# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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. 
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data_nicotinium_orotate_hemihydrate
_database_code_depnum_ccdc_archive 'CCDC 2161823'
loop_
_audit_author_name
_audit_author_address
'Devin J. Angevine'
;University at Buffalo
United States of America
;
_audit_update_record             
;
2022-03-24 deposited with the CCDC.	2022-08-05 downloaded from the CCDC.
;
_audit_creation_date             2022-03-03
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
devinang@buffalo.edu
jbb6@buffalo.edu
_chemical_name_common            ?
_chemical_name_systematic        '(S)-Nicotinium Orotate Hemihydrate'
_chemical_formula_moiety         '2(C10 H15 N2), 2(C5 H3 N2 O4), H2 O'
_chemical_formula_sum            'C30 H38 N8 O9'
_chemical_formula_weight         654.68
_chemical_absolute_configuration rm
_chemical_melting_point          408.65
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      orthorhombic
_space_group_IT_number           17
_space_group_name_H-M_alt        'P 2 2 21'
_space_group_name_Hall           'P 2c 2'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x, y, -z+1/2'
'x, -y, -z'

_cell_length_a                   6.9489(7)
_cell_length_b                   9.7256(10)
_cell_length_c                   23.026(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1556.1(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6162
_cell_measurement_temperature    90.0
_cell_measurement_theta_max      27.14
_cell_measurement_theta_min      2.27
_shelx_estimated_absorpt_T_max   0.998
_shelx_estimated_absorpt_T_min   0.985
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6787
_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 0.0599 after correction.
The Ratio of minimum to maximum transmission is 0.9103.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.397
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             692
_exptl_crystal_preparation       'slow evaporation from water'
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0524
_diffrn_reflns_av_unetI/netI     0.0299
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            27746
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.582
_diffrn_reflns_theta_min         1.769
_diffrn_ambient_temperature      90.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.720
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                3405
_reflns_number_total             3616
_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 (Bruker, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.242
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.052

_refine_ls_extinction_coef       0.0057(11)
_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   1.157
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     231
_refine_ls_number_reflns         3616
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0530
_refine_ls_R_factor_gt           0.0497
_refine_ls_restrained_S_all      1.157
_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)+(0.0188P)²+1.4976P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1075
_refine_ls_wR_factor_ref         0.1088
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C6(H6)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9a,H9b), C8(H8a,H8b), C7(H7a,H7b)
2.c Aromatic/amide H refined with riding coordinates:
 C13(H13), C2(H2a), C5(H5), C3(H3), C1(H1)
2.d Idealised Me refined as rotating group:
 C10(H10a,H10b,H10c)
;
_atom_sites_solution_hydrogens   mixed
_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
O1 O 0.5930(4) 0.8586(3) 0.53646(10) 0.0301(6) Uani 1 1 d . . . . .
O5 O 0.000000 0.0957(4) 0.250000 0.0285(8) Uani 1 2 d S T P . .
O2 O 0.4735(4) 0.6453(3) 0.53035(11) 0.0342(6) Uani 1 1 d . . . . .
O3 O 0.6897(4) 0.4832(2) 0.33986(11) 0.0299(6) Uani 1 1 d . . . . .
O4 O 0.7813(4) 0.9460(3) 0.33006(12) 0.0360(6) Uani 1 1 d . . . . .
N4 N 0.7379(4) 0.7149(3) 0.33618(11) 0.0186(5) Uani 1 1 d . . . . .
N1 N 0.2202(4) 0.6634(3) 0.28546(11) 0.0243(6) Uani 1 1 d . . . . .
N2 N 0.2934(4) 0.2426(3) 0.37400(12) 0.0216(6) Uani 1 1 d . . . . .
N3 N 0.6448(4) 0.6099(3) 0.42362(12) 0.0222(6) Uani 1 1 d . . . . .
C13 C 0.6903(4) 0.8514(3) 0.41974(12) 0.0160(6) Uani 1 1 d . . . . .
H13 H 0.691111 0.937412 0.439305 0.019 Uiso 1 1 calc R U . . .
C14 C 0.7405(5) 0.8458(3) 0.35991(13) 0.0212(6) Uani 1 1 d . . . . .
C4 C 0.1641(4) 0.4818(3) 0.35527(13) 0.0197(6) Uani 1 1 d . . . . .
C11 C 0.5636(5) 0.7481(4) 0.51073(13) 0.0213(7) Uani 1 1 d . . . . .
C15 C 0.6912(5) 0.5950(3) 0.36489(13) 0.0199(6) Uani 1 1 d . . . . .
C2 C 0.2134(5) 0.7140(3) 0.38756(14) 0.0230(7) Uani 1 1 d . . . . .
H2A H 0.222333 0.780211 0.417756 0.028 Uiso 1 1 calc R U . . .
C12 C 0.6414(4) 0.7364(3) 0.44921(13) 0.0195(6) Uani 1 1 d . . . . .
C5 C 0.1865(5) 0.5309(3) 0.29876(13) 0.0209(6) Uani 1 1 d . . . . .
H5 H 0.177256 0.466829 0.267745 0.025 Uiso 1 1 calc R U . . .
C6 C 0.1162(4) 0.3311(3) 0.36365(14) 0.0206(6) Uani 1 1 d . . . . .
H6 H 0.052886 0.297765 0.327277 0.025 Uiso 1 1 calc R U . . .
C3 C 0.1808(5) 0.5764(3) 0.40025(13) 0.0229(7) Uani 1 1 d . . . . .
H3 H 0.169875 0.547000 0.439460 0.028 Uiso 1 1 calc R U . . .
C1 C 0.2327(5) 0.7528(4) 0.32968(14) 0.0241(7) Uani 1 1 d . . . . .
H1 H 0.255747 0.846912 0.321096 0.029 Uiso 1 1 calc R U . . .
C9 C 0.2102(5) 0.1115(3) 0.39692(15) 0.0269(7) Uani 1 1 d . . . . .
H9A H 0.310082 0.054878 0.416085 0.032 Uiso 1 1 calc R U . . .
H9B H 0.149797 0.057187 0.365447 0.032 Uiso 1 1 calc R U . . .
C10 C 0.4186(5) 0.2223(4) 0.32259(15) 0.0308(8) Uani 1 1 d . . . . .
H10A H 0.341179 0.188330 0.290041 0.037 Uiso 1 1 calc R U . . .
H10B H 0.519133 0.155125 0.331869 0.037 Uiso 1 1 calc R U . . .
H10C H 0.478314 0.309997 0.311878 0.037 Uiso 1 1 calc R U . . .
C8 C 0.0606(5) 0.1605(4) 0.44043(16) 0.0309(8) Uani 1 1 d . . . . .
H8A H 0.119949 0.176660 0.478922 0.037 Uiso 1 1 calc R U . . .
H8B H -0.043772 0.091977 0.444697 0.037 Uiso 1 1 calc R U . . .
C7 C -0.0168(6) 0.2944(4) 0.41503(17) 0.0338(9) Uani 1 1 d . . . . .
H7A H -0.014386 0.368293 0.444604 0.041 Uiso 1 1 calc R U . . .
H7B H -0.150867 0.282171 0.401474 0.041 Uiso 1 1 calc R U . . .
H4 H 0.757(5) 0.709(4) 0.2981(16) 0.022(9) Uiso 1 1 d . . . . .
H2 H 0.353(6) 0.282(4) 0.4007(16) 0.025(10) Uiso 1 1 d . . . . .
H3A H 0.607(6) 0.520(4) 0.4430(18) 0.036(12) Uiso 1 1 d . . . . .
H5A H -0.056(7) 0.035(5) 0.2713(19) 0.052(15) Uiso 1 1 d . . . . .


_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
O1 C11 1.245(4) . ?
O5 H5A 0.86(4) . ?
O5 H5A 0.86(4) 3 ?
O2 C11 1.263(4) . ?
O3 C15 1.231(4) . ?
O4 C14 1.226(4) . ?
N4 C14 1.385(4) . ?
N4 C15 1.379(4) . ?
N4 H4 0.89(4) . ?
N1 C5 1.345(4) . ?
N1 C1 1.342(4) . ?
N2 C6 1.521(4) . ?
N2 C9 1.497(4) . ?
N2 C10 1.482(4) . ?
N2 H2 0.83(4) . ?
N3 C15 1.398(4) . ?
N3 C12 1.365(4) . ?
N3 H3A 1.02(4) . ?
C13 H13 0.9500 . ?
C13 C14 1.422(4) . ?
C13 C12 1.351(4) . ?
C4 C5 1.395(4) . ?
C4 C6 1.515(4) . ?
C4 C3 1.390(4) . ?
C11 C12 1.520(4) . ?
C2 H2A 0.9500 . ?
C2 C3 1.388(5) . ?
C2 C1 1.392(5) . ?
C5 H5 0.9500 . ?
C6 H6 1.0000 . ?
C6 C7 1.543(5) . ?
C3 H3 0.9500 . ?
C1 H1 0.9500 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C8 1.520(5) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C7 1.525(5) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?

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
H5A O5 H5A 94(6) . 3 ?
C14 N4 H4 116(2) . . ?
C15 N4 C14 126.2(3) . . ?
C15 N4 H4 117(2) . . ?
C1 N1 C5 117.3(3) . . ?
C6 N2 H2 105(3) . . ?
C9 N2 C6 103.0(2) . . ?
C9 N2 H2 109(3) . . ?
C10 N2 C6 115.2(3) . . ?
C10 N2 C9 113.2(3) . . ?
C10 N2 H2 111(3) . . ?
C15 N3 H3A 113(2) . . ?
C12 N3 C15 121.0(3) . . ?
C12 N3 H3A 126(2) . . ?
C14 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
C12 C13 C14 121.1(3) . . ?
O4 C14 N4 120.8(3) . . ?
O4 C14 C13 124.7(3) . . ?
N4 C14 C13 114.5(3) . . ?
C5 C4 C6 118.3(3) . . ?
C3 C4 C5 117.3(3) . . ?
C3 C4 C6 124.3(3) . . ?
O1 C11 O2 126.5(3) . . ?
O1 C11 C12 116.7(3) . . ?
O2 C11 C12 116.8(3) . . ?
O3 C15 N4 121.6(3) . . ?
O3 C15 N3 122.9(3) . . ?
N4 C15 N3 115.5(3) . . ?
C3 C2 H2A 120.7 . . ?
C3 C2 C1 118.6(3) . . ?
C1 C2 H2A 120.7 . . ?
N3 C12 C11 118.4(3) . . ?
C13 C12 N3 121.7(3) . . ?
C13 C12 C11 119.7(3) . . ?
N1 C5 C4 124.1(3) . . ?
N1 C5 H5 118.0 . . ?
C4 C5 H5 118.0 . . ?
N2 C6 H6 107.7 . . ?
N2 C6 C7 103.5(3) . . ?
C4 C6 N2 112.9(3) . . ?
C4 C6 H6 107.7 . . ?
C4 C6 C7 116.9(3) . . ?
C7 C6 H6 107.7 . . ?
C4 C3 H3 120.2 . . ?
C2 C3 C4 119.7(3) . . ?
C2 C3 H3 120.2 . . ?
N1 C1 C2 123.0(3) . . ?
N1 C1 H1 118.5 . . ?
C2 C1 H1 118.5 . . ?
N2 C9 H9A 111.1 . . ?
N2 C9 H9B 111.1 . . ?
N2 C9 C8 103.2(3) . . ?
H9A C9 H9B 109.1 . . ?
C8 C9 H9A 111.1 . . ?
C8 C9 H9B 111.1 . . ?
N2 C10 H10A 109.5 . . ?
N2 C10 H10B 109.5 . . ?
N2 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C8 H8A 110.8 . . ?
C9 C8 H8B 110.8 . . ?
C9 C8 C7 104.8(3) . . ?
H8A C8 H8B 108.9 . . ?
C7 C8 H8A 110.8 . . ?
C7 C8 H8B 110.8 . . ?
C6 C7 H7A 110.5 . . ?
C6 C7 H7B 110.5 . . ?
C8 C7 C6 106.3(3) . . ?
C8 C7 H7A 110.5 . . ?
C8 C7 H7B 110.5 . . ?
H7A C7 H7B 108.7 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C13 H13 O1 0.95 2.17 3.070(4) 157.6 4_576 yes
C5 H5 O3 0.95 2.65 3.338(4) 129.8 3_655 yes
C9 H9A O1 0.99 2.40 3.085(4) 125.6 4_566 yes
C10 H10C O3 0.98 2.33 3.185(5) 145.9 . yes
C8 H8B O1 0.99 2.61 3.297(5) 127.0 4_466 yes
C7 H7B O3 0.99 2.66 3.245(5) 118.2 1_455 yes
N4 H4 N1 0.89(4) 1.98(4) 2.860(4) 170(3) 3_655 yes
N2 H2 O1 0.83(4) 2.60(4) 3.092(4) 119(3) 4_566 yes
N2 H2 O2 0.83(4) 1.93(4) 2.758(4) 172(4) 4_566 yes
N3 H3A O2 1.02(4) 1.96(4) 2.950(4) 166(4) 4_566 yes
O5 H5A O4 0.86(4) 1.97(4) 2.798(3) 163(4) 1_445 yes

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
O1 C11 C12 N3 167.8(3) . . . . ?
O1 C11 C12 C13 -17.5(5) . . . . ?
O2 C11 C12 N3 -13.1(4) . . . . ?
O2 C11 C12 C13 161.6(3) . . . . ?
N2 C6 C7 C8 -16.7(4) . . . . ?
N2 C9 C8 C7 33.4(4) . . . . ?
C14 N4 C15 O3 178.7(3) . . . . ?
C14 N4 C15 N3 -0.7(5) . . . . ?
C14 C13 C12 N3 2.5(5) . . . . ?
C14 C13 C12 C11 -172.1(3) . . . . ?
C4 C6 C7 C8 -141.5(3) . . . . ?
C15 N4 C14 O4 -178.8(3) . . . . ?
C15 N4 C14 C13 0.4(5) . . . . ?
C15 N3 C12 C13 -2.9(5) . . . . ?
C15 N3 C12 C11 171.7(3) . . . . ?
C12 N3 C15 O3 -177.5(3) . . . . ?
C12 N3 C15 N4 1.9(4) . . . . ?
C12 C13 C14 O4 177.9(3) . . . . ?
C12 C13 C14 N4 -1.2(4) . . . . ?
C5 N1 C1 C2 0.4(5) . . . . ?
C5 C4 C6 N2 94.6(3) . . . . ?
C5 C4 C6 C7 -145.4(3) . . . . ?
C5 C4 C3 C2 1.6(5) . . . . ?
C6 N2 C9 C8 -44.3(3) . . . . ?
C6 C4 C5 N1 176.8(3) . . . . ?
C6 C4 C3 C2 -176.0(3) . . . . ?
C3 C4 C5 N1 -0.9(5) . . . . ?
C3 C4 C6 N2 -87.8(4) . . . . ?
C3 C4 C6 C7 32.1(5) . . . . ?
C3 C2 C1 N1 0.4(5) . . . . ?
C1 N1 C5 C4 -0.1(5) . . . . ?
C1 C2 C3 C4 -1.4(5) . . . . ?
C9 N2 C6 C4 164.9(3) . . . . ?
C9 N2 C6 C7 37.5(3) . . . . ?
C9 C8 C7 C6 -10.0(4) . . . . ?
C10 N2 C6 C4 -71.3(4) . . . . ?
C10 N2 C6 C7 161.3(3) . . . . ?
C10 N2 C9 C8 -169.3(3) . . . . ?

_olex2_exptl_crystal_mounting_method 'mounted with oil'
_olex2_submission_original_sample_id Nicotinium_Orotate_Hemihydrate
_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: Water'
