.1 . . ?
N8' C8' H8'A 109.1 . . ?
N8' C8' H8'B 109.1 . . ?
H8'A C8' H8'B 107.8 . . ?
C7' C8' N8' 112.6(2) . . ?
C7' C8' H8'A 109.1 . . ?
C7' C8' H8'B 109.1 . . ?
C2 C3 H3 119.7 . . ?
C4 C3 C2 120.6(3) . . ?
C4 C3 H3 119.7 . . ?
C1' C7' H7'A 108.6 . . ?
C1' C7' H7'B 108.6 . . ?
C8' C7' C1' 114.7(2) . . ?
C8' C7' H7'A 108.6 . . ?
C8' C7' H7'B 108.6 . . ?
H7'A C7' H7'B 107.6 . . ?
O4' C9' H9'A 109.5 . . ?
O4' C9' H9'B 109.5 . . ?
O4' C9' H9'C 109.5 . . ?
H9'A C9' H9'B 109.5 . . ?
H9'A C9' H9'C 109.5 . . ?
H9'B C9' H9'C 109.5 . . ?

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
_geom_torsion_publ_flag
O4' C4' C5' C6' -178.8(3) . . . . ?
O4' C4' C3' C2' 178.8(3) . . . . ?
N8' C8' C7' C1' -175.3(3) . . . . ?
C1 C6 C5 C4 -1.1(4) . . . . ?
C1 C2 C3 C4 -1.2(5) . . . . ?
C7 N8' C8' C7' -131.1(3) . . . . ?
C7 C1 C6 C5 -177.6(2) . . . . ?
C7 C1 C2 C3 178.8(3) . . . . ?
C6 C1 C7 O7 144.2(3) . . . . ?
C6 C1 C7 N8' -35.7(4) . . . . ?
C6 C1 C2 C3 0.6(4) . . . . ?
C6 C5 C4 C3 0.6(5) . . . . ?
C4' C5' C6' C1' 0.3(5) . . . . ?
C4' C3' C2' C1' -0.3(5) . . . . ?
C2 C1 C7 O7 -33.9(4) . . . . ?
C2 C1 C7 N8' 146.2(3) . . . . ?
C2 C1 C6 C5 0.5(4) . . . . ?
C5 C4 C3 C2 0.5(5) . . . . ?
C5' C4' C3' C2' -1.3(4) . . . . ?
C3' C4' C5' C6' 1.3(4) . . . . ?
C2' C1' C6' C5' -1.7(4) . . . . ?
C2' C1' C7' C8' -90.3(4) . . . . ?
C6' C1' C2' C3' 1.7(4) . . . . ?
C6' C1' C7' C8' 90.3(4) . . . . ?
C8' N8' C7 O7 1.3(4) . . . . ?
C8' N8' C7 C1 -178.8(3) . . . . ?
C7' C1' C2' C3' -177.8(3) . . . . ?
C7' C1' C6' C5' 177.8(3) . . . . ?
C9' O4' C4' C5' 10.8(5) . . . . ?
C9' O4' C4' C3' -169.2(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_riparin_II_100K
_database_code_depnum_ccdc_archive 'CCDC 1996920'
loop_
_audit_author_name
_audit_author_address
'Alejandro Pedro Ayala'
;Universidade Federal do Ceara
Brazil
;
_audit_update_record             
;
2020-04-15 deposited with the CCDC.	2020-10-12 downloaded from the CCDC.
;
_audit_creation_date             2020-04-14
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        'riparin II'
_chemical_formula_moiety         'C16 H17 N O3'
_chemical_formula_sum            'C16 H17 N O3'
_chemical_formula_weight         271.30
_chemical_absolute_configuration ad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_H-M_alt        'C 1 c 1'
_space_group_name_Hall           'C -2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'

_cell_length_a                   6.4257(3)
_cell_length_b                   29.1663(13)
_cell_length_c                   14.5886(6)
_cell_angle_alpha                90
_cell_angle_beta                 97.0550(10)
_cell_angle_gamma                90
_cell_volume                     2713.4(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9886
_cell_measurement_temperature    100.01
_cell_measurement_theta_max      72.37
_cell_measurement_theta_min      3.05
_shelx_estimated_absorpt_T_max   0.913
_shelx_estimated_absorpt_T_min   0.556
_exptl_absorpt_coefficient_mu    0.747
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.5808
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1666 before and 0.0502 after correction.
The Ratio of minimum to maximum transmission is 0.7707.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1152
_exptl_crystal_size_max          0.889
_exptl_crystal_size_mid          0.224
_exptl_crystal_size_min          0.124
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0337
_diffrn_reflns_av_unetI/netI     0.0334
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       36
_diffrn_reflns_limit_k_min       -37
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            17460
_diffrn_reflns_point_group_measured_fraction_full 0.894
_diffrn_reflns_point_group_measured_fraction_max 0.848
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         80.192
_diffrn_reflns_theta_min         6.069
_diffrn_ambient_temperature      100.01
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           1.1
_diffrn_source_power             0.055
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.753
_reflns_Friedel_fraction_full    0.804
_reflns_Friedel_fraction_max     0.731
_reflns_number_gt                4998
_reflns_number_total             5039
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.214
_refine_diff_density_min         -0.128
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details 
;
 Flack x determined using 2105 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.08(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     365
_refine_ls_number_reflns         5039
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0280
_refine_ls_R_factor_gt           0.0279
_refine_ls_restrained_S_all      1.039
_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)+(0.0420P)²+0.7493P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0747
_refine_ls_wR_factor_ref         0.0748
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C8B'(H8BA,H8BB), C7B'(H7BA,H7BB), C8A'(H8AA,H8AB), C7A'(H7AA,H7AB)
2.b Aromatic/amide H refined with riding coordinates:
 N8B'(H8B'), N8A'(H8A'), C3B'(H3B'), C5B'(H5B'), C6B(H6B), C2A'(H2A'),
 C2B'(H2B'), C6B'(H6B'), C6A(H6A), C3A'(H3A'), C5B(H5B), C6A'(H6A'), C5A'(H5A'),
  C3B(H3B), C4B(H4B), C4A(H4A), C5A(H5A), C3A(H3A)
2.c Idealised Me refined as rotating group:
 C9A'(H9AA,H9AB,H9AC), C9B'(H9BA,H9BB,H9BC)
2.d Idealised tetrahedral OH refined as rotating group:
 O2B(H2B), O2A(H2A)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
O7B O 0.71630(19) 0.60983(4) 0.42566(9) 0.0225(3) Uani 1 1 d . . . . .
O4A' O 1.1104(2) 1.01631(4) 0.58703(9) 0.0236(3) Uani 1 1 d . . . . .
O2B O 0.9625(2) 0.66502(4) 0.36339(10) 0.0262(3) Uani 1 1 d . . . . .
H2B H 0.919720 0.640318 0.384045 0.039 Uiso 1 1 calc R U . . .
O4B' O -0.1271(2) 0.37929(4) 0.39069(9) 0.0224(3) Uani 1 1 d . . . . .
O7A O 0.3270(2) 0.78418(4) 0.58048(10) 0.0263(3) Uani 1 1 d . . . . .
O2A O 0.0574(2) 0.72161(5) 0.56844(10) 0.0295(3) Uani 1 1 d . . . . .
H2A H 0.106107 0.748313 0.567783 0.044 Uiso 1 1 calc R U . . .
N8B' N 0.3683(2) 0.62486(5) 0.40692(10) 0.0182(3) Uani 1 1 d . . . . .
H8B' H 0.270908 0.646110 0.396884 0.022 Uiso 1 1 calc R U . . .
N8A' N 0.6706(2) 0.76617(5) 0.59055(10) 0.0203(3) Uani 1 1 d . . . . .
H8A' H 0.766032 0.744495 0.600052 0.024 Uiso 1 1 calc R U . . .
C7B C 0.5671(3) 0.63750(5) 0.40817(10) 0.0164(3) Uani 1 1 d . . . . .
C4A' C 1.0508(3) 0.97296(5) 0.60880(11) 0.0188(3) Uani 1 1 d . . . . .
C1B C 0.6099(3) 0.68622(5) 0.38425(10) 0.0163(3) Uani 1 1 d . . . . .
C3B' C 0.1316(3) 0.42613(6) 0.34087(12) 0.0197(3) Uani 1 1 d . . . . .
H3B' H 0.203482 0.399034 0.326951 0.024 Uiso 1 1 calc R U . . .
C5B' C -0.1662(3) 0.46278(6) 0.39592(12) 0.0193(3) Uani 1 1 d . . . . .
H5B' H -0.296859 0.461011 0.419941 0.023 Uiso 1 1 calc R U . . .
C6B C 0.4580(3) 0.72093(5) 0.38074(11) 0.0183(3) Uani 1 1 d . . . . .
H6B H 0.322960 0.714056 0.397300 0.022 Uiso 1 1 calc R U . . .
C2A' C 0.7697(3) 0.91785(6) 0.59324(11) 0.0213(3) Uani 1 1 d . . . . .
H2A' H 0.628358 0.910306 0.571527 0.026 Uiso 1 1 calc R U . . .
C2B' C 0.2170(3) 0.46876(6) 0.32551(12) 0.0201(3) Uani 1 1 d . . . . .
H2B' H 0.347572 0.470489 0.301457 0.024 Uiso 1 1 calc R U . . .
C6B' C -0.0779(3) 0.50536(5) 0.37933(11) 0.0189(3) Uani 1 1 d . . . . .
H6B' H -0.151170 0.532486 0.391968 0.023 Uiso 1 1 calc R U . . .
C1A' C 0.8979(3) 0.88515(6) 0.64220(11) 0.0205(3) Uani 1 1 d . . . . .
C7A C 0.4709(3) 0.75521(6) 0.59495(11) 0.0194(3) Uani 1 1 d . . . . .
C6A C 0.5745(3) 0.67517(6) 0.65152(12) 0.0229(4) Uani 1 1 d . . . . .
H6A H 0.715995 0.684880 0.665384 0.028 Uiso 1 1 calc R U . . .
C1B' C 0.1138(3) 0.50921(5) 0.34487(11) 0.0184(3) Uani 1 1 d . . . . .
C1A C 0.4224(3) 0.70659(6) 0.61600(11) 0.0186(3) Uani 1 1 d . . . . .
C4B' C -0.0595(3) 0.42296(5) 0.37667(11) 0.0174(3) Uani 1 1 d . . . . .
C3A' C 0.8452(3) 0.96112(6) 0.57585(12) 0.0200(3) Uani 1 1 d . . . . .
H3A' H 0.756630 0.982713 0.541419 0.024 Uiso 1 1 calc R U . . .
C2B C 0.8092(3) 0.69703(6) 0.36059(11) 0.0192(3) Uani 1 1 d . . . . .
C8B' C 0.3013(3) 0.57775(5) 0.42121(11) 0.0187(3) Uani 1 1 d . . . . .
H8BA H 0.194277 0.577699 0.464593 0.022 Uiso 1 1 calc R U . . .
H8BB H 0.422730 0.559536 0.449251 0.022 Uiso 1 1 calc R U . . .
C5B C 0.5015(3) 0.76502(6) 0.35355(12) 0.0216(3) Uani 1 1 d . . . . .
H5B H 0.398036 0.788358 0.352312 0.026 Uiso 1 1 calc R U . . .
C9A' C 1.3222(3) 1.02920(6) 0.61493(13) 0.0240(4) Uani 1 1 d . . . . .
H9AA H 1.416275 1.006626 0.591980 0.036 Uiso 1 1 calc R U . . .
H9AB H 1.347792 1.030390 0.682509 0.036 Uiso 1 1 calc R U . . .
H9AC H 1.348582 1.059458 0.589513 0.036 Uiso 1 1 calc R U . . .
C6A' C 1.1030(3) 0.89739(6) 0.67390(11) 0.0210(3) Uani 1 1 d . . . . .
H6A' H 1.192665 0.875520 0.706890 0.025 Uiso 1 1 calc R U . . .
C5A' C 1.1807(3) 0.94114(6) 0.65844(11) 0.0206(3) Uani 1 1 d . . . . .
H5A' H 1.320787 0.949042 0.681598 0.025 Uiso 1 1 calc R U . . .
C3B C 0.8521(3) 0.74144(6) 0.33147(12) 0.0232(4) Uani 1 1 d . . . . .
H3B H 0.986178 0.748583 0.314167 0.028 Uiso 1 1 calc R U . . .
C7B' C 0.2098(3) 0.55564(6) 0.33014(12) 0.0209(3) Uani 1 1 d . . . . .
H7BA H 0.101226 0.576072 0.298158 0.025 Uiso 1 1 calc R U . . .
H7BB H 0.322199 0.552054 0.289937 0.025 Uiso 1 1 calc R U . . .
C4B C 0.6986(3) 0.77480(5) 0.32803(12) 0.0231(4) Uani 1 1 d . . . . .
H4B H 0.727997 0.804844 0.307970 0.028 Uiso 1 1 calc R U . . .
C2A C 0.2130(3) 0.69203(6) 0.59901(11) 0.0210(3) Uani 1 1 d . . . . .
C4A C 0.3165(3) 0.61550(6) 0.64527(12) 0.0255(4) Uani 1 1 d . . . . .
H4A H 0.281639 0.584216 0.653229 0.031 Uiso 1 1 calc R U . . .
C8A' C 0.7383(3) 0.81243(6) 0.57072(12) 0.0211(3) Uani 1 1 d . . . . .
H8AA H 0.620036 0.829385 0.536311 0.025 Uiso 1 1 calc R U . . .
H8AB H 0.853160 0.810841 0.531390 0.025 Uiso 1 1 calc R U . . .
C5A C 0.5225(3) 0.62987(6) 0.66698(13) 0.0264(4) Uani 1 1 d . . . . .
H5A H 0.627182 0.608868 0.692223 0.032 Uiso 1 1 calc R U . . .
C3A C 0.1613(3) 0.64624(6) 0.61218(12) 0.0248(4) Uani 1 1 d . . . . .
H3A H 0.020186 0.636231 0.598497 0.030 Uiso 1 1 calc R U . . .
C7A' C 0.8143(3) 0.83798(6) 0.65989(12) 0.0249(4) Uani 1 1 d . . . . .
H7AA H 0.696600 0.840926 0.697388 0.030 Uiso 1 1 calc R U . . .
H7AB H 0.926083 0.819834 0.695950 0.030 Uiso 1 1 calc R U . . .
C9B' C -0.3209(3) 0.37422(6) 0.42772(13) 0.0252(4) Uani 1 1 d . . . . .
H9BA H -0.434926 0.386669 0.384018 0.038 Uiso 1 1 calc R U . . .
H9BB H -0.314283 0.390861 0.486368 0.038 Uiso 1 1 calc R U . . .
H9BC H -0.346819 0.341643 0.438250 0.038 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O7B C7B 1.255(2) . ?
O4A' C4A' 1.3697(19) . ?
O4A' C9A' 1.423(2) . ?
O2B H2B 0.8400 . ?
O2B C2B 1.354(2) . ?
O4B' C4B' 1.3689(19) . ?
O4B' C9B' 1.425(2) . ?
O7A C7A 1.251(2) . ?
O2A H2A 0.8400 . ?
O2A C2A 1.354(2) . ?
N8B' H8B' 0.8800 . ?
N8B' C7B 1.328(2) . ?
N8B' C8B' 1.4624(19) . ?
N8A' H8A' 0.8800 . ?
N8A' C7A 1.331(2) . ?
N8A' C8A' 1.458(2) . ?
C7B C1B 1.497(2) . ?
C4A' C3A' 1.393(3) . ?
C4A' C5A' 1.391(2) . ?
C1B C6B 1.403(2) . ?
C1B C2B 1.403(2) . ?
C3B' H3B' 0.9500 . ?
C3B' C2B' 1.388(2) . ?
C3B' C4B' 1.395(2) . ?
C5B' H5B' 0.9500 . ?
C5B' C6B' 1.399(2) . ?
C5B' C4B' 1.395(2) . ?
C6B H6B 0.9500 . ?
C6B C5B 1.385(2) . ?
C2A' H2A' 0.9500 . ?
C2A' C1A' 1.398(2) . ?
C2A' C3A' 1.387(2) . ?
C2B' H2B' 0.9500 . ?
C2B' C1B' 1.399(2) . ?
C6B' H6B' 0.9500 . ?
C6B' C1B' 1.391(2) . ?
C1A' C6A' 1.388(3) . ?
C1A' C7A' 1.511(2) . ?
C7A C1A 1.492(2) . ?
C6A H6A 0.9500 . ?
C6A C1A 1.393(2) . ?
C6A C5A 1.388(2) . ?
C1B' C7B' 1.514(2) . ?
C1A C2A 1.404(2) . ?
C3A' H3A' 0.9500 . ?
C2B C3B 1.401(2) . ?
C8B' H8BA 0.9900 . ?
C8B' H8BB 0.9900 . ?
C8B' C7B' 1.528(2) . ?
C5B H5B 0.9500 . ?
C5B C4B 1.393(3) . ?
C9A' H9AA 0.9800 . ?
C9A' H9AB 0.9800 . ?
C9A' H9AC 0.9800 . ?
C6A' H6A' 0.9500 . ?
C6A' C5A' 1.399(2) . ?
C5A' H5A' 0.9500 . ?
C3B H3B 0.9500 . ?
C3B C4B 1.382(3) . ?
C7B' H7BA 0.9900 . ?
C7B' H7BB 0.9900 . ?
C4B H4B 0.9500 . ?
C2A C3A 1.395(2) . ?
C4A H4A 0.9500 . ?
C4A C5A 1.388(3) . ?
C4A C3A 1.383(3) . ?
C8A' H8AA 0.9900 . ?
C8A' H8AB 0.9900 . ?
C8A' C7A' 1.526(2) . ?
C5A H5A 0.9500 . ?
C3A H3A 0.9500 . ?
C7A' H7AA 0.9900 . ?
C7A' H7AB 0.9900 . ?
C9B' H9BA 0.9800 . ?
C9B' H9BB 0.9800 . ?
C9B' H9BC 0.9800 . ?

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
_geom_angle_publ_flag
C4A' O4A' C9A' 117.54(13) . . ?
C2B O2B H2B 109.5 . . ?
C4B' O4B' C9B' 117.47(13) . . ?
C2A O2A H2A 109.5 . . ?
C7B N8B' H8B' 118.0 . . ?
C7B N8B' C8B' 123.95(14) . . ?
C8B' N8B' H8B' 118.0 . . ?
C7A N8A' H8A' 118.5 . . ?
C7A N8A' C8A' 123.01(15) . . ?
C8A' N8A' H8A' 118.5 . . ?
O7B C7B N8B' 122.28(15) . . ?
O7B C7B C1B 120.00(15) . . ?
N8B' C7B C1B 117.68(14) . . ?
O4A' C4A' C3A' 115.41(15) . . ?
O4A' C4A' C5A' 124.73(16) . . ?
C5A' C4A' C3A' 119.84(15) . . ?
C6B C1B C7B 123.11(15) . . ?
C2B C1B C7B 118.06(14) . . ?
C2B C1B C6B 118.77(15) . . ?
C2B' C3B' H3B' 119.9 . . ?
C2B' C3B' C4B' 120.22(15) . . ?
C4B' C3B' H3B' 119.9 . . ?
C6B' C5B' H5B' 120.5 . . ?
C4B' C5B' H5B' 120.5 . . ?
C4B' C5B' C6B' 118.99(16) . . ?
C1B C6B H6B 119.5 . . ?
C5B C6B C1B 121.09(16) . . ?
C5B C6B H6B 119.5 . . ?
C1A' C2A' H2A' 119.4 . . ?
C3A' C2A' H2A' 119.4 . . ?
C3A' C2A' C1A' 121.11(16) . . ?
C3B' C2B' H2B' 119.5 . . ?
C3B' C2B' C1B' 121.08(16) . . ?
C1B' C2B' H2B' 119.5 . . ?
C5B' C6B' H6B' 119.0 . . ?
C1B' C6B' C5B' 122.01(15) . . ?
C1B' C6B' H6B' 119.0 . . ?
C2A' C1A' C7A' 120.57(17) . . ?
C6A' C1A' C2A' 118.07(15) . . ?
C6A' C1A' C7A' 121.36(16) . . ?
O7A C7A N8A' 121.76(15) . . ?
O7A C7A C1A 120.51(16) . . ?
N8A' C7A C1A 117.72(15) . . ?
C1A C6A H6A 119.5 . . ?
C5A C6A H6A 119.5 . . ?
C5A C6A C1A 120.99(18) . . ?
C2B' C1B' C7B' 120.93(15) . . ?
C6B' C1B' C2B' 117.88(15) . . ?
C6B' C1B' C7B' 121.18(15) . . ?
C6A C1A C7A 123.17(16) . . ?
C6A C1A C2A 118.70(15) . . ?
C2A C1A C7A 118.12(15) . . ?
O4B' C4B' C3B' 115.32(14) . . ?
O4B' C4B' C5B' 124.87(15) . . ?
C5B' C4B' C3B' 119.81(15) . . ?
C4A' C3A' H3A' 120.0 . . ?
C2A' C3A' C4A' 120.07(15) . . ?
C2A' C3A' H3A' 120.0 . . ?
O2B C2B C1B 121.35(15) . . ?
O2B C2B C3B 118.50(16) . . ?
C3B C2B C1B 120.14(16) . . ?
N8B' C8B' H8BA 109.4 . . ?
N8B' C8B' H8BB 109.4 . . ?
N8B' C8B' C7B' 111.16(13) . . ?
H8BA C8B' H8BB 108.0 . . ?
C7B' C8B' H8BA 109.4 . . ?
C7B' C8B' H8BB 109.4 . . ?
C6B C5B H5B 120.4 . . ?
C6B C5B C4B 119.28(16) . . ?
C4B C5B H5B 120.4 . . ?
O4A' C9A' H9AA 109.5 . . ?
O4A' C9A' H9AB 109.5 . . ?
O4A' C9A' H9AC 109.5 . . ?
H9AA C9A' H9AB 109.5 . . ?
H9AA C9A' H9AC 109.5 . . ?
H9AB C9A' H9AC 109.5 . . ?
C1A' C6A' H6A' 119.2 . . ?
C1A' C6A' C5A' 121.60(16) . . ?
C5A' C6A' H6A' 119.2 . . ?
C4A' C5A' C6A' 119.29(16) . . ?
C4A' C5A' H5A' 120.4 . . ?
C6A' C5A' H5A' 120.4 . . ?
C2B C3B H3B 120.1 . . ?
C4B C3B C2B 119.72(16) . . ?
C4B C3B H3B 120.1 . . ?
C1B' C7B' C8B' 111.96(13) . . ?
C1B' C7B' H7BA 109.2 . . ?
C1B' C7B' H7BB 109.2 . . ?
C8B' C7B' H7BA 109.2 . . ?
C8B' C7B' H7BB 109.2 . . ?
H7BA C7B' H7BB 107.9 . . ?
C5B C4B H4B 119.5 . . ?
C3B C4B C5B 120.96(15) . . ?
C3B C4B H4B 119.5 . . ?
O2A C2A C1A 121.23(15) . . ?
O2A C2A C3A 118.44(17) . . ?
C3A C2A C1A 120.32(17) . . ?
C5A C4A H4A 119.6 . . ?
C3A C4A H4A 119.6 . . ?
C3A C4A C5A 120.70(16) . . ?
N8A' C8A' H8AA 109.5 . . ?
N8A' C8A' H8AB 109.5 . . ?
N8A' C8A' C7A' 110.78(13) . . ?
H8AA C8A' H8AB 108.1 . . ?
C7A' C8A' H8AA 109.5 . . ?
C7A' C8A' H8AB 109.5 . . ?
C6A C5A H5A 120.2 . . ?
C4A C5A C6A 119.50(18) . . ?
C4A C5A H5A 120.2 . . ?
C2A C3A H3A 120.2 . . ?
C4A C3A C2A 119.65(17) . . ?
C4A C3A H3A 120.2 . . ?
C1A' C7A' C8A' 112.47(14) . . ?
C1A' C7A' H7AA 109.1 . . ?
C1A' C7A' H7AB 109.1 . . ?
C8A' C7A' H7AA 109.1 . . ?
C8A' C7A' H7AB 109.1 . . ?
H7AA C7A' H7AB 107.8 . . ?
O4B' C9B' H9BA 109.5 . . ?
O4B' C9B' H9BB 109.5 . . ?
O4B' C9B' H9BC 109.5 . . ?
H9BA C9B' H9BB 109.5 . . ?
H9BA C9B' H9BC 109.5 . . ?
H9BB C9B' H9BC 109.5 . . ?

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
_geom_torsion_publ_flag
O7B C7B C1B C6B -167.78(15) . . . . ?
O7B C7B C1B C2B 14.9(2) . . . . ?
O4A' C4A' C3A' C2A' 179.37(14) . . . . ?
O4A' C4A' C5A' C6A' -178.11(15) . . . . ?
O2B C2B C3B C4B -179.94(16) . . . . ?
O7A C7A C1A C6A -166.01(17) . . . . ?
O7A C7A C1A C2A 14.0(2) . . . . ?
O2A C2A C3A C4A -178.60(16) . . . . ?
N8B' C7B C1B C6B 14.4(2) . . . . ?
N8B' C7B C1B C2B -162.84(15) . . . . ?
N8B' C8B' C7B' C1B' -172.53(14) . . . . ?
N8A' C7A C1A C6A 15.2(2) . . . . ?
N8A' C7A C1A C2A -164.79(15) . . . . ?
N8A' C8A' C7A' C1A' 176.62(15) . . . . ?
C7B N8B' C8B' C7B' -104.53(18) . . . . ?
C7B C1B C6B C5B -176.56(15) . . . . ?
C7B C1B C2B O2B -3.1(2) . . . . ?
C7B C1B C2B C3B 175.55(14) . . . . ?
C1B C6B C5B C4B 0.9(2) . . . . ?
C1B C2B C3B C4B 1.4(2) . . . . ?
C3B' C2B' C1B' C6B' -0.5(2) . . . . ?
C3B' C2B' C1B' C7B' 178.55(15) . . . . ?
C5B' C6B' C1B' C2B' 1.0(2) . . . . ?
C5B' C6B' C1B' C7B' -178.11(15) . . . . ?
C6B C1B C2B O2B 179.49(15) . . . . ?
C6B C1B C2B C3B -1.9(2) . . . . ?
C6B C5B C4B C3B -1.4(3) . . . . ?
C2A' C1A' C6A' C5A' 0.5(2) . . . . ?
C2A' C1A' C7A' C8A' 59.5(2) . . . . ?
C2B' C3B' C4B' O4B' -178.81(15) . . . . ?
C2B' C3B' C4B' C5B' 0.8(3) . . . . ?
C2B' C1B' C7B' C8B' -104.43(18) . . . . ?
C6B' C5B' C4B' O4B' 179.21(15) . . . . ?
C6B' C5B' C4B' C3B' -0.4(2) . . . . ?
C6B' C1B' C7B' C8B' 74.6(2) . . . . ?
C1A' C2A' C3A' C4A' -1.2(2) . . . . ?
C1A' C6A' C5A' C4A' -1.1(2) . . . . ?
C7A N8A' C8A' C7A' 96.7(2) . . . . ?
C7A C1A C2A O2A -3.0(2) . . . . ?
C7A C1A C2A C3A 176.07(15) . . . . ?
C6A C1A C2A O2A 177.00(15) . . . . ?
C6A C1A C2A C3A -3.9(2) . . . . ?
C1A C6A C5A C4A 1.1(3) . . . . ?
C1A C2A C3A C4A 2.3(2) . . . . ?
C4B' C3B' C2B' C1B' -0.4(3) . . . . ?
C4B' C5B' C6B' C1B' -0.5(2) . . . . ?
C3A' C4A' C5A' C6A' 0.5(2) . . . . ?
C3A' C2A' C1A' C6A' 0.7(2) . . . . ?
C3A' C2A' C1A' C7A' -179.41(15) . . . . ?
C2B C1B C6B C5B 0.7(2) . . . . ?
C2B C3B C4B C5B 0.3(3) . . . . ?
C8B' N8B' C7B O7B -2.9(2) . . . . ?
C8B' N8B' C7B C1B 174.78(13) . . . . ?
C9A' O4A' C4A' C3A' -176.75(15) . . . . ?
C9A' O4A' C4A' C5A' 1.9(2) . . . . ?
C6A' C1A' C7A' C8A' -120.60(18) . . . . ?
C5A' C4A' C3A' C2A' 0.6(2) . . . . ?
C8A' N8A' C7A O7A 1.3(2) . . . . ?
C8A' N8A' C7A C1A -179.90(14) . . . . ?
C5A C6A C1A C7A -177.76(16) . . . . ?
C5A C6A C1A C2A 2.2(2) . . . . ?
C5A C4A C3A C2A 1.1(3) . . . . ?
C3A C4A C5A C6A -2.8(3) . . . . ?
C7A' C1A' C6A' C5A' -179.42(15) . . . . ?
C9B' O4B' C4B' C3B' 179.63(15) . . . . ?
C9B' O4B' C4B' C5B' 0.0(2) . . . . ?

_olex2_submission_original_sample_id riparin_II_100K
_olex2_submission_special_instructions 'No special instructions were received'
