#------------------------------------------------------------------------------
#$Date: 2020-06-06 04:11:42 +0300 (Sat, 06 Jun 2020) $
#$Revision: 252959 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/82/1558223.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1558223
loop_
_publ_author_name
'Ding, Xiaodan'
'Unruh, Daniel K.'
'Groeneman , Ryan'
'Hutchins, Kristin M.'
_publ_section_title
;
 Controlling thermal expansion within mixed cocrystals by tuning molecular
 motion capability
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D0SC02795B
_journal_year                    2020
_chemical_formula_sum            'C16.51 H14 N3.49 O2'
_chemical_formula_weight         293.29
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2019-11-07T15:20:42-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2020-04-08 deposited with the CCDC.	2020-06-05 downloaded from the CCDC.
;
_cell_angle_alpha                93.3010(15)
_cell_angle_beta                 106.8700(17)
_cell_angle_gamma                113.897(2)
_cell_formula_units_Z            2
_cell_length_a                   8.01758(17)
_cell_length_b                   9.7320(2)
_cell_length_c                   10.86038(18)
_cell_measurement_reflns_used    6475
_cell_measurement_temperature    210(2)
_cell_measurement_theta_max      77.279
_cell_measurement_theta_min      4.322
_cell_volume                     726.41(3)
_computing_cell_refinement       'CrysAlisPro 1.171.40.61a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.61a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.61a (Rigaku OD, 2019)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      210(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.952
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0203814
_diffrn_orient_matrix_UB_12      -0.103266
_diffrn_orient_matrix_UB_13      0.1023517
_diffrn_orient_matrix_UB_21      -0.1950044
_diffrn_orient_matrix_UB_22      -0.1211712
_diffrn_orient_matrix_UB_23      -0.0988111
_diffrn_orient_matrix_UB_31      0.1078696
_diffrn_orient_matrix_UB_32      -0.0766998
_diffrn_orient_matrix_UB_33      -0.0514786
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0372
_diffrn_reflns_av_unetI/netI     0.0508
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.952
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            12586
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.952
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         77.421
_diffrn_reflns_theta_min         4.342
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.745
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.724
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
        CrysAlisPro 1.171.40.61a (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
                        a multifaceted crystal model
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_density_diffrn    1.341
_exptl_crystal_description       plate
_exptl_crystal_F_000             307
_exptl_crystal_size_max          0.206
_exptl_crystal_size_mid          0.157
_exptl_crystal_size_min          0.026
_refine_diff_density_max         0.173
_refine_diff_density_min         -0.169
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       0.0042(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   1.09
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     284
_refine_ls_number_reflns         2942
_refine_ls_number_restraints     507
_refine_ls_restrained_S_all      1.012
_refine_ls_R_factor_all          0.0523
_refine_ls_R_factor_gt           0.0442
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0718P)²+0.0823P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1256
_refine_ls_wR_factor_ref         0.1318
_reflns_Friedel_coverage         0
_reflns_number_gt                2484
_reflns_number_total             2942
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0sc02795b3.cif
_cod_data_source_block           A75_BA25_210
_cod_database_code               1558223
_shelx_estimated_absorpt_t_min   0.862
_shelx_estimated_absorpt_t_max   0.981
_shelx_shelxl_version_number     2018/3
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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 0.16575(14) 0.15725(12) 0.31168(10) 0.0494(3) Uani 1 1 d . . . . .
H1 H 0.19643 0.178637 0.392646 0.074 Uiso 1 1 calc R U . . .
O2 O 0.82176(15) 0.21831(14) 0.43541(11) 0.0575(3) Uani 1 1 d . . . . .
H2A H 0.825105 0.253147 0.508128 0.086 Uiso 1 1 calc R U . . .
N1 N 0.26145(18) 0.24845(15) -0.42117(12) 0.0495(3) Uani 1 1 d . . . . .
C1 C 0.31733(19) 0.15377(14) 0.28155(13) 0.0406(3) Uani 1 1 d . . . . .
C2 C 0.4929(2) 0.18567(14) 0.37812(13) 0.0410(3) Uani 1 1 d . . . . .
H2 H 0.508358 0.209305 0.467092 0.049 Uiso 1 1 calc R U . . .
C3 C 0.6458(2) 0.18282(15) 0.34391(13) 0.0438(3) Uani 1 1 d . . . . .
C4 C 0.6216(2) 0.14366(17) 0.21254(15) 0.0498(4) Uani 1 1 d . . . . .
H4 H 0.723035 0.138863 0.188533 0.06 Uiso 1 1 calc R U . . .
C5 C 0.4453(2) 0.11186(17) 0.11781(14) 0.0520(4) Uani 1 1 d . . . . .
H5 H 0.42877 0.086226 0.028892 0.062 Uiso 1 1 calc R U . . .
C6 C 0.2926(2) 0.11666(16) 0.14997(14) 0.0478(3) Uani 1 1 d . . . . .
H6 H 0.174399 0.095206 0.084006 0.057 Uiso 1 1 calc R U . . .
C7 C 0.3267(2) 0.39795(18) -0.37211(17) 0.0539(4) Uani 1 1 d . . . . .
H7 H 0.377435 0.469595 -0.421798 0.065 Uiso 1 1 calc R U . . .
C8 C 0.3236(2) 0.45213(17) -0.25343(16) 0.0527(4) Uani 1 1 d . . . . .
H8 H 0.372213 0.557868 -0.22235 0.063 Uiso 1 1 calc R U . . .
C9 C 0.2469(2) 0.34637(16) -0.18109(14) 0.0448(3) Uani 1 1 d D . . . .
C10 C 0.1823(2) 0.19188(16) -0.22900(14) 0.0460(3) Uani 1 1 d . . . . .
H10 H 0.131983 0.117977 -0.180883 0.055 Uiso 1 1 calc R U . . .
C11 C 0.1931(2) 0.14871(16) -0.34804(14) 0.0471(3) Uani 1 1 d . . . . .
H11 H 0.150372 0.043894 -0.379547 0.056 Uiso 1 1 calc R U . . .
N2A N 0.2115(7) 0.3765(4) -0.0572(4) 0.0391(9) Uani 0.690(12) 1 d D U P A 1
N3A N 0.2664(4) 0.5148(4) -0.0166(4) 0.0409(9) Uani 0.690(12) 1 d D U P A 1
C12A C 0.2315(9) 0.5543(6) 0.1002(5) 0.0367(9) Uani 0.690(12) 1 d . U P A 1
C13A C 0.2860(11) 0.7070(6) 0.1458(6) 0.0438(10) Uani 0.690(12) 1 d . U P A 1
H13A H 0.343514 0.782986 0.101587 0.053 Uiso 0.690(12) 1 calc R U P A 1
C14A C 0.2534(13) 0.7450(6) 0.2589(7) 0.0471(14) Uani 0.690(12) 1 d . U P A 1
H14A H 0.291271 0.849113 0.289701 0.057 Uiso 0.690(12) 1 calc R U P A 1
N4A N 0.1734(13) 0.6456(8) 0.3258(7) 0.0447(10) Uani 0.690(12) 1 d . U P A 1
C15A C 0.1202(10) 0.4992(7) 0.2794(6) 0.0446(9) Uani 0.690(12) 1 d . U P A 1
H15A H 0.060843 0.426162 0.325227 0.054 Uiso 0.690(12) 1 calc R U P A 1
C16A C 0.1459(8) 0.4472(5) 0.1692(5) 0.0408(9) Uani 0.690(12) 1 d . U P A 1
H16A H 0.106656 0.34214 0.141386 0.049 Uiso 0.690(12) 1 calc R U P A 1
C12B C 0.213(2) 0.5226(13) 0.1224(11) 0.039(2) Uani 0.310(12) 1 d DG U P A 2
C13B C 0.283(2) 0.6812(13) 0.1473(14) 0.047(2) Uani 0.310(12) 1 d G U P A 2
H13B H 0.342127 0.739139 0.092669 0.057 Uiso 0.310(12) 1 calc R U P A 2
C14B C 0.264(3) 0.7540(12) 0.2531(17) 0.050(3) Uani 0.310(12) 1 d G U P A 2
H14B H 0.311338 0.861197 0.269949 0.06 Uiso 0.310(12) 1 calc R U P A 2
N4B N 0.176(3) 0.6682(17) 0.3340(15) 0.050(3) Uani 0.310(12) 1 d G U P A 2
C15B C 0.107(2) 0.5097(16) 0.3091(13) 0.048(2) Uani 0.310(12) 1 d G U P A 2
H15B H 0.047113 0.451713 0.363744 0.058 Uiso 0.310(12) 1 calc R U P A 2
C16B C 0.1250(19) 0.4369(11) 0.2033(12) 0.049(2) Uani 0.310(12) 1 d G U P A 2
H16B H 0.0779 0.329653 0.186465 0.059 Uiso 0.310(12) 1 calc R U P A 2
C17 C 0.2340(17) 0.462(2) 0.0194(10) 0.046(2) Uani 0.254(15) 1 d D U P A 2
C18 C 0.254(2) 0.415(2) -0.0753(13) 0.047(3) Uani 0.254(15) 1 d D U P A 2
N2B N 0.296(5) 0.485(6) -0.057(4) 0.047(5) Uani 0.056(6) 1 d D U P A 3
N3B N 0.180(5) 0.395(5) -0.011(5) 0.048(6) Uani 0.056(6) 1 d D U P A 3
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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 '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'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-5 4 3 0.1092
4 0 0 0.0687
0 5 -5 0.001
-2 5 4 0.0741
3 -5 -4 0.107
-4 0 0 0.0879
3 3 -3 0.045
1 -5 5 0.0227
4 -4 -4 0.116
0 -4 -4 0.1248
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
C1 O1 H1 109.5 . . ?
C3 O2 H2A 109.5 . . ?
C11 N1 C7 117.18(13) . . ?
O1 C1 C2 121.79(12) . . ?
O1 C1 C6 118.11(12) . . ?
C2 C1 C6 120.10(13) . . ?
C1 C2 C3 120.36(12) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
O2 C3 C2 122.03(12) . . ?
O2 C3 C4 118.00(13) . . ?
C2 C3 C4 119.97(13) . . ?
C5 C4 C3 118.73(14) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 H4 120.6 . . ?
C6 C5 C4 122.05(13) . . ?
C6 C5 H5 119 . . ?
C4 C5 H5 119 . . ?
C5 C6 C1 118.77(14) . . ?
C5 C6 H6 120.6 . . ?
C1 C6 H6 120.6 . . ?
N1 C7 C8 123.78(14) . . ?
N1 C7 H7 118.1 . . ?
C8 C7 H7 118.1 . . ?
C7 C8 C9 118.04(14) . . ?
C7 C8 H8 121 . . ?
C9 C8 H8 121 . . ?
C18 C9 C8 110.1(9) . . ?
C18 C9 C10 130.9(9) . . ?
C8 C9 C10 118.96(14) . . ?
C8 C9 N2A 127.5(2) . . ?
C10 C9 N2A 113.42(19) . . ?
C8 C9 N2B 92.5(10) . . ?
C10 C9 N2B 148.4(10) . . ?
C11 C10 C9 118.82(14) . . ?
C11 C10 H10 120.6 . . ?
C9 C10 H10 120.6 . . ?
N1 C11 C10 123.18(13) . . ?
N1 C11 H11 118.4 . . ?
C10 C11 H11 118.4 . . ?
N3A N2A C9 112.9(5) . . ?
N2A N3A C12A 116.7(5) . . ?
C13A C12A C16A 118.3(3) . . ?
C13A C12A N3A 118.1(4) . . ?
C16A C12A N3A 123.5(3) . . ?
C12A C13A C14A 118.1(3) . . ?
C12A C13A H13A 121 . . ?
C14A C13A H13A 121 . . ?
N4A C14A C13A 124.5(3) . . ?
N4A C14A H14A 117.7 . . ?
C13A C14A H14A 117.7 . . ?
C14A N4A C15A 116.4(3) . . ?
N4A C15A C16A 124.6(3) . . ?
N4A C15A H15A 117.7 . . ?
C16A C15A H15A 117.7 . . ?
C15A C16A C12A 118.0(3) . . ?
C15A C16A H16A 121 . . ?
C12A C16A H16A 121 . . ?
C17 C12B C13B 116.3(9) . . ?
C17 C12B C16B 123.7(9) . . ?
C13B C12B C16B 120 . . ?
C12B C13B C14B 120 . . ?
C12B C13B H13B 120 . . ?
C14B C13B H13B 120 . . ?
N4B C14B C13B 120 . . ?
N4B C14B H14B 120 . . ?
C13B C14B H14B 120 . . ?
C14B N4B C15B 120 . . ?
N4B C15B C16B 120 . . ?
N4B C15B H15B 120 . . ?
C16B C15B H15B 120 . . ?
C15B C16B C12B 120 . . ?
C15B C16B H16B 120 . . ?
C12B C16B H16B 120 . . ?
C18 C17 C12B 176(2) . . ?
C17 C18 C9 171(2) . . ?
N3B N2B C9 93(5) . . ?
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 C1 1.3594(17) . ?
O1 H1 0.83 . ?
O2 C3 1.3596(17) . ?
O2 H2A 0.83 . ?
N1 C11 1.335(2) . ?
N1 C7 1.344(2) . ?
C1 C2 1.3889(19) . ?
C1 C6 1.3893(19) . ?
C2 C3 1.391(2) . ?
C2 H2 0.94 . ?
C3 C4 1.391(2) . ?
C4 C5 1.385(2) . ?
C4 H4 0.94 . ?
C5 C6 1.384(2) . ?
C5 H5 0.94 . ?
C6 H6 0.94 . ?
C7 C8 1.375(2) . ?
C7 H7 0.94 . ?
C8 C9 1.384(2) . ?
C8 H8 0.94 . ?
C9 C18 1.270(12) . ?
C9 C10 1.3864(19) . ?
C9 N2A 1.490(5) . ?
C9 N2B 1.68(6) . ?
C10 C11 1.374(2) . ?
C10 H10 0.94 . ?
C11 H11 0.94 . ?
N2A N3A 1.240(5) . ?
N3A C12A 1.439(6) . ?
C12A C13A 1.382(4) . ?
C12A C16A 1.389(4) . ?
C13A C14A 1.387(4) . ?
C13A H13A 0.94 . ?
C14A N4A 1.313(4) . ?
C14A H14A 0.94 . ?
N4A C15A 1.329(4) . ?
C15A C16A 1.375(5) . ?
C15A H15A 0.94 . ?
C16A H16A 0.94 . ?
C12B C17 1.320(11) . ?
C12B C13B 1.39 . ?
C12B C16B 1.39 . ?
C13B C14B 1.39 . ?
C13B H13B 0.94 . ?
C14B N4B 1.39 . ?
C14B H14B 0.94 . ?
N4B C15B 1.39 . ?
C15B C16B 1.39 . ?
C15B H15B 0.94 . ?
C16B H16B 0.94 . ?
C17 C18 1.180(15) . ?
N2B N3B 1.24(2) . ?
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
O1 H1 N1 0.83 1.94 2.7666(16) 173.4 1_556 yes
O2 H2A N4A 0.83 2 2.826(5) 173.8 2_666 yes
O2 H2A N4B 0.83 1.84 2.67(7) 177.6 2_666 yes
