#------------------------------------------------------------------------------
#$Date: 2020-06-06 04:11:42 +0300 (Sat, 06 Jun 2020) $
#$Revision: 252959 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/82/1558222.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_1558222
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            'C16.53 H14 N3.47 O2'
_chemical_formula_weight         293.15
_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             2019-11-07T15:14:14-00:00
_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                93.160(2)
_cell_angle_beta                 106.919(3)
_cell_angle_gamma                113.993(3)
_cell_formula_units_Z            2
_cell_length_a                   7.9981(2)
_cell_length_b                   9.7278(3)
_cell_length_c                   10.8484(3)
_cell_measurement_reflns_used    6964
_cell_measurement_temperature    190(2)
_cell_measurement_theta_max      75.615
_cell_measurement_theta_min      4.325
_cell_volume                     723.07(4)
_computing_cell_refinement       'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.63a (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      190(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.957
_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      -0.0086956
_diffrn_orient_matrix_UB_12      -0.0975026
_diffrn_orient_matrix_UB_13      0.1072505
_diffrn_orient_matrix_UB_21      -0.1966394
_diffrn_orient_matrix_UB_22      -0.1266289
_diffrn_orient_matrix_UB_23      -0.0930622
_diffrn_orient_matrix_UB_31      0.1079728
_diffrn_orient_matrix_UB_32      -0.0757554
_diffrn_orient_matrix_UB_33      -0.0526518
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.035
_diffrn_reflns_av_unetI/netI     0.0509
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.957
_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            12658
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.957
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         77.277
_diffrn_reflns_theta_min         4.346
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.748
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.731
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
        CrysAlisPro 1.171.40.63a (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    1.346
_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         0.206
_refine_diff_density_min         -0.169
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       0.0048(10)
_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   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     284
_refine_ls_number_reflns         2940
_refine_ls_number_restraints     507
_refine_ls_restrained_S_all      0.995
_refine_ls_R_factor_all          0.0468
_refine_ls_R_factor_gt           0.0419
_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)+(0.0644P)²+0.1093P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1159
_refine_ls_wR_factor_ref         0.1204
_reflns_Friedel_coverage         0
_reflns_number_gt                2582
_reflns_number_total             2940
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0sc02795b3.cif
_cod_data_source_block           A75_BA25_190
_cod_database_code               1558222
_shelx_estimated_absorpt_t_min   0.861
_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 0.16517(13) 0.15800(11) 0.31162(9) 0.0438(3) Uani 1 1 d . . . . .
H1 H 0.198076 0.183652 0.393443 0.066 Uiso 1 1 calc R U . . .
O2 O 0.82273(14) 0.21855(13) 0.43560(10) 0.0513(3) Uani 1 1 d . . . . .
H2A H 0.826203 0.254066 0.509147 0.077 Uiso 1 1 calc R U . . .
N1 N 0.26182(16) 0.24884(14) -0.42111(11) 0.0448(3) Uani 1 1 d . . . . .
C1 C 0.31701(18) 0.15430(13) 0.28157(12) 0.0362(3) Uani 1 1 d . . . . .
C2 C 0.49301(18) 0.18614(13) 0.37827(12) 0.0371(3) Uani 1 1 d . . . . .
H2 H 0.508931 0.210141 0.468276 0.044 Uiso 1 1 calc R U . . .
C3 C 0.64622(19) 0.18303(14) 0.34379(12) 0.0389(3) Uani 1 1 d . . . . .
C4 C 0.6219(2) 0.14352(15) 0.21230(14) 0.0446(3) Uani 1 1 d . . . . .
H4 H 0.724576 0.138365 0.188172 0.054 Uiso 1 1 calc R U . . .
C5 C 0.4452(2) 0.11188(16) 0.11735(13) 0.0465(3) Uani 1 1 d . . . . .
H5 H 0.428427 0.085894 0.027433 0.056 Uiso 1 1 calc R U . . .
C6 C 0.2920(2) 0.11698(15) 0.14957(13) 0.0428(3) Uani 1 1 d . . . . .
H6 H 0.17222 0.095406 0.082823 0.051 Uiso 1 1 calc R U . . .
C7 C 0.3267(2) 0.39824(16) -0.37179(15) 0.0492(3) Uani 1 1 d . . . . .
H7 H 0.377712 0.471004 -0.422086 0.059 Uiso 1 1 calc R U . . .
C8 C 0.3237(2) 0.45224(16) -0.25274(15) 0.0473(3) Uani 1 1 d . . . . .
H8 H 0.372931 0.559094 -0.221096 0.057 Uiso 1 1 calc R U . . .
C9 C 0.24662(19) 0.34575(15) -0.18092(13) 0.0400(3) Uani 1 1 d D . . . .
C10 C 0.18204(19) 0.19104(15) -0.22869(13) 0.0409(3) Uani 1 1 d . . . . .
H10 H 0.131148 0.116086 -0.180003 0.049 Uiso 1 1 calc R U . . .
C11 C 0.19323(19) 0.14837(15) -0.34822(13) 0.0419(3) Uani 1 1 d . . . . .
H11 H 0.150115 0.042489 -0.380246 0.05 Uiso 1 1 calc R U . . .
N2A N 0.2113(7) 0.3767(4) -0.0566(4) 0.0351(9) Uani 0.696(13) 1 d D U P A 1
N3A N 0.2669(4) 0.5152(4) -0.0170(4) 0.0361(8) Uani 0.696(13) 1 d D U P A 1
C12A C 0.2319(8) 0.5539(6) 0.0995(5) 0.0320(8) Uani 0.696(13) 1 d . U P A 1
C13A C 0.2866(10) 0.7073(5) 0.1452(5) 0.0379(9) Uani 0.696(13) 1 d . U P A 1
H13A H 0.344817 0.784098 0.100185 0.045 Uiso 0.696(13) 1 calc R U P A 1
C14A C 0.2541(12) 0.7454(5) 0.2582(7) 0.0419(14) Uani 0.696(13) 1 d . U P A 1
H14A H 0.292681 0.850776 0.289189 0.05 Uiso 0.696(13) 1 calc R U P A 1
N4A N 0.1734(11) 0.6459(7) 0.3255(6) 0.0394(9) Uani 0.696(13) 1 d . U P A 1
C15A C 0.1201(9) 0.4998(6) 0.2797(5) 0.0385(8) Uani 0.696(13) 1 d . U P A 1
H15A H 0.060144 0.426045 0.326328 0.046 Uiso 0.696(13) 1 calc R U P A 1
C16A C 0.1456(7) 0.4471(4) 0.1688(5) 0.0355(8) Uani 0.696(13) 1 d . U P A 1
H16A H 0.105213 0.340768 0.140864 0.043 Uiso 0.696(13) 1 calc R U P A 1
C12B C 0.2136(18) 0.5247(12) 0.1243(10) 0.034(2) Uani 0.304(13) 1 d DG U P A 2
C13B C 0.283(2) 0.6833(12) 0.1493(13) 0.046(3) Uani 0.304(13) 1 d G U P A 2
H13B H 0.343548 0.742374 0.09416 0.055 Uiso 0.304(13) 1 calc R U P A 2
C14B C 0.263(3) 0.7555(11) 0.2548(16) 0.045(3) Uani 0.304(13) 1 d G U P A 2
H14B H 0.310831 0.863911 0.271839 0.054 Uiso 0.304(13) 1 calc R U P A 2
N4B N 0.175(3) 0.6691(16) 0.3354(13) 0.047(2) Uani 0.304(13) 1 d G U P A 2
C15B C 0.1054(19) 0.5105(15) 0.3105(12) 0.044(2) Uani 0.304(13) 1 d G U P A 2
H15B H 0.044793 0.451444 0.365568 0.053 Uiso 0.304(13) 1 calc R U P A 2
C16B C 0.1249(16) 0.4383(10) 0.2049(12) 0.043(2) Uani 0.304(13) 1 d G U P A 2
H16B H 0.077508 0.329904 0.187889 0.052 Uiso 0.304(13) 1 calc R U P A 2
C17 C 0.2339(15) 0.4632(18) 0.0184(9) 0.043(2) Uani 0.263(14) 1 d D U P A 2
C18 C 0.253(2) 0.412(2) -0.0753(12) 0.042(2) Uani 0.263(14) 1 d D U P A 2
N2B N 0.292(7) 0.485(8) -0.055(6) 0.044(6) Uani 0.037(6) 1 d D U P A 3
N3B N 0.177(8) 0.378(7) -0.019(6) 0.052(8) Uani 0.037(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 -4 -4 0.116
3 3 -4 0.045
3 -5 -4 0.107
1 -5 5 0.0227
-1 5 -5 0.001
-2 5 4 0.0741
-4 0 0 0.0879
4 0 0 0.0687
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(12) . . ?
O1 C1 C2 121.80(11) . . ?
O1 C1 C6 118.10(12) . . ?
C2 C1 C6 120.10(12) . . ?
C1 C2 C3 120.24(11) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 H2 119.9 . . ?
O2 C3 C4 118.01(12) . . ?
O2 C3 C2 121.85(11) . . ?
C4 C3 C2 120.14(12) . . ?
C5 C4 C3 118.72(13) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 H4 120.6 . . ?
C4 C5 C6 121.97(12) . . ?
C4 C5 H5 119 . . ?
C6 C5 H5 119 . . ?
C5 C6 C1 118.79(13) . . ?
C5 C6 H6 120.6 . . ?
C1 C6 H6 120.6 . . ?
N1 C7 C8 123.98(13) . . ?
N1 C7 H7 118 . . ?
C8 C7 H7 118 . . ?
C7 C8 C9 117.76(13) . . ?
C7 C8 H8 121.1 . . ?
C9 C8 H8 121.1 . . ?
C18 C9 C8 110.5(9) . . ?
C18 C9 C10 130.2(9) . . ?
C8 C9 C10 119.29(13) . . ?
C8 C9 N2A 126.85(18) . . ?
C10 C9 N2A 113.74(18) . . ?
C8 C9 N2B 92.8(14) . . ?
C10 C9 N2B 147.8(14) . . ?
C11 C10 C9 118.64(13) . . ?
C11 C10 H10 120.7 . . ?
C9 C10 H10 120.7 . . ?
N1 C11 C10 123.10(12) . . ?
N1 C11 H11 118.5 . . ?
C10 C11 H11 118.5 . . ?
N3A N2A C9 112.7(5) . . ?
N2A N3A C12A 116.0(5) . . ?
C16A C12A C13A 118.1(3) . . ?
C16A C12A N3A 124.0(3) . . ?
C13A C12A N3A 117.9(4) . . ?
C14A C13A C12A 118.2(3) . . ?
C14A C13A H13A 120.9 . . ?
C12A C13A H13A 120.9 . . ?
N4A C14A C13A 124.5(3) . . ?
N4A C14A H14A 117.7 . . ?
C13A C14A H14A 117.7 . . ?
C14A N4A C15A 116.5(3) . . ?
N4A C15A C16A 124.6(3) . . ?
N4A C15A H15A 117.7 . . ?
C16A C15A H15A 117.7 . . ?
C15A C16A C12A 118.1(2) . . ?
C15A C16A H16A 121 . . ?
C12A C16A H16A 121 . . ?
C17 C12B C13B 116.4(8) . . ?
C17 C12B C16B 123.6(8) . . ?
C13B C12B C16B 120 . . ?
C14B C13B C12B 120 . . ?
C14B C13B H13B 120 . . ?
C12B 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 179(2) . . ?
C17 C18 C9 171.8(18) . . ?
N3B N2B C9 85(7) . . ?
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 1.3591(16) . ?
O1 H1 0.84 . ?
O2 C3 1.3607(16) . ?
O2 H2A 0.84 . ?
N1 C11 1.3354(18) . ?
N1 C7 1.3442(18) . ?
C1 C2 1.3885(18) . ?
C1 C6 1.3926(18) . ?
C2 C3 1.3921(18) . ?
C2 H2 0.95 . ?
C3 C4 1.3920(18) . ?
C4 C5 1.385(2) . ?
C4 H4 0.95 . ?
C5 C6 1.387(2) . ?
C5 H5 0.95 . ?
C6 H6 0.95 . ?
C7 C8 1.378(2) . ?
C7 H7 0.95 . ?
C8 C9 1.382(2) . ?
C8 H8 0.95 . ?
C9 C18 1.262(11) . ?
C9 C10 1.3879(18) . ?
C9 N2A 1.495(5) . ?
C9 N2B 1.72(8) . ?
C10 C11 1.3785(18) . ?
C10 H10 0.95 . ?
C11 H11 0.95 . ?
N2A N3A 1.238(5) . ?
N3A C12A 1.435(6) . ?
C12A C16A 1.387(4) . ?
C12A C13A 1.387(4) . ?
C13A C14A 1.387(4) . ?
C13A H13A 0.95 . ?
C14A N4A 1.316(4) . ?
C14A H14A 0.95 . ?
N4A C15A 1.324(4) . ?
C15A C16A 1.382(4) . ?
C15A H15A 0.95 . ?
C16A H16A 0.95 . ?
C12B C17 1.348(10) . ?
C12B C13B 1.39 . ?
C12B C16B 1.39 . ?
C13B C14B 1.39 . ?
C13B H13B 0.95 . ?
C14B N4B 1.39 . ?
C14B H14B 0.95 . ?
N4B C15B 1.39 . ?
C15B C16B 1.39 . ?
C15B H15B 0.95 . ?
C16B H16B 0.95 . ?
C17 C18 1.182(15) . ?
N2B N3B 1.25(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 0.84 1.93 2.7645(15) 176.1 1_556 yes
O2 H2A N4A 0.84 1.99 2.829(4) 174 2_666 yes
O2 H2A N4B 0.84 1.81 2.65(6) 177.9 2_666 yes
